Tetra­iodido[methyl­enebis(diphenyl­phosphine oxide)-κ2O:O′]tin(IV) chloro­form solvate

Caldwell, A.M.; Tanski, J.M.

doi:10.1107/S1600536808013627

metal-organic compounds

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Volume 64| Part 7| July 2008| Page m894

doi:10.1107/S1600536808013627

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Tetraiodido[methylenebis(diphenylphosphine oxide)-κ²O:O′]tin(IV) chloroform solvate

Allison M. Caldwell ^a and Joseph M. Tanski ^a ^*

^aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
^*Correspondence e-mail: jotanski@vassar.edu

(Received 24 April 2008; accepted 7 May 2008; online 7 June 2008)

The title compound, [SnI₄(C₂₅H₂₂O₂P₂)]·CHCl₃, crystallized from a chloroform solution of SnI₄ and the diphosphine CH₂(PPh₂)₂ exposed to air. The monomeric complex displays a distorted octahedral coordinaton for the tin(IV) atom with average Sn—I and Sn—O bond lengths of 2.79 (2) and 2.15 (1) Å, respectively.

Related literature

For examples of structurally characterized tin(IV)–halide complexes of phosphine oxide ligands, see: Genge et al. (1999 ); Davis et al. (2006a ,b ); Mohamed et al. (2004 ). For related literature, see: Levason et al. (2003 ); Woollins (2003 ).

Experimental

Crystal data

[SnI₄(C₂₅H₂₂O₂P₂)]·CHCl₃
M_r = 1162.02
Monoclinic, P 2₁
a = 9.2639 (5) Å
b = 19.0609 (11) Å
c = 10.1991 (6) Å
β = 108.479 (1)°
V = 1708.08 (17) Å³
Z = 2
Mo Kα radiation
μ = 4.71 mm⁻¹
T = 125 (2) K
0.14 × 0.13 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.558, T_max = 0.912
20220 measured reflections
7254 independent reflections
6994 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.045
S = 1.03
7254 reflections
344 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.50 e Å⁻³
Absolute structure: Flack (1983 ), 3512 Friedel pairs
Flack parameter: 0.004 (14)

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013627/wm2178sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013627/wm2178Isup2.hkl

checkCIF report

Comment top

Tin(IV) iodide may be readily prepared by oxidation of tin metal with iodine (Woollins, 2003). A relatively weak Lewis acid, SnI₄ nevertheless forms complexes with phosphines and phosphine oxides (Genge et al., 1999; Davis et al., 2006a). Similar phosphine and phosphine oxide complexes have been reported of the more Lewis acidic tin(IV) halides, SnX₄ (X = F, Cl, Br; Davis et al., 2006a, 2006b; Genge et al., 1999; Mohamed et al., 2004). The phosphine oxide complexes are chiefly obtained by air oxidation of the phosphine ligands in the presence of the tin(IV) halide (Levason et al., 2003).

Reaction of SnI₄ with CH₂(PPh₂)₂ in CHCl₃ in the presence of air afforded the title complex [{CH₂(P(O)Ph₂)₂}SnI₄]^.CHCl₃, (I).

Complex (I) exhibits a distorted octahedral coordination at tin. The bis(phosphine oxide) results in a cis coordination of the ligand, with Sn—O distances of 2.136 (3) and 2.157 (3) Å, and Sn—I distances of 2.7770 (4), 2.7805 (4), 2.7911 (4) and 2.8199 (4) Å. The smallest bond angle about the pseudooctahedral tin center, 81.1 (1)°, corresponds to the O1—Sn—O2 angle of the chelating bis(phosphine oxide) ligand, with the opposite I2—Sn—I3 angle in the SnO₂I₂ plane being the largest, 100.82 (1)°. These distances and angles are similar to those reported for the related bis(phosphine oxide) complex {o-C₆H₄(P(O)Ph₂)₂}SnI₄(Genge et al., 1999). The SnO₂P₂C six-membered heterocycle in complex (I) is in a distorted boat conformation.

Related literature top

For examples of structurally characterized tin(IV)–halide complexes of phosphine oxide ligands, see: Genge et al. (1999); Davis et al. (2006a,b); Mohamed et al. (2004). For related literature, see: Levason et al. (2003); Woollins (2003).

Experimental top

Complex (I) was prepared by treating a chloroform (ca 5 ml) solution of SnI₄ (655 mg, 1.1 mmol) with an excess of CH₂(PPh₂)₂ (922 mg, 2.6 mmol) in the presence of air. Suitable crystals for single crystal X-ray analysis formed within 1 week at room temperature. A small sample of crystals was separated for structural analysis, and the remaining crystals were collected by filtration on a glass frit, washed three times with ca 5 ml of chloroform, and dried briefly under vacuum (yield 659 mg (54%) of a red-orange product). Elemental analysis confirmed that the compound was obtained as the chloroform solvate: anal. calcd. for (I) C, 26.87%; H, 1.99%; N, 0.00%. Found C, 26.97%; H, 1.73%; N, <0.02%. (Elemental analysis performed by Robertson Microlit Laboratories, Madison, NJ, USA.)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of complex (I) with displacement ellipsoids shown at the 50% probability level. H atoms have been omitted for clarity.

Tetraiodido[methylenebis(diphenylphosphine oxide)-κ²O:O']tin(IV) chloroform solvate top

Crystal data top

[SnI₄(C₂₅H₂₂O₂P₂)]·CHCl₃	F(000) = 1076
M_r = 1162.02	D_x = 2.259 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9838 reflections
a = 9.2639 (5) Å	θ = 2.3–28.3°
b = 19.0609 (11) Å	µ = 4.71 mm⁻¹
c = 10.1991 (6) Å	T = 125 K
β = 108.479 (1)°	Plate, orange
V = 1708.08 (17) Å³	0.14 × 0.13 × 0.02 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	7254 independent reflections
Radiation source: fine-focus sealed tube	6994 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 26.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.558, T_max = 0.912	k = −24→24
20220 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.046	w = 1/[σ²(F_o²) + (0.0195P)² + 0.2278P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
7254 reflections	Δρ_max = 0.73 e Å⁻³
344 parameters	Δρ_min = −0.50 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3512 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (14)

Crystal data top

[SnI₄(C₂₅H₂₂O₂P₂)]·CHCl₃	V = 1708.08 (17) Å³
M_r = 1162.02	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.2639 (5) Å	µ = 4.71 mm⁻¹
b = 19.0609 (11) Å	T = 125 K
c = 10.1991 (6) Å	0.14 × 0.13 × 0.02 mm
β = 108.479 (1)°

Data collection top

Bruker APEXII CCD diffractometer	7254 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	6994 reflections with I > 2σ(I)
T_min = 0.558, T_max = 0.912	R_int = 0.027
20220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.046	Δρ_max = 0.73 e Å⁻³
S = 1.03	Δρ_min = −0.50 e Å⁻³
7254 reflections	Absolute structure: Flack (1983), 3512 Friedel pairs
344 parameters	Absolute structure parameter: 0.004 (14)
1 restraint

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. A suitable crystal was mounted in a nylon loop with Paratone-N cryoprotectant oil and data was collected on a Bruker APEX 2 CCD platform diffractometer. The data was cut off at 0.79 Å because data in the highest resolution range (0.75-0.78 Å) was very incomplete, acting to reduce the overall completeness to 99.4%. The structure was solved using direct methods and standard difference map techniques, and was refined by full-matrix least-squares procedures on F² with SHELXTL Version 6.14 (Sheldrick, 2008). One least squares restraint is required for the floating origin of space group P2₁. All non-hydrogen atoms were refined anisotropically. 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. EXTI refined to zero and was removed from the refinement.

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

	x	y	z	U_iso*/U_eq
Sn	0.83582 (3)	0.791335 (15)	0.25375 (3)	0.01631 (6)
I1	0.75473 (3)	0.673729 (13)	0.38291 (3)	0.02340 (7)
I2	0.98608 (3)	0.706487 (16)	0.11538 (3)	0.02731 (7)
I3	1.07128 (3)	0.821230 (17)	0.49436 (3)	0.02768 (7)
I4	0.89066 (3)	0.910079 (14)	0.11840 (3)	0.02389 (7)
P1	0.54635 (12)	0.85261 (5)	0.35831 (11)	0.0155 (2)
P2	0.45533 (11)	0.79067 (6)	0.06921 (10)	0.0162 (2)
O1	0.6960 (3)	0.85997 (14)	0.3271 (3)	0.0178 (6)
O2	0.6235 (3)	0.77647 (14)	0.0902 (3)	0.0166 (6)
C1	0.3884 (5)	0.8709 (2)	−0.0204 (4)	0.0193 (9)
C2	0.2576 (5)	0.9026 (3)	−0.0116 (5)	0.0329 (11)
H2A	0.2042	0.8827	0.0450	0.039*
C3	0.2044 (6)	0.9636 (3)	−0.0854 (6)	0.0420 (13)
H3A	0.1151	0.9859	−0.0789	0.050*
C4	0.2817 (7)	0.9918 (3)	−0.1683 (6)	0.0487 (15)
H4A	0.2453	1.0336	−0.2187	0.058*
C5	0.4107 (6)	0.9603 (3)	−0.1788 (5)	0.0372 (13)
H5A	0.4625	0.9798	−0.2371	0.045*
C6	0.4650 (5)	0.9000 (3)	−0.1042 (4)	0.0272 (10)
H6A	0.5551	0.8784	−0.1102	0.033*
C7	0.3424 (5)	0.7198 (2)	−0.0266 (4)	0.0187 (9)
C8	0.2165 (5)	0.7324 (3)	−0.1412 (4)	0.0269 (10)
H8A	0.1873	0.7791	−0.1699	0.032*
C9	0.1332 (5)	0.6761 (3)	−0.2139 (4)	0.0316 (11)
H9A	0.0471	0.6843	−0.2929	0.038*
C10	0.1755 (6)	0.6084 (3)	−0.1715 (5)	0.0303 (11)
H10A	0.1178	0.5701	−0.2210	0.036*
C11	0.3025 (6)	0.5957 (3)	−0.0562 (5)	0.0322 (11)
H11A	0.3310	0.5490	−0.0267	0.039*
C12	0.3863 (5)	0.6516 (2)	0.0146 (5)	0.0253 (10)
H12A	0.4744	0.6433	0.0918	0.030*
C13	0.4575 (5)	0.9369 (2)	0.3409 (4)	0.0194 (9)
C14	0.3480 (5)	0.9506 (2)	0.4051 (5)	0.0280 (10)
H14A	0.3271	0.9166	0.4649	0.034*
C15	0.2702 (5)	1.0132 (3)	0.3818 (6)	0.0341 (12)
H15A	0.1950	1.0220	0.4249	0.041*
C16	0.3002 (6)	1.0628 (2)	0.2971 (5)	0.0345 (12)
H16A	0.2462	1.1059	0.2820	0.041*
C17	0.4098 (6)	1.0500 (2)	0.2331 (5)	0.0320 (11)
H17A	0.4297	1.0841	0.1732	0.038*
C18	0.4897 (5)	0.9874 (2)	0.2569 (5)	0.0255 (10)
H18A	0.5667	0.9792	0.2156	0.031*
C19	0.5743 (5)	0.8157 (2)	0.5259 (4)	0.0181 (8)
C20	0.4710 (5)	0.7703 (2)	0.5528 (4)	0.0218 (9)
H20A	0.3760	0.7615	0.4841	0.026*
C21	0.5063 (5)	0.7376 (2)	0.6807 (4)	0.0244 (10)
H21A	0.4348	0.7069	0.6998	0.029*
C22	0.6457 (6)	0.7497 (2)	0.7807 (4)	0.0285 (10)
H22A	0.6704	0.7264	0.8674	0.034*
C23	0.7478 (5)	0.7954 (2)	0.7542 (4)	0.0272 (10)
H23A	0.8426	0.8038	0.8235	0.033*
C24	0.7148 (5)	0.8295 (2)	0.6282 (4)	0.0255 (9)
H24A	0.7853	0.8615	0.6110	0.031*
C25	0.4202 (4)	0.7925 (2)	0.2343 (4)	0.0168 (8)
H25A	0.4335	0.7447	0.2740	0.020*
H25B	0.3133	0.8067	0.2192	0.020*
C26	0.1709 (7)	0.5583 (3)	0.3620 (5)	0.0447 (14)
H26A	0.0865	0.5924	0.3219	0.054*
Cl1	0.3366 (3)	0.60552 (10)	0.4432 (2)	0.1039 (9)
Cl2	0.19826 (17)	0.50905 (9)	0.22600 (15)	0.0518 (4)
Cl3	0.11844 (19)	0.50376 (8)	0.47642 (15)	0.0522 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01542 (13)	0.01735 (13)	0.01582 (13)	0.00235 (11)	0.00450 (10)	0.00282 (10)
I1	0.02927 (16)	0.01839 (14)	0.02235 (14)	0.00030 (12)	0.00790 (12)	0.00269 (11)
I2	0.03002 (16)	0.03117 (15)	0.02356 (14)	0.01382 (13)	0.01252 (12)	0.00496 (13)
I3	0.01861 (14)	0.03691 (17)	0.02288 (14)	−0.00201 (13)	0.00001 (11)	0.00444 (13)
I4	0.02432 (14)	0.02220 (14)	0.02621 (15)	−0.00028 (12)	0.00951 (12)	0.00677 (11)
P1	0.0163 (5)	0.0144 (5)	0.0159 (5)	−0.0010 (4)	0.0053 (4)	−0.0008 (4)
P2	0.0160 (5)	0.0178 (5)	0.0132 (5)	0.0002 (5)	0.0027 (4)	0.0005 (4)
O1	0.0178 (14)	0.0193 (15)	0.0154 (14)	−0.0023 (11)	0.0041 (11)	−0.0042 (11)
O2	0.0173 (14)	0.0179 (15)	0.0133 (13)	0.0013 (11)	0.0029 (11)	0.0007 (11)
C1	0.024 (2)	0.015 (2)	0.016 (2)	−0.0008 (17)	0.0017 (17)	0.0056 (16)
C2	0.021 (2)	0.037 (3)	0.038 (3)	0.006 (2)	0.006 (2)	0.009 (2)
C3	0.035 (3)	0.037 (3)	0.050 (3)	0.012 (2)	0.006 (3)	0.019 (3)
C4	0.037 (3)	0.035 (3)	0.060 (4)	0.009 (2)	−0.005 (3)	0.023 (3)
C5	0.034 (3)	0.036 (3)	0.035 (3)	−0.009 (2)	0.003 (2)	0.017 (2)
C6	0.020 (2)	0.034 (3)	0.024 (2)	−0.001 (2)	0.0028 (18)	0.007 (2)
C7	0.018 (2)	0.022 (2)	0.0162 (19)	−0.0016 (17)	0.0069 (16)	−0.0033 (17)
C8	0.029 (3)	0.027 (2)	0.021 (2)	−0.006 (2)	0.0034 (19)	−0.0019 (18)
C9	0.030 (3)	0.040 (3)	0.018 (2)	−0.006 (2)	−0.0014 (19)	0.000 (2)
C10	0.033 (3)	0.033 (3)	0.023 (2)	−0.011 (2)	0.005 (2)	−0.007 (2)
C11	0.038 (3)	0.025 (3)	0.030 (3)	−0.003 (2)	0.006 (2)	−0.002 (2)
C12	0.029 (3)	0.023 (2)	0.019 (2)	−0.0035 (19)	0.0013 (19)	−0.0034 (18)
C13	0.017 (2)	0.0147 (19)	0.023 (2)	0.0010 (16)	0.0021 (17)	−0.0006 (17)
C14	0.026 (2)	0.020 (2)	0.043 (3)	−0.0018 (19)	0.019 (2)	−0.005 (2)
C15	0.026 (3)	0.026 (3)	0.058 (3)	0.000 (2)	0.025 (2)	−0.008 (2)
C16	0.035 (3)	0.016 (2)	0.046 (3)	0.006 (2)	0.004 (2)	−0.002 (2)
C17	0.040 (3)	0.023 (2)	0.033 (3)	0.000 (2)	0.012 (2)	0.004 (2)
C18	0.030 (2)	0.020 (2)	0.026 (2)	−0.0014 (19)	0.010 (2)	−0.0008 (18)
C19	0.025 (2)	0.016 (2)	0.0158 (19)	0.0014 (17)	0.0098 (17)	−0.0028 (16)
C20	0.017 (2)	0.025 (2)	0.024 (2)	−0.0006 (17)	0.0089 (18)	−0.0023 (17)
C21	0.028 (2)	0.027 (2)	0.023 (2)	0.0009 (19)	0.0145 (19)	0.0016 (18)
C22	0.046 (3)	0.027 (2)	0.014 (2)	0.005 (2)	0.011 (2)	0.0030 (18)
C23	0.032 (3)	0.033 (3)	0.015 (2)	0.004 (2)	0.0050 (18)	−0.0048 (19)
C24	0.026 (2)	0.026 (2)	0.022 (2)	−0.0040 (19)	0.0036 (18)	−0.0037 (19)
C25	0.0190 (19)	0.0148 (18)	0.0162 (19)	−0.0010 (18)	0.0048 (15)	0.0025 (17)
C26	0.059 (4)	0.027 (3)	0.036 (3)	−0.003 (3)	−0.002 (3)	0.010 (2)
Cl1	0.1176 (17)	0.0573 (12)	0.0806 (14)	−0.0501 (12)	−0.0484 (12)	0.0197 (10)
Cl2	0.0441 (8)	0.0688 (10)	0.0441 (8)	0.0007 (7)	0.0161 (7)	0.0017 (7)
Cl3	0.0719 (10)	0.0461 (8)	0.0415 (8)	0.0182 (8)	0.0221 (7)	0.0119 (7)

Geometric parameters (Å, º) top

Sn—O1	2.136 (3)	C10—H10A	0.9500
Sn—O2	2.157 (3)	C11—C12	1.379 (6)
Sn—I3	2.7770 (4)	C11—H11A	0.9500
Sn—I4	2.7805 (4)	C12—H12A	0.9500
Sn—I2	2.7911 (4)	C13—C18	1.383 (6)
Sn—I1	2.8199 (4)	C13—C14	1.395 (6)
P1—O1	1.524 (3)	C14—C15	1.375 (7)
P1—C13	1.788 (4)	C14—H14A	0.9500
P1—C19	1.790 (4)	C15—C16	1.366 (7)
P1—C25	1.828 (4)	C15—H15A	0.9500
P2—O2	1.527 (3)	C16—C17	1.392 (7)
P2—C1	1.788 (4)	C16—H16A	0.9500
P2—C7	1.795 (4)	C17—C18	1.383 (6)
P2—C25	1.814 (4)	C17—H17A	0.9500
C1—C2	1.383 (6)	C18—H18A	0.9500
C1—C6	1.388 (6)	C19—C20	1.381 (6)
C2—C3	1.389 (7)	C19—C24	1.411 (6)
C2—H2A	0.9500	C20—C21	1.387 (6)
C3—C4	1.378 (8)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.388 (6)
C4—C5	1.372 (8)	C21—H21A	0.9500
C4—H4A	0.9500	C22—C23	1.375 (7)
C5—C6	1.382 (7)	C22—H22A	0.9500
C5—H5A	0.9500	C23—C24	1.385 (6)
C6—H6A	0.9500	C23—H23A	0.9500
C7—C8	1.386 (6)	C24—H24A	0.9500
C7—C12	1.387 (6)	C25—H25A	0.9900
C8—C9	1.391 (6)	C25—H25B	0.9900
C8—H8A	0.9500	C26—Cl3	1.742 (6)
C9—C10	1.377 (7)	C26—Cl1	1.746 (6)
C9—H9A	0.9500	C26—Cl2	1.758 (6)
C10—C11	1.397 (7)	C26—H26A	1.0000

O1—Sn—O2	81.11 (10)	C9—C10—H10A	119.8
O1—Sn—I3	87.62 (7)	C11—C10—H10A	119.8
O2—Sn—I3	168.16 (7)	C12—C11—C10	119.4 (4)
O1—Sn—I4	84.36 (8)	C12—C11—H11A	120.3
O2—Sn—I4	89.34 (7)	C10—C11—H11A	120.3
I3—Sn—I4	93.196 (12)	C11—C12—C7	120.2 (4)
O1—Sn—I2	170.71 (7)	C11—C12—H12A	119.9
O2—Sn—I2	90.68 (7)	C7—C12—H12A	119.9
I3—Sn—I2	100.824 (13)	C18—C13—C14	119.5 (4)
I4—Sn—I2	91.247 (12)	C18—C13—P1	120.3 (3)
O1—Sn—I1	92.43 (8)	C14—C13—P1	120.1 (3)
O2—Sn—I1	86.79 (7)	C15—C14—C13	120.0 (4)
I3—Sn—I1	90.070 (12)	C15—C14—H14A	120.0
I4—Sn—I1	175.320 (14)	C13—C14—H14A	120.0
I2—Sn—I1	91.431 (12)	C16—C15—C14	120.6 (4)
O1—P1—C13	108.51 (18)	C16—C15—H15A	119.7
O1—P1—C19	111.71 (18)	C14—C15—H15A	119.7
C13—P1—C19	111.74 (19)	C15—C16—C17	120.0 (4)
O1—P1—C25	109.74 (17)	C15—C16—H16A	120.0
C13—P1—C25	108.71 (19)	C17—C16—H16A	120.0
C19—P1—C25	106.37 (19)	C18—C17—C16	119.9 (4)
O2—P2—C1	113.34 (18)	C18—C17—H17A	120.1
O2—P2—C7	109.60 (18)	C16—C17—H17A	120.1
C1—P2—C7	108.48 (19)	C13—C18—C17	120.0 (4)
O2—P2—C25	110.39 (17)	C13—C18—H18A	120.0
C1—P2—C25	108.8 (2)	C17—C18—H18A	120.0
C7—P2—C25	105.94 (19)	C20—C19—C24	120.3 (4)
P1—O1—Sn	135.20 (17)	C20—C19—P1	122.4 (3)
P2—O2—Sn	136.45 (16)	C24—C19—P1	117.0 (3)
C2—C1—C6	119.7 (4)	C19—C20—C21	119.7 (4)
C2—C1—P2	120.7 (3)	C19—C20—H20A	120.1
C6—C1—P2	119.6 (3)	C21—C20—H20A	120.1
C1—C2—C3	119.9 (5)	C20—C21—C22	120.3 (4)
C1—C2—H2A	120.0	C20—C21—H21A	119.8
C3—C2—H2A	120.0	C22—C21—H21A	119.8
C4—C3—C2	119.7 (5)	C23—C22—C21	119.9 (4)
C4—C3—H3A	120.2	C23—C22—H22A	120.1
C2—C3—H3A	120.2	C21—C22—H22A	120.1
C5—C4—C3	120.8 (5)	C22—C23—C24	121.1 (4)
C5—C4—H4A	119.6	C22—C23—H23A	119.5
C3—C4—H4A	119.6	C24—C23—H23A	119.5
C4—C5—C6	119.7 (5)	C23—C24—C19	118.7 (4)
C4—C5—H5A	120.1	C23—C24—H24A	120.7
C6—C5—H5A	120.1	C19—C24—H24A	120.7
C5—C6—C1	120.2 (4)	P2—C25—P1	113.0 (2)
C5—C6—H6A	119.9	P2—C25—H25A	109.0
C1—C6—H6A	119.9	P1—C25—H25A	109.0
C8—C7—C12	120.3 (4)	P2—C25—H25B	109.0
C8—C7—P2	121.2 (3)	P1—C25—H25B	109.0
C12—C7—P2	118.4 (3)	H25A—C25—H25B	107.8
C7—C8—C9	119.5 (4)	Cl3—C26—Cl1	112.4 (3)
C7—C8—H8A	120.2	Cl3—C26—Cl2	110.5 (3)
C9—C8—H8A	120.2	Cl1—C26—Cl2	108.9 (4)
C10—C9—C8	120.0 (4)	Cl3—C26—H26A	108.3
C10—C9—H9A	120.0	Cl1—C26—H26A	108.3
C8—C9—H9A	120.0	Cl2—C26—H26A	108.3
C9—C10—C11	120.4 (4)

C13—P1—O1—Sn	−154.2 (2)	C9—C10—C11—C12	−0.5 (8)
C19—P1—O1—Sn	82.2 (3)	C10—C11—C12—C7	1.6 (7)
C25—P1—O1—Sn	−35.5 (3)	C8—C7—C12—C11	−1.7 (7)
O2—Sn—O1—P1	54.1 (2)	P2—C7—C12—C11	179.9 (4)
I3—Sn—O1—P1	−122.2 (2)	O1—P1—C13—C18	24.9 (4)
I4—Sn—O1—P1	144.3 (2)	C19—P1—C13—C18	148.5 (4)
I1—Sn—O1—P1	−32.3 (2)	C25—P1—C13—C18	−94.4 (4)
C1—P2—O2—Sn	97.2 (3)	O1—P1—C13—C14	−159.1 (3)
C7—P2—O2—Sn	−141.4 (2)	C19—P1—C13—C14	−35.5 (4)
C25—P2—O2—Sn	−25.1 (3)	C25—P1—C13—C14	81.6 (4)
O1—Sn—O2—P2	−16.7 (2)	C18—C13—C14—C15	1.7 (7)
I3—Sn—O2—P2	1.4 (6)	P1—C13—C14—C15	−174.3 (4)
I4—Sn—O2—P2	−101.1 (2)	C13—C14—C15—C16	−0.7 (8)
I2—Sn—O2—P2	167.6 (2)	C14—C15—C16—C17	0.3 (8)
I1—Sn—O2—P2	76.2 (2)	C15—C16—C17—C18	−0.9 (8)
O2—P2—C1—C2	−159.9 (3)	C14—C13—C18—C17	−2.3 (7)
C7—P2—C1—C2	78.1 (4)	P1—C13—C18—C17	173.7 (3)
C25—P2—C1—C2	−36.7 (4)	C16—C17—C18—C13	1.9 (7)
O2—P2—C1—C6	22.7 (4)	O1—P1—C19—C20	−144.0 (3)
C7—P2—C1—C6	−99.3 (4)	C13—P1—C19—C20	94.2 (4)
C25—P2—C1—C6	145.9 (3)	C25—P1—C19—C20	−24.3 (4)
C6—C1—C2—C3	−0.5 (7)	O1—P1—C19—C24	30.0 (4)
P2—C1—C2—C3	−177.9 (4)	C13—P1—C19—C24	−91.8 (4)
C1—C2—C3—C4	0.6 (8)	C25—P1—C19—C24	149.7 (3)
C2—C3—C4—C5	0.1 (9)	C24—C19—C20—C21	−0.6 (6)
C3—C4—C5—C6	−0.8 (9)	P1—C19—C20—C21	173.2 (3)
C4—C5—C6—C1	0.9 (8)	C19—C20—C21—C22	−0.8 (7)
C2—C1—C6—C5	−0.3 (7)	C20—C21—C22—C23	1.5 (7)
P2—C1—C6—C5	177.1 (4)	C21—C22—C23—C24	−0.6 (7)
O2—P2—C7—C8	−130.5 (4)	C22—C23—C24—C19	−0.8 (7)
C1—P2—C7—C8	−6.3 (4)	C20—C19—C24—C23	1.4 (6)
C25—P2—C7—C8	110.4 (4)	P1—C19—C24—C23	−172.7 (3)
O2—P2—C7—C12	47.8 (4)	O2—P2—C25—P1	52.7 (3)
C1—P2—C7—C12	172.0 (3)	C1—P2—C25—P1	−72.2 (3)
C25—P2—C7—C12	−71.3 (4)	C7—P2—C25—P1	171.3 (2)
C12—C7—C8—C9	0.8 (7)	O1—P1—C25—P2	−27.7 (3)
P2—C7—C8—C9	179.1 (3)	C13—P1—C25—P2	90.8 (3)
C7—C8—C9—C10	0.3 (7)	C19—P1—C25—P2	−148.7 (2)
C8—C9—C10—C11	−0.5 (7)

Experimental details

Crystal data
Chemical formula	[SnI₄(C₂₅H₂₂O₂P₂)]·CHCl₃
M_r	1162.02
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	125
a, b, c (Å)	9.2639 (5), 19.0609 (11), 10.1991 (6)
β (°)	108.479 (1)
V (Å³)	1708.08 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.71
Crystal size (mm)	0.14 × 0.13 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.558, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	20220, 7254, 6994
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.046, 1.03
No. of reflections	7254
No. of parameters	344
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.50
Absolute structure	Flack (1983), 3512 Friedel pairs
Absolute structure parameter	0.004 (14)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Davis, M. F., Clarke, M., Levason, W., Reid, G. & Webster, M. (2006a). Eur. J. Inorg. Chem. pp. 2773–2782. Web of Science CSD CrossRef Google Scholar
Davis, M. F., Levason, W., Reid, G. & Webster, M. (2006b). Polyhedron, 25, 930–936. Web of Science CSD CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Genge, A. R. J., Levason, W. & Reid, G. (1999). Inorg. Chim. Acta, 288, 142–149. Web of Science CSD CrossRef CAS Google Scholar
Levason, W., Patel, R. & Reid, G. (2003). J. Organomet. Chem. 688, 280–282. Web of Science CrossRef CAS Google Scholar
Mohamed, E. M., Panchanatheswaran, K., Low, J. N. & Glidewell, C. (2004). Acta Cryst. C60, m172–m173. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Woollins, J. D. (2003). Inorganic Experiments: Second, Completely Revised and Enlarged Edition, edited by J. D. Woollins, pp. 36–37. Weinheim: Wiley. Google Scholar

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