( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one

Autores
Cuffini, Silvia Lucia; Howie, R. Alan; Tiekink, Edward R. T.; Wardell, James L.; Wardell, Solange M. S. V.
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two independent molecules comprise the crystallographic asymmetric unit in the title antiretroviral agent Efavirenz, C14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerneda compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedvia the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb in that two orientations of equal weight were discerned
Fil: Cuffini, Silvia Lucia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Howie, R. Alan. University of Aberdeen; Reino Unido
Fil: Tiekink, Edward R. T.. University of Malaya; Malasia
Fil: Wardell, James L.. Fundación Oswaldo Cruz; Brasil
Fil: Wardell, Solange M. S. V.. No especifíca;
Materia
Efavirenz
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/240756

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spelling ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-oneCuffini, Silvia LuciaHowie, R. AlanTiekink, Edward R. T.Wardell, James L.Wardell, Solange M. S. V.Efavirenzhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two independent molecules comprise the crystallographic asymmetric unit in the title antiretroviral agent Efavirenz, C14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerneda compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedvia the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb in that two orientations of equal weight were discernedFil: Cuffini, Silvia Lucia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Howie, R. Alan. University of Aberdeen; Reino UnidoFil: Tiekink, Edward R. T.. University of Malaya; MalasiaFil: Wardell, James L.. Fundación Oswaldo Cruz; BrasilFil: Wardell, Solange M. S. V.. No especifíca;Wiley Blackwell Publishing, Inc2009-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/240756Cuffini, Silvia Lucia; Howie, R. Alan; Tiekink, Edward R. T.; Wardell, James L.; Wardell, Solange M. S. V.; ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section E; 65; 12; 11-2009; o3170-o31711600-5368CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://journals.iucr.org/e/issues/2009/12/00/hg2596/index.htmlinfo:eu-repo/semantics/altIdentifier/doi/10.1107/S1600536809049101info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:11:31Zoai:ri.conicet.gov.ar:11336/240756instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:11:31.617CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
title ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
spellingShingle ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
Cuffini, Silvia Lucia
Efavirenz
title_short ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
title_full ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
title_fullStr ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
title_full_unstemmed ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
title_sort ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one
dc.creator.none.fl_str_mv Cuffini, Silvia Lucia
Howie, R. Alan
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author Cuffini, Silvia Lucia
author_facet Cuffini, Silvia Lucia
Howie, R. Alan
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author_role author
author2 Howie, R. Alan
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Efavirenz
topic Efavirenz
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two independent molecules comprise the crystallographic asymmetric unit in the title antiretroviral agent Efavirenz, C14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerneda compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedvia the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb in that two orientations of equal weight were discerned
Fil: Cuffini, Silvia Lucia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Howie, R. Alan. University of Aberdeen; Reino Unido
Fil: Tiekink, Edward R. T.. University of Malaya; Malasia
Fil: Wardell, James L.. Fundación Oswaldo Cruz; Brasil
Fil: Wardell, Solange M. S. V.. No especifíca;
description Two independent molecules comprise the crystallographic asymmetric unit in the title antiretroviral agent Efavirenz, C14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned14H9ClF3NO2, and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclopropylethynyl residue relative to the sixmembered heterocycle: this approaches an orthogonal disposition in molecule a compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerneda compared to a more flattened conformation in molecule b, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb, the difference being reflected in the Oring— C—C—Cethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedethyne torsion angles of 65 (4) and 159 (5), respectively. The independent molecules are connected via the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedvia the eightmembered { HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discerned HNC (O)}2 amide synthon. Disorder is noted in the cyclopropane ring of molecule b in that two orientations of equal weight were discernedb in that two orientations of equal weight were discerned
publishDate 2009
dc.date.none.fl_str_mv 2009-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/240756
Cuffini, Silvia Lucia; Howie, R. Alan; Tiekink, Edward R. T.; Wardell, James L.; Wardell, Solange M. S. V.; ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section E; 65; 12; 11-2009; o3170-o3171
1600-5368
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240756
identifier_str_mv Cuffini, Silvia Lucia; Howie, R. Alan; Tiekink, Edward R. T.; Wardell, James L.; Wardell, Solange M. S. V.; ( S )-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1 H -3,1-benzoxazin-2(4 H )-one; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section E; 65; 12; 11-2009; o3170-o3171
1600-5368
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
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info:eu-repo/semantics/altIdentifier/doi/10.1107/S1600536809049101
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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