Octa­kis(2-chloro­benz­yl)di-μ2-hydroxido-di-μ3-oxido-bis­(2-phenyl­acetato)tetra­tin(IV)

Peng, W.-B.; Li, G.-Q.; Yin, H.; Zhao, X.

doi:10.1107/S1600536810012559

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages m535-m536

https://doi.org/10.1107/S1600536810012559

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Octakis(2-chlorobenzyl)di-μ₂-hydroxido-di-μ₃-oxido-bis(2-phenylacetato)tetratin(IV)

Wei-Bing Peng,^a Guo-Qiang Li,^a Handong Yin ^b ^* and Xianhe Zhao ^b

^aKey Laboratory of Marine Drugs, Chinese Ministry of Education, Marine Drug and Food Institute, Ocean University of China, Qingdao 266003, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: guoqiangliouc@163.com

(Received 24 March 2010; accepted 3 April 2010; online 17 April 2010)

The asymmetric unit of the title compound, [Sn₄(C₇H₆Cl)₈(C₈H₇O₂)₂O₂(OH)₂], comprises one-half of the centrosymmetric tin(IV) complex. μ₃-Oxide and μ₂-hydroxide bridges link the four five-coordinate Sn^IV atoms to generate three fused four-membered Sn—O—Sn—O rings in a ladder-like structure. The two endocyclic Sn atoms each bind to two μ₃-oxide anions and a μ₂-hydroxide ligand, together with two 2-chlorobenzyl groups. The exocyclic Sn atoms each carry a monodentate phenylacetate ligand, two 2-chlorobenzyl groups, and μ₃-oxide and μ₂-hydroxide ligands. Both types of Sn atoms adopt a distorted trigonal–bipyramidal coordination geometry. The molecular conformation is stabilized by intramolecular O—H⋯O interactions involving the μ₂-hydroxide ligands and the C=O group of the phenylacetate ligand.

Related literature

For the antifungal activity of organotin compounds, see: Ruzicka et al. (2002 ); Nath et al. (1999 ). For a related structure, see: Wu et al. (2009 ).

Experimental

Crystal data

[Sn₄(C₇H₆Cl)₈(C₈H₇O₂)₂O₂(OH)₂]
M_r = 1815.59
Triclinic, $[P \overline 1]$
a = 10.7095 (14) Å
b = 11.4846 (16) Å
c = 15.2412 (18) Å
α = 98.311 (2)°
β = 90.982 (1)°
γ = 98.404 (2)°
V = 1833.6 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.69 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.40 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.491, T_max = 0.551
9422 measured reflections
6322 independent reflections
4437 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.121
S = 1.05
6322 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O3	2.023 (4)
Sn1—O2	2.114 (4)
Sn1—C9	2.145 (6)
Sn1—C16	2.145 (7)
Sn1—O4	2.157 (3)
Sn2—O4	2.033 (4)
Sn2—O4ⁱ	2.089 (3)
Sn2—C30	2.146 (6)
Sn2—O3	2.163 (4)
Sn2—C23	2.165 (6)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.82	1.78	2.554 (7)	157

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/S1600536810012559/sj2764sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012559/sj2764Isup2.hkl

checkCIF report

Comment top

Recently considerable attention has been paid to organotin(IV) derivatives, owing to their high in vitro antifungal activities against some medically important fungi (Ruzicka et al., 2002; Nath et al., 1999). As a continuation of our study of organotin compounds, we present here the synthesis and crystal structure of the title compound (I).

The title compound (Fig. 1, Table 1) is a centrosymmetric dimer and displays a ladder type structural motif. The ladder consists of four tin centers held together by two µ₃-oxygen atoms. According to their different coordination environments, the four tin atoms can be divided into two types, viz. two endocyclic and two exocyclic. The endo- and exocyclic tin centers are linked by µ₂-hydroxide anions and µ₃-oxide anions. Each of the tin atoms is five-coordinate, adopting approximate trigonal bipyramidal coordination. The 2-phenylacetato ligands coordinate to the exocyclic tin atoms in a monodentate fashion, and the molecular conformation is stabilized by intramolecular O3—H3···O1 hydrogen bonds (Table 2). The crystal structure of a similiar compound has been reported recently (Wu et al., 2009).

Related literature top

For the antifungal activity of organotin compounds, see: Ruzicka et al. (2002); Nath et al. (1999). For a related structure, see: Wu et al. (2009).

Experimental top

The reaction was carried out under a nitrogen atmosphere. 2-phenylacetic acid (2 mmol) and sodium ethoxide (2.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Bis(2-chlorobenzyl)dichlorostannane (4 mmol) was then added to the reactor. After stirring for 10 h at 323 K, a white paste was obtained and filtered off. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of dichloromethane/methanol (1:1 v/v) solution over a period of six days (yield 86%. m.p. 438 K ).

Structure description top

For the antifungal activity of organotin compounds, see: Ruzicka et al. (2002); Nath et al. (1999). For a related structure, see: Wu et al. (2009).

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 (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Octakis(2-chlorobenzyl)di-µ₂-hydroxido-di-µ₃-oxido- bis(2-phenylacetato)tetratin(IV) top

Crystal data top

[Sn₄(C₇H₆Cl)₈(C₈H₇O₂)₂O₂(OH)₂]	Z = 1
M_r = 1815.59	F(000) = 896
Triclinic, P1	D_x = 1.644 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7095 (14) Å	Cell parameters from 4098 reflections
b = 11.4846 (16) Å	θ = 2.3–27.0°
c = 15.2412 (18) Å	µ = 1.69 mm⁻¹
α = 98.311 (2)°	T = 298 K
β = 90.982 (1)°	Block, colourless
γ = 98.404 (2)°	0.49 × 0.48 × 0.40 mm
V = 1833.6 (4) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	6322 independent reflections
Radiation source: fine-focus sealed tube	4437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.491, T_max = 0.551	k = −7→13
9422 measured reflections	l = −18→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0507P)² + 2.5952P] where P = (F_o² + 2F_c²)/3
6322 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 1.18 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Sn₄(C₇H₆Cl)₈(C₈H₇O₂)₂O₂(OH)₂]	γ = 98.404 (2)°
M_r = 1815.59	V = 1833.6 (4) Å³
Triclinic, P1	Z = 1
a = 10.7095 (14) Å	Mo Kα radiation
b = 11.4846 (16) Å	µ = 1.69 mm⁻¹
c = 15.2412 (18) Å	T = 298 K
α = 98.311 (2)°	0.49 × 0.48 × 0.40 mm
β = 90.982 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	6322 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4437 reflections with I > 2σ(I)
T_min = 0.491, T_max = 0.551	R_int = 0.027
9422 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	Δρ_max = 1.18 e Å⁻³
6322 reflections	Δρ_min = −0.70 e Å⁻³
415 parameters

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

	x	y	z	U_iso*/U_eq
Sn2	0.37891 (4)	0.50151 (4)	0.43671 (3)	0.03405 (14)
Sn1	0.52617 (4)	0.29250 (4)	0.32149 (3)	0.03909 (15)
O1	0.2765 (5)	0.2430 (7)	0.1747 (4)	0.108 (3)
Cl1	0.7318 (2)	0.0520 (2)	0.31794 (16)	0.0817 (7)
Cl3	0.1945 (2)	0.7643 (2)	0.47210 (16)	0.0889 (7)
O4	0.5297 (4)	0.4138 (3)	0.4439 (2)	0.0333 (9)
O3	0.3714 (4)	0.3739 (4)	0.3168 (3)	0.0457 (11)
H3	0.3230	0.3382	0.2763	0.069*
C24	0.1584 (6)	0.3003 (6)	0.4525 (5)	0.0455 (16)
C30	0.3829 (6)	0.6432 (6)	0.3587 (4)	0.0424 (15)
H30A	0.4072	0.7196	0.3957	0.051*
H30B	0.4431	0.6349	0.3122	0.051*
O2	0.4756 (5)	0.2118 (4)	0.1896 (3)	0.0555 (13)
C26	0.1527 (8)	0.0966 (8)	0.4741 (7)	0.077 (3)
H26	0.1734	0.0419	0.5092	0.093*
C20	0.4618 (10)	−0.1761 (7)	0.1799 (6)	0.077 (3)
H20	0.4560	−0.2425	0.1363	0.092*
C36	0.2531 (6)	0.6347 (6)	0.3195 (4)	0.0416 (15)
C2	0.3728 (9)	0.1342 (8)	0.0521 (5)	0.078 (3)
H2A	0.4492	0.1657	0.0250	0.094*
H2B	0.3766	0.0512	0.0559	0.094*
C32	0.0369 (8)	0.6721 (9)	0.3344 (7)	0.087 (3)
H32	−0.0233	0.7094	0.3661	0.104*
C23	0.1962 (6)	0.4311 (6)	0.4814 (5)	0.0479 (17)
H23A	0.1975	0.4470	0.5457	0.057*
H23B	0.1328	0.4728	0.4590	0.057*
C31	0.1583 (7)	0.6850 (7)	0.3675 (5)	0.059 (2)
C17	0.4781 (7)	0.0212 (6)	0.3103 (4)	0.0475 (17)
C18	0.5837 (7)	−0.0225 (6)	0.2777 (5)	0.0513 (18)
C1	0.3705 (8)	0.2012 (7)	0.1456 (5)	0.058 (2)
C16	0.4855 (7)	0.1312 (6)	0.3779 (4)	0.0505 (18)
H16A	0.5508	0.1298	0.4226	0.061*
H16B	0.4058	0.1304	0.4073	0.061*
C28	0.0522 (8)	0.1387 (11)	0.3465 (6)	0.089 (3)
H28	0.0067	0.1113	0.2932	0.107*
C25	0.1922 (7)	0.2164 (7)	0.4999 (5)	0.0556 (19)
C22	0.3625 (8)	−0.0376 (7)	0.2728 (5)	0.063 (2)
H22	0.2887	−0.0098	0.2917	0.075*
C35	0.2176 (8)	0.5672 (7)	0.2378 (5)	0.064 (2)
H35	0.2773	0.5319	0.2041	0.076*
C29	0.0866 (7)	0.2605 (8)	0.3724 (5)	0.067 (2)
H29	0.0628	0.3145	0.3378	0.081*
C19	0.5779 (9)	−0.1213 (7)	0.2139 (5)	0.068 (2)
H19	0.6511	−0.1498	0.1944	0.082*
C21	0.3545 (9)	−0.1354 (7)	0.2086 (6)	0.074 (3)
H21	0.2761	−0.1736	0.1849	0.089*
Cl4	0.2865 (2)	0.2618 (2)	0.59644 (16)	0.0855 (7)
Cl2	0.5677 (3)	0.5040 (3)	0.1524 (2)	0.1111 (10)
C15	0.8327 (7)	0.2995 (7)	0.1657 (5)	0.064 (2)
H15	0.8699	0.2630	0.2078	0.077*
C10	0.7379 (7)	0.3672 (6)	0.1912 (4)	0.0533 (19)
C9	0.7019 (6)	0.3859 (6)	0.2859 (4)	0.0531 (19)
H9A	0.7004	0.4704	0.3031	0.064*
H9B	0.7687	0.3647	0.3215	0.064*
C3	0.2613 (8)	0.1411 (7)	−0.0071 (4)	0.058 (2)
C11	0.6853 (8)	0.4162 (7)	0.1265 (5)	0.065 (2)
C14	0.8730 (9)	0.2849 (8)	0.0798 (7)	0.083 (3)
H14	0.9381	0.2412	0.0647	0.100*
C4	0.2413 (9)	0.2473 (8)	−0.0274 (6)	0.078 (3)
H4	0.2943	0.3160	−0.0024	0.093*
C27	0.0837 (9)	0.0588 (9)	0.3973 (8)	0.090 (3)
H27	0.0577	−0.0222	0.3794	0.108*
C13	0.8155 (11)	0.3359 (9)	0.0172 (6)	0.094 (4)
H13	0.8412	0.3257	−0.0410	0.112*
C8	0.1816 (11)	0.0414 (8)	−0.0418 (6)	0.099 (3)
H8	0.1937	−0.0325	−0.0279	0.119*
C7	0.0792 (11)	0.0515 (12)	−0.0997 (7)	0.106 (4)
H7	0.0231	−0.0159	−0.1231	0.127*
C12	0.7206 (10)	0.4017 (9)	0.0394 (6)	0.087 (3)
H12	0.6811	0.4357	−0.0032	0.104*
C34	0.0942 (10)	0.5521 (9)	0.2061 (7)	0.087 (3)
H34	0.0711	0.5061	0.1513	0.105*
C33	0.0056 (10)	0.6040 (11)	0.2544 (9)	0.103 (4)
H33	−0.0774	0.5925	0.2323	0.124*
C5	0.1443 (11)	0.2550 (11)	−0.0843 (7)	0.098 (3)
H5	0.1334	0.3291	−0.0985	0.118*
C6	0.0637 (10)	0.1576 (14)	−0.1206 (6)	0.101 (4)
H6	−0.0018	0.1643	−0.1595	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn2	0.0364 (2)	0.0383 (3)	0.0277 (2)	0.00952 (19)	−0.00245 (17)	0.00236 (18)
Sn1	0.0458 (3)	0.0380 (3)	0.0327 (3)	0.0095 (2)	0.00195 (19)	−0.00089 (19)
O1	0.050 (4)	0.200 (8)	0.062 (4)	0.038 (4)	−0.011 (3)	−0.038 (4)
Cl1	0.0591 (13)	0.0889 (17)	0.0930 (17)	0.0115 (11)	0.0016 (12)	−0.0006 (13)
Cl3	0.0980 (18)	0.0925 (18)	0.0805 (16)	0.0418 (14)	0.0156 (13)	−0.0022 (13)
O4	0.040 (2)	0.035 (2)	0.025 (2)	0.0114 (18)	−0.0045 (17)	0.0011 (17)
O3	0.046 (3)	0.049 (3)	0.038 (2)	0.014 (2)	−0.009 (2)	−0.012 (2)
C24	0.035 (4)	0.048 (4)	0.052 (4)	0.002 (3)	0.007 (3)	0.009 (3)
C30	0.043 (4)	0.046 (4)	0.041 (4)	0.013 (3)	0.000 (3)	0.011 (3)
O2	0.072 (3)	0.050 (3)	0.042 (3)	0.010 (3)	−0.007 (3)	−0.005 (2)
C26	0.071 (6)	0.062 (6)	0.104 (8)	0.009 (5)	0.025 (5)	0.025 (5)
C20	0.111 (8)	0.047 (5)	0.067 (6)	0.004 (5)	−0.004 (6)	−0.001 (4)
C36	0.046 (4)	0.039 (4)	0.042 (4)	0.003 (3)	−0.006 (3)	0.016 (3)
C2	0.106 (7)	0.085 (6)	0.041 (5)	0.029 (5)	−0.004 (4)	−0.011 (4)
C32	0.054 (5)	0.109 (8)	0.112 (8)	0.016 (5)	−0.001 (5)	0.061 (7)
C23	0.041 (4)	0.056 (4)	0.048 (4)	0.009 (3)	0.008 (3)	0.009 (3)
C31	0.047 (4)	0.065 (5)	0.074 (5)	0.014 (4)	−0.002 (4)	0.031 (4)
C17	0.059 (4)	0.038 (4)	0.048 (4)	0.008 (3)	0.006 (3)	0.011 (3)
C18	0.057 (4)	0.049 (4)	0.048 (4)	0.009 (3)	0.002 (3)	0.005 (3)
C1	0.075 (6)	0.056 (5)	0.036 (4)	0.004 (4)	−0.009 (4)	−0.005 (3)
C16	0.068 (5)	0.038 (4)	0.048 (4)	0.011 (3)	0.015 (4)	0.008 (3)
C28	0.067 (6)	0.115 (9)	0.064 (6)	−0.026 (6)	0.010 (5)	−0.022 (6)
C25	0.046 (4)	0.056 (5)	0.065 (5)	0.002 (4)	0.019 (4)	0.011 (4)
C22	0.062 (5)	0.054 (5)	0.073 (5)	0.008 (4)	0.006 (4)	0.011 (4)
C35	0.082 (6)	0.059 (5)	0.049 (5)	−0.002 (4)	−0.021 (4)	0.018 (4)
C29	0.055 (5)	0.077 (6)	0.063 (5)	−0.001 (4)	0.007 (4)	−0.002 (4)
C19	0.089 (6)	0.055 (5)	0.063 (5)	0.027 (5)	0.016 (5)	−0.001 (4)
C21	0.084 (7)	0.050 (5)	0.080 (6)	−0.012 (5)	−0.013 (5)	0.006 (4)
Cl4	0.0702 (14)	0.1108 (19)	0.0823 (16)	0.0166 (13)	−0.0149 (12)	0.0361 (14)
Cl2	0.127 (2)	0.114 (2)	0.118 (2)	0.0578 (18)	0.0473 (18)	0.0594 (18)
C15	0.070 (5)	0.051 (5)	0.070 (5)	0.011 (4)	0.019 (4)	0.002 (4)
C10	0.063 (5)	0.051 (4)	0.039 (4)	−0.011 (4)	0.015 (3)	−0.002 (3)
C9	0.051 (4)	0.057 (5)	0.043 (4)	−0.005 (3)	0.007 (3)	−0.005 (3)
C3	0.079 (5)	0.064 (5)	0.032 (4)	0.019 (4)	−0.001 (4)	−0.003 (3)
C11	0.081 (6)	0.053 (5)	0.061 (5)	0.010 (4)	0.019 (4)	0.010 (4)
C14	0.098 (7)	0.066 (6)	0.082 (7)	0.008 (5)	0.041 (6)	−0.003 (5)
C4	0.099 (7)	0.070 (6)	0.064 (6)	0.020 (5)	0.000 (5)	0.002 (5)
C27	0.079 (7)	0.064 (6)	0.115 (9)	−0.015 (5)	0.043 (7)	−0.007 (6)
C13	0.144 (10)	0.074 (7)	0.054 (6)	−0.007 (7)	0.045 (6)	−0.002 (5)
C8	0.150 (10)	0.058 (6)	0.080 (7)	−0.002 (6)	−0.030 (7)	0.004 (5)
C7	0.114 (9)	0.111 (10)	0.077 (7)	−0.010 (7)	−0.028 (6)	−0.010 (7)
C12	0.119 (8)	0.088 (7)	0.053 (5)	0.009 (6)	0.018 (5)	0.015 (5)
C34	0.092 (7)	0.085 (7)	0.078 (7)	−0.024 (6)	−0.039 (6)	0.034 (5)
C33	0.058 (6)	0.125 (10)	0.130 (10)	−0.024 (6)	−0.039 (7)	0.077 (8)
C5	0.116 (9)	0.121 (10)	0.071 (7)	0.053 (7)	−0.007 (6)	0.024 (6)
C6	0.089 (8)	0.160 (12)	0.055 (6)	0.037 (8)	−0.008 (5)	0.006 (7)

Geometric parameters (Å, º) top

Sn1—O3	2.023 (4)	C18—C19	1.377 (10)
Sn1—O2	2.114 (4)	C16—H16A	0.9700
Sn1—C9	2.145 (6)	C16—H16B	0.9700
Sn1—C16	2.145 (7)	C28—C27	1.356 (14)
Sn1—O4	2.157 (3)	C28—C29	1.390 (12)
Sn2—O4	2.033 (4)	C28—H28	0.9300
Sn2—O4ⁱ	2.089 (3)	C25—Cl4	1.740 (8)
Sn2—C30	2.146 (6)	C22—C21	1.369 (11)
Sn2—O3	2.163 (4)	C22—H22	0.9300
Sn2—C23	2.165 (6)	C35—C34	1.377 (11)
Sn2—Sn2ⁱ	3.2130 (8)	C35—H35	0.9300
O1—C1	1.238 (9)	C29—H29	0.9300
Cl1—C18	1.745 (7)	C19—H19	0.9300
Cl3—C31	1.725 (8)	C21—H21	0.9300
O4—Sn2ⁱ	2.089 (3)	Cl2—C11	1.741 (8)
O3—H3	0.8200	C15—C14	1.379 (11)
C24—C25	1.370 (10)	C15—C10	1.395 (10)
C24—C29	1.412 (10)	C15—H15	0.9300
C24—C23	1.496 (9)	C10—C11	1.357 (11)
C30—C36	1.487 (8)	C10—C9	1.494 (9)
C30—H30A	0.9700	C9—H9A	0.9700
C30—H30B	0.9700	C9—H9B	0.9700
O2—C1	1.281 (8)	C3—C4	1.346 (11)
C26—C27	1.355 (13)	C3—C8	1.357 (11)
C26—C25	1.377 (11)	C11—C12	1.380 (11)
C26—H26	0.9300	C14—C13	1.371 (14)
C20—C21	1.359 (12)	C14—H14	0.9300
C20—C19	1.366 (11)	C4—C5	1.362 (12)
C20—H20	0.9300	C4—H4	0.9300
C36—C35	1.384 (9)	C27—H27	0.9300
C36—C31	1.405 (10)	C13—C12	1.371 (14)
C2—C3	1.503 (11)	C13—H13	0.9300
C2—C1	1.521 (9)	C8—C7	1.425 (14)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C7—C6	1.335 (15)
C32—C33	1.358 (14)	C7—H7	0.9300
C32—C31	1.366 (11)	C12—H12	0.9300
C32—H32	0.9300	C34—C33	1.364 (15)
C23—H23A	0.9700	C34—H34	0.9300
C23—H23B	0.9700	C33—H33	0.9300
C17—C18	1.374 (9)	C5—C6	1.352 (14)
C17—C22	1.392 (10)	C5—H5	0.9300
C17—C16	1.502 (9)	C6—H6	0.9300

O4—Sn2—O4ⁱ	77.61 (16)	C17—C16—H16A	109.0
O4—Sn2—C30	120.9 (2)	Sn1—C16—H16A	109.0
O4ⁱ—Sn2—C30	103.2 (2)	C17—C16—H16B	109.0
O4—Sn2—O3	72.95 (15)	Sn1—C16—H16B	109.0
O4ⁱ—Sn2—O3	150.47 (16)	H16A—C16—H16B	107.8
C30—Sn2—O3	90.1 (2)	C27—C28—C29	121.5 (9)
O4—Sn2—C23	121.1 (2)	C27—C28—H28	119.3
O4ⁱ—Sn2—C23	101.5 (2)	C29—C28—H28	119.3
C30—Sn2—C23	116.6 (3)	C24—C25—C26	121.9 (8)
O3—Sn2—C23	95.6 (2)	C24—C25—Cl4	119.4 (6)
O4—Sn2—Sn2ⁱ	39.43 (10)	C26—C25—Cl4	118.7 (7)
O4ⁱ—Sn2—Sn2ⁱ	38.18 (11)	C21—C22—C17	121.7 (8)
C30—Sn2—Sn2ⁱ	118.26 (17)	C21—C22—H22	119.2
O3—Sn2—Sn2ⁱ	112.35 (11)	C17—C22—H22	119.2
C23—Sn2—Sn2ⁱ	117.14 (19)	C34—C35—C36	120.4 (9)
O3—Sn1—O2	86.93 (17)	C34—C35—H35	119.8
O3—Sn1—C9	117.5 (3)	C36—C35—H35	119.8
O2—Sn1—C9	93.6 (2)	C28—C29—C24	118.5 (9)
O3—Sn1—C16	111.2 (2)	C28—C29—H29	120.8
O2—Sn1—C16	95.2 (2)	C24—C29—H29	120.8
C9—Sn1—C16	130.8 (3)	C20—C19—C18	118.2 (8)
O3—Sn1—O4	73.29 (15)	C20—C19—H19	120.9
O2—Sn1—O4	159.50 (18)	C18—C19—H19	120.9
C9—Sn1—O4	90.9 (2)	C20—C21—C22	119.6 (8)
C16—Sn1—O4	96.9 (2)	C20—C21—H21	120.2
Sn2—O4—Sn2ⁱ	102.39 (16)	C22—C21—H21	120.2
Sn2—O4—Sn1	106.75 (16)	C14—C15—C10	122.0 (9)
Sn2ⁱ—O4—Sn1	150.5 (2)	C14—C15—H15	119.0
Sn1—O3—Sn2	106.89 (18)	C10—C15—H15	119.0
Sn1—O3—H3	109.5	C11—C10—C15	116.4 (7)
Sn2—O3—H3	142.1	C11—C10—C9	123.4 (7)
C25—C24—C29	118.0 (7)	C15—C10—C9	120.2 (8)
C25—C24—C23	122.7 (6)	C10—C9—Sn1	118.6 (4)
C29—C24—C23	119.2 (7)	C10—C9—H9A	107.7
C36—C30—Sn2	106.7 (4)	Sn1—C9—H9A	107.7
C36—C30—H30A	110.4	C10—C9—H9B	107.7
Sn2—C30—H30A	110.4	Sn1—C9—H9B	107.7
C36—C30—H30B	110.4	H9A—C9—H9B	107.1
Sn2—C30—H30B	110.4	C4—C3—C8	119.5 (9)
H30A—C30—H30B	108.6	C4—C3—C2	119.6 (8)
C1—O2—Sn1	129.9 (5)	C8—C3—C2	120.9 (8)
C27—C26—C25	119.8 (9)	C10—C11—C12	123.5 (8)
C27—C26—H26	120.1	C10—C11—Cl2	119.6 (6)
C25—C26—H26	120.1	C12—C11—Cl2	116.8 (8)
C21—C20—C19	121.2 (8)	C13—C14—C15	118.9 (9)
C21—C20—H20	119.4	C13—C14—H14	120.5
C19—C20—H20	119.4	C15—C14—H14	120.5
C35—C36—C31	117.1 (7)	C3—C4—C5	120.6 (9)
C35—C36—C30	121.3 (7)	C3—C4—H4	119.7
C31—C36—C30	121.4 (6)	C5—C4—H4	119.7
C3—C2—C1	114.5 (7)	C26—C27—C28	120.2 (9)
C3—C2—H2A	108.6	C26—C27—H27	119.9
C1—C2—H2A	108.6	C28—C27—H27	119.9
C3—C2—H2B	108.6	C12—C13—C14	120.8 (8)
C1—C2—H2B	108.6	C12—C13—H13	119.6
H2A—C2—H2B	107.6	C14—C13—H13	119.6
C33—C32—C31	118.9 (10)	C3—C8—C7	119.1 (10)
C33—C32—H32	120.5	C3—C8—H8	120.5
C31—C32—H32	120.5	C7—C8—H8	120.5
C24—C23—Sn2	114.0 (4)	C6—C7—C8	120.2 (10)
C24—C23—H23A	108.8	C6—C7—H7	119.9
Sn2—C23—H23A	108.8	C8—C7—H7	119.9
C24—C23—H23B	108.8	C13—C12—C11	118.4 (10)
Sn2—C23—H23B	108.8	C13—C12—H12	120.8
H23A—C23—H23B	107.7	C11—C12—H12	120.8
C32—C31—C36	122.1 (8)	C33—C34—C35	120.6 (9)
C32—C31—Cl3	118.4 (7)	C33—C34—H34	119.7
C36—C31—Cl3	119.5 (5)	C35—C34—H34	119.7
C18—C17—C22	116.3 (6)	C32—C33—C34	120.9 (9)
C18—C17—C16	122.6 (6)	C32—C33—H33	119.5
C22—C17—C16	121.0 (7)	C34—C33—H33	119.5
C17—C18—C19	123.1 (7)	C6—C5—C4	121.5 (11)
C17—C18—Cl1	118.5 (5)	C6—C5—H5	119.2
C19—C18—Cl1	118.5 (6)	C4—C5—H5	119.2
O1—C1—O2	124.1 (6)	C7—C6—C5	119.1 (11)
O1—C1—C2	122.6 (7)	C7—C6—H6	120.5
O2—C1—C2	113.2 (7)	C5—C6—H6	120.5
C17—C16—Sn1	113.0 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	1.78	2.554 (7)	157

Experimental details

Crystal data
Chemical formula	[Sn₄(C₇H₆Cl)₈(C₈H₇O₂)₂O₂(OH)₂]
M_r	1815.59
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.7095 (14), 11.4846 (16), 15.2412 (18)
α, β, γ (°)	98.311 (2), 90.982 (1), 98.404 (2)
V (Å³)	1833.6 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.69
Crystal size (mm)	0.49 × 0.48 × 0.40

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.491, 0.551
No. of measured, independent and observed [I > 2σ(I)] reflections	9422, 6322, 4437
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.121, 1.05
No. of reflections	6322
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.70

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

Selected bond lengths (Å) top

Sn1—O3	2.023 (4)	Sn2—O4	2.033 (4)
Sn1—O2	2.114 (4)	Sn2—O4ⁱ	2.089 (3)
Sn1—C9	2.145 (6)	Sn2—C30	2.146 (6)
Sn1—C16	2.145 (7)	Sn2—O3	2.163 (4)
Sn1—O4	2.157 (3)	Sn2—C23	2.165 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	1.78	2.554 (7)	156.9

Acknowledgements

The authors acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. Y2008B48) for financial support.

References

Nath, M., Yadav, R., Eng, G. & Musigarimi, P. (1999). Appl. Organomet. Chem. 13, 29–37. CrossRef CAS Google Scholar
Ruzicka, A., Dostal, L. & Jambor, R. (2002). Appl. Organomet. Chem. 16, 315–322. 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 Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wu, X., Kang, W., Zhu, D., Zhu, C. & Liu, S. (2009). J. Organomet. Chem. 694, 2981–2986. Web of Science CSD CrossRef CAS Google Scholar

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