Cabraleahy­droxy­lactone from the leaves of Aglaia exima

Loong, X.M.; Mohamad, K.; Awang, K.; Aadi, A.H.; Ng, S.W.

doi:10.1107/S1600536810035208

Volume 66
Part 10
Page o2541
October 2010

Received 24 August 2010
Accepted 1 September 2010
Online 11 September 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R = 0.047
wR = 0.121
Data-to-parameter ratio = 8.2
Details

Cabraleahydroxylactone from the leaves of Aglaia exima

Xe Min Loong,^a Khalit Mohamad,^b Khalijah Awang,^a A. Hamid A. Hadi ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Pharmacy, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

Cabraleahydroxylactone, C₂₇H₄₄O₃, isolated from the leaves of Aglaia exima, has three six-membered rings fused together that adopt chair conformations. Its two five-membered rings are enveloped shaped. The hydroxy group is in an axial position. It is a hydrogen-bond donor to the carbonyl O atom of an adjacent molecule; the O-HO interactions lead to the formation of a helical chain that runs along the b axis. There are two independent molecules in the asymmetric unit.

Related literature

For the isolation and spectroscopic characterization of cabraleahydroxylactone from other Alglaia species, see: Su et al. (2006); Yang et al. (2008). For another compound from Aglaia exima, see: Awang et al. (2010).

Experimental

Crystal data

C₂₇H₄₄O₃
M_r = 416.62
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.2077 (5) Å
b = 20.8363 (15) Å
c = 30.464 (2) Å
V = 4575.2 (6) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 100 K
0.30 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
36097 measured reflections
4573 independent reflections
3803 reflections with I > 2(I)
R_int = 0.098

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.121
S = 1.07
4573 reflections
555 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O4ⁱ	0.84	2.02	2.836 (4)	163
O4-H4O2	0.84	2.03	2.858 (4)	169
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5334 ).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Awang, K., Loong, X. M., Mohamad, K., Chong, S. L. & Ng, S. W. (2010). Acta Cryst. E66, o2142.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Su, B.-N., Chai, H., Mi, Q., Riswan, S., Kardono, L. B. S., Afriastini, J. J., Santarsiero, B. D., Mesecar, A. D., Farnsworth, N. R., Cordell, G. A., Swanson, S. M. & Kinghorn, A. D. (2006). Bioorg. Med. Chem. 14, 960-972.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yang, S.-M., Tan, C.-H., Luo, H.-F., Wang, D.-X. & Zhu, D.-Y. (2008). Helv. Chim. Acta, 91, 333-337.

organic compounds