6α-Hy­droxy-5,6-dihydro­salviasperanol

Asik, S.I.J.; Razak, I.A.; Salae, A.W.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S160053681004208X

Volume 66
Part 11
Page o2899
November 2010

Received 15 October 2010
Accepted 17 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.107
Data-to-parameter ratio = 15.2
Details

6-Hydroxy-5,6-dihydrosalviasperanol

Safra Izuani Jama Asik,^a Ibrahim Abdul Razak,^a Abdul Wahab Salae,^b Suchada Chantrapromma ^b ⁺ and Hoong-Kun Fun ^a ^*⁺⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₀H₂₈O₄, a diterpenoid isolated from the roots of Premna obtusifolia (Verbenaceae), the five-membered ring is in a half-chair conformation. One six-membered ring exists in a twisted-boat conformation while the other is in half-boat conformation. The crystal packing is stabilized by intermolecular O-HO and weak C-HO interactions, generating (001) sheets.

Related literature

For background to Verbenaceae, diterpenes and their biological activity, see: Hymavathi et al. (2009); Bunluepuech & Tewtrakul (2009); Esquivel et al. (1995). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₀H₂₈O₄
M_r = 332.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2767 (2) Å
b = 11.7358 (4) Å
c = 23.7496 (7) Å
V = 1749.45 (10) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.49 × 0.36 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.959, T_max = 0.979
15028 measured reflections
3534 independent reflections
3079 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.107
S = 1.15
3534 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1O3O2ⁱ	0.85 (3)	2.01 (3)	2.8504 (17)	169 (3)
O4-H1O4O1ⁱⁱ	0.84 (3)	1.89 (3)	2.7089 (16)	165 (3)
C18-H18BO3ⁱⁱⁱ	0.96	2.55	3.407 (2)	149
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5689 ).

Acknowledgements

SIJA, IAR and HKF thank Universiti Sains Malaysia for the Research University Grant (No.1001/PFIZIK/811151). SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit.

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.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bunluepuech, K. & Tewtrakul, S. (2009). Songklanakarin J. Sci. Technol. 31, 289-292.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Esquivel, B., Flores, M., Hernandez-Ortega, S., Toscano, R. A. & Ramamoorthy, T. P. (1995). Phytochemistry, 39, 139-143.
Hymavathi, A., Babu, K. S., Naidu, V. G. M., Krishna, S. R., Diwan, P. V. & Rao, J. M. (2009). Bioorg. Med. Chem. Lett. 19, 5727-5731.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds