Proton-Transfer and Non-transfer Compounds of the Multi-purpose Drug Dapsone [4-(4-Aminophenylsulfonyl)aniline] with 3,5-Dinitrosalicylic Acid and 5-Nitroisophthalic Acid

Abstract

The structures of the compounds from the reaction of the drug dapsone [4-(4-aminophenylsulfonyl)aniline] with 3,5-dinitrosalicylic acid, the salt hydrate [4-(4-aminophenylsulfonyl)anilinium 2-carboxy-4,6-dinitrophenolate monohydrate] (1) and the 1:1 adduct with 5-nitroisophthalic acid [4-(4-aminophenylsulfonyl)aniline 5-nitrobenzene-1,3-dicarboxylic acid] (2) have been determined. Crystals of 1 are triclinic, space group P-1, with unit cell dimensions a = 8.2043(3), b = 11.4000(6), c = 11.8261(6) Å, α = 110.891(5)°, β = 91.927(3)°, γ = 98.590(4)° and Z = 4. Compound 2 is orthorhombic, space group Pbcn, with unit cell dimensions a = 20.2662(6), b = 12.7161(4), c = 15.9423(5) Å and Z = 8. In 1, intermolecular analinium N–H···O and water O–H···O and O–H···N hydrogen-bonding interactions with sulfone, carboxyl, phenolate and nitro O-atom and aniline N-atom acceptors give a two-dimensional layered structure. With 2, the intermolecular interactions involve both aniline N–H···O and carboxylic acid O–H···O and O–H···N hydrogen bonds to sulfone, carboxyl, nitro and aniline acceptors, giving a three-dimensional network structure. In both structures π–π aromatic ring associations are present. The structures of both an uncommon proton-transfer salt of the drug dapsone with 3,5-dinitrosalicylic acid and a molecular adduct with 5-nitroisophthalic acid are reported, together with their hydrogen-bonding patterns.