catena-Poly[[trimethyl­tin(IV)]-μ-2-(2-chloro­phenyl)­acetato]

Wen, L.; Yin, H.; Li, W.

doi:10.1107/S1600536809038872

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1261

doi:10.1107/S1600536809038872

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catena-Poly[[trimethyltin(IV)]-μ-2-(2-chlorophenyl)acetato]

Liyuan Wen,^a Handong Yin ^a ^* and Wenkuan Li ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 13 September 2009; accepted 25 September 2009; online 30 September 2009)

In the title polymeric coordination compound, [Sn(CH₃)₃(C₈H₆ClO₂)]_n, the Sn atoms exhibit a distorted trigonal-bipyramidal geometry with the carboxylate O atoms of the 2-chlorophenylacetato ligands in axial positions and with the equatorial sites occupied by the three methyl groups. Adjacent Sn atoms are bridged by coordination to the two O atoms of each 2-chlorophenylacetato ligand, forming a chain structure.

Related literature

For the biological activity of organotin compounds, see: Wang et al. (2007 ). For related structures, see: Wang et al. (2007); Ma et al. (2006 ).

Experimental

Crystal data

[Sn(CH₃)₃(C₈H₆ClO₂)]
M_r = 333.39
Monoclinic, P 2₁ /n
a = 7.0754 (9) Å
b = 28.306 (3) Å
c = 13.6721 (15) Å
β = 93.117 (2)°
V = 2734.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.05 mm⁻¹
T = 298 K
0.49 × 0.32 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.434, T_max = 0.749
14063 measured reflections
4820 independent reflections
3411 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.107
S = 1.05
4820 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C17	2.107 (7)
Sn1—C18	2.117 (7)
Sn1—C19	2.120 (7)
Sn1—O3	2.194 (4)
Sn1—O1	2.396 (5)
Sn2—C22	2.102 (7)
Sn2—C20	2.113 (7)
Sn2—C21	2.117 (7)
Sn2—O2	2.207 (5)
Sn2—O4ⁱ	2.432 (5)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536809038872/sj2651sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038872/sj2651Isup2.hkl

checkCIF report

Comment top

The chemistry of organotin(IV) derivatives is a subject of study with growing interest due to their significant antimicrobial properties as well as antitumor activities (Wang et al., 2007). As a part of our ongoing investigations in this field we have synthesized the title compound and present its crystal structure here. The title compound, which is shown in Fig.1 forms an extended one-dimensional chain structure arising from Sn—O bridges formed by the 2-(2-chlorophenyl)acetato ligands. The Sn—O bond distances in the compound (Sn(1)—O(1) = 2.396 (5) Å; Sn(1)—O(3) = 2.194 (4) Å) are comparable to those found in related organotin carboxylates (Ma et al., 2006). The Sn atom assumes a slightly distorted trigonal-bipyramidal coordination geometry, provided by and three methyl groups in the equatorial positions and two O atoms of symmetry related carboxylate groups in the axial positions.

Related literature top

For the biological activity of organotin compounds, see: Wang et al. (2007). For related structures, see: Wang et al. (2007); Ma et al. (2006).

Experimental top

The reaction was carried out under a nitrogen atmosphere. 2-(2-chlorophenyl)acetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (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 dichloromethane/methanol (1:1) to yield colourless blocks of the title compound (yield 81%. m.p.390 K). Anal. Calcd (%) for C₁₁H₁₅Cl₁O₂Sn₁ (Mr = 333.37): C,39.63; H, 4.54; Cl, 10.63. Found (%): C, 39.51; H, 4.64; Cl, 10.75.

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 50% 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-2-(2-chlorophenyl)acetato] top

Crystal data top

[Sn(CH₃)₃(C₈H₆ClO₂)]	F(000) = 1312
M_r = 333.39	D_x = 1.620 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4326 reflections
a = 7.0754 (9) Å	θ = 2.6–24.8°
b = 28.306 (3) Å	µ = 2.05 mm⁻¹
c = 13.6721 (15) Å	T = 298 K
β = 93.117 (2)°	Block, colourless
V = 2734.1 (5) Å³	0.49 × 0.32 × 0.15 mm
Z = 8

Data collection top

Siemens SMART CCD area-detector diffractometer	4820 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.434, T_max = 0.749	k = −33→33
14063 measured reflections	l = −10→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0224P)² + 9.0463P] where P = (F_o² + 2F_c²)/3
4820 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 1.09 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

[Sn(CH₃)₃(C₈H₆ClO₂)]	V = 2734.1 (5) Å³
M_r = 333.39	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.0754 (9) Å	µ = 2.05 mm⁻¹
b = 28.306 (3) Å	T = 298 K
c = 13.6721 (15) Å	0.49 × 0.32 × 0.15 mm
β = 93.117 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4820 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3411 reflections with I > 2σ(I)
T_min = 0.434, T_max = 0.749	R_int = 0.056
14063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	Δρ_max = 1.09 e Å⁻³
4820 reflections	Δρ_min = −0.92 e Å⁻³
277 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.02624 (7)	0.138217 (16)	0.88059 (3)	0.04764 (16)
Sn2	0.20583 (7)	0.212967 (17)	1.21572 (3)	0.04848 (16)
Cl1	0.4073 (6)	0.03321 (16)	1.1310 (3)	0.1655 (15)
Cl2	−0.2267 (4)	0.14040 (10)	0.36127 (15)	0.0943 (8)
O1	0.1070 (7)	0.14009 (16)	1.0530 (3)	0.0583 (13)
O2	0.1197 (7)	0.13802 (16)	1.2145 (3)	0.0572 (13)
O3	−0.0431 (7)	0.13733 (16)	0.7223 (3)	0.0564 (13)
O4	−0.1907 (7)	0.20535 (18)	0.7318 (3)	0.0620 (14)
C1	0.0842 (11)	0.1192 (3)	1.1319 (5)	0.0553 (19)
C2	0.0044 (13)	0.0697 (3)	1.1322 (6)	0.073 (2)
H2A	−0.1323	0.0720	1.1333	0.088*
H2B	0.0328	0.0546	1.0710	0.088*
C3	0.0721 (17)	0.0382 (3)	1.2138 (7)	0.079 (3)
C4	0.2486 (19)	0.0191 (4)	1.2200 (8)	0.103 (3)
C5	0.316 (2)	−0.0112 (4)	1.2941 (10)	0.127 (4)
H5	0.4382	−0.0237	1.2975	0.153*
C6	0.184 (3)	−0.0208 (4)	1.3620 (10)	0.121 (5)
H6	0.2224	−0.0410	1.4131	0.145*
C7	0.001 (2)	−0.0036 (4)	1.3623 (9)	0.115 (4)
H7	−0.0816	−0.0121	1.4100	0.138*
C8	−0.0504 (18)	0.0264 (3)	1.2880 (8)	0.100 (3)
H8	−0.1708	0.0397	1.2861	0.120*
C9	−0.1339 (10)	0.1720 (3)	0.6832 (5)	0.0504 (18)
C10	−0.1744 (10)	0.1690 (3)	0.5734 (5)	0.0553 (19)
H10A	−0.0690	0.1534	0.5443	0.066*
H10B	−0.1837	0.2007	0.5469	0.066*
C11	−0.3557 (10)	0.1423 (2)	0.5447 (5)	0.0514 (18)
C12	−0.3923 (11)	0.1278 (3)	0.4478 (6)	0.062 (2)
C13	−0.5520 (14)	0.1049 (3)	0.4182 (7)	0.079 (3)
H13	−0.5713	0.0958	0.3531	0.095*
C14	−0.6863 (13)	0.0950 (3)	0.4838 (7)	0.080 (3)
H14	−0.7967	0.0792	0.4633	0.097*
C15	−0.6576 (12)	0.1084 (3)	0.5797 (7)	0.072 (2)
H15	−0.7488	0.1020	0.6244	0.086*
C16	−0.4919 (11)	0.1317 (3)	0.6100 (6)	0.064 (2)
H16	−0.4723	0.1403	0.6754	0.077*
C17	0.1855 (13)	0.0758 (3)	0.8683 (6)	0.079 (3)
H17A	0.2891	0.0759	0.9167	0.119*
H17B	0.2338	0.0741	0.8041	0.119*
H17C	0.1062	0.0489	0.8785	0.119*
C18	−0.2588 (11)	0.1335 (3)	0.9193 (6)	0.077 (2)
H18A	−0.3086	0.1030	0.9012	0.115*
H18B	−0.3322	0.1576	0.8855	0.115*
H18C	−0.2649	0.1378	0.9887	0.115*
C19	0.1885 (11)	0.2012 (3)	0.8801 (5)	0.069 (2)
H19A	0.3035	0.1969	0.9196	0.103*
H19B	0.1171	0.2266	0.9062	0.103*
H19C	0.2183	0.2086	0.8141	0.103*
C20	−0.0375 (10)	0.2385 (3)	1.1363 (6)	0.067 (2)
H20A	−0.0001	0.2560	1.0803	0.100*
H20B	−0.1072	0.2588	1.1776	0.100*
H20C	−0.1158	0.2124	1.1149	0.100*
C21	0.2034 (13)	0.2164 (3)	1.3703 (5)	0.075 (3)
H21A	0.1478	0.2458	1.3891	0.112*
H21B	0.3308	0.2145	1.3980	0.112*
H21C	0.1306	0.1906	1.3939	0.112*
C22	0.4641 (10)	0.2008 (3)	1.1510 (6)	0.071 (2)
H22A	0.4750	0.1678	1.1356	0.107*
H22B	0.5669	0.2099	1.1957	0.107*
H22C	0.4684	0.2191	1.0920	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0547 (3)	0.0418 (3)	0.0458 (3)	0.0031 (2)	−0.0036 (2)	−0.0021 (2)
Sn2	0.0490 (3)	0.0512 (3)	0.0451 (3)	−0.0101 (2)	0.0020 (2)	−0.0036 (2)
Cl1	0.138 (3)	0.195 (4)	0.163 (3)	0.045 (3)	0.005 (3)	0.002 (3)
Cl2	0.1043 (18)	0.130 (2)	0.0492 (12)	−0.0172 (16)	0.0086 (12)	−0.0131 (13)
O1	0.083 (4)	0.046 (3)	0.045 (3)	−0.007 (3)	−0.002 (2)	0.000 (2)
O2	0.083 (4)	0.047 (3)	0.041 (3)	−0.015 (3)	−0.001 (2)	−0.003 (2)
O3	0.074 (3)	0.049 (3)	0.045 (3)	0.017 (3)	−0.008 (2)	−0.007 (2)
O4	0.073 (4)	0.058 (3)	0.054 (3)	0.022 (3)	−0.009 (3)	−0.005 (3)
C1	0.071 (5)	0.046 (4)	0.048 (4)	−0.003 (4)	−0.007 (4)	0.001 (4)
C2	0.102 (7)	0.057 (5)	0.059 (5)	−0.019 (5)	−0.013 (5)	0.001 (4)
C3	0.122 (9)	0.044 (5)	0.068 (6)	−0.019 (5)	−0.016 (6)	−0.006 (4)
C4	0.145 (11)	0.071 (7)	0.088 (7)	−0.001 (7)	−0.021 (8)	−0.002 (6)
C5	0.181 (14)	0.084 (9)	0.113 (10)	0.012 (9)	−0.035 (10)	−0.006 (8)
C6	0.195 (16)	0.064 (8)	0.101 (10)	−0.014 (9)	−0.027 (10)	0.006 (7)
C7	0.178 (14)	0.078 (8)	0.089 (8)	−0.040 (9)	−0.007 (9)	−0.002 (7)
C8	0.153 (10)	0.060 (6)	0.084 (7)	−0.026 (6)	−0.011 (7)	−0.003 (6)
C9	0.051 (4)	0.057 (5)	0.043 (4)	0.007 (4)	−0.002 (3)	0.001 (4)
C10	0.055 (5)	0.063 (5)	0.047 (4)	0.003 (4)	−0.006 (3)	−0.001 (4)
C11	0.050 (4)	0.053 (5)	0.051 (4)	0.007 (3)	−0.007 (3)	0.000 (3)
C12	0.064 (5)	0.061 (5)	0.060 (5)	0.002 (4)	−0.009 (4)	−0.010 (4)
C13	0.087 (7)	0.074 (6)	0.074 (6)	−0.010 (5)	−0.012 (5)	−0.010 (5)
C14	0.077 (6)	0.068 (6)	0.094 (7)	−0.012 (5)	−0.012 (5)	−0.002 (5)
C15	0.063 (5)	0.070 (6)	0.083 (6)	−0.010 (4)	0.008 (5)	0.005 (5)
C16	0.068 (5)	0.066 (5)	0.058 (5)	0.000 (4)	0.000 (4)	0.000 (4)
C17	0.106 (7)	0.071 (6)	0.060 (5)	0.036 (5)	−0.013 (5)	−0.009 (4)
C18	0.059 (5)	0.093 (7)	0.078 (6)	−0.008 (5)	0.006 (4)	0.006 (5)
C19	0.074 (5)	0.075 (6)	0.057 (5)	−0.017 (4)	0.000 (4)	0.012 (4)
C20	0.050 (5)	0.063 (5)	0.086 (6)	0.003 (4)	0.001 (4)	−0.010 (4)
C21	0.117 (7)	0.068 (6)	0.039 (4)	−0.029 (5)	0.005 (4)	−0.004 (4)
C22	0.057 (5)	0.082 (6)	0.076 (5)	−0.006 (4)	0.006 (4)	−0.003 (5)

Geometric parameters (Å, º) top

Sn1—C17	2.107 (7)	C10—C11	1.522 (9)
Sn1—C18	2.117 (7)	C10—H10A	0.9700
Sn1—C19	2.120 (7)	C10—H10B	0.9700
Sn1—O3	2.194 (4)	C11—C16	1.381 (10)
Sn1—O1	2.396 (5)	C11—C12	1.397 (10)
Sn2—C22	2.102 (7)	C12—C13	1.345 (11)
Sn2—C20	2.113 (7)	C13—C14	1.371 (12)
Sn2—C21	2.117 (7)	C13—H13	0.9300
Sn2—O2	2.207 (5)	C14—C15	1.369 (11)
Sn2—O4ⁱ	2.432 (5)	C14—H14	0.9300
Cl1—C4	1.746 (12)	C15—C16	1.389 (11)
Cl2—C12	1.747 (8)	C15—H15	0.9300
O1—C1	1.249 (8)	C16—H16	0.9300
O2—C1	1.263 (8)	C17—H17A	0.9600
O3—C9	1.273 (8)	C17—H17B	0.9600
O4—C9	1.235 (8)	C17—H17C	0.9600
O4—Sn2ⁱⁱ	2.432 (5)	C18—H18A	0.9600
C1—C2	1.510 (10)	C18—H18B	0.9600
C2—C3	1.487 (11)	C18—H18C	0.9600
C2—H2A	0.9700	C19—H19A	0.9600
C2—H2B	0.9700	C19—H19B	0.9600
C3—C4	1.359 (14)	C19—H19C	0.9600
C3—C8	1.411 (13)	C20—H20A	0.9600
C4—C5	1.395 (15)	C20—H20B	0.9600
C5—C6	1.380 (17)	C20—H20C	0.9600
C5—H5	0.9300	C21—H21A	0.9600
C6—C7	1.387 (17)	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
C7—C8	1.358 (14)	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.515 (9)

C17—Sn1—C18	119.2 (4)	C9—C10—H10B	108.9
C17—Sn1—C19	114.4 (4)	C11—C10—H10B	108.9
C18—Sn1—C19	125.2 (3)	H10A—C10—H10B	107.7
C17—Sn1—O3	90.2 (2)	C16—C11—C12	116.7 (7)
C18—Sn1—O3	94.6 (3)	C16—C11—C10	123.3 (6)
C19—Sn1—O3	95.6 (2)	C12—C11—C10	120.0 (7)
C17—Sn1—O1	89.8 (2)	C13—C12—C11	122.4 (8)
C18—Sn1—O1	86.3 (3)	C13—C12—Cl2	118.5 (7)
C19—Sn1—O1	83.4 (2)	C11—C12—Cl2	119.1 (6)
O3—Sn1—O1	178.93 (18)	C12—C13—C14	120.1 (8)
C22—Sn2—C20	122.9 (3)	C12—C13—H13	119.9
C22—Sn2—C21	118.9 (3)	C14—C13—H13	119.9
C20—Sn2—C21	116.5 (3)	C15—C14—C13	119.9 (8)
C22—Sn2—O2	94.9 (3)	C15—C14—H14	120.1
C20—Sn2—O2	96.2 (3)	C13—C14—H14	120.1
C21—Sn2—O2	92.0 (2)	C14—C15—C16	119.7 (8)
C22—Sn2—O4ⁱ	86.0 (3)	C14—C15—H15	120.1
C20—Sn2—O4ⁱ	87.3 (2)	C16—C15—H15	120.1
C21—Sn2—O4ⁱ	83.4 (2)	C11—C16—C15	121.2 (7)
O2—Sn2—O4ⁱ	175.08 (16)	C11—C16—H16	119.4
C1—O1—Sn1	143.5 (5)	C15—C16—H16	119.4
C1—O2—Sn2	117.0 (4)	Sn1—C17—H17A	109.5
C9—O3—Sn1	119.0 (4)	Sn1—C17—H17B	109.5
C9—O4—Sn2ⁱⁱ	141.7 (5)	H17A—C17—H17B	109.5
O1—C1—O2	122.9 (7)	Sn1—C17—H17C	109.5
O1—C1—C2	120.6 (6)	H17A—C17—H17C	109.5
O2—C1—C2	116.5 (6)	H17B—C17—H17C	109.5
C3—C2—C1	116.9 (7)	Sn1—C18—H18A	109.5
C3—C2—H2A	108.1	Sn1—C18—H18B	109.5
C1—C2—H2A	108.1	H18A—C18—H18B	109.5
C3—C2—H2B	108.1	Sn1—C18—H18C	109.5
C1—C2—H2B	108.1	H18A—C18—H18C	109.5
H2A—C2—H2B	107.3	H18B—C18—H18C	109.5
C4—C3—C8	117.4 (10)	Sn1—C19—H19A	109.5
C4—C3—C2	122.9 (10)	Sn1—C19—H19B	109.5
C8—C3—C2	119.8 (10)	H19A—C19—H19B	109.5
C3—C4—C5	124.7 (13)	Sn1—C19—H19C	109.5
C3—C4—Cl1	119.3 (9)	H19A—C19—H19C	109.5
C5—C4—Cl1	116.0 (12)	H19B—C19—H19C	109.5
C6—C5—C4	113.0 (14)	Sn2—C20—H20A	109.5
C6—C5—H5	123.5	Sn2—C20—H20B	109.5
C4—C5—H5	123.5	H20A—C20—H20B	109.5
C5—C6—C7	127.0 (13)	Sn2—C20—H20C	109.5
C5—C6—H6	116.5	H20A—C20—H20C	109.5
C7—C6—H6	116.5	H20B—C20—H20C	109.5
C8—C7—C6	115.4 (13)	Sn2—C21—H21A	109.5
C8—C7—H7	122.3	Sn2—C21—H21B	109.5
C6—C7—H7	122.3	H21A—C21—H21B	109.5
C7—C8—C3	122.5 (12)	Sn2—C21—H21C	109.5
C7—C8—H8	118.8	H21A—C21—H21C	109.5
C3—C8—H8	118.8	H21B—C21—H21C	109.5
O4—C9—O3	122.4 (6)	Sn2—C22—H22A	109.5
O4—C9—C10	121.7 (6)	Sn2—C22—H22B	109.5
O3—C9—C10	115.9 (6)	H22A—C22—H22B	109.5
C9—C10—C11	113.2 (6)	Sn2—C22—H22C	109.5
C9—C10—H10A	108.9	H22A—C22—H22C	109.5
C11—C10—H10A	108.9	H22B—C22—H22C	109.5

C17—Sn1—O1—C1	−67.1 (9)	Cl1—C4—C5—C6	179.9 (9)
C18—Sn1—O1—C1	52.3 (9)	C4—C5—C6—C7	−0.1 (19)
C19—Sn1—O1—C1	178.4 (9)	C5—C6—C7—C8	−1.2 (19)
O3—Sn1—O1—C1	−159 (9)	C6—C7—C8—C3	2.0 (15)
C22—Sn2—O2—C1	−66.8 (6)	C4—C3—C8—C7	−1.6 (14)
C20—Sn2—O2—C1	57.1 (6)	C2—C3—C8—C7	177.3 (8)
C21—Sn2—O2—C1	174.0 (6)	Sn2ⁱⁱ—O4—C9—O3	160.1 (5)
O4ⁱ—Sn2—O2—C1	−167 (2)	Sn2ⁱⁱ—O4—C9—C10	−22.1 (12)
C17—Sn1—O3—C9	−174.5 (6)	Sn1—O3—C9—O4	−2.7 (9)
C18—Sn1—O3—C9	66.2 (6)	Sn1—O3—C9—C10	179.3 (4)
C19—Sn1—O3—C9	−60.0 (6)	O4—C9—C10—C11	−91.2 (9)
O1—Sn1—O3—C9	−83 (10)	O3—C9—C10—C11	86.7 (8)
Sn1—O1—C1—O2	−163.3 (5)	C9—C10—C11—C16	14.6 (10)
Sn1—O1—C1—C2	14.4 (13)	C9—C10—C11—C12	−166.5 (7)
Sn2—O2—C1—O1	4.5 (10)	C16—C11—C12—C13	0.3 (11)
Sn2—O2—C1—C2	−173.3 (5)	C10—C11—C12—C13	−178.7 (8)
O1—C1—C2—C3	148.0 (8)	C16—C11—C12—Cl2	179.6 (6)
O2—C1—C2—C3	−34.2 (11)	C10—C11—C12—Cl2	0.6 (10)
C1—C2—C3—C4	−72.9 (11)	C11—C12—C13—C14	0.1 (13)
C1—C2—C3—C8	108.2 (9)	Cl2—C12—C13—C14	−179.1 (7)
C8—C3—C4—C5	0.2 (15)	C12—C13—C14—C15	−0.1 (14)
C2—C3—C4—C5	−178.7 (9)	C13—C14—C15—C16	−0.4 (13)
C8—C3—C4—Cl1	−179.1 (7)	C12—C11—C16—C15	−0.8 (11)
C2—C3—C4—Cl1	2.0 (13)	C10—C11—C16—C15	178.1 (7)
C3—C4—C5—C6	0.6 (17)	C14—C15—C16—C11	0.9 (12)

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₈H₆ClO₂)]
M_r	333.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.0754 (9), 28.306 (3), 13.6721 (15)
β (°)	93.117 (2)
V (Å³)	2734.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.05
Crystal size (mm)	0.49 × 0.32 × 0.15

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.434, 0.749
No. of measured, independent and observed [I > 2σ(I)] reflections	14063, 4820, 3411
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.107, 1.05
No. of reflections	4820
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.92

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

Selected bond lengths (Å) top

Sn1—C17	2.107 (7)	Sn2—C22	2.102 (7)
Sn1—C18	2.117 (7)	Sn2—C20	2.113 (7)
Sn1—C19	2.120 (7)	Sn2—C21	2.117 (7)
Sn1—O3	2.194 (4)	Sn2—O2	2.207 (5)
Sn1—O1	2.396 (5)	Sn2—O4ⁱ	2.432 (5)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support. This work was also supported by the Shangdong `Tai-Shan Scholar Research Fund'.

References

Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem. 691, 1713–1721. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA. Google Scholar
Wang, H., Yin, H. & Wang, D. (2007). Acta Cryst. E63, m2955. Web of Science CSD CrossRef IUCr Journals Google Scholar