Copper(I) halide and palladium(II) chloride complexes with tricyclic monastrol analogs containing the oxadiazocine ring have been synthesized and studied. The structures of the complexes were investigated with IR, NMR and UV spectroscopy. Two complexes, [Cu(L¹)₂Cl] and [Pd(L¹)₂Cl₂], were structurally characterized by X-ray single-crystal and powder diffraction respectively. All the obtained coordination compounds were mononuclear. The ligands were coordinated with copper(I) and palladium(II) only via the soft sulfur atoms of thiocarbamide fragments, while the harder nitrogen and oxygen atoms remained uncoordinated. The palladium center was coordinated by two Cl ions and two S atoms from two 4-thioxo[1,3,5]oxadiazocine ligands in a distorted square-planar geometry. Copper(I) formed a trigonal planar geometry. The complexes demonstrated significant antibacterial activity towards the Escherichia coli K12 TG 1 bacterial strain in contrast to the free ligands, which didn’t show any noticeable activity.