Publication Details

Wagner, P. & Kubicki, M. (2007). 5-Methoxy-2-methyl-4-nitro-1-phenyl-1H-imidazole. Acta Crystallographica Section E: Structure Reports Online, 63 (8), o3587.


The title compound, C11H11N3O3, contains two planar fragments, viz. the imidazole and phenyl rings. These rings are significantly twisted with respect one to another, with a dihedral angle of 63.99 (8)°. The nitro group is almost coplanar with the imidazole plane, while the methoxy group is almost perpendicular to it [the C—C—O—C torsion angle is 65.1 (4)°]. In spite of this, there is a short C(methoxy)—H...O(nitro) contact that might be regarded as an intramolecular hydrogen bond. Weak intermolecular C—H...N(imidazole) and C—H...O(nitro) hydrogen bonds create quite a complicated network that consists of stacks of imidazole rings strengthened by these hydrogen bonds. The significant twist between the planar fragments is a necessary condition for creating such a packing, which has also been observed in some other 1-aryl-4-nitroimidazole derivatives.



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