(E)-Benzyl(1-phenylethylidene)amine

The title compound, C15H15N, represents an E isomer. The molecule exhibits a minor [9.1 (2)%] disorder with methylbenzylidene and benzyl groups interchanging their positions. The C=N bond length is 1.292 (2) Å. The molecular geometry is essentially planar, with the maximal twist of 8.5 (3)° for the benzyl group. The herringbone packing arrangement does not exhibit any π-stacking interactions.

The title compound, C 15 H 15 N, represents an E isomer. The molecule exhibits a minor [9.1 (2)%] disorder with methylbenzylidene and benzyl groups interchanging their positions. The C N bond length is 1.292 (2) Å . The molecular geometry is essentially planar, with the maximal twist of 8.5 (3) for the benzyl group. The herringbone packing arrangement does not exhibit any -stacking interactions.

Experimental
The title compound was obtained using a hybrid procedure of that reported in the literature (Guthrie et al., 1973;Willoughby & Buchwald, 1994). A zinc catalyst was first prepared by adding 0.500 ml benzylamine to a mixture of 4 g of saturated ZnCl 2 solution and 2 ml of ethanol. The solid catalyst was filtered out with a fritted funnel.
The catalyst was added to a mixture of 23.5 ml (0.200 mol) acetophenone and 21.8 ml (0.200 mol) of benzylamine in 100 ml of toluene. A reflux was conducted in a mineral oil bath, under argon with a Dean-Stark apparatus for 22 hrs at 120°C. After cooling, the solution was filtered through Celite and the toluene pumped off using a vacuum line.
The reflux product was then purified by distillation under vacuum (65 mTorr). Distillate collected at a distillation flask temperature of 109°C and vapor temperature of 45°C contained no imine product and was discarded. Distillate collected at a distillation flask temperature of ~190°C and vapor temperature of 80°C contained imine product.
To crystallize the final product, 50 ml of pentane was added to the second distillate and pumped off under vacuum line.
Recrystallization by slow evaporation of a hexane solution produced X-ray quality crystals.

Refinement
All non-hydrogen atoms were refined anisotropically. Hydrogen atoms on carbon were included in calculated positions and refined using a riding model at C-H = 0.95, 0.98 and 0.99 Å and U iso (H) = 1.2, 1.5 and 1.2 × U eq (C) of the aryl, methyl and methylene C-atoms, respectively. The positions of the methyl H atoms were rotationally optimized. The disorder was modeled and refined with the help of similarity restraints on displacement parameters (SIMU), rigid bond restraints on 1-2 and 1-3 distances and anisotropic displacement parameters (DELU), and constraints on anisotropic supplementary materials sup-2 Acta Cryst. (2013). E69, o1289 displacement paramenters of the minor component (EADP). The extinction parameter (EXTI) refined to zero and was removed from the refinement.

Computing details
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov, et al., 2009) and Mercury (Macrae et al., 2006). 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 Occ. (