Structural study and Hirshfeld surface analysis of (Z)-4-(2-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one

Abstract

The title compound, C17H13NO3, adopts a Z configuration about the C=C bond. The isoxazole and methoxybenzylidene rings are almost coplanar with a dihedral angle of 9.63 (7)° between them. In contrast, the phenyl substituent is twisted significantly out of the plane of the oxazole ring, with the two rings inclined to each other by 46.22 (4)°. The crystal structure features C—H...O, C—H...N and C—H...π hydrogen bonds and π–π contacts. An analysis of the Hirshfeld surfaces points to the importance of H...H, H...C/C...H and H...O/O...H contacts. The included surface areas of the title compound were compared to those of the isomeric structure (Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one [Zhang et al. (2015). CrystEngComm, 17, 7316–7322].

Keywords

• crystal structure
• methoxybenzylidene
• isoxazole
• hydrogen bonding
• π–π stacking
• hirshfeld surface analysis