(Dimethyl sulfoxide-κO)trimeth­yl(2-methyl-3,5-dinitro­benzoato-κO 1)tin(IV)

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

doi:10.1107/S1600536811022240

. 2011 Jun 18;67(Pt 7):m923. doi: 10.1107/S1600536811022240

(Dimethyl sulfoxide-κO)trimethyl(2-methyl-3,5-dinitrobenzoato-κO ¹)tin(IV)

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

PMCID: PMC3151753 PMID: 21836907

Abstract

In the title mononuclear complex, [Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)], the Sn^IV ion is coordinated by three methyl groups in the equatorial plane, and by an O atom from a 2-methyl-3,5-dinitrobenzoate ligand and a dimethyl sulfoxide ligand in the axial sites, to form a slightly distorted trigonal–bipyramidal environment. The O atoms of one of the nitro groups are disordered over two sets of sites, with refined occupancies of 0.55 (4) and 0.45 (4). The closest intermolecular interaction is a weak C—H⋯O hydrogen bond.

Related literature

For the applications of trimethytin complexes, see: Gielen et al. (2005 ▶); Gielen (2002 ▶); Hameed et al. (2009 ▶); Ashhad et al. (2005 ▶). For the structure of a trimethyltin complex with a 2-methylbenzene-3-carboxylate ligand, see: Danish et al. (2010 ▶). For the structure of a triphenyltin complex with 2-methyl-3,5-dinitrobenzene carboxylate and methanol ligands, see: Danish et al. (2011 ▶).

Experimental

Crystal data

[Sn(CH₃)₃(C₇H₅N₂O₆)(C₂H₆OS)]
M _r = 467.06
Monoclinic,
a = 9.6180 (19) Å
b = 12.971 (3) Å
c = 15.612 (3) Å
β = 102.98 (3)°
V = 1897.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 293 K
0.42 × 0.24 × 0.08 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.753, T _max = 0.890
4755 measured reflections
4500 independent reflections
2464 reflections with I > 2σ(I)
R _int = 0.030
3 standard reflections every 200 reflections intensity decay: 0.2%

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.144
S = 1.01
4500 reflections
242 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 1.55 e Å⁻³
Δρ_min = −1.86 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 datablock(s) I, global. DOI: 10.1107/S1600536811022240/lh5258sup1.cif

e-67-0m923-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022240/lh5258Isup2.hkl

e-67-0m923-Isup2.hkl^{(220.5KB, 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
C11—H11C⋯O3ⁱ	0.96	2.59	3.509 (15)	162

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Organotin carboxylates are extensively studied bexcause of their potential diversified biological applications. Trimethyltin carboxylates find use as antifungal (Gielen et al., 2005; Gielen, 2002) and antibacterial agents (Hameed et al., 2009; Ashhad et al., 2005). The title compound is part of our continued effort in this area (Danish et al., 2010, 2011). The structure of the title compound is composed of mononuclear molecules in which an Sn atom is coordinated by three methyl C atoms, one carboxylato O atom donated by a 2-methyl-3,5-dinitrobenzenecarboxylate ligand and an O atom from a DMSO ligand forming slightly distorted trigonal bipyramidal environment. The methyl C atoms form the equatorial plane. The Sn atom is displaced by 0.1082 (2) Å from the plane towards the carboxylate O atom. The latter and the DMSO O atom are in the axial sites. The Sn—C bond lengths range from 2.097 (3) to 2.121 (3) Å and are close to those reported earlier in the structures of other trimethyltin complexes (e.g. Danish et al., 2010). The 2-methyl-3,5-dintro-benzenecarboxylate ligand molecule is essentially planar with an r.m.s. deviation of 0.0041 (1) Å. The O atoms of one of the nitro groups show positional disorder with a major component occupancy of 0.55 (4). The other nitro group forms a dihedral angle of 5.9 (2)° with the methylbenzene ring. The carboxylate group donates a single O atom to the Sn atom. The observed Sn—O bond length of 2.106 (3) Å is typical (e.g. Danish et al., 2010, 2011). The closest intermolecular interaction is a weak C—H···O hydrogen bond.

Experimental

The sodium salt of 3,5-dinitro-o-toluic acid (2.48 g, 0.01 mol) was suspended in 25 ml of dry chloroform contained in a 100 ml round-bottom flask; trimethyltin chloride (2.00 g, 0.01 mol) was dissolved in 25 ml of dry chloroform was then added dropwise with constant stirring at room temperature. The reaction mixture was then refluxed in chloroform for 6 h and then brought to room temperature. Filtration was carried out to remove sodium chloride formed during the reaction. After evaporation, the solid mass was recrystallized from DMSO. m.p. 395 K; yield 88%.