Ethyl 4-anilino-2,6-bis(4-chlorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

The title compound, C32H28Cl2N2O2, was synthesized by a multicomponent reaction of 4-chlorobenzaldehyde, aniline and ethyl acetoacetate. The central 1,2,5,6-tetrahydropyridine ring exhibits a distorted boat conformation and the two chlorophenyl rings attached to the central ring at positions 2 and 6 are oriented in opposite directions. The two O atoms of the ethoxycarbonyl group are involved in intramolecular N—H⋯O and C—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O hydrogen bonds link molecules related by translation along the b axis into chains.

The title compound, C 32 H 28 Cl 2 N 2 O 2 , was synthesized by a multicomponent reaction of 4-chlorobenzaldehyde, aniline and ethyl acetoacetate. The central 1,2,5,6-tetrahydropyridine ring exhibits a distorted boat conformation and the two chlorophenyl rings attached to the central ring at positions 2 and 6 are oriented in opposite directions. The two O atoms of the ethoxycarbonyl group are involved in intramolecular N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds. In the crystal, weak C-HÁ Á ÁO hydrogen bonds link molecules related by translation along the b axis into chains.
In the crystal, weak intermolecular C-H···O hydrogen bonds (Table 1) link the molecules related by translation along the b axis into chains.

Experimental
A 50 ml flask was charged with a magnetic stir bar, p-chlorobenzaldehyde (5 mmol), ethylacetoacetate (2.5 mmol) and bismuth nitrate (0.005 mmol) in 10 ml e thanol; the mixture was then started to stir at room temperature. After 1 h min, pchlorobenzaldehyde (5 mmol) was added to the reaction mixture and stirring was continued up to completion of the reaction as monitored by TLC. After completion of the reaction, a thick precipitate was obtained. The solid was dissolved in hot ethyl acetate-ethanol mixture, the filtrate on standing afforded crystals of the pure product.

Refinement
All H atoms were placed in geometrically idealized positions (C-H 0.93-0.97 Å, N-H 0.86 Å) and treated as riding on their parent atoms, with U iso (H) = 1.2-1.5U eq (C, N).  The molecular structure of the title compound showing the atomic numbering and 30% probabilty displacement ellipsoids. H atoms omitted for clarity.

Computing details
Ethyl 4-anilino-2,6-bis(4-chlorophenyl)-1-phenyl-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 Cl1