Crystal structure of 2-(4-acetyl-anilino)-2-oxoethyl 3-(4-hy-droxy-phen-yl)propionate

Acta Crystallogr E Crystallogr Commun. 2016 Jun 10;72(Pt 7):933-6. doi: 10.1107/S205698901600894X. eCollection 2016 Jul 1.

Abstract

In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms. The 4-hy-droxy-hydro-cinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12). The N-(C=O)-C plane of the acetamide group and the acetate O-(C=O)-C plane are almost co-planar; the acetamide plane makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the acetate planes of the major and minor occupancy components. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular sheet structure parallel to (102).

Keywords: N—H⋯O and O—H⋯O hydrogen bonds; cinnamate ester; crystal structure; tyrosinase inhibitor.