Two constitutional dynamic libraries (CDLs)-each containing two amines, two dialdehydes, and two metal salts-have been found to self-sort, generating two pairs of imine-based metallosupramolecular architectures (sharing no component) each with a [2 x 2] grid-like complex and a linear double helicate. These CDLs provided unique examples of a three-level self-sorting process, as only two imine-based ligand constituents, two metal complexes, and two architectures were selected during their assembly out of all the possible combinations of their initial components. The metallosupramolecular architectures assembled were characterized by NMR, mass spectroscopy, and X-ray crystallography.