Bis(μ-chloroacetato-κ2O:O′)bis(chloro­acetato-κO)di-μ3-oxido-tetrakis[dibenzyl­tin(IV)]

Li, J.; Yin, H.; Wang, D.

doi:10.1107/S1600536810054000

metal-organic compounds

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Volume 67| Part 2| February 2011| Page m147

doi:10.1107/S1600536810054000

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Bis(μ-chloroacetato-κ²O:O′)bis(chloroacetato-κO)di-μ₃-oxido-tetrakis[dibenzyltin(IV)]

Jing Li,^a Handong Yin ^a ^* and Daqi Wang ^a

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

(Received 24 November 2010; accepted 24 December 2010; online 8 January 2011)

The title tetranuclear complex molecule, [Sn₄(C₇H₇)₈(C₂H₂ClO₂)₄O₂], has crystallographically imposed inversion symmetry. Each Sn atom has a distorted trigonal–bipyramidal geometry, with the equatorial plane formed by an oxido O atom and two C atoms of two benzyl anions. The configuration of the complex is stabilized by a pair of C—H⋯O hydrogen bonds. In the crystal, complex molecules are linked into zigzag chains along [110] by C—H⋯O hydrogen bonds.

Related literature

For the biological activity of organotin derivatives, see: Gielen et al. (1988 ). For a related structure, see: Teoh et al. (2002 ).

Experimental

Crystal data

[Sn₄(C₇H₇)₈(C₂H₂ClO₂)₄O₂]
M_r = 1609.71
Triclinic, $[P \overline 1]$
a = 10.4377 (8) Å
b = 13.0091 (9) Å
c = 13.3920 (11) Å
α = 104.920 (2)°
β = 103.208 (1)°
γ = 106.498 (1)°
V = 1593.0 (2) Å³
Z = 1
Mo Kα radiation
μ = 1.77 mm⁻¹
T = 298 K
0.20 × 0.13 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS, Sheldrick, 1996 ) T_min = 0.718, T_max = 0.871
8386 measured reflections
5551 independent reflections
4110 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.054
S = 1.01
5551 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4	0.93	2.49	3.229 (6)	136
C4—H4A⋯O4ⁱ	0.97	2.44	3.291 (5)	146
Symmetry code: (i) -x+2, -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: 10.1107/S1600536810054000/rz2532sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054000/rz2532Isup2.hkl

checkCIF report

Comment top

Organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 1988). In our ongoing studies on chloroacetic acid and organotin, the title compound has been synthesized and we report herein its crystal structure.

The molecular structure of the tetranuclear title compound is shown in Fig. 1. Each Sn atom is five-coordinated by two carboxylic O atoms, an oxo O atom, and two C atoms of two benzyl anions into a distorted trigonal-bipyramidal geometry very similar to that observed in a related compound (Teoh et al., 2002). The Sn—O distances are in the range 2.024 (2)–2.217 (2) Å. The conformation of the complex molecule is stabilized by a pair of C—H···O hydrogen bonds (Table 1). In the crystal (Fig. 2), complex molecules are connected along the [110] direction forming zigzag chains by C—H···O hydrogen bonds.

Related literature top

For the biological activity of organotin derivatives, see: Gielen et al. (1988). For a related structure, see: Teoh et al. (2002).

Experimental top

The reaction was carried out under nitrogen atmosphere. Chloroacetic acid (4 mmol) was added to a mixture of ethanol and benzene (1:3 v/v, 30 ml) with sodium ethoxide (4 mmol). The mixture was stirred for 0.5 h and then dichlorodibenzyltin (4 mmol) was added and the mixture was stirred at room temperature for 12 h. Crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane–petroleum ether (1:2 v/v) solution over a period of two weeks. Analysis, calculated for [(C₆H₅CH₂)₈(C₂H₂ClO₂)₄O₂Sn₄] (Mr = 1609.71): C 47.75, H 4.00%; found: C 47.82, H 3.95%.

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 molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Symmetry code: (A) 1-x, -y, -z.
	Fig. 2. Crystal packing of the title compound, showing a one-dimensional chain formed by C—H···O hydrogen bonds (dashed lines).

Bis(µ-chloroacetato-κ²O:O')bis(chloroacetato- κO)di-µ₃-oxido-tetrakis[dibenzyltin(IV)] top

Crystal data top

[Sn₄(C₇H₇)₈(C₂H₂ClO₂)₄O₂]	Z = 1
M_r = 1609.71	F(000) = 796
Triclinic, P1	D_x = 1.678 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4377 (8) Å	Cell parameters from 3277 reflections
b = 13.0091 (9) Å	θ = 2.8–26.3°
c = 13.3920 (11) Å	µ = 1.77 mm⁻¹
α = 104.920 (2)°	T = 298 K
β = 103.208 (1)°	Block, colourless
γ = 106.498 (1)°	0.20 × 0.13 × 0.08 mm
V = 1593.0 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	5551 independent reflections
Radiation source: fine-focus sealed tube	4110 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −12→12
T_min = 0.718, T_max = 0.871	k = −15→15
8386 measured reflections	l = −11→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0103P)²] where P = (F_o² + 2F_c²)/3
5551 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Sn₄(C₇H₇)₈(C₂H₂ClO₂)₄O₂]	γ = 106.498 (1)°
M_r = 1609.71	V = 1593.0 (2) Å³
Triclinic, P1	Z = 1
a = 10.4377 (8) Å	Mo Kα radiation
b = 13.0091 (9) Å	µ = 1.77 mm⁻¹
c = 13.3920 (11) Å	T = 298 K
α = 104.920 (2)°	0.20 × 0.13 × 0.08 mm
β = 103.208 (1)°

Data collection top

Bruker SMART CCD diffractometer	5551 independent reflections
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	4110 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.871	R_int = 0.023
8386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.01	Δρ_max = 0.81 e Å⁻³
5551 reflections	Δρ_min = −0.59 e Å⁻³
370 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.64849 (3)	0.28126 (2)	0.12506 (2)	0.03004 (9)
Sn2	0.42902 (3)	−0.01234 (2)	0.09813 (2)	0.02829 (9)
Cl1	0.36275 (18)	0.18206 (12)	0.44052 (12)	0.0831 (5)
Cl2	0.8211 (2)	0.19683 (14)	−0.20870 (14)	0.1118 (7)
O1	0.5054 (3)	0.2782 (2)	0.2235 (2)	0.0383 (8)
O2	0.4600 (3)	0.1147 (2)	0.2565 (2)	0.0392 (8)
O3	0.7429 (3)	0.2483 (2)	−0.0057 (2)	0.0379 (8)
O4	0.8784 (4)	0.4294 (3)	0.0608 (3)	0.0715 (12)
O5	0.5589 (3)	0.10884 (18)	0.0586 (2)	0.0285 (7)
C1	0.4706 (4)	0.2167 (4)	0.2781 (3)	0.0315 (10)
C2	0.4360 (5)	0.2750 (3)	0.3763 (3)	0.0454 (13)
H2A	0.3700	0.3104	0.3532	0.055*
H2B	0.5217	0.3351	0.4291	0.055*
C3	0.8232 (5)	0.3343 (4)	−0.0136 (4)	0.0457 (13)
C4	0.8540 (6)	0.3327 (4)	−0.1197 (4)	0.082 (2)
H4A	0.9524	0.3793	−0.1021	0.098*
H4B	0.7970	0.3673	−0.1571	0.098*
C5	0.5445 (4)	0.3777 (3)	0.0550 (3)	0.0399 (12)
H5A	0.5691	0.3829	−0.0096	0.048*
H5B	0.4430	0.3385	0.0327	0.048*
C6	0.5849 (5)	0.4954 (3)	0.1341 (4)	0.0417 (12)
C7	0.5036 (6)	0.5190 (4)	0.1995 (4)	0.0570 (14)
H7	0.4217	0.4615	0.1926	0.068*
C8	0.5428 (7)	0.6268 (5)	0.2745 (5)	0.0718 (18)
H8	0.4860	0.6415	0.3165	0.086*
C9	0.6644 (7)	0.7124 (4)	0.2878 (5)	0.0757 (19)
H9	0.6917	0.7842	0.3401	0.091*
C10	0.7446 (6)	0.6917 (4)	0.2242 (4)	0.0681 (17)
H10	0.8261	0.7501	0.2318	0.082*
C11	0.7060 (5)	0.5837 (4)	0.1477 (4)	0.0536 (14)
H11	0.7626	0.5706	0.1051	0.064*
C12	0.8304 (4)	0.3392 (4)	0.2657 (3)	0.0464 (13)
H12A	0.8584	0.2747	0.2687	0.056*
H12B	0.9069	0.3945	0.2560	0.056*
C13	0.8156 (4)	0.3925 (4)	0.3739 (4)	0.0396 (12)
C14	0.8072 (5)	0.3359 (4)	0.4463 (4)	0.0579 (14)
H14	0.8108	0.2630	0.4278	0.069*
C15	0.7936 (6)	0.3835 (6)	0.5458 (5)	0.0804 (19)
H15	0.7890	0.3431	0.5938	0.097*
C16	0.7869 (6)	0.4895 (6)	0.5742 (5)	0.082 (2)
H16	0.7772	0.5218	0.6413	0.098*
C17	0.7944 (6)	0.5473 (5)	0.5041 (5)	0.080 (2)
H17	0.7899	0.6198	0.5232	0.096*
C18	0.8088 (5)	0.5004 (4)	0.4042 (4)	0.0581 (14)
H18	0.8140	0.5416	0.3569	0.070*
C19	0.5469 (4)	−0.0892 (3)	0.1865 (4)	0.0439 (12)
H19A	0.4798	−0.1469	0.2018	0.053*
H19B	0.5862	−0.1292	0.1374	0.053*
C20	0.6649 (5)	−0.0187 (3)	0.2916 (4)	0.0375 (11)
C21	0.6393 (6)	0.0059 (4)	0.3895 (4)	0.0545 (14)
H21	0.5465	−0.0156	0.3897	0.065*
C22	0.7473 (8)	0.0612 (5)	0.4867 (5)	0.0797 (19)
H22	0.7268	0.0766	0.5517	0.096*
C23	0.8841 (8)	0.0940 (5)	0.4894 (5)	0.087 (2)
H23	0.9570	0.1303	0.5559	0.105*
C24	0.9137 (6)	0.0732 (5)	0.3939 (6)	0.0766 (18)
H24	1.0070	0.0963	0.3948	0.092*
C25	0.8041 (5)	0.0174 (4)	0.2952 (4)	0.0532 (14)
H25	0.8249	0.0041	0.2302	0.064*
C26	0.2178 (4)	−0.0210 (3)	0.0304 (4)	0.0426 (12)
H26A	0.1959	−0.0431	−0.0482	0.051*
H26B	0.1548	−0.0822	0.0445	0.051*
C27	0.1819 (4)	0.0827 (3)	0.0679 (4)	0.0348 (11)
C28	0.1365 (4)	0.1037 (4)	0.1589 (4)	0.0433 (12)
H28	0.1303	0.0535	0.1977	0.052*
C29	0.1008 (5)	0.1986 (4)	0.1918 (4)	0.0530 (14)
H29	0.0704	0.2117	0.2524	0.064*
C30	0.1097 (5)	0.2725 (4)	0.1365 (4)	0.0578 (15)
H30	0.0862	0.3363	0.1596	0.069*
C31	0.1532 (5)	0.2540 (4)	0.0466 (4)	0.0554 (14)
H31	0.1588	0.3047	0.0085	0.066*
C32	0.1886 (4)	0.1591 (4)	0.0132 (4)	0.0473 (13)
H32	0.2178	0.1466	−0.0480	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03285 (19)	0.02216 (15)	0.02845 (19)	0.00660 (14)	0.00873 (15)	0.00303 (14)
Sn2	0.03113 (18)	0.02562 (16)	0.02665 (19)	0.00911 (13)	0.01113 (15)	0.00652 (14)
Cl1	0.1243 (14)	0.0792 (10)	0.0594 (10)	0.0315 (10)	0.0595 (10)	0.0254 (9)
Cl2	0.1501 (17)	0.1002 (12)	0.0655 (12)	0.0180 (12)	0.0631 (12)	0.0037 (10)
O1	0.0420 (19)	0.0355 (16)	0.0381 (19)	0.0139 (14)	0.0196 (16)	0.0084 (15)
O2	0.059 (2)	0.0364 (17)	0.0247 (18)	0.0227 (15)	0.0155 (16)	0.0069 (15)
O3	0.0494 (19)	0.0318 (16)	0.0343 (19)	0.0119 (15)	0.0240 (16)	0.0085 (15)
O4	0.083 (3)	0.0391 (19)	0.072 (3)	−0.0024 (19)	0.038 (2)	0.0014 (19)
O5	0.0342 (16)	0.0197 (13)	0.0275 (16)	0.0057 (12)	0.0137 (13)	0.0026 (13)
C1	0.022 (2)	0.041 (3)	0.027 (3)	0.013 (2)	0.003 (2)	0.008 (2)
C2	0.053 (3)	0.045 (3)	0.033 (3)	0.017 (2)	0.020 (3)	0.002 (2)
C3	0.049 (3)	0.041 (3)	0.061 (4)	0.019 (2)	0.034 (3)	0.024 (3)
C4	0.105 (5)	0.062 (3)	0.072 (4)	0.001 (3)	0.054 (4)	0.024 (3)
C5	0.042 (3)	0.035 (2)	0.039 (3)	0.013 (2)	0.010 (2)	0.010 (2)
C6	0.056 (3)	0.033 (2)	0.039 (3)	0.022 (2)	0.012 (3)	0.013 (2)
C7	0.070 (4)	0.050 (3)	0.058 (4)	0.031 (3)	0.025 (3)	0.017 (3)
C8	0.109 (5)	0.064 (4)	0.064 (4)	0.054 (4)	0.041 (4)	0.018 (3)
C9	0.133 (6)	0.039 (3)	0.051 (4)	0.036 (4)	0.022 (4)	0.010 (3)
C10	0.091 (5)	0.038 (3)	0.060 (4)	0.010 (3)	0.018 (4)	0.015 (3)
C11	0.067 (4)	0.038 (3)	0.054 (4)	0.020 (3)	0.015 (3)	0.017 (3)
C12	0.037 (3)	0.056 (3)	0.041 (3)	0.017 (2)	0.011 (2)	0.009 (3)
C13	0.029 (3)	0.043 (3)	0.028 (3)	0.008 (2)	−0.005 (2)	−0.001 (2)
C14	0.063 (4)	0.059 (3)	0.049 (4)	0.024 (3)	0.013 (3)	0.017 (3)
C15	0.077 (5)	0.114 (5)	0.048 (4)	0.029 (4)	0.017 (4)	0.033 (4)
C16	0.060 (4)	0.108 (6)	0.037 (4)	0.015 (4)	0.007 (3)	−0.015 (4)
C17	0.079 (5)	0.062 (4)	0.071 (5)	0.027 (3)	0.014 (4)	−0.015 (4)
C18	0.065 (4)	0.051 (3)	0.045 (3)	0.019 (3)	0.008 (3)	0.007 (3)
C19	0.044 (3)	0.034 (2)	0.043 (3)	0.014 (2)	−0.001 (2)	0.011 (2)
C20	0.052 (3)	0.031 (2)	0.031 (3)	0.019 (2)	0.008 (2)	0.012 (2)
C21	0.070 (4)	0.048 (3)	0.048 (4)	0.018 (3)	0.020 (3)	0.022 (3)
C22	0.126 (6)	0.067 (4)	0.038 (4)	0.036 (4)	0.011 (4)	0.018 (3)
C23	0.108 (6)	0.059 (4)	0.056 (5)	0.023 (4)	−0.028 (4)	0.015 (4)
C24	0.052 (4)	0.069 (4)	0.088 (5)	0.016 (3)	−0.004 (4)	0.024 (4)
C25	0.059 (4)	0.050 (3)	0.055 (4)	0.023 (3)	0.020 (3)	0.020 (3)
C26	0.032 (3)	0.040 (3)	0.039 (3)	0.009 (2)	0.003 (2)	−0.001 (2)
C27	0.020 (2)	0.033 (2)	0.039 (3)	0.0040 (19)	0.004 (2)	0.004 (2)
C28	0.031 (3)	0.047 (3)	0.045 (3)	0.013 (2)	0.009 (2)	0.010 (2)
C29	0.042 (3)	0.063 (3)	0.046 (3)	0.025 (3)	0.013 (3)	0.000 (3)
C30	0.041 (3)	0.047 (3)	0.069 (4)	0.022 (3)	0.008 (3)	−0.003 (3)
C31	0.049 (3)	0.049 (3)	0.069 (4)	0.018 (3)	0.016 (3)	0.023 (3)
C32	0.040 (3)	0.051 (3)	0.046 (3)	0.015 (2)	0.017 (3)	0.010 (3)

Geometric parameters (Å, º) top

Sn1—O5	2.024 (2)	C13—C14	1.363 (6)
Sn1—C12	2.131 (4)	C13—C18	1.384 (6)
Sn1—C5	2.132 (4)	C14—C15	1.376 (6)
Sn1—O1	2.205 (3)	C14—H14	0.9300
Sn1—O3	2.206 (2)	C15—C16	1.359 (7)
Sn2—O5	2.037 (2)	C15—H15	0.9300
Sn2—C19	2.135 (4)	C16—C17	1.348 (8)
Sn2—C26	2.142 (4)	C16—H16	0.9300
Sn2—O5ⁱ	2.202 (2)	C17—C18	1.381 (6)
Sn2—O2	2.217 (2)	C17—H17	0.9300
Cl1—C2	1.759 (4)	C18—H18	0.9300
Cl2—C4	1.745 (5)	C19—C20	1.497 (5)
O1—C1	1.251 (4)	C19—H19A	0.9700
O2—C1	1.249 (4)	C19—H19B	0.9700
O3—C3	1.239 (4)	C20—C21	1.372 (6)
O4—C3	1.247 (5)	C20—C25	1.380 (6)
O5—Sn2ⁱ	2.202 (2)	C21—C22	1.367 (7)
C1—C2	1.514 (5)	C21—H21	0.9300
C2—H2A	0.9700	C22—C23	1.359 (8)
C2—H2B	0.9700	C22—H22	0.9300
C3—C4	1.523 (6)	C23—C24	1.361 (7)
C4—H4A	0.9700	C23—H23	0.9300
C4—H4B	0.9700	C24—C25	1.388 (7)
C5—C6	1.497 (5)	C24—H24	0.9300
C5—H5A	0.9700	C25—H25	0.9300
C5—H5B	0.9700	C26—C27	1.495 (5)
C6—C11	1.383 (6)	C26—H26A	0.9700
C6—C7	1.389 (6)	C26—H26B	0.9700
C7—C8	1.380 (6)	C27—C32	1.374 (6)
C7—H7	0.9300	C27—C28	1.397 (5)
C8—C9	1.369 (7)	C28—C29	1.384 (6)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.354 (7)	C29—C30	1.352 (6)
C9—H9	0.9300	C29—H29	0.9300
C10—C11	1.391 (6)	C30—C31	1.369 (6)
C10—H10	0.9300	C30—H30	0.9300
C11—H11	0.9300	C31—C32	1.383 (6)
C12—C13	1.501 (5)	C31—H31	0.9300
C12—H12A	0.9700	C32—H32	0.9300
C12—H12B	0.9700

O5—Sn1—C12	112.97 (14)	Sn1—C12—H12A	108.1
O5—Sn1—C5	117.57 (13)	C13—C12—H12B	108.1
C12—Sn1—C5	129.31 (16)	Sn1—C12—H12B	108.1
O5—Sn1—O1	88.99 (9)	H12A—C12—H12B	107.3
C12—Sn1—O1	92.54 (13)	C14—C13—C18	117.3 (4)
C5—Sn1—O1	84.79 (14)	C14—C13—C12	121.1 (4)
O5—Sn1—O3	79.27 (9)	C18—C13—C12	121.6 (5)
C12—Sn1—O3	100.37 (13)	C13—C14—C15	121.8 (5)
C5—Sn1—O3	92.56 (13)	C13—C14—H14	119.1
O1—Sn1—O3	165.15 (10)	C15—C14—H14	119.1
O5—Sn2—C19	110.68 (14)	C16—C15—C14	120.2 (6)
O5—Sn2—C26	107.18 (14)	C16—C15—H15	119.9
C19—Sn2—C26	142.10 (17)	C14—C15—H15	119.9
O5—Sn2—O5ⁱ	76.12 (9)	C17—C16—C15	119.2 (6)
C19—Sn2—O5ⁱ	92.46 (13)	C17—C16—H16	120.4
C26—Sn2—O5ⁱ	94.86 (13)	C15—C16—H16	120.4
O5—Sn2—O2	91.45 (9)	C16—C17—C18	121.1 (6)
C19—Sn2—O2	88.45 (13)	C16—C17—H17	119.5
C26—Sn2—O2	92.33 (13)	C18—C17—H17	119.5
O5ⁱ—Sn2—O2	167.03 (9)	C17—C18—C13	120.4 (5)
C1—O1—Sn1	131.6 (3)	C17—C18—H18	119.8
C1—O2—Sn2	129.1 (3)	C13—C18—H18	119.8
C3—O3—Sn1	115.4 (3)	C20—C19—Sn2	121.1 (3)
Sn1—O5—Sn2	133.37 (12)	C20—C19—H19A	107.1
Sn1—O5—Sn2ⁱ	122.44 (11)	Sn2—C19—H19A	107.1
Sn2—O5—Sn2ⁱ	103.88 (9)	C20—C19—H19B	107.1
O2—C1—O1	125.8 (4)	Sn2—C19—H19B	107.1
O2—C1—C2	119.9 (4)	H19A—C19—H19B	106.8
O1—C1—C2	114.3 (4)	C21—C20—C25	117.2 (5)
C1—C2—Cl1	113.8 (3)	C21—C20—C19	121.0 (5)
C1—C2—H2A	108.8	C25—C20—C19	121.6 (4)
Cl1—C2—H2A	108.8	C22—C21—C20	121.5 (5)
C1—C2—H2B	108.8	C22—C21—H21	119.2
Cl1—C2—H2B	108.8	C20—C21—H21	119.2
H2A—C2—H2B	107.7	C23—C22—C21	120.8 (6)
O3—C3—O4	123.6 (4)	C23—C22—H22	119.6
O3—C3—C4	121.5 (4)	C21—C22—H22	119.6
O4—C3—C4	114.8 (4)	C24—C23—C22	119.5 (6)
C3—C4—Cl2	114.5 (3)	C24—C23—H23	120.3
C3—C4—H4A	108.6	C22—C23—H23	120.3
Cl2—C4—H4A	108.6	C23—C24—C25	119.7 (6)
C3—C4—H4B	108.6	C23—C24—H24	120.1
Cl2—C4—H4B	108.6	C25—C24—H24	120.1
H4A—C4—H4B	107.6	C20—C25—C24	121.3 (5)
C6—C5—Sn1	111.6 (3)	C20—C25—H25	119.4
C6—C5—H5A	109.3	C24—C25—H25	119.4
Sn1—C5—H5A	109.3	C27—C26—Sn2	119.1 (3)
C6—C5—H5B	109.3	C27—C26—H26A	107.6
Sn1—C5—H5B	109.3	Sn2—C26—H26A	107.6
H5A—C5—H5B	108.0	C27—C26—H26B	107.6
C11—C6—C7	117.4 (4)	Sn2—C26—H26B	107.6
C11—C6—C5	121.8 (4)	H26A—C26—H26B	107.0
C7—C6—C5	120.8 (4)	C32—C27—C28	117.5 (4)
C8—C7—C6	120.8 (5)	C32—C27—C26	121.7 (4)
C8—C7—H7	119.6	C28—C27—C26	120.8 (4)
C6—C7—H7	119.6	C29—C28—C27	120.4 (5)
C9—C8—C7	120.7 (5)	C29—C28—H28	119.8
C9—C8—H8	119.6	C27—C28—H28	119.8
C7—C8—H8	119.6	C30—C29—C28	120.5 (5)
C10—C9—C8	119.5 (5)	C30—C29—H29	119.8
C10—C9—H9	120.3	C28—C29—H29	119.8
C8—C9—H9	120.3	C29—C30—C31	120.5 (5)
C9—C10—C11	120.5 (5)	C29—C30—H30	119.7
C9—C10—H10	119.8	C31—C30—H30	119.7
C11—C10—H10	119.8	C30—C31—C32	119.3 (5)
C6—C11—C10	121.1 (5)	C30—C31—H31	120.4
C6—C11—H11	119.5	C32—C31—H31	120.4
C10—C11—H11	119.5	C27—C32—C31	121.8 (4)
C13—C12—Sn1	116.7 (3)	C27—C32—H32	119.1
C13—C12—H12A	108.1	C31—C32—H32	119.1

O5—Sn1—O1—C1	45.3 (3)	C7—C8—C9—C10	2.0 (9)
C12—Sn1—O1—C1	−67.7 (4)	C8—C9—C10—C11	−1.5 (9)
C5—Sn1—O1—C1	163.1 (4)	C7—C6—C11—C10	0.2 (7)
O3—Sn1—O1—C1	82.8 (6)	C5—C6—C11—C10	−177.8 (5)
O5—Sn2—O2—C1	38.0 (3)	C9—C10—C11—C6	0.5 (8)
C19—Sn2—O2—C1	148.6 (4)	O5—Sn1—C12—C13	−108.9 (3)
C26—Sn2—O2—C1	−69.3 (4)	C5—Sn1—C12—C13	66.4 (4)
O5ⁱ—Sn2—O2—C1	54.4 (7)	O1—Sn1—C12—C13	−18.9 (3)
O5—Sn1—O3—C3	178.8 (3)	O3—Sn1—C12—C13	168.5 (3)
C12—Sn1—O3—C3	−69.5 (4)	Sn1—C12—C13—C14	106.5 (4)
C5—Sn1—O3—C3	61.2 (3)	Sn1—C12—C13—C18	−73.0 (5)
O1—Sn1—O3—C3	140.5 (4)	C18—C13—C14—C15	−0.5 (7)
C12—Sn1—O5—Sn2	79.0 (2)	C12—C13—C14—C15	−180.0 (5)
C5—Sn1—O5—Sn2	−96.9 (2)	C13—C14—C15—C16	0.6 (9)
O1—Sn1—O5—Sn2	−13.3 (2)	C14—C15—C16—C17	−0.3 (10)
O3—Sn1—O5—Sn2	175.8 (2)	C15—C16—C17—C18	0.0 (10)
C12—Sn1—O5—Sn2ⁱ	−108.46 (17)	C16—C17—C18—C13	0.1 (9)
C5—Sn1—O5—Sn2ⁱ	75.62 (19)	C14—C13—C18—C17	0.1 (7)
O1—Sn1—O5—Sn2ⁱ	159.21 (15)	C12—C13—C18—C17	179.6 (4)
O3—Sn1—O5—Sn2ⁱ	−11.65 (14)	O5—Sn2—C19—C20	58.2 (4)
C19—Sn2—O5—Sn1	−99.1 (2)	C26—Sn2—C19—C20	−124.6 (3)
C26—Sn2—O5—Sn1	82.6 (2)	O5ⁱ—Sn2—C19—C20	134.3 (4)
O5ⁱ—Sn2—O5—Sn1	173.5 (3)	O2—Sn2—C19—C20	−32.8 (4)
O2—Sn2—O5—Sn1	−10.2 (2)	Sn2—C19—C20—C21	86.8 (5)
C19—Sn2—O5—Sn2ⁱ	87.36 (15)	Sn2—C19—C20—C25	−97.7 (5)
C26—Sn2—O5—Sn2ⁱ	−90.86 (14)	C25—C20—C21—C22	−1.7 (7)
O5ⁱ—Sn2—O5—Sn2ⁱ	0.0	C19—C20—C21—C22	174.0 (4)
O2—Sn2—O5—Sn2ⁱ	176.25 (12)	C20—C21—C22—C23	0.1 (9)
Sn2—O2—C1—O1	−21.5 (6)	C21—C22—C23—C24	1.2 (9)
Sn2—O2—C1—C2	156.7 (3)	C22—C23—C24—C25	−1.0 (9)
Sn1—O1—C1—O2	−32.2 (6)	C21—C20—C25—C24	1.9 (7)
Sn1—O1—C1—C2	149.5 (3)	C19—C20—C25—C24	−173.7 (4)
O2—C1—C2—Cl1	−7.2 (5)	C23—C24—C25—C20	−0.7 (8)
O1—C1—C2—Cl1	171.2 (3)	O5—Sn2—C26—C27	−61.4 (4)
Sn1—O3—C3—O4	18.4 (6)	C19—Sn2—C26—C27	121.3 (4)
Sn1—O3—C3—C4	−157.4 (4)	O5ⁱ—Sn2—C26—C27	−138.4 (3)
O3—C3—C4—Cl2	−21.1 (7)	O2—Sn2—C26—C27	30.8 (4)
O4—C3—C4—Cl2	162.7 (4)	Sn2—C26—C27—C32	93.4 (5)
O5—Sn1—C5—C6	157.5 (3)	Sn2—C26—C27—C28	−88.4 (4)
C12—Sn1—C5—C6	−17.6 (4)	C32—C27—C28—C29	−0.3 (6)
O1—Sn1—C5—C6	71.4 (3)	C26—C27—C28—C29	−178.7 (4)
O3—Sn1—C5—C6	−123.3 (3)	C27—C28—C29—C30	−0.2 (7)
Sn1—C5—C6—C11	84.2 (5)	C28—C29—C30—C31	0.5 (8)
Sn1—C5—C6—C7	−93.7 (5)	C29—C30—C31—C32	−0.3 (7)
C11—C6—C7—C8	0.3 (8)	C28—C27—C32—C31	0.5 (6)
C5—C6—C7—C8	178.2 (5)	C26—C27—C32—C31	178.9 (4)
C6—C7—C8—C9	−1.3 (9)	C30—C31—C32—C27	−0.2 (7)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4	0.93	2.49	3.229 (6)	136
C4—H4A···O4ⁱⁱ	0.97	2.44	3.291 (5)	146

Symmetry code: (ii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Sn₄(C₇H₇)₈(C₂H₂ClO₂)₄O₂]
M_r	1609.71
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.4377 (8), 13.0091 (9), 13.3920 (11)
α, β, γ (°)	104.920 (2), 103.208 (1), 106.498 (1)
V (Å³)	1593.0 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.77
Crystal size (mm)	0.20 × 0.13 × 0.08

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS, Sheldrick, 1996)
T_min, T_max	0.718, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	8386, 5551, 4110
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.054, 1.01
No. of reflections	5551
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.59

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4	0.93	2.49	3.229 (6)	136
C4—H4A···O4ⁱ	0.97	2.44	3.291 (5)	146

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053), the National Basic Research Program (No. 2010CB234601) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

Gielen, M., Vanbellinghen, C., Gelan, J. & Willem, R. (1988). Bul. Soc. Chim. Belg. 97, 873–876. 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
Teoh, S.-G., Kok, L.-Y. & Looi, E.-S. (2002). J. Coord. Chem. 55, 697–703. Web of Science CSD CrossRef CAS Google Scholar

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