catena-Poly[[trimethyl­tin(IV)]-μ-5-methyl­thio­phene-2-carboxyl­ato-κ2O:O′]

Zhu, Q.; Zhang, R.

doi:10.1107/S1600536811049713

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1834

https://doi.org/10.1107/S1600536811049713

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catena-Poly[[trimethyltin(IV)]-μ-5-methylthiophene-2-carboxylato-κ²O:O′]

Qi Zhu ^a and Rufen Zhang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: macl@lcu.edu.cn.

(Received 18 November 2011; accepted 21 November 2011; online 25 November 2011)

In the title polymeric coordination compound, [Sn(CH₃)₃(C₆H₅O₂S)]_n, which contains two formula units in the asymmetric unit, the Sn^IV atom has a distorted trigonal–bipyramidal geometry, with two O atoms of the ligands in axial positions and three methyl groups in equatorial positions. Adjacent Sn^IV atoms are bridged by the ligands, thereby forming a chain propagating in [010].

Related literature

For the biological activity of organotin compounds, see: Dubey & Roy (2003 ). For related structures, see: Wang et al. (2007); Ma et al. (2008 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₆H₅O₂S)]
M_r = 304.95
Triclinic, $[P \overline 1]$
a = 9.9591 (8) Å
b = 10.0655 (11) Å
c = 13.9890 (12) Å
α = 69.385 (1)°
β = 72.225 (1)°
γ = 75.038 (2)°
V = 1231.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.21 mm⁻¹
T = 298 K
0.44 × 0.15 × 0.09 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.443, T_max = 0.826
6219 measured reflections
4293 independent reflections
2340 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.242
S = 0.97
4293 reflections
243 parameters
H-atom parameters constrained
Δρ_max = 3.71 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C7	2.098 (12)
Sn1—C9	2.115 (14)
Sn1—C8	2.126 (16)
Sn1—O3	2.159 (9)
Sn1—O1	2.526 (10)
Sn2—C11	2.104 (14)
Sn2—C10	2.128 (16)
Sn2—C12	2.153 (15)
Sn2—O2	2.177 (10)
Sn2—O4ⁱ	2.502 (11)
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049713/hb6523sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049713/hb6523Isup2.hkl

checkCIF report

Comment top

Organotin complexes are attracting more and more attention because of their considerable structural diversity and interesting topologies (Murugavel et al. 2001). Herein, we report the crystal structure of the title compound. The title compound,which is shown in Fig.2 forms an extended one-dimensional chain structure arising from Sn—O bridges formed by the 5-methyl-2-thiophenecarboxylic acid ligands. The Sn—O bond distances in the compound [Sn1—O1 = 2.526 (10) Å; Sn1—O3 = 2.159 (9) Å] are comparable to those found in a related organotin carboxylate (Ma et al., 2008). The Sn atom is five-coordinate in a slightly distorted trigonal-bipyramidal coordination geometry, provided by the methyl groups in the equatorial positions and the two coordinated O atoms in the axial positions.

Related literature top

For the biological activity of organotin compounds, see: Dubey & Roy (2003). For related structures, see: Wang et al. (2007); Ma et al. (2008).

Experimental top

The reaction was carried out under a nitrogen atmosphere. 5-methyl-2-thiophenecarboxylic acid (1 mmol) and potassium hydroxide (1 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of diethyl ether to yield colorless blocks of the title compound (yield 76%). Anal. Calcd (%) for C₁₈H₂₈O₄S₂Sn₂(Mr = 609.90):C, 35.44; H, 4.63. Found (%): C, 35.71; H, 4.39.

Structure description top

For the biological activity of organotin compounds, see: Dubey & Roy (2003). For related structures, see: Wang et al. (2007); Ma et al. (2008).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. A view of the one-dimensional extended chain structure in the title compound.

catena-Poly[[trimethyltin(IV)]-µ-5-methylthiophene-2-carboxylato- κ²O:O'] top

Crystal data top

[Sn(CH₃)₃(C₆H₅O₂S)]	Z = 4
M_r = 304.95	F(000) = 600
Triclinic, P1	D_x = 1.644 Mg m⁻³
a = 9.9591 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0655 (11) Å	Cell parameters from 2063 reflections
c = 13.9890 (12) Å	θ = 2.8–26.3°
α = 69.385 (1)°	µ = 2.21 mm⁻¹
β = 72.225 (1)°	T = 298 K
γ = 75.038 (2)°	Block, colorless
V = 1231.9 (2) Å³	0.44 × 0.15 × 0.09 mm

Data collection top

Siemens SMART CCD diffractometer	4293 independent reflections
Radiation source: fine-focus sealed tube	2340 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
phi and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.443, T_max = 0.826	k = −11→11
6219 measured reflections	l = −15→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.242	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1385P)²] where P = (F_o² + 2F_c²)/3
4293 reflections	(Δ/σ)_max = 0.021
243 parameters	Δρ_max = 3.71 e Å⁻³
0 restraints	Δρ_min = −0.97 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₆H₅O₂S)]	γ = 75.038 (2)°
M_r = 304.95	V = 1231.9 (2) Å³
Triclinic, P1	Z = 4
a = 9.9591 (8) Å	Mo Kα radiation
b = 10.0655 (11) Å	µ = 2.21 mm⁻¹
c = 13.9890 (12) Å	T = 298 K
α = 69.385 (1)°	0.44 × 0.15 × 0.09 mm
β = 72.225 (1)°

Data collection top

Siemens SMART CCD diffractometer	4293 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2340 reflections with I > 2σ(I)
T_min = 0.443, T_max = 0.826	R_int = 0.048
6219 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.242	H-atom parameters constrained
S = 0.97	Δρ_max = 3.71 e Å⁻³
4293 reflections	Δρ_min = −0.97 e Å⁻³
243 parameters

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
C18	−0.5657 (19)	1.292 (2)	0.007 (2)	0.118 (8)
H18A	−0.6534	1.2537	0.0384	0.177*
H18B	−0.5268	1.2810	−0.0618	0.177*
H18C	−0.5841	1.3919	0.0029	0.177*
C17	−0.4596 (16)	1.2104 (15)	0.0749 (16)	0.073 (5)
Sn1	−0.05517 (11)	0.58071 (10)	0.21992 (7)	0.0541 (4)
Sn2	0.05372 (12)	0.02160 (10)	0.27985 (8)	0.0585 (4)
S1	0.3647 (5)	0.1708 (5)	0.4326 (4)	0.0753 (12)
S2	−0.3972 (5)	1.0294 (5)	0.0923 (4)	0.0834 (14)
O2	0.2015 (11)	0.1158 (10)	0.3134 (9)	0.070 (3)
O3	−0.2091 (11)	0.7772 (10)	0.1936 (9)	0.073 (3)
O1	0.1153 (12)	0.3438 (10)	0.2374 (9)	0.072 (3)
C15	−0.3124 (18)	1.1534 (15)	0.1843 (14)	0.076 (5)
H15	−0.2632	1.1724	0.2236	0.091*
C2	0.4377 (16)	0.295 (2)	0.4463 (15)	0.075 (5)
C6	0.1916 (14)	0.2509 (14)	0.2919 (11)	0.051 (3)
C8	−0.172 (2)	0.4864 (19)	0.1640 (17)	0.099 (7)
H8A	−0.1552	0.3837	0.1941	0.149*
H8B	−0.1417	0.5104	0.0888	0.149*
H8C	−0.2724	0.5226	0.1840	0.149*
C14	−0.2966 (15)	1.0243 (15)	0.1721 (11)	0.055 (4)
C13	−0.1981 (16)	0.8909 (16)	0.2101 (12)	0.060 (4)
C7	−0.0941 (18)	0.5333 (18)	0.3835 (10)	0.075 (5)
H7A	−0.1854	0.5857	0.4093	0.113*
H7B	−0.0206	0.5606	0.4004	0.113*
H7C	−0.0941	0.4319	0.4158	0.113*
C5	0.2827 (15)	0.2953 (15)	0.3406 (12)	0.058 (4)
C9	0.1179 (17)	0.6752 (18)	0.1082 (11)	0.081 (5)
H9A	0.1680	0.7069	0.1426	0.122*
H9B	0.0823	0.7560	0.0554	0.122*
H9C	0.1820	0.6054	0.0758	0.122*
C10	−0.1218 (18)	0.097 (2)	0.3910 (13)	0.089 (5)
H10A	−0.1401	0.2000	0.3687	0.133*
H10B	−0.0993	0.0624	0.4585	0.133*
H10C	−0.2052	0.0612	0.3959	0.133*
O4	−0.1108 (12)	0.8892 (11)	0.2585 (9)	0.078 (3)
C11	0.0877 (18)	0.120 (2)	0.1165 (11)	0.083 (5)
H11A	−0.0009	0.1408	0.0960	0.125*
H11B	0.1566	0.0569	0.0806	0.125*
H11C	0.1228	0.2085	0.0984	0.125*
C12	0.175 (2)	−0.1893 (17)	0.334 (2)	0.125 (9)
H12A	0.1702	−0.2493	0.2950	0.187*
H12B	0.1350	−0.2312	0.4074	0.187*
H12C	0.2724	−0.1816	0.3236	0.187*
C3	0.398 (2)	0.4268 (19)	0.3810 (18)	0.095 (6)
H3	0.4261	0.5099	0.3771	0.114*
C4	0.3110 (19)	0.4263 (16)	0.3212 (14)	0.075 (5)
H4	0.2759	0.5082	0.2726	0.090*
C16	−0.4115 (16)	1.2583 (17)	0.1315 (14)	0.072 (5)
H16	−0.4397	1.3516	0.1366	0.087*
C1	0.5226 (19)	0.261 (2)	0.5266 (18)	0.114 (8)
H1A	0.5870	0.1712	0.5275	0.171*
H1B	0.4587	0.2526	0.5947	0.171*
H1C	0.5763	0.3361	0.5090	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C18	0.082 (13)	0.078 (14)	0.20 (2)	0.003 (11)	−0.076 (15)	−0.026 (15)
C17	0.056 (10)	0.031 (8)	0.103 (13)	0.008 (7)	−0.012 (9)	−0.003 (8)
Sn1	0.0729 (7)	0.0382 (6)	0.0567 (7)	−0.0075 (5)	−0.0288 (5)	−0.0104 (5)
Sn2	0.0853 (8)	0.0349 (6)	0.0607 (7)	−0.0059 (5)	−0.0363 (6)	−0.0077 (5)
S1	0.078 (3)	0.059 (3)	0.101 (3)	−0.011 (2)	−0.043 (2)	−0.021 (2)
S2	0.087 (3)	0.054 (3)	0.129 (4)	0.006 (2)	−0.059 (3)	−0.034 (3)
O2	0.086 (7)	0.041 (6)	0.098 (8)	−0.010 (5)	−0.046 (6)	−0.018 (5)
O3	0.094 (8)	0.031 (5)	0.117 (9)	0.003 (5)	−0.063 (7)	−0.026 (6)
O1	0.090 (8)	0.039 (6)	0.088 (8)	0.003 (5)	−0.035 (6)	−0.018 (5)
C15	0.098 (13)	0.034 (8)	0.105 (14)	0.001 (8)	−0.038 (11)	−0.026 (9)
C2	0.054 (9)	0.079 (13)	0.104 (14)	−0.001 (8)	−0.023 (9)	−0.047 (11)
C6	0.060 (9)	0.033 (8)	0.059 (9)	−0.006 (6)	−0.015 (7)	−0.013 (7)
C8	0.124 (16)	0.066 (12)	0.153 (19)	0.005 (11)	−0.096 (15)	−0.048 (12)
C14	0.062 (9)	0.043 (8)	0.062 (9)	−0.013 (7)	−0.009 (7)	−0.020 (7)
C13	0.065 (10)	0.048 (9)	0.064 (10)	−0.003 (7)	−0.027 (8)	−0.008 (7)
C7	0.103 (12)	0.074 (11)	0.036 (8)	0.005 (9)	−0.026 (8)	−0.007 (8)
C5	0.063 (9)	0.036 (8)	0.076 (10)	−0.004 (7)	−0.014 (8)	−0.023 (7)
C9	0.094 (12)	0.078 (12)	0.048 (9)	−0.027 (10)	−0.012 (9)	0.014 (8)
C10	0.104 (14)	0.106 (15)	0.068 (11)	−0.023 (11)	−0.015 (10)	−0.040 (11)
O4	0.098 (8)	0.040 (6)	0.109 (9)	−0.004 (5)	−0.056 (7)	−0.019 (6)
C11	0.093 (12)	0.106 (14)	0.045 (9)	−0.025 (11)	−0.019 (8)	−0.009 (9)
C12	0.17 (2)	0.028 (9)	0.21 (3)	0.010 (11)	−0.13 (2)	−0.020 (12)
C3	0.090 (13)	0.054 (11)	0.17 (2)	−0.002 (10)	−0.043 (14)	−0.065 (13)
C4	0.085 (12)	0.040 (9)	0.100 (13)	−0.005 (8)	−0.019 (10)	−0.028 (9)
C16	0.060 (10)	0.046 (9)	0.096 (13)	0.002 (8)	−0.005 (9)	−0.023 (9)
C1	0.074 (13)	0.137 (19)	0.17 (2)	0.014 (12)	−0.053 (14)	−0.091 (18)

Geometric parameters (Å, º) top

C18—C17	1.51 (2)	C8—H8B	0.9600
C18—H18A	0.9600	C8—H8C	0.9600
C18—H18B	0.9600	C14—C13	1.478 (19)
C18—H18C	0.9600	C13—O4	1.247 (17)
C17—C16	1.31 (2)	C7—H7A	0.9600
C17—S2	1.720 (15)	C7—H7B	0.9600
Sn1—C7	2.098 (12)	C7—H7C	0.9600
Sn1—C9	2.115 (14)	C5—C4	1.34 (2)
Sn1—C8	2.126 (16)	C9—H9A	0.9600
Sn1—O3	2.159 (9)	C9—H9B	0.9600
Sn1—O1	2.526 (10)	C9—H9C	0.9600
Sn2—C11	2.104 (14)	C10—H10A	0.9600
Sn2—C10	2.128 (16)	C10—H10B	0.9600
Sn2—C12	2.153 (15)	C10—H10C	0.9600
Sn2—O2	2.177 (10)	O4—Sn2ⁱⁱ	2.502 (11)
Sn2—O4ⁱ	2.502 (11)	C11—H11A	0.9600
S1—C2	1.690 (17)	C11—H11B	0.9600
S1—C5	1.694 (15)	C11—H11C	0.9600
S2—C14	1.694 (15)	C12—H12A	0.9600
O2—C6	1.270 (15)	C12—H12B	0.9600
O3—C13	1.281 (17)	C12—H12C	0.9600
O1—C6	1.232 (15)	C3—C4	1.37 (2)
C15—C14	1.333 (19)	C3—H3	0.9300
C15—C16	1.41 (2)	C4—H4	0.9300
C15—H15	0.9300	C16—H16	0.9300
C2—C3	1.36 (2)	C1—H1A	0.9600
C2—C1	1.50 (2)	C1—H1B	0.9600
C6—C5	1.51 (2)	C1—H1C	0.9600
C8—H8A	0.9600

C17—C18—H18A	109.5	O4—C13—O3	121.8 (13)
C17—C18—H18B	109.5	O4—C13—C14	121.0 (14)
H18A—C18—H18B	109.5	O3—C13—C14	117.1 (13)
C17—C18—H18C	109.5	Sn1—C7—H7A	109.5
H18A—C18—H18C	109.5	Sn1—C7—H7B	109.5
H18B—C18—H18C	109.5	H7A—C7—H7B	109.5
C16—C17—C18	127.8 (16)	Sn1—C7—H7C	109.5
C16—C17—S2	111.3 (13)	H7A—C7—H7C	109.5
C18—C17—S2	120.7 (16)	H7B—C7—H7C	109.5
C7—Sn1—C9	125.7 (7)	C4—C5—C6	128.5 (15)
C7—Sn1—C8	116.7 (8)	C4—C5—S1	111.4 (13)
C9—Sn1—C8	116.3 (8)	C6—C5—S1	120.1 (10)
C7—Sn1—O3	97.3 (5)	Sn1—C9—H9A	109.5
C9—Sn1—O3	94.5 (6)	Sn1—C9—H9B	109.5
C8—Sn1—O3	89.4 (5)	H9A—C9—H9B	109.5
C7—Sn1—O1	87.2 (5)	Sn1—C9—H9C	109.5
C9—Sn1—O1	86.3 (5)	H9A—C9—H9C	109.5
C8—Sn1—O1	84.9 (5)	H9B—C9—H9C	109.5
O3—Sn1—O1	173.9 (4)	Sn2—C10—H10A	109.5
C11—Sn2—C10	123.3 (7)	Sn2—C10—H10B	109.5
C11—Sn2—C12	117.6 (9)	H10A—C10—H10B	109.5
C10—Sn2—C12	117.7 (9)	Sn2—C10—H10C	109.5
C11—Sn2—O2	99.4 (6)	H10A—C10—H10C	109.5
C10—Sn2—O2	92.2 (6)	H10B—C10—H10C	109.5
C12—Sn2—O2	89.8 (6)	C13—O4—Sn2ⁱⁱ	147.4 (10)
C11—Sn2—O4ⁱ	86.2 (6)	Sn2—C11—H11A	109.5
C10—Sn2—O4ⁱ	87.3 (6)	Sn2—C11—H11B	109.5
C12—Sn2—O4ⁱ	84.7 (6)	H11A—C11—H11B	109.5
O2—Sn2—O4ⁱ	173.5 (3)	Sn2—C11—H11C	109.5
C2—S1—C5	92.3 (8)	H11A—C11—H11C	109.5
C14—S2—C17	91.5 (9)	H11B—C11—H11C	109.5
C6—O2—Sn2	122.2 (9)	Sn2—C12—H12A	109.5
C13—O3—Sn1	123.0 (9)	Sn2—C12—H12B	109.5
C6—O1—Sn1	145.3 (9)	H12A—C12—H12B	109.5
C14—C15—C16	113.1 (16)	Sn2—C12—H12C	109.5
C14—C15—H15	123.5	H12A—C12—H12C	109.5
C16—C15—H15	123.5	H12B—C12—H12C	109.5
C3—C2—C1	127.4 (18)	C2—C3—C4	114.1 (16)
C3—C2—S1	109.6 (13)	C2—C3—H3	122.9
C1—C2—S1	122.8 (16)	C4—C3—H3	122.9
O1—C6—O2	125.7 (13)	C5—C4—C3	112.5 (17)
O1—C6—C5	119.8 (12)	C5—C4—H4	123.7
O2—C6—C5	114.5 (12)	C3—C4—H4	123.7
Sn1—C8—H8A	109.5	C17—C16—C15	112.9 (15)
Sn1—C8—H8B	109.5	C17—C16—H16	123.5
H8A—C8—H8B	109.5	C15—C16—H16	123.5
Sn1—C8—H8C	109.5	C2—C1—H1A	109.5
H8A—C8—H8C	109.5	C2—C1—H1B	109.5
H8B—C8—H8C	109.5	H1A—C1—H1B	109.5
C15—C14—C13	128.9 (15)	C2—C1—H1C	109.5
C15—C14—S2	111.0 (12)	H1A—C1—H1C	109.5
C13—C14—S2	119.8 (10)	H1B—C1—H1C	109.5

C16—C17—S2—C14	−3.4 (14)	C17—S2—C14—C13	−174.2 (12)
C18—C17—S2—C14	−179.0 (16)	Sn1—O3—C13—O4	−12 (2)
C11—Sn2—O2—C6	58.4 (13)	Sn1—O3—C13—C14	169.9 (9)
C10—Sn2—O2—C6	−65.9 (12)	C15—C14—C13—O4	−2 (3)
C12—Sn2—O2—C6	176.4 (13)	S2—C14—C13—O4	171.4 (13)
O4ⁱ—Sn2—O2—C6	−152 (3)	C15—C14—C13—O3	175.9 (16)
C7—Sn1—O3—C13	65.4 (13)	S2—C14—C13—O3	−10.4 (19)
C9—Sn1—O3—C13	−61.4 (13)	O1—C6—C5—C4	−11 (2)
C8—Sn1—O3—C13	−177.8 (14)	O2—C6—C5—C4	169.6 (15)
O1—Sn1—O3—C13	−158 (3)	O1—C6—C5—S1	169.1 (11)
C7—Sn1—O1—C6	−23.1 (18)	O2—C6—C5—S1	−10.3 (17)
C9—Sn1—O1—C6	103.0 (18)	C2—S1—C5—C4	0.3 (13)
C8—Sn1—O1—C6	−140.2 (19)	C2—S1—C5—C6	−179.8 (12)
O3—Sn1—O1—C6	−160 (3)	O3—C13—O4—Sn2ⁱⁱ	146.7 (14)
C5—S1—C2—C3	0.1 (14)	C14—C13—O4—Sn2ⁱⁱ	−35 (3)
C5—S1—C2—C1	175.3 (15)	C1—C2—C3—C4	−175.3 (18)
Sn1—O1—C6—O2	136.9 (14)	S1—C2—C3—C4	0 (2)
Sn1—O1—C6—C5	−42 (2)	C6—C5—C4—C3	179.5 (15)
Sn2—O2—C6—O1	−11 (2)	S1—C5—C4—C3	−0.5 (19)
Sn2—O2—C6—C5	167.9 (9)	C2—C3—C4—C5	1 (2)
C16—C15—C14—C13	176.4 (14)	C18—C17—C16—C15	−179.6 (18)
C16—C15—C14—S2	2.2 (19)	S2—C17—C16—C15	5 (2)
C17—S2—C14—C15	0.6 (14)	C14—C15—C16—C17	−5 (2)

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₆H₅O₂S)]
M_r	304.95
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.9591 (8), 10.0655 (11), 13.9890 (12)
α, β, γ (°)	69.385 (1), 72.225 (1), 75.038 (2)
V (Å³)	1231.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.21
Crystal size (mm)	0.44 × 0.15 × 0.09

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.443, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	6219, 4293, 2340
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.242, 0.97
No. of reflections	4293
No. of parameters	243
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.71, −0.97

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—C7	2.098 (12)	Sn2—C11	2.104 (14)
Sn1—C9	2.115 (14)	Sn2—C10	2.128 (16)
Sn1—C8	2.126 (16)	Sn2—C12	2.153 (15)
Sn1—O3	2.159 (9)	Sn2—O2	2.177 (10)
Sn1—O1	2.526 (10)	Sn2—O4ⁱ	2.502 (11)

Symmetry code: (i) x, y−1, z.

Acknowledgements

We thank the National Natural Science Foundation of China (20971096) for financial support.

References

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