Six new homobimetallic bis-diorganotin(IV) complexes: [Mehave been synthesized and structurally characterized by means of elemental analysis, mass spectroscopy, FT-IR, NMR ( 1 H, 13 C{ 1 H}, 119 Sn) and single-crystal X-ray diffraction. Spectroscopic studies indicate coordination of the ligand to the diorganotin(IV) moieties via iminolic oxygen, nitrogen and phenolic oxygen atoms generating pentacoordinated tin centers. Single-crystal X-ray analysis of (1) revealed homobimetallic nature of complex with dimethyltin moieties oriented in trans-conformation. The ligand is nonplanar with each Sn atom in a distorted square pyramidal coordination geometry. Packing diagrams suggest the essential role of C-H … N and C-H … O interactions in generating supramolecular assembly. The ligand and complexes were screened for in vitro antimicrobial activity and cytotoxicity. Compound (4) exhibits highest cytotoxicity.