68 (1) 1999

3
548.31

.., ..
. ..
117813 , ., 28, (095)135 5085

. ,

,
, ..
.
122 .

I.
II.
III.
IV.
V.
VI.
VII.
VIII.
IX.

--


?

I.

() ,
( , ,
)
, , - ,
, / .
,
(
C7C C7H).
,

... ,

. : (095)135 9343.
: ,
, .
... - , , , .
: (095)135 9215, e-mail: mishan@xray.ineos.ac.ru
: , .
23 1998 .

3
5
6
8
11
13
17
19
20

(,
.).
, .

.
181000 ;
7000 8000 .
,
,
.
.


.


(,
, ).
, .
.1 4

, . .



.
. ,
- , 5 6

( ,
).
( ),
,7
. 1970-
1980- . ,

,
. (, , )
, .
, (),
, . ,
16 .
1955 . 7.
, , .9, 10
.11, 12

.


(. 13, 14)
.
,
. ( )

.
,
,
, 1960- .


.

, , . ,
,
.
, , .

:

.., ..

181 000 , 41 500 ,

11 000 ,
} 1500 .
.15
.
,
()
16, 17 .18 20

. ,

--

,21, 22
( ,23 27
_(N), Hal_Hal 28 33).
, ,
,
, ,
.
34,

.

.35
,
, ,

c .

.
,36 44
42,
45.
,
.
, ,
- -.46, 47
, ,

(, 48), ,
() . ,

,49
, , .50
,
, ,
Cambridge Structural Database, University of Cambridge, UK.
Inorganic Crystal Sructure Database, University of Bonn, FRG.
Metals Data File, National Research Council of Canada, Ottawa,
Canada.
} Protein Data Bank, Brookhaven National Laboratories, USA.

 68 (1) 1999

.3
,
,
(Z 0 ).45
.51, 52
Z 0 > 1 . , ?
- ? ?
? Z 0 > 1
- ?
.53 ,
.
,54
.55
, , , Z 0 > 1. 56
Z 0 > 1
, .57 59


( ),
,
.60 62
,
, , . , , : , , ,
. ,

,
.
, ,
63. ,
( , , ), ( )
/ - .
,
. ,

. ,
, -

.

,
.

.

II.

,

, , .
,
1025 (
1998 .).
,
. , 40

1998 .
150 . 64
:


.

.

, , ,
, .
QUEST,
.
1D, 2D, 3D.
QUEST1D
, ,
, R-, ( , ..).
QUEST2D
,
, ,
.
QUEST3D , ..
, ,
, , 2D-.

(BILD, SEARCH QUEST),


BITSCREEN.
QUEST3D
FDAT,
GSTAT(VISTA) () PLUTO.
GSTAT 65
- . GSTAT
, -

.66 VISTA ( GSTAT) ,

, .
PLUTO , .

, , .

.
.
,
. R-,
, AS-,
. QUEST ( ), GSTAT (
).

(., ,67 69). ,
, . ,
(, ,
). ( ),
.
,
.
, . ,
,69 ,
AS. , AS,
1.2, , ,
. GSTAT

.
, , . ,
( , ).

/
. ,
. .70
, (, ) ,
.

III. --



,
.7 - () . ,
, -

.., ..

( )
, , .
71, 72, ,
, , .73
.

- ,
, , . ,
7 .
1 4
X_Y
.
: ,5 ,7 ,6 ,74 ,75 .76 () 6 , 71, 74, 77.
.74
,22
,23 26, 78
, , N, O, F, P, S, Cl, Br, I
,
30 . 1995 .,
126 353 .
(R- < 5%) , , .
,
, . 28403 , . A
B , (RA + RB)  1.5 
A, RA RB .
,

.

22 0.1 
A.
:
(n)
(_); (Cl_Cl);
(H_F) ,
, ,
(C_N) (. 1).
,
.
, 22 d,
, -

,
( , _),
--
(7) . .
, 22 -- _.

 68 (1) 1999
n . 1075

7
n . 1073

1.0
0.5
0

2.0

3.0

n . 1073

3.9

1.0

1.0

0.5

0.5

n . 1074

n . 1074

5
d

2.2

3.0

4.0 4.5

2.2

3.0

4.0 4.5

1.5

0
3.0

2.5

3.0

1.0

5.0

n . 1073

2.0

, 
A

1.0

0.5

n . 1073

4.0

0
2.4

4.7

, 
A
. 1. :22
H_H (a), Cl_Cl (b), H_F (c), C_N (d ).

(. 2).
. , (
)

. d
,
.
_, N_O,
N_N , (. 3). 22
-- , NH OH- ;
, H-,
.
, d (. 1)
(,N)H_N(O) , (C)H_O(N) (. 4); (O,N)H_Cl(Br), ,
d , ()_l(Br).
, OH- NH-
n
nk

3.0

. 3. O_O (a),
O_N (b), N_N (c).22

4.0 4.6

, 
A

, ,
. , (
H- NH-) .
, d _, _N, H_S 22 .
d - (. . 1) (ri),
i- ,

XX
i

j<i

wij dij ri rj 2 ,

dij d i, j; wij
(wij = 1 0.1 
A wij = 0.25 0.2 
A);
.
, d 22
,
- , d
. ,
ri (Rw):
ri = cRwi , . ,
c .
1. d (
A).22

nk/2

, 
A

. 2. d.22
nk .
, , , ,
.

H
C
N
O
F
S
Cl
Br
I

3.02
2.59

3.02
3.59
3.31
3.24

2.59
3.31
3.43
3.28
3.13
3.42
3.41

2.54
2.91
2.88
2.99
3.14

3.61

O
3.24
3.28
3.00
3.45
3.33
3.48

Cl

Br

2.54

2.91
3.61
3.42
3.45

2.88

2.99 3.14

3.41
3.33

3.48

3.60
3.55

3.55
3.50

3.13
3.00
2.90

3.70
4.05

.., ..
n . 1073
6

n . 1073
4

2
2

n . 1073

n . 1074

4
d

3
2

1
0

, 
A

. 4.
(O,N)H_O (a), (C)H_O (b), (O,N)H_N (c), (C)H_N (d ).22

ri , ,
,
. 2. , ri . 22 , , ,
. ,
,
, . ,
0.1 
A.
_,
,
, 1.19 
A.
, .
_ _N
. , , _ . ,
, , _ . , _
- . 22 , ,
_ ,
2. -- (
A).

II

III

IV

VI

VII

H
C
N
O
F
S
Cl
Br
I

1.2
7
1.5
1.40
1.35
1.85
1.80
1.95
2.12

1.17
1.72
1.57
1.36
7
2.02
1.78
7
7

1.16
1.71
1.50
1.29
7
1.84
1.90
7
7

7
7
1.60
1.54
1.38
2.03
1.78
1.84
2.13

1.2
1.7
1.6
1.5
1.4
1.85
1.8
1.9
2.1

1.2
1.7
1.55
1.52
1.47
1.80
1.75
1.85
1.98

1.10
1.77
1.64
1.58
1.46
1.81
1.76
1.87
2.03

. RW : I ,5 II ,7 III ,74 IV
,75 V ,76 VI ,6 VII ri ,
.22

, . . rN d
N_N. 22 , N_N .
, ,
,
*0.1 
A.
( ) .76

, .
, ,

. ,
( 0.2 
A), ( 71008C )
.

IV.



1955 .7 ,
, , ,
, ,
5 . 71.
c .1 4
,


, .35

,
.
4 ,

? , .
63.

/
.
.

.
34
, -
.
.
1996 . (160 000 )
82% : 1
(19%), 21 (6%), 21/c (35%), 2/c (7%), 212121 (9%), bca

 68 (1) 1999

(4%), nma (2%).

QUEST ,
,
(Z 0 = 1),
.
Pnma,
, m, Z 0 = 1/2.

,
( ,
).
, .
PLUTO CSD,
VISTA.


, .
.

1. 1

1 967 , . . 5.
(.. ,
)
(. 5,b) ,
, x = 0.25, y = 0.25, z = 0.25. ,
y

0.75

0.75

0.75

0.25

0.25

0.25

0.25

0.75

0.25

0.75

0.25

0.75

0.50

0.50

2. 21
21 1000 .
,
. ,

(x, z) = (0.25, 0.25) (. 6). (x, z) = (0, 0),
(1.0, 0.5), (0.5, 0), (0.5, 0.5), .. ,
.
( ).

0.50

0.25

0.25

0.50

0.25

0.25

0.50

0.25

0.50

0.25
0

0.25

400

b
0.50

: (x, y) = (0.25, 0.25)
(x, y) = (x, z) = (y, z) = (0, 0), (0, 0.5),
(0.5, 0), (0.5, 0.5).
, .. .
,34

.
,
, ,
. ,
, , ,

, d
. , .
,
, , (, ). ,
, ,
.

180
120

200
0.25
z

0.50

60
0.25 0.50
z

0.25 0.50
x

. 6. (a) P21 (b).34

N
360

240

400

400

3. 21/cc

120

200

200

21/c Z 0 > 1
994 . (. 7)
x.
y (0.125, 0.375, 0.5) z (0.125, 0.25, 0.375)
.

= 0.25,
.
(x, z) :
(0, 0), (0, 0.5), (0.5, 0), (0.5, 0.5).

0.25
x

0.50

0.25
y

0.50

0.25
z

0.50

. 5. 1.34
a ; b , ; c

. N
.

10

.., ..

0.50

0.50

0.25

0.25

0.25

0.25

0.50

5. 212121

0.50

0.25

0.50

0.25

600

180

400

120

200

60

0.25
x

0.50

0.50

6. Pbca

N
180
120
60

0.25
y

0.50

0.25
z

0.50

. 7. (a)
P21/ (b).34

4. 2/c
2/c 984 . x = 0.125, 0.375 (. 8).
,
y = 0.25. z 0.125, 0.375,
x. xy (x = 0.125
0.375).

(x, z) = (0, 0.25) (0.5, 0.25), .
, , , ,
.
,
.

0.50

0.50

0.25
0

a
0.50

0.25
x

0.50

N
400

180

300
200
100
0

120

0.25
y

0.50

0.50

0.25
z

0.50

0.25
z

0.50

N
250
120

60
0.25
x

0.25

0.25

0.25
y

0.50

212121 999 .
.
, z.

. 8. (a)
C2/c (b).34

Pbca (999 ) 0.125 0.375.

(0.125, 0.375)
.
. ,

1 212121.

7. Pnma
Pnma
731 .

,
(x, z).
(0.25, 0) (0.25, 0.5), .
(0, 0),
(0.5, 0), (0.5, 0.5), .
,
,
.
,
, *45%
,
. ,
21/c

(126 ),
.

PLUTO
, 7 .79

. , 74.18 . 71.
12 14,
.7 -
;79
.
,
, ,

. ,
. , .

,
.
,
,

 68 (1) 1999

.
.
.
.

V.




.

, , . ,
.
7 , 230


; ,
. . . ,
,
(),
( ).

P21/c 1.
40,
51,
52,
80

9, 10 .

: P21/c, 1, P1, P21 , P212121, Pbca,

C2/c, Pna21, Pnma. 79.2%
. ,

: 50%

P21/c 1. ,
.

,
(,36 39 .,41
.,42, 81 .,44, 82 45),
(,43 .,44, 82
83).

,

66 75%.
( ,
1992 .) 78%.
, ;
.41
, ( ) -

11

. , , -
,
, .
, , .

,

.
, , :
,
. ,
, . ,
() .
52
.
, , 230
, 7
28
.83 .
, , ;7, 80
.
, 18 ( 83) 92.71%
; 42 ,
89.8% . ,
(. 3, 4), (. 9).
3. .42

n, %

1
2
3
4
5
6
7
8
9

P21/c
P212121

1
P21
C2/c
Pbca
Pna21
Pnma
Pca21

7634
3052
2658
1684
1149
998
414
257
199

37.97
15.18
13.22
8.38
5.71
4.96
2.06
1.28
1.00

. : ; m ; n
.

18
,
56.86% .
,
, .
, .

12

.., ..
a

4. .42

n, %

2823
11061
5563
360
268
32

14.04
55.01
27.67
1.79
1.33
0.16

. : m
; n
.

, (. . 9),
, .

,
.


, , . , , 3m,
4/mmm, 6/mmm, m3m, 31.58%
.
0.63%.
,45
(13% 16% ),
(3
2% ). 2 2221
13 5%, (
) 4 1%. (95.38%) ,
a
0
P21/c
P212121
P21
Pna21
P1
Cc
Pca21
P21212
P2/c
Pc
Fdd 2
I41/a

P1
C2/c
Pbca
Pnma
Pbcn
C2
P21/m
C2/m

R3
Pccn
P41212
C2221

10

15

20

25 30

35 n, %

b
0

Pnma

Fm3m
C2/c
C2/m

Fd3m
Cmcm

Pm3m
P6/mmm
P21/m
P63/m
Pna2
1
F43m

10 n, %

P21/c

P1
P63/mmc
I4/mmm

R3
m
P3m1
R3
Pbca

R3c
P212121
P4/nmm
I4/mcm

. 9.
() (b) ( ).83

10

20

30 40

50

0 10 20 30 n, %

1
2
2/m m
222 mm2
mmm
4

4/m 4
4mm 422
42m
4/mm

3
3
32
3m
3m
6

6/m 6
6mm 622
6m2
6/mmm
23

m3
432
4m
m3m

. 10. (a)
(b).83

(. 10).

48.92% . , : 18
(. . 10).

, ,
.
, .

,
. , , ,
. .


, .
,
,38, 39, 45, 84
. 45
7 ,
(2)
(m). ,7 ,
m, , m:
m
. , -

 68 (1) 1999

13

, (
Pnma ).
2 , ,
( )
, 2 .
, 2, ,
. , , 2,
, .41

, 45

. , , 21
, . ,7
21 ,
, .
,

, . ,
, ,
, . ,
, .
,
,
(Z 0 )
( ).
Z 0 ,51, 80 .
.
.41 , Z 0 > 1
, 1. , 1991 .,45 ,
, Z 0 > 1 ,
:

nZ 0 > 1 , %

P1
45.0

P21
14.0

C2
11.2

P212121
4.5

1
11.3

P21/c C2/c Pbca

5.7
3.0
3.0

,
Z 0 > 1 . , 55 P21 256
Z 0 = 2 P21/c.

1, 2, 21 , t.
.

VI.

?
1.

,
, , .49 ,
,46, 47

.



, , ,
.
( - )
.7 ,85, 86 ,
C=O N:C, , -
.
, 49 ,
,

,
.
(
1994 .) ,
: 1, 1 P21 .
. 11
. 1 - t,
,
. 1 . P21


( y ).
(m) ,
AM1.87
a

c
y

. 11.
1 (a), 1 (b), P21 (c).

,
m.

: 1) d- ; 2) ;
3) , ; 4) ,
; 5) ,
(.. , NH).

28 1, 161 ( 1229) 1 179 (

722) P21 .

14

.., ..

5.
.49

m,

m,

P1

P1
P21

28
161
179

3.41
3.33
3.14

0.37
0.15
0.15

3.36
3.22
3.04

. : n
, s m; m
.

, 49, . 5
(. 12). ,
.

P21 . ,

. ,
,
, ,
. -,
;
, .
, ,
.
,
, .
a

n (m)

40

5
0

n (m)
20

m,

c
40
20
0

?
, , .
, 89 12
4 .
(
*0.15%) . ,90 14
9 .
,
.
.50 (
1989 .). :
(*25%
), (*75%
).
.
, , .
, ,

.
. ,
, . (Dr)
(Dh)
DD

100Dr Dh
.
0:5Dr Dh

129 . (
), DD, (. 13).
, .
DD 129 0.56%,
,
, .
DD,
.
,
; -

m,

. 12.

1 (a), 1 (b), P21 (c).49

n (DD)
24
8

2.

,
, .88
, .
, , ,
, 1895 .88
:89
, -

0
24
8
0

710

75

+5

+10 DD, %

. 13. DD 129 (
).50

 68 (1) 1999

15

n (DD)

n (DD)

12
0
12
0
710 75

+5

DD, %

710 75

+5

DD, %

. 14. DD 64 ( , ) (a) 65
( ) (b).50

, .

:91
,
. ' ( )
, ,
.
(, ) .
64 DD
*+0.20% (. 14,). , .
DD ,
65 , +0.92% (. 14,b).
*1% , ' .
, 50 ,
, , ,
.
,
DD
.

,

, .


. ,
:
1 . 71. , ,
.
.
, ,

. ,
, . , ,
, . , . ,
,
, .
DD.

.89 36 , .
, DH, DS T,
7.54 . 71, 18.5 . 71 . 71
405 K 6.28 . 71,
15.7 . 71 . 71 395 K .
,
, .

, ( )
. , , ' ,
, ,
.
,

.

3.


.
, ,
,
..4, 92 98 ,

.

() .

, .
,
' ( ..),


,
.

,3
1993 .
, C, H, N, O, Cl, S,

.
163 , ; 147
, 13 3 , 345
.
,
3, 86, 99, 100.
6-exp ,98, 100 .
(- ,
), ,
,
. ,
, .

16

.., ..

,
DD ; (%) (P)

40

40

20

20

DE, %

n (DS)

160

20

80

8 DS, . K71 . 71

16 DD, %

n (DZ 0 )

40

n (DD)
60

10

715
730

60

20

710

204.
: D , V ,
K ,
E , S ,
G , Z 0
.
. 15
DD, DE, DS DZ 0 . ,
: 93% DD
5%, , 50.
,
, , -, . DD > 7%
,
.

DE: , , .

. DS (. . 15).
, ,
. Z 0 : 62 (18% ) Z 0 > 1 ( ,
(8.3%)), 46 (28%) 163
Z 0 .

( ). DD DE (. 16,a) ,
a

DG, %
15

100Pi Pj
DP
, j>i.
Pj

n (DE)

DE, %

1 DZ 0

. 15. DE (a), DD (b), DS (c),

DZ 0 (d ).3

720

745
745 730 715
0

DH, %

DD, %
DZ 0 , %

DS, %

10
2

5
0

75

72

710
715

74
0

DD, %

DE, %

. 16. DE DD (a), DG DH (b),

DS DD (c), DZ 0 DE (d ).3

.

.
DG (. 16,b)
, DE. , (. 16,c).
, .
DZ 0 DE . 16,d. Z 0 > 1 *50% . ,

.
, , , , .
.
28%
; 82% P21/, 18%

1, Pbca, 2/ P212121.

P21/.
,
Z 0 > 1. ,
,
.
,
.
, 20 '
(24%)
.

 68 (1) 1999

17

H
C
O

. 17.

2,6--4-()-2,5- (DMFUSC).101, 102

10 P21/ P212121 , 6 P21/ P21 , 4

P21/ 4 P21/ n21 .
3, 49, 50
. ,
, , ,
.
- 1996 .
102 . : 45 (44.1%) P21/c P212121 , 17
(16.7%) P21/c P21 , 14 (13.6%) P21/c Pna21 , 10

(9.8%) P21/c Pc, 3 (2.9%) P21/c 1, 7 (6.9%)

1 P212121 , 2 (2.0%) 1 P21 , 2 (2.0%) 1 Pc,

2 (2.0%) 1 Pna21 .
-
.

P21/c P212121 . 2,6--4-()-2,5- 101, 102 (DMFUSC)}
. (. 17) ; ,
, .

H
C
O
. 18. DMFUSC
( xy0).
.

(. 18).
b- (P212121) , a-
(P21/c) . a- b- 383 K.
,

, .
(1-) 103
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CAMBRIDGE STRUCTURAL DATABASE AS A RESEARCH TOOL IN ESSENTIAL

PRINCIPLES OF ORGANIC MOLECULAR CRYSTAL PACKING INVESTIGATIONS
L.N.Kuleshova, M.Yu.Antipin
A.N.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
28, Ul. Vavilova, 117813 Moscow, Russian Federation, Fax +7(095)135 5085
Data on application of the Cambridge Structural Database to study the general features of the structure
of molecular crystals are analysed and reviewed. It was shown that Cambridge Structural Database
opportunities allow one to check a workability of main well known concepts of organic crystal
chemistry the close packing principle, space groups distribution, the preference of the centrosymmetrical molecular crystal in comparison with eccentric ones. Examples of the Cambridge Structural
Database use for a molecular crystal engineering and a systematical search for crystals with special
physical properties are given.
Bibliography 122 references.
Received 23rd April 1998