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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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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. |
format | Online Article Text |
id | pubmed-3998537 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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