Structure of six organic acid–base adducts from 6-bromobenzo[d]thiazol-2-amine and acidic compounds

• Six supramolecular compounds with 1D–3D structure have been prepared and characterized.
• The noncovalent interaction between 2-aminothiazole derivative and acids have been discussed.
• The NH⋯O/OH⋯N hydrogen bond is the primary force in a family of structures containing the OH⋯2-aminothiazole synthons.
• Except 1, all compounds bear the heterosynthon R22(8).

Six anhydrous organic acid–base adducts of 6-bromobenzo[d]thiazol-2-amine were prepared with organic acids as 2,4,6-trinitrophenol, salicylic acid, 3,5-dinitrobenzoic acid, 3,5-dinitrosalicylic acid, malonic acid and sebacic acid. The compounds 1–6 were characterized by X-ray diffraction analysis, IR, and elemental analysis. The melting points of all the adducts were given. Of the six adducts, 1, 3, 4, and 5 are organic salts, while 2, and 6 are cocrystals. The supramolecular arrangement in the crystals 2–6 is based on the R22(8) synthon. Analysis of the crystal packing of 1–6 suggests that there are strong NH⋯O, OH⋯N, and OH⋯O hydrogen bonds (charge assisted or neutral) between acid and base components in the supramolecular assemblies. When the hydroxyl group is present in the ortho position of the carboxy, the intramolecular S6 synthon is present, as expected. Besides the classical hydrogen bonding interactions, other noncovalent interactions also play important roles in structure extension. Due to the synergetic effect of these weak interactions, compounds 1–6 display 1D–3D framework structure.