(Methanol-κO)(2-methyl-3-nitrobenzoato-κO)triphenyltin(IV)

The five-coordinate Sn atom in the title compound, [Sn(C6H5)3(C8H6NO4)(CH3OH)], exists in a trans-C3SnO2 trigonal-bipyramidal coordination polyhedron of which the O atoms of the methanol molecule and carboxylate group occupy the apical sites. In the crystal, adjacent molecules are linked by intermolecular O—H⋯O interactions, generating a helical hydrogen-bonded chain running along the b axis.

The five-coordinate Sn atom in the title compound, [Sn(C 6 H 5 ) 3 (C 8 H 6 NO 4 )(CH 3 OH)], exists in a trans-C 3 SnO 2 trigonal-bipyramidal coordination polyhedron of which the O atoms of the methanol molecule and carboxylate group occupy the apical sites. In the crystal, adjacent molecules are linked by intermolecular O-HÁ Á ÁO interactions, generating a helical hydrogen-bonded chain running along the b axis.
The condensation of triphenyltin hydroxide and 2-methyl-3-nitrobenzoic acid in methanol gave the expected product as a methanol-coordinated compound (Scheme I, Fig. 1). The five-coordinate tin atom in Sn(C 6 H 5 ) 3 (CH 4 O)(C 8 H 6 NO 4 ) exists in a trans-C 3 SnO 2 trigonal bipyramidal coordination polyhedron for which the O atoms of the methanol and carboxylate occupy the apical sites. As found in the other examples, the tin-oxygen alcohol bond is longer than the tin-oxygen carboxylate bond (Table 1). However, the C 3 Sn girdle is nearly planar [Σ angles 358.6 (5) °]. Adjacent molecules are linked by an O-H···O interaction to generate a helical hydrogen-bonded chain running along the b-axis of the monoclinic unit cell (Fig. 2, Table 2).

Experimental
Triphenyltin hydroxide (0.73 g, 2 mmol) and 2-methyl-3-nitrobenzoic acid (0.36 g, 2 mmole) were heated in methanol (50 ml) for an hour. The mixture was filtered to give a clear yellow solution. The filtrate was set aside for the formation of crystals, which were isolated in 80% yield; m.p. 394.5 K. CHN&Sn elemental analysis for C 27

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).
The methanol H-atom was located in a difference Fourier map, and was refined isotropically with a distance restraint The final difference Fourier map had two peaks in the vicinity of Sn1. Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.    (17 122 (4) C16-C17-C18 120.0 (6) O4-N1-O3