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Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol
The title compound, C(20)H(24)BrNO(2), is chiral at the carbon atoms on either side of the oxygen atom of the oxazolidine ring and crystallizes as a racemate. The 1,3-oxazolidine ring adopts an envelope conformation with the N atom in an endo position. The mean plane of the oxazolidine ring makes di...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9260360/ https://www.ncbi.nlm.nih.gov/pubmed/35855370 http://dx.doi.org/10.1107/S2056989022005928 |
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author | Khalilov, Ali N. Khrustalev, Victor N. Fortalnova, Elena A. Akkurt, Mehmet Yıldırım, Sema Öztürk Bhattarai, Ajaya Mamedov, İbrahim G. |
author_facet | Khalilov, Ali N. Khrustalev, Victor N. Fortalnova, Elena A. Akkurt, Mehmet Yıldırım, Sema Öztürk Bhattarai, Ajaya Mamedov, İbrahim G. |
author_sort | Khalilov, Ali N. |
collection | PubMed |
description | The title compound, C(20)H(24)BrNO(2), is chiral at the carbon atoms on either side of the oxygen atom of the oxazolidine ring and crystallizes as a racemate. The 1,3-oxazolidine ring adopts an envelope conformation with the N atom in an endo position. The mean plane of the oxazolidine ring makes dihedral angles of 77.74 (10) and 45.50 (11)°, respectively, with the 4-bromophenol and 1,3,5-trimethylbenzene rings. In the crystal, adjacent molecules are connected via C—H⋯O hydrogen bonds and C—H⋯π interactions into layers parallel to the (200) plane. The packing is strengthened by van der Waals interactions between parallel molecular layers. A Hirshfeld surface analysis shows that H⋯H (58.2%), C⋯H/H⋯C (18.9%), and Br⋯H/H⋯Br (11.5%) interactions are the most abundant in the crystal packing. |
format | Online Article Text |
id | pubmed-9260360 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-92603602022-07-18 Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol Khalilov, Ali N. Khrustalev, Victor N. Fortalnova, Elena A. Akkurt, Mehmet Yıldırım, Sema Öztürk Bhattarai, Ajaya Mamedov, İbrahim G. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(20)H(24)BrNO(2), is chiral at the carbon atoms on either side of the oxygen atom of the oxazolidine ring and crystallizes as a racemate. The 1,3-oxazolidine ring adopts an envelope conformation with the N atom in an endo position. The mean plane of the oxazolidine ring makes dihedral angles of 77.74 (10) and 45.50 (11)°, respectively, with the 4-bromophenol and 1,3,5-trimethylbenzene rings. In the crystal, adjacent molecules are connected via C—H⋯O hydrogen bonds and C—H⋯π interactions into layers parallel to the (200) plane. The packing is strengthened by van der Waals interactions between parallel molecular layers. A Hirshfeld surface analysis shows that H⋯H (58.2%), C⋯H/H⋯C (18.9%), and Br⋯H/H⋯Br (11.5%) interactions are the most abundant in the crystal packing. International Union of Crystallography 2022-06-10 /pmc/articles/PMC9260360/ /pubmed/35855370 http://dx.doi.org/10.1107/S2056989022005928 Text en © Khalilov et al. 2022 https://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. |
spellingShingle | Research Communications Khalilov, Ali N. Khrustalev, Victor N. Fortalnova, Elena A. Akkurt, Mehmet Yıldırım, Sema Öztürk Bhattarai, Ajaya Mamedov, İbrahim G. Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
title | Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
title_full | Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
title_fullStr | Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
title_short | Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
title_sort | crystal structure and hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9260360/ https://www.ncbi.nlm.nih.gov/pubmed/35855370 http://dx.doi.org/10.1107/S2056989022005928 |
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