To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylphenyl 4-methylbenzenesulfonate, C₁₄H₁₂O₄S, 3a, 2-formylphenyl 4-chlorobenzenesulfonate, C₁₃H₉ClO₄S, 3b, 2-formylphenyl 4-bromobenzenesulfonate, C₁₃H₉BrO₄S, 3c, 4-formylphenyl 4-methylbenzenesulfonate, C₁₄H₁₂O₄S, 4a, 4-formylphenyl 4-chlorobenzenesulfonate, 4b, C₁₃H₉ClO₄S, and 4-formylphenyl 4-bromobenzenesulfonate, C₁₃H₉BrO₄S, 4c. The title compounds were synthesized under basic conditions from salicylaldehyde/4-hydroxybenzaldehydes and various aryl sulfonyl chlorides. Remarkably, halogen-bonding interactions are found to be important to rationalize the solid-state crystal structures. In particular, the formation of O...X (X = Cl and Br) and type I X...X halogen-bonding interactions have been analyzed by means of density functional theory (DFT) calculations and characterized using Bader's theory of `atoms in molecules' and molecular electrostatic potential (MEP) surfaces, confirming the relevance and stabilizing nature of these interactions. They have been compared to antiparallel π-stacking interactions that are formed between the arylsulfonates.