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Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one
The title compound, C(14)H(12)ClNO(3), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the molecule is stabilized by a strong intra...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6399700/ https://www.ncbi.nlm.nih.gov/pubmed/30867950 http://dx.doi.org/10.1107/S2056989019002123 |
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author | Demir Kanmazalp, Sibel Doĝan, Onur Erman Taşdemir, Volkan Dege, Necmi Aĝar, Erbil Fritsky, Igor O. |
author_facet | Demir Kanmazalp, Sibel Doĝan, Onur Erman Taşdemir, Volkan Dege, Necmi Aĝar, Erbil Fritsky, Igor O. |
author_sort | Demir Kanmazalp, Sibel |
collection | PubMed |
description | The title compound, C(14)H(12)ClNO(3), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the molecule is stabilized by a strong intramolecular N—H⋯O hydrogen bond. In the crystal, pairs of centrosymmetrically related molecules are linked by O—H⋯O hydrogen bonds, forming R (2) (2)(10) rings. Besides this, the molecules form stacks along the [001] direction with C—H⋯π and C—H⋯Cl contacts between the stacks. The intermolecular interactions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H⋯H contacts (30.8%). |
format | Online Article Text |
id | pubmed-6399700 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-63997002019-03-13 Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one Demir Kanmazalp, Sibel Doĝan, Onur Erman Taşdemir, Volkan Dege, Necmi Aĝar, Erbil Fritsky, Igor O. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(14)H(12)ClNO(3), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the molecule is stabilized by a strong intramolecular N—H⋯O hydrogen bond. In the crystal, pairs of centrosymmetrically related molecules are linked by O—H⋯O hydrogen bonds, forming R (2) (2)(10) rings. Besides this, the molecules form stacks along the [001] direction with C—H⋯π and C—H⋯Cl contacts between the stacks. The intermolecular interactions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H⋯H contacts (30.8%). International Union of Crystallography 2019-02-12 /pmc/articles/PMC6399700/ /pubmed/30867950 http://dx.doi.org/10.1107/S2056989019002123 Text en © Demir Kanmazalp et al. 2019 http://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.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Demir Kanmazalp, Sibel Doĝan, Onur Erman Taşdemir, Volkan Dege, Necmi Aĝar, Erbil Fritsky, Igor O. Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
title | Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
title_full | Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
title_fullStr | Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
title_short | Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
title_sort | crystal structure and hirshfeld surface analysis of a schiff base: (z)-6-[(5-chloro-2-methoxyanilino)methylidene]-2-hydroxycyclohexa-2,4-dien-1-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6399700/ https://www.ncbi.nlm.nih.gov/pubmed/30867950 http://dx.doi.org/10.1107/S2056989019002123 |
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