Unexpected synthesis of novel 2-pyrone derivatives: crystal structures, Hirshfeld surface analysis and computational studies

Here we report synthesis of three new compounds namely, 1-acetyl-1H-benzimidazolo-2(3H)-one (<b>I</b>), <i>N</i>-(5-acetyl-6-methyl-2-oxo-2H-pyran-4-yl)-<i>N</i>-(2-acetamidophenyl)acetamide (<b>II</b>) and <i>N</i>-(2-acetamidophenyl)-<i>N</i>-2-oxo-2H-pyran-4-yl)acetamide (<b>III</b>) have been synthesized and characterized by single crystal X-ray diffraction. Compounds <b>I</b> and <b>II</b> crystallize in the monoclinic space groups P21/n, and P21/c, respectively, while <b>III</b> crystallizes in the triclinic space group P-1. The theoretical parameters of <b>I</b>–<b>III</b> have been calculated through density functional theory (DFT) by using the hybrid functional B3LYP and basis set 6-311++G**. These theoretical parameters have been compared with the experimental ones obtained by XRD. The significant intermolecular interactions arising in crystal packing are rationalized by means of the Hirshfeld surface analysis method. The major intermolecular contacts in the Hirshfeld surfaces of <b>I</b>–<b>III</b> are from H…H contacts. In addition, binding modes of <b>I</b>–<b>III</b> within Tyrosine-protein kinase JAK2 were investigated using molecular docking and molecular dynamics simulation studies. Communicated by Ramaswamy H. Sarma