(2E,2′E)-Dimethyl 2,2′-[(phenylazanediyl)bis(methylene)]bis(3-phenylacrylate)

The C=C double bonds in the title compound, C28H27NO4, adopt an E conformation. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers.

The C C double bonds in the title compound, C 28 H 27 NO 4 , adopt an E conformation. In the crystal, pairs of C-HÁ Á ÁO hydrogen bonds link the molecules into inversion dimers.

Experimental
gives average values of 1.340 Å and 1.447 Å respectively for these bonds (Varghese et al., 1986).
The crystal packing is stabilized by intermolecular nonclassical C-H···O hydrogen bonds linking the molecules into centrosymmetric dimers. A packing view of the title compound is shown in Fig. 2.

Experimental
A mixture of (Z)-methyl 2-(bromomethyl)-3-phenylacrylate (2 mmol) and aniline (1 mmol) in the presence of potassium carbonate (4 mmol) in dry acetonitrile (10 ml) was stirred at room temperature for 3 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3 x 20 ml). The organic layer was washed with brine (2 x 20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which successfully provide the crude final product ((2E,2′E)-dimethyl 2,2′-(phenylazanediyl)bis(methylene)bis(3-phenylacrylate)). The final product was purified by column chromatography on silica gel to afford the title compound in 35% yields.

Refinement
The hydrogen atoms were placed in calculated positions with C-H = 0.93 Å to 0.97 Å and refined in the riding model with fixed isotropic displacement parameters: U iso (H) = 1.5U eq (C) for methyl group and U iso (H) = 1.2U eq (C) for other groups.  The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms.

(2E,2′E)-Dimethyl 2,2′-[(phenylazanediyl)bis(methylene)]bis(3-phenylacrylate)
Crystal data C 28 H 27 NO 4 M r = 441.51 Triclinic, P1 Hall symbol: -P 1 a = 9.9099 (2) Å b = 11.7327 (2) Å c = 12.4079 (4) Å α = 101.131 (2)  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.