1,1′-[1,4-Phenyl­enebis(methyl­ene)]bis­(2-methyl-1H-imidazol-3-ium) 2,4-dicarb­oxy­benzene-1,5-dicarboxyl­ate monohydrate

Gui-Ying Dong; Tong-Fei Liu; Cui-Hong He; Xiao-Chen Deng; Xiao-Ge Shi

doi:10.1107/S160053681102263X

. 2011 Jun 18;67(Pt 7):o1696. doi: 10.1107/S160053681102263X

1,1′-[1,4-Phenylenebis(methylene)]bis(2-methyl-1H-imidazol-3-ium) 2,4-dicarboxybenzene-1,5-dicarboxylate monohydrate

Gui-Ying Dong ^a,^*, Tong-Fei Liu ^a, Cui-Hong He ^a, Xiao-Chen Deng ^b, Xiao-Ge Shi ^b

PMCID: PMC3151773 PMID: 21837093

Abstract

In the dication of the title compound, C₁₆H₂₀N₄ ²⁺·C₁₀H₄O₈ ²⁻·H₂O, the dihedral angles formed by mean planes of the imidazolium rings and the benzene ring are 69.05 (18) and 89.1 (2)°. In the crystal, the components are linked into a three-dimensional network by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the synthesis of 1,4-bis(2-methyl-1H-imidazole-3-ium)benzene, see: Hoskins et al. (1997 ▶). For related complexes, see: Liu Wu, Wan et al. (2011 ▶); Liu, Wu, Zhang & Cui (2011 ▶).

Experimental

Crystal data

C₁₆H₂₀N₄ ²⁺·C₁₀H₄O₈ ²⁻·H₂O
M _r = 538.51
Monoclinic,
a = 9.7139 (19) Å
b = 19.428 (4) Å
c = 13.856 (3) Å
β = 97.39 (3)°
V = 2593.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.968, T _max = 0.971
20668 measured reflections
4571 independent reflections
3075 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.144
S = 1.10
4571 reflections
356 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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) I, global. DOI: 10.1107/S160053681102263X/lh5268sup1.cif

e-67-o1696-sup1.cif^{(28.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102263X/lh5268Isup2.hkl

e-67-o1696-Isup2.hkl^{(223.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102263X/lh5268Isup3.cml

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
O1—H1⋯O6ⁱ	0.82	1.76	2.575 (3)	172
O1W—H1A⋯O6	0.86	1.90	2.747 (3)	168
O1W—H1B⋯O5ⁱⁱ	0.85	1.98	2.743 (3)	149
N4—H1C⋯O4ⁱⁱⁱ	0.98	1.75	2.679 (4)	158
N2—H2⋯O1W^iv	1.07	1.59	2.651 (4)	172
O8—H8⋯O3^v	0.82	1.81	2.586 (3)	157

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

Acknowledgments

The authors thank Hebei United University for supporting this work.

supplementary crystallographic information

Comment

1,4-bis(2-methylimidazole-1-methyl)benzene is a flexible bridging ligand, which can participate in the construction of coordination polymers and can provide information on the influences of 2-substituted derivatives of imidazole on the structures and properties of resulting complexes (Liu et al., 2011a,2011b). In our attempt to synthesize a zinc complex with this ligand, we unexpectedly obtained the title compound (I) and report herein its synthesis and crystal structure determination.

The asymmetric unit of (I) is shown in (Fig. 1). Bond distances and angles are as found in other structures (Liu Wu, Wan et al., 2011); Liu, Wu, Zhang & Cui, 2011). In the dication, the dihedral angles formed by the mean-planes of the imidazole rings and the benzene ring (C11-C16) are 69.05 (18)° (N1/N2/C18/C19/C20) and 89.1 (2)° (N3/N4/C23/C24/C25). In the crystal, the components are linked into a three-dimensional network by intermolecular N—H···O and O—H···O hydrogen bonds.

Experimental

1,4-Bis(2-methylimidazole-1-methyl)benzene was prepared by the method of Hoskins et al. (1997). A mixture of Zn(NO₃)₂.6H₂O (298 mg,1 mmol), 1,4-bis(2-methylimidazole-1-methyl)benzene (1.0 mmol, 266.4 mg), 1,2,4,5-benzenetetracarboxylic acid (1.0 mmol, 254.2 mg) and H₂O (12 mL) was placed in a Teflon-lined stainless vessel and heated to 393 K for 4 days under autogenous pressure, and then cooled to room temperature in 24 h. block-shaped colourless crystals of (I) suitable for single-crystal X-ray diffraction analysis were obtained.