4-Bromo-2-meth­oxy-6-(1-phenyl-1H-benzimidazol-2-yl)phenol

Shunsheng Zhao; Xiangrong Liu; Xingqiang Lü; Weixu Feng

doi:10.1107/S1600536812007313

. 2012 Feb 24;68(Pt 3):o852. doi: 10.1107/S1600536812007313

4-Bromo-2-methoxy-6-(1-phenyl-1H-benzimidazol-2-yl)phenol

Shunsheng Zhao ^a,^*, Xiangrong Liu ^a, Xingqiang Lü ^b, Weixu Feng ^b

PMCID: PMC3297907 PMID: 22412710

Abstract

The title compound, C₂₀H₁₅BrN₂O₂, crystallized with three independent molecules in the asymmetric unit. Intramolecular O—H⋯N hydrogen bonds induce coplanarity of the substituted benzene ring and the benzimidazole ring, with mean deviations from the planes of 0.0931 (10), 0.0448 (10) and 0.0083 (11) Å in the three molecules.

Related literature

For the properties and applications of similar compounds and their complexes, see: Piguet et al. (1993 ▶); Yang et al. (2006 ▶).

Experimental

Crystal data

C₂₀H₁₅BrN₂O₂
M _r = 395.25
Triclinic,
a = 12.377 (2) Å
b = 13.201 (2) Å
c = 17.474 (3) Å
α = 87.812 (3)°
β = 89.045 (3)°
γ = 64.652 (2)°
V = 2578.2 (8) Å³
Z = 6
Mo Kα radiation
μ = 2.41 mm⁻¹
T = 296 K
0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.379, T _max = 0.645
12738 measured reflections
8707 independent reflections
4152 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.178
S = 0.91
8707 reflections
679 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 and local programs.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007313/fy2036sup1.cif

e-68-0o852-sup1.cif^{(31.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007313/fy2036Isup2.hkl

e-68-0o852-Isup2.hkl^{(425.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812007313/fy2036Isup3.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
O2—H2B⋯N2	0.82	1.84	2.563 (6)	146
O4—H4A⋯N4	0.82	1.79	2.521 (7)	147
O6—H6B⋯N6	0.82	1.81	2.539 (7)	148

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Acknowledgments

The project was supported by the National Natural Science Foundation of China (grant Nos. 21103135, 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011), the Cultivation Foundation of Xi’an University of Science and Technology (program No. 2010023) and the Open Foundation of the Ministry of Education Key Laboratory of Synthetic and Natural Functional Molecular Chemistry at Northwest University (grant Nos. Z511025, 2010025).

supplementary crystallographic information

Comment

The title compound contains three coordination sites (Fig. 1) and could form chelate compounds with several metals (Piguet et al., 1993). A crystal packing diagram is shown in Fig. 2. The synthesis and structure of the title compound have not been reported previously, however, the synthesis and structure of a similar benzimidazole ligand and its 3d-4f bimetallic complex were described by Yang et al. (2006). Yang et al. (2006) also indicated that benzimidazole ligands could be synthesized from the reaction of substituted benzaldehyde and phenylene diamine.

Experimental

The solution of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (231.5 mg, 1.0 mmol) in ethanol (15 ml) was added to the solution of N-phenyl-1,2-phenylenediamine (184 mg, 1.0 mmol) in ethanol (10 ml) at room temperature. The mixture was stirred for 1 h before being heated to reflux, and was kept refluxing for another 2 h. Then it was cooled down to room temperature. The single crystal of the title compound suitble for X-ray diffraction was obtained by slow evaporation of the ethanolic solution.