1,4-Bis(imidazol-1-yl)benzene–terephthalic acid (1/1)

Shiyong Zhang; Yurong Tang; Zhihua Mao; Mingliang Li; Jingbo Lan; Xiaoyu Su

doi:10.1107/S1600536808040324

. 2008 Dec 6;65(Pt 1):o26. doi: 10.1107/S1600536808040324

1,4-Bis(imidazol-1-yl)benzene–terephthalic acid (1/1)

Shiyong Zhang ^a, Yurong Tang ^a, Zhihua Mao ^b, Mingliang Li ^a, Jingbo Lan ^a, Xiaoyu Su ^a,^*

PMCID: PMC2967945 PMID: 21581669

Abstract

In the title compound, C₁₂H₁₀N₄·C₈H₆O₄, 1,4-bis(imidazol-1-yl)benzene and terephthalic acid molecules are joined via strong O—H⋯N hydrogen bonds to form infinite zigzag chains. Both molecules are located on crystallographic inversion centers. The O—H⋯N hydrogen-bonded chains are assembled into two-dimensional layers through weak C—H⋯O and strong π–π stacking interactions [centroid–centroid distance = 3.818 (2) Å], leading to the formation of a three-dimensional supramolecular structure.

Related literature

For general background, see: Aakeröy et al. (2006 ▶); Aakeröy & Seddon (1993 ▶); Desiraju, 2007 ▶; Corna et al. (2004 ▶); Dobrzanska et al. (2006); Van Roey et al. (1991 ▶). For similar structures, see: Wang et al. (2007 ▶); Su et al. (2007 ▶).

Experimental

Crystal data

C₁₂H₁₀N₄·C₈H₆O₄
M _r = 376.37
Monoclinic,
a = 5.2780 (17) Å
b = 10.599 (5) Å
c = 15.449 (5) Å
β = 91.17 (3)°
V = 864.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.25 × 0.22 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1895 measured reflections
1538 independent reflections
904 reflections with I > 2σ(I)
R _int = 0.008
3 standard reflections every 200 reflections intensity decay: 2.5%

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.132
S = 0.95
1538 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040324/zl2155sup1.cif

e-65-00o26-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040324/zl2155Isup2.hkl

e-65-00o26-Isup2.hkl^{(75.9KB, 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
O1—H1⋯N2ⁱ	0.82	1.79	2.60885	178
C2—H2⋯O2ⁱⁱ	0.93	2.54	3.376 (3)	150
C4—H4⋯O2ⁱⁱⁱ	0.93	2.56	3.463 (3)	162

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

Acknowledgments

This work was supported by grants from the National Natural Science Foundation of China (grant No. 20702035) and Sichuan University experimental technical project (grant No. 07-57, 07-61).

supplementary crystallographic information

Comment

Supramolecular architectures assembled via various delicate noncovalent interactions such as hydrogen bonds, π—π stacking and electrostatic interactions, etc., have attracted intense interest in recent years because of their fascinating structural diversity and potential applications for functional materials (Desiraju, 2007; Corna et al., 2004). Especially, the application of intermolecular hydrogen bonds is a well known and efficient tool in the field of organic crystal design owing to its strength and directional properties (Aakeröy & Seddon, 1993). Imidazoles, as excellent N-donor compounds, have attracted special attention in the construction of organic cocrystals in recent years (Aakeröy et al., 2006; Van Roey et al., 1991). We recently presented organic crystals composed of flexible diimidazole compounds and dicarboxylic acids (Wang et al., 2007; Su et al., 2007). In further development of such interesting hydrogen-bonded supramolecular systems and as a continuation of our research in this area, we report herein the crystal structure of the title compound formed from rigid diimidazole and dicarboxylic acids molecules.

As shown in Figure 1, the asymmetric unit of the title compound contains each half a molecule of 1,4-bis(1-imidazolyl)benzene and terephthalic acid which are both located on crystallographic inversion centers. The carboxyl groups of the terephthalic acid interact with the imidazol-1-yl nitrogen atoms of 1,4-bis(1-imidazolyl)benzene via O1—H1···N2 hydrogen bonds (O1···N2 = 2.608 (8) Å and O1—H1···N2 = 178°), and thus the hydrogen bonds further propagate the acid-base subunits into an infinite one-dimensional zig-zag chain. Meanwhile, these chains are assembled into two-dimensional layers through weak C2—H2···O2 and C4—H4···O2 hydrogen bonds, with C2···O2 = 3.376 (3) Å, C2—H2···O2 = 150° and C4···O2 = 3.463 (3) Å, C4—H4···O2 = 162° (Figure 2). Moreover, the supramolecular layers are further stablized by intermolecular π—π interactions to form a three-dimensional stucture as depicted in Figure 3. A relative strong π—π interaction between one imidazole ring (Cg1: N1—C4—N2—C5—C6) and contiguous phenyl ring (Cg2: C1—C3—C2—C1b—C3b—C2b) of 1,4-bis(1-imidazolyl)benzene from another chain (centroid-centroid distance = 3.818 (2) Å, dihedral angle = 27.12) plays an important part in the connection of adjacent layers, where Cg1 is the centroid of the imidazole ring of the molecule at (1 - x, 1 - y, -z) and (-1 + x, y, z), and Cg2 is the centroid of the phenyl ring of the molecule at (1 - x, 1 - y, -z) and (1 + x, y, z).

Experimental

A methanol solution (5 ml) of 1,4-bis(1-imidazolyl)benzene (0.05 mmol, 10.5 mg) was added slowly with constant stirring to a solution of terephthalic acid (0.05 mmol, 8.3 mg) in methanol (2 ml) and water (0.5 ml) to give a clear solution. Then the reaction mixture was filtered and left to stand at room temperature. Colorless block crystals suitable for X-ray analysis were obtained after one week by slow evaporation of the solvent. Yield, 85%; ¹H NMR (400 MHz, DMSO-d6): δ 8.34 (s, 2H), 8.04 (s, 4H), 7.83 (t, 6H), 7.13 (s, 2H).