(7aR)-1-[(2R,5S,E)-6-Hy­droxy-5,6-dimethyl­hept-3-en-2-yl]-7a-methyl­hexa­hydro-1H-inden-4(2H)-one

Rivadulla, M.L.; Sene, M.; González, M.; Covelo, B.

doi:10.1107/S1600536812051343

Volume 69
Part 2
Page o218
February 2013

Received 13 December 2012
Accepted 19 December 2012
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.048
wR = 0.152
Data-to-parameter ratio = 16.6
Details

(7aR)-1-[(2R,5S,E)-6-Hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methylhexahydro-1H-inden-4(2H)-one

Marcos L. Rivadulla,^a ^* Massene Sene,^a María González ^a and Berta Covelo ^b

^aDpto. Química Orgánica, Facultade de Química, Universidade de Vigo, E-36310 Vigo, Spain, and ^bUnidad de Difracción de Raios X de Monocristal, Servicio Determinación Estructural, Proteómica e Xenómica, CACTI-Universidade de Vigo, E-36310 Vigo, Spain
Correspondence e-mail: m.lois@uvigo.es

The chiral title compound, C₁₉H₃₂O₂, contains a [4.3.0]-bicyclic moiety in which the shared C-C bond presents a trans configuration and a side chain in which the C=C double bond shows an E conformation. The conformations of five- and six-membered rings are envelope (with the bridgehead atom bearing the methyl substituent as the flap) and chair, respectively, with a dihedral angle of 4.08 (17)° between the idealized planes of the rings. In the crystal, the molecules are self-assembled via classical O-HO hydrogen bonds, forming chains along [112]; these chains are linked by weak non-classical C-HO hydrogen bonds, giving a two-dimensional supramolecular structure parallel to (010). The absolute configuration was established according to the configuration of the starting material.

Related literature

The title compound is a precursor of the hormonally active form of vitamin D3. For general background to vitamin D3, see: Heaney (2008); Henry (2011). For related structures, see: Maehr & Uskokovic (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₉H₃₂O₂
M_r = 292.45
Monoclinic, C 2
a = 20.057 (4) Å
b = 7.3816 (15) Å
c = 13.700 (3) Å
= 112.324 (4)°
V = 1876.3 (6) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 293 K
0.45 × 0.36 × 0.18 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.602, T_max = 0.745
4958 measured reflections
3254 independent reflections
2389 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.152
S = 1.02
3254 reflections
196 parameters
1 restraint
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.11 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O7'-H7'O4ⁱ	0.82	2.08	2.876 (3)	164
C3A-H3A1O7'ⁱⁱ	0.98	2.56	3.523 (3)	166
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+1]$ ; (ii) -x+1, y, -z+2.

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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2614 ).

Acknowledgements

This work was supported financially by the Spanish Ministry of Foreign Affairs and Cooperation (PCIA/030052/10) and the Xunta de Galicia (INCITE845B, INCITE08PXIB314255PR).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Heaney, R. P. (2008). Clin. J. Am. Soc. Nephrol. 3, 1535-1541.
Henry, H. L. (2011). Best Pract. Res. Clin. Endocrinol. Metab. 25, 531-541.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Maehr, H. & Uskokovic, M. R. (2004). Eur. J. Org. Chem. pp. 1703-1713.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds