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Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position
The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C(10)H(8)Cl(3)NOS), 1 and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C(10)H(7)Cl(4)NOS) 2, are structurally related with one atom substitution difference in the para position of the benzene ring. In both s...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6176436/ https://www.ncbi.nlm.nih.gov/pubmed/30319812 http://dx.doi.org/10.1107/S2056989018013257 |
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author | Nuriye, Ahmed Yennawar, Hemant Cannon, Kevin Tierney, John |
author_facet | Nuriye, Ahmed Yennawar, Hemant Cannon, Kevin Tierney, John |
author_sort | Nuriye, Ahmed |
collection | PubMed |
description | The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C(10)H(8)Cl(3)NOS), 1 and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C(10)H(7)Cl(4)NOS) 2, are structurally related with one atom substitution difference in the para position of the benzene ring. In both structures, the thiazolidinone ring adopts an envelope conformation with the S atom as the flap. The dihedral angles between the rings [48.72 (11) in 1 and 48.42 (9)° in 2] are very similar and the molecules are almost superimposable. In both crystal structures, C—H⋯O ‘head-to-tail’ interactions between the chiral carbon atoms and the thiazolidinone oxygen atoms result in infinite monochiral chains along the direction of the shortest unit-cell parameter, namely a in 1 and b in 2. C—H⋯π interactions between the thiazolidinone carbon atom at the 4-position and the phenyl ring of the neighboring enantiomer also help to stabilize the packing in each case, although the crystals are not isostructural. |
format | Online Article Text |
id | pubmed-6176436 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-61764362018-10-12 Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position Nuriye, Ahmed Yennawar, Hemant Cannon, Kevin Tierney, John Acta Crystallogr E Crystallogr Commun Research Communications The title compounds 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-one (C(10)H(8)Cl(3)NOS), 1 and 3-(4-chlorophenyl)-2-trichloromethyl-1,3-thiazolidin-4-one (C(10)H(7)Cl(4)NOS) 2, are structurally related with one atom substitution difference in the para position of the benzene ring. In both structures, the thiazolidinone ring adopts an envelope conformation with the S atom as the flap. The dihedral angles between the rings [48.72 (11) in 1 and 48.42 (9)° in 2] are very similar and the molecules are almost superimposable. In both crystal structures, C—H⋯O ‘head-to-tail’ interactions between the chiral carbon atoms and the thiazolidinone oxygen atoms result in infinite monochiral chains along the direction of the shortest unit-cell parameter, namely a in 1 and b in 2. C—H⋯π interactions between the thiazolidinone carbon atom at the 4-position and the phenyl ring of the neighboring enantiomer also help to stabilize the packing in each case, although the crystals are not isostructural. International Union of Crystallography 2018-09-28 /pmc/articles/PMC6176436/ /pubmed/30319812 http://dx.doi.org/10.1107/S2056989018013257 Text en © Nuriye et al. 2018 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 Nuriye, Ahmed Yennawar, Hemant Cannon, Kevin Tierney, John Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
title | Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
title_full | Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
title_fullStr | Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
title_full_unstemmed | Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
title_short | Crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
title_sort | crystal structures of two thiazolidinone derivatives bearing a trichloromethyl substituent at the 2-position |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6176436/ https://www.ncbi.nlm.nih.gov/pubmed/30319812 http://dx.doi.org/10.1107/S2056989018013257 |
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