N-(1,4-Dioxo-1,4-dihydro­naphthalen-2-yl)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 Å 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)°, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51 (3)°, makes the naphtho­quinone 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].