7,16-Dibenzyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane, C ₂₆H₃₈N₂O₄, (I), crystallizes in space group P2₁/c, with two independent molecules adopting different conformations. The 'free' crowns adopt a typical 'parallelogram' shape, in which two methylene groups are turned inward toward the center of the ring and the benzyl groups splay out from the ring. In 7,16-dibenzyl-1,4,10,13-tetraoxa-7,16- diazoniacyclooctadecane bis(tetrafluoroborate) monohydrate, C₂₆H ₄₀N₂O₄2⁺·2BF₄ ^-·H₂O, (II), the macrocycle is centrosymmetric, and the protonated N atoms adopt an endo-endo orientation that is stabilized by a bifurcated N-H⋯O hydrogen bond, where the O atoms of the macrocycle act as hydrogen-bond acceptors. The phenyl groups of the benzyl side arms are turned above and below the macrocycle; C-H⋯π interactions between the phenyl substituents and two macrocyclic methylene H atoms govern the overall conformation of the macrocycle. Bridging tetrafluoroborate anions link the macrocyclic cations via weak C-H⋯F hydrogen bonds into channels running along [100], which are filled by the weakly hydrogen-bonded water molecules.