3-(3-NITROANILINO)CYCLOHEX-2-EN-1-ONE - AN UNEXPECTED PRODUCT FROM THE COCRYSTALLIZATION OF M-NITROANILINE WITH 1,3-CYCLOHEXANEDIONE

The title compound, C12H12N2O3, is composed of a nitroanilino moiety and a cyclic alpha,beta-unsaturated ketone moiety. The nitro group is oriented anti to the carbonyl group and the cyclic ketone ring is in a puckered conformation with C9 as the out-of-plane atom, The shortened C11-N2 and C7-C12 bond lengths suggest that the amino group is conjugated with the alpha,beta-unsaturated ketone group. Intermolecular hydrogen bonds between the carbonyl O atom and the amino group link the molecules into infinite chains [N-H 0.88(3), H ... O-i 1.98(3), N ... O-i 2.858(3)Angstrom, N-H ... O-i 175(1)degrees; symmetry code: (i) 1 + x, y, z].