Journal of inclusion phenomena

, Volume 6, Issue 5, pp 443–460 | Cite as

Crystal structures of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin complexes with (R)- and (S)-Flurbiprofen

  • Kazuaki Harata
  • Kaneto Uekama
  • Teruko Imai
  • Fumitoshi Hirayama
  • Masaki Otagiri


Hepatakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CDx) forms crystalline complexes with (R)-Flubiprofen (R-FP), C63H112O35C15H13O2F·H2O, and (S)-Flurbiprofen (S-FP), C63H112O35C15H13O2F. The crystal structures were determined by X-ray analysis. Crystals of both compounds are orthorhombic and the space group isP212121 with cell dimensions:a=15.092(2),b=21.714(3), andc=28.269(4) Å for theR-FP complex, anda=15.271(2),b=21.451(3) andc=27.895(3) Å for theS-FP complex. The macrocyclic ring of TM-β-CDx is markedly distorted because of the inability to form intramolecular hydrogen bonds and the steric hindrance involving methyl groups. In both complexes, the phenyl group is inserted into the host cavity from the O(2), O(3) side, which is wider than the O(6) side. The biphenyl moiety ofR-FP is fixed in theR-configuration within the host cavity. The phenyl group ofS-FP is disordered, andR-andS-configurations are statistically distributed with equal probability. TM-β-CDx molecules are stacked along theb axis to form a column structure. The TM-β-CDx molecule is laterally shifted with respect to the column axis, and a half of the guest molecule protrudes outside from the crevis of the column. The carboxyl group ofR-FP forms a hydrogen bond with water located outside the host cavity, while the carboxyl group ofS-FP is hydrogen-bonded to an oxygen atom of an adjacent TM-β-CDx.

Key words

Methylated cyclodextrin inclusion complex host-guest interaction chiral recognition crystal structure Flurbiprofen 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    K. Harata:Chem. Lett., 2057 (1986).Google Scholar
  2. 2.
    M. Czugler, E. Eckle, and J. J. Stezowski:J. Chem. Soc., Chem. Commun., 1291 (1981).Google Scholar
  3. 3.
    K. Harata:Chem. Lett., 1641 (1984).Google Scholar
  4. 4.
    K. Harata, K. Uekama, M. Otagiri, and F. Hirayama:Bull. Chem. Soc. Jpn. 60, 497 (1987).Google Scholar
  5. 5.
    K. Harata, K. Uekama, M. Otagiri, and F. Hirayama:Bull. Chem. Soc. Jpn. 56, 1732 (1983).Google Scholar
  6. 6.
    K. Harata:Bull. Chem. Soc. Jpn. 55, 1367 (1982).Google Scholar
  7. 7.
    K. Uekama, F. Hirayama, T. Imai, M. Otagiri, and K. Harata:Chem. Pharm. Bull. 31, 3363 (1983).Google Scholar
  8. 8.
    K. Harata, F. Hirayama, T. Imai, K. Uekama, and M. Otagiri:Chem. Lett. 1549 (1984).Google Scholar
  9. 9.
    K. Lindner and W. Saenger:Carbohydr. Res. 99, 103 (1982).Google Scholar
  10. 10.
    K. Uekama, T. Imai, F. Hirayama, M. Otagiri, and K. Harata:Chem. Pharm. Bull. 32, 1662 (1984).Google Scholar
  11. 11.
    J. L. Flippen and R. D. Gilardi:Acta Crystallogr., Sect. B 31, 926 (1975).Google Scholar
  12. 12.
    A. D. French and V. G. Murphy:Carbohydr. Res. 27, 391 (1973).Google Scholar
  13. 13.
    K. Harata:Bull. Chem. Soc. Jpn. 50, 1416 (1977).Google Scholar
  14. 14.
    K. Harata,Bull. Chem. Soc. Jpn. 55, 2315 (1982).Google Scholar

Copyright information

© Kluwer Academic Publishers 1988

Authors and Affiliations

  • Kazuaki Harata
    • 1
  • Kaneto Uekama
    • 2
  • Teruko Imai
    • 2
  • Fumitoshi Hirayama
    • 2
  • Masaki Otagiri
    • 2
  1. 1.Research Institute for Polymers and TextilesTsukuba, IbarakiJapan
  2. 2.Faculty of Pharmaceutical SciencesKumamoto UniversityKumamotoJapan

Personalised recommendations