N-(4-Methyl-phen-yl)-3-nitro-pyridin-2-amine

Abstract

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(12)H(11)N(3)O(2). These differ in terms of the relative orientations of the benzene rings as seen in the respective dihedral angles formed between the pyridine and benzene rings [17.42 (16) and 34.64 (16)°]. Both mol-ecules are twisted about the amine-tolyl N-C bonds [respective torsion angles = 22.3 (5) and 35.9 (5)°] but only about the amine-pyridine N-C bond in the first independent mol-ecule [respective torsion angles = -11.7 (5) and 0.8 (5)°]. Intra-molecular N-H⋯O hydrogen bonds preclude the amine H atoms from forming significant inter-molecular inter-actions. The crystal packing features inter-molecular C-H⋯O and C-H⋯π and π-π [centroid-centroid distance: pyridine-benzene = 3.6442 (19) Å and pyridine-pyridine = 3.722 (2) Å] contacts.

Fig. 1.

The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 2.

The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 3.

Overlay diagram of the first independent molecule (shown in red) and the second independent molecule (shown in blue).

Fig. 4.

Unit-cell contents for (I) shown in projection down the a axis. The C–H···π and π–π contacts are shown as blue and purple dashed lines, respectively. The C–H···O interactions are largely obscured in this projection.