11β,17,21-Trihydr­oxy-6α-methyl-3,20-dioxopregna-1,4-dien-21-yl 3-carboxy­propionate

Hui-Mei An; Ning-Bo Gong; Yang Lu

doi:10.1107/S1600536809011969

. 2009 Apr 8;65(Pt 5):o987. doi: 10.1107/S1600536809011969

11β,17,21-Trihydroxy-6α-methyl-3,20-dioxopregna-1,4-dien-21-yl 3-carboxypropionate

Hui-Mei An ^a, Ning-Bo Gong ^a, Yang Lu ^a,^*

PMCID: PMC2977682 PMID: 21584025

Abstract

The molecule of the title compound, C₂₆H₃₄O₈, a prednisolone derivative, contains three six-membered rings (A, B and C) and one five-membered ring (D). Ring A is planar and rings B and C adopt chair conformations, while ring D adopts an envelope conformation with the C atom bonded to the methyl group at the flap. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds

Related literature

For the preparation, see: Anderson et al. (1984 ▶). For bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₆H₃₄O₈
M _r = 474.53
Orthorhombic,
a = 8.3125 (1) Å
b = 10.1765 (1) Å
c = 28.8472 (3) Å
V = 2440.25 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
8346 measured reflections
3397 independent reflections
3365 reflections with I > 2σ(I)
R _int = 0.018
θ_max = 58.8°

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.101
S = 1.07
3397 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ▶), 1388 Friedel pairs
Flack parameter: 0.0 (2)

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011969/sj2598sup1.cif

e-65-0o987-sup1.cif^{(26.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011969/sj2598Isup2.hkl

e-65-0o987-Isup2.hkl^{(166.6KB, 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—H2A⋯O4ⁱ	0.82	2.30	3.115 (2)	172
O3—H3A⋯O7ⁱⁱ	0.82	2.13	2.943 (2)	173
O8—H8B⋯O1ⁱⁱⁱ	0.82	1.82	2.640 (3)	176

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

Acknowledgments

We acknowledge financial assistance from the International Centre for Diffraction Data. We also acknowledge the Innovation Method Funds of the Ministry of Science and Technology of China (grant No. 2008IMO22200).

supplementary crystallographic information

Comment

The title compound,(I)(Fig. 1),is a prednisolone derivative. It is prepared according to the procedure of Anderson et al. (Anderson et al., 1984) and recrystallized from methanol. Its crystal structure is reported here for the first time, Fig, 1.

Bond lengths within the molecule are normal (Allen et al., 1987). The molecule contains three six-membered rings(A/B/C) and one five-membered ring (D). Ring A is planar and ring B and C adopt chair conformations, while ring D adopts an envelope conformation wit hatom C13 at the flap. Rings B, C and D are trans-fused. The dihedral angles between the least-squares planes fitted through all non-H atoms of the rings are A/B = 139.0 (2) °,B/C = 5.9 (2) °, C/D = 7.3 (3) °.

The structure is stablized by intermolecular hydrogen bonds (Table 2), which link the molecules into infinite chains. The hydrogen-bonding arrangement is shown in Fig.2.

Experimental

The title compound was prepared according to the procedure of Anderson et al. (1984). Crystals suitable for data collection were obtained by slow evaporation from methanol solution at 283 K over a period of two weeks.