Crystal structure of methyl (E)-4-[2-(8-hydroxyquinolin-2-yl)vinyl]benzoate

Abstract

The title compound, C19H15NO3, was synthesized by a Perkin reaction of 2-methyl-8-hydroxyquinoline and 4-formyl-2-methylbenzoate in acetic anhydride under a nitrogen atmosphere. The molecule has an E conformation about the C=C bond, and the quinoline ring system and the benzene ring are inclined to one another by 29.22 (7)°. There is an intramolecular O—H...N hydrogen bond in the 8-hydroxyquinoline moiety. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with an R22(28) ring motif. The dimers are linked by C—H...O hydrogen bonds and C—H...π interactions, forming sheets parallel to plane (10-1).

Keywords

• crystal structure
• 8-hydroxyquinoline derivative
• vinyl
• inversion dimer
• hydrogen bonding
• inversion dimers
• C—H...π interactions