A new polymorph of the title compound, C10H13NO, was obtained by recrystallization of the commercial product from a water/ethanol mixture (1:1 v/v). Crystals of the previously reported racemic and homochiral forms of 2-phenyl-butyramide were grown from water-aceto-nitrile solution in 1:1 volume ratio [Khrustalev et al. (2014 ▸). Cryst. Growth Des. 14, 3360-3369]. While the previously reported racemic and enanti-opure forms of the title compound adopt very similar supra-molecular structures (hydrogen-bonded ribbons), the new racemic polymorph is stabilized by a single N-H⋯O hydrogen bond that links mol-ecules into chains along the c-axis direction with an anti-parallel (centrosymmetric) packing in the crystal. Hirshfeld mol-ecular surface analysis was employed to compare the inter-molecular inter-actions in the polymorphs of the title compound.
Keywords: 2-phenylbutyramide; Hirshfeld surface analysis; crystal structure; hydrogen bonds; racemate.