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Crystal structure of orellanine hydrate

  • Maciej Kubicki
  • Teresa Borowiak
  • Wiesław Z. Antkowiak
Article

Abstract

Orellanine hydrate crystallizes in the monoclinic space groupC2/c with unit cell parametersa=11.516(1) Å,b=8.573(1) Å,c=11.167(2) Å,β=110.92(1)°. The finalR andRw equal 0.041 and 0.046, respectively. The water molecule in the hydrate binds bothN-oxide oxygens of the orellanine molecule by hydrogen bonds, thus fixing the conformation. The hydrate so formed occupies a special position on a twofold axis which passes through the midpoint of the C2-C2′ bond distance and the OW atom. Both of the hydroxy-groups participate also in intermolecular hydrogen bonds. As a consequence of the rigid hydrogen bonded network, the dihedral angle between these two pyridil rings of the orellanine molecule is equal to 90.20(5)°.

Keywords

Oxygen Hydrogen Physical Chemistry Hydrate Crystal Structure 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Antkowiak, W. Z., and Gessner, W. P. (1979)Tetrahedron Lett. 19, 1931.Google Scholar
  2. Antkowiak, W. Z., and Gessner, W. P. (1984)Tetrahedron Lett. 25, 4045.Google Scholar
  3. Antkowiak, W. Z. and Gessner, W. P. (1985)Experientia 41, 769.Google Scholar
  4. Chiang, J. F. (1974)J. Chem. Phys. 61, 1280.Google Scholar
  5. Cohen-Addad, C., Richard, J.-M., and Guitel, J.-C. (1987)Acta Crystallogr. C43, 504.Google Scholar
  6. Eichhorn, K. (1987)Acta Crystallogr. B 43, 111.Google Scholar
  7. Grzymała, S. (1959)Mykologisches Mitteilungsblatt 3, 91.Google Scholar
  8. Grzymała, S. (1962)Bull. Soc. Mycol. Fr. 78, 394.Google Scholar
  9. Jaskólski, M. (1982)Collected Abstracts of the Fourth Symposium on Organic Crystal Chemistry, Poznań, September 1982, Z. Kałuski (ed.). (Adam Mickiewicz Univ., Poznań, Poland), pp. 70, 71.Google Scholar
  10. Johnson, C. K. (1976)OrtepII. Report ORNL-5138. (Oak Ridge National Laboratory, Tenn.).Google Scholar
  11. Kubicki, M., Borowiak, T., Antkowiak, R., and Antkowiak, W. Z. (1990)J. Crystallogr. Spectr. Res. 20, 381.Google Scholar
  12. Lehmann, M. S., and Larsen, F. K. (1974)Acta Crystallogr. A 30, 580.Google Scholar
  13. Motherwell, W. D. S., and Clegg, W. (1978)Pluto78,Program for drawing molecular and crystal structures. (Univ. of Cambridge, Cambridge, England).Google Scholar
  14. Nardelli, M. (1983)Comput. Chem. 7, 95.Google Scholar
  15. Rapior, S., Andary, C., and Rivat, G. (1988)Mycologia 80, 741.Google Scholar
  16. Sheldrick, G. M. (1976)Shelx76,Program for crystal structure determination. (Univ. of Cambridge, Cambridge, England).Google Scholar
  17. Sheldrick, G. M. (1986)Shelx86,Program for crystal structure determination. (Univ. of Cambridge, Cambridge, England).Google Scholar
  18. Wenkert, D., and Woodward, R. B. (1983)J. Org. Chem. 48, 283.Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • Maciej Kubicki
    • 1
  • Teresa Borowiak
    • 1
  • Wiesław Z. Antkowiak
    • 2
  1. 1.Laboratory of Crystallography, Faculty of ChemistryAdam Mickiewicz UniversityPoznańPoland
  2. 2.Laboratory of Organic Spectrochemistry, Faculty of ChemistryAdam Mickiewicz UniversityPoznańPoland

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