(Benzyl phenyl sulfoxide-κO)­chlorido­triphenyl­tin(IV)

Tan, G.-X.; Zhang, C.-F.

doi:10.1107/S1600536812005910

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m304

doi:10.1107/S1600536812005910

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(Benzyl phenyl sulfoxide-κO)chloridotriphenyltin(IV)

Guo-Xia Tan ^a ^* and Chang-Fa Zhang ^b

^aSchool of Chemistry and Chemical Engineering, Linyi University, Linyi 276000, People's Republic of China, and ^bShandong Water Polytechnic, Rizhao 276826, People's Republic of China
^*Correspondence e-mail: guoxiatan@163.com

(Received 10 January 2012; accepted 10 February 2012; online 17 February 2012)

The Sn^IV atom in the title compound, [Sn(C₆H₅)₃Cl(C₁₃H₁₂OS)], is situated within a distorted C₃ClO trigonal–bipyramidal coordination geometry with a mean Sn—C distance of 2.136 (6) Å and with an Sn—O distance of 2.393 (4) Å. The Sn^IV atom lies 0.171 (3) Å out of the equatorial C₃ plane in the direction of the axially bound Cl atom.

Related literature

For background to the structures, biological activities and industrial applications of triorganotin(IV) complexes, see: Davies et al. (2008 ); Tian et al. (2005 ). For related organotin sulfoxide structures, see: Fuller et al. (2009 ); Kumar et al. (2009 ); Filgueiras et al. (1982 ); Dokorou et al. (2011 ).

Experimental

Crystal data

[Sn(C₆H₅)₃Cl(C₁₃H₁₂OS)]
M_r = 601.73
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.744 (5) Å
b = 10.016 (3) Å
c = 28.840 (5) Å
V = 2814.7 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 295 K
0.32 × 0.28 × 0.21 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (XSCANS; Bruker, 1996 ) T_min = 0.720, T_max = 0.802
3690 measured reflections
3463 independent reflections
2794 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 97 reflections intensity decay: 2.3%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.067
S = 1.02
3463 reflections
306 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.40 e Å⁻³
Absolute structure: Flack (1983 ), 626 Friedel pairs
Flack parameter: 0.02 (3)

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005910/tk5048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005910/tk5048Isup2.hkl

checkCIF report

Comment top

Triorganotin compounds have received considerable attention due to their structural diversity and increasing numbers of industrial, agricultural and biological applications (Davies et al., 2008; Tian et al., 2005). Several structures of triorganotin sulfoxide complexes, such as chloro(dimethylsulfoxide)triphenyltin (Kumar et al., 2009), 1,2-bis(n-propylsulfinyl)ethylene)bis(chlorotriphenyltin) (Filgueiras et al., 1982), and (2-((2,3-dichlorophenyl)amino)benzoato)(dimethylsulfoxide)triphenyltin (Dokorou et al., 2011), have been reported. As a continuation of these studies, the structure of the title compound, (I), is described herein.

The coordination environment of the tin^IV atom in (I) can be described as a distorted trigonal bipyramid with three phenyl groups occupying the equatorial positions whereas the axial positions are occupied by the Cl1 atom and the sulfoxide O1 atom (Fig. 1).The Sn atom is slightly displaced from the equatorial plane defined by the C₃ set by 0.171 (3) Å in the direction of the Cl1 atom. The Sn—C and Sn—Cl bond lengths are similar to these found in chloro(dimethylsulfoxide-κO)triphenyltin (Kumar et al., 2009). However, the Sn—O length (2.393 (4) Å) is longer than that in the above mentioned structure (2.310 (2) Å). The S═O bond length (1.524 (4) Å) is longer than that in the free ligand (1.500 (2) Å) (Fuller et al., 2009) due to the O1 atom coordination to Sn atom. The dihedral angle between two phenyl rings in the sulfoxide ligand is 54.56 (5)°.

Related literature top

For background to the structures, biological activities and industrial applications of triorganotin(IV) complexes, see: Davies et al. (2008); Tian et al. (2005). For related organotin sulfoxide structures, see: Fuller et al. (2009); Kumar et al. (2009); Filgueiras et al. (1982); Dokorou et al. (2011).

Experimental top

Benzylphenylsulfoxide (0.43 g, 2 mmol) and triphenyltin chloride (0.77 g, 2 mmol) in ethanol (40 ml) were refluxed for 1 h, and then the colourless solution was reduced to 15 ml under reduce pressure. The colourless crystals suitable for X-ray analysis were obtained by slow evaporation of the solution at room temperature (yield: 62%; M.pt.: 385–386 K).

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: XSCANS (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids are drawn at the 30% probability level.

(Benzyl phenyl sulfoxide-κO)chloridotriphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃Cl(C₁₃H₁₂OS)]	F(000) = 1216
M_r = 601.73	D_x = 1.420 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 35 reflections
a = 9.744 (5) Å	θ = 5.1–12.5°
b = 10.016 (3) Å	µ = 1.10 mm⁻¹
c = 28.840 (5) Å	T = 295 K
V = 2814.7 (17) Å³	Block, colourless
Z = 4	0.32 × 0.28 × 0.21 mm

Data collection top

Bruker P4 diffractometer	2794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −1→11
Absorption correction: ψ scan (XSCANS; Bruker, 1996)	k = −1→11
T_min = 0.720, T_max = 0.802	l = −1→34
3690 measured reflections	3 standard reflections every 97 reflections
3463 independent reflections	intensity decay: 2.3%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.024P)² + 0.0502P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.067	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.37 e Å⁻³
3463 reflections	Δρ_min = −0.40 e Å⁻³
306 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00117 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 626 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (3)

Crystal data top

[Sn(C₆H₅)₃Cl(C₁₃H₁₂OS)]	V = 2814.7 (17) Å³
M_r = 601.73	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.744 (5) Å	µ = 1.10 mm⁻¹
b = 10.016 (3) Å	T = 295 K
c = 28.840 (5) Å	0.32 × 0.28 × 0.21 mm

Data collection top

Bruker P4 diffractometer	2794 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Bruker, 1996)	R_int = 0.021
T_min = 0.720, T_max = 0.802	3 standard reflections every 97 reflections
3690 measured reflections	intensity decay: 2.3%
3463 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.37 e Å⁻³
S = 1.02	Δρ_min = −0.40 e Å⁻³
3463 reflections	Absolute structure: Flack (1983), 626 Friedel pairs
306 parameters	Absolute structure parameter: 0.02 (3)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.09780 (5)	0.65032 (4)	0.122403 (15)	0.04029 (13)
O1	−0.1431 (4)	0.6938 (4)	0.12855 (16)	0.0497 (12)
Cl1	0.34939 (15)	0.60290 (16)	0.12177 (6)	0.0534 (4)
S1	−0.19603 (16)	0.83689 (17)	0.13031 (6)	0.0502 (4)
C1	0.0329 (7)	0.4480 (6)	0.1119 (2)	0.0423 (17)
C2	−0.0971 (9)	0.4170 (7)	0.0986 (2)	0.064 (2)
H2	−0.1620	0.4846	0.0959	0.077*
C3	−0.1346 (9)	0.2866 (8)	0.0890 (3)	0.086 (3)
H3	−0.2243	0.2680	0.0800	0.103*
C4	−0.0424 (9)	0.1856 (7)	0.0925 (3)	0.076 (3)
H4	−0.0676	0.0985	0.0854	0.091*
C5	0.0869 (9)	0.2137 (7)	0.1067 (3)	0.079 (3)
H5	0.1504	0.1452	0.1101	0.095*
C6	0.1254 (7)	0.3454 (7)	0.1162 (2)	0.066 (2)
H6	0.2147	0.3636	0.1256	0.079*
C7	0.1114 (6)	0.7524 (5)	0.18703 (12)	0.0494 (18)
C8	0.2066 (6)	0.8553 (5)	0.19079 (17)	0.089 (3)
H8	0.2597	0.8792	0.1653	0.107*
C9	0.2224 (6)	0.9224 (5)	0.2326 (2)	0.122 (4)
H9	0.2861	0.9912	0.2351	0.146*
C10	0.1431 (7)	0.8867 (6)	0.27072 (15)	0.111 (4)
H10	0.1536	0.9316	0.2987	0.133*
C11	0.0479 (6)	0.7838 (6)	0.26696 (13)	0.098 (4)
H11	−0.0052	0.7599	0.2924	0.117*
C12	0.0321 (5)	0.7167 (5)	0.22511 (18)	0.070 (2)
H12	−0.0316	0.6479	0.2226	0.084*
C13	−0.2771 (7)	0.8539 (7)	0.1851 (2)	0.0495 (16)
C14	−0.3607 (8)	0.7581 (7)	0.2023 (3)	0.066 (2)
H14	−0.3769	0.6807	0.1853	0.079*
C15	−0.4224 (9)	0.7757 (8)	0.2452 (3)	0.078 (2)
H15	−0.4808	0.7106	0.2570	0.093*
C16	−0.3965 (10)	0.8893 (9)	0.2701 (3)	0.087 (3)
H16	−0.4384	0.9019	0.2988	0.105*
C17	−0.3094 (9)	0.9846 (9)	0.2530 (3)	0.088 (3)
H17	−0.2907	1.0608	0.2703	0.106*
C18	−0.2498 (8)	0.9676 (7)	0.2103 (3)	0.066 (2)
H18	−0.1912	1.0325	0.1985	0.079*
C19	−0.3445 (6)	0.8314 (7)	0.0924 (2)	0.0564 (19)
H19A	−0.3179	0.7908	0.0632	0.068*
H19B	−0.4140	0.7750	0.1064	0.068*
C20	−0.4055 (8)	0.9656 (7)	0.0828 (2)	0.0556 (17)
C21	−0.4840 (8)	1.0320 (8)	0.1156 (3)	0.074 (2)
H21A	−0.4991	0.9929	0.1444	0.088*
C22	−0.5403 (9)	1.1564 (10)	0.1058 (4)	0.103 (3)
H22A	−0.5896	1.2019	0.1285	0.124*
C23	−0.5235 (11)	1.2117 (10)	0.0632 (5)	0.109 (4)
H23A	−0.5649	1.2932	0.0566	0.131*
C24	−0.4459 (10)	1.1491 (10)	0.0294 (4)	0.104 (4)
H24A	−0.4332	1.1880	0.0004	0.125*
C25	−0.3872 (9)	1.0254 (8)	0.0401 (3)	0.076 (2)
H25A	−0.3344	0.9821	0.0178	0.091*
C26	0.0997 (7)	0.7770 (6)	0.06277 (19)	0.0376 (14)
C27	0.2015 (7)	0.8674 (7)	0.0545 (2)	0.0555 (19)
H27	0.2750	0.8713	0.0750	0.067*
C28	0.2003 (9)	0.9535 (7)	0.0170 (3)	0.067 (2)
H28	0.2710	1.0146	0.0127	0.080*
C29	0.0934 (11)	0.9471 (7)	−0.0136 (2)	0.069 (2)
H29	0.0913	1.0040	−0.0391	0.082*
C30	−0.0101 (8)	0.8575 (9)	−0.0068 (2)	0.068 (2)
H30	−0.0821	0.8530	−0.0279	0.082*
C31	−0.0087 (7)	0.7734 (7)	0.0310 (2)	0.0533 (19)
H31	−0.0806	0.7137	0.0355	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0418 (2)	0.0370 (2)	0.0421 (2)	−0.0018 (3)	0.0005 (3)	0.0007 (2)
O1	0.038 (2)	0.037 (2)	0.074 (3)	0.0086 (19)	0.003 (2)	−0.006 (2)
Cl1	0.0402 (9)	0.0677 (10)	0.0523 (8)	0.0007 (8)	0.0055 (10)	0.0088 (10)
S1	0.0432 (9)	0.0374 (8)	0.0701 (11)	−0.0007 (9)	−0.0056 (9)	−0.0031 (11)
C1	0.044 (4)	0.034 (3)	0.049 (4)	0.002 (3)	0.004 (3)	−0.004 (3)
C2	0.051 (5)	0.046 (4)	0.094 (5)	0.007 (5)	−0.017 (5)	−0.009 (4)
C3	0.063 (6)	0.069 (5)	0.125 (7)	−0.018 (5)	−0.013 (5)	−0.014 (6)
C4	0.081 (6)	0.040 (5)	0.107 (6)	−0.012 (5)	0.012 (5)	−0.007 (4)
C5	0.067 (5)	0.044 (4)	0.126 (8)	0.008 (5)	−0.004 (6)	−0.012 (4)
C6	0.051 (4)	0.046 (3)	0.100 (5)	0.009 (4)	0.000 (5)	−0.011 (6)
C7	0.054 (5)	0.047 (4)	0.047 (4)	0.011 (5)	−0.001 (4)	−0.004 (3)
C8	0.105 (7)	0.083 (6)	0.080 (5)	−0.021 (7)	0.011 (5)	−0.042 (6)
C9	0.131 (9)	0.124 (9)	0.111 (8)	−0.033 (8)	0.008 (8)	−0.075 (7)
C10	0.120 (10)	0.144 (10)	0.068 (6)	0.055 (8)	−0.017 (6)	−0.043 (7)
C11	0.134 (10)	0.112 (7)	0.047 (5)	0.058 (7)	0.006 (5)	−0.005 (5)
C12	0.085 (6)	0.077 (5)	0.048 (4)	0.013 (5)	0.010 (4)	0.009 (4)
C13	0.047 (4)	0.041 (4)	0.060 (4)	0.006 (4)	−0.004 (4)	−0.009 (4)
C14	0.079 (6)	0.046 (4)	0.073 (5)	−0.002 (5)	0.010 (5)	−0.009 (4)
C15	0.078 (7)	0.090 (6)	0.066 (5)	−0.011 (6)	0.008 (5)	0.008 (5)
C16	0.082 (6)	0.115 (8)	0.065 (5)	0.022 (7)	−0.009 (6)	−0.029 (6)
C17	0.089 (8)	0.077 (6)	0.099 (7)	0.006 (6)	−0.017 (6)	−0.044 (6)
C18	0.060 (6)	0.061 (5)	0.077 (5)	−0.004 (5)	−0.009 (5)	−0.024 (5)
C19	0.050 (4)	0.054 (5)	0.065 (4)	0.003 (4)	−0.008 (4)	−0.009 (4)
C20	0.043 (4)	0.053 (4)	0.071 (4)	−0.003 (5)	−0.016 (5)	−0.001 (4)
C21	0.054 (5)	0.071 (5)	0.096 (6)	0.010 (5)	−0.019 (5)	−0.007 (6)
C22	0.072 (6)	0.075 (6)	0.163 (10)	0.024 (6)	−0.038 (7)	−0.020 (7)
C23	0.081 (8)	0.061 (6)	0.185 (13)	0.000 (6)	−0.077 (9)	0.020 (7)
C24	0.098 (9)	0.090 (7)	0.125 (8)	−0.016 (8)	−0.038 (7)	0.047 (7)
C25	0.068 (6)	0.080 (6)	0.080 (5)	−0.012 (6)	−0.017 (5)	0.011 (5)
C26	0.034 (3)	0.037 (3)	0.042 (3)	0.001 (4)	−0.001 (4)	0.001 (3)
C27	0.055 (5)	0.056 (5)	0.055 (4)	−0.008 (5)	−0.006 (4)	0.001 (4)
C28	0.086 (6)	0.044 (4)	0.070 (5)	−0.004 (5)	0.014 (5)	0.011 (4)
C29	0.098 (6)	0.056 (4)	0.051 (4)	0.004 (6)	0.013 (6)	0.011 (4)
C30	0.076 (5)	0.087 (6)	0.042 (4)	0.026 (6)	−0.013 (4)	−0.002 (5)
C31	0.053 (4)	0.061 (5)	0.046 (4)	−0.008 (4)	0.000 (4)	−0.003 (4)

Geometric parameters (Å, º) top

Sn1—C7	2.130 (3)	C14—H14	0.9300
Sn1—C26	2.138 (5)	C15—C16	1.369 (10)
Sn1—C1	2.145 (6)	C15—H15	0.9300
Sn1—O1	2.394 (4)	C16—C17	1.369 (11)
Sn1—Cl1	2.4972 (19)	C16—H16	0.9300
O1—S1	1.524 (4)	C17—C18	1.371 (10)
S1—C13	1.774 (6)	C17—H17	0.9300
S1—C19	1.815 (6)	C18—H18	0.9300
C1—C2	1.359 (9)	C19—C20	1.496 (9)
C1—C6	1.373 (8)	C19—H19A	0.9700
C2—C3	1.384 (9)	C19—H19B	0.9700
C2—H2	0.9300	C20—C25	1.380 (9)
C3—C4	1.357 (10)	C20—C21	1.386 (9)
C3—H3	0.9300	C21—C22	1.391 (10)
C4—C5	1.354 (10)	C21—H21A	0.9300
C4—H4	0.9300	C22—C23	1.358 (12)
C5—C6	1.398 (9)	C22—H22A	0.9300
C5—H5	0.9300	C23—C24	1.384 (13)
C6—H6	0.9300	C23—H23A	0.9300
C7—C8	1.3900	C24—C25	1.399 (11)
C7—C12	1.3900	C24—H24A	0.9300
C8—C9	1.3900	C25—H25A	0.9300
C8—H8	0.9300	C26—C27	1.364 (8)
C9—C10	1.3900	C26—C31	1.398 (8)
C9—H9	0.9300	C27—C28	1.382 (9)
C10—C11	1.3900	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.367 (11)
C11—C12	1.3900	C28—H28	0.9300
C11—H11	0.9300	C29—C30	1.364 (10)
C12—H12	0.9300	C29—H29	0.9300
C13—C14	1.353 (9)	C30—C31	1.379 (9)
C13—C18	1.378 (9)	C30—H30	0.9300
C14—C15	1.388 (9)	C31—H31	0.9300

C7—Sn1—C26	114.73 (19)	C15—C14—H14	120.1
C7—Sn1—C1	126.6 (2)	C16—C15—C14	119.6 (8)
C26—Sn1—C1	116.7 (2)	C16—C15—H15	120.2
C7—Sn1—O1	84.78 (19)	C14—C15—H15	120.2
C26—Sn1—O1	87.7 (2)	C17—C16—C15	120.3 (9)
C1—Sn1—O1	83.87 (19)	C17—C16—H16	119.8
C7—Sn1—Cl1	92.09 (16)	C15—C16—H16	119.8
C26—Sn1—Cl1	95.67 (19)	C16—C17—C18	120.0 (8)
C1—Sn1—Cl1	96.24 (18)	C16—C17—H17	120.0
O1—Sn1—Cl1	176.15 (12)	C18—C17—H17	120.0
S1—O1—Sn1	120.4 (2)	C17—C18—C13	119.7 (8)
O1—S1—C13	105.7 (3)	C17—C18—H18	120.2
O1—S1—C19	102.8 (3)	C13—C18—H18	120.2
C13—S1—C19	100.7 (3)	C20—C19—S1	113.6 (5)
C2—C1—C6	117.8 (6)	C20—C19—H19A	108.8
C2—C1—Sn1	122.0 (5)	S1—C19—H19A	108.8
C6—C1—Sn1	120.1 (5)	C20—C19—H19B	108.8
C1—C2—C3	121.2 (7)	S1—C19—H19B	108.8
C1—C2—H2	119.4	H19A—C19—H19B	107.7
C3—C2—H2	119.4	C25—C20—C21	118.2 (7)
C4—C3—C2	120.9 (8)	C25—C20—C19	120.2 (8)
C4—C3—H3	119.5	C21—C20—C19	121.6 (7)
C2—C3—H3	119.5	C20—C21—C22	120.6 (9)
C5—C4—C3	118.9 (7)	C20—C21—H21A	119.7
C5—C4—H4	120.5	C22—C21—H21A	119.7
C3—C4—H4	120.5	C23—C22—C21	120.1 (10)
C4—C5—C6	120.3 (7)	C23—C22—H22A	120.0
C4—C5—H5	119.8	C21—C22—H22A	120.0
C6—C5—H5	119.8	C22—C23—C24	121.3 (10)
C1—C6—C5	120.8 (7)	C22—C23—H23A	119.4
C1—C6—H6	119.6	C24—C23—H23A	119.4
C5—C6—H6	119.6	C23—C24—C25	117.9 (10)
C8—C7—C12	120.0	C23—C24—H24A	121.0
C8—C7—Sn1	117.8 (3)	C25—C24—H24A	121.0
C12—C7—Sn1	122.2 (3)	C20—C25—C24	121.9 (9)
C7—C8—C9	120.0	C20—C25—H25A	119.0
C7—C8—H8	120.0	C24—C25—H25A	119.0
C9—C8—H8	120.0	C27—C26—C31	116.9 (6)
C10—C9—C8	120.0	C27—C26—Sn1	122.8 (5)
C10—C9—H9	120.0	C31—C26—Sn1	120.3 (5)
C8—C9—H9	120.0	C26—C27—C28	123.0 (7)
C9—C10—C11	120.0	C26—C27—H27	118.5
C9—C10—H10	120.0	C28—C27—H27	118.5
C11—C10—H10	120.0	C29—C28—C27	118.8 (8)
C10—C11—C12	120.0	C29—C28—H28	120.6
C10—C11—H11	120.0	C27—C28—H28	120.6
C12—C11—H11	120.0	C30—C29—C28	120.1 (7)
C11—C12—C7	120.0	C30—C29—H29	119.9
C11—C12—H12	120.0	C28—C29—H29	119.9
C7—C12—H12	120.0	C29—C30—C31	120.5 (7)
C14—C13—C18	120.6 (6)	C29—C30—H30	119.8
C14—C13—S1	121.7 (5)	C31—C30—H30	119.8
C18—C13—S1	117.7 (6)	C30—C31—C26	120.7 (7)
C13—C14—C15	119.8 (7)	C30—C31—H31	119.7
C13—C14—H14	120.1	C26—C31—H31	119.7

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃Cl(C₁₃H₁₂OS)]
M_r	601.73
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	9.744 (5), 10.016 (3), 28.840 (5)
V (Å³)	2814.7 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.32 × 0.28 × 0.21

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	ψ scan (XSCANS; Bruker, 1996)
T_min, T_max	0.720, 0.802
No. of measured, independent and observed [I > 2σ(I)] reflections	3690, 3463, 2794
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.067, 1.02
No. of reflections	3463
No. of parameters	306
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.40
Absolute structure	Flack (1983), 626 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: XSCANS (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Acknowledgements

This work was supported by Shandong Provincial Natural Science Foundation, China (grant No. ZR2010BL012).

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