2-{[(Dimethylamino)methylidene]amino}-5-nitrobenzonitrile

Abstract

The title molecule, C10H10N4O2, is almost planar and adopts an E configuration of the azomethine [C=N = 1.298 (2) Å] double bond. The benzene ring is attached to an essentially planar (r.m.s. deviation = 0.0226 Å) amidine moiety (N=CN/Me2), the dihedral angle between the two mean planes being 18.42 (11)°. The cyano group lies in the plane of the benzene ring [the C and N atoms deviating by 0.030 (3) and 0.040 (3) Å, respectively], while the nitro group makes a dihedral angle 5.8 (3)° with the benzene ring. There are two distinct intermolecular hydrogen bonds, C—H...O and C—H...N, that stabilize the crystal structure; the former interactions result in centrosymmetric dimers about inversion centers resulting in ten-membered rings, while the later give rise to chains of molecules running parallel to the b axis.