(E)-4-{[(Morpholin-4-yl)imino]methyl}benzonitrile

In the title compound, C12H13N3O, the morpholine ring adopts a chair conformation and its mean plane is inclined to that of the benzene ring by 16.78 (12)°. The N—N=C—C bridge, which has an E conformation, has a torsion angle of 173.80 (19)°. In the crystal, molecules stack along the a axis but there are no significant intermolecular interactions present.

In the title compound, C 12 H 13 N 3 O, the morpholine ring adopts a chair conformation and its mean plane is inclined to that of the benzene ring by 16.78 (12) . The N-N C-C bridge, which has an E conformation, has a torsion angle of 173.80 (19) . In the crystal, molecules stack along the a axis but there are no significant intermolecular interactions present.

Comment
Schiff bases, also known as imines or azomethines, are some of the most widely used organic compounds, for example, as pigments and dyes, catalysts, polymer stabilizers, and as intermediates in organic synthesis in particular for the preparation of heterocycles (Dhar & Taploo 1982;Zheng et al., 2009;Guzen et al., 2007). Schiff bases also play an important role in biological systems with several applications, for example, as antifungal, anticancer, antibacterial, antimalarial, antiproliferative, anti-inflammatory and antiviral agents in addition to other biological performances (Asif, 2014;Hisaindee et al., 2013). In view of this interest we synthesized the title compound and report herein on its crystal structure.
In the title molecule, Fig.1 In the crystal structure, there are no classical hydrogen bonds. The crystal packing is stabilized by van der Waals interactions.

Experimental
The title compound was synthesized by refluxing 4-aminomorpholine (1.00 mmol) with 4-cyanobenzeldehyde (1.00 mmol) in ethanol for 30 min. It was then recrystallized from ethanol to give light-yellow prismatic crystals (Yield 86%; M.p.: 401-403 K). Spectroscopic data for the title compound are available in the archived CIF.

Refinement
All H atoms were placed in calculated positions and refined as riding: C-H = 0.93 and 0.97 Å for CH and CH 2 H atoms, respectively, with U iso (H) = 1.2U eq (C). The crystals were of poor quality and weakly diffracting, which accounts for the low fraction of measured reflections. Repeated attempts to grow larger crystals were unsuccessful.

Figure 1
The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.  The crystal packing of the title compound, viewed along the a axis. Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.