Synthesis, supramolecularity and in vitro antimicrobial activity of 3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-one

The solid-state structure of 3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-one (3) was determined using X-ray single crystal technique. Its non-covalent interactions were analyzed carefully in terms of crystal engineering and supramolecular chemistry. Multiple sulfur–hydrogen and oxygen–hydrogen interactions are present in the structure, most commonly involving bifurcated H⋯S⋯H motifs which resulted in formation interesting centrosymmetric dimmers. This compound demonstrated comparable antimicrobial activity to that of clinically used antimicrobial agents against selected microorganisms.

► A 1:1 adduct (3) has been synthesized in 100% yield by the reaction of ninhydrin with thiourea. ► The structure was assigned on the basis of spectral analysis and single crystal X-ray analysis. ► O, S and N cause interesting intermolecular non-covalent interactions in its solid-state motifs.