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Hydrogen-bonded sheet structures in methyl 4-(4-chloroanilino)-3-nitrobenzoate and methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate. 2013

Edwar Cortés, and Rodrigo Abonía, and Justo Cobo, and Christopher Glidewell
Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.

In methyl 4-(4-chloroanilino)-3-nitrobenzoate, C(14)H(11)ClN(2)O(4), (I), there is an intramolecular N-H...O hydrogen bond and the intramolecular distances provide evidence for electronic polarization of the o-quinonoid type. The molecules are linked into sheets built from N-H...O, C-H...O and C-H...π(arene) hydrogen bonds, together with an aromatic π-π stacking interaction. The molecules of methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate, C(22)H(17)ClN(2)O(2), (II), are also linked into sheets, this time by a combination of C-H...π(arene) hydrogen bonds and aromatic π-π stacking interactions.

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