Data collection: CrysAlis PRO (Agilent, 2011 ^▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ^▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ^▶); molecular graphics: X-SEED (Barbour, 2001 ^▶) and DIAMOND (Brandenburg, 2006 ^▶); software used to prepare material for publication: publCIF (Westrip, 2010 ^▶).

The synthesis and crystal structure of the title compound was determined in connection with recent structural studies of organotin chlorido derivatives of thiosemicarbazones (Salam et al., 2010).

The Sn atom in the title compound, Fig. 1, exists within a six atom C₂ClN₂S donor set defined by the tridentate monodeprotonated 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, Table 1. There are distortions from the ideal octahedral geometry which are ascribed to the restricted bite angles formed by the Schiff base ligand which result in an angle of 145.90 (5)° for the nominally trans S1—–Sn—–N1 angle. The disposition of donor atoms resembles that found in the structure of the N-4-morpholinyl derivative (de 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 SnSN₂C and SnN₂C₂ 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)°.

The most significant feature in the crystal packing of the title compound is the formation of centrosymmetric dimers via N—H···S hydrogen bonds that lead to flat, eight-membered {···HNCS}₂ synthons, Table 1. The dimeric aggregates are connected into a three dimensional architecture by C—H···Cl and C—H···π interactions, Table 1, as well as π—π interactions occurring between centrosymmetrically related pyridyl rings [centroid···centroid distance = 3.6322 (13) Å for symmetry operation: 1 - x, 1 - y, 2 - z], Fig. 2.

2-Acetylpyridine-N-cyclohexylthiosemicarbazone (0.28 g, 1 mmol) was dissolved in methanol (10 ml) in a Schlenk flask under a nitrogen atmosphere. Diphenyltin(IV) dichloride (0.34 g, 1 mmol) dissolved in methanol (10 ml) was added. The yellow solution was refluxed for 4 h. Slow evaporation of the solvent gave a yellow compound (0.423 g). Recrystallization from a chloroform/methanol (1/1) mixture gave small dark-yellow prisms embedded in large light-yellow blocks. A small light-yellow specimen was cut from a light-yellow block for the diffraction measurements. The dark-yellow specimen proved to be (C₆H₅)Sn(C₁₄H₁₉N₄S)Cl₂ from unit cell determination (Salam et al., 2010).

Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95 to 1.00 Å, U_iso(H) = 1.2 to 1.5U_eq(C)] and were included in the refinement in the riding model approximation. The amino H-atom was similarly treated [N—H = 0.88 Å with U_iso(H) = 1.2U_eq(N)]. Owing to poor agreement, several reflections, i.e. (2 6 8), (2 5 8), (2 6 7) and (2 4 8), were omitted from the final refinement.

Cg1 is the centroid of the C7–C12 ring.

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+2; (iii) x, y+1, z; (iv) −x+1, −y+1, −z+2.