N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis

Abstract

The title molecule, C11H8F3NO3, adopts a cis configuration across the –C=C– double bond in the side chain and the dihedral angle between the phenyl ring and side chain is 47.35 (1)°. The –COOH group adopts a syn conformation (O=C—O—H = 0°), unlike the anti conformation observed in related maleamic acids. In the crystal, inversion dimers linked by pairs of O—H...O hydrogen bonds are connected via N—H...O hydrogen bonds and C—H...O interactions into (100) sheets, which are cross-linked by another C—H...O interaction to result in a three-dimensional network. The Hirshfeld surface fingerprint plots show that the highest contribution to surface contacts arises from O...H/H...O contacts (26.5%) followed by H...F/F...H (23.4%) and H...H (17.3%).

Keywords

• crystal structure
• hydrogen bonds
• maleamic acids
• Hirshfeld surface