Ethyl 2,6-bis(4-chlorophenyl)-4-(4-fluoroanilino)-1-(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

In the title compound, C32H26Cl2F2N2O2, the tetrahydropyridine ring adopts a distorted boat conformation. The chlorophenyl rings are inclined to one another by 55.2 (1)°, while for the fluorophenyl rings the dihedral angle is 80.7 (1)°. The amino group and carbonyl O atom are involved in an intramolecular N—H⋯O hydrogen bond. In the crystal, weak C—H⋯O, C—H⋯F and C—H⋯Cl interactions link the molecules into a three-dimensional network.

A packing view down the a axis is shown in Fig.2.

Experimental
An oven-dried screw cap reaction tube was charged with a magnetic stir bar, 4-fluoroaniline (2 mmol), ethyl acetoacetate (1 mmol) and Bi(NO 3 ) 3 .5H 2 O (10 mol%) in 4 ml e thanol; the mixture was stirred at room temperature for 20 min, and afterthen 4-chlorobenzaldehyde (2 mmol) was added to the reaction mixture and stirring was continued up to 18 h to complete the reaction (monitored by TLC

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent C/N atoms, with C-H distances of 0.93-0.98 Å and N-H distance of 0.86 Å; and with U iso (H) = 1.2U eq (C/N), except for the methyl groups where U iso (H) = 1.5U eq (C),. The poor diffraction quality of the crystals prevented the obtention of a better data set with a larger N obs /N total reflection ratio.

Computing details
Data  The packing arrangement of molecules viewed down the a axis.
Ethyl 2,6-bis(4-chlorophenyl)-4-(4-fluoroanilino)-1-(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq