Ethenzamide-gentisic acid-acetic acid (2/1/1)

Abstract

In the title co-crystal solvate, 2-ethoxy-benzamide-2,5-dihydroxy-benzoic acid-ethanoic acid (2/1/1), 2C9H11NO2· C7H6O4·C2H4O 2, two nonsteroidal anti-inflammatory drugs, ethenzamide (systematic name: 2-ethoxy-benzamide) and gentisic acid (systematic name: 2,5-dihydroxy-benzoic acid), together with acetic acid (systematic name: ethanoic acid) form a four-component molecular assembly held together by N - H⋯O and O - H⋯O hydrogen bonds. This assembly features two symmetry-independent molecules of ethenzamide, forming supra-molecular acid-amide heterosynthons with gentisic acid and acetic acid. These heterosynthons involve quite strong O - H⋯O [O⋯O = 2.5446 (15) and 2.5327 (15) Å] and less strong N - H⋯O [N⋯O = 2.9550 (17) and 2.9542 (17) Å] hydrogen bonds. The overall crystal packing features several C - H⋯O and π-π stacking interactions [centroid-centroid distance = 3.7792 (11) Å]. © 2010.