A monomeric fourfold-coordinated indium dihalide with an unusual coordination geometry

The single-crystal X-ray analysis of the title compound, {[dimeth­yl(2-pyrid­yl)sil­yl]bis­(trimethyl­silyl)meth­yl}diiodoindium(III), [In(C₁₄H₂₈NSi₃)I₂], revealed monomeric mol­ecules containing tetra­coordinated In with an unusual trigonal-pyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.041
• wR factor = 0.104
• Data-to-parameter ratio = 40.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  I1     -   In1     ..       9.17 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  I2     -   In1     ..       5.67 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

We recently synthesized the first [1]alumina- and [1]gallaferrocenophanes (eq. 1) (Schachner et al., 2005a). We intended to use a similar procedure to prepare a hitherto unknown [1]indaferrocenophane and synthesized the starting material, (Pytsi)InCl₂, (I) [Pytsi = C(SiMe₃)₂SiMe₂(C₅H₄N-2); Schachner et al., 2005b]. In contrast with the respective dichlorides of aluminium and gallium (eq. 1), indane (I) is a chloro-bridged dimer in the solid state (eq. 2). Compound (I) reacted with dilithioferrocene, but did not gave the targeted [1]ferrocenophane. Instead, an unusual ferrocene derivative could be isolated, in which the two Cp ligands were bridged by an In(µ-Cl)₂In moiety (eq. 2). This result might suggest that a monomeric indium dihalide is needed for the synthesis of the target [1]indaferrocenophane.

Reaction of InI₃ with Li(THF)(Pytsi) (THF is tetrahydrofuran) in a 1:1 ratio resulted in (Pytsi)InI₂, (II), in a moderate isolated yield of 56%. In contrast with the dichloride, (I), the title compound, (II), crystallizes as a monomer (Fig. 1).

The In atom in compound (II) is fourfold-coordinated by atoms I1, I2, C7 and N1. The In1/I1/I2/C7 subset can be described as a trigonal pyramid, with atom In1 at the centre of the trigonal base and atom N1 at the apex. The sum of the three angles I1—In1—I2, C7—In1—I1 and C7—In1—I2 is 356.4 (13)°, which is only a few degrees away from an idealized planar coordination. At first glance, the coordination of the In centre looks like that of a trigonal–bipyramid with one apical position unoccupied. A close inspection of the packing of the molecules shows an I atom at a distance of 4.3421 (4) Å, approximately along the axis of the trigonal pyramid, with the N1—In1—I1ⁱ angle being 165.79 (11)° [symmetry code: (i) Please provide symmetry code]. The In1—I1ⁱ distance is ~0.4 Å greater than the sum of the usually accepted van der Waals radii, which are 1.93 and 1.96 Å, respectively (Bondi, 1964).

Compound (II) is an example of a structurally characterized indium dihalide species with only fourfold-coordinated In atoms with monomeric molecular units in the crystal structure. A search of the Cambridge Structural Database (Version?; Allen, 2002) for indium dihalides with at least one In—C or one In—N bond revealed that several species with fourfold coordination (Veith & Recktenwald, 1984; Veith et al., 1991; Annan et al., 1991; de Souza et al., 1993; Cowley et al., 1995; Fischer et al., 1996; Jutzi et al., 1996; Black et al., 1997; Delpech et al., 2002; Kuhner et al., 1998; Abernethy et al., 2000; Felix et al., 2000; Stender et al., 2001; Peppe et al., 2001; Cheng et al., 2002; Baker et al., 2002; Schulte & Gabbai, 2002; Bock et al., 2004) and one species with threefold coordination are known (Schulz et al., 1993; Petrie et al., 1993). However, all known species with tetra-coordination exhibit In in a tetrahedral environment. From the study of Lewis acid–base adducts, it is known that the pyramidalization of the Lewis acid moiety becomes more pronounced with increasing donor bond strength (see, for example, Jiao et al., 1994; Jonas et al., 1994). If this effect were to be of importance in species (II), then the nearly planar I₂InC moiety would suggest a very weak In—N donor interaction. The weakness of the bond should be evident in an unusually long In—N bond. However, the known indium dichloride (η¹-Me₄C₅CH₂CH₂NMe₂)InCl₂, in which the In atom shows a similar set of coordinated atoms to those in compound (II), exhibits tetrahedrally surrounded In atoms, with an In—N bond length of 2.265 (5) Å (Jutzi et al., 1996). Within the standard uncertainty, the In—N distance in compound (II) is the same (Table 1).

We can only speculate that the unusual coordination geometry of In in compound (II) results mainly from steric crowding in the vicinity of In. It may be that the large I atoms and two bulky SiMe₃ groups do not allow for a pyramidalization of the Lewis acid moiety. To the best of our knowledge, compound (II) is the first indium dihalide with such an unusual coordination polyhedron (Fig. 1).

S2. Experimental

InI₃ (1.642 g, 3.31 mmol) in tetrahydrofuran (THF; 25 ml) at 195 K was added to Li(THF)(Pytsi) (Al-Juaid et al., 2000; 1.236 g, 3.31 mmol) in THF (10 ml) at 195 K, resulting in a green solution. The solution was stirred for 1 h at 195 K before being allowed to warm to room temperature. After the mixture had been stirred for an additional 16 h, all volatiles were removed in vacuo and a green solid was left behind. This crude product was washed with diethyl? ether (3 × 15 ml) and the washings were combined and filtered. Subsequently, the solvent was removed in vacuo and the remaining solid was heated to 373 K under vacuum to remove unreacted starting materials by a flask-to-flask condensation. Diethyl ether (10 ml) was added to the remaining solid, and the resulting solution was filtered and finally kept at 248 K to afford (II) (1.237 g, 56%). Spectroscopic analysis: ¹H NMR (500 MHz, C₆D₆, 298 K, δ, p.p.m.): 0.26 (18H, s, SiMe₃), 0.36 (6H, s, SiMe₂), 6.32 (1H, pst, 5-H), 6.72 (1H, pst, 4-H), 6.79 (1H, d, J = 7.6 Hz, 3-H), 8.46 (1H, d, J = 5.4 Hz, 6-H); ¹³C NMR: 3.97 (SiMe₂), 6.55 (SiMe₃), 125.50 (5-C), 129.48 (3-C), 138.83 (4-C), 147.81 (6-C), 169.32 (ipso-C); MS: m/z = 536 (100) [C₁₄H₂₈IInNSi₃]⁺, 264 (85) [C₁₂H₂₂NSi₃]⁺.

S3. Refinement

H atoms were placed in calculated positions, with C—H distances in the range 0.95–0.99 Å, and included in the refinement in the riding-model approximation, with U_iso(H) constrained to be 1.2U_eq(C) for all aromatic H atoms and 1.5U_eq(C) for all methyl H atoms.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

Fig. 1. A view of the molecule of (II), with displacement ellipsoids drawn at the 50% probability level.

{[Dimethyl(2-pyridyl)silyl]bis(trimethylsilyl)methyl}diiodoindium(III)

Crystal data

[In(C14H28NSi3)I2]	F(000) = 1264
Mr = 663.26	Dx = 1.929 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8085 reflections
a = 9.9492 (1) Å	θ = 1.0–32.0°
b = 13.6254 (2) Å	µ = 3.89 mm^−1
c = 18.9012 (3) Å	T = 173 K
β = 116.972 (1)°	Block, colourless
V = 2283.58 (6) Å^3	0.10 × 0.10 × 0.08 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	6166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Horizonally mounted graphite crystal monochromator	θmax = 32.0°, θmin = 2.8°
Detector resolution: 9 pixels mm^-1	h = −14→14
ϕ scans and ω scans with κ offsets	k = −18→20
14706 measured reflections	l = −28→28
7936 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0364P)^2 + 7.7352P] where P = (Fo^2 + 2Fc^2)/3
7936 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 1.75 e Å^−3
0 restraints	Δρmin = −2.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.00511 (4)	0.44337 (2)	0.10409 (2)	0.04218 (9)
I2	−0.19124 (3)	0.25594 (3)	−0.098127 (19)	0.04147 (9)
In1	0.06587 (3)	0.29119 (2)	0.034296 (15)	0.02094 (7)
Si1	0.29101 (11)	0.11236 (7)	0.08153 (6)	0.01908 (19)
Si2	0.42933 (12)	0.32016 (8)	0.14016 (6)	0.0214 (2)
Si3	0.32542 (13)	0.25380 (8)	−0.03794 (6)	0.0228 (2)
N1	0.0622 (4)	0.1728 (3)	0.11794 (19)	0.0237 (6)
C2	−0.0344 (5)	0.1688 (3)	0.1504 (3)	0.0290 (8)
H2	−0.1102	0.2177	0.1367	0.035*
C3	−0.0258 (5)	0.0960 (4)	0.2025 (3)	0.0341 (10)
H3	−0.0947	0.0946	0.2246	0.041*
C4	0.0835 (5)	0.0256 (4)	0.2223 (3)	0.0345 (10)
H4	0.0914	−0.0254	0.2582	0.041*
C5	0.1826 (5)	0.0296 (3)	0.1891 (2)	0.0295 (8)
H5	0.2589	−0.0189	0.2023	0.035*
C6	0.1702 (4)	0.1046 (3)	0.1365 (2)	0.0209 (7)
C7	0.2918 (4)	0.2440 (3)	0.0531 (2)	0.0179 (6)
C8	0.4779 (5)	0.0575 (3)	0.1481 (3)	0.0314 (9)
H8A	0.5249	0.0950	0.1977	0.047*
H8B	0.5430	0.0594	0.1218	0.047*
H8C	0.4641	−0.0108	0.1599	0.047*
C9	0.1926 (5)	0.0270 (3)	−0.0037 (2)	0.0302 (9)
H9A	0.1935	−0.0395	0.0163	0.045*
H9B	0.2444	0.0270	−0.0372	0.045*
H9C	0.0880	0.0485	−0.0351	0.045*
C10	0.4095 (5)	0.2913 (3)	0.2322 (2)	0.0282 (8)
H10A	0.3061	0.3054	0.2228	0.042*
H10B	0.4802	0.3317	0.2763	0.042*
H10C	0.4318	0.2217	0.2456	0.042*
C11	0.6305 (5)	0.2966 (4)	0.1617 (3)	0.0355 (10)
H11A	0.6984	0.3262	0.2128	0.053*
H11B	0.6495	0.3257	0.1196	0.053*
H11C	0.6485	0.2257	0.1639	0.053*
C12	0.3989 (5)	0.4556 (3)	0.1242 (3)	0.0336 (9)
H12A	0.4890	0.4906	0.1621	0.050*
H12B	0.3121	0.4753	0.1323	0.050*
H12C	0.3796	0.4720	0.0699	0.050*
C13	0.3810 (6)	0.3791 (3)	−0.0542 (3)	0.0404 (11)
H13A	0.3017	0.4260	−0.0602	0.061*
H13B	0.3948	0.3794	−0.1023	0.061*
H13C	0.4756	0.3979	−0.0085	0.061*
C14	0.4824 (6)	0.1698 (4)	−0.0286 (3)	0.0359 (10)
H14A	0.5733	0.1847	0.0205	0.054*
H14B	0.5031	0.1794	−0.0741	0.054*
H14C	0.4526	0.1015	−0.0274	0.054*
C15	0.1575 (6)	0.2215 (4)	−0.1331 (3)	0.0423 (12)
H15A	0.1866	0.2194	−0.1761	0.063*
H15B	0.0787	0.2710	−0.1451	0.063*
H15C	0.1192	0.1570	−0.1279	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0583 (2)	0.03714 (17)	0.04479 (18)	0.01212 (14)	0.03535 (16)	0.00036 (13)
I2	0.02854 (15)	0.04648 (19)	0.03682 (16)	−0.00403 (13)	0.00380 (12)	−0.00015 (14)
In1	0.01992 (12)	0.02310 (13)	0.02236 (12)	0.00204 (10)	0.01184 (10)	0.00261 (10)
Si1	0.0214 (5)	0.0175 (4)	0.0203 (4)	−0.0006 (4)	0.0110 (4)	−0.0002 (4)
Si2	0.0202 (5)	0.0220 (5)	0.0226 (5)	−0.0050 (4)	0.0103 (4)	−0.0055 (4)
Si3	0.0278 (5)	0.0235 (5)	0.0232 (5)	−0.0013 (4)	0.0170 (4)	0.0009 (4)
N1	0.0234 (15)	0.0280 (16)	0.0233 (15)	−0.0026 (13)	0.0138 (12)	0.0005 (13)
C2	0.0274 (19)	0.036 (2)	0.031 (2)	−0.0015 (17)	0.0194 (16)	0.0005 (17)
C3	0.041 (2)	0.041 (2)	0.032 (2)	−0.011 (2)	0.0266 (19)	−0.0018 (19)
C4	0.045 (3)	0.036 (2)	0.029 (2)	−0.010 (2)	0.0222 (19)	0.0032 (18)
C5	0.035 (2)	0.029 (2)	0.0260 (19)	−0.0002 (17)	0.0146 (17)	0.0052 (16)
C6	0.0231 (17)	0.0231 (17)	0.0201 (16)	−0.0064 (14)	0.0130 (13)	−0.0036 (13)
C7	0.0183 (15)	0.0203 (16)	0.0178 (15)	−0.0006 (13)	0.0106 (12)	−0.0016 (12)
C8	0.031 (2)	0.028 (2)	0.036 (2)	0.0121 (17)	0.0163 (18)	0.0078 (17)
C9	0.039 (2)	0.0256 (19)	0.029 (2)	−0.0081 (17)	0.0178 (18)	−0.0075 (16)
C10	0.029 (2)	0.032 (2)	0.0208 (17)	−0.0027 (17)	0.0093 (15)	−0.0049 (16)
C11	0.0213 (19)	0.042 (3)	0.041 (2)	−0.0076 (18)	0.0127 (18)	−0.008 (2)
C12	0.038 (2)	0.023 (2)	0.042 (2)	−0.0063 (17)	0.021 (2)	−0.0055 (18)
C13	0.058 (3)	0.029 (2)	0.048 (3)	−0.008 (2)	0.036 (3)	0.002 (2)
C14	0.039 (2)	0.040 (3)	0.043 (2)	0.005 (2)	0.031 (2)	−0.002 (2)
C15	0.049 (3)	0.059 (3)	0.0211 (19)	−0.009 (2)	0.0178 (19)	−0.001 (2)

Geometric parameters (Å, º)

In1—I1	2.7172 (4)	C5—H5	0.9500
In1—I2	2.6891 (4)	C8—H8A	0.9800
In1—N1	2.270 (3)	C8—H8B	0.9800
In1—C7	2.207 (3)	C8—H8C	0.9800
In1—I1^i	4.3421 (4)	C9—H9A	0.9800
Si1—C8	1.865 (4)	C9—H9B	0.9800
Si1—C9	1.865 (4)	C9—H9C	0.9800
Si1—C7	1.873 (4)	C10—H10A	0.9800
Si1—C6	1.916 (4)	C10—H10B	0.9800
Si2—C12	1.873 (4)	C10—H10C	0.9800
Si2—C10	1.880 (4)	C11—H11A	0.9800
Si2—C11	1.880 (4)	C11—H11B	0.9800
Si2—C7	1.901 (4)	C11—H11C	0.9800
Si3—C13	1.862 (5)	C12—H12A	0.9800
Si3—C15	1.869 (5)	C12—H12B	0.9800
Si3—C14	1.879 (5)	C12—H12C	0.9800
Si3—C7	1.901 (3)	C13—H13A	0.9800
N1—C6	1.341 (5)	C13—H13B	0.9800
N1—C2	1.357 (5)	C13—H13C	0.9800
C2—C3	1.372 (6)	C14—H14A	0.9800
C2—H2	0.9500	C14—H14B	0.9800
C3—C4	1.369 (7)	C14—H14C	0.9800
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.389 (6)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C5—C6	1.391 (5)
N1—In1—C7	91.00 (12)	Si1—C8—H8A	109.5
N1—In1—I2	102.26 (8)	Si1—C8—H8B	109.5
N1—In1—I1	96.56 (9)	H8A—C8—H8B	109.5
N1—In1—I1^i	165.79 (11)	Si1—C8—H8C	109.5
I1—In1—I2	103.958 (14)	H8A—C8—H8C	109.5
C7—In1—I1	127.91 (9)	H8B—C8—H8C	109.5
C7—In1—I2	124.57 (9)	Si1—C9—H9A	109.5
C8—Si1—C9	107.8 (2)	Si1—C9—H9B	109.5
C8—Si1—C7	116.40 (19)	H9A—C9—H9B	109.5
C9—Si1—C7	114.73 (18)	Si1—C9—H9C	109.5
C8—Si1—C6	106.91 (19)	H9A—C9—H9C	109.5
C9—Si1—C6	102.79 (18)	H9B—C9—H9C	109.5
C7—Si1—C6	107.09 (16)	Si2—C10—H10A	109.5
C12—Si2—C10	106.1 (2)	Si2—C10—H10B	109.5
C12—Si2—C11	106.3 (2)	H10A—C10—H10B	109.5
C10—Si2—C11	108.2 (2)	Si2—C10—H10C	109.5
C12—Si2—C7	113.49 (19)	H10A—C10—H10C	109.5
C10—Si2—C7	110.51 (17)	H10B—C10—H10C	109.5
C11—Si2—C7	111.83 (19)	Si2—C11—H11A	109.5
C13—Si3—C15	105.1 (3)	Si2—C11—H11B	109.5
C13—Si3—C14	106.1 (2)	H11A—C11—H11B	109.5
C15—Si3—C14	106.8 (2)	Si2—C11—H11C	109.5
C13—Si3—C7	113.6 (2)	H11A—C11—H11C	109.5
C15—Si3—C7	114.01 (19)	H11B—C11—H11C	109.5
C14—Si3—C7	110.62 (19)	Si2—C12—H12A	109.5
C6—N1—C2	120.1 (3)	Si2—C12—H12B	109.5
C6—N1—In1	114.3 (2)	H12A—C12—H12B	109.5
C2—N1—In1	125.6 (3)	Si2—C12—H12C	109.5
N1—C2—C3	121.9 (4)	H12A—C12—H12C	109.5
N1—C2—H2	119.1	H12B—C12—H12C	109.5
C3—C2—H2	119.1	Si3—C13—H13A	109.5
C4—C3—C2	119.0 (4)	Si3—C13—H13B	109.5
C4—C3—H3	120.5	H13A—C13—H13B	109.5
C2—C3—H3	120.5	Si3—C13—H13C	109.5
C3—C4—C5	119.2 (4)	H13A—C13—H13C	109.5
C3—C4—H4	120.4	H13B—C13—H13C	109.5
C5—C4—H4	120.4	Si3—C14—H14A	109.5
C4—C5—C6	120.0 (4)	Si3—C14—H14B	109.5
C4—C5—H5	120.0	H14A—C14—H14B	109.5
C6—C5—H5	120.0	Si3—C14—H14C	109.5
N1—C6—C5	119.8 (3)	H14A—C14—H14C	109.5
N1—C6—Si1	116.4 (3)	H14B—C14—H14C	109.5
C5—C6—Si1	123.6 (3)	Si3—C15—H15A	109.5
Si1—C7—Si3	110.64 (18)	Si3—C15—H15B	109.5
Si1—C7—Si2	111.69 (18)	H15A—C15—H15B	109.5
Si3—C7—Si2	113.08 (18)	Si3—C15—H15C	109.5
Si1—C7—In1	100.88 (15)	H15A—C15—H15C	109.5
Si3—C7—In1	114.72 (17)	H15B—C15—H15C	109.5
Si2—C7—In1	105.13 (15)
C7—In1—N1—C6	−13.1 (3)	C9—Si1—C7—In1	81.4 (2)
I2—In1—N1—C6	112.7 (3)	C6—Si1—C7—In1	−31.99 (19)
I1—In1—N1—C6	−141.5 (3)	C13—Si3—C7—Si1	−163.9 (2)
C7—In1—N1—C2	164.9 (3)	C15—Si3—C7—Si1	75.7 (3)
I2—In1—N1—C2	−69.4 (3)	C14—Si3—C7—Si1	−44.7 (3)
I1—In1—N1—C2	36.5 (3)	C13—Si3—C7—Si2	−37.8 (3)
C6—N1—C2—C3	−0.1 (6)	C15—Si3—C7—Si2	−158.2 (2)
In1—N1—C2—C3	−177.9 (3)	C14—Si3—C7—Si2	81.5 (3)
N1—C2—C3—C4	0.0 (7)	C13—Si3—C7—In1	82.8 (3)
C2—C3—C4—C5	0.0 (7)	C15—Si3—C7—In1	−37.6 (3)
C3—C4—C5—C6	0.0 (7)	C14—Si3—C7—In1	−158.0 (2)
C2—N1—C6—C5	0.1 (6)	C12—Si2—C7—Si1	−164.5 (2)
In1—N1—C6—C5	178.2 (3)	C10—Si2—C7—Si1	−45.4 (2)
C2—N1—C6—Si1	175.8 (3)	C11—Si2—C7—Si1	75.2 (2)
In1—N1—C6—Si1	−6.1 (4)	C12—Si2—C7—Si3	70.0 (2)
C4—C5—C6—N1	−0.1 (6)	C10—Si2—C7—Si3	−171.0 (2)
C4—C5—C6—Si1	−175.5 (3)	C11—Si2—C7—Si3	−50.4 (3)
C8—Si1—C6—N1	152.5 (3)	C12—Si2—C7—In1	−55.9 (2)
C9—Si1—C6—N1	−94.2 (3)	C10—Si2—C7—In1	63.1 (2)
C7—Si1—C6—N1	27.1 (3)	C11—Si2—C7—In1	−176.2 (2)
C8—Si1—C6—C5	−31.9 (4)	N1—In1—C7—Si1	25.44 (15)
C9—Si1—C6—C5	81.4 (4)	I2—In1—C7—Si1	−80.23 (15)
C7—Si1—C6—C5	−157.4 (3)	I1—In1—C7—Si1	124.56 (11)
C8—Si1—C7—Si3	86.7 (2)	N1—In1—C7—Si3	144.36 (19)
C9—Si1—C7—Si3	−40.5 (3)	I2—In1—C7—Si3	38.7 (2)
C6—Si1—C7—Si3	−153.82 (18)	I1—In1—C7—Si3	−116.52 (15)
C8—Si1—C7—Si2	−40.2 (3)	N1—In1—C7—Si2	−90.79 (16)
C9—Si1—C7—Si2	−167.37 (19)	I2—In1—C7—Si2	163.55 (8)
C6—Si1—C7—Si2	79.3 (2)	I1—In1—C7—Si2	8.3 (2)
C8—Si1—C7—In1	−151.49 (18)

Symmetry code: (i) −x, −y+1, −z.