N-(1,4-Dioxo-1,4-dihydro-naphthalen-2-yl)benzamide.

The title compound, C(17)H(11)NO(3), was an inter-mediate synthesized during bis-acyl-ation of 2-amino-1,4-naphtho-quinone 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 naphtho-quinone scaffold is roughly planar (r.m.s. deviation = 0.047†à 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 naphtho-quinone ring system and the amide group of 3.56†(3)°, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51†(3)°, makes the naphtho-quinone ring essentially coplanar with the phenyl ring [dihedral angle = 7.12†(1)°]. In the crystal, molecules are linked by a weak N-H⋯O hydrogen bond and by two weak C-H⋯O interactions leading to the formation of zigzag chains along [010].