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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 [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.152
Data-to-parameter ratio = 16.6
Details
Open access

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

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-H...O hydrogen bonds, forming chains along [112]; these chains are linked by weak non-classical C-H...O 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[Heaney, R. P. (2008). Clin. J. Am. Soc. Nephrol. 3, 1535-1541.]); Henry (2011[Henry, H. L. (2011). Best Pract. Res. Clin. Endocrinol. Metab. 25, 531-541.]). For related structures, see: Maehr & Uskokovic (2004[Maehr, H. & Uskokovic, M. R. (2004). Eur. J. Org. Chem. pp. 1703-1713.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C19H32O2

  • Mr = 292.45

  • Monoclinic, C 2

  • a = 20.057 (4) Å

  • b = 7.3816 (15) Å

  • c = 13.700 (3) Å

  • [beta] = 112.324 (4)°

  • V = 1876.3 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.602, Tmax = 0.745

  • 4958 measured reflections

  • 3254 independent reflections

  • 2389 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.152

  • S = 1.02

  • 3254 reflections

  • 196 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O7'-H7'...O4i 0.82 2.08 2.876 (3) 164
C3A-H3A1...O7'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[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2006[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.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


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.  [CrossRef] [ChemPort] [ISI]
Heaney, R. P. (2008). Clin. J. Am. Soc. Nephrol. 3, 1535-1541.  [CrossRef] [PubMed] [ChemPort]
Henry, H. L. (2011). Best Pract. Res. Clin. Endocrinol. Metab. 25, 531-541.  [CrossRef] [ChemPort] [PubMed]
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.  [ISI] [CrossRef] [ChemPort] [details]
Maehr, H. & Uskokovic, M. R. (2004). Eur. J. Org. Chem. pp. 1703-1713.  [CSD] [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o218  [ doi:10.1107/S1600536812051343 ]

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