Dichlorido{1-[N-(5-chloro-2-oxidophenyl)carboximidoyl]naphthalen-2-olato-κ3 O,N,O′}(methanol-κO)tin(IV)

In the title complex, [Sn(C17H10ClNO2)Cl2(CH3OH)], the SnIV atom features a distorted octahedral geometry defined by the O,N,O′-donors of the dianion, two Cl atoms and the methanol O atom. The six-membered chelate ring has a half-chair conformation with the Sn atom lying 0.449 (4) Å out of the plane defined by the remaining atoms (r.m.s. deviation = 0.0238 Å). Supramolecular helical chains along [100], mediated by O—H⋯O hydrogen bonds, feature in the crystal packing. Chains are linked by C—H⋯O, C—H⋯Cl and π–π [centroid–centroid distance = 3.598 (2) Å] interactions.

In the title complex, [Sn(C 17 H 10 ClNO 2 )Cl 2 (CH 3 OH)], the Sn IV atom features a distorted octahedral geometry defined by the O,N,O 0 -donors of the dianion, two Cl atoms and the methanol O atom. The six-membered chelate ring has a halfchair conformation with the Sn atom lying 0.449 (4) Å out of the plane defined by the remaining atoms (r.m.s. deviation = 0.0238 Å ). Supramolecular helical chains along [100], mediated by O-HÁ Á ÁO hydrogen bonds, feature in the crystal packing. Chains are linked by C-HÁ Á ÁO, C-HÁ Á ÁCl and -[centroid-centroid distance = 3.598 (2) Å ] interactions.

Related literature
For background to related Sn(IV) Schiff base compounds and a closely related structure, see: Pettinari et al. (2001). For specialized crystallization techniques, see: Harrowfield et al. (1996).
In (I), Fig. 1, the Sn IV atom is coordinated by the tridentate, dinegative Schiff base, two Cl atoms and the O atom of a methanol molecule to define a distorted octahedral geometry within a Cl 2 NO 3 donor set, Table 1. The five-membered chelate ring is approximately planar with a r.m.s. deviation of 0.058 Å. By contrast, the six-membered chelate ring has a half-chair conformation as the Sn atom lies 0.449 (4) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.024 Å). The Sn-Cl2 bond length is significantly longer than that of Sn-Cl1, a difference which is correlated with the Cl2 atom being trans to the methanol-O atom.

Experimental
A solution of 2-amino-4-chlorophenol (10 mmol) in EtOH (30 ml) was added drop-wise to the solution of 2-hydroxy-1naphthaldehyde (10 mmol) in EtOH (20 ml). The mixture was refluxed for 5 h. The yellow precipitate was removed by filtration and recrystallized from MeOH solution. The ligand (0.5 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and tin(IV) chloride (0.5 mmol) in the other. Methanol was then added to fill both arms, the tube sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature.
After three weeks crystals deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air-dried. Yield: 68%. M.pt.: 571 K (dec.).

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95 to 0.98 Å and with U iso (H) = 1.2 to 1.5U eq (C)] and were included in the refinement in the riding model approximation. The hydroxy H-atom was located in a difference Fourier map and was refined with a distance restraint of O-H = 0.84±0.01 Å; U iso was refined. The (0 1 1) reflection was omitted from the final refinement owing to poor agreement.

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.  A view in projection down the a axis of the unit-cell contents of (I). The C-H···O, C-H···Cl and π-π interactions are shown as orange, blue and purple dashed lines.

Dichlorido{1-[N-(5-chloro-2-oxidophenyl)carboximidoyl]naphthalen-2-olato-κ 3 O,N,O′}(methanol-κO)tin(IV)
Crystal data  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 cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. 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 R-factors(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 Sn 0.39500 (