Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of new 2-oxo-1,2-dihydroquinoline-4-carboxylate derivative

Abstract

• A new 2-oxo-1,2-dihydroquinoline-4-carboxylate derivative has been synthesized. • It is characterized using NMR spectroscopy and X-ray crystallography. • Intercontacts between crystal units are identified by Hirshfeld surface analysis. • Good correlations are obtained between the X-ray data with the predicted ones. Prop-2-ynyl 6‑chloro-1,2-dihydro-2-oxo-1-(prop‑2-ynyl)quinoline-4-carboxylate was synthesized by an alkylation reaction under phase transfer catalysis (PTC) conditions. This compound was characterized through 1 H- and 13 C NMR spectroscopy and single crystal X-ray diffraction techniques. The crystal belongs to the monoclinic space group C2/c. The lattice parameters obtained are: a = 22.3050(12) Å, 11.9577(6) Å, c = 13.4295(7) Å, α = 90°, β = 124.939(2)°, γ = 90° and Z = 4. In addition, Hirshfeld surface analysis (2D and 3D) was performed to understand the different intermolecular interactions in the crystal structure and to determine the percentage contributions of these interactions on the surface. Theoretical calculations were carried out using Density functional theory (DFT) to develop optimized geometry and frontier molecular orbital analysis.