Aquachlorido{2-[2-(cyclohexylcarbamothioyl-κS)hydrazinylidene-κN 1]propanoato(2−)}phenyltin(IV)

In the title organotin compound, [Sn(C6H5)(C10H15N3O2S)Cl(H2O)], the Sn atom is coordinated by the S, O, and imine N atoms of the dinegative tridentate ligand, a chloride ligand, the ipso-C atom of a phenyl ligand and by a water molecule in a distorted octahedral coordination environment. Coordinated water molecules link the organotin molecules by forming O—H⋯O hydrogen bonds with both carbonyl and carboxylate O atoms, leading to 12-membered {⋯OCO⋯HOH⋯}2 synthons. This results in the formation of supramolecular chains along the c axis. The chains pack in the ac plane and stack along the b axis with links between layers afforded by N—H⋯Cl hydrogen bonds.


Related literature
For background to the biological activity of tin/organotin compounds, see: Gielen & Tiekink (2005). For related studies on organotin compounds, see: Affan et al. (2009)

Comment
Organotin compounds continue to attract considerable owing to the wide variety of biological properties (Gielen & Tiekink, 2005). In continuation of our work in this area Zukerman-Schpector et al., 2009;Affan et al. 2010), the title organotin compound, (I), was synthesized and structurally characterized.
The Sn atom is coordinated via the S, O, and imine-N atoms of the dinegative tridentate ligand, thereby forming two planar five-membered chelate rings. The distorted CClNO 2 S octahedral coordination geometry is completed by an aqua ligand, a chloride atom, and the ipso-C atom of the phenyl group, Table 1. The greatest distortion from the ideal octahedral geometry is found in the O1-Sn-S1 angle of 153.73 (6) °, a feature which arises due to the restricted bite distances of the chelate rings.
The most notable feature of the crystal packing is the formation of O-H···O and N-H···Cl hydrogen bonds, Table 1

Experimental
The pyruvic acid cyclohexyl thiosemicarbazone ligand (0.243 g, 1.0 mmol) was dissolved in dry methanol (10 ml) in a Schlenk apparatus under a purified dry nitrogen atmosphere. Phenyltin(IV) trichloride (0.302 g, 1.0 mmol) dissolved in absolute methanol (10 ml) was added drop-wise. The resulting mixture was refluxed for 5 h. The resulting solid was filtered and dried in vacuo over silica gel. Re-crystallization was by slow evaporation of its methanol solution yielded light-brown crystals of (I).  Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.  Crystal data [Sn(C 6

Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The 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 > 2σ(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.