trans-Tetra­iodidobis(tri-p-tolyl­phosphine oxide-κO)tin(IV)

Hitosugi-Levesque, M.; Tanski, J.M.

doi:10.1107/S1600536808023945

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1107

doi:10.1107/S1600536808023945

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trans-Tetraiodidobis(tri-p-tolylphosphine oxide-κO)tin(IV)

Marina Hitosugi-Levesque ^a and Joseph M. Tanski ^a ^*

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

(Received 15 July 2008; accepted 28 July 2008; online 6 August 2008)

The centrosymmetric title compound, [SnI₄(C₂₁H₂₁OP)₂], is a monomeric complex that displays a nearly octahedral coordination of tin(IV), with an Sn—O bond distance of 2.159 (2) Å and an average Sn—I bond distance of 2.79 (3) Å.

Related literature

For examples of structurally characterized tin(IV) halide complexes of phosphine oxide ligands, see: Tursina et al. (1985 ); Tursina, Aslanov et al. (1986 ); Tursina, Yatsenko et al. (1986 ); Tudela et al. (1993 ); Genge et al. (1999 ); Szymanska-Buzar et al. (2001 ); Davis, Clarke et al. (2006 ); Davis, Levason et al. (2006 ); Caldwell & Tanski (2008 ). For related literature, see: Levason et al. (2003 ); Woollins (2003 ).

Experimental

Crystal data

[SnI₄(C₂₁H₂₁OP)₂]
M_r = 1266.99
Orthorhombic, P b c a
a = 18.6013 (11) Å
b = 11.9677 (7) Å
c = 19.3335 (11) Å
V = 4303.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.57 mm⁻¹
T = 125 (2) K
0.20 × 0.20 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.535, T_max = 0.842
53839 measured reflections
5331 independent reflections
4841 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.07
5331 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn—O1	2.1590 (15)
Sn—I1	2.76735 (17)
Sn—I2	2.8158 (2)
O1—P1	1.5207 (16)

O1—Sn—O1ⁱ	180
O1—Sn—I1	89.84 (4)
O1ⁱ—Sn—I1	90.16 (4)
I1—Sn—I1ⁱ	180
O1—Sn—I2ⁱ	93.59 (4)
O1ⁱ—Sn—I2ⁱ	86.41 (4)
Symmetry code: (i) -x, -y+1, -z+1.

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/S1600536808023945/pv2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023945/pv2089Isup2.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, Clarke et al. 2006; Caldwell & Tanski, 2008). 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). The crystal and molecular structures of the bis(triphenyl phosphine oxide) adducts of SnX₄, where X = F, Cl, Br and I, have all been previously reported. In the case of the fluoride, trans-[Ph₃PO]₂SnF₄, the the phospine oxides are mutually trans (Davis, Clarke et al. 2006). The chloride, cis-[Ph₃PO]₂SnCl₄, exhibits cis phospine oxides ligands (Tursina et al. 1985; Szymanska-Buzar et al. 2001), although it has been reported that both the cis and trans isomers are observed in solution by ³¹P NMR (Davis, Levason et al. 2006<). The structures of both cis-[Ph₃PO]₂SnBr₄ and trans-[Ph₃PO]₂SnBr₄ are known for the bromide (Tudela et al. 1993; Tursina, Yatsenko et al. 1986). In the structure of the iodide, the triphenyl phosphine oxide ligands of cis-[Ph₃PO]₂SnI₄ are found to be cis (Tursina, Aslanov et al. 1986). As reported here, tri(p-tolyl) phosphine oxide results in an iodide complex wherein the phosphine oxide ligands are found to be trans.

Reaction of SnI₄ with tri(p-tolyl) phosphine, (p-CH₃C₆H₄)₃P, in CHCl₃ in the presence of air afforded the title complex [(p-CH₃C₆H₄)₃PO]₂SnI₄, (I).

Complex (I) exhibits a nearly octahedral coordination at tin, which resides on a crystallographic inversion center. The phosphine oxide ligands are mutually trans, with an Sn—O distance of 2.159 (2) Å, and Sn—I distances of 2.7674 (2) and 2.8158 (2) Å. Relevant bond lengths and angles can be found in Table 1. Despite the p-CH₃ substituent and trans orientation of the phosphine oxide ligands in (I), the Sn—O and Sn—I distances in (I) are very similar to those found in cis-[Ph₃PO]₂SnI₄, wherein the Sn—O distances are 2.15 (2) and 2.11 (2) Å, and the Sn—I distances range from 2.781 (2) to 2.816 (2) Å (Tursina, Aslanov et al. 1986).

Related literature top

For examples of structurally characterized tin(IV) halide complexes of phosphine oxide ligands, see: Tursina et al. (1985); Tursina, Aslanov, Chernyshev et al. (1986); Tursina, Yatsenko et al. (1986); Tudela et al. (1993); Genge et al. (1999); Szymanska-Buzar et al. (2001); Davis, Clarke et al. (2006); Davis, Levason et al. (2006); Caldwell & Tanski (2008). For related literature, see: Levason et al. (2003); Woollins (2003).

Experimental top

Complex (I) was prepared by treating a chloroform (ca 10 ml) solution of SnI₄ (626 mg, 1.00 mmol) with an excess of (p-CH₃C₆H₄)₃P (647 mg, 2.13 mmol) in the presence of air. Suitable crystals for single-crystal X-ray analysis separated as orange plates within 2 weeks at room temperature.

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. Symmetry code: i = -x, -y+1, -z+1

trans-Tetraiodidobis(tri-p-tolylphosphine oxide-κO)tin(IV) top

Crystal data top

[SnI₄(C₂₁H₂₁OP)₂]	F(000) = 2408
M_r = 1266.99	D_x = 1.955 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ac2ab	Cell parameters from 9901 reflections
a = 18.6013 (11) Å	θ = 2.8–28.3°
b = 11.9677 (7) Å	µ = 3.57 mm⁻¹
c = 19.3335 (11) Å	T = 125 K
V = 4303.9 (4) Å³	Plate, orange
Z = 4	0.20 × 0.20 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	5331 independent reflections
Radiation source: fine-focus sealed tube	4841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −24→24
T_min = 0.535, T_max = 0.842	k = −15→15
53839 measured reflections	l = −25→25

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0232P)² + 4.4313P] where P = (F_o² + 2F_c²)/3
5331 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[SnI₄(C₂₁H₂₁OP)₂]	V = 4303.9 (4) Å³
M_r = 1266.99	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 18.6013 (11) Å	µ = 3.57 mm⁻¹
b = 11.9677 (7) Å	T = 125 K
c = 19.3335 (11) Å	0.20 × 0.20 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	5331 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4841 reflections with I > 2σ(I)
T_min = 0.535, T_max = 0.842	R_int = 0.032
53839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.07	Δρ_max = 0.56 e Å⁻³
5331 reflections	Δρ_min = −0.50 e Å⁻³
235 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. 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 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). All non-hydrogen atoms were refined anisotropically. Refinement of F² against ALL reflections. 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	0.0000	0.5000	0.5000	0.01453 (5)
I1	0.071249 (8)	0.378968 (13)	0.399124 (8)	0.02266 (4)
I2	0.042286 (8)	0.699279 (12)	0.434117 (8)	0.02186 (4)
O1	−0.09443 (8)	0.50578 (13)	0.43516 (8)	0.0188 (3)
P1	−0.15379 (3)	0.44482 (5)	0.39642 (3)	0.01603 (11)
C1	−0.17934 (12)	0.52832 (19)	0.32327 (11)	0.0194 (4)
C2	−0.23667 (13)	0.4945 (2)	0.28165 (13)	0.0265 (5)
H2A	−0.2605	0.4259	0.2910	0.032*
C3	−0.25902 (13)	0.5601 (2)	0.22692 (13)	0.0266 (5)
H3A	−0.2976	0.5355	0.1985	0.032*
C4	−0.22576 (12)	0.6619 (2)	0.21282 (12)	0.0221 (5)
C5	−0.25292 (14)	0.7344 (2)	0.15496 (13)	0.0291 (5)
H5A	−0.2205	0.7982	0.1488	0.044*
H5B	−0.3012	0.7615	0.1663	0.044*
H5C	−0.2547	0.6908	0.1121	0.044*
C6	−0.16762 (13)	0.6945 (2)	0.25375 (13)	0.0242 (5)
H6A	−0.1433	0.7624	0.2438	0.029*
C7	−0.14473 (13)	0.6286 (2)	0.30905 (12)	0.0222 (5)
H7A	−0.1055	0.6522	0.3369	0.027*
C8	−0.23153 (12)	0.43203 (19)	0.45048 (11)	0.0181 (4)
C9	−0.24193 (13)	0.5130 (2)	0.50135 (12)	0.0224 (5)
H9A	−0.2060	0.5679	0.5092	0.027*
C10	−0.30407 (13)	0.5139 (2)	0.54033 (13)	0.0245 (5)
H10A	−0.3103	0.5696	0.5748	0.029*
C11	−0.35776 (13)	0.4346 (2)	0.53003 (13)	0.0242 (5)
C12	−0.42613 (15)	0.4397 (2)	0.57128 (16)	0.0351 (6)
H12A	−0.4445	0.5165	0.5713	0.053*
H12B	−0.4166	0.4161	0.6189	0.053*
H12C	−0.4620	0.3899	0.5505	0.053*
C13	−0.34695 (13)	0.3523 (2)	0.47927 (13)	0.0238 (5)
H13A	−0.3827	0.2970	0.4719	0.029*
C14	−0.28479 (12)	0.3509 (2)	0.43988 (12)	0.0209 (4)
H14A	−0.2782	0.2948	0.4056	0.025*
C15	−0.12942 (12)	0.31033 (19)	0.36393 (11)	0.0181 (4)
C16	−0.13571 (12)	0.21535 (19)	0.40494 (12)	0.0204 (4)
H16A	−0.1573	0.2205	0.4494	0.024*
C17	−0.11054 (14)	0.1132 (2)	0.38123 (13)	0.0246 (5)
H17A	−0.1159	0.0486	0.4094	0.029*
C18	−0.07758 (14)	0.1039 (2)	0.31675 (13)	0.0275 (5)
C19	−0.05059 (18)	−0.0075 (3)	0.29219 (16)	0.0406 (7)
H19A	−0.0021	0.0011	0.2731	0.061*
H19B	−0.0828	−0.0365	0.2563	0.061*
H19C	−0.0492	−0.0599	0.3311	0.061*
C20	−0.07179 (14)	0.1986 (2)	0.27588 (13)	0.0293 (5)
H20A	−0.0499	0.1932	0.2316	0.035*
C21	−0.09738 (13)	0.3010 (2)	0.29838 (12)	0.0249 (5)
H21A	−0.0933	0.3649	0.2695	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01273 (9)	0.01808 (10)	0.01278 (9)	−0.00027 (7)	0.00002 (7)	0.00045 (7)
I1	0.02116 (8)	0.02856 (9)	0.01826 (7)	0.00429 (6)	0.00170 (5)	−0.00372 (6)
I2	0.02329 (8)	0.02232 (8)	0.01999 (8)	−0.00454 (6)	0.00017 (6)	0.00311 (6)
O1	0.0151 (7)	0.0217 (8)	0.0195 (8)	−0.0017 (6)	−0.0029 (6)	0.0009 (6)
P1	0.0144 (2)	0.0187 (3)	0.0150 (3)	−0.0020 (2)	−0.0015 (2)	0.0013 (2)
C1	0.0182 (10)	0.0223 (11)	0.0177 (10)	−0.0002 (9)	−0.0020 (8)	0.0027 (8)
C2	0.0247 (12)	0.0271 (12)	0.0276 (12)	−0.0088 (10)	−0.0078 (10)	0.0076 (10)
C3	0.0203 (11)	0.0366 (14)	0.0229 (12)	−0.0047 (10)	−0.0068 (9)	0.0041 (10)
C4	0.0193 (10)	0.0288 (12)	0.0182 (11)	0.0042 (9)	0.0010 (9)	0.0037 (9)
C5	0.0272 (12)	0.0343 (14)	0.0259 (12)	0.0038 (11)	−0.0023 (10)	0.0100 (11)
C6	0.0237 (11)	0.0236 (11)	0.0253 (12)	−0.0030 (9)	0.0001 (9)	0.0056 (9)
C7	0.0202 (11)	0.0246 (12)	0.0216 (11)	−0.0041 (9)	−0.0039 (9)	0.0009 (9)
C8	0.0158 (10)	0.0217 (11)	0.0169 (10)	−0.0011 (8)	−0.0010 (8)	0.0022 (8)
C9	0.0197 (11)	0.0244 (11)	0.0231 (11)	−0.0022 (9)	−0.0029 (9)	−0.0030 (9)
C10	0.0249 (11)	0.0270 (12)	0.0215 (11)	0.0029 (10)	0.0007 (9)	−0.0019 (9)
C11	0.0209 (11)	0.0264 (12)	0.0254 (12)	0.0024 (9)	0.0041 (9)	0.0062 (10)
C12	0.0284 (13)	0.0333 (14)	0.0436 (16)	0.0016 (11)	0.0146 (12)	−0.0003 (12)
C13	0.0200 (11)	0.0226 (11)	0.0289 (12)	−0.0052 (9)	−0.0005 (9)	0.0041 (10)
C14	0.0197 (11)	0.0209 (11)	0.0220 (11)	−0.0013 (9)	−0.0012 (9)	−0.0009 (9)
C15	0.0169 (10)	0.0214 (11)	0.0161 (10)	−0.0022 (8)	−0.0013 (8)	−0.0020 (8)
C16	0.0213 (11)	0.0228 (11)	0.0172 (10)	−0.0007 (9)	−0.0009 (9)	−0.0010 (8)
C17	0.0297 (12)	0.0204 (11)	0.0236 (12)	−0.0003 (9)	−0.0027 (10)	−0.0011 (9)
C18	0.0270 (12)	0.0315 (13)	0.0239 (12)	0.0038 (10)	−0.0072 (10)	−0.0113 (10)
C19	0.0497 (17)	0.0370 (16)	0.0350 (15)	0.0097 (13)	−0.0074 (13)	−0.0184 (12)
C20	0.0285 (13)	0.0412 (15)	0.0183 (11)	0.0026 (11)	0.0011 (10)	−0.0072 (10)
C21	0.0251 (12)	0.0301 (13)	0.0193 (11)	−0.0016 (10)	0.0018 (9)	−0.0005 (10)

Geometric parameters (Å, º) top

Sn—O1	2.1590 (15)	C9—C10	1.380 (3)
Sn—O1ⁱ	2.1591 (15)	C9—H9A	0.9500
Sn—I1	2.7674 (2)	C10—C11	1.392 (3)
Sn—I1ⁱ	2.7674 (2)	C10—H10A	0.9500
Sn—I2ⁱ	2.8158 (2)	C11—C13	1.404 (4)
Sn—I2	2.8158 (2)	C11—C12	1.502 (3)
O1—P1	1.5207 (16)	C12—H12A	0.9800
P1—C15	1.786 (2)	C12—H12B	0.9800
P1—C8	1.791 (2)	C12—H12C	0.9800
P1—C1	1.796 (2)	C13—C14	1.385 (3)
C1—C7	1.389 (3)	C13—H13A	0.9500
C1—C2	1.396 (3)	C14—H14A	0.9500
C2—C3	1.382 (3)	C15—C16	1.391 (3)
C2—H2A	0.9500	C15—C21	1.405 (3)
C3—C4	1.393 (4)	C16—C17	1.387 (3)
C3—H3A	0.9500	C16—H16A	0.9500
C4—C6	1.396 (3)	C17—C18	1.394 (4)
C4—C5	1.503 (3)	C17—H17A	0.9500
C5—H5A	0.9800	C18—C20	1.387 (4)
C5—H5B	0.9800	C18—C19	1.502 (4)
C5—H5C	0.9800	C19—H19A	0.9800
C6—C7	1.395 (3)	C19—H19B	0.9800
C6—H6A	0.9500	C19—H19C	0.9800
C7—H7A	0.9500	C20—C21	1.384 (4)
C8—C9	1.394 (3)	C20—H20A	0.9500
C8—C14	1.402 (3)	C21—H21A	0.9500

O1—Sn—O1ⁱ	180.0	C9—C8—P1	117.67 (17)
O1—Sn—I1	89.84 (4)	C14—C8—P1	122.98 (17)
O1—Sn—I1	89.84 (4)	C10—C9—C8	120.5 (2)
O1ⁱ—Sn—I1	90.16 (4)	C10—C9—H9A	119.8
O1—Sn—I1ⁱ	90.16 (4)	C8—C9—H9A	119.8
O1ⁱ—Sn—I1ⁱ	89.84 (4)	C9—C10—C11	121.2 (2)
I1—Sn—I1ⁱ	180.0	C9—C10—H10A	119.4
O1—Sn—I2ⁱ	93.59 (4)	C11—C10—H10A	119.4
O1ⁱ—Sn—I2ⁱ	86.41 (4)	C10—C11—C13	118.4 (2)
I1—Sn—I2ⁱ	90.529 (6)	C10—C11—C12	120.2 (2)
I1ⁱ—Sn—I2ⁱ	89.471 (6)	C13—C11—C12	121.4 (2)
O1—Sn—I2	86.41 (4)	C11—C12—H12A	109.5
O1ⁱ—Sn—I2	93.59 (4)	C11—C12—H12B	109.5
I1—Sn—I2	89.469 (6)	H12A—C12—H12B	109.5
I1ⁱ—Sn—I2	90.531 (6)	C11—C12—H12C	109.5
I2ⁱ—Sn—I2	180.0	H12A—C12—H12C	109.5
P1—O1—Sn	149.47 (10)	H12B—C12—H12C	109.5
O1—P1—C15	114.91 (10)	C14—C13—C11	120.8 (2)
O1—P1—C8	109.87 (10)	C14—C13—H13A	119.6
C15—P1—C8	109.46 (11)	C11—C13—H13A	119.6
O1—P1—C1	108.25 (10)	C13—C14—C8	120.1 (2)
C15—P1—C1	106.96 (11)	C13—C14—H14A	120.0
C8—P1—C1	107.07 (10)	C8—C14—H14A	120.0
C7—C1—C2	119.4 (2)	C16—C15—C21	119.0 (2)
C7—C1—P1	120.92 (17)	C16—C15—P1	120.96 (17)
C2—C1—P1	119.66 (17)	C21—C15—P1	119.77 (18)
C3—C2—C1	120.4 (2)	C17—C16—C15	120.2 (2)
C3—C2—H2A	119.8	C17—C16—H16A	119.9
C1—C2—H2A	119.8	C15—C16—H16A	119.9
C2—C3—C4	120.9 (2)	C16—C17—C18	121.0 (2)
C2—C3—H3A	119.6	C16—C17—H17A	119.5
C4—C3—H3A	119.6	C18—C17—H17A	119.5
C3—C4—C6	118.5 (2)	C20—C18—C17	118.6 (2)
C3—C4—C5	120.1 (2)	C20—C18—C19	121.3 (2)
C6—C4—C5	121.4 (2)	C17—C18—C19	120.1 (3)
C4—C5—H5A	109.5	C18—C19—H19A	109.5
C4—C5—H5B	109.5	C18—C19—H19B	109.5
H5A—C5—H5B	109.5	H19A—C19—H19B	109.5
C4—C5—H5C	109.5	C18—C19—H19C	109.5
H5A—C5—H5C	109.5	H19A—C19—H19C	109.5
H5B—C5—H5C	109.5	H19B—C19—H19C	109.5
C7—C6—C4	120.9 (2)	C21—C20—C18	121.2 (2)
C7—C6—H6A	119.6	C21—C20—H20A	119.4
C4—C6—H6A	119.6	C18—C20—H20A	119.4
C1—C7—C6	119.9 (2)	C20—C21—C15	120.0 (2)
C1—C7—H7A	120.1	C20—C21—H21A	120.0
C6—C7—H7A	120.0	C15—C21—H21A	120.0
C9—C8—C14	119.1 (2)

I1—Sn—O1—P1	60.78 (19)	C1—P1—C8—C14	84.5 (2)
I1ⁱ—Sn—O1—P1	−119.22 (19)	C14—C8—C9—C10	−0.6 (3)
I2ⁱ—Sn—O1—P1	−29.74 (19)	P1—C8—C9—C10	173.90 (18)
I2—Sn—O1—P1	150.26 (19)	C8—C9—C10—C11	0.0 (4)
Sn—O1—P1—C15	−31.2 (2)	C9—C10—C11—C13	0.7 (4)
Sn—O1—P1—C8	92.7 (2)	C9—C10—C11—C12	−177.7 (2)
Sn—O1—P1—C1	−150.70 (18)	C10—C11—C13—C14	−0.7 (4)
O1—P1—C1—C7	1.8 (2)	C12—C11—C13—C14	177.7 (2)
C15—P1—C1—C7	−122.5 (2)	C11—C13—C14—C8	0.1 (4)
C8—P1—C1—C7	120.2 (2)	C9—C8—C14—C13	0.5 (3)
O1—P1—C1—C2	−175.57 (19)	P1—C8—C14—C13	−173.65 (18)
C15—P1—C1—C2	60.1 (2)	O1—P1—C15—C16	86.7 (2)
C8—P1—C1—C2	−57.2 (2)	C8—P1—C15—C16	−37.4 (2)
C7—C1—C2—C3	−0.2 (4)	C1—P1—C15—C16	−153.10 (19)
P1—C1—C2—C3	177.2 (2)	O1—P1—C15—C21	−87.5 (2)
C1—C2—C3—C4	−1.1 (4)	C8—P1—C15—C21	148.36 (18)
C2—C3—C4—C6	2.2 (4)	C1—P1—C15—C21	32.7 (2)
C2—C3—C4—C5	−177.3 (2)	C21—C15—C16—C17	0.1 (3)
C3—C4—C6—C7	−2.2 (4)	P1—C15—C16—C17	−174.16 (18)
C5—C4—C6—C7	177.4 (2)	C15—C16—C17—C18	1.1 (4)
C2—C1—C7—C6	0.3 (4)	C16—C17—C18—C20	−1.4 (4)
P1—C1—C7—C6	−177.14 (19)	C16—C17—C18—C19	179.9 (2)
C4—C6—C7—C1	0.9 (4)	C17—C18—C20—C21	0.6 (4)
O1—P1—C8—C9	27.6 (2)	C19—C18—C20—C21	179.3 (3)
C15—P1—C8—C9	154.69 (18)	C18—C20—C21—C15	0.5 (4)
C1—P1—C8—C9	−89.72 (19)	C16—C15—C21—C20	−0.9 (3)
O1—P1—C8—C14	−158.13 (18)	P1—C15—C21—C20	173.47 (19)
C15—P1—C8—C14	−31.1 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[SnI₄(C₂₁H₂₁OP)₂]
M_r	1266.99
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	125
a, b, c (Å)	18.6013 (11), 11.9677 (7), 19.3335 (11)
V (Å³)	4303.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.57
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.535, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	53839, 5331, 4841
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.07
No. of reflections	5331
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.50

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

Selected geometric parameters (Å, º) top

Sn—O1	2.1590 (15)	Sn—I2	2.8158 (2)
Sn—I1	2.7674 (2)	O1—P1	1.5207 (16)

O1—Sn—O1ⁱ	180.0	I1—Sn—I1ⁱ	180.0
O1—Sn—I1	89.84 (4)	O1—Sn—I2ⁱ	93.59 (4)
O1ⁱ—Sn—I1	90.16 (4)	O1ⁱ—Sn—I2ⁱ	86.41 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

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

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