(Methanol-κO)(2-methyl-3,5-dinitro­benzoato-κO)triphenyl­tin(IV)

Muhammad Danish; Sabiha Ghafoor; Nazir Ahmad; Wojciech Starosta; Janusz Leciejewicz

doi:10.1107/S1600536811011184

. 2011 Apr 7;67(Pt 5):m519. doi: 10.1107/S1600536811011184

(Methanol-κO)(2-methyl-3,5-dinitrobenzoato-κO)triphenyltin(IV)

Muhammad Danish ^a,^*, Sabiha Ghafoor ^b, Nazir Ahmad ^b, Wojciech Starosta ^c, Janusz Leciejewicz ^c

PMCID: PMC3089075 PMID: 21754262

Abstract

In the title complex, [Sn(C₆H₅)₃(C₈H₅N₂O₆)(CH₃OH)], the Sn(IV) ion is coordinated in a slightly distorted trigonal–bipyramidal geometry by three phenyl ligands in the equatorial plane and by a 2-methyl-3,5-dinitrobenzenecarboxylato ligand and a methanol ligand at the apical sites. In the crystal, complex molecules are linked via intermolecular O—H⋯O hydrogen bonds, forming chains along [100].

Related literature

For the crystal structures of two triphenyltin complexes with a 2,3-dinitrobenzoate ligand, see: Azir-ur-Rehman et al. (2006 ▶); Win et al. (2006 ▶). For the structure of a tin complex with a 2-methylbenzoate ligand, see: Danish et al. (2010) ▶. For applications of organotin compounds, see: Reisi et al. (2006 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₈H₅N₂O₆)(CH₄O)]
M _r = 607.17
Monoclinic,
a = 8.0597 (16) Å
b = 20.094 (4) Å
c = 16.022 (3) Å
β = 95.29 (3)°
V = 2583.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 293 K
0.31 × 0.23 × 0.07 mm

Data collection

Kuma KM4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008) ▶ T _min = 0.842, T _max = 0.930
6387 measured reflections
6141 independent reflections
3440 reflections with I > 2σ(I)
R _int = 0.024
3 standard reflections every 200 reflections intensity decay: 7.5%

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.133
S = 1.04
6141 reflections
340 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Data collection: KM-4 Software (Kuma, 1996 ▶); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011184/lh5223sup1.cif

e-67-0m519-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011184/lh5223Isup2.hkl

e-67-0m519-Isup2.hkl^{(300.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O51—H51⋯O12ⁱ	0.81 (2)	1.91 (4)	2.654 (6)	153 (8)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Triphenyltin hydroxide, chloride and acetate compounds are used against a number of fungal diseases to control the attacks of fungi on potato, sugar beat, onion and rice. They are used to protect against tropical diseases in coffee, cocoa and as antifouling agents in paint coating in ships (Reisi et al. 2006). The title compound is a continuation of our research invovling the synthesis of new organotin compounds of potential biological activity (Danish et al., 2010).

The molecular structure of the title compound is shown in Fig.1. The structure contains discrete molecules. The central Sn atom is coordinated by three phenyl ligands, a dinitrotoluene carboxylate ligand and a methanol ligand. Three phenyl ligands coordinate the Sn atom through Sn—C bonds whose lengths fall in the narrow range of 2.122((5)Å to 2.132 (5) Å, which was earlier observed in triphenyl tin complexes (Azir-ur-Rehman et al., 2006; Win et al., 2006). The coordinating C atoms form an equatorial plane of a trigonal bipyramid. The Sn atom deviates from this plane by 0.0666 (2) Å. The benzene rings as expected are essentially planar with r.m.s. deviations of 0.0026 (1), 0.0100 (1) and 0.0070 (1)Å and form dihedral angles of 49.8 (2), 57.6 (2) and 5.5 (1)° with the equatorial plane. The dinitrotoluene carboxylate ligand chelates the Sn atom using a single carboxylato O atom, which forms one apex of the coordination bipyramid. The second carboxylato O atom is not coordinated. The Sn—O bond length is 2.162 (3) Å, which is characteristic (Danish et al., 2010). The toluene group is essentially planar [r.m.s. 0.0154 (2) Å] and forms dihedral angles of 40.9 (2) and 5.8 (1)° with nitro groups, N11/O13/O14 and N12/O15/O16 respectively. The dihedral angle between the carboxylate C17/O11/O12 group and the toluene ring is 52.3 (2)°. The methanol hydroxy O51 atom is the apical site with with an Sn—O bond of 2.393 (3) Å. The methanol ligand originates from the solvent used in the course of chemical synthesis. In the crystal, molecules are linked by hydrogen bonds in which the methanol hydroxyl group act as donors and the unccordinated carboxylato O12 atoms acts as an acceptor to form chains propagating along the a axis (Fig. 2).

Experimental

0.124 g.(0.0005 mol) of sodium 3,5-dinitro-toluate and 0.192 g.(0.0005 mol) of triphenyltin chloride were suspended in dry methanol and refluxed for six hours. Sodium chloride, which was formed, was removed by filtration. The solid obtained from the concentration of the filtrate was repeatedly crystallized from chloroform until pale yellow single-crystal plates were found. M.p = 369 K. Yield 80%.