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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...

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Autores principales: Kansiz, Sevgi, Dege, Necmi, Aydin, Alev Sema, Ağar, Erbil, Matushko, Igor P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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.
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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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