Crystal structure, Hirshfeld surface analysis and DFT calculations of ethyl 2-[4-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]acetate

Abstract

The asymmetric unit of the title compound, C10H12N4O2S, contains two molecules differing slightly in the orientations of the methyl groups. In the crystal, a sandwich-type structure extending parallel to the ab plane is formed by weak C—H...O and C—H...N hydrogen bonds together with slipped π-stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (43.5%), H...O/O...H (17.9%) and H...N/N...H (17.4%) interactions. The molecular structure optimized by density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. Further calculations include the HOMO–LUMO energies and molecular electrostatic potential (MEP) surfaces.