(3Z)-1,1,1-Trifluoro-4-phenyl-4-[(2-{[(1Z)-4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl]amino}ethyl)amino]but-3-en-2-one

In the title compound, C22H18F6N2O2, the five atoms comprising each O=C—C=C—N fragment are almost coplanar (the r.m.s. deviation for the fitted atoms being 0.008 and 0.002 Å) and form a dihedral angle of 47.70 (12)°. The phenyl ring attached to each of the O=C—C=C—N fragments is twisted out of the respective plane with dihedral angles of 64.46 (11) and 61.82 (10)°, respectively. An almost orthogonal relationship for the phenyl rings is indicated by the dihedral angle between them of 78.19 (14)°. The conformation about each ethylene bond is Z, which allows for the formation of intramolecular N—H⋯O hydrogen bonds which close S(6) loops. The most prominent feature of the crystal packing are N—H⋯O hydrogen bonds that result in supramolecular chains along the a axis. The F atoms of one –CF3 groups are disordered over three sets of sites with site-occupation factors of 0.318 (4), 0.360 (10) and 0.322 (9).

In the title compound, C 22 H 18 F 6 N 2 O 2 , the five atoms comprising each O C-C C-N fragment are almost coplanar (the r.m.s. deviation for the fitted atoms being 0.008 and 0.002 Å ) and form a dihedral angle of 47.70 (12) . The phenyl ring attached to each of the O C-C C-N fragments is twisted out of the respective plane with dihedral angles of 64.46 (11) and 61.82 (10) , respectively. An almost orthogonal relationship for the phenyl rings is indicated by the dihedral angle between them of 78.19 (14) . The conformation about each ethylene bond is Z, which allows for the formation of intramolecular N-HÁ Á ÁO hydrogen bonds which close S(6) loops. The most prominent feature of the crystal packing are N-HÁ Á ÁO hydrogen bonds that result in supramolecular chains along the a axis. The F atoms of one -CF 3 groups are disordered over three sets of sites with site-occupation factors of 0.318 (4), 0.360 (10) and 0.322 (9).

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95-0.99 Å, U iso (H) = 1.2U eq (C)] and were included in the refinement in the riding model approximation. The N-bound H-atoms were located in a difference were refined freely. One trifluoromethyl group is disordered over three positions in respect to the F atoms. The C-F distances were restrained to within 1.35±0.01 Å, and the F···F distances to 2.21±0.01 Å. The disordered F atoms were refined isotropically and the final site occupancies were 0.318 (4), 0.360 (10) and 0.322 (9) for the unprimed, primed and doubly primed atoms, respectively.

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The C1-CF 3 group is disordered over three positions. The orientation with a site occupancy factor = 0.318 (4)

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