[μ-2,2′-Dimethyl-2,2′-(p-phenyl­ene)diprop­yl]bis­[chloridobis(2-methyl-2-phenyl­prop­yl)tin(IV)]

Chunliu Sun; Chong Liang; Wanli Kang; Dongsheng Zhu

doi:10.1107/S1600536810011670

. 2010 Apr 10;66(Pt 5):m495. doi: 10.1107/S1600536810011670

[μ-2,2′-Dimethyl-2,2′-(p-phenylene)dipropyl]bis[chloridobis(2-methyl-2-phenylpropyl)tin(IV)]

Chunliu Sun ^a, Chong Liang ^b, Wanli Kang ^c,^*, Dongsheng Zhu ^d

PMCID: PMC2979286 PMID: 21578997

Abstract

The molecular structure of the title compound, [Sn₂(C₁₀H₁₃)₄(C₁₄H₂₀)Cl₂], is a binuclear centrosymmetric complex, in which the Sn atoms are four-coordinated by three C atoms and one Cl atom in a distorted tetrahedral geometry.

Related literature

For general background to organotin compounds, see: Chandrasekhar et al. (2002 ▶); Wu et al. (2009 ▶); For related structures, see: Tarassoli et al. (2002 ▶).

Experimental

Crystal data

[Sn₂(C₁₀H₁₃)₄(C₁₄H₂₀)Cl₂]
M _r = 1029.40
Monoclinic,
a = 15.0769 (19) Å
b = 17.773 (2) Å
c = 18.914 (2) Å
β = 94.674 (2)°
V = 5051.4 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 185 K
0.34 × 0.32 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.688, T _max = 0.721
14065 measured reflections
4976 independent reflections
3284 reflections with I > 2σ(I)
R _int = 0.073

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.113
S = 1.02
4976 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL-Plus.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011670/pb2026sup1.cif

e-66-0m495-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011670/pb2026Isup2.hkl

e-66-0m495-Isup2.hkl^{(243.8KB, hkl)}

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

Acknowledgments

We thank the State Key Development Program for Basic Research of China (2005CB221304) for support.

supplementary crystallographic information

Comment

The increasing interest in organotin compounds that has arisen in the last few decades is attributed to their significantly important biological properties like antiviral and anticancer agents, in vitro antibacterial and antifungal agents, wood preservatives and pesticides, etc. (Chandrasekhar et al., 2002; & Wu et al., 2009). Therefore, synthesis of new organotin compounds with different structural features will be beneficial in the development of pharmaceutical organotin and in other properties and application. herein, we present the synthesis and crystal structure of the title compound (I).

The structure of the title compound (Fig.1) consists of two symmetry equivalent tin moieties, where the tin atoms are tetrahedrally coordinated by the three C atoms and one Cl atom. The bond lengths for Sn(1)—C(1), Sn(1)—C(8) and Sn(1)—C(18) are 2.146 (5), 2.152 (5) and 2.149 (5) Å, respectively, which are slightly shorter than the Bz₃Sn(EtACDA) reported by Tarassoli et al. (Tarassoli et al., 2002). Around the tin, the angles C(1)—Sn(1)—C(8), C(1)—Sn(1)—C(18) and C(8)—Sn(1)—C(18) are wider while the C(1)—Sn(1)—Cl(1), C(8)—Sn(1)—Cl(1) and C(18)—Sn(1)—Cl(1) are narrower than the ideal tetrahedral angle. Thus, the environment of tin is best described as distorted tetrahedral.

Experimental

A small iodine grain, magnesium powder(0.24 g 10 mmol), and 1,4-bis(1- chloro-2-methylpropan-2-yl)benzene (0.52 g, 2 mmol) were added to 2 ml of anhydrous ether under stirring. The reaction mixture is then heated to 50 –60°C by hot-water bath and maintained slight boiling state. When the purplish red of iodine disappeared, which indicated the reaction were initiated, the hot-water bath was removed. The reaction were keeping the slight boiling state, then a solution of 1,4-bis(1-chloro-2-methylpropan- 2-yl)benzene (2.59 g, 10 mmol) in 10 ml anhydrous ether were added dropwise. After finished, the mixture was refluxed for 1 h to allow magnesium to proceed to completion, then cooled to 0–5°C by ice-salt bath. A solution of dichlorobis(2-methyl-2-phenylpropyl)stannane (4.56 g,10 mmol) in 15 mL THF were then added dropwise. After finished, the ice-salt bath was removed, and the reaction mixture were stirred for 0.5 h at room temprature then refluxed for another 1.5 h. Finally, the mixture were again cooled to 0°C, and acidified by dropwise adding a solution containing 2.5 g fuming HCl and 15 ml water. The layers were separated, the organic phase was dried over anhydrous calcium chloride. Following filtration and evaporation of the solvent, the residue was recrystallized by THF and the colorless block crystals of (I) were abtained.