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

Abstract

In the title co-crystal solvate, 2-ethoxy­benzamide–2,5-dihydroxy­benzoic acid–ethanoic acid (2/1/1), 2C9H11NO2·C7H6O4·C2H4O2, two nonsteroidal anti-inflammatory drugs, ethenzamide (systematic name: 2-ethoxy­benzamide) and gentisic acid (systematic name: 2,5-dihydroxy­benzoic 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 supra­molecular 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].