[Journal logo]

Volume 70 
Part 5 
Pages o530-o531  
May 2014  

Received 24 March 2014
Accepted 3 April 2014
Online 9 April 2014

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.044
wR = 0.102
Data-to-parameter ratio = 8.9
Details
Open access

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

aLaboratoire de Chimie Biomoleculaire, Substances Naturelles et Réactivité URAC16, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, BP 1014, Avenue Ibn Battouta, Rabat, Morocco
Correspondence e-mail: loubidim@gmail.com

The title compound, C25H34N2O5, was synthesized from 9[alpha]-hy­droxy­parthenolide (9[alpha]-hy­droxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one), which in turn was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule comprises a ten-membered ring fused to a five-membered ring with an additional ep­oxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hy­droxy­phenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intra­molecular O-H...N hydrogen-bond stabilizes the mol­ecular conformation. In the crystal, C-H...O hydrogen bonds link the mol­ecules into zigzag chains running along the a-axis direction.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996[Abdel Sattar, E., Galal, A. M. & Mossa, J. S. (1996). J. Nat. Prod. 59, 403-405.]); 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.]). 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.]); 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 a related synthetic procedure, see: Moumou et al. (2012[Moumou, M., Benharref, A., Daran, J.-C., Mellouki, F. & Berraho, M. (2012). Acta Cryst. E68, o589-o590.]). For conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C25H34N2O5

  • Mr = 442.54

  • Monoclinic, C 2

  • a = 29.880 (5) Å

  • b = 6.841 (5) Å

  • c = 11.999 (5) Å

  • [beta] = 102.307 (5)°

  • V = 2396 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.5 × 0.03 × 0.03 mm

Data collection
  • Bruker X8 APEX Diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.639, Tmax = 0.747

  • 13097 measured reflections

  • 2868 independent reflections

  • 1830 reflections with I > 2[sigma](I)

  • Rint = 0.055

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

  • wR(F2) = 0.102

  • S = 1.08

  • 2868 reflections

  • 322 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...N1 0.82 2.22 3.030 (4) 169
C2-H2...O4i 0.98 2.45 3.243 (4) 138
C4-H4A...O2ii 0.97 2.43 3.315 (5) 151
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+1]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: SJ5394 ).


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.  [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
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. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [CrossRef] [PubMed] [ChemPort]
Moumou, M., Benharref, A., Daran, J.-C., Mellouki, F. & Berraho, M. (2012). Acta Cryst. E68, o589-o590.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Neelakantan, S., Nasim, Sh., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346-4349.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o530-o531   [ doi:10.1107/S1600536814007430 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.