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2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry

The title compound, C(15)H(13)BrO(2)S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromo­phen­yl)sulfanyl, benzaldehyde and meth­oxy residues: crystal symmetry generates a racemic mixture. A twist in the mol­ecule is evident about the methine-C—C(ca...

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Autores principales: Caracelli, Ignez, Zukerman-Schpector, Julio, Traesel, Henrique J., Olivato, Paulo R., Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658945/
https://www.ncbi.nlm.nih.gov/pubmed/31391973
http://dx.doi.org/10.1107/S2056989019006765
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author Caracelli, Ignez
Zukerman-Schpector, Julio
Traesel, Henrique J.
Olivato, Paulo R.
Jotani, Mukesh M.
Tiekink, Edward R. T.
author_facet Caracelli, Ignez
Zukerman-Schpector, Julio
Traesel, Henrique J.
Olivato, Paulo R.
Jotani, Mukesh M.
Tiekink, Edward R. T.
author_sort Caracelli, Ignez
collection PubMed
description The title compound, C(15)H(13)BrO(2)S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromo­phen­yl)sulfanyl, benzaldehyde and meth­oxy residues: crystal symmetry generates a racemic mixture. A twist in the mol­ecule is evident about the methine-C—C(carbon­yl) bond as evidenced by the O—C—C—O torsion angle of −20.8 (7)°. The dihedral angle between the bromo­benzene and phenyl rings is 43.2 (2)°, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supra­molecular chains as a result of methyl- and methine-C—H⋯O(carbon­yl) inter­actions. The chains assemble into a three-dimensional architecture without directional inter­actions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent inter­action plots and inter­action energy calculations. These point to the importance of weaker H⋯H and C—H⋯C inter­actions in the consolidation of the structure.
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spelling pubmed-66589452019-08-07 2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry Caracelli, Ignez Zukerman-Schpector, Julio Traesel, Henrique J. Olivato, Paulo R. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(15)H(13)BrO(2)S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromo­phen­yl)sulfanyl, benzaldehyde and meth­oxy residues: crystal symmetry generates a racemic mixture. A twist in the mol­ecule is evident about the methine-C—C(carbon­yl) bond as evidenced by the O—C—C—O torsion angle of −20.8 (7)°. The dihedral angle between the bromo­benzene and phenyl rings is 43.2 (2)°, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supra­molecular chains as a result of methyl- and methine-C—H⋯O(carbon­yl) inter­actions. The chains assemble into a three-dimensional architecture without directional inter­actions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent inter­action plots and inter­action energy calculations. These point to the importance of weaker H⋯H and C—H⋯C inter­actions in the consolidation of the structure. International Union of Crystallography 2019-05-17 /pmc/articles/PMC6658945/ /pubmed/31391973 http://dx.doi.org/10.1107/S2056989019006765 Text en © Caracelli 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
Caracelli, Ignez
Zukerman-Schpector, Julio
Traesel, Henrique J.
Olivato, Paulo R.
Jotani, Mukesh M.
Tiekink, Edward R. T.
2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
title 2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
title_full 2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
title_fullStr 2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
title_full_unstemmed 2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
title_short 2-[(4-Bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
title_sort 2-[(4-bromo­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure, hirshfeld surface analysis and computational chemistry
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658945/
https://www.ncbi.nlm.nih.gov/pubmed/31391973
http://dx.doi.org/10.1107/S2056989019006765
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