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Volume 67 
Part 5 
Page o1220  
May 2011  

Received 8 April 2011
Accepted 20 April 2011
Online 29 April 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.033
wR = 0.087
Data-to-parameter ratio = 9.0
Details
Open access

Absolute configuration of 3[beta]-acetoxyolean-11,12-aziridin-28,13-[beta]-olide

Wen Nee Tan,a Keng Chong Wong,a Melati Khairuddean,a Madhukar Hemamalinib and Hoong-Kun Funb*+

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The title compound, C32H49NO4, has been isolated from the dichloromethane extract of the stem bark of Garcinia atroviridis Griff. ex T. Anders. Rings A and B, B and C, and C and D are trans-fused, whereas rings D and E are cis-fused. Rings A, B, C and E have slightly distorted chair conformations, while ring D is most heavily distorted towards a half-chair conformation owing to the strain induced by the lactonization. The ester group attached to ring A is in an equatorial position.

Related literature

For details and applications of Garcinia atroviridis Griff. ex T. Anders, see: Permana et al. (2001[Permana, D., Lajis, N. H., Mackeen, M. M., Ali, A. M., Aimi, N., Kitajima, M. & Takayama, H. (2001). J. Nat. Prod. 64, 976-979.]); Amran et al. (2009[Amran, A. A., Zaiton, Z., Faizah, O. & Morat, P. (2009). Singapore Med. J. 50, 295-299.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C32H49NO4

  • Mr = 511.72

  • Monoclinic, C 2

  • a = 13.0197 (2) Å

  • b = 6.7460 (1) Å

  • c = 32.0674 (5) Å

  • [beta] = 100.6452 (4)°

  • V = 2768.04 (7) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 100 K

  • 0.73 × 0.15 × 0.14 mm
Data collection

  • Bruker SMART APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.659, Tmax = 0.917

  • 8407 measured reflections

  • 3061 independent reflections

  • 3050 reflections with I > 2[sigma](I)

  • Rint = 0.018
Refinement

  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.087

  • S = 1.02

  • 3061 reflections

  • 342 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 721 Friedel pairs

  • Flack parameter: 0.1 (2)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2699 ).

Acknowledgements

TWN, WKC and MK wish to acknowledge the research grant RU1001/PKIMIA/811129 provided by the Universiti Sains Malaysia, Penang, that has resulted in this article. TWN would like to thank USM for the award of a postgraduate fellowship. MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Amran, A. A., Zaiton, Z., Faizah, O. & Morat, P. (2009). Singapore Med. J. 50, 295-299.  [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Permana, D., Lajis, N. H., Mackeen, M. M., Ali, A. M., Aimi, N., Kitajima, M. & Takayama, H. (2001). J. Nat. Prod. 64, 976-979.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2011). E67, o1220  [ doi:10.1107/S1600536811014875 ]

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