Journal of Chemical Crystallography

, Volume 46, Issue 1, pp 28–33 | Cite as

Synthesis of the 4-Picoline (4-Pic) Complex of 4-Trifluoromethylphenylboronic Acid Catechol Ester (TFCB): The Unusual Co-crystal Structure—5(4-Pic·TFCB)·4-Pic

Original Paper
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Abstract

A novel complex of 4-picoline (4-Pic) with 4-trifluoromethylphenyl catechol boronate (TFCB) has been prepared and characterized by 1H NMR, 13C NMR, and X-ray diffraction analysis. When crystallized by evaporation from toluene a remarkable co-crystal was formed: 5(4-Pic·TFCB)·4-Pic (monoclinic P21, a = 13.4536(2) Å, b = 24.4320(3) Å, c = 14.0960(2) Å, β = 96.4340(10)°, vol. = 4604.15(11) Å3, Z = 2). The likely cause of the co-crystallization is π-stacking between complexed and free 4-Pic.

Graphical Abstract

A novel picoline-boronate complex has been prepared and characterized by 1H NMR, 13C NMR, and X-ray diffraction analysis. The solid-state structure of this simple complex reveals a remarkable co-crystal of 5(4-Pic·TFCB)·4-Pic.

Keywords

Amine–boronate complex Boroxine Boronate Dative bond X-ray diffraction Co-crystal Z′ > 1 

Notes

Acknowledgments

NJW and WRK would like to thank the Department of Chemistry & Physics at Western Carolina University. RDP would like to acknowledge the support of NSF (CHE-0443345) and the College of William and Mary for the purchase of X-ray equipment.

References

  1. 1.
    Brown HC, Kim KW, Cole TE, Singaram B (1986) J Am Chem Soc 108(21):6761–6764CrossRefGoogle Scholar
  2. 2.
    Coutts IGC, Goldschmid HR, Musgrave OC (1970) J Chem Soc C 3:488–493CrossRefGoogle Scholar
  3. 3.
    Ritchey JM (1968) Synthesis and properties of addition complexes of boroxines and other selected boron-containing systems. University of ColoradoGoogle Scholar
  4. 4.
    Beckett MA, Strickland GC, Sukumar VK, Hibbs DE, Hursthouse MB, Abdul Malik KM (1995) Polyhedron 14(19):2623–2630CrossRefGoogle Scholar
  5. 5.
    Beckett MA, Strickland GC, Varma KS, Hibbs DE, Hursthouse MB, Malik KMA (1997) J Organomet Chem 535(1–2):33–41CrossRefGoogle Scholar
  6. 6.
    Beckett MA, Hibbs DE, Hursthouse MB, Owen P, Abdul Malik AM, Varma KS (1998) Main Gr Chem 2:251–258CrossRefGoogle Scholar
  7. 7.
    Beckett MA, Brassington DS, Owen P, Hursthouse MB, Light ME, Malik KMA, Varma KS (1999) J Organomet Chem 585(1):7–11CrossRefGoogle Scholar
  8. 8.
    Iovine PM, Fletcher MN, Lin S (2006) Macromolecules 39(19):6324–6326CrossRefGoogle Scholar
  9. 9.
    Sheepwash E, Luisier N, Krause MR, Noe S, Kubik S, Severin K (2012) Chem Commun 48(63):7808–7810CrossRefGoogle Scholar
  10. 10.
    Christinat N, Croisier E, Scopelliti R, Cascella M, Röthlisberger U, Severin K (2007) Eur J Inorg Chem 30:5177–5181CrossRefGoogle Scholar
  11. 11.
    Christinat N, Scopelliti R, Severin K (2008) Angew Chem Int Ed 47:1848–1852CrossRefGoogle Scholar
  12. 12.
    Christinat N, Scopelliti R, Severin K (2008) Chem Commun 31:3660–3662CrossRefGoogle Scholar
  13. 13.
    Perttu EK, Arnold M, Iovine PM (2005) Tetrahedron Lett 46(50):8753–8756CrossRefGoogle Scholar
  14. 14.
    Campbell NL, Clowes R, Ritchie LK, Cooper AI (2009) Chem Mater 21(9):204–206CrossRefGoogle Scholar
  15. 15.
    SAINT PLUS: Bruker Analytical X-ray Systems: Madison, WI, 2001Google Scholar
  16. 16.
    SADABS: Bruker Analytical X-ray Systems: Madison, WI, 2001Google Scholar
  17. 17.
    Sheldrick GM (2008) Acta Crystallogr Sect A 64:112–122CrossRefGoogle Scholar
  18. 18.
    Hubschle CB, Sheldrick GM, Dittick B (2011) J Appl Cryst 44:1281–1284CrossRefGoogle Scholar
  19. 19.
    Wu QG, Wu G, Brancaleon L, Wang S (1999) Organometallics 18(13):2553–2556CrossRefGoogle Scholar
  20. 20.
    http://sdbs.db.aist.go.jp. Accessed 15 Apr 2015
  21. 21.
    Steed JW (2003) CrystEngComm 5:169–179CrossRefGoogle Scholar
  22. 22.
    Anderson KM, Afarinkia K, Yu H-W, Goeta AE, Steed JW (2006) Cryst Growth Des 6:2109–2113CrossRefGoogle Scholar
  23. 23.
    Desiraju GR (2007) CrystEngComm 9:91–92CrossRefGoogle Scholar
  24. 24.
    Anderson KM, Steed JW (2007) CrystEngComm 9:328–330CrossRefGoogle Scholar
  25. 25.
    van Eijck BP, Kroon J (2000) Acta Crystallogr Sect B 56:535–542CrossRefGoogle Scholar
  26. 26.
    Nichol GS, Clegg W (2006) Cryst Growth Des 6:451–460CrossRefGoogle Scholar
  27. 27.
    Clegg W, Scott AJ, Souza FES, Marder TB (1999) Acta Cryst Sect C 55:1885–1888CrossRefGoogle Scholar
  28. 28.
    Chikkali S, Magens S, Gudat D, Nieger M, Hartenbach I, Schleid T (2008) Eur J Inorg Chem 2207–2213:31Google Scholar
  29. 29.
    Neu RC, Jiang C, Stephan DW (2013) Dalton Trans 42:726–736CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Department of Chemistry & PhysicsWestern Carolina UniversityCullowheeUSA
  2. 2.Chemistry DepartmentThe College of William and MaryWilliamsburgUSA

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