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O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate

In the title compound, C(15)H(17)NO(4)S(2), synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro­propano­yl)-4-phenyl­oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C—C bond. The phenyl ring is inclined to the mean pl...

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Autores principales: García-Merinos, J. Pablo, López-Ruiz, Heraclio, López, Yliana, Rojas-Lima, Susana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011202/
https://www.ncbi.nlm.nih.gov/pubmed/24860384
http://dx.doi.org/10.1107/S1600536814007636
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author García-Merinos, J. Pablo
López-Ruiz, Heraclio
López, Yliana
Rojas-Lima, Susana
author_facet García-Merinos, J. Pablo
López-Ruiz, Heraclio
López, Yliana
Rojas-Lima, Susana
author_sort García-Merinos, J. Pablo
collection PubMed
description In the title compound, C(15)H(17)NO(4)S(2), synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro­propano­yl)-4-phenyl­oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C—C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°. In the chain the methine H atom is involved in a C—H⋯S and a C—H⋯O intra­molecular inter­action. In the crystal, mol­ecules are linked by C—H⋯π inter­actions, forming chains along [001]. The S configuration at the C atom to which the xanthate group is attached was determined by comparison to the known R configuration of the C atom to which the phenyl group is attached.
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spelling pubmed-40112022014-05-23 O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate García-Merinos, J. Pablo López-Ruiz, Heraclio López, Yliana Rojas-Lima, Susana Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(15)H(17)NO(4)S(2), synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro­propano­yl)-4-phenyl­oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C—C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°. In the chain the methine H atom is involved in a C—H⋯S and a C—H⋯O intra­molecular inter­action. In the crystal, mol­ecules are linked by C—H⋯π inter­actions, forming chains along [001]. The S configuration at the C atom to which the xanthate group is attached was determined by comparison to the known R configuration of the C atom to which the phenyl group is attached. International Union of Crystallography 2014-04-18 /pmc/articles/PMC4011202/ /pubmed/24860384 http://dx.doi.org/10.1107/S1600536814007636 Text en © García-Merinos et al. 2014 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 Organic Papers
García-Merinos, J. Pablo
López-Ruiz, Heraclio
López, Yliana
Rojas-Lima, Susana
O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
title O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
title_full O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
title_fullStr O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
title_full_unstemmed O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
title_short O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
title_sort o-ethyl s-{(s)-1-oxo-1-[(r)-2-oxo-4-phenyl­oxazolidin-3-yl]propan-2-yl} carbonodi­thio­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011202/
https://www.ncbi.nlm.nih.gov/pubmed/24860384
http://dx.doi.org/10.1107/S1600536814007636
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