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

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 77; no. 5; pp. 564 - 568
• Main Authors: Benouatas, Assia, Laroum, Rima, Hamdouni, Noudjoud, Zemamouche, Wissame, Debache, Abdelmadjid, Boudjada, Ali
• Format: Journal Article
• Language: English
• Published: International Union of Crystallography 01-05-2021
• Subjects: crystal structure; hirshfeld surface analysis; hydrogen bonding; isoxazole; methoxybenzylidene; π–π stacking
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989021004308

The title compound, C
17
H
13
NO
3
, 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(4
H
)-one [Zhang
et al.
(2015).
CrystEngComm
,
17
, 7316–7322].