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Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole
(Z)-5-[2-(Benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole methanol monosolvate, C(19)H(16)N(4)O(2)S·CH(3)OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,5-dimethoxyphenyl)acrylonitrile with tributyltin azide via a [3 + 2]cycloaddition az...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908540/ https://www.ncbi.nlm.nih.gov/pubmed/27308011 http://dx.doi.org/10.1107/S2056989016005600 |
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author | Penthala, Narsimha Reddy Yadlapalli, Jaishankar K. B. Parkin, Sean Crooks, Peter A. |
author_facet | Penthala, Narsimha Reddy Yadlapalli, Jaishankar K. B. Parkin, Sean Crooks, Peter A. |
author_sort | Penthala, Narsimha Reddy |
collection | PubMed |
description | (Z)-5-[2-(Benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole methanol monosolvate, C(19)H(16)N(4)O(2)S·CH(3)OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,5-dimethoxyphenyl)acrylonitrile with tributyltin azide via a [3 + 2]cycloaddition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole, C(20)H(18)N(4)O(3)S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile with tributyltin azide. Crystals of (I) have two molecules in the asymmetric unit (Z′ = 2), whereas crystals of (II) have Z′ = 1. The benzothiophene rings in (I) and (II) are almost planar, with r.m.s deviations from the mean plane of 0.0084 and 0.0037 Å in (I) and 0.0084 Å in (II). The tetrazole rings of (I) and (II) make dihedral angles with the mean planes of the benzothiophene rings of 88.81 (13) and 88.92 (13)° in (I), and 60.94 (6)° in (II). The dimethoxyphenyl and trimethoxyphenyl rings make dihedral angles with the benzothiophene rings of 23.91 (8) and 24.99 (8)° in (I) and 84.47 (3)° in (II). In both structures, molecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetrazole and methanol, and are parallel to the b axis. In (II), molecules are linked into chains parallel to the a axis by N—H⋯N hydrogen bonds between adjacent tetrazole rings. |
format | Online Article Text |
id | pubmed-4908540 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-49085402016-06-15 Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole Penthala, Narsimha Reddy Yadlapalli, Jaishankar K. B. Parkin, Sean Crooks, Peter A. Acta Crystallogr E Crystallogr Commun Research Communications (Z)-5-[2-(Benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole methanol monosolvate, C(19)H(16)N(4)O(2)S·CH(3)OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,5-dimethoxyphenyl)acrylonitrile with tributyltin azide via a [3 + 2]cycloaddition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole, C(20)H(18)N(4)O(3)S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile with tributyltin azide. Crystals of (I) have two molecules in the asymmetric unit (Z′ = 2), whereas crystals of (II) have Z′ = 1. The benzothiophene rings in (I) and (II) are almost planar, with r.m.s deviations from the mean plane of 0.0084 and 0.0037 Å in (I) and 0.0084 Å in (II). The tetrazole rings of (I) and (II) make dihedral angles with the mean planes of the benzothiophene rings of 88.81 (13) and 88.92 (13)° in (I), and 60.94 (6)° in (II). The dimethoxyphenyl and trimethoxyphenyl rings make dihedral angles with the benzothiophene rings of 23.91 (8) and 24.99 (8)° in (I) and 84.47 (3)° in (II). In both structures, molecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetrazole and methanol, and are parallel to the b axis. In (II), molecules are linked into chains parallel to the a axis by N—H⋯N hydrogen bonds between adjacent tetrazole rings. International Union of Crystallography 2016-04-08 /pmc/articles/PMC4908540/ /pubmed/27308011 http://dx.doi.org/10.1107/S2056989016005600 Text en © Penthala et al. 2016 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 Penthala, Narsimha Reddy Yadlapalli, Jaishankar K. B. Parkin, Sean Crooks, Peter A. Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole |
title | Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole |
title_full | Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole |
title_fullStr | Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole |
title_full_unstemmed | Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole |
title_short | Crystal structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole |
title_sort | crystal structures of (z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1h-tetrazole and (z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1h-tetrazole |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908540/ https://www.ncbi.nlm.nih.gov/pubmed/27308011 http://dx.doi.org/10.1107/S2056989016005600 |
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