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Volume 68 
Part 12 
Page o3471  
December 2012  

Received 11 September 2012
Accepted 13 November 2012
Online 28 November 2012

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.157
Data-to-parameter ratio = 22.6
Details
Open access

3[beta]-Chloro-N-methoxy-N-methylcholest-5-ene-24-carboxamide

Karilys González,a* Karinel Nievesa and Abimael D. Rodrígueza

aDepartment of Chemistry, University of Puerto Rico, PO Box 23346, San Juan 00931-3346, Puerto Rico
Correspondence e-mail: karilysgn@yahoo.com

The title compound, C26H42ClNO2, is a 3[beta]-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.

Related literature

The title compound was obtained as part of our studies on the synthesis of chlorinated steroids as antimalarial agents. For chlorination of 3[beta]-hydroxyl-5-[Delta] steroids, see: Liu et al. (2005[Liu, F.-W., Liu, H.-M., Zhang, Y.-B., Zhang, J.-Y. & Tian, L.-H. (2005). Steroids, 70, 825-830.]). For antimalarial steroids, see: Corrales et al. (2011[Corrales, R. C. N. R., de Souza, N. B., Pinheiro, L. S., Abramo, C., Coimbra, E. S. & Da Silva, A. D. (2011). Biomed. Pharmacother. 65, 198-203.]); Sharma et al. (2008[Sharma, U., Srivastava, K., Puri, S. K. & Singh, C. (2008). Med. Chem. Res. 17, 326-334.]). For the emerging role of chlorinated lipids and fatty acids in pathology, see: Spickett (2007[Spickett, C. M. (2007). Pharmacol. Ther. 115, 400-409.]). For the use of steryl chlorides as synthetic intermediates, see: Ochi et al. (1977[Ochi, K., Matsunaga, I. & Shindo, M. (1977). Steroids, 30, 795-803.]). For liquid crystal properties of steryl chlorides, see: Leder (1971[Leder, L. B. (1971). J. Chem. Phys. 54, 4671-4675.]). For chloroquine-resistant malaria, see: Wellems & Plowe (2001[Wellems, T. E. & Plowe, C. V. (2001). J. Infect. Dis. 184, 770-776.]). For drug resistance in malaria, see: Bloland (2001[Bloland, P. B. (2001). World Health Organization, WHO/CDS/CSR/DRS/2001.4. http://www.who.int/emc .]).

[Scheme 1]

Experimental

Crystal data

  • C26H42ClNO2

  • Mr = 436.06

  • Orthorhombic, P 21 21 21

  • a = 7.5263 (2) Å

  • b = 16.2157 (4) Å

  • c = 20.8850 (5) Å

  • V = 2548.89 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 296 K

  • 0.31 × 0.09 × 0.08 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.949, Tmax = 0.987

  • 23203 measured reflections

  • 6244 independent reflections

  • 3307 reflections with I > 2[sigma](I)

  • Rint = 0.035
Refinement

  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.157

  • S = 1.01

  • 6244 reflections

  • 276 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2662 Friedel pairs

  • Flack parameter: -0.04 (9)

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2071 ).

Acknowledgements

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).

References

Bloland, P. B. (2001). World Health Organization, WHO/CDS/CSR/DRS/2001.4. http://www.who.int/emc .
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Corrales, R. C. N. R., de Souza, N. B., Pinheiro, L. S., Abramo, C., Coimbra, E. S. & Da Silva, A. D. (2011). Biomed. Pharmacother. 65, 198-203.  [CrossRef] [ChemPort] [PubMed]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Leder, L. B. (1971). J. Chem. Phys. 54, 4671-4675.  [CrossRef] [ChemPort]
Liu, F.-W., Liu, H.-M., Zhang, Y.-B., Zhang, J.-Y. & Tian, L.-H. (2005). Steroids, 70, 825-830.  [CSD] [CrossRef] [PubMed] [ChemPort]
Ochi, K., Matsunaga, I. & Shindo, M. (1977). Steroids, 30, 795-803.  [CrossRef] [ChemPort] [PubMed]
Sharma, U., Srivastava, K., Puri, S. K. & Singh, C. (2008). Med. Chem. Res. 17, 326-334.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spickett, C. M. (2007). Pharmacol. Ther. 115, 400-409.  [CrossRef] [PubMed] [ChemPort]
Wellems, T. E. & Plowe, C. V. (2001). J. Infect. Dis. 184, 770-776.  [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2012). E68, o3471  [ doi:10.1107/S160053681204679X ]

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.