(N-Benzoyl-N′-phenylthiourea-κS)chlorido(η4-1,5-cyclooctadiene)rhodium(I)

The title compound, [RhCl(C8H12)(C14H12N2OS)], is a rhodium(I) derivative with a functionalized thiourea ligand. Despite the presence of several heteroatoms, the thiourea ligand coordinates only in a monodentate fashion via the S atom. The geometry of the coordination sphere is approximately square planar about the RhI atom, with two bonds to the π-electrons of the 1,5-cyclooctadiene ligand, one bond to the Cl− ligand and one bond to the S atom of the thiourea ligand. The molecular structure is stabilized by intramolecular N—H⋯O and N—H⋯Cl hydrogen bonding. Intermolecular N—H⋯O hydrogen-bonding interactions lead to the formation of layers extending parallel to (011).

The title compound, [RhCl(C 8 H 12 )(C 14 H 12 N 2 OS)], is a rhodium(I) derivative with a functionalized thiourea ligand. Despite the presence of several heteroatoms, the thiourea ligand coordinates only in a monodentate fashion via the S atom. The geometry of the coordination sphere is approximately square planar about the Rh I atom, with two bonds to the -electrons of the 1,5-cyclooctadiene ligand, one bond to the Cl À ligand and one bond to the S atom of the thiourea ligand. The molecular structure is stabilized by intramolecular N-HÁ Á ÁO and N-HÁ Á ÁCl hydrogen bonding. Intermolecular N-HÁ Á ÁO hydrogen-bonding interactions lead to the formation of layers extending parallel to (011).

Experimental
Crystal data [RhCl(C 8 H 12 Cauzzi et al. (1995), Leipoldt et al. (1977Leipoldt et al. ( , 1980, Roodt et al. (2003), Steyl et al. (2004. The title compound, [Rh(C 8 H 12 )(C 14 H 12 N 2 OS)Cl], features a functionalized thiourea ligand, which has been shown by previous authors (Kemp et al., 1996(Kemp et al., , 1997Roodt et al., 1994)) to have the ability to co-ordinate in a bidentate fashion as many other hetero-atom bidentate ligands do, including β-diketones and derivatives. However, in the title compound this ligand only co-ordinates in a monodentate fashion via the sulfur atom to the rhodium atom.
The rhodium(I) complex is found to have a slightly distorted square-planar coordination about the rhodium centre with a chlorine atom cis to the sulfur atom ( Fig. 1). The packing of the complex is well established by the presence of intra-and intermolecular hydrogen bonding. Intramolecular hydrogen bonding occurs between O1 and N2 with a distance of 1.99 Å. The same observation was made with the free ligand (Yamin & Yusof, 2003). This interaction suggests the prefered orientation of the free ligand to have its oxygen trans to the sulfur atom and it clearly translates to the orientation found in the title compound. Hydrogen bonding was also observed between the nitrogen atom N1 and the chlorine atom Cl1, with a distance of 2.47 Å, which added onto the effect of stabilizing the orientation found in the title compound. Since two molecules are orientated about an inversion centre, the oxygen atom O1 as well as the nitrogen atom N2 were found in close approximation to the oxygen atom in the next molecule. As a result, intermolecular hydrogen bonding between the two oxygen atoms as well as between N2 and O1 were established with distances of 2.980 Å and 3.053 Å, respectively. The intermolecular hydrogen bonding leads to a layered assembly of the molecules, extending approximately parallel to (011).
In addition, a vast variety of short contacts via van der Waals interactions are found to be present amongst various atoms.
These short contacts are suspected to be the cause of the distortion found in the cyclo-octadiene ring as six of its atoms are pulled in various directions.

Refinement
The aliphatic as well as aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with U iso (H) = 1.2Ueq(C). The highest residual electron density was located 0.79 Å from C15 and the deepest hole was 0.88 Å from Rh1. supplementary materials sup-2 Figures Fig. 1. : A representation of the title compound, displaying the numbering scheme and displacement ellipsoids at the 50% probability level.