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

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...

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Autores principales: Benouatas, Assia, Laroum, Rima, Hamdouni, Noudjoud, Zemamouche, Wissame, Debache, Abdelmadjid, Boudjada, Ali
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100271/
https://www.ncbi.nlm.nih.gov/pubmed/34026266
http://dx.doi.org/10.1107/S2056989021004308
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author Benouatas, Assia
Laroum, Rima
Hamdouni, Noudjoud
Zemamouche, Wissame
Debache, Abdelmadjid
Boudjada, Ali
author_facet Benouatas, Assia
Laroum, Rima
Hamdouni, Noudjoud
Zemamouche, Wissame
Debache, Abdelmadjid
Boudjada, Ali
author_sort Benouatas, Assia
collection PubMed
description 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(4H)-one [Zhang et al. (2015 ▸). CrystEngComm, 17, 7316–7322].
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spelling pubmed-81002712021-05-21 Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one Benouatas, Assia Laroum, Rima Hamdouni, Noudjoud Zemamouche, Wissame Debache, Abdelmadjid Boudjada, Ali Acta Crystallogr E Crystallogr Commun Research Communications 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(4H)-one [Zhang et al. (2015 ▸). CrystEngComm, 17, 7316–7322]. International Union of Crystallography 2021-04-27 /pmc/articles/PMC8100271/ /pubmed/34026266 http://dx.doi.org/10.1107/S2056989021004308 Text en © Benouatas et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Benouatas, Assia
Laroum, Rima
Hamdouni, Noudjoud
Zemamouche, Wissame
Debache, Abdelmadjid
Boudjada, Ali
Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one
title Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one
title_full Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one
title_fullStr Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one
title_full_unstemmed Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one
title_short Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one
title_sort structural study and hirshfeld surface analysis of (z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4h)-one
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100271/
https://www.ncbi.nlm.nih.gov/pubmed/34026266
http://dx.doi.org/10.1107/S2056989021004308
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