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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...
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/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. |
format | Online Article Text |
id | pubmed-6658948 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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