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Crystal structures of vortioxetine and its methanol monosolvate
Vortioxetine, C(18)H(22)N(2)S, (1), systematic name 1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine, a new drug used to treat patients with major depressive disorder, has been crystallized as the free base and its methanol monosolvate, C(18)H(22)N(2)S·CH(3)OH, (2). In both structures, the...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571347/ https://www.ncbi.nlm.nih.gov/pubmed/26396746 http://dx.doi.org/10.1107/S2056989015012256 |
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author | Zhou, Xin-Bo Gu, Jian-Ming Sun, Meng-ying Hu, Xiu-Rong Wu, Su-Xiang |
author_facet | Zhou, Xin-Bo Gu, Jian-Ming Sun, Meng-ying Hu, Xiu-Rong Wu, Su-Xiang |
author_sort | Zhou, Xin-Bo |
collection | PubMed |
description | Vortioxetine, C(18)H(22)N(2)S, (1), systematic name 1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine, a new drug used to treat patients with major depressive disorder, has been crystallized as the free base and its methanol monosolvate, C(18)H(22)N(2)S·CH(3)OH, (2). In both structures, the vortioxetine molecules have similar conformations: in (1), the dihedral angle between the aromatic rings is 80.04 (16)° and in (2) it is 84.94 (13)°. The C—S—C bond angle in (1) is 102.76 (14)° and the corresponding angle in (2) is 103.41 (11)°. The piperazine ring adopts a chair conformation with the exocyclic N—C bond in a pseudo-equatorial orientation in both structures. No directional interactions beyond normal van der Waals contacts could be identified in the crystal of (1), whereas in (2), the vortioxetine and methanol molecules are linked by N—H⋯O and O—H⋯N hydrogen bonds, generating [001] chains. |
format | Online Article Text |
id | pubmed-4571347 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45713472015-09-22 Crystal structures of vortioxetine and its methanol monosolvate Zhou, Xin-Bo Gu, Jian-Ming Sun, Meng-ying Hu, Xiu-Rong Wu, Su-Xiang Acta Crystallogr E Crystallogr Commun Research Communications Vortioxetine, C(18)H(22)N(2)S, (1), systematic name 1-{2-[(2,4-dimethylphenyl)sulfanyl]phenyl}piperazine, a new drug used to treat patients with major depressive disorder, has been crystallized as the free base and its methanol monosolvate, C(18)H(22)N(2)S·CH(3)OH, (2). In both structures, the vortioxetine molecules have similar conformations: in (1), the dihedral angle between the aromatic rings is 80.04 (16)° and in (2) it is 84.94 (13)°. The C—S—C bond angle in (1) is 102.76 (14)° and the corresponding angle in (2) is 103.41 (11)°. The piperazine ring adopts a chair conformation with the exocyclic N—C bond in a pseudo-equatorial orientation in both structures. No directional interactions beyond normal van der Waals contacts could be identified in the crystal of (1), whereas in (2), the vortioxetine and methanol molecules are linked by N—H⋯O and O—H⋯N hydrogen bonds, generating [001] chains. International Union of Crystallography 2015-07-04 /pmc/articles/PMC4571347/ /pubmed/26396746 http://dx.doi.org/10.1107/S2056989015012256 Text en © Zhou et al. 2015 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 Zhou, Xin-Bo Gu, Jian-Ming Sun, Meng-ying Hu, Xiu-Rong Wu, Su-Xiang Crystal structures of vortioxetine and its methanol monosolvate |
title | Crystal structures of vortioxetine and its methanol monosolvate |
title_full | Crystal structures of vortioxetine and its methanol monosolvate |
title_fullStr | Crystal structures of vortioxetine and its methanol monosolvate |
title_full_unstemmed | Crystal structures of vortioxetine and its methanol monosolvate |
title_short | Crystal structures of vortioxetine and its methanol monosolvate |
title_sort | crystal structures of vortioxetine and its methanol monosolvate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571347/ https://www.ncbi.nlm.nih.gov/pubmed/26396746 http://dx.doi.org/10.1107/S2056989015012256 |
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