A structural study of Si₆-ring-containing [Si₆Cl₁₄]^2- chloro­silicates

The crystal structures of four substituted-ammonium dichloride dodeca­chloro­hexa­silanes are presented. Each is crystallized with a different cation and one of the structures contains a benzene solvent mol­ecule: bis­(tetra­ethyl­ammonium) dichloride dodeca­chloro­hexa­silane, 2C₈H₂₀N⁺·2Cl^-·Cl₁₂Si₆, (I), tetra­butyl­ammonium tri­butyl­methyl­ammonium dichloride dodeca­chloro­hexa­silane, C₁₆H₃₆N⁺·C₁₃H₃₀N⁺·2Cl^-·Cl₁₂Si₆, (II), bis­(tetra­butyl­ammonium) di­chlo­ride dodeca­chloro­hexa­silane benzene disolvate, 2C₁₆H₃₆N⁺·2Cl^-·Cl₁₂Si₆·2C₆H₆, (III), and bis­(benzyl­tri­phenyl­phospho­nium) dichloride dodeca­chloro­hexa­silane, 2C₂₅H₂₂P⁺·2Cl^-·Cl₁₂Si₆, (IV). In all four structures, the dodeca­chloro­hexa­silane ring is located on a crystallographic centre of inversion. The geometry of the dichloride dodeca­chloro­hexa­silanes in the different structures is almost the same, irrespective of the cocrystallized cation and solvent. However, the crystal structure of the parent dodeca­chloro­hexa­silane mol­ecule shows that this mol­ecule adopts a chair conformation. In (IV), the P atom and the benzyl group of the cation are disordered over two sites, with a site-occupation factor of 0.560 (5) for the major-occupied site.

S1. Introduction

Thin films of nanocrystalline, microcrystalline and amorphous silicon (Si) are and will be an important element of present and future semiconductors. Until today, such Si films are made through gas-phase deposition of smaller silanes. Those silanes are obtained from the reduction of the corresponding chloro­silanes. A promising approach to improve the manufacturing of Si films are solution-based methods, such as spin, spray or printing processes. Therefore, higher oligosilanes with boiling points significantly higher than their deposition temperatures are in demand. It is expected that silanes consisting of ten or more Si atoms meet those requirements best. Known synthetic routes are much too laborious and expensive to be used in large-scale production, it is a necessity to develop synthesis strategies that give easy access to precursor oligo­chloro­silanes. The amine-induced disproportionation of Si₂Cl₆ leading to Si(SiCl₃)₄ and SiCl₄ has been known for years (Urry, 1970; Meyer-Wegner et al., 2011). Recently, we have established convenient access to chloro­silicates of the type [Si₆Cl₁₄]^2-, [Si₇Cl₁₆]^2- and [Si₈Cl₁₈]^2- by chloride-induced disproportionation of Si₂Cl₆ (Tillmann et al., 2012, 2014). The Si₆ rings of the chloro­silicate are coordinated at both faces by chloride ions and therefore show an inverse sandwich structure. This structural motif was first described by Choi et al. (2001).

In this context, it should be noted that chloro­silicates can be easily transformed into the corresponding silanes by treatment of these compounds with LiAlH₄.

In the course of our investigations, we have prepared a series of complexes, namely [Et₄N]₂Cl₂[Si₆Cl₁₄], (I), [nBu₄N][nBu₃MeN]Cl₂[Si₆Cl₁₄], (II), [nBu₄N]₂Cl₂[Si₆Cl₁₄].2C₆H₆, (III), and [Ph₃BnP]₂Cl₂[Si₆Cl₁₄], (IV), the crystal structures of which we report here.

S2. Experimental

S2.1. Synthesis and crystallization

Synthesis of the chloro­silicates [Et₄N]₂[Si₆Cl₁₄], (I), [nBu₄N][nBu₃MeN][Si₆Cl₁₄], (II), [nBu₄N]₂[Si₆Cl₁₄] . 2C₆H₆, (III), [Ph₃BnP]₂[Si₆Cl₁₄], (IV):

Si₂Cl₆ [0.3 ml, 1.7 mmol for (I); 0.5 ml, 2.9 mmol for (II); 0.3 ml, 1.7 mmol for (IV)] was added to solutions of the related ammonium or phospho­nium chloride, namely [Et₄N]Cl (92 mg, 0.6 mmol) for (I), [nBu₄N]Cl (100 mg, 0.4 mmol) along with nBu₃N {the ammonium salt [nBu₃MeN]Cl is formed from nBu₃N and two molecules of CH₂Cl₂ (Tillmann et al., 2012)} (60 mg, 0.3 mmol) for (II), and [Ph₃BnP]Cl (220 mg, 0.6 mmol) for (IV), all in CH₂Cl₂ (0.3–0.5 ml). When the reaction mixtures were allowed to stand at room temperature, single crystals of the Si₆-ring containing chloro­silicates [Si₆Cl₁₄]^2- grew after a few days. The crystalline yields were (I) < 15%, (II) < 20% and (IV) 40%. In addition, the chloro­silicates [(Cl₃Si)Si₆Cl₁₃]^2-, [1,1-(Cl₃Si)₂Si₆Cl₁₂]^2- and [1,4-(Cl₃Si)₂Si₆Cl₁₂]^2- were obtained as side products of these reactions. Single crystals of (III) were grown from a cooled (279 K) solution of [nBu₄N]₂[Si₆Cl₁₄] (10 mg) after one week.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms in all structures were refined using a riding model, with aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å or methyl­ene C—H = 0.99 Å and with U_iso(H) = 1.5U_eq(C) for methyl H atoms or 1.2U_eq(C) otherwise.

The P atom and the benzyl group of the phospho­nium cation of (IV) are disordered over two sites with a site-occupation factor of 0.560 (5) for the major-occupied site. The C1'—C41 bond was restrained to 1.540 (5) Å. The disordered C atoms were refined isotropically.

S3. Results and discussion

\ Bis(tetra­ethyl­ammonium) dichloride dodeca­chloro­hexasilane, (I) (Fig. 1), crystallizes with discrete cations, anions and half a molecule of dodeca­chloro­hexasilane, which is located on a centre of inversion, in the asymmetric unit. The crystal packing diagram (Fig. 2) shows the arrangement of alternating cations and anions in the unit cell. The hexasilane ring is exactly planar and the two chloride anions are located almost exactly over the centre of the hexasilane ring (cog) (Table 2). The nonbonding Cl···Si distances range from 2.9471(10 (Cl1···Si2) to 3.0285 (10) Å [Cl1···Si1ⁱ; symmetry code: (i) -x+1, -y+1, -z+1].

Tetra­butyl­ammonium tri­butyl­methyl­ammonium dichloride dodeca­chloro­hexasilane, (Figs. 3, 4, 5 and 6), (II), crystallizes with two cations, two anions and two half molecules of dodeca­chloro­hexasilane, which are both located on a centre of inversion, in the asymmetric unit. The hexasilane ring is almost planar and the two chloride anions are located almost exactly over the centre of the hexasilane ring (Table 2). The Cl···Si distances range from 2.9473 (16) [Cl1···Si3ⁱ; symmetry code: (i) -x+1, -y+1, -z] to 3.0837 (16)Å (Si2···Cl1) and from 2.9896 (14) [Cl2···Si5ⁱⁱ; symmetry code: (ii) -x, -y+2, -z+1] to 3.0483 (14) Å [Cl2···Si4ⁱⁱ; symmetry code: (ii) -x, -y+2, -z+1]. The crystal packing (Fig. 7,) shows how the anions and cations are neatly separated.

Bis(tetra­butyl­ammonium) dichloride dodeca­chloro­hexasilane di­benzene solvate, (III) (Figs. 8 and 9) crystallizes with one cation, one anion, half a molecule of dodeca­chloro­hexasilane, which is located on a centre of inversion, and one benzene molecule in the asymmetric unit. The hexasilane ring is essentially planar and the two chloride anions are located almost exactly over the centre of the hexasilane ring (Table 2). The Cl1···Si distances range from 2.9618 (13) [Cl1···Si1ⁱ; symmetry code: (i) -x+1, -y+1, -z+1] to 3.0355 (12) Å (Cl1···Si2). The crystal packing diagram (Fig. 10) shows how the benzene solvent molecule is surrounded by the butyl chains of two cations.

Bis(benzyl­tri­phenyl­phospho­nium) dichloride dodeca­chloro­hexasilane, (IV) (Figs. 11 and 12), crystallizes with one cation, one anion and half a molecule of dodeca­chloro­hexasilane, which is located on a centre of inversion, in the asymmetric unit. The hexasilane ring is almost planar and the two chloride anions are located almost exactly over the centre of the hexasilane ring (Table 2). The Cl···Si distances range from 2.967 (2) [Cl1···Si2ⁱ; symmetry code: (i) -x+1, -y+2, -z] to 3.051 (2) Å (Cl1···Si3ⁱ). The packing diagram (Fig. 13) shows the arrangement of the different entities in the unit cell. Anions and cations are once again neatly separated.

A search in the Cambridge Structural Database (CSD, Version 3.5, with three updates; Groom & Allen, 2014) for the dichloride dodeca­chloro­hexasilane fragment yielded only 2 hits, namely bis­[2-(di­methyl­amino)-N,N,N-tri­methyl­ethanaminium] dichloride dodeca­chloro­hexasilane (CSD refcode LECXIC; Tillmann et al., 2012) and bis­[(N,N,N',N",N"-\ penta­ethyl­diethylenetri­amine-κ³N,N',N")\ chloridodihydridosilicon] dodeca­chloro­cyclo­hexasilane dichloride (NENLOH; Choi et al., 2001). Table 2 lists the most important geometric parameters of the dichloride dodeca­chloro­hexasilane fragments in all six structures. The six-membered ring is planar throughout all structures. The average Si—Si bond length and average Si—Cl bond length are almost identical in all structures. The Cl···Cg distance is also essentially the same in all structures. Only the distance from the Cl anion to the centre of the Si₆ ring shows minor deviations. As a result, it can be stated that the geometric parameters of the dichloride dodeca­chloro­hexasilane fragment is almost invariable. It does not change if it is crystallized with a different anion or solvent.

It is of inter­est to note that the the dichloride dodeca­chloro­hexasilane fragment shows the tendency to crystallize on a crystallographic centre of inversion. The only exception is the structure NENLOH with a complete Cl₁₂Si₆.2Cl^- fragment in the asymmetric unit.

If dodeca­chloro­hexasilane is crystallized with two iodide anions (Dai et al., 2011), the resulting structure, namely bis­(tetra­butyl­ammonium) dodeca­chloro­hexasilane bis­(iodide) di­chloro­methane solvate, shows the same features as the already discussed structures: the six-membered ring is essentially planar (r.m.s. deviation = 0.023Å), the average Si—Si bond is 2.337 (9) Å and the average Si—Cl bond is 2.084 (8) Å. In accordance with the increased size of a iodide anion compared with a chloride anion, the average Si···I distance is increased to 3.29 (3) Å and the distance from the iodide anions to the centre of the ring is 2.328 Å for I1 and 2.304 Å for I2.

If dodeca­chloro­hexasilane is crystallized for itself without any additional ion or solvent, the hexasilane ring is no longer planar but adopts a chair conformation (Dai et al., 2011). In this compound, the average Si—Si bond is slightly longer [2.342 (4) Å] and the average Si—Cl bond is significantly shortened [2.029 (4) Å].

Computing details

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures

	Fig. 1. Perspective view of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. Atoms with suffixes A, B and C were generated using the symmetry code (-x+1, -y+1, -z+1).
	Fig. 2. Packing diagram of (I), viewed in the ac plane. H atoms have been omitted for clarity.
	Fig. 3. Perspective view of the first dichloride dodecachlorohexasilane in the asymmetric unit of (II), with displacement ellipsoids drawn at the 50% probability level. Atoms with suffixes A, B and C were generated using the symmetry code (-x+1, -y+1, -z).
	Fig. 4. Perspective view of the second dichloride dodecachlorohexasilane in the asymmetric unit of (II), with displacement ellipsoids drawn at the 50% probability level. Atoms with suffixes A, B and C were generated using the symmetry code (-x, -y+2, -z+1).
	Fig. 5. Perspective view of the tetrabutylammonium cation of (II), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 6. Perspective view of the tributylmethylammonium cation of (II), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 7. Packing diagram of (II), viewed in the ab plane. H atoms have been omitted for clarity.
	Fig. 8. Perspective view of dichloride dodecachlorohexasilane (III), with displacement ellipsoids drawn at the 50% probability level. Atoms with suffixes A, B and C were generated using the symmetry code (-x+1, -y+1, -z+1).
	Fig. 9. Perspective view of the tetrabutylammonium cation of (III), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 10. Packing diagram of (III), viewed in the bc plane. H atoms have been omitted for clarity.
	Fig. 11. Perspective view of dichloride dodecachlorohexasilane of (IV), with displacement ellipsoids drawn at the 50% probability level. Atoms with suffixes A, B and C were generated using the symmetry code (-x+1, -y+2, -z).
	Fig. 12. Perspective view of the cation of (IV), with displacement ellipsoids drawn at the 50% probability level. H atoms and the minor-occupied sites of the disordered atoms have been omitted for clarity.
	Fig. 13. Packing diagram of (IV), viewed in the bc plane. H atoms have been omitted for clarity.

(I) Bis(tetraethylammonium) dichloride dodecachlorohexasilane

Crystal data

2C8H20N^+·2Cl^−·Cl12Si6	Dx = 1.540 Mg m^−3
Mr = 925.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 26169 reflections
a = 13.6864 (5) Å	θ = 2.3–26.1°
b = 20.6309 (9) Å	µ = 1.16 mm^−1
c = 14.1328 (8) Å	T = 173 K
V = 3990.6 (3) Å^3	Needle, colourless
Z = 4	0.26 × 0.03 × 0.03 mm
F(000) = 1888

Data collection

Stoe IPDS II two-circle diffractometer	3004 reflections with I > 2σ(I)
ω scans	Rint = 0.105
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θmax = 25.7°, θmin = 2.3°
	h = −16→14
42017 measured reflections	k = −24→24
3747 independent reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0304P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3747 reflections	Δρmax = 0.37 e Å^−3
172 parameters	Δρmin = −0.24 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.52334 (5)	0.53665 (3)	0.61863 (4)	0.02761 (15)
Si1	0.60333 (5)	0.57854 (3)	0.43229 (5)	0.02563 (17)
Si2	0.66489 (5)	0.47991 (3)	0.48509 (5)	0.02603 (17)
Si3	0.56306 (6)	0.40302 (3)	0.55310 (5)	0.02525 (16)
Cl11	0.64343 (6)	0.59070 (4)	0.29179 (5)	0.04215 (19)
Cl12	0.67825 (6)	0.65384 (3)	0.49852 (5)	0.03832 (18)
Cl21	0.73734 (6)	0.43561 (4)	0.37356 (6)	0.0430 (2)
Cl22	0.77618 (6)	0.50021 (4)	0.57992 (6)	0.04176 (19)
Cl31	0.58281 (6)	0.31686 (3)	0.47745 (5)	0.03665 (17)
Cl32	0.61633 (6)	0.37946 (4)	0.68617 (5)	0.04084 (19)
N1	0.49084 (17)	0.14614 (11)	0.63519 (16)	0.0284 (5)
C1	0.5738 (2)	0.14210 (14)	0.7064 (2)	0.0315 (6)
H1A	0.5454	0.1343	0.7698	0.038*
H1B	0.6147	0.1041	0.6904	0.038*
C2	0.6389 (3)	0.20079 (15)	0.7121 (3)	0.0465 (8)
H2A	0.6898	0.1935	0.7597	0.070*
H2B	0.6693	0.2084	0.6503	0.070*
H2C	0.5998	0.2387	0.7299	0.070*
C3	0.4237 (2)	0.08845 (14)	0.6494 (2)	0.0337 (7)
H3A	0.3966	0.0904	0.7143	0.040*
H3B	0.3682	0.0923	0.6047	0.040*
C4	0.4706 (2)	0.02304 (14)	0.6355 (2)	0.0367 (7)
H4A	0.4220	−0.0111	0.6460	0.055*
H4B	0.4960	0.0198	0.5708	0.055*
H4C	0.5244	0.0179	0.6806	0.055*
C5	0.4321 (2)	0.20764 (15)	0.6481 (2)	0.0388 (7)
H5A	0.3770	0.2071	0.6028	0.047*
H5B	0.4741	0.2451	0.6319	0.047*
C6	0.3915 (3)	0.21771 (18)	0.7471 (3)	0.0541 (9)
H6A	0.3547	0.2584	0.7492	0.081*
H6B	0.3482	0.1816	0.7634	0.081*
H6C	0.4455	0.2196	0.7926	0.081*
C7	0.5352 (2)	0.14618 (15)	0.53629 (19)	0.0356 (7)
H7A	0.5789	0.1842	0.5307	0.043*
H7B	0.5762	0.1069	0.5295	0.043*
C8	0.4634 (3)	0.14792 (18)	0.4553 (2)	0.0507 (9)
H8A	0.4991	0.1478	0.3952	0.076*
H8B	0.4209	0.1098	0.4584	0.076*
H8C	0.4237	0.1873	0.4596	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0308 (3)	0.0288 (3)	0.0232 (3)	0.0012 (3)	−0.0017 (3)	−0.0050 (3)
Si1	0.0253 (4)	0.0243 (4)	0.0274 (4)	−0.0010 (3)	0.0001 (3)	−0.0008 (3)
Si2	0.0205 (4)	0.0244 (4)	0.0332 (4)	0.0002 (3)	−0.0004 (3)	−0.0035 (3)
Si3	0.0263 (4)	0.0224 (4)	0.0271 (4)	0.0014 (3)	−0.0019 (3)	0.0001 (3)
Cl11	0.0449 (5)	0.0500 (4)	0.0316 (4)	−0.0045 (4)	0.0096 (3)	0.0062 (3)
Cl12	0.0347 (4)	0.0286 (3)	0.0517 (5)	−0.0070 (3)	−0.0046 (3)	−0.0052 (3)
Cl21	0.0324 (4)	0.0406 (4)	0.0559 (5)	−0.0017 (3)	0.0159 (4)	−0.0152 (4)
Cl22	0.0298 (4)	0.0386 (4)	0.0569 (5)	−0.0013 (3)	−0.0167 (3)	−0.0021 (3)
Cl31	0.0443 (4)	0.0223 (3)	0.0434 (4)	0.0019 (3)	0.0048 (3)	−0.0037 (3)
Cl32	0.0476 (5)	0.0396 (4)	0.0353 (4)	0.0050 (4)	−0.0123 (3)	0.0068 (3)
N1	0.0254 (13)	0.0284 (12)	0.0314 (12)	0.0004 (10)	0.0003 (10)	0.0086 (10)
C1	0.0298 (16)	0.0273 (14)	0.0373 (15)	−0.0030 (12)	−0.0055 (13)	0.0092 (12)
C2	0.043 (2)	0.0377 (17)	0.059 (2)	−0.0112 (15)	−0.0122 (16)	0.0102 (15)
C3	0.0251 (15)	0.0395 (16)	0.0363 (15)	−0.0103 (13)	−0.0040 (12)	0.0116 (12)
C4	0.0444 (19)	0.0311 (15)	0.0348 (15)	−0.0101 (14)	0.0000 (14)	0.0007 (12)
C5	0.0370 (18)	0.0378 (16)	0.0416 (17)	0.0092 (14)	−0.0023 (14)	0.0086 (13)
C6	0.055 (2)	0.051 (2)	0.056 (2)	0.0166 (18)	0.0111 (18)	−0.0025 (17)
C7	0.0416 (19)	0.0339 (15)	0.0313 (15)	−0.0011 (13)	0.0085 (13)	0.0086 (12)
C8	0.063 (3)	0.057 (2)	0.0322 (17)	−0.0051 (18)	−0.0046 (16)	0.0056 (15)

Geometric parameters (Å, º)

Si1—Cl11	2.0753 (10)	C2—H2C	0.9800
Si1—Cl12	2.0836 (10)	C3—C4	1.507 (4)
Si1—Si3^i	2.3181 (11)	C3—H3A	0.9900
Si1—Si2	2.3254 (10)	C3—H3B	0.9900
Si2—Cl22	2.0716 (10)	C4—H4A	0.9800
Si2—Cl21	2.0744 (10)	C4—H4B	0.9800
Si2—Si3	2.3200 (11)	C4—H4C	0.9800
Si3—Cl32	2.0747 (10)	C5—C6	1.520 (5)
Si3—Cl31	2.0919 (10)	C5—H5A	0.9900
Si3—Si1^i	2.3181 (11)	C5—H5B	0.9900
N1—C5	1.513 (4)	C6—H6A	0.9800
N1—C3	1.517 (4)	C6—H6B	0.9800
N1—C1	1.520 (4)	C6—H6C	0.9800
N1—C7	1.524 (3)	C7—C8	1.509 (4)
C1—C2	1.505 (4)	C7—H7A	0.9900
C1—H1A	0.9900	C7—H7B	0.9900
C1—H1B	0.9900	C8—H8A	0.9800
C2—H2A	0.9800	C8—H8B	0.9800
C2—H2B	0.9800	C8—H8C	0.9800
Cl11—Si1—Cl12	102.10 (4)	C4—C3—N1	115.3 (2)
Cl11—Si1—Si3^i	108.98 (4)	C4—C3—H3A	108.5
Cl12—Si1—Si3^i	108.73 (4)	N1—C3—H3A	108.5
Cl11—Si1—Si2	108.48 (4)	C4—C3—H3B	108.5
Cl12—Si1—Si2	109.27 (4)	N1—C3—H3B	108.5
Si3^i—Si1—Si2	118.10 (4)	H3A—C3—H3B	107.5
Cl22—Si2—Cl21	103.26 (5)	C3—C4—H4A	109.5
Cl22—Si2—Si3	108.17 (4)	C3—C4—H4B	109.5
Cl21—Si2—Si3	107.50 (4)	H4A—C4—H4B	109.5
Cl22—Si2—Si1	107.28 (4)	C3—C4—H4C	109.5
Cl21—Si2—Si1	108.35 (4)	H4A—C4—H4C	109.5
Si3—Si2—Si1	120.90 (4)	H4B—C4—H4C	109.5
Cl32—Si3—Cl31	102.64 (4)	N1—C5—C6	114.8 (2)
Cl32—Si3—Si1^i	107.63 (4)	N1—C5—H5A	108.6
Cl31—Si3—Si1^i	108.17 (4)	C6—C5—H5A	108.6
Cl32—Si3—Si2	108.95 (4)	N1—C5—H5B	108.6
Cl31—Si3—Si2	106.96 (4)	C6—C5—H5B	108.6
Si1^i—Si3—Si2	120.99 (4)	H5A—C5—H5B	107.5
C5—N1—C3	108.7 (2)	C5—C6—H6A	109.5
C5—N1—C1	111.3 (2)	C5—C6—H6B	109.5
C3—N1—C1	108.8 (2)	H6A—C6—H6B	109.5
C5—N1—C7	108.8 (2)	C5—C6—H6C	109.5
C3—N1—C7	111.3 (2)	H6A—C6—H6C	109.5
C1—N1—C7	108.0 (2)	H6B—C6—H6C	109.5
C2—C1—N1	115.7 (2)	C8—C7—N1	115.9 (3)
C2—C1—H1A	108.4	C8—C7—H7A	108.3
N1—C1—H1A	108.4	N1—C7—H7A	108.3
C2—C1—H1B	108.4	C8—C7—H7B	108.3
N1—C1—H1B	108.4	N1—C7—H7B	108.3
H1A—C1—H1B	107.4	H7A—C7—H7B	107.4
C1—C2—H2A	109.5	C7—C8—H8A	109.5
C1—C2—H2B	109.5	C7—C8—H8B	109.5
H2A—C2—H2B	109.5	H8A—C8—H8B	109.5
C1—C2—H2C	109.5	C7—C8—H8C	109.5
H2A—C2—H2C	109.5	H8A—C8—H8C	109.5
H2B—C2—H2C	109.5	H8B—C8—H8C	109.5
C5—N1—C1—C2	−51.4 (4)	C3—N1—C5—C6	64.5 (3)
C3—N1—C1—C2	−171.1 (3)	C1—N1—C5—C6	−55.3 (4)
C7—N1—C1—C2	68.0 (3)	C7—N1—C5—C6	−174.2 (3)
C5—N1—C3—C4	178.0 (2)	C5—N1—C7—C8	−60.9 (3)
C1—N1—C3—C4	−60.7 (3)	C3—N1—C7—C8	58.8 (3)
C7—N1—C3—C4	58.2 (3)	C1—N1—C7—C8	178.2 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

(II) Tetrabutylammonium tributylmethylammonium dichloride dodecachlorohexasilane

Crystal data

C16H36N^+·C13H30N^+·2Cl^−·Cl12Si6	Z = 2
Mr = 1107.67	F(000) = 1152
Triclinic, P1	Dx = 1.374 Mg m^−3
a = 11.1071 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.3992 (12) Å	Cell parameters from 23095 reflections
c = 16.7434 (12) Å	θ = 3.1–26.0°
α = 89.672 (6)°	µ = 0.88 mm^−1
β = 88.689 (6)°	T = 173 K
γ = 89.854 (6)°	Plate, colourless
V = 2677.1 (4) Å^3	0.15 × 0.13 × 0.04 mm

Data collection

Stoe IPDS II two-circle diffractometer	6918 reflections with I > 2σ(I)
ω scans	Rint = 0.071
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θmax = 25.7°, θmin = 3.3°
	h = −13→13
32914 measured reflections	k = −17→17
10052 independent reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0716P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
10052 reflections	Δρmax = 1.00 e Å^−3
460 parameters	Δρmin = −0.37 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.59130 (9)	0.44934 (8)	0.08400 (6)	0.0431 (2)
Si1	0.38480 (12)	0.36385 (9)	0.00184 (8)	0.0473 (3)
Si2	0.31960 (11)	0.49176 (9)	0.07561 (8)	0.0450 (3)
Si3	0.44345 (12)	0.62216 (9)	0.07842 (7)	0.0448 (3)
Cl11	0.39893 (15)	0.24881 (9)	0.07672 (9)	0.0728 (4)
Cl12	0.24724 (13)	0.32432 (11)	−0.07179 (10)	0.0761 (4)
Cl21	0.28594 (13)	0.44869 (11)	0.19303 (8)	0.0670 (4)
Cl22	0.14895 (11)	0.52832 (10)	0.04044 (9)	0.0645 (4)
Cl31	0.49314 (14)	0.64296 (10)	0.19628 (8)	0.0674 (4)
Cl32	0.33795 (12)	0.73898 (9)	0.05674 (9)	0.0645 (4)
Cl2	0.08954 (8)	0.96573 (6)	0.40564 (5)	0.0318 (2)
Si4	−0.15792 (9)	0.90659 (7)	0.45815 (6)	0.0299 (2)
Si5	−0.00936 (9)	0.84674 (7)	0.53850 (7)	0.0312 (2)
Si6	0.15065 (9)	0.93762 (7)	0.57871 (6)	0.0299 (2)
Cl41	−0.17337 (11)	0.82655 (8)	0.35615 (7)	0.0506 (3)
Cl42	−0.32296 (9)	0.88148 (7)	0.51580 (7)	0.0426 (2)
Cl51	0.06109 (10)	0.72997 (7)	0.48056 (8)	0.0490 (3)
Cl52	−0.09220 (10)	0.79026 (8)	0.63974 (7)	0.0484 (3)
Cl61	0.31183 (8)	0.87639 (7)	0.54097 (7)	0.0416 (2)
Cl62	0.16165 (10)	0.92755 (8)	0.70182 (6)	0.0462 (3)
N1	0.1656 (3)	0.5466 (2)	0.7100 (2)	0.0420 (8)
C1	0.2961 (4)	0.5686 (3)	0.7224 (3)	0.0461 (10)
H1A	0.3109	0.5653	0.7805	0.055*
H1B	0.3452	0.5192	0.6966	0.055*
C2	0.3407 (5)	0.6598 (4)	0.6921 (4)	0.0699 (15)
H2A	0.2999	0.7110	0.7213	0.084*
H2B	0.3236	0.6666	0.6346	0.084*
C3	0.4773 (5)	0.6637 (5)	0.7048 (5)	0.0809 (18)
H3A	0.4929	0.6460	0.7608	0.097*
H3B	0.5167	0.6168	0.6700	0.097*
C4	0.5329 (7)	0.7527 (6)	0.6887 (6)	0.111 (3)
H4A	0.6194	0.7485	0.6984	0.167*
H4B	0.5205	0.7704	0.6329	0.167*
H4C	0.4966	0.7997	0.7239	0.167*
C5	0.1431 (4)	0.4537 (3)	0.7504 (3)	0.0501 (11)
H5A	0.2049	0.4092	0.7307	0.060*
H5B	0.1542	0.4612	0.8085	0.060*
C6	0.0210 (5)	0.4121 (4)	0.7381 (4)	0.0619 (13)
H6A	0.0137	0.3938	0.6815	0.074*
H6B	−0.0421	0.4588	0.7504	0.074*
C7	0.0025 (6)	0.3271 (4)	0.7918 (4)	0.0699 (16)
H7A	0.0707	0.2835	0.7837	0.084*
H7B	0.0010	0.3466	0.8484	0.084*
C8	−0.1136 (6)	0.2786 (5)	0.7736 (5)	0.096 (2)
H8A	−0.1235	0.2244	0.8088	0.144*
H8B	−0.1812	0.3215	0.7824	0.144*
H8C	−0.1116	0.2585	0.7178	0.144*
C9	0.0929 (5)	0.6396 (4)	0.8346 (3)	0.0571 (13)
H9A	0.0677	0.5837	0.8652	0.068*
H9B	0.1776	0.6533	0.8474	0.068*
C10	0.0836 (4)	0.6213 (3)	0.7456 (3)	0.0487 (11)
H10A	0.1003	0.6802	0.7167	0.058*
H10B	−0.0007	0.6040	0.7349	0.058*
C11	0.0137 (5)	0.7209 (4)	0.8584 (3)	0.0617 (13)
H11A	0.0364	0.7753	0.8250	0.074*
H11B	−0.0710	0.7054	0.8471	0.074*
C12	0.0221 (6)	0.7467 (5)	0.9446 (4)	0.0827 (19)
H12A	−0.0312	0.7996	0.9560	0.124*
H12B	−0.0022	0.6937	0.9782	0.124*
H12C	0.1053	0.7637	0.9561	0.124*
C13	0.1397 (4)	0.5420 (4)	0.6222 (3)	0.0492 (11)
H13A	0.1508	0.6050	0.5991	0.059*
H13B	0.0538	0.5255	0.6166	0.059*
C14	0.2150 (4)	0.4744 (3)	0.5725 (3)	0.0497 (11)
H14A	0.3009	0.4919	0.5749	0.060*
H14B	0.2061	0.4111	0.5952	0.060*
C15	0.1768 (5)	0.4743 (4)	0.4862 (3)	0.0596 (13)
H15A	0.0925	0.4524	0.4840	0.072*
H15B	0.1792	0.5387	0.4653	0.072*
C16	0.2536 (6)	0.4147 (4)	0.4337 (4)	0.0732 (16)
H16A	0.2243	0.4177	0.3789	0.110*
H16B	0.3369	0.4368	0.4344	0.110*
H16C	0.2502	0.3504	0.4530	0.110*
N2	0.5719 (3)	0.0642 (2)	0.7209 (2)	0.0394 (8)
C17	0.6715 (4)	−0.0021 (3)	0.7442 (3)	0.0424 (10)
H17A	0.6343	−0.0571	0.7705	0.051*
H17B	0.7131	−0.0239	0.6947	0.051*
C18	0.7639 (4)	0.0363 (3)	0.7984 (3)	0.0486 (11)
H18A	0.7229	0.0622	0.8465	0.058*
H18B	0.8072	0.0876	0.7707	0.058*
C19	0.8538 (5)	−0.0365 (4)	0.8238 (3)	0.0616 (13)
H19A	0.8871	−0.0681	0.7757	0.074*
H19B	0.8121	−0.0836	0.8575	0.074*
C20	0.9562 (5)	0.0049 (5)	0.8699 (4)	0.0777 (17)
H20A	1.0122	−0.0445	0.8851	0.117*
H20B	0.9988	0.0508	0.8363	0.117*
H20C	0.9238	0.0352	0.9181	0.117*
C21	0.4947 (4)	0.0929 (3)	0.7921 (3)	0.0456 (11)
H21A	0.5445	0.1311	0.8275	0.055*
H21B	0.4288	0.1329	0.7728	0.055*
C22	0.4403 (5)	0.0161 (4)	0.8409 (3)	0.0593 (13)
H22A	0.5048	−0.0198	0.8669	0.071*
H22B	0.3963	−0.0265	0.8057	0.071*
C23	0.3539 (7)	0.0549 (5)	0.9043 (5)	0.094 (2)
H23A	0.3973	0.1003	0.9372	0.112*
H23B	0.2878	0.0884	0.8777	0.112*
C24	0.3015 (9)	−0.0185 (7)	0.9575 (6)	0.139 (4)
H24A	0.2468	0.0100	0.9970	0.209*
H24B	0.2568	−0.0629	0.9254	0.209*
H24C	0.3663	−0.0511	0.9849	0.209*
C25	0.6287 (4)	0.1505 (3)	0.6825 (3)	0.0395 (9)
H25A	0.6664	0.1872	0.7250	0.047*
H25B	0.6938	0.1302	0.6452	0.047*
C26	0.5451 (4)	0.2132 (3)	0.6378 (3)	0.0413 (10)
H26A	0.4771	0.2318	0.6735	0.050*
H26B	0.5117	0.1790	0.5922	0.050*
C27	0.6099 (4)	0.2990 (3)	0.6071 (3)	0.0474 (11)
H27A	0.6412	0.3340	0.6529	0.057*
H27B	0.6794	0.2801	0.5728	0.057*
C28	0.5285 (6)	0.3603 (4)	0.5604 (5)	0.085 (2)
H28A	0.5732	0.4150	0.5415	0.128*
H28B	0.4986	0.3261	0.5146	0.128*
H28C	0.4604	0.3799	0.5946	0.128*
C29	0.4966 (4)	0.0162 (3)	0.6606 (3)	0.0502 (11)
H29A	0.5474	−0.0020	0.6148	0.075*
H29B	0.4597	−0.0392	0.6850	0.075*
H29C	0.4332	0.0585	0.6428	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0475 (6)	0.0563 (6)	0.0260 (5)	0.0126 (5)	−0.0114 (4)	−0.0027 (4)
Si1	0.0545 (7)	0.0497 (7)	0.0378 (7)	0.0050 (6)	−0.0067 (6)	−0.0025 (5)
Si2	0.0441 (6)	0.0556 (7)	0.0351 (7)	0.0119 (5)	−0.0019 (5)	−0.0001 (5)
Si3	0.0526 (7)	0.0492 (7)	0.0328 (7)	0.0131 (5)	−0.0059 (5)	−0.0099 (5)
Cl11	0.1013 (11)	0.0531 (7)	0.0637 (9)	−0.0010 (7)	0.0026 (8)	0.0097 (6)
Cl12	0.0676 (8)	0.0844 (10)	0.0772 (11)	−0.0120 (7)	−0.0200 (7)	−0.0134 (8)
Cl21	0.0720 (8)	0.0856 (9)	0.0426 (7)	0.0163 (7)	0.0115 (6)	0.0092 (6)
Cl22	0.0443 (6)	0.0762 (9)	0.0731 (9)	0.0147 (6)	−0.0055 (6)	0.0057 (7)
Cl31	0.0918 (10)	0.0765 (9)	0.0345 (7)	0.0136 (7)	−0.0093 (6)	−0.0228 (6)
Cl32	0.0670 (8)	0.0541 (7)	0.0725 (9)	0.0236 (6)	−0.0066 (7)	−0.0086 (6)
Cl2	0.0310 (4)	0.0381 (5)	0.0262 (5)	0.0054 (4)	0.0025 (4)	−0.0007 (4)
Si4	0.0305 (5)	0.0313 (5)	0.0281 (6)	0.0034 (4)	−0.0048 (4)	−0.0016 (4)
Si5	0.0303 (5)	0.0284 (5)	0.0351 (6)	0.0029 (4)	−0.0039 (4)	0.0047 (4)
Si6	0.0285 (5)	0.0339 (5)	0.0274 (6)	0.0048 (4)	−0.0032 (4)	0.0034 (4)
Cl41	0.0587 (7)	0.0520 (6)	0.0416 (6)	0.0033 (5)	−0.0104 (5)	−0.0158 (5)
Cl42	0.0314 (5)	0.0497 (6)	0.0467 (6)	−0.0051 (4)	−0.0009 (4)	0.0023 (5)
Cl51	0.0506 (6)	0.0304 (5)	0.0662 (8)	0.0108 (4)	−0.0047 (5)	−0.0046 (5)
Cl52	0.0494 (6)	0.0510 (6)	0.0449 (6)	−0.0063 (5)	−0.0049 (5)	0.0205 (5)
Cl61	0.0318 (5)	0.0470 (6)	0.0461 (6)	0.0131 (4)	−0.0045 (4)	−0.0026 (4)
Cl62	0.0490 (6)	0.0627 (7)	0.0272 (5)	0.0022 (5)	−0.0072 (4)	0.0077 (5)
N1	0.0411 (19)	0.046 (2)	0.039 (2)	0.0053 (15)	−0.0086 (16)	0.0064 (16)
C1	0.044 (2)	0.054 (3)	0.041 (3)	0.006 (2)	−0.011 (2)	0.003 (2)
C2	0.063 (3)	0.061 (3)	0.086 (4)	0.003 (3)	−0.007 (3)	0.006 (3)
C3	0.052 (3)	0.096 (5)	0.095 (5)	−0.011 (3)	0.003 (3)	0.004 (4)
C4	0.083 (5)	0.105 (6)	0.145 (8)	−0.008 (4)	−0.004 (5)	0.047 (5)
C5	0.054 (3)	0.053 (3)	0.043 (3)	0.005 (2)	−0.003 (2)	0.007 (2)
C6	0.060 (3)	0.063 (3)	0.062 (4)	−0.008 (2)	0.008 (3)	−0.004 (3)
C7	0.082 (4)	0.059 (3)	0.068 (4)	−0.016 (3)	0.021 (3)	−0.009 (3)
C8	0.095 (5)	0.085 (5)	0.108 (6)	−0.040 (4)	0.022 (4)	−0.021 (4)
C9	0.061 (3)	0.062 (3)	0.048 (3)	0.011 (2)	−0.005 (2)	0.010 (2)
C10	0.046 (2)	0.053 (3)	0.047 (3)	0.009 (2)	−0.009 (2)	0.006 (2)
C11	0.064 (3)	0.064 (3)	0.057 (3)	0.011 (3)	0.004 (3)	0.006 (3)
C12	0.098 (5)	0.079 (4)	0.070 (4)	0.026 (4)	0.014 (4)	0.001 (3)
C13	0.047 (2)	0.061 (3)	0.040 (3)	0.008 (2)	−0.013 (2)	0.003 (2)
C14	0.045 (2)	0.056 (3)	0.048 (3)	0.006 (2)	−0.010 (2)	0.000 (2)
C15	0.054 (3)	0.072 (3)	0.054 (3)	0.007 (2)	−0.011 (2)	−0.004 (3)
C16	0.078 (4)	0.080 (4)	0.062 (4)	0.001 (3)	−0.004 (3)	−0.018 (3)
N2	0.0354 (17)	0.0396 (18)	0.043 (2)	−0.0004 (14)	0.0024 (15)	−0.0121 (15)
C17	0.044 (2)	0.035 (2)	0.048 (3)	0.0015 (17)	0.002 (2)	0.0000 (19)
C18	0.054 (3)	0.047 (3)	0.045 (3)	0.004 (2)	−0.003 (2)	0.000 (2)
C19	0.055 (3)	0.074 (3)	0.056 (3)	0.006 (3)	−0.004 (2)	0.005 (3)
C20	0.066 (4)	0.094 (4)	0.074 (4)	0.015 (3)	−0.019 (3)	0.010 (3)
C21	0.041 (2)	0.050 (3)	0.045 (3)	0.0023 (19)	0.009 (2)	−0.010 (2)
C22	0.056 (3)	0.059 (3)	0.062 (3)	0.000 (2)	0.014 (3)	0.004 (3)
C23	0.092 (5)	0.096 (5)	0.090 (5)	0.011 (4)	0.049 (4)	0.019 (4)
C24	0.129 (7)	0.160 (9)	0.125 (8)	0.004 (6)	0.064 (6)	0.055 (7)
C25	0.033 (2)	0.041 (2)	0.045 (3)	−0.0025 (17)	0.0014 (18)	−0.0043 (18)
C26	0.037 (2)	0.049 (2)	0.038 (2)	0.0022 (18)	−0.0032 (18)	−0.0097 (19)
C27	0.046 (2)	0.048 (2)	0.048 (3)	0.0041 (19)	0.007 (2)	−0.005 (2)
C28	0.086 (4)	0.065 (4)	0.105 (6)	0.003 (3)	−0.021 (4)	0.024 (4)
C29	0.052 (3)	0.046 (3)	0.053 (3)	−0.005 (2)	−0.007 (2)	−0.012 (2)

Geometric parameters (Å, º)

Si1—Cl12	2.068 (2)	C12—H12B	0.9800
Si1—Cl11	2.0795 (19)	C12—H12C	0.9800
Si1—Si3^i	2.3167 (19)	C13—C14	1.521 (7)
Si1—Si2	2.3282 (18)	C13—H13A	0.9900
Si2—Cl22	2.0637 (17)	C13—H13B	0.9900
Si2—Cl21	2.0840 (18)	C14—C15	1.516 (7)
Si2—Si3	2.332 (2)	C14—H14A	0.9900
Si3—Cl32	2.0824 (17)	C14—H14B	0.9900
Si3—Cl31	2.0848 (18)	C15—C16	1.485 (8)
Si3—Si1^i	2.3167 (19)	C15—H15A	0.9900
Si4—Cl41	2.0764 (16)	C15—H15B	0.9900
Si4—Cl42	2.0835 (14)	C16—H16A	0.9800
Si4—Si5	2.3144 (15)	C16—H16B	0.9800
Si4—Si6^ii	2.3242 (14)	C16—H16C	0.9800
Si5—Cl52	2.0731 (15)	N2—C29	1.498 (6)
Si5—Cl51	2.0875 (15)	N2—C21	1.511 (5)
Si5—Si6	2.3241 (15)	N2—C17	1.517 (5)
Si6—Cl62	2.0719 (15)	N2—C25	1.526 (5)
Si6—Cl61	2.0805 (13)	C17—C18	1.495 (7)
Si6—Si4^ii	2.3242 (14)	C17—H17A	0.9900
N1—C1	1.503 (6)	C17—H17B	0.9900
N1—C13	1.507 (6)	C18—C19	1.512 (7)
N1—C5	1.515 (6)	C18—H18A	0.9900
N1—C10	1.522 (6)	C18—H18B	0.9900
C1—C2	1.489 (7)	C19—C20	1.514 (8)
C1—H1A	0.9900	C19—H19A	0.9900
C1—H1B	0.9900	C19—H19B	0.9900
C2—C3	1.537 (8)	C20—H20A	0.9800
C2—H2A	0.9900	C20—H20B	0.9800
C2—H2B	0.9900	C20—H20C	0.9800
C3—C4	1.445 (10)	C21—C22	1.491 (7)
C3—H3A	0.9900	C21—H21A	0.9900
C3—H3B	0.9900	C21—H21B	0.9900
C4—H4A	0.9800	C22—C23	1.523 (8)
C4—H4B	0.9800	C22—H22A	0.9900
C4—H4C	0.9800	C22—H22B	0.9900
C5—C6	1.503 (7)	C23—C24	1.490 (10)
C5—H5A	0.9900	C23—H23A	0.9900
C5—H5B	0.9900	C23—H23B	0.9900
C6—C7	1.526 (8)	C24—H24A	0.9800
C6—H6A	0.9900	C24—H24B	0.9800
C6—H6B	0.9900	C24—H24C	0.9800
C7—C8	1.505 (9)	C25—C26	1.503 (6)
C7—H7A	0.9900	C25—H25A	0.9900
C7—H7B	0.9900	C25—H25B	0.9900
C8—H8A	0.9800	C26—C27	1.512 (6)
C8—H8B	0.9800	C26—H26A	0.9900
C8—H8C	0.9800	C26—H26B	0.9900
C9—C11	1.512 (7)	C27—C28	1.493 (7)
C9—C10	1.521 (7)	C27—H27A	0.9900
C9—H9A	0.9900	C27—H27B	0.9900
C9—H9B	0.9900	C28—H28A	0.9800
C10—H10A	0.9900	C28—H28B	0.9800
C10—H10B	0.9900	C28—H28C	0.9800
C11—C12	1.498 (8)	C29—H29A	0.9800
C11—H11A	0.9900	C29—H29B	0.9800
C11—H11B	0.9900	C29—H29C	0.9800
C12—H12A	0.9800
Cl12—Si1—Cl11	101.77 (9)	C11—C12—H12C	109.5
Cl12—Si1—Si3^i	106.74 (8)	H12A—C12—H12C	109.5
Cl11—Si1—Si3^i	110.19 (8)	H12B—C12—H12C	109.5
Cl12—Si1—Si2	108.28 (8)	N1—C13—C14	116.8 (4)
Cl11—Si1—Si2	109.64 (8)	N1—C13—H13A	108.1
Si3^i—Si1—Si2	118.80 (7)	C14—C13—H13A	108.1
Cl22—Si2—Cl21	101.33 (8)	N1—C13—H13B	108.1
Cl22—Si2—Si1	108.93 (8)	C14—C13—H13B	108.1
Cl21—Si2—Si1	108.37 (8)	H13A—C13—H13B	107.3
Cl22—Si2—Si3	110.44 (7)	C15—C14—C13	111.3 (4)
Cl21—Si2—Si3	108.08 (8)	C15—C14—H14A	109.4
Si1—Si2—Si3	118.31 (7)	C13—C14—H14A	109.4
Cl32—Si3—Cl31	101.92 (7)	C15—C14—H14B	109.4
Cl32—Si3—Si1^i	106.80 (8)	C13—C14—H14B	109.4
Cl31—Si3—Si1^i	107.69 (8)	H14A—C14—H14B	108.0
Cl32—Si3—Si2	108.16 (7)	C16—C15—C14	113.5 (5)
Cl31—Si3—Si2	108.00 (8)	C16—C15—H15A	108.9
Si1^i—Si3—Si2	122.40 (7)	C14—C15—H15A	108.9
Cl41—Si4—Cl42	101.29 (6)	C16—C15—H15B	108.9
Cl41—Si4—Si5	110.23 (6)	C14—C15—H15B	108.9
Cl42—Si4—Si5	107.37 (6)	H15A—C15—H15B	107.7
Cl41—Si4—Si6^ii	108.92 (6)	C15—C16—H16A	109.5
Cl42—Si4—Si6^ii	108.34 (6)	C15—C16—H16B	109.5
Si5—Si4—Si6^ii	119.16 (6)	H16A—C16—H16B	109.5
Cl52—Si5—Cl51	102.76 (6)	C15—C16—H16C	109.5
Cl52—Si5—Si4	108.00 (6)	H16A—C16—H16C	109.5
Cl51—Si5—Si4	106.91 (6)	H16B—C16—H16C	109.5
Cl52—Si5—Si6	108.15 (6)	C29—N2—C21	110.2 (3)
Cl51—Si5—Si6	108.12 (6)	C29—N2—C17	107.6 (3)
Si4—Si5—Si6	121.36 (6)	C21—N2—C17	112.0 (3)
Cl62—Si6—Cl61	101.83 (6)	C29—N2—C25	109.1 (4)
Cl62—Si6—Si5	108.34 (6)	C21—N2—C25	109.2 (3)
Cl61—Si6—Si5	109.30 (6)	C17—N2—C25	108.7 (3)
Cl62—Si6—Si4^ii	108.88 (6)	C18—C17—N2	115.8 (3)
Cl61—Si6—Si4^ii	107.63 (6)	C18—C17—H17A	108.3
Si5—Si6—Si4^ii	119.43 (6)	N2—C17—H17A	108.3
C1—N1—C13	110.6 (3)	C18—C17—H17B	108.3
C1—N1—C5	106.0 (3)	N2—C17—H17B	108.3
C13—N1—C5	111.0 (4)	H17A—C17—H17B	107.4
C1—N1—C10	111.4 (3)	C17—C18—C19	112.2 (4)
C13—N1—C10	106.9 (3)	C17—C18—H18A	109.2
C5—N1—C10	110.9 (3)	C19—C18—H18A	109.2
C2—C1—N1	117.1 (4)	C17—C18—H18B	109.2
C2—C1—H1A	108.0	C19—C18—H18B	109.2
N1—C1—H1A	108.0	H18A—C18—H18B	107.9
C2—C1—H1B	108.0	C18—C19—C20	112.2 (5)
N1—C1—H1B	108.0	C18—C19—H19A	109.2
H1A—C1—H1B	107.3	C20—C19—H19A	109.2
C1—C2—C3	108.1 (5)	C18—C19—H19B	109.2
C1—C2—H2A	110.1	C20—C19—H19B	109.2
C3—C2—H2A	110.1	H19A—C19—H19B	107.9
C1—C2—H2B	110.1	C19—C20—H20A	109.5
C3—C2—H2B	110.1	C19—C20—H20B	109.5
H2A—C2—H2B	108.4	H20A—C20—H20B	109.5
C4—C3—C2	115.4 (6)	C19—C20—H20C	109.5
C4—C3—H3A	108.4	H20A—C20—H20C	109.5
C2—C3—H3A	108.4	H20B—C20—H20C	109.5
C4—C3—H3B	108.4	C22—C21—N2	116.3 (4)
C2—C3—H3B	108.4	C22—C21—H21A	108.2
H3A—C3—H3B	107.5	N2—C21—H21A	108.2
C3—C4—H4A	109.5	C22—C21—H21B	108.2
C3—C4—H4B	109.5	N2—C21—H21B	108.2
H4A—C4—H4B	109.5	H21A—C21—H21B	107.4
C3—C4—H4C	109.5	C21—C22—C23	110.5 (5)
H4A—C4—H4C	109.5	C21—C22—H22A	109.6
H4B—C4—H4C	109.5	C23—C22—H22A	109.6
C6—C5—N1	115.7 (4)	C21—C22—H22B	109.6
C6—C5—H5A	108.4	C23—C22—H22B	109.6
N1—C5—H5A	108.4	H22A—C22—H22B	108.1
C6—C5—H5B	108.4	C24—C23—C22	112.8 (7)
N1—C5—H5B	108.4	C24—C23—H23A	109.0
H5A—C5—H5B	107.4	C22—C23—H23A	109.0
C5—C6—C7	110.5 (5)	C24—C23—H23B	109.0
C5—C6—H6A	109.6	C22—C23—H23B	109.0
C7—C6—H6A	109.6	H23A—C23—H23B	107.8
C5—C6—H6B	109.6	C23—C24—H24A	109.5
C7—C6—H6B	109.6	C23—C24—H24B	109.5
H6A—C6—H6B	108.1	H24A—C24—H24B	109.5
C8—C7—C6	111.0 (6)	C23—C24—H24C	109.5
C8—C7—H7A	109.4	H24A—C24—H24C	109.5
C6—C7—H7A	109.4	H24B—C24—H24C	109.5
C8—C7—H7B	109.4	C26—C25—N2	116.1 (3)
C6—C7—H7B	109.4	C26—C25—H25A	108.3
H7A—C7—H7B	108.0	N2—C25—H25A	108.3
C7—C8—H8A	109.5	C26—C25—H25B	108.3
C7—C8—H8B	109.5	N2—C25—H25B	108.3
H8A—C8—H8B	109.5	H25A—C25—H25B	107.4
C7—C8—H8C	109.5	C25—C26—C27	111.1 (4)
H8A—C8—H8C	109.5	C25—C26—H26A	109.4
H8B—C8—H8C	109.5	C27—C26—H26A	109.4
C11—C9—C10	110.2 (4)	C25—C26—H26B	109.4
C11—C9—H9A	109.6	C27—C26—H26B	109.4
C10—C9—H9A	109.6	H26A—C26—H26B	108.0
C11—C9—H9B	109.6	C28—C27—C26	111.5 (4)
C10—C9—H9B	109.6	C28—C27—H27A	109.3
H9A—C9—H9B	108.1	C26—C27—H27A	109.3
C9—C10—N1	117.2 (4)	C28—C27—H27B	109.3
C9—C10—H10A	108.0	C26—C27—H27B	109.3
N1—C10—H10A	108.0	H27A—C27—H27B	108.0
C9—C10—H10B	108.0	C27—C28—H28A	109.5
N1—C10—H10B	108.0	C27—C28—H28B	109.5
H10A—C10—H10B	107.2	H28A—C28—H28B	109.5
C12—C11—C9	113.7 (5)	C27—C28—H28C	109.5
C12—C11—H11A	108.8	H28A—C28—H28C	109.5
C9—C11—H11A	108.8	H28B—C28—H28C	109.5
C12—C11—H11B	108.8	N2—C29—H29A	109.5
C9—C11—H11B	108.8	N2—C29—H29B	109.5
H11A—C11—H11B	107.7	H29A—C29—H29B	109.5
C11—C12—H12A	109.5	N2—C29—H29C	109.5
C11—C12—H12B	109.5	H29A—C29—H29C	109.5
H12A—C12—H12B	109.5	H29B—C29—H29C	109.5
C13—N1—C1—C2	62.9 (5)	N1—C13—C14—C15	178.0 (4)
C5—N1—C1—C2	−176.7 (5)	C13—C14—C15—C16	175.6 (5)
C10—N1—C1—C2	−55.9 (5)	C29—N2—C17—C18	174.5 (4)
N1—C1—C2—C3	−175.3 (5)	C21—N2—C17—C18	−64.3 (5)
C1—C2—C3—C4	−171.8 (7)	C25—N2—C17—C18	56.4 (5)
C1—N1—C5—C6	−173.5 (4)	N2—C17—C18—C19	175.4 (4)
C13—N1—C5—C6	−53.3 (5)	C17—C18—C19—C20	172.7 (5)
C10—N1—C5—C6	65.4 (5)	C29—N2—C21—C22	65.0 (5)
N1—C5—C6—C7	−171.2 (4)	C17—N2—C21—C22	−54.7 (5)
C5—C6—C7—C8	−173.8 (5)	C25—N2—C21—C22	−175.1 (4)
C11—C9—C10—N1	175.1 (4)	N2—C21—C22—C23	−173.5 (5)
C1—N1—C10—C9	−58.9 (5)	C21—C22—C23—C24	−177.1 (7)
C13—N1—C10—C9	−179.8 (4)	C29—N2—C25—C26	48.4 (5)
C5—N1—C10—C9	59.0 (5)	C21—N2—C25—C26	−72.0 (5)
C10—C9—C11—C12	−177.2 (5)	C17—N2—C25—C26	165.5 (4)
C1—N1—C13—C14	56.1 (5)	N2—C25—C26—C27	176.4 (3)
C5—N1—C13—C14	−61.3 (5)	C25—C26—C27—C28	178.3 (5)
C10—N1—C13—C14	177.6 (4)

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

(III) Bis(tetrabutylammonium) dichloride dodecachlorohexasilane benzene disolvate

Crystal data

2C16H36N^+·2Cl^−·Cl12Si6·2C6H6	Dx = 1.322 Mg m^−3
Mr = 1305.97	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 57758 reflections
a = 15.4687 (4) Å	θ = 1.8–26.7°
b = 18.5439 (5) Å	µ = 0.73 mm^−1
c = 22.8784 (7) Å	T = 173 K
V = 6562.7 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.18 × 0.15 mm
F(000) = 2736

Data collection

Stoe IPDS II two-circle diffractometer	5439 reflections with I > 2σ(I)
ω scans	Rint = 0.077
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θmax = 26.2°, θmin = 1.9°
	h = −19→19
80026 measured reflections	k = −22→22
6554 independent reflections	l = −28→28

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 6.5182P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
6554 reflections	Δρmax = 0.80 e Å^−3
298 parameters	Δρmin = −0.65 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.57098 (5)	0.57015 (4)	0.53754 (4)	0.0460 (2)
Si1	0.46847 (6)	0.57957 (5)	0.42612 (4)	0.0461 (2)
Si2	0.37993 (6)	0.57596 (5)	0.50763 (4)	0.0364 (2)
Si3	0.41146 (6)	0.49536 (5)	0.58214 (4)	0.0439 (2)
Cl11	0.51169 (8)	0.68479 (6)	0.41618 (7)	0.0905 (5)
Cl12	0.38966 (8)	0.56708 (9)	0.35290 (4)	0.0856 (4)
Cl21	0.37059 (7)	0.67897 (5)	0.54255 (4)	0.0563 (2)
Cl22	0.25360 (6)	0.55793 (5)	0.47953 (4)	0.0508 (2)
Cl31	0.42110 (9)	0.55539 (7)	0.65884 (4)	0.0774 (4)
Cl32	0.30481 (7)	0.43083 (6)	0.59782 (6)	0.0775 (4)
N1	0.17777 (17)	0.35475 (15)	0.36163 (12)	0.0433 (6)
C1	0.1084 (3)	0.3518 (2)	0.40847 (17)	0.0558 (10)
H1A	0.0532	0.3677	0.3907	0.067*
H1B	0.1009	0.3008	0.4202	0.067*
C2	0.1229 (3)	0.3958 (3)	0.46311 (17)	0.0664 (12)
H2A	0.1278	0.4475	0.4530	0.080*
H2B	0.1772	0.3806	0.4824	0.080*
C3	0.0468 (4)	0.3841 (3)	0.5041 (2)	0.0763 (14)
H3A	−0.0072	0.3980	0.4837	0.092*
H3B	0.0428	0.3322	0.5138	0.092*
C4	0.0543 (5)	0.4268 (3)	0.5596 (2)	0.0947 (18)
H4A	0.0038	0.4174	0.5843	0.142*
H4B	0.1070	0.4125	0.5804	0.142*
H4C	0.0570	0.4783	0.5503	0.142*
C5	0.2639 (2)	0.32705 (19)	0.38386 (16)	0.0472 (8)
H5A	0.2817	0.3574	0.4173	0.057*
H5B	0.3074	0.3338	0.3526	0.057*
C6	0.2667 (3)	0.2489 (2)	0.4031 (2)	0.0722 (13)
H6A	0.2559	0.2170	0.3692	0.087*
H6B	0.2211	0.2399	0.4326	0.087*
C7	0.3565 (3)	0.2320 (3)	0.4296 (2)	0.0766 (14)
H7A	0.3657	0.2629	0.4644	0.092*
H7B	0.3576	0.1811	0.4428	0.092*
C8	0.4290 (4)	0.2441 (3)	0.3870 (3)	0.0864 (16)
H8A	0.4843	0.2327	0.4058	0.130*
H8B	0.4209	0.2129	0.3529	0.130*
H8C	0.4291	0.2947	0.3745	0.130*
C9	0.1939 (2)	0.43164 (18)	0.34194 (15)	0.0446 (8)
H9A	0.2194	0.4584	0.3752	0.053*
H9B	0.2379	0.4305	0.3105	0.053*
C10	0.1170 (2)	0.4739 (2)	0.31991 (17)	0.0510 (8)
H10A	0.0745	0.4800	0.3519	0.061*
H10B	0.0887	0.4471	0.2878	0.061*
C11	0.1461 (3)	0.5473 (2)	0.2981 (2)	0.0670 (11)
H11A	0.1737	0.5740	0.3306	0.080*
H11B	0.1898	0.5407	0.2669	0.080*
C12	0.0718 (4)	0.5916 (3)	0.2743 (2)	0.0809 (14)
H12A	0.0935	0.6384	0.2608	0.121*
H12B	0.0449	0.5659	0.2416	0.121*
H12C	0.0288	0.5992	0.3052	0.121*
C13	0.1437 (2)	0.3086 (2)	0.31165 (16)	0.0497 (8)
H13A	0.1337	0.2593	0.3268	0.060*
H13B	0.0869	0.3282	0.2996	0.060*
C14	0.2000 (3)	0.3030 (3)	0.25803 (19)	0.0652 (11)
H14A	0.2567	0.2824	0.2690	0.078*
H14B	0.2100	0.3518	0.2418	0.078*
C15	0.1579 (4)	0.2555 (3)	0.2114 (2)	0.0876 (16)
H15A	0.0953	0.2665	0.2104	0.105*
H15B	0.1822	0.2690	0.1729	0.105*
C16	0.1673 (7)	0.1835 (4)	0.2182 (4)	0.154 (4)
H16A	0.1381	0.1584	0.1861	0.231*
H16B	0.2289	0.1713	0.2179	0.231*
H16C	0.1418	0.1688	0.2555	0.231*
C21	0.8956 (3)	0.4256 (4)	0.2655 (3)	0.0842 (16)
H21	0.9071	0.4569	0.2336	0.101*
C22	0.8545 (3)	0.4506 (3)	0.3136 (3)	0.0852 (15)
H22	0.8364	0.4995	0.3150	0.102*
C23	0.8387 (3)	0.4068 (3)	0.3597 (2)	0.0794 (14)
H23	0.8102	0.4253	0.3933	0.095*
C24	0.8634 (3)	0.3366 (3)	0.3581 (2)	0.0790 (14)
H24	0.8526	0.3063	0.3908	0.095*
C25	0.9036 (3)	0.3095 (3)	0.3098 (3)	0.0770 (14)
H25	0.9196	0.2601	0.3083	0.092*
C26	0.9207 (3)	0.3545 (4)	0.2631 (2)	0.0822 (16)
H26	0.9496	0.3364	0.2296	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0436 (4)	0.0356 (4)	0.0588 (5)	−0.0027 (3)	−0.0099 (4)	−0.0098 (3)
Si1	0.0460 (5)	0.0481 (5)	0.0442 (5)	0.0109 (4)	0.0045 (4)	0.0135 (4)
Si2	0.0386 (4)	0.0326 (4)	0.0379 (4)	0.0016 (3)	−0.0030 (3)	−0.0003 (3)
Si3	0.0459 (5)	0.0467 (5)	0.0391 (5)	0.0097 (4)	0.0047 (4)	0.0075 (4)
Cl11	0.0735 (7)	0.0509 (6)	0.1469 (13)	0.0165 (5)	0.0404 (8)	0.0485 (7)
Cl12	0.0760 (7)	0.1419 (12)	0.0388 (5)	0.0476 (8)	−0.0076 (5)	0.0075 (6)
Cl21	0.0668 (6)	0.0392 (4)	0.0630 (6)	0.0089 (4)	−0.0084 (5)	−0.0125 (4)
Cl22	0.0393 (4)	0.0518 (5)	0.0611 (5)	0.0020 (4)	−0.0082 (4)	−0.0014 (4)
Cl31	0.0949 (8)	0.1005 (9)	0.0368 (5)	0.0414 (7)	−0.0026 (5)	−0.0081 (5)
Cl32	0.0540 (6)	0.0695 (7)	0.1090 (9)	0.0082 (5)	0.0279 (6)	0.0364 (6)
N1	0.0376 (14)	0.0510 (16)	0.0412 (15)	−0.0110 (12)	−0.0001 (12)	−0.0045 (12)
C1	0.053 (2)	0.061 (2)	0.054 (2)	−0.0230 (18)	0.0136 (17)	−0.0062 (18)
C2	0.077 (3)	0.076 (3)	0.046 (2)	−0.026 (2)	0.013 (2)	−0.0065 (19)
C3	0.102 (4)	0.067 (3)	0.061 (3)	−0.019 (3)	0.033 (3)	−0.003 (2)
C4	0.127 (5)	0.091 (4)	0.065 (3)	−0.012 (3)	0.032 (3)	−0.016 (3)
C5	0.0427 (19)	0.051 (2)	0.0482 (19)	−0.0131 (15)	−0.0052 (15)	0.0048 (15)
C6	0.066 (3)	0.063 (3)	0.088 (3)	−0.018 (2)	−0.018 (2)	0.029 (2)
C7	0.071 (3)	0.068 (3)	0.091 (3)	−0.014 (2)	−0.022 (3)	0.030 (3)
C8	0.089 (4)	0.072 (3)	0.099 (4)	0.012 (3)	−0.028 (3)	0.002 (3)
C9	0.0442 (18)	0.0485 (19)	0.0410 (17)	−0.0087 (15)	0.0028 (14)	−0.0020 (14)
C10	0.0484 (19)	0.058 (2)	0.0465 (19)	0.0027 (17)	0.0013 (16)	−0.0051 (16)
C11	0.069 (3)	0.060 (2)	0.071 (3)	0.003 (2)	−0.007 (2)	0.001 (2)
C12	0.094 (4)	0.067 (3)	0.081 (3)	0.021 (3)	−0.012 (3)	−0.001 (2)
C13	0.0445 (18)	0.050 (2)	0.054 (2)	−0.0069 (16)	−0.0071 (16)	−0.0125 (17)
C14	0.059 (2)	0.082 (3)	0.055 (2)	0.001 (2)	−0.0038 (19)	−0.022 (2)
C15	0.092 (4)	0.097 (4)	0.073 (3)	0.022 (3)	−0.024 (3)	−0.037 (3)
C16	0.195 (9)	0.089 (5)	0.178 (9)	−0.004 (5)	−0.046 (7)	−0.040 (5)
C21	0.049 (2)	0.114 (4)	0.089 (4)	−0.014 (3)	−0.013 (2)	0.030 (3)
C22	0.059 (3)	0.078 (3)	0.119 (5)	0.006 (2)	−0.010 (3)	−0.004 (3)
C23	0.067 (3)	0.101 (4)	0.071 (3)	0.010 (3)	0.000 (2)	−0.012 (3)
C24	0.063 (3)	0.105 (4)	0.068 (3)	−0.003 (3)	−0.015 (2)	0.016 (3)
C25	0.060 (3)	0.074 (3)	0.097 (4)	0.014 (2)	−0.031 (3)	−0.007 (3)
C26	0.039 (2)	0.141 (5)	0.066 (3)	0.009 (3)	−0.009 (2)	−0.022 (3)

Geometric parameters (Å, º)

Si1—Cl11	2.0751 (15)	C8—H8C	0.9800
Si1—Cl12	2.0847 (15)	C9—C10	1.511 (5)
Si1—Si2	2.3146 (13)	C9—H9A	0.9900
Si1—Si3^i	2.3272 (13)	C9—H9B	0.9900
Si2—Cl21	2.0756 (12)	C10—C11	1.519 (6)
Si2—Cl22	2.0841 (12)	C10—H10A	0.9900
Si2—Si3	2.3192 (12)	C10—H10B	0.9900
Si3—Cl32	2.0693 (15)	C11—C12	1.513 (6)
Si3—Cl31	2.0834 (15)	C11—H11A	0.9900
Si3—Si1^i	2.3272 (13)	C11—H11B	0.9900
N1—C5	1.516 (4)	C12—H12A	0.9800
N1—C9	1.516 (4)	C12—H12B	0.9800
N1—C1	1.518 (4)	C12—H12C	0.9800
N1—C13	1.523 (4)	C13—C14	1.508 (6)
C1—C2	1.509 (5)	C13—H13A	0.9900
C1—H1A	0.9900	C13—H13B	0.9900
C1—H1B	0.9900	C14—C15	1.530 (6)
C2—C3	1.520 (6)	C14—H14A	0.9900
C2—H2A	0.9900	C14—H14B	0.9900
C2—H2B	0.9900	C15—C16	1.351 (9)
C3—C4	1.500 (7)	C15—H15A	0.9900
C3—H3A	0.9900	C15—H15B	0.9900
C3—H3B	0.9900	C16—H16A	0.9800
C4—H4A	0.9800	C16—H16B	0.9800
C4—H4B	0.9800	C16—H16C	0.9800
C4—H4C	0.9800	C21—C22	1.351 (8)
C5—C6	1.516 (5)	C21—C26	1.376 (8)
C5—H5A	0.9900	C21—H21	0.9500
C5—H5B	0.9900	C22—C23	1.354 (8)
C6—C7	1.548 (6)	C22—H22	0.9500
C6—H6A	0.9900	C23—C24	1.356 (8)
C6—H6B	0.9900	C23—H23	0.9500
C7—C8	1.503 (8)	C24—C25	1.364 (8)
C7—H7A	0.9900	C24—H24	0.9500
C7—H7B	0.9900	C25—C26	1.380 (8)
C8—H8A	0.9800	C25—H25	0.9500
C8—H8B	0.9800	C26—H26	0.9500
Cl11—Si1—Cl12	101.82 (8)	C7—C8—H8C	109.5
Cl11—Si1—Si2	107.83 (6)	H8A—C8—H8C	109.5
Cl12—Si1—Si2	107.35 (6)	H8B—C8—H8C	109.5
Cl11—Si1—Si3^i	107.18 (6)	C10—C9—N1	117.2 (3)
Cl12—Si1—Si3^i	109.58 (6)	C10—C9—H9A	108.0
Si2—Si1—Si3^i	121.36 (5)	N1—C9—H9A	108.0
Cl21—Si2—Cl22	101.60 (5)	C10—C9—H9B	108.0
Cl21—Si2—Si1	108.94 (5)	N1—C9—H9B	108.0
Cl22—Si2—Si1	108.12 (5)	H9A—C9—H9B	107.2
Cl21—Si2—Si3	108.96 (5)	C9—C10—C11	110.0 (3)
Cl22—Si2—Si3	108.69 (5)	C9—C10—H10A	109.7
Si1—Si2—Si3	119.11 (5)	C11—C10—H10A	109.7
Cl32—Si3—Cl31	102.72 (7)	C9—C10—H10B	109.7
Cl32—Si3—Si2	109.41 (6)	C11—C10—H10B	109.7
Cl31—Si3—Si2	106.85 (6)	H10A—C10—H10B	108.2
Cl32—Si3—Si1^i	107.77 (6)	C12—C11—C10	112.3 (4)
Cl31—Si3—Si1^i	109.29 (6)	C12—C11—H11A	109.1
Si2—Si3—Si1^i	119.53 (5)	C10—C11—H11A	109.1
C5—N1—C9	105.9 (2)	C12—C11—H11B	109.1
C5—N1—C1	111.9 (3)	C10—C11—H11B	109.1
C9—N1—C1	111.1 (3)	H11A—C11—H11B	107.9
C5—N1—C13	111.5 (3)	C11—C12—H12A	109.5
C9—N1—C13	111.3 (3)	C11—C12—H12B	109.5
C1—N1—C13	105.4 (3)	H12A—C12—H12B	109.5
C2—C1—N1	117.4 (3)	C11—C12—H12C	109.5
C2—C1—H1A	108.0	H12A—C12—H12C	109.5
N1—C1—H1A	108.0	H12B—C12—H12C	109.5
C2—C1—H1B	108.0	C14—C13—N1	116.7 (3)
N1—C1—H1B	108.0	C14—C13—H13A	108.1
H1A—C1—H1B	107.2	N1—C13—H13A	108.1
C1—C2—C3	108.6 (4)	C14—C13—H13B	108.1
C1—C2—H2A	110.0	N1—C13—H13B	108.1
C3—C2—H2A	110.0	H13A—C13—H13B	107.3
C1—C2—H2B	110.0	C13—C14—C15	111.2 (4)
C3—C2—H2B	110.0	C13—C14—H14A	109.4
H2A—C2—H2B	108.4	C15—C14—H14A	109.4
C4—C3—C2	112.8 (4)	C13—C14—H14B	109.4
C4—C3—H3A	109.0	C15—C14—H14B	109.4
C2—C3—H3A	109.0	H14A—C14—H14B	108.0
C4—C3—H3B	109.0	C16—C15—C14	116.3 (6)
C2—C3—H3B	109.0	C16—C15—H15A	108.2
H3A—C3—H3B	107.8	C14—C15—H15A	108.2
C3—C4—H4A	109.5	C16—C15—H15B	108.2
C3—C4—H4B	109.5	C14—C15—H15B	108.2
H4A—C4—H4B	109.5	H15A—C15—H15B	107.4
C3—C4—H4C	109.5	C15—C16—H16A	109.5
H4A—C4—H4C	109.5	C15—C16—H16B	109.5
H4B—C4—H4C	109.5	H16A—C16—H16B	109.5
N1—C5—C6	116.5 (3)	C15—C16—H16C	109.5
N1—C5—H5A	108.2	H16A—C16—H16C	109.5
C6—C5—H5A	108.2	H16B—C16—H16C	109.5
N1—C5—H5B	108.2	C22—C21—C26	119.6 (5)
C6—C5—H5B	108.2	C22—C21—H21	120.2
H5A—C5—H5B	107.3	C26—C21—H21	120.2
C5—C6—C7	109.4 (3)	C21—C22—C23	120.9 (5)
C5—C6—H6A	109.8	C21—C22—H22	119.6
C7—C6—H6A	109.8	C23—C22—H22	119.6
C5—C6—H6B	109.8	C22—C23—C24	120.2 (5)
C7—C6—H6B	109.8	C22—C23—H23	119.9
H6A—C6—H6B	108.2	C24—C23—H23	119.9
C8—C7—C6	112.6 (4)	C23—C24—C25	120.2 (5)
C8—C7—H7A	109.1	C23—C24—H24	119.9
C6—C7—H7A	109.1	C25—C24—H24	119.9
C8—C7—H7B	109.1	C24—C25—C26	119.5 (5)
C6—C7—H7B	109.1	C24—C25—H25	120.3
H7A—C7—H7B	107.8	C26—C25—H25	120.3
C7—C8—H8A	109.5	C21—C26—C25	119.6 (5)
C7—C8—H8B	109.5	C21—C26—H26	120.2
H8A—C8—H8B	109.5	C25—C26—H26	120.2
C5—N1—C1—C2	61.2 (5)	N1—C9—C10—C11	−175.9 (3)
C9—N1—C1—C2	−56.9 (5)	C9—C10—C11—C12	178.9 (4)
C13—N1—C1—C2	−177.5 (4)	C5—N1—C13—C14	−59.5 (4)
N1—C1—C2—C3	−179.2 (4)	C9—N1—C13—C14	58.5 (4)
C1—C2—C3—C4	−179.0 (5)	C1—N1—C13—C14	179.0 (4)
C9—N1—C5—C6	−176.5 (3)	N1—C13—C14—C15	−179.8 (4)
C1—N1—C5—C6	62.3 (4)	C13—C14—C15—C16	−81.5 (8)
C13—N1—C5—C6	−55.4 (4)	C26—C21—C22—C23	0.9 (8)
N1—C5—C6—C7	−174.8 (4)	C21—C22—C23—C24	−0.6 (8)
C5—C6—C7—C8	−59.8 (6)	C22—C23—C24—C25	−0.6 (8)
C5—N1—C9—C10	−177.4 (3)	C23—C24—C25—C26	1.5 (7)
C1—N1—C9—C10	−55.7 (4)	C22—C21—C26—C25	0.0 (7)
C13—N1—C9—C10	61.3 (4)	C24—C25—C26—C21	−1.2 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

(IV) Bis(benzyltriphenylphosphonium) dichloride dodecachlorohexasilane

Crystal data

2C25H22P^+·2Cl^−·Cl12Si6	Z = 1
Mr = 1371.64	F(000) = 696
Triclinic, P1	Dx = 1.520 Mg m^−3
a = 11.0097 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.7082 (18) Å	Cell parameters from 10444 reflections
c = 13.0269 (18) Å	θ = 3.3–26.0°
α = 61.618 (10)°	µ = 0.85 mm^−1
β = 72.804 (11)°	T = 173 K
γ = 71.605 (11)°	Block, colourless
V = 1498.3 (4) Å^3	0.20 × 0.10 × 0.10 mm

Data collection

Stoe IPDS II two-circle diffractometer	3338 reflections with I > 2σ(I)
ω scans	Rint = 0.071
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θmax = 26.2°, θmin = 3.3°
	h = −13→13
12339 measured reflections	k = −15→12
5906 independent reflections	l = −16→16

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0697P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
5906 reflections	Δρmax = 0.64 e Å^−3
328 parameters	Δρmin = −0.35 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.64801 (14)	0.89235 (12)	−0.04341 (12)	0.0493 (4)
Si1	0.59281 (16)	0.96447 (14)	0.15446 (14)	0.0443 (4)
Si2	0.45368 (17)	0.84461 (14)	0.18314 (14)	0.0465 (4)
Si3	0.36905 (17)	0.87192 (15)	0.02644 (14)	0.0484 (4)
Cl11	0.76863 (17)	0.85127 (15)	0.20446 (16)	0.0662 (5)
Cl12	0.52054 (15)	1.03489 (13)	0.28126 (12)	0.0511 (4)
Cl21	0.5505 (2)	0.66318 (13)	0.25723 (15)	0.0676 (5)
Cl22	0.30171 (17)	0.85440 (14)	0.31973 (13)	0.0598 (4)
Cl31	0.16870 (18)	0.88910 (18)	0.07583 (15)	0.0731 (5)
Cl32	0.42928 (19)	0.71247 (13)	0.00173 (14)	0.0634 (5)
P1	0.8445 (3)	0.6830 (2)	0.6904 (2)	0.0394 (10)	0.567 (5)
C1	0.8358 (10)	0.8364 (8)	0.6619 (9)	0.043 (2)*	0.567 (5)
H1A	0.8125	0.8906	0.5824	0.052*	0.567 (5)
H1B	0.7641	0.8577	0.7202	0.052*	0.567 (5)
C11	0.9593 (10)	0.8645 (9)	0.6666 (8)	0.036 (2)*	0.567 (5)
C12	0.9716 (13)	0.8778 (11)	0.7657 (12)	0.037 (3)*	0.567 (5)
H12	0.9057	0.8586	0.8341	0.045*	0.567 (5)
C13	1.0735 (12)	0.9168 (11)	0.7670 (11)	0.045 (3)*	0.567 (5)
H13	1.0722	0.9404	0.8265	0.054*	0.567 (5)
C14	1.1842 (15)	0.9198 (14)	0.6712 (13)	0.060 (4)*	0.567 (5)
H14	1.2619	0.9372	0.6715	0.072*	0.567 (5)
C15	1.1757 (11)	0.8981 (9)	0.5829 (10)	0.045 (2)*	0.567 (5)
H15	1.2480	0.9028	0.5203	0.054*	0.567 (5)
C16	1.0684 (10)	0.8694 (9)	0.5778 (9)	0.045 (2)*	0.567 (5)
H16	1.0683	0.8528	0.5140	0.054*	0.567 (5)
P1'	0.9289 (4)	0.7062 (3)	0.6925 (3)	0.0409 (13)	0.433 (5)
C1'	0.7663 (12)	0.7911 (10)	0.6601 (12)	0.046 (3)*	0.433 (5)
H1'1	0.7197	0.8240	0.7198	0.055*	0.433 (5)
H1'2	0.7738	0.8611	0.5814	0.055*	0.433 (5)
C11'	1.0185 (13)	0.8020 (11)	0.6923 (10)	0.036 (3)*	0.433 (5)
C12'	1.1420 (12)	0.8082 (11)	0.6295 (11)	0.041 (3)*	0.433 (5)
H12'	1.1797	0.7629	0.5831	0.049*	0.433 (5)
C13'	1.2124 (14)	0.8783 (12)	0.6320 (13)	0.040 (3)*	0.433 (5)
H13'	1.2993	0.8791	0.5906	0.048*	0.433 (5)
C14'	1.1560 (17)	0.9461 (14)	0.6943 (14)	0.045 (4)*	0.433 (5)
H14'	1.2055	0.9910	0.7010	0.055*	0.433 (5)
C15'	1.0292 (17)	0.9511 (15)	0.7475 (14)	0.053 (4)*	0.433 (5)
H15'	0.9947	0.9987	0.7920	0.063*	0.433 (5)
C16'	0.949 (2)	0.8940 (16)	0.7422 (16)	0.049 (6)*	0.433 (5)
H16'	0.8576	0.9102	0.7674	0.059*	0.433 (5)
C21	0.8779 (7)	0.5787 (5)	0.8374 (5)	0.0590 (17)
C22	0.9073 (7)	0.4586 (6)	0.8580 (6)	0.0645 (18)
H22	0.9406	0.4348	0.7943	0.077*
C23	0.8877 (9)	0.3724 (7)	0.9734 (8)	0.092 (3)
H23	0.9093	0.2880	0.9899	0.111*
C24	0.8373 (8)	0.4077 (8)	1.0644 (7)	0.096 (3)
H24	0.8224	0.3476	1.1435	0.115*
C25	0.8090 (6)	0.5249 (7)	1.0434 (5)	0.0610 (17)
H25	0.7746	0.5477	1.1077	0.073*
C26	0.8287 (7)	0.6125 (6)	0.9312 (6)	0.0607 (17)
H26	0.8090	0.6962	0.9169	0.073*
C31	0.9946 (8)	0.6421 (6)	0.5878 (6)	0.0655 (19)
C32	0.9745 (8)	0.6873 (7)	0.4735 (6)	0.085 (3)
H32	0.8941	0.7402	0.4523	0.103*
C33	1.0676 (7)	0.6575 (6)	0.3903 (6)	0.0620 (17)
H33	1.0528	0.6905	0.3115	0.074*
C34	1.1798 (9)	0.5818 (8)	0.4201 (8)	0.083 (2)
H34	1.2443	0.5592	0.3630	0.099*
C35	1.2017 (9)	0.5373 (9)	0.5316 (10)	0.107 (3)
H35	1.2822	0.4842	0.5519	0.129*
C36	1.1100 (9)	0.5675 (7)	0.6155 (7)	0.075 (2)
H36	1.1272	0.5362	0.6933	0.090*
C41	0.6864 (7)	0.7089 (9)	0.6613 (6)	0.086 (3)
C42	0.6194 (8)	0.6194 (9)	0.7552 (6)	0.093 (3)
H42	0.6486	0.5750	0.8292	0.112*
C43	0.5151 (7)	0.5955 (5)	0.7421 (6)	0.0616 (17)
H43	0.4690	0.5378	0.8071	0.074*
C44	0.4777 (8)	0.6539 (7)	0.6366 (7)	0.083 (2)
H44	0.4063	0.6355	0.6261	0.100*
C45	0.5405 (8)	0.7400 (7)	0.5435 (7)	0.081 (2)
H45	0.5126	0.7809	0.4690	0.097*
C46	0.6430 (6)	0.7672 (5)	0.5574 (6)	0.0556 (16)
H46	0.6847	0.8285	0.4925	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0527 (9)	0.0458 (8)	0.0506 (8)	−0.0172 (7)	0.0130 (7)	−0.0296 (7)
Si1	0.0450 (10)	0.0424 (8)	0.0452 (9)	−0.0159 (7)	0.0061 (7)	−0.0220 (7)
Si2	0.0582 (11)	0.0421 (8)	0.0419 (8)	−0.0235 (7)	0.0095 (8)	−0.0221 (7)
Si3	0.0575 (11)	0.0487 (9)	0.0430 (9)	−0.0291 (8)	0.0118 (8)	−0.0230 (7)
Cl11	0.0511 (10)	0.0666 (10)	0.0723 (11)	−0.0056 (8)	−0.0102 (9)	−0.0270 (9)
Cl12	0.0564 (10)	0.0571 (9)	0.0481 (8)	−0.0197 (7)	0.0004 (7)	−0.0293 (7)
Cl21	0.0991 (14)	0.0414 (8)	0.0602 (9)	−0.0182 (8)	−0.0130 (9)	−0.0181 (7)
Cl22	0.0682 (11)	0.0702 (10)	0.0466 (8)	−0.0387 (8)	0.0182 (8)	−0.0303 (8)
Cl31	0.0596 (11)	0.0998 (13)	0.0628 (10)	−0.0442 (10)	0.0142 (9)	−0.0339 (10)
Cl32	0.0963 (13)	0.0469 (8)	0.0570 (9)	−0.0342 (8)	−0.0016 (9)	−0.0246 (7)
P1	0.043 (2)	0.0337 (13)	0.0424 (15)	−0.0116 (11)	−0.0035 (12)	−0.0166 (11)
P1'	0.040 (3)	0.0433 (19)	0.047 (2)	−0.0137 (16)	0.0031 (16)	−0.0279 (16)
C21	0.084 (5)	0.044 (3)	0.047 (3)	−0.009 (3)	−0.006 (3)	−0.024 (3)
C22	0.076 (5)	0.061 (4)	0.076 (5)	−0.018 (4)	−0.018 (4)	−0.039 (4)
C23	0.111 (7)	0.048 (4)	0.096 (6)	−0.031 (4)	0.007 (6)	−0.018 (4)
C24	0.084 (6)	0.068 (5)	0.070 (5)	−0.013 (4)	0.022 (5)	0.001 (4)
C25	0.049 (4)	0.082 (5)	0.044 (4)	−0.020 (3)	0.005 (3)	−0.025 (4)
C26	0.073 (5)	0.049 (3)	0.061 (4)	−0.020 (3)	0.007 (4)	−0.030 (3)
C31	0.090 (6)	0.045 (3)	0.053 (4)	−0.001 (4)	−0.009 (4)	−0.025 (3)
C32	0.073 (5)	0.092 (6)	0.053 (4)	0.010 (4)	0.004 (4)	−0.025 (4)
C33	0.063 (5)	0.072 (4)	0.060 (4)	−0.022 (4)	0.005 (4)	−0.039 (4)
C34	0.078 (6)	0.078 (5)	0.082 (6)	−0.027 (5)	0.032 (5)	−0.046 (5)
C35	0.050 (5)	0.109 (7)	0.122 (9)	−0.016 (5)	0.003 (6)	−0.027 (6)
C36	0.082 (6)	0.079 (5)	0.075 (5)	−0.033 (4)	−0.027 (5)	−0.023 (4)
C41	0.051 (5)	0.174 (9)	0.051 (4)	−0.050 (5)	0.013 (4)	−0.057 (5)
C42	0.048 (5)	0.166 (9)	0.043 (4)	−0.013 (5)	−0.003 (4)	−0.035 (5)
C43	0.057 (4)	0.043 (3)	0.064 (4)	−0.003 (3)	−0.008 (4)	−0.013 (3)
C44	0.096 (6)	0.086 (5)	0.086 (5)	−0.058 (5)	−0.026 (5)	−0.021 (5)
C45	0.068 (5)	0.093 (6)	0.062 (4)	−0.033 (4)	−0.028 (4)	0.002 (4)
C46	0.048 (4)	0.049 (3)	0.061 (4)	−0.017 (3)	0.000 (3)	−0.017 (3)

Geometric parameters (Å, º)

Si1—Cl11	2.083 (2)	C13'—H13'	0.9500
Si1—Cl12	2.084 (2)	C14'—C15'	1.36 (2)
Si1—Si3^i	2.315 (2)	C14'—H14'	0.9500
Si1—Si2	2.324 (2)	C15'—C16'	1.34 (2)
Si2—Cl22	2.074 (2)	C15'—H15'	0.9500
Si2—Cl21	2.080 (2)	C16'—H16'	0.9500
Si2—Si3	2.324 (2)	C21—C22	1.363 (8)
Si3—Cl32	2.072 (2)	C21—C26	1.390 (8)
Si3—Cl31	2.078 (3)	C22—C23	1.378 (10)
Si3—Si1^i	2.315 (2)	C22—H22	0.9500
P1—C1	1.777 (10)	C23—C24	1.369 (12)
P1—C41	1.787 (8)	C23—H23	0.9500
P1—C21	1.804 (7)	C24—C25	1.327 (10)
P1—C31	1.898 (7)	C24—H24	0.9500
C1—C11	1.536 (13)	C25—C26	1.357 (9)
C1—H1A	0.9900	C25—H25	0.9500
C1—H1B	0.9900	C26—H26	0.9500
C11—C16	1.393 (13)	C31—C36	1.352 (10)
C11—C12	1.427 (15)	C31—C32	1.377 (10)
C12—C13	1.370 (18)	C32—C33	1.363 (9)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.46 (2)	C33—C34	1.335 (11)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.339 (19)	C34—C35	1.352 (12)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.369 (15)	C35—C36	1.365 (12)
C15—H15	0.9500	C35—H35	0.9500
C16—H16	0.9500	C36—H36	0.9500
P1'—C31	1.774 (7)	C41—C46	1.347 (9)
P1'—C1'	1.829 (13)	C41—C42	1.417 (11)
P1'—C11'	1.792 (12)	C42—C43	1.351 (11)
P1'—C21	1.883 (7)	C42—H42	0.9500
C1'—C41	1.556 (5)	C43—C44	1.334 (10)
C1'—H1'1	0.9900	C43—H43	0.9500
C1'—H1'2	0.9900	C44—C45	1.366 (10)
C11'—C12'	1.368 (17)	C44—H44	0.9500
C11'—C16'	1.50 (2)	C45—C46	1.360 (9)
C12'—C13'	1.368 (19)	C45—H45	0.9500
C12'—H12'	0.9500	C46—H46	0.9500
C13'—C14'	1.35 (2)
Cl11—Si1—Cl12	102.03 (10)	C13'—C14'—C15'	120.8 (14)
Cl11—Si1—Si3^i	109.96 (10)	C13'—C14'—H14'	119.6
Cl12—Si1—Si3^i	106.62 (8)	C15'—C14'—H14'	119.6
Cl11—Si1—Si2	108.98 (9)	C16'—C15'—C14'	125.0 (16)
Cl12—Si1—Si2	107.43 (9)	C16'—C15'—H15'	117.5
Si3^i—Si1—Si2	120.23 (9)	C14'—C15'—H15'	117.5
Cl22—Si2—Cl21	102.09 (10)	C15'—C16'—C11'	113.0 (16)
Cl22—Si2—Si1	108.46 (8)	C15'—C16'—H16'	123.5
Cl21—Si2—Si1	107.01 (10)	C11'—C16'—H16'	123.5
Cl22—Si2—Si3	108.85 (10)	C22—C21—C26	120.4 (6)
Cl21—Si2—Si3	107.85 (9)	C22—C21—P1	113.9 (5)
Si1—Si2—Si3	120.95 (8)	C26—C21—P1	121.1 (5)
Cl32—Si3—Cl31	103.06 (10)	C22—C21—P1'	124.7 (5)
Cl32—Si3—Si1^i	108.97 (9)	C26—C21—P1'	113.8 (4)
Cl31—Si3—Si1^i	106.90 (10)	C21—C22—C23	118.4 (7)
Cl32—Si3—Si2	109.48 (10)	C21—C22—H22	120.8
Cl31—Si3—Si2	108.85 (9)	C23—C22—H22	120.8
Si1^i—Si3—Si2	118.47 (8)	C24—C23—C22	120.3 (7)
C1—P1—C41	96.1 (4)	C24—C23—H23	119.8
C1—P1—C21	111.0 (4)	C22—C23—H23	119.8
C41—P1—C21	118.2 (4)	C25—C24—C23	120.7 (7)
C1—P1—C31	106.1 (4)	C25—C24—H24	119.6
C41—P1—C31	120.0 (4)	C23—C24—H24	119.6
C21—P1—C31	104.4 (3)	C24—C25—C26	120.8 (7)
C11—C1—P1	116.3 (7)	C24—C25—H25	119.6
C11—C1—H1A	108.2	C26—C25—H25	119.6
P1—C1—H1A	108.2	C25—C26—C21	119.4 (6)
C11—C1—H1B	108.2	C25—C26—H26	120.3
P1—C1—H1B	108.2	C21—C26—H26	120.3
H1A—C1—H1B	107.4	C36—C31—C32	118.3 (7)
C16—C11—C12	116.8 (9)	C36—C31—P1'	106.8 (6)
C16—C11—C1	121.2 (8)	C32—C31—P1'	129.8 (6)
C12—C11—C1	121.8 (9)	C36—C31—P1	128.4 (6)
C13—C12—C11	123.3 (11)	C32—C31—P1	113.0 (6)
C13—C12—H12	118.4	C33—C32—C31	121.2 (7)
C11—C12—H12	118.4	C33—C32—H32	119.4
C12—C13—C14	115.7 (11)	C31—C32—H32	119.4
C12—C13—H13	122.1	C34—C33—C32	119.6 (7)
C14—C13—H13	122.1	C34—C33—H33	120.2
C15—C14—C13	119.7 (13)	C32—C33—H33	120.2
C15—C14—H14	120.2	C33—C34—C35	119.9 (8)
C13—C14—H14	120.2	C33—C34—H34	120.0
C14—C15—C16	123.5 (11)	C35—C34—H34	120.0
C14—C15—H15	118.2	C34—C35—C36	121.1 (8)
C16—C15—H15	118.2	C34—C35—H35	119.4
C15—C16—C11	119.8 (9)	C36—C35—H35	119.4
C15—C16—H16	120.1	C31—C36—C35	119.8 (8)
C11—C16—H16	120.1	C31—C36—H36	120.1
C31—P1'—C1'	104.2 (5)	C35—C36—H36	120.1
C31—P1'—C11'	116.9 (5)	C46—C41—C42	116.8 (6)
C1'—P1'—C11'	110.9 (5)	C46—C41—C1'	106.8 (8)
C31—P1'—C21	106.3 (3)	C42—C41—C1'	132.1 (8)
C1'—P1'—C21	97.5 (5)	C46—C41—P1	129.7 (5)
C11'—P1'—C21	118.4 (5)	C42—C41—P1	109.5 (6)
C41—C1'—P1'	111.7 (7)	C43—C42—C41	121.6 (7)
C41—C1'—H1'1	109.3	C43—C42—H42	119.2
P1'—C1'—H1'1	109.3	C41—C42—H42	119.2
C41—C1'—H1'2	109.3	C44—C43—C42	119.1 (7)
P1'—C1'—H1'2	109.3	C44—C43—H43	120.4
H1'1—C1'—H1'2	107.9	C42—C43—H43	120.4
C12'—C11'—C16'	118.6 (12)	C43—C44—C45	121.0 (7)
C12'—C11'—P1'	121.3 (9)	C43—C44—H44	119.5
C16'—C11'—P1'	119.1 (11)	C45—C44—H44	119.5
C13'—C12'—C11'	121.6 (12)	C46—C45—C44	120.1 (7)
C13'—C12'—H12'	119.2	C46—C45—H45	120.0
C11'—C12'—H12'	119.2	C44—C45—H45	120.0
C14'—C13'—C12'	118.7 (13)	C41—C46—C45	121.3 (6)
C14'—C13'—H13'	120.7	C41—C46—H46	119.4
C12'—C13'—H13'	120.7	C45—C46—H46	119.4
C41—P1—C1—C11	−175.5 (7)	C22—C23—C24—C25	−1.4 (15)
C21—P1—C1—C11	61.1 (8)	C23—C24—C25—C26	0.4 (14)
C31—P1—C1—C11	−51.8 (8)	C24—C25—C26—C21	0.6 (12)
P1—C1—C11—C16	72.2 (11)	C22—C21—C26—C25	−0.6 (11)
P1—C1—C11—C12	−103.0 (11)	P1—C21—C26—C25	153.8 (6)
C16—C11—C12—C13	12.5 (17)	P1'—C21—C26—C25	−169.0 (6)
C1—C11—C12—C13	−172.1 (11)	C1'—P1'—C31—C36	−173.7 (6)
C11—C12—C13—C14	−12.5 (18)	C11'—P1'—C31—C36	63.5 (8)
C12—C13—C14—C15	7.0 (19)	C21—P1'—C31—C36	−71.3 (6)
C13—C14—C15—C16	−2 (2)	C1'—P1'—C31—C32	32.7 (10)
C14—C15—C16—C11	1.6 (18)	C11'—P1'—C31—C32	−90.1 (10)
C12—C11—C16—C15	−6.4 (15)	C21—P1'—C31—C32	135.1 (8)
C1—C11—C16—C15	178.2 (9)	C1—P1—C31—C36	106.9 (7)
C31—P1'—C1'—C41	54.0 (9)	C41—P1—C31—C36	−145.9 (7)
C11'—P1'—C1'—C41	−179.4 (7)	C21—P1—C31—C36	−10.5 (8)
C21—P1'—C1'—C41	−55.0 (8)	C1—P1—C31—C32	−79.6 (7)
C31—P1'—C11'—C12'	−11.1 (12)	C41—P1—C31—C32	27.6 (7)
C1'—P1'—C11'—C12'	−130.4 (11)	C21—P1—C31—C32	163.0 (6)
C21—P1'—C11'—C12'	118.2 (10)	C36—C31—C32—C33	0.3 (12)
C31—P1'—C11'—C16'	157.2 (11)	P1'—C31—C32—C33	151.5 (7)
C1'—P1'—C11'—C16'	37.9 (13)	P1—C31—C32—C33	−173.9 (6)
C21—P1'—C11'—C16'	−73.6 (13)	C31—C32—C33—C34	1.0 (12)
C16'—C11'—C12'—C13'	14 (2)	C32—C33—C34—C35	−1.5 (12)
P1'—C11'—C12'—C13'	−177.9 (10)	C33—C34—C35—C36	0.7 (13)
C11'—C12'—C13'—C14'	−3 (2)	C32—C31—C36—C35	−1.2 (12)
C12'—C13'—C14'—C15'	−4 (2)	P1'—C31—C36—C35	−158.4 (7)
C13'—C14'—C15'—C16'	−1 (3)	P1—C31—C36—C35	172.0 (7)
C14'—C15'—C16'—C11'	12 (3)	C34—C35—C36—C31	0.7 (13)
C12'—C11'—C16'—C15'	−18 (2)	P1'—C1'—C41—C46	−126.9 (8)
P1'—C11'—C16'—C15'	173.8 (12)	P1'—C1'—C41—C42	78.0 (13)
C1—P1—C21—C22	−169.6 (6)	C1—P1—C41—C46	72.7 (9)
C41—P1—C21—C22	80.8 (7)	C21—P1—C41—C46	−169.4 (7)
C31—P1—C21—C22	−55.7 (7)	C31—P1—C41—C46	−39.8 (10)
C1—P1—C21—C26	34.5 (8)	C1—P1—C41—C42	−131.0 (7)
C41—P1—C21—C26	−75.1 (7)	C21—P1—C41—C42	−13.2 (8)
C31—P1—C21—C26	148.4 (6)	C31—P1—C41—C42	116.4 (6)
C31—P1'—C21—C22	9.7 (8)	C46—C41—C42—C43	−1.5 (13)
C1'—P1'—C21—C22	117.0 (7)	C1'—C41—C42—C43	151.7 (10)
C11'—P1'—C21—C22	−124.3 (8)	P1—C41—C42—C43	−161.2 (7)
C31—P1'—C21—C26	177.5 (6)	C41—C42—C43—C44	2.9 (13)
C1'—P1'—C21—C26	−75.2 (6)	C42—C43—C44—C45	−2.2 (13)
C11'—P1'—C21—C26	43.5 (8)	C43—C44—C45—C46	0.1 (14)
C26—C21—C22—C23	−0.3 (11)	C42—C41—C46—C45	−0.7 (12)
P1—C21—C22—C23	−156.4 (7)	C1'—C41—C46—C45	−160.2 (8)
P1'—C21—C22—C23	166.7 (7)	P1—C41—C46—C45	154.2 (7)
C21—C22—C23—C24	1.3 (13)	C44—C45—C46—C41	1.4 (13)

Symmetry code: (i) −x+1, −y+2, −z.