5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one

Moumou, M.; Benharref, A.; Berraho, M.; El Ammari, L.; Akssira, M.; Elhakmaoui, A.

doi:10.1107/S160053681102352X

Volume 67
Part 7
Pages o1760-o1761
July 2011

Received 13 June 2011
Accepted 16 June 2011
Online 22 June 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 9.2
Details

5,9-Dihydroxy-9-methyl-3,6-dimethylene-3a,4,5,6,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2(3H)-one

Mohamed Moumou,^a ^* Ahmed Benharref,^a Moha Berraho,^a Lahcen El Ammari,^b Mohamed Akssira ^c and Ahmed Elhakmaoui ^c

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco,^bLaboratoire de Chimie du Solide Appliqueé, Faculté des Sciences, Avenue Ibn, Battouta BP 1014 Rabat, Morocco, 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, C₁₅H₂₀O₄, was synthesized from 9 [alpha] -hydroxyparthenolide (9 [alpha] -hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69 (10)°. In the crystal, molecules are linked into chains propagating along the c axis by intermolecular O-HO hydrogen bonds; an intramolecular O-HO link also occurs.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996); Bellakhdar (1997); El Hassany et al. (2004); Qureshi et al. (1990). For the reactivity of this sesquiterpene, see: El Haib et al. (2011). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₅H₂₀O₄
M_r = 264.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.4210 (14) Å
b = 13.504 (3) Å
c = 15.619 (3) Å
V = 1354.4 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.50 × 0.33 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
14445 measured reflections
1610 independent reflections
1473 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.097
S = 1.08
1610 reflections
175 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O3	0.82	2.42	3.015 (2)	131
O4-H4O2ⁱ	0.82	2.03	2.819 (2)	162
Symmetry code: (i) $[-x-{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 and 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: SJ5165 ).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Abdel Sattar, E., Galal, A. M. & Mossa, J. S. (1996). J. Nat. Prod. 59, 403-405.
Bellakhdar, J. (1997). La Pharmacopée Marocaine Traditionnelle, pp. 272-274. Paris: Edition Ibis Press.
Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
El Haib, A., Benharref, A., Sandra, P.-M., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.
El Hassany, B., El Hanbali, F., Akssira, M., Mellouki, F., Haidou, A. & Barero, A. F. (2004). Fitoterapia, 75, 573-576.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Qureshi, S., Ageel, A. M., Al-Yahya, M. A., Tariq, M., Mossa, J. S. & Shah, A. H. (1990). J. Ethnopharmacol. 28, 157-162.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds