We present a crystallographic study that systematically investigates the effects of the n-alkyl side-chain length on the crystal packing in shape-persistent macrocycles. The solid-state packing of carbazole–ethynylene-containing macrocycles is sensitive to the alkyl-chain length. In macrocycles containing n-alkyl side chains up to nine carbons in length, face-on aromatic π interactions predominate, while the addition of one carbon leads to a ...