organic compounds
4-Amino-trans-azobenzene {or 4-[(E)-phenyldiazenyl]aniline} can form isomeric salts depending on the site of protonation. Both orange bis{4-[(E)-phenyldiazenyl]anilinium} hydrogen phosphate, 2C12H12N3+·HPO42−, and purple 4-[(E)-phenyldiazenyl]anilinium dihydrogen phosphate phosphoric acid solvate, C12H12N3+·H2PO4−·H3PO4, (II), have layered structures formed through O—HO and N—HO hydrogen bonds. Additionally, azobenzene fragments in (I) are assembled through C—Hπ interactions and in (II) through π–π interactions. Arguments for the colour difference are tentatively proposed.