Z. Kristallogr.

NCS 2017; 232(5): 765–767

Open Access

Guo qiang Li, Rui ping Zhou, Xiao fang Luo, Hong Zhou and Qiang Xu*

Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-

diylbis(oxy))bis(2,1-phenylene))bis(azanyl-
ylidene))bis(methanylylidene))bis(naphthalen-2-
olato-κ3O,O′,N)zinc(II), C36H26N2O4Zn

Abstract
C36 H26 N2 O4 Zn, monoclinic, C2/c (no. 15), a = 43.237(10) Å,
b = 17.201(4) Å, c = 11.271(2) Å, β = 103.009(5)°, V = 8168(3) Å3 ,
Z = 12, Rgt (F) = 0.0442, wRref (F 2 ) = 0.1530, T = 100(2) K.

CCDC no.: 1494369

Table 1: Data collection and handling.

Crystal: Yellow block

Size: 0.20 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
µ: 9.5 cm−1
Diffractometer, scan mode: Bruker APEXII, φ and ω-scans
2θmax , completeness: 50°, >99%
N(hkl)measured , N(hkl)unique , Rint : 28278, 7220, 0.055
Criterion for Iobs , N(hkl)gt : Iobs > 2 σ(Iobs ), 4975
N(param)refined : 582
Programs: Bruker [1], SHELX [2]

The crystal structure is shown in the figure. The radii of the el-
lipsoids are drawn with an arbitrary probability. Tables 1 and
DOI 10.1515/ncrs-2017-0025 2 contain details on crystal structure and measurement con-
Received January 20, 2017; accepted July 18, 2017; available ditions and a list of the atoms including atomic coordinates
online August 5, 2017 and displacement parameters.

*Corresponding author: Qiang Xu, Chongqing Key Laboratory
of Environmental Materials and Remediation, Technologies,
Chongqing University of Arts and Sciences, Chongqing, 402160,
P. R. China, e-mail: 1050573038@qq.com
Guo qiang Li: Chongqing Key Laboratory of Environmental Materials
and Remediation, Technologies, Chongqing University of Arts and
Sciences, Chongqing, 402160, P. R. China
Rui ping Zhou and Hong Zhou: Chongqing University of Arts and
Sciences, Chongqing, 402160, P. R. China
Xiao fang Luo: Third Branch of Chongqing Academy of Metrology
and Quality Inspection, Chongqing, 402160, P. R. China
© 2017 Guo qiang Li et al., published by De Gruyter.
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.
Source of material
The educt 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-
phenylene))bis(azanylylidene))bis(methanylylidene))bis
(naphthalen-2-ol) (H2 L) used in the present work was
synthesized via a standard Schiff base condensation reaction
of 2-hydroxy-1-naphthaldehyde (0.6887 g, 4 mmol) and
bis(4-aminophenoxy)ethane (0.4886 g, 2 mmol) following
a modified literature procedure [3]. All other reagents were
commercially available and used without further purification.
The title compound was prepared by a vapor diffusion
method. To a yellow MeOH solution (15 mL) of H2 L (0.552 g,
Unauthenticated
Download Date | 6/3/18 4:50 PM
766 | Li et al.: C36 H26 N2 O4 Zn

Table 2: Fractional atomic coordinates and isotropic or equivalent Table 2 (continued)

isotropic displacement parameters (Å2 ).
Atom x y z Uiso */Ueq
Atom x y z Uiso */Ueq
C33 0.39838(11) 0.9750(3) 0.0023(4) 0.0474(11)
Zn1 0.326086(10) 0.75276(3) 0.19582(4) 0.03364(16) C14 0.20548(9) 0.8239(2) 0.2182(3) 0.0378(10)
Zn2 0.5000 0.64801(4) 0.2500 0.0460(2) H14 0.1830 0.8207 0.1942 0.045*
O4 0.32703(6) 0.83457(17) 0.0738(2) 0.0429(7) C7 0.21350(10) 0.4890(2) −0.1343(4) 0.0416(10)
O2 0.30372(6) 0.84088(15) 0.3154(2) 0.0357(6) H7 0.1910 0.4919 −0.1562 0.050*
O5 0.48755(6) 0.53334(16) 0.3529(2) 0.0389(7) C41 0.38972(9) 0.5277(3) 0.3036(4) 0.0441(11)
O1 0.33563(6) 0.65285(17) 0.1268(3) 0.0493(8) H41 0.3673 0.5270 0.2935 0.053*
O3 0.33409(6) 0.70345(16) 0.4095(2) 0.0368(7) C28 0.40658(9) 0.9205(2) 0.0985(4) 0.0391(10)
N2 0.37246(7) 0.77719(19) 0.2829(3) 0.0310(7) C24 0.41929(10) 0.7243(3) 0.4342(4) 0.0455(11)
N1 0.27853(7) 0.72479(18) 0.1610(3) 0.0276(7) H24 0.4337 0.7462 0.3909 0.055*
O6 0.50315(7) 0.7127(2) 0.1094(4) 0.0850(13) C19 0.31757(10) 0.7504(3) 0.4819(4) 0.0439(11)
N3 0.45247(7) 0.63266(18) 0.1848(3) 0.0344(8) H19A 0.3280 0.7452 0.5693 0.053*
C4 0.27939(9) 0.4828(2) −0.0741(3) 0.0335(9) H19B 0.2953 0.7325 0.4702 0.053*
C20 0.36676(9) 0.6999(2) 0.4562(3) 0.0357(10) C40 0.40816(10) 0.4763(3) 0.3837(4) 0.0488(12)
C12 0.25723(9) 0.7751(2) 0.2050(3) 0.0271(8) H40 0.3986 0.4398 0.4276 0.059*
C17 0.27090(9) 0.8333(2) 0.2864(3) 0.0313(9) C37 0.50182(9) 0.4647(2) 0.3175(4) 0.0473(11)
C9 0.26383(9) 0.5450(2) −0.0280(3) 0.0285(8) H37A 0.4915 0.4180 0.3425 0.057*
C13 0.22406(9) 0.7716(2) 0.1717(3) 0.0314(9) H37B 0.5246 0.4632 0.3583 0.057*
H13 0.2141 0.7327 0.1162 0.038* C23 0.43095(11) 0.6829(3) 0.5378(4) 0.0514(12)
C38 0.45439(8) 0.5301(2) 0.3330(3) 0.0319(9) H23 0.4532 0.6764 0.5653 0.062*
C10 0.28304(9) 0.6043(2) 0.0478(3) 0.0276(8) C2 0.33060(10) 0.5369(2) 0.0178(4) 0.0419(10)
C43 0.43624(9) 0.5817(2) 0.2497(3) 0.0314(9) H2 0.3531 0.5336 0.0322 0.050*
C11 0.26688(9) 0.6635(2) 0.0977(3) 0.0284(8) C6 0.22914(11) 0.4265(3) −0.1751(4) 0.0482(12)
H11 0.2445 0.6577 0.0832 0.034* H6 0.2174 0.3864 −0.2231 0.058*
C36 0.35037(9) 0.8790(2) 0.0614(3) 0.0366(9) C22 0.41076(11) 0.6502(3) 0.6031(4) 0.0536(12)
C45 0.44768(9) 0.7265(2) 0.0161(4) 0.0392(10) H22 0.4191 0.6226 0.6763 0.064*
C54 0.42445(10) 0.7656(2) −0.0809(4) 0.0395(10) C47 0.48962(12) 0.7918(3) −0.0609(6) 0.0788(19)
C25 0.38669(9) 0.7354(2) 0.3903(3) 0.0331(9) H47 0.5116 0.8006 −0.0562 0.095*
C26 0.38994(9) 0.8253(2) 0.2372(3) 0.0344(9) C52 0.37124(12) 0.7985(3) −0.1874(4) 0.0582(13)
H26 0.4115 0.8284 0.2801 0.041* H52 0.3490 0.7930 −0.1956 0.070*
C1 0.31657(9) 0.6011(2) 0.0677(3) 0.0361(9) C51 0.38228(14) 0.8474(3) −0.2669(4) 0.0631(14)
C21 0.37842(10) 0.6581(2) 0.5608(4) 0.0446(11) H51 0.3678 0.8741 −0.3296 0.076*
H21 0.3643 0.6348 0.6037 0.054* C50 0.41344(14) 0.8563(3) −0.2537(4) 0.0629(14)
C44 0.43629(9) 0.6744(2) 0.0948(4) 0.0362(9) H50 0.4212 0.8906 −0.3065 0.075*
H44 0.4139 0.6693 0.0800 0.043* C34 0.36654(12) 0.9824(3) −0.0581(4) 0.0543(12)
C5 0.26136(11) 0.4244(2) −0.1450(4) 0.0434(11) H34 0.3609 1.0204 −0.1203 0.065*
H5 0.2720 0.3822 −0.1727 0.052* C35 0.34375(11) 0.9380(3) −0.0316(4) 0.0487(12)
C16 0.25213(10) 0.8856(2) 0.3334(3) 0.0392(10) H35 0.3225 0.9455 −0.0755 0.058*
H16 0.2618 0.9248 0.3889 0.047* C48 0.46833(13) 0.8271(3) −0.1492(5) 0.0766(18)
C27 0.38154(9) 0.8738(2) 0.1325(3) 0.0332(9) H48 0.4756 0.8607 −0.2042 0.092*
C39 0.44050(10) 0.4788(3) 0.3987(4) 0.0460(11) C31 0.45295(14) 1.0100(4) 0.0203(5) 0.0792(18)
H39 0.4535 0.4447 0.4552 0.055* H31 0.4686 1.0406 −0.0052 0.095*
C3 0.31287(10) 0.4815(2) −0.0488(4) 0.0408(10) C30 0.46182(12) 0.9569(4) 0.1145(5) 0.0783(18)
H3 0.3232 0.4400 −0.0799 0.049* H30 0.4836 0.9506 0.1533 0.094*
C46 0.48059(12) 0.7414(3) 0.0266(5) 0.0616(14) C29 0.43869(11) 0.9128(3) 0.1517(4) 0.0580(13)
C15 0.21953(10) 0.8806(2) 0.2993(3) 0.0414(10) H29 0.4451 0.8762 0.2157 0.070*
H15 0.2067 0.9160 0.3316 0.050* C32 0.42222(13) 1.0180(3) −0.0344(5) 0.0657(15)
C8 0.23043(9) 0.5459(2) −0.0628(3) 0.0337(9) H32 0.4164 1.0538 −0.0998 0.079*
H8 0.2193 0.5874 −0.0359 0.040*
C53 0.39141(11) 0.7580(2) −0.0980(4) 0.0455(11)
H53 0.3830 0.7242 −0.0466 0.055*
C18 0.31827(10) 0.8338(3) 0.4434(3) 0.0434(11) 1 mmol) was added slowly a MeOH solution (10 mL) of
H18A 0.3067 0.8664 0.4914 0.052*
Zn(CH3 COO)2 ·2H2 O (0.220 mg, 1 mmol), and the resulting
H18B 0.3405 0.8523 0.4589 0.052*
solution was stirred for 30 min to afford a clear pale-gold
C42 0.40346(9) 0.5799(2) 0.2382(3) 0.0378(10)
H42 0.3904 0.6153 0.1845 0.045* colored solution. The solvent was evaporated in air to give
C49 0.43530(12) 0.8156(3) −0.1625(4) 0.0542(13) a yellow powder, which was isolated by filtration, washed

Unauthenticated
Download Date | 6/3/18 4:50 PM

with cold MeOH, and dried under vacuum over P4 O10 . The
yellow block-shaped crystals suitable for X-ray analysis were
obtained from a acetone solution of the powdered solid after
about 3 days.
Experimental details
All of the hydrogen atoms were placed in the calculated posi-
tions and all the non-hydrogen atoms were refined anisotrop-
ically.
Discussion
Schiff base is one of the oldest compound bearing the
—N=CH— functional group, which can be readily synthe-
sized by the condensation reaction of carbonyl-containing
compounds with primary amines. For a long time, nu-
merous chemists from different disciplines have redirected
their efforts to Schiff-base complexes due to their potential
application in photocatalysis [4], bioscience [5] and magnetic
properties [6]. As part of our work, a novel zinc(II) com-
plex with a Salen-type bisoxime ligand was synthesized and
characterized by X-ray diffraction.
The title complex is a mononuclear structure. The central
zinc(II) is hexa-coordinated by two nitrogen atoms (N(1), N(2))
and four oxygen atoms (O(1), O(2), O(3), O(4)), resulting a
slightly distored-octahedral geometry. The equatorial plane is
defined by two ether O atoms (O2 and O3) and two aromatic-
oxide O atoms (O1 and O4; cf. the figure) with the Zn—O
bond distance in the range of 1.968(3) Å to 2.410(3) Å, and
the O—Zn—O bond angles around the Zn(II) atom vary from
70.11(13)° to 158.49(11)°. The axial positions are occupied by
Li et al.: C36 H26 N2 O4 Zn | 767
two imine nitrogen atoms with the N(1)-Zn(1)-N(2) bond angle
is 163.15(12)°, and the bond length of Zn(1)-N(1), Zn(1)-N(2) are
2.063(3) Å and 2.067(3) Å, respectively.
All bond lengths and angles in the organic ligand system
are in the expected ranges.
Acknowledgements: I acknowledge support for the pub-
lication fee by the Scientific Research Fund of Chongqing
Municipal Education Commissionthe (KJ1601115), Chongqing
University of Arts and Sciences (Z2015CH02), Chongqing Uni-
versity of Arts and Sciences (XSKY2016058) and Chongqing
University of Arts and Sciences (XSKY2016067).
References
1. Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison,
Wisconsin, USA, 2009.
2. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta
Crystallogr. C71 (2015) 3–8.
3. Zhang, Q. L.; Zhang, Y. Q.; Zhu, B. X.: Crystal structure of
Ag(I) schiff base complex. Chinese. J. Inorg. Chem. 27 (2011)
2191–2194.
4. Song, Q.; Ma, W. H.; Jia, M. K.; Johnson, D.; Huang, Y. P.:
Degradation of organic pollutants in waters by a water-insoluble
iron(III) Schiff base complex. Applied Catalysis A: General. 505
(2015) 70–76.
5. Wang, H.; Gan, G. Q.; Qu, Y.; Chen, H.; Lin, Z. D.: Syn-
thesis, charaterization and DNA interactions of 2,4-
dihydroxybenzoylhydrazone coordinated to Cu(II). Chinese.
J. Inorg. Chem. 28 (2012) 1217–1221.
6. Pait, M.; Bauza, A.; Frontera, A.; Colacio, E.; Ray, D.: A new
family of Ni4 and Ni6 aggregates from the self-assembly of [Ni2 ]
building units: role of carboxylate and carbonate bridges. Inorg.
Chem. 54 (2015) 4709–4723.
Unauthenticated
Download Date | 6/3/18 4:50 PM