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Volume 66 
Part 11 
Page o3013  
November 2010  

Received 30 September 2010
Accepted 13 October 2010
Online 31 October 2010

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Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.120
Data-to-parameter ratio = 8.9
Details
Open access

Yuzurimine from of Daphniphyllum macropodum Miq.

Ying Chenga,b and Xing-Jin Hea*

aCollege of Science, Sichuan University, People's Republic of China, and bLeshan Teachers College, People's Republic of China
Correspondence e-mail: xingjinhe@yahoo.com.cn

The title compound, C27H37NO7, is a Daphniphyllum alkaloid isolated from a branch of Daphniphyllum macropodum Miq. All of the five-membered rings adopt envelope conformations while the six- and seven-membered ring adopt chair conformations. Classical intermolecular O-H...O and weak C-H...N hydrogen bonds are present in the crystal structure.

Related literature

For the chemical structure of the title compound established from NMR and MS data, see: Li et al. (2009[Li, Z.-Y., Gu, Y.-C., Irwin, D., Sheridan, J., Clough, J., Chen, P., Peng, S.-Y., Yang, Y.-M. & Guo, Y.-W. (2009). Chem. Biodivers. 6, 1744-1750.]). For structures of Daphniphyllum alkaloids, see: Yamamura & Terada (1976[Yamamura, S. & Terada, Y. (1976). Chem. Lett. 5, 1381-1385.]); Kubota et al. (2006[Kubota, T., Matsuno, Y., Morita, H., Shinzato, T., Sekiguchi, M. & Kobayashi, J. (2006). Tetrahedron, 62, 4743-4746.]).

[Scheme 1]

Experimental

Crystal data

  • C27H37NO7

  • Mr = 487.58

  • Orthorhombic, P 21 21 21

  • a = 9.5980 (3) Å

  • b = 9.7437 (2) Å

  • c = 26.0986 (6) Å

  • V = 2440.74 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 294 K

  • 0.60 × 0.45 × 0.20 mm
Data collection

  • Oxford Xcalibur diffractometer with an Eos CCD detector

  • 8335 measured reflections

  • 2836 independent reflections

  • 2236 reflections with I > 2[sigma](I)

  • Rint = 0.019
Refinement

  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.120

  • S = 1.04

  • 2836 reflections

  • 317 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.82 2.43 3.216 (3) 161
C22-H22B...N1ii 0.96 2.41 3.354 (4) 169
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5044 ).

Acknowledgements

This project was supported by grants from the PhD Programs Foundation of the Ministry of Education of China (grant No. 20090181110064) and the Scientific Reseach Fund of Leshan Teachers' College, China (grant No. Z0975). We thank Professor F.-Z. Chen of Leshan Teachers College for the isolation of the title compound.

References

Kubota, T., Matsuno, Y., Morita, H., Shinzato, T., Sekiguchi, M. & Kobayashi, J. (2006). Tetrahedron, 62, 4743-4746.  [CrossRef] [ChemPort]
Li, Z.-Y., Gu, Y.-C., Irwin, D., Sheridan, J., Clough, J., Chen, P., Peng, S.-Y., Yang, Y.-M. & Guo, Y.-W. (2009). Chem. Biodivers. 6, 1744-1750.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yamamura, S. & Terada, Y. (1976). Chem. Lett. 5, 1381-1385.  [CrossRef]

Acta Cryst (2010). E66, o3013  [ doi:10.1107/S1600536810041188 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.