4-(Morpholin-4-yl)-3-(trifluoromethyl)benzonitrile

In the title benzonitrile compound, C12H11F3N2O, an intramolecular C—H⋯F hydrogen bond generates an S(7) ring motif. The trifluoromethyl group is disordered over two orientations with a refined occupancy ratio of 0.549 (16):0.451 (16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04 (10)° with each other. In the crystal, molecules are connected by intermolecular C—H⋯F and C—H⋯O interactions to form R 2 2(8) ring motifs. These interactions also link the molecules into chains parallel to the [10] direction.

In the title benzonitrile compound, C 12 H 11 F 3 N 2 O, an intramolecular C-HÁ Á ÁF hydrogen bond generates an S(7) ring motif. The trifluoromethyl group is disordered over two orientations with a refined occupancy ratio of 0.549 (16):0.451 (16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04 (10) with each other. In the crystal, molecules are connected by intermolecular C-HÁ Á ÁF and C-HÁ Á ÁO interactions to form R 2 2 (8) ring motifs. These interactions also link the molecules into chains parallel to the [101] direction.
The reaction mixture was heated to 353 K for 12 h. The reaction mixture was cooled to 298-299 K, concentrated under vacuum and the crude product was diluted with water (100 ml) and extracted with ethyl acetate (2x100 ml). The ethyl acetate layer was further washed with water (100 ml), brine solution, dried over Na 2 SO 4 and concentrated to get the desired product as colourless crystalline solid, recrystallised from ethanol (Klemann et al., 2001). Yield 3.8 g (94%), M.p.: 408-410 K.

Refinement
Atoms F1, F2 and F3 are disordered over two sets of sites with a refined occupancy ratio of 0.549 (16)

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 > 2sigma(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. (