Crystal structure, Hirshfeld surface analysis, inter-action energy and DFT calculations and energy frameworks of methyl 6-chloro-1-methyl-2-oxo-1,2-di-hydro-quinoline-4-carboxyl-ate.

In the title compound, C12H10ClNO3, the di-hydro-quinoline moiety is not planar with a dihedral angle between the two ring planes of 1.61 (6)°. An intra-molecular C-H⋯O hydrogen bond helps to establish the rotational orientation of the carboxyl group. In the crystal, sheets of mol-ecules parallel to (10) are generated by C-H⋯O and C-H⋯Cl hydrogen bonds, and are stacked through slipped π-stacking inter-actions between inversion-related di-hydro-quinoline 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%) inter-actions. 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 mol-ecular structure in the solid state, and the HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbamo-yl]-2-oxo-1,2-di-hydro-quinolin-1-yl}acetate.

The title com-pound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetra-hydro-2-oxo-quinolin-1-yl)acetate and 4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbomoyl] units, where the oxo-quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C-HOxqn⋯OEthx and C-HPh-yl⋯OCarbx (Oxqn = oxoquinolin, Ethx = eth-oxy, Phyl = phenyl and Carbx = carboxyl-ate) weak hydrogen bonds link the mol-ecules into a three-dimensional network sturucture. A π-π inter-action between the constituent rings of the oxo-quinoline unit, with a centroid-centroid distance of 3.675 (1) Šmay further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (53.9%), H⋯O/O⋯H (28.5%) and H⋯C/C⋯H (11.8%) inter-actions. Weak inter-molecular hydrogen-bond inter-actions and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO mol-ecular orbital behaviour was elucidated to determine the energy gap.

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-chloro-ethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

The title compound, C15H12ClNO3, consists of a 1,2-di-hydro-quinoline-4-carb-oxyl-ate unit with 2-chloro-ethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the mol-ecules form zigzag stacks along the a-axis direction through slightly offset π-stacking inter-actions between inversion-related quinoline moieties which are tied together by inter-molecular C-HPrpn-yl⋯OCarbx and C-HChlethy⋯OCarbx (Prpnyl = propynyl, Carbx = carboxyl-ate and Chlethy = chloro-eth-yl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (29.9%), H⋯O/O⋯H (21.4%), H⋯C/C⋯ H (19.4%), H⋯Cl/Cl⋯H (16.3%) and C⋯C (8.6%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPrpn-yl⋯OCarbx and C-HChlethy⋯OCarbx hydrogen bond energies are 67.1 and 61.7 kJ mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.