Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide

Abstract

In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004Å) and makes a dihedral angle of 66.16(17)° with the benzene ring of the methoxyphenyl group. Two intramolecular N - H⋯O and N - H⋯N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C - H⋯O hydrogen bonds link the molecules into inversion dimers with R 2 2(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C - H⋯π and π-π-stacking interactions [centroid-to-centroid distances = 3.631(2) and 3.631(2)Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H⋯H (39.3%), C⋯H/H⋯C (18.0%), O⋯H/H⋯O (15.6) and S⋯H/H⋯S (10.2%) interactions.