Benzyl­triphenyl­phospho­nium dichlorido­triphenyl­stannate(IV)

Bocar Traore; Mouhamadou Sembene Boye; Mamadou Sidibe; Libasse Diop; Philippe Guionneau

doi:10.1107/S1600536812049689

. 2012 Dec 12;69(Pt 1):m42. doi: 10.1107/S1600536812049689

Benzyltriphenylphosphonium dichloridotriphenylstannate(IV)

Bocar Traore ^a, Mouhamadou Sembene Boye ^a, Mamadou Sidibe ^a, Libasse Diop ^a,^*, Philippe Guionneau ^b

PMCID: PMC3588253 PMID: 23476339

Abstract

The crystal structure of the title salt, (C₂₅H₂₂P)[Sn(C₆H₅)₃Cl₂] or (PhCH₂PPh₃)[SnPh₃Cl₂], consists of [PhCH₂PPh₃]⁺ cations and [SnPh₃Cl₂]⁻ anions in which the Sn^IV atom is linked to two Cl atoms and three phenyl groups in a trigonal–bipyramidal geometry, with the Cl atoms in trans positions. The cation adopts a tetrahedral geometry. In the crystal, the cations and the anions are connected by C—H⋯Cl hydrogen bonds, leading to an infinite chain propagating along the c direction.

Related literature

For the [SnPh₃Cl₂]⁻ anion, see: Harrison et al. (1978 ▶); Ng (1995 ▶). For applications of tin based materials, see: Dutrecq et al. (1992 ▶).

Experimental

Crystal data

(C₂₅H₂₂P)[Sn(C₆H₅)₃Cl₂]
M _r = 774.29
Monoclinic,
a = 10.0222 (2) Å
b = 17.1480 (3) Å
c = 21.2925 (4) Å
β = 92.042 (1)°
V = 3657.02 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 293 K
0.25 × 0.25 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T _min = 0.803, T _max = 0.803
29025 measured reflections
9370 independent reflections
6243 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.102
S = 1.03
9370 reflections
425 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Data collection: COLLECT (Nonius, 2003 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(29.6KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049689/pk2448sup1.cif

e-69-00m42-sup1.cif^{(29.6KB, cif)}

Click here for additional data file.^{(449.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049689/pk2448Isup2.hkl

e-69-00m42-Isup2.hkl^{(449.1KB, 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
C35—H35⋯Cl2	0.93	2.94	3.696 (3)	139
C37—H37A⋯Cl1ⁱ	0.97	2.84	3.743 (3)	155
C30—H30⋯Cl1ⁱ	0.93	2.67	3.596 (3)	171

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The structure of [SnPh₃Cl₂]^- stabilized with different counterions have been reported (Harrison et al., 1978; Ng, 1995). In the scope of our research work toward new organotin (IV) compounds, owing to their various applications: agrochemicals, surface disinfectants, wood preservatives, and marine-antifouling paints (Dutrecq et al., 1992), we report here the crystal structure of [PhCH₂PPh₃][SnPh₃Cl₂].

In the asymmetric unit of the title compound (Fig. 1), the anion [SnPh₃Cl₂]^- adopts a trigonal bipyramidal geometry, the chloride atoms occupy the apical positions while the phenyl groups are equatorial. The Sn—C bonds are [2.135 (3); 2.142 (3); 2.153 (3) Å] while the Sn—Cl distances [2.5795 (7); 2.6127 (7) Å] are very similar to the unique Sn—Cl distance value [2.598 (1) Å] (Ng, 1995) but respectively longer and shorter than those [2.573 (7); 2.689 (6) Å] reported (Harrison et al., 1978) within the same anion. The sum of the equatorial angles (360°) is consistent with almost perfectly planar SnPh₃ residue, while the Cl—Sn—Cl deviates from linearity [175.77 (3)°].

[SnPh₃Cl₂]^- and [PhCH₂PPh₃]⁺ are linked through short C—H···Cl contacts (Table1 & Fig.2).

Experimental

All chemicals were purchased from Aldrich (Germany) and used without any further purification. The studied adduct is obtained following a two stage reaction. Synthesis of (PhCH₂PPh₃)₂PhAsO₃: this salt is obtained by neutralization of PhAsO₃H₂ (9.899 mmol in water) by PhCH₂Ph₃PCl (19.798 mmol in ethanolic solution) according to the following reaction:

PhAsO₃H₂ + 2(PhCH₂PPh₃Cl) → [(PhCH₂PPh₃)₂PhAsO₃] + 2HCl

Synthesis of [PhCH₂PPh₃][SnPh₃Cl₂]: this compound was obtained by mixing ethanolic solutions of (PhCH₂PPh₃)₂PhAsO₃ (0.5 mmol) and SnPh₃Cl (1.0 mmoL) in a 1/2 ratio. The mixture was stirred for around two hours at room temperature. Suitable crystals for X-ray diffraction were obtained after slow solvent evaporation. (m.p. 393 K). The title compound was isolated according to the following reaction:

[PhCH₂PPh₃]₂[PhAsO₃] + 2SnPh₃Cl → [PhCH₂PPh₃][SnPh₃Cl₂] + [PhCH₂PPh₃.PhAsO₃][SnPh₃]