Synthesis, crystal structure, Hirshfeld surface analysis, DFT and NBO study of ethyl 1-(4-fluoro­phen­yl)-4-[(4-fluoro­phen­yl)amino]-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

The title com­pound, C(32)H(28)F(2)N(2)O(2), a highly functionalized tetra­hydro­pyridine, was synthesized by a one-pot multi-com­ponent reaction of 4-fluoro­aniline, ethyl aceto­acetate and benzaldehyde at room temperature using sodium lauryl sulfate as a catalyst. The com­pound crystallizes with two mol­ecules in the asymmetric unit. The tetra­hydro­pyridine ring adopts a distorted boat conformation in both mol­ecules and the dihedral angles between the planes of the fluoro-substituted rings are 77.1 (6) and 77.3 (6)°. The amino group and carbonyl O atom are involved in an intra­molecular N—H⋯O hydrogen bond, thereby generating an S(6) ring motif. In the crystal, mol­ecules are linked by C—H⋯F hydrogen bonds forming a three-dimensional network and C—H⋯π inter­actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (47.9%), C⋯H/H⋯C (30.7%) and F⋯H/H⋯F (12.4%) contacts. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6-311+G(2d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was used to determine the energy gap and the Natural Bond Orbital (NBO) analysis was done to study donor–acceptor interconnections.