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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 [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.110
Data-to-parameter ratio = 8.7
Details
Open access

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

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[9.3.0.02,4]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-H...O hydrogen bonds connect the molecules into layers parallel to (001). An intramolecular O-H...N hydrogen bond is also present.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: El Hassany et al. (2004[El Hassany, B., El Hanbali, F., Akssira, M., Mellouki, F., Haidou, A. & Barero, A. F. (2004). Fitoterapia, 75, 573-576.]); Qureshi et al. (1990[Qureshi, S., Ageel, A. M., Al-Yahya, M. A., Tariq, M., Mossa, J. S. & Shah, A. H. (1990). J. Ethnopharmacol. 28, 157-162.]). For the reactivity of this sesquiterpene, see: Hwang et al. (2006[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.]); Neukirch et al. (2003[Neukirch, H., Kaneider, N. C., Wiedermann, C. J., Guerriero, A. & D?Ambrosio, M. (2003). Bioorg. Med. Chem. 11, 1503-1510.]); Neelakantan et al. (2009[Neelakantan, S., Nasim, Sh., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346-4349.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the synthesis see: Moumou et al. (2010[Moumou, M., Akssira, M., El Ammari, L., Benharref, A. & Berraho, M. (2010). Acta Cryst. E66, o2395.]).

[Scheme 1]

Experimental

Crystal data
  • C19H29NO6

  • Mr = 367.43

  • Monoclinic, P 21

  • a = 11.6772 (9) Å

  • b = 6.9524 (4) Å

  • c = 11.8244 (9) Å

  • [beta] = 102.160 (2)°

  • V = 938.42 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.110

  • S = 1.07

  • 2069 reflections

  • 239 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N 0.82 2.23 3.048 (3) 178
C1-H1...O2i 0.98 2.32 3.169 (4) 145
C2-H2...O5ii 0.98 2.50 3.260 (3) 134
C4-H4B...O3iii 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[Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick,2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick,2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia,1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.])and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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

Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
El Hassany, B., El Hanbali, F., Akssira, M., Mellouki, F., Haidou, A. & Barero, A. F. (2004). Fitoterapia, 75, 573-576.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
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.
Moumou, M., Akssira, M., El Ammari, L., Benharref, A. & Berraho, M. (2010). Acta Cryst. E66, o2395.  [CSD] [CrossRef] [details]
Neelakantan, S., Nasim, Sh., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346-4349.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o167-o168   [ doi:10.1107/S1600536811053207 ]

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