Supporting Information

Stereomutation of Substituted Bullvalenes

Oussama Yahiaoui,[a] ‡ Harshal D. Patel,[a] ‡ Kylie S. Chinner,[a] Lukáš F. Pašteka,*[b] and Thomas Fallon*[a]

[a] Department of Chemistry, The University of Adelaide, Adelaide, SA 5005 (Australia),

thomas.fallon@adelaide.edu.au
[b] Department of Physical and Theoretical Chemistry, Faculty of Natural Sciences, Comenius University,
Bratislava, Slovakia, lukas.f.pasteka@uniba.sk

1. GENERAL INFORMATION.................................................................................................................................. 2
2 EXPERIMENTAL PROCEDURES ........................................................................................................................ 3
3. NMR DATA .......................................................................................................................................................... 8
4. NETWORK ANALYSIS ...................................................................................................................................... 27
5. COMPUTATIONAL ANALYSIS ......................................................................................................................... 29
CARTESIAN COORDINATES .................................................................................................................................... 32
6. REFERENCES ................................................................................................................................................... 97

S1
1. General Information

NMR spectra were recorded using either an Agilent 500 MHz DD2 console, Agilent 600 MHz DD2 console with an
Oxford 600 MHz magnet and Agilent cryoprobe, or Bruker UltraShield Avance III 600 MHz NMR Spectrometer.
Residual solvent peaks were used as an internal reference for 1H NMR spectra [CDCl3 d 7.26 ppm, TMS in CDCl3
d 0.00 ppm] and for 13C NMR spectra [CDCl3 d 77.16 ppm].1 The following abbreviations, or combinations thereof,
were used to describe 1H NMR multiplicities: s = singlet, d = doublet, t = triplet, m = multiplet, ap. = apparent, br. =
broad).

ESI-HRMS measurements (electrospray ionization - ESI) were recorded on an Agilent 6230 time-of-flight LC/MS
system.

IR spectra were recorded neat on a Perkin Elmer spectrum 100 FT-IR Spectrometer with an ATR.

Analytical thin-layer chromatography was conducted with commercial aluminium sheets coated with 0.25 mm silica
gel (E. Merck, silica gel 60 F254). Compounds were either visualized under UV-light at 254 nm, or by dipping the
plates in aqueous potassium permanganate or cerium ammonium molybdenite solution followed by heating.

Flash column chromatography was performed using a Biotage IsoleraTM One Flash Chromatography System using
iLOKTM Empty Solid Load Cartridges, and Carl Roth silica gel 60 (230 - 400 mesh grade). Hexanes and ethyl
acetate (EtOAc) were distilled prior to use in chromatography.

Melting points (m.p.) were determined using open ended capillary tubes and measured on a DigiMelt MPA161
melting point apparatus and are uncorrected.

Dimethyl sulfoxide was dried following the rapid purification procedure outlined in Purification of Laboratory
Chemicals (5th Edition, by Amarego and Chai), and stored over 4 Å molecular sieves under an atmosphere of
nitrogen. Tetrahydrofuran (THF) and dichloromethane were purified by a Pure SolvTM Micro solvent purification
system; tetrahydrofuran was then stored over 4 Å molecular sieves under an atmosphere of nitrogen.

Compounds bis-Bpin-Bullvalene 52, methylenehydroxy-trimethylsilyl-bullvalene 73, and bis-(methylenehydroxy)-

bullvalene 104 were synthesized according to procedures developed in our laboratory. 2-methylmalonic acid was
synthesised from diethyl malonate according to the procedure by Lu5 using MeI in place of CD3I. All other chemicals
were purchased from commercial suppliers and used as received.

S2
2 Experimental Procedures

Synthesis of trimethylsilyl-aldehyde-bullvalene 1 – Swern oxidation of methanol-trimethylsilyl-bullvalene 7

TMS Under a nitrogen atmosphere, an oven dried 10 mL round bottom flask was charged with oxalyl
chloride (18 µL, 0.20 mmol, 1.2 eq) and anhydrous dichloromethane (2 mL). The solution was
cooled down to – 78 °C. A mixture of anhydrous dimethyl sulfoxide (31 µL, 0.43 mmol, 2.5 eq) and
O dichloromethane (2 mL) was added slowly to the reaction mixture. After 5 minutes, methanol-
trimethylsilyl-bullvalene 7 (40 mg, 0.17 mmol, 1.0 eq) in dichloromethane (2 mL) was added. The reaction was
stirred for another 30 minutes, then triethylamine (120 µL, 0.86 mmol, 5.0 eq) was added. After 30 minutes, the
reaction was quenched by addition of ammonium chloride salt, followed by addition of water, and warming up
slowly to room temperature. The aqueous layer was extracted with dichloromethane. The organic phase was
washed three times with distilled water, once with saturated aqueous sodium chloride, dried over MgSO4, filtered,
and the solvent was evaporated under vacuum. The crude product was purified through flash column
chromatography using a 10/90 mixture of EtOAc/hexanes with 3% NEt3 and isolated as an oil (5 mg, 12% yield).
Rf = 0.25 (EtOAc/hexanes 10:90). IR (ATR): v/cm-1 = 3029, 2954, 2812, 2721, 1674, 1632, 1401, 1307, 1247,
1157, 1042, 910, 870, 832, 754, 730, 690. 1H NMR (600 MHz, CDCl3, – 60 °C) d = 9.03 (1H, s), 6.89 – 6.84 (1H,
m), 6.34 – 6.28 (1H, m), 5.99 – 5.92 (1H, m), 5.78 (1H, dd, J = 11.0, 8.7 Hz), 3.39 (1H, d, J = 8.7 Hz), 2.66 – 2.58
(3H, m), 0.03 (9H, s). 13C NMR (150 MHz, CDCl3, – 60 °C) d = 191.7 (CH) 151.6 (CH), 144.1 (C), 139.5 (C), 134.5
(CH), 128.4 (CH), 127.3 (CH), 26.9 (CH), 24.4 (CH), 23.5 (CH), 23.2 (CH), -2.5 (TMS). HRMS (ESI, m/z) calculated
for ([M+H]+) C14H19OSi+ 231.1200 found 231.1199.

Synthesis of bullvalene 2 – MeLi 1,2-addition to trimethylsilyl-aldehyde-bullvalene 1

HO Under a nitrogen atmosphere, an oven dried 5 mL round bottom flask was

Me TMS
charged with trimethylsilyl-aldehyde- bullvalene 1 (13 mg, 56 µmol, 1.0 eq)
OH and anhydrous tetrahydrofuran (1 mL). The solution was cooled to – 78
TMS
°C. Methyllithium lithium bromide (75 µL, 1.50 M in diethyl ether, 110 µmol,
2 major isomer 2:A 2.0 eq) was added slowly and the reaction stirred for 2 hours at – 78 °C.
The reaction was quenched with saturated ammonium chloride and
extracted with dichloromethane. The organic layer was washed with distilled water, then saturated aqueous sodium
chloride, dried over MgSO4, and filtered. The solvent was evaporated under vacuum. The desired product was
obtained as a yellow oil without any further purification (10 mg, 77% yield). IR (ATR): v/cm-1 = 3392, 3024, 2953,
2927, 1710, 1641, 1608, 1439, 1403, 1364, 1246, 1155, 1062, 1045, 886, 831, 747, 6789. 1H NMR (600 MHz,
CDCl3, – 60 °C) d = 6.30 (2.5H, d, J = 7.5 Hz, isomer 2:A), 6.27 – 6.17 (1.8H, m), 5.99 – 5.66 (18.8H, m), 4.23 –
4.10 (3.2H, m), 3.28 – 3.17 (1.1H, m), 2.75 (1H, d, J = 8.5 Hz, isomer 2:A), 2.55 – 2.43 (3.8H, m), 2.37 – 2.25
13
(9.2H, m), 1.82 (1.7H, br. s), 1.55 (1.9H, br. s), 1.35 – 1.15 (24.5H, m), 0.10 – -0.01 (45.0H, m). C NMR (150
MHz, CDCl3, – 60 °C) δ = 145.7, 145.3, 135.3, 135.1, 128.7, 128.2, 126.9, 126.7, 126.1, 121.4, 119.2, 73.4, 72.2,
33.0, 32.1, 31.5, 22.5, 21.9, 21.5, 21.4, 20.3, 20.2, 19.6, 19.5, 0.1, -1.6, -1.7, -2.1, -2.2, -2.2, -2.2, -2.2. HRMS (ESI,
m/z) calculated for ([M+K]+) C15H22OSiK+ 285.1072 found 285.1072.

S3
Synthesis of dialdehyde-bullvalene 3 – Swern oxidation of dimethanol-bullvalene 9
O Under a nitrogen atmosphere, an oven dried 100 mL round bottom flask was
O
charged with oxalyl chloride (0.54 mL, 6.3 mmol, 2.4 eq) and anhydrous
dichloromethane (25 mL). The solution was cooled down to – 78 °C. A mixture of
anhydrous dimethyl sulfoxide (0.93 mL, 13 mmol, 5.0 eq) in dichloromethane (15
O
O
mL) was added slowly to the reaction mixture. After 5 minutes dimethanol-

isomer a isomer b bullvalene 10 (500 mg, 2.63 mmol, 1.0 eq) in dichloromethane (10 mL) was
added. The reaction was stirred for another 2 hours, then triethylamine (3.7 mL,
26 mmol, 10.0 eq) was added. After 2 hours the reaction was quenched by addition of ammonium chloride salt,
followed by addition of water, and warming up slowly to room temperature. The mixture was extracted with
dichloromethane and the organic phase was washed three times with distilled water, three times with saturated
aqueous sodium chloride solution, dried over MgSO4, filtered, and the solvent was evaporated under vacuum. The
desired product was obtained as a yellow solid without any further purification (383 mg, 78% yield). Dialdehyde-
bullvalene 3 has been previously synthesised by Schröder.6 m.p. 107-118 °C. IR (ATR): v/cm-1 = 2924, 2831, 2734,
1665, 1629, 1403, 1349, 1307, 1194, 1165, 1145, 1009, 974, 927, 884, 852, 783, 762, 688, 665. 1H NMR (600
MHz, CDCl3, – 60 °C, isomer a : b ratio 73 : 27) d = 9.16 (0.3H, s), 8.96 (2.1H, s), 6.89 – 6.81 (2.3H, m), 6.73 (0.4H,
d, J = 8.9 Hz), 5.96 – 5.87 (1.4H, m), 5.67 – 5.55 (1.5H, m), 4.08 (1H, d, J = 8.9 Hz, isomer a), 3.60 (0.4H, ap. t, J
13
= 8.8 Hz, isomer b), 3.23 (0.4H, ap. t, J = 8.5 Hz), 2.88 – 2.76 (3.1H, m), 2.65 – 2.56 (0.8H, m). C NMR (150
MHz, CDCl3, – 60 °C) d = 193.7 (CH, isomer b), 191.0 (CH, isomer b), 190.8 (CH, isomer a), 151.8 (CH, isomer
b), 149.9 (CH, isomer a), 147.8 (CH, isomer b), 139.3 (C, isomer b), 138.4 (C, isomer a), 136.3 (C, isomer b),
128.8 (CH, isomer b), 127.6 (CH, isomer a), 127.1 (CH, isomer a), 124.7 (CH, isomer b), 25.3 (CH, isomer b),
25.3 (CH, isomer a), 24.7 (CH, isomer a), 22.1 (CH, isomer b), 21.1 (CH, isomer b), 20.5 (CH, isomer a), 18.6
(CH, isomer b). HRMS (ESI, m/z) calculated for ([M+H]+) C12H11O2+ 187.0754 found 187.0757.

Synthesis of bullvalene 4a – MeLi 1,2-addition to dialdehyde-bullvalene 3

HO Under a nitrogen atmosphere, an oven dried 25 mL round bottom flask was charged with
Me
dialdehyde-bullvalene 3 (200 mg, 1.07 mmol, 1.0 eq) and anhydrous tetrahydrofuran (7 mL). The
Me solution was cooled to – 78 °C. Methyllithium lithium bromide (1.9 mL, 1.50 M in diethyl ether, 2.9

OH
mmol, 2.65 eq) was added slowly and the reaction stirred for 2 hours at – 78 °C. The reaction was
quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic layer was washed
with distilled water, then saturated aqueous sodium chloride solution, dried with MgSO4, and filtered. The solvent
was evaporated under vacuum. The desired product was purified by flash column chromatography using a 20/80
mixture of EtOAc/hexanes with a gradient to 70/30 EtOAc/hexanes. The product was obtained as a yellow oil (149
mg, 64% yield). Rf = 0.20 (EtOAc/hexanes 50:50). IR (ATR): v/cm-1 = 3338, 3025, 2964, 2923, 2853, 1655, 1368,
1260, 1153, 1062, 1012, 881, 806, 765, 742, 701. 1H NMR (600 MHz, CDCl3, – 60 °C) d = 5.98 – 5.62 (m, 18.4H),
5.29 – 5.19 (m, 2.3H), 5.02 (ap. d, J = 16.3 Hz, 2.3H), 4.27 – 4.19 (m, 1.5H), 4.16 – 3.97 (m, 6.5H), 3.16 – 3.06
(m, 0.8H), 2.80 (ap. d, J = 8.8 Hz, 1H), 2.58 (ap. d, J = 9.1 Hz, 1.6H), 2.52 – 2.33 (m, 2.0H), 2.30 – 2.04 (m, 10.0H),
1.94 – 1.85 (m, 0.9H), 1.29 – 1.11 (m, 24.6H). 13C NMR (150 MHz, CDCl3, – 60 °C) d = 143.4 (C), 143.3 (C), 143.2
(C), 140.0 (C), 128.5 (CH), 127.8 (CH), 127.5 (CH), 127.1 (CH), 127.0 (CH), 126.1 (CH), 126.0 (CH), 122.2 (CH),
121.4 (CH), 119.0 (CH), 76.0 (CH), 74.8 (CH), 74.4 (CH), 73.4 (CH), 70.7 (CH), 70.5 (CH), 33.7 (C), 32.4 (C), 32.0
(CH), 29.5 (CH), 26.9 (CH), 26.1 (CH), 23.8 (CH), 23.1 (CH), 23.0 (CH), 22.1 (CH3), 21.6 (CH3), 21.4 (CH3), 21.1
(CH3), 20.9 (CH3), 20.2 (CH), 19.9 (CH), 19.9 (CH), 19.8 (CH), 19.5 (CH), 19.1 (CH), 18.9 (CH), 18.6 (CH), 18.5
(CH). HRMS (ESI, m/z) calculated for ([M+NH4]+) C14H22O2N+ 236.1645 found 236.1647.

S4
Synthesis of bullvalene 4b – 1-bromo-4-methoxybenzene 1,2-addition to dialdehyde-bullvalene 3
MeO Under a nitrogen atmosphere, an oven dried 5 mL round bottom flask was charged with 1-
bromo-4-methoxybenzene (130 µL, 670 µmol, 2.5 eq) and anhydrous tetrahydrofuran (2 mL).
OH
The solution was cooled to – 78 °C. N-butyllithium (270 µL, 2.50 M in cyclohexane, 670 µmol,
2.5 eq) was added slowly and the reaction stirred for 2 hours at – 78 °C. Dialdehyde-
bullvalene 3 (50 mg, 270 µmol, 1.0 eq) was added and the reaction stirred for 1 hour at – 78
OH
°C, and 3 hours at room temperature. The reaction was quenched with saturated aqueous
ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed
MeO
with water, then saturated aqueous sodium chloride solution, dried with MgSO4, and filtered.
The solvent was evaporated under vacuum. Purification through flash column chromatography using a 10/90
mixture of EtOAc/hexanes yielded the target compound as an oil (70 mg, 65% yield). Rf = 0.25 (EtOAc/hexanes
10:90). IR (ATR): v/cm-1 = 3368, 3090, 3028, 2836, 1610, 1584, 1509, 1463, 1441, 1302, 1244, 1171, 1108, 1032,
907, 832, 727. 1H NMR (600 MHz, CDCl3, – 60 °C) δ = 7.29 (3.0H, ap. d, J = 8.0 Hz), 7.24 – 7.07 (10.4H, m), 6.86
– 6.71 (14.4H, m), 6.06 (1.2H, br. s), 5.89 (3.4H, br. s), 5.82 – 5.67 (4.8H, m), 5.30 – 5.16 (3.4H, m), 5.00 – 4.78
(3.4H, m), 4.78 – 4.61 (3.6H, m), 3.81 – 3.69 (23.0H, m), 2.55 – 2.41 (2.0H, m), 2.27 (1H, ap. d, J = 9.1 Hz), 2.24
– 2.05 (8.7H, m). 13C NMR (150 MHz, CDCl3, – 60 °C) δ = 158.2, 157.8, 157.6, 142.5, 142.3, 135.0, 132.8, 128.5,
128.3, 127.7, 126.9, 126.5, 123.9, 112.9, 112.8, 55.2, 55.2, 55.2, 55.2, 32.4, 31.8, 21.4, 19.6, 19.4, 19.1, 14.5,
14.1. HRMS (ESI, m/z) calculated for ([M+Na]+) C26H26O4Na+ 425.1723 found 425.1728.

Synthesis of bullvalene 4c – 4-bromo-1,2-dimethoxybenzene 1,2-addition to dialdehyde-bullvalene

OMe Under a nitrogen atmosphere, an oven dried 5 mL round bottom flask was charged with 4-
OMe
bromo-1,2-dimethoxybenzene (60 µL, 400 µmol, 2.5 eq) and anhydrous tetrahydrofuran
HO
(2 mL). The solution was cooled to – 78 °C. N-butyllithium (160 µL, 2.50 M in cyclohexane,
400 µmol, 2.5 eq) was added slowly and the reaction stirred for 2 hours at – 78 °C.
OH Dialdehyde-bullvalene 3 (30 mg, 160 µmol, 1.0 eq) was added and the reaction stirred for
1 hour at – 78 °C and 3 hours at room temperature. The reaction was quenched with
MeO saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The
MeO organic layer was washed with water, then saturated aqueous sodium chloride solution,
dried with MgSO4, and filtered. The solvent was evaporated under vacuum. Purification through flash column
chromatography using a 20/80 mixture of EtOAc/hexanes yielded the target compound as an oil (30 mg, 40%
yield). Rf = 0.23 (EtOAc/hexanes 20:80). IR (ATR): v/cm-1 = 3486, 2934, 2835, 1732, 1510, 1462, 1414, 1256,
1230, 1133, 1024, 864, 811, 745. 1H NMR (600 MHz, CDCl3, – 60 °C) d = 6.99 (1.0H, ap. d, J = 8.0 Hz), 6.91 –
6.64 (13.7H, m), 6.00 – 5.93 (1.3H, m), 5.88 (2.9H, br. s), 5.81 – 5.74 (1.7H, m), 5.60 – 5.53 (1.2H, m), 5.29 (1.2H,
ap. t, J = 9.9 Hz), 5.24 (0.9H, br. s), 5.00 (1.7H, br. s), 4.75 (1.0H, br. s), 4.72 – 4.61 (1.8H, m), 3.92 – 3.69 (30.9H,
m), 2.51 (1H, ap. d, J = 8.9 Hz), 2.24 – 2.18 (2.9H, m), 2.18 – 2.08 (3.7H, m). 13C NMR (150 MHz, CDCl3, – 60 °C)
d = 147.7, 147.6, 147.4, 147.4, 146.9, 146.7, 142.4, 142.0, 141.8, 135.5, 135.2, 132.9, 127.8, 127.1, 126.5, 124.3,
119.4, 117.5, 117.2, 109.6, 109.3, 108.4, 107.8, 55.8, 55.8, 55.7, 55.7, 55.6, 32.8, 28.1, 19.7, 19.5, 19.3. HRMS
(ESI, m/z) calculated for ([M+Na]+) C28H30O6Na+ 485.1935 found 485.1937.

S5
Synthesis of bullvalene 6a – bis-Bpin-bullvalene 5 1,4-addition to ethyl cinnamate
CO2Et Bis-Bpin-bullvalene 5 (20 mg, 52 μmol, 1.0 eq), ethyl cinnamate (20 mg, 120 μmol, 2.2 eq),
Ph
[Rh(COD)Cl]2 (6 mg, 10 μmol, 25 mol%), nitrogen degassed THF (0.25 mL), and nitrogen
degassed 10% aqueous NaHCO3 solution (0.1 mL) were added to a seal tube under an
CO2Et
atmosphere of nitrogen. The mixture was stirred at 60 °C for 2.5 hours. After cooling to room
Ph
temperature, the reaction was diluted with saturated aqueous NH4Cl solution and extracted
with DCM. The organic layer was dried with MgSO4 and filtered through a short plug of cotton wool. The solvents
were removed in vacuo and the material was purified by flash column chromatography using a 10/90 mixture of
EtOAc/hexanes. The product was obtained as a pale-yellow oil (12 mg, 48% yield). Rf = 0.16 (EtOAc/hexanes
10:90). IR (ATR): v/cm-1 = 2980, 1731, 1369, 1253, 1153, 1032, 756, 699. 1H NMR (600 MHz, CDCl3, – 60 °C) d =
7.40 (ap. t, J = 7.4 Hz, 5.4H), 7.36 – 7.27 (m, 37.5H), 7.25 – 7.17 (m, 31.1H), 7.16 – 7.13 (m, 2.8H), 7.13 – 7.04
(m, 23.0H), 6.84 (d, J = 7.4 Hz, 5.3H), 5.88 – 5.55 (m, 31.6H), 5.43 (ap. t, J = 9.7 Hz, 2.0H), 5.41 – 5.34 (m, 3.1H),
5.25 (d, J = 9.1 Hz, 1.3H), 5.22 (d, J = 9.1 Hz, 1H), 5.14 (ap. t, J = 9.9 Hz, 2.6H), 5.01 (ap. t, J = 10.0 Hz, 2.1H),
4.10 – 3.90 (m, 38.1H), 3.89 – 3.75 (m, 16.1H), 3.64 – 3.59 (m, 2.6H), 3.22 – 3.16 (m, 1.0H), 2.98 – 2.90 (br. s,
3.6H), 2.82 – 2.54 (m, 26.3H), 2.53 – 2.37 (m, 15.3H), 2.35 – 2.20 (m, 18.3H), 2.18 – 1.95 (m, 20.3H), 1.92 – 1.81
(m, 9.1H), 1.80 – 1.74 (m, 3.0H), 1.22 – 1.03 (m, 74.1H). 13
C NMR (150 MHz, CDCl3, – 60 °C) d = 172.4, 172.4,
172.4, 172.4, 172.4, 172.3, 172.1, 172.1, 172.1, 143.0, 142.6, 142.4, 142.3, 142.2, 142.1, 142.1, 142.0, 141.9,
141.7, 141.5, 141.4, 140.6, 138.4, 137.6, 128.8, 128.5, 128.4, 128.4, 128.3, 128.3, 128.2, 128.2, 128.0, 128.0,
128.0, 127.9, 127.7, 127.7, 127.4, 126.9, 126.8, 126.6, 126.5, 126.3, 126.1, 120.2, 118.5, 118.4, 60.7, 60.6, 60.6,
60.5, 60.5, 60.3, 50.2, 49.7, 49.5, 49.5, 49.3, 49.0, 48.4, 47.3, 39.6, 39.4, 38.8, 38.6, 38.1, 35.4, 33.9, 32.8, 20.0,
19.8, 19.7, 19.6, 19.4, 18. 9, 18.7, 18.4, 14.2, 14.2, 14.1, 14.1, 14.1, 14.1. HRMS (ESI, m/z) calculated for ([M+Na]+)
C32H34O4Na+ 505.2349 found 505.2353.

Synthesis of bullvalene 6b – bis-Bpin-bullvalene 5 1,4-addition to dimethyl fumarate

CO2Me Bis-Bpin-bullvalene 5 (20 mg, 52 μmol, 1.0 eq), dimethyl fumarate (17 mg, 120 μmol, 2.2
MeO2C
eq), [Rh(COD)Cl]2 (6 mg, 10 μmol, 25 mol%), nitrogen degassed THF (0.25 mL), and
nitrogen degassed 10% aqueous NaHCO3 solution (0.1 mL) were added to a seal tube
CO2Me
under an atmosphere of nitrogen. The mixture was stirred at 60 °C for 1 hour. After cooling
CO2Me
to room temperature, the reaction was diluted with saturated aqueous NH4Cl solution and
extracted with DCM. The organic layer was dried with MgSO4 and filtered through a short plug of cotton wool. The
solvents were removed in vacuo and the material was purified by flash column chromatography using a 10/90
mixture of EtOAc/hexanes with a gradient to 30/70 EtOAc/hexanes. The product was obtained as a pale-yellow oil
(16 mg, 73% yield). Rf = 0.20 (EtOAc/hexanes 30:70). IR (ATR): v/cm-1 = 2953, 1728, 1436, 1253, 1162, 1006,
730. 1H NMR (600 MHz, CDCl3, – 60 °C) d = 5.93 – 5.72 (m, 12.8H), 5.72 – 5.49 (m, 10.3H), 3.76 (br. s, 3.6H),
3.74 – 3.62 (m, 61.8H), 3.53 – 3.37 (m, 9.4H), 3.28 (ap. dd, J = 11.5, 3.2 Hz, 1H), 3.07 – 2.84 (m, 11.0H), 2.56 –
2.32 (m, 16.1H), 2.32 – 2.07 (m, 17.3H), 2.07 – 1.94 (m, 1.6H). 13
C NMR (150 MHz, CDCl3, – 60 °C) d = 173.6,
173.5, 173.5, 173.5, 173.4, 173.4, 173.3, 173.3, 173.2, 172.6, 172.6, 172.5, 172.5, 172.4, 172.4, 172.4, 172.4,
172.3, 136.5, 136.3, 136.1, 136.0, 135.6, 135.3, 135.3, 134.9, 134.1, 134.0, 133.8, 133.8, 127.8, 127.3, 127.3,
127.2, 126.3, 126.0, 125.8, 125.5, 125.0, 124.8, 124.5, 124.2, 123.8, 123.6, 123.4, 123.0, 53.2, 53.0, 53.0, 52.9,
52.9, 52.9, 52.9, 52.8, 52.8, 52.8, 52.8, 52.8, 52.4, 52.4, 52.4, 52.4, 52.4, 52.3, 51.1, 50.9, 50.8, 50.1, 49.9, 49.8,
49.8, 49.6, 49.5, 49.2, 37.4, 36.3, 36.1, 35.9, 35.8, 35.7, 35.4, 35.3, 35.2, 35.0, 31.4, 31.3, 31.0, 21.1, 20.9, 20.7,
20.5, 20.2, 20.2, 20.1, 19.9, 19.8, 19.8, 19.7, 19.6, 19.6, 19.2, 19.2, 19.1. HRMS (ESI, m/z) calculated for ([M+Na]+)
C22H26O8Na+ 441.1520 found 441.1524.

S6
Synthesis of bullvalene 6c – bis-Bpin-bullvalene 5 1,4-addition to 2-cyclohexen-1-one
O Bis-Bpin-bullvalene 5 (20 mg, 52 μmol, 1.0 eq), 2-cyclohexen-1-one (11 μL, 120 μmol, 2.2 eq),
[Rh(COD)Cl]2 (6 mg, 10 μmol, 25 mol%), nitrogen degassed THF (0.25 mL), and nitrogen
degassed 10% aqueous NaOH solution (0.1 mL) were added to a seal tube under an
atmosphere of nitrogen. The mixture was stirred at 60 °C and judged complete by TLC within
O 1 hour. After cooling to room temperature, the reaction was diluted with saturated aqueous
NH4Cl solution and extracted with DCM. The organic layer was dried with MgSO4 and filtered
through a short plug of cotton wool. The solvents were removed in vacuo and the material was purified by flash
column chromatography using a 10/90 mixture of EtOAc/hexanes with a gradient to 40/60 EtOAc/hexanes. The
product was obtained as a pale-yellow oil (12 mg, 71% yield). Rf = 0.20 (EtOAc/hexanes 30:70). IR (ATR): v/cm-
1
= 3024, 2935, 2864, 1706, 1420, 1315, 1222, 912, 729. 1H NMR (600 MHz, CDCl3, – 60 °C) d = 5.94 – 5.68 (m,
6.3H), 5.66 – 5.53 (m, 2.2H), 5.52 – 5.43 (m, 1H), 2.55 – 1.78 (m, 41.3H), 1.74 – 1.37 (m, 10.1H). 13C NMR (150
MHz, CDCl3, – 60 °C) d = 213.2, 213.0, 212.7, 212.6, 143.6, 143.5, 142.9, 142.8, 142.7, 142.7, 140.4, 140.4, 140.3,
127.2, 127.1, 126.9, 126.9, 126.6, 126.5, 126.1, 119.7, 119.7, 119.4, 119.2, 119.1, 119.0, 118.9, 118.9, 47.9, 47.8,
47.7, 47.6, 47.5, 47.1, 47.0, 46.9, 46.8, 46.7, 46.6, 46.6, 46.3, 46.1, 45.9, 41.4, 41.3, 41.2, 41.1, 38.6, 38.0, 32.9,
32.8, 32.8, 31.2, 30.9, 30.3, 30.3, 29.9, 29.9, 29.6, 29.4, 29.2, 29.1, 25.3, 24.9, 24.7, 24.7, 24.6, 24.5, 24.4, 22.0,
21.9, 20.0, 19.7, 19.7, 19.2, 19.2, 18.8, 18.8. HRMS (ESI, m/z) calculated for ([M+H]+) C22H27O2+ 323.2006 found
323.2007.

Synthesis of tethered bullvalene dimer 8 – Steglich esterification of methanol-trimethylsilyl-bullvalene 7 with 2-

methylmalonic acid
O O TMS Under a nitrogen atmosphere, an oven dried 5 mL

O O
round bottom flask was charged with 2-methylmalonic
O
Me acid (6 mg, 50 µmol, 0.5 eq), 4-dimethylaminopyridine
TMS
TMS (3 mg, 20 µmol, 0.2 eq), N,N’-dicyclohexylcarbodiimide
8 isomer A
major by NMR (22 mg, 110 µmol, 1.0 eq), and anhydrous
dichloromethane (2 mL) with stirring for 30 minutes at 0 °C. Methanol-trimethylsilyl-bullvalene 7 (25 mg, 110 µmol,
1.0 eq) was added and the reaction stirred at room temperature overnight. The suspension was passed through a
pad of celite. The organic layer was washed three times with 1M aqueous sodium hydroxide, and the solvent was
evaporated under vacuum. The crude product was purified through flash column chromatography using a 5/95
mixture of EtOAc/hexanes. The desired product was obtained as yellow oil (20 mg, 34% yield). Rf = 0.13
(EtOAc/hexanes 5:95). IR (ATR): v/cm-1 = 3026, 2953, 2925, 1735, 1608, 1459, 1377, 1342, 1246, 1175, 1081,
1042, 1005, 950, 833, 751, 690. 1H NMR (600 MHz, CDCl3, – 60 °C) d = 6.34 – 6.28 (1.0H, m, isomer A), 6.26
(0.4H, m), 6.07 – 5.97 (1.3H, m), 5.97 – 5.75 (5.1H, m), 4.54 (0.5H, ap. t, J = 12.3 Hz), 4.45 (0.9H, ap. d, J = 12.0
Hz), 4.40 (0.3H, ap. d, J = 12.2 Hz), 4.35 (0.8H, ap. d, J = 12.0 Hz), 4.30 (0.2H, ap. d, J = 12.5 Hz), 3.07 (1H, br.
s), 2.47 (0.8H, ap. d, J = 8.6 Hz, isomer A), 2.45 – 2.20 (8.1H, m), 1.96 (2.4H, br. s), 1.72 (2.8H, br. s), 1.63 – 1.54
(2.0H, m), 1.50 – 1.37 (2.3H, m), 1.33 – 0.99 (24.7H, m), 0.89 – 0.69 (7.0H, m), 0.10 – 0.01 (16.2H, m). 13C NMR
(150 MHz, CDCl3, – 60 °C) d = 177.7, 175.1, 172.9, 142.4 (isomer A), 135.7, 135.6 (isomer A), 135.0 (isomer A),
134.3, 132.8, 127.8, 127.5 (isomer A), 127.5, 127.2, 127.2 (isomer A), 127.0, 126.6 (isomer A), 126.1, 125.5,
70.0, 69.0, 56.0, 35.0, 34.2, 33.9, 33.8, 32.0, 31.7, 29.9, 29.6, 27.5, 27.4, 27.3, 26.1, 25.2, 25.1, 22.9, 22.1, 21.7,
20.7, 20.4, 20.4, 20.2, 20.1, 19.4, 19.3, 19.0, 14.5, 9.1, 9.1, 9.0, 0.1, -1.2, -1.9, -2.1, -2.2, -2.3, -2.3. HRMS (ESI,
m/z) calculated for ([M+Na]+) C32H42O4Si2Na+ 569.2514 found 569.2506.

S7
 3. NMR Data

7.26 CDCl3
TMS

O
1
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S1: 1H NMR of trimethylsilyl-aldehyde-bullvalene 1 at room temperature.

7.26 CDCl3

TMS
9.03

6.87
6.87
6.86
6.86
6.86
6.31
6.31
6.30
5.97
5.96
5.95
5.94
5.94
5.80
5.78
5.78
5.77
3.40
3.39
2.63
2.63
2.63
2.62

0.03

O
1
600 MHz 1H NMR
CDCl3, -60 oC
1.00

1.06

1.01
1.38
1.29

0.91

3.01

8.86

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S2: 1H NMR of trimethylsilyl-aldehyde-bullvalene 1 at - 60 °C.

S8
 77.2 CDCl3
191.7

151.6
144.1
139.5
134.5
128.4
127.3

26.9
24.4
23.5
23.2

-2.5
TMS

O
1
150 MHz 13C NMR
CDCl3, -60 oC

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
f1 (ppm)

Figure S3: 13C NMR of trimethylsilyl-aldehyde-bullvalene 1 at - 60 °C.

7.26 CDCl3

HO
Me

TMS

2
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S4: 1H NMR of bullvalene 2 at room temperature.

S9
 7.26 CDCl3
HO
Me

TMS

2
600 MHz 1H NMR
CDCl3, -60 oC

18.79

24.46

45.01
2.50
1.78

3.17

1.09
1.00
3.77
9.15

1.69
1.90
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S5: 1H NMR of bullvalene 2 at - 60 °C.

77.2 CDCl3
145.7
145.3
135.3
135.1
128.7
128.2
126.9
126.7
126.1
121.4
119.2

73.4
72.2
33.0
32.1
31.5
22.5
21.9
21.5
21.4
20.3
20.2
19.6
19.5

-1.6
-1.7
-2.1
-2.2
-2.2
-2.2
-2.2
0.1

HO
Me

TMS

2
150 MHz 13C NMR
CDCl3, -60 oC

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
f1 (ppm)

Figure S6: 13C NMR of bullvalene 2 at - 60 °C.

S10
 7.26 CDCl3
H TMS
H
OH

major isomer 2:A

600 MHz 1H NMR
CDCl3, -60 oC
2.50

1.00
6.8 6.6 6.4 6.2 6.0 5.8 3.2 3.0 2.8 2.6 2.4
f1 (ppm) f1 (ppm)
18.79

24.46

45.01
2.50
1.78

3.17

1.09
1.00
3.77
9.15

1.69
1.90
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S7: 1H NMR of bullvalene 2 at - 60 °C (figure S5) – Assignment of isomer A 2:A. A distinctive downfield
methine doublet is characteristic of an apical bridgehead proton being flanked by two substituents. A
characteristically downfield alkenic doublet is typical of the proton being adjacent to a TMS group.3

S11
 7.26 CDCl3
O

3
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S8: 1H NMR of dialdehyde-bullvalene 3 at room temperature.

7.26 CDCl3
9.16
8.96

6.87
6.86
6.85
6.84
6.74
6.72
5.93
5.92
5.91
5.90
5.89
5.65
5.63
5.61
5.60
5.59
5.58
4.09
4.08
3.62
3.60
3.59
3.25
3.23
3.22
2.85
2.84
2.83
2.82
2.81
2.80
2.79
2.62
2.61
2.60
2.58
O

3
600 MHz 1H NMR
CDCl3, -60 oC
0.34
2.13

2.33
0.38

1.41
1.52

1.00
0.35
0.38
3.10
0.81

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S9: 1H NMR of dialdehyde-bullvalene 3 at - 60 °C.

S12
 77.2 CDCl3
193.7
191.0
190.8

151.8
149.9
147.8
139.3
138.4
136.3
128.8
127.6
127.1
124.7

25.3
25.3
24.7
22.1
21.1
20.5
18.6
O

3
150 MHz 13C NMR
CDCl3, -60 oC

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
f1 (ppm)

Figure S10: 13C NMR of dialdehyde-bullvalene 3 at - 60 °C.

7.26 CDCl3

HO
Me

Me

OH
4a
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S11: 1H NMR of bullvalene 4a at room temperature.

S13
 7.26 CDCl3
HO
Me

Me

OH
4a
600 MHz 1H NMR
CDCl3, -60 oC

18.37

24.59
2.32
2.25

1.45
6.52

0.83
1.00
1.64
2.01
9.96
0.93
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S12: 1H NMR of bullvalene 4a at - 60 °C.

77.2 CDCl3
143.4
143.3
143.2
140.0
128.5
127.8
127.5
127.1
127.0
126.1
126.0
122.2
121.4
119.0

76.0
74.8
74.4
73.4
70.7
70.5
33.7
32.4
32.0
29.5
26.9
26.1
23.8
23.1
23.0
22.1
21.6
21.4
21.1
20.9
20.2
19.9
19.9
19.8
19.5
19.1
18.9
18.6
18.5
HO
Me

Me

OH
4a
150 MHz 13C NMR
CDCl3, -60 oC

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
f1 (ppm)

Figure S13: 13C NMR of bullvalene 4a at - 60 °C.

S14
 0.00 TMS
MeO

OH

OH

MeO

4b
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S14: 1H NMR of bullvalene 4b at room temperature.

7.26 CDCl3

MeO

OH

OH

MeO

4b
600 MHz 1H NMR
CDCl3, -60 oC
10.39
14.36

22.96
2.99

1.20
3.40
4.80

3.38
3.36
3.62

2.00
1.00
8.68

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S15: 1H NMR of bullvalene 4b at - 60 °C.

S15
 77.2 CDCl3
158.2
157.8
157.6
142.5
142.3
135.0
132.8
128.5
128.3
127.7
126.9
126.5
123.9
112.9
112.8

55.2
55.2
55.2
55.2

32.4
31.8
21.4
19.6
19.4
19.1
14.5
14.1
MeO

OH

OH

MeO

4b
150 MHz 13C NMR
CDCl3, -60 oC

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
f1 (ppm)

Figure S16: 13C NMR of bullvalene 4b at - 60 °C.

7.26 CDCl3

OMe
OMe

HO

OH

MeO

MeO

4c
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S17: 1H NMR of bullvalene 4c at room temperature.

S16
 7.26 CDCl3
OMe
OMe

HO

OH

MeO

MeO

4c
600 MHz 1H NMR
CDCl3, -60 oC
13.66

30.85
1.02

1.34
2.88
1.70
1.18
1.22
0.88
1.70
0.96
1.84

1.00
2.89
3.69
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S18: 1H NMR of bullvalene 4c at - 60 °C.

77.2 CDCl3
147.7
147.6
147.4
147.4
146.9
146.7
142.4
142.0
141.8
135.5
135.2
132.9
127.8
127.1
126.5
124.3

109.6
109.3
108.4
107.8
119.4
117.5
117.2

55.8
55.8
55.7
55.7
55.6

32.8
28.1
19.7
19.5
19.3

OMe
OMe

HO

OH

MeO

MeO

4c
150 MHz 13C NMR
CDCl3, -60 oC

210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10
f1 (ppm)

Figure S19: 13C NMR of bullvalene 4c at - 60 °C.

S17
 7.26 CDCl3
CO2Et
Ph

CO2Et

Ph

6a
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S20: 1H NMR of bullvalene 6a at room temperature.

7.26 CDCl3

CO2Et
Ph

CO2Et

Ph

6a
600 MHz 1H NMR
CDCl3, -60 oC
37.51
31.07

22.95

31.65

38.07
16.06

26.28
15.33
18.33
20.34

74.07
5.43

2.81

5.29

2.03
3.08
1.26
1.00
2.62

2.57
1.02
3.55

9.12
3.01
2.11

10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S21: 1H NMR of bullvalene 6a at - 60 °C.

S18
 Ph
120.2 172.4
172.3
118.5 172.4
172.1
172.4

6a
Ph
118.4 172.1
172.4

CO2Et
143.0
172.4
142.6

CDCl3, -60 oC
172.3
142.3

Ph
CO2Et
172.1

150 MHz 13C NMR

142.0
172.1
141.5
172.1
141.4

6a
Ph
128.8

CO2Et
77.2 CDCl3 128.5

120 115 110 105 100 95

60.7 143.0 128.4

CDCl3, -60 oC
60.6 142.6 128.4

CO2Et

150 MHz 13C NMR

90
60.6 142.4 128.3
60.5 142.3 128.3
60.5

85
142.2 128.2

Ph
60.3 142.1 128.2
50.2 142.1

80
128.0
49.7 142.0 128.0

6a
Ph
Figure S22: 13C NMR of bullvalene 6a at - CO
49.5 141.9

75
128.0

602Et
49.5 141.7 127.9

°C.
49.3 141.5 127.7

CDCl3, -60 oC
49.0 141.4 126.9

CO2Et

150 MHz 13C NMR

48.4 140.6 126.6

f1 (ppm)
47.3 138.4

f1 (ppm)
f1 (ppm)
126.3

210 200 190 180 170 160 150 140 130 120 110 100 90
39.6 137.6 77.2 CDCl3

70 65 60
39.4 128.8 60.7

80
38.8 128.5 60.6

55
38.6 128.4 60.6

70
38.1 128.4 60.5

50
35.4 128.3 60.5

60
33.9 128.3 60.3

45
32.8 128.2 49.0
50
20.0 128.2 48.4

Figure S23: Expanded 13C NMR of bullvalene 6a at - 60 °C from figure S22.

40
19.8 128.0 40 38.6
19.7 128.0 38.1

35
19.6 128.0 19.8
30

19.4 127.9 19.7

30
18.9 127.7 19.6
20

18.7 127.7 19.4

25
18.4 127.4 18.9
10

14.2 126.9 14.2

20
14.2 126.8 14.2
0

14.1 126.6 14.1

15
14.1 126.5 14.1
-10

14.1 126.3 14.1

10
14.1 126.1 14.1

174 172 170 168 166 164 162 160 158 156 154 152 150 148 146 144 142 140 138 136 134 132 130 128 126 124

S19
 7.26 CDCl3
CO2Me
MeO2C

CO2Me

CO2Me

6b
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S24: 1H NMR of bullvalene 6b at room temperature.

7.26 CDCl3

CO2Me
MeO2C

CO2Me

CO2Me

6b
600 MHz 1H NMR
CDCl3, -60 oC
12.79
10.29

61.79

10.98
16.06
17.33
3.65

9.41
1.00

1.59

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S25: 1H NMR of bullvalene 6b at - 60 °C.

S20
 173.6 173.5

190
173.5

MeO2C
173.5
173.5 173.5
173.5 173.4

185
37.4

6b
173.4 173.4
36.3 53.2 173.4 173.3

180
CO2Me
36.1 173.3

CO2Me
53.0 173.3

CDCl3, -60 oC
35.9 53.0 173.3 173.2

150 MHz 13C NMR

35.8 173.2 172.5

175
52.9

CO2Me
35.7 52.9 172.6 172.4
35.4 52.9 172.6 172.4

170
35.3 52.9 172.5 172.4
35.2 52.8 172.5 172.3
35.0 172.4

165
52.8 135.6
52.8 172.4 134.9
52.8 172.4 134.1

160
31.4 172.4
52.8 127.8
31.3 172.3
52.4 127.2
31.0

155
52.4 136.5 126.3
52.4 136.3 77.2 CDCl3
52.4 136.1 53.2

150
Figure S26: 13C NMR of bullvalene 6b at - 60 °C.
52.4 136.0 53.0
52.3 135.6 52.9
51.1 135.3 52.9

f1 (ppm)
f1 (ppm)
135.3

f1 (ppm)
f1 (ppm)
50.9 52.9

210 200 190 180 170 160 150 140 130 120 110 100 90
134.9 52.9

145 140
50.8
134.1 52.8

80
21.1 134.0 52.8
50.1

135
20.9 133.8 52.8
49.9

70
20.7 133.8 52.8
49.8 127.8 52.4

130
20.5 49.8

60
20.2 127.3 52.4
49.6 127.3 52.4
20.2

125
49.5
50
127.2 52.4

Figure S27: Expanded 13C NMR of bullvalene 6b at - 60 °C from figure S26.

20.1 49.2
19.9 126.3 40 52.4
126.0

120
19.8 52.3
19.8 125.8 51.1
30

MeO2C
19.7 125.5 50.1

115
19.6 125.0 49.8
20

19.6 124.8 49.5

6b
110
19.2 124.5 35.4
10

19.2 124.2 20.2

CO2Me

CO2Me
19.1 123.8 20.2

105

CDCl3, -60 oC
0

MeO2C
123.6 20.1

150 MHz C NMR

123.4 19.8

CO2Me
-10

123.0 19.7

6b
19.2

56.0 55.5 55.0 54.5 54.0 53.5 53.0 52.5 52.0 51.5 51.0 50.5 50.0 49.5 49.0 48.5 48.0 1347.5 47.0 46.5

41 40 39 38 37 36 35 34 33 32 31 30 29 28 27 26 25 24 23 22 21 20 19 18 17 16 15 14 13
CO2Me

100 CO2Me

CDCl3, -60 oC
150 MHz 13C NMR
CO2Me

S21
 7.26 CDCl3
O

6c
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S28: 1H NMR of bullvalene 6c at room temperature.

7.26 CDCl3

6c
600 MHz 1H NMR
CDCl3, -60 oC
41.31

10.05
6.29
2.19
1.00

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S29: 1H NMR of bullvalene 6c at - 60 °C.

S22
 213.2

35
213.2
213.0

150 MHz
213.0
212.7

6c
212.7

34
212.6
142.9
32.9 142.8

CDCl3, -60 oC

33
32.8 142.7

O
6c

C NMR
54 13 53 52
32.8 O 142.7
31.2 140.3

32
51
30.9 127.2

CDCl3, -60 oC
O
30.3 127.1

150 MHz 13C NMR

31
30.3 126.9

50
47.9

6c
29.9 126.6

O
47.8

30
29.9 119.7
47.7

49
29.6 119.7

CDCl3, -60 oC
47.6
29.4 119.2

29
47.5

150 MHz 13C NMR

48
29.2 119.1
47.1
29.1 77.2 CDCl3
47.0

28
47.9

47
46.9
47.8
46.8
47.0

27
46.7

46
46.8
46.6

Figure S30: 13C NMR of bullvalene 6c at - 60 °C.

25.3 46.7
46.6

26
24.9 143.6 46.6
46.3
24.7 143.5 46.6
46.1

f1 (ppm)

f1 (ppm)

f1 (ppm)
f1 (ppm)
46.1

25
45 44
24.7 45.9 142.9

210 200 190 180 170 160 150 140 130 120 110 100 90
24.6 142.8 45.9
24.5 142.7 41.4

24
43
80
24.4 142.7 41.3
140.4 41.2

70

42

23
41.4 140.4 41.1
41.3 140.3 38.6

60
22.0 41.2 31.2

41
127.2

22
21.9 41.1 127.1 30.9
50
126.9 29.9

Figure S31: Expanded 13C NMR of bullvalene 6c at - 60 °C from figure S30.

40

21
126.9 29.6
20.0
40
126.6 29.2
19.7

39
29.1

20
19.7 126.5
30

38.6 24.9
19.2 126.1
38.0 24.7

38
119.7

19
19.2
20

119.7 24.7
18.8 20.0
119.4

37
10

18.8 19.7

18
119.2
119.1 19.7
0

36
119.0 19.2

17
118.9 19.2
-10

18.8

35
118.9

215 210 205 200 195 190 185 180 175 170 165 160 155 150 145 140 135 130 125 120 115 110 105

16
18.8

S23
 7.26 CDCl3
O O

O O
Me

TMS TMS
8
500 MHz 1H NMR
CDCl3, RT

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S32: 1H NMR of tethered bullvalene dimer 8 at room temperature.

7.26 CDCl3

O O

O O
Me

TMS TMS
8
600 MHz 1H NMR
CDCl3, -60 oC
24.71

16.17
1.02
0.38
1.33
5.06

0.51
0.89
0.25
0.78
0.22

1.00

0.79
8.09
2.41
2.76
1.98
2.31

6.97

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S33: 1H NMR of tethered bullvalene dimer 8 at - 60 °C.

S24
 175.1

TMS

185
142.4
70.0

70
135.7
69.0 135.6

180
135.0

65
127.5

O
177.7
175.1 127.5
56.0

175
Me
172.9 127.2

60
35.0 O
127.2
34.2
O
127.0
33.9

CDCl3, -60 oC
126.6

55
170
33.8

150 MHz 13C NMR

TMS
TMS
77.2 CDCl3
32.0
70.0
31.7

50
69.0
29.9

165
56.0
29.6

150
TMS

O
O
35.0
27.5

45
34.2

O
O

CDCl
27.4

160
33.9

3
MHz
,
27.3

88
Me
Me
33.8

40
26.1

O
O

150 MHz 13C

32.0

CDCl3 , -60
25.2

O
O
31.7

155
25.1

-60 oCC
29.9

35
22.9

13 NMR
C oNMR
29.6
22.1
27.5

f1 (ppm)
150
21.7

f1 (ppm)
f1 (ppm)

30
27.4
20.7

210 200 190 180 170 160 150 140 130 120 110 100 90
27.3

TMS
20.4

TMS
25.2
20.4

80

25
145
25.1

Figure S34: 13C NMR of tethered bullvalene dimer 8 at - 60 °C.

20.2
142.4 22.9
20.1

70
22.1
19.4

20
21.7

140
19.3

60
20.7
19.0 135.7 20.4

15
14.5 135.6
50
20.2

135
135.0 20.1
9.1 134.3
40
19.4

10
9.1 132.8 19.3
9.0 127.8
30

130
19.0

5
127.5 14.5
0.1
127.5
20

-1.2 9.1

Figure S35: Expanded 13C NMR of tethered bullvalene dimer 8 at - 60 °C from figure S34.
127.2 9.1

125
-1.9

0
127.2
10

-2.1 9.0
127.0 -1.2
-2.2
0

126.6 -2.1
-2.3

-5
120
126.1 -2.2
-2.3
125.5
-10

-2.3
-2.3

S25
 H TMS
H
O

7.26 CDCl3
8
isomer A
major by NMR
600 MHz 1H NMR
CDCl3, -60 oC

0.79
1.02

6.6 6.5 6.4 6.3 6.2 6.1 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0
f1 (ppm) f1 (ppm)

24.71

16.17
1.02
0.38
1.33
5.06

0.51
0.89
0.25
0.78
0.22

1.00

0.79
8.09
2.41
2.76
1.98
2.31

6.97
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5
f1 (ppm)

Figure S36: 1H NMR of bullvalene 8 at - 60 °C (figure S33) – Assignment of isomer A. A distinctive downfield
methine doublet is characteristic of an apical bridgehead proton being flanked by two substituents. A
characteristically downfield alkenic signal is typical of the proton being adjacent to a TMS group.3 Low
temperature 13C NMR indicated a set of 6 olefinic carbon signals with high intensity which indicates a single
major isomer, isomer A: 142.4, 135.6, 135.0, 127.5, 127.2, 126.6. Spectroscopically, we cannot observe distinct
connections between the two bullvalene units. We expect, given the distance between the bullvalene units, that
the isomer identity of one bullvalene will not significantly change the chemical environment of the other
bullvalene.

S26
4. Network Analysis

The network diagrams of the stereochemical variants of disubstituted bullvalenes are shown in Figure S37 and
Figure S38. For a disubstituted bullvalene with two identical and non-stereogenic substituents, e.g.
dimethylbullvalene, the network diagram has an internal plane of symmetry with achiral isomers shown in green,
chiral isomers are shown in red and blue as enantiomer pairs placed at lateral positions (Figure S37a). The R,R
and S,S reaction networks of 4a are enantiomeric with respect to one another. In this case, all isomers are chiral,
green isomers are non-stereogenic with respect to the bullvalene. Blue and red isomers are stereogenic with
respect to the bullvalene and are in diastereomeric relation (Figure S37b-c).

a) dimethyl network
Me

Me

b) R,R network c) S,S network

HO R Me HO S Me

Me Me
R S
HO HO
4a:R,R 4a:S,S

mirror plane

Figure S37: Network diagrams of (a) dimethylbullvalene, (b) 4a:R,R and, (c) 4a:S,S.

For network graphs of disubstituted bullvalene with two unique substituents, e.g. 7 (Figure S38a), and the R,S form
of the same stereogenic substituent, e.g. 4a:R,S (Figure S38b), both graphs are isomorphic, however, their spatial
rearrangement reflects the inner symmetry of each network. In both networks, isomers placed on the central axis

S27
are achiral while isomers placed in the symmetric lateral positions represent enantiomeric pairs. Colour coding
represents: green - isomers achiral in network a and chiral in network b (i.e. pseudoachiral); red - isomers chiral in
network a and achiral in network b (i.e. pseudosymmetric); blue - isomers chiral in both networks, but forming
different enantiomeric pairs in a and b.

HO R Me
a) b)
TMS

Me
S
OH HO
7 4a:R,S

Figure S38: Network diagram of (a) 7, and (b) 4a:R,S.

Network analysis of the reaction graph of tethered bis-bullvalene 8 required the generation of the complete 20-digit
isomer code list, and isomer interconversion list (Figure S39). This is achieved by permutation of the differentially
disubstituted bullvalene reaction graph,4 and is given in the supplementary spreadsheet file. Stereochemical
descriptors were applied through logical operations. The Cahn-Ingold-Prelog priority ranking for bullvalene isomers
was constructed using ChemDraw by examining pairwise comparisons of bullvalene units within the dimer to
establish the descending order of priority shown in Figure S40.

TMS R/S/r/s/A/a
TMS Cahn-Ingold-Prelog priority ranking of bullvalene isomers. (1 = TMS, 2 = tether)
O O
ensemble of Isomer CIP rank Isomer CIP rank Isomer CIP rank
O O 000 100 200 0 P 21r 000 000 201 0 a 13 000 000 020 1 a 6
900 isomers
Me 000 200 100 0 M 21s 000 000 010 2 a 12 000 000 102 0 a 5
30 isomers mutating 30 isomers 000 000 210 0 a 20 000 001 200 0 M 11r 000 020 010 0 M 4r
000 000 001 2 a 19 000 200 001 0 P 11s 000 010 020 0 P 4s
mutating P/M point chirality mutating P/M
000 000 120 0 a 18 000 000 200 1 a 10 000 002 010 0 M 3r
axial chirality and identity axial chirality and identity
000 000 002 1 a 17 000 000 100 2 a 9 000 010 002 0 P 3s
1st bullvalene tether 2nd bullvalene 000 000 021 0 a 16 000 100 020 0 P 8r 000 020 001 0 P 2r
000 000 012 0 a 15 000 020 100 0 M 8s 000 001 020 0 M 2s
123 456 789 0 - P/M/a R/S/r/s/A/a 123 456 789 0 - P/M/a 000 010 200 0 M 14r 000 002 001 0 M 7r 000 100 002 0 P 1r
000 200 010 0 P 14s 000 001 002 0 P 7s 000 002 100 0 M 1s
bullvalene code axial chirality point chirality bullvalene code axial chirality
configuration configuration configuration

Figure S39: Barcode and CIP ranking of for tethered bis-bullvalene 8.

S28
TMS TMS TMS TMS TMS
TMS
TMS TMS
O O O O O O O
O O O
TMS
O O O O O O TMS O O
O O
Me Me Me Me
Me
000 100 200 0 P - r - 000 200 100 0 M 000 000 021 0 a - R - 000 000 012 0 a 000 001 200 0 M - r - 000 200 001 0 P 000 002 001 0 M - R - 000 001 002 0 P 000 002 010 0 M - r - 000 010 002 0 P
1-(((1S,2R,8S)-2- 1-(((1R,8S)-4- 1-(((1R,2R,8R)-4- 1-(((1R,8R)-6- 1-(((1R,8R)-7-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-1-yl)methyl) 3-(((1S,2S)-2- trien-3-yl)methyl) 3-(((1R,8S)-3- trien-1-yl)methyl) 3-(((1R,2S)-4- yl)methyl) 3-(((1S,8S)-6- trien-4-yl)methyl) 3-(((1S,8S)-7-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-1-yl)methyl) (2R)-2-methylmalonate trien-4-yl)methyl) (2R)-2-methylmalonate trien-1-yl)methyl) (2R)-2-methylmalonate yl)methyl) (2r)-2-methylmalonate trien-4-yl)methyl) (2r)-2-methylmalonate

TMS TMS TMS TMS

TMS
TMS
TMS
TMS
O O O O O O
TMS O O
O O
O O TMS O O O O
O O
Me O O Me Me
Me
Me
000 200 100 0 M - R - 000 000 210 0 a 000 000 012 0 a - R - 000 010 200 0 M 000 200 001 0 P - R - 000 000 200 1 a 000 001 002 0 P - R - 000 000 020 1 a 000 010 002 0 P - R - 000 020 001 0 P
1-(((1S,2S)-2- 1-(((1R,2S,8R)-3- 1-(((1R,2S)-4- 1-(((1R,8S)-5- 1-(((1S,8R)-6-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9 (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-3- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-3-
trien-1-yl)methyl) 3-(((1r,2R,8S)-9- -trien-1-yl)methyl) 3-(((1R,8S)-3- yl)methyl) 3-(((1s,2R,8S)-5- yl)methyl) 3-(((1S,8S)-6- yl)methyl) 3-(((1S,8S)-7-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9 (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4-
trien-1-yl)methyl) (2R)-2-methylmalonate -trien-4-yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate

TMS TMS TMS TMS TMS TMS

O O O O TMS
O O TMS TMS
O O O
O O O O O
TMS
O O Me Me O O
O O
Me Me
Me
000 000 210 0 a - R - 000 000 001 2 a 000 010 200 0 M - r - 000 200 010 0 P 000 000 200 1 a - R - 000 000 100 2 a 000 000 020 1 a - R - 000 000 102 0 a 000 020 001 0 P - r - 000 001 020 0 M
1-(((1r,2R,8S)-9- 1-(((1R,2R)-3- 1-(((1s,2R,8S)-5- 1-(((1R,8S)-5- 1-(((1R,8S)-6-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-3- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-1-yl)methyl) 3-(((1S,2R)-4- yl)methyl) 3-(((1R,2S,8R)-3- yl)methyl) 3-(((1S,2R,8S)-1- yl)methyl) 3-(((1R,2S,8S)-2- trien-3-yl)methyl) 3-(((1S,8R)-6-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-5- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-5-yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate trien-3-yl)methyl) (2r)-2-methylmalonate

TMS TMS TMS TMS TMS

TMS
O O
TMS
O O TMS O O O O
TMS O O O O
O O Me TMS O O
O O
Me O O
Me Me
Me
000 000 001 2 a - R - 000 000 120 0 a 000 200 010 0 P - R - 000 000 201 0 a 000 000 100 2 a - R - 000 100 020 0 P 000 000 102 0 a - R - 000 020 010 0 M 000 002 010 0 M - R - 000 100 002 0 P

1-(((1R,2S,8S)-2- 1-(((1R,2R)-3- 1-(((1R,8S)-1- 1-(((2S,8R)-7- 1-(((1R,8S)-6-

(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-3- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-3-yl)methyl) 3-(((1S,2R)-4- yl)methyl) 3-(((1s,2R,8S)-10- yl)methyl) 3-(((1S,2R,8S)-1- trien-3-yl)methyl) 3-(((1R,2S,8S)-2- trien-3-yl)methyl) 3-(((1R,8S)-1-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-1- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-5- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-5-yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate yl)methyl) (2R)-2-methylmalonate trien-4-yl)methyl) (2R)-2-methylmalonate trien-4-yl)methyl) (2R)-2-methylmalonate

TMS TMS TMS TMS

TMS
TMS
TMS
TMS
O O O O
O O TMS O O O O
TMS O O O O
O O O O O O
Me Me
Me Me Me
000 000 120 0 a - R - 000 000 002 1 - a 000 000 201 0 a - R - 000 000 010 2 a 000 100 020 0 P - r - 000 020 100 0 M 000 020 010 0 M - r - 000 010 020 0 P 000 100 002 0 P - r - 000 002 100 0 M
1-(((1R,2S,8S)-2- 1-(((1s,2R,8S)-10- 1-(((1R,8S)-1- 1-(((1S,8S)-7- 1-(((1R,8S)-1-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-3- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4-
trien-3-yl)methyl) 3-(((1R,8S)-5- trien-1-yl)methyl) 3-(((1S,2R)-3- yl)methyl) 3-(((1S,8R)-1- trien-3-yl)methyl) 3-(((2S,8R)-7- yl)methyl) 3-(((1S,8R)-1-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-3- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-trien-4-
trien-4-yl)methyl) (2R)-2-methylmalonate trien-5-yl)methyl) (2R)-2-methylmalonate yl)methyl) (2r)-2-methylmalonate trien-3-yl)methyl) (2R)-2-methylmalonate yl)methyl) (2r)-2-methylmalonate

TMS TMS
TMS TMS
TMS
O O TMS TMS O O
O O O O
O O O O TMS
O O Me O O
Me
Me Me
000 000 002 1 a - R - 000 000 021 0 a 000 000 010 2 a - R - 000 001 200 0 M 000 020 100 0 M - R - 000 002 001 0 M 000 010 020 0 P - R - 000 002 010 0 M
1-(((1R,8S)-4- 1-(((1R,2R,8R)-4- 1-(((1S,8R)-1- 1-(((1S,8S)-7-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6, (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-3-yl)methyl) 3-(((1R,8S)-5- trien-1-yl)methyl) 3-(((1S,2R)-3- trien-3-yl)methyl) 3-(((1R,8R)-7-
(trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9- 9-trien-3-yl)methyl) 3-(((1R,8R)-6- (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6,9-
trien-4-yl)methyl) (2R)-2-methylmalonate trien-5-yl)methyl) (2R)-2-methylmalonate (trimethylsilyl)tricyclo[3.3.2.02,8]deca-3,6, trien-4-yl)methyl) (2R)-2-methylmalonate
9-trien-4-yl)methyl) (2R)-2-
methylmalonate

Figure S40: Pairwise stereochemical comparisons of bullvalene units in descending order of CIP priority.

5. Computational Analysis

Bullvalene isomer codes were generated using our previously reported algorithm transformed into corresponding
starting geometries.4

All ab initio calculations were performed using the program package ORCA 4.0.7 The structures of the considered
isomers were optimized in a multi-step fashion. Initially, all internal rotations within the substituents were scanned
and optimized using an inexpensive but robust semiempirical HF-3c method.8 Selected lowest-energy rotamers
were further reoptimized using DFT with the hybrid dispersion-corrected B3LYP-D3BJ9 functional and the Def2-

S29
SVP basis set.10 Finally, a single rotamer with the lowest energy for each isomer/TS was kept and used as a
starting geometry for the full optimization using the same level of theory. Subsequently, the single point energies
were calculated with the same functional and the larger Def2-TZVPPd basis set,11 with and without the use of the
implicit continuous solvation model CPCM.12

Table S1. Computational relative energies and ratios for bullvalene 2.

gas phase chloroform

isomer
Erel (kJ/mol) pop. -60°C pop. 25°C Erel (kJ/mol) pop. -60°C pop. 25°C
000 001 002 0 * 0.00 82.04% 61.21% 0.00 52.60% 36.88%
000 002 001 0 * 4.84 5.36% 8.70% 1.76 19.46% 18.12%
000 001 020 0 * 5.64 3.41% 6.30% 3.77 6.26% 8.05%
000 020 001 0 * 5.77 3.16% 5.96% 3.79 6.19% 7.98%
000 000 201 0 * 8.40 0.72% 2.07% 5.12 2.93% 4.67%
000 002 010 0 * 6.87 1.70% 3.83% 5.19 2.82% 4.55%
000 010 002 0 * 7.11 1.49% 3.48% 5.30 2.64% 4.35%
000 001 200 0 * 9.01 0.51% 1.62% 5.50 2.36% 4.01%
000 200 001 0 * 9.12 0.48% 1.55% 5.55 2.29% 3.92%
000 000 102 0 * 10.62 0.20% 0.84% 8.41 0.46% 1.24%
000 010 020 0 * 10.48 0.22% 0.89% 8.59 0.41% 1.15%
000 200 010 0 * 12.15 0.09% 0.46% 8.80 0.37% 1.06%
000 100 002 0 * 11.19 0.15% 0.67% 8.95 0.34% 1.00%
000 020 010 0 * 10.86 0.18% 0.77% 9.13 0.30% 0.93%
000 002 100 0 * 11.39 0.13% 0.62% 9.21 0.29% 0.90%
000 100 020 0 * 12.62 0.07% 0.38% 10.64 0.13% 0.50%
000 010 200 0 * 12.43 0.07% 0.41% 10.81 0.12% 0.47%
000 020 100 0 * 13.68 0.04% 0.25% 12.90 0.04% 0.20%
000 000 010 2 * 23.91 0.00% 0.00% 21.41 0.00% 0.01%
000 000 021 0 * 23.25 0.00% 0.01% 21.82 0.00% 0.01%
000 000 012 0 * 23.27 0.00% 0.01% 22.25 0.00% 0.00%
000 000 100 2 * 29.20 0.00% 0.00% 25.89 0.00% 0.00%
000 000 020 1 * 29.32 0.00% 0.00% 26.63 0.00% 0.00%
000 000 200 1 * 32.96 0.00% 0.00% 28.76 0.00% 0.00%
000 200 100 0 * 35.28 0.00% 0.00% 31.77 0.00% 0.00%
000 100 200 0 * 33.07 0.00% 0.00% 31.95 0.00% 0.00%
000 000 120 0 * 41.04 0.00% 0.00% 38.95 0.00% 0.00%
000 000 001 2 * 41.17 0.00% 0.00% 40.25 0.00% 0.00%
000 000 210 0 * 41.27 0.00% 0.00% 40.99 0.00% 0.00%
000 000 002 1 * 53.08 0.00% 0.00% 52.72* 0.00% 0.00%
* Computed using the SMD solvent model and compared with the energy of the 000 001 002 0 isomer at the same level of theory.

S30
Table S2. Computational relative energies and ratios for bullvalene 4a-R,R.

gas phase chloroform

isomer
Erel (kJ/mol) pop. -60°C pop. 25°C Erel (kJ/mol) pop. -60°C pop. 25°C
000 001 001 0 * 0.00 72.89% 56.06% 0.00 25.16% 21.79%
000 010 001 0 * 3.88 8.18% 11.73% 0.18 22.73% 20.26%
000 001 010 0 * 3.24 11.69% 15.15% 0.23 22.07% 19.84%
000 000 101 0 * 6.25 2.15% 4.51% 1.53 10.62% 11.76%
000 100 001 0 * 6.59 1.77% 3.93% 2.03 7.99% 9.60%
000 001 100 0 * 6.69 1.67% 3.77% 2.30 6.89% 8.63%
000 100 010 0 * 8.97 0.46% 1.50% 4.23 2.31% 3.95%
000 010 010 0 * 7.49 1.06% 2.73% 4.36 2.15% 3.76%
000 010 100 0 * 11.27 0.13% 0.59% 10.07 0.09% 0.38%
000 000 010 1 * 20.66 0.00% 0.01% 16.45 0.00% 0.03%
000 000 100 1 * 24.84 0.00% 0.00% 19.01 0.00% 0.01%
000 000 011 0 * 24.05 0.00% 0.00% 20.73 0.00% 0.01%
000 100 100 0 * 32.10 0.00% 0.00% 28.04 0.00% 0.00%
000 000 110 0 * 42.03 0.00% 0.00% 39.57 0.00% 0.00%
000 000 001 1 * 47.00 0.00% 0.00% 43.60 0.00% 0.00%

Table S3. Computational relative energies and ratios for bullvalene 4a-R,S.

gas phase chloroform

isomer Erel (kJ/mol) pop. -60°C pop. 25°C Erel (kJ/mol) pop. -60°C pop. 25°C
000 002 001 0 0.00 88.14% 67.92% 0.00 44.21% 28.89%
000 002 010 0 * 6.71 4.00% 9.08% 2.92 17.06% 17.82%
000 001 020 0 * 6.60 4.26% 9.50% 3.81 10.32% 12.44%
000 000 102 0 * 9.47 0.84% 2.97% 4.00 9.25% 11.51%
000 002 100 0 * 9.97 0.63% 2.43% 4.44 7.20% 9.62%
000 001 200 0 * 9.81 0.70% 2.60% 4.45 7.19% 9.61%
000 020 010 0 10.36 0.26% 1.04% 6.25 1.30% 2.32%
000 001 002 0 8.29 0.82% 2.40% 6.76 0.97% 1.89%
000 010 200 0 * 12.25 0.18% 0.97% 7.72 1.14% 2.57%
000 020 100 0 * 12.68 0.14% 0.81% 7.80 1.08% 2.48%
000 010 020 0 13.81 0.04% 0.26% 9.00 0.28% 0.77%
000 200 100 0 22.24 0.00% 0.01% 17.55 0.00% 0.02%
000 000 010 2 * 23.88 0.00% 0.01% 18.90 0.00% 0.03%
000 000 012 0 * 25.32 0.00% 0.00% 20.46 0.00% 0.02%
000 000 100 2 * 27.29 0.00% 0.00% 20.85 0.00% 0.01%
000 000 001 2 * 33.62 0.00% 0.00% 31.65 0.00% 0.00%
000 100 200 0 41.70 0.00% 0.00% 34.69 0.00% 0.00%
000 000 120 0 * 38.10 0.00% 0.00% 44.56 0.00% 0.00%

S31
Table S4. Computational relative energies and ratios for bullvalene 9.

gas phase chloroform

isomer
Erel (kJ/mol) pop. -60°C pop. 25°C Erel (kJ/mol) pop. -60°C pop. 25°C
000 001 002 0 * 0.00 95.05% 83.43% 0.00 88.51% 73.11%
000 001 020 0 * 8.33 0.87% 2.90% 5.12 4.92% 9.27%
000 000 201 0 7.36 0.75% 2.14% 5.70 1.77% 3.66%
000 001 200 0 * 7.89 1.11% 3.46% 6.30 2.54% 5.77%
000 010 200 0 * 7.32 1.53% 4.36% 7.93 1.01% 2.99%
000 010 020 0 * 10.81 0.21% 1.07% 9.31 0.46% 1.71%
000 002 010 0 * 10.76 0.22% 1.09% 9.39 0.44% 1.66%
000 002 100 0 * 13.88 0.04% 0.31% 10.82 0.20% 0.93%
000 000 102 0 13.22 0.03% 0.20% 12.11 0.05% 0.28%
000 020 100 0 * 10.96 0.20% 1.00% 12.13 0.09% 0.55%
000 000 010 2 17.85 0.00% 0.03% 15.57 0.01% 0.07%
000 000 100 2 23.66 0.00% 0.00% 20.63 0.00% 0.01%
000 000 021 0 25.87 0.00% 0.00% 24.93 0.00% 0.00%
000 000 012 0 24.31 0.00% 0.00% 26.01 0.00% 0.00%
000 000 001 2 31.08 0.00% 0.00% 29.10 0.00% 0.00%
000 000 020 1 31.05 0.00% 0.00% 29.45 0.00% 0.00%
000 000 200 1 31.79 0.00% 0.00% 29.50 0.00% 0.00%
000 100 200 0 * 29.72 0.00% 0.00% 30.17 0.00% 0.00%
000 000 120 0 35.98 0.00% 0.00% 35.25 0.00% 0.00%
000 000 210 0 35.82 0.00% 0.00% 35.33 0.00% 0.00%
000 000 002 1 47.80 0.00% 0.00% 46.87 0.00% 0.00%

Cartesian Coordinates

Compound 2, isomer 000 000 001 2

C 0.02971271128819 0.02108422140419 0.05799874581074
C 1.49957521957618 0.00956424599947 0.01596689694054
C 2.29534497928753 1.08736977376483 -0.04620102954991
C -0.82337227696191 1.04599131165674 -0.66791250465743
C -0.27131704036792 2.12817565994783 -1.49958933418484
C 0.86904542706972 2.79662546067320 -1.27263857030347
C -0.70137353346825 1.10817751693676 0.86236351066361
C 0.01252826530915 2.19367983824444 1.55839311480411
C 1.12552406883136 2.88804843946609 1.20039329810794
C 1.84001066936687 2.53875075011436 -0.12913154170975
H -0.42873982638833 -0.96833423641984 0.13116934219515
H 1.97024421023615 -0.97462056065747 0.10457074889887
H 3.37467240484872 0.91829815666696 0.01633566770610
H -1.78152104708124 0.65287957836355 -1.01736688510688
H -0.89581446679064 2.44338725499042 -2.34151675561093
H 1.10464886904194 3.64743095733646 -1.91596322117845
H -1.58380291545298 0.75019857425428 1.39887625273192

S32
 H -0.46587004057688 2.45946193802895 2.50462745030698
Si 1.58247987690575 4.30136916009300 2.40040965474868
C 0.78950186352223 5.93015553204078 1.86769200867069
H 1.03105001002715 6.73728668631293 2.58030762156617
H 1.13261601871827 6.22172957705915 0.86568564712611
H -0.30726385906528 5.82086631186620 1.83782456795154
C 0.86060996962501 3.87507849342230 4.10492276796658
H 1.19411381825360 4.63416176933802 4.83279196257929
H -0.24113417322531 3.87749312257424 4.11825539884172
H 1.20433884078317 2.89080493051834 4.46290146003629
C 3.43835949334564 4.52783901565512 2.71689405553504
H 3.56815198505013 5.19285058400510 3.58751736266810
H 3.92789417787550 3.57007735343426 2.95849608654992
H 3.96247257547621 4.98544708538623 1.86673754628826
C 3.10941866629319 3.39036863499445 -0.36549222220430
C 3.85578841334383 3.06722974109520 -1.66006388022694
O 2.70787866822972 4.75357440090020 -0.36026651245138
H 3.48632723434476 5.30697639310327 -0.50255795605580
H 3.78787891456305 3.19498027542008 0.48578767548245
H 4.74298104405955 3.71694353658336 -1.75040570442004
H 4.20688021298946 2.02606665863321 -1.68575484592210
H 3.21868805112360 3.23529900903115 -2.54057699190883

Compound 2, isomer 000 000 002 1

C 0.04399839758370 -0.00933261297051 -0.27040131293424
C 1.49303159048562 0.06958294993578 -0.50633213165022
C 2.26055663152245 1.16454338550825 -0.38198196973161
C -0.91051120068668 1.13242433981508 -0.60863689500418
C -0.46473434355928 2.39906239842769 -1.21353468361785
C 0.68912899350794 3.04468086605903 -0.96911349251248
C -0.60537755491917 0.79272871641814 0.85871711189351
C 0.14640134350922 1.71142728730970 1.72687359085058
C 1.17580778200765 2.52763056192387 1.40787046197371
C 1.77826942442896 2.56968725204142 -0.00792762078053
H -0.38456102781735 -1.00401457647327 -0.41668397517502
H 1.98164295824568 -0.87199101536676 -0.77778050572901
H 3.33161876807310 1.02367381763525 -0.55917822514833
H -1.89546999708343 0.79863378642601 -0.94467048843770
H -1.17149578502888 2.85907535929221 -1.91200495007043
H 0.83841823742377 3.99954661182333 -1.48549015362147
H -1.41566306262801 0.26706357702310 1.37043611579825
H -0.21087246986259 1.76632087964394 2.75974701633748
C 1.65264737092902 3.49817085549924 2.48497255610939
C 0.80285739284890 4.76762899707938 2.50297842289198
O 1.57556341948162 2.95098386143806 3.79267884164333
H 2.00403461179995 2.08445621249648 3.76766246523820
H 2.69956460071983 3.77895865708749 2.27214676005116
H 1.21074157811969 5.49535388682904 3.22222401578138
H 0.75752805059010 5.23193696685508 1.50931372963042
H -0.22169352967221 4.50521186515895 2.80720648080248
Si 3.33167320514246 3.69166605507769 -0.31725943830393
C 3.75569673272299 3.48695040452748 -2.14964791049451
H 4.66202747896823 4.06892498768166 -2.38749033374227
H 3.94794312659666 2.43686355150224 -2.41820889148034
H 2.94333712649120 3.85181625126506 -2.79790353821939
C 3.04801445235289 5.53828417614233 -0.02672249916038
H 3.87967314891075 6.09435937655193 -0.49172468197509
H 2.11490208477448 5.89262586716894 -0.49325168372309

S33
 H 3.01994713451692 5.80975743943827 1.03818765849063
C 4.83253748361635 3.12418625809094 0.68735860226148
H 5.71393436519353 3.71117503338450 0.37801955593214
H 4.70518835536700 3.26584205029192 1.77162741858791
H 5.06687983039528 2.06225935891058 0.51283091901063

Compound 2, isomer 000 000 010 2

C 0.23952264940408 -0.09263611282628 0.20066387845654
C 1.70061288137336 0.07317289075195 0.14607699527468
C 2.37134375189552 1.23337410862729 0.03038382531758
C -0.70591365631700 0.79169260268930 -0.64005270180538
C -0.18631484282052 1.83153065293524 -1.54448807494385
C 0.86669229775857 2.63437982682064 -1.31803080455879
C -0.68749497389121 0.92016220428630 0.87715572297219
C -0.17889111901422 2.11099759630463 1.60158612235173
C 0.87624462583694 2.84594085633808 1.19162134588124
C 1.71504911884253 2.60871225040603 -0.05654327436199
H -0.08836921642316 -1.13125992315102 0.29084615448103
H 2.27988658402848 -0.85531256781855 0.17154551020500
H 3.46416237423312 1.18703488562758 -0.05632813364316
H -1.57412673877121 0.25519451737808 -1.03114070277086
H -0.70594208373837 1.92189617071336 -2.50361600820842
H 1.16357460403785 3.32901870078137 -2.10921484574698
H -1.55219069988643 0.44261465517471 1.34792691208889
H 1.21556463060495 3.67335948237804 1.81960541696464
Si -1.06854501671059 2.55655469928935 3.20485077153023
C -0.95567749498714 1.09131708628797 4.39516802657170
H -1.49745614804703 1.29965439757124 5.33312344932383
H -1.39016048010794 0.17904503407522 3.95409751524316
H 0.09484749922102 0.87340358604073 4.64876011041975
C -0.28584823092271 4.08031334638196 3.99242459040845
H -0.81386230822376 4.33806274214584 4.92554789259753
H 0.77379052905661 3.90915768366397 4.24217273727084
H -0.34050865707552 4.95427293399900 3.32326962819854
C -2.88814891015357 2.89819993324523 2.82028975564247
H -3.45182549273708 3.12581598622126 3.74069135469607
H -2.98917009137133 3.75709968575892 2.13658945089237
H -3.36894278725015 2.02970606260641 2.34058576878742
C 2.83228247742446 3.68569175155682 -0.13495426910885
C 2.33250643330734 5.11126919968701 -0.32632373422860
O 3.60861909521393 3.69212242423326 1.05152255480431
H 3.80384851239449 2.77724421794260 1.29504965406843
H 3.46730686636129 3.41638582193006 -1.00625145631464
H 3.18914476354456 5.79977638720083 -0.27834846361092
H 1.83499554205160 5.24408796015515 -1.29698474253508
H 1.62532892189767 5.39410623920015 0.46776572723863

Compound 2, isomer 000 000 012 0

C 0.23697279002363 -0.10257079444901 0.20321278139663
C 1.70220645880738 0.04029025919407 0.13505417844001

S34
 C 2.36623551339409 1.20170179278155 0.02450739883103
C -0.72560779001212 0.77875690772557 -0.60366066828935
C -0.26410888011516 1.85172648388280 -1.50128151341467
C 0.79101501893435 2.65217187141555 -1.27904754146173
C -0.66077667047203 0.90792694766120 0.92342373431581
C -0.17266521498238 2.11716470838247 1.64111755398153
C 0.89363316968745 2.84880142430214 1.21926531401528
C 1.68045357019363 2.54886185499038 -0.05593892670059
H -0.10190327099896 -1.13678862292836 0.30622497357499
H 2.27412661806523 -0.89172851072668 0.18484590747206
H 3.46013382122627 1.18774808602065 -0.01256089983471
H -1.61137953195193 0.24833030408771 -0.96277671230977
H -0.84889411699599 1.99261540984626 -2.41593745999119
H 1.03950618526026 3.42216655895039 -2.01640163502706
H -1.50893989770242 0.42088867814252 1.40431930246636
H 2.44761871387378 3.32539243940164 -0.15115232231555
Si -1.19130755391654 2.61260201107516 3.17998031862635
C -1.98905848558018 4.31168685710771 2.91773944403156
H -2.59801202551506 4.59224485013750 3.79377816310848
H -1.25554301353810 5.11476355135991 2.74773141333396
H -2.65748151979769 4.27821727947374 2.04111126495515
C -2.60743977605426 1.38326954121365 3.43254994833836
H -3.19822649305871 1.69340310265206 4.31087371416453
H -3.29147349066644 1.34858155402115 2.56900510104134
H -2.24339605248538 0.36047685893670 3.62384999765637
C -0.16421898193779 2.58080680937330 4.76977491507234
H -0.81692821516771 2.73838322685144 5.64519217654194
H 0.32457102063663 1.59917496379957 4.88640134258400
H 0.62225548402461 3.34989303638157 4.79445562834838
C 1.39198949864967 4.07294930548895 1.96257292676723
C 2.79420791065745 3.89701657450988 2.53537674711426
O 1.42697400092254 5.20593178162751 1.09647940107543
H 0.56764297203105 5.25659671406471 0.65545355682247
H 0.71867986726608 4.28462833536330 2.80805019034268
H 3.12024186795722 4.83717202524409 3.00671561597932
H 2.80164555975727 3.09575099164407 3.28889897246112
H 3.52063562557041 3.64280852815037 1.74862082442009

Compound 2, isomer 000 000 020 1

C -0.16142742037749 0.19518918641285 -0.04853672656951
C 1.30734053050105 0.07809983353422 -0.06617020936309
C 2.18820262769757 1.09361674198143 -0.05157221597554
C -0.90682643339890 1.31095035499237 -0.79506013825662
C -0.19900836878892 2.34528786347263 -1.56978164505480
C 0.97929620850002 2.91184351252381 -1.25471575191539
C -0.89947702698631 1.28185085545773 0.73287422977907
C -0.20321992468865 2.30085712741384 1.54810119600783
C 0.98418714240941 2.85846624774026 1.24073748225462
C 1.79963283635407 2.56840753168386 -0.01429430930676
H -0.68340784181870 -0.76510983332775 -0.06131643589346
H 1.69689139915805 -0.94485220906536 -0.09971801496872
H 3.25278091354655 0.83490961187348 -0.07473919500859
H -1.85227488720409 0.98934762942441 -1.23939547074364
H -0.69831757445613 2.66780782384686 -2.48937917278860
H 1.37032346525251 3.66875000230666 -1.94389845944039
H -1.82940025711391 0.93383608295942 1.18709314394283
H 1.37827053037942 3.59340083655554 1.95371253077552
C -0.93712732512423 2.72455494760572 2.80968524028610
C -2.19820141182055 3.52896824531557 2.51266965005053

S35
 O -1.34004198918341 1.59575502044286 3.57757879960483
H -0.55824451100764 1.04383231901081 3.71543692269609
H -0.24938315861440 3.36426094498508 3.39907450123459
H -2.71274287268996 3.77639032296394 3.45412266463839
H -1.94403573957789 4.45999445734505 1.98468649309641
H -2.89408861622718 2.95017863728885 1.88577046345596
Si 3.38965032335884 3.64299914372758 0.00977542972408
C 2.90501375573204 5.46699310266465 0.05291412081253
H 3.80389986381892 6.10572904114558 0.06748463978021
H 2.30839032479075 5.74705230260863 -0.83013288555162
H 2.30890953258534 5.70591949051543 0.94828041347482
C 4.40309997341605 3.21650715291942 1.54449502807068
H 5.32504270313758 3.82075801653035 1.57845420661580
H 3.83885261758061 3.41419345083692 2.47010065888707
H 4.69741720212295 2.15466804678810 1.55220320401355
C 4.40425231893001 3.28954511307734 -1.54218479610688
H 5.32286653678242 3.89976599612050 -1.54981476781311
H 4.70450415453197 2.23082388801415 -1.59750737534384
H 3.83801690498099 3.52449737243713 -2.45777350759084

Compound 2, isomer 000 000 021 0

C 0.09639926082252 0.04115017517864 -0.03637815028068
C 1.55522369258466 0.18590678170252 -0.18278932272493
C 2.22283179192652 1.35077144172209 -0.19404270607744
C -0.90917857823283 1.01389290713834 -0.66637723680212
C -0.49505206120746 2.18615020673519 -1.45667056861714
C 0.57918248946542 2.95179347997182 -1.20585035028692
C -0.73753313413730 0.96610124339693 0.85134668533147
C -0.17087191252744 2.07881337155526 1.65287647510497
C 0.87788561265075 2.87123214169752 1.30246467538146
C 1.55184771502438 2.70409277132792 -0.06889629427119
H -0.24919951183872 -0.99582674076662 -0.02624192031857
H 2.11933383803587 -0.74672444754955 -0.28472869042115
H 3.31193985514511 1.33577320112918 -0.30492778799638
H -1.82331926184982 0.53214526302054 -1.02278379265716
H -1.13563751361362 2.43957059259710 -2.30727623788797
H 0.78067673767398 3.80629401881302 -1.85985459777527
H -1.53682030158766 0.43931218100010 1.37521588254551
H 2.33960615438941 3.45846545016399 -0.16030035942651
C -0.90002746438243 2.26289719532579 2.97698485632700
C -2.33956487616714 2.73359026039049 2.80005942154378
O -0.93834822244269 1.04704156904351 3.71870525289203
H -0.03588497149694 0.70119076915947 3.75254850544422
H -0.37769015724055 3.03185580032394 3.56692110032788
H -2.82442286959993 2.81681554586316 3.78511158075706
H -2.36075898731469 3.71597368488775 2.30535949733202
H -2.92158247801590 2.02447242770667 2.19242617311449
Si 1.62652795038832 4.17305996386801 2.47358722597031
C 2.25499117885370 3.35245800610144 4.06337687324033
H 2.71572286045055 4.10233440812041 4.72855986523460
H 1.46302973952018 2.84146869726162 4.63237997645469
H 3.02578266775884 2.60331168483697 3.81631332081338
C 3.13257062908948 4.96821488306559 1.64961026375699
H 3.58650533515373 5.68978299365445 2.34964685803176
H 3.90611151667746 4.22697642417058 1.39019162445687
H 2.86630618662544 5.52019612681562 0.73330648351535
C 0.42225671629749 5.57864771310894 2.87235633215882
H 0.93609080827637 6.36902822965686 3.44556461229715
H 0.04269968353501 6.02998280013318 1.94052246868428

S36
 H -0.44729629740802 5.24806363203172 3.46042808223798

Compound 2, isomer 000 000 100 2

C -0.13830574889253 0.09259417945400 -0.18677442521534
C 1.32893151454148 0.05439753780768 -0.29931780170573
C 2.17200568089279 1.10030182555126 -0.23271968100089
C -0.96226618809158 1.25473887610752 -0.74982087462646
C -0.33074410097965 2.38946973892109 -1.44646396220766
C 0.84649326151540 2.96468974688447 -1.14998962159761
C -0.89400075055227 1.04116952913985 0.77024573360616
C -0.12580520747946 1.97613680610048 1.62959985406755
C 1.00675478590726 2.63064859326828 1.32923426328613
C 1.74386678919039 2.54562700817995 0.00273128893692
H -0.60651208582291 -0.88665989543250 -0.31722043825262
H 1.75554260848003 -0.93598150148490 -0.48799055083546
H 3.23981170991603 0.90751235970300 -0.39576536950449
H -1.90442704888654 0.94071972782126 -1.20663235453247
H -0.88334863036202 2.76927297599009 -2.31172572600447
H 1.20127620783327 3.77204094790147 -1.79712003330637
H -0.52454001622186 2.12995113089552 2.63891591372851
H 1.47382266146495 3.24430308362155 2.10348410497975
Si -2.44336548728091 0.34272914553409 1.60875763410754
C -3.56698315519874 1.78228048694195 2.08266691773634
H -4.48033335484280 1.42500242663387 2.58695947360514
H -3.05850516208034 2.48349816213717 2.76379261084111
H -3.87206252535108 2.34849586771191 1.18715357059865
C -3.37781629584234 -0.81876010455802 0.44831819048447
H -4.25961859735393 -1.22431060938598 0.97209247162573
H -3.74197087761668 -0.30214457325949 -0.45446167061081
H -2.76394875669704 -1.67631060947592 0.12839182679579
C -1.90953279876035 -0.61290102944313 3.14587113802488
H -2.78045124892646 -1.03113748322864 3.67759906570025
H -1.24466039369153 -1.44881531132779 2.87225283602442
H -1.36187042661151 0.03181536261185 3.85207325495137
C 3.01514380499063 3.43669566507362 0.05549447496771
C 2.74536526649236 4.92895224640980 0.19264844289962
O 3.83510331836561 3.07832272873746 1.15500177576463
H 3.88798172297907 2.11409787420030 1.19708296379492
H 3.55734448257709 3.26426997710995 -0.89913976365529
H 3.70392808587681 5.45524037670211 0.31265852214811
H 2.23493375489947 5.33666187787060 -0.69082516285355
H 2.12863767189465 5.14132290653631 1.07878588159404

Compound 2, isomer 000 000 102 0

C -0.01780463120876 -0.07332770915943 0.11104820633792
C 1.45003963885554 -0.12105117942558 0.25144720033060
C 2.27777126075873 0.93594733005829 0.29920631864493
C -0.73968846779491 0.97336990456971 -0.72902055911551
C -0.03243333335722 2.03468051315380 -1.47016724769846
C 1.08824910211827 2.66404042572304 -1.07872274767575

S37
 C -0.89786643896197 0.98897861372176 0.80936562335070
C -0.27596530837412 2.07028662247602 1.61072177745196
C 0.90044927927326 2.69397337316143 1.40506527370350
C 1.80579568730771 2.37291915411731 0.22462665451631
H -0.47533450940743 -1.06493814131594 0.05902951123018
H 1.88140119605238 -1.12459948904418 0.32360064762529
H 3.35279523241600 0.76098835569206 0.40820357867655
H -1.60985424326483 0.58243232250549 -1.26313645947230
H -0.48227446370005 2.31851914846276 -2.42707205528789
H 1.51539582274614 3.43569903218407 -1.72718585111509
H -0.84789016034835 2.39973307825088 2.48787623728888
H 2.67445831328289 3.03957401986518 0.28387297925984
Si -2.55738869106125 0.39957924568630 1.50582334245311
C -2.27245573192901 -0.25899351719879 3.25126538709037
H -3.21531794775478 -0.60567734919719 3.70621357707169
H -1.56973416535379 -1.10845032498049 3.23536659838245
H -1.84561175773639 0.51487504687136 3.90952901034562
C -3.74716853797008 1.86455761356040 1.54230327980739
H -4.72701789375683 1.57156755960233 1.95489668440274
H -3.35540423008525 2.68860616169206 2.16025067935404
H -3.91055901441226 2.25766034282226 0.52518902518675
C -3.29713592331665 -0.97086491574999 0.43687329420064
H -4.25973246531923 -1.29041222936882 0.87012955612447
H -3.49681601107641 -0.63536222015996 -0.59371570265488
H -2.64836109993387 -1.86032346732785 0.38795349113998
C 1.38155401196201 3.77388129069813 2.34931096315329
C 2.61933371277255 3.36248795900065 3.13929882648905
O 1.72588553072820 4.95572631622485 1.63171528680339
H 0.97271218143358 5.18156107600814 1.06878211448784
H 0.56502688809455 3.98641457788819 3.06990152942528
H 2.96155103100843 4.20513564610964 3.75987502856837
H 2.39404805407864 2.50372408765427 3.78864506605967
H 3.44232081823144 3.08342698530720 2.46289020794729

Compound 2, isomer 000 000 120 0

C 0.15013962429287 -0.07927095510376 0.24083356208547
C 1.61722792062982 0.01614250660045 0.36790317307252
C 2.35228854210680 1.13618418104991 0.27077679585686
C -0.65230323996581 0.81857455975330 -0.68701989048949
C -0.05535610362106 1.84911479726908 -1.55596505213177
C 1.01594052600767 2.60379716460333 -1.26844235610723
C -0.83646102129212 0.95077375835177 0.85380973259578
C -0.29191301326434 2.15813187945517 1.55344548486051
C 0.81676675629507 2.84129748373262 1.19957909759087
C 1.74740654667822 2.51046812068725 0.05383599542178
H -0.20843263626671 -1.11061604901065 0.27088937956773
H 2.13368044402305 -0.93257730216936 0.54549399677368
H 3.43969389148042 1.06739970708032 0.37390657452487
H -1.47831969590575 0.30214681977927 -1.17981808684166
H -0.54610386324929 1.98207903933735 -2.52551207570017
H 1.37309905879736 3.32968186237746 -2.00541628607093
H 1.08660035275873 3.69640411846029 1.82588819399175
H 2.56050501193755 3.24891525067902 0.05318461522887
Si -2.53965608173973 0.22027750513400 1.34413739141887
C -2.86365297848703 -1.36820103082779 0.36051312109798
H -3.88949815327165 -1.70103802038883 0.59226126925723

S38
 H -2.79952252481170 -1.25126077049048 -0.73195082115559
H -2.18526973374977 -2.18405630058188 0.65870541396593
C -2.72567934785912 -0.31460246391118 3.14982178317701
H -3.65274841490779 -0.90589702742068 3.24040693249711
H -1.88978311642893 -0.96378761213843 3.45813087934243
H -2.79065140853801 0.51783532654929 3.86387427737511
C -3.88014007769088 1.46676542856598 0.87177770606760
H -4.88336984822343 1.04451884399219 1.04916006804271
H -3.80663090246041 2.40570940515547 1.44233681297973
H -3.80417923324755 1.71977658437902 -0.19859964612887
C -0.98626111220379 2.62297764928308 2.83706054870586
C -0.36091605765275 1.97128713653906 4.06798429578707
O -0.89658324356263 4.02434816126009 3.03693744251567
H -1.16376383573537 4.45113109939589 2.21125757617828
H -2.05234365436529 2.33883496306458 2.79011214739314
H -0.92076705354134 2.24268367321921 4.97675286705415
H -0.34154791535486 0.87742594061821 3.97324383030668
H 0.67538148984841 2.32684023537973 4.17100678791899

Compound 2, isomer 000 000 200 1

C -0.15089293134181 0.16379101993757 -0.08548511674145
C 1.31797466186692 0.10548954097463 -0.19546740166955
C 2.16047879125921 1.15197590395380 -0.17371179443768
C -0.98187254118481 1.29446114310150 -0.70501250237090
C -0.36775081073334 2.40658399785945 -1.44975600186532
C 0.81269323600089 2.99394877085145 -1.18365699169322
C -0.88422332847972 1.14186737241279 0.82556064473935
C -0.15739674304585 2.15374901478095 1.62313903740639
C 0.97051652323091 2.80006778609613 1.28490455962186
C 1.72797819669360 2.60719055071979 -0.02487323593705
H -0.63716179794499 -0.81391646723151 -0.14995001923925
H 1.74070768822070 -0.89793379565898 -0.31105707257407
H 3.22982919691493 0.93447697024658 -0.27332963478817
H -1.93693804438107 0.95528263718116 -1.11780117290192
H -0.94395267197798 2.77116504107449 -2.30673999777957
H 1.12579573729039 3.80909995460195 -1.84575234116085
H -0.63708800667915 2.41295777996999 2.57136214029777
H 1.35294560647968 3.53595907622896 2.00135616299210
C -2.13418130754045 0.58318067445752 1.50844493386665
C -1.81667964418687 -0.23690929931670 2.75068224229445
O -3.00613139544534 1.62804839977694 1.90331514174966
H -3.11118058048044 2.22468055609596 1.14949580959434
H -2.64028422305298 -0.08155029625919 0.77631139245145
H -2.74929843273216 -0.59434376948556 3.21273161839145
H -1.19186400337324 -1.10474994226602 2.49155489820369
H -1.27790473542660 0.37029934997015 3.49362553190172
Si 3.28154668570015 3.73401948890845 -0.03343836885896
C 4.20563126061574 3.50314442812589 -1.66330713195884
H 5.10207357295265 4.14481022297975 -1.69351905958799
H 4.53515213088366 2.46034397232458 -1.79778293683950
H 3.57433500202679 3.76815766045604 -2.52673272807385
C 2.74544586392902 5.53545823599921 0.14341426607324
H 3.62427715917112 6.20167901015377 0.13802620609434
H 2.08553622905152 5.84421772574279 -0.68325726193663
H 2.20167966372999 5.70548170066964 1.08650800010720
C 4.39908151444229 3.25534085964339 1.41007236894275
H 5.29952235292480 3.89174948787619 1.43036692016250
H 3.88230031619915 3.37343834922366 2.37605719941911
H 4.73037874699120 2.20719390739682 1.33421781163451

S39
Compound 2, isomer 000 000 201 0
C -0.03144560748697 -0.05619916941876 -0.01269560205674
C 1.43474486662002 -0.15432587202806 0.12134358293324
C 2.28763536402177 0.88045630274441 0.18354034082254
C -0.72573496728937 1.02380150978596 -0.84809996423776
C 0.01455410825279 2.06404978851565 -1.58434985619047
C 1.15458354906288 2.65334312344050 -1.18555110131103
C -0.86117161296062 1.01509328847269 0.68922432049101
C -0.23340605125067 2.08676374506206 1.49497069484925
C 0.95345809076912 2.70132432987985 1.29928966489278
C 1.85676867410604 2.33227060698231 0.12020772174871
H -0.53530538645499 -1.02586770716553 -0.06194591678841
H 1.83828561562205 -1.17039244539678 0.17410015620870
H 3.35778778633506 0.67560283762574 0.28763500546609
H -1.61985384904061 0.66204993830769 -1.36509015683826
H -0.42314503986770 2.36810293624689 -2.54059569336203
H 1.60332810757748 3.41910288431948 -1.82610022729308
H -0.86248144676927 2.42415648826256 2.32410549856628
H 2.76653065222180 2.94785272341845 0.16605697541333
C -2.21373127701942 0.54397320172185 1.22738477003860
C -2.10344220512842 -0.16108150299782 2.57176771922446
O -3.10116559104983 1.63637350417169 1.39511156336768
H -3.07776053616716 2.16212579383632 0.58376324362674
H -2.63014203466773 -0.17719234767568 0.49220986239106
H -3.10332072092392 -0.45547073038831 2.92468206266113
H -1.47641240624165 -1.06110970328538 2.48545750637037
H -1.65624387983713 0.50356750900404 3.32627746573298
Si 1.54052757685822 4.07034581511070 2.44710474637147
C 3.19282619708182 3.55307424368984 3.20760050992670
H 3.60177767525798 4.34983364747823 3.85149799751623
H 3.07434610320902 2.64441567742428 3.82034119217170
H 3.94235361272645 3.33645440616024 2.42843680600382
C 1.79781568478636 5.64526903375468 1.43178002285241
H 2.19027890812548 6.46336671248639 2.05900173698533
H 2.51532196646529 5.48133424994955 0.61070500504627
H 0.84823759561351 5.98200731715388 0.98452938059085
C 0.27497253364526 4.38438617970344 3.80954881877478
H 0.62547454936088 5.18539172065934 4.48142143180096
H -0.69695171115721 4.69600166132051 3.39352497636094
H 0.10895277006318 3.48231061093407 4.42070072631434

Compound 2, isomer 000 000 210 0

C -0.07023859122353 -0.03350418099311 -0.13217826974649
C 1.39356735951145 -0.16228928535094 -0.01874358915739
C 2.26112347297863 0.85079668369599 0.12173469072521
C -0.76783733746215 1.11276012548845 -0.85784305106565

S40
 C -0.03075861045753 2.22056830182415 -1.49299496727180
C 1.12444723022261 2.75287944229378 -1.06187852897156
C -0.92938498985028 0.95546494848758 0.67091264553167
C -0.31482240113302 1.96418936120404 1.60022633251757
C 0.89895151106881 2.53014456917576 1.38833151279208
C 1.82183599318398 2.29786760380494 0.20676674352839
H -0.57228683590048 -0.99555274965457 -0.25515572902384
H 1.78146915553802 -1.18483571851120 -0.06706388051307
H 3.33221016000379 0.63596663627480 0.18485660691341
H -1.64174284758456 0.79995773988378 -1.42963288739916
H -0.47880687801815 2.61857764250563 -2.40905285272241
H 1.58117013600762 3.56776757015151 -1.63195786942883
H 1.25880696422142 3.27423650463682 2.10279029170825
H 2.71497450402239 2.92085199730098 0.35071619932806
C -2.22028438105557 0.29806245487503 1.19498769943546
C -3.20470272285056 -0.23415315089681 0.16508531404576
O -1.90323029314356 -0.79474264699385 2.05158815670044
H -1.12883595509662 -0.54787139359021 2.57433891140284
H -2.76559771113518 1.06367150634269 1.77332068147272
H -4.02435169735103 -0.73907874974285 0.69741895202609
H -3.63204853397155 0.58091557807823 -0.43658462091842
H -2.74471040228779 -0.97440656534489 -0.50756987777780
Si -1.26805272065145 2.69329376341624 3.08980043614868
C -2.78309333270367 3.65819773877207 2.48700266878873
H -3.26021803391895 4.17833060281446 3.33491104652404
H -2.47265788736997 4.42083072499926 1.75355694878059
H -3.54799803550796 3.02692631085529 2.00955051801358
C -1.77075727826873 1.40242643018636 4.38150373251869
H -2.28740854173221 1.90926684176802 5.21417561699639
H -2.43338030499394 0.61326399556409 3.99874688866151
H -0.87409101939463 0.91595520009252 4.80313841069036
C -0.16905035233734 3.93445635733872 4.00025531199555
H -0.72807239010418 4.32446709473630 4.86745095824937
H 0.75577627580151 3.47295457931605 4.38250786403016
H 0.10844766092786 4.79470517364653 3.37058745653538

Compound 2, isomer, 000 001 002 0

C -0.14391160795937 0.13822109106179 0.05223558555210
C 1.31051804685404 0.05902881432582 -0.17741713804392
C 2.15057962574846 1.10346436603012 -0.28047419971454
C -1.01159577642050 1.24492487362943 -0.56695367106742
C -0.44438689444668 2.29220266859644 -1.43660802512270
C 0.75347846540727 2.90642331336801 -1.31145474007492
C -0.78354309795909 1.20798852043012 0.94394309031648
C 0.00965167261303 2.22832963915079 1.65095616417953
C 1.12208950425985 2.83758119599182 1.19920889352703
C 1.71376670321131 2.54994704245697 -0.17351301730806
H -0.64162253039011 -0.83359472078250 0.10270262223385
H 1.71938506377557 -0.95184106246741 -0.27231576517426
H 3.21337472940022 0.90916543322605 -0.45703188622484
H -2.00489144844584 0.90543572337935 -0.87185216600495
H -1.08441805515043 2.56462646014382 -2.28260807045472
H -1.64750067737408 0.84918002074023 1.50914118982383
H -0.34662060982434 2.49043917175999 2.65380031571937
H 2.60623503329878 3.18114197780801 -0.27143494955386

S41
 Si 1.35279787153785 4.14832184319721 -2.59529805270345
C 3.01697153955233 3.54330717567352 -3.25912821139241
H 3.42407508761002 4.24565640188803 -4.00576910703098
H 3.75991142174651 3.45145798261194 -2.44979036017357
H 2.91496505060868 2.55501745643999 -3.73648349455756
C 0.11260036027920 4.28512271066064 -4.01190110287620
H 0.47603753998087 5.00290687616781 -4.76608212187509
H -0.03779074382323 3.31597574700287 -4.51483494165927
H -0.86863616873949 4.64274339379510 -3.65868315876495
C 1.59238865445232 5.84338761273588 -1.79718936846861
H 2.01475081274575 6.56143289794035 -2.52018288615873
H 0.62810943109309 6.24954033359364 -1.44660041244502
H 2.27153953866096 5.78051534009370 -0.93315928068784
C 1.86036099201500 3.82917217628991 2.07193822373699
C 3.24903158750691 3.34762383404502 2.47822208466831
O 2.03887026167089 5.07515220401903 1.40220375773712
H 1.17533200314700 5.36078406930692 1.07422830758928
H 1.26318254185121 3.97838335005204 2.99424893522820
H 3.75271768877725 4.12613820690254 3.07173583106025
H 3.17870875047911 2.42684221388550 3.07562922136208
H 3.87013979933858 3.14379680107028 1.59206417561222

Compound 2, isomer 000 001 020 0

C -0.24067179477885 -0.00098511701886 -0.11547667210785
C 1.21858813127897 -0.13494933778429 -0.28178253271004
C 2.10202925673993 0.87644637688431 -0.29827484282008
C -1.03128290687519 1.15920911573292 -0.74231819695529
C -0.38147113527969 2.22660380525146 -1.52484931763493
C 0.82964385060871 2.78811844242367 -1.30705830415549
C -0.89290421634782 1.05003771114426 0.77801885846480
C -0.12772174799940 2.03393020462747 1.57675707068872
C 1.03102491796529 2.59639887236318 1.18677789487924
C 1.71224809683728 2.33274168381840 -0.14034285066905
H -0.77843188440376 -0.95248844072091 -0.13200170907749
H 1.58893703389481 -1.15669310397851 -0.41310298642210
H 3.16285324374793 0.64993436056545 -0.44471578829851
H -2.01563592128851 0.86984551900515 -1.11939367790414
H -0.97541134370844 2.58311038408048 -2.37342725488719
H -1.78681470386518 0.68826651168579 1.29022900669417
H 1.50968780754173 3.31531516922773 1.86127155498718
H 2.63968888569479 2.92302006654489 -0.15221270437865
Si 1.50243924442050 4.15368510254842 -2.40978265449505
C 3.14041009273279 3.57661458567216 -3.15787867807014
H 3.60038203420149 4.37063100521826 -3.76995276821180
H 3.86360598190089 3.29937125830311 -2.37310258185980
H 2.98819136261089 2.69355992638164 -3.79985997410140
C 0.28149389098819 4.57242736786481 -3.78550683864196
H 0.68540400420698 5.37556660085396 -4.42407702433171
H 0.08392572927555 3.69987659928878 -4.42940467486409
H -0.68135651279199 4.92120730137565 -3.37768950664585
C 1.81821924547386 5.68534006656983 -1.34587990699492
H 2.26758772308852 6.49823613307512 -1.94080385974186
H 0.87750195383077 6.05957864971467 -0.90978283016539
H 2.50664077987539 5.46082131457332 -0.51434285557475
C -0.75754936993690 2.41746711428284 2.90464502520394
C -2.02917316684439 3.24202961390563 2.73390983137841

S42
 O -1.11332994597426 1.26445498757988 3.65993498298985
H -0.32882735894812 0.70254606052779 3.72025022317482
H -0.02002786405987 3.02976863683038 3.46171585848352
H -2.46836544823427 3.45738773439837 3.72031427223964
H -1.80606629500965 4.19060545297380 2.22341263886989
H -2.77654525450633 2.69279188097777 2.14050952033465

Compound 2, isomer 000 001 200 0

C -0.22713398954715 0.08643374567749 0.00456139174156
C 1.23519589184190 -0.05780940516145 -0.12820978191880
C 2.12014750135552 0.94986849738861 -0.18779970242445
C -1.00686557435287 1.21627722048806 -0.68368252453568
C -0.35025308638372 2.24798926582158 -1.50587846191417
C 0.86341876316940 2.81267014513626 -1.31087879723566
C -0.90058580216248 1.15524352430967 0.85479418523079
C -0.12611119482795 2.18973866505159 1.57734805215298
C 1.02411924806336 2.75469157798010 1.17882190998159
C 1.73509596491895 2.41389317541575 -0.11517380585075
H -0.76557389379603 -0.86572638337700 0.00541982241389
H 1.60554069321978 -1.08565367992491 -0.19436985378151
H 3.18252746356168 0.71236861425155 -0.30158789782079
H -1.98177330275777 0.89928390197143 -1.06691744764860
H -0.93939424492229 2.56871111470146 -2.37207534738529
H -0.58786842522811 2.54129153103274 2.50407219913938
H 1.46985900398362 3.53199644210947 1.80771438474652
H 2.66445493878070 3.00040074013718 -0.14665090959981
Si 1.54761144183496 4.12033068471831 -2.47605860877578
C 3.18596397360249 3.49810686482620 -3.18575187299473
H 3.65098388186898 4.25721977435749 -3.83702459749932
H 3.90523830718758 3.26038628401552 -2.38461377527972
H 3.03305819785505 2.58295543311538 -3.78088659928234
C 0.33522140718807 4.47261246798511 -3.87802702076958
H 0.74718929553895 5.23871236302133 -4.55574331983625
H 0.13596663827327 3.56855333683952 -4.47635543458329
H -0.62767319667093 4.84825828419773 -3.49484576388108
C 1.86383359651922 5.70273223911645 -1.49030800337934
H 2.31529518655831 6.48340086814713 -2.12545746614777
H 0.92319679577161 6.10028081736437 -1.07525321225411
H 2.55077462907790 5.52025336780528 -0.64739288632709
C -2.17154818783549 0.70542490197805 1.57814786651049
C -1.88497278404350 -0.03742608668913 2.87523370707789
O -2.99179706285706 1.81530088379491 1.89902181309537
H -3.07613009139468 2.35888227328014 1.10360305627585
H -2.71206714764353 0.01436992815590 0.89682623449250
H -2.83059356522158 -0.31628874070510 3.36416749075629
H -1.30318563588920 -0.95032172599228 2.67799831405979
H -1.31402943467005 0.59542070535076 3.57125750254384

S43
Compound 2, isomer 000 002 001 0
C 0.10631046976125 -0.10987863600048 -0.02125977971022
C 1.55975540555095 0.03029642019597 -0.22617069972490
C 2.23747948763967 1.18867841050760 -0.28307342998076
C -0.90644201125849 0.87893231416783 -0.60037684054882
C -0.51602355036841 2.04631567218337 -1.41132821552945
C 0.57463602976604 2.81492396591276 -1.23558650720218
C -0.68110840433055 0.81933743774879 0.91437127457500
C -0.04404745632269 1.91860045420610 1.66173017207211
C 0.96257878750899 2.72143229725327 1.24812506040155
C 1.59194068035813 2.55158781868810 -0.13675972922811
H -0.24454626051890 -1.14489043115494 -0.00589649402653
H 2.11531747707177 -0.90611116413092 -0.33811383879222
H 3.32077114166591 1.15835407021269 -0.43698726816830
H -1.84041551964836 0.41109659185197 -0.92226815532214
H -1.18153825557118 2.29913065968550 -2.24156023051196
H -1.48102029816455 0.31545440293350 1.46306054102417
H -0.45699659752112 2.07631310861052 2.66396976296891
H 2.38946663183907 3.30194079082297 -0.24568715264322
C 0.86833308859343 3.98723656121247 -2.15480431927825
C 1.98766335147657 3.66159141575569 -3.14199465897793
O -0.24860616961446 4.39149671912127 -2.92210738728983
H -0.96874927311394 4.58497718870688 -2.30643394466019
H 1.21021866946503 4.82706275166402 -1.51162408961324
H 2.21517605272415 4.54308704428723 -3.76083821599143
H 2.90376567002693 3.35090773882477 -2.61772431248403
H 1.66630842084641 2.83949362983317 -3.79944833577729
Si 1.66526925961771 4.06893660847243 2.35497845424615
C 1.47579153783504 5.74221007564140 1.49196977515366
H 1.87267459748301 6.55678890430391 2.12088051576303
H 2.02152501873939 5.76745995086482 0.53462505767691
H 0.41570698124111 5.95950246019445 1.28141872168519
C 0.76953990262134 4.11028898296349 4.01470971839681
H 1.19158717721931 4.90163893868349 4.65622906047244
H -0.30549649552714 4.31905915074693 3.88910100396588
H 0.87120106022459 3.15352241108279 4.55246584894944
C 3.50545289457533 3.72935718480797 2.62675279277754
H 3.97365543116825 4.52843223790794 3.22583801641786
H 3.65302324101048 2.77317800454815 3.15490785736351
H 4.04820231108634 3.66936842578484 1.66883483840747

Compound 2, isomer 000 002 010 0

C 0.43608839628587 -0.03208460905389 0.25227588877051
C 1.87863355957432 0.27160991173638 0.20907555833753
C 2.41968786578964 1.49269237538560 0.06536162090259
C -0.58625446585524 0.72430710957230 -0.60634996633711

S44
 C -0.20252665900758 1.80688133725721 -1.52904325003651
C 0.74965004400893 2.73724362738130 -1.32608120530180
C -0.58685531721370 0.89405618595569 0.91638062860971
C -0.22974253442532 2.16500121709988 1.59606202145405
C 0.74269042768428 2.99623418561617 1.15950934853696
C 1.60476774798137 2.76509184669298 -0.06555106732346
H 0.20948636525641 -1.09484441994911 0.37062886964735
H 2.54734629996739 -0.59020163894859 0.30139309903577
H 3.50985298418865 1.59038570704637 0.04669081446740
H -1.39689693978184 0.09370851277916 -0.98044794258415
H -0.76683178337984 1.84819926337155 -2.46788665477724
H -1.39863111797348 0.34111010494412 1.39869776714529
H 0.94048393285145 3.91879628865566 1.71537898235030
H 2.30845621867616 3.60010846436276 -0.16667156991625
C 1.02359057694904 3.81365218835271 -2.35278504275860
C 0.63639712652454 5.20647701986082 -1.86652033696741
O 2.41016141323246 3.86271132584200 -2.67709796837331
H 2.68334143703301 2.96600672525349 -2.91466012015202
H 0.42500964325368 3.58316208946236 -3.25789820205977
H 0.91590170685857 5.95565546499814 -2.62340330239682
H -0.44686970924262 5.26372880214968 -1.68446144467268
H 1.16200529756329 5.45643315233919 -0.93156767189442
Si -1.23244233269656 2.59089910242883 3.13667822172201
C -1.02107131800634 1.20717900595568 4.40755381689743
H -1.62328438545943 1.40300938697591 5.31069123598943
H -1.33825507039303 0.23352627001586 3.99912159078982
H 0.03396673933863 1.11441524804280 4.71353851102440
C -0.65449781006322 4.22709934640042 3.87571438540541
H -1.24548639401761 4.46575147776597 4.77557288487261
H 0.40612509773925 4.18529278310611 4.17255338465795
H -0.77760825648312 5.05934461007257 3.16365945750747
C -3.05790952877365 2.71771279913962 2.65994365001673
H -3.68483452449952 2.92862245480533 3.54263878381609
H -3.21563141266532 3.52647533352697 1.92752149718608
H -3.42195415685267 1.78061232989440 2.20748389111468

Compound 2, isomer 000 002 100 0

C -0.15176588521774 0.01707421601830 -0.24684295120097
C 1.31277232486323 -0.09454859326116 -0.38394351175391
C 2.19279529878660 0.91995222511179 -0.34602065858740
C -0.93790387253522 1.20140448735373 -0.79762708393611
C -0.29912514116981 2.32433161919863 -1.50670005062799
C 0.90134700299950 2.87462522042354 -1.24284121272705
C -0.84089739061472 0.99538892902482 0.73168984966547
C -0.03058893130477 1.92502323655269 1.55896177495692
C 1.11600133856000 2.53692352147287 1.21623620482118
C 1.79952321320663 2.36703314107507 -0.12317194828614
H -0.66736889534686 -0.94079988435076 -0.35589566406588
H 1.69411697916098 -1.10978826974747 -0.53384046559491
H 3.25864391004053 0.70036288043703 -0.46480194806113
H -1.90530477570671 0.92392135280596 -1.22458742627120
H -0.88303585613615 2.74736373572588 -2.33243817722045
H -0.42035706097416 2.13350796047124 2.56190123479326
H 1.59269349221711 3.20155286133546 1.94410496141013
H 2.71631974544146 2.96862688965202 -0.13778239700548
C 1.42073749458388 4.04193193347224 -2.05281834067787
C 1.50146428895480 5.33391768544848 -1.24640334148156
O 2.73481297952969 3.77694850709424 -2.53588245409186
H 2.71029129980032 2.92155977837538 -2.98624122053120

S45
 H 0.72500470895552 4.20554557871905 -2.90121003011606
H 1.94380998205345 6.13068057268341 -1.86430540750599
H 0.49937596146718 5.64612622043754 -0.91751180256574
H 2.13672950598307 5.20282497860001 -0.35643300840823
Si -2.39944377286785 0.36915877264865 1.60707993755017
C -3.47840948429602 1.85485773951234 2.04340081575736
H -4.39575170528061 1.54040218922395 2.56856802189320
H -2.94395483983828 2.56459119545690 2.69529338297484
H -3.77765998591047 2.39871167527235 1.13215086649295
C -3.38113389449161 -0.80248379765402 0.49652870424818
H -4.28158160108670 -1.14306040527151 1.03471336869690
H -3.71955479730547 -0.31398018677884 -0.43157851735424
H -2.80517078387395 -1.70068304297934 0.22082962457721
C -1.88111077551522 -0.55038475255174 3.17145382800948
H -2.75939882722481 -0.92601152033377 3.72256224745241
H -1.24216390593529 -1.41330878884667 2.92090963480042
H -1.30993374703687 0.10118323096018 3.85229759172051

Compound 2, isomer 000 010 002 0

C 0.47594941696758 0.06554321845782 -0.22852354520003
C 1.92117033145269 0.35990187816515 -0.25146573076924
C 2.47512152841702 1.58252392711147 -0.19974904352369
C -0.56329805432469 0.95410766619727 -0.91809222422747
C -0.22154111975373 2.18098400585008 -1.68106195898644
C 0.76755088028510 3.02963489617967 -1.32224119318572
C -0.51726319180193 0.87935160657261 0.61162392805785
C -0.10828254746893 2.02054531639584 1.44899888530291
C 0.86003926544736 2.91490229648522 1.17346078146041
C 1.67147614968591 2.86402968292631 -0.11470669843540
H 0.24046636706781 -1.00093027020768 -0.27408295757791
H 2.58055259999737 -0.51178969809992 -0.31139771757721
H 3.56599298706661 1.67072107687906 -0.21855306984134
H -1.39176516056868 0.37820731015815 -1.34151291110051
H 0.95530190808820 3.91565099080666 -1.93798090235932
H -1.32004392026943 0.27898586324969 1.04730274446064
H -0.65655119214692 2.13367350405324 2.39143272540969
H 2.36121307568131 3.71647743445865 -0.10060434280126
Si -1.26329939419944 2.51759535157772 -3.21794343809657
C -1.08069695990918 1.06340241731575 -4.41197763699623
H -1.70409035075456 1.20773632587455 -5.31042279664386
H -0.03299517439849 0.95322979531444 -4.73676881912786
H -1.38704839506954 0.11471027776396 -3.94139194064129
C -3.07695068945713 2.67113492699521 -2.70460896230783
H -3.72511249428550 2.83078555280926 -3.58270542102398
H -3.42871069885157 1.76149081330816 -2.19063056571015
H -3.21939716151098 3.52067895567108 -2.01649456965784
C -0.70781676187922 4.10887778332271 -4.06475457162805
H -1.32292556852343 4.29493754201046 -4.96084606222149
H -0.81299107884096 4.98147769632677 -3.39964190776335
H 0.34456663764310 4.05026106948973 -4.38688753179516
C 1.18308884113323 4.03833734452254 2.13351832748134
C 2.56628288700690 3.90484826923710 2.76161925082303
O 1.15576881293679 5.29631380875857 1.46433419309231
H 0.30930623449274 5.35851793616546 1.00093206232422

S46
 H 0.42906419490137 4.01927505680250 2.94692364216770
H 2.77068222730100 4.77892445003648 3.39916218063078
H 2.62637344543264 2.99131970984574 3.37128922381138
H 3.34739516367529 3.86060540509240 1.98661130969477

Compound 2, isomer 000 010 020 0

C -0.21592984879114 -0.04650632381072 0.05477509872011
C 1.24740212871115 -0.22699919064604 0.02198262030263
C 2.15934723397844 0.75764234400483 -0.02328609634052
C -0.93305477348270 1.05852023991732 -0.73121293535150
C -0.22819563077332 2.04226904951468 -1.59054733410483
C 0.98306335824161 2.56323124738406 -1.29197974124813
C -0.90213641195454 1.10221144447763 0.79668520930244
C -0.16514742305986 2.13923322540594 1.55275924429076
C 1.03574895530547 2.63457431941597 1.20004844542679
C 1.79362093634351 2.23025777148607 -0.05057105552602
H -0.77499904358612 -0.98492133691598 0.09672417524605
H 1.59706210267565 -1.26439223750016 0.03296046901074
H 3.22197426694847 0.49694192996032 -0.04860547736142
H -1.90162682383583 0.73324296169310 -1.12292729333653
H 1.43264288448635 3.28765660835716 -1.97905555337215
H -1.83582176309136 0.80815871938482 1.28052868982801
H 1.49016963999559 3.39954079642680 1.83950471754231
H 2.72447322839222 2.81246493357299 -0.08626053721174
Si -1.14156198808359 2.56988802814907 -3.15508722306151
C -2.79461290561962 3.33948474470305 -2.65490958682260
H -3.38186330559794 3.63159757880066 -3.54171032836359
H -3.40492426353798 2.63449239366125 -2.06685218256729
H -2.63588504253114 4.23936831124730 -2.03806792913895
C -0.12619224847555 3.82428753942962 -4.13149295941985
H -0.67120367444734 4.12466079759939 -5.04184778899561
H 0.06910108589740 4.73496264495541 -3.54218964230646
H 0.84371182320464 3.40483005607284 -4.44481803974231
C -1.46540601075423 1.04453264845617 -4.22396373933972
H -2.03636694248080 1.30974697890216 -5.12969328107917
H -0.51702784137580 0.58064241532377 -4.54140774442758
H -2.04363041401364 0.28288802872764 -3.67549206639465
C -0.87766785861826 2.66498616501443 2.78698490722038
C -2.10644183220016 3.49902284521606 2.43902416462587
O -1.32501284133440 1.60086913786398 3.61988041845353
H -0.56605802660420 1.02709165980345 3.79181160436010
H -0.16450975923291 3.31087838653405 3.33791296592154
H -2.61226966273299 3.82095012097203 3.36247116581971
H -1.81579806584764 4.38688955804388 1.85817928838169
H -2.82298991700273 2.91176919667268 1.84409555933159

S47
Compound 2, isomer 000 010 200 0
C 0.14134693259532 0.15835951574262 0.07686316727296
C 1.60588899580082 0.29971419465860 0.19259403774283
C 2.28278997543678 1.45828285637792 0.20686240690849
C -0.71598039612849 1.08720337310917 -0.78416076375963
C -0.19041644907181 2.22601995929924 -1.57342452255893
C 0.85349983795717 2.99104919657711 -1.18356220440632
C -0.85545804771105 1.09881580066324 0.75206504854906
C -0.40986236456499 2.27837222834700 1.52673600584183
C 0.66549697425892 3.04430095775608 1.28122929961251
C 1.61670660173845 2.81851033375607 0.11944315227195
H -0.19826658345629 -0.88124783962567 0.05433353980810
H 2.16762958846031 -0.63692393658829 0.26545681516360
H 3.37355928574139 1.43325587387091 0.29209997877351
H -1.53998812520433 0.55124867598597 -1.26736662999697
H 1.16563147767040 3.82676335194196 -1.81872490589867
H -1.06553841917174 2.55401084127710 2.35732197324950
H 0.85898517567696 3.90120915254913 1.93419954436347
H 2.40065469203815 3.58683568450532 0.16099839749523
Si -1.15522586287698 2.62562350462955 -3.14304390401918
C -1.11391400026238 1.14052592193077 -4.31082623394048
H -1.71935773227220 1.32880865133386 -5.21336907084213
H -0.08166603330961 0.92360243671843 -4.63136886201775
H -1.51112559961305 0.23399774933663 -3.82532833164880
C -2.94759700207649 2.96121028378501 -2.63110137340495
H -3.58483119707587 3.17726988225411 -3.50481914446160
H -3.38486186197894 2.09136917269908 -2.11221196681682
H -3.00126501751585 3.82591183533381 -1.94875310996050
C -0.44042868773365 4.14114610551086 -4.00653503393342
H -1.01815807420604 4.36911437486488 -4.91760636958474
H -0.47376094213583 5.03007845797295 -3.35593950988200
H 0.60729731685553 3.97663291423804 -4.30695356230855
C -2.13262030689317 0.44495009516722 1.28009663531682
C -1.97174035237460 -0.16396942022915 2.66521725161971
O -3.18576733814032 1.39132834664455 1.34867507204251
H -3.19840670544021 1.87996558611830 0.51385156679473
H -2.39882211977967 -0.37171651138569 0.57569904075559
H -2.92668688547820 -0.59892559897784 2.99691885387736
H -1.20606624822842 -0.95428775428813 2.65182045834698
H -1.67155287441301 0.59930710607101 3.39875629070877

Compound 2, isomer 000 020 001 0

C -0.02447609914618 0.05726473761616 -0.10151272250412

S48
 C 1.43184094242824 -0.01566655880487 0.11868482221877
C 2.26435334795967 1.03360117265543 0.22491410420494
C -0.68001470664088 1.12304922042726 -0.97521226663290
C 0.08720613867278 2.16127711939327 -1.69990534149453
C 1.18012300571855 2.77897484865257 -1.21482962119787
C -0.88913188966716 1.15540063498349 0.53995786597188
C -0.32460939841823 2.20318282221119 1.41018103848540
C 0.86705499845748 2.82851791116159 1.27905511438838
C 1.81452795381385 2.47873000213364 0.12777764143506
H -0.51781455035200 -0.91695336939425 -0.14912828658596
H 1.84749297314185 -1.02424178807852 0.20879650691275
H 3.32868973341246 0.84701283767813 0.39935080341878
H -1.56037151779151 0.78267615372493 -1.52418104850432
H 1.65863490726001 3.54560070493636 -1.83463566237212
H -1.87734170406232 0.80778830000994 0.85226852704696
H -0.96810444151332 2.47921148073547 2.25274519336180
H 2.71254742557801 3.10761593866400 0.21066584333233
C -0.43811443379209 2.50609994975305 -3.08270382359685
C -0.24249015641166 1.37378807514920 -4.08530077060565
O -1.83315704587206 2.78834165457035 -3.04824553340621
H -1.97693814267137 3.46100751301249 -2.36879465322529
H 0.12450802998065 3.39028369096672 -3.44453399018654
H -0.67617834218120 1.65777148182723 -5.05665223167811
H 0.82811991949772 1.15817379776874 -4.21730229199213
H -0.74471665918666 0.45558668710668 -3.74321731549816
Si 1.43915516683573 4.14170741871781 2.49612881243696
C 3.07099183325499 3.57987755210437 3.26857553662701
H 3.47108464986128 4.34525320440790 3.95471458082700
H 2.93337821254522 2.64646639003410 3.83853002590266
H 3.83563466816738 3.39125528566841 2.49694781614855
C 1.72883178034349 5.75612298069801 1.55396200093822
H 2.11796746991970 6.54247343569447 2.22249224533961
H 2.45901487283569 5.62022545685855 0.73901248010381
H 0.79066211609920 6.12207730992637 1.10544775064838
C 0.15092472296487 4.41415557807260 3.84718812898484
H 0.49639134800648 5.18570465474790 4.55519955731551
H -0.81045469928293 4.75201353258661 3.42680866916180
H -0.03286898670767 3.49103664666915 4.42084401782924

Compound 2, isomer 000 020 010 0

C -0.27368652243982 -0.01932462761461 -0.04881226978911
C 1.18557659061283 -0.23035072364562 -0.02486793616017
C 2.11981424061828 0.73403073482633 0.02123625770371
C -0.92853377787461 1.14811296495828 -0.79029400535350
C -0.15645056538561 2.14944114853205 -1.55958965055558
C 1.04081850836138 2.64072793479680 -1.18947489314234
C -0.95628925739958 1.10785211702015 0.73746107241658
C -0.22469903131278 2.06391531551066 1.60595413463362
C 0.99713494883862 2.55852937591396 1.30751009204728
C 1.79097540808409 2.21592086943637 0.05896493786717
H -0.85477146495387 -0.94445601504216 -0.08526017911954
H 1.51325601516990 -1.27459700517421 -0.04651039718848
H 3.17619942624303 0.44839321023183 0.03567274196259
H -1.89191949337004 0.91271402827549 -1.24713256544350
H 1.51738909208300 3.38806697298308 -1.83359499716273
H -1.93472523384623 0.80992506147026 1.12641874024527

S49
 H 1.47166722529600 3.25885127721292 2.00275180398526
H 2.73619525485120 2.77458693632650 0.09327181127497
C -0.80662883558834 2.61041350846003 -2.85293362691426
C -0.83299251706033 1.52072435411494 -3.91938818892114
O -2.15657685224420 3.00770101458673 -2.63698266812168
H -2.15958162435864 3.64693349776491 -1.91157847076780
H -0.21284819681454 3.46193474138073 -3.24225381915306
H -1.35169379448938 1.89116902960730 -4.81716135668498
H 0.19096090895287 1.22418989592886 -4.19093291863904
H -1.37073417410010 0.63053181667283 -3.55788565357353
Si -1.10974208436105 2.58110544264451 3.19018438150163
C -2.74286446832335 3.41414061649747 2.72527261229311
H -3.31861162655934 3.69037184294365 3.62459927573123
H -2.56151629244046 4.33212593752949 2.14201115868661
H -3.37495779259591 2.74801794413102 2.11521890375839
C -1.47295658046508 1.04057228469591 4.22365626215600
H -2.02369146565659 1.30133356031994 5.14306933820909
H -2.08332891799585 0.31349159820800 3.66330093431526
H -0.53722302644795 0.53682947820891 4.51690948674250
C -0.04852219832926 3.77942520750253 4.18798622536678
H -0.57647970929427 4.07466372502812 5.10997989340137
H 0.90998481171454 3.32191917350411 4.48251877732848
H 0.17119322874682 4.69766512957036 3.61933896430171

Compound 2, isomer 000 020 100 0

C -0.15355884663958 -0.02159813004587 -0.03921921968329
C 1.31484290811808 -0.13227528498618 -0.12832960973300
C 2.18511883248139 0.88963807562355 -0.17679325364894
C -0.93497438301032 1.09246193879376 -0.70633211430713
C -0.33474502353328 2.18142875857797 -1.50630360195062
C 0.86191101400319 2.74534905353428 -1.25768223583166
C -0.86791221040680 1.03860767176631 0.83748100016330
C -0.07482713135641 2.04089834192262 1.58942152758886
C 1.07457772791743 2.62757086647722 1.21034566317100
C 1.76908214449492 2.34716390093965 -0.10933918918169
H -0.66064143606749 -0.98945774232162 -0.06635685091655
H 1.70840061985268 -1.15334168863524 -0.15892815910623
H 3.25523616562800 0.67044319274475 -0.24454283993015
H -1.90272687699041 0.77700053562029 -1.10276769882491
H 1.19372918052557 3.56796813436984 -1.90078002783052
H -0.47404766387531 2.32528540700903 2.56932291129983
H 1.54537998018449 3.34689388201755 1.88813120204656
H 2.67554011373576 2.96544165432139 -0.16048224098084
C -1.20997914628552 2.70282438133159 -2.63261785324391
C -1.45937136201499 1.68114766811938 -3.73529470337180
O -2.48860462289441 3.09403261266304 -2.13213257241959
H -2.33838578151364 3.70173191656288 -1.39492051355780
H -0.69562159136006 3.57584327260172 -3.08131708542757
H -2.12582666793351 2.11222944510920 -4.49813002378884
H -0.51056027273128 1.38958940173591 -4.20979720587947
H -1.94304702927114 0.77662296075011 -3.33540566904939
Si -2.53501854471779 0.59976162593762 1.62316324416255
C -2.33220839356612 0.25408533361014 3.46785388636114
H -3.30009000179427 -0.02236421078775 3.91864174303648
H -1.63005626976301 -0.57917946468900 3.63649233998602
H -1.95066181215898 1.13178446813605 4.01390828464931
C -3.65647912830522 2.08994746330345 1.33482765428598

S50
 H -4.67984035983528 1.92102984000173 1.70834775750185
H -3.25529298046979 2.98502931512950 1.83901049208542
H -3.71169511130387 2.30521161158226 0.25485523902121
C -3.27882859011664 -0.92621553528885 0.79527389541464
H -4.29047217438050 -1.10604318622276 1.19576672508534
H -3.37471477405755 -0.80789395296446 -0.29602579802293
H -2.67971472356305 -1.83040675105545 0.99157108930253

Compound 2, isomer 000 100 002 0

C -0.02137317104183 0.11529074951823 0.11313021577460
C 1.45397375453206 0.12531032959890 0.10214745467068
C 2.23989996993295 1.20958701607691 -0.00505392770767
C -0.88435342263296 1.03574692740670 -0.78024653759150
C -0.24121164834550 2.04077268331711 -1.66316944479856
C 0.87744331105661 2.74507319596565 -1.42012297047465
C -0.84826651649878 1.22328102308574 0.75452365026199
C -0.24759099955534 2.39943463079318 1.40842241206369
C 0.88524541383593 3.03576264889843 1.05446506461983
C 1.70619479514682 2.61858409473580 -0.15804494915961
H -0.44180489168612 -0.88354167878094 0.25741062117214
H 1.92985665694256 -0.85591552079092 0.19766147139857
H 3.32651414949094 1.07816915633668 0.00792045015578
H -0.74210092789537 2.22528447587314 -2.62056508106387
H 1.22577178217719 3.45388578645207 -2.17856895870948
H -1.74340248479589 0.86196259364062 1.26783889642598
H -0.79330869320396 2.77750019725513 2.28077161552478
H 2.54932872360455 3.31489865909050 -0.24090183544301
Si -2.46368318380826 0.28757316212022 -1.50991560743450
C -3.71114855161090 1.67792204499301 -1.78099761612682
H -4.64642613171944 1.29489238067339 -2.22227722800123
H -3.96171300482635 2.16754178576280 -0.82537853825083
H -3.31171480897948 2.45069254272257 -2.45758423678023
C -2.03642215158385 -0.54062395847616 -3.15102571244762
H -2.93178253856774 -0.98422836718443 -3.61768814893545
H -1.60531373442780 0.17792836197194 -3.86666811503951
H -1.29782768762724 -1.34513109669073 -2.99971567666724
C -3.20932771275866 -0.99835701332580 -0.34417338176582
H -4.13586039310527 -1.39880617638381 -0.78864637456915
H -2.53139238495895 -1.85080043932266 -0.17601066081470
H -3.47394022326778 -0.57219225698192 0.63708858186173
C 1.39087362427598 4.22564837881405 1.83961489172702
C 2.70117323846124 3.94270751840742 2.56680395680499
O 1.63137517341529 5.33434081744764 0.97705772695732
H 0.82851307956074 5.47478782081511 0.45664415144978
H 0.62303801835171 4.48699021176725 2.59637847886186
H 3.05384457516869 4.85799136463085 3.06696820145080
H 2.56213416937491 3.15137989285917 3.31800601550906
H 3.48138279730213 3.62076351097458 1.85941532542103

Compound 2, isomer 000 100 020 0

S51
 C -0.12525159326122 -0.01562867451945 0.19328883687677
C 1.33440327647132 -0.21900318575376 0.25254460983059
C 2.27157027195046 0.74226361400402 0.21055654535937
C -0.79897808738006 1.02741698749000 -0.73496578513538
C 0.03652211532382 1.92913488700977 -1.56592635160436
C 1.22982620931246 2.46286844514382 -1.25056648251910
C -0.82501217494086 1.18775676203807 0.79946776759001
C -0.12775892387956 2.27980998113586 1.51363492618325
C 1.10591325929952 2.72958340253410 1.21840424400593
C 1.94578611325214 2.21673377359278 0.06445605160081
H -0.69126473525493 -0.94517524677608 0.29759754333957
H 1.66009688701111 -1.26082922117199 0.33735862682430
H 3.32688259596206 0.45673309560245 0.26177150450593
H -0.37137558266187 2.18308001733501 -2.55108930218452
H 1.72316916535242 3.11197424616424 -1.98108010864977
H -1.77927993049332 0.93960556124518 1.26911939638138
H 1.51986794183939 3.54600103538042 1.82063150424340
H 2.88990118346646 2.77806127326649 0.05327300085874
Si -2.44288701923073 0.54494392528451 -1.54019519891337
C -3.44378669664154 2.12256217661688 -1.80729481796331
H -4.41481775174451 1.90678017268352 -2.28324693754670
H -3.64017631339093 2.62311522608070 -0.84482938693482
H -2.90420519241010 2.83691358384255 -2.45004197303704
C -2.09501130387028 -0.30348680597908 -3.18996325867833
H -3.03275462991198 -0.58935748500844 -3.69513475622817
H -1.53183397663101 0.35222802357036 -3.87350337099971
H -1.49876259296014 -1.21836685939294 -3.03748028230804
C -3.41801724317460 -0.63186027427680 -0.43105709060279
H -4.38429751600242 -0.86693384516615 -0.90782923972747
H -2.89011583222490 -1.58612188662990 -0.27150117069030
H -3.63563229290188 -0.19192893387884 0.55549767149764
C -0.93360912316397 2.92803751055378 2.62616526465878
C -2.11625699241807 3.73122361093962 2.09414642760460
O -1.46843555696500 1.95426809989220 3.51710718505381
H -0.73757397542696 1.39084921882834 3.80563692854607
H -0.26074860741714 3.61940510706250 3.17222271826653
H -2.69208929030634 4.14922138035239 2.93421817598454
H -1.76625286611187 4.55229914369852 1.45131191168367
H -2.79000158817809 3.08985300203912 1.50494879658584

Compound 2, isomer 000 100 200 0

C -0.07517317822798 -0.02826065787765 0.14436440528717
C 1.39702647763202 -0.11788853197941 0.21636687013587
C 2.25856442609377 0.90889806298611 0.15439640752745
C -0.83784270484993 0.92608978332541 -0.80700788054167
C -0.09049422115068 1.93303636721105 -1.60659946119891
C 1.06433474726982 2.55252514650823 -1.30403676262600
C -0.89448422738244 1.08947258386084 0.75635027223849
C -0.25189485155033 2.25174921377564 1.41582218765477
C 0.93482539066912 2.80983611348451 1.12934966935020
C 1.82486099153214 2.35187249973841 -0.00852013329864
H -0.55688094160339 -1.00518122126583 0.23949401577138
H 1.79914298406630 -1.13046518257391 0.32395934456369
H 3.33192752187529 0.70392552042175 0.21525190363106
H -0.54367358931962 2.20663387172768 -2.56340924720718
H 1.46611966106541 3.27778377182058 -2.01892727778987
H -0.85120591955481 2.69982546138367 2.21285787341685

S52
 H 1.26081663272398 3.67579362184043 1.71427922848246
H 2.72280211492881 2.98414617148408 -0.02859862385254
Si -2.28453064062637 0.15708630224973 -1.79982423876762
C -1.82008666570705 0.17302748714214 -3.63346624132812
H -2.54572977885442 -0.43414859821554 -4.20018677113097
H -1.82821186601573 1.18568741285712 -4.06638997031983
H -0.81804368189570 -0.25632886069527 -3.79636487107458
C -2.59835370457496 -1.65698012617726 -1.36352301823340
H -3.39061367693730 -2.04734963861523 -2.02446191101957
H -1.69407242694823 -2.26259878245936 -1.54032069737998
H -2.92275091027191 -1.82548131358875 -0.32573587649627
C -3.86951786023099 1.16539975052738 -1.58206363203798
H -4.64828464965072 0.80827134808382 -2.27651777104057
H -4.27745645226300 1.09872885821983 -0.56156928409155
H -3.68677013207608 2.22897484232981 -1.81268461421202
C -2.18068943403038 0.66333682299311 1.47029900045310
C -1.92292741723308 0.10025857169612 2.86153038068373
O -3.07773062844466 1.75475712459680 1.61313556994487
H -3.10981687931456 2.22385307684940 0.76882693610103
H -2.65860018042734 -0.13358590736499 0.87394676646894
H -2.87783105706301 -0.16499762867016 3.34013755658475
H -1.29354513730785 -0.80034336162846 2.80111643595109
H -1.41309057250963 0.83861534370814 3.49803639326993

Compound 2, isomer 000 200 001 0

C 0.15535946011798 -0.01767645958042 -0.14603285905955
C 1.62322182302240 0.10037183879454 -0.20786700117822
C 2.32464918931952 1.24620108147521 -0.17833657414327
C -0.81348091375334 0.97563586120580 -0.81283327483947
C -0.29213284903485 2.12510936513556 -1.58661736896438
C 0.79070016119938 2.86287323182334 -1.29620499879547
C -0.70346692243594 0.92478582824809 0.70883387514111
C -0.13086342442090 2.01502836335668 1.52132588874721
C 0.92663180833031 2.79929095904725 1.21704061854448
C 1.68821562342565 2.62083034623245 -0.09907654887333
H -0.20907879275181 -1.04955455559028 -0.14874057603222
H 2.17089137954573 -0.84543020946409 -0.27065072793452
H 3.41731027664039 1.19591317304712 -0.21891831869449
H -0.84840054439060 2.35030597173958 -2.50066818280489
H 1.06268075930109 3.67985916734442 -1.97220448291819
H -1.54992462402115 0.42192738587349 1.18562541604111
H -0.64366567909563 2.17724423704654 2.47552798668605
H 2.49915137395565 3.36214260264559 -0.13846987235301
C -2.08781802440112 0.35795175141791 -1.39231786066290
C -3.28574512250910 1.29454964441429 -1.32724142331718
O -1.90421821050406 0.00065486370967 -2.75115526935796
H -1.07569837497415 -0.49381819255371 -2.81665118631039
H -2.32253103367047 -0.54393311982871 -0.78771097256429
H -4.16573472926713 0.80922224371956 -1.77565376558751
H -3.51623028132636 1.55576373376077 -0.28351778857272
H -3.08792419849996 2.22359563760043 -1.88282853354676
Si 1.52492685694998 4.14981446362892 2.38061412783607
C 1.42915478809751 5.80942506409587 1.47958876287268
H 1.81825900745326 6.62683380730672 2.10977348044967
H 2.01984041358362 5.79596194199538 0.54869170950612
H 0.38732349146491 6.04955447788429 1.21127511196818
C 0.46815580319733 4.20811017277403 3.94223415440005
H 0.82717952985572 5.00318816186246 4.61668191557030
H -0.58785400540175 4.41979177142525 3.70757211708818
H 0.51132539195585 3.25532188222614 4.49484213630854
C 3.32620879546813 3.80071905692453 2.83856879989187

S53
 H 3.73320100507229 4.59728865188622 3.48395820316734
H 3.41546052505743 2.84355724154924 3.37800030664875
H 3.96420392062459 3.74045374413687 1.94132266637920

Compound 2, isomer 000 200 010 0

C 0.17396616853986 0.10724137311879 0.02700071855909
C 1.63111372652232 0.29429733428987 -0.08937130438993
C 2.27365512455850 1.47271715714937 -0.15267676909770
C -0.86191758565446 1.00672595510072 -0.68216336313609
C -0.40990621477834 2.12025082205950 -1.54641149078016
C 0.64120957545016 2.92758569754540 -1.33383130557534
C -0.71816488526265 1.05485923661831 0.83472533588804
C -0.21715863433620 2.23071212206116 1.59020462531928
C 0.79783322109779 3.01251095179653 1.16312487028020
C 1.56297441330558 2.81484088979884 -0.13341879881074
H -0.13455800236859 -0.94059699832284 0.09453537783347
H 2.22427769661770 -0.62539809961700 -0.11970016016080
H 3.36495650780707 1.47653076536273 -0.23517085151599
H -0.98831753022739 2.24654273037462 -2.46584237859940
H 0.86903555082133 3.69914477711171 -2.07607728388037
H -1.52965002803352 0.51911510601813 1.33807640244714
H 1.10666182239724 3.86409184810861 1.77829711808265
H 2.32158704332786 3.60601529758953 -0.20559864542959
C -2.11671046942818 0.29254333987874 -1.18832541115872
C -3.35570114044220 1.17574913041648 -1.14464789734596
O -1.95273751396098 -0.14139620805985 -2.52715518824543
H -1.10377423646634 -0.60079502007485 -2.58596759406807
H -2.29076379865727 -0.57930953344652 -0.52234135915375
H -4.22451474551501 0.62425090364634 -1.53450779937183
H -3.56791635463558 1.49342321690358 -0.11294271915875
H -3.21639455368394 2.07560811384832 -1.76258435193323
Si -1.10557692630310 2.60283555741561 3.21207983335934
C -0.91637608601107 1.12161798506198 4.37156841972485
H -1.46302377417527 1.28459557416084 5.31563748218356
H -1.30926611364877 0.19909819889990 3.91321579012600
H 0.14450123830986 0.94843098589522 4.61620072289566
C -0.38990913711347 4.14615051623212 4.02583429810411
H -0.91871280489230 4.35648270406406 4.97030950039768
H 0.67947238335704 4.02092312778569 4.26159655187848
H -0.49596042344279 5.03118982653230 3.37760046070404
C -2.94253002230271 2.86654495604887 2.84681739502344
H -3.50314700710957 3.08587217535321 3.77098605667498
H -3.08749980190069 3.70886189566516 2.15058734682402
H -3.39416851408041 1.97118875230646 2.38893567036698

Compound 2, isomer 000 200 100 0

C -0.06685441742185 0.01391600583844 -0.16917059162340
C 1.40402454323150 -0.06951327049772 -0.23460333195465
C 2.26623087873360 0.95702182948377 -0.15076970828589
C -0.90150709673534 1.15659232351268 -0.75517707982510

S54
 C -0.22671708293978 2.29800582729626 -1.42468740034183
C 0.96045835221777 2.84780498820179 -1.12581636934132
C -0.83700868617968 0.96446039048515 0.77987487107847
C -0.08777634028269 1.95087455204093 1.61004418464775
C 1.06732044670352 2.57459195236461 1.32715096463444
C 1.82983118224634 2.39835852255783 0.03119419505071
H -0.55132688971446 -0.96214228421566 -0.27805025644264
H 1.80946069273024 -1.07887768813845 -0.36059624839806
H 3.33958934997595 0.75307614573113 -0.21476529418939
H -0.76160311571528 2.68467546662339 -2.29554307142806
H 1.32439700939435 3.67393444596247 -1.74494275103747
H -0.54041840635692 2.19497257902680 2.57688069577168
H 1.47503978776137 3.27403644736928 2.06397514224518
H 2.72644777421630 3.03198237654867 0.06402994443284
C -2.17322120285211 0.73291752460847 -1.49854894889776
C -3.30098746424112 1.74842850914463 -1.39683246381509
O -1.90060001039400 0.54602517544551 -2.88052119075014
H -1.10789388984195 -0.00320059589650 -2.95238979998191
H -2.52097933769097 -0.21789714582266 -1.06459592663300
H -4.16767196007525 1.40515637933349 -1.98186325939765
H -3.60913091645938 1.88191657428308 -0.35063757564280
H -2.98835447886122 2.72696606392015 -1.79107010855523
Si -2.16215472384115 0.13800449170042 1.88095941091710
C -1.18119152010595 -0.68686478206142 3.26986412791504
H -1.85621839517743 -1.18643862385844 3.98464589367707
H -0.49969133278331 -1.44901184491044 2.85668945199495
H -0.56806923367071 0.03670560069031 3.82908604861990
C -3.32601252311228 1.43642402277717 2.60983110645018
H -4.00818828151814 0.96237918754290 3.33548534331383
H -2.78163175478462 2.23498804965561 3.13777192786508
H -3.94452980326364 1.91159469481826 1.83183400664255
C -3.21970639740411 -1.21247457749589 1.08382847262095
H -3.75192041976923 -1.73752354186849 1.89567136320157
H -3.97955407381859 -0.81572290580085 0.39400598933030
H -2.62256625996549 -1.96622493205488 0.54644575568235

Compound 4a-R,R, isomer 000 000 001 1

C -0.10986718038709 0.07466578101551 0.14915046314604
C 1.32370762184552 -0.06423408542935 0.43941384999313
C 2.23361653461796 0.92274667305880 0.44231248627359
C -0.67170442261541 1.07353347584286 -0.84964726156634
C 0.16702092601743 1.98149657885698 -1.65075869020098
C 1.30480655130213 2.57045315217733 -1.25441217733966
C -0.87101800195764 1.31690592444015 0.65073078014419
C -0.20014723367936 2.40605036241963 1.37600859036724
C 1.03147669969067 2.93689553397724 1.19302472282991
C 1.97786402966399 2.38691157335889 0.09920759232538
H -0.67808776939287 -0.85633305600245 0.21781421923932
H 1.65155032272673 -1.06338358552338 0.74343480305209
H 3.24596177774910 0.66896586376075 0.77057859740383
H -1.57001466606094 0.72130777726954 -1.36305731496365
H -0.22236805279636 2.23174682191358 -2.64270799577162
H 1.77118264328711 3.29777617981172 -1.92265485660551
H -1.88121139930257 1.10591350321688 1.01086392631973
H -0.78820391749908 2.84037043618408 2.18971469140010
C 1.42776230029547 4.09543094082806 2.11438365777387

S55
 C 0.87802407258279 5.43346447959823 1.62589577826589
O 0.92138713849501 3.91524389852780 3.43308632155823
H 1.14892394805471 3.01702398202810 3.70883120593739
H 2.52784569149543 4.17142137686126 2.15160301276132
H 1.18462934349123 6.23643985082759 2.31509199409524
H 1.25406068348360 5.65279868943008 0.61982879831602
H -0.22200077175132 5.39249915720585 1.60398461693577
C 3.36144674087369 3.08704202223506 0.05580760435858
C 4.32906703238215 2.48143833316019 -0.96315316076851
O 3.14795428952316 4.45764531120161 -0.24313983694667
H 4.00686982008475 4.89082052478437 -0.32617462816889
H 3.80996333253113 2.98103197077414 1.06442263128611
H 5.27350814550498 3.05204099543048 -0.95880120983588
H 4.57757802518507 1.43534440169658 -0.73729308930194
H 3.91010266416464 2.52181095755202 -1.97935411163871

Compound 4a-R,R, isomer 000 000 010 1

C -0.19178320738457 0.17916386992512 0.03275348848293
C 1.27367703084173 0.04914206420133 0.00119820976578
C 2.16671234471900 1.05512540512111 0.00090105810184
C -0.92059160950967 1.30399512368175 -0.73664442044222
C -0.17485267910386 2.29169467663660 -1.53513569967961
C 1.01064523564346 2.84274081814246 -1.22296055392638
C -0.92008606293069 1.29286191119221 0.78370897222959
C -0.20331012471652 2.29718101648691 1.60155328294378
C 0.99229995386341 2.82929987533398 1.29415934209156
C 1.80067017499493 2.53624085971723 0.04026075602348
H -0.72434209393376 -0.77515060321584 0.02787979740235
H 1.65300823806465 -0.97570929933181 -0.06315414583022
H 3.22955169017539 0.79745957032187 -0.08819543090261
H -1.86538615529199 0.98758946380752 -1.18576589059657
H -0.63534821643468 2.56858066715564 -2.48864774267849
H 1.46373427654995 3.52907535320333 -1.94427440104718
H -1.85701284531616 0.96267985407287 1.23680811672808
H 1.45133567701756 3.51372136704597 2.01312295130013
C -0.91374472320076 2.71232240876556 2.87892774975320
C -2.16252836528604 3.54527110590234 2.61001990847497
O -1.33102043120786 1.57723649840466 3.63021923331702
H -0.55434682181606 1.01834478214526 3.76849327034959
H -0.20695660810903 3.32775836478260 3.47078810668043
H -2.66220523268267 3.78490449803581 3.56137510291129
H -1.89671745833740 4.48087179214613 2.09619982509114
H -2.87625110032872 2.99104589473107 1.98069534085603
C 3.11328219388329 3.36802297401573 0.07125288254265
C 2.91630711687119 4.87640326264782 0.00765775187008
O 3.84258039215426 3.11104268564093 1.25929161337020
H 3.85962039899666 2.15602619310425 1.40758395530938
H 3.70316978938410 3.05378150011629 -0.81630181451788
H 3.89320338683883 5.36936840721836 0.12060865751270
H 2.47744983214574 5.19176921907220 -0.94899313877673
H 2.26359401976134 5.22718169784065 0.82098204702552

S56
Compound 4a-R,R, isomer 000 000 011 0
C -0.16170617335091 0.17142611597832 -0.03767688568914
C 1.30356884682322 0.01394309767779 -0.05285838761004
C 2.19212674754650 1.01997931896900 -0.02859675372186
C -0.88478862450954 1.30492606815964 -0.78208398904686
C -0.16843818018214 2.32343456660445 -1.57016390820310
C 1.01846465933803 2.86445303816102 -1.24825111888191
C -0.85850897999173 1.28205935760771 0.74645212996641
C -0.15574177627124 2.29321221842117 1.57773625810634
C 1.03313986906669 2.85960297712396 1.25812716004426
C 1.80356561555128 2.48328181589081 -0.00815573739812
H -0.71161220287506 -0.77327340812651 -0.04172287659441
H 1.67273319795671 -1.01619655715302 -0.08127959951193
H 3.26100681314517 0.78378219514459 -0.03881303714507
H -1.84543788922556 1.00517713723193 -1.20887117126891
H -0.66483870288027 2.65082742119917 -2.48924607822838
H 1.45910647408997 3.61513343159675 -1.91231470206845
H -1.79407754785608 0.95535977285412 1.20248609291910
H 2.71972222391632 3.08351768124003 -0.01133889071803
C -0.94387216851041 2.66247087322829 2.83623789630787
C -2.11962676400094 3.58284996644351 2.52522654852438
O -1.48240922920309 1.50328056009696 3.46604473446666
H -0.75353123926273 0.88681251321430 3.61960115300500
H -0.28119387834879 3.17771758023477 3.55027196482123
H -2.70702377209750 3.76263812639650 3.43896619415532
H -1.76037907812002 4.54652600562089 2.13364775282320
H -2.78306505169473 3.12970494828963 1.77244249671648
C 1.70601802983481 3.95409234411245 2.07389485454114
C 2.95798326656704 3.46167903667535 2.79247565953476
O 2.11058814758856 5.02704275879036 1.22399352096752
H 1.33858810242808 5.29620136857314 0.70732608973551
H 1.00878969414470 4.34596324163808 2.83249248385848
H 3.46299370925875 4.30797731749824 3.28339753687833
H 2.69512576561561 2.71056542914218 3.55251045132739
H 3.66675498381546 3.00442657485137 2.08481939314211

Compound 4a-R,R, isomer 000 000 100 1

C -0.02654261074268 0.01073627810922 -0.12392973918886
C 1.44643027282995 -0.02041225734264 -0.17000807863608
C 2.26962007141294 1.03928915492868 -0.12103210351574
C -0.85983324689330 1.12560490382618 -0.74992538932662
C -0.26071068120962 2.26721373623908 -1.46311244525950
C 0.89878274790784 2.87441886126867 -1.16496514144146
C -0.80030367863826 0.97291612614726 0.78302531446258
C -0.09279136382545 1.97692454673034 1.60446654149287

S57
 C 1.03469880483987 2.63858827168772 1.29389652962250
C 1.81155552874767 2.48504265758545 -0.01031110890016
H -0.49210472790266 -0.97596592503105 -0.20124183745724
H 1.89288663822534 -1.01789542261228 -0.22933668135268
H 3.34719191473973 0.85211210354757 -0.12722914062232
H -1.80041447794520 0.77204715942521 -1.18324077319004
H -0.84285868376844 2.65234157654975 -2.30647322383309
H 1.20089959560167 3.74532250450773 -1.75134332874991
H -0.56935090690361 2.19574689026156 2.56391967762564
H 1.43928735493195 3.32836411390989 2.04540121643511
C -2.05353494714886 0.39196222611430 1.44029903016492
C -1.74762770302946 -0.44155935547590 2.67661052706200
O -2.94063854332862 1.42348957160661 1.83605507360249
H -3.05584730333090 2.01936349631601 1.08312809675572
H -2.54156819989415 -0.26814004983162 0.69209302134637
H -2.68383298944467 -0.81651975819366 3.11682308305852
H -1.10774360866878 -1.29814977033931 2.41704378687529
H -1.23021445628053 0.16116152471773 3.43823109362119
C 3.03699644037109 3.44035301311031 0.02595253636772
C 3.96419828607985 3.33559965038051 -1.17736663768442
O 2.61936292508396 4.79342172383453 0.08678222505685
H 1.91862453146585 4.87053838468680 0.74786639054944
H 3.61313507949494 3.17502075103054 0.93817393369125
H 4.74143083507343 4.10989826751255 -1.09710234353787
H 4.45709169621152 2.35518621833815 -1.23239642448677
H 3.41609100257898 3.50204685734461 -2.11686466407739

Compound 4a-R,R, isomer 000 000 101 0

C 0.01962778006756 0.06667535273522 0.08917624137596
C 1.49000162674730 0.16983647167141 0.01472655244690
C 2.19269459535316 1.30739636994616 -0.10919358780109
C -0.92325132866366 0.97556029442646 -0.71085626217104
C -0.43195168126510 2.03570249460664 -1.60963555119620
C 0.65704796002004 2.79825271454782 -1.41022265234477
C -0.85598562839293 1.07527592678590 0.82646609321977
C -0.29098865519458 2.28349031141507 1.46641714673614
C 0.76975381666324 3.00765601646496 1.06518126013327
C 1.55888917265906 2.68038540246349 -0.19538549859515
H -0.34521586589799 -0.96120732298502 0.17191320001761
H 2.03319506472376 -0.77897705444376 0.06570075177262
H 3.28488331343776 1.25136523538170 -0.15386749788253
H -1.81553444373831 0.45853289935945 -1.07709705322999
H -1.02116150988340 2.19489917306989 -2.51849255692046
H 0.91814197699646 3.55265856835745 -2.15923161973649
H -0.84111387271512 2.62661593420215 2.34865938306912
H 2.34975178792305 3.43330190356258 -0.29469428349082
C -2.04964237238221 0.47607654903444 1.57378259907864
C -1.67463531408612 -0.08839326153964 2.93646407799756
O -3.05751282439382 1.45015588822568 1.78299716792713
H -3.22293760120278 1.88861897971092 0.93707742031984
H -2.44416588057336 -0.35532753215004 0.95205754768233
H -2.57051371929948 -0.48459064547124 3.43780176126374
H -0.93808484209702 -0.89886857934005 2.83009904117194
H -1.24125139617786 0.69328875803064 3.57843365003091
C 1.21304989710599 4.22899920759083 1.84118595078114
C 2.57088670091355 4.04301461000144 2.50975295573238
O 1.33011738862063 5.35887222172060 0.98080622587137

S58
 H 0.49114266281445 5.45133382057258 0.50901316709270
H 0.45984179242355 4.42308313711957 2.63165789725427
H 2.87272205664062 4.97898681857736 3.00473230514444
H 2.52510034533147 3.23771797823771 3.25758040146332
H 3.34331552753969 3.78790321047789 1.76728905193094

Compound 4a-R,R, isomer 000 000 110 0

C 0.19703725447355 -0.04620247710416 0.25766248309295
C 1.66546200218829 0.08349787866489 0.24135021554750
C 2.35173531036691 1.22672038600837 0.09289830818915
C -0.73660374612096 0.81345202372324 -0.59998181994418
C -0.23771493506047 1.85802710129685 -1.51506757672224
C 0.83336022668016 2.64099252280371 -1.31124016336979
C -0.77843860733085 0.94228250580498 0.92914401078695
C -0.24968348353803 2.18595801315438 1.59642279342542
C 0.82144492958870 2.88204533716230 1.16389605704985
C 1.67334731690117 2.57451464212884 -0.05014148242091
H -0.13212378424103 -1.08656465868793 0.32447346829225
H 2.22220065213822 -0.85375220085983 0.34221913716800
H 3.44542009272221 1.19742684008369 0.07898498671552
H -1.57356621137874 0.25287670260819 -1.01601034793735
H -0.79739879138903 1.96902692230514 -2.44921006152727
H 1.11666855020996 3.36832136049435 -2.07829732720708
H 1.11482840753517 3.77100321108396 1.72514797225268
H 2.45273996225481 3.34552720352298 -0.11579517424981
C -1.93894102063338 0.24666994932389 1.66923214164315
C -2.74939144487569 -0.78513126985260 0.88593237599209
O -1.44746858618883 -0.33066520559185 2.87830363224946
H -0.65633821681816 -0.84151470239309 2.65607715783361
H -2.64033955836923 1.02906706486589 1.98381040865123
H -3.46708441825285 -1.24425765061052 1.58124876062356
H -3.31979829959838 -0.32497811529427 0.06526837107420
H -2.13071900650068 -1.59719392550936 0.46948531100540
C -1.04952571038210 2.71573206308029 2.78755986380127
C -0.36977784385521 3.77947123542376 3.64389491404459
O -2.32152970431937 3.19470786317846 2.32971612291492
H -2.14420415280624 3.81708348726405 1.60982758038211
H -1.28499897016547 1.86597185765245 3.44165817422816
H -1.04504998394787 4.04314225312219 4.47109116577336
H 0.58008598690511 3.41822173250246 4.06711208979539
H -0.16876705559601 4.70221088516492 3.07546805400499

S59
Compound 4a-R,R, isomer 0000010010
C 0.20315930628231 -0.01580384209442 0.06546693433837
C 1.66432053822065 0.12446049446353 -0.06614696410228
C 2.33272896207069 1.28507433277561 -0.16349204563497
C -0.77388898076212 0.92422552266021 -0.64682367606775
C -0.33882357180125 2.03672840791312 -1.51409531894760
C 0.73052232734543 2.83446937018776 -1.33244681156102
C -0.64700548630873 0.96666641492685 0.87974608004500
C -0.07728814465706 2.12806908568131 1.58438569643855
C 0.94687966954506 2.89819428736471 1.17053292772672
C 1.67073998055648 2.64723539193416 -0.14514655293228
H -0.14293365907327 -1.05072992808711 0.12608423142751
H 2.23254538530981 -0.81065939588521 -0.08831526536146
H 3.42259746697203 1.25908106262110 -0.26013356260051
H -1.68222885274766 0.42702070552064 -0.99643747259695
H -0.97783787080008 2.21043840094035 -2.38298640535161
H -1.48025766502617 0.49490244108001 1.40652131940184
H -0.55667639059616 2.38255692302219 2.53654860027715
H 2.46771653724085 3.39754553972226 -0.23286483134779
C 1.08873192628326 3.98792548122780 -2.25587408201226
C 0.24399210956682 4.11345968337176 -3.51226344594361
O 0.98892355241729 5.23471081518823 -1.57423947686699
H 1.51574018166586 5.21126293101224 -0.75776434112747
H 2.14369296925119 3.82254965724055 -2.56970211946636
H 0.59712076644166 4.97567094733048 -4.09653958773790
H 0.31111814780249 3.21030684919165 -4.13639793084800
H -0.81031480396384 4.29395110301131 -3.25165265794358
C 1.39893507533455 4.08763647979037 1.98701719409529
C 2.83621254462759 3.98167140670015 2.48043209381122
O 1.31520920762181 5.28990147932356 1.21053917714990
H 0.40594476421657 5.37013367268096 0.88444989456342
H 0.73331831460119 4.17309297585043 2.86765039669157
H 3.11036590358759 4.89487867920290 3.03037166942431
H 2.94992667902686 3.11260097517307 3.14488955394996
H 3.53733727097378 3.87108856547254 1.63849588890944

Compound 4a-R,R, isomer 000 001 010 0

C 0.55403805684883 -0.13453838249352 0.19730646749016
C 1.98263336904482 0.22809499227228 0.14236345435327
C 2.47305044969689 1.47539258426493 0.04875937276456

S60
 C -0.51283748468199 0.61373524324431 -0.61655060589251
C -0.18112121943425 1.74967783494612 -1.49449409768994
C 0.73592271797809 2.70845725051455 -1.26021976818256
C -0.49905206288167 0.71497428189126 0.90936428602636
C -0.18341531145550 1.97255823947416 1.62467319318572
C 0.75305654815459 2.85830740003732 1.23613274867309
C 1.60454999074720 2.71736670967735 -0.00793180961046
H 0.37166403371184 -1.20952594402065 0.27409294451638
H 2.68583742189147 -0.61026697423270 0.17606041874254
H 3.55777736021728 1.61761707723957 0.01008471030062
H -1.30049090410839 -0.03392266806979 -1.00999325175661
H -0.75408185233153 1.80714825610882 -2.42709300308274
H -1.26480822137239 0.12065896180397 1.41202147195084
H 0.90246648867677 3.75593674797802 1.84673086543497
H 2.27174409615865 3.58457052550288 -0.07960698918370
C 0.95936165478018 3.83464436249586 -2.24539148895157
C 0.52197228670500 5.19118930789087 -1.70255497058520
O 2.34049129302245 3.95088168476035 -2.57568245865983
H 2.64505914538345 3.07759453007668 -2.85806709280988
H 0.36343732137545 3.61663239694093 -3.15522881396894
H 0.76489539216679 5.97934401926197 -2.43194101339161
H -0.56106774055312 5.19841047191210 -1.51058873035390
H 1.04577364557037 5.42611489335914 -0.76269703802298
C -1.02394164219026 2.23920206993894 2.86176808303489
C -2.47677479080524 2.55922936998970 2.52583804776009
O -1.04133852977379 1.10964832173271 3.72769880117823
H -0.12315022430677 0.86087210484085 3.90053021363898
H -0.58752349380569 3.11588737651406 3.38140153188510
H -3.05071898828948 2.70170471319447 3.45454202869385
H -2.53814469330644 3.47537690399482 1.91992575200134
H -2.94020877381702 1.73496494365248 1.96176456841826

Compound 4a-R,R, isomer 000 001 100 0

C 0.08833610423325 0.11781237646092 0.23582087438610
C 1.54929565976044 0.29720530940255 0.33923519354261
C 2.20798383265493 1.46090042371173 0.21551092175102
C -0.77249115853889 0.92096850199021 -0.74877388834254
C -0.20258267884854 1.93285122208573 -1.65436032665309
C 0.80829941837803 2.78219393167418 -1.38519042474482
C -0.92635826655255 1.12269240922717 0.77232278789026
C -0.51044680355509 2.40037183118534 1.39496971191413
C 0.55348285980086 3.14802570405142 1.06154145394379
C 1.52820382957420 2.79170314393608 -0.04169852549295
H -0.23658194083431 -0.92113245658738 0.34302065532551
H 2.12583374078859 -0.61415257880727 0.52666289613878
H 3.29872762304210 1.46359604279073 0.30763787875482
H -1.58060920686711 0.33345387418849 -1.19515619353336
H -0.66184076004872 1.98500658613976 -2.64835290503105
H -1.18348148130939 2.76718077255906 2.17473151802433
H 0.72215472451229 4.08731155772136 1.59796769935093
H 2.30946249567844 3.55939714392755 -0.09267264812252
C 1.28555169445541 3.78047273782918 -2.41702322183553
C 0.98576120581569 5.22460488101268 -2.02902721693028
O 2.69606262569952 3.68715564987303 -2.59291321641560
H 2.90517780217551 2.76063527923360 -2.77442982723586
H 0.76344665100301 3.56199546299213 -3.37113313131294

S61
 H 1.40839310574856 5.90674021956451 -2.78282490531781
H -0.09974629413688 5.38890258911712 -1.96180926111438
H 1.43835384627237 5.47228222604231 -1.05617682679646
C -2.18429535771929 0.50741473639229 1.38944578043144
C -1.97728286371842 0.04797364591446 2.82553109333463
O -3.25362228288477 1.43688512416535 1.39282723240936
H -3.31299705108147 1.82148978410895 0.50752685196088
H -2.45143231521271 -0.38100141307862 0.77831812117828
H -2.91530883608072 -0.36520503666741 3.22595580998395
H -1.19702825784168 -0.72624454424113 2.87490855230153
H -1.67346307484096 0.88948902516940 3.46620345178454

Compound 4a-R,R, isomer 000 010 001 0

C 0.07468166611371 -0.00709956631403 -0.14766721542919
C 1.53282273773480 0.02878435244286 0.07225399762742
C 2.27535063396472 1.13448148129154 0.25291235718203
C -0.66573812755818 1.05493858513713 -0.96119905050795
C 0.01994740725118 2.19487302949072 -1.61093077303289
C 1.05374061535136 2.87007095294697 -1.07415170144929
C -0.88367393274571 0.97081080768331 0.54985037884253
C -0.41966408907329 2.00723762321785 1.48907577352884
C 0.72197015369728 2.71669208720481 1.40471128419664
C 1.70422782762611 2.53859517950688 0.25440362936903
H -0.33313894089259 -1.01445130001830 -0.26470645999488
H 2.03216736328268 -0.94503185178023 0.09079162512421
H 3.35286766172140 1.02730868851490 0.41283119425676
H -1.50890770340398 0.67739697139295 -1.54318641606935
H 1.47936550660589 3.70466460622456 -1.64288169167836
H -1.84082771168155 0.52208600341751 0.82769271986134
H -1.07811513096983 2.19604127344862 2.34494120213927
H 2.52017139511816 3.25485970764629 0.40863252237119
C -0.50982723103861 2.56988820397992 -2.98455441379967
C -0.18071250595844 1.52345168391997 -4.04404280741561
O -1.92643644268089 2.71106332331441 -2.97296747392308
H -2.15263701554664 3.32778150092827 -2.26371963890168
H -0.03044385039912 3.52485353068336 -3.28022318149614
H -0.61985001150002 1.82027526256341 -5.00906487165235
H 0.90860721824570 1.42254962944398 -4.15894251294638
H -0.59580763732385 0.54172562860666 -3.76791420267803
C 1.09194975541834 3.73336135789192 2.46198709835744
C 2.30625469013581 3.31650509549167 3.28519142902708
O 1.41119927635894 4.98877174742485 1.86793520481517
H 0.67410200847475 5.23216270200432 1.29152070389788
H 0.22759794577795 3.84169958724649 3.14876959399842
H 2.56606368737695 4.11661442856644 3.99548748434424
H 2.09498320990897 2.39248486176021 3.84306769774754
H 3.17917245407406 3.14204710564550 2.63688489104076

S62
Compound 4a-R,R, isomer 000 010 010 0
C 0.60654217394486 0.07605018855088 -0.05382416761451
C 2.03665174747929 0.43630443944841 -0.03629919989540
C 2.53354081942914 1.68260548583253 0.03493492472786
C -0.44976037912032 0.91737105693517 -0.77686677899316
C -0.11778456077042 2.15262824963416 -1.52170248100292
C 0.80308104164239 3.05586788243084 -1.13479705609825
C -0.45389122012761 0.83796143691748 0.74717448103326
C -0.13975239429613 1.99042047925381 1.62134983965396
C 0.80468599635276 2.91327289503806 1.35987407426182
C 1.66303668707904 2.92436110608316 0.10894988644592
H 0.42136591948861 -0.99986775558735 -0.10818220825472
H 2.73703592259695 -0.40332776773682 -0.08963383266687
H 3.61906096137186 1.82182982128798 0.03668166317645
H -1.25034866946280 0.34010655353243 -1.24376996388181
H 0.95778308326677 3.94033817836193 -1.76270562089157
H -1.22755339846581 0.18934132085761 1.16319755311640
H 0.95834384681647 3.72050351617815 2.08467574539122
H 2.32295788915601 3.80093410337125 0.15877387209836
C -0.89484524499707 2.35572824961725 -2.81123379196576
C -0.50468133319138 1.35750593167712 -3.89611510884989
O -2.29416733334905 2.20535087017266 -2.59794432874909
H -2.54206163898847 2.78676815851255 -1.86632600485863
H -0.66969334663957 3.37605279518811 -3.18200092958696
H -1.12442807126706 1.52010894105293 -4.79147846879123
H 0.55544221945757 1.47652581035025 -4.16467192056012
H -0.66503564259242 0.32340411163776 -3.55380559026514
C -0.99063427747518 2.09921533039103 2.87527318569025
C -2.43706143576331 2.47414490815290 2.56816083147537
O -1.02795954919921 0.86649152386993 3.58490786883939
H -0.11435650730995 0.58428743803605 3.72807946129465
H -0.55374450150680 2.89608600380904 3.51042393453048
H -3.02284014077019 2.49480822170433 3.50013183427683
H -2.48366160545729 3.46504690025933 2.09223123730062
H -2.89820639819399 1.73722947074038 1.89220251036033

Compound 4a-R,R, isomer 000 010 100 0

C -0.03607983896595 -0.12959727378385 -0.04290126097110
C 1.43121394572125 -0.25187550334399 -0.15456001811300

S63
 C 2.29404701916132 0.77146533001076 -0.23878225264288
C -0.82305818610700 0.97413957327995 -0.72184710074744
C -0.27925390956986 2.11067432078800 -1.48783200978495
C 0.92892856902677 2.66480292433516 -1.27261696248017
C -0.73887541688084 0.93085216740086 0.81722236570075
C 0.03909508361029 1.95621891807215 1.54336110100518
C 1.19108731827428 2.53047956990214 1.15125725693875
C 1.87903537080912 2.22801661637228 -0.17137735673007
H -0.55886370176459 -1.09036667387782 -0.04767456439653
H 1.82306126512900 -1.27352673897117 -0.17919580392024
H 3.36346300062707 0.55630530809279 -0.32567303733414
H -1.79576062251421 0.63812408567070 -1.08706230887608
H 1.19794343586436 3.56481910528961 -1.83680764532117
H -0.39909730053640 2.28567134060969 2.48895106645477
H 1.64919380343045 3.28339905528775 1.80045534805963
H 2.78596587227837 2.84374221166253 -0.23900706361811
C -1.30310757493611 2.81041312369929 -2.36303482562868
C -1.90011115575127 1.96364313491079 -3.47687338082897
O -2.39037520251914 3.24097600898356 -1.52748588256745
H -2.01174438980756 3.81733283181105 -0.84773761008373
H -0.81582034228579 3.69194038726822 -2.82196249404711
H -2.64909218110128 2.55028599812779 -4.03021427015472
H -1.11259377627265 1.64020972566465 -4.17401376250912
H -2.40222089213374 1.06903985424322 -3.07825913915917
C -2.08325828121602 0.56020358777490 1.44562897042389
C -2.00134167609490 0.06919440421412 2.88232836034837
O -2.94284832220395 1.68565072535607 1.41190804040647
H -2.95582563354372 2.01686345999172 0.49890353810723
H -2.50677632264882 -0.26459560961865 0.83351964134979
H -3.00672068699707 -0.19628811617827 3.24251652594687
H -1.35312846304894 -0.81802554261729 2.94996836569749
H -1.60123317667415 0.84698262629193 3.54956311550721

Compound 4a-R,R, isomer 000 100 001 0

C 0.07413985417537 0.04654196946038 -0.08688263328111
C 1.54138673624930 0.14055223765475 -0.19614110269889
C 2.26691233959542 1.27126627959531 -0.15076400653275
C -0.89689173348300 1.07969075171069 -0.69315412348868
C -0.37274680641569 2.24284253185236 -1.44452775430818
C 0.73258917922963 2.94992431491788 -1.16068393081776
C -0.74404592920065 0.97447097113861 0.82103853227025
C -0.13324782197426 2.02834161803259 1.65135755585838
C 0.93550195597845 2.78313125323621 1.33505765626227
C 1.65978913983829 2.65193316884576 0.00156848964023
H -0.30877885253748 -0.97824352851139 -0.11548918168651
H 2.06708735331813 -0.81230752682785 -0.31454802678141
H 3.35610518541884 1.20331674032479 -0.23532590105499
H -0.94579175255811 2.50461278186242 -2.33830735057267
H 1.00897424470885 3.77762385045950 -1.82184131694785
H -1.58606295029933 0.47066899335329 1.30439449275389
H -0.60462320846877 2.19074446479868 2.62741020015401
H 2.46162525825740 3.39973273321677 -0.01042945598590
C -2.19635448573294 0.50308291961969 -1.25887251682968
C -3.37515798130095 1.45767053744025 -1.13335480932834
O -2.05392796908282 0.18650703865545 -2.63243690649067
H -1.23753269603286 -0.32164942366566 -2.73512646246987
H -2.43190530178660 -0.41338599283461 -0.67695446427939

S64
 H -4.27499563142178 1.00206650056313 -1.57342503503513
H -3.57430531421067 1.68970721800952 -0.07633201829547
H -3.17498389767554 2.40004692922313 -1.66523165469110
C 1.47435015564885 3.81751593512866 2.29861412181715
C 2.85205160437887 3.45713551996832 2.84462411288023
O 1.60492144091658 5.08370647312991 1.65901047230185
H 0.75372574538251 5.29155107492088 1.24985437792516
H 0.77014985333676 3.88871876383033 3.15274573120006
H 3.22114712139829 4.27138032934575 3.48722333310483
H 2.80389863407771 2.52787520612390 3.43111199161560
H 3.57503320940428 3.31740923037959 2.02576105204998

Compound 4a-R,R, isomer 000 100 010 0

C -0.08280761003884 0.08428563980087 0.02094101745657
C 1.38437052742919 -0.02956405538204 -0.05844810900224
C 2.25748826614377 0.99213916921374 -0.05703577950623
C -0.89213968024388 1.19965727630764 -0.68010295093530
C -0.19069506497403 2.22547147994531 -1.48447136821476
C 0.99520919977270 2.79222822702364 -1.20930830132393
C -0.79428681690362 1.16444448179723 0.83811456807558
C -0.08304912463671 2.18531689880764 1.64123992963661
C 1.08859107223334 2.74850925125647 1.29465012811648
C 1.83464230824355 2.44928053632378 0.00847187684594
H -0.60122871359907 -0.87929930446951 0.04024141839539
H 1.77574519648939 -1.05003378362241 -0.12275301889797
H 3.32799881034899 0.77450685271578 -0.12341706737732
H -0.69688579968541 2.49935369250899 -2.41425172486506
H 1.40171146591975 3.52540931051066 -1.91305978405832
H -1.69548073658363 0.79375275555269 1.33256917323079
H 1.53032840431619 3.48694667179305 1.97288555875679
H 2.74021212579892 3.07045152181589 -0.01166668043256
C -2.24260115775450 0.76672894896987 -1.25412081387429
C -3.28293158568957 1.87712627008951 -1.22333097298019
O -2.11112804224662 0.34778737650937 -2.60144373167960
H -1.37225160517384 -0.27455422151030 -2.64575181679081
H -2.61386187573383 -0.07082850615288 -0.62647549278578
H -4.22430684791202 1.52159072304877 -1.66852605395744
H -3.47666088123147 2.19541761655138 -0.18837125004741
H -2.94113498592930 2.75122277570859 -1.79795551817453
C -0.78246811674131 2.59580621481496 2.92584184110860
C -2.05484788698704 3.39686793293233 2.67115500333021
O -1.16163858642026 1.45878582516279 3.69399862668176
H -0.37308445923853 0.91280112202221 3.81628466745522
H -0.08106106516205 3.23268880048114 3.50142494118208
H -2.53816902267937 3.64328272002380 3.62907737042763
H -1.82336754050059 4.32771799145846 2.13282996873181
H -2.77007304824210 2.81389207675272 2.07055742395160

S65
Compound 4a-R,R, isomer 000 100 100 0
C -0.02309233818300 0.01357008242698 0.12059450171725
C 1.44708813117468 -0.05622354737838 0.23017225092500
C 2.29491965261019 0.98313128807317 0.16906495884593
C -0.78097147109866 0.96818236367390 -0.82001664749303
C -0.03379520153222 1.94864784065970 -1.64722854165488
C 1.11116547037446 2.58020935668340 -1.34259381013835
C -0.87278293325177 1.13235008995794 0.72231147808389
C -0.23984375762176 2.29960746565675 1.38961280256649
C 0.93983891209603 2.87081159689959 1.10409055231239
C 1.84416780445996 2.41897560804882 -0.02467888870958
H -0.50909660937061 -0.96483369425880 0.19649231363129
H 1.86129401127123 -1.05974518648813 0.37125941984368
H 3.36915723765044 0.79505467489046 0.26065908917124
H -0.46423404243686 2.12362191963446 -2.63631765293479
H 1.54166528364263 3.26307252667836 -2.08189622530819
H -0.83840219482831 2.73238133098976 2.19526380871587
H 1.25899621291313 3.73405978878753 1.69661136834930
H 2.73418180995001 3.06231835157505 -0.03903966461716
C -1.94567678196817 0.33162051861657 -1.59917357745180
C -3.11010775672701 1.27898549433631 -1.85758330888596
O -1.48798059249360 -0.11820455627559 -2.86566493808166
H -0.66693897007942 -0.61036409545609 -2.72713629851553
H -2.32545825717706 -0.53190827725768 -1.02363642277323
H -3.81652431036402 0.80954807092818 -2.55838163156376
H -3.65075934336866 1.49724403466614 -0.92515507784465
H -2.76547670086230 2.22514432667116 -2.30186033519796
C -2.15445329538115 0.69145447670922 1.44349414632289
C -1.87497439604613 0.12180480094941 2.82845306541021
O -3.05013010488383 1.78304508942249 1.60745829028329
H -3.03996547496587 2.30540592925636 0.79480195497890
H -2.64225100274002 -0.10250494396464 0.85131988706423
H -2.82417355594705 -0.13455471673027 3.32280815573259
H -1.25727478564404 -0.78588316641411 2.75494338082049
H -1.34609374711006 0.85245347408955 3.45826824213630

Compound 4a-R,S, isomer 000 000 001 2

C -0.09673571137828 0.05448294891930 0.02189701992857
C 1.36956234924894 -0.00523075120731 0.15730850257491
C 2.20592713847404 1.04216021722634 0.15272251312976
C -0.81705221110232 1.06297522260845 -0.85319271659613
C -0.13508508723981 2.10720450025811 -1.63279353868556
C 0.98943806574256 2.75192385166985 -1.28381943916369

S66
 C -0.89237606801569 1.18425234587366 0.68390024508951
C -0.25810957715099 2.29923031947864 1.40239212411528
C 0.91463354087589 2.93160463469157 1.15716438849831
C 1.81967242752675 2.50225504257601 -0.03166089178199
H -0.59408570404187 -0.91755822142263 0.07206897981478
H 1.78958268505105 -1.00240367861407 0.32352556212021
H 3.26677499056411 0.86779514093674 0.34692359619990
H -1.73415488539854 0.68327970476019 -1.31053479999747
H -0.64432837089839 2.41996491494815 -2.54977581862558
H 1.31958562858608 3.57117999704039 -1.92862994664342
H -1.84936230660854 0.87519764422817 1.11160417860435
H -0.86081079991414 2.66800849545959 2.23524074838537
C 1.35140334110017 4.06423481965814 2.07411804516295
C 0.26507923244240 4.74022263061922 2.90335638810657
O 2.40547693844752 3.60310036562093 2.94943287562010
H 2.10222291207841 2.77086835699770 3.34281368085581
H 1.83445222713161 4.84521684491619 1.46884460148868
H 0.71926382096873 5.55447205156349 3.48669131311973
H -0.52533042152288 5.15962908552672 2.26285674872579
H -0.20028156665500 4.04275223763061 3.61759598850350
C 3.15325688346430 3.31796596759300 -0.17113264648836
C 3.91555343258547 2.98861384568895 -1.45466178395004
O 4.05760423078590 3.07533361731059 0.87734171588550
H 3.62071786864547 3.25907447087017 1.73187903612068
H 2.87295618266440 4.39211255099158 -0.21641538837991
H 4.87481203694564 3.52584533551669 -1.42916464411883
H 3.37352345908441 3.28243181948731 -2.36321727505786
H 4.13303822852304 1.91163859265312 -1.51524240184592

Compound 4a-R,S, isomer 000 000 010 2

C -0.10087398356485 -0.00456507916195 -0.10448296213762
C 1.35905171386459 -0.05821853731491 -0.29130439576601
C 2.20169724392679 0.98816978711593 -0.30626611989288
C -0.95465280435697 1.12090359533275 -0.73105064053058
C -0.33822803833891 2.19908473371794 -1.52040109175640
C 0.84801380274802 2.78876266186001 -1.28374163321507
C -0.79935590508214 1.01134000127571 0.78507445748696
C -0.08153623840843 2.03556075584805 1.57642065319914
C 1.04877632244138 2.65350482939997 1.19226130902208
C 1.77767260919182 2.43682027302915 -0.12451477100215
H -0.58800735331388 -0.98276085347652 -0.12357599763600
H 1.77365264875341 -1.05612919753677 -0.46572114992542
H 3.25944439051678 0.79502930654581 -0.50768042600706
H -1.92347823907827 0.78587731164909 -1.10979913631748
H -0.90250998985938 2.51673480483811 -2.40288431066823
H 1.19776314150329 3.54101330285737 -2.00181157433992
H -1.67232037677641 0.60710808901059 1.30163152096356
H 1.45758130320287 3.42981094237915 1.84546337623503
C -0.74394349442487 2.41107989699366 2.89141377536677
C -2.05327168386900 3.16773415855266 2.69446734283664
O -1.04995746983852 1.25397916905086 3.66252931299107
H -0.23562609847458 0.74059685024504 3.75258153188098
H -0.04335767861255 3.06820110373133 3.44426073914541
H -2.51195449131732 3.37839243124541 3.67292971487220
H -1.87269563248975 4.11732611664338 2.16928840252047
H -2.76719014330417 2.57167062924636 2.10502898233983

S67
 C 3.01656007391909 3.37329046150912 -0.18386498100980
C 4.09184067132540 3.07542933664515 0.85201170276428
O 2.63588460913345 4.72423186610991 0.01391558571284
H 1.84869748489941 4.90223113973681 -0.51816605823443
H 3.45805068023923 3.24356690755709 -1.19520670904392
H 4.87653392416703 3.84335626001640 0.78372728830016
H 4.55461419075326 2.09196991780509 0.69063283539724
H 3.67960588968734 3.10215725472705 1.87187905532272

Compound 4a-R,S, isomer 000 000 012 0

C -0.18953186054720 0.16015646496875 -0.04112417560476
C 1.27291378636634 -0.02385242160500 -0.02836944314452
C 2.17966829635903 0.96574141645389 0.01112472085096
C -0.87606796690781 1.30424340092185 -0.80438082817879
C -0.12521911356928 2.30966776346796 -1.57613279799389
C 1.06124162128217 2.83192217802139 -1.22493609991672
C -0.88394053605300 1.28538819086378 0.72372430746741
C -0.18054541283573 2.28095017918245 1.57413554864943
C 1.03504055974017 2.81205470041504 1.29057136374140
C 1.81438251820369 2.43691773093782 0.02864906058435
H -0.75577787447465 -0.77479086267171 -0.05450715594444
H 1.62373080921881 -1.06055384494088 -0.05526324361949
H 3.24465542910848 0.71150247713008 0.01138807248148
H -1.83193297517081 1.01997106430452 -1.25195503778956
H -0.59620600230171 2.64770136256590 -2.50453355566069
H 1.52447270575498 3.58041490877394 -1.87569817624547
H -1.83601681593203 0.97827749288551 1.15867052073379
H 2.75251176319431 3.00136384267989 0.06045205350827
C -1.01364325448290 2.70200075758274 2.78247537245608
C -2.13036181171748 3.66640205528932 2.39318945811897
O -1.63649796319198 1.58222484353798 3.40574694017637
H -0.94643387398958 0.93586706959535 3.60709826423015
H -0.36886071256876 3.21076891583312 3.51879494910076
H -2.75059053368291 3.89470535156966 3.27378677799784
H -1.70984641137765 4.60237688861537 1.99664472651242
H -2.77786312652253 3.22338551361296 1.62077696335152
C 1.73422471463075 3.85431329545285 2.14756379925554
C 1.68183470950104 5.24632252592408 1.52397534721788
O 3.11324461057223 3.53073569767860 2.31682992123208
H 3.16165268651784 2.62357306722139 2.64795115076687
H 1.25446213411424 3.91185047523113 3.13963692473519
H 2.27242283168473 5.94892400050110 2.13209684985697
H 0.64321967903237 5.60419477946457 1.46741595540029
H 2.10092269186776 5.23795611154878 0.50595611088650

Compound 4a-R,S, isomer 000 000 100 2

C -0.04620076541705 -0.03944361326867 -0.13351355035555

S68
 C 1.42850937916207 -0.06460373882184 -0.16356936939824
C 2.24110344480018 1.00091928532687 -0.11087266822201
C -0.87469284094840 1.06052660931383 -0.79239176206351
C -0.27226148386427 2.20247077301634 -1.49951844728765
C 0.87918626392630 2.82254718755245 -1.18845900862702
C -0.83586740860436 0.91931422999377 0.75051322929317
C -0.17321690136054 1.96671362142141 1.55446105183123
C 0.94826222542965 2.64191738700170 1.25090587499924
C 1.77417266059080 2.44579328327907 -0.01723639213245
H -0.50657603947576 -1.02874534507474 -0.21019766445562
H 1.88139768158946 -1.05962847485060 -0.21667613685835
H 3.32093759304875 0.83664291889180 -0.09196023516774
H -1.80604940482283 0.69909766004325 -1.23879688713912
H -0.84621653179538 2.58188120237364 -2.35090902501833
H 1.17605846438871 3.68596743495585 -1.79094212173840
H -0.71625687958668 2.25044039163408 2.46031296847001
H 1.25867980611280 3.44300400533721 1.93364298082546
C -2.09579043133263 0.33626128573687 1.39254338842444
C -1.80027949894909 -0.46155887050720 2.65460069099145
O -3.00814447050786 1.36126907655152 1.74562749580025
H -3.12042350229693 1.93529731751253 0.97545075468572
H -2.55744075447206 -0.34880267931308 0.65016508259098
H -2.73822410364994 -0.84037696072395 3.08775201835827
H -1.14212634510827 -1.31372433006171 2.42830728661807
H -1.30571450938532 0.16934077397443 3.40866482668273
C 3.00936067388516 3.38564737580347 0.04849320923296
C 3.87796726417740 3.39001860646319 -1.20188186082101
O 3.85788342365665 3.02147447752265 1.12328001675351
H 3.31159062583388 2.85935638492944 1.90422134347438
H 2.61300895037149 4.41226643102818 0.20283179813410
H 4.76302230469938 4.01746049936290 -1.01985061721533
H 3.34121282778215 3.79290850458338 -2.07201727193599
H 4.22670299943481 2.37593358108037 -1.44813309070988

Compound 4a-R,S, isomer 000 000 102 0

C -0.08877298773542 -0.04243067152577 -0.08422946514077
C 1.37323650943599 -0.24196066855122 -0.07578544554246
C 2.29756952377165 0.72877112348046 0.00549910307343
C -0.76338854516726 1.15024022711965 -0.77456966582375
C -0.00165191370452 2.19420317976522 -1.48401908539868
C 1.20227896438421 2.67453946685882 -1.12792452880855
C -0.79098158133715 1.01545785961866 0.76148496505055
C -0.03498265407923 1.96508682005863 1.60716814824261
C 1.16549028605950 2.51758409524265 1.35351709400792
C 1.96489317475803 2.20549235313475 0.09556658178139
H -0.65999883630788 -0.97076614197528 -0.17543574966104
H 1.70938295822295 -1.28123395378276 -0.14651440460323
H 3.35657068510300 0.45191555583645 -0.00200189934022
H -1.71355375494890 0.89166152435386 -1.25200797731811
H -0.47939122738973 2.59782663397823 -2.38244830360438
H 1.66260458326816 3.45382582445236 -1.74348679551636
H -0.55789599391950 2.27464445088176 2.51805076653800
H 2.91077926556959 2.75628027350339 0.16159739565382
C -2.13323959878787 0.58486113679407 1.35740700599476
C -1.98294883984903 -0.24416678340522 2.62486651623260
O -2.92835015002108 1.71187537830210 1.68235174979953
H -2.93149581106651 2.30144264199832 0.91575714200730
H -2.64702722103589 -0.03954827744001 0.59596557512511

S69
 H -2.97547548733321 -0.50518279291507 3.02193958808780
H -1.42740255461119 -1.17105180150939 2.41754819378406
H -1.44265906537241 0.31963849247070 3.40029752075870
C 1.77959148126750 3.51165045161361 2.31557498807472
C 1.85621779867961 4.92286459979520 1.74274378854381
O 3.11137829120445 3.13221073949698 2.65104440549161
H 3.08189398698678 2.21713096796134 2.96218089386192
H 1.14657335642949 3.54031627258823 3.22561843602279
H 2.36292249797481 5.58747562723919 2.45948223768380
H 0.84756083268273 5.31212406261231 1.54060223420786
H 2.43146864765885 4.93595761842536 0.80374476388662

Compound 4a-R,S, isomer 000 000 120 0

C -0.17403690414223 0.15379957391584 -0.19601754961518
C 1.28901935589498 -0.01784112388401 -0.18990410241047
C 2.20027125244697 0.96482167238139 -0.10103245061097
C -0.86751951027582 1.35949147210074 -0.82889593674768
C -0.14365355758150 2.45603747563546 -1.49853430839200
C 1.05552429883740 2.94189615618417 -1.14558979883315
C -0.94554465468674 1.14170094828220 0.69462082293597
C -0.17717468547106 2.05101628246182 1.62138457834941
C 1.01535400826839 2.61172772187998 1.32428389806874
C 1.81962593202565 2.42501753763292 0.05544137878695
H -0.71332107509305 -0.78687240818035 -0.32410592258103
H 1.64065421109178 -1.04997962707479 -0.28624693600506
H 3.26487351465138 0.71279587125040 -0.12683172643418
H -1.78938951257503 1.09766921068646 -1.34571466451619
H -0.64484281262662 2.88208659588039 -2.37361617135308
H 1.50372870331054 3.74904170195235 -1.73283586706950
H 1.47911175133851 3.25465099359258 2.07459213752099
H 2.74213287349344 3.01262078799053 0.15586556042710
C -2.27628316259643 0.55220566062206 1.23791417516926
C -3.26531729942169 0.03087321914306 0.20028303429676
O -2.03055204263311 -0.51842930316630 2.12276366561574
H -1.48906878807297 -0.16946481113109 2.85568975087635
H -2.80573323784006 1.37372570755582 1.75885985189114
H -4.10296819972357 -0.42736623375453 0.74556342492572
H -3.66440752706213 0.83448255638721 -0.43452737067258
H -2.82796219189804 -0.75099745306075 -0.43981733410713
C -0.72314859367208 2.25322746505484 3.03472219640181
C -0.17991037602868 3.43732919507076 3.82611484114337
O -0.52668669348906 1.03824721927530 3.79083994652981
H 0.40992518441155 0.80419172714403 3.70162676355280
H -1.81429117984508 2.36814366549762 2.99557890447929
H -0.68963518461877 3.47332838801457 4.80002092195456
H -0.35454173396043 4.38737668225035 3.29893044904404
H 0.89958902969307 3.34273875082811 4.02261535215251

S70
Compound 4a-R,S, isomer 000 001 002 0
C -0.14811433274763 0.12434196533907 0.07488936913910
C 1.32253466564194 0.06204043491318 0.13444608337730
C 2.15188877849840 1.11646429915676 0.07192664936160
C -0.88539550948946 1.13692154696381 -0.80797916669300
C -0.18757686358459 2.11161282904138 -1.66928895784989
C 0.95214159040247 2.77063196117402 -1.38747850604649
C -0.94584068876022 1.26630738970834 0.71569106327706
C -0.31146577657848 2.38169435754349 1.44107426883724
C 0.84945541738225 2.98807455088935 1.12742166374422
C 1.68914016954681 2.55286425407822 -0.06860445299160
H -0.64146115140688 -0.84860379242159 0.14178175094678
H 1.75393593053013 -0.93895693080064 0.23311990820281
H 3.23086706219308 0.94029458061232 0.12059400863462
H -1.80420734083398 0.74277510967513 -1.24959731507716
H -0.67179729277983 2.29484833717546 -2.63125837145599
H -1.89663017299823 0.94621799927945 1.14914049469455
H -0.86882647462591 2.73344476602823 2.31277854554298
H 2.58860961631700 3.18365529260420 -0.08230784221395
C 1.59895179878249 3.77441424926937 -2.32926966962142
C 0.98068243634614 3.87052451364363 -3.71407641948996
O 1.56915459882749 5.08593058283032 -1.78026278019855
H 1.91315556195254 5.07438644764927 -0.87026674563122
H 2.65604684828114 3.44658469131347 -2.45224473081708
H 1.53300983023879 4.61940041268293 -4.30036098588547
H 1.01869080932646 2.90668061480826 -4.24273424080146
H -0.06624358998049 4.20454902537710 -3.64675111724148
C 1.40060293003022 4.17289895920557 1.89354707832625
C 0.65048614962815 4.57561210252326 3.15570417815381
O 1.52364208544980 5.29889077003918 1.00760288482603
H 0.64039620512489 5.48478327207586 0.65180805925975
H 2.44500782063262 3.94006857947702 2.16817470884078
H 1.14020039179269 5.45238628073377 3.60377557756124
H 0.64055184253095 3.76097449734677 3.89559790003381
H -0.39345016035743 4.84848092689973 2.92993901823646

Compound 4a-R,S, isomer 000 001 020 0

S71
 C -0.28711459377008 -0.01462832784140 -0.09014966528695
C 1.16742940485366 -0.25025177191247 -0.15248004816591
C 2.11866751457724 0.69931483963705 -0.16091489589646
C -0.95116088624803 1.17236447634598 -0.80499884264914
C -0.18533304390510 2.14406004926405 -1.60544966758470
C 1.03910602143574 2.62989492947901 -1.32533136041496
C -0.90630979720485 1.12289393285419 0.72260210383109
C -0.10283679315140 2.06249909175932 1.53773867565281
C 1.09796669731912 2.55291196918125 1.17691976513518
C 1.82656080040284 2.18704072526419 -0.09901867968762
H -0.88780889000151 -0.92773032243884 -0.10062725437020
H 1.47572864762928 -1.29956002886530 -0.19848206152181
H 3.16917131221891 0.39564921260872 -0.21132034815290
H -1.93405103826090 0.93685910951915 -1.22109067090839
H -0.68020868438226 2.49711825178056 -2.51761193535083
H -1.87049579117061 0.88429283535813 1.17615142503204
H 1.59729313844575 3.25331351654626 1.85588962011680
H 2.78799936926512 2.71390156490234 -0.12047893816134
C 1.70958931335962 3.63649751902472 -2.23400915243636
C 1.86625561979607 5.00835602719217 -1.58616358786756
O 3.01801076025280 3.20046942968471 -2.59122190714527
H 2.93886185081693 2.30150649355513 -2.93875645590118
H 1.08090704169000 3.75050987945880 -3.14081741104389
H 2.41485562069571 5.67952389862989 -2.26493440779414
H 0.88128003661781 5.44551544903409 -1.36544723311810
H 2.43653329386411 4.93654466826781 -0.64677338946476
C -0.72203108853009 2.45391123560087 2.86859728730714
C -0.74817927921563 1.30022220830316 3.86557724636326
O -2.06846687821489 2.88603060415093 2.70433706267976
H -2.07159590949541 3.57969327741695 2.03085299510744
H -0.10605283662997 3.26940140555516 3.29831121275098
H -1.24195609757786 1.62298556713770 4.79520919421855
H 0.27501375843957 0.96890791109251 4.09663936711258
H -1.30995924335484 0.44418362153598 3.46063273845471

Compound 4a-R,S, isomer 000 001 200 0

C 0.12084267241338 0.01171075201525 0.10768015027567
C 1.58855177248277 0.13568704542521 0.05226635816393
C 2.28090991860989 1.28403210212123 -0.04199685217069
C -0.80874109704108 0.94608135892036 -0.67815842522718
C -0.30655080455452 2.02632952952384 -1.54669341103812
C 0.76116260132155 2.81293631594106 -1.31626154990661
C -0.79351407981601 1.01013340977627 0.84614079421788
C -0.20901684634961 2.16183202458096 1.57082249823034
C 0.84459090095686 2.90098512022873 1.18897268042093
C 1.63584415872028 2.65711016441006 -0.07939042771868
H -0.23769266694101 -1.02133868656030 0.15052797033908
H 2.14370511120873 -0.80733023090218 0.08447319574627
H 3.37407311094399 1.24028961715655 -0.07913389825801
H -1.68971810271751 0.43686607875468 -1.07934934972179
H -0.87574447868705 2.19172597344529 -2.46859101032217
H -0.68511043991839 2.38568929431767 2.52934957383477
H 1.17462054561595 3.71747365963943 1.83924417398273
H 2.43909236961574 3.40014822203540 -0.15005659212556
C 1.15710047007298 3.89856420736964 -2.29279731974528
C 0.96891505982774 5.30173216782118 -1.72580774260144
O 2.53162395230934 3.78005659186595 -2.64840155859664
H 2.67582343321980 2.87274440566439 -2.95023246953931

S72
 H 0.51670155802609 3.79876854482539 -3.19299830424285
H 1.32837639043090 6.04691376742046 -2.45219135674979
H -0.09271118810391 5.49113739079888 -1.50934035720597
H 1.54416507980661 5.43010596968835 -0.79563144843520
C -2.01254732910310 0.39169285293067 1.53427355559353
C -3.21378031362351 1.32568817299710 1.56707834871885
O -1.71419159675156 0.03981757704075 2.87376641430760
H -0.88235806691965 -0.45343270731185 2.87133997879217
H -2.29476495823379 -0.51280981466471 0.95438404409440
H -4.05100894944706 0.84110438531303 2.09165387359059
H -3.53337046660805 1.58081299854218 0.54554929240045
H -2.97108111843228 2.25800237231833 2.09890848557900

Compound 4a-R,S, isomer 000 002 001 0

C 0.21434654912641 -0.01494284006387 0.07289930116309
C 1.67928290363035 0.11746177102339 -0.02828667165390
C 2.35689009421714 1.27380990041675 -0.11105047046873
C -0.74519950248538 0.92455728988076 -0.66337063942345
C -0.28970079061099 2.04097065018169 -1.51268628446847
C 0.78220983721927 2.82928972089970 -1.30749711354623
C -0.64860460735173 0.97176798168526 0.86714597753785
C -0.09346667714945 2.13711520224551 1.57796576170523
C 0.94438991310880 2.90038268538560 1.18624046362543
C 1.70234957897821 2.63851067893513 -0.10739913152126
H -0.13685444557405 -1.04841965043274 0.12919129062219
H 2.24212269005177 -0.82112207110031 -0.03829195424389
H 3.44847218977627 1.24200785445692 -0.18572910011419
H -1.64793063367598 0.43048688160036 -1.03143383275834
H -0.91330202423870 2.24523761525748 -2.38996301342442
H -1.49417328216028 0.50435160302379 1.37795643415330
H -0.59971724344352 2.40305157077786 2.51286372750306
H 2.50104842963013 3.38769650184171 -0.17287333354195
C 1.10534210850330 3.97208275133442 -2.24967500935449
C 2.44991848251078 3.79142253045330 -2.95902032102916
O 1.04136384951809 5.23074450652617 -1.58662515048871
H 1.68564401483128 5.24082106825063 -0.85954821754884
H 0.31182662687218 4.01110821456828 -3.01398176238263
H 2.63946590800139 4.65089554356490 -3.62024722124044
H 2.46081134785052 2.86706748021998 -3.55738346263508
H 3.27973587767308 3.73502821756534 -2.23441325142557
C 1.38707216246808 4.09432270986396 2.00265368924456
C 2.78801866385510 3.94310402589074 2.58337024175936
O 1.39814635492529 5.27891976740933 1.20056739668045
H 0.53657352670269 5.35333289412669 0.76182007761724
H 0.67390730758871 4.22057291624090 2.84077828970619
H 3.07102610174191 4.86268609535438 3.11825575025833
H 2.82510027881410 3.09388964364600 3.28133681198374
H 3.52979006935060 3.77283543195422 1.78715299763937

S73
Compound 4a-R,S, isomer 000 002 010 0
C 0.60882679181202 -0.06344150693336 0.16958641646576
C 2.03687689424646 0.30505150255406 0.20309097674141
C 2.52626224037771 1.55626599040585 0.20419112507529
C -0.42702710395250 0.72643330756932 -0.64507983844287
C -0.07221912750450 1.91864821147695 -1.43505411481276
C 0.84671819150061 2.85153773637605 -1.11824965607917
C -0.48064489847224 0.73750677642151 0.88322993564755
C -0.20493838022478 1.95452375851776 1.68006646096684
C 0.74228582829475 2.86357253343508 1.38180699977220
C 1.65422276563244 2.79475757116620 0.17291949114633
H 0.42961562809837 -1.14171296368661 0.17544385516557
H 2.74109920890930 -0.53284366221095 0.22005335937344
H 3.61110958963130 1.70110703026256 0.22075978541656
H -1.19366569944783 0.10060380610673 -1.10901297611435
H -0.61720970494861 2.03756482604628 -2.37855897952987
H -1.26378853507388 0.11223015268657 1.31672147016300
H 0.86376036681575 3.72449508637852 2.04899224126726
H 2.29637395241371 3.68332765527322 0.19512557618747
C 1.12197149923034 4.02109403443446 -2.03761847714396
C 2.51233409625936 3.97079911764266 -2.66216159166115
O 1.03587733905786 5.25305615641454 -1.32657163580478
H 0.18240814079492 5.26551190344218 -0.87215993526955
H 0.37301500808095 3.99608258026144 -2.85540396235757
H 2.67979489156180 4.87396432554733 -3.26916404489891
H 2.61592179251283 3.08176711701559 -3.30144887920930
H 3.29160600583907 3.93568396006577 -1.88478670862426
C -1.09664568343523 2.14596423469106 2.89507549395794
C -2.53868625991196 2.47177658577159 2.52009143852031
O -1.13652664942788 0.96992096896606 3.69555922336934
H -0.22337649540457 0.71804711295600 3.88941118723339
H -0.69047011927148 2.99600475943126 3.47957272603108
H -3.14998206399782 2.55732365967089 3.43175703939794
H -2.58665547981180 3.42007014758477 1.96437687311586
H -2.97096673409782 1.67654476510541 1.89315384581608

Compound 4a-R,S, isomer 000 002 100 0

C 0.15320468523358 0.03244791149226 -0.00969511936810
C 1.61563087288150 0.19027046127466 0.11104180498976
C 2.27365314702993 1.35559413115248 0.22144961172678
C -0.72380112977916 1.01743375860920 -0.79442337304407
C -0.17760970912439 2.20508048665099 -1.47260161113035
C 0.85245306050823 2.96977443823896 -1.06037502033761
C -0.85592707844559 0.89870835791008 0.73758453245037

S74
 C -0.43312813354103 2.02464382060706 1.60147693787230
C 0.62577207335772 2.82787343108164 1.41198122142387
C 1.58939800611135 2.70663562409310 0.24770186638374
H -0.16938420638537 -1.00742138592380 -0.11508348956469
H 2.19372572048042 -0.73899307388706 0.09752696357685
H 3.36565298510692 1.34090294591325 0.29445537915559
H -1.53854745225467 0.53238763589415 -1.34075162700994
H -0.66624628441318 2.47292273219687 -2.41662306511041
H -1.09453529589842 2.22200755768341 2.44956078677959
H 0.80487434207691 3.63697423096947 2.12753477481595
H 2.34882490845602 3.48964927041418 0.35965461484143
C 1.32054135818551 4.15527180575472 -1.87540502817856
C 2.71237357390290 3.95469044618574 -2.46559971280548
O 1.38155489326998 5.32908122651607 -1.07044828047998
H 0.52309637073479 5.42883249812289 -0.63661472629071
H 0.60601827195664 4.29899198682298 -2.71173175727187
H 3.02687856444380 4.86830172020320 -2.99337101834741
H 2.71445958716948 3.11107286634050 -3.17137032191889
H 3.44926743819151 3.75025257419389 -1.67316876428383
C -2.10379877926407 0.16352396281364 1.23105669159610
C -1.87873943150546 -0.57540176812188 2.54235575999837
O -3.17700341959151 1.06644897235251 1.43353359978918
H -3.25294713948818 1.61567261520343 0.64123834475930
H -2.37388604587426 -0.58429987414173 0.45540188443851
H -2.81038893933793 -1.06737447117996 2.86007925364303
H -1.09437222748298 -1.33836900490987 2.42686854005463
H -1.57204448724592 0.12118832587419 3.33711820951405

Compound 4a-R,S, isomer 000 010 020 0

C -0.18573784070879 0.03249682908091 -0.02273635142716
C 1.27601027064969 -0.16225319755811 0.00294359419958
C 2.19869361146812 0.81440281031452 0.00490754762392
C -0.85516242362478 1.16665034046589 -0.80795951252926
C -0.10272659644374 2.14924640893344 -1.61873060721481
C 1.09697980913149 2.65783637171760 -1.28288180305273
C -0.88159661589079 1.17709920894545 0.71848157230901
C -0.14582809347916 2.16982137438257 1.53453321180436
C 1.05824379354492 2.68035145847320 1.21492416847598
C 1.85194902115581 2.29229527170694 -0.01900697761813
H -0.75739634657738 -0.89914519420796 -0.02732052583239
H 1.61464258640227 -1.20296283767554 0.02248634752178
H 3.25838193169713 0.54155341154642 0.02730524608049
H -1.80935770961777 0.87292667274379 -1.25565469511808
H 1.54299198839482 3.39861459456677 -1.95203817792213
H -1.85701917922129 0.92146639124687 1.13726446665655
H 1.50587953346565 3.41664751592559 1.89166606618626
H 2.79077808250705 2.86228232559086 -0.01030550167401
C -0.81273564955507 2.60982147451955 -2.88664001073670
C -1.93181335106815 3.59986344117287 -2.56971862234290
O 0.04908092380587 3.24866512015816 -3.80604868758522
H 0.78347978468131 2.64533287216782 -3.98471889663679
H -1.27054900183453 1.71019160680981 -3.35366606246464

S75
 H -2.45636826276759 3.88849935411487 -3.49338476849336
H -2.66052151139951 3.16499965143760 -1.86902792876032
H -1.49984494402084 4.50317059453744 -2.11188926625084
C -0.84447484340348 2.59443272758032 2.81480379475619
C -0.90343322248716 1.47869907402079 3.85257566106720
O -2.18800536624104 2.99027368385792 2.55891776819153
H -2.16618927890282 3.66012217697171 1.86198989881687
H -0.27043096717483 3.43887996662585 3.24650954258547
H -1.45365954230729 1.82554983926110 4.74090744779254
H 0.11166973688827 1.17821136475989 4.15161214307853
H -1.42562400613539 0.59611388971617 3.45169821566962

Compound 4a-R,S, isomer 000 010 200 0

C 0.01686978771527 0.02234958210942 0.06217835992284
C 1.48898538491098 0.06278293474907 0.12553957758696
C 2.25110414976593 1.16837421966439 0.07183456018204
C -0.79700840826553 0.99335094944640 -0.78709461732495
C -0.21394806565536 2.06229407794393 -1.62787299625653
C 0.88173321615956 2.77252416530688 -1.30365051801652
C -0.89298319362278 1.08007108474099 0.73041366646843
C -0.29220784282075 2.19550774282998 1.49451009516734
C 0.83004447496489 2.86790431168116 1.19000811427675
C 1.68364375643075 2.57341877910818 -0.03122883578020
H -0.40225698068857 -0.98832951970183 0.08591168665604
H 1.98515945332182 -0.90850638075444 0.21931313368735
H 3.33906636896053 1.06340181385872 0.12679833338877
H -1.68501941118483 0.54108576952930 -1.23428517479032
H 1.21072978053142 3.56274470889174 -1.98754105106895
H -0.81787162434386 2.44499675233691 2.42056512418096
H 1.16991887896689 3.65738818457511 1.86778627519901
H 2.52308098989642 3.28155332790936 -0.04421917740176
C -0.99039302803334 2.37409275947021 -2.89464211010503
C -0.98406050660107 1.23559568500989 -3.90746012301778
O -2.35666735844487 2.64765838860162 -2.58614868214089
H -2.36900896313715 3.35154765062744 -1.92305835685938
H -0.52137855074345 3.25992401964841 -3.36712831637995
H -1.59269710644278 1.51256910216683 -4.78193778648005
H 0.04328044734022 1.02101791206672 -4.23744054731579
H -1.41150071472229 0.31805692104100 -3.47451139202858
C -2.21913159102381 0.57045786546770 1.29925622500232
C -3.34148845914965 1.58485442301752 1.12592814472089
O -2.11501267554086 0.27703765473563 2.68107100088478
H -1.34340900086970 -0.29259993333646 2.80476491959873
H -2.49076629465315 -0.34502137815909 0.73239883164579
H -4.28207781070053 1.18499367673285 1.53369431203306
H -3.48186505028515 1.81754214235284 0.05957249114642
H -3.10626428399179 2.51729882999974 1.66207385900656

S76
Compound 4a-R,S, isomer 000 020 010 0
C 0.64578788421296 -0.08434410336741 0.04350416754100
C 2.06242494156920 0.32573630655421 0.06458688324923
C 2.51436911431221 1.59050674375856 0.06540292087930
C -0.43246095414861 0.66908558346348 -0.74135152126237
C -0.15079798479576 1.88007093001126 -1.54440580125304
C 0.75448633801038 2.82206388880541 -1.21815923837194
C -0.45748712569699 0.67711225065140 0.78459493815023
C -0.20220191013593 1.89651008265724 1.58373537947226
C 0.71347151308985 2.83518254221579 1.27753277888049
C 1.59731104776600 2.79956465473797 0.04401691707410
H 0.50055558343112 -1.16774946934289 0.04685421223060
H 2.79159670480411 -0.49077710465864 0.08080866883693
H 3.59389519398797 1.76974455687769 0.08217317622414
H -1.16937270327323 0.01140914364189 -1.20688388103368
H 0.88194465764516 3.67534529591756 -1.89358555275041
H -1.20929326744085 0.02413159657980 1.23257954218477
H 0.81887713132039 3.69554784253708 1.94775164808503
H 2.22311038107636 3.70218392787416 0.04956381494822
C -0.99341716349472 2.03001029381659 -2.79959592796068
C -2.45589400492779 2.32981442155121 -2.48665037711781
O -0.97521486708540 0.84072160399208 -3.58101347762553
H -0.04976919525773 0.60520139731000 -3.73222559809478
H -0.58230411684018 2.87929275868524 -3.38180292405922
H -3.03330894077011 2.38598068542293 -3.42239698809211
H -2.54542124992816 3.28565312692129 -1.94948826202683
H -2.89410883627741 1.53577671898841 -1.86229176256750
C -1.08551649574745 2.05940699947476 2.80899103695888
C -2.53698348413607 2.35526034593115 2.44521736837788
O -1.09277054183317 0.87843688562031 3.60309033198302
H -0.17273782262523 0.64490929294817 3.78691642031061
H -0.69376955754056 2.91499716193057 3.39530166322994
H -3.14474587501344 2.42049846025876 3.36094301340101
H -2.60913266515167 3.30563938058956 1.89587997700660
H -2.95435817896490 1.55478563451921 1.81483675630830

Compound 4a-R,S, isomer 000 020 100 0

C -0.06324389012305 -0.00336909359265 -0.12825707275241
C 1.40064699175914 -0.18656419392897 -0.16186629073584
C 2.31524201903661 0.79584541686160 -0.14216161131909

S77
 C -0.77834663554919 1.16055763386287 -0.81369739225846
C -0.08248934500345 2.22425017239159 -1.56847923784846
C 1.13757055282717 2.70776727241065 -1.26680303072557
C -0.76250165412798 1.05904949967546 0.72107577280117
C 0.00586231632009 2.03809019585774 1.52248538367241
C 1.19408809085861 2.58043733911332 1.20916724006798
C 1.95671388399749 2.26821422916519 -0.06648733753745
H -0.62368679880491 -0.94093419698157 -0.18686756683184
H 1.74667064206068 -1.22398738735653 -0.20920384778777
H 3.37704523562542 0.53251544698304 -0.17209088258104
H -1.72627756402927 0.86701966021725 -1.27210240468006
H 1.55309519943744 3.50045915020393 -1.89886161665886
H -0.48760614761000 2.36203892188544 2.44288481944309
H 1.63565800273250 3.30863163077175 1.89676718599184
H 2.88977028017038 2.84756524245407 -0.06039264406583
C -0.87335861831437 2.80396657715519 -2.72874057259388
C -2.07787513894663 3.61453145028049 -2.25962491527385
O -1.37696568146215 1.78094434844351 -3.58016057176989
H -0.63184035915991 1.22031897322393 -3.83579441817508
H -0.19987397305314 3.47946698117601 -3.29345709115158
H -2.64320674583954 3.98395505110873 -3.12894301819601
H -1.75352122688996 4.47017728468942 -1.64912019985883
H -2.75795153673604 2.98911121092255 -1.65916961950063
C -2.09003871721984 0.63245629719469 1.34961442483119
C -1.91934195397603 -0.13830132609124 2.65031343122331
O -2.89751718824632 1.76355972910245 1.62841753957938
H -2.91455108377696 2.31673982395575 0.83529172714851
H -2.60047146614120 -0.03089374893028 0.61991974525173
H -2.90528703568048 -0.40050170796152 3.06280158186034
H -1.34778014123423 -1.06289475830382 2.47881887831637
H -1.38619165892643 0.46677077773128 3.39903083832828

Compound 4a-R,S, isomer 000 100 200 0

C -0.02754155749876 -0.01205091191484 0.08915034750121
C 1.44306240669515 -0.07517538054256 0.17321006066978
C 2.28842543245184 0.96777951810613 0.13284895937131
C -0.80814895097755 0.96890021171848 -0.80387155371785
C -0.07498250000141 1.97946470697245 -1.60878198241656
C 1.06978714810980 2.60817717013923 -1.30060172153507
C -0.88650714752387 1.08063256877143 0.73882091433631
C -0.22896513935973 2.20846284220367 1.44829828197220
C 0.94560473723212 2.79473666486300 1.16755787473213
C 1.82523947371287 2.40658176211399 -0.00211987531902
H -0.50434213949054 -0.99388219925770 0.16305879909592
H 1.86246566235889 -1.08078557975636 0.27972092105398
H 3.36461767336792 0.78247126603134 0.20398225331316
H -0.51283010800520 2.17923938355385 -2.58954856941890
H 1.48989652304784 3.31113600780116 -2.02684284433286
H -0.77426954763328 2.59909699955884 2.31233315962275
H 1.28441216884788 3.61500531059492 1.80834257278157
H 2.70904488524084 3.05858125832399 -0.00623420189087
C -1.95938167779340 0.33572505818312 -1.60315014802813
C -3.08990955386521 1.29424412694479 -1.94912061632253
O -1.45617435685593 -0.16887594579683 -2.83167295072679
H -0.65416333418859 -0.67334026693687 -2.63729551877196
H -2.38203399630464 -0.49819016264803 -1.01416225342693
H -3.80812189246919 0.78805219199231 -2.61149219946544
H -3.61766358197086 1.62258222248753 -1.04353643435680

S78
 H -2.71305373399520 2.18474336731087 -2.47364041701882
C -2.11385440196920 0.54142645423605 1.49372574099737
C -3.16090774584313 1.60045451412887 1.84649427480984
O -1.70290025981897 -0.17197917725985 2.65126837109055
H -1.12138874009327 0.40575152646011 3.16500005207879
H -2.60243680631362 -0.21825176070915 0.86993864809139
H -4.04723036930129 1.11003367599109 2.27603855512043
H -3.46836334281396 2.17958408799259 0.96302695143646
H -2.78379020556662 2.31132231527922 2.59788895163934

Compound 4a-R,S, isomer 000 200 100 0

C 0.04624024559905 -0.15133010660681 -0.01394886740986
C 1.52287240637391 -0.14715731480334 -0.01961207574947
C 2.30761028882342 0.94114971587732 -0.02411807770864
C -0.81804581623464 0.84996245252165 -0.77136692765671
C -0.23685821530369 2.01066030600522 -1.48523592798481
C 0.89674203615712 2.67080225093877 -1.20138689319015
C -0.81325749702052 0.83554454454670 0.78975393069927
C -0.18005555824033 1.94636834850834 1.54006867090727
C 0.94675677867303 2.61524834548052 1.24259004567275
C 1.77308946499859 2.36011169695679 -0.00308854641489
H -0.37955086065813 -1.15975203621901 -0.02597516936691
H 1.99761187443715 -1.13351906994136 -0.02645419674165
H 3.39401040425882 0.80937149793974 -0.03303096777562
H -0.84654159218462 2.37457540970680 -2.31584633414237
H 1.17501801281648 3.52710947865612 -1.82371322892403
H -0.69936392448197 2.25186110039878 2.45437087726441
H 1.27112728204581 3.41549438577553 1.91523894366180
H 2.62677772642424 3.05109028386943 -0.00373408125232
C -2.04906862640076 0.27099205958754 -1.49311205709722
C -1.74041012109138 -0.14953459074472 -2.92526965705840
O -3.10480280076257 1.20311468740642 -1.51815031482229
H -3.33009785766429 1.38568358159284 -0.58728987390894
H -2.35728724753484 -0.64846259526176 -0.96072748466359
H -2.63646567666331 -0.60347360464881 -3.37468800969244
H -0.91930236116855 -0.88261660080420 -2.94675941713839
H -1.45297126697429 0.71208529851970 -3.54494944928686
C -2.05812959791248 0.27157218785194 1.47955384482762
C -1.83590886063451 -0.14545247685207 2.93097127018292
O -3.15804677369347 1.18386138395262 1.35832346433304
H -2.89423315860029 2.02714363609256 1.75425652589209
H -2.39058355060875 -0.62010098006572 0.93520088987921
H -2.75328818860944 -0.60221009387386 3.33150397196109
H -1.01603074271599 -0.87774785621368 2.99812430925294
H -1.57485115716168 0.70852968737192 3.57481356627150

S79
Compound 9, isomer 000 000 001 2
C -0.19814885736796 -0.05795214946051 0.15894946890342
C 1.25156635697068 -0.04905673443405 -0.09581517689871
C 2.02552995154679 1.03770697223611 -0.24165626836041
C -1.15531778596249 0.97100953931903 -0.43228297784051
C -0.71107659042294 2.05671319146092 -1.32184019020412
C 0.44650386371523 2.72867252403105 -1.23296125869497
C -0.84280751591234 0.99740631243469 1.06784638739068
C -0.06806306448609 2.07971231094926 1.69889615706239
C 0.98634023663427 2.78699696877785 1.21794822229465
C 1.53512650233810 2.48082667910165 -0.19551717836866
H -0.63112646740193 -1.05564605279953 0.26653209216208
H 1.73204988434943 -1.03177251919691 -0.13166398624584
H 3.10077229955939 0.89136017957974 -0.37648501054065
H -2.14414747444045 0.57027435422729 -0.66917015156910
H -1.41258220623407 2.33787687883802 -2.11354057310618
H 0.64327544723188 3.51708138528882 -1.96486310620661
H -1.64770828521236 0.61074024278024 1.69801801927598
H -0.42667201437117 2.31895473952258 2.70321752289597
Si 1.67907194243273 4.12795835553801 2.37899657383395
C 1.37121746347536 5.86502365019185 1.68856495453229
H 1.63280368042105 6.62126384731380 2.44815946130637
H 1.96353035685742 6.08641804023792 0.78736151719812
H 0.30674682985503 5.99591255898509 1.43320776273126
C 0.78719113410639 4.03254442700602 4.04366431055095
H 1.20700060109952 4.80169212614038 4.71338713006180
H -0.29380651058470 4.22607994214498 3.95445754655032
H 0.92391961530358 3.05420786602512 4.53191522173385
C 3.52702331560242 3.90397633205370 2.72722346402083
H 3.80364395325049 4.48626832640364 3.62242302616834
H 3.76678117417169 2.84673241895686 2.92661541163768
H 4.16957365150843 4.24538432326448 1.90175911711188
C 2.72302418614573 3.39240653046367 -0.53452056756277
O 3.14449138006997 3.17595760442343 -1.88849581625581
H 2.42644303100713 4.44746954180951 -0.47735947509607
H 3.56866303332151 3.20612163784183 0.13554005611048
C 4.33115958458128 2.57368382645716 -2.11375368412405
O 5.08967823660265 2.22510316540976 -1.24240072715666
C 4.55568004490456 2.38996529133505 -3.59258847183577
H 5.55824554877593 1.98201134865285 -3.76757500533038
H 3.79442422330728 1.69961256682896 -3.98910692329877
H 4.43128281830767 3.34871527018533 -4.11796634873898

Compound 9, isomer 000 000 002 1

C -0.02526916017157 0.13630557011810 -0.34190549277677
C 1.40981168470365 0.17631669845008 -0.66889042916311

S80
 C 2.21127332773616 1.25438098487129 -0.62529464511864
C -0.98080228706238 1.28187811847301 -0.65455797931430
C -0.54742638187997 2.53025019162485 -1.30177002291289
C 0.63000791874346 3.15154942814167 -1.12484783222928
C -0.60792713006559 0.98203530009800 0.80040550005556
C 0.22799441926831 1.87892336674982 1.61014980976273
C 1.28282111466618 2.63410536365170 1.22431167269431
C 1.77736290519929 2.66720117848300 -0.23499581890437
H -0.47783892177287 -0.85450699571901 -0.43034855652603
H 1.85467670475707 -0.78415569730189 -0.94903148636038
H 3.26691433779477 1.09124779057269 -0.86813144962595
H -1.98758693961430 0.95750802227172 -0.92948823151242
H -1.28217727311951 2.99900433111707 -1.96450961359219
H 0.76320820538866 4.09723002301546 -1.66054139933898
H -1.39336186119878 0.47973213237812 1.37034226743022
H -0.02249933209999 1.89196523980270 2.67455518951291
C 2.01334066252216 3.37719167289631 2.31220820667986
O 3.22557962310889 2.68298623213798 2.69455418257956
H 2.35524720500814 4.36774229344408 1.99216169893848
H 1.37810450993121 3.48641404891336 3.20075988136615
C 3.11648378309164 1.70091971465498 3.61356007046112
O 2.10209966650740 1.45210973758373 4.21669526112637
C 4.42484832244985 0.96578395003202 3.76167257674425
H 4.36926539658255 0.27877875588427 4.61465807685946
H 4.61947899611573 0.39626293241339 2.83860054546536
H 5.25511196415562 1.67605957794252 3.88908423866386
Si 3.26784689474275 3.82884248636008 -0.68064268825839
C 3.51534090621914 3.64739058748312 -2.54765307248175
H 4.38228074925668 4.25126583290462 -2.86474872054318
H 3.71304165411367 2.60132999445793 -2.83039758449129
H 2.63998946659686 3.98700559930410 -3.12242990491311
C 2.88006587095462 5.64781865307499 -0.32006571027180
H 3.55700255133473 6.28765536037381 -0.91073759070743
H 1.84751383331318 5.91513858789494 -0.59571256737613
H 3.02521286818914 5.91196259838773 0.73907846738934
C 4.88967240659779 3.34997684245747 0.15385040190968
H 5.70673988592088 3.94811401099332 -0.28407669189542
H 4.86628127461853 3.51987208921172 1.23807249484010
H 5.13070436985989 2.28742987646483 -0.01090359092874

Compound 9, isomer 000 000 010 2

C -0.20235060902022 -0.18974684078742 -0.17611097798712
C 1.24955527505685 -0.27777293813255 -0.41241501018685
C 2.10306432347070 0.75317687130803 -0.51516395337459
C -1.06795689693610 0.92341108613398 -0.77815033999738
C -0.50880813259709 1.98530057125289 -1.63224997613188
C 0.69388471777981 2.56768344157041 -1.49623065446851
C -0.82108012325109 0.87216776784135 0.73463218411878
C -0.02877417268012 1.89624330921162 1.45662220736683
C 1.07695179140382 2.49127949234312 0.95760306998864
C 1.69841960798744 2.21731918316701 -0.40729473838721
H -0.70475799096626 -1.15930617075183 -0.12947216349068
H 1.65103877951736 -1.29177241877635 -0.50641576683951
H 3.16536918984037 0.54487092752236 -0.67102306859085
H -2.06679150837113 0.59415308730179 -1.07548116150656
H -1.15407837390771 2.32047468688467 -2.45032731959043
H 0.97687169012349 3.35376202031601 -2.20534841200432
H -1.68759369663587 0.49951353151082 1.28910187441435

S81
 H 1.57280394427589 3.26069509160563 1.55460180778565
Si -0.64942726729310 2.38747756596787 3.17093002008871
C -0.69643606706892 0.84386727927190 4.26291772736889
H -1.08790033654917 1.08100123064760 5.26653436518728
H -1.34135449488983 0.06191355879246 3.82913582311185
H 0.31317498358247 0.41740005375028 4.38235936478076
C 0.48830308300606 3.67939850277553 3.93831132841152
H 0.12452455027526 3.95566084354790 4.94198266651480
H 1.51854671438159 3.30333071203512 4.04492463407591
H 0.53255171506547 4.59755317499927 3.33081471436014
C -2.40086100650609 3.08208646325327 3.01285249441083
H -2.81486895762412 3.34313506799567 4.00135457503026
H -2.40577145241408 3.99133877756550 2.38952107426644
H -3.08307820222087 2.35205758432649 2.54676553933099
C 2.93186363696628 3.10720919789637 -0.60887799115194
O 3.98477326330683 2.75062167391257 0.29554397025863
H 3.33865558795974 2.95479311640573 -1.61977888993658
H 2.67163867254911 4.16581703518391 -0.47073331049462
C 4.22805407643141 3.53651277740179 1.36603904955770
O 3.63209940067407 4.55786917990528 1.60601940435524
C 5.32363926154307 2.94584204220955 2.21566026338794
H 5.59831019710279 3.65165296531389 3.00851232570668
H 4.96193027731683 2.00595277082211 2.66260620781879
H 6.19808716680883 2.69745100007970 1.59621605972534

Compound 9, isomer 000 000 012 0

C -0.21003928720804 0.30669243676567 -0.28169504937827
C 1.25877296477328 0.20008799218195 -0.24177527138326
C 2.10341526355055 1.21487807286495 -0.00157859771819
C -0.93832654440435 1.52994421313780 -0.86070302298360
C -0.22795127091235 2.69168713500135 -1.42312889280384
C 0.91833640048201 3.20630041893924 -0.94968745330222
C -0.98907601261986 1.24160109731148 0.64247604788580
C -0.39076513560817 2.12086290337369 1.68775664349527
C 0.79664967688468 2.75452509669618 1.51674615704559
C 1.65037614048046 2.63876194684222 0.25037077187123
H -0.71916693357139 -0.64015553427006 -0.47928635666556
H 1.67050364250812 -0.79764166976943 -0.42366883838557
H 3.18017208595535 1.01921422411544 0.00304234912825
H -1.86444001850812 1.28062459458473 -1.38496253261035
H -0.69412312564213 3.15739987340106 -2.29712118876783
H 1.36021482799395 4.07531441741993 -1.44724252082339
H -1.94935125980297 0.80972301375847 0.93149088212123
H 2.54639392537512 3.25329597695223 0.40433455142688
Si -1.58926607033981 2.23916596105420 3.17295816679182
C -1.00907739263561 3.09526159114237 4.75376393521222
H -1.79357365596475 2.95049220537087 5.51629568939802
H -0.07738539706030 2.66648760540098 5.15674327837689
H -0.87841973669098 4.17618424691824 4.60321483908849
C -3.14457229512298 3.10666160300959 2.55086246279569
H -3.92754933445696 3.11283635641323 3.32772964978806
H -2.89512177929692 4.14832069265586 2.29575296366580
H -3.55966245290184 2.61859142076014 1.65451898716876
C -1.99759819739717 0.45561387002405 3.67651528019160
H -2.70840964147775 0.46140437825089 4.52018498606883
H -2.45197007102302 -0.13510061752986 2.86601481056057
H -1.08858867740123 -0.07411581692688 4.00773132401474

S82
 C 1.37022525228976 3.72875189033101 2.50765917657523
O 1.47214963432578 5.03793662555445 1.88919997288925
H 0.78635455463346 3.80602427462621 3.42557043400343
H 2.41078074226242 3.47356371051259 2.75803297795801
C 0.34191034070089 5.76504048284217 1.82281679702060
O -0.68745353419850 5.46075534270794 2.37742357739089
C 0.52596881872258 6.97667798325089 0.94593203855101
H -0.26136755036268 7.71083009716625 1.15696315500128
H 1.52351132922093 7.41664342652542 1.08374716051040
H 0.44283715971334 6.65431782479257 -0.10535044694333

Compound 9, isomer 000 000 020 1

C 0.12223203677330 0.21697403522701 0.45839864629440
C 1.58982549215203 0.26776999523667 0.33862082783573
C 2.33361955227518 1.36611909215772 0.11934539300576
C -0.80150969294464 1.11371240172442 -0.37574648945004
C -0.28480167138107 2.08098463454334 -1.36187641384750
C 0.83392762566187 2.81820112798008 -1.24735689243149
C -0.68367400304690 1.32730753821502 1.13495450581480
C -0.05404415077760 2.52980189704804 1.72413004790041
C 1.01482026086874 3.17226545863362 1.21449318103549
C 1.77021809184556 2.77471088927395 -0.04585700640128
H -0.27642921911500 -0.78572781103749 0.63265628137493
H 2.10356815035296 -0.69405775571161 0.43884121819318
H 3.41906989404428 1.23096795831332 0.05651235443474
H -1.73093770884245 0.62503824184726 -0.67914122409056
H -0.88564827197364 2.18934851522107 -2.27090316474854
H 1.08138703949171 3.49018331662808 -2.07685964170803
H -1.54264773131858 0.95940119414233 1.70262668776586
H 1.38420505097644 4.02581159993149 1.79101667780539
C -0.62113901265802 2.99127639859877 3.04144369087684
O -0.20524191810455 2.10469796517582 4.10660967663931
H -0.29554171720723 4.01347181123436 3.27523822657902
H -1.71943276988850 2.94036121030688 3.05619939817466
C 1.02025828242549 2.31948409511955 4.62808032341800
O 1.71945252592888 3.26099345262874 4.34103524580623
C 1.39349914054755 1.22167398701558 5.59214894074936
H 2.26647087710316 1.52827024688346 6.18118048232457
H 0.54626955820890 0.97323939958403 6.24745313936089
H 1.64347173711469 0.31558052412437 5.01630369819380
Si 3.22350350167106 4.00860215521009 -0.27608697369010
C 4.18339876533710 3.56067712300393 -1.83876402401194
H 5.03791197106671 4.24420762554901 -1.97628336012863
H 4.58003655766684 2.53379657563660 -1.78958661187403
H 3.54927652713792 3.63209307768515 -2.73725091016357
C 2.52485055042333 5.75444260340413 -0.44000130727001
H 3.33837886968782 6.48185428912161 -0.59888905762052
H 1.83221872815187 5.83306896418142 -1.29361801316931
H 1.97680194331846 6.05780604892336 0.46628824288556
C 4.34469942140462 3.89356947691274 1.23700703808194
H 5.11013136673533 4.68718271835406 1.21558436056740
H 3.77331980050110 3.99463844671482 2.17403490085107
H 4.86968010778054 2.92521295340959 1.27240780117863

S83
Compound 9, isomer 000 000 021 0
C -0.08517011773758 0.00850813607462 -0.06739661094973
C 1.36757643558870 -0.10929812797976 0.14622659774960
C 2.22527647266678 0.91916990232837 0.24555650572022
C -0.71108205264700 1.08347067388109 -0.96295466788838
C 0.08498499549244 2.09223614940463 -1.68172592178904
C 1.19434815082063 2.68393385136974 -1.21130970853940
C -0.91144108749388 1.13784934661123 0.55312733344751
C -0.33907750801365 2.19354773603491 1.42775275091658
C 0.88518979157703 2.77330590142530 1.29706970412511
C 1.81167354073687 2.37359814414567 0.13804592074395
H -0.61206663557326 -0.94858771187118 -0.09821354684390
H 1.75541886929161 -1.12912201008241 0.23450115174146
H 3.28657666063344 0.70876312946436 0.41245546133371
H -1.59617389091703 0.74127373946645 -1.50501191542690
H -0.28355557196109 2.37439396145349 -2.67303105385317
H 1.69816355484423 3.43115552631724 -1.83274490000229
H -1.90652842358046 0.81951846395220 0.86817653565402
H 2.72706348892628 2.96935282074922 0.20837777951213
C -1.27203032791560 2.57599195052097 2.55376799834482
O -1.22681482876028 1.60465471516001 3.62680322343284
H -0.99239146670618 3.52560595368887 3.01883926806967
H -2.30891749893504 2.64743756688577 2.19598204829296
C -2.19741225467090 0.67407472759507 3.70550287125751
O -3.11732342938083 0.58521659008192 2.92790595116573
C -1.96802406772986 -0.23197688539659 4.88904560181666
H -2.76872600508156 -0.97906922271535 4.94334860039323
H -0.99050836650165 -0.72851570491918 4.78816274929791
H -1.93674091113067 0.36133577758151 5.81575412313753
Si 1.57682909230308 4.03810885798991 2.54547286382494
C 0.61727666278208 5.67072822348319 2.49062261596441
H 1.10486218420692 6.41758002970347 3.14006762232124
H 0.60746699674950 6.07085642187542 1.46319058948648
H -0.42939192502252 5.57659790933864 2.81909753346922
C 1.59561912854101 3.32352950294221 4.29535489784535
H 1.98992173470622 4.06715152396517 5.00862445951076
H 0.60483233417941 2.99611713137169 4.64117920466925
H 2.25684724786020 2.44132841026922 4.32541991779533
C 3.36838661126109 4.44881515123544 2.09924293969417
H 3.77534902965621 5.14141452258339 2.85525438830310
H 4.01015352440331 3.55259619764882 2.09213581238382
H 3.45705655582316 4.94221474300247 1.11761553193224

Compound 9, isomer 000 000 100 2

C -0.15280193453769 -0.24742688503430 -0.01691417289011
C 1.31567048694953 -0.15022950840963 -0.07751093429033
C 2.04101465166381 0.96615570608012 -0.25475301663699
C -1.07159783427309 0.63922023879764 -0.84697878324133
C -0.56355722340704 1.65931050404639 -1.78185734384513
C 0.53087239799162 2.41992521262896 -1.62278590014956

S84
 C -1.03453906146349 0.81389841856811 0.68611920913530
C -0.40245031180278 2.01324700406115 1.28839942945622
C 0.66361865779082 2.70225376280902 0.84682511511967
C 1.44958542926925 2.35976338341711 -0.41086804574316
H -0.51227948748676 -1.27372692770181 0.09481805427563
H 1.85181554500483 -1.09722633887938 0.04020659287763
H 3.13346181442878 0.88108411260693 -0.27053434396185
H -1.96159787758277 0.12262149196177 -1.21597087548682
H -1.15729427269416 1.79634790056531 -2.69129189570276
H 0.77832135036138 3.15503036331154 -2.39381953195111
H -0.85533338716915 2.36964579809614 2.22059712761089
H 1.01813462041839 3.55021208977397 1.43919557583980
Si -2.53067878628235 0.17651876608648 1.65824112896807
C -3.83399702010099 1.54032868951855 1.70639494237855
H -4.72303361119593 1.22289737787957 2.27649994612788
H -3.44125770529280 2.45606111642817 2.17711426172257
H -4.15974101879677 1.80243472650507 0.68616537730197
C -3.26717221017427 -1.35908337267164 0.84056307268472
H -4.13559717995258 -1.70275541348212 1.42713859249561
H -3.62179854200872 -1.15909385052680 -0.18356383957328
H -2.54943498768789 -2.19433675980876 0.79797179061641
C -1.96980136007499 -0.26184108719009 3.40575742702287
H -2.81433405623974 -0.62475382161974 4.01507032010378
H -1.20321788636996 -1.05394355911687 3.38135066448300
H -1.53333888153794 0.60911292689974 3.92068779435683
C 2.61522831082627 3.33868991793397 -0.59771422593389
O 2.14639700723280 4.66121772831929 -0.88581380980739
H 3.24896981764779 3.36098382726695 0.29955468570454
H 3.21570633502896 3.03396393684431 -1.46800314179853
C 2.21827471348255 5.60755769270637 0.07511516699365
O 2.67679537680689 5.42093767264254 1.17505534504276
C 1.64068081295902 6.90771058171158 -0.42266747390408
H 1.75423307603335 7.68143993448388 0.34581466151608
H 2.14348061950528 7.21306701697275 -1.35280386386580
H 0.57476499495414 6.76495446012797 -0.66011653425259

Compound 9, isomer 000 000 102 0

C -0.24648537885132 0.11240418291278 -0.17813370677956
C 1.22408473145345 0.02439077951793 -0.23892036542632
C 2.08655304189248 1.05351564583492 -0.18306014105569
C -1.04311809636905 1.26195975954720 -0.78215085284483
C -0.40278972163217 2.38743009067802 -1.49087567303113
C 0.78059635661714 2.94633004850964 -1.18868719856741
C -0.99571576207764 1.10306471798564 0.74995871655435
C -0.22531863057539 2.04838450880487 1.58806440972242
C 0.92550636301860 2.68284383497773 1.29321613040124
C 1.65211900823899 2.49832002245720 -0.03159623587406
H -0.73802964943179 -0.85957749045513 -0.27388782143601
H 1.62837265618122 -0.98842645317893 -0.33456439265813
H 3.16060301542459 0.84980297674378 -0.23475194759375
H -1.98878992036242 0.94944479933457 -1.23307920952813
H -0.96365800070484 2.78595407310609 -2.34234381004145
H 1.14346247735463 3.77584046831355 -1.80354576060602
H -0.61811696686578 2.21845964557128 2.59589503641340
H 2.55461225413471 3.12424848193703 -0.01486740718199
Si -2.51062143817731 0.40506738532202 1.64974490608632
C -3.59590007163587 1.83619724815193 2.22925533858342
H -4.48958119697036 1.46343752724821 2.75714801277893
H -3.05437537373711 2.50331630766392 2.91885873589870

S85
 H -3.93527942980089 2.44138663472690 1.37228821121424
C -3.52142432682790 -0.70781746339916 0.50586266369548
H -4.36798668166816 -1.13810272791035 1.06675595163858
H -3.94191286734416 -0.14968670909621 -0.34661595050268
H -2.93153065951393 -1.54906635117717 0.10732502853777
C -1.86953363215462 -0.58703248578248 3.11947618958045
H -2.69127227839541 -0.93216215887085 3.76871439134223
H -1.31657936395638 -1.47487998533986 2.77019922533966
H -1.17540801644761 0.01243051353457 3.73107517946859
C 1.61370331113805 3.50800948353498 2.34050334202062
O 2.80858533460487 2.82631995987077 2.79225825594008
H 1.98210610805333 4.46288885676974 1.93749017658260
H 0.95524759444359 3.69742210224974 3.19936490650997
C 2.63021895715842 1.84049296901058 3.69747939809149
O 1.57835778241671 1.61022018899254 4.24224766285521
C 3.90643330140981 1.06492672911029 3.90371411067422
H 3.83126773011309 0.46293409059162 4.81758838949693
H 4.04840046860687 0.39514834189571 3.03943515379129
H 4.77349448464511 1.73931883988400 3.94719840369806

Compound 9, isomer 000 000 120 0

C 0.14046594111149 -0.25594752210367 0.22741443931201
C 1.60031296102314 -0.41159359491171 0.36647519979022
C 2.50886091425203 0.57486147857982 0.33384684219494
C -0.51629842439197 0.78132715674330 -0.67063490364394
C 0.25511257888119 1.74781736563075 -1.47456781111931
C 1.43027037435382 2.30446239452859 -1.13775671665143
C -0.69243025272174 0.88798208776624 0.86852118132301
C 0.01204912550034 1.98372983316535 1.61056631455677
C 1.23808444222203 2.47254323836602 1.32077269712620
C 2.12894750980525 2.03251177692308 0.18061584170327
H -0.37390784336674 -1.21913688431287 0.22305921495088
H 1.94942987723562 -1.44091970463440 0.49706556023666
H 3.56999790708604 0.32920165423219 0.43832314368043
H -1.40066468463726 0.41096838012181 -1.19364989831825
H -0.18970136744501 2.01418621785878 -2.43874961535690
H 1.90408592591561 3.00667101147967 -1.83043935788050
H 1.60140849022759 3.30359228977245 1.93101547150602
H 3.04580673483844 2.63570535689176 0.21644943570814
Si -2.36540144368387 0.21007540134182 1.50889952055049
C -3.05111590869726 -1.07011943726262 0.29045763699093
H -3.96379200057945 -1.50053728944637 0.73613373767835
H -3.34479365198005 -0.61498706115606 -0.66925321836264
H -2.36741751037853 -1.90663819505390 0.07927556074102
C -2.06689218429543 -0.68449831565659 3.14826351661813
H -2.99360295643592 -1.17021026313023 3.49709173445378
H -1.30242515952235 -1.46857685925962 3.01997299874628
H -1.72076669619873 -0.01361787810080 3.94984758609075
C -3.72699341365113 1.50708316834580 1.67419657710139
H -4.68996037872462 0.99105162701303 1.82805117791733
H -3.57372537012425 2.21282849317719 2.50066731643450
H -3.80448140287276 2.10126364559859 0.74917776927126
C -0.72003332399447 2.68926579354035 2.72924203384564
O -1.65020569388943 3.66333691031152 2.20181004848384
H -1.33805411559303 2.01396957796662 3.33235248941004
H -0.01010426222984 3.20361248150670 3.38852424406646
C -1.18682317991399 4.90907760168645 1.97186729678824

S86
 O -0.08147718739806 5.28594619737017 2.27459872147886
C -2.23340124216520 5.74443630522722 1.27806042141041
H -1.91930003762257 6.79511213390745 1.26465169234325
H -2.34961566516320 5.38196790162682 0.24381515904063
H -3.20823561384578 5.63535087303854 1.77547226236103

Compound 9, isomer 000 000 200 1

C 0.08101811874779 0.13032150459509 -0.03999174908787
C 1.55074917299030 0.03979176796315 0.02791864400102
C 2.41541632738086 1.06866854858469 0.02673209286009
C -0.64464180564815 1.19766304326627 -0.86186473184989
C 0.07554103901381 2.21677774132802 -1.64500364468155
C 1.23407481190070 2.81327660110063 -1.31461619911063
C -0.72079789668560 1.22803709784661 0.67315535585074
C -0.04348304868424 2.29060848459019 1.44900663214023
C 1.13356967863830 2.87499843345018 1.17105890280426
C 2.01083122194239 2.53870541944891 -0.02999249797032
H -0.42004856606391 -0.84165756989152 -0.04667845968382
H 1.95591502415829 -0.97647370347336 0.07225005375076
H 3.48263456730709 0.82407435309640 0.07146919402398
H -1.57097366944540 0.85198209088315 -1.32343334745151
H -0.39987155491557 2.49713196620647 -2.59057508183710
H 1.63616447047621 3.55075130107012 -2.01833112008902
H -0.58961212381438 2.63109162140387 2.33477706992743
H 1.47652039877755 3.65201504719634 1.86365612447639
C -2.02611626226650 0.75985974957006 1.27999094788383
O -2.96435122370657 1.84110380213280 1.41750943031311
H -2.47887210345280 -0.03841696489287 0.67603365320520
H -1.86204031561790 0.39532220782463 2.30509145758539
C -3.82020938335369 2.06770001824156 0.39919564684483
O -3.88050403141456 1.38671793633656 -0.59547234414893
C -4.68001426622174 3.27253177768155 0.68455811274371
H -5.40814550111720 3.40725744166395 -0.12405327786809
H -5.19593349786357 3.14819970607482 1.64879152602000
H -4.04132246489158 4.16567673957130 0.76976270142410
Si 3.58669348370426 3.63317840329131 0.00599745866748
C 3.08150269857778 5.45056152537691 -0.06851612675409
H 3.97264383471174 6.10002530074508 -0.05122495971947
H 2.51931753660155 5.67636160219411 -0.98889236272373
H 2.44657894730753 5.72929680038571 0.78784180086684
C 4.53662033209201 3.30112687350161 1.60320058007178
H 5.44710781391679 3.92192939240649 1.64695669365137
H 3.92826834558828 3.53494603301428 2.49172182372986
H 4.84603784487092 2.24625073518526 1.67820233063659
C 4.66968831649780 3.21041222659782 -1.48086756961580
H 5.58138016496524 3.83096901267926 -1.48328284855976
H 4.98299400735559 2.15411518391236 -1.46612926661786
H 4.13988147813776 3.38868112368721 -2.43040653242896

S87
Compound 9, isomer 000 000 201 0
C 0.02814995057009 0.11700283732548 0.14908204516190
C 1.49122986734426 0.21335957872417 -0.00638086645470
C 2.19974343634591 1.34638809426389 -0.14148640667114
C -0.94665546623313 1.06793361222914 -0.54222976167047
C -0.51531826583424 2.16525109396458 -1.42943015526193
C 0.59260664032777 2.90868380726931 -1.27889237319146
C -0.78240730172691 1.12536565280665 0.98448370768737
C -0.12284727912669 2.27344798146297 1.64794905945647
C 0.91602162834914 3.01539782796448 1.20647887858721
C 1.58025127320652 2.73051664793400 -0.14259547805792
H -0.34300866227651 -0.90413027278854 0.24984696444669
H 2.02591668784174 -0.74157716592082 -0.00374720642358
H 3.28763330065470 1.28022604398586 -0.24248679226803
H -1.87401754308630 0.58330144608265 -0.86020770524793
H -1.17197415124955 2.37058396637010 -2.28068493033195
H 0.80074492376972 3.69692717005058 -2.00926662363950
H -0.54644676440779 2.51046554898131 2.62970974167737
H 2.39218652300583 3.45583469688594 -0.29584244065424
C -1.94562022938136 0.55501342271788 1.76749944686045
O -1.54003569225088 0.12509111198471 3.07867145516878
H -2.70309552671278 1.33247205257043 1.94756253139054
H -2.40711589019609 -0.28848018626507 1.23565478228369
C -1.13037344938174 -1.15224743259633 3.22512644807277
O -1.13785685114313 -1.96873289584455 2.33636726652797
C -0.67058857002233 -1.40494702660573 4.63824473270925
H -0.41263562319144 -2.46365952612221 4.75981385907552
H 0.20825108163700 -0.77675664896478 4.85316811337521
H -1.45876283687424 -1.11665619632562 5.35011822085005
Si 1.61505289790001 4.42837161374254 2.23157052110263
C 1.47388112125479 6.02898991361301 1.23491595984836
H 1.92070469403586 6.87780756856036 1.77945309556252
H 1.99261111354067 5.94445561393357 0.26563442868661
H 0.41821140105840 6.27098645966579 1.02971375297118
C 0.67799194586950 4.60177130929974 3.85976889510616
H 1.09565163575426 5.43019887207048 4.45570345802910
H -0.38984330557269 4.81621915235451 3.69035879933867
H 0.74919464201892 3.68355794587012 4.46539501323953
C 3.44073746966329 4.07655110206594 2.57656401564908
H 3.90745450275267 4.90549697780961 3.13484075292139
H 3.55673462170776 3.15499310109027 3.17017747677512
H 4.00719071046596 3.94461768687854 1.63987787056050

Compound 9, isomer 000 000 210 0

C -0.47763738230465 0.21966345491558 -0.14881660394747
C 0.96072690420500 -0.09816056861969 -0.20095126282944

S88
 C 1.96381318462720 0.78473209513170 -0.08268538993459
C -1.07923374285093 1.51057422273497 -0.72451759032288
C -0.25806100137317 2.55209362404851 -1.36718188275792
C 0.99131525861185 2.89913804798253 -1.01749886168619
C -1.10348362540395 1.25522774925294 0.79071914348723
C -0.28310767507145 2.08607278362772 1.73293523034034
C 0.96839849173151 2.50996247692003 1.43482015952028
C 1.73128694316154 2.26495462008913 0.14623607251947
H -1.12571276182652 -0.64538752811827 -0.30380851757188
H 1.20539085721666 -1.15263103773363 -0.36433206886859
H 2.99799418292344 0.43354579424133 -0.15004899158884
H -2.04887660607746 1.35066712796972 -1.19874522422263
H -0.72492796529026 3.06401182517747 -2.21476046903872
H 1.50561089312434 3.68213149557387 -1.58321941072507
H 1.49914973736037 3.12267501040695 2.16755861893370
H 2.70965991583151 2.75570417425307 0.23877826989320
C -2.44286592121693 0.83510476412426 1.37412182711895
O -3.23794201584282 0.14694645409783 0.40389028475095
H -2.28909086308936 0.16777276025861 2.23382373775423
H -3.01221542780379 1.70705527990730 1.72870794053678
C -4.43696695905712 -0.30149465114067 0.83425635690384
O -4.83471580872831 -0.13631244746106 1.96039320644281
C -5.17565023993655 -1.01476189592095 -0.26935555570646
H -6.14491123289967 -1.36584377089509 0.10391134006780
H -5.32258076823968 -0.33472072643911 -1.12272060876746
H -4.57848846680409 -1.86636233103544 -0.63063425604055
Si -0.98033757795442 2.76136967412744 3.38046366560658
C -2.26174671555613 4.10800829817912 3.02159733465364
H -2.60021054143969 4.57235133494417 3.96336069619050
H -1.81938473780953 4.89719784897799 2.39163046426193
H -3.15420862404032 3.72502249215969 2.50233709465457
C -1.75138896695118 1.44068587300437 4.49832391740713
H -1.86657879821437 1.85908473881293 5.51266012592326
H -2.74574399148620 1.10908360326685 4.16390570802015
H -1.10169939145680 0.55328715959296 4.57854114455081
C 0.41788081569160 3.56101672202310 4.37007135613571
H 0.01080922172973 3.90844725770018 5.33439510286663
H 1.23048398693077 2.84882445014851 4.58656101561674
H 0.85219415244861 4.43603711321375 3.86110601860589

Compound 9, isomer 000 001 002 0

C 0.33908661235670 -0.19014468215897 -0.00034891395642
C 1.79699078311554 -0.01093938484532 0.13786164789340
C 2.44339332402181 1.16577170747975 0.14279231990355
C -0.50969231048643 0.69982893181229 -0.91535479767920
C 0.05984916500521 1.80612607929946 -1.70777075981017
C 1.06057100884569 2.64265365167413 -1.35210929298523
C -0.67346283105834 0.77950973698458 0.60975349838485
C -0.28014092945496 1.97221774641377 1.37896337472003
C 0.77790187610607 2.77011828219145 1.13835716028262
C 1.75888879636108 2.50943775471799 0.00306510605234
H 0.01376257005365 -1.23340045664327 0.02126784043586
H 2.38081107053133 -0.93138008263521 0.23753429542840

S89
 H 3.53343657625380 1.16760539040254 0.24298042666966
H -1.32250635014872 0.16819308587993 -1.41695384197763
H -0.40794674866040 1.94017141977371 -2.68908385606870
H -1.57988808030245 0.29463517406773 0.98076880056543
H -0.93840202123226 2.22849683076072 2.21632474764966
H 2.53651808442253 3.27921844615575 0.06020318452530
Si 1.66144265066696 4.02448588843505 -2.48307046784365
C 3.51793469069420 3.80154632559888 -2.76167360544420
H 3.91327879204157 4.59176785173592 -3.42192598777673
H 4.06690859059002 3.86443838039374 -1.80768479614728
H 3.74033577233992 2.82533597371938 -3.22267433742673
C 0.74597601708205 3.96590464744340 -4.13301557433365
H 1.10770157770908 4.76787469026807 -4.79784426689719
H 0.90304779754194 3.00488235089060 -4.64966636710406
H -0.33890345555287 4.10858314814276 -3.99859804731852
C 1.37478222609392 5.68519606156677 -1.63211882640949
H 1.68549571018269 6.51687419667275 -2.28705400963133
H 0.30952929168362 5.82698504692477 -1.38517791421705
H 1.96386150352005 5.75146102306541 -0.70340990516098
C 1.01159228137657 3.99142325926719 1.97710758347015
O 2.25811901234338 3.89311977380473 2.70764911813392
H 1.04613430249410 4.89872526423262 1.35594633590061
H 0.22862652734155 4.09934702256511 2.74060297530448
C 3.33051389968004 4.56737832840102 2.25820031362191
O 3.33853640471043 5.25463499339825 1.26319312495227
C 4.51931316446258 4.33660153118032 3.15699156277840
H 5.37843232599818 4.90991778756876 2.78906357126376
H 4.27405268135483 4.63334802996539 4.18811797452615
H 4.76023650837201 3.26232598399571 3.17723848329991

Compound 9, isomer 000 020 001 0

C 0.00679590681676 -0.21530196946636 -0.40453404800733
C 1.47251695925444 -0.14261565529349 -0.25660673431806
C 2.19237938799692 0.98190245319859 -0.11042387801956
C -0.95099184562296 0.72720860549635 0.32094654319941
C -0.49849942388601 1.79081011536151 1.24764148426524
C 0.62315326400039 2.51786952872928 1.09137741633927
C -0.78766340975476 0.83334205408502 -1.19765932451246
C -0.14521143795907 1.98911871291802 -1.85081452410049
C 0.90536379123799 2.71058379364758 -1.39906254082392
C 1.58408094568987 2.37010491608187 -0.06920176641975
H -0.37904091948590 -1.23185135371767 -0.51626082846188
H 1.99892632753895 -1.10204567043323 -0.27821618008179
H 3.28000417109037 0.90469693310601 -0.01682125987702
H -1.88131559443038 0.24532937781470 0.63276700046412
H 0.87314440474933 3.25170948256059 1.86317305156500
H -1.62614411642712 0.41610332249823 -1.76123831507160
H -0.59514494004898 2.26764123298043 -2.80991121756943
H 2.40448845749440 3.08234576885527 0.09738224928948

S90
C -1.37299633991495 2.00816735287648 2.45342240916095
O -1.37709499636577 0.83924065190465 3.30123944702570
H -2.42708693071858 2.13888252029695 2.16499216998790
H -1.03719822160953 2.87951011437061 3.03091249001974
C -0.35907274075678 0.72808087815916 4.18289725576527
O 0.46852530053034 1.58577622955011 4.36337239201586
C -0.40447576891637 -0.60578053597896 4.88568180836764
H 0.29791440402816 -0.60312786613707 5.72796938152643
H -0.11890589630274 -1.39629005892148 4.17283672016326
H -1.42526033596221 -0.82717905361953 5.23011107711900
Si 1.59829878685659 4.16694302005642 -2.36604087509802
C 1.47116679043184 5.71849191585821 -1.29260045477688
H 1.91578393591780 6.59084374215946 -1.80053449691750
H 1.99804855307350 5.58726462664331 -0.33299423626370
H 0.41809905331645 5.95356694262151 -1.06689791232967
C 0.64454172784562 4.42161969874745 -3.97375990842072
H 1.05919206871172 5.27722181355458 -4.53228742811972
H -0.42067884803099 4.63121871123348 -3.78288354450096
H 0.70707752761958 3.53453804512201 -4.62506443057306
C 3.41919926951620 3.82904478928295 -2.74735556349378
H 3.88049403250385 4.68301392943644 -3.27137701120519
H 3.52716996755657 2.93649626506554 -3.38515660471515
H 3.99636805241373 3.65318694992427 -1.82453269905798

Compound 9, isomer 000 001 200 0

C 0.28640153316913 0.05151659375085 0.15641332999824
C 1.70427450229725 -0.08985115188110 -0.22629532913263
C 2.58082444078084 0.91528602381044 -0.38224674710115
C -0.57986092880999 1.22251647710229 -0.31566249445712
C -0.05939326289527 2.30471197291182 -1.17096758612266
C 1.17651996659398 2.85290084212251 -1.15535660393280
C -0.21456333941537 1.08329511168666 1.17362093914376
C 0.70512394175672 2.04727071129733 1.82023267409154
C 1.77915568529392 2.62756143186875 1.26253684232040
C 2.23782930165876 2.37510810473724 -0.15931903354234
H -0.25412650723883 -0.89820576654989 0.19861063297503
H 2.04390779310213 -1.11393421411223 -0.41039614335004
H 3.60464392478285 0.67849020259901 -0.68848614527206
H -1.61758384122660 0.95497963505146 -0.52127087733854
H -0.78871201593475 2.68414171153656 -1.89461612260406
H 0.44692258648337 2.31328415407665 2.84998627125288
H 2.36063965785006 3.33542974882296 1.86175223711870
H 3.15695473253300 2.95706207802942 -0.31829509625696
Si 1.66102223164627 4.23628003480925 -2.33231217934623
C 2.16065289626909 5.74929824754826 -1.31304181356099
H 2.50161469872705 6.57227162706688 -1.96357206401648
H 1.31077328916397 6.11556805679709 -0.71412141218750
H 2.98267292662766 5.51179323515848 -0.61756369941190
C 3.14640627041604 3.66791223439338 -3.35556601264870
H 3.49675251363645 4.46938701728544 -4.02754937957467
H 3.99246997634697 3.38123684501656 -2.70918757147799
H 2.88510010457002 2.79280821002565 -3.97281651559995
C 0.22789841126123 4.68064784834380 -3.47531773743858
H 0.52370027664401 5.49074629123316 -4.16247027463503
H -0.08194017960487 3.81803380191011 -4.08756367561935
H -0.65005576615013 5.02765284200767 -2.90631225358998
C -1.32068997642338 0.58665609088162 2.08005282439354

S91
 O -2.11532942888145 1.67188338548767 2.58848430615579
H -1.97197119611691 -0.12561967647153 1.55522147609335
H -0.89516054213796 0.10482656362968 2.97305685177412
C -3.20433293213830 2.04181170303250 1.88256743900712
O -3.58343688064681 1.48016045230250 0.88385094427968
C -3.86432871698061 3.24219096338054 2.51146457597662
H -4.81452203367680 3.44978384730146 2.00512134666898
H -4.02673628892398 3.07010783111424 3.58583847488728
H -3.19492544353962 4.11224022175255 2.41752825706944

Compound 9, isomer 000 002 010 0

C 0.04590413116959 -0.25311407794876 0.08349481179102
C 1.51510418424901 -0.37510226961234 0.00184869524256
C 2.38232593308689 0.64756164622263 -0.00664928615147
C -0.72561773975958 0.86012840737975 -0.62084156727938
C -0.09471771170901 1.96682060770500 -1.35340129005291
C 1.08896609517287 2.54541521639582 -1.07521193331365
C -0.66096928118906 0.80997144064195 0.92170604484838
C 0.03173831146858 1.85028583590262 1.72151815966328
C 1.21352840017242 2.40533052179131 1.36955404264798
C 1.96908073080311 2.10086083104558 0.08885254644810
H -0.47624764731317 -1.21343496872887 0.07315641007684
H 1.90448537647557 -1.39602497426508 -0.06348034193745
H 3.45317053056975 0.43287709524603 -0.07592307133269
H -1.68754751058614 0.54664170940107 -1.03364247765274
H -0.70264709044193 2.40981670432499 -2.14800159782934
H -1.59150729887846 0.44625723682363 1.36707693382106
H 1.64356087260286 3.18774507871328 2.00337172737417
H 2.87765738897437 2.71771311440636 0.07877627444737
C 1.50914525029172 3.79623942743187 -1.78997555740765
O 1.63992594404026 4.88776310053247 -0.84803368623673
H 2.51541168389976 3.70603329006229 -2.22655265709841
H 0.78867887098618 4.06836249105091 -2.57455183278006
C 0.49666589531559 5.43224332106932 -0.37890771521099
O -0.60086161510191 5.15479351289001 -0.79507188403152
C 0.78261122314956 6.39585624665994 0.74485007097477
H -0.07643334200412 7.06291463297632 0.88799213729302
H 0.93875179965390 5.81309133737033 1.66733550144008
H 1.69986070670885 6.96948784769475 0.55276705451015
Si -0.94303577939678 2.56603376026331 3.17050966426891
C -1.53852940804236 1.18321209879316 4.31287413010522
H -2.14906523654324 1.59009943176007 5.13643467082345
H -2.15804990666429 0.44827446942528 3.77323066030759
H -0.68577547841219 0.64306329259453 4.75632103967511
C 0.12122336675613 3.77265204223433 4.15835594768046
H -0.44706339589408 4.15400268753642 5.02291191414047
H 1.03441696493055 3.28903585047375 4.54166291194986
H 0.42365697937661 4.64255408805174 3.55371957968586
C -2.42287870872229 3.47538764242734 2.42696953389972
H -3.00612659072909 4.00603973805969 3.19816662506159
H -2.08241036388982 4.20733828902965 1.67561902676830
H -3.10181543338886 2.77304530697018 1.91558370458055

S92
Compound 9, isomer 000 002 100 0
C -0.24491315887924 -0.11471227147572 -0.36106048042079
C 1.17031629721325 -0.49124963341834 -0.54015141367401
C 2.22854712008577 0.32914134006997 -0.43704426085231
C -0.79833234972291 1.23759484632912 -0.78733747300726
C 0.02286753378986 2.29906720323636 -1.39176341343558
C 1.31454671707949 2.57073467695317 -1.12775060390411
C -0.72772983948291 0.88049908755672 0.71817974353755
C 0.25187393173080 1.56586021208001 1.59822449875451
C 1.49150806542876 1.97781751388987 1.28082159943407
C 2.11735375405163 1.79968921749815 -0.08769926340160
H -0.93473918036035 -0.94377962055194 -0.54004600363420
H 1.34884913068698 -1.54389362121694 -0.78192204795829
H 3.23116274109642 -0.07992116129508 -0.59578611061028
H -1.80572792297657 1.18736976842014 -1.20845071917470
H -0.49668813582074 2.94503961910299 -2.10604399964045
H -0.08275569062295 1.75736752563269 2.62415256415215
H 2.09330254157059 2.47424332714476 2.04886123986607
H 3.12793667100389 2.22809684741181 -0.05630833041013
C 2.00304595248410 3.73135943019175 -1.78252975225516
O 2.37904779490307 4.71071873350906 -0.78736266036404
H 2.95820383484724 3.42967351908508 -2.23882519827886
H 1.36271249092405 4.20269608836908 -2.54053663399569
C 1.41288126653534 5.56951709991221 -0.39270477973789
O 0.33017731816311 5.64737508327438 -0.91662246834290
C 1.87160591509233 6.38225083378881 0.79179062780161
H 1.20373021782506 7.24086257136895 0.93284249938611
H 1.83412692465617 5.74311724946060 1.68940630220967
H 2.91250988609999 6.71148436918871 0.66225458428940
Si -2.37331536408505 0.49576858894367 1.57461478629812
C -3.13718432753750 2.12260196243208 2.14778028919619
H -4.10026527181102 1.95414536563195 2.65792611444544
H -2.47376566387797 2.65504270022257 2.84828134282767
H -3.31802138710765 2.78957459481169 1.28874348402359
C -3.56601962856808 -0.37169185750005 0.39438030640030
H -4.51136530701789 -0.58176865502500 0.92216687809915
H -3.81156221752170 0.24855715300448 -0.48282331534259
H -3.17101586461969 -1.33523855143430 0.03360424967576
C -2.03210114846532 -0.63122148663103 3.04958750580261
H -2.96189692173862 -0.86743601169414 3.59356298088495
H -1.58191058928749 -1.58125914559603 2.71725354689919
H -1.33482813858681 -0.16285603632262 3.76291580427844

Compound 9, isomer 000 020 010 0

C 0.23815050202369 0.06151104535068 -0.04736112942563
C 1.70804388811960 0.18821004391700 -0.02917381090335
C 2.39392207044911 1.33981247619868 0.03868200067465
C -0.68438738907337 0.97565248010431 0.75784817918804

S93
C -0.20106719119965 2.08754991479750 1.60753559842190
C 0.86245452593808 2.86372459359306 1.32930838901570
C -0.67307546169003 1.05656631271824 -0.77293895044638
C -0.18039845913167 2.24291422249537 -1.51635754416775
C 0.89468350398320 2.97063377649500 -1.13912548738399
C 1.73442691469289 2.70426508449147 0.09886936339513
H -0.11455267152545 -0.97164639084598 -0.10247746881578
H 2.26573528505007 -0.75261155828100 -0.07535810002157
H 3.48770750545707 1.30615455235171 0.04583636339352
H -1.56706828932957 0.47341397697563 1.16170265127534
H 1.08296338718209 3.69931885886717 1.99994124983712
H -1.54449460779507 0.57401252443666 -1.22571493987981
H 1.18144936139830 3.84296404387193 -1.73514646312332
H 2.52571979905366 3.46445840607827 0.14377194765776
C -1.04639878347092 2.37490638546852 2.82020229884677
O -2.40627763083704 2.67318929939920 2.43862502931409
H -0.63137216837777 3.21112940186943 3.39930477210840
H -1.13888243234164 1.48831420413504 3.46603436422271
C -2.64948007568764 3.92092171589560 1.97946000810303
O -1.83014672337810 4.80494563367933 1.97717012735370
C -4.06146323047646 4.03455715906558 1.46191231277843
H -4.32789537952736 5.09247622663705 1.34760671540460
H -4.76680167620270 3.52286031270742 2.13208723008342
H -4.11744329573741 3.54137626091701 0.47812942808704
Si -1.21800291587063 2.77650745199869 -2.99827495131672
C -1.37661792995202 1.33924642955720 -4.21566345133074
H -2.01900692210584 1.61457021381670 -5.06898846377470
H -1.81937133910130 0.44957867180264 -3.73853434148739
H -0.38906246805536 1.05063101362388 -4.61175628504061
C -0.43963578082303 4.25995279132293 -3.86313972500127
H -1.05179628842887 4.55671583068920 -4.73097973818407
H 0.57336750236906 4.02784497054982 -4.23035615186072
H -0.36912498876041 5.12971306036642 -3.19005013836512
C -2.93507704263864 3.24473421580307 -2.35548908501300
H -3.60778975207138 3.54342880599510 -3.17677437500361
H -2.85900533392268 4.08787897795468 -1.64929232186856
H -3.40555751236996 2.39952966580580 -1.82613918516042

Compound 9, isomer 000 010 200 0

C 0.17279833174011 -0.12121594252554 0.06228149641557
C 1.54615337330655 -0.47591304332120 -0.34317393496116
C 2.53855593863931 0.38946152156844 -0.60597810454995
C -0.56171825614696 1.11080446864701 -0.46862719986109
C 0.02316793746257 2.05996520701428 -1.44915033401234
C 1.33003774377750 2.40285187443212 -1.47373735708332
C -0.14975397815185 1.04408318850598 1.01147180236373
C 0.91699003660843 1.91946226421448 1.54944882630651
C 2.03351214817589 2.30785111800585 0.91413608246021
C 2.38356504580745 1.89596299109061 -0.50346314325524
H -0.47856833620564 -0.98825361642232 0.20319760021161
H 1.74698013279863 -1.54741024133273 -0.44168258129366
H 3.51512837108916 -0.00125487734672 -0.90828271559844
H -1.63253932030016 0.93885583980942 -0.59572373941949
H 1.67941161625192 3.10723770873699 -2.23563984668094
H 0.74591988581628 2.28504344046807 2.56693472422484
H 2.73475234919915 2.96384978188099 1.43936738863611

S94
 H 3.34388873081765 2.35852038626091 -0.76888638538944
Si -1.18339871957628 2.80242046627476 -2.70045806820627
C -2.45830488165034 3.85566570309411 -1.78715049994040
H -3.15190850521086 4.33345121957163 -2.49966995974023
H -3.05425311755808 3.24319648818489 -1.09253623442339
H -1.96190963522273 4.65384053533848 -1.20993033455250
C -0.25446024698246 3.87204651793166 -3.94795161095449
H -0.96137279543526 4.28928071564497 -4.68438025015296
H 0.25522552246472 4.71851636542045 -3.45927600842499
H 0.50138235313312 3.29017947945729 -4.50022307256825
C -2.07074682982715 1.39900138345081 -3.60243007207665
H -2.79761974806548 1.79734865900661 -4.33013134993252
H -1.35366384402149 0.76359699783579 -4.14784174367303
H -2.62391206606019 0.75788297839384 -2.89686253559371
C -1.26691002521632 0.76895645027024 1.99442242706140
O -1.91897122827161 1.98901636001501 2.39540957759845
H -2.01258592557773 0.08371108682850 1.56956552087672
H -0.86553442557066 0.34263654169176 2.92573080529647
C -2.99284116696721 2.38936333137885 1.68911855061158
O -3.49057025353417 1.74439583192393 0.79544903557341
C -3.46081323125785 3.75064274262553 2.13134018929359
H -4.51578788841044 3.88400507840446 1.86116498029614
H -3.30492138978730 3.89716556370397 3.20863568066897
H -2.86417036307584 4.50683295299909 1.59452251363980

Compound 9, isomer 000 020 100 0

C 0.17530483333317 0.17133720513623 0.43065792910459
C 1.61547628595427 0.43572171681405 0.60170909261304
C 2.24124214347864 1.60026493867822 0.36494253853733
C -0.66627227652637 0.80941651850537 -0.65809283666483
C -0.14926078987423 1.77139178973052 -1.65745608025675
C 0.83009050426211 2.66783733115393 -1.42784785075670
C -0.93027211926739 1.18881359533670 0.81605711339179
C -0.54871793521812 2.52802504864796 1.32496676136540
C 0.50456585169888 3.27838119122546 0.95495338940504
C 1.51944919090315 2.85398610904443 -0.09056533790403
H -0.09495861546490 -0.86950586420043 0.62931867325957
H 2.21064292259652 -0.41349698183547 0.95256017767660
H 3.32117849620245 1.66646439475870 0.52890566281859
H -1.42141080376665 0.14408446834673 -1.07539887802063
H 1.12067667698410 3.34198738615845 -2.24067355163280
H -1.20409553530760 2.94764413398722 2.09688783484702
H 0.64964369847004 4.25213373593796 1.43346963041773
H 2.26017326873268 3.65765885399451 -0.19920844197518
C -0.84697887268094 1.77146552175318 -2.99418472338153
O -2.05032679084744 2.58179604162866 -2.96280684564519
H -0.22063791648865 2.24606582887500 -3.76021967660772
H -1.11873063013103 0.75486800184032 -3.31445470397633
C -3.20112430749228 2.01707533337814 -2.56754309081218
O -3.32134835315472 0.85016168401261 -2.26939370759384
C -4.31000133997344 3.03738686452788 -2.51119239448018
H -5.27915540714672 2.52689112703865 -2.45472832606619
H -4.17302321555232 3.65197446814128 -1.60645810681912
H -4.26963096233818 3.71070487282605 -3.37896630639383
Si -2.51743650948875 0.48719242400993 1.58041369739172
C -3.91675177470734 1.72735149167060 1.31773588860100

S95
 H -4.83196596232636 1.40387884639806 1.84117497722109
H -3.65784961104193 2.73435580161375 1.68230817246528
H -4.14956830465023 1.79460524456254 0.24343210611197
C -2.99963839464442 -1.13649304108660 0.75226155469692
H -3.87237010797155 -1.56792960196642 1.27062375662500
H -3.28486220695121 -0.96331846914887 -0.29765044708118
H -2.19542060729609 -1.88951102582638 0.78052915765274
C -2.20990257080786 0.22092688996162 3.42440337175339
H -3.11144297056212 -0.16457983875621 3.92925139723267
H -1.39522543094128 -0.50513399643848 3.58229609065935
H -1.92014407845947 1.16046364362148 3.92282925188638

Compound 9, isomer 000 100 200 0

C 0.18136845224062 0.16739388707031 -0.03539598977320
C 1.65509743081428 0.15817380606090 -0.11037941676559
C 2.45301913963013 1.22053143219636 -0.30256744908529
C -0.71997796890382 1.05223126969341 -0.92413584356303
C -0.11853287420162 2.06475763534937 -1.83411970025916
C 1.02748131740974 2.74946560798334 -1.67845457634955
C -0.63008872896976 1.28336950788097 0.61857457534058
C 0.03967007731416 2.47851726523469 1.18882677923715
C 1.15987207926237 3.07947421644268 0.75840154280418
C 1.93107274165323 2.63453241872877 -0.46778829734618
H -0.23709911930537 -0.82137593219790 0.15789012873630
H 2.11803424284920 -0.82793155674801 -0.00170834538564
H 3.53633539551447 1.06987148620260 -0.34243815847314
H -0.68355099343851 2.27391644427334 -2.74678860675149
H 1.31679673105132 3.46084025926854 -2.45868258449817
H -0.44590729491156 2.88926500309025 2.07964919676553
H 1.52763411173962 3.95416414217161 1.30398851482637
H 2.78789190014840 3.30771170439804 -0.60647564687279
Si -2.23675812947715 0.19043324811106 -1.71424423578613
C -1.96883881339635 0.11356970916311 -3.58512621552606
H -2.72675920772375 -0.55008679229018 -4.03432077992945
H -2.06066385901886 1.09711678648350 -4.07222581662529
H -0.97472889321715 -0.29527442416624 -3.82940347794122
C -2.43504451569538 -1.59588882064277 -1.13491104361483
H -3.36525471030150 -2.00862028664361 -1.56097731968993
H -1.59926807551178 -2.20533745398855 -1.51794603555534
H -2.46556089935023 -1.73672575769014 -0.04466590422875
C -3.80314163466921 1.19629099780281 -1.38367600856682
H -4.64370659621893 0.80834444761827 -1.98332484268824
H -4.10759215573196 1.17107927899163 -0.32597230467598
H -3.64916102968828 2.25161895065035 -1.66418324156253
C -1.81715016861414 0.85807798655126 1.45938531832066
O -1.39564275742782 0.50652204941482 2.79138034873632
H -2.51320284701174 1.69899021987143 1.59057050982400
H -2.35316299256656 0.00951434703249 1.02553665373449
C -1.16414167029124 -0.79310787184403 3.05697003173305
O -1.35746088256719 -1.68958651433877 2.26999978531015
C -0.63417565874242 -0.96656619191631 4.45710812216271
H -0.53847424391562 -2.03416512664100 4.68782736155318
H 0.34861165416045 -0.47538234819534 4.53565158793582
H -1.30284640887615 -0.47414007421862 5.17907751180861

S96
6. References

(1) Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512–7515.
(2) Patel, H. D.; Tran, T.-H.; Sumby, C. J.; Pašteka, L. F.; Fallon, T. J. Am. Chem. Soc. 2020, 142, 3680–3685.
(3) Yahiaoui, O.; Pašteka, L. F.; Blake, C. J.; Newton, C. G.; Fallon, T. Org. Lett. 2019, 21, 9574–9578.
(4) Yahiaoui, O.; Pašteka, L. F.; Judeel, B.; Fallon, T. Angew. Chem. Int. Ed. 2018, 57, 2570–2574.
(5) H. Wu, B. Yang, L. Zhu, R. Lu, G. Li, and H. Lu, Org. Lett. 2016, 18, 5804-5807.
(6) Sarma, K.; Witt, W.; Schröder, G. Chem. Ber. 1983, 116, 3800–3812.
(7) Neese, F. WIREs Comput. Mol. Sci. 2012, 2, 73.
(8) Sure, R.; Grimme S. Comp. Chem. 2013, 34, 1672.
(9) a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648; Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785, b)
Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comp. Chem. 2011, 32, 1456.
(10) Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297.
(11) Rappoport, D.; Furche, F. J. Chem. Phys. 2010, 133, 134105.
(12) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995; Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J.
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