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Volume 68 
Part 1 
Page o165  
January 2012  

Received 12 December 2011
Accepted 13 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.114
Data-to-parameter ratio = 9.9
Details
Open access

Methyl 2-(8a-hydroxy-4a-methyl-8-methylenedecahydronaphthalen-2-yl)acrylate

abLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco,bUniversite Blaise Pascal, Laboratoire des Mate'riaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubie`re, France, and cLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco
Correspondence e-mail: mberraho@yahoo.fr

The title compound, C16H24O3, was synthesized from ilicic acid which was isolated from the aerial part of Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter]. The molecule contains two fused six-membered rings both in chair conformations. In the crystal, molecules are linked into chains running parallel to the a axis by O-H...O hydrogen bonds.

Related literature

For the synthesis, see: Barrero et al. (2009[Barrero, A. F., Herrador, M. M., Arteaga, J. & Catalan, V. (2009). Eur. J. Org. Chem. pp. 3589-3594.]). For the medicinal and pharmacological properties of Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter], see: Shtacher & Kasshman (1970[Shtacher, G. & Kasshman, Y. (1970). J. Med. Chem. 13, 1221-1223.]); Bohlmann et al. (1977[Bohlmann, F., Czerson, H. & Schoneweib, S. (1977). Chem. Ber. 110, 1330-1334.]); Chiappini et al. (1982[Chiappini, I., Fardella, G., Menghini, A. & Rossi, C. (1982). Planta Med. 44, 159-161.]); Azoulay et al. (1986[Azoulay, P., Reynier, J. P., Balansard, G., Gasquet, M. & Timon-David, P. (1986). Pharm. Acta Helv. 61, 345-352.]); Bohlmann et al. (1977[Bohlmann, F., Czerson, H. & Schoneweib, S. (1977). Chem. Ber. 110, 1330-1334.]); Ceccherelli et al. (1988[Ceccherelli, P., Curini, M. & Marcotullio, M. C. (1988). J. Nat. Prod. 51, 1006-1009.]). For background to phytochemical studies of plants, see: Geissman & Toribio (1967[Geissman, T. A. & Toribio, F. P. (1967). Phytochemistry, 6, 1563-1567.]). For conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24O3

  • Mr = 264.35

  • Orthorhombic, P 21 21 21

  • a = 6.0666 (5) Å

  • b = 10.0900 (9) Å

  • c = 23.747 (2) Å

  • V = 1453.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.65 × 0.45 × 0.26 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 6831 measured reflections

  • 1745 independent reflections

  • 1202 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.114

  • S = 1.04

  • 1745 reflections

  • 176 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.82 2.24 3.033 (4) 161
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2005[Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5751 ).


Acknowledgements

We thank Professor Daniel Avignant for the data collection.

References

Azoulay, P., Reynier, J. P., Balansard, G., Gasquet, M. & Timon-David, P. (1986). Pharm. Acta Helv. 61, 345-352.  [ChemPort] [PubMed] [ISI]
Barrero, A. F., Herrador, M. M., Arteaga, J. & Catalan, V. (2009). Eur. J. Org. Chem. pp. 3589-3594.  [CrossRef]
Bohlmann, F., Czerson, H. & Schoneweib, S. (1977). Chem. Ber. 110, 1330-1334.  [CrossRef] [ChemPort]
Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ceccherelli, P., Curini, M. & Marcotullio, M. C. (1988). J. Nat. Prod. 51, 1006-1009.  [CrossRef] [ChemPort] [PubMed] [ISI]
Chiappini, I., Fardella, G., Menghini, A. & Rossi, C. (1982). Planta Med. 44, 159-161.  [CrossRef] [PubMed] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Geissman, T. A. & Toribio, F. P. (1967). Phytochemistry, 6, 1563-1567.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shtacher, G. & Kasshman, Y. (1970). J. Med. Chem. 13, 1221-1223.  [CrossRef] [ChemPort] [PubMed] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o165  [ doi:10.1107/S1600536811053712 ]

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