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

Abstract

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 6-311g+(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].