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Volume 65 
Part 5 
Page o1125  
May 2009  

Received 18 April 2009
Accepted 20 April 2009
Online 25 April 2009

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.023
wR = 0.057
Data-to-parameter ratio = 21.7
Details

(20S)-22-Iodomethyl-6[beta]-methoxy-3[alpha],5-dihydro-3'H-cyclopropa[3[alpha],5]-5[alpha]-pregnane

Kamal Aziz Ketuly,a A. Hamid A. Hadia and Seik Weng Nga*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title steroid derivative, C23H37IO, the fused cyclopropane unit that comprises part of the A ring has a [beta]-configuration, and the associated cyclopentane ring has an envelope conformation.

Related literature

This iodo-substituted steroid was synthesized from 22-(p-toluenesulfonyloxymethyl)-6[beta]-methoxy-3[alpha],5-cyclo-5[alpha]-pregnane; for its crystal structure, see: Ketuly et al. (1997[Ketuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981-982.]).

[Scheme 1]

Experimental

Crystal data

  • C23H37IO

  • Mr = 456.43

  • Monoclinic, P 21

  • a = 7.4001 (1) Å

  • b = 9.8862 (1) Å

  • c = 14.8768 (2) Å

  • [beta] = 100.593 (1)°

  • V = 1069.82 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.51 mm-1

  • T = 100 K

  • 0.35 × 0.20 × 0.05 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.605, Tmax = 0.746 (expected range = 0.752-0.928)

  • 10136 measured reflections

  • 4895 independent reflections

  • 4652 reflections with I > 2[sigma](I)

  • Rint = 0.021
Refinement

  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.057

  • S = 0.91

  • 4895 reflections

  • 226 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 1.08 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2124 Friedel pairs

  • Flack parameter: 0.00 (1)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2434 ).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [ChemPort] [details]
Ketuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981-982.  [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.

Acta Cryst (2009). E65, o1125  [ doi:10.1107/S1600536809014597 ]

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