catena-Poly[[[aqua­(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)zinc]-μ-3-chloro­benzene-1,2-dicaboxylato-κ2O2:O3] [[(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)zinc]-μ-3-chloro­benzene-1,2-dicaboxylato-κ2O2:O3]]

Zhu, Y.; Li, H.-Y.; Ma, M.-L.

doi:10.1107/S1600536812014006

Volume 68
Part 5
Pages m574-m575
May 2012

Received 27 February 2012
Accepted 31 March 2012
Online 13 April 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.009 Å
R = 0.056
wR = 0.104
Data-to-parameter ratio = 12.3
Details

catena-Poly[[[aqua(4,4'-dimethyl-2,2'-bipyridine-²N,N')zinc]--3-chlorobenzene-1,2-dicaboxylato-²O²:O³] [[(4,4'-dimethyl-2,2'-bipyridine-²N,N')zinc]--3-chlorobenzene-1,2-dicaboxylato-²O²:O³]]

Yu Zhu,^a ^* Hai-Yang Li ^a and Ming-Li Ma ^a

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: zhuyu@zzu.edu.cn

In the title compound, {[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]}_n, one Zn²⁺ ion is five-coordinated by two O atoms from two different 3-chlorobenzene-1,2-dicarboxylate ligands, one O atom from a water molecule and two N atoms from a 4,4'-dimethyl-2,2'-bipyridine ligand, while the second Zn²⁺ ion is four-coordinated by two O atoms from two different 3-chlorobenzene-1,2-dicarboxylate ligands, and two N atoms from a 4,4'-bimethyl-2,2'-bipyridine ligand. The crystal structure exhibits a three-dimensional supramolecular structure composed of alternate Zn(C₈H₃O₄Cl)(C₁₂H₁₂N₂) and Zn(C₈H₃O₄Cl)(C₁₂H₁₂N₂)(H₂O) chains, which are linked together by face-to-face [pi] - [pi] interactions [shortest centroid-centroid distances of 3.661 (4) and 3.6901 (3) Å], O-HO and C-HO hydrogen bonds.

Related literature

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2011). For related O-HO hydrogen bonds, see: Desiraju et al. (2004). For related [pi] - [pi] interactions, see: Zang et al. (2010). For related C-HO hydrogen bonds, see: Desiraju et al. (1996). For related C-H [pi] interactions, see: Nishio et al. (1998).

Experimental

Crystal data

[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]
M_r = 914.38
Orthorhombic, P n a 2₁
a = 34.050 (4) Å
b = 14.1831 (10) Å
c = 7.8764 (6) Å
V = 3803.8 (6) Å³
Z = 4
Mo K radiation
= 1.47 mm^-1
T = 291 K
0.20 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.971, T_max = 1.000
10533 measured reflections
6396 independent reflections
5076 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.104
S = 1.07
6396 reflections
518 parameters
1 restraint
H-atom parameters constrained
_max = 0.63 e Å^-3
_min = -0.37 e Å^-3
Absolute structure: Flack (1983), 2200 Friedel pairs
Flack parameter: 0.093 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WAO4ⁱ	0.85	2.10	2.768 (6)	135
O1W-H1WBO4ⁱⁱ	0.85	1.79	2.644 (6)	179
O1W-H1WBO3ⁱⁱ	0.85	2.43	2.930 (5)	118
C17-H17O4ⁱ	0.93	2.36	3.202 (8)	150
C20-H20O6ⁱⁱⁱ	0.93	2.28	3.171 (8)	160
C23-H23O6ⁱⁱⁱ	0.93	2.40	3.306 (8)	164
C32-H32O2ⁱ	0.93	2.57	3.459 (8)	161
C35-H35O2ⁱ	0.93	2.45	3.353 (8)	165
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2156 ).

References

Desiraju, G. R. (1996). Acc. Chem. Res. 29, 441-449.
Desiraju, G. R. (2004). Hydrogen Bonding in Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 658-665. New York: Marcel Dekker Inc.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Maspoch, D., Ruiz-Molina, D. & Veciana, J. (2007). Chem. Soc. Rev. 36, 770-818.
Nishio, M., Hirota, M. & Umezawa, Y. (1998). In The C-H Interaction: Evidence, Nature and Consequences. Weinheim: Wiley-VCH.
Ockwig, N. W., Delgado-Friedrichs, O., O'Keefee, M. & Yaghi, O. M. (2005). Acc. Chem. Res. 38, 176-182.
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zang, S.-Q., Fan, Y.-J., Liang, R., Hou, H.-W. & Mak, T. C. W. (2011). Cryst. Growth Des. 11, 3395-3405.
Zang, S.-Q., Liang, R., Fan, Y.-J., Hou, H.-W. & Mak, T. C. W. (2010). Dalton Trans. 39, 8022-8032.

metal-organic compounds

catena-Poly[[[aqua(4,4'-dimethyl-2,2'-bipyridine-2N,N')zinc]--3-chlorobenzene-1,2-dicaboxylato-2O2:O3] [[(4,4'-dimethyl-2,2'-bipyridine-2N,N')zinc]--3-chlorobenzene-1,2-dicaboxylato-2O2:O3]]