Syntheses and Structures of Diorganotin Compounds Containing a Pentadentate Schiff Base Featuring Two Chiral Centers

A pentadentate Schiff base pro‐ligand, suitable for the generation of metal complexes containing two chiral centers, is synthesized. The pro‐ligand H 2 L Me is reacted with diorganotin precursors to yield the tin compounds [Me 2 Sn(L Me )] ( 1 ), [ n‐ Bu 2 Sn(L Me )] ( 2 ), [ t‐ Bu 2 Sn(L Me )] ( 3 ), [Bn 2 Sn(L Me )] ( 4 ), and [ n‐ Oct 2 Sn(L Me )] ( 5 ), where L Me = N ‐[( E )‐1‐[6‐[( E )‐ N ‐( p ‐tolylsulfonamido)‐ C ‐methylcarbonimidoyl]pyridin‐2‐yl]ethylideneamino]‐ p ‐tolylsulfonamide. Characterization in solution (NMR spectroscopy and high‐resolution mass spectrometry) and solid state (Fourier transform infrared spectroscopy and single crystal X‐ray diffraction analysis) confirms for each compound a seven‐coordinate C 2 SnN 3 O 2 environment with pentagonal‐bipyramidal geometry. The 119 Sn NMR spectra exhibit high field‐shifted signals, consistent with seven coordinated diorganotin Schiff base derivatives. In the solid state, the S(O)C 6 H 4 Me moieties in 1 – 4 are mutually anti ‐oriented, resulting in molecular topologies similar to those found in Jacobsen's catalyst. In addition to van der Waals interactions, the molecular arrangements in the 3D solid‐state structures are primarily controlled by CH⋯O hydrogen bonds, along with CH⋯N, CH⋯π, and π⋯π interactions giving macrocyclic or cage‐type assemblies.