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Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide

A new polymorph of the title compound, C(10)H(13)NO, was obtained by recrystallization of the commercial product from a water/ethanol mixture (1:1 v/v). Crystals of the previously reported racemic and homochiral forms of 2-phenyl­butyramide were grown from water–aceto­nitrile solution in 1:1 volume...

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Autores principales: Rigin, Sergei, Armijo, Beatrice, Krivoshein, Arcadius V., Fonari, Marina, Timofeeva, Tatiana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658964/
https://www.ncbi.nlm.nih.gov/pubmed/31391975
http://dx.doi.org/10.1107/S2056989019007011
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author Rigin, Sergei
Armijo, Beatrice
Krivoshein, Arcadius V.
Fonari, Marina
Timofeeva, Tatiana
author_facet Rigin, Sergei
Armijo, Beatrice
Krivoshein, Arcadius V.
Fonari, Marina
Timofeeva, Tatiana
author_sort Rigin, Sergei
collection PubMed
description A new polymorph of the title compound, C(10)H(13)NO, was obtained by recrystallization of the commercial product from a water/ethanol mixture (1:1 v/v). Crystals of the previously reported racemic and homochiral forms of 2-phenyl­butyramide were grown from water–aceto­nitrile solution in 1:1 volume ratio [Khrustalev et al. (2014 ▸). Cryst. Growth Des. 14, 3360–3369]. While the previously reported racemic and enanti­opure forms of the title compound adopt very similar supra­molecular structures (hydrogen-bonded ribbons), the new racemic polymorph is stabilized by a single N—H⋯O hydrogen bond that links mol­ecules into chains along the c-axis direction with an anti­parallel (centrosymmetric) packing in the crystal. Hirshfeld mol­ecular surface analysis was employed to compare the inter­molecular inter­actions in the polymorphs of the title compound.
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spelling pubmed-66589642019-08-07 Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide Rigin, Sergei Armijo, Beatrice Krivoshein, Arcadius V. Fonari, Marina Timofeeva, Tatiana Acta Crystallogr E Crystallogr Commun Research Communications A new polymorph of the title compound, C(10)H(13)NO, was obtained by recrystallization of the commercial product from a water/ethanol mixture (1:1 v/v). Crystals of the previously reported racemic and homochiral forms of 2-phenyl­butyramide were grown from water–aceto­nitrile solution in 1:1 volume ratio [Khrustalev et al. (2014 ▸). Cryst. Growth Des. 14, 3360–3369]. While the previously reported racemic and enanti­opure forms of the title compound adopt very similar supra­molecular structures (hydrogen-bonded ribbons), the new racemic polymorph is stabilized by a single N—H⋯O hydrogen bond that links mol­ecules into chains along the c-axis direction with an anti­parallel (centrosymmetric) packing in the crystal. Hirshfeld mol­ecular surface analysis was employed to compare the inter­molecular inter­actions in the polymorphs of the title compound. International Union of Crystallography 2019-05-21 /pmc/articles/PMC6658964/ /pubmed/31391975 http://dx.doi.org/10.1107/S2056989019007011 Text en © Rigin et al. 2019 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 Communications
Rigin, Sergei
Armijo, Beatrice
Krivoshein, Arcadius V.
Fonari, Marina
Timofeeva, Tatiana
Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
title Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
title_full Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
title_fullStr Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
title_short Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
title_sort crystal structure and hirshfeld surface analysis of new polymorph of racemic 2-phenyl­butyramide
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658964/
https://www.ncbi.nlm.nih.gov/pubmed/31391975
http://dx.doi.org/10.1107/S2056989019007011
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