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(E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism
A new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, C(13)H(10)BrNO, is reported, together with a low-temperature structure determination of the previously published polymorph. Both polymorphs were found to have an intramolecular O—H⋯N hydrogen bond between the phenol OH group and th...
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/PMC7642768/ https://www.ncbi.nlm.nih.gov/pubmed/33148875 http://dx.doi.org/10.1107/S2053229620011560 |
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author | Mason, Helen E. Howard, Judith A. K. Sparkes, Hazel A. |
author_facet | Mason, Helen E. Howard, Judith A. K. Sparkes, Hazel A. |
author_sort | Mason, Helen E. |
collection | PubMed |
description | A new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, C(13)H(10)BrNO, is reported, together with a low-temperature structure determination of the previously published polymorph. Both polymorphs were found to have an intramolecular O—H⋯N hydrogen bond between the phenol OH group and the imine N atom, forming an S(6) ring. The crystals were observed to have different colours at room temperature, with the previously published polymorph being more orange and the new polymorph more yellow. The planarity of the molecule in the two polymorphs was found to be significantly different, with dihedral angles (Φ) between the two aromatic rings for the previously published ‘orange’ polymorph of Φ = 1.8 (2)° at 120 K, while the new ‘yellow’ polymorph had Φ = 45.6 (1)° at 150 K. It was also observed that both polymorphs displayed some degree of thermochromism and upon cooling the ‘orange’ polymorph became more yellow, while the ‘yellow’ polymorph became paler upon cooling. |
format | Online Article Text |
id | pubmed-7642768 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-76427682020-11-17 (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism Mason, Helen E. Howard, Judith A. K. Sparkes, Hazel A. Acta Crystallogr C Struct Chem Research Papers A new polymorph of (E)-4-bromo-2-[(phenylimino)methyl]phenol, C(13)H(10)BrNO, is reported, together with a low-temperature structure determination of the previously published polymorph. Both polymorphs were found to have an intramolecular O—H⋯N hydrogen bond between the phenol OH group and the imine N atom, forming an S(6) ring. The crystals were observed to have different colours at room temperature, with the previously published polymorph being more orange and the new polymorph more yellow. The planarity of the molecule in the two polymorphs was found to be significantly different, with dihedral angles (Φ) between the two aromatic rings for the previously published ‘orange’ polymorph of Φ = 1.8 (2)° at 120 K, while the new ‘yellow’ polymorph had Φ = 45.6 (1)° at 150 K. It was also observed that both polymorphs displayed some degree of thermochromism and upon cooling the ‘orange’ polymorph became more yellow, while the ‘yellow’ polymorph became paler upon cooling. International Union of Crystallography 2020-10-08 /pmc/articles/PMC7642768/ /pubmed/33148875 http://dx.doi.org/10.1107/S2053229620011560 Text en © Mason 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 Papers Mason, Helen E. Howard, Judith A. K. Sparkes, Hazel A. (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
title | (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
title_full | (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
title_fullStr | (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
title_full_unstemmed | (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
title_short | (E)-4-Bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
title_sort | (e)-4-bromo-2-[(phenylimino)methyl]phenol: a new polymorph and thermochromism |
topic | Research Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7642768/ https://www.ncbi.nlm.nih.gov/pubmed/33148875 http://dx.doi.org/10.1107/S2053229620011560 |
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