Skip to main content
Log in

Fine-tuning of packing architecture: symmetrically bridge-disubstituted tetramethoxycalix[4]arenes

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Three acetonitrile solvates of tetramethoxycalix[4]arenes equally substituted on opposite methylene bridges are described with respect to their conformation and packing behaviour. All of the host molecules adopt a 1,2-alternate conformation, their packing architecture seems to be affected by the spatial demand of the bridge substituents only. This results in the synthetically implemented fine-tuning of the molecular arrangement. The engineering of the relevant packing motif, the “synthon” may be discussed most appropriate by the term “synthon engineering” following the expression of crystal engineering.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Vicens J, Harrowfield J (2007) Calixarenes in the nanoworld. Springer, Dordrecht

    Book  Google Scholar 

  2. Park SY, Yoon JH, Hong CS, Souane R, Kim JS, Matthews SE, Vicens J (2008) J Org Chem 73:8212

    Article  CAS  Google Scholar 

  3. Fischer C, Lin G, Seichter W, Weber E (2009) Acta Crystallogr E65:o1704

    CAS  Google Scholar 

  4. Gruner M, Fischer C, Gruber T, Weber E (2010) Supramol Chem 22:256

    Article  CAS  Google Scholar 

  5. Gruber T, Gruner M, Fischer C, Seichter W, Bombicz P, Weber E (2010) New J Chem 34:250

    Article  CAS  Google Scholar 

  6. Fischer C, Gruber T, Seichter W, Weber E (2011) Org Biomol Chem 9:4347

    Article  CAS  Google Scholar 

  7. Fischer C, Seichter W, Weber E (2011) Beilstein J Org Chem 7:1602

    Article  CAS  Google Scholar 

  8. Fischer C, Lin G, Bombicz P, Seichter W, Weber E (2011) Struct Chem 22:433

    Article  CAS  Google Scholar 

  9. Fischer C, Lin G, Seichter E, Weber E (2011) Tetrahedron 67:5656

    Article  CAS  Google Scholar 

  10. Fischer C, Bombicz P, Katzsch F, Seichter W, Weber E (2012) Cryst Growth Des 12:2445

    Article  CAS  Google Scholar 

  11. Gutsche CD, Dhawan B, Levine JA, No KH, Bauer LJ (1983) Tetrahedron 39:409

    Article  CAS  Google Scholar 

  12. Scully PA, Hamilton TM, Bennett JL (2001) Org Lett 3:2741

    Article  CAS  Google Scholar 

  13. Sheldrick GM (2008) Acta Crystallogr A64:112

    CAS  Google Scholar 

  14. Kálmán A, Párkányi L (1997) In: Hargittai M, Hargittai I (eds) Advances in molecular structure research, vol 3. JAI Press, Greenwich, pp 189–226

    Chapter  Google Scholar 

  15. Kálmán A, Párkányi L, Argay Gy (1993) Acta Crystallogr B 49:1039

    Article  Google Scholar 

  16. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J (2006) J Appl Crystallogr 39:453

    Article  CAS  Google Scholar 

  17. Kitaigorodskii AI (1973) Molecular crystals and molecules. Academic Press, New York

    Google Scholar 

  18. Spek AL (2009) Acta Crystallogr D65:148

    CAS  Google Scholar 

  19. Fischer C, Gruber T, Schindler D, Seichter W, Weber E (2011) Cryst Growth Des 11:1989

    Article  CAS  Google Scholar 

  20. Desiraju GR, Steiner T (1999) The weak hydrogen bond. Oxford University Press, Oxford

    Google Scholar 

  21. Nishio M, Umezawa Y, Honda K, Tsuboyama S, Suezawa H (2009) CrystEngComm 11:1757

    Article  CAS  Google Scholar 

  22. Fischer C, Gruber T, Seichter W, Schindler D, Weber E (2008) Acta Crystallogr E64:o673

    CAS  Google Scholar 

  23. Katzsch F, Eißmann D, Weber E (2012) Struct Chem 23:245

    Article  CAS  Google Scholar 

  24. Desiraju GR (1995) Angew Chem Int Ed 34:2311

    Article  CAS  Google Scholar 

Download references

Acknowledgments

C. F. acknowledges Prof. Dr. E. Weber for supervision and Dr. T. Gruber for persistent scientific discussion. P. B. acknowledges the support from the National Scientific Research Foundation (OTKA K-100801).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Conrad Fischer or Petra Bombicz.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fischer, C., Bombicz, P., Seichter, W. et al. Fine-tuning of packing architecture: symmetrically bridge-disubstituted tetramethoxycalix[4]arenes. Struct Chem 24, 535–541 (2013). https://doi.org/10.1007/s11224-012-0104-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-012-0104-1

Keywords

Navigation