Poly[[μ2-2,2′-diethyl-1,1′-(butane-1,4-di­yl)diimidazole-κ2 N 3:N 3′](μ2-5-hydroxy­isophthalato-κ2 O 1:O 3)zinc]

Ying-Ying Liu; Xing Wang; Yong-Sheng Yan

doi:10.1107/S1600536811039377

. 2011 Oct 5;67(Pt 11):m1477. doi: 10.1107/S1600536811039377

Poly[[μ₂-2,2′-diethyl-1,1′-(butane-1,4-diyl)diimidazole-κ² N ³:N ^3′](μ₂-5-hydroxyisophthalato-κ² O ¹:O ³)zinc]

Ying-Ying Liu ^a, Xing Wang ^a, Yong-Sheng Yan ^a,^*

PMCID: PMC3246914 PMID: 22219734

Abstract

In the title coordination polymer, [Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]_n, the Zn^II cation is coordinated by an O₂N₂ donor set in a distorted tetrahedral geometry. The Zn^II ions are linked by μ₂-OH-bdc (OH-H₂bdc = 5-hydroxyisophthalic acid) and bbie ligands [bbie = 2,2′-diethyl-1,1′-(butane-1,4-diyl)diimidazole], forming a two-dimensional layer parallel to the ab plane. The layers are further connected through intermolecular C—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional supramolecular structure. In the bbie ligand, the two C atoms in the ethyl group are each disordered over two positions with a site-occupancy ratio of 0.69:0.31.

Related literature

For background information on bis(imidazole) ligands, see: Kan et al. (2011 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

[Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]
M _r = 491.84
Monoclinic,
a = 13.5120 (12) Å
b = 12.765 (1) Å
c = 13.5910 (12) Å
β = 103.933 (2)°
V = 2275.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 K
0.28 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.73, T _max = 0.79
13890 measured reflections
5467 independent reflections
3988 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.087
S = 1.03
5467 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039377/fj2452sup1.cif

e-67-m1477-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039377/fj2452Isup2.hkl

e-67-m1477-Isup2.hkl^{(262.3KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Zn1—O1	1.9662 (15)
Zn1—O4ⁱ	1.9682 (14)
Zn1—N4ⁱⁱ	2.0020 (18)
Zn1—N1	2.0286 (17)

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O1—Zn1—O4ⁱ	102.54 (6)
O1—Zn1—N4ⁱⁱ	117.20 (7)
O4ⁱ—Zn1—N4ⁱⁱ	118.18 (7)
O1—Zn1—N1	115.96 (7)
O4ⁱ—Zn1—N1	98.33 (6)
N4ⁱⁱ—Zn1—N1	103.59 (7)

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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
C10—H10⋯O1ⁱⁱⁱ	0.93	2.62	3.417 (3)	144
C14—H14⋯O5ⁱⁱⁱ	0.93	2.49	3.398 (3)	166
O5—H5⋯O2^iv	0.82	1.88	2.697 (2)	171

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Symmetry code: (iii) Inline graphic ; (iv) .

Acknowledgments

We thank the China Postdoctoral Science Foundation (20100471379) for support.

supplementary crystallographic information

Comment

As part of an investigation of the transition metal application there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound, (I), is described.

As shown in Fig. 1, the Zn^II ions is four-coordinated by two oxygen atoms from two oxygen atoms of two OH-bdc anions and two nitrogen atoms of two bbie ligands. Each carboxylate group of OH-bdc acts in a monodentate mode, and the hydroxyl group is not involved in coordination. The bbie molecule coordinates to two Zn^II cations through its two aromatic N atoms, thus acing as a bridging bidentate ligand. As illustrated in Fig. 2, The Zn^II cations are connected by OH-bdc and bbie ligands to form a layer parallel to the ab plane. There exist hydrogen-binding interactions among adjacent layers. The layers are further connected by these hydrogen bonds to a 3D supramolecular architecture.

Experimental

The ligand bbie was synthesized according to the literature Liu et al., (2007), but 2-phenylimidazole was replaced by 2-ethylimidazole. A mixture of ZnCO₃ (0.050 g, 0.40 mmol), OH—H²bdc (0.043 g, 0.40 mmol), bbie (0.099 g, 0.40 mmol), and water (8 ml) was sealed in a Teflon reactor (18 ml) and heated at 140 °C for 3 days. After the mixture had been cooled to room temperature at 10 °C.h^-1, colorless crystals of (I) were obtained. Yield: 43%.