Two new dinuclear diorganotin(IV) dithiocarbamate (dtc) macrocycles, [Me2Sn(dtc)]2 (1) and [nBu2Sn(dtc)]2 (2), have been synthesized from R2SnCl2 (R = Me, nBu) and the bis(dithiocarbamate) derivative of N,N -dibenzylhexamethylene-1,6-diamine. These complexes have been characterized by elemental analysis, FAB mass spectrometry, IR and NMR (H, C, Sn) spectroscopy, as well as single crystal X-ray crystallography. The dtc ligands are coordinated to the tin atoms in the anisobidentate manner, both in solution and the solid state. The metal centers are hexacoordinated and the coordination polyhedron of the tin atoms can be described as bicapped tetrahedron or skew trapezoidal bipyramid. The cavities of the 26-membered macrocycles are hydrophobic with four sulfur atoms directed into the interior and have an inner diameter of approximately 4.1 x 5.6 A. The crystal structure of [Me2Sn(dtc)]2 (1) is stabilized by the presence of two chloroform molecules per asymmetric unit, which participate in intermolecular C-H⋅⋅⋅S, C-H⋅⋅⋅Cl hydrogen bonding and S⋅⋅⋅Cl donor acceptor interactions. On the other hand, the crystal structure of [nBu2Sn(dtc]2 (2) is stabilized additionally by intermolecular C-H⋅⋅⋅π interactions.