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Volume 68 
Part 11 
Pages o3089-o3090  
November 2012  

Received 29 August 2009
Accepted 24 September 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.058
wR = 0.162
Data-to-parameter ratio = 13.7
Details
Open access

3-epi-Dammarenediol II 1.075 hydrate: a dammarane triterpene from the bark of Aglaia eximia

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia,cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and dDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia
Correspondence e-mail: hkfun@usm.my

The title dammarane tritepene, 3[alpha],20(S)-dihydroxydammar-24-ene, which crystallized out in a hydrated form, C30H52O2.1.075H2O, was isolated from the Aglaia eximia bark. The three cyclohexane rings adopt chair conformations. The cyclopentane has an envelope conformation with the quaternary C at position 14 as the flap atom with the maximum deviation of 0.288 (2) Å. The methylheptene side chain is disordered over two positions with 0.505 (1):0.495 (1) site occupancies and is axially attached with an (+)-syn-clinal conformation. The hydroxyl group at position 3 of dammarane is in a different conformation to the corresponding hydroxyl in Dammarenediol II. In the crystal, the dammarane and water molecules are linked by ODammarane-H...Owater and Owater-H...ODammarane hydrogen bonds into a three-dimensional network.

Related literature

For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to Aglaia plants, triterpenoids and their biological activity, see: Asakawa et al. (1977[Asakawa, J., Kasai, R., Yamasaki, K. & Tanaka, O. (1977). Tetrahedron, 33, 1935-1939.]); Chairgulprasert et al. (2006[Chairgulprasert, V., Krisornpornsan, B. & Hamad, A. (2006). Songklanakarin J. Sci. Technol. 28, 321-326.]); Greger et al. (2001[Greger, H., Pacher, T., Bream, B., Bacher, M. & Hofer, O. (2001). Phytochemistry, 57, 57-64.]); Grosvenor et al. (1995[Grosvenor, P. W., Supriono, A. & Gray, D. O. (1995). J. Ethnopharm. 45, 97-111.]); Lima et al. (2004[Lima, M. da P., Braga, P. A. de C., Macedo, M. L., Silva, M. F., da das, G. F., Ferreira, A. G., Fernandes, J. B. & Vierira, P. C. (2004). J. Braz. Chem. Soc. 15, 385-394.]); Qiu et al. (2001[Qiu, S.-X., van Hung, N., Xuan, L. T., Gu, J.-Q., Lobkovsky, E., Khanh, T. C., Soejarto, D. D., Clardy, J., Pezzuto, J. M., Dong, Y., Tri, M. V., Huong, L. M. & Fong, H. H. S. (2001). Phytochem. 56 775-780.]); Roux et al. (1998[Roux, D., Martin, M.-T., Adeline, M.-T., Sevenet, T., Hadi, A. H. A. & Pais, M. (1998). Phytochemistry, 49, 1745-1748.]); Yodsaoue et al. (2012[Yodsaoue, O., Sonprasit, J., Karalai, C., Ponglimanont, C., Tewtrakul, S. & Chantrapromma, S. (2012). Phytochemistry, 76, 83-91.]); Zhang et al. (2010[Zhang, F., Wang, J. S., Gu, J. S. & Kong, L. Y. (2010). J. Nat. Prod. 73, 2042-2046.]). For related structures, see: Qiu et al. (2001[Qiu, S.-X., van Hung, N., Xuan, L. T., Gu, J.-Q., Lobkovsky, E., Khanh, T. C., Soejarto, D. D., Clardy, J., Pezzuto, J. M., Dong, Y., Tri, M. V., Huong, L. M. & Fong, H. H. S. (2001). Phytochem. 56 775-780.]). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C30H52O2·1.075H2O

  • Mr = 463.99

  • Tetragonal, P 42

  • a = 19.9481 (13) Å

  • c = 7.3410 (7) Å

  • V = 2921.2 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.39 × 0.11 × 0.10 mm

Data collection
  • Bruker APEX Duo CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.994

  • 24864 measured reflections

  • 4543 independent reflections

  • 3887 reflections with I > 2[sigma](I)

  • Rint = 0.064

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.162

  • S = 1.07

  • 4543 reflections

  • 332 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H1O2...O1W 0.84 2.02 2.816 (3) 157
O1W-H1W1...O1i 0.84 1.94 2.783 (3) 175
O2W-H1W2...O2ii 0.83 1.89 2.718 (3) 177
Symmetry codes: (i) [y, -x+1, z+{\script{1\over 2}}]; (ii) x, y, z+1.

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 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2209 ).


Acknowledgements

AS, DH and US thank Padjadjaran University for financial support. HKF and SC thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Asakawa, J., Kasai, R., Yamasaki, K. & Tanaka, O. (1977). Tetrahedron, 33, 1935-1939.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chairgulprasert, V., Krisornpornsan, B. & Hamad, A. (2006). Songklanakarin J. Sci. Technol. 28, 321-326.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Greger, H., Pacher, T., Bream, B., Bacher, M. & Hofer, O. (2001). Phytochemistry, 57, 57-64.  [ISI] [CrossRef] [PubMed] [ChemPort]
Grosvenor, P. W., Supriono, A. & Gray, D. O. (1995). J. Ethnopharm. 45, 97-111.  [CrossRef] [ChemPort]
Lima, M. da P., Braga, P. A. de C., Macedo, M. L., Silva, M. F., da das, G. F., Ferreira, A. G., Fernandes, J. B. & Vierira, P. C. (2004). J. Braz. Chem. Soc. 15, 385-394.  [CrossRef] [ChemPort]
Qiu, S.-X., van Hung, N., Xuan, L. T., Gu, J.-Q., Lobkovsky, E., Khanh, T. C., Soejarto, D. D., Clardy, J., Pezzuto, J. M., Dong, Y., Tri, M. V., Huong, L. M. & Fong, H. H. S. (2001). Phytochem. 56 775-780.  [CSD] [CrossRef] [ChemPort]
Roux, D., Martin, M.-T., Adeline, M.-T., Sevenet, T., Hadi, A. H. A. & Pais, M. (1998). Phytochemistry, 49, 1745-1748.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yodsaoue, O., Sonprasit, J., Karalai, C., Ponglimanont, C., Tewtrakul, S. & Chantrapromma, S. (2012). Phytochemistry, 76, 83-91.  [ISI] [CrossRef] [ChemPort] [PubMed]
Zhang, F., Wang, J. S., Gu, J. S. & Kong, L. Y. (2010). J. Nat. Prod. 73, 2042-2046.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3089-o3090   [ doi:10.1107/S1600536812040366 ]

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