Poly[[[μ2-1,1′-(butane-1,4-di­yl)bis­(1H-imidazole)-κ2 N 3:N 3′](μ2-2,6-di­methyl­pyridine-3,5-dicarboxyl­ato-κ2 O 3:O 5)zinc] dihydrate]

Yu-Mei Yue; Lei Qian; Zheng-Hao Zhu; Cheng Wang; Ting Gao

doi:10.1107/S1600536811039481

. 2011 Sep 30;67(Pt 10):m1471–m1472. doi: 10.1107/S1600536811039481

Poly[[[μ₂-1,1′-(butane-1,4-diyl)bis(1H-imidazole)-κ² N ³:N ^3′](μ₂-2,6-dimethylpyridine-3,5-dicarboxylato-κ² O ³:O ⁵)zinc] dihydrate]

Yu-Mei Yue ^a,^*, Lei Qian ^b, Zheng-Hao Zhu ^c, Cheng Wang ^d, Ting Gao ^d

PMCID: PMC3201321 PMID: 22058724

Abstract

In the title coordination polymer, {[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O}_n, the Zn^II ion displays a distorted tetrahedral geometry with two imidazole N atoms from two 1,1′-(butane-1,4-diyl)bis(imidazole) (bbi) ligands and two carboxylate O atoms from two 2,6-dimethylpyridine-3,5-dicarboxylate (dpdc) ligands. The bbi and dpdc ligands bridge the Zn^II ions, forming layers parallel to (011). O—H⋯O and O—H⋯N hydrogen bonds and π–π interactions between the imidazole rings [centroid–centroid distance = 3.807 (5) Å] connect the layers. Two of the three uncoordinated water molecules are disordered, each over two 0.25-occupancy positions.

Related literature

For transition metal complexes derived from 2,6-dimethylpyridine-3,5-dicarboxylic acid, see: Chen et al. (2009 ▶); Huang et al. (2008 ▶); Zhang et al. (2008a ▶); Zhou et al. (2009 ▶). For metal complexes derived from 1,1′-(butane-1,4-diyl)bis(imidazole) and carboxylic acids, see: Lan et al. (2008 ▶); Tian et al. (2009 ▶); Zhang et al. (2008b ▶).

Experimental

Crystal data

[Zn(C₉H₇NO₄)(C₁₀H₁₄N₄)]·2H₂O
M _r = 484.82
Orthorhombic,
a = 17.8088 (12) Å
b = 9.4003 (4) Å
c = 15.5798 (8) Å
V = 2608.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 K
0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.807, T _max = 0.823
14228 measured reflections
4717 independent reflections
3753 reflections with I > 2σ(I)
R _int = 0.087

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.175
S = 1.03
4717 reflections
315 parameters
36 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.64 e Å⁻³
Absolute structure: Flack (1983 ▶), 2186 Friedel pairs
Flack parameter: 0.03 (2)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039481/hy2452sup1.cif

e-67-m1471-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039481/hy2452Isup2.hkl

e-67-m1471-Isup2.hkl^{(231.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected bond lengths (Å).

Zn1—O1	1.954 (4)
Zn1—O4ⁱ	1.965 (3)
Zn1—N2	1.994 (6)
Zn1—N4ⁱⁱ	2.032 (6)

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Symmetry codes: (i) Inline graphic ; (ii) .

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1B⋯O2ⁱⁱⁱ	0.87 (4)	1.99 (4)	2.820 (9)	160 (4)
O1W—H1A⋯N1	0.87 (3)	1.95 (3)	2.736 (10)	149 (5)

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Symmetry code: (iii) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support from the Education Department of Heilongjiang Province (grant Nos. 11551335, 11551334 and 11551339) and Heilongjiang University.

supplementary crystallographic information

Comment

In recent years, great interest has been focused on the crystal engineering of coordination frameworks. As is already known, pyridine-3,5-dicarboxylic acid is a rigid and linear ligand that possesses the capability to bridge metal atoms in various coordination modes through the carboxylate O atoms and the pyridine N atom (Chen et al., 2009; Huang et al., 2008; Zhang et al., 2008a; Zhou et al., 2009). Flexible 1,1'-(butane-1,4-diyl)bis(imidazole) (bbi) ligand with organic carboxylic acids can build diverse topological architectures (Lan et al., 2008; Tian et al., 2009; Zhang et al., 2008b). Herein, we report the crystal structure of the title compound obtained by reacting bbi and 2,6-dimethylpyridine-3,5-dicarboxylic acid (H₂dpdc) with Zn(NO₃)₂.

In the title compound (Fig. 1), the Zn^II ion has a distorted tetrahedral geometry with two imidazole N atoms from two different bbi ligands and two carboxylate O atoms from two different dpdc ligands (Table 1). The bbi and dpdc ligands bridge the Zn^II ions into a layer parallel to (0 1 1) (Fig. 2). O—H···O and O—H···N hydrogen bonds (Table 2) and π–π interactions between the imidazole rings [centroid–centroid distance = 3.807 (5) Å] connect the layers.

Experimental

The title complex was obtained by the reaction of zinc(II) nitrate (59.5 mg, 0.2 mmol) with bbi (37.6 mg, 0.2 mmol) and H₂dpdc (39.4 mg, 0.2 mmol) in DMF/ethanol/water (10/10/5 ml). The mixture was stirred for 1 h and the solution was placed at room temperature for solvent volatilization. Single crystals were obtained after several days. Analysis, calculated for C₁₉H₂₅N₅O₆Zn: C 47.96, H 5.08, N 14.72%; found: C 48.08, H 5.49, N 14.52%.