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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1494.
Published online 2009 October 31. doi:  10.1107/S1600536809045176
PMCID: PMC2971409

Dichloridoocta­kis(2-chloro­benz­yl)di-μ2-hydroxido-di-μ3-oxido-tetra­tin(IV)

Abstract

The title tetra­nuclear SnIV compound, [Sn4(C7H6Cl)8Cl2O2(OH)2], has site symmetry An external file that holds a picture, illustration, etc.
Object name is e-65-m1494-efi1.jpg. Two O2− and two OH anions bridge four SnIV cations to form the tetra­nuclear compound. The two independent SnIV cations assume SnO3C2 and SnO2C2Cl distorted trigonal-bipyramidal coordination geometries. Intra­molecular O—H(...)Cl hydrogen bonding is present in the structure. One Cl atom of a chloro­benzyl ligand is disordered over two sites with an occupancy ratio of 0.693 (2):0.307 (2).

Related literature

For a related structure, see: Li et al. (2006 [triangle]). For the corresponding bond distances in an organotin compound, see: Lo & Ng (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1494-scheme1.jpg

Experimental

Crystal data

  • [Sn4(C7H6Cl)8Cl2O2(OH)2]
  • M r = 1616.22
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1494-efi2.jpg
  • a = 10.986 (2) Å
  • b = 11.227 (2) Å
  • c = 13.573 (3) Å
  • α = 74.656 (2)°
  • β = 67.942 (2)°
  • γ = 75.753 (2)°
  • V = 1475.9 (6) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.17 mm−1
  • T = 298 K
  • 0.44 × 0.37 × 0.33 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.449, T max = 0.535
  • 7669 measured reflections
  • 5112 independent reflections
  • 3865 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.074
  • S = 1.04
  • 5112 reflections
  • 338 parameters
  • H-atom parameters constrained
  • Δρmax = 1.27 e Å−3
  • Δρmin = −0.57 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045176/xu2652sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045176/xu2652Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province, China (Y2008B48) for financial support.

supplementary crystallographic information

Comment

The title compound, (I), was obtained as an adventitious product of the partial hydrolysis of di(2-chlorobenzyl)dichloridotin(IV) during the attempted preparation of adducts of this tin precursor complex with 5-chlorosalicylaldehyde benzoyldrazone in benzene and ethanol. It crystallizes from dichloromethane and ethanol. From Fig. 1, it can be seen that complex (I) contains two independent penta-coordinated Sn atoms. It is a centrosymmetric complex, where one half of the molecule comprises the crystallographic asymmetric unit and the other half is generated by an inversion centre. Each of the two independent Sn atoms is five-coordinate, adopting approximate trigonal bipyramidal coordination (Table 1). These are similar to those in the related organotin compound (Li et al., 2006). The molecular conformation is stabilized by O1—H1···Cl2 hydrogen bond (Table 2). The Sn—C distances lie in the rather narrow range 2.126 (5)–2.149 (5) Å, which are closed to the corresponding distances reported in the organotin compound (Lo & Ng, 2009).

Experimental

Di(2-chlorobenzyl)dichloridotin(IV) (2 mmol) and 5-chlorosalicylaldehyde benzoyldrazone(2 mmol) was added to a solution of sodium methoxide (3 mmol) in benzene (15 ml) and ethanol (15 ml, 95%). The mixture was then heated under reflux with stirring for 5 h and the solvent was removed by evaporation in vacuo. The crude adduct was recrystallized from dichloromethane/ethanol and colourless crystals suitable for X-ray diffraction were obtained.

Refinement

The H atoms were positioned geometrically, with methylene C—H distances of 0.97 Å, aromatic C—H distances of 0.93 Å, O—H distances of 0.862 Å and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C,O). The Cl2 atom is disordered, the C2-phenyl part was refined as a rigid hexagon and the temperature factors of the carbon atoms were restrained to be nearly isotropic. The highest peak in the difference map is 1.21 Å apart from Cl1 atom.

Figures

Fig. 1.
The molecular structure of the compound showing 50% probability displacement ellipsoids [symmetry code: (A) = 1-x, 1-y, 1-z].

Crystal data

[Sn4(C7H6Cl)8Cl2O2(OH)2]Z = 1
Mr = 1616.22F(000) = 788
Triclinic, P1Dx = 1.818 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.986 (2) ÅCell parameters from 4036 reflections
b = 11.227 (2) Åθ = 2.6–27.4°
c = 13.573 (3) ŵ = 2.17 mm1
α = 74.656 (2)°T = 298 K
β = 67.942 (2)°Block, colourless
γ = 75.753 (2)°0.44 × 0.37 × 0.33 mm
V = 1475.9 (6) Å3

Data collection

Bruker SMART CCD area-detector diffractometer5112 independent reflections
Radiation source: fine-focus sealed tube3865 reflections with I > 2σ(I)
graphiteRint = 0.015
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.449, Tmax = 0.535k = −13→13
7669 measured reflectionsl = −16→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0262P)2 + 2.2448P] where P = (Fo2 + 2Fc2)/3
5112 reflections(Δ/σ)max = 0.001
338 parametersΔρmax = 1.27 e Å3
0 restraintsΔρmin = −0.57 e Å3

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

xyzUiso*/UeqOcc. (<1)
Sn10.59257 (3)0.37338 (3)0.44839 (2)0.03438 (10)
Sn20.49384 (3)0.58881 (3)0.25330 (2)0.03713 (10)
Cl10.35586 (14)0.79133 (11)0.28147 (11)0.0516 (3)
Cl20.6318 (2)0.0780 (2)0.34868 (19)0.0704 (6)0.693 (2)
Cl2'0.2326 (5)0.3325 (5)0.5648 (4)0.0704 (6)0.307 (2)
Cl30.96390 (18)0.40745 (16)0.17259 (15)0.0897 (6)
Cl40.09931 (19)0.5877 (2)0.36984 (14)0.0927 (6)
Cl50.6057 (2)0.72167 (16)−0.03870 (14)0.0908 (6)
O10.6121 (3)0.3933 (3)0.2815 (2)0.0444 (8)
H10.64080.32970.25030.053*
O20.4776 (3)0.5414 (3)0.4119 (2)0.0365 (7)
C10.4860 (7)0.2203 (6)0.5202 (5)0.077 (2)
H1A0.54860.14460.53140.092*
H1B0.42380.23360.59080.092*
C20.4103 (7)0.2003 (5)0.4555 (5)0.0597 (16)
C30.4702 (6)0.1302 (5)0.3739 (5)0.0646 (17)
H3A0.56050.09820.35880.077*0.307 (2)
C40.4013 (7)0.1078 (6)0.3160 (5)0.0697 (18)
H40.44400.05920.26290.084*
C50.2691 (8)0.1581 (7)0.3376 (6)0.078 (2)
H50.22100.14310.29980.093*
C60.2087 (7)0.2301 (6)0.4146 (6)0.0775 (19)
H60.11970.26630.42770.093*
C70.2776 (8)0.2497 (6)0.4731 (5)0.0724 (18)
H7A0.23350.29800.52630.087*0.693 (2)
C80.8018 (5)0.3527 (5)0.4200 (4)0.0541 (14)
H8A0.83370.42960.37660.065*
H8B0.81660.33770.48870.065*
C90.8788 (5)0.2460 (5)0.3625 (4)0.0469 (12)
C100.9489 (5)0.2595 (5)0.2531 (4)0.0510 (13)
C111.0141 (5)0.1589 (6)0.2019 (5)0.0630 (16)
H111.05980.17190.12780.076*
C121.0104 (6)0.0399 (6)0.2620 (6)0.080 (2)
H121.0524−0.02870.22850.096*
C130.9448 (7)0.0222 (6)0.3713 (7)0.086 (2)
H130.9450−0.05870.41210.103*
C140.8791 (6)0.1218 (6)0.4213 (5)0.0666 (16)
H140.83370.10740.49550.080*
C150.3720 (6)0.5022 (5)0.2102 (4)0.0541 (14)
H15A0.43080.45230.15680.065*
H15B0.32870.44460.27400.065*
C160.2673 (6)0.5833 (5)0.1664 (4)0.0488 (13)
C170.1427 (6)0.6287 (5)0.2294 (5)0.0596 (15)
C180.0470 (7)0.7033 (6)0.1868 (6)0.0728 (18)
H18−0.03570.73430.23230.087*
C190.0748 (7)0.7312 (6)0.0775 (6)0.080 (2)
H190.01100.78120.04800.096*
C200.1997 (8)0.6846 (6)0.0096 (5)0.0760 (19)
H200.21850.7022−0.06500.091*
C210.2924 (6)0.6141 (5)0.0526 (5)0.0632 (16)
H210.37540.58460.00650.076*
C220.6829 (5)0.6492 (5)0.1629 (4)0.0546 (14)
H22A0.73180.63460.21260.066*
H22B0.73220.59570.11030.066*
C230.6833 (5)0.7819 (4)0.1041 (4)0.0445 (12)
C240.6538 (5)0.8249 (5)0.0094 (4)0.0491 (13)
C250.6586 (6)0.9448 (5)−0.0481 (4)0.0566 (14)
H250.63750.9697−0.11160.068*
C260.6952 (6)1.0277 (5)−0.0102 (5)0.0672 (17)
H260.70001.1093−0.04870.081*
C270.7244 (7)0.9914 (6)0.0830 (5)0.0712 (18)
H270.74871.04800.10850.085*
C280.7178 (6)0.8692 (6)0.1404 (5)0.0666 (16)
H280.73700.84540.20470.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0413 (2)0.02862 (17)0.03475 (19)−0.00165 (14)−0.01569 (15)−0.00788 (13)
Sn20.0458 (2)0.03431 (18)0.03224 (19)−0.00562 (15)−0.01628 (15)−0.00401 (14)
Cl10.0610 (8)0.0372 (6)0.0546 (8)0.0030 (6)−0.0240 (7)−0.0085 (6)
Cl20.0727 (14)0.0590 (12)0.0858 (15)−0.0032 (10)−0.0315 (12)−0.0237 (10)
Cl2'0.0727 (14)0.0590 (12)0.0858 (15)−0.0032 (10)−0.0315 (12)−0.0237 (10)
Cl30.0743 (11)0.0692 (11)0.0932 (13)−0.0020 (9)−0.0141 (10)0.0080 (9)
Cl40.0917 (13)0.1304 (16)0.0571 (10)−0.0280 (12)−0.0216 (9)−0.0155 (10)
Cl50.1487 (18)0.0662 (10)0.0763 (12)−0.0408 (11)−0.0494 (12)−0.0049 (8)
O10.054 (2)0.0381 (18)0.0397 (19)−0.0030 (16)−0.0209 (16)−0.0015 (14)
O20.0440 (19)0.0304 (16)0.0341 (17)0.0006 (14)−0.0169 (15)−0.0051 (13)
C10.137 (6)0.064 (4)0.056 (4)−0.059 (4)−0.052 (4)0.014 (3)
C20.097 (5)0.048 (3)0.048 (3)−0.043 (3)−0.034 (3)0.011 (3)
C30.081 (5)0.060 (4)0.067 (4)−0.028 (3)−0.041 (4)0.003 (3)
C40.099 (5)0.068 (4)0.063 (4)−0.032 (4)−0.038 (4)−0.013 (3)
C50.093 (6)0.082 (5)0.084 (5)−0.041 (4)−0.051 (4)−0.002 (4)
C60.074 (5)0.074 (4)0.090 (5)−0.029 (4)−0.031 (4)−0.003 (4)
C70.101 (6)0.065 (4)0.061 (4)−0.042 (4)−0.027 (4)0.000 (3)
C80.047 (3)0.063 (4)0.064 (4)0.000 (3)−0.022 (3)−0.033 (3)
C90.035 (3)0.054 (3)0.055 (3)−0.001 (2)−0.019 (2)−0.016 (3)
C100.039 (3)0.058 (3)0.058 (4)−0.003 (3)−0.020 (3)−0.013 (3)
C110.045 (3)0.075 (4)0.068 (4)0.005 (3)−0.015 (3)−0.031 (3)
C120.062 (4)0.068 (4)0.108 (6)0.004 (3)−0.016 (4)−0.044 (4)
C130.069 (5)0.052 (4)0.112 (6)−0.008 (3)−0.016 (4)0.003 (4)
C140.051 (4)0.064 (4)0.069 (4)0.004 (3)−0.014 (3)−0.007 (3)
C150.065 (4)0.048 (3)0.060 (4)−0.013 (3)−0.029 (3)−0.013 (3)
C160.061 (4)0.045 (3)0.055 (3)−0.013 (3)−0.030 (3)−0.014 (2)
C170.063 (4)0.067 (4)0.057 (4)−0.013 (3)−0.026 (3)−0.015 (3)
C180.064 (4)0.079 (4)0.085 (5)−0.005 (3)−0.038 (4)−0.020 (4)
C190.082 (5)0.077 (5)0.095 (6)−0.004 (4)−0.057 (5)−0.005 (4)
C200.106 (6)0.083 (5)0.058 (4)−0.030 (4)−0.045 (4)−0.005 (3)
C210.066 (4)0.063 (4)0.074 (4)−0.011 (3)−0.030 (3)−0.025 (3)
C220.047 (3)0.046 (3)0.058 (3)−0.004 (2)−0.016 (3)0.005 (3)
C230.033 (3)0.041 (3)0.048 (3)−0.006 (2)−0.006 (2)−0.002 (2)
C240.049 (3)0.044 (3)0.047 (3)−0.008 (2)−0.009 (3)−0.006 (2)
C250.064 (4)0.046 (3)0.048 (3)−0.005 (3)−0.013 (3)−0.002 (3)
C260.072 (4)0.039 (3)0.070 (4)−0.002 (3)−0.007 (3)−0.007 (3)
C270.089 (5)0.065 (4)0.062 (4)−0.033 (4)−0.011 (4)−0.016 (3)
C280.065 (4)0.076 (4)0.061 (4)−0.020 (3)−0.024 (3)−0.005 (3)

Geometric parameters (Å, °)

Sn1—O12.148 (3)C9—C141.412 (7)
Sn1—O22.050 (3)C10—C111.385 (8)
Sn1—O2i2.146 (3)C11—C121.370 (8)
Sn1—C12.126 (5)C11—H110.9300
Sn1—C82.146 (5)C12—C131.368 (9)
Sn2—O12.276 (3)C12—H120.9300
Sn2—O22.025 (3)C13—C141.367 (9)
Sn2—C152.147 (5)C13—H130.9300
Sn2—C222.149 (5)C14—H140.9300
Sn2—Cl12.4376 (13)C15—C161.489 (7)
Cl2—C31.658 (7)C15—H15A0.9700
Cl2—H3A0.7301C15—H15B0.9700
Cl2'—C71.606 (8)C16—C171.368 (8)
Cl2'—H7A0.7242C16—C211.424 (7)
Cl3—C101.737 (6)C17—C181.381 (8)
Cl4—C171.742 (6)C18—C191.361 (9)
Cl5—C241.735 (5)C18—H180.9300
O1—H10.8590C19—C201.399 (9)
C1—C21.503 (7)C19—H190.9300
C1—H1A0.9700C20—C211.345 (8)
C1—H1B0.9700C20—H200.9300
C2—C71.379 (9)C21—H210.9300
C2—C31.391 (8)C22—C231.492 (6)
C3—C41.379 (7)C22—H22A0.9700
C3—H3A0.9301C22—H22B0.9700
C4—C51.371 (9)C23—C241.377 (7)
C4—H40.9300C23—C281.388 (7)
C5—C61.359 (9)C24—C251.369 (7)
C5—H50.9300C25—C261.374 (8)
C6—C71.371 (8)C25—H250.9300
C6—H60.9300C26—C271.355 (8)
C7—H7A0.9300C26—H260.9300
C8—C91.502 (7)C27—C281.391 (8)
C8—H8A0.9700C27—H270.9300
C8—H8B0.9700C28—H280.9300
C9—C101.379 (7)
O2—Sn1—C1114.2 (2)C10—C9—C8124.6 (5)
O2—Sn1—O2i73.49 (12)C14—C9—C8119.6 (5)
C1—Sn1—O2i97.25 (19)C9—C10—C11123.1 (5)
O2—Sn1—C8123.37 (17)C9—C10—Cl3120.6 (4)
C1—Sn1—C8122.4 (3)C11—C10—Cl3116.3 (5)
O2i—Sn1—C897.54 (16)C12—C11—C10119.1 (6)
O2—Sn1—O174.51 (12)C12—C11—H11120.5
C1—Sn1—O1100.54 (17)C10—C11—H11120.5
O2i—Sn1—O1147.55 (11)C13—C12—C11119.8 (6)
C8—Sn1—O195.50 (17)C13—C12—H12120.1
O2—Sn2—C15114.44 (17)C11—C12—H12120.1
O2—Sn2—C22108.14 (17)C14—C13—C12120.9 (6)
C15—Sn2—C22131.7 (2)C14—C13—H13119.6
O2—Sn2—O172.21 (11)C12—C13—H13119.6
C15—Sn2—O185.91 (16)C13—C14—C9121.3 (6)
C22—Sn2—O186.30 (16)C13—C14—H14119.4
O2—Sn2—Cl190.33 (9)C9—C14—H14119.4
C15—Sn2—Cl1102.16 (15)C16—C15—Sn2118.8 (3)
C22—Sn2—Cl199.22 (15)C16—C15—H15A107.6
O1—Sn2—Cl1162.53 (9)Sn2—C15—H15A107.6
C3—Cl2—H3A3.0C16—C15—H15B107.6
C7—Cl2'—H7A15.7Sn2—C15—H15B107.6
Sn1—O1—Sn2100.13 (13)H15A—C15—H15B107.0
Sn1—O1—H1120.9C17—C16—C21115.9 (5)
Sn2—O1—H1137.0C17—C16—C15124.1 (5)
Sn2—O2—Sn1112.76 (14)C21—C16—C15119.9 (5)
Sn2—O2—Sn1i139.33 (14)C16—C17—C18123.0 (6)
Sn1—O2—Sn1i106.51 (12)C16—C17—Cl4119.2 (4)
C2—C1—Sn1114.9 (3)C18—C17—Cl4117.8 (5)
C2—C1—H1A108.5C19—C18—C17119.4 (6)
Sn1—C1—H1A108.5C19—C18—H18120.3
C2—C1—H1B108.5C17—C18—H18120.3
Sn1—C1—H1B108.5C18—C19—C20119.8 (6)
H1A—C1—H1B107.5C18—C19—H19120.1
C7—C2—C3115.8 (5)C20—C19—H19120.1
C7—C2—C1122.3 (6)C21—C20—C19119.8 (6)
C3—C2—C1121.9 (6)C21—C20—H20120.1
C4—C3—C2122.6 (6)C19—C20—H20120.1
C4—C3—Cl2121.9 (6)C20—C21—C16122.0 (6)
C2—C3—Cl2115.4 (5)C20—C21—H21119.0
C4—C3—H3A119.9C16—C21—H21119.0
C2—C3—H3A117.5C23—C22—Sn2118.1 (3)
Cl2—C3—H3A2.4C23—C22—H22A107.8
C5—C4—C3119.1 (6)Sn2—C22—H22A107.8
C5—C4—H4120.5C23—C22—H22B107.8
C3—C4—H4120.5Sn2—C22—H22B107.8
C6—C5—C4119.7 (6)H22A—C22—H22B107.1
C6—C5—H5120.2C24—C23—C28115.7 (5)
C4—C5—H5120.2C24—C23—C22122.7 (5)
C5—C6—C7120.7 (7)C28—C23—C22121.5 (5)
C5—C6—H6119.7C25—C24—C23123.7 (5)
C7—C6—H6119.7C25—C24—Cl5118.1 (4)
C6—C7—C2122.1 (7)C23—C24—Cl5118.1 (4)
C6—C7—Cl2'130.8 (7)C24—C25—C26118.6 (5)
C2—C7—Cl2'107.1 (5)C24—C25—H25120.7
C6—C7—H7A119.0C26—C25—H25120.7
C2—C7—H7A119.0C27—C26—C25120.4 (5)
Cl2'—C7—H7A12.1C27—C26—H26119.8
C9—C8—Sn1111.3 (3)C25—C26—H26119.8
C9—C8—H8A109.4C26—C27—C28119.8 (6)
Sn1—C8—H8A109.4C26—C27—H27120.1
C9—C8—H8B109.4C28—C27—H27120.1
Sn1—C8—H8B109.4C23—C28—C27121.7 (6)
H8A—C8—H8B108.0C23—C28—H28119.2
C10—C9—C14115.9 (5)C27—C28—H28119.2
O2—Sn1—O1—Sn24.51 (11)Sn1—C8—C9—C10100.7 (5)
C1—Sn1—O1—Sn2116.9 (2)Sn1—C8—C9—C14−77.6 (5)
O2i—Sn1—O1—Sn2−5.2 (3)C14—C9—C10—C111.2 (8)
C8—Sn1—O1—Sn2−118.63 (17)C8—C9—C10—C11−177.1 (5)
O2—Sn2—O1—Sn1−4.61 (11)C14—C9—C10—Cl3−176.6 (4)
C15—Sn2—O1—Sn1−121.91 (19)C8—C9—C10—Cl35.0 (7)
C22—Sn2—O1—Sn1105.78 (19)C9—C10—C11—C12−0.5 (9)
Cl1—Sn2—O1—Sn1−3.5 (4)Cl3—C10—C11—C12177.4 (5)
C15—Sn2—O2—Sn182.0 (2)C10—C11—C12—C13−1.2 (10)
C22—Sn2—O2—Sn1−74.7 (2)C11—C12—C13—C142.0 (11)
O1—Sn2—O2—Sn15.17 (13)C12—C13—C14—C9−1.3 (10)
Cl1—Sn2—O2—Sn1−174.49 (13)C10—C9—C14—C13−0.3 (8)
C15—Sn2—O2—Sn1i−114.1 (3)C8—C9—C14—C13178.1 (6)
C22—Sn2—O2—Sn1i89.3 (3)O2—Sn2—C15—C16118.1 (4)
O1—Sn2—O2—Sn1i169.1 (3)C22—Sn2—C15—C16−92.2 (5)
Cl1—Sn2—O2—Sn1i−10.5 (2)O1—Sn2—C15—C16−173.6 (4)
C1—Sn1—O2—Sn2−100.2 (2)Cl1—Sn2—C15—C1622.1 (5)
O2i—Sn1—O2—Sn2169.2 (2)Sn2—C15—C16—C17−83.9 (6)
C8—Sn1—O2—Sn281.0 (2)Sn2—C15—C16—C2198.5 (5)
O1—Sn1—O2—Sn2−5.41 (13)C21—C16—C17—C18−2.0 (8)
C1—Sn1—O2—Sn1i90.6 (2)C15—C16—C17—C18−179.7 (5)
O2i—Sn1—O2—Sn1i0.000 (1)C21—C16—C17—Cl4176.0 (4)
C8—Sn1—O2—Sn1i−88.2 (2)C15—C16—C17—Cl4−1.6 (7)
O1—Sn1—O2—Sn1i−174.57 (16)C16—C17—C18—C191.9 (9)
O2—Sn1—C1—C255.6 (6)Cl4—C17—C18—C19−176.2 (5)
O2i—Sn1—C1—C2130.8 (5)C17—C18—C19—C20−0.2 (10)
C8—Sn1—C1—C2−125.5 (5)C18—C19—C20—C21−1.1 (10)
O1—Sn1—C1—C2−22.0 (6)C19—C20—C21—C160.9 (9)
Sn1—C1—C2—C7−94.6 (6)C17—C16—C21—C200.6 (8)
Sn1—C1—C2—C385.5 (6)C15—C16—C21—C20178.4 (5)
C7—C2—C3—C4−1.9 (8)O2—Sn2—C22—C23−116.2 (4)
C1—C2—C3—C4178.0 (5)C15—Sn2—C22—C2392.7 (5)
C7—C2—C3—Cl2176.7 (4)O1—Sn2—C22—C23173.9 (4)
C1—C2—C3—Cl2−3.4 (7)Cl1—Sn2—C22—C23−22.8 (4)
C2—C3—C4—C51.3 (9)Sn2—C22—C23—C24−74.9 (6)
Cl2—C3—C4—C5−177.2 (5)Sn2—C22—C23—C28107.0 (5)
C3—C4—C5—C60.7 (9)C28—C23—C24—C250.8 (8)
C4—C5—C6—C7−2.0 (10)C22—C23—C24—C25−177.4 (5)
C5—C6—C7—C21.3 (9)C28—C23—C24—Cl5−178.4 (4)
C5—C6—C7—Cl2'177.9 (6)C22—C23—C24—Cl53.5 (7)
C3—C2—C7—C60.6 (8)C23—C24—C25—C260.2 (9)
C1—C2—C7—C6−179.3 (5)Cl5—C24—C25—C26179.3 (4)
C3—C2—C7—Cl2'−176.7 (4)C24—C25—C26—C27−0.8 (9)
C1—C2—C7—Cl2'3.3 (7)C25—C26—C27—C280.3 (10)
O2—Sn1—C8—C9−131.3 (3)C24—C23—C28—C27−1.3 (8)
C1—Sn1—C8—C950.0 (5)C22—C23—C28—C27176.9 (5)
O2i—Sn1—C8—C9153.6 (4)C26—C27—C28—C230.7 (10)
O1—Sn1—C8—C9−56.2 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···Cl20.862.803.386 (4)127

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2652).

References

  • Li, G., Yin, H. & Wang, D. (2006). Acta Cryst. E62, m366–m368.
  • Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m593. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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