The syntheses of four supramolecular reagents (SRs) based on (N-pyridylmethylene)-aminobenzamides are reported. The crystal structure of 4'-(N-4-pyridylmethylene) aminobenzamide is dominated by an amide-py N-(HN)-N-... hydrogen bond and an amide-carbonyl N-(HO)-O-... hydrogen bond. The crystal structure of 4'-(N-3-pyridylmethylene)aminobenzamide contains the same N-(HN)-N-... interaction but this time it is accompanied by an amide-imine N-(HN)-N-... hydrogen bond. Finally, the crystal structure of 3'-(N-3-pyridylmethylene) aminobenzamide contains a well-known amide-amide ribbon constructed from two inequivalent N-(HO)-O-... hydrogen bonds. The hydrogen-bond interactions in these three similar compounds are very different which indicates a structural flexibility that may be beneficial for successful co-crystallization reactions.