N-(2-Chlorobenzoyl)-N′-(3-pyridyl)thiourea

In the molecule of the title compound, C13H10ClN3OS, the dihedral angles between the plane through the thiourea group and the pyridine and benzene rings are 53.08 (3) and 87.12 (3)°, respectively. The molecules are linked by intermolecular N—H⋯N hydrogen-bonding interactions to form a supramolecular chain structure along the a axis. An intramolecular N—H⋯O hydrogen bond is also present.

In the molecule of the title compound, C 13 H 10 ClN 3 OS, the dihedral angles between the plane through the thiourea group and the pyridine and benzene rings are 53.08 (3) and 87.12 (3) , respectively. The molecules are linked by intermolecular N-HÁ Á ÁN hydrogen-bonding interactions to form a supramolecular chain structure along the a axis. An intramolecular N-HÁ Á ÁO hydrogen bond is also present. = 112.532 (4) V = 670.9 (5) Å 3 Z = 2 Mo K radiation = 0.43 mm À1 T = 298 (2) K 0.32 Â 0.11 Â 0.07 mm
It has been shown that the redox properties of thiourea are markedly influenced by electronic factors (Guillon et al., 1996), and the biological activity of thiourea derivatives has also been reported in the literature (Teoh et al., 1999;Campo et al., 2002). However, the study of S···H interactions may have fundamental importance in biochemical research due to the fact that living systems contain several important sulfur-containing molecules, such as the aminoacids cysteine and methionine (Krepps et al., 2001). Related to the biological relevance of S···H interactions, Uckum and coworkers have recently reported a structural study of a series of thiourea compounds (Venkatachalam et al., 2004). Here we report the synthesis and crystal structure of a new benzoylthiourea derivative, N-(o-chloro)benzoyl-N'-(3-pyridyl)thiourea. The molecular structure of the title compound is shown in Figure 1.
The dihedral angles formed by the plane through the thiourea group and the pyridine and benzene rings of 53.08 (3) and 87.12 (3)°, respectively. The molecular conformation is stabilized by an intramolecular N-H···O hydrogen bonding interaction (Table 1), forming a planar six-membered ring. In contrast to other thiourea compounds, the H1···S1 separation is 2.662 (2) Å, indicating that S1 is not involved in hydrogen bonding. This situation is similar to that found in the structure

Refinement
H atoms were treated as riding atoms with C-H = 0.93 Å, N-H = 0.86 Å, and U iso (H) = 1.2 U eq (C, N). Fig. 1. The molecule structure of the title compound with atom numbering. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

N-(2-Chlorobenzoyl)-N'-(3-pyridyl)thiourea
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