2-Amino-5-nitro­phenyl 2-chloro­phenyl ketone

In the title compound, C(13)H(9)ClN(2)O(3), an intra­molecular hydrogen bond between the carbonyl O and an amine H atom from the 2-amino­benzoyl group stabilizes the mol­ecule, 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-amino­benzoyl and 2-chloro­benzoyl groups is 73.8 (6)°. The crystal packing is stabilized by a collection of inter­mediate hydrogen-bonding inter­actions 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 inter­actions in the same direction, producing a two-dimensional inter­molecular 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 inter­actions provide added support to the crystal stability. A MOPAC computational calculation gives support to these observations.