119Sn NMR characterization, X-ray structural studies, and Hirshfeld surface analysis of organotin(IV) macroheterocycles synthesized by a Barbier approach via ultrasound activation.

Two series of dinuclear organotin macroheterocycles of general formula [R2Sn{Ch(C6H4CH2)2}2SnR2] [Ch = O with R = n-Bu (2a), Bn (3a), Ph (4a) and Ch = S with R = n-Bu (2b), Bn (3b), Ph (4b)] were easily synthetized by a Barbier-type reaction assisted by sonochemical activation of metallic magnesium. The 119Sn{1H} NMR data for all compounds and the X-ray single-crystal diffraction studies for 2a and 4a confirmed the presence of a central Sn atom in a four-coordinate environment. The molecular structures of 2a and 4a showed puckered 16-membered macroheterocycles. The tin and oxygen atoms are in the interior of the cavity of the macrocycle, surrounded by hydrophobic C–H bonds. A Hirshfeld surface analyses of 2a and 4a showed that the macrocycles are linked by weak C–H···π, C···C, and H···H non-covalent interactions. The pairwise interaction energies showed that the cohesion between the macrocycles are mainly due to dispersion forces. [ABSTRACT FROM AUTHOR]