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(S)-6-Chloro-4-cyclo-propyl-ethynyl-4-trifluoro-methyl-1H-3,1-benzoxazin-2(4H)-one.

ABSTRACT: Two independent mol-ecules comprise the crystallographic asymmetric unit in the title anti-retroviral 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-cyclo-propyl-ethynyl residue relative to the six-membered heterocycle: this approaches an orthogonal disposition in mol-ecule a compared to a more flattened conformation in mol-ecule b, the difference being reflected in the O(ring)-C-C-C(ethyne) torsion angles of 65 (4) and 159 (5)°, respectively. The independent mol-ecules are connected via the eight-membered {⋯HNC (O)}(2) amide synthon. Disorder is noted in the cyclo-propane ring of mol-ecule b in that two orientations of equal weight were discerned.

SUBMITTER: Cuffini S 

PROVIDER: S-EPMC2971961 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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(S)-6-Chloro-4-cyclo-propyl-ethynyl-4-trifluoro-methyl-1H-3,1-benzoxazin-2(4H)-one.

Cuffini Silvia S   Howie R Alan RA   Tiekink Edward R T ER   Wardell James L JL   Wardell Solange M S V SM  

Acta crystallographica. Section E, Structure reports online 20091121 Pt 12

Two independent mol-ecules comprise the crystallographic asymmetric unit in the title anti-retroviral 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-cyclo-propyl-ethynyl residue relative to the six-membered heterocycle: this approaches an orthogonal disposition in mol-ecule a compared to a more flattened conformation in mol-ecule b, the difference being reflected in the O(ring)-C-C-C(ethyne) t  ...[more]

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