2-n-Butyl-6-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole–2-n-butyl-5-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole (0.759/0.241)

Abstract

The title compound, 0.759C19H21ClN2O2S·0.241C19H21ClN2O2S, was synthesized by aryl­sulfonyl­ation of 2-n-butyl-5-chloro-1H-benzimidazole in the presence of triethyl­amine. The crystal structure is composed of two mol­ecules, 2-n-butyl-6-chloro-1-(2,4-dimethylphenyl­sulfon­yl)-1H-benzimidazole and 1-(2,4-dimethylphenyl­sulfon­yl)-2-n-butyl-5-chloro-1H-benz­imidazole, in the refined ratio of 0.759 (4):0.241 (4) disordered at the same position in the unit cell. The mol­ecule has three essentially planar fragments viz. benzimidazole, dimethyl­benzene and n-butyl (r.m.s. deviations of 0.009, 0.024 and 0.003 Å, respectively). The angle between the benzimidazole and dimethyl­benzene fragments is 86.0 (1)°. In the crystal, pairs of inter­molecular C—H⋯π inter­actions form centrosymmetrical dimers, which are linked by weak inter­molecular C—H⋯O hydrogen bonds.

Crystal structures of arylsulfonylation products of 2-alkyl-5-substituted-1H-benzimidazoles

“…6). Similar C-HÁ Á Á and C-HÁ Á ÁO interactions were observed in the previously studied mixed crystal of 2-n-butyl-6-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole and 2-n-butyl-5-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole (Abdireymov et al, 2011).…”

“…The angles between the fragments are 83.4 (1) for (IA), 79.3 (1) for (IB), 87.1 (1) for (II), and 86.6 (1) for (III). These values do not differ significantly from the previously reported structures of related benzimidazole derivatives (Abdireymov et al, 2011). However, the orientation of the entities along the N1-S1 and S1-C8 bonds is different (Tables 1, 2 and 3).…”

“…Of these, five are 1-arylsulfonyl-2-alkyl(aryl)-1Hbenzimidazole derivatives. The most similar structures are 6-chloro-2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole (MEZDAY; Alla et al, 2013), and the mixed crystals of 2-n-butyl-6-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole and 2-n-butyl-5-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole (OCEVEZ; Abdireymov et al, 2011).…”