N-(4-Methoxy-3-nitrophenyl)acetamide

Abstract

The title compound, C9H10N2O4, crystallizes with a disordered nitro group in twinned crystals. Both the methoxy group and the acetamide groups are nearly coplanar with the phenyl ring, and the C—N—C—O torsion angle [0.2 (4)°] is also insignificantly different from zero. Overall, the 12-atom methoxyphenylacetamide group is nearly planar, with an r.m.s. deviation of 0.042 Å. The nitro group is twisted out of this plane by about 30°, disordered into two orientations with opposite senses of twist. In the crystal, the N—H group donates a hydrogen bond to a nitro oxygen atom, generating chains propagating in the [101] direction. The amide carbonyl oxygen atom is not involved in the hydrogen bonding.

Keywords

• n-alkoxyacetanilides
• phenacetin congeners
• nitro products
• crystal structure
• hydrogen bonding