Chlorido{4-cyclohexyl-1-[1-(pyridin-2-yl-κN)ethylidene]thiosemicarbazidato-κ2 N 1,S}diphenyltin(IV)

The distorted octahedral geometry about the SnIV atom in the title compound, [Sn(C6H5)2(C14H19N4S)Cl], is defined by the N,N,S-tridentate Schiff base ligand, two mutually trans ipso-C atoms of the Sn-bound phenyl groups, and the Cl atom which is trans to the azo N atom. The two five-membered chelate rings and pyridyl ring are almost coplanar with the dihedral angle between the outer five-membered chelate and pyridine rings being 5.39 (8)°. Centrosymmetric dimers feature in the crystal packing mediated by N—H⋯S hydrogen bonds, leading to eight-membered {⋯HNCS}2 synthons. The dimeric aggregates are connected into a three-dimensional architecture by C—H⋯Cl and C—H⋯π interactions, as well as π–π interactions occurring between centrosymmetrically related pyridine rings [centroid–centroid distance = 3.6322 (13) Å].

The distorted octahedral geometry about the Sn IV atom in the title compound, [Sn(C 6 H 5 ) 2 (C 14 H 19 N 4 S)Cl], is defined by the N,N,S-tridentate Schiff base ligand, two mutually trans ipso-C atoms of the Sn-bound phenyl groups, and the Cl atom which is trans to the azo N atom. The two five-membered chelate rings and pyridyl ring are almost coplanar with the dihedral angle between the outer five-membered chelate and pyridine rings being 5.39 (8) . Centrosymmetric dimers feature in the crystal packing mediated by N-HÁ Á ÁS hydrogen bonds, leading to eight-membered {Á Á ÁHNCS} 2 synthons. The dimeric aggregates are connected into a three-dimensional architecture by C-HÁ Á ÁCl and C-HÁ Á Á interactions, as well asinteractions occurring between centrosymmetrically related pyridine rings [centroid-centroid distance = 3.6322 (13) Å ].

Related literature
For the crystal structure of the dichloridophenyl analogue, see: Salam et al. (2010). For a related structure, see: de Sousa et al. (2007).
We thank MOSTI (grant No. 06-01-09-SF0046) and the Universiti Malaysia Sarawak for supporting this study. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3). Sousa et al., 2007). Both five-membered rings are essentially planar with the r.m.s. deviations being 0.111 and 0.020 Å for the SnSN 2 C and SnN 2 C 2 rings, respectively; the former ring has a small twist about the Sn-S1 bond with Sn and S1 atoms lying 0.068 (1) and -0.081 (1) Å out of the least-squares plane, respectively. The dihedral angle between the chelate rings is 3.42 (7)° and those between each of these and the pyridyl ring are 5.39 (8) and 2.29 (9)°, respectively, indicating an essentially planar arrangement of fused rings. Finally, the Sn-bound benzene rings are almost parallel with the dihedral angle being 8.72 (12)°.
Recrystallization from a chloroform/methanol (1/1) mixture gave small dark-yellow prisms embedded in large lightyellow blocks. A small light-yellow specimen was cut from a light-yellow block for the diffraction measurements. The dark-yellow specimen proved to be (C 6 H 5 )Sn(C 14 H 19 N 4 S)Cl 2 from unit cell determination (Salam et al., 2010).

Figure 1
The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.