17β-Hy­droxy-17α-methyl­androsta-1,4-dien-3-one

Karpinska, J.; Erxleben, A.; McArdle, P.

doi:10.1107/S1600536812049860

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 (C-C) = 0.009 Å
R = 0.072
wR = 0.199
Data-to-parameter ratio = 11.6
Details

17-Hydroxy-17-methylandrosta-1,4-dien-3-one

Jolanta Karpinska,^a Andrea Erxleben ^a and Patrick McArdle ^a ^*

^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-HO 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); Lewis et al. (2005); Desiraju et al. (2002). For related structures of other anabolic steroids, see: Verma et al. (2006). For related structures of steroid compounds with non-hydrogen-bonded OH or C=O motifs, see: Karpinska et al. (2011); Danaci et al. (1988); Chakrabarti et al. (1981); McPhail et al. (1977); Delettré et al. (1975). For applications of methandrostenolone, see: Druzhinina et al. (2008). For a previously reported mono hydrate (with no unused hydrogen-bonding capacity), see: Duax et al. (1982).

Experimental

Crystal data

C₂₀H₂₈O₂
M_r = 300.42
Monoclinic, C 2
a = 28.317 (2) Å
b = 9.4539 (5) Å
c = 13.7684 (10) Å
= 111.017 (9)°
V = 3440.7 (4) Å³
Z = 8
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis171. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.985, T_max = 1.000
7321 measured reflections
4697 independent reflections
2893 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.072
wR(F²) = 0.199
S = 1.03
4697 reflections
404 parameters
1 restraint
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O2O4ⁱ	0.82	2.00	2.808 (7)	167
O4-H4O4O3ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: CIFTAB (Sheldrick, 2008).

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.
Chakrabarti, P., Banerjee, D. K. & Venkatesan, K. (1981). Steroids, 37, 269-279.
Danaci, S., Kendi, E., Moers, F. G., Behm, H. & Beurskens, P. T. (1988). Acta Cryst. C44, 1677-1679.
Delettré, J., Mornon, J.-P. & Lepicard, G. (1975). Acta Cryst. B31, 450-453.
Desiraju, G. R. (2002). CrystEngComm, 4, 499-499.
Druzhinina, A., Andryushina, V., Stytsenko, T. & Voishvillo, N. (2008). Appl. Biochem. Microbiol. 44, 580-584.
Duax, W. L., Rohrer, D. C. & Segaloff, A. (1982). Acta Cryst. B38, 531-534.
Karpinska, J., Erxleben, A. & McArdle, P. (2011). Cryst. Growth Des. 11, 2829-2838.
Lewis, T. C., Tocher, D. A. & Price, S. L. (2005). Cryst. Growth Des. 5, 983-993.
McArdle, P. (1995). J. Appl. Cryst. 28, 65.
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.
Verma, R., Jasrotia, D. & Bhat, M. (2006). J. Chem. Crystallogr. 36, 283-287.

organic compounds