4-Chloro-N-[N-(6-methyl-2-pyridyl)carbamothioyl]benzamide

In the title compound, C14H12ClN3OS, the short exocyclic N—C bond lengths indicate resonance in the thiourea part of the molecule. The title compound is stabilized by an intramolecular N—H⋯N hydrogen bond, which results in the formation of a six-membered ring. In addition, it shows a synperiplanar conformation between the thiocarbonyl group and the pyridine group. Intermolecular N—H⋯S and C—H⋯O interactions are also present.

In the title compound, C 14 H 12 ClN 3 OS, the short exocyclic N-C bond lengths indicate resonance in the thiourea part of the molecule. The title compound is stabilized by an intramolecular N-HÁ Á ÁN hydrogen bond, which results in the formation of a six-membered ring. In addition, it shows a synperiplanar conformation between the thiocarbonyl group and the pyridine group. Intermolecular N-HÁ Á ÁS and C-HÁ Á ÁO interactions are also present.

Data collection
Our team focused on the synthesis, characterization, crystal structure, thermal behavior and antimicrobial activity of new thiourea derivatives (Mansuroğlu et al., 2008;Arslan et al., 2003aArslan et al., , 2003bArslan et al., , 2006aArslan et al., , 2006bArslan et al., , 2007Uğur et al., 2006;Özpozan et al., 2000). In this article, we report the preparation and characterization of a novel thiourea compound, 4-chloro-N-(6methylpyridin-2-yl-carbamothioyl)benzamide (I), and its crystal structure. The title compound was purified by re-crystallization from ethanol:dichloromethane mixture (1:2) and characterized by elemental analysis. The analytical data is consistent with the proposed structure given in Scheme 1.
The molecular structure and packing diagram are depicted in Figure 1 and 2, respectively. The bond lengths and angles in the thiourea moiety are typical for thiourea derivatives; the C8-S1 and C7-O1 bonds both show a typical double-bond character with 1.655 (5) and 1.203 (6) Å, respectively. The short bond lengths of the N1-C7, 1.395 (7); N1-C8, 1.376 (6) and N2-C8, 1.364 (6) Å bonds indicate partial double bond character. These results can be explained by the existence of resonance in this part of the molecule. The other C-N bond length is within the expected range.
The crystal packing is shown in Fig. 2 The compound was prepared with a procedure similar to that reported in the literature (Arslan et al., 2003b(Arslan et al., , 2006a. A solution of 4-chloro-benzoyl chloride (0.01 mol) in acetone (50 cm 3 ) was added dropwise to a suspension of potassium thiocyanate (0.01 mol) in acetone (30 cm 3 ). The reaction mixture was heated under reflux for 30 min, and then cooled to room temperature. A solution of 6-methylpyridin-2-amine (0.01 mol) in acetone (10 cm 3 ) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 cm 3 ) was added to the solution, which was then filtered. The solid product was washed with water and purifed by recrystalization from an ethanol:dichloromethane mixture (1:2). Anal.

4-Chloro-N-[N-(6-methyl-2-pyridyl)carbamothioyl]benzamide
Crystal data  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 > σ(F 2 ) is used only for calculating Rfactors(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  (8)