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

ABSTRACT: In the title compound, C(13)H(9)ClN(2)O(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] ?-ring inter-actions provide added support to the crystal stability. A MOPAC computational calculation gives support to these observations.

SUBMITTER: Jasinski JP 

PROVIDER: S-EPMC2977436 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature