Crystal structure and Hirshfeld surface analyses, inter­action energy calculations and energy frameworks of methyl 2-[(4-cyano­phen­yl)meth­oxy]quinoline-4-carboxyl­ate

Abstract

The crystal structure of new quinoline-4-carboxyl­ate derivative exhibits a range of weak inter­actions, which were assessed using Hirshfeld surface analysis and inter­action energy calculations to support the dominant significance of the dispersion forces.

The title compound, C₁₉H₁₄N₂O₃, features competition and inter­play of a range of weak inter­actions, which actualize under the absence of conventional hydrogen-bond donors. Two kinds of stacking inter­actions, namely slipped anti­parallel inter­actions of cyano­phenyl groups as well as quinoline and carb­oxy groups, are primarily important. In combination with relatively short tetrel OCH₃⋯N≡C bonds [C⋯N = 3.146 (3) Å] they are responsible for the generation of the layers, while the inter­layer bonding occurs via C—H⋯O and C—H⋯N weak hydrogen bonds. These findings are consistent with the results of Hirshfeld surface analysis and calculated inter­action energies. Contributions of the C⋯C, C⋯N/N⋯C and C⋯O/O⋯C contacts originating in the stacking inter­actions account for 17.0% to the surface area. The largest inter­actions energies are associated with the two kinds of stacks (−45.8 and −24.3 kJ mol⁻¹) and they are superior to the energies of weak hydrogen bond and tetrel inter­actions (−12.4 to −22.4 kJ mol⁻¹). Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the consolidation is dominated via the dispersion energy contributions.