1-(2-Methyl-phen-yl)-4,4'-bipyridin-1-ium tetra-fluorido-borate.

Claire E Welton,Bradley W Smucker,Vladimir N Nesterov

doi:10.1107/s2414314622002486

Abstract

Crystals of the title compound, C17H15N2 +·BF4 -, were unexpectedly grown from crystallization attempts of [Pt(4,4'-bpy)4](BF4)2 [Smith et al. (2019 ▸). Comments Inorg. Chem. 39, 188-215] using toluene and aceto-nitrile. The tetra-fluoro-borate anion and the central pyridinium ring of the cation are disordered, with atomic site occupancies close to ½. The tolyl group of the cation has a 75.31 (11)° twist relative to the unsubstituted pyridyl group. This rotation allows for a centrosymmetric dimer of cations with weak hydrogen bonding between the pyridyl nitro-gen atom and a methyl H atom on the neighbouring cation.

Highlights

For each cation of the title structure, the ring of the tolyl group is twisted relative to the monosubstituted 4,40-bipyridinium with a 75.31 (11) rotation between planes (comprised of the tolyl ring (C11–C16) versus the unsubstituted pyridyl ring (N1/C1–C5) (Fig. 1) ; the central pyridinium ring (C6, C7, C9, C10) is disordered over two orientations with refined occupancies of 0.507 (6) and 0.493 (6)
The twisted conformation in the title compound allows for head-to-tail packing between two cations (Fig. 2)
The C—N distance between the pyridinium and tolyl group is 1.487 (4) A. This is longer than the C—N bond lengths observed in N-aryl structures of monosubstituted 4,40-bipyridinium in: N-phenyl [1.460 (2) A ; Coe et al, 1998], N-naphthyl [1.455 (2) A ; Lin & Zhao, 2015], or N-biphenyl [1.449 (5) A ; Schoder et al, 2019]

Summary

Structure description

For each cation of the title structure, the ring of the tolyl group is twisted relative to the monosubstituted 4,40-bipyridinium with a 75.31 (11) rotation between planes (comprised of the tolyl ring (C11–C16) versus the unsubstituted pyridyl ring (N1/C1–C5) (Fig. 1) ; the central pyridinium ring (C6, C7, C9, C10) is disordered over two orientations with refined occupancies of 0.507 (6) and 0.493 (6). This twist is similar to the 78.12 between corresponding planes of a N-naphthyl monosubstituted 4,40-bipyridinium cation The position of this adjacent dimer results in an N1Á Á ÁH10 (À12 + x, 32 À y, À12 + z) distance of 2.369 Abetween the pyridyl nitrogen atom and the hydrogen atom on the other pyridinium ring (Fig. 2)

HÁ Á ÁA

Synthesis and crystallization

No of restraints

Data collection