Anion-controlled networks of intermolecular interactions in the crystal structure of 9-aminoacridinium salts

A series of salts, with the 9-aminoacridinium cation (9-AA) and aromatic carboxylic acid: benzoate (1), ortho-phthalate (2), and salicylate (3) anions have been synthesized and characterized using X-ray diffraction. In the crystal packing, the ions are linked via N–H⋯O, O–H⋯O, and C–H⋯O hydrogen bonds. Analysis of the hydrogen bonds in the crystal lattices of the title compounds shows that the cations and anions form tetramers. The ions in these tetramers are linked via N(amino)–H⋯O(carboxy) hydrogen bonds forming R22(8) (1 and 3) or R24(15) (2) hydrogen bond ring motifs. The cations interact through π–π interactions in the ABBA (1), AB (2) or ABA (3) arrangement to form columns (1 and 2) or chains (3).