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2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate
The title compound, C(17)H(15)Br(2)NO(6)S(2)·C(2)H(5)OH, is the esterification reaction product of 2-(8,10-dibromo-2,6-dioxo-3,5,5a,11b-tetrahydro-2H,6H-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5a-yl)acetic acid. Cleavage of the lactone ring and formation of ethoxycarbonyl and hydroxy group...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435735/ https://www.ncbi.nlm.nih.gov/pubmed/22969606 http://dx.doi.org/10.1107/S1600536812035325 |
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author | Kowiel, M. Zelisko, N. Atamanyuk, D. Lesyk, R. Gzella, A. K. |
author_facet | Kowiel, M. Zelisko, N. Atamanyuk, D. Lesyk, R. Gzella, A. K. |
author_sort | Kowiel, M. |
collection | PubMed |
description | The title compound, C(17)H(15)Br(2)NO(6)S(2)·C(2)H(5)OH, is the esterification reaction product of 2-(8,10-dibromo-2,6-dioxo-3,5,5a,11b-tetrahydro-2H,6H-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5a-yl)acetic acid. Cleavage of the lactone ring and formation of ethoxycarbonyl and hydroxy groups from its structural elements were observed. On the other hand, the carboxymethyl group was not esterified. The H atom and carboxymethyl group, both at stereogenic centres, show a cis conformation. The six-membered dihydrothiopyran ring adopts a half-chair conformation. All NH and OH groups participate in the three-dimensional hydrogen-bond network, which is additionally strengthened by C—H⋯O and C—H⋯S interactions. Intramolecular O—H⋯Br and C—H⋯O interactions also occur. |
format | Online Article Text |
id | pubmed-3435735 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-34357352012-09-11 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate Kowiel, M. Zelisko, N. Atamanyuk, D. Lesyk, R. Gzella, A. K. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(17)H(15)Br(2)NO(6)S(2)·C(2)H(5)OH, is the esterification reaction product of 2-(8,10-dibromo-2,6-dioxo-3,5,5a,11b-tetrahydro-2H,6H-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5a-yl)acetic acid. Cleavage of the lactone ring and formation of ethoxycarbonyl and hydroxy groups from its structural elements were observed. On the other hand, the carboxymethyl group was not esterified. The H atom and carboxymethyl group, both at stereogenic centres, show a cis conformation. The six-membered dihydrothiopyran ring adopts a half-chair conformation. All NH and OH groups participate in the three-dimensional hydrogen-bond network, which is additionally strengthened by C—H⋯O and C—H⋯S interactions. Intramolecular O—H⋯Br and C—H⋯O interactions also occur. International Union of Crystallography 2012-08-15 /pmc/articles/PMC3435735/ /pubmed/22969606 http://dx.doi.org/10.1107/S1600536812035325 Text en © Kowiel et al. 2012 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 Kowiel, M. Zelisko, N. Atamanyuk, D. Lesyk, R. Gzella, A. K. 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
title | 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
title_full | 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
title_fullStr | 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
title_full_unstemmed | 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
title_short | 2-[7-(3,5-Dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5H-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
title_sort | 2-[7-(3,5-dibromo-2-hydroxyphenyl)-6-ethoxycarbonyl-2-oxo-5h-2,3,6,7-tetrahydrothiopyrano[2,3-d][1,3]thiazol-6-yl]acetic acid ethanol monosolvate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3435735/ https://www.ncbi.nlm.nih.gov/pubmed/22969606 http://dx.doi.org/10.1107/S1600536812035325 |
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