N-(1,4-Dioxo-1,4-dihydronaphthalen-2yl)benzamide

The title compound, C17H11NO3, was an intermediate synthesized during bisacylation of 2-amino-1,4-naphthoquinone with benzoyl chloride. A mixture of block-and needle-shaped crystals were obtained after column chromatography. The block-shaped crystals were identified as the imide and the needles were the title amide. The naphthoquinone scaffold is roughly planar (r.m.s. deviation = 0.047 A for the C atoms). The N-H and C=O bonds of the amide group are anti to each other. A dihedral angle between the naphthoquinone ring system and the amide group of 3.56 (3)degrees, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51 (3)degrees, makes the naphthoquinone ring essentially coplanar with the phenyl ring [dihedral angle = 7.12 (1)degrees]. In the crystal, molecules are linked by a weak N-H center dot center dot center dot O hydrogen bond and by two weak C-H center dot center dot center dot O interactions leading to the formation of zigzag chains along [010].