(4-Chloro-3-nitrobenzoato)triphenyltin(IV)

In the title compound, [Sn(C6H5)3(C7H3ClNO4)], the four-coordinate SnIV atom exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. The conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(5) ring. The aromatic ring of the 4-chloro-3-nitrobenzoate ligand makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12)° with the three phenyl ligands. The O atoms of the nitro group are disordered over two sets of sites in a 0.817 (5):0.183 (5) ratio. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds into chains running parallel to [010].

In the title compound, [Sn(C 6 H 5 ) 3 (C 7 H 3 ClNO 4 )], the fourcoordinate Sn IV atom exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. The conformation is stabilized by an intramolecular C-HÁ Á ÁO hydrogen bond, which generates an S(5) ring. The aromatic ring of the 4-chloro-3-nitrobenzoate ligand makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12) with the three phenyl ligands. The O atoms of the nitro group are disordered over two sets of sites in a 0.817 (5):0.183 (5) ratio. In the crystal, molecules are linked via intermolecular C-HÁ Á ÁO hydrogen bonds into chains running parallel to [010].

Related literature
For general background to and the metal coordination environment of the title complex, see: Win et al. (2008Win et al. ( , 2010Win et al. ( , 2011a. For reference bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Comment
The study of triphenyltin(IV) carboxylate complexes have received tremendous attention due to their structural diversity for which their structure could be monomeric or polymeric although the reaction was carried out in 1:1 molar ratio between the triphenyltin(IV) hydroxide and the respective acid (Win et al., 2008;2010;2011a,b). In this study, the structure of the title complex is similar to (2-chloro-4-nitrobenzoato)(methanol) triphenyltin(IV) (Win et al., 2011a). The only exceptions are that the methanol is not part of the crystal structure and the 2-chloro-4-nitrobenzoic acid is substituted with 4-chloro-3-nitrobenzoic acid.

Refinement
All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93 Å and U iso (H) = 1.2 U eq (C).
Oxygen atoms (O3/O4) of the nitro group are disordered over two positions with refined site-occupancies of 0.817 (5) and 0.183 (5). The highest residual electron density peak and the deepest hole are located at 0.79 and 0.71 Å from atom Sn1, respectively.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 )