N-(4-Meth-oxy-phen-yl)-6-methyl-2-phenyl-5-{[4-(tri-fluoro-meth-yl)anilino]meth-yl}pyrimidin-4-amine

Abstract

The title compound, C26H23F3N4O, crystallizes with two symmetry-independent mol-ecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the meth-oxy-phenyl ring. The -CF3 group of mol-ecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853 (4). The dihedral angles between the pyrimidine ring and the attached phenyl, meth-oxy-phenyl and tri-fluoro-methyl-phenyl rings are 8.1 (2), 37.5 (2) and 70.7 (2)°, respectively, in mol-ecule A, and 9.3 (2), 5.3 (2) and 79.7 (2)° in mol-ecule B. An intra-molecular N-H⋯N hydrogen bond occurs in each mol-ecule. In the crystal, two crystallographically independent mol-ecules associate into a dimer via a pair of N-H⋯N hydrogen bonds, with a resulting R 2 (2)(12) ring motif and π-π stacking inter-actions [centroid-centroid distance = 3.517 (4) Å] between the pyrimidine rings. For the A mol-ecules, there are inter-molecular C-H⋯O hydrogen bonds between an aryl C atom of meth-oxy-phenyl ring and a meth-oxy O atom of an adjacent mol-ecule. A similar inter-action is lacking in the B mol-ecules.

Fig. 1.

View of two symmetry independent molecules of the title compound with labelling scheme and displacement ellipsoids drawn at the 50% probability level. F atoms with the occupancy fator of 0.147 (4) and H atoms are shown as small spheres of arbitrary radii. The dotted lines indicate intramolecular N—H···O hydrogen bonds. Thick dashed lines represent fragment of a minor component of the disordered CF3 group.

Fig. 2.

The arrangement of molecules A (light orange line) and B (black line), showing the intermolecular N—H···N and C—H···O hydrogen bonds (thick dashed lines). Thin dashed lines indicate intramolecular N—H···O interactions. The atoms of disordered CF3 group (with the smaller occupancy factor) and H atoms not involved in hydrogen bonding have been omitted for clarity.