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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m593.
Published online 2009 April 30. doi:  10.1107/S1600536809015128
PMCID: PMC2977629

Dichloridoocta­kis(4-chloro­benz­yl)di-μ2-hydroxido-di-μ3-oxido-tetra­tin(IV) toluene solvate

Abstract

The title stannoxane is a toluene-solvated dimer, [Sn4(C7H6Cl)8Cl2O2(OH)2]·C7H8, the tetra­nuclear mol­ecule lying across a center of inversion. The Sn4O4 framework, whose two independent Sn atoms show trigonal bipyramidal coordination, is essentially planar (r.m.s deviation = 0.02 Å). One of the two chloro­benzyl groups of the chloridodiorganyltin unit is disordered over two positions with the chloro­phenyl residue refined over two positions in a 50:50 ratio. The solvent mol­ecule is disordered about a twofold axis.

Related literature

The distannoxane is a hydrolysed product of di(4-chloro­benz­yl)dichloridotin(IV); for the synthesis of the organotin compound by the direct reaction of 4-chloro­benzyl chloride and metallic tin, see: Shishido et al. (1961 [triangle]). For octa­benzyl­dichloridodi-μ2-hydroxo-di-μ3-oxo-tetra­tin, which crystallizes as a toluene disolvate, see: Mohamed et al. (2004 [triangle]). For octa­(4-methyl­benz­yl)dichloridodi-μ2-hydroxo-di-μ3-oxo-tetra­tin, see: Wang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m593-scheme1.jpg

Experimental

Crystal data

  • [Sn4(C7H6Cl)8Cl2O2(OH)2]·C7H8
  • M r = 1708.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m593-efi1.jpg
  • a = 26.6531 (3) Å
  • b = 10.8342 (1) Å
  • c = 25.8025 (3) Å
  • β = 121.546 (1)°
  • V = 6349.8 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.02 mm−1
  • T = 100 K
  • 0.36 × 0.12 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.564, T max = 0.746 (expected range = 0.643–0.851)
  • 21584 measured reflections
  • 7288 independent reflections
  • 6556 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.118
  • S = 0.97
  • 7288 reflections
  • 389 parameters
  • 127 restraints
  • H-atom parameters constrained
  • Δρmax = 1.08 e Å−3
  • Δρmin = −1.53 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015128/tk2437sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015128/tk2437Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (FS339/2008 A) for supporting this study.

supplementary crystallographic information

Experimental

Di(4-chlorobenzyl)tin dichloride (1 g, 2.2 mmol) (Shishido et al., 1961) was recrystallized from toluene in the presence of excess pyridine (1 ml) to give well formed, colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–0.99 Å) and were included in the refinement in the riding model approximation with U(H) set to 1.2–1.5U(C). The oxygen-bound H-atom was similarly treated (O–H 0.84 Å, U(H) 1.5U(O)).

One of the four chlorobenzyl groups, with the methylene-C1 atom, has its chlorophenyl residue disordered over two positions. As the occupancy refined to nearly 50:50, the occupancy was fixed as exactly 50:50. The phenyl ring was refined as a rigid hexagon of 1.39 Å. The temperature factors of the two chlorophenyl portions were restrained to be nearly isotropic.

The toluene molecule is disordered about a 2-fold axis; the phenyl part was also refined as a rigid hexagon, and the temperature factors of the carbon atoms were similarly restrained to be nearly isotropic.

The final difference Fourier map had a peak near Cl3 and a hole near the Sn2 atom.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [Sn2Cl(C7H6Cl)4O(OH)]2.C7H8 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. For reasons of clarity, the disorder in the chlorophenyl group is not shown nor is the disordered ...

Crystal data

[Sn4(C7H6Cl)8Cl2O2(OH)2]·C7H8F(000) = 3352
Mr = 1708.35Dx = 1.787 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9991 reflections
a = 26.6531 (3) Åθ = 2.5–28.3°
b = 10.8342 (1) ŵ = 2.02 mm1
c = 25.8025 (3) ÅT = 100 K
β = 121.546 (1)°Block, colorless
V = 6349.8 (1) Å30.36 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer7288 independent reflections
Radiation source: fine-focus sealed tube6556 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −34→34
Tmin = 0.564, Tmax = 0.746k = −14→14
21584 measured reflectionsl = −33→33

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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
7288 reflections(Δ/σ)max = 0.001
389 parametersΔρmax = 1.08 e Å3
127 restraintsΔρmin = −1.53 e Å3

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

xyzUiso*/UeqOcc. (<1)
Sn10.327847 (9)0.98788 (2)0.507504 (10)0.01694 (9)
Sn20.275327 (9)0.70201 (2)0.456210 (9)0.01484 (9)
Cl10.44736 (9)1.2278 (2)0.33532 (10)0.0402 (5)0.50
Cl1'0.47812 (11)1.3027 (2)0.39056 (13)0.0466 (6)0.50
Cl20.56752 (4)1.39884 (11)0.58933 (5)0.0421 (3)
Cl30.42907 (6)0.44291 (13)0.75877 (5)0.0566 (4)
Cl40.27115 (4)0.87250 (9)0.18192 (4)0.0302 (2)
Cl50.29674 (4)1.10490 (8)0.56878 (4)0.02368 (18)
O10.33270 (10)0.8384 (2)0.45170 (10)0.0201 (5)
H20.35150.83540.43380.030*
O20.27917 (10)0.8466 (2)0.50928 (10)0.0167 (4)
C10.28989 (16)1.1114 (4)0.43078 (17)0.0255 (8)
H1A0.25411.07310.39660.031*0.50
H1B0.27801.18880.44190.031*0.50
H1C0.25821.06750.39490.031*0.50
H1D0.27191.18250.43920.031*0.50
C20.3321 (3)1.1416 (7)0.4104 (3)0.019 (3)0.50
C30.3242 (2)1.0776 (6)0.3600 (3)0.0192 (17)0.50
H30.29441.01650.34130.023*0.50
C40.3600 (2)1.1032 (5)0.3369 (2)0.0224 (14)0.50
H40.35461.05950.30240.027*0.50
C50.4036 (2)1.1927 (6)0.3643 (3)0.0240 (18)0.50
C60.4115 (2)1.2566 (5)0.4148 (3)0.0246 (19)0.50
H60.44131.31780.43350.030*0.50
C70.3757 (3)1.2310 (6)0.4378 (3)0.0190 (18)0.50
H70.38111.27470.47230.023*0.50
C2'0.3344 (3)1.1548 (7)0.4162 (3)0.017 (3)0.50
C3'0.3450 (3)1.0990 (6)0.3743 (3)0.0242 (19)0.50
H3'0.32201.03020.35140.029*0.50
C4'0.3891 (3)1.1441 (6)0.3660 (3)0.0277 (18)0.50
H4'0.39641.10600.33740.033*0.50
C5'0.4227 (2)1.2449 (6)0.3996 (3)0.028 (2)0.50
C6'0.4121 (2)1.3006 (5)0.4415 (3)0.0279 (17)0.50
H6'0.43501.36950.46450.033*0.50
C7'0.3679 (3)1.2556 (6)0.4498 (3)0.0177 (18)0.50
H7'0.36071.29360.47840.021*0.50
C80.41833 (15)0.9705 (3)0.57839 (17)0.0237 (7)
H8A0.42060.96320.61780.028*
H8B0.43430.89330.57200.028*
C90.45657 (9)1.07721 (16)0.58191 (10)0.0195 (6)
C100.49762 (10)1.06170 (16)0.56468 (11)0.0251 (7)
H100.50220.98330.55120.030*
C110.53194 (9)1.1609 (2)0.56725 (11)0.0270 (8)
H110.56001.15030.55550.032*
C120.52521 (9)1.27552 (18)0.58704 (12)0.0286 (8)
C130.48416 (10)1.29103 (16)0.60427 (11)0.0253 (7)
H130.47961.36940.61780.030*
C140.44984 (9)1.19187 (19)0.60170 (11)0.0219 (7)
H140.42181.20250.61350.026*
C150.34351 (17)0.5660 (4)0.49764 (18)0.0281 (8)
H15A0.32910.48880.47370.034*
H15B0.37770.59500.49560.034*
C160.36408 (10)0.5374 (2)0.56319 (8)0.0217 (7)
C170.40371 (11)0.61529 (19)0.60939 (11)0.0465 (13)
H170.41700.68820.59970.056*
C180.42397 (12)0.5865 (2)0.66972 (10)0.0543 (15)
H180.45110.63980.70130.065*
C190.40460 (11)0.4799 (2)0.68384 (7)0.0331 (9)
C200.36497 (10)0.40193 (18)0.63764 (10)0.0232 (7)
H200.35170.32900.64730.028*
C210.34471 (9)0.43068 (19)0.57732 (8)0.0218 (7)
H210.31760.37740.54570.026*
C220.20707 (16)0.7021 (4)0.36242 (16)0.0257 (8)
H22A0.19210.61670.35050.031*
H22B0.17420.75370.35750.031*
C230.22529 (9)0.7490 (2)0.31922 (9)0.0198 (7)
C240.19185 (8)0.8399 (2)0.27705 (10)0.0253 (7)
H240.15900.87490.27680.030*
C250.20642 (10)0.8794 (2)0.23531 (9)0.0274 (8)
H250.18360.94150.20650.033*
C260.25443 (10)0.8281 (2)0.23573 (9)0.0223 (7)
C270.28787 (9)0.7373 (2)0.27789 (10)0.0259 (7)
H270.32070.70220.27820.031*
C280.27330 (9)0.6977 (2)0.31963 (9)0.0244 (7)
H280.29620.63560.34840.029*
C290.4229 (5)0.9306 (13)0.2428 (6)0.033 (2)0.50
H29A0.40381.00720.24360.050*0.50
H29B0.43150.87920.27770.050*0.50
H29C0.39670.88580.20500.050*0.50
C300.47904 (19)0.9607 (5)0.2457 (3)0.0256 (15)0.50
C310.4921 (3)1.0827 (4)0.2406 (3)0.032 (2)0.50
H310.46521.14650.23510.039*0.50
C320.5444 (3)1.1115 (4)0.2438 (3)0.043 (2)0.50
H320.55331.19480.24030.052*0.50
C330.5837 (2)1.0182 (6)0.2519 (3)0.038 (2)0.50
H330.61951.03780.25410.046*0.50
C340.5707 (2)0.8962 (5)0.2570 (4)0.036 (3)0.50
H340.59760.83240.26250.043*0.50
C350.5183 (2)0.8675 (4)0.2538 (3)0.0278 (16)0.50
H350.50940.78410.25730.033*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01971 (14)0.01661 (14)0.01916 (14)−0.00310 (8)0.01341 (11)0.00117 (8)
Sn20.01654 (13)0.01655 (14)0.01512 (13)0.00008 (8)0.01083 (10)0.00288 (8)
Cl10.0258 (9)0.0584 (13)0.0445 (12)0.0056 (9)0.0240 (9)0.0273 (10)
Cl1'0.0477 (12)0.0421 (12)0.0787 (17)0.0062 (9)0.0528 (13)0.0182 (11)
Cl20.0310 (5)0.0405 (6)0.0516 (6)−0.0154 (4)0.0194 (5)0.0024 (5)
Cl30.0672 (8)0.0566 (8)0.0172 (5)0.0364 (6)0.0022 (5)−0.0001 (5)
Cl40.0372 (5)0.0391 (5)0.0220 (4)−0.0055 (4)0.0209 (4)0.0018 (4)
Cl50.0323 (4)0.0210 (4)0.0269 (4)−0.0033 (3)0.0217 (4)−0.0027 (3)
O10.0228 (12)0.0213 (12)0.0204 (12)−0.0058 (10)0.0141 (10)−0.0004 (10)
O20.0211 (11)0.0176 (11)0.0178 (11)−0.0034 (9)0.0145 (9)0.0006 (9)
C10.0288 (18)0.0257 (19)0.0308 (19)0.0052 (14)0.0217 (16)0.0083 (15)
C20.023 (5)0.009 (4)0.025 (5)0.000 (4)0.012 (4)0.008 (4)
C30.024 (4)0.019 (4)0.018 (4)−0.010 (3)0.013 (3)0.000 (3)
C40.023 (3)0.029 (4)0.017 (3)−0.001 (3)0.011 (3)0.001 (3)
C50.017 (3)0.028 (4)0.029 (4)0.005 (3)0.013 (3)0.014 (4)
C60.022 (4)0.023 (4)0.023 (4)−0.009 (3)0.007 (3)0.010 (3)
C70.027 (4)0.016 (4)0.017 (4)−0.005 (3)0.014 (3)−0.001 (3)
C2'0.025 (6)0.019 (5)0.017 (4)0.004 (4)0.018 (4)0.002 (4)
C3'0.031 (5)0.021 (4)0.023 (4)−0.004 (3)0.016 (4)−0.003 (3)
C4'0.037 (5)0.032 (4)0.028 (4)0.006 (4)0.026 (4)−0.002 (4)
C5'0.028 (4)0.033 (4)0.035 (5)0.004 (3)0.024 (4)0.010 (4)
C6'0.023 (3)0.032 (4)0.026 (4)0.003 (3)0.012 (3)0.004 (3)
C7'0.024 (4)0.022 (4)0.012 (3)−0.005 (3)0.013 (3)0.001 (3)
C80.0234 (17)0.0237 (18)0.0258 (18)−0.0008 (14)0.0141 (15)0.0019 (14)
C90.0186 (15)0.0239 (17)0.0131 (14)−0.0027 (13)0.0061 (12)0.0018 (13)
C100.0263 (17)0.0274 (19)0.0233 (17)−0.0002 (15)0.0140 (15)0.0007 (15)
C110.0202 (16)0.032 (2)0.0310 (19)−0.0012 (15)0.0152 (15)0.0036 (16)
C120.0171 (16)0.036 (2)0.0262 (19)−0.0058 (15)0.0064 (14)0.0020 (16)
C130.0201 (16)0.0267 (19)0.0206 (17)−0.0071 (13)0.0047 (14)−0.0063 (14)
C140.0202 (16)0.0261 (18)0.0179 (16)−0.0005 (13)0.0090 (13)−0.0009 (13)
C150.0310 (19)0.0249 (19)0.041 (2)0.0145 (15)0.0271 (17)0.0182 (16)
C160.0155 (15)0.0196 (17)0.0331 (19)0.0043 (13)0.0148 (14)0.0068 (14)
C170.027 (2)0.022 (2)0.055 (3)−0.0061 (16)−0.0030 (19)0.015 (2)
C180.043 (3)0.019 (2)0.043 (3)−0.0004 (18)−0.017 (2)−0.0012 (19)
C190.032 (2)0.031 (2)0.0193 (18)0.0152 (17)0.0018 (16)0.0017 (16)
C200.0198 (16)0.0273 (19)0.0231 (17)0.0038 (14)0.0118 (14)0.0055 (14)
C210.0221 (16)0.0234 (17)0.0222 (16)−0.0017 (13)0.0132 (14)−0.0005 (14)
C220.0193 (16)0.042 (2)0.0158 (16)−0.0063 (15)0.0093 (14)0.0031 (15)
C230.0196 (15)0.0276 (18)0.0119 (14)−0.0072 (13)0.0081 (12)−0.0032 (13)
C240.0271 (17)0.0284 (19)0.0252 (18)0.0011 (15)0.0171 (15)0.0019 (15)
C250.0343 (19)0.0260 (19)0.0236 (18)0.0033 (15)0.0163 (16)0.0077 (15)
C260.0284 (17)0.0239 (18)0.0172 (16)−0.0084 (14)0.0138 (14)−0.0050 (13)
C270.0252 (17)0.031 (2)0.0267 (18)0.0005 (15)0.0172 (15)0.0001 (16)
C280.0260 (18)0.0260 (19)0.0231 (18)0.0028 (14)0.0141 (15)0.0022 (14)
C290.029 (4)0.031 (5)0.039 (5)0.001 (4)0.017 (4)−0.003 (4)
C300.026 (3)0.025 (4)0.018 (3)0.001 (3)0.006 (3)0.002 (3)
C310.035 (5)0.026 (3)0.031 (6)0.003 (4)0.015 (5)−0.001 (3)
C320.058 (5)0.036 (4)0.032 (4)−0.013 (4)0.021 (4)0.002 (3)
C330.033 (4)0.050 (5)0.027 (4)−0.008 (4)0.013 (3)0.003 (4)
C340.038 (6)0.036 (6)0.021 (4)−0.003 (4)0.007 (4)−0.002 (4)
C350.033 (4)0.023 (4)0.025 (3)0.000 (3)0.014 (4)0.000 (3)

Geometric parameters (Å, °)

Sn1—O22.023 (2)C10—H100.9500
Sn1—C82.140 (4)C11—C121.3900
Sn1—C12.154 (4)C11—H110.9500
Sn1—O12.215 (2)C12—C131.3900
Sn1—Cl52.4834 (8)C13—C141.3900
Sn2—O22.047 (2)C13—H130.9500
Sn2—O2i2.129 (2)C14—H140.9500
Sn2—C222.135 (3)C15—C161.512 (4)
Sn2—C152.141 (3)C15—H15A0.9900
Sn2—O12.173 (2)C15—H15B0.9900
Cl1—C51.725 (4)C16—C171.3900
Cl1'—C5'1.730 (4)C16—C211.3900
Cl2—C121.7292 (17)C17—C181.3900
Cl3—C191.733 (2)C17—H170.9500
Cl4—C261.7335 (16)C18—C191.3900
O1—H20.8400C18—H180.9500
O2—Sn2i2.129 (2)C19—C201.3900
C1—C2'1.495 (5)C20—C211.3900
C1—C21.505 (4)C20—H200.9500
C1—H1A0.9900C21—H210.9500
C1—H1B0.9900C22—C231.518 (4)
C1—H1C0.9900C22—H22A0.9900
C1—H1D0.9901C22—H22B0.9900
C2—C31.3900C23—C241.3900
C2—C71.3900C23—C281.3900
C3—C41.3900C24—C251.3900
C3—H30.9500C24—H240.9500
C4—C51.3900C25—C261.3900
C4—H40.9500C25—H250.9500
C5—C61.3900C26—C271.3900
C6—C71.3900C27—C281.3900
C6—H60.9500C27—H270.9500
C7—H70.9500C28—H280.9500
C2'—C3'1.3900C29—C301.493 (10)
C2'—C7'1.3900C29—H29A0.9800
C3'—C4'1.3900C29—H29B0.9800
C3'—H3'0.9500C29—H29C0.9800
C4'—C5'1.3900C30—C311.3900
C4'—H4'0.9500C30—C351.3900
C5'—C6'1.3900C31—C321.3900
C6'—C7'1.3900C31—H310.9500
C6'—H6'0.9500C32—C331.3900
C7'—H7'0.9500C32—H320.9500
C8—C91.512 (4)C33—C341.3900
C8—H8A0.9900C33—H330.9500
C8—H8B0.9900C34—C351.3900
C9—C101.3900C34—H340.9500
C9—C141.3900C35—H350.9500
C10—C111.3900
O2—Sn1—C8111.30 (12)C10—C9—C14120.0
O2—Sn1—C1119.52 (12)C10—C9—C8120.45 (19)
C8—Sn1—C1128.14 (14)C14—C9—C8119.54 (19)
O2—Sn1—O173.60 (8)C9—C10—C11120.0
C8—Sn1—O193.91 (12)C9—C10—H10120.0
C1—Sn1—O190.90 (12)C11—C10—H10120.0
O2—Sn1—Cl586.57 (6)C10—C11—C12120.0
C8—Sn1—Cl595.92 (10)C10—C11—H11120.0
C1—Sn1—Cl596.62 (10)C12—C11—H11120.0
O1—Sn1—Cl5159.98 (6)C13—C12—C11120.0
O2—Sn2—O2i73.49 (10)C13—C12—Cl2120.27 (14)
O2—Sn2—C22118.21 (13)C11—C12—Cl2119.73 (14)
O2i—Sn2—C2296.37 (11)C14—C13—C12120.0
O2—Sn2—C15117.40 (14)C14—C13—H13120.0
O2i—Sn2—C15101.99 (11)C12—C13—H13120.0
C22—Sn2—C15124.29 (16)C13—C14—C9120.0
O2—Sn2—O174.04 (8)C13—C14—H14120.0
O2i—Sn2—O1147.53 (9)C9—C14—H14120.0
C22—Sn2—O198.35 (11)C16—C15—Sn2114.6 (2)
C15—Sn2—O193.30 (12)C16—C15—H15A108.6
Sn2—O1—Sn1100.39 (9)Sn2—C15—H15A108.6
Sn2—O1—H2129.8C16—C15—H15B108.6
Sn1—O1—H2129.8Sn2—C15—H15B108.6
Sn1—O2—Sn2111.85 (9)H15A—C15—H15B107.6
Sn1—O2—Sn2i141.49 (12)C17—C16—C21120.0
Sn2—O2—Sn2i106.51 (10)C17—C16—C15120.2 (2)
C2'—C1—Sn1112.0 (4)C21—C16—C15119.8 (2)
C2—C1—Sn1112.2 (4)C16—C17—C18120.0
C2'—C1—H1A115.4C16—C17—H17120.0
C2—C1—H1A109.2C18—C17—H17120.0
Sn1—C1—H1A109.2C19—C18—C17120.0
C2'—C1—H1B102.9C19—C18—H18120.0
C2—C1—H1B109.2C17—C18—H18120.0
Sn1—C1—H1B109.2C18—C19—C20120.0
H1A—C1—H1B107.9C18—C19—Cl3120.66 (16)
C2'—C1—H1C108.4C20—C19—Cl3119.34 (16)
C2—C1—H1C101.8C21—C20—C19120.0
Sn1—C1—H1C108.8C21—C20—H20120.0
C2'—C1—H1D110.5C19—C20—H20120.0
C2—C1—H1D116.4C20—C21—C16120.0
Sn1—C1—H1D109.3C20—C21—H21120.0
H1C—C1—H1D107.8C16—C21—H21120.0
C3—C2—C7120.0C23—C22—Sn2115.0 (2)
C3—C2—C1116.4 (4)C23—C22—H22A108.5
C7—C2—C1123.6 (4)Sn2—C22—H22A108.5
C2—C3—C4120.0C23—C22—H22B108.5
C2—C3—H3120.0Sn2—C22—H22B108.5
C4—C3—H3120.0H22A—C22—H22B107.5
C5—C4—C3120.0C24—C23—C28120.0
C5—C4—H4120.0C24—C23—C22119.5 (2)
C3—C4—H4120.0C28—C23—C22120.5 (2)
C4—C5—C6120.0C25—C24—C23120.0
C4—C5—Cl1120.6 (4)C25—C24—H24120.0
C6—C5—Cl1119.4 (4)C23—C24—H24120.0
C7—C6—C5120.0C24—C25—C26120.0
C7—C6—H6120.0C24—C25—H25120.0
C5—C6—H6120.0C26—C25—H25120.0
C6—C7—C2120.0C27—C26—C25120.0
C6—C7—H7120.0C27—C26—Cl4119.67 (13)
C2—C7—H7120.0C25—C26—Cl4120.28 (13)
C3'—C2'—C7'120.0C26—C27—C28120.0
C3'—C2'—C1124.7 (4)C26—C27—H27120.0
C7'—C2'—C1115.2 (4)C28—C27—H27120.0
C2'—C3'—C4'120.0C27—C28—C23120.0
C2'—C3'—H3'120.0C27—C28—H28120.0
C4'—C3'—H3'120.0C23—C28—H28120.0
C5'—C4'—C3'120.0C31—C30—C35120.0
C5'—C4'—H4'120.0C31—C30—C29119.7 (7)
C3'—C4'—H4'120.0C35—C30—C29120.3 (7)
C4'—C5'—C6'120.0C30—C31—C32120.0
C4'—C5'—Cl1'121.1 (4)C30—C31—H31120.0
C6'—C5'—Cl1'118.9 (4)C32—C31—H31120.0
C5'—C6'—C7'120.0C31—C32—C33120.0
C5'—C6'—H6'120.0C31—C32—H32120.0
C7'—C6'—H6'120.0C33—C32—H32120.0
C6'—C7'—C2'120.0C34—C33—C32120.0
C6'—C7'—H7'120.0C34—C33—H33120.0
C2'—C7'—H7'120.0C32—C33—H33120.0
C9—C8—Sn1114.0 (2)C33—C34—C35120.0
C9—C8—H8A108.8C33—C34—H34120.0
Sn1—C8—H8A108.8C35—C34—H34120.0
C9—C8—H8B108.8C34—C35—C30120.0
Sn1—C8—H8B108.8C34—C35—H35120.0
H8A—C8—H8B107.6C30—C35—H35120.0
O2—Sn2—O1—Sn1−2.43 (8)C1—C2'—C7'—C6'177.6 (7)
O2i—Sn2—O1—Sn1−1.4 (2)O2—Sn1—C8—C9−176.63 (19)
C22—Sn2—O1—Sn1114.63 (13)C1—Sn1—C8—C915.2 (3)
C15—Sn2—O1—Sn1−120.01 (13)O1—Sn1—C8—C9109.5 (2)
O2—Sn1—O1—Sn22.47 (9)Cl5—Sn1—C8—C9−88.0 (2)
C8—Sn1—O1—Sn2113.53 (12)Sn1—C8—C9—C10−108.9 (2)
C1—Sn1—O1—Sn2−118.14 (12)Sn1—C8—C9—C1470.2 (3)
Cl5—Sn1—O1—Sn2−5.8 (3)C14—C9—C10—C110.0
C8—Sn1—O2—Sn2−90.57 (14)C8—C9—C10—C11179.1 (2)
C1—Sn1—O2—Sn278.73 (16)C9—C10—C11—C120.0
O1—Sn1—O2—Sn2−2.78 (10)C10—C11—C12—C130.0
Cl5—Sn1—O2—Sn2174.40 (10)C10—C11—C12—Cl2−179.31 (19)
C8—Sn1—O2—Sn2i94.6 (2)C11—C12—C13—C140.0
C1—Sn1—O2—Sn2i−96.1 (2)Cl2—C12—C13—C14179.30 (19)
O1—Sn1—O2—Sn2i−177.6 (2)C12—C13—C14—C90.0
Cl5—Sn1—O2—Sn2i−0.40 (18)C10—C9—C14—C130.0
O2i—Sn2—O2—Sn1−176.62 (18)C8—C9—C14—C13−179.1 (2)
C22—Sn2—O2—Sn1−88.21 (14)O2—Sn2—C15—C1637.0 (3)
C15—Sn2—O2—Sn188.19 (15)O2i—Sn2—C15—C16−40.4 (3)
O1—Sn2—O2—Sn12.82 (10)C22—Sn2—C15—C16−146.8 (2)
O2i—Sn2—O2—Sn2i0.0O1—Sn2—C15—C16110.8 (2)
C22—Sn2—O2—Sn2i88.41 (14)Sn2—C15—C16—C17−80.2 (3)
C15—Sn2—O2—Sn2i−95.18 (14)Sn2—C15—C16—C21101.8 (2)
O1—Sn2—O2—Sn2i179.45 (12)C21—C16—C17—C180.0
O2—Sn1—C1—C2'−145.1 (3)C15—C16—C17—C18−177.9 (2)
C8—Sn1—C1—C2'22.2 (4)C16—C17—C18—C190.0
O1—Sn1—C1—C2'−73.5 (3)C17—C18—C19—C200.0
Cl5—Sn1—C1—C2'125.1 (3)C17—C18—C19—Cl3−179.7 (2)
O2—Sn1—C1—C2−137.2 (3)C18—C19—C20—C210.0
C8—Sn1—C1—C230.1 (4)Cl3—C19—C20—C21179.7 (2)
O1—Sn1—C1—C2−65.6 (3)C19—C20—C21—C160.0
Cl5—Sn1—C1—C2133.0 (3)C17—C16—C21—C200.0
C2'—C1—C2—C3−170 (5)C15—C16—C21—C20177.9 (2)
Sn1—C1—C2—C3100.5 (4)O2—Sn2—C22—C2398.0 (3)
C2'—C1—C2—C77(5)O2i—Sn2—C22—C23172.7 (2)
Sn1—C1—C2—C7−81.9 (5)C15—Sn2—C22—C23−78.1 (3)
C7—C2—C3—C40.0O1—Sn2—C22—C2321.7 (3)
C1—C2—C3—C4177.7 (6)Sn2—C22—C23—C24−129.00 (19)
C2—C3—C4—C50.0Sn2—C22—C23—C2854.1 (3)
C3—C4—C5—C60.0C28—C23—C24—C250.0
C3—C4—C5—Cl1−178.6 (5)C22—C23—C24—C25−176.9 (2)
C4—C5—C6—C70.0C23—C24—C25—C260.0
Cl1—C5—C6—C7178.7 (5)C24—C25—C26—C270.0
C5—C6—C7—C20.0C24—C25—C26—Cl4177.44 (18)
C3—C2—C7—C60.0C25—C26—C27—C280.0
C1—C2—C7—C6−177.5 (7)Cl4—C26—C27—C28−177.45 (18)
Sn1—C1—C2'—C3'93.2 (5)C26—C27—C28—C230.0
C2—C1—C2'—C7'−178 (5)C24—C23—C28—C270.0
Sn1—C1—C2'—C7'−84.3 (4)C22—C23—C28—C27176.9 (2)
C7'—C2'—C3'—C4'0.0C35—C30—C31—C320.0
C1—C2'—C3'—C4'−177.4 (7)C29—C30—C31—C32179.6 (9)
C2'—C3'—C4'—C5'0.0C30—C31—C32—C330.0
C3'—C4'—C5'—C6'0.0C31—C32—C33—C340.0
C3'—C4'—C5'—Cl1'179.7 (5)C32—C33—C34—C350.0
C4'—C5'—C6'—C7'0.0C33—C34—C35—C300.0
Cl1'—C5'—C6'—C7'−179.7 (5)C31—C30—C35—C340.0
C5'—C6'—C7'—C2'0.0C29—C30—C35—C34−179.6 (9)
C3'—C2'—C7'—C6'0.0

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2437).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mohamed, E. M., Panchanatheswaran, K., Low, J. N. & Glidewell, C. (2004). Acta Cryst. E60, m489–m491.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shishido, K., Yoshiyuki, T. & Jiro, K. (1961). J. Am. Chem. Soc.83, 538–541.
  • Wang, J.-Q., Zhang, F.-X., Kuang, D.-Z., Feng, Y.-L., Xu, Z.-F. & Chen, Z.-M. (2007). Chin. J. Inorg. Chem.23, 871–874.
  • Westrip, S. P. (2009). publCIF In preparation.

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