Acta Cryst. (2012). E68, o2775-o2776
[ doi:10.1107/S1600536812034150 ]

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

Y. Brandy, R. J. Butcher and O. Bakare

Abstract: 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-HO hydrogen bond and by two weak C-HO interactions leading to the formation of zigzag chains along [010].

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