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Volume 66 
Part 8 
Page o2161  
August 2010  

Received 5 July 2010
Accepted 27 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.049
wR = 0.139
Data-to-parameter ratio = 8.3
Details
Open access

3[beta]-Acetoxy-8[beta],10[beta]-dihydroxy-6[beta]-methoxyeremophil-7(11)-en-8,12-olide

aCollege of Life and Environment Science, Minzu University of China, Beijing 100081, People's Republic of China
Correspondence e-mail: wangwshu@gmail.com

The title compound, C18H26O7, is an eremophilenolide which has been isolated from the plant Ligularia duciformis for the first time. The present study confirms the atomic connectivity assigned on the basis of 1H and 13C NMR spectroscopy. The molecule contains three fused rings, two six-membered rings in chair confomations and a five-membered ring in a flattened envelope conformation. Two hydroxy groups are involved in formation of intra- and intermolecular O-H...O hydrogen bonds. The latter ones link molecules into chains propagating in [010].

Related literature

For related compounds extracted from Ligularia duciformis and Cacalia roborowski, see Wang et al. (2008[Wang, W. S., Dai, X., Hong, L. Y., Lu, P., Feng, J. C. & Jiao, Y. G. (2008). Helv. Chim. Acta, 91, 1118-1123.]) and Zhang et al. (1998[Zhang, S. M., Zhao, G. L., Li, R. & Lin, G. Q. (1998). Phytochemistry, 48, 519-524.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C18H26O7

  • Mr = 354.39

  • Orthorhombic, P 21 21 21

  • a = 7.3036 (15) Å

  • b = 9.789 (2) Å

  • c = 25.553 (5) Å

  • V = 1826.9 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.50 × 0.50 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID IP diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.952, Tmax = 0.980

  • 12058 measured reflections

  • 1885 independent reflections

  • 1203 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.139

  • S = 0.89

  • 1885 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O3 0.82 2.19 2.879 (4) 142
O3-H3A...O2i 0.82 2.06 2.755 (4) 143
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 2000[Rigaku (2000). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000[Rigaku/MSC (2000). Crystal Structure. Rigaku/MSC, Tokyo, Japan.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2743 ).


Acknowledgements

The project was supported by the 985 Project (MUC985) Minzu University of China, and the Major Project for Young Teachers in Minzu University of China CUN10A, together with the `Programme of Introducing Talents of Discipline to Universities' (B08044), and the `Project for Scientific and Technical Achievements in Industrialization', Beijing Education Commission.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2000). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2000). Crystal Structure. Rigaku/MSC, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, W. S., Dai, X., Hong, L. Y., Lu, P., Feng, J. C. & Jiao, Y. G. (2008). Helv. Chim. Acta, 91, 1118-1123.  [CrossRef]
Zhang, S. M., Zhao, G. L., Li, R. & Lin, G. Q. (1998). Phytochemistry, 48, 519-524.  [ISI] [CrossRef]


Acta Cryst (2010). E66, o2161  [ doi:10.1107/S1600536810029831 ]

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