N-(2-Nitrophenyl)benzamide

Abstract

In the title compound, C13H10N2O3, the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitrobenzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intramolecular N—H...O interaction to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C—H...O contacts generate two centrosymmetric ring systems with R22(14) and R22(20) graph-set motifs, forming zigzag chains down the a axis. π–π interactions between adjacent phenyl and nitrobenzene rings [centroid–centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C—H...O hydrogen bond generate an extensive three-dimensional network structure.