2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(2-methylphenyl)acetamide

In the title compound, C13H15NOS, the plane of the pyrimidine ring makes a dihedral angle of 54.73 (9)° with that of the o-tolyl ring. The molecule adopts an extended conformation, which is evident from the C—C(=O)—N—Car (ar = aromatic) torsion angle of 178.42 (15)°. In the crystal, molecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds, with the O atom accepting three such interactions, forming sheets parallel to (100).

In the title compound, C 13 H 15 NOS, the plane of the pyrimidine ring makes a dihedral angle of 54.73 (9) with that of the o-tolyl ring. The molecule adopts an extended conformation, which is evident from the C-C( O)-N-C ar (ar = aromatic) torsion angle of 178.42 (15) . In the crystal, molecules are linked via pairs of N-HÁ Á ÁN hydrogen bonds, forming inversion dimers with an R 2 2 (8) ring motif. The dimers are linked by N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds, with the O atom accepting three such interactions, forming sheets parallel to (100).
In the crystal, molecules are linked by pairs of N-H···N hydrogen bonds forming inversion dimers and enclosing R 2 2 (8) ring motifs (Table 1 and Fig. 2). The dimers are linked via trifurcated N-H···O and C-H···O hydrogen bonds involving atom O1 as an acceptor (Table 1 and Fig. 2) forming forming sheets parallel to (100).

Experimental
The title compound was synthesized according to the reported procedure (Xu et al., 2010). To a solution of 4,6-diaminopyrimidine-2-thiol (0.5 g; 3.52 mmol) in 25 ml of ethanol was added potassium hydroxide(0.2g; 3.52 mmol) and the mixture was refluxed for 30 mins. Then 3.52 mmol of 2-chloro-N-phenylacetamide was added and the mixture refluxed for 1-4 h. At the end of the reaction, monitored by TLC, ethanol was evaporated in vacuo and cold water was added. The precipitate formed was filtered and dried to give the title compound as a crystalline powder (Yield of 88-96%). Block-like colourless crystals were obtained by slow evaporation of a solution in methanol at room temperature.

Refinement
The NH and C-bound H atoms were placed in idealized positions and refined using a riding model: N-H = 0.86 Å, C-H = 0.93, 0.97 and 0.96 Å for CH, CH 2 and CH 3 H atoms, respectively, with U iso (H) = 1.5U eq (C-methyl) and = 1.2U eq (N,C) for other H atoms.  The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.  The crystal packing of the title compound, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details; the C and N-bound H-atoms not involved in hydrogen bonding have been omitted for clarity). where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.25 e Å −3 Δρ min = −0.23 e Å −3 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq C1 0.44402 (7