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Three new organotin(IV) complexes, [Me₃Sn(H₂L)]₂ (<b>1</b>), Bu₃Sn(H₂L) (<b>2</b>), and [(Bu₂Sn(H₂L))₂O]₂ (<b>3</b>) were synthesized by the reaction of 2-[4-hydroxy-3-((2-hydroxyethylimino)methyl)phenylazo]benzoic acid (<b>H₃L</b>) with appropriate alkyltin(IV) precursors. The complexes were characterized by elemental analysis, IR, and multinuclear (¹H, ¹³C and ¹¹⁹Sn) NMR spectroscopy. Further, the complex <b>1</b> was analyzed by single-crystal X-ray analysis. It displays a 24-membered cyclic dimeric Me₃Sn^IV(H₂L) unit where the ligand act as a bridging framework using its carboxylate-O and phenoxy-O atoms. The Sn(IV) adopts distorted trigonal-bipyramidal geometry. In the solution state, the structures were determined by ¹¹⁹Sn-NMR spectroscopy, and the complexes <b>1</b> and <b>2</b> have distorted tetrahedral geometry, whereas complex <b>3</b> shows distorted trigonal-bipyramidal geometry around the tin centres. The Hirshfeld surface analysis and DFT calculations, together with a topological analysis of the electron density distribution in the crystal structure of complex <b>1</b>, indicate that its molecular packing determined by various noncovalent interactions, including stacking and hydrogen bonding. The antibacterial studies of the ligand and the complexes (<b>1–3</b>) against gram-negative bacteria <i>viz. Klebsiella pneumoniae (A),Vibrio cholerae (M)</i> and <i>Shigella boydii (Q)</i> and gram-positive bacteria <i>viz.Staphylococcus aureus</i> (J), <i>Streptococcus pneumonia</i> (K) are promising and the compounds can be treated as potential common antibacterial materials.