2-Amino-5-nitro-phenyl 2-chloro-phenyl ketone

Abstract

In the title compound, C13H9ClN2O 3, an intra-molecular hydrogen bond between the carbonyl O and an amine H atom from the 2-amino-benzoyl group stabilizes the mol-ecule, keeping these two groups nearly in the same plane [dihedral angle 14.6 (6)°]. The dihedral angle between the mean planes of the planar 2-amino-benzoyl and 2-chloro-benzoyl groups is 73.8 (6)°. The crystal packing is stabilized by a collection of inter-mediate hydrogen-bonding inter-actions which forms an infinite N - H⋯O⋯H - N - H⋯O hydrogen-bonded chain along the c axis in concert with weak N - H⋯Cl inter-actions in the same direction, producing a two-dimensional inter-molecular bonding network parallel to (001). Additional weak C - Cl⋯Cg [Cl⋯Cg = 3.858 (3) Å] and N - O⋯Cg [O⋯Cg = 3.574 (1) and 3.868 (6) Å] π-ring inter-actions provide added support to the crystal stability. A MOPAC computational calculation gives support to these observations. © 2009 Jasinski et al.