21-(3-Carboxy­propano­yl)-11β,17-dihydroxy­pregn-4-ene-3,20-dione monohydrate

Hongliang Wang; Junhai Xiao; Pengfei Chen; Tie-Min Sun

doi:10.1107/S160053681001648X

. 2010 May 12;66(Pt 6):o1331. doi: 10.1107/S160053681001648X

21-(3-Carboxypropanoyl)-11β,17-dihydroxypregn-4-ene-3,20-dione monohydrate

Hongliang Wang ^a, Junhai Xiao ^b, Pengfei Chen ^b, Tie-Min Sun ^a,^*

PMCID: PMC2979527 PMID: 21579421

Abstract

In the title compound, C₂₅H₃₄O₈·H₂O, the two crylohexane rings adopt chair conformations. In the crystal, the organic molecule and the water molecule are linked by O—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to glucocorticoids, see: Schäcke et al. (2002 ▶). For the synthesis, see: Fang et al. (2007 ▶).

Experimental

Crystal data

C₂₅H₃₄O₈·H₂O
M _r = 480.54
Orthorhombic,
a = 7.2672 (15) Å
b = 16.606 (3) Å
c = 20.009 (4) Å
V = 2414.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.16 × 0.14 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
21231 measured reflections
2848 independent reflections
2562 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.106
S = 1.06
2848 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S160053681001648X/hb5414sup1.cif

e-66-o1331-sup1.cif^{(26KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001648X/hb5414Isup2.hkl

e-66-o1331-Isup2.hkl^{(139.8KB, 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
O2—H2⋯O8ⁱ	0.82	2.06	2.828 (3)	155
O3—H3A⋯O9	0.82	1.91	2.720 (2)	170
O7—H7⋯O1ⁱⁱ	0.82	1.91	2.716 (2)	167
O9—H2W⋯O2ⁱⁱⁱ	0.85	2.08	2.884 (3)	158
O9—H1W⋯O1^iv	0.85	1.95	2.795 (3)	174

Open in a new tab

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

Acknowledgments

The authors thank Dr Yi-Ying Gao (Institute of Process Engineering, Chinese Academy of Science, Beijing) for the structure analysis.

supplementary crystallographic information

Comment

Glucocorticoids (GCs) process varied biological properties such as anti-inflammatory, immunosuppressive and countershock activities (Schäcke et al., 2002). In view of these importances and to determine the molecular conformation, a crystallographic study of the title compound has been carried out.

The molecular structure is shown in Fig. 1. All the bond lengths and angles are within normal ranges. The molecule contains three six-membered rings (A ring atoms C1-C5/C18; B ring atoms C5-C8/C17/C18; C ring atoms C8/C9/C13/C15-C17) and a five-member ring (D ring atoms C9-C13). Ring B and C adopt chair conformations.

In the crystal structure, the molecules are linked via intermolecular O2—H2···O8, O7—H7···O1 interactions. The molecules and water are additionally linked by strong O3—H3A···O9, O9—H2W···O2, O9—H1W···O1 actions (Fig. 2).

Experimental

To a solution of hydrocortisone (5.43 g, 15 mmol) in pyridine (75 ml), succinic anhydride (3 g, 30 mmol) was added dropwise with stirring at room temperature. The mixture was refluxed for 8 hrs. After pouring the solution to ice water (100 ml) and adjusting pH to 5.0-5.5 with 5% HCl (aq), the resulting white solid was obtained and then collected by filtration, washed with water and dried (Fang et al., 2007). Colourless prisms of (I) were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days, presumably the water of crystallisation was absorbed from the atmosphere.