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

Two independent mol­ecules comprise the crystallographic asymmetric unit in the title anti­retroviral agent Efavirenz, C(14)H(9)ClF(3)NO(2), and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclo­propyl­ethynyl residue relative to the si...

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Detalles Bibliográficos
Autores principales: Cuffini, Silvia, Howie, R. Alan, Tiekink, Edward R. T., Wardell, James L., Wardell, Solange M. S. V.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971961/
https://www.ncbi.nlm.nih.gov/pubmed/21578886
http://dx.doi.org/10.1107/S1600536809049101
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author Cuffini, Silvia
Howie, R. Alan
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author_facet Cuffini, Silvia
Howie, R. Alan
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
author_sort Cuffini, Silvia
collection PubMed
description Two independent mol­ecules comprise the crystallographic asymmetric unit in the title anti­retroviral agent Efavirenz, C(14)H(9)ClF(3)NO(2), and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclo­propyl­ethynyl residue relative to the six-membered heterocycle: this approaches an orthogonal disposition in mol­ecule a compared to a more flattened conformation in mol­ecule b, the difference being reflected in the O(ring)—C—C—C(ethyne) torsion angles of 65 (4) and 159 (5)°, respectively. The independent mol­ecules are connected via the eight-membered {⋯HNC (O)}(2) amide synthon. Disorder is noted in the cyclo­propane ring of mol­ecule b in that two orientations of equal weight were discerned.
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spelling pubmed-29719612010-12-30 (S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one Cuffini, Silvia Howie, R. Alan Tiekink, Edward R. T. Wardell, James L. Wardell, Solange M. S. V. Acta Crystallogr Sect E Struct Rep Online Organic Papers Two independent mol­ecules comprise the crystallographic asymmetric unit in the title anti­retroviral agent Efavirenz, C(14)H(9)ClF(3)NO(2), and these have noteworthy differences in conformation. The major difference relates to the orientation of the 2-cyclo­propyl­ethynyl residue relative to the six-membered heterocycle: this approaches an orthogonal disposition in mol­ecule a compared to a more flattened conformation in mol­ecule b, the difference being reflected in the O(ring)—C—C—C(ethyne) torsion angles of 65 (4) and 159 (5)°, respectively. The independent mol­ecules are connected via the eight-membered {⋯HNC (O)}(2) amide synthon. Disorder is noted in the cyclo­propane ring of mol­ecule b in that two orientations of equal weight were discerned. International Union of Crystallography 2009-11-21 /pmc/articles/PMC2971961/ /pubmed/21578886 http://dx.doi.org/10.1107/S1600536809049101 Text en © Cuffini et al. 2009 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 Organic Papers
Cuffini, Silvia
Howie, R. Alan
Tiekink, Edward R. T.
Wardell, James L.
Wardell, Solange M. S. V.
(S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one
title (S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one
title_full (S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one
title_fullStr (S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one
title_full_unstemmed (S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one
title_short (S)-6-Chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1H-3,1-benzoxazin-2(4H)-one
title_sort (s)-6-chloro-4-cyclo­propyl­ethynyl-4-trifluoro­methyl-1h-3,1-benzoxazin-2(4h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971961/
https://www.ncbi.nlm.nih.gov/pubmed/21578886
http://dx.doi.org/10.1107/S1600536809049101
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