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Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione
The title compound, C(18)H(20)N(4)O(2)S(2), is a new 1,3,4-oxadiazole and a key pharmacophore of several biologically active agents. It is composed of a methyl(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione moiety linked to a 2-methoxyphenyl unit via a piperazine ring that has a chair conformati...
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/PMC4770969/ https://www.ncbi.nlm.nih.gov/pubmed/26958404 http://dx.doi.org/10.1107/S2056989016000992 |
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author | Al-Alshaikh, Monirah A. Abuelizz, Hatem A. El-Emam, Ali A. Abdelbaky, Mohammed S. M. Garcia-Granda, Santiago |
author_facet | Al-Alshaikh, Monirah A. Abuelizz, Hatem A. El-Emam, Ali A. Abdelbaky, Mohammed S. M. Garcia-Granda, Santiago |
author_sort | Al-Alshaikh, Monirah A. |
collection | PubMed |
description | The title compound, C(18)H(20)N(4)O(2)S(2), is a new 1,3,4-oxadiazole and a key pharmacophore of several biologically active agents. It is composed of a methyl(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione moiety linked to a 2-methoxyphenyl unit via a piperazine ring that has a chair conformation. The thiophene ring mean plane lies almost in the plane of the oxadiazole ring, with a dihedral angle of 4.35 (9)°. The 2-methoxyphenyl ring is almost normal to the oxadiazole ring, with a dihedral angle of 84.17 (10)°. In the crystal, molecules are linked by weak C—H⋯S hydrogen bonds and C—H⋯π interactions, forming layers parallel to the bc plane. The layers are linked via weak C—H⋯O hydrogen bonds and slipped parallel π–π interactions [intercentroid distance = 3.6729 (10) Å], forming a three-dimensional structure. The thiophene ring has an approximate 180° rotational disorder about the bridging C—C bond. |
format | Online Article Text |
id | pubmed-4770969 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47709692016-03-08 Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione Al-Alshaikh, Monirah A. Abuelizz, Hatem A. El-Emam, Ali A. Abdelbaky, Mohammed S. M. Garcia-Granda, Santiago Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(18)H(20)N(4)O(2)S(2), is a new 1,3,4-oxadiazole and a key pharmacophore of several biologically active agents. It is composed of a methyl(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione moiety linked to a 2-methoxyphenyl unit via a piperazine ring that has a chair conformation. The thiophene ring mean plane lies almost in the plane of the oxadiazole ring, with a dihedral angle of 4.35 (9)°. The 2-methoxyphenyl ring is almost normal to the oxadiazole ring, with a dihedral angle of 84.17 (10)°. In the crystal, molecules are linked by weak C—H⋯S hydrogen bonds and C—H⋯π interactions, forming layers parallel to the bc plane. The layers are linked via weak C—H⋯O hydrogen bonds and slipped parallel π–π interactions [intercentroid distance = 3.6729 (10) Å], forming a three-dimensional structure. The thiophene ring has an approximate 180° rotational disorder about the bridging C—C bond. International Union of Crystallography 2016-01-30 /pmc/articles/PMC4770969/ /pubmed/26958404 http://dx.doi.org/10.1107/S2056989016000992 Text en © Al-Alshaikh 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 Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Al-Alshaikh, Monirah A. Abuelizz, Hatem A. El-Emam, Ali A. Abdelbaky, Mohammed S. M. Garcia-Granda, Santiago Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione |
title | Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione |
title_full | Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione |
title_fullStr | Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione |
title_full_unstemmed | Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione |
title_short | Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione |
title_sort | crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3h)-thione |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770969/ https://www.ncbi.nlm.nih.gov/pubmed/26958404 http://dx.doi.org/10.1107/S2056989016000992 |
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