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


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.


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



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.


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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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