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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
Descripción
Sumario: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.