metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Gielen, M., Vanbellinghen, C., Gelan, J. & Willem, R. (1988). Bul. Soc. Chim. Belg. 97, 873-876.]). For a related structure, see: Teoh et al. (2002[Teoh, S.-G., Kok, L.-Y. & Looi, E.-S. (2002). J. Coord. Chem. 55, 697-703.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn4(C7H7)8(C2H2ClO2)4O2]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.718, Tmax = 0.871

  • 8386 measured reflections

  • 5551 independent reflections

  • 4110 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.054

  • S = 1.01

  • 5551 reflections

  • 370 parameters

  • H-atom parameters constrained

  • Δρmax = 0.81 e Å−3

  • Δρmin = −0.59 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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%.

Refinement top

All H atoms were positioned geometrically and refined as riding on their parent atoms, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C).

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
[Figure 1] 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.
[Figure 2] 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
Mr = 1609.71F(000) = 796
Triclinic, P1Dx = 1.678 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4377 (8) ÅCell parameters from 3277 reflections
b = 13.0091 (9) Åθ = 2.8–26.3°
c = 13.3920 (11) ŵ = 1.77 mm1
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 tube4110 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
phi and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS, Sheldrick, 1996)
h = 1212
Tmin = 0.718, Tmax = 0.871k = 1515
8386 measured reflectionsl = 1115
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0103P)2]
where P = (Fo2 + 2Fc2)/3
5551 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.59 e Å3
Crystal data top
[Sn4(C7H7)8(C2H2ClO2)4O2]γ = 106.498 (1)°
Mr = 1609.71V = 1593.0 (2) Å3
Triclinic, P1Z = 1
a = 10.4377 (8) ÅMo Kα radiation
b = 13.0091 (9) ŵ = 1.77 mm1
c = 13.3920 (11) ÅT = 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)
Tmin = 0.718, Tmax = 0.871Rint = 0.023
8386 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.054H-atom parameters constrained
S = 1.01Δρmax = 0.81 e Å3
5551 reflectionsΔρmin = 0.59 e Å3
370 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.64849 (3)0.28126 (2)0.12506 (2)0.03004 (9)
Sn20.42902 (3)0.01234 (2)0.09813 (2)0.02829 (9)
Cl10.36275 (18)0.18206 (12)0.44052 (12)0.0831 (5)
Cl20.8211 (2)0.19683 (14)0.20870 (14)0.1118 (7)
O10.5054 (3)0.2782 (2)0.2235 (2)0.0383 (8)
O20.4600 (3)0.1147 (2)0.2565 (2)0.0392 (8)
O30.7429 (3)0.2483 (2)0.0057 (2)0.0379 (8)
O40.8784 (4)0.4294 (3)0.0608 (3)0.0715 (12)
O50.5589 (3)0.10884 (18)0.0586 (2)0.0285 (7)
C10.4706 (4)0.2167 (4)0.2781 (3)0.0315 (10)
C20.4360 (5)0.2750 (3)0.3763 (3)0.0454 (13)
H2A0.37000.31040.35320.055*
H2B0.52170.33510.42910.055*
C30.8232 (5)0.3343 (4)0.0136 (4)0.0457 (13)
C40.8540 (6)0.3327 (4)0.1197 (4)0.082 (2)
H4A0.95240.37930.10210.098*
H4B0.79700.36730.15710.098*
C50.5445 (4)0.3777 (3)0.0550 (3)0.0399 (12)
H5A0.56910.38290.00960.048*
H5B0.44300.33850.03270.048*
C60.5849 (5)0.4954 (3)0.1341 (4)0.0417 (12)
C70.5036 (6)0.5190 (4)0.1995 (4)0.0570 (14)
H70.42170.46150.19260.068*
C80.5428 (7)0.6268 (5)0.2745 (5)0.0718 (18)
H80.48600.64150.31650.086*
C90.6644 (7)0.7124 (4)0.2878 (5)0.0757 (19)
H90.69170.78420.34010.091*
C100.7446 (6)0.6917 (4)0.2242 (4)0.0681 (17)
H100.82610.75010.23180.082*
C110.7060 (5)0.5837 (4)0.1477 (4)0.0536 (14)
H110.76260.57060.10510.064*
C120.8304 (4)0.3392 (4)0.2657 (3)0.0464 (13)
H12A0.85840.27470.26870.056*
H12B0.90690.39450.25600.056*
C130.8156 (4)0.3925 (4)0.3739 (4)0.0396 (12)
C140.8072 (5)0.3359 (4)0.4463 (4)0.0579 (14)
H140.81080.26300.42780.069*
C150.7936 (6)0.3835 (6)0.5458 (5)0.0804 (19)
H150.78900.34310.59380.097*
C160.7869 (6)0.4895 (6)0.5742 (5)0.082 (2)
H160.77720.52180.64130.098*
C170.7944 (6)0.5473 (5)0.5041 (5)0.080 (2)
H170.78990.61980.52320.096*
C180.8088 (5)0.5004 (4)0.4042 (4)0.0581 (14)
H180.81400.54160.35690.070*
C190.5469 (4)0.0892 (3)0.1865 (4)0.0439 (12)
H19A0.47980.14690.20180.053*
H19B0.58620.12920.13740.053*
C200.6649 (5)0.0187 (3)0.2916 (4)0.0375 (11)
C210.6393 (6)0.0059 (4)0.3895 (4)0.0545 (14)
H210.54650.01560.38970.065*
C220.7473 (8)0.0612 (5)0.4867 (5)0.0797 (19)
H220.72680.07660.55170.096*
C230.8841 (8)0.0940 (5)0.4894 (5)0.087 (2)
H230.95700.13030.55590.105*
C240.9137 (6)0.0732 (5)0.3939 (6)0.0766 (18)
H241.00700.09630.39480.092*
C250.8041 (5)0.0174 (4)0.2952 (4)0.0532 (14)
H250.82490.00410.23020.064*
C260.2178 (4)0.0210 (3)0.0304 (4)0.0426 (12)
H26A0.19590.04310.04820.051*
H26B0.15480.08220.04450.051*
C270.1819 (4)0.0827 (3)0.0679 (4)0.0348 (11)
C280.1365 (4)0.1037 (4)0.1589 (4)0.0433 (12)
H280.13030.05350.19770.052*
C290.1008 (5)0.1986 (4)0.1918 (4)0.0530 (14)
H290.07040.21170.25240.064*
C300.1097 (5)0.2725 (4)0.1365 (4)0.0578 (15)
H300.08620.33630.15960.069*
C310.1532 (5)0.2540 (4)0.0466 (4)0.0554 (14)
H310.15880.30470.00850.066*
C320.1886 (4)0.1591 (4)0.0132 (4)0.0473 (13)
H320.21780.14660.04800.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03285 (19)0.02216 (15)0.02845 (19)0.00660 (14)0.00873 (15)0.00303 (14)
Sn20.03113 (18)0.02562 (16)0.02665 (19)0.00911 (13)0.01113 (15)0.00652 (14)
Cl10.1243 (14)0.0792 (10)0.0594 (10)0.0315 (10)0.0595 (10)0.0254 (9)
Cl20.1501 (17)0.1002 (12)0.0655 (12)0.0180 (12)0.0631 (12)0.0037 (10)
O10.0420 (19)0.0355 (16)0.0381 (19)0.0139 (14)0.0196 (16)0.0084 (15)
O20.059 (2)0.0364 (17)0.0247 (18)0.0227 (15)0.0155 (16)0.0069 (15)
O30.0494 (19)0.0318 (16)0.0343 (19)0.0119 (15)0.0240 (16)0.0085 (15)
O40.083 (3)0.0391 (19)0.072 (3)0.0024 (19)0.038 (2)0.0014 (19)
O50.0342 (16)0.0197 (13)0.0275 (16)0.0057 (12)0.0137 (13)0.0026 (13)
C10.022 (2)0.041 (3)0.027 (3)0.013 (2)0.003 (2)0.008 (2)
C20.053 (3)0.045 (3)0.033 (3)0.017 (2)0.020 (3)0.002 (2)
C30.049 (3)0.041 (3)0.061 (4)0.019 (2)0.034 (3)0.024 (3)
C40.105 (5)0.062 (3)0.072 (4)0.001 (3)0.054 (4)0.024 (3)
C50.042 (3)0.035 (2)0.039 (3)0.013 (2)0.010 (2)0.010 (2)
C60.056 (3)0.033 (2)0.039 (3)0.022 (2)0.012 (3)0.013 (2)
C70.070 (4)0.050 (3)0.058 (4)0.031 (3)0.025 (3)0.017 (3)
C80.109 (5)0.064 (4)0.064 (4)0.054 (4)0.041 (4)0.018 (3)
C90.133 (6)0.039 (3)0.051 (4)0.036 (4)0.022 (4)0.010 (3)
C100.091 (5)0.038 (3)0.060 (4)0.010 (3)0.018 (4)0.015 (3)
C110.067 (4)0.038 (3)0.054 (4)0.020 (3)0.015 (3)0.017 (3)
C120.037 (3)0.056 (3)0.041 (3)0.017 (2)0.011 (2)0.009 (3)
C130.029 (3)0.043 (3)0.028 (3)0.008 (2)0.005 (2)0.001 (2)
C140.063 (4)0.059 (3)0.049 (4)0.024 (3)0.013 (3)0.017 (3)
C150.077 (5)0.114 (5)0.048 (4)0.029 (4)0.017 (4)0.033 (4)
C160.060 (4)0.108 (6)0.037 (4)0.015 (4)0.007 (3)0.015 (4)
C170.079 (5)0.062 (4)0.071 (5)0.027 (3)0.014 (4)0.015 (4)
C180.065 (4)0.051 (3)0.045 (3)0.019 (3)0.008 (3)0.007 (3)
C190.044 (3)0.034 (2)0.043 (3)0.014 (2)0.001 (2)0.011 (2)
C200.052 (3)0.031 (2)0.031 (3)0.019 (2)0.008 (2)0.012 (2)
C210.070 (4)0.048 (3)0.048 (4)0.018 (3)0.020 (3)0.022 (3)
C220.126 (6)0.067 (4)0.038 (4)0.036 (4)0.011 (4)0.018 (3)
C230.108 (6)0.059 (4)0.056 (5)0.023 (4)0.028 (4)0.015 (4)
C240.052 (4)0.069 (4)0.088 (5)0.016 (3)0.004 (4)0.024 (4)
C250.059 (4)0.050 (3)0.055 (4)0.023 (3)0.020 (3)0.020 (3)
C260.032 (3)0.040 (3)0.039 (3)0.009 (2)0.003 (2)0.001 (2)
C270.020 (2)0.033 (2)0.039 (3)0.0040 (19)0.004 (2)0.004 (2)
C280.031 (3)0.047 (3)0.045 (3)0.013 (2)0.009 (2)0.010 (2)
C290.042 (3)0.063 (3)0.046 (3)0.025 (3)0.013 (3)0.000 (3)
C300.041 (3)0.047 (3)0.069 (4)0.022 (3)0.008 (3)0.003 (3)
C310.049 (3)0.049 (3)0.069 (4)0.018 (3)0.016 (3)0.023 (3)
C320.040 (3)0.051 (3)0.046 (3)0.015 (2)0.017 (3)0.010 (3)
Geometric parameters (Å, º) top
Sn1—O52.024 (2)C13—C141.363 (6)
Sn1—C122.131 (4)C13—C181.384 (6)
Sn1—C52.132 (4)C14—C151.376 (6)
Sn1—O12.205 (3)C14—H140.9300
Sn1—O32.206 (2)C15—C161.359 (7)
Sn2—O52.037 (2)C15—H150.9300
Sn2—C192.135 (4)C16—C171.348 (8)
Sn2—C262.142 (4)C16—H160.9300
Sn2—O5i2.202 (2)C17—C181.381 (6)
Sn2—O22.217 (2)C17—H170.9300
Cl1—C21.759 (4)C18—H180.9300
Cl2—C41.745 (5)C19—C201.497 (5)
O1—C11.251 (4)C19—H19A0.9700
O2—C11.249 (4)C19—H19B0.9700
O3—C31.239 (4)C20—C211.372 (6)
O4—C31.247 (5)C20—C251.380 (6)
O5—Sn2i2.202 (2)C21—C221.367 (7)
C1—C21.514 (5)C21—H210.9300
C2—H2A0.9700C22—C231.359 (8)
C2—H2B0.9700C22—H220.9300
C3—C41.523 (6)C23—C241.361 (7)
C4—H4A0.9700C23—H230.9300
C4—H4B0.9700C24—C251.388 (7)
C5—C61.497 (5)C24—H240.9300
C5—H5A0.9700C25—H250.9300
C5—H5B0.9700C26—C271.495 (5)
C6—C111.383 (6)C26—H26A0.9700
C6—C71.389 (6)C26—H26B0.9700
C7—C81.380 (6)C27—C321.374 (6)
C7—H70.9300C27—C281.397 (5)
C8—C91.369 (7)C28—C291.384 (6)
C8—H80.9300C28—H280.9300
C9—C101.354 (7)C29—C301.352 (6)
C9—H90.9300C29—H290.9300
C10—C111.391 (6)C30—C311.369 (6)
C10—H100.9300C30—H300.9300
C11—H110.9300C31—C321.383 (6)
C12—C131.501 (5)C31—H310.9300
C12—H12A0.9700C32—H320.9300
C12—H12B0.9700
O5—Sn1—C12112.97 (14)Sn1—C12—H12A108.1
O5—Sn1—C5117.57 (13)C13—C12—H12B108.1
C12—Sn1—C5129.31 (16)Sn1—C12—H12B108.1
O5—Sn1—O188.99 (9)H12A—C12—H12B107.3
C12—Sn1—O192.54 (13)C14—C13—C18117.3 (4)
C5—Sn1—O184.79 (14)C14—C13—C12121.1 (4)
O5—Sn1—O379.27 (9)C18—C13—C12121.6 (5)
C12—Sn1—O3100.37 (13)C13—C14—C15121.8 (5)
C5—Sn1—O392.56 (13)C13—C14—H14119.1
O1—Sn1—O3165.15 (10)C15—C14—H14119.1
O5—Sn2—C19110.68 (14)C16—C15—C14120.2 (6)
O5—Sn2—C26107.18 (14)C16—C15—H15119.9
C19—Sn2—C26142.10 (17)C14—C15—H15119.9
O5—Sn2—O5i76.12 (9)C17—C16—C15119.2 (6)
C19—Sn2—O5i92.46 (13)C17—C16—H16120.4
C26—Sn2—O5i94.86 (13)C15—C16—H16120.4
O5—Sn2—O291.45 (9)C16—C17—C18121.1 (6)
C19—Sn2—O288.45 (13)C16—C17—H17119.5
C26—Sn2—O292.33 (13)C18—C17—H17119.5
O5i—Sn2—O2167.03 (9)C17—C18—C13120.4 (5)
C1—O1—Sn1131.6 (3)C17—C18—H18119.8
C1—O2—Sn2129.1 (3)C13—C18—H18119.8
C3—O3—Sn1115.4 (3)C20—C19—Sn2121.1 (3)
Sn1—O5—Sn2133.37 (12)C20—C19—H19A107.1
Sn1—O5—Sn2i122.44 (11)Sn2—C19—H19A107.1
Sn2—O5—Sn2i103.88 (9)C20—C19—H19B107.1
O2—C1—O1125.8 (4)Sn2—C19—H19B107.1
O2—C1—C2119.9 (4)H19A—C19—H19B106.8
O1—C1—C2114.3 (4)C21—C20—C25117.2 (5)
C1—C2—Cl1113.8 (3)C21—C20—C19121.0 (5)
C1—C2—H2A108.8C25—C20—C19121.6 (4)
Cl1—C2—H2A108.8C22—C21—C20121.5 (5)
C1—C2—H2B108.8C22—C21—H21119.2
Cl1—C2—H2B108.8C20—C21—H21119.2
H2A—C2—H2B107.7C23—C22—C21120.8 (6)
O3—C3—O4123.6 (4)C23—C22—H22119.6
O3—C3—C4121.5 (4)C21—C22—H22119.6
O4—C3—C4114.8 (4)C24—C23—C22119.5 (6)
C3—C4—Cl2114.5 (3)C24—C23—H23120.3
C3—C4—H4A108.6C22—C23—H23120.3
Cl2—C4—H4A108.6C23—C24—C25119.7 (6)
C3—C4—H4B108.6C23—C24—H24120.1
Cl2—C4—H4B108.6C25—C24—H24120.1
H4A—C4—H4B107.6C20—C25—C24121.3 (5)
C6—C5—Sn1111.6 (3)C20—C25—H25119.4
C6—C5—H5A109.3C24—C25—H25119.4
Sn1—C5—H5A109.3C27—C26—Sn2119.1 (3)
C6—C5—H5B109.3C27—C26—H26A107.6
Sn1—C5—H5B109.3Sn2—C26—H26A107.6
H5A—C5—H5B108.0C27—C26—H26B107.6
C11—C6—C7117.4 (4)Sn2—C26—H26B107.6
C11—C6—C5121.8 (4)H26A—C26—H26B107.0
C7—C6—C5120.8 (4)C32—C27—C28117.5 (4)
C8—C7—C6120.8 (5)C32—C27—C26121.7 (4)
C8—C7—H7119.6C28—C27—C26120.8 (4)
C6—C7—H7119.6C29—C28—C27120.4 (5)
C9—C8—C7120.7 (5)C29—C28—H28119.8
C9—C8—H8119.6C27—C28—H28119.8
C7—C8—H8119.6C30—C29—C28120.5 (5)
C10—C9—C8119.5 (5)C30—C29—H29119.8
C10—C9—H9120.3C28—C29—H29119.8
C8—C9—H9120.3C29—C30—C31120.5 (5)
C9—C10—C11120.5 (5)C29—C30—H30119.7
C9—C10—H10119.8C31—C30—H30119.7
C11—C10—H10119.8C30—C31—C32119.3 (5)
C6—C11—C10121.1 (5)C30—C31—H31120.4
C6—C11—H11119.5C32—C31—H31120.4
C10—C11—H11119.5C27—C32—C31121.8 (4)
C13—C12—Sn1116.7 (3)C27—C32—H32119.1
C13—C12—H12A108.1C31—C32—H32119.1
O5—Sn1—O1—C145.3 (3)C7—C8—C9—C102.0 (9)
C12—Sn1—O1—C167.7 (4)C8—C9—C10—C111.5 (9)
C5—Sn1—O1—C1163.1 (4)C7—C6—C11—C100.2 (7)
O3—Sn1—O1—C182.8 (6)C5—C6—C11—C10177.8 (5)
O5—Sn2—O2—C138.0 (3)C9—C10—C11—C60.5 (8)
C19—Sn2—O2—C1148.6 (4)O5—Sn1—C12—C13108.9 (3)
C26—Sn2—O2—C169.3 (4)C5—Sn1—C12—C1366.4 (4)
O5i—Sn2—O2—C154.4 (7)O1—Sn1—C12—C1318.9 (3)
O5—Sn1—O3—C3178.8 (3)O3—Sn1—C12—C13168.5 (3)
C12—Sn1—O3—C369.5 (4)Sn1—C12—C13—C14106.5 (4)
C5—Sn1—O3—C361.2 (3)Sn1—C12—C13—C1873.0 (5)
O1—Sn1—O3—C3140.5 (4)C18—C13—C14—C150.5 (7)
C12—Sn1—O5—Sn279.0 (2)C12—C13—C14—C15180.0 (5)
C5—Sn1—O5—Sn296.9 (2)C13—C14—C15—C160.6 (9)
O1—Sn1—O5—Sn213.3 (2)C14—C15—C16—C170.3 (10)
O3—Sn1—O5—Sn2175.8 (2)C15—C16—C17—C180.0 (10)
C12—Sn1—O5—Sn2i108.46 (17)C16—C17—C18—C130.1 (9)
C5—Sn1—O5—Sn2i75.62 (19)C14—C13—C18—C170.1 (7)
O1—Sn1—O5—Sn2i159.21 (15)C12—C13—C18—C17179.6 (4)
O3—Sn1—O5—Sn2i11.65 (14)O5—Sn2—C19—C2058.2 (4)
C19—Sn2—O5—Sn199.1 (2)C26—Sn2—C19—C20124.6 (3)
C26—Sn2—O5—Sn182.6 (2)O5i—Sn2—C19—C20134.3 (4)
O5i—Sn2—O5—Sn1173.5 (3)O2—Sn2—C19—C2032.8 (4)
O2—Sn2—O5—Sn110.2 (2)Sn2—C19—C20—C2186.8 (5)
C19—Sn2—O5—Sn2i87.36 (15)Sn2—C19—C20—C2597.7 (5)
C26—Sn2—O5—Sn2i90.86 (14)C25—C20—C21—C221.7 (7)
O5i—Sn2—O5—Sn2i0.0C19—C20—C21—C22174.0 (4)
O2—Sn2—O5—Sn2i176.25 (12)C20—C21—C22—C230.1 (9)
Sn2—O2—C1—O121.5 (6)C21—C22—C23—C241.2 (9)
Sn2—O2—C1—C2156.7 (3)C22—C23—C24—C251.0 (9)
Sn1—O1—C1—O232.2 (6)C21—C20—C25—C241.9 (7)
Sn1—O1—C1—C2149.5 (3)C19—C20—C25—C24173.7 (4)
O2—C1—C2—Cl17.2 (5)C23—C24—C25—C200.7 (8)
O1—C1—C2—Cl1171.2 (3)O5—Sn2—C26—C2761.4 (4)
Sn1—O3—C3—O418.4 (6)C19—Sn2—C26—C27121.3 (4)
Sn1—O3—C3—C4157.4 (4)O5i—Sn2—C26—C27138.4 (3)
O3—C3—C4—Cl221.1 (7)O2—Sn2—C26—C2730.8 (4)
O4—C3—C4—Cl2162.7 (4)Sn2—C26—C27—C3293.4 (5)
O5—Sn1—C5—C6157.5 (3)Sn2—C26—C27—C2888.4 (4)
C12—Sn1—C5—C617.6 (4)C32—C27—C28—C290.3 (6)
O1—Sn1—C5—C671.4 (3)C26—C27—C28—C29178.7 (4)
O3—Sn1—C5—C6123.3 (3)C27—C28—C29—C300.2 (7)
Sn1—C5—C6—C1184.2 (5)C28—C29—C30—C310.5 (8)
Sn1—C5—C6—C793.7 (5)C29—C30—C31—C320.3 (7)
C11—C6—C7—C80.3 (8)C28—C27—C32—C310.5 (6)
C5—C6—C7—C8178.2 (5)C26—C27—C32—C31178.9 (4)
C6—C7—C8—C91.3 (9)C30—C31—C32—C270.2 (7)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O40.932.493.229 (6)136
C4—H4A···O4ii0.972.443.291 (5)146
Symmetry code: (ii) x+2, y+1, z.

Experimental details

Crystal data
Chemical formula[Sn4(C7H7)8(C2H2ClO2)4O2]
Mr1609.71
Crystal system, space groupTriclinic, 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)
V3)1593.0 (2)
Z1
Radiation typeMo Kα
µ (mm1)1.77
Crystal size (mm)0.20 × 0.13 × 0.08
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS, Sheldrick, 1996)
Tmin, Tmax0.718, 0.871
No. of measured, independent and
observed [I > 2σ(I)] reflections
8386, 5551, 4110
Rint0.023
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.054, 1.01
No. of reflections5551
No. of parameters370
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C11—H11···O40.932.493.229 (6)136
C4—H4A···O4i0.972.443.291 (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

First citationGielen, M., Vanbellinghen, C., Gelan, J. & Willem, R. (1988). Bul. Soc. Chim. Belg. 97, 873–876.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationTeoh, 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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