A new synthetic route for the preparation of 2,2′,5′-trimethyl-7-oxo-4,7-dihydro-[6,7′-bipyrazolo[1,5-a]pyrimidine]-3,3′-dicarbonitrile, structural elucidation, Hirshfeld surface analysis, energy framework, density functional theory and molecular docking investigations

A new bipyrazolo [1,5-a]pyrimidine derivative, 2,2′,5′-trimethyl-7-oxo-4,7-dihydro-[6,7′-bipyrazolo[1,5-a]pyrimidine]-3,3′-dicarbonitrile dihydrate acetic acid solvate (3) has been synthesized via two different methods and characterized by single-crystal X-ray diffraction (XRD) and spectroscopic techniques. A plausible reaction mechanism in the synthesis of 3 through the two synthetic routes used has been proposed. The XRD analysis reveals that the two bicyclic moieties in 3 are close to perpendicular to one another. Some formal double bonds appear localized while others appear to involve some delocalization. In the crystal structure, a layer structure is formed by O-H-O, O-H-N and N-H-O hydrogen bonds, along with weak C-H-O and π-stacking interactions. The energy framework indicates that the packing of 3 is mainly determined by dispersion interactions between molecules. The frontier molecular orbital analysis shows that 3 may act more as a nucleophile than an electrophile. The analysis of the Hirshfeld surface maps and 2D fingerprint plots of 3 reveal that intermolecular hydrogen bonding and H-H, N-H and O-H contacts are the major ones between the units of 3. The antibacterial activity of 3 is explored by its molecular docking into the binding site of tyrosyl-tRNA synthetase, where it formed a stable complex with the amino acids of tyrosyl-tRNA synthetase mainly through hydrogen bonding.