12-Anilinomethyl-9α-hy­droxy-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

Moumou, M.; Benharref, A.; Berraho, M.; Avignant, D.; Oudahmane, A.; Akssira, M.

doi:10.1107/S1600536811015303

Volume 67
Part 6
Pages o1388-o1389
June 2011

Received 13 April 2011
Accepted 22 April 2011
Online 11 May 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.044
wR = 0.131
Data-to-parameter ratio = 8.4
Details

12-Anilinomethyl-9-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one

Mohamed Moumou,^a Ahmed Benharref,^b Moha Berraho,^b Daniel Avignant,^c Abdelghani Oudahmane ^c and Mohamed Akssira ^a ^*

^aLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco,^bLaboratoire de Chimie des Substances Naturelles, URAC16, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^cUniversité Blaise Pascal, Laboratoire des Matériaux, Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubière, France
Correspondence e-mail: abenharref@yahoo.fr

The title compound, C₂₁H₂₇NO₄, was synthesized from 9 [alpha] -hydroxyparthenolide, which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent molecules. In each, the ten-membered ring displays an approximative chair-chair conformation. Each of the five-membered rings adopts a flattened envelope conformation, the C(H)-C-C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.443 (2) and 0.553 (2) Å. The dihedral angle between the least-squares planes through the ten- and five-membered rings in the two molecules are similar [22.54 (17) and 23.39 (14)°]. In the crystal, molecules are linked by O-HO, O-HN and N-HO hydrogen bonds.

Related literature

For the isolation and biological activity of 9 [alpha] -hydroxyparthenolide, see: El Hassany et al. (2004). For the reactivity of this sesquiterpene, see: Castaneda-Acosta et al. (1997); Neukirch et al. (2003); Der-Ren et al. (2006); Neelakantan et al.(2009). For conformations of ten-membered rings, see: Watson & Zabel (1982). For conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₁H₂₇NO₄
M_r = 357.44
Monoclinic, P 2₁
a = 11.1067 (8) Å
b = 11.9406 (9) Å
c = 14.6930 (11) Å
= 106.315 (2)°
V = 1870.1 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.27 × 0.18 × 0.12 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
18091 measured reflections
4005 independent reflections
3651 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.131
S = 1.04
4005 reflections
474 parameters
1 restraint
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO6ⁱ	0.86	2.54	3.311 (3)	150
O1-H01N2	0.82	2.41	3.221 (4)	169
O5-H05O1	0.82	1.97	2.778 (3)	170
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

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 (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: TK2738 ).

Acknowledgements

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

References

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