1,4-Bis(1H-benzimidazol-1-yl)benzene

Guo-Feng Sun; Jian-Ping Hu; Dian-Yong Tang; Yuan-Qin Zhang

doi:10.1107/S1600536811031278

. 2011 Aug 11;67(Pt 9):o2286. doi: 10.1107/S1600536811031278

1,4-Bis(1H-benzimidazol-1-yl)benzene

Guo-Feng Sun ^a,^*, Jian-Ping Hu ^a, Dian-Yong Tang ^a, Yuan-Qin Zhang ^a

PMCID: PMC3200633 PMID: 22058929

Abstract

In the title compound, C₂₀H₁₄N₄, the dihedral angles between the central benzene ring and the pendant benzimidazole ring systems are 46.60 (15) and 47.89 (16)°. The dihedral angle between the benzimidazole ring systems is 85.62 (12)° and the N atoms lie to the same side of the molecule. In the crystal, molecules are linked by C—H⋯N interactions and weak aromatic π–π stacking [shortest centroid–centroid separation = 3.770 (2) Å] is observed.

Related literature

For background to benzimidazole derivatives as ligands in crystal engineering, see: Li et al. (2009 ▶); Vijayan et al. (2006 ▶).

Experimental

Crystal data

C₂₀H₁₄N₄
M _r = 310.35
Orthorhombic,
a = 9.5458 (19) Å
b = 20.499 (4) Å
c = 7.9283 (16) Å
V = 1551.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.18 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.980, T _max = 0.985
12744 measured reflections
1479 independent reflections
1298 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.104
S = 1.17
1479 reflections
231 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031278/hb6340sup1.cif

e-67-o2286-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031278/hb6340Isup2.hkl

e-67-o2286-Isup2.hkl^{(73KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031278/hb6340Isup3.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
C1—H1⋯N4ⁱ	0.93	2.50	3.359 (5)	153
C6—H6⋯N4ⁱⁱ	0.93	2.56	3.447 (5)	159

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

supplementary crystallographic information

Comment

In recent years, benzimidazole has been well used in crystal engineering, because they exhibit a strong networking ability (Vijayan et al., 2006). To our knowledge, the research on benzimidazole ligands bearing rigid spacers is still less developed (Li et al., 2009), and the title compound was well designed for building polymer architecture. We report here the structure and conformation of a rigid benzimidazole derivative, and further explore the ligand coordination. As shown in Fig. 1, the title compound is trans-conformation and tends to trans-coordination. The molecule has no inversion centre because two benzimidazole rings are not coplanar.

Experimental

The ligand 1,4-di(1H-benzimidazol-1-yl)benzene was prepared by a modified method (Li et al., 2009). A mixture of 1,4-dibromophenyl (3.72 g, 12.0 mmol), benzimidazole (4.25 g, 36.0 mmol), CuI (0.38 g, 2.0 mmol), 1,10-phenanthroline (0.72 g, 4.0 mmol), and Cs₂CO₃ (2.48 g, 18.0 mmol) was suspended in DMF (50 ml) and refluxed for 48 h to afford (I) as off-white powder, yield: 25% (based on 1,4-dibromophenyl), Mp: 291°C. Colourless blocks of (I) were obtained by recrystallizing from a mixed solvent of methanol and water (1:1).