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Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one

The title compound, C(15)H(15)NO(2), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The mol­ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra­molecular N—H⋯O hydrogen bond present forming...

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Autores principales: Kansiz, Sevgi, Aydin, Alev Sema, Dege, Necmi, Agar, 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/PMC6658948/
https://www.ncbi.nlm.nih.gov/pubmed/31391966
http://dx.doi.org/10.1107/S2056989019006583
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author Kansiz, Sevgi
Aydin, Alev Sema
Dege, Necmi
Agar, Erbil
Fritsky, Igor O.
author_facet Kansiz, Sevgi
Aydin, Alev Sema
Dege, Necmi
Agar, Erbil
Fritsky, Igor O.
author_sort Kansiz, Sevgi
collection PubMed
description The title compound, C(15)H(15)NO(2), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The mol­ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra­molecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers with an R (2) (2)(18) ring motif. The dimers are linked by very weak π–π inter­actions, forming layers parallel to ([Image: see text]01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol­ecular electrostatic potential surfaces were used to analyse the inter­molecular inter­actions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) inter­actions.
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spelling pubmed-66589482019-08-07 Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one Kansiz, Sevgi Aydin, Alev Sema Dege, Necmi Agar, Erbil Fritsky, Igor O. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(15)H(15)NO(2), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The mol­ecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intra­molecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers with an R (2) (2)(18) ring motif. The dimers are linked by very weak π–π inter­actions, forming layers parallel to ([Image: see text]01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the mol­ecular electrostatic potential surfaces were used to analyse the inter­molecular inter­actions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) inter­actions. International Union of Crystallography 2019-05-14 /pmc/articles/PMC6658948/ /pubmed/31391966 http://dx.doi.org/10.1107/S2056989019006583 Text en © Kansiz 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
Kansiz, Sevgi
Aydin, Alev Sema
Dege, Necmi
Agar, Erbil
Fritsky, Igor O.
Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
title Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
title_full Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
title_fullStr Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
title_short Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
title_sort crystal structure and hirshfeld surface analysis of (z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658948/
https://www.ncbi.nlm.nih.gov/pubmed/31391966
http://dx.doi.org/10.1107/S2056989019006583
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