Crystal structure of a new monoclinic polymorph of N-(4-methylphenyl)-3-nitropyridin-2-amine

The title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z′ = 4) of the previously reported monoclinic (P21/c, with Z′ = 2) form [Akhmad Aznan et al. (2010). Acta Cryst. E66, o2400]. Four independent molecules comprise the asymmetric unit, which have the common features of a syn disposition of the pyridine N atom and the toluene ring, and an intramolecular amine–nitro N—H...O hydrogen bond. The differences between molecules relate to the dihedral angles between the rings which range from 2.92 (19) to 26.24 (19)°. The geometry-optimized structure [B3LYP level of theory and 6–311 g+(d,p) basis set] has the same features except that the entire molecule is planar. In the crystal, the three-dimensional architecture is consolidated by a combination of C—H...O, C—H...π, nitro-N—O...π and π–π interactions [inter-centroid distances = 3.649 (2)–3.916 (2) Å].