12-{[4-(2-Fluoro­phen­yl)piperazin-1-yl]­meth­yl}-9α-hy­droxy-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

Moumou, M.; Benharref, A.; Daran, J.C.; Outouch, R.; Berraho, M.

doi:10.1107/S1600536812006411

Volume 68
Part 3
Pages o741-o742
March 2012

Received 12 February 2012
Accepted 13 February 2012
Online 17 February 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.007 Å
R = 0.068
wR = 0.197
Data-to-parameter ratio = 8.7
Details

12-{[4-(2-Fluorophenyl)piperazin-1-yl]methyl}-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 Jean Claude Daran,^c Rachid Outouch ^b ^* and Moha Berraho ^b

^aLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco,^bLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences, Semlalia, BP 2390, Boulevard My Abdellah, 40000 Marrakech, Morocco, and ^cLaboratoire de Chimie de Coordination, 205 Route de Narbonne, 31077 Toulouse Cedex 04, France
Correspondence e-mail: mberraho@yahoo.fr

The title compound, C₂₅H₃₃FN₂O₄, 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 asymmetric unit contains two independent molecules. In each molecule, the ten-membered ring displays an approximative chair-chair conformation. Each of the piperazine rings adopts a perfect chair conformation, while both lactone rings show an envelope conformation, one with the C atom bearing the piperazin-1-ylmethyl group as the flap, the other with the junction C atom not attached to the ring O atom as the flap. The dihedral angles between the least-squares planes through the ten- and five-membered rings in the two molecules are similar [19.1 (3) and 16.2 (3)°]. An intramolecular O-HN hydrogen bond stabilizes the molecular conformation. The crystal packing is stabilized by C-HO hydrogen bonds.

Related literature

For background to the medicinal uses of the plant Anvillea adiata, see: El Hassany et al. (2004); Qureshi et al. (1990). For the reactivity of this sesquiterpene, see: Castaneda-Acosta et al. (1997); Hwang et al. (2006); Neukirch et al. (2003); Neelakantan et al. (2009). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₅H₃₃FN₂O₄
M_r = 444.53
Monoclinic, P 2₁
a = 14.583 (2) Å
b = 6.3366 (17) Å
c = 24.697 (3) Å
= 93.598 (14)°
V = 2277.7 (8) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 180 K
0.56 × 0.36 × 0.1 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.789, T_max = 1.000
24656 measured reflections
5050 independent reflections
4582 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.197
S = 1.12
5050 reflections
583 parameters
1 restraint
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1BN1	0.82	2.19	2.979 (6)	163
O1A-H1A1N2A	0.82	2.08	2.882 (6)	164
C1-H1O3ⁱ	0.98	2.47	3.035 (7)	116
C13-H131O3ⁱⁱ	0.97	2.51	3.394 (7)	152
C10-H10O1	0.98	2.36	2.861 (6)	111
C10A-H10AO1A	0.98	2.36	2.860 (6)	111
C13A-H13AO3Aⁱⁱⁱ	0.97	2.57	3.391 (6)	143
C11A-H11AO3A^iv	0.98	2.60	3.338 (6)	132
C15-H15FO1^v	0.96	2.42	3.375 (7)	171
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: BT5817 ).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
Castaneda-Acosta, J., Pentes, H. G., Fronczek, F. R. & Fischer, N. H. (1997). J. Chem. Crystallogr. 27, 635-639.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
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.
Hwang, D.-R., Wu, Y.-S., Chang, C.-W., Lien, T.-W., Chen, W.-C., Tan, U.-K., Hsu, J. T. A. & Hsieh, H.-P. (2006). Bioorg. Med. Chem. 14, 83-91.
Neelakantan, S., Nasim, Sh., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346-4349.
Neukirch, H., Kaneider, N. C., Wiedermann, C. J., Guerriero, A. & D'Ambrosio, M. (2003). Bioorg. Med. Chem. 11, 1503-1510.
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

12-{[4-(2-Fluorophenyl)piperazin-1-yl]methyl}-9-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one