6,8-Dihy­droxy-8a-methyl-3,5-dimethyl­idenedeca­hydro­naphtho­[2,3-b]furan-2(3H)-one

Liu, T.; Wu, H.-B.; Wang, W.-S.

doi:10.1107/S160053681204425X

Volume 68
Part 11
Page o3251
November 2012

Received 1 August 2012
Accepted 25 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 133 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.124
Data-to-parameter ratio = 10.8
Details

6,8-Dihydroxy-8a-methyl-3,5-dimethylidenedecahydronaphtho[2,3-b]furan-2(3H)-one

Ting-ting Liu,^a Hai-Bo Wu ^a and Wen-Shu Wang ^a ^*

^aCollege of Life and Environment Science, Minzu University of China, Beijing 100081, People's Republic of China
Correspondence e-mail: wangws@muc.edu.cn

The title compound, C₁₅H₂₀O₄, is a eudesmanolide isolated from the Chinese medicinal plant Carpesium triste Maxim. The molecule contains three rings, viz. two fused six-membered rings in chair conformations and a five-membered ring in a flattened envelope conformation. In the crystal, two hydroxy groups are involved in the formation of intra- and intermolecular O-HO hydrogen bonds. The H atoms in these groups are split, with site-occupation factors of 0.5. The intermolecular hydrogen bonds link molecules into chains propagating in [010].

Related literature

For related compounds extracted from Carpesium triste Maxim, see: Masao & Fumiko (1975).

Experimental

Crystal data

C₁₅H₂₀O₄
M_r = 264.31
Tetragonal, P 4₁ 2₁ 2
a = 6.4737 (4) Å
c = 62.438 (8) Å
V = 2616.7 (5) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 133 K
0.54 × 0.48 × 0.32 mm

Data collection

Rigaku AFC10/Saturn-724+ CCD diffractometer
19607 measured reflections
1990 independent reflections
1826 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.124
S = 1.00
1990 reflections
185 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2OO2ⁱ	0.84 (1)	1.90 (1)	2.733 (3)	173 (5)
O2-H2O'O3	0.84 (1)	1.94 (2)	2.690 (2)	148 (2)
O3-H3O'O2	0.84 (1)	1.97 (4)	2.690 (2)	143 (5)
O3-H3OO3ⁱⁱ	0.83 (1)	1.88 (2)	2.697 (3)	168 (6)
Symmetry codes: (i) y, x, -z; (ii) y+1, x-1, -z.

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2376 ).

Acknowledgements

The project was supported by the 985 Project (grant Nos. MUC98504-14, MUC98507-08), Minzu University of China, together with the `Programme of Introducing Talents of Discipline to Universities' (grant No. B08044), and the `Project for Scientific and Technical Achievements in Industrialization', Beijing Education Commission.

References

Masao, M. & Fumiko, S. (1975). Phytochemistry, 14, 2247-2248.
Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds