N-[2-Chloro-6-(4-chloro-6-methoxypyrimidin-2-ylsulfanyl)benzyl]-3,4-dimethylaniline

In the title molecule, C20H19Cl2N3OS, the dihedral angle between the two benzene rings is 79.3 (7)°. The 4-chloro-6-methoxypyrimidine group is rotationally disordered over two sites by approximately 180°, the ratio of the refined occupancies being 0.6772 (15):0.3228 (15). Both disorder components of disorder are involved in intramolecular N—H⋯N hydrogen bonds.

In the title molecule, C 20 H 19 Cl 2 N 3 OS, the dihedral angle between the two benzene rings is 79.3 (7) . The 4-chloro-6methoxypyrimidine group is rotationally disordered over two sites by approximately 180 , the ratio of the refined occupancies being 0.6772 (15):0.3228 (15). Both disorder components of disorder are involved in intramolecular N-HÁ Á ÁN hydrogen bonds.

D-HÁ
The molecular structure is shown in Fig. 1. The bond lengths and angles are as expected. The the dihedral angle between the two benzene rings is 79.3 (7)°. The 4-chloro-6-methoxypyrimidine group is rotationlly disordered over two sites by approximately 180° with the ratio of the refined occupancies being 0.6772 (15):0.3228 (15). Both the major and minor components of disorder are involved in intramolecular N-H···N hydrogen bonds.
After evaporation of the solvent, the residue was purified by column chromatography on silica gel to afford the title compound as a colorless solid (yield 90%). The title compound was recrystallized from CH 2 Cl 2 at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Refinement
All H atoms were positioned geometrically and treated as riding, with C-H bond lengths constrained to 0.93 Å (aromatic CH); 0.97 Å (methylene CH 2 ); 0.96 Å (methyl), and with Uĩso~(H) = 1.2U eq (C) or 1.5U eq (methyl C). Fig. 1. The molecular structure of the title compound with the atom numbering scheme and 30% probability displacement ellipsoids. The disorder is not shown. N-

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.