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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...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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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. |
format | Text |
id | pubmed-2971961 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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