Crystal structure, Hirshfeld surface analysis, interaction energy and energy framework calculations, as well as density functional theory (DFT) computation, of methyl 2-oxo-1-(prop-2-ynyl)-1,2-dihydroquinoline-4-carboxylate

In the title molecule, C14H11NO3, the dihydroquinoline core deviates slightly from planarity, indicated by the dihedral angle of 1.07 (3)degrees between the two six-membered rings. In the crystal, layers of molecules almost parallel to the bc plane are formed by C-H center dot center dot center dot O hydrogen bonds. These are joined by pi-pi stacking interactions. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H center dot center dot center dot H (36.0%), H center dot center dot center dot C/C center dot center dot center dot H (28.9%) and H center dot center dot center dot O/O center dot center dot H (23.5%) interactions. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the dispersion energy contribution. Moreover, the molecular structure optimized by density functional theory (DFT) at the B3LYP/6-311G(d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.