10α-Hy­droxy-4,9-dimethyl-13-(morph­o­lin-4-ylmeth­yl)-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

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

doi:10.1107/S1600536811053207

Volume 68
Part 1
Pages o167-o168
January 2012

Received 5 December 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.044
wR = 0.110
Data-to-parameter ratio = 8.7
Details

10-Hydroxy-4,9-dimethyl-13-(morpholin-4-ylmethyl)-3,8,15-trioxatetracyclo[10.3.0.0^2,4.0^7,9]pentadecan-14-one

Mohamed Moumou,^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, C₁₉H₂₉NO₆, 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 molecule contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair-chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hydroxy group forming the flap. In the crystal, weak C-HO hydrogen bonds connect the molecules into layers parallel to (001). An intramolecular O-HN hydrogen bond is also present.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: El Hassany et al. (2004); Qureshi et al. (1990). For the reactivity of this sesquiterpene, see: Hwang et al. (2006); Neukirch et al. (2003); Neelakantan et al. (2009). For ring puckering parameters, see: Cremer & Pople (1975). For the synthesis see: Moumou et al. (2010).

Experimental

Crystal data

C₁₉H₂₉NO₆
M_r = 367.43
Monoclinic, P 2₁
a = 11.6772 (9) Å
b = 6.9524 (4) Å
c = 11.8244 (9) Å
= 102.160 (2)°
V = 938.42 (12) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.65 × 0.45 × 0.26 mm

Data collection

Bruker X8 APEXII CCD diffractometer
7793 measured reflections
2069 independent reflections
1661 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.110
S = 1.07
2069 reflections
239 parameters
1 restraint
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN	0.82	2.23	3.048 (3)	178
C1-H1O2ⁱ	0.98	2.32	3.169 (4)	145
C2-H2O5ⁱⁱ	0.98	2.50	3.260 (3)	134
C4-H4BO3ⁱⁱⁱ	0.97	2.52	3.367 (4)	146
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+1]$ .

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: LH5393 ).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for financial support.

References

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