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Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-eth-oxy-quinoline-4-carboxyl-ate.

ABSTRACT: In the title quinoline derivative, C₁₄H₁₄ClNO₃, there is an intra-molecular C-H⋯O hydrogen bond forming an S(6) graph-set motif. The mol-ecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-eth-oxy-quinoline mean plane. In the crystal, offset π-π inter-actions with a centroid-to-centroid distance of 3.4731 (14) Å link inversion-related mol-ecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H⋯H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

SUBMITTER: Bouzian Y

PROVIDER: S-EPMC6658954 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of ethyl 2,4-di-chloro-quinoline-3-carboxyl-ate.

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Crystal structure, Hirshfeld surface analysis, DFT and mol-ecular docking investigation of 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 2-[2-(2-oxo-1,3-oxazolidin-3-yl)eth-oxy]quinoline-4-carboxyl-ate.

Project description:In the mol-ecular structure of the title compound, C20H21N3O7, the quinoline ring system is slightly bent, with a dihedral angle between the phenyl and the pyridine rings of 3.47?(7)°. In the crystal, corrugated layers of mol-ecules extending along the ab plane are generated by C-H?O hydrogen bonds. The inter-molecular inter-actions were qu-anti-fied by Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are from H?H (42.3%), H?O/O?H (34.5%) and H?C/ C?H (17.6%) contacts. Mol-ecular orbital calculations providing electron-density plots of the HOMO and LUMO as well as mol-ecular electrostatic potentials (MEP) were computed, both with the DFT/B3LYP/6-311?G++(d,p) basis set. A mol-ecular docking study between the title mol-ecule and the COVID-19 main protease (PDB ID: 6LU7) was performed, showing that it is a good agent because of its affinity and ability to adhere to the active sites of the protein.

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2-Bromo-ethyl 2-chloro-6-methyl-quinoline-3-carboxyl-ate.

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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.

Project description: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 ?-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.

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Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl}indoline-2,3-dione.

Project description:The title compound, C14H15BrClNO4, consists of a 5-bromo-indoline-2,3-dione unit linked to a 1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl} moiety. In the crystal, a series of C-H?O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R 2 2(8), R 2 2(12), R 2 2(18) and R 2 2(22) ring motifs. ?-? contacts between the five-membered dione rings may further stabilize the structure, with a centroid-centroid distance of 3.899?(2)?Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (28.1%), H?O/O?H (23.5%), H?Br/Br?H (13.8%), H?Cl/Cl?H (13.0%) and H?C/C?H (10.2%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(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. The chloro-eth-oxy-ethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665?(8):0.335?(6).

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