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Crystal structure of 3-bromo-2-hydroxybenzonitrile
The crystal structure of the title compound, C(7)H(4)BrNO, has been determined, revealing a partial molecular packing disorder such that a 180° rotation of the molecule about the phenol C—O bond results in disorder of the bromine and nitrile groups. The disorder has been parameterized as a disorde...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518954/ https://www.ncbi.nlm.nih.gov/pubmed/26279943 http://dx.doi.org/10.1107/S2056989015011974 |
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author | Dickinson, Sean R. Müller, Peter Tanski, Joseph M. |
author_facet | Dickinson, Sean R. Müller, Peter Tanski, Joseph M. |
author_sort | Dickinson, Sean R. |
collection | PubMed |
description | The crystal structure of the title compound, C(7)H(4)BrNO, has been determined, revealing a partial molecular packing disorder such that a 180° rotation of the molecule about the phenol C—O bond results in disorder of the bromine and nitrile groups. The disorder has been parameterized as a disorder of only the bromine and nitrile substituents on a unique phenol ring. An intramolecular O—H⋯Br contact occurs. In the crystal, O—H⋯Br/O—H⋯N(nitrile) hydrogen bonding is present between the disordered bromine and nitrile substituents and the phenol group, forming a spiral chain about a twofold screw axis extending parallel to the b-axis direction. Within this spiral chain, the molecules also interact, forming offset face-to-face π-stacking interactions with plane-to-centroid distance of 3.487 (1) Å. |
format | Online Article Text |
id | pubmed-4518954 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45189542015-08-14 Crystal structure of 3-bromo-2-hydroxybenzonitrile Dickinson, Sean R. Müller, Peter Tanski, Joseph M. Acta Crystallogr E Crystallogr Commun Data Reports The crystal structure of the title compound, C(7)H(4)BrNO, has been determined, revealing a partial molecular packing disorder such that a 180° rotation of the molecule about the phenol C—O bond results in disorder of the bromine and nitrile groups. The disorder has been parameterized as a disorder of only the bromine and nitrile substituents on a unique phenol ring. An intramolecular O—H⋯Br contact occurs. In the crystal, O—H⋯Br/O—H⋯N(nitrile) hydrogen bonding is present between the disordered bromine and nitrile substituents and the phenol group, forming a spiral chain about a twofold screw axis extending parallel to the b-axis direction. Within this spiral chain, the molecules also interact, forming offset face-to-face π-stacking interactions with plane-to-centroid distance of 3.487 (1) Å. International Union of Crystallography 2015-06-27 /pmc/articles/PMC4518954/ /pubmed/26279943 http://dx.doi.org/10.1107/S2056989015011974 Text en © Dickinson et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Data Reports Dickinson, Sean R. Müller, Peter Tanski, Joseph M. Crystal structure of 3-bromo-2-hydroxybenzonitrile |
title | Crystal structure of 3-bromo-2-hydroxybenzonitrile |
title_full | Crystal structure of 3-bromo-2-hydroxybenzonitrile |
title_fullStr | Crystal structure of 3-bromo-2-hydroxybenzonitrile |
title_full_unstemmed | Crystal structure of 3-bromo-2-hydroxybenzonitrile |
title_short | Crystal structure of 3-bromo-2-hydroxybenzonitrile |
title_sort | crystal structure of 3-bromo-2-hydroxybenzonitrile |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518954/ https://www.ncbi.nlm.nih.gov/pubmed/26279943 http://dx.doi.org/10.1107/S2056989015011974 |
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