2-[(1H-Benzimidazol-2-yl)imino­meth­yl]-4,6-dibromo­phenol ethanol hemisolvate

Jie Liu; Zheng Liu; Shuai Yuan

doi:10.1107/S1600536813002031

. 2013 Feb 9;69(Pt 3):o362. doi: 10.1107/S1600536813002031

2-[(1H-Benzimidazol-2-yl)iminomethyl]-4,6-dibromophenol ethanol hemisolvate

Jie Liu ^a,^*, Zheng Liu ^a, Shuai Yuan ^a

PMCID: PMC3588477 PMID: 23476552

Abstract

The title compound, C₁₄H₉Br₂N₃O·0.5C₂H₅OH, crystallizes with two 2-[(1H-benzimidazol-2-yl)iminomethyl]-4,6-dibromophenol molecules and one ethanol solvent molecule in the asymmetric unit. The benzene and benzimidazole rings subtend dihedral angles of 4.5 (3) and 5.2 (2)° in the two molecules. In the crystal, one molecule presents π–π stacking with the equivalent molecule related by inversion, at a distance of 3.30 Å (separation between molecular mean planes). A three-dimensional network is formed through N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For background to benzimidazole compounds, see: Zhang et al. (2008 ▶, 2011 ▶). graphic file with name e-69-0o362-scheme1.jpg

Experimental

Crystal data

C₁₄H₉Br₂N₃O·0.5C₂H₆O
M _r = 836.19
Monoclinic,
a = 14.5300 (15) Å
b = 16.8190 (14) Å
c = 13.8491 (17) Å
β = 111.656 (13)°
V = 3145.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 5.16 mm⁻¹
T = 293 K
0.23 × 0.22 × 0.21 mm

Data collection

Agilent SuperNova Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.436, T _max = 1.000
19465 measured reflections
6390 independent reflections
4189 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.133
S = 1.03
6390 reflections
392 parameters
H-atom parameters constrained
Δρ_max = 1.55 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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

Click here for additional data file.^{(24.4KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002031/bh2461sup1.cif

e-69-0o362-sup1.cif^{(24.4KB, cif)}

Click here for additional data file.^{(312.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002031/bh2461Isup2.hkl

e-69-0o362-Isup2.hkl^{(312.8KB, hkl)}

Click here for additional data file.^{(3.8KB, cdx)}

Supplementary material file. DOI: 10.1107/S1600536813002031/bh2461Isup3.cdx

Click here for additional data file.^{(6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813002031/bh2461Isup4.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
N5—H5⋯N3	0.86	2.14	2.997 (4)	172
N2—H2A⋯O3ⁱ	0.86	2.00	2.816 (4)	157
O1—H1⋯N1	0.82	1.90	2.618 (6)	146
O2—H2⋯N4	0.82	1.92	2.640 (6)	147
O3—H3⋯N6ⁱⁱ	0.82	2.08	2.900 (5)	176

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

Acknowledgments

The authors acknowledge financial support by the National Natural Science Foundation of China (No. 2126606).

supplementary crystallographic information

Comment

Benzimidazole compounds exhibit a large range of biological activities and so far various types of benzimidazole drugs have been extensively used in clinic practice (Zhang et al., 2008, 2011). Herein, we have synthesized a new benzimidazole compound.

In the title compound, the benzene and benzimidazole rings are almost in the same plane, and the dihedral angle between the benzene and benzimidazole rings is 4.5 (3) and 5.2 (2)° for each crystallographically independent molecule (Fig. 1). π–π stacking interactions are observed between the benzene and benzimidazole rings of molecules C1···C14 related by inversion: the dihedral angle between stacked molecules is 0°, and the separation between mean planes formed by the benzene and the benzimidazole rings in the molecules is 3.487 Å (Fig. 2). The title compound forms a three-dimensional network in the crystal structure, through N—H···N, N—H···O and O—H···N hydrgoen bonds (Fig. 3).

Experimental

3,5-Dibromosalicylaldehyde (3.0 mmol) was dissolved in a round bottom flask containing ethanol (20 ml). To this solution, an ethanolic solution (10 ml) of 2-aminobenzimidazole (3.0 mmol) was then added dropwise, and the mixture was refluxed for 4 h. After cooling down to room temperature, the resulting orange precipitate was filtered off, and recrystallized from ethanol. Orange block-like crystals of the title compound were obtained by slow evaporation of the filtrate at room temperature.