(E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol

Hernández Linares, M.-G.; Sandoval Ramírez, J.; Meza Reyes, S.; Montiel Smith, S.; Bernès, S.

doi:10.1107/S1600536808004509

Volume 64
Part 3
Page o613
March 2008

Received 4 February 2008
Accepted 14 February 2008
Online 22 February 2008

Key indicators
Single-crystal X-ray study
T = 296 KP 101 kPa
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.038
wR = 0.097
Data-to-parameter ratio = 7.9
Details

(E)-(25S)-23-Acetyl-5-furost-22-ene-3,26-diol

María-Guadalupe Hernández Linares,^a Jesús Sandoval Ramírez,^b Socorro Meza Reyes,^b Sara Montiel Smith ^b and Sylvain Bernès ^c ^*

^aEscuela de Ingeniería Química, Universidad del Istmo, Ciudad Universitaria S/N, 70760 Sto. Domingo Tehuantepec, Oax., Mexico,^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, San Manuel, 72000 Puebla, Pue., Mexico, and ^cDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico
Correspondence e-mail: sylvain_bernes@hotmail.com

The title steroid, C₂₉H₄₆O₄, is a furostene derivative with a C=C double-bond length of 1.353 (3) Å and an E configuration. The side chain is oriented toward the [alpha] face of the A-E steroidal nucleus and presents a disordered terminal CH₂-OH group [occupancies for resolved sites are 0.591 (9) and 0.409 (9)]. The methyl group at C20 attached to ring E is also oriented toward the [alpha] face, avoiding steric hindrance with the carbonyl O atom of the acetyl group. The furostene and acetyl functionalities form an [alpha] , [beta] -unsaturated ketone system, with an s-cis configuration. All hydroxy and carbonyl groups are involved in weak intermolecular hydrogen bonds. The absolute configuration was assigned from the synthesis.

Related literature

The diacetate of the title compound has been characterized by X-ray crystallography (Sandoval-Ramírez et al., 2003), as well as a related furost-22-ene derivate with the C20 site substituted by a methyl group and an acetyl group (Meza-Reyes et al., 2004).

Experimental

Crystal data

C₂₉H₄₆O₄
M_r = 458.66
Monoclinic, C 2
a = 23.568 (2) Å
b = 7.8420 (9) Å
c = 14.7840 (14) Å
= 101.046 (5)°
V = 2681.7 (5) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 296 (1) K
0.65 × 0.35 × 0.32 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
4351 measured reflections
2559 independent reflections
2121 reflections with I > 2(I)
R_int = 0.026
3 standard reflections every 97 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.097
S = 1.02
2559 reflections
323 parameters
2 restraints
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.13 e Å^-3

Table 1
Selected torsion angles (°)

C20-C22-C23-C23'	-3.5 (4)
C20-C22-C23-C24	175.4 (3)
O22'-C22-C23-C23'	179.3 (2)
O22'-C22-C23-C24	-1.8 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3'-H3'O23"ⁱ	0.98	1.89	2.841 (3)	163
O26A-H26EO3'ⁱⁱ	0.82	2.20	2.951 (6)	153
O26B-H26FO3'ⁱⁱ	0.82	2.24	2.919 (16)	140
Symmetry codes: (i) x, y, z-1; (ii) x, y+1, z+1.

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Release 5.10; Sheldrick, 2008); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2197 ).

Acknowledgements

This work was supported by CONACyT (grant 60397).

References

Meza-Reyes, S., Montiel-Smith, S., Sandoval-Ramírez, J., Bernès, S., Hernández-Linares, G., Santillan, R. L. & Rincón, S. (2004). Acta Cryst. E60, o1137-o1139.
Sandoval-Ramírez, J., Meza-Reyes, S., Montiel-Smith, S., Bernès, S., Hernández-Linares, G. & Bravo, O. V. (2003). Acta Cryst. E59, o1817-o1819.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). XSCANS. Version 2.21. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds