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Volume 67 
Part 2 
Page o402  
February 2011  

Received 8 December 2010
Accepted 10 January 2011
Online 15 January 2011

[hg2768sup1]
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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.008 Å
R = 0.105
wR = 0.249
Data-to-parameter ratio = 11.2
Details
Open access

(-)-Crebanine

Tanwawan Duangthongyou,a Arthit Makarasen,b Supanna Techasakul,a Nitirat Chimnoib and Sutatip Siripaisarnpipata*

aCenter of Excellence in Functional Materials, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10930, Thailand, and bChulabhorn Research Institute,Vibhavadee-Rangsit Highway, Laksi, Bangkok 10210, Thailand
Correspondence e-mail: fscists@ku.ac.th

The asymmetric unit of the title compound [systematic name: 9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline], C20H21NO4, contains two independent molecules with very similar bond lengths and angles. The crystal packing exhibits voids of 131 Å3.

Related literature

For related structures, see: Israilov et al. (1980[Israilov, I. A., Karimova, S. U., Yunusov, M. S. & Yunusov, S. Yu. (1980). Chem. Nat. Compd, 16, 197-225.]); Blanchfield et al. (2003[Blanchfield, J. T., Sands, D. P. A., Kennard, C. H. L., Byriel, K. A. & Kitching, W. (2003). Phytochemistry, 63, 711-720.]). For the chemistry, pharmacology and traditional uses of the title compound, see; Montririttigri et al. (2008[Montririttigri, K., Moongkarndi, P., Joongsomboonkusol, S., Chitkul, B. & Pattanapanyasat, K. (2008). Mahidol Univ. J. Pharm. Sci. 35, 52-56.]) and Semwal et al. (2010[Semwal, D. K., Badoni, R., Semwal, R., Kothiyal, S. K., Singh, G. J. P. & Rawat, U. (2010). J. Ethnopharmacol. 132, 369-383.]).

[Scheme 1]

Experimental

Crystal data

  • C20H21NO4

  • Mr = 339.38

  • Orthorhombic, P 21 21 21

  • a = 4.4029 (3) Å

  • b = 20.5847 (15) Å

  • c = 39.612 (3) Å

  • V = 3590.2 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.22 × 0.16 × 0.12 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • 31211 measured reflections

  • 5054 independent reflections

  • 3592 reflections with I > 2[sigma](I)

  • Rint = 0.071
Refinement

  • R[F2 > 2[sigma](F2)] = 0.105

  • wR(F2) = 0.249

  • S = 1.2

  • 5054 reflections

  • 453 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.].

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2768 ).

Acknowledgements

The authors thank Dr Narongsuk Chaichit, Department of Physics, Faculty of Science, Thammasart University, for the data collection and the Department of Chemistry, Faculty of Science, Kasetsart University, for financial support.

References

Blanchfield, J. T., Sands, D. P. A., Kennard, C. H. L., Byriel, K. A. & Kitching, W. (2003). Phytochemistry, 63, 711-720.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Israilov, I. A., Karimova, S. U., Yunusov, M. S. & Yunusov, S. Yu. (1980). Chem. Nat. Compd, 16, 197-225.  [CrossRef]
Montririttigri, K., Moongkarndi, P., Joongsomboonkusol, S., Chitkul, B. & Pattanapanyasat, K. (2008). Mahidol Univ. J. Pharm. Sci. 35, 52-56.  [ChemPort]
Semwal, D. K., Badoni, R., Semwal, R., Kothiyal, S. K., Singh, G. J. P. & Rawat, U. (2010). J. Ethnopharmacol. 132, 369-383.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2011). E67, o402  [ doi:10.1107/S1600536811001231 ]

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