5-[(3,5-Dichloro-anilino)meth-yl]-N-(3,5-dichloro-phen-yl)-6-methyl-2-phenyl-pyrimidin-4-amine

Abstract

In the title compound, C24H18Cl4N4, the pyrimidine ring makes dihedral angles of 19.1 (2), 4.1 (2) and 67.5 (2)°, respectively, with phenyl and two benzene rings, and the mol-ecular conformation is stabilized by an intra-molecular N-H⋯N hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of inter-molecular N-H⋯N hydrogen bonds connect two mol-ecules, forming inversion dimers with R2(2)(12) motifs. C-H⋯π inter-actions links the dimers into a chain running along the a-axis direction. There are also π-π stacking inter-actions [centroid-centroid distance = 3.666 (4) Å] between the benzene rings of adjacent chains.

Fig. 1.

The molecule of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dotted line indicates the intramolecular N—H···N hydrogen bond.

Fig. 2.

Part of the crystal structure of 5-[(3,5-dichloroanilino)methyl]-N-(3,5-dichlorophenyl)-6-methyl-2-phenylpyrimidin-4-amine, showing N—H···N and C—H···π interactions. Dashed lines indicate intra- and intermolecular hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity.