Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol

The title compound, C(15)H(14)ClNO, was synthesized by condensation reaction of 2-hy­droxy-5-methyl­benzaldehyde and 3-chloro-4-methyl­aniline, and crystallizes in the monoclinic space group P2(1)/c. The 3-chloro­benzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the...

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Autores principales: Faizi, Md. Serajul Haque, Cinar, Emine Berrin, Aydin, Alev Sema, Agar, Erbil, Dege, Necmi, Mashrai, Ashraf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7405573/
https://www.ncbi.nlm.nih.gov/pubmed/32844022
http://dx.doi.org/10.1107/S2056989020009421
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author Faizi, Md. Serajul Haque
Cinar, Emine Berrin
Aydin, Alev Sema
Agar, Erbil
Dege, Necmi
Mashrai, Ashraf
author_facet Faizi, Md. Serajul Haque
Cinar, Emine Berrin
Aydin, Alev Sema
Agar, Erbil
Dege, Necmi
Mashrai, Ashraf
author_sort Faizi, Md. Serajul Haque
collection PubMed
description The title compound, C(15)H(14)ClNO, was synthesized by condensation reaction of 2-hy­droxy-5-methyl­benzaldehyde and 3-chloro-4-methyl­aniline, and crystallizes in the monoclinic space group P2(1)/c. The 3-chloro­benzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intra­molecular O—H⋯N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (43.8%) and C⋯H/H⋯C (26.7%) 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.
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spelling pubmed-74055732020-08-24 Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol Faizi, Md. Serajul Haque Cinar, Emine Berrin Aydin, Alev Sema Agar, Erbil Dege, Necmi Mashrai, Ashraf Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(15)H(14)ClNO, was synthesized by condensation reaction of 2-hy­droxy-5-methyl­benzaldehyde and 3-chloro-4-methyl­aniline, and crystallizes in the monoclinic space group P2(1)/c. The 3-chloro­benzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intra­molecular O—H⋯N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (43.8%) and C⋯H/H⋯C (26.7%) 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. International Union of Crystallography 2020-07-21 /pmc/articles/PMC7405573/ /pubmed/32844022 http://dx.doi.org/10.1107/S2056989020009421 Text en © Faizi 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
Faizi, Md. Serajul Haque
Cinar, Emine Berrin
Aydin, Alev Sema
Agar, Erbil
Dege, Necmi
Mashrai, Ashraf
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
title Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
title_full Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
title_fullStr Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
title_full_unstemmed Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
title_short Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
title_sort crystal structure, hirshfeld surface analysis and dft studies of (e)-2-{[(3-chloro-4-methyl­phen­yl)imino]­meth­yl}-4-methyl­phenol
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7405573/
https://www.ncbi.nlm.nih.gov/pubmed/32844022
http://dx.doi.org/10.1107/S2056989020009421
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