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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...

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Autores principales: Mason, Helen E., Howard, Judith A. K., Sparkes, Hazel A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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