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Volume 69 
Part 6 
Pages o938-o939  
June 2013  

Received 13 May 2013
Accepted 16 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.138
Data-to-parameter ratio = 18.0
Details
Open access

(1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-2-yl acetate

aLaboratoire de Synthèse Organique Modélisation et Optimisation des Procédés Chimiques, Université Badji-Mokhtar Annaba, BP12, 23000 Annaba, Algeria, and bUniversité de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
Correspondence e-mail: muriel.pipelier@univ-nantes.fr

The title compound, C15H20O5, presents a bisnorsesquiterpene skeleton, with a trans-decaline backbone constrained by the lactone bridge. The [alpha]-hydroxy substituent and the methyl group belonging to the two decaline rings are in axial positions, whereas the other methyl group and the acyl group occupy the sterically preferred equatorial positions. The molecular structure is stabilized by an intramolecular C-H...O hydrogen bond. In the crystal, molecules are linked into chains along [010] by O-H...O hydrogen bonds

Related literature

For the synthesis, see: Selaimia-Ferdjani et al. (2013[Selaimia-Ferdjani, O., Kar, A., Chavan, S. P., Horeau, M., Viault, G., Pouessel, J., Guillory, X., Blot, V., Tessier, A., Bidjou-Haiour, C., Planchat, A., Jacquemin, D., Dubreuil, D. & Pipelier, M. (2013). Org. Lett. Submitted.]). For the biological activity of the natural lactone Paralemnolide A analogue of the title compound, see: Wang et al. (2012[Wang, S.-K., Lee, Y.-S. & Duh, C.-Y. (2012). Mar. Drugs, 10, 1528-1535.]) and of related nardosinane sesquiterpene derivatives, see: Bishara et al. (2008[Bishara, A., Yeffet, D., Sisso, M., Shmul, G., Schleyer, M., Benayahu, Y., Rudi, A. & Kashman, Y. (2008). J. Nat. Prod. 71, 375-380.]); Huang et al. (2011[Huang, H.-C., Su, J.-H., Cheng, S.-Y., Wen, Z.-H., Hsu, C.-H., Dai, C.-F., Sheu, J.-H. & Sung, P.-J. (2011). Mar. Drugs, 9, 1543-1553.]); Petit et al. (2004[Petit, K. E., Biard, J. F., Lapied, B., Grolleau, F. & Hamon, A. D. (2004). US Patent N2982US/DLR-ABA/40320.]); Lu et al. (2011[Lu, Y., Li, P.-J., Hung, W.-Y., Su, J.-H., Wen, Z.-H., Hsu, C.-H., Dai, C.-F., Chiang, M. Y. & Sheu, J.-H. (2011). J. Nat. Prod. 74, 169-174.]). For related nardosinane sesquiterpenes whose biological activity has not been investigated, see: El-Gamal et al. (2005[El-Gamal, A. A. H., Chiu, E. P., Li, C.-H., Cheng, S.-Y., Dai, C.-F. & Duh, C.-Y. (2005). J. Nat. Prod. 68, 1749-1753.]); Huang et al. (2006[Huang, H.-C., Wen, Z.-H., Chao, C.-H., Ahmed, A. F., Chiang, M. Y., Kuo, Y.-H., Hsu, C.-H. & Sheu, J.-H. (2006). Tetrahedron Lett. 47, 8751-8755.]); Wang & Duh (2007[Wang, S.-K. & Duh, C.-Y. (2007). Chem. Pharm. Bull. 55, 762-765.]); Wang et al. (2010[Wang, G.-H., Huang, H.-C., Su, J.-H., Wu, Y.-C. & Sheu, J.-H. (2010). Chem. Pharm. Bull. 58, 30-33.]).

[Scheme 1]

Experimental

Crystal data
  • C15H20O5

  • Mr = 280.3

  • Monoclinic, P 21

  • a = 10.3312 (10) Å

  • b = 7.1692 (8) Å

  • c = 10.8502 (6) Å

  • [beta] = 115.958 (5)°

  • V = 722.56 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.48 × 0.42 × 0.30 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: gaussian (JANA2006; Petrícek et al., 2006)[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic.] Tmin = 0.967, Tmax = 0.972

  • 12282 measured reflections

  • 3328 independent reflections

  • 2774 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.138

  • S = 1.84

  • 3328 reflections

  • 185 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H3c10...O4 0.96 2.31 2.946 (4) 122.91
O4-H1...O9i 0.83 (5) 2.10 (4) 2.907 (2) 165 (4)
Symmetry code: (i) x, y+1, z.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); data reduction: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006)[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic.]; molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: JANA2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic.].


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6907 ).


Acknowledgements

The authors thank the Profas Programme for a 18 month PhD felloship for OS-F in the CEISAM laboratory at Nantes University.

References

Bishara, A., Yeffet, D., Sisso, M., Shmul, G., Schleyer, M., Benayahu, Y., Rudi, A. & Kashman, Y. (2008). J. Nat. Prod. 71, 375-380.  [ISI] [CrossRef] [PubMed] [ChemPort]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [ISI] [CrossRef] [ChemPort] [details]
El-Gamal, A. A. H., Chiu, E. P., Li, C.-H., Cheng, S.-Y., Dai, C.-F. & Duh, C.-Y. (2005). J. Nat. Prod. 68, 1749-1753.  [ISI] [PubMed] [ChemPort]
Huang, H.-C., Su, J.-H., Cheng, S.-Y., Wen, Z.-H., Hsu, C.-H., Dai, C.-F., Sheu, J.-H. & Sung, P.-J. (2011). Mar. Drugs, 9, 1543-1553.  [CrossRef] [ChemPort] [PubMed]
Huang, H.-C., Wen, Z.-H., Chao, C.-H., Ahmed, A. F., Chiang, M. Y., Kuo, Y.-H., Hsu, C.-H. & Sheu, J.-H. (2006). Tetrahedron Lett. 47, 8751-8755.  [ISI] [CSD] [CrossRef] [ChemPort]
Lu, Y., Li, P.-J., Hung, W.-Y., Su, J.-H., Wen, Z.-H., Hsu, C.-H., Dai, C.-F., Chiang, M. Y. & Sheu, J.-H. (2011). J. Nat. Prod. 74, 169-174.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Petit, K. E., Biard, J. F., Lapied, B., Grolleau, F. & Hamon, A. D. (2004). US Patent N2982US/DLR-ABA/40320.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic.
Selaimia-Ferdjani, O., Kar, A., Chavan, S. P., Horeau, M., Viault, G., Pouessel, J., Guillory, X., Blot, V., Tessier, A., Bidjou-Haiour, C., Planchat, A., Jacquemin, D., Dubreuil, D. & Pipelier, M. (2013). Org. Lett. Submitted.
Wang, S.-K. & Duh, C.-Y. (2007). Chem. Pharm. Bull. 55, 762-765.  [CrossRef] [PubMed] [ChemPort]
Wang, G.-H., Huang, H.-C., Su, J.-H., Wu, Y.-C. & Sheu, J.-H. (2010). Chem. Pharm. Bull. 58, 30-33.  [CSD] [CrossRef] [ChemPort] [PubMed]
Wang, S.-K., Lee, Y.-S. & Duh, C.-Y. (2012). Mar. Drugs, 10, 1528-1535.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o938-o939   [ doi:10.1107/S1600536813013524 ]

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