Crystal structure determination, Hirshfeld surface, crystal void, intermolecular interaction energy analyses, as well as DFT and energy framework calculations of 2-(4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid

Abstract

In the title molecule, C7H6N4O3, the bicyclic ring system is planar with the carboxymethyl group inclined by 81.05 (5)° to this plane. In the crystal, corrugated layers parallel to (010) are generated by N—H...O, O—H...N and C—H...O hydrogen-bonding interactions. The layers are associated through C—H...π(ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...O/O...H (34.8%), H...N/N...H (19.3%) and H...H (18.1%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 176.30 Å3 and 10.94%, showing that there is no large cavity in the crystal packing. Computational methods revealed O—H...N, N—H...O and C—H...O hydrogen-bonding energies of 76.3, 55.2, 32.8 and 19.1 kJ mol−1, respectively. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated via dispersion energy contributions. Moreover, the optimized molecular structure, using density functional theory (DFT) at the B3LYP/6–311G(d,p) level, was compared with the experimentally determined one. The HOMO–LUMO energy gap was determined and the molecular electrostatic potential (MEP) surface was calculated at the B3LYP/6–31G level to predict sites for electrophilic and nucleophilic attacks.