14-De­oxyxyloccensin K from Chisocheton ceramicus (Meliaceae)

Najmuldeen, I.A.; Abdul Hadi, A.H.; Awang, K.; Mohamad, K.; Ng, S.W.

doi:10.1107/S160053681002564X

Volume 66
Part 8
Page o1927
August 2010

Received 29 June 2010
Accepted 29 June 2010
Online 7 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.098
Data-to-parameter ratio = 10.0
Details

14-Deoxyxyloccensin K from Chisocheton ceramicus (Meliaceae)

Ibrahim A. Najmuldeen,^a Abdul Hamid Abdul Hadi,^a Khalijah Awang,^a Khalit Mohamad ^b and Seik Weng Ng ^a ^*

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

The title limonoid 14-deoxyxyloccensin K, C₂₇H₃₄O₇, isolated from Chisocheton ceramicus (Meliaceae), features an oxygen linkage between carbon-3 and carbon-8 along with a tetrahydrofuryl sub-unit. The six-membered rings adopt chair configurations and the tetrahydrofuryl sub-unit has an envelope shape.

Related literature

For the synthesis of 14-deoxyxyloccensin K from xyloccensin K, see: Kim et al. (2004). For the crystal structure of xyloccensin K, see: Kokpol et al. (1996). For a description of other xyloccensin limonoids, see: Wu et al. (2003).

Experimental

Crystal data

C₂₇H₃₄O₇
M_r = 470.54
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7174 (6) Å
b = 11.7401 (8) Å
c = 23.1106 (16) Å
V = 2365.2 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
22814 measured reflections
3083 independent reflections
2674 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.098
S = 1.03
3083 reflections
307 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.20 e Å^-3

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: BT5284 ).

Acknowledgements

We thank the University of Malaya (PPP PS378/009B) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kim, J.-G., Cho, D. H. & Jang, D. O. (2004). Tetrahedron Lett. 45, 3031-3033.
Kokpol, U., Chavasiri, W., Tip-Pyang, S., Veerachato, G., Zhao, F., Simpson, J. & Weavers, R. T. (1996). Phytochemistry, 41, 903-905.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Wu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Xiao, Z.-H. & Long, L.-J. (2003). Z. Naturforsch. Teil B, 58, 1216-1219.

organic compounds