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Volume 69 
Part 1 
Page o60  
January 2013  

Received 6 November 2012
Accepted 5 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.009 Å
R = 0.072
wR = 0.199
Data-to-parameter ratio = 11.6
Details
Open access

17[beta]-Hydroxy-17[alpha]-methylandrosta-1,4-dien-3-one

aSchool of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland
Correspondence e-mail: patrick.mcardle@nuigalway.ie

The title compound, C20H28O2, is a steroid with strong anabolic properties. The present solvent-free form crystallizes with two molecules per asymmetric unit. In the crystal, both molecules are involved in the formation of O-H...O hydrogen-bonded chains which extend along the b-axis direction.

Related literature

For examples of other compounds with unused hydrogen-bonding capacity, see: Bhatt et al. (2006[Bhatt, P. M. & Desiraju, G. R. (2006). Acta Cryst. C62, o362-o363.]); Lewis et al. (2005[Lewis, T. C., Tocher, D. A. & Price, S. L. (2005). Cryst. Growth Des. 5, 983-993.]); Desiraju et al. (2002[Desiraju, G. R. (2002). CrystEngComm, 4, 499-499.]). For related structures of other anabolic steroids, see: Verma et al. (2006[Verma, R., Jasrotia, D. & Bhat, M. (2006). J. Chem. Crystallogr. 36, 283-287.]). For related structures of steroid compounds with non-hydrogen-bonded OH or C=O motifs, see: Karpinska et al. (2011[Karpinska, J., Erxleben, A. & McArdle, P. (2011). Cryst. Growth Des. 11, 2829-2838.]); Danaci et al. (1988[Danaci, S., Kendi, E., Moers, F. G., Behm, H. & Beurskens, P. T. (1988). Acta Cryst. C44, 1677-1679.]); Chakrabarti et al. (1981[Chakrabarti, P., Banerjee, D. K. & Venkatesan, K. (1981). Steroids, 37, 269-279.]); McPhail et al. (1977[McPhail, A. T., Luhan, P. A., Tschang, P.-S. W. & Onan, K. D. (1977). J. Chem. Soc. Perkin Trans. 2, pp. 379-383.]); Delettré et al. (1975[Delettré, J., Mornon, J.-P. & Lepicard, G. (1975). Acta Cryst. B31, 450-453.]). For applications of methandrostenolone, see: Druzhinina et al. (2008[Druzhinina, A., Andryushina, V., Stytsenko, T. & Voishvillo, N. (2008). Appl. Biochem. Microbiol. 44, 580-584.]). For a previously reported mono hydrate (with no unused hydrogen-bonding capacity), see: Duax et al. (1982[Duax, W. L., Rohrer, D. C. & Segaloff, A. (1982). Acta Cryst. B38, 531-534.]).

[Scheme 1]

Experimental

Crystal data
  • C20H28O2

  • Mr = 300.42

  • Monoclinic, C 2

  • a = 28.317 (2) Å

  • b = 9.4539 (5) Å

  • c = 13.7684 (10) Å

  • [beta] = 111.017 (9)°

  • V = 3440.7 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 298 K

  • 0.50 × 0.40 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis171; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis171. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.985, Tmax = 1.000

  • 7321 measured reflections

  • 4697 independent reflections

  • 2893 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.199

  • S = 1.03

  • 4697 reflections

  • 404 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2O2...O4i 0.82 2.00 2.808 (7) 167
O4-H4O4...O3ii 0.82 2.09 2.858 (7) 156
Symmetry codes: (i) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) -x+1, y+1, -z+2.

Data collection: CrysAlis171 (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis171. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis171; data reduction: CrysAlis171; 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: ORTEX (McArdle, 1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]); software used to prepare material for publication: CIFTAB (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2491 ).


Acknowledgements

The authors thank the Science Foundation Ireland (SFI) for funding for the Solid State Pharmaceuticals Cluster (SSPC).

References

Bhatt, P. M. & Desiraju, G. R. (2006). Acta Cryst. C62, o362-o363.  [CSD] [CrossRef] [details]
Chakrabarti, P., Banerjee, D. K. & Venkatesan, K. (1981). Steroids, 37, 269-279.  [CrossRef] [ChemPort] [PubMed]
Danaci, S., Kendi, E., Moers, F. G., Behm, H. & Beurskens, P. T. (1988). Acta Cryst. C44, 1677-1679.  [CrossRef] [details]
Delettré, J., Mornon, J.-P. & Lepicard, G. (1975). Acta Cryst. B31, 450-453.  [CrossRef] [details] [ISI]
Desiraju, G. R. (2002). CrystEngComm, 4, 499-499.  [ISI] [CrossRef] [ChemPort]
Druzhinina, A., Andryushina, V., Stytsenko, T. & Voishvillo, N. (2008). Appl. Biochem. Microbiol. 44, 580-584.  [ISI] [CrossRef] [ChemPort]
Duax, W. L., Rohrer, D. C. & Segaloff, A. (1982). Acta Cryst. B38, 531-534.  [CrossRef] [ISI] [details]
Karpinska, J., Erxleben, A. & McArdle, P. (2011). Cryst. Growth Des. 11, 2829-2838.  [CrossRef] [ChemPort]
Lewis, T. C., Tocher, D. A. & Price, S. L. (2005). Cryst. Growth Des. 5, 983-993.  [CSD] [CrossRef] [ChemPort]
McArdle, P. (1995). J. Appl. Cryst. 28, 65.  [CrossRef] [details]
McPhail, A. T., Luhan, P. A., Tschang, P.-S. W. & Onan, K. D. (1977). J. Chem. Soc. Perkin Trans. 2, pp. 379-383.
Oxford Diffraction (2010). CrysAlis171. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Verma, R., Jasrotia, D. & Bhat, M. (2006). J. Chem. Crystallogr. 36, 283-287.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o60  [ doi:10.1107/S1600536812049860 ]

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