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5-Methoxy-2-methyl-4-nitro-1-phenyl-1H-imidazole

Journal Article


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Abstract


  • 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.

UOW Authors


Publication Date


  • 2007

Citation


  • 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.

Scopus Eid


  • 2-s2.0-34547799162

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2056&context=aiimpapers

Ro Metadata Url


  • http://ro.uow.edu.au/aiimpapers/1055

Start Page


  • o3587

Volume


  • 63

Issue


  • 8

Abstract


  • 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.

UOW Authors


Publication Date


  • 2007

Citation


  • 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.

Scopus Eid


  • 2-s2.0-34547799162

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2056&context=aiimpapers

Ro Metadata Url


  • http://ro.uow.edu.au/aiimpapers/1055

Start Page


  • o3587

Volume


  • 63

Issue


  • 8