Tetra­kis[3,5-bis­(trifluoro­meth­yl)phenyl]tin(IV)

Foucher, D.; Miles, D.; Lough, A.J.

doi:10.1107/S1600536809019588

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m704

doi:10.1107/S1600536809019588

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Tetrakis[3,5-bis(trifluoromethyl)phenyl]tin(IV)

Daniel Foucher,^a Damion Miles ^a and Alan J. Lough ^b ^*

^aDepartment of Chemistry and Biology, Ryerson University, Toronto, Ontario, Canada M5B 2K3, and ^bDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 21 May 2009; accepted 22 May 2009; online 6 June 2009)

The title molecule, [Sn(C₈H₃F₆)₄], lies on a twofold rotation axis with the Sn^IV ion in a distorted tetrahedral coordination environment. Both –CF₃ groups attached to one of the unique benzene rings are disordered over two sets of sites, with the ratios of refined occupancies being 0.719 (14):0.281 (14) and 0.63 (5):0.37 (5).

Related literature

For synthesis of the title compound, see King et al. (1986 ). Additional preparative details of similar compounds are given by Lu & Tilley (2000 ). For related crystal structures, see: Young et al. (2005 ); Smith et al. (1994 ); Wharf & Simard (1997 ). For further details of geometric distortions in related compounds, see Charissé et al. (1998 ).

Experimental

Crystal data

[Sn(C₈H₃F₆)₄]
M_r = 971.11
Monoclinic, C 2/c
a = 17.3506 (8) Å
b = 20.8038 (11) Å
c = 9.8944 (3) Å
β = 109.998 (3)°
V = 3356.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 150 K
0.28 × 0.24 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.798, T_max = 0.897
10930 measured reflections
3818 independent reflections
3142 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.097
S = 1.06
3818 reflections
314 parameters
211 restraints
H-atom parameters constrained
Δρ_max = 1.80 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C9	2.146 (3)
Sn1—C1	2.150 (3)

C9—Sn1—C9ⁱ	109.73 (16)
C9—Sn1—C1	104.69 (11)
C9—Sn1—C1ⁱ	108.35 (11)
C1—Sn1—C1ⁱ	120.82 (17)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019588/pk2165sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019588/pk2165Isup2.hkl

checkCIF report

Comment top

The preparation of polymerizable dialkyl or diaryl tin monomers bearing either chlorine or hydride groups (Lu & Tilley, 2000) is accessed through the initial comportionation reactions involving the tetraalkyl- or tetraryltin(IV) compounds and tin(IV) tetrachloride. The incorporation of perfluorinated species in the backbone of polystannanes should by design impart an improved stability towards nucleophilic attack. Our interest in the distortions from tetrahedral geometry of other tin aryl compounds (Charissé et al., 1998), prompted us to determine the crystal structure of the title compound which was previously synthesized by King et al. (1986).

The title molecule (Fig. 1) lies on a twofold rotation axis. The Sn^IV ion is in a distorted tetrahedral coordination environment (Table 1). The angular disortion from the ideal values of 109.5° is most likely a consequence of the steric crowding caused by the 3,5 substitution of the bulky trifluoromethyl groups on the benzene rings. The Sn—C bond distances in the title compound are the same within experimental error and are comparable to those in the para-substituted and meta-substituted tetrakis[(trifluoromethyl)phenyl]stannane structures (Young et al., 2005; Smith et al., 1994) but are significantly longer than the Sn—C bonds in the related triaryltin(IV)chloride compounds (Wharf & Simard, 1997).

Related literature top

For synthesis of the title compound, see King et al. (1986). Additional preparative details of similar compounds are given by Lu & Tilley (2000). For related crystal structures, see: Young et al. (2005); Smith et al. (1994); Wharf & Simard (1997). For further details of geometric distortions in related compounds, see Charissé et al. (1998).

Experimental top

The title compound was prepared from the refluxing Grignard reaction of 3,5-trifluoromethylphenyl magnesium bromide (12.5 mmol) in ether with anhydrous tin tetrachloride (3.125 mmol). The reaction mixture was refluxed overnight, cooled and filtered to remove salts. The crude compound was purified first by sublimation, and then recrystallization from ether to yield long large needles suitable for X-ray diffraction. Yield 1.33 g, 44%. m.p. 426 K (literature 436 K; King et al., 1986).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probabilty level. The minor comonent of disorder is not shown [symmetry code (a): -x + 1, y, -z + 1/2].

Tetrakis[3,5-bis(trifluoromethyl)phenyl]tin(IV) top

Crystal data top

[Sn(C₈H₃F₆)₄]	F(000) = 1880
M_r = 971.11	D_x = 1.922 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10930 reflections
a = 17.3506 (8) Å	θ = 2.9–27.5°
b = 20.8038 (11) Å	µ = 0.92 mm⁻¹
c = 9.8944 (3) Å	T = 150 K
β = 109.998 (3)°	Block, colourless
V = 3356.1 (3) Å³	0.28 × 0.24 × 0.12 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3818 independent reflections
Radiation source: fine-focus sealed tube	3142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ scans and ω scans with κ offsets	h = −22→20
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −24→26
T_min = 0.798, T_max = 0.897	l = −10→12
10930 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0382P)² + 9.7798P] where P = (F_o² + 2F_c²)/3
3818 reflections	(Δ/σ)_max = 0.001
314 parameters	Δρ_max = 1.80 e Å⁻³
211 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Sn(C₈H₃F₆)₄]	V = 3356.1 (3) Å³
M_r = 971.11	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.3506 (8) Å	µ = 0.92 mm⁻¹
b = 20.8038 (11) Å	T = 150 K
c = 9.8944 (3) Å	0.28 × 0.24 × 0.12 mm
β = 109.998 (3)°

Data collection top

Nonius KappaCCD diffractometer	3818 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3142 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.897	R_int = 0.038
10930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	211 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.06	Δρ_max = 1.80 e Å⁻³
3818 reflections	Δρ_min = −0.69 e Å⁻³
314 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.5000	0.204875 (15)	0.2500	0.02382 (11)
C1	0.44875 (18)	0.25591 (16)	0.3883 (3)	0.0241 (7)
C2	0.4192 (2)	0.21779 (17)	0.4754 (3)	0.0308 (7)
H2A	0.4214	0.1723	0.4688	0.037*
C3	0.3864 (2)	0.24535 (19)	0.5721 (4)	0.0358 (8)
C4	0.3826 (2)	0.31171 (19)	0.5823 (4)	0.0376 (9)
H4A	0.3609	0.3307	0.6489	0.045*
C5	0.4109 (2)	0.35008 (17)	0.4942 (4)	0.0301 (7)
C6	0.44410 (19)	0.32238 (16)	0.3985 (3)	0.0269 (7)
H6A	0.4638	0.3491	0.3395	0.032*
C7	0.3561 (3)	0.2031 (2)	0.6667 (5)	0.0518 (11)
C8	0.4071 (3)	0.42168 (19)	0.5053 (4)	0.0420 (9)
C9	0.40171 (18)	0.14550 (15)	0.1187 (3)	0.0225 (6)
C10	0.32103 (18)	0.15735 (15)	0.1095 (3)	0.0232 (6)
H10A	0.3099	0.1908	0.1654	0.028*
C11	0.25646 (19)	0.12090 (15)	0.0196 (3)	0.0234 (6)
C12	0.27116 (19)	0.07233 (15)	−0.0643 (3)	0.0254 (7)
H12A	0.2272	0.0477	−0.1264	0.030*
C13	0.3514 (2)	0.06033 (16)	−0.0559 (3)	0.0273 (7)
C14	0.4159 (2)	0.09614 (16)	0.0350 (3)	0.0270 (7)
H14A	0.4705	0.0869	0.0402	0.032*
C15	0.1714 (2)	0.13382 (18)	0.0164 (4)	0.0315 (8)
C16	0.3678 (2)	0.00755 (19)	−0.1447 (4)	0.0402 (9)
F1	0.3387 (8)	0.1480 (5)	0.6254 (12)	0.110 (5)	0.510 (14)
F2	0.2865 (4)	0.2297 (5)	0.6815 (9)	0.060 (3)	0.510 (14)
F3	0.4062 (4)	0.2039 (7)	0.8017 (6)	0.098 (4)	0.510 (14)
F1A	0.3073 (6)	0.1557 (6)	0.5899 (12)	0.074 (3)	0.490 (14)
F2A	0.3197 (9)	0.2296 (5)	0.7385 (15)	0.151 (6)	0.490 (14)
F3A	0.4188 (4)	0.1697 (6)	0.7542 (13)	0.122 (5)	0.490 (14)
F4	0.3437 (13)	0.4405 (10)	0.539 (3)	0.113 (5)	0.62 (5)
F5	0.4721 (11)	0.4474 (7)	0.5986 (12)	0.078 (4)	0.62 (5)
F6	0.3982 (8)	0.4522 (6)	0.3803 (8)	0.062 (2)	0.62 (5)
F4A	0.3656 (14)	0.4402 (16)	0.587 (3)	0.081 (5)	0.38 (5)
F5A	0.4839 (9)	0.4429 (9)	0.574 (2)	0.064 (4)	0.38 (5)
F6A	0.3803 (18)	0.4473 (12)	0.3853 (13)	0.094 (8)	0.38 (5)
F7	0.16383 (14)	0.12649 (15)	0.1440 (2)	0.0607 (7)
F8	0.14807 (14)	0.19481 (11)	−0.0251 (3)	0.0595 (7)
F9	0.11541 (12)	0.09611 (11)	−0.0743 (2)	0.0456 (6)
F10	0.3779 (2)	−0.04902 (12)	−0.0768 (3)	0.0724 (8)
F11	0.30798 (17)	0.00107 (16)	−0.2707 (3)	0.0828 (10)
F12	0.43615 (16)	0.01590 (12)	−0.1746 (3)	0.0568 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02302 (16)	0.02508 (18)	0.02467 (17)	0.000	0.00986 (12)	0.000
C1	0.0201 (14)	0.0296 (17)	0.0228 (15)	0.0012 (13)	0.0078 (12)	−0.0006 (13)
C2	0.0345 (18)	0.0299 (19)	0.0295 (17)	−0.0011 (14)	0.0128 (14)	−0.0008 (14)
C3	0.040 (2)	0.040 (2)	0.0312 (18)	−0.0052 (16)	0.0169 (16)	−0.0034 (16)
C4	0.041 (2)	0.044 (2)	0.0323 (18)	−0.0032 (17)	0.0187 (16)	−0.0084 (16)
C5	0.0286 (17)	0.0303 (18)	0.0311 (17)	−0.0019 (14)	0.0096 (14)	−0.0071 (15)
C6	0.0245 (16)	0.0284 (17)	0.0272 (16)	0.0001 (14)	0.0082 (13)	−0.0012 (14)
C7	0.074 (3)	0.048 (3)	0.047 (2)	−0.003 (2)	0.040 (2)	0.002 (2)
C8	0.054 (2)	0.031 (2)	0.045 (2)	−0.0021 (19)	0.022 (2)	−0.0098 (18)
C9	0.0243 (15)	0.0221 (16)	0.0216 (15)	−0.0004 (12)	0.0086 (12)	0.0005 (12)
C10	0.0243 (15)	0.0240 (16)	0.0212 (15)	0.0004 (13)	0.0079 (12)	0.0012 (13)
C11	0.0257 (15)	0.0233 (16)	0.0217 (15)	0.0023 (13)	0.0087 (12)	0.0038 (13)
C12	0.0270 (16)	0.0260 (17)	0.0214 (15)	−0.0001 (13)	0.0060 (12)	0.0016 (13)
C13	0.0319 (17)	0.0243 (17)	0.0264 (16)	0.0036 (14)	0.0108 (13)	−0.0021 (13)
C14	0.0262 (16)	0.0276 (17)	0.0293 (16)	0.0009 (13)	0.0120 (13)	−0.0002 (14)
C15	0.0275 (17)	0.036 (2)	0.0311 (17)	−0.0016 (15)	0.0099 (14)	−0.0050 (15)
C16	0.035 (2)	0.038 (2)	0.047 (2)	0.0041 (16)	0.0125 (17)	−0.0124 (18)
F1	0.232 (14)	0.034 (4)	0.131 (10)	−0.017 (7)	0.149 (11)	−0.013 (6)
F2	0.033 (3)	0.096 (6)	0.061 (4)	−0.002 (3)	0.028 (3)	0.017 (4)
F3	0.050 (4)	0.204 (12)	0.041 (3)	−0.010 (5)	0.015 (3)	0.054 (5)
F1A	0.058 (4)	0.083 (7)	0.081 (5)	−0.038 (4)	0.023 (4)	0.018 (4)
F2A	0.314 (18)	0.066 (6)	0.175 (13)	−0.029 (10)	0.215 (13)	−0.028 (8)
F3A	0.084 (6)	0.194 (12)	0.080 (7)	−0.029 (6)	0.019 (5)	0.094 (8)
F4	0.127 (8)	0.037 (5)	0.227 (14)	0.020 (5)	0.128 (9)	−0.004 (10)
F5	0.118 (8)	0.044 (4)	0.041 (4)	−0.003 (5)	−0.013 (4)	−0.012 (3)
F6	0.105 (5)	0.029 (4)	0.058 (5)	−0.003 (3)	0.036 (5)	−0.005 (3)
F4A	0.135 (12)	0.044 (8)	0.108 (11)	−0.004 (10)	0.098 (9)	−0.026 (7)
F5A	0.060 (7)	0.030 (5)	0.110 (12)	−0.026 (4)	0.037 (7)	−0.030 (6)
F6A	0.149 (14)	0.045 (8)	0.041 (7)	0.028 (9)	−0.030 (9)	0.012 (6)
F7	0.0406 (13)	0.110 (2)	0.0408 (13)	0.0007 (14)	0.0263 (10)	−0.0102 (14)
F8	0.0309 (12)	0.0405 (14)	0.104 (2)	0.0091 (10)	0.0197 (13)	0.0040 (13)
F9	0.0249 (10)	0.0544 (14)	0.0565 (14)	−0.0069 (10)	0.0125 (9)	−0.0180 (11)
F10	0.107 (2)	0.0271 (13)	0.110 (2)	0.0066 (14)	0.072 (2)	−0.0060 (14)
F11	0.0602 (17)	0.101 (2)	0.0673 (18)	0.0213 (16)	−0.0035 (14)	−0.0584 (17)
F12	0.0640 (16)	0.0546 (16)	0.0696 (16)	−0.0009 (12)	0.0458 (14)	−0.0217 (13)

Geometric parameters (Å, º) top

Sn1—C9	2.146 (3)	C8—F5	1.302 (11)
Sn1—C9ⁱ	2.146 (3)	C8—F4	1.313 (12)
Sn1—C1	2.150 (3)	C8—F4A	1.314 (16)
Sn1—C1ⁱ	2.150 (3)	C8—F5A	1.346 (14)
C1—C6	1.391 (5)	C8—F6	1.351 (10)
C1—C2	1.392 (5)	C9—C14	1.393 (4)
C2—C3	1.393 (5)	C9—C10	1.393 (4)
C2—H2A	0.9500	C10—C11	1.393 (4)
C3—C4	1.387 (5)	C10—H10A	0.9500
C3—C7	1.504 (5)	C11—C12	1.386 (4)
C4—C5	1.390 (5)	C11—C15	1.489 (5)
C4—H4A	0.9500	C12—C13	1.389 (4)
C5—C6	1.391 (5)	C12—H12A	0.9500
C5—C8	1.497 (5)	C13—C14	1.388 (5)
C6—H6A	0.9500	C13—C16	1.493 (5)
C7—F1	1.220 (10)	C14—H14A	0.9500
C7—F2A	1.231 (9)	C15—F7	1.323 (4)
C7—F3	1.321 (7)	C15—F9	1.330 (4)
C7—F3A	1.331 (7)	C15—F8	1.352 (4)
C7—F1A	1.351 (10)	C16—F11	1.328 (4)
C7—F2	1.381 (8)	C16—F12	1.328 (4)
C8—F6A	1.239 (14)	C16—F10	1.337 (5)

C9—Sn1—C9ⁱ	109.73 (16)	F6A—C8—F4A	111.1 (12)
C9—Sn1—C1	104.69 (11)	F6A—C8—F5A	109.0 (12)
C9ⁱ—Sn1—C1	108.35 (11)	F4A—C8—F5A	104.5 (9)
C9—Sn1—C1ⁱ	108.35 (11)	F5—C8—F6	104.9 (7)
C9ⁱ—Sn1—C1ⁱ	104.69 (11)	F4—C8—F6	104.3 (8)
C1—Sn1—C1ⁱ	120.82 (17)	F6A—C8—C5	111.7 (11)
C6—C1—C2	118.6 (3)	F5—C8—C5	114.3 (8)
C6—C1—Sn1	125.7 (2)	F4—C8—C5	112.2 (9)
C2—C1—Sn1	115.6 (2)	F4A—C8—C5	112.6 (15)
C1—C2—C3	121.0 (3)	F5A—C8—C5	107.6 (9)
C1—C2—H2A	119.5	F6—C8—C5	113.2 (6)
C3—C2—H2A	119.5	C14—C9—C10	118.0 (3)
C4—C3—C2	120.0 (3)	C14—C9—Sn1	121.2 (2)
C4—C3—C7	120.1 (3)	C10—C9—Sn1	120.7 (2)
C2—C3—C7	119.9 (4)	C11—C10—C9	121.1 (3)
C3—C4—C5	119.4 (3)	C11—C10—H10A	119.5
C3—C4—H4A	120.3	C9—C10—H10A	119.5
C5—C4—H4A	120.3	C12—C11—C10	120.5 (3)
C4—C5—C6	120.4 (3)	C12—C11—C15	120.2 (3)
C4—C5—C8	119.5 (3)	C10—C11—C15	119.3 (3)
C6—C5—C8	120.1 (3)	C11—C12—C13	118.8 (3)
C1—C6—C5	120.6 (3)	C11—C12—H12A	120.6
C1—C6—H6A	119.7	C13—C12—H12A	120.6
C5—C6—H6A	119.7	C14—C13—C12	120.8 (3)
F1—C7—F2A	119.8 (9)	C14—C13—C16	120.1 (3)
F1—C7—F3	110.7 (7)	C12—C13—C16	119.0 (3)
F2A—C7—F3A	109.0 (6)	C13—C14—C9	120.9 (3)
F2A—C7—F1A	107.7 (6)	C13—C14—H14A	119.6
F3—C7—F1A	130.4 (9)	C9—C14—H14A	119.6
F3A—C7—F1A	101.6 (6)	F7—C15—F9	106.7 (3)
F1—C7—F2	106.6 (6)	F7—C15—F8	106.3 (3)
F3—C7—F2	100.6 (5)	F9—C15—F8	105.9 (3)
F3A—C7—F2	133.7 (7)	F7—C15—C11	112.3 (3)
F1—C7—C3	116.1 (6)	F9—C15—C11	113.4 (3)
F2A—C7—C3	117.1 (7)	F8—C15—C11	111.6 (3)
F3—C7—C3	111.8 (6)	F11—C16—F12	105.9 (3)
F3A—C7—C3	109.2 (6)	F11—C16—F10	108.0 (3)
F1A—C7—C3	111.2 (7)	F12—C16—F10	104.7 (3)
F2—C7—C3	109.6 (6)	F11—C16—C13	112.5 (3)
F6A—C8—F5	116.9 (15)	F12—C16—C13	113.5 (3)
F5—C8—F4	107.2 (7)	F10—C16—C13	111.7 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₈H₃F₆)₄]
M_r	971.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	17.3506 (8), 20.8038 (11), 9.8944 (3)
β (°)	109.998 (3)
V (Å³)	3356.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.28 × 0.24 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.798, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	10930, 3818, 3142
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.097, 1.06
No. of reflections	3818
No. of parameters	314
No. of restraints	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.80, −0.69

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Sn1—C9	2.146 (3)	Sn1—C1	2.150 (3)

C9—Sn1—C9ⁱ	109.73 (16)	C9—Sn1—C1ⁱ	108.35 (11)
C9—Sn1—C1	104.69 (11)	C1—Sn1—C1ⁱ	120.82 (17)

Symmetry code: (i) −x+1, y, −z+1/2.

Acknowledgements

The authors acknowledge NSERC Canada, the University of Toronto, the NSERC Discovery fund and the Dean's Seed Fund Initiative (Ryerson University) for funding.

References

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