Abstract
The title compound, C(19)H(14)N(2)O(3), features competition and inter-play of a range of weak inter-actions, which actualize under the absence of conventional hydrogen-bond donors. Two kinds of stacking inter-actions, namely slipped anti-parallel inter-actions of cyano-phenyl groups as well as quinoline and carb-oxy groups, are primarily important. In combination with relatively short tetrel OCH(3)⋯N≡C bonds [C⋯N = 3.146 (3) Å] they are responsible for the generation of the layers, while the inter-layer 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 inter-action energies. Contributions of the C⋯C, C⋯N/N⋯C and C⋯O/O⋯C contacts originating in the stacking inter-actions account for 17.0% to the surface area. The largest inter-actions 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 inter-actions (-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.