Diiodobis(4-methylpentan-2-onato-C⁴,O)tin(IV): a comparison with diiodobis(3-methoxy-3-oxopropyl-C,O)tin(IV)

The title compound, [SnI₂(C₆H₁₁O)₂], contains a six-coordinate tin centre as a consequence of intramolecular Sn-O interactions. The Sn-O bond lengths range between 2.428 (4) and 2.439 (4) Å.

S1. Comment

3-(Halostannyl)propanoic esters, so called estertin compounds, such as X₂Sn(CH₂CH₂CO₂R)₂ and X₃SnCH₂CH₂CO₂R, have been known for almost 25 years (Hutton & Oakes, 1976). The initial interest in these compounds as precursors of PVC stabilizers has long since waned, but interest persists in their coordination chemistry (Balasubramanian et al., 1997, and references therein). (3-Halostannyl)alkanones, e.g. X₂Sn(CR₂CH₂COR)₂, have been known for a similar period (Hutton & Oakes, 1976), but have been less extensively investigated, especially in regard to their coordination chemistry. Comparison of the structures of the title compound, I₂Sn(CMe₂CH₂COMe)₂, (I), now reported, and that of I₂Sn(CH₂CH₂CO₂Me)₂, (II), reported previously by Balasubramanian et al. (1997), allows the relative donor abilities of the intramolecular ester and ketone groups to be assessed. \sch

Both (I) and (II) exist as molecular compounds, but with different degrees of octahedral distortion. The organic groups act as C,O-chelating ligands, with the O atoms trans to the cis-iodides. Selected geometric parameters for both compounds are listed in Table 1.

The ketone group in (I) is a stronger donor than the ester group in (II), as shown by the shorter Sn—O bonds and the longer Sn—I bonds. For comparison, Sn—I bond lengths in four-coordinate tetrahedral diorganotin diiodides are in the range 2.649–2.719 Å (Balasubramanian et al., 1997). Longer Sn—I bond lengths [2.965 (1) and 3.009 (1) Å] were found in octahedral [(p-MeC₆H₄){2,6-(Me₂NCH₂)₂C₆H₃—C,N,N''}SnI₂], but here the iodides were in a trans arrangement (Jastrzebski et al., 1991).

The chelate bite angles in (I) [74.66 (17)–75.15 (17)°] are slightly larger than those in (II) [73.9 (4) and 72.8 (3)°; Balasubramanian et al., 1997]. The bite angles result in octahedral distortions and there are significant differences between the C—Sn—C angles in (I) and (II): 144.0 (5)° in (II), and 160.4 (2) and 163.1 (2)° in the two independent molecules of (I).

S2. Experimental

Compound (I) was prepared by the halogen exchange reaction between Cl₂Sn(CMe₂CH₂COMe)₂ (Hutton & Oakes, 1976) and excess NaI in acetone solution. Crystals were obtained from solution in EtOH. The compound decomposed on heating at 444–445 K.

S3. Refinement

H atoms were placed in calculated positions and refined with a riding model. Maximum and minimum Δρ were found 1.01 Å from I1B and 0.87 Å from Sn1B, respectively.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. A view of molecule A of (I), showing the atom-labelling scheme used for both molecules of the asymmetric unit, which are differentiated in the text by suffix A or B. Displacement ellipsoids are at the 50% probability level and H atoms have been omitted for clarity.

Diiodobis(4-methylpentan-2-onato-C⁴,O)tin(IV)

Crystal data

[SnI2(C6H11O)2]	Z = 4
Mr = 570.79	F(000) = 1064
Triclinic, P1	Dx = 2.127 Mg m^−3
a = 7.8655 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.8464 (4) Å	Cell parameters from 28392 reflections
c = 16.4602 (4) Å	θ = 1.5–27.5°
α = 108.0591 (14)°	µ = 4.89 mm^−1
β = 102.0352 (14)°	T = 150 K
γ = 90.0908 (14)°	Plate, colourless
V = 1782.73 (8) Å^3	0.12 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD area detector diffractometer	8156 independent reflections
Radiation source: Nonius FR591 rotating anode	6019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.5°
ϕ and ω scans to fill the Ewald sphere	h = −10→9
Absorption correction: empirical (using intensity measurements) (SORTAV; Blessing, 1997)	k = −19→19
Tmin = 0.692, Tmax = 0.795	l = −21→21
28392 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.100	Calculated w = 1/[σ^2(Fo^2) + (0.0464P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
8156 reflections	Δρmax = 2.36 e Å^−3
320 parameters	Δρmin = −1.62 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: heavy-atom method	Extinction coefficient: 0.00079 (12)

Special details

Experimental. The only known problem with this structure is a checkcif level C alert questioning the appropriateness of the correction for absorption applied to the intensity data arising from a slight incompatibility between the reported crystal dimensions and the minimum and maximum transmission factors. The reported values faithfully replicate those provided by the EPSRC crystallographic service at Southampton and are not therefore under the control of the authors.

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.

One reflection showing particularly bad agreement (0,0,1) omitted.

H in calculated positions and refined with a riding model.

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

	x	y	z	Uiso*/Ueq
Sn1A	0.11370 (5)	−0.02131 (3)	0.25486 (2)	0.02026 (11)
I1A	0.06194 (5)	0.13162 (3)	0.39941 (2)	0.03335 (12)
I2A	−0.17183 (5)	−0.02428 (3)	0.11437 (2)	0.03248 (12)
O1A	0.3556 (5)	−0.0673 (3)	0.3484 (3)	0.0378 (10)
C1A	0.0007 (7)	−0.1339 (4)	0.2945 (4)	0.0279 (13)
C2A	0.1156 (8)	−0.1303 (5)	0.3823 (4)	0.0339 (14)
H2A1	0.0765	−0.0805	0.4290	0.041*
H2A2	0.0974	−0.1918	0.3921	0.041*
C3A	0.3057 (8)	−0.1110 (4)	0.3917 (4)	0.0310 (13)
C4A	0.4330 (11)	−0.1416 (6)	0.4571 (5)	0.058 (2)
H4A1	0.5491	−0.1122	0.4644	0.087*
H4A2	0.4358	−0.2108	0.4366	0.087*
H4A3	0.3977	−0.1218	0.5134	0.087*
C5A	−0.0011 (8)	−0.2294 (4)	0.2260 (4)	0.0357 (15)
H5A1	0.1178	−0.2421	0.2185	0.054*
H5A2	−0.0749	−0.2290	0.1702	0.054*
H5A3	−0.0476	−0.2791	0.2448	0.054*
C6A	−0.1860 (8)	−0.1130 (5)	0.3057 (5)	0.0424 (16)
H6A1	−0.2606	−0.1166	0.2489	0.064*
H6A2	−0.1854	−0.0492	0.3471	0.064*
H6A3	−0.2312	−0.1599	0.3281	0.064*
O2A	0.2440 (6)	−0.1430 (3)	0.1536 (3)	0.0356 (10)
C7A	0.2984 (7)	0.0573 (4)	0.2115 (4)	0.0255 (12)
C8A	0.3089 (7)	−0.0055 (4)	0.1199 (4)	0.0276 (13)
H8A1	0.2109	0.0072	0.0772	0.033*
H8A2	0.4182	0.0137	0.1069	0.033*
C9A	0.3039 (8)	−0.1091 (5)	0.1054 (4)	0.0325 (14)
C10A	0.3651 (10)	−0.1713 (5)	0.0297 (5)	0.052 (2)
H10A	0.3166	−0.2366	0.0158	0.078*
H10B	0.4927	−0.1697	0.0441	0.078*
H10C	0.3268	−0.1491	−0.0209	0.078*
C11A	0.4753 (8)	0.0726 (5)	0.2748 (4)	0.0331 (14)
H11A	0.5569	0.1083	0.2565	0.050*
H11B	0.5198	0.0110	0.2745	0.050*
H11C	0.4630	0.1085	0.3340	0.050*
C12A	0.2304 (8)	0.1521 (4)	0.2075 (4)	0.0348 (14)
H12A	0.2260	0.1926	0.2666	0.052*
H12B	0.1132	0.1414	0.1698	0.052*
H12C	0.3083	0.1834	0.1836	0.052*
Sn1B	0.32888 (5)	0.52263 (3)	0.74656 (2)	0.02034 (11)
I1B	0.16777 (5)	0.52768 (3)	0.88798 (2)	0.03311 (12)
I2B	0.15322 (5)	0.36794 (3)	0.60251 (2)	0.03290 (12)
O1B	0.5463 (5)	0.6459 (3)	0.8471 (3)	0.0330 (9)
C1B	0.5515 (7)	0.4457 (4)	0.7914 (4)	0.0256 (12)
C2B	0.6441 (8)	0.5097 (5)	0.8822 (4)	0.0317 (14)
H2B1	0.5842	0.4984	0.9258	0.038*
H2B2	0.7647	0.4904	0.8950	0.038*
C3B	0.6521 (8)	0.6123 (4)	0.8942 (4)	0.0307 (14)
C4B	0.7825 (9)	0.6758 (5)	0.9695 (5)	0.0492 (19)
H4B1	0.7575	0.7421	0.9769	0.074*
H4B2	0.8997	0.6658	0.9582	0.074*
H4B3	0.7762	0.6612	1.0229	0.074*
C5B	0.6712 (7)	0.4291 (4)	0.7266 (4)	0.0312 (14)
H5B1	0.7669	0.3918	0.7435	0.047*
H5B2	0.7188	0.4904	0.7272	0.047*
H5B3	0.6045	0.3945	0.6676	0.047*
C6B	0.4871 (8)	0.3507 (4)	0.7962 (4)	0.0329 (14)
H6B1	0.5859	0.3201	0.8208	0.049*
H6B2	0.4315	0.3096	0.7372	0.049*
H6B3	0.4024	0.3617	0.8337	0.049*
O2B	0.4908 (5)	0.5684 (3)	0.6528 (3)	0.0366 (10)
C7B	0.1774 (7)	0.6324 (4)	0.7044 (4)	0.0262 (12)
C8B	0.2174 (8)	0.6287 (5)	0.6172 (4)	0.0353 (15)
H8B1	0.1389	0.5781	0.5704	0.042*
H8B2	0.1895	0.6897	0.6068	0.042*
C9B	0.4002 (8)	0.6109 (4)	0.6087 (4)	0.0329 (14)
C10B	0.4718 (11)	0.6402 (6)	0.5430 (5)	0.056 (2)
H10D	0.4950	0.7093	0.5633	0.084*
H10E	0.3871	0.6207	0.4868	0.084*
H10F	0.5805	0.6097	0.5357	0.084*
C11B	0.2354 (9)	0.7295 (4)	0.7719 (4)	0.0376 (15)
H11D	0.1682	0.7780	0.7534	0.056*
H11E	0.3597	0.7437	0.7771	0.056*
H11F	0.2157	0.7295	0.8288	0.056*
C12B	−0.0174 (7)	0.6108 (5)	0.6929 (4)	0.0367 (15)
H12D	−0.0824	0.6573	0.6701	0.055*
H12E	−0.0428	0.6145	0.7496	0.055*
H12F	−0.0521	0.5469	0.6516	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1A	0.0228 (2)	0.0186 (2)	0.0211 (2)	0.00286 (15)	0.00440 (15)	0.00891 (16)
I1A	0.0493 (3)	0.0240 (2)	0.0250 (2)	0.00642 (18)	0.01022 (17)	0.00400 (16)
I2A	0.0269 (2)	0.0417 (3)	0.0280 (2)	0.00377 (18)	−0.00081 (15)	0.01439 (18)
O1A	0.030 (2)	0.045 (3)	0.044 (3)	0.004 (2)	−0.0034 (19)	0.030 (2)
C1A	0.034 (3)	0.025 (3)	0.030 (3)	0.002 (3)	0.005 (2)	0.019 (3)
C2A	0.045 (4)	0.036 (4)	0.029 (3)	−0.002 (3)	0.007 (3)	0.022 (3)
C3A	0.044 (4)	0.022 (3)	0.028 (3)	0.009 (3)	0.004 (3)	0.013 (3)
C4A	0.068 (5)	0.054 (5)	0.052 (5)	−0.001 (4)	−0.016 (4)	0.036 (4)
C5A	0.042 (4)	0.022 (3)	0.044 (4)	−0.005 (3)	0.008 (3)	0.013 (3)
C6A	0.042 (4)	0.040 (4)	0.059 (4)	0.000 (3)	0.022 (3)	0.027 (4)
O2A	0.047 (3)	0.027 (2)	0.038 (2)	0.008 (2)	0.021 (2)	0.010 (2)
C7A	0.026 (3)	0.026 (3)	0.029 (3)	0.006 (2)	0.008 (2)	0.012 (3)
C8A	0.022 (3)	0.033 (3)	0.028 (3)	0.006 (2)	0.008 (2)	0.009 (3)
C9A	0.027 (3)	0.040 (4)	0.027 (3)	0.008 (3)	0.005 (2)	0.004 (3)
C10A	0.066 (5)	0.041 (4)	0.041 (4)	−0.005 (4)	0.024 (4)	−0.006 (3)
C11A	0.029 (3)	0.033 (4)	0.040 (4)	0.000 (3)	0.008 (3)	0.015 (3)
C12A	0.043 (4)	0.023 (3)	0.050 (4)	0.007 (3)	0.016 (3)	0.025 (3)
Sn1B	0.0219 (2)	0.0189 (2)	0.0213 (2)	0.00041 (15)	0.00304 (15)	0.00912 (16)
I1B	0.0310 (2)	0.0446 (3)	0.0290 (2)	0.00362 (18)	0.01157 (16)	0.01597 (19)
I2B	0.0439 (2)	0.0228 (2)	0.0261 (2)	−0.00591 (17)	0.00019 (17)	0.00429 (16)
O1B	0.034 (2)	0.025 (2)	0.034 (2)	−0.0017 (18)	−0.0028 (18)	0.0079 (19)
C1B	0.021 (3)	0.028 (3)	0.034 (3)	0.006 (2)	0.008 (2)	0.017 (3)
C2B	0.028 (3)	0.043 (4)	0.028 (3)	0.004 (3)	0.003 (2)	0.018 (3)
C3B	0.028 (3)	0.036 (4)	0.030 (3)	0.005 (3)	0.011 (3)	0.010 (3)
C4B	0.038 (4)	0.042 (4)	0.046 (4)	0.003 (3)	−0.011 (3)	−0.004 (3)
C5B	0.023 (3)	0.032 (3)	0.040 (3)	0.010 (3)	0.009 (3)	0.012 (3)
C6B	0.036 (3)	0.027 (3)	0.046 (4)	0.008 (3)	0.008 (3)	0.026 (3)
O2B	0.036 (2)	0.045 (3)	0.042 (3)	0.006 (2)	0.0141 (19)	0.029 (2)
C7B	0.028 (3)	0.023 (3)	0.030 (3)	0.000 (2)	0.005 (2)	0.013 (3)
C8B	0.049 (4)	0.031 (4)	0.028 (3)	0.005 (3)	0.001 (3)	0.017 (3)
C9B	0.048 (4)	0.022 (3)	0.032 (3)	0.000 (3)	0.012 (3)	0.010 (3)
C10B	0.084 (6)	0.051 (5)	0.056 (5)	0.015 (4)	0.037 (4)	0.033 (4)
C11B	0.050 (4)	0.026 (3)	0.039 (4)	0.008 (3)	0.010 (3)	0.014 (3)
C12B	0.027 (3)	0.032 (4)	0.050 (4)	0.002 (3)	0.000 (3)	0.017 (3)

Geometric parameters (Å, º)

Sn1A—C1A	2.219 (6)	Sn1B—C1B	2.215 (5)
Sn1A—C7A	2.220 (6)	Sn1B—C7B	2.218 (6)
Sn1A—O1A	2.428 (4)	Sn1B—O2B	2.435 (4)
Sn1A—O2A	2.438 (4)	Sn1B—O1B	2.439 (4)
Sn1A—I1A	2.8354 (5)	Sn1B—I2B	2.8378 (5)
Sn1A—I2A	2.8572 (5)	Sn1B—I1B	2.8551 (5)
O1A—C3A	1.218 (7)	O1B—C3B	1.230 (7)
C1A—C5A	1.511 (8)	C1B—C2B	1.527 (8)
C1A—C2A	1.522 (8)	C1B—C6B	1.527 (8)
C1A—C6A	1.538 (8)	C1B—C5B	1.529 (8)
C2A—C3A	1.489 (9)	C2B—C3B	1.474 (9)
C3A—C4A	1.491 (9)	C3B—C4B	1.490 (9)
O2A—C9A	1.227 (7)	O2B—C9B	1.227 (7)
C7A—C12A	1.522 (8)	C7B—C8B	1.517 (8)
C7A—C11A	1.523 (8)	C7B—C11B	1.521 (8)
C7A—C8A	1.527 (7)	C7B—C12B	1.525 (8)
C8A—C9A	1.480 (9)	C8B—C9B	1.489 (9)
C9A—C10A	1.475 (8)	C9B—C10B	1.491 (9)
C1A—Sn1A—C7A	160.4 (2)	C1B—Sn1B—C7B	161.1 (2)
C1A—Sn1A—O1A	74.67 (18)	C1B—Sn1B—O2B	90.18 (17)
C7A—Sn1A—O1A	90.28 (17)	C7B—Sn1B—O2B	75.15 (17)
C1A—Sn1A—O2A	89.19 (18)	C1B—Sn1B—O1B	74.74 (18)
C7A—Sn1A—O2A	74.66 (17)	C7B—Sn1B—O1B	89.86 (18)
O1A—Sn1A—O2A	75.67 (15)	O2B—Sn1B—O1B	75.37 (14)
C1A—Sn1A—I1A	95.55 (15)	C1B—Sn1B—I2B	97.10 (15)
C7A—Sn1A—I1A	97.15 (14)	C7B—Sn1B—I2B	94.90 (15)
O1A—Sn1A—I1A	90.51 (11)	O2B—Sn1B—I2B	90.57 (11)
O2A—Sn1A—I1A	163.68 (11)	O1B—Sn1B—I2B	163.49 (10)
C1A—Sn1A—I2A	96.87 (15)	C1B—Sn1B—I1B	93.98 (14)
C7A—Sn1A—I2A	94.22 (14)	C7B—Sn1B—I1B	96.75 (14)
O1A—Sn1A—I2A	163.11 (11)	O2B—Sn1B—I1B	162.56 (11)
O2A—Sn1A—I2A	89.82 (11)	O1B—Sn1B—I1B	89.39 (10)
I1A—Sn1A—I2A	105.037 (16)	I2B—Sn1B—I1B	105.675 (16)
C3A—O1A—Sn1A	111.8 (4)	C3B—O1B—Sn1B	110.3 (4)
C5A—C1A—C2A	111.6 (5)	C2B—C1B—C6B	110.3 (5)
C5A—C1A—C6A	109.7 (5)	C2B—C1B—C5B	111.3 (5)
C2A—C1A—C6A	109.5 (5)	C6B—C1B—C5B	110.1 (5)
C5A—C1A—Sn1A	109.9 (4)	C2B—C1B—Sn1B	106.2 (4)
C2A—C1A—Sn1A	106.1 (4)	C6B—C1B—Sn1B	110.5 (4)
C6A—C1A—Sn1A	110.0 (4)	C5B—C1B—Sn1B	108.4 (4)
C3A—C2A—C1A	115.6 (5)	C3B—C2B—C1B	115.6 (5)
O1A—C3A—C2A	119.8 (5)	O1B—C3B—C2B	121.1 (6)
O1A—C3A—C4A	120.6 (6)	O1B—C3B—C4B	120.4 (6)
C2A—C3A—C4A	119.5 (6)	C2B—C3B—C4B	118.3 (6)
C9A—O2A—Sn1A	110.4 (4)	C9B—O2B—Sn1B	110.8 (4)
C12A—C7A—C11A	110.4 (5)	C8B—C7B—C11B	110.5 (5)
C12A—C7A—C8A	109.8 (5)	C8B—C7B—C12B	109.8 (5)
C11A—C7A—C8A	111.1 (4)	C11B—C7B—C12B	110.2 (5)
C12A—C7A—Sn1A	110.6 (4)	C8B—C7B—Sn1B	106.1 (4)
C11A—C7A—Sn1A	109.1 (4)	C11B—C7B—Sn1B	109.5 (4)
C8A—C7A—Sn1A	105.7 (4)	C12B—C7B—Sn1B	110.7 (4)
C9A—C8A—C7A	116.1 (5)	C9B—C8B—C7B	115.9 (5)
O2A—C9A—C10A	120.5 (6)	O2B—C9B—C8B	120.5 (5)
O2A—C9A—C8A	120.7 (5)	O2B—C9B—C10B	119.2 (6)
C10A—C9A—C8A	118.8 (6)	C8B—C9B—C10B	120.2 (6)
C1A—Sn1A—O1A—C3A	−16.9 (4)	C1B—Sn1B—O1B—C3B	−19.1 (4)
C7A—Sn1A—O1A—C3A	175.9 (4)	C7B—Sn1B—O1B—C3B	172.0 (4)
O2A—Sn1A—O1A—C3A	−110.0 (4)	O2B—Sn1B—O1B—C3B	−113.4 (4)
I1A—Sn1A—O1A—C3A	78.8 (4)	I2B—Sn1B—O1B—C3B	−81.0 (5)
I2A—Sn1A—O1A—C3A	−78.4 (6)	I1B—Sn1B—O1B—C3B	75.2 (4)
C7A—Sn1A—C1A—C5A	−52.9 (8)	C7B—Sn1B—C1B—C2B	63.8 (7)
O1A—Sn1A—C1A—C5A	−94.0 (4)	O2B—Sn1B—C1B—C2B	102.2 (4)
O2A—Sn1A—C1A—C5A	−18.7 (4)	O1B—Sn1B—C1B—C2B	27.5 (3)
I1A—Sn1A—C1A—C5A	177.0 (4)	I2B—Sn1B—C1B—C2B	−167.2 (3)
I2A—Sn1A—C1A—C5A	71.1 (4)	I1B—Sn1B—C1B—C2B	−60.8 (3)
C7A—Sn1A—C1A—C2A	67.9 (8)	C7B—Sn1B—C1B—C6B	−176.6 (5)
O1A—Sn1A—C1A—C2A	26.8 (4)	O2B—Sn1B—C1B—C6B	−138.1 (4)
O2A—Sn1A—C1A—C2A	102.1 (4)	O1B—Sn1B—C1B—C6B	147.1 (4)
I1A—Sn1A—C1A—C2A	−62.2 (4)	I2B—Sn1B—C1B—C6B	−47.5 (4)
I2A—Sn1A—C1A—C2A	−168.2 (4)	I1B—Sn1B—C1B—C6B	58.9 (4)
C7A—Sn1A—C1A—C6A	−173.8 (5)	C7B—Sn1B—C1B—C5B	−55.9 (8)
O1A—Sn1A—C1A—C6A	145.1 (4)	O2B—Sn1B—C1B—C5B	−17.4 (4)
O2A—Sn1A—C1A—C6A	−139.5 (4)	O1B—Sn1B—C1B—C5B	−92.2 (4)
I1A—Sn1A—C1A—C6A	56.1 (4)	I2B—Sn1B—C1B—C5B	73.2 (4)
I2A—Sn1A—C1A—C6A	−49.8 (4)	I1B—Sn1B—C1B—C5B	179.5 (4)
C5A—C1A—C2A—C3A	81.5 (6)	C6B—C1B—C2B—C3B	−157.2 (5)
C6A—C1A—C2A—C3A	−156.8 (5)	C5B—C1B—C2B—C3B	80.3 (6)
Sn1A—C1A—C2A—C3A	−38.2 (6)	Sn1B—C1B—C2B—C3B	−37.5 (6)
Sn1A—O1A—C3A—C2A	0.4 (7)	Sn1B—O1B—C3B—C2B	3.7 (6)
Sn1A—O1A—C3A—C4A	−176.7 (5)	Sn1B—O1B—C3B—C4B	−171.2 (5)
C1A—C2A—C3A—O1A	26.1 (8)	C1B—C2B—C3B—O1B	23.0 (8)
C1A—C2A—C3A—C4A	−156.7 (6)	C1B—C2B—C3B—C4B	−161.9 (5)
C1A—Sn1A—O2A—C9A	170.0 (4)	C1B—Sn1B—O2B—C9B	175.5 (4)
C7A—Sn1A—O2A—C9A	−21.3 (4)	C7B—Sn1B—O2B—C9B	−16.5 (4)
O1A—Sn1A—O2A—C9A	−115.7 (4)	O1B—Sn1B—O2B—C9B	−110.3 (4)
I1A—Sn1A—O2A—C9A	−82.8 (5)	I2B—Sn1B—O2B—C9B	78.4 (4)
I2A—Sn1A—O2A—C9A	73.1 (4)	I1B—Sn1B—O2B—C9B	−80.5 (5)
C1A—Sn1A—C7A—C12A	−177.3 (5)	C1B—Sn1B—C7B—C8B	66.5 (8)
O1A—Sn1A—C7A—C12A	−137.9 (4)	O2B—Sn1B—C7B—C8B	26.4 (4)
O2A—Sn1A—C7A—C12A	147.1 (4)	O1B—Sn1B—C7B—C8B	101.3 (4)
I1A—Sn1A—C7A—C12A	−47.3 (4)	I2B—Sn1B—C7B—C8B	−62.9 (4)
I2A—Sn1A—C7A—C12A	58.4 (4)	I1B—Sn1B—C7B—C8B	−169.3 (4)
C1A—Sn1A—C7A—C11A	−55.6 (8)	C1B—Sn1B—C7B—C11B	−52.8 (8)
O1A—Sn1A—C7A—C11A	−16.2 (4)	O2B—Sn1B—C7B—C11B	−92.8 (4)
O2A—Sn1A—C7A—C11A	−91.3 (4)	O1B—Sn1B—C7B—C11B	−18.0 (4)
I1A—Sn1A—C7A—C11A	74.3 (4)	I2B—Sn1B—C7B—C11B	177.9 (4)
I2A—Sn1A—C7A—C11A	−179.9 (4)	I1B—Sn1B—C7B—C11B	71.4 (4)
C1A—Sn1A—C7A—C8A	64.0 (7)	C1B—Sn1B—C7B—C12B	−174.5 (5)
O1A—Sn1A—C7A—C8A	103.3 (3)	O2B—Sn1B—C7B—C12B	145.5 (4)
O2A—Sn1A—C7A—C8A	28.3 (3)	O1B—Sn1B—C7B—C12B	−139.7 (4)
I1A—Sn1A—C7A—C8A	−166.1 (3)	I2B—Sn1B—C7B—C12B	56.2 (4)
I2A—Sn1A—C7A—C8A	−60.4 (3)	I1B—Sn1B—C7B—C12B	−50.3 (4)
C12A—C7A—C8A—C9A	−156.6 (5)	C11B—C7B—C8B—C9B	81.0 (6)
C11A—C7A—C8A—C9A	80.9 (6)	C12B—C7B—C8B—C9B	−157.2 (5)
Sn1A—C7A—C8A—C9A	−37.4 (5)	Sn1B—C7B—C8B—C9B	−37.6 (6)
Sn1A—O2A—C9A—C10A	−170.5 (5)	Sn1B—O2B—C9B—C8B	0.3 (7)
Sn1A—O2A—C9A—C8A	6.8 (7)	Sn1B—O2B—C9B—C10B	−176.4 (5)
C7A—C8A—C9A—O2A	20.8 (8)	C7B—C8B—C9B—O2B	25.8 (9)
C7A—C8A—C9A—C10A	−161.9 (6)	C7B—C8B—C9B—C10B	−157.4 (6)