6β-Acet­oxy-1α,7β,11β,15β-tetra­hydr­oxy-7α,20-ep­oxy-ent-kaur-16-ene

Yan, F.-L.; Li, P.; Di, X.-M.; Feng, C.; Hou, R.-J.

doi:10.1107/S1600536810000231

Volume 66
Part 2
Page o295
February 2010

Received 20 December 2009
Accepted 4 January 2010
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.064
Data-to-parameter ratio = 8.6
Details

6-Acetoxy-1,7,11,15-tetrahydroxy-7,20-epoxy-ent-kaur-16-ene

Fu-Lin Yan,^a ^* Peng Li,^a Xue-Mei Di,^a Chuang Feng ^a and Rui-Jie Hou ^a

^aSchool of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, People's Republic of China
Correspondence e-mail: yannz2009@163.com

The title compound, C₂₂H₃₂O₇, a natural ent-kaurane diterpenoid also referred to as Maoyecrystal F, was obtained from the medicinal plant Isodon nervosa. There are four rings with the expected cis and trans junctions. Cyclohexane ring A adopts a chair conformation, rings B and C adopt boat conformations, while the five-membered ring has an envelope conformation. The molecules stack along the a axis in the crystal and are linked together by intermolecular O-HO hydrogen bonds.

Related literature

For related literature on the genus Isodon and diterpenoids, see: Sun et al. (2001); Zhang et al. (2003); Yan et al. (2008).

Experimental

Crystal data

C₂₂H₃₂O₇
M_r = 408.21
Monoclinic, P 2₁
a = 9.759 (3) Å
b = 6.6712 (17) Å
c = 14.927 (4) Å
= 90.002 (4)°
V = 971.8 (4) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 93 K
0.50 × 0.33 × 0.23 mm

Data collection

Rigaku AFC10 Saturn724+ diffractometer
7880 measured reflections
2412 independent reflections
2262 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.064
S = 1.00
2412 reflections
281 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2OO5	0.85 (3)	1.75 (3)	2.5539 (19)	156 (2)
O4-H4OO6ⁱ	0.82 (3)	2.03 (3)	2.843 (2)	172 (2)
O5-H5OO2ⁱⁱ	0.82 (2)	1.85 (2)	2.6467 (18)	165 (2)
O6-H6OO3	0.81 (2)	2.07 (3)	2.7743 (18)	145 (2)
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: CrystalClear (Rigaku, 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: HG2621 ).

Acknowledgements

This work was supported by the Henan Province Science and Technology Foundation of China (No. 611042600)

References

Rigaku (2008). CrystalClear. Rigaku Corporation, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, H. D., Xu, Y. L. & Jiang, B. (2001). Diterpenoids from Isodon Species, pp. 4-17. Beijing: Science Press.
Yan, F. L., Guo, L. Q., Bai, S. P. & Sun, H. D. (2008). J. Chin. Chem. Soc. 55, 933-936.
Zhang, J. X., Han, Q. B., Zhao, A. H. & Sun, H. D. (2003). Fitoterapia, 74, 435-438.

organic compounds