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Volume 69 
Part 3 
Page o447  
March 2013  

Received 18 January 2013
Accepted 20 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.077
Data-to-parameter ratio = 17.2
Details
Open access

1[beta],15[alpha]-Dihydroxy-16[alpha],17-epoxypregn-4-ene-3,20-dione

aKey Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science and Technology), Ministry of Education, College of Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, People's Republic of China
Correspondence e-mail: minw@tust.edu.cn

The title molecule, C21H28O5, is composed of three six-membered rings (A/B/C) and a five-membered ring (D). Ring A adopts a 1[alpha]-sofa conformation, while rings B and C adopt chair conformations. Cyclopentane ring D adopts a 14[alpha]-envelope conformation. In the crystal, O-H...O hydrogen bonds lead to the formation of ribbons running along the a axis. The structure is further consolidated by C-H...O interactions, which link the molecules head-to-tail into ribbons along the a axis.

Related literature

For background to 16[alpha],17[alpha]-epoxyprogesterone, see: Breskvar et al. (1995[Breskvar, K., Ferencak, Z. & Hudnik-Plevnik, T. (1995). J. Steroid Biochem. Mol. Biol. 52, 271-275.]); Zhou et al. (2009[Zhou, H., Lu, W., Wen, J. & Ma, L. (2009). J. Mol. Catal. B Enzym. 56, 136-141.]). For the crystal structure of a related compound, see: Nie et al. (2005[Nie, Q., Wang, J.-K., Wang, S. & Zhang, M.-J. (2005). Acta Cryst. E61, o912-o913.]).

[Scheme 1]

Experimental

Crystal data
  • C21H28O5

  • Mr = 360.43

  • Orthorhombic, P 21 21 21

  • a = 7.6372 (10) Å

  • b = 13.7067 (16) Å

  • c = 17.083 (2) Å

  • V = 1788.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 113 K

  • 0.22 × 0.18 × 0.14 mm

Data collection
  • Rigaku Saturn 724CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.980, Tmax = 0.987

  • 18889 measured reflections

  • 4237 independent reflections

  • 3529 reflections with I > 2[sigma](I)

  • Rint = 0.062

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.077

  • S = 0.94

  • 4237 reflections

  • 246 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 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
O1-H1...O4i 0.88 (2) 2.06 (2) 2.929 (2) 168
O3-H3...O5ii 0.86 (2) 1.95 (2) 2.767 (2) 159
C1-H1A...O3i 1.00 2.59 3.527 (2) 157
C6-H6A...O1ii 0.99 2.59 3.527 (2) 158
C12-H12B...O3iii 0.99 2.52 3.468 (2) 161
C21-H21B...O2iv 0.98 2.53 3.501 (2) 170
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (ii) x-1, y, z; (iii) x+1, y, z; (iv) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2620 ).


Acknowledgements

This work was supported by the National High Technology Research and Development of China (2011AA02A211) and the National Natural Science Foundation of China (Nos. 21076158 and 21276196).

References

Breskvar, K., Ferencak, Z. & Hudnik-Plevnik, T. (1995). J. Steroid Biochem. Mol. Biol. 52, 271-275.  [CrossRef] [ChemPort] [PubMed]
Nie, Q., Wang, J.-K., Wang, S. & Zhang, M.-J. (2005). Acta Cryst. E61, o912-o913.  [CrossRef] [details]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhou, H., Lu, W., Wen, J. & Ma, L. (2009). J. Mol. Catal. B Enzym. 56, 136-141.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o447  [ doi:10.1107/S1600536813005023 ]

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