Dinuclear Monomeric and Macrocyclic Organotin Dithiocarbamates Derived from 1,10-Diaza-18-crown-6 and 4,4-Trimethylenedipiperidine

1,10-Diaza-18-crown-6 and 4,4-trimethylenedipiperidine were transformed into bis-dithiocarbamate ligands, which were then reacted in situ with different di- and triorganotin(IV) chlorides to generate dinuclear monomeric or macrocyclic products. The identity of the compounds was established by elemental analysis, multinuclear NMR spectroscopy (1H, 13C, and 119Sn), IR spectroscopy, mass spectrometry, and for representative examples additionally by single-crystal X-ray diffraction analysis. In combination with DFT calculations, the structural characterization showed that diaryltin and dialkyltin fragments give macrocycles of different conformation owing to changes in the coordination stereochemistry (cis vs. trans isomers). The macrocycle cavities are suitable for the inclusion of guest molecules. At the supramolecular level, the Sn complex molecules are linked through intermolecular CH center dot center dot center dot S and CH center dot center dot center dot Cl interactions in the solid state.