An isomeric series of S2O macrocycles incorporating a xylyl group at the ortho (L1), meta (L2), and para (L3) positions were employed to examine the influence of the ring rigidity on silver(I) coordination modes in resulting supramolecular complexes (1-3); L1 and L3 afforded sandwich (1; Ag:L1 = 1:2) and infinite 1-D (3) complexes, respectively; otherwise, L2 gave the 1-D polymer (2a), 2:3 club sandwich (2b), and unique 2:4 bridged dinuclear complex (2c) complexes, in which their topologies vary with the solvent used.