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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...

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Detalles Bibliográficos
Autores principales: Dickinson, Sean R., Müller, Peter, Tanski, Joseph M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
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.
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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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