Structure determination and Hirshfeld surface analysis of new cocrystal and salt forms of 5‐aminotetrazole with hydroxy‐ and nitro‐substituted carboxylic acids

Two new crystalline solids, namely, 5‐aminotetrazole–3,5‐dihydroxybenzoic acid–water (1/4/6), CH3N5·4C7H6O4·6H2O (I), and 5‐aminotetrazolium 3,5‐dinitrosalicylate, CH4N5+·C7H3N2O7− (II), have been synthesized and characterized by single‐crystal X‐ray diffraction and Hirshfeld surface analysis. The crystal packing arrangements of I and II are governed by N—H…O and O—H…O hydrogen‐bonding interactions. In cocrystal I, adjacent acid molecules are linked through O—H…O hydrogen bonds, forming a dimer with an R22(8) motif. In salt II, the tetrazolium cation and acid anion are linked through N—H…O hydrogen bonds to also form a dimer with an R22(8) motif. Further N—H…O and O—H…O hydrogen bonds help to stabilize the crystal packing, along with aromatic π–π stacking interactions in I and carbonyl…π interactions in II. The Hirshfeld surface analysis and fingerprint plots reveal that O…H/H…O interactions contribute 34.4% of the total interactions in the crystal packing of cocrystal I and 36.7% in salt II. In two crystalline solids (a cocrystal and a salt) of 5‐aminotetrazole, the crystal packing arrangements are governed by N—H…O and O—H…O hydrogen‐bonding interactions. The Hirshfeld surface analysis and fingerprint plots reveal that O…H/H…O interactions contribute 34.4% of the total interactions in the crystal packing of the cocrystal and 36.7% in the salt.