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Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one
The title compound, C(14)H(12)N(2)O(4), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond form...
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/PMC6658968/ https://www.ncbi.nlm.nih.gov/pubmed/31391972 http://dx.doi.org/10.1107/S205698901900673X |
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author | Kansiz, Sevgi Dege, Necmi Aydin, Alev Sema Ağar, Erbil Matushko, Igor P. |
author_facet | Kansiz, Sevgi Dege, Necmi Aydin, Alev Sema Ağar, Erbil Matushko, Igor P. |
author_sort | Kansiz, Sevgi |
collection | PubMed |
description | The title compound, C(14)H(12)N(2)O(4), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related molecules are linked by pairs of O—H⋯O hydrogen bonds, forming dimers with an R (2) (2)(18) ring motif. The dimers are linked by pairs of C—H⋯O contacts with an R (2) (2)(10) ring motif, forming ribbons extended along the [2[Image: see text]0] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (33.9%), O⋯H/H⋯O (29.8%) and C⋯H/H⋯C (17.3%) interactions. |
format | Online Article Text |
id | pubmed-6658968 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-66589682019-08-07 Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one Kansiz, Sevgi Dege, Necmi Aydin, Alev Sema Ağar, Erbil Matushko, Igor P. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(14)H(12)N(2)O(4), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, the rings making a dihedral angle of 4.99 (7)°. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related molecules are linked by pairs of O—H⋯O hydrogen bonds, forming dimers with an R (2) (2)(18) ring motif. The dimers are linked by pairs of C—H⋯O contacts with an R (2) (2)(10) ring motif, forming ribbons extended along the [2[Image: see text]0] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (33.9%), O⋯H/H⋯O (29.8%) and C⋯H/H⋯C (17.3%) interactions. International Union of Crystallography 2019-05-17 /pmc/articles/PMC6658968/ /pubmed/31391972 http://dx.doi.org/10.1107/S205698901900673X 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 Dege, Necmi Aydin, Alev Sema Ağar, Erbil Matushko, Igor P. Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
title | Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
title_full | Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
title_fullStr | Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
title_short | Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
title_sort | crystal structure and hirshfeld surface analysis of (z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658968/ https://www.ncbi.nlm.nih.gov/pubmed/31391972 http://dx.doi.org/10.1107/S205698901900673X |
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