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

The title compound, C(12)H(11)N(3)O(2), is a second monoclinic polymorph (P2(1), with Z′ = 4) of the previously reported monoclinic (P2(1)/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].