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Acta Cryst. (2009). E65, m593    [ doi:10.1107/S1600536809015128 ]

Dichloridooctakis(4-chlorobenzyl)di-[mu]2-hydroxido-di-[mu]3-oxido-tetratin(IV) toluene solvate

K. M. Lo and S. W. Ng

Abstract top

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 top

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). For octabenzyldichloridodi-µ2-hydroxo-di-µ3-oxo-tetratin, which crystallizes as a toluene disolvate, see: Mohamed et al. (2004). For octa(4-methylbenzyl)dichloridodi-µ2-hydroxo-di-µ3-oxo-tetratin, see: Wang et al. (2007).

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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 solvent molecule. Unlabelled atoms are related to the labelled atoms by a centre of inversion.
Dichloridooctakis(4-chlorobenzyl)di-µ2-hydroxido-di-µ3-oxido-tetratin(IV) toluene solvate top
Crystal data top
[Sn4(C7H6Cl)8Cl2O2(OH)2]·C7H8F(000) = 3352
Mr = 1708.35Dx = 1.787 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		7288 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 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
7288 reflections(Δ/σ)max = 0.001
389 parametersΔρmax = 1.08 e Å−3
127 restraintsΔρmin = −1.53 e Å−3
Crystal data top
[Sn4(C7H6Cl)8Cl2O2(OH)2]·C7H8V = 6349.8 (1) Å3
Mr = 1708.35Z = 4
Monoclinic, C2/cMo Kα radiation
a = 26.6531 (3) ŵ = 2.02 mm−1
b = 10.8342 (1) ÅT = 100 K
c = 25.8025 (3) Å0.36 × 0.12 × 0.08 mm
β = 121.546 (1)°
Data collection top
Bruker SMART APEX
diffractometer		7288 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6556 reflections with I > 2σ(I)
Tmin = 0.564, Tmax = 0.746Rint = 0.025
21584 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.118Δρmax = 1.08 e Å−3
S = 0.97Δρmin = −1.53 e Å−3
7288 reflectionsAbsolute structure: ?
389 parametersFlack parameter: ?
127 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Acknowledgements top

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

references
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