N-(2-Chlorophenyl)-2-(4,6-dimethylpyrimidin-2-ylsulfanyl)acetamide

In the title compound, C14H14ClN3OS, the 4,6-dimethylpyrimidine ring and the chlorobenzene ring subtend a dihedral angle of 80.0 (2)°. The length of the Csp 2—S bond is significantly shorter than that of the Csp 3—S bond. The crystal structure is stabilized by intermolecular N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonding, and C—H⋯π interactions.

In the title compound, C 14 H 14 ClN 3 OS, the 4,6-dimethylpyrimidine ring and the chlorobenzene ring subtend a dihedral angle of 80.0 (2) . The length of the Csp 2 -S bond is significantly shorter than that of the Csp 3 -S bond. The crystal structure is stabilized by intermolecular N-HÁ Á ÁO, C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonding, and C-HÁ Á Á interactions.

Comment
The heteroatom-rich compounds have been intensively studied due to their applications including effective precursors for active molecule (Ye et al., 2006;Huynh et al., 2005). Now, we have synthesized the title compound, (I), from 4,6-dimethylpyrimidin-2-thiol with 2-chlorophenyl carbamic chloride. Here we report the crystal structure determination of the title compound.
The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The molecule contains a benzene ring and a pyrimidine ring. The dihedral angle between the benzene ring and benzo[d]thiazole ring is 80.0 (2)°, which indicate the two rings are close to be perpendicular. Cl atom attached to the benzene ring is coplanar to the benzene ring with an r.m.s deviation of 0.0130 (3) Å. The deviations with the pyrimidine ring plane of C13 and C14 atoms are 0.0544 (3) and 0.0005 (3) Å, respectively. The C6-N1-C7-C8 torsion angle of 177.61 (15)° indicates that the acylamide group are nearly coplanar with the benzene ring plane. As a result of π-π conjugation, the Csp 2 -S bond [S1-C9 = 1.7646 (17) Å] is significantly shorter than the Csp 3 -S bond [S1-C8 = 1.7947 (17) Å]. These values compare with the values of 1.772 (3) and 1.801 (2) Å reported in the literature (Gao et al., 2007).
The crystal structure is stabilized by inter molecular C-H···O and C-H···N hydrogen bonding, and C-H···π interactions (Table 1).

Experimental
The title compound was synthesized by the reaction of from the 4,6-dimethylpyrimidin-2-thiol with 2-chlorophenyl carbamic chloride in the refluxing ethanol. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform/acetone.

Refinement
The H atoms attached to N atom was located in a different density map and the atomic coordinates allowed to refine freely.