Synthesis, crystal and molecular structures of 1-n-butyl-2-(3'-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3',4'-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile by C. Kazak, V. T. Yilmaz, H. Goker, and C. Kus

Crystal Research and Technology

Cryst. Res. Technol. 41, 528 (2006) - Abstract -

Synthesis, crystal and molecular structures of 1-n-butyl-2-(3'-chlorophenyl)-1H-benzimidazole-5-carbonitrile hemihydrate and 1-n-butyl-2-(3',4'-dimethoxyphenyl)-1H-benzimidazole-5-carbonitrile

C. Kazak, V. T. Yilmaz*, H. Goker**, and C. Kus**

Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Kurupelit, Samsun, Turkey
*Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Kurupelit, Samsun, Turkey
**Department of Pharmaceutical Chemistry, University of Ankara, Faculty of Pharmacy, Ankara, Turkey

Keywords	benzimidazole, 5-cyanobenzimidazole derivatives, crystal structure
PACS	61.66.Hq
DOI	10.1002/crat.200510617

Two types of 5-cyanobenzimidazole derivatives with 1-n-butyl-2-(3'-chlorophenyl), (C₁₈H₁₆N₃Cl)₂^.H₂O (1) and 1-n-butyl-2-(3',4'-dimethoxyphenyl), (C₂₀H₂₁N₃O₂) (2) were prepared and their crystal structures were solved and reported. (1) crystallizes in the triclinic space group P-1 with a = 8.7682(7), b = 12.9392(10), c = 15.4435(12) Å, α = 81.401(6)°, β = 76.073(6)°, γ = 77.479(6)°, Z = 2, V = 1651.4(2) Å³, while (2) crystallizes in the monoclinic space group C2/c with a = 23.1981(15), b = 9.2959(4), c = 16.5505(11) Å, α = 90.00°, β = 95.850(5)°, γ = 90.00°, Z = 8, V = 3550.5(4) Å³. There are two distinct molecules with similar conformations in the asymmetric unit of (1). The imidazole and phenyl rings, forming the benzimidazole system are coplanar, and the bicyclic benzimidazole and the phenyl rings are essentially planar. The benzimidazole ring systems make dihedral angles of 28.97(0.08) and 49.29(0.06)° with the phenyl rings in (1) and (2), respectively. The structure of (1) is defined by weak aromatic π-π interactions and intermolecular hydrogen bonds, while there are no conventional hydrogen bonds in (2), and its crystal packing is dominated by van der Waal's and dipole-dipole interactions.

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