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

Tebbaa, M.; Benharref, A.; Oudahmane, A.; Mellouki, F.; Berraho, M.

doi:10.1107/S1600536811053712

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 (C-C) = 0.004 Å
R = 0.046
wR = 0.114
Data-to-parameter ratio = 9.9
Details

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

Mohamed Tebbaa,^a Ahmed Benharref,^a Abdelghani Oudahmane,^b Fouad Mellouki ^c ^* and Moha Berraho ^a

^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-HO hydrogen bonds.

Related literature

For the synthesis, see: Barrero et al. (2009). For the medicinal and pharmacological properties of Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter], see: Shtacher & Kasshman (1970); Bohlmann et al. (1977); Chiappini et al. (1982); Azoulay et al. (1986); Bohlmann et al. (1977); Ceccherelli et al. (1988). For background to phytochemical studies of plants, see: Geissman & Toribio (1967). For conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₆H₂₄O₃
M_r = 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 radiation
= 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(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.114
S = 1.04
1745 reflections
176 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3ⁱ	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); 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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Barrero, A. F., Herrador, M. M., Arteaga, J. & Catalan, V. (2009). Eur. J. Org. Chem. pp. 3589-3594.
Bohlmann, F., Czerson, H. & Schoneweib, S. (1977). Chem. Ber. 110, 1330-1334.
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.
Chiappini, I., Fardella, G., Menghini, A. & Rossi, C. (1982). Planta Med. 44, 159-161.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Geissman, T. A. & Toribio, F. P. (1967). Phytochemistry, 6, 1563-1567.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shtacher, G. & Kasshman, Y. (1970). J. Med. Chem. 13, 1221-1223.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds