Bis{1-[(1H-benzimidazol-2-yl)meth­yl]-1H-imidazole-κN 3}­bis­(3,5-dicarb­oxy­benzoato-κO 1)zinc octa­hydrate

Lei Zhao; Bingtao Liu; Ting Li; Xiangru Meng

doi:10.1107/S160053681200147X

. 2012 Jan 18;68(Pt 2):m162. doi: 10.1107/S160053681200147X

Bis{1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole-κN ³}bis(3,5-dicarboxybenzoato-κO ¹)zinc octahydrate

Lei Zhao ^a, Bingtao Liu ^b, Ting Li ^c, Xiangru Meng ^c,^*

PMCID: PMC3274892 PMID: 22346839

Abstract

In the title complex, [Zn(C₉H₅O₆)₂(C₁₁H₁₀N₄)₂]·8H₂O, the Zn^II ion exhibits site symmetry 2. It shows a distorted tetrahedral coordination defined by two N atoms from two symmetry-related 1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole ligands and by two O atoms from two symmetry-related monodeprotonated 3,5-dicarboxybenzoate anions. In the crystal, complex molecules and solvent water molecules are linked through intermolecular O—H⋯O, O—H⋯N, and N—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For background information on Zn^II complexes constructed from both aromatic carboxylates and N-heterocyclic ligands, see: Lin et al. (2008 ▶); Tian et al. (2010 ▶).

Experimental

Crystal data

[Zn(C₉H₅O₆)₂(C₁₁H₁₀N₄)₂]·8H₂O
M _r = 1024.22
Monoclinic,
a = 20.870 (4) Å
b = 15.008 (3) Å
c = 15.472 (3) Å
β = 109.51 (3)°
V = 4567.9 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 293 K
0.18 × 0.15 × 0.14 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T _min = 0.896, T _max = 0.917
15325 measured reflections
4127 independent reflections
3898 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.158
S = 1.07
4127 reflections
314 parameters
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200147X/ff2052sup1.cif

e-68-0m162-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200147X/ff2052Isup2.hkl

e-68-0m162-Isup2.hkl^{(202.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O9	0.85	2.22	2.936 (8)	142
O9—H9A⋯O4	0.85	2.15	2.634 (7)	115
O9—H9B⋯O10	0.85	2.24	2.783 (12)	122
O10—H10A⋯O9	0.85	1.93	2.783 (12)	179
N4—H4⋯O7ⁱ	0.86	1.97	2.808 (4)	163
O3—H3⋯O10ⁱⁱ	0.82	2.56	3.341 (10)	159
O5—H5⋯N3ⁱⁱⁱ	0.82	1.77	2.577 (3)	165
O7—H7A⋯O2^iv	0.85	1.98	2.784 (4)	156
O7—H7B⋯O8^v	0.85	1.95	2.796 (5)	179
O8—H8B⋯O6^vi	0.85	2.02	2.799 (6)	152
O10—H10B⋯O6^vii	0.85	2.03	2.728 (9)	139

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Acknowledgments

We gratefully acknowledge financial support by the National Natural Science Foundation of China (No. J0830412).

supplementary crystallographic information

Comment

It is well known that the Zn^II ion is able to coordinate simultaneously to both oxygen-containing and nitrogen-containing ligands and the final products can exhibit attractive structures and useful functional properties. A great number of Zn^II complexes containing both aromatic carboxylates and N-heterocyclic ligands have been reported (Lin et al., 2008; Tian et al., 2010). In order to further explore such compounds with new structures, we selected 1-((1H-benzimidazol-1-yl)methyl)-1H-imidazole and 1,3,5-benzenetricarboxylic acid as ligands to self-assemble with Zn(NO₃)₂ and obtained the title complex, {[Zn(C₉H₅O₆)₂(C₁₁H₁₀N₄)₂] (H₂O)₈}, the crystal structure of which is reported herein. As shown in Figure 1, two 1-((1H-benzimidazol-1-yl)methyl)-1H-imidazole ligands and two monodeprotonated 1,3,5-benzenetricarboxylic acid anions coordinate to the Zn^II ion which is located on a twofold rotation axis. The Zn—O bond length is slightly shorter than the Zn—N bond length. The environment around the Zn^II ion can be best described as distorted tetrahedral. O—H···O, O—H···N, and N—H···O hydrogen bonds between solvent water/water molecules, between solvent water molecules and carboxylate O atoms, between carboxyl groups and solvent water molecules, between carboxyl groups and benzimidazole N atoms, between benzimidazole units and solvent water molecules of adjacent molecules consolidate the crystal packing (Figure 2).

Experimental

A mixture of Zn(NO₃)₂ (0.1 mmol), 1-((1H-benzimidazol-1-yl)methyl)-1H-imidazole (0.1 mmol), 1,3,5-benzenetricarboxylic acid (0.1 mmol) and water (10 ml) was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 120 °C for 72 h, then cooled to room temperature. Colourless crystals were obtained from the filtrate and dried in air.