4,4′-Bis(2,2,2-trifluoroethoxymethyl)-2,2′-bipyridine

As part of a homologous series of novel polyfluorinated bipyridyl (bpy) ligands, the title compound, C16H14F6N2O2, contains the smallest fluorinated group, viz. CF3. The molecule resides on a crystallographic inversion centre at the mid-point of the pyridine C-ipso-C-ipso bond. Therefore, the bpy skeleton lies in an anti conformation to avoid repulsion between the two pyridyl N atoms. Weak intramolecular C-H center dot center dot center dot N and C-H center dot center dot center dot O interactions are observed, similar to those in related polyfluorinated bpy-metal complexes. A pi-pi interaction is observed between the bpy rings of adjacent molecules and this is probably a primary driving force in crystallization. Weak intermolecular C-H center dot center dot center dot N hydrogen bonding is present between one of the CF3CH2-methylene H atoms and a pyridyl N atom related by translation along the [010] direction, in addition to weak benzyl-type C-H center dot center dot center dot F interactions to atoms of the terminal CF3 group. It is of note that the O-CH2CF3 bond is almost perpendicular to the bpy plane.