3β-Acet­oxy-19-hy­droxy-Δ5-pregnen-20-one

Meier zu Greffen, A.; Kranz, D.P.; Neudörfl, J.-M.; Schmalz, H.-G.

doi:10.1107/S1600536813002493

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 (C-C) = 0.003 Å
R = 0.037
wR = 0.079
Data-to-parameter ratio = 9.9
Details

3-Acetoxy-19-hydroxy-⁵-pregnen-20-one

Aike Meier zu Greffen,^a Darius P. Kranz,^a Jörg-M. Neudörfl ^a and Hans-Günther Schmalz ^a ^*

^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-HO hydrogen bonds, forming chains along the b axis.

Related literature

For an overview of steroids as biologically important molecules, see: Fieser & Fieser (1961); Hanson (2010). For examples of steroids possessing a rearranged A/B-ring system, see: Du et al. (2008); Aoki et al. (2006); Flyer et al. (2010). For related C-19-functionalized steroids, see: El Sheikh et al. (2007); Shenvi et al. (2008). For an overview of remote functionalization, see: Reese (2001); Heusler & Kalvoda (1964). For the first synthesis of the title compound, see: Halpern et al. (1963). For examples of the title compound as an intermediate for rearranged A/B-ring systems, see: Knox et al. (1965); Kranz et al. (2011). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₂₃H₃₄O₄
M_r = 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 radiation
= 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(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.079
S = 0.99
2457 reflections
247 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AO2ⁱ	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); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SCHAKAL99 (Keller, 1999); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Aoki, S., Watanabe, Y., Sanagawa, M., Setiawan, A., Kotoku, N. & Kobayashi, M. (2006). J. Am. Chem. Soc. 128, 3148-3149.
Du, L., Zhu, T., Fang, Y., Gu, Q. & Zhu, W. (2008). J. Nat. Prod. 71, 1343-1351.
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.
Halpern, O., Villotti, W. & Bowers, A. (1963). Chem. Ind. (London), 116, 38-39.
Hanson, J. R. (2010). Nat. Prod. Rep. 27, 887-899.
Heusler, K. & Kalvoda, J. (1964). Angew. Chem. Int. Ed. Engl. 3, 525-596.
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.
Kranz, D. P., Meier zu Greffen, A., El Sheikh, S., Neudörfl, J. M. & Schmalz, H. G. (2011). Eur. J. Org. Chem. pp. 2860-2866.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shenvi, R. A., Guerrero, C. A., Shi, J., Li, C. C. & Baran, P. S. (2008). J. Am. Chem. Soc. 130, 7241-7243.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds

3-Acetoxy-19-hydroxy-5-pregnen-20-one