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Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate
The asymmetric unit of the enantiomerically pure title compound, C(18)H(18)N(2)O(3)S, comprises two independent molecules (A and B) having almost identical conformations. When overlayed, the alignment–r.m.s. deviation value is 0.30 Å. The six-membered heterocycle has a twisted half-chair conformat...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730286/ https://www.ncbi.nlm.nih.gov/pubmed/29250349 http://dx.doi.org/10.1107/S2056989017012488 |
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author | Yennawar, Hemant P. Noble, Duncan J. Silverberg, Lee J. |
author_facet | Yennawar, Hemant P. Noble, Duncan J. Silverberg, Lee J. |
author_sort | Yennawar, Hemant P. |
collection | PubMed |
description | The asymmetric unit of the enantiomerically pure title compound, C(18)H(18)N(2)O(3)S, comprises two independent molecules (A and B) having almost identical conformations. When overlayed, the alignment–r.m.s. deviation value is 0.30 Å. The six-membered heterocycle has a twisted half-chair conformation in both molecules. The O atom on the S atom of the ring is pseudo-axial on the thiazine ring and trans to both a phenyl group substituent and the acetamide group in each case. The two benzene rings in each molecule are almost orthogonal to each other, with interplanar dihedral angles of 83.79 (17) and 86.95 (16)°. The acetamide group is pseudo-equatorial and a phenyl ring is pseudo-axial on the thiazine ring. Both molecules show a weak intramolecular C—H⋯O interaction between H-atom donors of one of the phenyl rings and the acetamide group. In the crystal, an intermolecular N—H⋯O(thiazine) hydrogen bond links B molecules along the 2(1) (b) screw axis and, in addition, an N—H⋯O(acetamide) hydrogen bond links A and B molecules across a. A two-dimensional layered structure lying parallel to (001) is generated, also involving weak intermolecular C—H⋯O interactions. |
format | Online Article Text |
id | pubmed-5730286 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-57302862017-12-15 Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate Yennawar, Hemant P. Noble, Duncan J. Silverberg, Lee J. Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric unit of the enantiomerically pure title compound, C(18)H(18)N(2)O(3)S, comprises two independent molecules (A and B) having almost identical conformations. When overlayed, the alignment–r.m.s. deviation value is 0.30 Å. The six-membered heterocycle has a twisted half-chair conformation in both molecules. The O atom on the S atom of the ring is pseudo-axial on the thiazine ring and trans to both a phenyl group substituent and the acetamide group in each case. The two benzene rings in each molecule are almost orthogonal to each other, with interplanar dihedral angles of 83.79 (17) and 86.95 (16)°. The acetamide group is pseudo-equatorial and a phenyl ring is pseudo-axial on the thiazine ring. Both molecules show a weak intramolecular C—H⋯O interaction between H-atom donors of one of the phenyl rings and the acetamide group. In the crystal, an intermolecular N—H⋯O(thiazine) hydrogen bond links B molecules along the 2(1) (b) screw axis and, in addition, an N—H⋯O(acetamide) hydrogen bond links A and B molecules across a. A two-dimensional layered structure lying parallel to (001) is generated, also involving weak intermolecular C—H⋯O interactions. International Union of Crystallography 2017-09-05 /pmc/articles/PMC5730286/ /pubmed/29250349 http://dx.doi.org/10.1107/S2056989017012488 Text en © Yennawar et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ 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/2.0/uk/ |
spellingShingle | Research Communications Yennawar, Hemant P. Noble, Duncan J. Silverberg, Lee J. Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
title | Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
title_full | Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
title_fullStr | Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
title_full_unstemmed | Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
title_short | Crystal structure of (1S,2S,5R)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
title_sort | crystal structure of (1s,2s,5r)-5-acetylamino-4-oxo-2,3-diphenyl-1,3-thiazinan-1-ium-1-olate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730286/ https://www.ncbi.nlm.nih.gov/pubmed/29250349 http://dx.doi.org/10.1107/S2056989017012488 |
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