3β-Hydroxy­friedelan-17β-carboxylic acid

Chen, H.-Y.; Lin, C.-W.; Chen, G.-Y.; Ou, G.-C.

doi:10.1107/S1600536808010295

Volume 64
Part 5
Page o890
May 2008

Received 2 March 2008
Accepted 15 April 2008
Online 23 April 2008

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 11.2
Details

3-Hydroxyfriedelan-17-carboxylic acid

Hai-Yan Chen,^a Cui-Wu Lin,^a ^* Guang-Ying Chen ^b and Guang-Chuan Ou ^c

^aCollege of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China,^bDepartment of Chemistry, Hainan Normal University, Haikou 571158, People's Republic of China, and ^cDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, People's Republic of China
Correspondence e-mail: lincuiwu@gxu.edu.cn

The title compound, C₃₀H₅₀O₃, which was isolated from a marine endophytic fungus, is a new friedelan derivative. The molecule contains five six-membered rings, which exhibit boat (ring A), distorted boat (ring B) and chair (rings C-E) conformations. The crystal structure is stabilized by intermolecular O-HO hydrogen bonds, which link neighbouring molecules into 12-membered rings.

Related literature

For general background, see: Chen et al. (2003, 2005, 2006a,b); Lin et al. (2001a,b, 2002). For related structures, see: Dhaneshwar et al. (1987); Fun et al. (2007); Mo (1977); Mo et al. (1989); Sun et al. (2004).

Experimental

Crystal data

C₃₀H₅₀O₃
M_r = 458.70
Orthorhombic, P 2₁ 2₁ 2
a = 13.238 (3) Å
b = 24.141 (5) Å
c = 8.7349 (17) Å
V = 2791.5 (10) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 153 (2) K
0.51 × 0.48 × 0.46 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
18448 measured reflections
3466 independent reflections
3010 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.112
S = 1.04
3466 reflections
308 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O35-H35O41ⁱ	0.84	1.83	2.644 (2)	163
O41-H41O34ⁱⁱ	0.84	1.89	2.721 (2)	168
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2405 ).

Acknowledgements

The project was supported by Guangxi Science Foundation (Guikezi0728257, Guikeji0144002) and the National Natural Science Foundation of China (20562004). The X-ray data were collected at the Instrumentation Analysis and Research Center of Sun Yat-sen (Zhongshan) University; the authors thank the staff for all their help and advice. We acknowledge Dr S. Parkin at the University of Kentucky (Lexington) and Dr Z. Ma at the University of Guangxi (Nanning) for their advice.

References

Bruker, (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. Y., Lin, Y. C., Chen, G. Y., Hu, G. P., Wang, L. & Vrijmoed, L. L. P. (2006a). Chem. Nat. Compd. 42, 407-409.
Chen, H.-Y., Lin, Y.-C., Vrijmoed, L. L. P. & Jones, E. B. G. (2006b). Acta Cryst. E62, o836-o837.
Chen, G. Y., Lin, Y. C., Wen, L., Vrijmoed, L. L. P. & Gareth, E. B. J. (2003). Tetrahedron, 59, 4907-4909.
Chen, H. Y., Qi, P., Lin, Y. C., Chen, G. Y., Wang, L. & Vrijmoed, L. L. P. (2005). Zhongshan Daxue Xuebao (Ziran Kexueban), 44, 122-123.
Dhaneshwar, N. N., Sawaikar, D. D., Narayanan, C. R., Tavale, S. S. & Guru Row, T. N. (1987). Acta Cryst. C43, 66-68.
Fun, H.-K., Boonnak, N. & Chantrapromma, S. (2007). Acta Cryst. E63, o2014-o2016.
Lin, Y. C., Wu, X. Y., Deng, Z. J., Wang, J., Zhou, S. N., Vrijmoed, L. L. P. & Gareth, E. B. J. (2002). Phytochemistry, 59, 469-471.
Lin, Y. C., Wu, X. Y., Feng, S., Jiang, G. C., Luo, J. H., Zhou, S. N., Vrijmoed, L. L. P., Gareth, E. B. J., Krohn, K., Steingrover, K. & Zsila, F. (2001a). J. Org. Chem. 66, 6252-6256.
Lin, Y. C., Wu, X. Y., Feng, S., Jiang, G. C., Zhou, S. N., Vrijmoed, L. L. P. & Gareth, E. B. J. (2001b). Tetrahedron Lett. 42, 449-451.
Mo, F. (1977). Acta Cryst. B33, 641-649.
Mo, F., Winther, S. & Scrimgeour, S. N. (1989). Acta Cryst. B45, 261-270.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, J., Zhang, H. G., Zhang, J. M., Zhang, T. B., Guo, B. & Zhang, H. Q. (2004). J. Chin. Pharm. Sci. 13, 291-292.

organic compounds