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Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol

In the title compound, C(15)H(15)NO, the configuration of the C=N bond of the Schiff base is E, and an intra­molecular O—H⋯N hydrogen bond is observed, forming an intra­molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol­ecules...

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Autores principales: Yagci, Nermin Kahveci, Faizi, Md. Serajul Haque, Aydin, Alev Sema, Dege, Necmi, Dogan, Onur Erman, Agar, Erbil, Mashrai, Ashraf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7336782/
https://www.ncbi.nlm.nih.gov/pubmed/32695455
http://dx.doi.org/10.1107/S2056989020007847
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author Yagci, Nermin Kahveci
Faizi, Md. Serajul Haque
Aydin, Alev Sema
Dege, Necmi
Dogan, Onur Erman
Agar, Erbil
Mashrai, Ashraf
author_facet Yagci, Nermin Kahveci
Faizi, Md. Serajul Haque
Aydin, Alev Sema
Dege, Necmi
Dogan, Onur Erman
Agar, Erbil
Mashrai, Ashraf
author_sort Yagci, Nermin Kahveci
collection PubMed
description In the title compound, C(15)H(15)NO, the configuration of the C=N bond of the Schiff base is E, and an intra­molecular O—H⋯N hydrogen bond is observed, forming an intra­molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol­ecules are linked along the b axis by O—H⋯N and C—H⋯O hydrogen bonds, forming polymeric chains. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (56.9%) and H⋯C/C⋯H (31.2%) inter­actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined mol­ecular structure, and the HOMO–LUMO energy gap is provided. The crystal studied was refined as an inversion twin.
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spelling pubmed-73367822020-07-20 Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol Yagci, Nermin Kahveci Faizi, Md. Serajul Haque Aydin, Alev Sema Dege, Necmi Dogan, Onur Erman Agar, Erbil Mashrai, Ashraf Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, C(15)H(15)NO, the configuration of the C=N bond of the Schiff base is E, and an intra­molecular O—H⋯N hydrogen bond is observed, forming an intra­molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol­ecules are linked along the b axis by O—H⋯N and C—H⋯O hydrogen bonds, forming polymeric chains. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (56.9%) and H⋯C/C⋯H (31.2%) inter­actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined mol­ecular structure, and the HOMO–LUMO energy gap is provided. The crystal studied was refined as an inversion twin. International Union of Crystallography 2020-06-16 /pmc/articles/PMC7336782/ /pubmed/32695455 http://dx.doi.org/10.1107/S2056989020007847 Text en © Yagci et al. 2020 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
Yagci, Nermin Kahveci
Faizi, Md. Serajul Haque
Aydin, Alev Sema
Dege, Necmi
Dogan, Onur Erman
Agar, Erbil
Mashrai, Ashraf
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
title Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
title_full Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
title_fullStr Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
title_full_unstemmed Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
title_short Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
title_sort crystal structure, hirshfeld surface analysis and dft studies of (e)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7336782/
https://www.ncbi.nlm.nih.gov/pubmed/32695455
http://dx.doi.org/10.1107/S2056989020007847
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