1D and 3D supramolecular architectures in the salts of meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane with (2E)-2-cyano-2-(hydroxyimino)acetamide and 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl) hydrazinecarboxamide sustained by charge-assisted and conventional hydrogen bonds

Meso-5,7,7,12,12,14-hexamethyl-1,4,8,1 1-tetraazacyclotetradecane (tet-a) - (2E)-2-cyano-2-(hydroxyimino)acetamide (caH) (1:4) (1) is a salt [tet-aH(2)](2+)center dot 2[caH]center dot 2[ca](-) containing both neutral and deprotonated acetamide units. The acetamide units of the two types are linked by NH center dot center dot center dot O and OH center dot center dot center dot O hydrogen bonds into negatively charged chains; the chains are connected by the macrocyclic cations to form H-bonded ribbons. Tet-a and 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazinecarboxamide (urH) form a salt of 1:2:2 stoichiometry, [tet-aH(2)](2+)center dot 2[ur](-)center dot 2H(2)O (2). In (2), the deprotonated ur(-) units form a negatively charged 2D network substructure, and the layers are linked by the cations and water molecules to form a 3D framework. The tetraazamacrocycle shows different modes of the protonation of amine functionalities that depend on a substrate.