Trimethyl­ammonium dichlorido­triphenyl­stannate(IV)

Tidiane Diop; Libasse Diop; Jerry P Jasinski; Amanda C Keeley

doi:10.1107/S1600536812038457

. 2012 Sep 19;68(Pt 10):m1279. doi: 10.1107/S1600536812038457

Trimethylammonium dichloridotriphenylstannate(IV)

Tidiane Diop ^a,^*, Libasse Diop ^a, Jerry P Jasinski ^b, Amanda C Keeley ^b

PMCID: PMC3470157 PMID: 23125601

Abstract

In the structure of the title monomeric coordination salt, (C₃H₁₀N)[Sn(C₆H₅)₃Cl₂], the Sn^IV atom is five coordinate, with the SnC₃Cl₂ entity in a trans trigonal–bipyramidal arrangement and the chlorine atoms in apical positions. In the crystal, the cations and anions are connected by N—H⋯Cl hydrogen bonds.

Related literature

For medical applications of tin(IV) compounds, see: Evans & Karpel (1985 ▶); Gielen (2002 ▶); Davies et al. (2008 ▶). For literature on organotin(IV) compounds, see: Chandrasekhar & Baskar (2003 ▶); Samuel et al. (2002 ▶); Nath et al. (2003 ▶). For related structures, see: Ng (1999 ▶, 1995 ▶); Harrison et al. (1978 ▶); Nayek et al. (2010 ▶); Sow et al. (2012 ▶); De Lorentiis et al. (2011 ▶).

Experimental

Crystal data

(C₃H₁₀N)[Sn(C₆H₅)Cl₂]
M _r = 481.01
Monoclinic,
a = 9.2650 (2) Å
b = 15.6882 (4) Å
c = 14.7891 (3) Å
β = 90.941 (2)°
V = 2149.32 (8) Å³
Z = 4
Cu Kα radiation
μ = 11.75 mm⁻¹
T = 173 K
0.34 × 0.22 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.328, T _max = 1.000
13300 measured reflections
4143 independent reflections
3739 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.083
S = 1.06
4143 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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, I-2, New_Global_Publ_Block. DOI: 10.1107/S1600536812038457/pk2438sup1.cif

e-68-m1279-sup1.cif^{(27.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038457/pk2438Isup2.hkl

e-68-m1279-Isup2.hkl^{(203.1KB, 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
N1—H1⋯Cl1ⁱ	0.91	2.21	3.087 (3)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

The interest in synthesis of new organotin(IV) derivatives is related to their applications in different fields (agrochemicals, surface disinfectants and marine antifouling paints) (Evans & Karpel, 1985; Gielen, 2002; Davies et al., 2008) and explains the involvement of many groups in the search for new organotin compounds (Chandrasekhar & Baskar, 2003; Samuel et al., 2002; Nath et al., 2003). Many compounds containing the [SnPh₃Cl₂]^- ion in the trans conformation have been reported (Ng, 1995, 1999; Harrison et al., 1978; Nayek et al., 2010; Sow et al., 2012). In our search for new organotin(IV) compounds we have initiated here the study of the interactions between (CH₃)₃N.HCl and SnPh₃Cl, which led to the title compound. In the [SnPh₃Cl₂]^- anion, the tin atom is located on a centre of inversion and is bonded to two Cl atoms and three phenyl groups giving a trigonal bipyramidal geometry with the chloride atoms in trans-positions (Fig. 1). The sum of the angles at atom Sn by the ipso-carbons [128.08 (12)°, 113.70 (12)°, 117.83 (12)°] is 359.61°. The corresponding axial Cl₁—Sn—Cl₂ angle is 171.62 (3)°, indicating a slight deviation from linearity. The Sn—C bond distances (2.135 (3) Å, 2.142 (3) Å and 2.151 (3) Å) are similar to those reported for bis(triphenylphosphanylidene)iminium dichloridotriphenylstannate(IV) (2.134 (3) Å, 2.1476 (19) Å and 2.1476 (19) Å) (De Lorentiis et al., 2011). The two axial Sn—Cl distances, [Sn—Cl 2.5227 (7) Å and 2.6983 (8) Å], are very close to those reported (Sow et al., 2012). The two types of Sn—Cl binding are due to disruption of NH ··· Cl hydrogen bonding on one of the chlorine atoms. The C–N–C angles of the cation are close to 109°, in agreement with the expected sp³ hybridization. The cation and the anion are connected by N—H···.Cl hydrogen bonds (Fig. 2).

Experimental

Crystals of the title compound, [C₃H₁₀N⁺] [Sn(C₆H₅)₃Cl₂^-], were obtained by reacting SnPh₃Cl with (CH₃)₃N.HCl in ethanol in a 1/1 ratio. (CH₃)₃N.HCl (Merck) and SnPh₃Cl (Aldrich) were used without further purification. The title compound was obtained by mixing in a 1/1 ratio (CH₃)₃N.HCl dissolved in methanol and a minimum of water and SnPh₃Cl dissolved in methanol. The mixture was stirred for around two hours at room temperature and upon slow solvent evaporation gave prismatic crystals suitable for X-ray diffraction analysis.