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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...

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Autores principales: Kowiel, M., Zelisko, N., Atamanyuk, D., Lesyk, R., Gzella, A. K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
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.
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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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