4-(4-Chlorophenyl)-6-(methylsulfanyl)pyrimidin-2-amine

In the title compound, C11H10ClN3S, the dihedral angle between the benzene and pyrimidine rings is 3.99 (4)°. In the crystal, intermolecular N—H⋯N hydrogen bonds link the molecules into ribbons of R 2 2(8) rings parallel to [100]. Weak C—H⋯S contacts connect adjacent ribbons into a two-dimensional undulating layer-like structure extending parallel to (110). The benzene and pyrimidine rings of adjacent molecules have the offset face-to-face π–π stacking interactions in a zigzag fashion along the c axis, with perpendicular ring distances of 3.463 and 3.639 Å, and a dihedral angle between the planes of 3.99 (2)°. The distance between the ring centroids is 4.420 (2) Å.

In the title compound, C 11 H 10 ClN 3 S, the dihedral angle between the benzene and pyrimidine rings is 3.99 (4) . In the crystal, intermolecular N-HÁ Á ÁN hydrogen bonds link the molecules into ribbons of R 2 2 (8) rings parallel to [100]. Weak C-HÁ Á ÁS contacts connect adjacent ribbons into a twodimensional undulating layer-like structure extending parallel to (110). The benzene and pyrimidine rings of adjacent molecules have the offset face-to-facestacking interactions in a zigzag fashion along the c axis, with perpendicular ring distances of 3.463 and 3.639 Å , and a dihedral angle between the planes of 3.99 (2) . The distance between the ring centroids is 4.420 (2) Å .
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).  (Mathews & Asokan, 2007). Meanwhile, these organic compounds can be used as new organic N-donor ligands, which can construct a wide range of coordination polymers with novel architectures and special properties. The selection and synthesis of proper ligands are the most important tasks (Li et al., 2007;Cui & Lan, 2007). Herein, the crystal structure of the title compound is reported. Its synthetic method followed the procedure given by Lin et al., (2008).

Structure Reports Online
In the title compound ( Fig. 1), all atoms are almost in the same plane and the largest distortion from the mean plane being 0.3127Å for C11, atoms S1 and Cl1 being 0.1338 (6) and 0.1251 (5) Å out-of-plane. The two aromatic rings of the molecule make a dihedral angle of 3.99 (4)°.

Experimental
All chemicals used were commercially available. We first got the title compound using the reported method (Lin et al., 2008). After that 1 mmol (0.025 g) 4-(4-Chlorophenyl)-6-(methylthio)pyrimidin-2-amine was dissolved in a mixture of 15 ml methyl cyanide and 5 ml water. Then the solution was stirred for 40 min at room temperature. The solvent was removed gradually for a few weeks and faint yellow crystals for X-ray data collection were obtained by the slow evaporation method.

Refinement
H atoms bonded to C and N atoms were calculated geometrically and allowed to ride on the C and N atoms with distance restraints of C-H = 0.93 Å and N-H = 0.86 Å, with U iso (H) = 1.2U eq (C, N).
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.   about twice as large as those based on F, and R-factors based on ALL data will be even larger.