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Volume 69 
Part 2 
Page o313  
February 2013  

Received 9 July 2012
Accepted 24 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.079
Data-to-parameter ratio = 9.9
Details
Open access

3[beta]-Acetoxy-19-hydroxy-[Delta]5-pregnen-20-one

aDepartment für Chemie der Universität zu Köln, Greinstrasse 4, 50939 Köln, Germany
Correspondence e-mail: schmalz@uni-koeln.de

In the title compound, C23H34O4, the C/D and D/E rings are trans fused and the A/B ring possesses an anti fusion. The two cyclohexane rings adopt a chair conformation while the cyclohexene ring exhibits a half-chair conformation. The cyclopentane ring displays an envelope conformation with the C atom bearing the methyl group as the flap. In the crystal, the molecules are linked by O-H...O hydrogen bonds, forming chains along the b axis.

Related literature

For an overview of steroids as biologically important molecules, see: Fieser & Fieser (1961)[Fieser & Fieser (1961). Please supply full reference.]; Hanson (2010[Hanson, J. R. (2010). Nat. Prod. Rep. 27, 887-899.]). For examples of steroids possessing a rearranged A/B-ring system, see: Du et al. (2008[Du, L., Zhu, T., Fang, Y., Gu, Q. & Zhu, W. (2008). J. Nat. Prod. 71, 1343-1351.]); Aoki et al. (2006[Aoki, S., Watanabe, Y., Sanagawa, M., Setiawan, A., Kotoku, N. & Kobayashi, M. (2006). J. Am. Chem. Soc. 128, 3148-3149.]); Flyer et al. (2010[Flyer, A. N., Si, C. & Myers, A. G. (2010). Nat. Chem. 2, 886-892.]). For related C-19-functionalized steroids, see: El Sheikh et al. (2007[El Sheikh, S., Meier zu Greffen, A., Lex, J., Neudörfl, J. M. & Schmalz, H. G. (2007). Synlett, pp. 1881-1884.]); Shenvi et al. (2008[Shenvi, R. A., Guerrero, C. A., Shi, J., Li, C. C. & Baran, P. S. (2008). J. Am. Chem. Soc. 130, 7241-7243.]). For an overview of remote functionalization, see: Reese (2001[Reese, P. B. (2001). Steroids, 66, 481-497.]); Heusler & Kalvoda (1964[Heusler, K. & Kalvoda, J. (1964). Angew. Chem. Int. Ed. Engl. 3, 525-596.]). For the first synthesis of the title compound, see: Halpern et al. (1963[Halpern, O., Villotti, W. & Bowers, A. (1963). Chem. Ind. (London), 116, 38-39.]). For examples of the title compound as an intermediate for rearranged A/B-ring systems, see: Knox et al. (1965[Knox, L. H., Velarde, E., Berger, S., Delfin, I. & Grezemkovsky, R. (1965). J. Org. Chem. 30, 4160-4165.]); Kranz et al. (2011[Kranz, D. P., Meier zu Greffen, A., El Sheikh, S., Neudörfl, J. M. & Schmalz, H. G. (2011). Eur. J. Org. Chem. pp. 2860-2866.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C23H34O4

  • Mr = 374.50

  • Orthorhombic, P 21 21 21

  • a = 8.6960 (6) Å

  • b = 12.3708 (4) Å

  • c = 18.3303 (10) Å

  • V = 1971.91 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.3 × 0.3 × 0.3 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 9889 measured reflections

  • 2457 independent reflections

  • 1943 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.079

  • S = 0.99

  • 2457 reflections

  • 247 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O2i 0.84 2.19 2.9305 (19) 147
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Hooft 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO; 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: SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiburg, Germany.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2076 ).


References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Aoki, S., Watanabe, Y., Sanagawa, M., Setiawan, A., Kotoku, N. & Kobayashi, M. (2006). J. Am. Chem. Soc. 128, 3148-3149.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Du, L., Zhu, T., Fang, Y., Gu, Q. & Zhu, W. (2008). J. Nat. Prod. 71, 1343-1351.  [CrossRef] [PubMed] [ChemPort]
El Sheikh, S., Meier zu Greffen, A., Lex, J., Neudörfl, J. M. & Schmalz, H. G. (2007). Synlett, pp. 1881-1884.
Fieser & Fieser (1961). Please supply full reference.
Flyer, A. N., Si, C. & Myers, A. G. (2010). Nat. Chem. 2, 886-892.  [CrossRef] [ChemPort] [PubMed]
Halpern, O., Villotti, W. & Bowers, A. (1963). Chem. Ind. (London), 116, 38-39.
Hanson, J. R. (2010). Nat. Prod. Rep. 27, 887-899.  [CrossRef] [ChemPort] [PubMed]
Heusler, K. & Kalvoda, J. (1964). Angew. Chem. Int. Ed. Engl. 3, 525-596.  [CrossRef]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Keller, E. (1999). SCHAKAL99. University of Freiburg, Germany.
Knox, L. H., Velarde, E., Berger, S., Delfin, I. & Grezemkovsky, R. (1965). J. Org. Chem. 30, 4160-4165.  [CrossRef] [ChemPort] [PubMed]
Kranz, D. P., Meier zu Greffen, A., El Sheikh, S., Neudörfl, J. M. & Schmalz, H. G. (2011). Eur. J. Org. Chem. pp. 2860-2866.  [CrossRef]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Reese, P. B. (2001). Steroids, 66, 481-497.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shenvi, R. A., Guerrero, C. A., Shi, J., Li, C. C. & Baran, P. S. (2008). J. Am. Chem. Soc. 130, 7241-7243.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o313  [ doi:10.1107/S1600536813002493 ]

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