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Herein, an intra- and intercavity cooperative strategy has been developed by rationally installing rigid arms at the macrocyclic periphery to disrupt their tight crystal packing, thereby generating additional inter-ring cavities. Based on this, A,A\u2032-ortho-bis(pyridyl-hydrazone)-conjugated pillar[5]arene (o-PYP5) was synthesized. Unlike traditional macrocyclic hosts that rely solely on a single intrinsic cavity for guest encapsulation, o-PYP5 can self-assemble into hydrogen-bonded dimers, which further organize into a hydrogen-bonded dimer network crystal (HBDC) in the solid state, featuring both its intrinsic inner cavity and additional inter-ring cavities. 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