Acta Crystallographica Section E: Crystallographic Communications

Acta Crystallogr E Crystallogr Commun. 73(Pt 12): 1903-1907

Decachlorocyclopentasilanes coordinated by pairs of chloride anions, with different cations, but the same solvent molecules

Maximilian Moxtera, Julian Teichmanna, Hans-Wolfram Lernera, https://orcid.org/0000-0001-5296-6251Michael Boltea*, Matthias Wagnera‡

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

‡. Correspondence e-mail for synthetic work: Matthias.Wagner@chemie.uni-frankfurt.de.

© Moxter et al. 2017

DOI: 10.1107/S2056989017016310

Published online: 21 November 2017

Abstract

The planar decachlorocyclopentasilane rings in the title compounds are coordinated by two chloride ions to generate inverse-sandwich complexes.

Abstract

We have determined the crystal structures of two decachlorocyclopentasilanes, namely bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate, 2C₁₆H₃₆N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂, (I), and bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate, 2C₈H₂₀N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂, (II), both of which crystallize with discrete cations, anions, and solvent molecules. In (I), the complete decachlorocyclopentasilane ring is generated by a crystallographic twofold rotation axis. In (II), one cation is located on a general position and the other two are disordered about centres of inversion. These are the first structures featuring the structural motif of a five-membered cyclopentasilane ring coordinated from both sides by a chloride ion. The extended structures of (I) and (II) feature numerous C—H⋯Cl interactions. In (II), the N atoms are located on centres of inversion and as a result, the ethylene chains are disordered over equally occupied orientations.

Chemical context  

The title compounds are the first known halide diadducts of the long-known perchlorinated cyclopentasilane Si₅Cl₁₀ (Hengge & Kovar, 1977 ▸). Their structures can be seen as inverse-sandwich complexes, in which two chloride ions lie above and below the planar five-membered silicon ring.

In the recent years, new and facile synthetic protocols for the Cl⁻ diadduct [Si₆Cl₁₄]2– of dodecachlorocyclohexasilane have been developed. It can either be prepared through the chloride-induced disproportionation of Si₂Cl₆, which leads directly to [Si₆Cl₁₄]2– (Tillmann et al., 2012 ▸, 2014 ▸; Tillmann, Moxter et al., 2015 ▸), or the Lewis acidic uncomplexed Si₆Cl₁₂ can be used as the starting material. In the latter case, mere addition of soluble chloride salts [R ₄N]Cl (R = nBu or Et) leads to the formation of [Si₆Cl₁₄]2– (Dai et al., 2010 ▸). Given this background, it was of interest to investigate the Lewis acidity and ability of Si₅Cl₁₀ to bind Cl⁻ ions.

Structural commentary  

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate, 2C₁₆H₃₆N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂, (I), crystallizes with discrete cations, anions, and solvent molecules (Fig. 1 ▸). The five-membered decachlorocyclopentasilane ring is located on a twofold rotation axis. The Si—Cl bond lengths range from 2.081 (3) Å for Si2—Cl21 to 2.100 (3) Å for Si2—Cl22. The Si—Si bond lengths do not vary markedly: they range from 2.339 (3) Å (Si1—Si2) to 2.347 (3) Å (Si2—Si3).

The almost planar ring (r.m.s. deviation 0.002 Å) is coordinated by two chloride anions located above and below the ring. The distances of the chloride ions to the Si atoms [Cl1⋯Si1 2.907 (3), Cl1⋯Si2 2.914 (3), Cl1⋯Si3 2.930 (3) Å,] show that the chloride ions are located almost exactly above the centroid of the ring [distance Cl1⋯Cg = 2.1434 (16) Å].

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate, 2C₈H₂₀N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂, (II), crystallizes as (I) with discrete cations, anions, and solvent molecules (Fig. 2 ▸). The Si—Cl bonds again lie in a quite narrow range [2.0805 (9) Å (Si1—Cl12) to 2.1102 (8) Å (Si2—Cl22)] and the Si—Si bond lengths are also very similar [2.3386 (8) Å (Si1—Si2) to 2.3473 (7) Å (Si4—Si5)].

The five-membered decachlorocyclopentasilane ring is almost planar (r.m.s. deviation = 0.017 Å) and coordinated by two chloride anions located above and below the ring with a Cl⋯Cg distance of 2.1781 (5) Å for Cl1 and 2.1237 (5) Å for Cl2. The Cl⋯Si distances range from 2.9381 (7) Å (Cl1⋯Si5) to 2.9645 (7) Å (Cl1⋯Si2) and from 2.8759 (8) Å (Cl2⋯Si2) to 2.9510 (7) Å (Cl2⋯Si5). Since the Cl⋯Si distances have a broader range for Cl2, it can be said that this ion is slightly displaced from a position directly over the ring centroid.

It is interesting to note that (I) and (II) have – apart from the different cations – the same molecular stoichiometry, i.e. one Si₅Cl₁₀ ring coordinated by two chloride anions, two cations and two solvent dichloromethane molecules. However, since (I) has twofold rotation symmetry, there are only half of the chemical entities in the asymmetric unit.

Supramolecular features  

The components of (I) and (II) are linked by a plethora of C—H⋯Cl contacts (Tables 1 ▸ and 2 ▸, respectively); in particular the chloride ions are surrounded by C—H groups. For an example, see Fig. 3 ▸. As a result of the disorder of the N2 and N3 cations in (II), a plot showing the coordination of the Cl ions looks extremely crowded and is therefore omitted.

Database survey  

The present structures are the first examples of a decachlorocyclopentasilane ring coordinated by two anions. There are only two structures of a decachlorocyclopentasilane ring in the CSD (Version 5.38 of November 2016 plus three updates; Groom et al., 2016 ▸), namely decachlorocyclopentasilane 4-methylbenzonitrile solvate (refcode ELAFON; Dai et al., 2010 ▸) and decachlorocyclopentasilane acetonitrile solvate (ELAFIH; Dai et al., 2010 ▸). In both of them, the decachlorocyclopentasilane ring is almost planar (0.017 Å for ELAFON and 0.001 Å for ELAFIH) and shows almost no variation in the Si—Si (2.358–2.368 Å for ELAFON and 2.342–2.349 Å for ELAFIH) and Si—Cl (2.030–2.059 Å for ELAFON and 2.034– 2.038 Å for ELAFIH) bond lengths.

The distance of the N atom to the centroid of the ring is 2.152 and 2.196 Å for ELAFON and 2.234 Å for ELAFIH. This difference could be due to the steric demand of the benzene ring in ELAFIH. The N⋯Cg distances are in the same range as the Cl⋯Cg distances in (I) and (II).

Mean values of the structural parameters of the four compared structures and dichloride dodecachlorocyclohexasilanes (Tillmann, Lerner & Bolte, 2015 ▸) are compiled in Table 3 ▸. It is remarkable that the Si—Si and Si—Cl bond lengths do not vary significantly between the five and six-membered Si rings, but the Cl⋯Cg distance in the dodecachlorocyclohexasilanes is significantly shorter than for decachlorocyclopentasilane. This might be due to the fact that the Cl ligands form a narrower cone in five- compared to six-membered rings.

Synthesis and crystallization  

The addition of a solution of [R ₄N]Cl (R = nBu or Et) in CH₂Cl₂ at 195 K to a solution of Si₅Cl₁₀ in CH₂Cl₂ furnished the Cl⁻ diadducts [R ₄N]₂[Si₅Cl₁₂] (R = nBu or Et) (Fig. 4 ▸). Crystals of [R ₄N]₂[Si₅Cl₁₂] (R = nBu or Et) could be harvested after storage of the reaction solution for one week at 195 K in 89% and 93% yield, respectively. Both adducts are stable in the solid phase under inert conditions. However, in solution a rapid transformation of [nBu₄N]₂[Si₅Cl₁₂] to [nBu₄N]₂[Si₆Cl₁₄] and [nBu₄N]₂[Si₇Cl₁₆] (Fig. 5 ▸) can be observed via ²⁹Si NMR spectroscopy (for the NMR spectrum see Fig. S1 in the Supporting information), while [Et₄N]₂[Si₅Cl₁₂] is not soluble. For comparison, a ²⁹Si CP/MAS NMR spectrum of single crystals of [nBu₄N]₂[Si₅Cl₁₂] was recorded (Fig. S2 in the Supporting information).

Refinement details  

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. H atoms were refined using a riding model, with Cmethyl—H = 0.98 Å or Cmethylene—H = 0.99 Å and with U iso(H) = 1.5U eq(Cmethyl) or 1.2U eq(C).

The Cl atoms of the dichloromethane solvent molecule in (I) have rather large displacement ellipsoids, but since no valid disorder model for splitting this molecule could be found, refinement with enlarged ADPs was preferred. In (II), atoms N2 and N3 are located on centres of inversion. As a result, the ethylene chains are disordered over equally occupied orientations.

Figure 1View larger versionFigure 1. Perspective view of (I) with displacement ellipsoids drawn at the 50% probability level. For clarity, H atoms are omitted and only the symmetry independent molecules are labelled. Atoms without labels are generated by the symmetry operator −x + 1, y, −z + .

Figure 2View larger versionFigure 2. Perspective view of (II) with displacement ellipsoids drawn at the 50% probability level. For clarity, H atoms are omitted and only one of the two disordered sites of the tetraethylammonium cations are shown.

Figure 3View larger versionFigure 3. Perspective view of (I) showing the environment of the Cl anion. The contact to the centre of the five-membered ring is drawn as an open dashed bond. H⋯Cl contacts less than 3.5 Å are drawn as dashed lines.

Figure 4View larger versionFigure 4. Synthesis of [R ₄N]₂[Si₅Cl₁₂] (R = nBu or Et).

Figure 5View larger versionFigure 5. Transformation of [nBu₄N]₂[Si₅Cl₁₂] (I) to [nBu₄N]₂[Si₆Cl₁₄] (R = R′ = Cl) and [nBu₄N]₂[Si₇Cl₁₆] (R = Cl; R′ = SiCl₃).

See full table Table 1. Hydrogen-bond geometry (Å, °) for (I)

See full table Table 2. Hydrogen-bond geometry (Å, °) for (II)

See full tableTable 3. Mean values (Å) of Si—Si, Si—Cl bond lengths and Cl/N⋯Cg contacts in the title compounds and related structures X = Cl for (I) and (II) and X = N for ELAFON and ELAFIH. The row for Si₆Cl₁₂ contains data for dichloride dodecachlorohexasilanes (Tillmann, Lerner & Bolte, 2015 ▸).

See full table Table 4. Experimental details

Supplementary Material

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Acknowledgments

The authors wish to thank Johanna Becker-Baldus for the recording of the ²⁹Si CP/MAS NMR spectrum.

supplementary crystallographic information

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Crystal data

See full table

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Data collection

See full table

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Refinement

See full table

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Special details

See full table

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

See full table

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Atomic displacement parameters (Å²)

See full table

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Geometric parameters (Å, º)

See full table

Symmetry code: (i) −x+1, y, −z+3/2.

Bis(tetra-n-butylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (I) . Hydrogen-bond geometry (Å, º)

See full table

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+3/2, z−1/2.

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Crystal data

See full table

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Data collection

See full table

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Refinement

See full table

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Special details

See full table

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

See full table

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Atomic displacement parameters (Å²)

See full table

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Geometric parameters (Å, º)

See full table

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Bis(tetraethylammonium) dichloride decachlorocyclopentasilane dichloromethane disolvate (II) . Hydrogen-bond geometry (Å, º)

See full table

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z; (iv) x, y, z−1; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+2, −z+1.

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References

Dai, X., Anderson, K. J., Schulz, D. L. & Boudjouk, P. (2010). Dalton Trans. 39, 11188–11192.

Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.

Hengge, E. & Kovar, D. (1977). J. Organomet. Chem. 125, C29–C32.

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

Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.

Stoe & Cie (2001). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

Tillmann, J., Lerner, H.-W. & Bolte, M. (2015). Acta Cryst. C71, 883–888.

Tillmann, J., Meyer, L., Schweizer, J. I., Bolte, M., Lerner, H.-W., Wagner, M. & Holthausen, M. C. (2014). Chem. Eur. J. 20, 9234–9239.

Tillmann, J., Meyer-Wegner, F., Nadj, A., Becker-Baldus, J., Sinke, T., Bolte, M., Holthausen, M. C., Wagner, M. & Lerner, H.-W. (2012). Inorg. Chem. 51, 8599–8606.

Tillmann, J., Moxter, M., Bolte, M., Lerner, H.-W. & Wagner, M. (2015). Inorg. Chem. 54, 9611–9618.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

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2C₁₆H₃₆N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂ | F(000) = 2544
Mr = 1220.61 | Dx = 1.341 Mg m⁻³
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å
a = 20.9091 (15) Å | Cell parameters from 30920 reflections
b = 15.7423 (7) Å | θ = 3.3–25.8°
c = 19.8734 (16) Å | µ = 0.85 mm⁻¹
β = 112.451 (6)° | T = 173 K
V = 6045.7 (7) Å³ | Needle, colourless
Z = 4 | 0.27 × 0.16 × 0.12 mm

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Stoe IPDS II two-circle diffractometer | 4428 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.060
ω scans | θmax = 25.8°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −25→25
Tmin = 0.543, Tmax = 1.000 | k = −18→19
32650 measured reflections | l = −24→24
5699 independent reflections |

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Refinement on F² | 0 restraints
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.103 | H-atom parameters constrained
wR(F²) = 0.199 | w = 1/[σ²(Fo²) + (0.0209P)² + 98.7944P] where P = (Fo² + 2Fc²)/3
S = 1.15 | (Δ/σ)max < 0.001
5699 reflections | Δρmax = 1.50 e Å⁻³
258 parameters | Δρmin = −1.46 e Å⁻³

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Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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| x | y | z | Uiso*/Ueq |
Cl1 | 0.44920 (9) | 0.65838 (13) | 0.63371 (9) | 0.0392 (4) |
Si1 | 0.55353 (9) | 0.75962 (13) | 0.74394 (10) | 0.0312 (4) |
Si2 | 0.58692 (10) | 0.61853 (14) | 0.73977 (10) | 0.0329 (4) |
Si3 | 0.5000 | 0.53144 (19) | 0.7500 | 0.0368 (7) |
Cl11 | 0.55030 (11) | 0.83349 (15) | 0.65484 (12) | 0.0536 (5) |
Cl12 | 0.62942 (10) | 0.82642 (15) | 0.82814 (12) | 0.0535 (6) |
Cl21 | 0.60720 (11) | 0.58866 (16) | 0.64782 (11) | 0.0534 (6) |
Cl22 | 0.68493 (9) | 0.59548 (15) | 0.82099 (11) | 0.0499 (5) |
Cl31 | 0.46207 (13) | 0.44593 (15) | 0.66352 (15) | 0.0667 (7) |
N1 | 0.3868 (3) | 0.7205 (4) | 0.4082 (3) | 0.0278 (12) |
C1 | 0.4614 (3) | 0.6993 (5) | 0.4564 (4) | 0.0309 (15) |
H1A | 0.4668 | 0.6368 | 0.4578 | 0.037* |
H1B | 0.4699 | 0.7185 | 0.5065 | 0.037* |
C2 | 0.5172 (4) | 0.7380 (5) | 0.4335 (4) | 0.0373 (17) |
H2A | 0.5102 | 0.7188 | 0.3838 | 0.045* |
H2B | 0.5135 | 0.8008 | 0.4329 | 0.045* |
C3 | 0.5881 (4) | 0.7115 (6) | 0.4859 (4) | 0.047 (2) |
H3A | 0.5894 | 0.6489 | 0.4913 | 0.056* |
H3B | 0.5969 | 0.7367 | 0.5343 | 0.056* |
C4 | 0.6455 (4) | 0.7395 (6) | 0.4601 (6) | 0.060 (3) |
H4A | 0.6905 | 0.7210 | 0.4956 | 0.090* |
H4B | 0.6375 | 0.7137 | 0.4127 | 0.090* |
H4C | 0.6450 | 0.8015 | 0.4557 | 0.090* |
C5 | 0.3758 (4) | 0.8156 (5) | 0.3999 (4) | 0.0351 (16) |
H5A | 0.3258 | 0.8265 | 0.3728 | 0.042* |
H5B | 0.4007 | 0.8374 | 0.3700 | 0.042* |
C6 | 0.3994 (4) | 0.8659 (5) | 0.4706 (4) | 0.0440 (19) |
H6A | 0.3744 | 0.8457 | 0.5010 | 0.053* |
H6B | 0.4495 | 0.8568 | 0.4981 | 0.053* |
C7 | 0.3852 (4) | 0.9597 (5) | 0.4545 (5) | 0.055 (2) |
H7A | 0.3348 | 0.9685 | 0.4288 | 0.066* |
H7B | 0.4082 | 0.9787 | 0.4219 | 0.066* |
C8 | 0.4110 (5) | 1.0135 (6) | 0.5234 (6) | 0.078 (3) |
H8A | 0.4008 | 1.0734 | 0.5104 | 0.116* |
H8B | 0.3877 | 0.9957 | 0.5554 | 0.116* |
H8C | 0.4611 | 1.0059 | 0.5485 | 0.116* |
C9 | 0.3385 (3) | 0.6853 (5) | 0.4418 (4) | 0.0303 (15) |
H9A | 0.2910 | 0.7045 | 0.4120 | 0.036* |
H9B | 0.3513 | 0.7107 | 0.4908 | 0.036* |
C10 | 0.3372 (4) | 0.5894 (5) | 0.4494 (4) | 0.0396 (17) |
H10A | 0.3273 | 0.5623 | 0.4015 | 0.047* |
H10B | 0.3830 | 0.5693 | 0.4835 | 0.047* |
C11 | 0.2824 (4) | 0.5642 (5) | 0.4778 (4) | 0.044 (2) |
H11A | 0.2364 | 0.5815 | 0.4420 | 0.053* |
H11B | 0.2906 | 0.5951 | 0.5237 | 0.053* |
C12 | 0.2818 (4) | 0.4698 (6) | 0.4915 (5) | 0.059 (2) |
H12A | 0.2455 | 0.4567 | 0.5097 | 0.088* |
H12B | 0.2727 | 0.4389 | 0.4459 | 0.088* |
H12C | 0.3268 | 0.4525 | 0.5276 | 0.088* |
C13 | 0.3714 (4) | 0.6817 (5) | 0.3333 (3) | 0.0348 (16) |
H13A | 0.4026 | 0.7085 | 0.3125 | 0.042* |
H13B | 0.3834 | 0.6206 | 0.3400 | 0.042* |
C14 | 0.2978 (4) | 0.6896 (6) | 0.2779 (4) | 0.0412 (18) |
H14A | 0.2839 | 0.7501 | 0.2711 | 0.049* |
H14B | 0.2657 | 0.6589 | 0.2953 | 0.049* |
C15 | 0.2940 (4) | 0.6515 (7) | 0.2051 (4) | 0.057 (2) |
H15A | 0.3294 | 0.6789 | 0.1907 | 0.068* |
H15B | 0.3049 | 0.5901 | 0.2118 | 0.068* |
C16 | 0.2249 (5) | 0.6627 (9) | 0.1459 (5) | 0.083 (4) |
H16A | 0.2251 | 0.6375 | 0.1009 | 0.124* |
H16B | 0.1898 | 0.6346 | 0.1594 | 0.124* |
H16C | 0.2143 | 0.7234 | 0.1383 | 0.124* |
C1L | 0.1235 (8) | 0.4569 (8) | 0.2807 (9) | 0.110 (5) |
H1L1 | 0.1317 | 0.4857 | 0.3275 | 0.132* |
H1L2 | 0.0904 | 0.4924 | 0.2416 | 0.132* |
Cl1L | 0.19998 (18) | 0.4539 (3) | 0.2681 (2) | 0.1200 (15) |
Cl2L | 0.0881 (5) | 0.3685 (5) | 0.2810 (5) | 0.294 (6) |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
Cl1 | 0.0321 (9) | 0.0584 (12) | 0.0230 (8) | −0.0037 (9) | 0.0059 (7) | −0.0024 (8)
Si1 | 0.0233 (9) | 0.0364 (11) | 0.0327 (10) | −0.0031 (8) | 0.0092 (8) | −0.0029 (8)
Si2 | 0.0281 (9) | 0.0417 (12) | 0.0302 (10) | 0.0050 (9) | 0.0124 (8) | −0.0018 (9)
Si3 | 0.0373 (15) | 0.0330 (16) | 0.0421 (16) | 0.000 | 0.0174 (13) | 0.000
Cl11 | 0.0498 (11) | 0.0575 (14) | 0.0576 (13) | −0.0087 (10) | 0.0251 (10) | 0.0109 (11)
Cl12 | 0.0345 (10) | 0.0572 (14) | 0.0600 (13) | −0.0137 (9) | 0.0082 (9) | −0.0193 (11)
Cl21 | 0.0526 (12) | 0.0739 (15) | 0.0441 (11) | 0.0101 (11) | 0.0302 (10) | −0.0056 (10)
Cl22 | 0.0276 (9) | 0.0708 (15) | 0.0470 (11) | 0.0139 (9) | 0.0095 (8) | 0.0056 (10)
Cl31 | 0.0663 (15) | 0.0501 (13) | 0.0859 (18) | −0.0109 (12) | 0.0315 (13) | −0.0313 (13)
N1 | 0.027 (3) | 0.032 (3) | 0.028 (3) | 0.003 (2) | 0.014 (2) | 0.002 (2)
C1 | 0.025 (3) | 0.036 (4) | 0.030 (4) | 0.002 (3) | 0.009 (3) | 0.000 (3)
C2 | 0.044 (4) | 0.035 (4) | 0.039 (4) | −0.006 (3) | 0.023 (3) | −0.005 (3)
C3 | 0.030 (4) | 0.065 (6) | 0.045 (4) | −0.006 (4) | 0.014 (3) | −0.011 (4)
C4 | 0.045 (5) | 0.054 (6) | 0.096 (7) | −0.011 (4) | 0.043 (5) | −0.018 (5)
C5 | 0.032 (4) | 0.035 (4) | 0.040 (4) | 0.009 (3) | 0.015 (3) | 0.003 (3)
C6 | 0.052 (5) | 0.039 (4) | 0.046 (4) | 0.001 (4) | 0.024 (4) | −0.007 (4)
C7 | 0.042 (5) | 0.038 (5) | 0.082 (7) | 0.005 (4) | 0.020 (4) | −0.012 (4)
C8 | 0.063 (6) | 0.052 (6) | 0.116 (9) | −0.004 (5) | 0.033 (6) | −0.034 (6)
C9 | 0.024 (3) | 0.042 (4) | 0.025 (3) | 0.000 (3) | 0.010 (3) | 0.003 (3)
C10 | 0.039 (4) | 0.043 (4) | 0.041 (4) | −0.002 (4) | 0.019 (3) | 0.003 (4)
C11 | 0.028 (4) | 0.057 (5) | 0.049 (5) | 0.001 (4) | 0.016 (3) | 0.016 (4)
C12 | 0.043 (5) | 0.059 (6) | 0.079 (7) | −0.005 (4) | 0.027 (5) | 0.019 (5)
C13 | 0.040 (4) | 0.043 (4) | 0.025 (3) | 0.004 (3) | 0.017 (3) | −0.002 (3)
C14 | 0.036 (4) | 0.055 (5) | 0.030 (4) | −0.003 (4) | 0.010 (3) | −0.005 (3)
C15 | 0.044 (5) | 0.082 (7) | 0.045 (5) | 0.005 (5) | 0.018 (4) | −0.005 (5)
C16 | 0.056 (6) | 0.150 (12) | 0.035 (5) | 0.004 (7) | 0.009 (4) | −0.019 (6)
C1L | 0.143 (13) | 0.077 (9) | 0.149 (13) | 0.017 (9) | 0.100 (11) | −0.003 (9)
Cl1L | 0.087 (2) | 0.168 (4) | 0.114 (3) | −0.022 (2) | 0.048 (2) | −0.065 (3)
Cl2L | 0.471 (12) | 0.237 (7) | 0.350 (10) | −0.225 (8) | 0.355 (10) | −0.183 (7)

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Si1—Cl12 | 2.097 (3) | C7—H7A | 0.9900
Si1—Cl11 | 2.098 (3) | C7—H7B | 0.9900
Si1—Si2 | 2.339 (3) | C8—H8A | 0.9800
Si1—Si1i | 2.341 (4) | C8—H8B | 0.9800
Si2—Cl21 | 2.081 (3) | C8—H8C | 0.9800
Si2—Cl22 | 2.100 (3) | C9—C10 | 1.519 (10)
Si2—Si3 | 2.347 (3) | C9—H9A | 0.9900
Si3—Cl31 | 2.086 (3) | C9—H9B | 0.9900
Si3—Cl31i | 2.086 (3) | C10—C11 | 1.509 (9)
Si3—Si2i | 2.347 (3) | C10—H10A | 0.9900
N1—C9 | 1.513 (8) | C10—H10B | 0.9900
N1—C5 | 1.515 (9) | C11—C12 | 1.513 (12)
N1—C1 | 1.523 (8) | C11—H11A | 0.9900
N1—C13 | 1.525 (8) | C11—H11B | 0.9900
C1—C2 | 1.531 (9) | C12—H12A | 0.9800
C1—H1A | 0.9900 | C12—H12B | 0.9800
C1—H1B | 0.9900 | C12—H12C | 0.9800
C2—C3 | 1.510 (10) | C13—C14 | 1.518 (10)
C2—H2A | 0.9900 | C13—H13A | 0.9900
C2—H2B | 0.9900 | C13—H13B | 0.9900
C3—C4 | 1.538 (10) | C14—C15 | 1.539 (10)
C3—H3A | 0.9900 | C14—H14A | 0.9900
C3—H3B | 0.9900 | C14—H14B | 0.9900
C4—H4A | 0.9800 | C15—C16 | 1.485 (12)
C4—H4B | 0.9800 | C15—H15A | 0.9900
C4—H4C | 0.9800 | C15—H15B | 0.9900
C5—C6 | 1.521 (10) | C16—H16A | 0.9800
C5—H5A | 0.9900 | C16—H16B | 0.9800
C5—H5B | 0.9900 | C16—H16C | 0.9800
C6—C7 | 1.516 (11) | C1L—Cl2L | 1.578 (14)
C6—H6A | 0.9900 | C1L—Cl1L | 1.711 (13)
C6—H6B | 0.9900 | C1L—H1L1 | 0.9900
C7—C8 | 1.522 (13) | C1L—H1L2 | 0.9900
Cl12—Si1—Cl11 | 99.57 (12) | C6—C7—H7B | 109.2
Cl12—Si1—Si2 | 111.06 (11) | C8—C7—H7B | 109.2
Cl11—Si1—Si2 | 114.22 (11) | H7A—C7—H7B | 107.9
Cl12—Si1—Si1i | 112.32 (12) | C7—C8—H8A | 109.5
Cl11—Si1—Si1i | 111.28 (12) | C7—C8—H8B | 109.5
Si2—Si1—Si1i | 108.28 (6) | H8A—C8—H8B | 109.5
Cl21—Si2—Cl22 | 99.76 (11) | C7—C8—H8C | 109.5
Cl21—Si2—Si1 | 114.16 (12) | H8A—C8—H8C | 109.5
Cl22—Si2—Si1 | 110.71 (12) | H8B—C8—H8C | 109.5
Cl21—Si2—Si3 | 111.61 (12) | N1—C9—C10 | 116.6 (6)
Cl22—Si2—Si3 | 113.15 (11) | N1—C9—H9A | 108.1
Si1—Si2—Si3 | 107.47 (10) | C10—C9—H9A | 108.1
Cl31—Si3—Cl31i | 99.6 (2) | N1—C9—H9B | 108.1
Cl31—Si3—Si2 | 111.65 (9) | C10—C9—H9B | 108.1
Cl31i—Si3—Si2 | 112.64 (9) | H9A—C9—H9B | 107.3
Cl31—Si3—Si2i | 112.64 (9) | C11—C10—C9 | 110.0 (6)
Cl31i—Si3—Si2i | 111.65 (9) | C11—C10—H10A | 109.7
Si2—Si3—Si2i | 108.50 (16) | C9—C10—H10A | 109.7
C9—N1—C5 | 108.1 (5) | C11—C10—H10B | 109.7
C9—N1—C1 | 109.8 (5) | C9—C10—H10B | 109.7
C5—N1—C1 | 111.2 (5) | H10A—C10—H10B | 108.2
C9—N1—C13 | 110.9 (5) | C10—C11—C12 | 112.6 (7)
C5—N1—C13 | 108.8 (5) | C10—C11—H11A | 109.1
C1—N1—C13 | 108.0 (5) | C12—C11—H11A | 109.1
N1—C1—C2 | 116.1 (6) | C10—C11—H11B | 109.1
N1—C1—H1A | 108.3 | C12—C11—H11B | 109.1
C2—C1—H1A | 108.3 | H11A—C11—H11B | 107.8
N1—C1—H1B | 108.3 | C11—C12—H12A | 109.5
C2—C1—H1B | 108.3 | C11—C12—H12B | 109.5
H1A—C1—H1B | 107.4 | H12A—C12—H12B | 109.5
C3—C2—C1 | 110.1 (6) | C11—C12—H12C | 109.5
C3—C2—H2A | 109.6 | H12A—C12—H12C | 109.5
C1—C2—H2A | 109.6 | H12B—C12—H12C | 109.5
C3—C2—H2B | 109.6 | C14—C13—N1 | 116.9 (6)
C1—C2—H2B | 109.6 | C14—C13—H13A | 108.1
H2A—C2—H2B | 108.1 | N1—C13—H13A | 108.1
C2—C3—C4 | 112.1 (7) | C14—C13—H13B | 108.1
C2—C3—H3A | 109.2 | N1—C13—H13B | 108.1
C4—C3—H3A | 109.2 | H13A—C13—H13B | 107.3
C2—C3—H3B | 109.2 | C13—C14—C15 | 108.9 (6)
C4—C3—H3B | 109.2 | C13—C14—H14A | 109.9
H3A—C3—H3B | 107.9 | C15—C14—H14A | 109.9
C3—C4—H4A | 109.5 | C13—C14—H14B | 109.9
C3—C4—H4B | 109.5 | C15—C14—H14B | 109.9
H4A—C4—H4B | 109.5 | H14A—C14—H14B | 108.3
C3—C4—H4C | 109.5 | C16—C15—C14 | 112.5 (7)
H4A—C4—H4C | 109.5 | C16—C15—H15A | 109.1
H4B—C4—H4C | 109.5 | C14—C15—H15A | 109.1
N1—C5—C6 | 115.6 (6) | C16—C15—H15B | 109.1
N1—C5—H5A | 108.4 | C14—C15—H15B | 109.1
C6—C5—H5A | 108.4 | H15A—C15—H15B | 107.8
N1—C5—H5B | 108.4 | C15—C16—H16A | 109.5
C6—C5—H5B | 108.4 | C15—C16—H16B | 109.5
H5A—C5—H5B | 107.4 | H16A—C16—H16B | 109.5
C7—C6—C5 | 110.1 (7) | C15—C16—H16C | 109.5
C7—C6—H6A | 109.6 | H16A—C16—H16C | 109.5
C5—C6—H6A | 109.6 | H16B—C16—H16C | 109.5
C7—C6—H6B | 109.6 | Cl2L—C1L—Cl1L | 116.2 (8)
C5—C6—H6B | 109.6 | Cl2L—C1L—H1L1 | 108.2
H6A—C6—H6B | 108.2 | Cl1L—C1L—H1L1 | 108.2
C6—C7—C8 | 112.3 (8) | Cl2L—C1L—H1L2 | 108.2
C6—C7—H7A | 109.2 | Cl1L—C1L—H1L2 | 108.2
C8—C7—H7A | 109.2 | H1L1—C1L—H1L2 | 107.4
C9—N1—C1—C2 | −174.3 (6) | C5—N1—C9—C10 | 175.4 (6)
C5—N1—C1—C2 | −54.8 (7) | C1—N1—C9—C10 | −63.2 (7)
C13—N1—C1—C2 | 64.6 (7) | C13—N1—C9—C10 | 56.1 (8)
N1—C1—C2—C3 | −179.8 (6) | N1—C9—C10—C11 | −175.2 (6)
C1—C2—C3—C4 | 172.9 (7) | C9—C10—C11—C12 | −176.1 (7)
C9—N1—C5—C6 | 68.4 (7) | C9—N1—C13—C14 | 55.2 (8)
C1—N1—C5—C6 | −52.2 (7) | C5—N1—C13—C14 | −63.6 (8)
C13—N1—C5—C6 | −171.0 (6) | C1—N1—C13—C14 | 175.6 (6)
N1—C5—C6—C7 | −179.9 (6) | N1—C13—C14—C15 | 176.8 (7)
C5—C6—C7—C8 | −177.3 (7) | C13—C14—C15—C16 | −175.4 (9)

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D—H···A | D—H | H···A | D···A | D—H···A
C1—H1B···Cl1 | 0.99 | 2.88 | 3.686 (7) | 139
C2—H2A···Cl31ii | 0.99 | 2.89 | 3.596 (8) | 129
C5—H5A···Cl22iii | 0.99 | 2.99 | 3.945 (7) | 163
C9—H9B···Cl1 | 0.99 | 2.91 | 3.652 (7) | 132
C1L—H1L1···Cl12iii | 0.99 | 2.96 | 3.528 (13) | 119

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2C₈H₂₀N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂ | Z = 2
Mr = 996.20 | F(000) = 1016
Triclinic, P1 | Dx = 1.525 Mg m⁻³
a = 10.3596 (4) Å | Mo Kα radiation, λ = 0.71073 Å
b = 13.9612 (5) Å | Cell parameters from 153722 reflections
c = 16.0205 (6) Å | θ = 3.3–30.8°
α = 89.959 (3)° | µ = 1.17 mm⁻¹
β = 72.484 (3)° | T = 173 K
γ = 79.534 (3)° | Block, colourless
V = 2169.29 (15) Å³ | 0.23 × 0.23 × 0.20 mm

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Stoe IPDS II two-circle diffractometer | 11976 reflections with I > 2σ(I)
ω scans | Rint = 0.043
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | θmax = 30.5°, θmin = 3.4°
Tmin = 0.408, Tmax = 1.000 | h = −14→14
62962 measured reflections | k = −19→19
13044 independent reflections | l = −22→22

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Refinement on F² | 0 restraints
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048 | H-atom parameters constrained
wR(F²) = 0.131 | w = 1/[σ²(Fo²) + (0.0683P)² + 1.6519P] where P = (Fo² + 2Fc²)/3
S = 1.08 | (Δ/σ)max = 0.001
13044 reflections | Δρmax = 0.87 e Å⁻³
409 parameters | Δρmin = −0.84 e Å⁻³

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Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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| x | y | z | Uiso*/Ueq | Occ. (<1)
Cl1 | 0.68362 (5) | 0.71247 (4) | 0.37887 (3) | 0.03357 (10) |
Cl2 | 0.55394 (6) | 0.71721 (4) | 0.14756 (3) | 0.03425 (11) |
Si1 | 0.79603 (6) | 0.63165 (4) | 0.19539 (4) | 0.03316 (12) |
Si2 | 0.74595 (6) | 0.80223 (4) | 0.20699 (4) | 0.02939 (11) |
Si3 | 0.51729 (5) | 0.85241 (4) | 0.29623 (3) | 0.02570 (10) |
Si4 | 0.42527 (5) | 0.71172 (4) | 0.33588 (3) | 0.02431 (10) |
Si5 | 0.59853 (6) | 0.57465 (4) | 0.27696 (4) | 0.02724 (11) |
Cl11 | 0.97197 (6) | 0.57714 (6) | 0.23162 (6) | 0.0628 (2) |
Cl12 | 0.86579 (9) | 0.57414 (5) | 0.06642 (4) | 0.0632 (2) |
Cl21 | 0.88627 (7) | 0.86092 (6) | 0.25209 (5) | 0.05179 (16) |
Cl22 | 0.78501 (6) | 0.86177 (4) | 0.08273 (4) | 0.04303 (13) |
Cl31 | 0.49581 (7) | 0.94164 (4) | 0.40573 (4) | 0.04399 (13) |
Cl32 | 0.39997 (6) | 0.94686 (4) | 0.23306 (4) | 0.04020 (12) |
Cl41 | 0.33929 (5) | 0.71094 (4) | 0.47227 (3) | 0.03436 (10) |
Cl42 | 0.24659 (5) | 0.71209 (4) | 0.29964 (4) | 0.03703 (11) |
Cl51 | 0.63586 (6) | 0.47736 (4) | 0.36927 (4) | 0.04057 (12) |
Cl52 | 0.53223 (8) | 0.48498 (4) | 0.20041 (4) | 0.04831 (15) |
N1 | 0.27041 (18) | 0.79721 (13) | −0.00541 (11) | 0.0299 (3) |
C1 | 0.2204 (4) | 0.7299 (2) | 0.06657 (18) | 0.0551 (7) |
H1A | 0.1238 | 0.7262 | 0.0717 | 0.066* |
H1B | 0.2206 | 0.7590 | 0.1228 | 0.066* |
C2 | 0.3050 (4) | 0.62647 (19) | 0.0530 (2) | 0.0551 (7) |
H2A | 0.2656 | 0.5882 | 0.1024 | 0.083* |
H2B | 0.3034 | 0.5959 | −0.0016 | 0.083* |
H2C | 0.4004 | 0.6288 | 0.0497 | 0.083* |
C3 | 0.2867 (3) | 0.7533 (2) | −0.09498 (16) | 0.0438 (5) |
H3A | 0.3641 | 0.6966 | −0.1089 | 0.053* |
H3B | 0.3126 | 0.8021 | −0.1387 | 0.053* |
C4 | 0.1610 (4) | 0.7201 (3) | −0.1052 (3) | 0.0648 (9) |
H4A | 0.1816 | 0.6928 | −0.1651 | 0.097* |
H4B | 0.1357 | 0.6701 | −0.0636 | 0.097* |
H4C | 0.0842 | 0.7759 | −0.0934 | 0.097* |
C5 | 0.1640 (3) | 0.89268 (19) | 0.0117 (2) | 0.0470 (6) |
H5A | 0.1863 | 0.9314 | −0.0407 | 0.056* |
H5B | 0.0721 | 0.8767 | 0.0192 | 0.056* |
C6 | 0.1555 (3) | 0.9554 (2) | 0.0910 (2) | 0.0545 (7) |
H6A | 0.0852 | 1.0145 | 0.0967 | 0.082* |
H6B | 0.1306 | 0.9187 | 0.1438 | 0.082* |
H6C | 0.2451 | 0.9736 | 0.0837 | 0.082* |
C7 | 0.4085 (3) | 0.81784 (18) | −0.00349 (18) | 0.0412 (5) |
H7A | 0.3980 | 0.8424 | 0.0566 | 0.049* |
H7B | 0.4756 | 0.7554 | −0.0155 | 0.049* |
C8 | 0.4683 (3) | 0.8892 (2) | −0.0662 (2) | 0.0517 (6) |
H8A | 0.5568 | 0.8970 | −0.0594 | 0.078* |
H8B | 0.4826 | 0.8651 | −0.1264 | 0.078* |
H8C | 0.4048 | 0.9523 | −0.0540 | 0.078* |
N2 | 0.0000 | 0.5000 | 0.5000 | 0.0260 (4) |
C21 | −0.0005 (4) | 0.6091 (3) | 0.5117 (3) | 0.0331 (8) | 0.5
H21A | −0.0855 | 0.6483 | 0.5040 | 0.040* | 0.5
H21B | 0.0800 | 0.6270 | 0.4675 | 0.040* | 0.5
C21' | 0.0128 (5) | 0.5139 (3) | 0.5909 (3) | 0.0350 (8) | 0.5
H21C | 0.1013 | 0.4755 | 0.5941 | 0.042* | 0.5
H21D | −0.0633 | 0.4912 | 0.6352 | 0.042* | 0.5
C22 | 0.0063 (3) | 0.6300 (3) | 0.6105 (2) | 0.0638 (9) |
H22A | 0.0061 | 0.6994 | 0.6197 | 0.096* | 0.5
H22B | −0.0740 | 0.6122 | 0.6536 | 0.096* | 0.5
H22C | 0.0908 | 0.5910 | 0.6173 | 0.096* | 0.5
H22D | 0.0144 | 0.6403 | 0.6690 | 0.096* | 0.5
H22E | 0.0823 | 0.6518 | 0.5665 | 0.096* | 0.5
H22F | −0.0818 | 0.6675 | 0.6075 | 0.096* | 0.5
C23 | 0.1319 (4) | 0.4394 (3) | 0.5085 (3) | 0.0294 (7) | 0.5
H23A | 0.1285 | 0.3693 | 0.5040 | 0.035* | 0.5
H23B | 0.1411 | 0.4544 | 0.5666 | 0.035* | 0.5
C23' | 0.1182 (4) | 0.5289 (3) | 0.4300 (3) | 0.0321 (7) | 0.5
H23C | 0.1196 | 0.5986 | 0.4398 | 0.039* | 0.5
H23D | 0.1063 | 0.5197 | 0.3717 | 0.039* | 0.5
C24 | 0.2624 (2) | 0.4624 (2) | 0.4327 (2) | 0.0533 (7) |
H24A | 0.3471 | 0.4228 | 0.4389 | 0.080* | 0.5
H24B | 0.2538 | 0.4467 | 0.3753 | 0.080* | 0.5
H24C | 0.2662 | 0.5317 | 0.4377 | 0.080* | 0.5
H24D | 0.3391 | 0.4813 | 0.3871 | 0.080* | 0.5
H24E | 0.2743 | 0.4723 | 0.4903 | 0.080* | 0.5
H24F | 0.2610 | 0.3935 | 0.4224 | 0.080* | 0.5
N3 | 0.0000 | 1.0000 | 0.5000 | 0.0324 (5) |
C31 | −0.0124 (7) | 1.0998 (4) | 0.5376 (4) | 0.0522 (13) | 0.5
H31A | −0.0599 | 1.1032 | 0.6015 | 0.063* | 0.5
H31B | −0.0684 | 1.1477 | 0.5106 | 0.063* | 0.5
C31' | 0.1452 (5) | 1.0189 (5) | 0.4881 (4) | 0.0509 (13) | 0.5
H31C | 0.2003 | 1.0076 | 0.4255 | 0.061* | 0.5
H31D | 0.1910 | 0.9729 | 0.5221 | 0.061* | 0.5
C32 | 0.1392 (6) | 1.1271 (4) | 0.5199 (3) | 0.0956 (17) |
H32A | 0.1294 | 1.1930 | 0.5450 | 0.143* | 0.5
H32B | 0.1941 | 1.0803 | 0.5474 | 0.143* | 0.5
H32C | 0.1855 | 1.1246 | 0.4566 | 0.143* | 0.5
H32D | 0.2330 | 1.1379 | 0.5118 | 0.143* | 0.5
H32E | 0.0951 | 1.1727 | 0.4856 | 0.143* | 0.5
H32F | 0.0857 | 1.1380 | 0.5821 | 0.143* | 0.5
C33 | −0.0905 (5) | 1.0176 (4) | 0.5927 (3) | 0.0412 (10) | 0.5
H33A | −0.1850 | 1.0092 | 0.5967 | 0.049* | 0.5
H33B | −0.0952 | 1.0851 | 0.6140 | 0.049* | 0.5
C33' | 0.0691 (5) | 0.9243 (4) | 0.5529 (3) | 0.0459 (11) | 0.5
H33C | 0.1629 | 0.9350 | 0.5479 | 0.055* | 0.5
H33D | 0.0765 | 0.8572 | 0.5296 | 0.055* | 0.5
C34 | −0.0250 (4) | 0.9384 (3) | 0.6531 (2) | 0.0724 (11) |
H34A | −0.0833 | 0.9490 | 0.7144 | 0.109* | 0.5
H34B | −0.0212 | 0.8719 | 0.6318 | 0.109* | 0.5
H34C | 0.0683 | 0.9475 | 0.6490 | 0.109* | 0.5
H34D | 0.0162 | 0.8916 | 0.6879 | 0.109* | 0.5
H34E | −0.0314 | 1.0050 | 0.6756 | 0.109* | 0.5
H34F | −0.1175 | 0.9274 | 0.6574 | 0.109* | 0.5
C1L | 0.1880 (4) | 0.3162 (2) | 0.1144 (2) | 0.0565 (7) |
H1L1 | 0.2330 | 0.2960 | 0.0516 | 0.068* |
H1L2 | 0.0997 | 0.3611 | 0.1200 | 0.068* |
Cl1A | 0.29537 (8) | 0.37721 (5) | 0.15334 (6) | 0.05663 (17) |
Cl1B | 0.15522 (9) | 0.21224 (6) | 0.17452 (6) | 0.05883 (18) |
C2L | 0.4865 (4) | 0.7900 (3) | 0.6208 (2) | 0.0642 (8) |
H2L1 | 0.5201 | 0.8228 | 0.5657 | 0.077* |
H2L2 | 0.4831 | 0.7222 | 0.6050 | 0.077* |
Cl2A | 0.60192 (10) | 0.78831 (6) | 0.68194 (6) | 0.0634 (2) |
Cl2B | 0.32076 (10) | 0.85079 (10) | 0.67916 (6) | 0.0828 (3) |

[Back]

[Back]

| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
Cl1 | 0.0361 (2) | 0.0429 (3) | 0.0274 (2) | −0.01369 (19) | −0.01464 (17) | 0.00581 (17)
Cl2 | 0.0424 (3) | 0.0357 (2) | 0.0271 (2) | −0.00201 (19) | −0.01742 (18) | −0.00062 (16)
Si1 | 0.0284 (2) | 0.0311 (3) | 0.0307 (3) | 0.0042 (2) | −0.0012 (2) | 0.0051 (2)
Si2 | 0.0258 (2) | 0.0307 (3) | 0.0279 (2) | −0.00452 (19) | −0.00314 (19) | 0.00405 (19)
Si3 | 0.0266 (2) | 0.0229 (2) | 0.0245 (2) | −0.00328 (17) | −0.00405 (18) | −0.00117 (17)
Si4 | 0.0239 (2) | 0.0234 (2) | 0.0246 (2) | −0.00303 (17) | −0.00662 (17) | −0.00054 (16)
Si5 | 0.0287 (2) | 0.0228 (2) | 0.0295 (2) | −0.00127 (18) | −0.00988 (19) | −0.00119 (18)
Cl11 | 0.0288 (3) | 0.0663 (4) | 0.0855 (5) | 0.0061 (3) | −0.0147 (3) | 0.0272 (4)
Cl12 | 0.0766 (5) | 0.0475 (3) | 0.0344 (3) | 0.0162 (3) | 0.0127 (3) | −0.0050 (2)
Cl21 | 0.0423 (3) | 0.0669 (4) | 0.0530 (3) | −0.0301 (3) | −0.0132 (3) | 0.0083 (3)
Cl22 | 0.0427 (3) | 0.0432 (3) | 0.0342 (2) | −0.0043 (2) | −0.0008 (2) | 0.0144 (2)
Cl31 | 0.0582 (3) | 0.0344 (2) | 0.0360 (3) | −0.0095 (2) | −0.0090 (2) | −0.0121 (2)
Cl32 | 0.0410 (3) | 0.0302 (2) | 0.0445 (3) | 0.00368 (19) | −0.0119 (2) | 0.00648 (19)
Cl41 | 0.0336 (2) | 0.0416 (3) | 0.0253 (2) | −0.01096 (19) | −0.00306 (17) | 0.00253 (17)
Cl42 | 0.0285 (2) | 0.0429 (3) | 0.0433 (3) | −0.00619 (18) | −0.01663 (19) | 0.0021 (2)
Cl51 | 0.0404 (3) | 0.0343 (2) | 0.0516 (3) | −0.0089 (2) | −0.0198 (2) | 0.0174 (2)
Cl52 | 0.0629 (4) | 0.0337 (3) | 0.0529 (3) | −0.0081 (2) | −0.0251 (3) | −0.0133 (2)
N1 | 0.0310 (8) | 0.0304 (8) | 0.0275 (7) | −0.0052 (6) | −0.0080 (6) | 0.0030 (6)
C1 | 0.0746 (19) | 0.0423 (13) | 0.0395 (12) | −0.0160 (13) | −0.0016 (12) | 0.0076 (10)
C2 | 0.085 (2) | 0.0343 (12) | 0.0522 (15) | −0.0151 (13) | −0.0287 (15) | 0.0117 (10)
C3 | 0.0530 (14) | 0.0456 (12) | 0.0365 (11) | −0.0105 (10) | −0.0187 (10) | −0.0010 (9)
C4 | 0.069 (2) | 0.0598 (18) | 0.087 (2) | −0.0171 (15) | −0.0524 (19) | −0.0019 (16)
C5 | 0.0357 (11) | 0.0378 (12) | 0.0634 (16) | −0.0041 (9) | −0.0110 (11) | 0.0002 (11)
C6 | 0.0512 (15) | 0.0407 (13) | 0.0554 (15) | −0.0079 (11) | 0.0070 (12) | −0.0096 (11)
C7 | 0.0378 (11) | 0.0392 (11) | 0.0498 (13) | −0.0028 (9) | −0.0208 (10) | 0.0006 (9)
C8 | 0.0378 (12) | 0.0480 (14) | 0.0643 (17) | −0.0150 (10) | −0.0042 (11) | −0.0017 (12)
N2 | 0.0230 (9) | 0.0267 (10) | 0.0268 (10) | −0.0036 (8) | −0.0063 (8) | 0.0051 (8)
C21 | 0.0329 (18) | 0.0228 (16) | 0.040 (2) | −0.0042 (14) | −0.0058 (16) | 0.0055 (14)
C21' | 0.0330 (19) | 0.043 (2) | 0.0293 (17) | −0.0049 (16) | −0.0108 (15) | 0.0050 (15)
C22 | 0.0471 (15) | 0.073 (2) | 0.0663 (19) | −0.0141 (14) | −0.0078 (13) | −0.0342 (16)
C23 | 0.0252 (16) | 0.0297 (17) | 0.0327 (17) | −0.0030 (13) | −0.0095 (14) | 0.0056 (14)
C23' | 0.0275 (17) | 0.0336 (18) | 0.0322 (18) | −0.0082 (14) | −0.0031 (14) | 0.0067 (14)
C24 | 0.0240 (9) | 0.0589 (16) | 0.0671 (17) | −0.0074 (10) | 0.0005 (10) | −0.0163 (13)
N3 | 0.0243 (10) | 0.0345 (12) | 0.0329 (11) | 0.0000 (9) | −0.0037 (9) | −0.0037 (9)
C31 | 0.072 (4) | 0.037 (2) | 0.040 (2) | −0.006 (2) | −0.009 (2) | −0.0055 (19)
C31' | 0.030 (2) | 0.081 (4) | 0.043 (3) | −0.015 (2) | −0.0107 (18) | 0.013 (2)
C32 | 0.146 (4) | 0.103 (3) | 0.080 (3) | −0.084 (3) | −0.061 (3) | 0.023 (2)
C33 | 0.034 (2) | 0.049 (2) | 0.0292 (18) | 0.0039 (18) | 0.0004 (16) | −0.0031 (17)
C33' | 0.033 (2) | 0.055 (3) | 0.045 (2) | 0.0018 (19) | −0.0118 (19) | 0.009 (2)
C34 | 0.083 (2) | 0.110 (3) | 0.0381 (14) | −0.048 (2) | −0.0207 (15) | 0.0216 (16)
C1L | 0.0620 (17) | 0.0570 (16) | 0.0647 (18) | −0.0176 (14) | −0.0369 (15) | 0.0150 (13)
Cl1A | 0.0500 (3) | 0.0452 (3) | 0.0797 (5) | −0.0104 (3) | −0.0265 (3) | 0.0018 (3)
Cl1B | 0.0613 (4) | 0.0527 (4) | 0.0685 (5) | −0.0195 (3) | −0.0237 (4) | 0.0092 (3)
C2L | 0.0639 (19) | 0.078 (2) | 0.0503 (16) | 0.0043 (16) | −0.0266 (14) | −0.0118 (15)
Cl2A | 0.0746 (5) | 0.0622 (4) | 0.0588 (4) | 0.0015 (4) | −0.0367 (4) | −0.0093 (3)
Cl2B | 0.0612 (5) | 0.1170 (9) | 0.0576 (5) | 0.0084 (5) | −0.0143 (4) | 0.0110 (5)

[Back]

[Back]

Si1—Cl12 | 2.0805 (9) | C22—H22B | 0.9800
Si1—Cl11 | 2.0906 (9) | C22—H22C | 0.9800
Si1—Si2 | 2.3386 (8) | C22—H22D | 0.9800
Si1—Si5 | 2.3469 (8) | C22—H22E | 0.9800
Si2—Cl21 | 2.0910 (8) | C22—H22F | 0.9800
Si2—Cl22 | 2.1102 (8) | C23—C24 | 1.604 (5)
Si2—Si3 | 2.3465 (7) | C23—H23A | 0.9900
Si3—Cl31 | 2.0849 (7) | C23—H23B | 0.9900
Si3—Cl32 | 2.0967 (8) | C23'—C24 | 1.622 (5)
Si3—Si4 | 2.3419 (7) | C23'—H23C | 0.9900
Si4—Cl41 | 2.0977 (7) | C23'—H23D | 0.9900
Si4—Cl42 | 2.0993 (7) | C24—H24A | 0.9800
Si4—Si5 | 2.3473 (7) | C24—H24B | 0.9800
Si5—Cl51 | 2.0814 (7) | C24—H24C | 0.9800
Si5—Cl52 | 2.0890 (8) | C24—H24D | 0.9800
N1—C3 | 1.510 (3) | C24—H24E | 0.9800
N1—C1 | 1.516 (3) | C24—H24F | 0.9800
N1—C7 | 1.519 (3) | N3—C31ii | 1.487 (5)
N1—C5 | 1.533 (3) | N3—C31 | 1.487 (5)
C1—C2 | 1.526 (4) | N3—C33ii | 1.491 (4)
C1—H1A | 0.9900 | N3—C33 | 1.491 (4)
C1—H1B | 0.9900 | N3—C31'ii | 1.530 (5)
C2—H2A | 0.9800 | N3—C31' | 1.530 (5)
C2—H2B | 0.9800 | N3—C33'ii | 1.561 (5)
C2—H2C | 0.9800 | N3—C33' | 1.561 (5)
C3—C4 | 1.511 (4) | C31—C32 | 1.625 (8)
C3—H3A | 0.9900 | C31—H31A | 0.9900
C3—H3B | 0.9900 | C31—H31B | 0.9900
C4—H4A | 0.9800 | C31'—C32 | 1.579 (8)
C4—H4B | 0.9800 | C31'—H31C | 0.9900
C4—H4C | 0.9800 | C31'—H31D | 0.9900
C5—C6 | 1.514 (4) | C32—H32A | 0.9800
C5—H5A | 0.9900 | C32—H32B | 0.9800
C5—H5B | 0.9900 | C32—H32C | 0.9800
C6—H6A | 0.9800 | C32—H32D | 0.9800
C6—H6B | 0.9800 | C32—H32E | 0.9800
C6—H6C | 0.9800 | C32—H32F | 0.9800
C7—C8 | 1.495 (4) | C33—C34 | 1.656 (6)
C7—H7A | 0.9900 | C33—H33A | 0.9900
C7—H7B | 0.9900 | C33—H33B | 0.9900
C8—H8A | 0.9800 | C33'—C34 | 1.599 (6)
C8—H8B | 0.9800 | C33'—H33C | 0.9900
C8—H8C | 0.9800 | C33'—H33D | 0.9900
N2—C23'i | 1.508 (4) | C34—H34A | 0.9800
N2—C23' | 1.508 (4) | C34—H34B | 0.9800
N2—C23i | 1.514 (4) | C34—H34C | 0.9800
N2—C23 | 1.514 (4) | C34—H34D | 0.9800
N2—C21'i | 1.517 (4) | C34—H34E | 0.9800
N2—C21' | 1.517 (4) | C34—H34F | 0.9800
N2—C21 | 1.533 (4) | C1L—Cl1A | 1.765 (3)
N2—C21i | 1.533 (4) | C1L—Cl1B | 1.769 (3)
C21—C22 | 1.633 (6) | C1L—H1L1 | 0.9900
C21—H21A | 0.9900 | C1L—H1L2 | 0.9900
C21—H21B | 0.9900 | C2L—Cl2B | 1.746 (4)
C21'—C22 | 1.636 (6) | C2L—Cl2A | 1.757 (3)
C21'—H21C | 0.9900 | C2L—H2L1 | 0.9900
C21'—H21D | 0.9900 | C2L—H2L2 | 0.9900
C22—H22A | 0.9800 |  |
Cl12—Si1—Cl11 | 98.50 (4) | C21—C22—H22A | 109.5
Cl12—Si1—Si2 | 113.28 (3) | C21—C22—H22B | 109.5
Cl11—Si1—Si2 | 111.32 (4) | H22A—C22—H22B | 109.5
Cl12—Si1—Si5 | 111.49 (4) | C21—C22—H22C | 109.5
Cl11—Si1—Si5 | 113.90 (4) | H22A—C22—H22C | 109.5
Si2—Si1—Si5 | 108.23 (3) | H22B—C22—H22C | 109.5
Cl21—Si2—Cl22 | 98.77 (4) | C21'—C22—H22D | 109.5
Cl21—Si2—Si1 | 112.27 (4) | C21'—C22—H22E | 109.5
Cl22—Si2—Si1 | 111.72 (3) | H22D—C22—H22E | 109.5
Cl21—Si2—Si3 | 112.69 (3) | C21'—C22—H22F | 109.5
Cl22—Si2—Si3 | 113.01 (3) | H22D—C22—H22F | 109.5
Si1—Si2—Si3 | 108.26 (3) | H22E—C22—H22F | 109.5
Cl31—Si3—Cl32 | 100.07 (3) | N2—C23—C24 | 110.3 (3)
Cl31—Si3—Si4 | 111.69 (3) | N2—C23—H23A | 109.6
Cl32—Si3—Si4 | 111.61 (3) | C24—C23—H23A | 109.6
Cl31—Si3—Si2 | 114.12 (3) | N2—C23—H23B | 109.6
Cl32—Si3—Si2 | 111.88 (3) | C24—C23—H23B | 109.6
Si4—Si3—Si2 | 107.47 (3) | H23A—C23—H23B | 108.1
Cl41—Si4—Cl42 | 98.87 (3) | N2—C23'—C24 | 109.6 (3)
Cl41—Si4—Si3 | 111.22 (3) | N2—C23'—H23C | 109.7
Cl42—Si4—Si3 | 112.22 (3) | C24—C23'—H23C | 109.7
Cl41—Si4—Si5 | 112.75 (3) | N2—C23'—H23D | 109.7
Cl42—Si4—Si5 | 113.01 (3) | C24—C23'—H23D | 109.7
Si3—Si4—Si5 | 108.60 (3) | H23C—C23'—H23D | 108.2
Cl51—Si5—Cl52 | 99.88 (3) | C23—C24—H24A | 109.5
Cl51—Si5—Si1 | 113.02 (3) | C23—C24—H24B | 109.5
Cl52—Si5—Si1 | 112.15 (3) | H24A—C24—H24B | 109.5
Cl51—Si5—Si4 | 114.27 (3) | C23—C24—H24C | 109.5
Cl52—Si5—Si4 | 110.11 (3) | H24A—C24—H24C | 109.5
Si1—Si5—Si4 | 107.38 (3) | H24B—C24—H24C | 109.5
C3—N1—C1 | 111.90 (19) | C23'—C24—H24D | 109.5
C3—N1—C7 | 108.98 (18) | C23'—C24—H24E | 109.5
C1—N1—C7 | 109.2 (2) | H24D—C24—H24E | 109.5
C3—N1—C5 | 108.79 (19) | C23'—C24—H24F | 109.5
C1—N1—C5 | 108.2 (2) | H24D—C24—H24F | 109.5
C7—N1—C5 | 109.76 (17) | H24E—C24—H24F | 109.5
N1—C1—C2 | 115.0 (2) | C31ii—N3—C31 | 180.0 (4)
N1—C1—H1A | 108.5 | C31ii—N3—C33ii | 66.3 (3)
C2—C1—H1A | 108.5 | C31—N3—C33ii | 113.7 (3)
N1—C1—H1B | 108.5 | C31ii—N3—C33 | 113.7 (3)
C2—C1—H1B | 108.5 | C31—N3—C33 | 66.3 (3)
H1A—C1—H1B | 107.5 | C33ii—N3—C33 | 180.0
C1—C2—H2A | 109.5 | C31'ii—N3—C31' | 180.0 (7)
C1—C2—H2B | 109.5 | C31'ii—N3—C33'ii | 72.4 (3)
H2A—C2—H2B | 109.5 | C31'—N3—C33'ii | 107.6 (3)
C1—C2—H2C | 109.5 | C31'ii—N3—C33' | 107.6 (3)
H2A—C2—H2C | 109.5 | C31'—N3—C33' | 72.4 (3)
H2B—C2—H2C | 109.5 | C33'ii—N3—C33' | 180.0 (3)
N1—C3—C4 | 115.5 (2) | N3—C31—C32 | 110.4 (4)
N1—C3—H3A | 108.4 | N3—C31—H31A | 109.6
C4—C3—H3A | 108.4 | C32—C31—H31A | 109.6
N1—C3—H3B | 108.4 | N3—C31—H31B | 109.6
C4—C3—H3B | 108.4 | C32—C31—H31B | 109.6
H3A—C3—H3B | 107.5 | H31A—C31—H31B | 108.1
C3—C4—H4A | 109.5 | N3—C31'—C32 | 110.7 (4)
C3—C4—H4B | 109.5 | N3—C31'—H31C | 109.5
H4A—C4—H4B | 109.5 | C32—C31'—H31C | 109.5
C3—C4—H4C | 109.5 | N3—C31'—H31D | 109.5
H4A—C4—H4C | 109.5 | C32—C31'—H31D | 109.5
H4B—C4—H4C | 109.5 | H31C—C31'—H31D | 108.1
C6—C5—N1 | 115.2 (2) | C31—C32—H32A | 109.5
C6—C5—H5A | 108.5 | C31—C32—H32B | 109.5
N1—C5—H5A | 108.5 | H32A—C32—H32B | 109.5
C6—C5—H5B | 108.5 | C31—C32—H32C | 109.5
N1—C5—H5B | 108.5 | H32A—C32—H32C | 109.5
H5A—C5—H5B | 107.5 | H32B—C32—H32C | 109.5
C5—C6—H6A | 109.5 | C31'—C32—H32D | 109.5
C5—C6—H6B | 109.5 | C31'—C32—H32E | 109.5
H6A—C6—H6B | 109.5 | H32D—C32—H32E | 109.5
C5—C6—H6C | 109.5 | C31'—C32—H32F | 109.5
H6A—C6—H6C | 109.5 | H32D—C32—H32F | 109.5
H6B—C6—H6C | 109.5 | H32E—C32—H32F | 109.5
C8—C7—N1 | 116.3 (2) | N3—C33—C34 | 108.3 (3)
C8—C7—H7A | 108.2 | N3—C33—H33A | 110.0
N1—C7—H7A | 108.2 | C34—C33—H33A | 110.0
C8—C7—H7B | 108.2 | N3—C33—H33B | 110.0
N1—C7—H7B | 108.2 | C34—C33—H33B | 110.0
H7A—C7—H7B | 107.4 | H33A—C33—H33B | 108.4
C7—C8—H8A | 109.5 | N3—C33'—C34 | 107.8 (3)
C7—C8—H8B | 109.5 | N3—C33'—H33C | 110.1
H8A—C8—H8B | 109.5 | C34—C33'—H33C | 110.1
C7—C8—H8C | 109.5 | N3—C33'—H33D | 110.1
H8A—C8—H8C | 109.5 | C34—C33'—H33D | 110.1
H8B—C8—H8C | 109.5 | H33C—C33'—H33D | 108.5
C23'i—N2—C23' | 180.0 | C33—C34—H34A | 109.5
C23i—N2—C23 | 180.0 (3) | C33—C34—H34B | 109.5
C23'i—N2—C21'i | 111.7 (2) | H34A—C34—H34B | 109.5
C23'—N2—C21'i | 68.3 (2) | C33—C34—H34C | 109.5
C23'i—N2—C21' | 68.3 (2) | H34A—C34—H34C | 109.5
C23'—N2—C21' | 111.7 (2) | H34B—C34—H34C | 109.5
C21'i—N2—C21' | 180.0 | C33'—C34—H34D | 109.5
C23i—N2—C21 | 69.5 (2) | C33'—C34—H34E | 109.5
C23—N2—C21 | 110.5 (2) | H34D—C34—H34E | 109.5
C23i—N2—C21i | 110.5 (2) | C33'—C34—H34F | 109.5
C23—N2—C21i | 69.5 (2) | H34D—C34—H34F | 109.5
C21—N2—C21i | 180.0 (4) | H34E—C34—H34F | 109.5
N2—C21—C22 | 107.8 (3) | Cl1A—C1L—Cl1B | 110.64 (16)
N2—C21—H21A | 110.2 | Cl1A—C1L—H1L1 | 109.5
C22—C21—H21A | 110.2 | Cl1B—C1L—H1L1 | 109.5
N2—C21—H21B | 110.2 | Cl1A—C1L—H1L2 | 109.5
C22—C21—H21B | 110.2 | Cl1B—C1L—H1L2 | 109.5
H21A—C21—H21B | 108.5 | H1L1—C1L—H1L2 | 108.1
N2—C21'—C22 | 108.4 (3) | Cl2B—C2L—Cl2A | 111.70 (18)
N2—C21'—H21C | 110.0 | Cl2B—C2L—H2L1 | 109.3
C22—C21'—H21C | 110.0 | Cl2A—C2L—H2L1 | 109.3
N2—C21'—H21D | 110.0 | Cl2B—C2L—H2L2 | 109.3
C22—C21'—H21D | 110.0 | Cl2A—C2L—H2L2 | 109.3
H21C—C21'—H21D | 108.4 | H2L1—C2L—H2L2 | 107.9
C3—N1—C1—C2 | 52.6 (3) | C23'i—N2—C21'—C22 | −117.4 (3)
C7—N1—C1—C2 | −68.1 (3) | C23'—N2—C21'—C22 | 62.6 (3)
C5—N1—C1—C2 | 172.4 (3) | C21—N2—C23—C24 | −62.3 (3)
C1—N1—C3—C4 | 53.9 (3) | C21i—N2—C23—C24 | 117.7 (3)
C7—N1—C3—C4 | 174.8 (2) | C21'i—N2—C23'—C24 | −119.9 (3)
C5—N1—C3—C4 | −65.6 (3) | C21'—N2—C23'—C24 | 60.1 (3)
C3—N1—C5—C6 | −168.9 (2) | C33ii—N3—C31—C32 | −49.5 (5)
C1—N1—C5—C6 | 69.3 (3) | C33—N3—C31—C32 | 130.5 (5)
C7—N1—C5—C6 | −49.8 (3) | C33'ii—N3—C31'—C32 | 57.8 (4)
C3—N1—C7—C8 | 61.8 (3) | C33'—N3—C31'—C32 | −122.2 (4)
C1—N1—C7—C8 | −175.7 (2) | C31ii—N3—C33—C34 | 60.0 (5)
C5—N1—C7—C8 | −57.2 (3) | C31—N3—C33—C34 | −120.0 (5)
C23i—N2—C21—C22 | 118.2 (3) | C31'ii—N3—C33'—C34 | −58.6 (5)
C23—N2—C21—C22 | −61.8 (3) | C31'—N3—C33'—C34 | 121.4 (5)

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D—H···A | D—H | H···A | D···A | D—H···A
C1—H1B···Cl42 | 0.99 | 2.99 | 3.829 (3) | 144
C2—H2C···Cl2 | 0.98 | 2.95 | 3.753 (3) | 139
C3—H3A···Cl52iii | 0.99 | 2.79 | 3.643 (3) | 144
C3—H3B···Cl2Biv | 0.99 | 2.98 | 3.804 (3) | 142
C5—H5B···Cl22v | 0.99 | 2.89 | 3.850 (3) | 165
C6—H6B···Cl21v | 0.98 | 2.86 | 3.630 (3) | 136
C7—H7A···Cl2 | 0.99 | 2.86 | 3.394 (2) | 115
C22—H22C···Cl51vi | 0.98 | 2.89 | 3.847 (4) | 165
C22—H22E···Cl41 | 0.98 | 2.90 | 3.859 (3) | 165
C23—H23B···Cl1vi | 0.99 | 2.98 | 3.465 (4) | 111
C23′—H23C···Cl42 | 0.99 | 2.87 | 3.497 (4) | 122
C24—H24C···Cl41 | 0.98 | 2.84 | 3.793 (3) | 164
C24—H24E···Cl51vi | 0.98 | 2.81 | 3.771 (3) | 165
C24—H24F···Cl2Avi | 0.98 | 2.92 | 3.778 (3) | 147
C31′—H31C···Cl31 | 0.99 | 2.95 | 3.434 (5) | 111
C32—H32F···Cl21vii | 0.98 | 2.76 | 3.584 (4) | 142
C33—H33A···Cl32ii | 0.99 | 2.94 | 3.515 (4) | 118
C33′—H33D···Cl41 | 0.99 | 2.98 | 3.630 (5) | 124
C34—H34A···Cl1Bi | 0.98 | 2.93 | 3.556 (3) | 123
C34—H34C···Cl2B | 0.98 | 2.89 | 3.716 (4) | 142
C34—H34A···Cl1Bi | 0.98 | 2.93 | 3.556 (3) | 123
C1L—H1L1···Cl12iii | 0.99 | 2.90 | 3.421 (3) | 114
C2L—H2L2···Cl41 | 0.99 | 2.96 | 3.465 (3) | 113

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Figure 1.

Perspective view of (I) with displacement ellipsoids drawn at the 50% probability level. For clarity, H atoms are omitted and only the symmetry independent molecules are labelled. Atoms without labels are generated by the symmetry operator −x + 1, y, −z + .

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Figure 2.

Perspective view of (II) with displacement ellipsoids drawn at the 50% probability level. For clarity, H atoms are omitted and only one of the two disordered sites of the tetraethylammonium cations are shown.

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Figure 3.

Perspective view of (I) showing the environment of the Cl anion. The contact to the centre of the five-membered ring is drawn as an open dashed bond. H⋯Cl contacts less than 3.5 Å are drawn as dashed lines.

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Figure 4.

Synthesis of [R ₄N]₂[Si₅Cl₁₂] (R = nBu or Et).

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Figure 5.

Transformation of [nBu₄N]₂[Si₅Cl₁₂] (I) to [nBu₄N]₂[Si₆Cl₁₄] (R = R′ = Cl) and [nBu₄N]₂[Si₇Cl₁₆] (R = Cl; R′ = SiCl₃).

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Table 1. Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A
C1—H1B⋯Cl1 | 0.99 | 2.88 | 3.686 (7) | 139
C2—H2A⋯Cl31i | 0.99 | 2.89 | 3.596 (8) | 129
C5—H5A⋯Cl22ii | 0.99 | 2.99 | 3.945 (7) | 163
C9—H9B⋯Cl1 | 0.99 | 2.91 | 3.652 (7) | 132
C1L—H1L1⋯Cl12ii | 0.99 | 2.96 | 3.528 (13) | 119

Symmetry codes: (i) ; (ii) .

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Table 2. Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A
C1—H1B⋯Cl42 | 0.99 | 2.99 | 3.829 (3) | 144
C2—H2C⋯Cl2 | 0.98 | 2.95 | 3.753 (3) | 139
C3—H3A⋯Cl52i | 0.99 | 2.79 | 3.643 (3) | 144
C3—H3B⋯Cl2B ii | 0.99 | 2.98 | 3.804 (3) | 142
C5—H5B⋯Cl22iii | 0.99 | 2.89 | 3.850 (3) | 165
C6—H6B⋯Cl21iii | 0.98 | 2.86 | 3.630 (3) | 136
C7—H7A⋯Cl2 | 0.99 | 2.86 | 3.394 (2) | 115
C22—H22C⋯Cl51iv | 0.98 | 2.89 | 3.847 (4) | 165
C22—H22E⋯Cl41 | 0.98 | 2.90 | 3.859 (3) | 165
C23—H23B⋯Cl1iv | 0.99 | 2.98 | 3.465 (4) | 111
C23′—H23C⋯Cl42 | 0.99 | 2.87 | 3.497 (4) | 122
C24—H24C⋯Cl41 | 0.98 | 2.84 | 3.793 (3) | 164
C24—H24E⋯Cl51iv | 0.98 | 2.81 | 3.771 (3) | 165
C24—H24F⋯Cl2A iv | 0.98 | 2.92 | 3.778 (3) | 147
C31′—H31C⋯Cl31 | 0.99 | 2.95 | 3.434 (5) | 111
C32—H32F⋯Cl21v | 0.98 | 2.76 | 3.584 (4) | 142
C33—H33A⋯Cl32vi | 0.99 | 2.94 | 3.515 (4) | 118
C33′—H33D⋯Cl41 | 0.99 | 2.98 | 3.630 (5) | 124
C34—H34A⋯Cl1B vii | 0.98 | 2.93 | 3.556 (3) | 123
C34—H34C⋯Cl2B | 0.98 | 2.89 | 3.716 (4) | 142
C34—H34A⋯Cl1B vii | 0.98 | 2.93 | 3.556 (3) | 123
C1L—H1L1⋯Cl12i | 0.99 | 2.90 | 3.421 (3) | 114
C2L—H2L2⋯Cl41 | 0.99 | 2.96 | 3.465 (3) | 113

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

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Table 3. Mean values (Å) of Si—Si, Si—Cl bond lengths and Cl/N⋯Cg contacts in the title compounds and related structures

X = Cl for (I) and (II) and X = N for ELAFON and ELAFIH. The row for Si₆Cl₁₂ contains data for dichloride dodecachlorohexasilanes (Tillmann, Lerner & Bolte, 2015 ▸).

Structure | Si—Si | Si—Cl | X⋯Cg
(I) | 2.342 | 2.092 | 2.143
(II) | 2.344 | 2.092 | 2.151
ELAFON | 2.363 | 2.049 | 2.174
ELAFIH | 2.348 | 2.036 | 2.234
Si₆Cl₁₂ | 2.322 | 2.078 | 1.90

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Table 4. Experimental details

| (I) | (II)
Crystal data
Chemical formula | 2C₁₆H₃₆N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂ | 2C₈H₂₀N⁺·2Cl⁻·Si₅Cl₁₀·2CH₂Cl₂
M r | 1220.61 | 996.20
Crystal system, space group | Monoclinic, C2/c | Triclinic, P
Temperature (K) | 173 | 173
a, b, c (Å) | 20.9091 (15), 15.7423 (7), 19.8734 (16) | 10.3596 (4), 13.9612 (5), 16.0205 (6)
α, β, γ (°) | 90, 112.451 (6), 90 | 89.959 (3), 72.484 (3), 79.534 (3)
V (Å³) | 6045.7 (7) | 2169.29 (15)
Z | 4 | 2
Radiation type | Mo Kα | Mo Kα
μ (mm⁻¹) | 0.85 | 1.17
Crystal size (mm) | 0.27 × 0.16 × 0.12 | 0.23 × 0.23 × 0.20
Data collection
Diffractometer | Stoe IPDS II two-circle | Stoe IPDS II two-circle
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001 ▸) | Multi-scan (X-AREA; Stoe & Cie, 2001 ▸)
T min, T max | 0.543, 1.000 | 0.408, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections | 32650, 5699, 4428 | 62962, 13044, 11976
R int | 0.060 | 0.043
(sin θ/λ)max (Å⁻¹) | 0.612 | 0.715
Refinement
R[F ² > 2σ(F ²)], wR(F ²), S | 0.103, 0.199, 1.15 | 0.048, 0.131, 1.08
No. of reflections | 5699 | 13044
No. of parameters | 258 | 409
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained
Δρmax, Δρmin (e Å⁻³) | 1.50, −1.46 | 0.87, −0.84

Computer programs: X-AREA (Stoe & Cie, 2001 ▸), XP in SHELXTL-Plus and SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸) and publCIF (Westrip, 2010 ▸).

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