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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
Descripción
Sumario: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.