Hydrogen-bonding one-dimensional arrangement in the crystal of N-phenyl-2-hydroxyacetamide

The N-phenyl-2-hydroxyacetamide was obtained in crystalline form by a direct reaction of aniline with glycolic acid. The whole molecule in the crystal is non-planar, but the planar 2-hydroxyacetamide group is inclined by 7.8(1)° to the plane of the phenyl ring that is cis located to the carbonyl oxygen atom. The hydroxyl group is in trans position to the carbonyl oxygen atom. The molecules are linked by the NH⋯O and OH⋯O hydrogen bonds into one-dimensional chains along the a-axis. Additionally, the CH⋯π interactions interconnect the chains stabilizing the crystal structure. The X-ray geometry of the N-phenyl-2-hydroxyacetamide molecule has been compared with that obtained by the ab-initio molecular orbital calculated results that represents the geometry in the gas-phase.