N-(3-Chloro-phen-yl)-3-nitro-pyridin-2-amine

Acta Crystallogr Sect E Struct Rep Online. 2011 Nov;67(Pt 11):o3076. doi: 10.1107/S1600536811044011. Epub 2011 Oct 29.

Abstract

The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65 (10)°, indicating a twisted mol-ecule. The amine H and nitro O atoms form a donor-acceptor pair for an intra-molecular N-H⋯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O-N-C-C torsion angle = 7.4 (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C-H⋯Cl inter-actions that lead to undulating supra-molecular chains along [101]. These are connected into sheets by π-π inter-actions occurring between the benzene rings and between the pyridine rings of translationally related mol-ecules along the b axis [centroid-centroid distances = length of b axis = 3.7157 (2) Å].