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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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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. |
format | Online Article Text |
id | pubmed-7336782 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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