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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...

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Autores principales: Demir Kanmazalp, Sibel, Doĝan, Onur Erman, Taşdemir, Volkan, Dege, Necmi, Aĝar, Erbil, Fritsky, Igor O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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%).
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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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