Cyano–cyano and chloro–cyano interactions in two imidazole derivatives

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In two closely related 1-aryl-2-methyl-4-nitro-5-cyano­imid­azoles, namely 2-methyl-4-nitro-1-phenyl-1H-imidazole-5-carbo­nitrile, C11H8N4O2, and 1-(4-chloro­phenyl)-2-methyl-4-nitro-1H-imidazole-5-carbo­nitrile, C11H7ClN4O2, different weak intermolecular interactions determine the crystal packing. In the 1-phenyl derivative, dipole–dipole interactions between antiparallel cyano groups connect mol­ecules into centrosymmetric dimers, while in the 1-(4-chloro­phenyl) derivative, the dimers are connected by C≡N…Cl—C halogen bonds. These interactions, together with weak C—H…O(N) hydrogen bonds, connect mol­ecules related by subsequent centres of inversion into infinite tapes.

Document Type: Research Article


Publication date: April 1, 2004

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