Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases

In the title N-Mannich bases, 3-(adamantan-1-yl)-4-(4-fluoro­phen­yl)-1-[(4-phenyl­piperazin-1-yl)meth­yl]-4,5-di­hydro-1H-1,2,4-triazole-5-thione (C29H34FN5S) (I), and 3-(adamantan-1-yl)-4-(4-fluoro­phen­yl)-1-{[4-(2-meth­oxyphen­yl)piperazin-1-yl]-meth­yl}-4,5-di­hydro-1H-1,2,4-triazole-5-thione (...

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Detalles Bibliográficos
Autores: Al-Alshaikh, Monirah A., Al-Mutairi, A. A., Ghabbour, Hazem A., El-Emam, Ali A., Abdelbaky, Mohammed S. M., García-Granda, Santiago
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/173314
Acceso en línea:http://hdl.handle.net/10261/173314
Access Level:acceso abierto
Palabra clave:Adamantane
C—H...F hydrogen bonding: C—H...π inter­actions
Biological activities
Piperazine
Crystal structures
1,2,4-triazole-5-thione
N-Mannich bases
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spelling Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich basesAl-Alshaikh, Monirah A.Al-Mutairi, A. A.Ghabbour, Hazem A.El-Emam, Ali A.Abdelbaky, Mohammed S. M.García-Granda, SantiagoAdamantaneC—H...F hydrogen bonding: C—H...π inter­actionsBiological activitiesPiperazineCrystal structures1,2,4-triazole-5-thioneN-Mannich basesIn the title N-Mannich bases, 3-(adamantan-1-yl)-4-(4-fluoro­phen­yl)-1-[(4-phenyl­piperazin-1-yl)meth­yl]-4,5-di­hydro-1H-1,2,4-triazole-5-thione (C29H34FN5S) (I), and 3-(adamantan-1-yl)-4-(4-fluoro­phen­yl)-1-{[4-(2-meth­oxyphen­yl)piperazin-1-yl]-meth­yl}-4,5-di­hydro-1H-1,2,4-triazole-5-thione (C30H36FN5OS) (II), fluoro­phenyl, adamantane and piperazine moieties are linked to a planar triazole ring. There is an additional phenyl ring on the piperazine ring in (I) and a meth­oxy­phenyl ring in (II). In compound (I), the fluoro­phenyl and phenyl rings are inclined to the triazole ring by 86.55 (13) and 60.52 (12)°, respectively, and the two aryl rings are inclined to one another by 66.37 (13)°. In compound (II), the corresponding dihedral angles are 83.35 (13), 71.38 (15) and 11.97 (16)°, respectively. The crystal structure of (I) shows pairs of C—H...F hydrogen bonds forming inversion dimers, while in the crystal of compound (II), in addition to the C—H...F hydrogen bonds that generate chains parallel to the b axis, there are C—H...π inter­actions present that link the chains to form layers parallel to the ab plane.Financial support from the Spanish Ministerio de Economía y Competitividad (MINECO-13-MAT2013–40950-R, MAT2016–78155-C2–1-R and FPI grant BES-2011–046948 to MSMA), Gobierno del Principado de Asturias (GRUPIN14– 060) and FEDER funding, is also gratefully acknowledged.Peer ReviewedInternational Union of CrystallographyPrincipado de AsturiasMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2018201820172018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/173314reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2013-40950-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2016–78155-C2–1-Rhttps://doi.org/10.1107/S2056989017009756Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1733142026-05-22T06:33:51Z
dc.title.none.fl_str_mv Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
title Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
spellingShingle Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
Al-Alshaikh, Monirah A.
Adamantane
C—H...F hydrogen bonding: C—H...π inter­actions
Biological activities
Piperazine
Crystal structures
1,2,4-triazole-5-thione
N-Mannich bases
title_short Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
title_full Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
title_fullStr Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
title_full_unstemmed Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
title_sort Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases
dc.creator.none.fl_str_mv Al-Alshaikh, Monirah A.
Al-Mutairi, A. A.
Ghabbour, Hazem A.
El-Emam, Ali A.
Abdelbaky, Mohammed S. M.
García-Granda, Santiago
author Al-Alshaikh, Monirah A.
author_facet Al-Alshaikh, Monirah A.
Al-Mutairi, A. A.
Ghabbour, Hazem A.
El-Emam, Ali A.
Abdelbaky, Mohammed S. M.
García-Granda, Santiago
author_role author
author2 Al-Mutairi, A. A.
Ghabbour, Hazem A.
El-Emam, Ali A.
Abdelbaky, Mohammed S. M.
García-Granda, Santiago
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Principado de Asturias
Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Adamantane
C—H...F hydrogen bonding: C—H...π inter­actions
Biological activities
Piperazine
Crystal structures
1,2,4-triazole-5-thione
N-Mannich bases
topic Adamantane
C—H...F hydrogen bonding: C—H...π inter­actions
Biological activities
Piperazine
Crystal structures
1,2,4-triazole-5-thione
N-Mannich bases
description In the title N-Mannich bases, 3-(adamantan-1-yl)-4-(4-fluoro­phen­yl)-1-[(4-phenyl­piperazin-1-yl)meth­yl]-4,5-di­hydro-1H-1,2,4-triazole-5-thione (C29H34FN5S) (I), and 3-(adamantan-1-yl)-4-(4-fluoro­phen­yl)-1-{[4-(2-meth­oxyphen­yl)piperazin-1-yl]-meth­yl}-4,5-di­hydro-1H-1,2,4-triazole-5-thione (C30H36FN5OS) (II), fluoro­phenyl, adamantane and piperazine moieties are linked to a planar triazole ring. There is an additional phenyl ring on the piperazine ring in (I) and a meth­oxy­phenyl ring in (II). In compound (I), the fluoro­phenyl and phenyl rings are inclined to the triazole ring by 86.55 (13) and 60.52 (12)°, respectively, and the two aryl rings are inclined to one another by 66.37 (13)°. In compound (II), the corresponding dihedral angles are 83.35 (13), 71.38 (15) and 11.97 (16)°, respectively. The crystal structure of (I) shows pairs of C—H...F hydrogen bonds forming inversion dimers, while in the crystal of compound (II), in addition to the C—H...F hydrogen bonds that generate chains parallel to the b axis, there are C—H...π inter­actions present that link the chains to form layers parallel to the ab plane.
publishDate 2017
dc.date.none.fl_str_mv 2017
2018
2018
2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/173314
url http://hdl.handle.net/10261/173314
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2013-40950-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2016–78155-C2–1-R
https://doi.org/10.1107/S2056989017009756
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv International Union of Crystallography
publisher.none.fl_str_mv International Union of Crystallography
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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