Skip to main content
Log in

X-ray crystallographic studies of tricarbonylchromium complexes of calix[4]arene conformers: On an unusual conformation which appears in cone conformers

  • General Papers
  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

The structures of three arene-tricarbonylchromium complexes prepared from cone and 1,3-alternate-25, 26,27,28-tetrapropoxycalix[4]arene(1) and Cr(CO)6 were determined by single crystal X-ray studies. Crystal data for 1,3-alternate-Cr(CO)3 are space groupP21/a,a=19.496(3)Å,b=11.118(2)Å,c=19.121(2)Å, β=109.95°(1) andV=3895Å3. The structure was refined toRw=0.068. Crystal data for cone-Cr(CO)3 are space groupP21/a,a=21.457(4)Å,b=12.184(1)Å,c=14.816(2)Å, β=91.61°(1) andV=3872Å3. The structure was refined toRw=0.077. Crystal data for cone-2Cr(CO)3 are space groupP21/a,a=18.019(3)Å,b=41.347(4)Å,c=11.743(2)Å, β=97.39°(1) andV=8676Å3. The single crystal included two similar but slightly different structures but the data were successfully refined toRw=0.092. The structure of 1,3-alternate-Cr(CO)3 differs only slightly from that of the regular 1,3-alternate calix[4]arene. In contrast, cone-Cr(CO)3 and cone-2Cr(CO)3 show an unusual conformation with a pair of faced gablelike roofs, which is considerbly distorted from the regular cone calix[4]arene. The origin of this distortion is discussed in combination with the spectral studies.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. G. Bott, A. Coleman and J. L. Atwood:J. Chem. Soc., Chem. Commun., 610 (1986).

  2. S. G. Bott, A. Coleman and J. L. Atwood:J. Chem. Soc.,108, 1709 (1986).

    Google Scholar 

  3. J. L. Atwood, G. W. Orr, F. Hamada, R. L. Vincent, S. G. Bott. and K. D. Robinson:J. Am. Chem. Soc.,113, 2760 (1991).

    Google Scholar 

  4. S. G. Bott, A. Coleman and J. L. Atwood:J. Inclusion Phenom.,5, 747 (1987).

    Google Scholar 

  5. G. D. Andreetti, A. Pochini and R. Ungaro:J. Chem. Soc., Perkin Trans. 2, 1773 (1983).

    Google Scholar 

  6. R. Ungaro, A. Pochini, G. D. Andreetti and P. Domiano:J. Chem. Soc., Perkin Trans. 2, 197 (1985).

    Google Scholar 

  7. A. Arduini, A. Pochini, S. Reverberi, R. Ungaro, G. D. Andreetti and F. Ugozzoli,Tetrahedron,42, 2089 (1986).

    Google Scholar 

  8. G. D. Andreetti, R. Ungaro and A. Pochini:J. Chem. Soc., Chem. Commun., 4955 (1979).

  9. F. Arnaud-New, E. M. Collins, M. Deasy, G. Ferguson, S. J. Harris, B. Kaitner, A. J. Lough, M. A. McKervey, E. Marques, B. L. Ruhl, M. J. Schwing-Weill and E. M. Seward:J. Am. Chem. Soc.,111, 8681 (1989).

    Google Scholar 

  10. P. D. J. Grootenhuis, P. A. Kollman, L. C. Groenen, D. N. Reinhoudt, G. J. Van Hummel, F. Ugozzoli and G. D. Andreetti,J. Am. Chem. Soc.,112, 4165 (1990).

    Google Scholar 

  11. For a comprehensive review see J. L. Atwood and S. G. Bott,Top Inclusion Sci.,3, 199 (1991).

    Google Scholar 

  12. K. Iwamoto, K. Araki and S. Shinkai:J. Org. Chem. 56, 4955 (1991).

    Google Scholar 

  13. S. Shinkai, K. Fujimoto, T. Otsuka and H. L. Ammon,J. Org. Chem.,57, 1516 (1992).

    Google Scholar 

  14. K. Fujimoto, N. Nishiyama, H. Tsuzuki and S. Shinkai:J. Chem. Soc., Perkin Trans. 2 643 (1992).

    Google Scholar 

  15. H. Iki, T. Kikuchi and S. Shinkai:J. Chem. Soc., Perkin Trans. 1, 2109 (1992). Idem:ibid. 205 (1993).

    Google Scholar 

  16. For a comprehensive review see A. Solladie-Cavallo:Polyhedron,4, 901 (1985).

    Google Scholar 

  17. E. Langer, H. Lehner:Tetrahedron,29, 375 (1973).

    Google Scholar 

  18. M. Uemura: inAdvances in Metal-Organic Chemistry: Tricarbonyl(η 6-arene)-chromium Complexes in Organic Synthesis, L. S. Liebeskind, (Eds.), JAI Press, Greenwich (1991) vol. 2, p. 195.

    Google Scholar 

  19. M. J. Aroney, M. K. Cooper, P. A. Englert and R. K. Pierens:J. Mol. Str.,77, 99 (1981).

    Google Scholar 

  20. T. Kikuchi, H. Iki, H. Tsuzuki and S. Shinkai:Supramol. Chem.,1, 103 (1993).

    Google Scholar 

  21. P. Main, S. J. Fiske, S. E. Hull, L. Lessinger, G. Germain, J. P. DeClerg and M. M. Woolfson: University of York England (1980).

  22. M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, G. Poldori, R. Spagna and D. Viterbo:J. Appl. Cryst. 22, 389 (1989).

    Google Scholar 

  23. W. Verboom, S. Datta, Z. Asfari and D. N. Reinhoudt:J. Org. Chem. 57, 5384 (1992).

    Google Scholar 

  24. P. D. J. Grootenhuis, P. A. Koolman, D. N. Reinhoudt, G. J. van Hummel, F. Ugozzoli and G. D. Andreetti:J. Am. Chem. Soc. 112, 4165 (1990).

    Google Scholar 

  25. T. Harada, J. M. Rudzinski and S. Shinkai:J. Chem. Soc., Perkin Trans. 2 2109 (1992).

    Google Scholar 

  26. B. Rees and P. Coppens:Acta Cryst. B29, 2515 (1973).

    Google Scholar 

  27. F. van Meurs and H. van Koningskveld:J. Organomet. Chem. 131, 423 (1977).

    Google Scholar 

  28. O. L. Carter, A. T. McPhail and G. A. Sim:J. Chem. Soc. (A) 822 (1966).

  29. The similar shift of Cr to thep-position side is also seen for 1,3-alternate-Cr(CO)3: the distances from Cr to 3-, 4- and 5-carbons are 2.20, 2.18 and 2.21 Å, respectively whereas those to 1-, 2- and 6- carbons are 2.26, 2.28 and 2.26 Å, respectively.

  30. H. Ohno, H. Horita, T. Otsubo, Y. Sakata and S. Misumi:Tetrahedron Lett. 265 (1977).

Download references

Author information

Authors and Affiliations

Authors

Additional information

This paper is dedicated to the commemorative issue of the 50th anniversary of calixarenes.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Iki, H., Kikuchi, T., Tsuzuki, H. et al. X-ray crystallographic studies of tricarbonylchromium complexes of calix[4]arene conformers: On an unusual conformation which appears in cone conformers. J Incl Phenom Macrocycl Chem 19, 227–236 (1994). https://doi.org/10.1007/BF00708984

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00708984

Key Words

Navigation