Acta Crystallographica Section E: Structure Reports Online

Acta Crystallogr Sect E Struct Rep Online. 64(Pt 6): m803-m803

Dichloridobis(di-tert-butylmethylphosphine oxide-κO)diphenyltin(IV)

Manuela Müllera, Hans-Wolfram Lernera, Michael Boltea*

a. Institut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany

Correspondence e-mail: bolte@chemie.uni-frankfurt.de

© Müller et al. 2008

DOI: 10.1107/S1600536808013809

Published online: 10 May 2008

Abstract

The complete molecule of the title compound, [Sn(C₆H₅)₂Cl₂(C₉H₂₁OP)₂], is generated by crystallographic inversion symmetry, the Sn atom is located on a special position of site symmetry . The Sn atom adopts an all-trans SnC₂O₂Cl₂ octahedral geometry. As a consequence of the bulky substituents at the O atom, the P—O—Sn bond angle is 163.9 (3)°.

Related literature

For related literature, see: Lerner et al. (2005 ▶); Ruth et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

[Sn(C₆H₅)₂Cl₂(C₉H₂₁OP)₂]

M r = 696.25

Monoclinic,

a = 12.1782 (19) Å

b = 9.0866 (8) Å

c = 16.339 (2) Å

β = 111.518 (11)°

V = 1682.0 (4) Å³

Z = 2

Mo Kα radiation

μ = 1.04 mm⁻¹

T = 173 (2) K

0.13 × 0.09 × 0.07 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.877, T max = 0.931

11731 measured reflections

3145 independent reflections

1754 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F ² > 2σ(F ²)] = 0.058

wR(F ²) = 0.098

S = 0.88

3145 reflections

169 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å⁻³

Δρmin = −0.83 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

See full table Table 1. Selected bond lengths (Å)

Supplementary Material

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2731).

supplementary crystallographic information

Comment

We are interested in Lewis-acidic Sn(IV) compounds and their reactivity towards Lewis bases. Recently we have reported the synthesis and structure of {Zn[Sn(CH₂SMe)₄]0.5Cl₂}n and Sn(CH₂PPh₂)₄ (Ruth et al., 2007). In contrast to [SnCl₄].[CH₃SCH₃]₂ which forms an adduct in solid state with a six-coordinated Sn atom (Ruth et al., 2005), the Sn(IV) centers in {Zn[Sn(CH₂SMe)₄]0.5Cl₂}n and Sn(CH₂PPh₂)₄ are tetra-coordinated. However, Me₃SnCl forms an adduct with Me₃SnOH and H₂O in which the Sn atoms possess the coordination number five. It is interesting to note that this adduct represents an intermediate in Me₃SnCl hydrolysis (Lerner et al., 2005). We report here the X-ray crystal structure analysis of the title adduct [Ph₂SnCl₂].[tBu₂MePO]₂, (I). The synthesis of (I) was achieved by treatment of Ph₂SnCl₂ with two equivalents of tBu₂MePO as indicated in the equation below.

Compound (I) has crystallographic inversion symmetry with just half a molecule in the asymmetric unit. The Sn atom is hexacoordinated by three pairs of different ligands in an octahedral fashion (Table 1). All ligand pairs of the same kind are mutually trans at the Sn atom (Fig. 1). As a consequence of the bulky substituents at the O atom the P—O—Sn angle is enlarged to 163.9 (3)°.

Experimental

tBu₂MePO (2.05 mmol) was added with stirring at ambient temperature to a solution of Ph₂SnCl₂ (0.58 mmol) in 25 ml THF. Colourless blocks of (I) were grown by storing this solution at room temperature for several weeks.

Refinement

The H atoms were geometrically positioned (C—H = 0.95-0.98Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(methyl C).

Figures

Fig. 1.View larger versionFig. 1. Perspective view of (I) with displacement ellipsoids drawn at the 50% probability level; H atoms are omitted for clarity. Symmetry operator for generating equivalent atoms: (A) 1 - x, 1 - y, 1 - z.

Crystal data

See full table

Data collection

See full table

Refinement

See full table

Special details

See full table

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

See full table

Atomic displacement parameters (Å²)

See full table

Geometric parameters (Å, °)

See full table

Symmetry codes: (i) −x+1, −y+1, −z+1.

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References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Lerner, H.-W., Haghiri Ilkechi, A., Bolte, M. & Wagner, M. (2005). Z. Naturforsch. Teil B, 60, 413–415.

Ruth, K., Lerner, H.-W. & Bolte, M. (2005). Acta Cryst. E61, m1852–m1853.

Ruth, K., Müller, M., Bolte, M., Bats, J. W., Wagner, M. & Lerner, H.-W. (2007). Z. Anorg. Allg. Chem.633, 1485–1489.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.

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Fig. 1.

Perspective view of (I) with displacement ellipsoids drawn at the 50% probability level; H atoms are omitted for clarity. Symmetry operator for generating equivalent atoms: (A) 1 - x, 1 - y, 1 - z.

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[Sn(C₆H₅)₂Cl₂(C₉H₂₁OP)₂] | F(000) = 724
Mr = 696.25 | Dx = 1.375 Mg m⁻³
Monoclinic, P2₁/c | Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc | Cell parameters from 4261 reflections
a = 12.1782 (19) Å | θ = 3.5–25.4°
b = 9.0866 (8) Å | µ = 1.04 mm⁻¹
c = 16.339 (2) Å | T = 173 K
β = 111.518 (11)° | Block, colourless
V = 1682.0 (4) Å³ | 0.13 × 0.09 × 0.07 mm
Z = 2 |

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Stoe IPDSII two-circle diffractometer | 3145 independent reflections
Radiation source: fine-focus sealed tube | 1754 reflections with I > 2σ(I)
graphite | Rint = 0.087
ω scans | θmax = 25.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −14→14
Tmin = 0.877, Tmax = 0.931 | k = −10→11
11731 measured reflections | l = −19→19

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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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098 | H-atom parameters constrained
S = 0.88 | w = 1/[σ²(Fo²) + (0.0102P)²] where P = (Fo² + 2Fc²)/3
3145 reflections | (Δ/σ)max < 0.001
169 parameters | Δρmax = 0.44 e Å⁻³
0 restraints | Δρmin = −0.83 e Å⁻³

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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.

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| x | y | z | Uiso*/Ueq |
Sn1 | 0.5000 | 0.5000 | 0.5000 | 0.02649 (18) |
Cl1 | 0.46725 (18) | 0.3097 (2) | 0.60405 (11) | 0.0361 (5) |
P1 | 0.31774 (17) | 0.7748 (2) | 0.56073 (11) | 0.0271 (4) |
O1 | 0.3737 (4) | 0.6468 (5) | 0.5312 (3) | 0.0300 (11) |
C1 | 0.2236 (7) | 0.7021 (8) | 0.6188 (4) | 0.0340 (17) |
C2 | 0.2381 (6) | 0.8878 (8) | 0.4633 (4) | 0.0337 (17) |
C3 | 0.4234 (7) | 0.8947 (8) | 0.6369 (4) | 0.0360 (18) |
H3A | 0.4684 | 0.8398 | 0.6903 | 0.054* |
H3B | 0.3822 | 0.9768 | 0.6521 | 0.054* |
H3C | 0.4774 | 0.9331 | 0.6100 | 0.054* |
C11 | 0.3017 (7) | 0.5921 (9) | 0.6885 (5) | 0.043 (2) |
H11A | 0.3721 | 0.6430 | 0.7282 | 0.064* |
H11B | 0.3257 | 0.5114 | 0.6589 | 0.064* |
H11C | 0.2568 | 0.5523 | 0.7225 | 0.064* |
C12 | 0.1142 (8) | 0.6241 (10) | 0.5567 (5) | 0.058 (3) |
H12A | 0.0656 | 0.6940 | 0.5126 | 0.086* |
H12B | 0.0686 | 0.5850 | 0.5903 | 0.086* |
H12C | 0.1380 | 0.5431 | 0.5273 | 0.086* |
C13 | 0.1867 (8) | 0.8238 (9) | 0.6696 (5) | 0.045 (2) |
H13A | 0.2574 | 0.8731 | 0.7101 | 0.068* |
H13B | 0.1428 | 0.7798 | 0.7031 | 0.068* |
H13C | 0.1366 | 0.8958 | 0.6279 | 0.068* |
C21 | 0.1735 (8) | 0.7857 (10) | 0.3860 (5) | 0.054 (2) |
H21A | 0.1137 | 0.7289 | 0.3994 | 0.081* |
H21B | 0.2303 | 0.7182 | 0.3762 | 0.081* |
H21C | 0.1351 | 0.8446 | 0.3329 | 0.081* |
C22 | 0.3310 (6) | 0.9731 (9) | 0.4389 (4) | 0.036 (2) |
H22A | 0.3744 | 1.0397 | 0.4871 | 0.054* |
H22B | 0.2916 | 1.0304 | 0.3853 | 0.054* |
H22C | 0.3862 | 0.9035 | 0.4288 | 0.054* |
C23 | 0.1515 (7) | 0.9993 (15) | 0.4782 (5) | 0.064 (3) |
H23A | 0.0918 | 0.9463 | 0.4938 | 0.096* |
H23B | 0.1128 | 1.0558 | 0.4242 | 0.096* |
H23C | 0.1950 | 1.0664 | 0.5261 | 0.096* |
C41 | 0.3564 (7) | 0.4098 (7) | 0.3934 (4) | 0.0276 (16) |
C42 | 0.2454 (7) | 0.3792 (8) | 0.3993 (5) | 0.0368 (18) |
H42 | 0.2346 | 0.3983 | 0.4530 | 0.044* |
C43 | 0.1523 (8) | 0.3224 (9) | 0.3291 (5) | 0.049 (2) |
H43 | 0.0771 | 0.3099 | 0.3334 | 0.059* |
C44 | 0.1696 (8) | 0.2832 (9) | 0.2512 (5) | 0.046 (2) |
H44 | 0.1076 | 0.2388 | 0.2039 | 0.055* |
C45 | 0.2763 (8) | 0.3097 (9) | 0.2440 (4) | 0.042 (2) |
H45 | 0.2876 | 0.2845 | 0.1912 | 0.051* |
C46 | 0.3695 (7) | 0.3738 (8) | 0.3140 (4) | 0.0347 (18) |
H46 | 0.4424 | 0.3930 | 0.3074 | 0.042* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
Sn1 | 0.0255 (4) | 0.0305 (4) | 0.0254 (3) | 0.0007 (6) | 0.0116 (3) | −0.0013 (5)
Cl1 | 0.0442 (12) | 0.0352 (11) | 0.0335 (9) | −0.0015 (10) | 0.0198 (9) | 0.0010 (8)
P1 | 0.0226 (11) | 0.0324 (11) | 0.0262 (8) | 0.0000 (9) | 0.0086 (8) | −0.0023 (8)
O1 | 0.031 (3) | 0.029 (3) | 0.033 (2) | 0.006 (2) | 0.015 (2) | −0.002 (2)
C1 | 0.032 (5) | 0.037 (4) | 0.036 (4) | −0.005 (4) | 0.017 (3) | −0.010 (3)
C2 | 0.024 (4) | 0.045 (5) | 0.034 (4) | 0.001 (4) | 0.013 (3) | −0.003 (3)
C3 | 0.032 (5) | 0.052 (5) | 0.025 (3) | −0.003 (4) | 0.012 (3) | 0.000 (3)
C11 | 0.051 (6) | 0.039 (5) | 0.046 (4) | −0.005 (4) | 0.027 (4) | 0.004 (4)
C12 | 0.055 (6) | 0.072 (7) | 0.058 (5) | −0.030 (5) | 0.034 (5) | −0.027 (5)
C13 | 0.048 (6) | 0.052 (5) | 0.046 (4) | −0.006 (5) | 0.029 (4) | −0.003 (4)
C21 | 0.038 (5) | 0.078 (7) | 0.036 (4) | 0.003 (5) | 0.002 (4) | 0.001 (4)
C22 | 0.034 (4) | 0.040 (6) | 0.039 (3) | 0.015 (4) | 0.018 (3) | 0.009 (4)
C23 | 0.057 (6) | 0.087 (6) | 0.059 (4) | 0.056 (8) | 0.033 (4) | 0.026 (7)
C41 | 0.036 (5) | 0.021 (4) | 0.021 (3) | 0.000 (3) | 0.004 (3) | −0.004 (3)
C42 | 0.024 (4) | 0.047 (5) | 0.043 (4) | −0.009 (4) | 0.017 (4) | −0.013 (4)
C43 | 0.033 (5) | 0.052 (6) | 0.066 (5) | 0.000 (5) | 0.022 (4) | 0.000 (4)
C44 | 0.036 (5) | 0.041 (5) | 0.048 (4) | −0.002 (4) | 0.003 (4) | −0.006 (4)
C45 | 0.043 (5) | 0.047 (5) | 0.029 (4) | −0.004 (4) | 0.004 (4) | 0.001 (3)
C46 | 0.036 (5) | 0.032 (5) | 0.035 (4) | 0.007 (4) | 0.012 (4) | 0.008 (3)

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Sn1—C41i | 2.128 (7) | C12—H12C | 0.9800
Sn1—C41 | 2.128 (7) | C13—H13A | 0.9800
Sn1—O1 | 2.232 (4) | C13—H13B | 0.9800
Sn1—O1i | 2.232 (4) | C13—H13C | 0.9800
Sn1—Cl1i | 2.5567 (16) | C21—H21A | 0.9800
Sn1—Cl1 | 2.5567 (16) | C21—H21B | 0.9800
P1—O1 | 1.513 (4) | C21—H21C | 0.9800
P1—C3 | 1.794 (7) | C22—H22A | 0.9800
P1—C2 | 1.842 (7) | C22—H22B | 0.9800
P1—C1 | 1.858 (7) | C22—H22C | 0.9800
C1—C12 | 1.522 (10) | C23—H23A | 0.9800
C1—C11 | 1.552 (10) | C23—H23B | 0.9800
C1—C13 | 1.545 (9) | C23—H23C | 0.9800
C2—C22 | 1.541 (10) | C41—C46 | 1.402 (8)
C2—C21 | 1.533 (11) | C41—C42 | 1.418 (10)
C2—C23 | 1.544 (11) | C42—C43 | 1.383 (10)
C3—H3A | 0.9800 | C42—H42 | 0.9500
C3—H3B | 0.9800 | C43—C44 | 1.412 (10)
C3—H3C | 0.9800 | C43—H43 | 0.9500
C11—H11A | 0.9800 | C44—C45 | 1.367 (11)
C11—H11B | 0.9800 | C44—H44 | 0.9500
C11—H11C | 0.9800 | C45—C46 | 1.409 (10)
C12—H12A | 0.9800 | C45—H45 | 0.9500
C12—H12B | 0.9800 | C46—H46 | 0.9500
C41i—Sn1—C41 | 180.0 | C1—C12—H12B | 109.5
C41i—Sn1—O1 | 90.6 (2) | H12A—C12—H12B | 109.5
C41—Sn1—O1 | 89.4 (2) | C1—C12—H12C | 109.5
C41i—Sn1—O1i | 89.4 (2) | H12A—C12—H12C | 109.5
C41—Sn1—O1i | 90.6 (2) | H12B—C12—H12C | 109.5
O1—Sn1—O1i | 180.0 | C1—C13—H13A | 109.5
C41i—Sn1—Cl1i | 90.10 (18) | C1—C13—H13B | 109.5
C41—Sn1—Cl1i | 89.90 (18) | H13A—C13—H13B | 109.5
O1—Sn1—Cl1i | 92.09 (12) | C1—C13—H13C | 109.5
O1i—Sn1—Cl1i | 87.91 (12) | H13A—C13—H13C | 109.5
C41i—Sn1—Cl1 | 89.90 (18) | H13B—C13—H13C | 109.5
C41—Sn1—Cl1 | 90.10 (18) | C2—C21—H21A | 109.5
O1—Sn1—Cl1 | 87.91 (12) | C2—C21—H21B | 109.5
O1i—Sn1—Cl1 | 92.09 (12) | H21A—C21—H21B | 109.5
Cl1i—Sn1—Cl1 | 180.0 | C2—C21—H21C | 109.5
O1—P1—C3 | 113.3 (3) | H21A—C21—H21C | 109.5
O1—P1—C2 | 108.0 (3) | H21B—C21—H21C | 109.5
C3—P1—C2 | 106.1 (3) | C2—C22—H22A | 109.5
O1—P1—C1 | 108.9 (3) | C2—C22—H22B | 109.5
C3—P1—C1 | 106.4 (3) | H22A—C22—H22B | 109.5
C2—P1—C1 | 114.3 (3) | C2—C22—H22C | 109.5
P1—O1—Sn1 | 163.9 (3) | H22A—C22—H22C | 109.5
C12—C1—C11 | 109.9 (7) | H22B—C22—H22C | 109.5
C12—C1—C13 | 109.6 (6) | C2—C23—H23A | 109.5
C11—C1—C13 | 106.7 (6) | C2—C23—H23B | 109.5
C12—C1—P1 | 112.3 (4) | H23A—C23—H23B | 109.5
C11—C1—P1 | 106.1 (5) | C2—C23—H23C | 109.5
C13—C1—P1 | 112.0 (5) | H23A—C23—H23C | 109.5
C22—C2—C21 | 107.1 (6) | H23B—C23—H23C | 109.5
C22—C2—C23 | 108.7 (7) | C46—C41—C42 | 116.8 (7)
C21—C2—C23 | 110.7 (7) | C46—C41—Sn1 | 120.6 (5)
C22—C2—P1 | 107.5 (5) | C42—C41—Sn1 | 122.6 (5)
C21—C2—P1 | 108.9 (5) | C43—C42—C41 | 122.0 (6)
C23—C2—P1 | 113.8 (4) | C43—C42—H42 | 119.0
P1—C3—H3A | 109.5 | C41—C42—H42 | 119.0
P1—C3—H3B | 109.5 | C42—C43—C44 | 119.6 (7)
H3A—C3—H3B | 109.5 | C42—C43—H43 | 120.2
P1—C3—H3C | 109.5 | C44—C43—H43 | 120.2
H3A—C3—H3C | 109.5 | C45—C44—C43 | 119.6 (8)
H3B—C3—H3C | 109.5 | C45—C44—H44 | 120.2
C1—C11—H11A | 109.5 | C43—C44—H44 | 120.2
C1—C11—H11B | 109.5 | C44—C45—C46 | 120.7 (7)
H11A—C11—H11B | 109.5 | C44—C45—H45 | 119.6
C1—C11—H11C | 109.5 | C46—C45—H45 | 119.6
H11A—C11—H11C | 109.5 | C41—C46—C45 | 121.1 (7)
H11B—C11—H11C | 109.5 | C41—C46—H46 | 119.4
C1—C12—H12A | 109.5 | C45—C46—H46 | 119.4
C3—P1—O1—Sn1 | −21.3 (11) | C1—P1—C2—C21 | −79.8 (6)
C2—P1—O1—Sn1 | 95.9 (10) | O1—P1—C2—C23 | 165.5 (7)
C1—P1—O1—Sn1 | −139.5 (9) | C3—P1—C2—C23 | −72.7 (7)
C41i—Sn1—O1—P1 | 31.6 (10) | C1—P1—C2—C23 | 44.2 (8)
C41—Sn1—O1—P1 | −148.4 (10) | O1—Sn1—C41—C46 | 142.0 (5)
Cl1i—Sn1—O1—P1 | −58.5 (10) | O1i—Sn1—C41—C46 | −38.0 (5)
Cl1—Sn1—O1—P1 | 121.5 (10) | Cl1i—Sn1—C41—C46 | 49.9 (5)
O1—P1—C1—C12 | −69.5 (6) | Cl1—Sn1—C41—C46 | −130.1 (5)
C3—P1—C1—C12 | 168.1 (6) | O1—Sn1—C41—C42 | −39.9 (6)
C2—P1—C1—C12 | 51.4 (7) | O1i—Sn1—C41—C42 | 140.1 (6)
O1—P1—C1—C11 | 50.5 (5) | Cl1i—Sn1—C41—C42 | −132.0 (6)
C3—P1—C1—C11 | −71.9 (5) | Cl1—Sn1—C41—C42 | 48.0 (6)
C2—P1—C1—C11 | 171.4 (5) | C46—C41—C42—C43 | −2.7 (11)
O1—P1—C1—C13 | 166.6 (5) | Sn1—C41—C42—C43 | 179.1 (6)
C3—P1—C1—C13 | 44.2 (6) | C41—C42—C43—C44 | 4.7 (12)
C2—P1—C1—C13 | −72.5 (6) | C42—C43—C44—C45 | −3.8 (12)
O1—P1—C2—C22 | −74.1 (5) | C43—C44—C45—C46 | 0.8 (12)
C3—P1—C2—C22 | 47.7 (5) | C42—C41—C46—C45 | −0.3 (10)
C1—P1—C2—C22 | 164.5 (5) | Sn1—C41—C46—C45 | 178.0 (6)
O1—P1—C2—C21 | 41.6 (6) | C44—C45—C46—C41 | 1.2 (12)
C3—P1—C2—C21 | 163.4 (5) |  |

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Table 1. Selected bond lengths (Å)

Sn1—C41 | 2.128 (7)
Sn1—O1 | 2.232 (4)
Sn1—Cl1 | 2.5567 (16)

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