Received 11 September 2012
The title compound, C26H42ClNO2, is a 3-chloro steroid with a Weinreb amide at the C-24 position. The two cyclohexane and the cyclohexene rings adopt chair and boat conformations, respectively. The cyclopentane ring has an envelope conformation.
The title compound was obtained as part of our studies on the synthesis of chlorinated steroids as antimalarial agents. For chlorination of 3-hydroxyl-5- steroids, see: Liu et al. (2005). For antimalarial steroids, see: Corrales et al. (2011); Sharma et al. (2008). For the emerging role of chlorinated lipids and fatty acids in pathology, see: Spickett (2007). For the use of steryl chlorides as synthetic intermediates, see: Ochi et al. (1977). For liquid crystal properties of steryl chlorides, see: Leder (1971). For chloroquine-resistant malaria, see: Wellems & Plowe (2001). For drug resistance in malaria, see: Bloland (2001).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2071 ).
The authors thank the Instituto de Investigaciones Científicas y Servicios de Alta Tecnología (INDICASAT) in Panama for the antimalarial bioassay and Dr Raphel G. Raptis for the use of the X-ray facilitites. Mass spectrometry determinations were provided by the Mass Spectrometry Laboratory of the University of Illinois at Urbana-Champaign. Financial support to KN was provided by the UPR-RISE Fellowship Program (grant 2R25GM061151-11).
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