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(Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine

In the title compound, C(17)H(18)O(5)S, an analogue of the potent anti­cancer agent combretastatin A-4, the alkene C=C bond has a cis conformation and the C—C=C—C torsion angle is 9.0 (3)°. The dihedral angle between the benzene and thio­phene rings is 54.07 (4)°. The dioxene ring adopts a half-chai...

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Autores principales: Liu, Yu-Tao, Chu, Gang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998537/
https://www.ncbi.nlm.nih.gov/pubmed/24826109
http://dx.doi.org/10.1107/S1600536814004437
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author Liu, Yu-Tao
Chu, Gang
author_facet Liu, Yu-Tao
Chu, Gang
author_sort Liu, Yu-Tao
collection PubMed
description In the title compound, C(17)H(18)O(5)S, an analogue of the potent anti­cancer agent combretastatin A-4, the alkene C=C bond has a cis conformation and the C—C=C—C torsion angle is 9.0 (3)°. The dihedral angle between the benzene and thio­phene rings is 54.07 (4)°. The dioxene ring adopts a half-chair conformation, with the C atoms of the methyl­ene groups displaced by −0.325 (2) and 0.341 (3) Å from the plane of the other atoms. The C atoms of the two meta-meth­oxy groups are close to being coplanar with their attached benzene ring [displacements = −0.025 (2) and −0.196 (2) Å], whereas the C atom of the para-meth­oxy group is significantly displaced [by −1.107 (2) Å]. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into [0-11] chains, which feature two different types of R (2) (2)(6) loops.
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spelling pubmed-39985372014-05-13 (Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine Liu, Yu-Tao Chu, Gang Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(17)H(18)O(5)S, an analogue of the potent anti­cancer agent combretastatin A-4, the alkene C=C bond has a cis conformation and the C—C=C—C torsion angle is 9.0 (3)°. The dihedral angle between the benzene and thio­phene rings is 54.07 (4)°. The dioxene ring adopts a half-chair conformation, with the C atoms of the methyl­ene groups displaced by −0.325 (2) and 0.341 (3) Å from the plane of the other atoms. The C atoms of the two meta-meth­oxy groups are close to being coplanar with their attached benzene ring [displacements = −0.025 (2) and −0.196 (2) Å], whereas the C atom of the para-meth­oxy group is significantly displaced [by −1.107 (2) Å]. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into [0-11] chains, which feature two different types of R (2) (2)(6) loops. International Union of Crystallography 2014-03-05 /pmc/articles/PMC3998537/ /pubmed/24826109 http://dx.doi.org/10.1107/S1600536814004437 Text en © Liu and Chu 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
Liu, Yu-Tao
Chu, Gang
(Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
title (Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
title_full (Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
title_fullStr (Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
title_full_unstemmed (Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
title_short (Z)-5-(3,4,5-Tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
title_sort (z)-5-(3,4,5-tri­meth­oxy­styr­yl)-2,3-di­hydro­thieno[3,4-b][1,4]dioxine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998537/
https://www.ncbi.nlm.nih.gov/pubmed/24826109
http://dx.doi.org/10.1107/S1600536814004437
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