Skip to main content
SpringerLink
Log in

Crystal structure and theoretical calculations of 1-(4-trifluoromethyl-2,3,5,6-tetrafluorophenyl)-3-benzylimidazolium bromide

  • Brief Communications
  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

The salt 1-(4-trifluoromethyl-2,3,5,6-tetrafluorophenyl)-3-benzylimidazolium bromide [(CF3C6F4)NC3H3N(CH2Ph)]+·Br– is crystallized from methanol in the space group P-421 c of the tetragonal crystal system with unit cell parameters a = b = 21.6531(3) Å, c = 8.1968(2) Å, V = 3843.13(13) Å3, Z = 8, d calc = 1.5732 g/cm3. The structure possesses square channels with a width of ca. 5.2 Å, which accounts for 14% of the volume, and contains one methanol molecule per ion pair. The cation interacts with three bromide ions through an anion–π interaction and two C–H⋯Br– interactions. These interactions are investigated by DFT calculations.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

References

  1. The Importance of Pi-interactions in Crystal Engineering: Frontiers in Crystal Engineering, E. R. Tiekink and J. Zukerman-Schpector (eds.), Chichester: John Wiley & Sons Ltd, UK (2012).

  2. M. Egli and S. Sarkhel, Acc. Chem. Res., 40, 197–205 (2007).

    Article  CAS  Google Scholar 

  3. S. K. Singh and A. Das, Phys. Chem. Chem. Phys., 17, 9596–9612 (2015).

    Article  CAS  Google Scholar 

  4. G. R. Desiraju, Angew. Chem., Int. Ed., 50, 52–59 (2011).

    Article  CAS  Google Scholar 

  5. E. Arunan, G. R. Desiraju, R. A. Klein, et al., Pure Appl. Chem., 83, 1637–1641 (2011).

    CAS  Google Scholar 

  6. J. M. Serrano-Becerra, S. Hernández-Ortega, D. Morales-Morales, and J. Valdés-Martínez, CrystEngComm., 11, 226–228 (2009).

    Article  CAS  Google Scholar 

  7. G. C. Saunders, CrystEngComm., 13, 1801–1803 (2011).

    Article  CAS  Google Scholar 

  8. V. L. Arcus, D. R. Bernstein, C. W. Crombie, and G. C. Saunders, CrystEngComm., 15, 9841–9843 (2013).

    Article  CAS  Google Scholar 

  9. O. V. Dolomanov, L. J. Bourhis, Gildea, et al., J. Appl. Crystallogr., 42, 339–341 (2009).

    Article  CAS  Google Scholar 

  10. L. J. Bourhis, O. V. Dolomanov, R. J. Gildea, et al., Acta Crystallogr., A71, 59–75 (2015).

    Google Scholar 

  11. H. D. Flack, Acta Crystallogr., A39, 876–881 (1983).

    Article  CAS  Google Scholar 

  12. M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 09, Revision A.2., Gaussian, Inc., Wallingford CT (2009).

    Google Scholar 

  13. J.-D. Chai and M. Head-Gordon, Phys. Chem. Chem. Phys., 10, 6615–6620 (2008).

    Article  CAS  Google Scholar 

  14. H. I. Althagbi, A. J. Edwards, B. K. Nicholson, et al., Cryst. Growth Des., 16, 174–188 (2016).

    Article  CAS  Google Scholar 

  15. A. Bondi, J. Phys. Chem., 68, 441–451 (1964).

    Article  CAS  Google Scholar 

  16. C. Estarellas, A. Bauzá, A. Frontera, et al., Phys. Chem. Chem. Phys., 13, 5696–5702 (2011).

    Article  CAS  Google Scholar 

  17. D. Quiñonero, C. Garau, C. Rotger, et al., Angew. Chem., Int. Ed., 41, 3389–3392 (2002).

    Article  Google Scholar 

  18. B. L. Schottel, H. T. Chifotides, and K. R. Dunbar, Chem. Soc. Rev., 37, 68–83 (2008).

    Article  CAS  Google Scholar 

  19. M. Giese, M. Albrecht, A. Valkonen, and K. Rissanen, Chem. Sci., 6, 354–359 (2015).

    Article  CAS  Google Scholar 

  20. T. V. Rybalova and I. Yu. Bagryanskaya, J. Struct. Chem., 50, 741–753 (2009).

    Article  CAS  Google Scholar 

  21. S. Tsuzuki, H. Tokuda, and M. Mikami, Phys. Chem. Chem. Phys., 9, 4780–4784 (2007).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Science, University of Waikato, Hamilton, New Zealand

    G. C. Saunders & H. P. Thomas

Authors
  1. G. C. Saunders
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. P. Thomas
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. C. Saunders.

Additional information

The text was submitted by the authors in English.

Zhurnal Strukturnoi Khimii, Vol. 58, No. 1, pp. 217-221, January-February, 2017.

Original Russian Text © 2017 G. C. Saunders, H. P. Thomas.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Saunders, G.C., Thomas, H.P. Crystal structure and theoretical calculations of 1-(4-trifluoromethyl-2,3,5,6-tetrafluorophenyl)-3-benzylimidazolium bromide. J Struct Chem 58, 211–215 (2017). https://doi.org/10.1134/S0022476617010310

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476617010310

Keywords

Search

Navigation