3β,12β,14α-Trihydroxy­pregnan-20-one

Hefang Shi; Yingxia Li

doi:10.1107/S1600536809013853

. 2009 Apr 25;65(Pt 5):o1102. doi: 10.1107/S1600536809013853

3β,12β,14α-Trihydroxypregnan-20-one

Hefang Shi ^a, Yingxia Li ^a,^*

PMCID: PMC2977780 PMID: 21583916

Abstract

The title compound, C₂₁H₃₄O₄, is a steriod of the pregnane family prepared by the sequential oxidation and reduction of 3β,12β-diacetoxy-20-ethylenedioxypregnan-14-ene. The conformations of the six-membered rings are close to chair forms, while the five-membered ring adopts an envelope conformation. All the rings are trans-fused and an intramolecular O—H⋯O hydrogen bond occurs. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into a two-dimensional network.

Related literature

For the synthesis, see: Templeton & Yan (1992 ▶); Fell & Heathcock (2002 ▶). For background on hecogenin, see: Ranu & Samanta (2003 ▶).

Experimental

Crystal data

C₂₁H₃₄O₄
M _r = 350.48
Monoclinic,
a = 6.1364 (7) Å
b = 12.1472 (13) Å
c = 12.7593 (14) Å
β = 101.513 (2)°
V = 931.94 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.50 × 0.44 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.729, T _max = 0.97
5569 measured reflections
2194 independent reflections
1930 reflections with I > 2σ(I)
R _int = 0.107

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.125
S = 1.01
2194 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013853/hb2940sup1.cif

e-65-o1102-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013853/hb2940Isup2.hkl

e-65-o1102-Isup2.hkl^{(103.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.81 (4)	2.19 (4)	2.916 (3)	150 (3)
O2—H2⋯O4	0.80 (4)	2.01 (4)	2.771 (3)	158 (3)
O1—H1⋯O2ⁱⁱ	0.88 (5)	2.05 (6)	2.928 (3)	170 (4)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 30572245).

supplementary crystallographic information

Comment

The title compound was obtained by oxidation and reduction of the corresponding 3β,12β-diacetoxypregnan-20-ethylenedioxy-14-ene, which was prepared from hecogenin (Fell & Heathcock, 2002; Ranu & Samanta, 2003). We have undertaken the X-ray crystal structure determination of (I) in order to establish its molecular conformation and relative stereochemistry.

The hydroxyl group at C12 and the acetyl group at C17 are beta-oriented respectively, whereas the hydroxyl group at C14 is alpha-oriented (Fig. 1). The conformation of the six-membered rings in both molecules are close to chair forms, while the five-membered ring adopts an envelope conformation. All rings in both molecules are trans-fused. The molecules of (I) are held together by an extensive O—H···O hydrogen-bonding two-dimensional network (Table 1, Fig. 2).

Experimental

The title compound was prepared according to the literature method (Fell & Heathcock, 2002; Templeton & Yan 1992). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature (m.p. 343–347 K).