Crystal structure, Hirshfeld surface analysis, inter­action energy and DFT calculations and energy frameworks of methyl 6-chloro-1-methyl-2-oxo-1,2-di­hydro­quinoline-4-carboxyl­ate

In the title compound, C(12)H(10)ClNO(3), the di­hydro­quinoline moiety is not planar with a dihedral angle between the two ring planes of 1.61 (6)°. An intra­molecular C—H⋯O hydrogen bond helps to establish the rotational orientation of the carboxyl group. In the crystal, sheets of mol­ecules parallel to (10 [Image: see text] ) are generated by C—H⋯O and C—H⋯Cl hydrogen bonds, and are stacked through slipped π-stacking inter­actions between inversion-related di­hydro­quinoline units. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (34.2%), H⋯O/O⋯H (19.9%), H⋯Cl/Cl⋯H (12.8%), H⋯C/C⋯H (10.3%) and C⋯C (9.7%) inter­actions. Computational chemistry indicates that in the crystal, the C—H⋯Cl hydrogen-bond energy is −37.4 kJ mol(−1), while the C—H⋯O hydrogen-bond energies are −45.4 and −29.2 kJ mol(−1). An evaluation of the electrostatic, dispersion and total energy frameworks revealed that the stabilization is dominated via the dispersion energy contribution. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined mol­ecular structure in the solid state, and the HOMO—LUMO behaviour was elucidated to determine the energy gap.