syn-Tri-μ-chlorido-bis­{[(R,R)/(S,S)-2,2′-bis­(diphenyl­phosphino)-1,1′-bi­phenyl]hydridoiridium(III)} tetra­fluorido­borate dichloro­methane disolvate

In the structure of the title compound, [Ir₂Cl₃H₂(C₃₆H₂₈P₂)₂]BF₄·2CH₂Cl₂, the bimetallic cation features a confacial bi­octa­hedral structure that is held together by three bridging chloride ions and is very close to C₂ symmetric. The hydrides are in a syn orientation (trans to the same halide bridge), and the chelating bis­(phosphine) atropisomers display a racemic (R,R)/(S,S) configuration. Because of the high trans-bond-weakening influence of the hydride ligands, the Ir—Cl bonds trans to Ir—H [2.5262 (7) and 2.5365 (7) Å] are significantly longer than those opposite the Ir—P linkages [2.4287 (7)–2.4672 (8) Å]. The Ir—P distances vary between 2.2464 (9) and 2.2565 (8) Å. This study illustrates the usefulness of steri­cally demanding biaryl-based P₂ ligands in the synthesis of halide-bridged Ir₂ complexes, which are valuable precursors of versatile catalysts for homogeneous C=O hydrogenation.

S1. Comment

Recently, we reported on the oxidative addition of HCl to several bis(phosphine)-coordinated (cyclooctadiene)iridium(I) complexes, namely [Ir(η⁴-1,5-C₈H₁₂)L₂]BF₄ with L₂ = (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(R)-binap)], (2S,4S)-2,4-bis(diphenylphosphino)pentane [(S,S)-bdpp], and (1S,2S)-bis(diphenylphosphino)cyclopentane [(S,S)-bdpcp]. Whereas reactions between hydrogen chloride and [Ir(η⁴-1,5-C₈H₁₂){(S,S)-bdpp}]BF₄ or [Ir(η⁴-1,5-C₈H₁₂){(S,S)-bdpcp}]BF₄ yielded the usual mononuclear adducts, similar treatment of [Ir(η⁴-1,5-C₈H₁₂){(R)-binap}]BF₄ furnished the triply chlorido-bridged diiridium complex [Ir₂(H)₂{(R)-binap}₂(µ-Cl)₃]BF₄. We proposed that the action of HCl on the (R)-binap-containing precursor also produces a mononuclear iridium(III) complex as a first intermediate, where the greater bulkiness of the two `Ph<sub>2</sub>Pnaphthyl' building blocks of the binap ligand compared with that of the two `Ph₂Palkyl' halves of the bdpp and bdpcp chelate phosphines facilitates the decoordination of the diene ligand through steric pressure. Bridge-closing combination of the remaining [Ir(H)(Cl){(R)-binap}]⁺ fragments would then lead to [Ir₂(H)₂{(R)-binap}₂(µ-Cl)₂]²⁺, which stabilizes to [Ir₂(H)₂{(R)-binap}₂(µ-Cl)₃]⁺ by the addition of an extra chloride ion provided by the excess of HCl (Dahlenburg et al., 2007). We expected that the formation of triply halido-bridged diiridium complexes [Ir₂(H)₂(L₂)(µ-X)₃]⁺ from hydrogen halides HX and iridium(I) cations [Ir(η⁴-1,5-C₈H₁₂)L₂]⁺ bearing sterically congested bis(phosphines) similar to, or different from, the binap ligand could be a general reaction. Hence, we set out to prepare additional members of this family of compounds because previous work had shown that opening of the µ-Cl bridges of [Ir₂(H)₂{(R)-binap}₂(µ-Cl)₃]BF₄ by various N,N nucleophiles presents a useful method of synthesis for the otherwise involved mixed-ligand bis(chelates) [Ir(H)(Cl){(R)-binap}(1,2-diamine)]BF₄, which are of interest as (pre)catalysts for the enantioselective hydrogenation of ketones (Dahlenburg et al., 2007).

In this context, we came across the reaction between hydrogen chloride and [Ir(η⁴-1,5-C₈H₁₂)(rac-biphep)]BF₄, where rac-biphep is racemic 2,2'-bis(diphenylphosphino)-1,1'-biphenyl as an examplary binap-like chelate ligand which, because of its chiral flexibility, cannot be obtained as resolved enantiomers but can adopt stereochemically robust atropisomeric conformations in metal complexes bearing enantiopure coligands (Becker et al., 2001; Korenaga et al., 2001; Mikami et al., 2001, 2002, 2004, 2005a,b). As anticipated, bimetallic [Ir₂(H)₂(biphep)₂(µ-Cl)₃]BF₄ was isolated from the reaction solution. ¹H and ³¹P{¹H} NMR spectroscopy proved the presence, in a 1:1 molar ratio, of two diastereomers, (I) and (II), differing only in the relative disposition of the hydride ligands and the pairwise configuration of the axially chiral bis(phosphine) chelates, which is syn or anti (trans to the same or to two different bridging chlorides) with regard to the orientation of the two Ir—H bonds, and (R,R)/(S,S) or (R,S) with regard to the chirality of the pair of possible biphep atropisomers. The racemic syn form, (I), with the two biphep ligands in an (R,R) or (S,S) configuration, could be separated as the title addition compound (I)·2CH₂Cl₂ by crystallizing the isomeric mixture from CH₂Cl₂–diethyl ether, and this structure is presented here.

The molecular structure of the title (S,S) enantiomeric complex salt, including the CH₂Cl₂ solvent molecules, is shown in Fig. 1. While a few structural studies on biphep complexes of Ru, Rh, Pd and Pt have been reported in recent years (Becker et al., 2001; Doherty et al., 2005; Korenaga et al., 2001; Mikami et al., 2001, 2002, 2004, 2005a,b; Osawara et al., 2000), the title compound appears to be the first crystallographically characterized example with iridium as the central metal (Cambridge Structural Database, Version 5.28; Allen, 2002).

The geometry of the bimetallic cation can be described as triply chlorido-bridged confacial bioctahedral, with two syn-aligned Ir—H bonds trans to the same halide bridge. The overall structure of the cationic component is virtually C₂ symmetric, with the twofold rotation axis passing through the midpoints of the Ir···Ir vector and the chloride ligand Cl1 trans to both hydrides.

The pairwise shared coordination planes spanned by one metal centre and two bridging chloride ligands are inclined to each other at angles between 120.81 (5) and 127.01 (5)°, with the interplanar angles of the three Ir(µ-Cl)Ir bridges varying from 118.20 (2) to 121.61 (2)°. All of these parameters compare favourably with those determined previously for the related binap complex [Ir₂(H)₂{(R)-binap}₂(µ-Cl)₃]BF₄ (Dahlenburg et al., 2007). The greater chiral flexibility of the biphep system than that of the binap ligand is mirrored by the angles between the normals to the two pairs of phenyl planes in the biphenyl units, which amount to 61.0 (1) and 65.7 (1)° and thus clearly fall below the range of 68–81° spanned by the corresponding dihedral angles between the naphthyl planes in [Ir₂(H)₂{(R)-binap}₂(µ-Cl)₃]BF₄ (Dahlenburg et al., 2007) and [Ir₂(H)₂{(R)-binap}₂(µ-Cl)(µ-OCH₃)₂]Cl (Tani et al., 1998a,b).

As a result of the high trans-bond-weakening influence of the hydride ligands, the Ir—Cl bonds trans to Ir—H are much longer than those opposite Ir—P (Table 1) and are amongst the longest Ir^III—µ-Cl distances reported to date (Dahlenburg et al., 2007). The Ir—P bond lengths and the obtuse P—Ir—P angles agree well with the corresponding distances and valence angles of structurally characterized iridium complexes of the binap ligand (Dahlenburg et al., 2007; Dorta et al., 1997; Tani et al.,1998a,b; Yamagata et al., 1997, 2006).

Related literature

For related literature, see: Allen (2002); Becker et al. (2001); Dahlenburg et al. (2007); Doherty et al. (2005); Dorta et al. (1997); Korenaga et al. (2001); Mikami et al. (2001, 2002, 2004, 2005a, 2005b); Osawara et al. (2000); Tani et al. (1998a, 1998b); Yamagata et al. (1997, 2006).

S2. Experimental

A solution of dry hydrogen chloride in diethyl ether was added dropwise to a THF solution (30 ml) of [Ir(η⁴-1,5-C₈H₁₂)(rac-biphep)]BF₄ (142 mg, 0.16 mmol), which was obtained from [Ir₂(η⁴-1,5-C₈H₁₂)₂(µ-Cl)₂] and the phosphine in the presence of AgBF₄, similar to the procedure previously described for the preparation of [Ir(η⁴-1,5-C₈H₁₂){(R)-binap}]BF₄ and related complex salts (Dahlenburg et al., 2007). The dark-red mixture gradually became pale yellow and the addition of HCl was stopped when no further alteration of the colour was discernible. After stirring for an additional 30 min and concentration of the solution to ~1 ml, the product was precipitated by adding diethyl ether (50 ml), washed with 3 × 2 ml of the same solvent and dried under vacuum. Yield: 120 mg (95%) of colourless [Ir₂(H)₂(biphep)₂(µ-Cl)₃]BF₄ as a 1:1 molar mixture of the syn-(R,R)/(S,S) diastereomer, (I), and the anti-(R,S) form, (II). Elemental analysis, found: C 53.74, H 3.85%; calculated for C₇₂H₅₈BCl₃F₄Ir₂P₄ (1624.75): C 53.23, H 3.60%. Spectroscopic analysis for (I): ¹H NMR (CDCl₃, δ, p.p.m.): -23.04 (dd, ²J_P,H = 15.61, ²J_P',H = 21.67 Hz, 2 IrH); ³¹P{¹H} NMR (CDCl₃, δ, p.p.m.): -1.67, -7.52 (both d, ²J_P,_P' = 20.0 Hz, 1 P each). Spectroscopic analysis for (II): ¹H NMR (CDCl₃, δ, p.p.m.): -22.47 (dd, ²J_P,H = 16.07, ²J_P',H = 22.01 Hz, 1 IrH), -22.73 (dd, ²J_P,H = 16.66, ²J_P',H = 21.43 Hz, 1 IrH); ³¹P{¹H} NMR (CDCl₃, δ, p.p.m.): 0.00, -1.96, -4.14, -7.43 (all d, ²J_P,_P' = 18.0 Hz each, all 1 P).

Slow diffusion of diethyl ether into a saturated solution of the isomeric mixture in CH₂Cl₂ resulted in the deposition of single crystals of the title addition compound (I)·2CH₂Cl₂.

S3. Refinement

Carbon-bonded H atoms were positioned geometrically, with C—H = 0.95–0.99 Å, and refined using appropriate riding models, with U_iso(H) = 1.2U_eq(C). The positions of the two hydride ligands were derived from a final ΔF map; during refinement, their U_iso values were fixed at 1.5U_eq(Ir).

Computing details

Data collection: COLLECT (Bruker, 2002); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL (Bruker, 2002); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Version 1.9.2; Westrip, 2008).

Figures

Fig. 1. The structure of (I)·2CH2Cl2, including the two CH2Cl2 solvent molecules, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Carbon-bonded H atoms of the complex cation have been omitted for clarity.

syn-Tri-µ-chlorido-bis{[(R,R)/(S,S)-2,2'-bis(diphenylphosphino)-1,1'- biphenyl]hydridoiridium(III)} tetrafluoridoborate dichloromethane disolvate

Crystal data

[Ir2Cl3H2(C36H28P2)2]BF4·2CH2Cl2	Z = 2
Mr = 1794.48	F(000) = 1760
Triclinic, P1	Dx = 1.717 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 13.6578 (14) Å	Cell parameters from 339 reflections
b = 14.7640 (6) Å	θ = 6.0–20.0°
c = 18.5300 (11) Å	µ = 4.25 mm^−1
α = 68.701 (3)°	T = 150 K
β = 86.357 (6)°	Irregular, colourless
γ = 86.228 (5)°	0.17 × 0.14 × 0.14 mm
V = 3470.5 (4) Å^3

Data collection

Bruker Nonius KappaCCD diffractometer	16517 independent reflections
Radiation source: fine-focus sealed tube	13333 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 9 pixels mm^-1	θmax = 27.9°, θmin = 3.3°
ω–rotations with 1.90 ° and 123 sec per frame scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −19→19
Tmin = 0.463, Tmax = 0.550	l = −24→24
85276 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: geom except Ir bound hydrogens difmap
wR(F^2) = 0.052	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.014P)^2 + 7.4384P] where P = (Fo^2 + 2Fc^2)/3
16517 reflections	(Δ/σ)max = 0.002
835 parameters	Δρmax = 2.05 e Å^−3
0 restraints	Δρmin = −1.07 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ir1	0.863382 (9)	0.661588 (8)	0.684299 (7)	0.01511 (3)
H1	0.906 (2)	0.657 (2)	0.6124 (19)	0.023*
Ir2	0.739005 (9)	0.861637 (8)	0.689832 (6)	0.01460 (3)
H2	0.721 (2)	0.943 (2)	0.6196 (19)	0.022*
Cl1	0.78098 (6)	0.70047 (5)	0.79624 (4)	0.01786 (15)
Cl2	0.71081 (6)	0.74837 (5)	0.62574 (4)	0.02013 (15)
Cl3	0.90771 (6)	0.82950 (5)	0.64792 (4)	0.01879 (15)
P1	1.00653 (6)	0.59680 (5)	0.73916 (4)	0.01594 (16)
P2	0.81485 (6)	0.51544 (6)	0.69107 (5)	0.01937 (17)
P3	0.58106 (6)	0.87799 (6)	0.72688 (4)	0.01616 (16)
P4	0.78729 (6)	0.98078 (5)	0.72661 (4)	0.01591 (16)
C1	0.9909 (2)	0.4781 (2)	0.81594 (17)	0.0176 (6)
C2	0.9808 (3)	0.4755 (2)	0.89223 (19)	0.0243 (7)
H2A	0.9878	0.5332	0.9025	0.029*
C3	0.9608 (3)	0.3897 (3)	0.95296 (19)	0.0290 (8)
H3A	0.9522	0.3893	1.0044	0.035*
C4	0.9534 (3)	0.3051 (2)	0.9391 (2)	0.0276 (8)
H4A	0.9408	0.2461	0.9810	0.033*
C5	0.9644 (3)	0.3061 (2)	0.8645 (2)	0.0249 (7)
H5A	0.9614	0.2468	0.8557	0.030*
C6	0.9797 (2)	0.3923 (2)	0.80133 (18)	0.0197 (7)
C7	0.9820 (2)	0.3865 (2)	0.72275 (18)	0.0203 (7)
C8	1.0518 (3)	0.3232 (2)	0.7059 (2)	0.0260 (7)
H8A	1.0974	0.2873	0.7437	0.031*
C9	1.0559 (3)	0.3116 (3)	0.6351 (2)	0.0348 (9)
H9A	1.1044	0.2685	0.6243	0.042*
C10	0.9895 (3)	0.3629 (3)	0.5800 (2)	0.0373 (9)
H10A	0.9927	0.3557	0.5310	0.045*
C11	0.9180 (3)	0.4247 (3)	0.5961 (2)	0.0312 (8)
H11A	0.8717	0.4586	0.5582	0.037*
C12	0.9128 (2)	0.4381 (2)	0.66702 (19)	0.0205 (7)
C13	1.0693 (2)	0.6649 (2)	0.78717 (17)	0.0195 (6)
C14	1.0231 (3)	0.7354 (2)	0.81171 (18)	0.0235 (7)
H14A	0.9550	0.7508	0.8041	0.028*
C15	1.0754 (3)	0.7840 (3)	0.8475 (2)	0.0277 (8)
H15A	1.0427	0.8330	0.8632	0.033*
C16	1.1730 (3)	0.7621 (3)	0.8601 (2)	0.0326 (9)
H16A	1.2084	0.7960	0.8841	0.039*
C17	1.2199 (3)	0.6901 (3)	0.8377 (3)	0.0461 (11)
H17A	1.2875	0.6735	0.8472	0.055*
C18	1.1684 (3)	0.6420 (3)	0.8013 (2)	0.0363 (9)
H18A	1.2013	0.5928	0.7858	0.044*
C19	1.1034 (2)	0.5841 (2)	0.67083 (17)	0.0182 (6)
C20	1.1126 (3)	0.6600 (2)	0.59978 (19)	0.0251 (7)
H20A	1.0657	0.7133	0.5868	0.030*
C21	1.1895 (3)	0.6586 (3)	0.54787 (19)	0.0301 (8)
H21A	1.1958	0.7112	0.4997	0.036*
C22	1.2575 (3)	0.5803 (3)	0.5663 (2)	0.0287 (8)
H22A	1.3096	0.5786	0.5303	0.034*
C23	1.2496 (3)	0.5049 (2)	0.63685 (19)	0.0238 (7)
H23A	1.2963	0.4515	0.6495	0.029*
C24	1.1734 (2)	0.5071 (2)	0.68928 (18)	0.0197 (7)
H24A	1.1688	0.4557	0.7383	0.024*
C25	0.7598 (2)	0.4300 (2)	0.7795 (2)	0.0225 (7)
C26	0.7349 (3)	0.4547 (2)	0.8439 (2)	0.0283 (8)
H26A	0.7455	0.5182	0.8426	0.034*
C27	0.6943 (3)	0.3858 (3)	0.9107 (2)	0.0393 (10)
H27A	0.6775	0.4025	0.9550	0.047*
C28	0.6785 (3)	0.2934 (3)	0.9127 (3)	0.0441 (11)
H28A	0.6506	0.2469	0.9582	0.053*
C29	0.7032 (3)	0.2686 (3)	0.8488 (3)	0.0413 (10)
H29A	0.6923	0.2050	0.8505	0.050*
C30	0.7436 (3)	0.3357 (3)	0.7826 (2)	0.0323 (8)
H30A	0.7606	0.3180	0.7388	0.039*
C31	0.7215 (3)	0.5375 (2)	0.6190 (2)	0.0268 (8)
C32	0.6267 (3)	0.5074 (3)	0.6415 (2)	0.0331 (9)
H32A	0.6111	0.4683	0.6939	0.040*
C33	0.5543 (3)	0.5350 (3)	0.5870 (3)	0.0462 (11)
H33A	0.4892	0.5146	0.6024	0.055*
C34	0.5759 (3)	0.5910 (3)	0.5116 (3)	0.0490 (13)
H34A	0.5256	0.6100	0.4752	0.059*
C35	0.6704 (4)	0.6201 (3)	0.4879 (2)	0.0411 (11)
H35A	0.6855	0.6573	0.4350	0.049*
C36	0.7432 (3)	0.5946 (2)	0.5418 (2)	0.0315 (9)
H36A	0.8078	0.6162	0.5261	0.038*
C37	0.5708 (2)	0.8909 (2)	0.82169 (17)	0.0168 (6)
C38	0.5480 (2)	0.8120 (2)	0.88836 (19)	0.0231 (7)
H38A	0.5313	0.7526	0.8843	0.028*
C39	0.5494 (2)	0.8194 (2)	0.96044 (18)	0.0216 (7)
H39A	0.5363	0.7642	1.0056	0.026*
C40	0.5696 (2)	0.9061 (2)	0.96781 (19)	0.0238 (7)
H40A	0.5695	0.9109	1.0175	0.029*
C41	0.5898 (2)	0.9853 (2)	0.90182 (19)	0.0217 (7)
H41A	0.6025	1.0453	0.9066	0.026*
C42	0.5920 (2)	0.9798 (2)	0.82814 (17)	0.0175 (6)
C43	0.6133 (2)	1.0712 (2)	0.76059 (17)	0.0172 (6)
C44	0.5465 (2)	1.1504 (2)	0.74946 (19)	0.0231 (7)
H44A	0.4892	1.1431	0.7825	0.028*
C45	0.5623 (3)	1.2395 (2)	0.6911 (2)	0.0288 (8)
H45A	0.5152	1.2921	0.6834	0.035*
C46	0.6466 (3)	1.2511 (2)	0.6444 (2)	0.0302 (8)
H46A	0.6582	1.3123	0.6047	0.036*
C47	0.7143 (3)	1.1741 (2)	0.65520 (19)	0.0264 (8)
H47A	0.7728	1.1832	0.6233	0.032*
C48	0.6982 (2)	1.0831 (2)	0.71230 (17)	0.0183 (6)
C49	0.5116 (2)	0.7734 (2)	0.73181 (19)	0.0204 (7)
C50	0.5394 (3)	0.6791 (2)	0.7797 (2)	0.0256 (7)
H50A	0.5917	0.6691	0.8136	0.031*
C51	0.4915 (3)	0.5997 (3)	0.7784 (2)	0.0317 (8)
H51A	0.5100	0.5360	0.8122	0.038*
C52	0.4169 (3)	0.6132 (3)	0.7281 (2)	0.0364 (9)
H52A	0.3844	0.5588	0.7268	0.044*
C53	0.3898 (3)	0.7061 (3)	0.6795 (2)	0.0389 (9)
H53A	0.3390	0.7154	0.6445	0.047*
C54	0.4360 (3)	0.7860 (3)	0.6815 (2)	0.0300 (8)
H54A	0.4161	0.8497	0.6484	0.036*
C55	0.5052 (2)	0.9803 (2)	0.66626 (18)	0.0204 (7)
C56	0.4162 (3)	1.0031 (3)	0.6984 (2)	0.0274 (8)
H56A	0.3993	0.9689	0.7516	0.033*
C57	0.3524 (3)	1.0750 (3)	0.6534 (2)	0.0335 (9)
H57A	0.2922	1.0905	0.6759	0.040*
C58	0.3756 (3)	1.1243 (3)	0.5761 (2)	0.0378 (10)
H58A	0.3309	1.1727	0.5451	0.045*
C59	0.4635 (3)	1.1032 (3)	0.5440 (2)	0.0401 (10)
H59A	0.4802	1.1381	0.4909	0.048*
C60	0.5283 (3)	1.0307 (3)	0.5888 (2)	0.0298 (8)
H60A	0.5886	1.0159	0.5661	0.036*
C61	0.8238 (2)	0.9573 (2)	0.82518 (18)	0.0190 (6)
C62	0.8528 (3)	1.0351 (3)	0.8435 (2)	0.0283 (8)
H62A	0.8528	1.0987	0.8052	0.034*
C63	0.8815 (3)	1.0195 (3)	0.9174 (2)	0.0348 (9)
H63A	0.9014	1.0724	0.9298	0.042*
C64	0.8814 (3)	0.9271 (3)	0.9734 (2)	0.0317 (8)
H64A	0.9031	0.9164	1.0236	0.038*
C65	0.8500 (3)	0.8501 (3)	0.95661 (19)	0.0275 (8)
H65A	0.8480	0.7871	0.9957	0.033*
C66	0.8213 (2)	0.8654 (2)	0.88226 (18)	0.0215 (7)
H66A	0.7998	0.8126	0.8705	0.026*
C67	0.8949 (2)	1.0313 (2)	0.66480 (19)	0.0213 (7)
C68	0.8876 (3)	1.0664 (2)	0.58386 (19)	0.0264 (8)
H68A	0.8254	1.0710	0.5623	0.032*
C69	0.9698 (3)	1.0942 (2)	0.5353 (2)	0.0319 (9)
H69A	0.9640	1.1186	0.4807	0.038*
C70	1.0597 (3)	1.0867 (3)	0.5660 (3)	0.0466 (11)
H70A	1.1162	1.1060	0.5324	0.056*
C71	1.0693 (3)	1.0516 (4)	0.6448 (3)	0.0488 (12)
H71A	1.1322	1.0460	0.6656	0.059*
C72	0.9862 (3)	1.0239 (3)	0.6945 (2)	0.0332 (9)
H72A	0.9928	0.9999	0.7491	0.040*
B1	0.6658 (4)	0.7034 (3)	0.1944 (2)	0.0326 (10)
F11	0.60863 (17)	0.77401 (15)	0.14101 (12)	0.0376 (5)
F12	0.67463 (19)	0.72846 (17)	0.25906 (13)	0.0453 (6)
F13	0.75870 (19)	0.6974 (2)	0.16131 (15)	0.0573 (7)
F14	0.6224 (2)	0.61524 (18)	0.21617 (17)	0.0687 (9)
C100	0.7413 (3)	0.9350 (3)	0.1381 (2)	0.0366 (9)
H10B	0.7493	0.8936	0.1061	0.044*
H10C	0.6996	0.9009	0.1845	0.044*
Cl11	0.85706 (9)	0.95000 (10)	0.16734 (8)	0.0577 (3)
Cl12	0.68270 (9)	1.04513 (9)	0.08503 (8)	0.0564 (3)
C200	0.3078 (4)	0.4082 (5)	0.9488 (4)	0.0719 (16)
H20B	0.3031	0.4449	0.8925	0.086*
H20C	0.3144	0.3380	0.9570	0.086*
Cl21	0.41236 (10)	0.44210 (9)	0.98166 (8)	0.0609 (3)
Cl22	0.20185 (11)	0.43078 (12)	0.99651 (9)	0.0786 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01962 (7)	0.01236 (6)	0.01465 (6)	0.00167 (5)	−0.00436 (5)	−0.00625 (5)
Ir2	0.01946 (7)	0.01146 (6)	0.01296 (6)	0.00000 (5)	−0.00029 (5)	−0.00469 (5)
Cl1	0.0236 (4)	0.0148 (3)	0.0150 (3)	−0.0018 (3)	−0.0013 (3)	−0.0049 (3)
Cl2	0.0255 (4)	0.0181 (3)	0.0201 (4)	0.0052 (3)	−0.0090 (3)	−0.0105 (3)
Cl3	0.0227 (4)	0.0138 (3)	0.0191 (4)	−0.0007 (3)	0.0041 (3)	−0.0058 (3)
P1	0.0197 (4)	0.0132 (4)	0.0161 (4)	−0.0004 (3)	−0.0034 (3)	−0.0063 (3)
P2	0.0231 (4)	0.0150 (4)	0.0231 (4)	0.0023 (3)	−0.0101 (3)	−0.0096 (3)
P3	0.0193 (4)	0.0136 (4)	0.0161 (4)	−0.0018 (3)	−0.0020 (3)	−0.0056 (3)
P4	0.0201 (4)	0.0130 (4)	0.0151 (4)	−0.0028 (3)	0.0036 (3)	−0.0060 (3)
C1	0.0163 (15)	0.0162 (14)	0.0181 (15)	−0.0023 (12)	−0.0049 (12)	−0.0028 (12)
C2	0.0288 (19)	0.0228 (16)	0.0214 (16)	−0.0070 (14)	−0.0041 (14)	−0.0067 (14)
C3	0.036 (2)	0.0323 (19)	0.0165 (16)	−0.0077 (16)	−0.0037 (14)	−0.0049 (14)
C4	0.0287 (19)	0.0204 (16)	0.0245 (17)	−0.0053 (14)	−0.0053 (14)	0.0040 (14)
C5	0.0252 (18)	0.0170 (15)	0.0310 (18)	−0.0016 (14)	−0.0063 (14)	−0.0059 (14)
C6	0.0176 (16)	0.0171 (15)	0.0235 (16)	0.0015 (12)	−0.0085 (13)	−0.0054 (13)
C7	0.0263 (18)	0.0125 (14)	0.0229 (16)	−0.0007 (13)	−0.0057 (13)	−0.0067 (13)
C8	0.0284 (19)	0.0182 (16)	0.0317 (19)	0.0041 (14)	−0.0093 (15)	−0.0090 (14)
C9	0.037 (2)	0.032 (2)	0.043 (2)	0.0129 (17)	−0.0091 (18)	−0.0241 (18)
C10	0.049 (3)	0.037 (2)	0.037 (2)	0.0134 (19)	−0.0122 (18)	−0.0265 (18)
C11	0.043 (2)	0.0265 (18)	0.0302 (19)	0.0115 (16)	−0.0186 (17)	−0.0172 (16)
C12	0.0241 (17)	0.0149 (15)	0.0263 (17)	0.0016 (13)	−0.0075 (14)	−0.0113 (13)
C13	0.0231 (17)	0.0195 (15)	0.0166 (15)	−0.0053 (13)	−0.0016 (13)	−0.0065 (13)
C14	0.0251 (18)	0.0257 (17)	0.0225 (16)	−0.0016 (14)	−0.0024 (14)	−0.0118 (14)
C15	0.036 (2)	0.0255 (17)	0.0276 (18)	−0.0050 (16)	−0.0005 (15)	−0.0160 (15)
C16	0.033 (2)	0.041 (2)	0.035 (2)	−0.0145 (17)	0.0006 (16)	−0.0252 (18)
C17	0.024 (2)	0.070 (3)	0.067 (3)	0.000 (2)	−0.0119 (19)	−0.049 (3)
C18	0.027 (2)	0.044 (2)	0.051 (2)	0.0039 (17)	−0.0095 (18)	−0.034 (2)
C19	0.0200 (16)	0.0188 (15)	0.0181 (15)	0.0002 (13)	−0.0039 (12)	−0.0089 (13)
C20	0.0297 (19)	0.0200 (16)	0.0217 (16)	0.0049 (14)	−0.0032 (14)	−0.0036 (13)
C21	0.037 (2)	0.0288 (18)	0.0174 (16)	0.0035 (16)	0.0030 (15)	−0.0007 (14)
C22	0.0291 (19)	0.035 (2)	0.0229 (17)	0.0023 (16)	0.0013 (14)	−0.0130 (15)
C23	0.0240 (18)	0.0228 (16)	0.0264 (17)	0.0038 (14)	−0.0059 (14)	−0.0109 (14)
C24	0.0210 (17)	0.0193 (15)	0.0194 (15)	0.0008 (13)	−0.0069 (13)	−0.0068 (13)
C25	0.0184 (16)	0.0160 (15)	0.0327 (18)	−0.0025 (13)	−0.0071 (14)	−0.0069 (14)
C26	0.0268 (19)	0.0199 (16)	0.037 (2)	−0.0031 (14)	−0.0004 (15)	−0.0085 (15)
C27	0.040 (2)	0.034 (2)	0.039 (2)	−0.0062 (18)	0.0103 (18)	−0.0090 (18)
C28	0.033 (2)	0.026 (2)	0.061 (3)	−0.0117 (17)	0.011 (2)	−0.0014 (19)
C29	0.034 (2)	0.0232 (19)	0.066 (3)	−0.0126 (17)	−0.002 (2)	−0.013 (2)
C30	0.0257 (19)	0.0252 (18)	0.052 (2)	−0.0045 (15)	−0.0092 (17)	−0.0196 (17)
C31	0.034 (2)	0.0187 (16)	0.0346 (19)	0.0097 (15)	−0.0185 (16)	−0.0175 (15)
C32	0.031 (2)	0.0289 (19)	0.050 (2)	0.0094 (16)	−0.0197 (18)	−0.0257 (18)
C33	0.034 (2)	0.050 (3)	0.071 (3)	0.016 (2)	−0.029 (2)	−0.039 (2)
C34	0.051 (3)	0.047 (3)	0.066 (3)	0.028 (2)	−0.044 (2)	−0.039 (2)
C35	0.065 (3)	0.030 (2)	0.038 (2)	0.021 (2)	−0.032 (2)	−0.0230 (18)
C36	0.042 (2)	0.0248 (18)	0.036 (2)	0.0116 (16)	−0.0201 (17)	−0.0202 (16)
C37	0.0157 (15)	0.0182 (15)	0.0166 (15)	−0.0013 (12)	−0.0011 (12)	−0.0063 (12)
C38	0.0244 (18)	0.0212 (16)	0.0230 (17)	−0.0036 (14)	0.0004 (14)	−0.0069 (14)
C39	0.0154 (16)	0.0208 (16)	0.0196 (16)	−0.0034 (13)	0.0038 (12)	0.0031 (13)
C40	0.0225 (17)	0.0335 (19)	0.0166 (15)	−0.0024 (15)	0.0012 (13)	−0.0107 (14)
C41	0.0198 (17)	0.0243 (16)	0.0258 (17)	−0.0012 (13)	0.0000 (13)	−0.0148 (14)
C42	0.0165 (15)	0.0180 (15)	0.0172 (15)	−0.0007 (12)	0.0017 (12)	−0.0058 (12)
C43	0.0212 (16)	0.0164 (14)	0.0174 (15)	−0.0035 (13)	−0.0007 (12)	−0.0097 (12)
C44	0.0228 (17)	0.0205 (16)	0.0282 (17)	−0.0009 (13)	0.0019 (14)	−0.0120 (14)
C45	0.034 (2)	0.0201 (17)	0.0326 (19)	0.0057 (15)	−0.0019 (16)	−0.0116 (15)
C46	0.043 (2)	0.0138 (15)	0.0286 (18)	−0.0010 (15)	0.0062 (16)	−0.0024 (14)
C47	0.036 (2)	0.0168 (16)	0.0238 (17)	−0.0014 (14)	0.0100 (15)	−0.0060 (14)
C48	0.0259 (18)	0.0123 (14)	0.0175 (15)	−0.0012 (13)	0.0013 (13)	−0.0069 (12)
C49	0.0216 (17)	0.0174 (15)	0.0250 (17)	−0.0050 (13)	0.0013 (13)	−0.0108 (13)
C50	0.0240 (18)	0.0234 (17)	0.0322 (19)	−0.0052 (14)	0.0007 (15)	−0.0127 (15)
C51	0.028 (2)	0.0204 (17)	0.046 (2)	−0.0061 (15)	0.0070 (17)	−0.0121 (16)
C52	0.035 (2)	0.0275 (19)	0.054 (3)	−0.0137 (17)	0.0046 (19)	−0.0222 (18)
C53	0.037 (2)	0.041 (2)	0.048 (2)	−0.0083 (19)	−0.0097 (19)	−0.024 (2)
C54	0.031 (2)	0.0278 (18)	0.035 (2)	−0.0039 (16)	−0.0058 (16)	−0.0147 (16)
C55	0.0235 (17)	0.0171 (15)	0.0221 (16)	0.0005 (13)	−0.0064 (13)	−0.0083 (13)
C56	0.0258 (19)	0.0302 (19)	0.0282 (18)	0.0033 (15)	−0.0048 (15)	−0.0130 (15)
C57	0.029 (2)	0.038 (2)	0.039 (2)	0.0089 (17)	−0.0105 (17)	−0.0215 (18)
C58	0.043 (2)	0.0282 (19)	0.044 (2)	0.0161 (18)	−0.0236 (19)	−0.0150 (18)
C59	0.053 (3)	0.035 (2)	0.0235 (19)	0.0079 (19)	−0.0120 (18)	0.0002 (16)
C60	0.033 (2)	0.0277 (18)	0.0251 (18)	0.0028 (16)	−0.0031 (15)	−0.0058 (15)
C61	0.0173 (16)	0.0224 (16)	0.0199 (15)	−0.0014 (13)	0.0010 (12)	−0.0109 (13)
C62	0.036 (2)	0.0260 (18)	0.0262 (18)	−0.0088 (16)	0.0031 (15)	−0.0123 (15)
C63	0.040 (2)	0.041 (2)	0.035 (2)	−0.0130 (18)	0.0011 (17)	−0.0261 (18)
C64	0.031 (2)	0.049 (2)	0.0219 (17)	−0.0056 (17)	−0.0019 (15)	−0.0199 (17)
C65	0.0304 (19)	0.0321 (19)	0.0193 (16)	0.0010 (16)	−0.0016 (14)	−0.0089 (15)
C66	0.0230 (17)	0.0219 (16)	0.0220 (16)	0.0005 (13)	−0.0002 (13)	−0.0113 (14)
C67	0.0275 (18)	0.0128 (14)	0.0255 (17)	−0.0071 (13)	0.0094 (14)	−0.0100 (13)
C68	0.033 (2)	0.0172 (16)	0.0262 (18)	−0.0011 (14)	0.0086 (15)	−0.0059 (14)
C69	0.040 (2)	0.0211 (17)	0.0317 (19)	−0.0044 (16)	0.0178 (17)	−0.0082 (15)
C70	0.044 (3)	0.051 (3)	0.049 (3)	−0.028 (2)	0.028 (2)	−0.024 (2)
C71	0.030 (2)	0.073 (3)	0.055 (3)	−0.025 (2)	0.014 (2)	−0.036 (3)
C72	0.030 (2)	0.043 (2)	0.034 (2)	−0.0159 (17)	0.0089 (16)	−0.0208 (18)
B1	0.043 (3)	0.023 (2)	0.030 (2)	0.0067 (19)	−0.0082 (19)	−0.0076 (17)
F11	0.0452 (14)	0.0332 (12)	0.0292 (11)	0.0089 (10)	−0.0106 (10)	−0.0053 (9)
F12	0.0616 (17)	0.0434 (13)	0.0302 (12)	0.0071 (12)	−0.0106 (11)	−0.0126 (11)
F13	0.0485 (16)	0.0715 (18)	0.0565 (16)	0.0227 (14)	−0.0083 (13)	−0.0319 (15)
F14	0.102 (2)	0.0303 (13)	0.0666 (18)	−0.0134 (15)	−0.0338 (17)	−0.0016 (13)
C100	0.033 (2)	0.039 (2)	0.044 (2)	−0.0077 (18)	0.0019 (18)	−0.0217 (19)
Cl11	0.0445 (7)	0.0784 (8)	0.0685 (8)	0.0069 (6)	−0.0221 (6)	−0.0465 (7)
Cl12	0.0570 (7)	0.0489 (6)	0.0690 (8)	0.0105 (6)	−0.0258 (6)	−0.0264 (6)
C200	0.054 (3)	0.095 (4)	0.090 (4)	0.006 (3)	−0.023 (3)	−0.059 (4)
Cl21	0.0541 (7)	0.0497 (7)	0.0836 (9)	−0.0070 (6)	−0.0114 (7)	−0.0276 (7)
Cl22	0.0504 (8)	0.0973 (11)	0.0725 (9)	−0.0026 (8)	0.0027 (7)	−0.0130 (8)

Geometric parameters (Å, º)

Ir1—P1	2.2518 (8)	C33—H33A	0.9500
Ir1—P2	2.2565 (8)	C34—C35	1.381 (7)
Ir1—Cl3	2.4287 (7)	C34—H34A	0.9500
Ir1—Cl2	2.4672 (8)	C35—C36	1.391 (5)
Ir1—Cl1	2.5262 (7)	C35—H35A	0.9500
Ir1—H1	1.44 (3)	C36—H36A	0.9500
Ir2—P3	2.2464 (9)	C37—C38	1.391 (4)
Ir2—P4	2.2526 (8)	C37—C42	1.411 (4)
Ir2—Cl2	2.4374 (7)	C38—C39	1.381 (5)
Ir2—Cl3	2.4563 (8)	C38—H38A	0.9500
Ir2—Cl1	2.5365 (7)	C39—C40	1.382 (5)
Ir2—H2	1.44 (3)	C39—H39A	0.9500
P1—C19	1.821 (3)	C40—C41	1.379 (5)
P1—C1	1.828 (3)	C40—H40A	0.9500
P1—C13	1.843 (3)	C41—C42	1.395 (4)
P2—C25	1.819 (3)	C41—H41A	0.9500
P2—C31	1.833 (3)	C42—C43	1.500 (4)
P2—C12	1.840 (3)	C43—C44	1.397 (4)
P3—C55	1.824 (3)	C43—C48	1.398 (4)
P3—C37	1.830 (3)	C44—C45	1.385 (5)
P3—C49	1.836 (3)	C44—H44A	0.9500
P4—C61	1.827 (3)	C45—C46	1.377 (5)
P4—C67	1.827 (3)	C45—H45A	0.9500
P4—C48	1.828 (3)	C46—C47	1.382 (5)
C1—C2	1.398 (4)	C46—H46A	0.9500
C1—C6	1.407 (4)	C47—C48	1.396 (4)
C2—C3	1.384 (5)	C47—H47A	0.9500
C2—H2A	0.9500	C49—C54	1.392 (5)
C3—C4	1.373 (5)	C49—C50	1.395 (5)
C3—H3A	0.9500	C50—C51	1.388 (5)
C4—C5	1.377 (5)	C50—H50A	0.9500
C4—H4A	0.9500	C51—C52	1.380 (6)
C5—C6	1.399 (4)	C51—H51A	0.9500
C5—H5A	0.9500	C52—C53	1.381 (6)
C6—C7	1.488 (4)	C52—H52A	0.9500
C7—C8	1.392 (5)	C53—C54	1.387 (5)
C7—C12	1.413 (4)	C53—H53A	0.9500
C8—C9	1.380 (5)	C54—H54A	0.9500
C8—H8A	0.9500	C55—C60	1.382 (5)
C9—C10	1.380 (5)	C55—C56	1.395 (5)
C9—H9A	0.9500	C56—C57	1.382 (5)
C10—C11	1.386 (5)	C56—H56A	0.9500
C10—H10A	0.9500	C57—C58	1.377 (6)
C11—C12	1.395 (5)	C57—H57A	0.9500
C11—H11A	0.9500	C58—C59	1.374 (6)
C13—C14	1.382 (4)	C58—H58A	0.9500
C13—C18	1.391 (5)	C59—C60	1.393 (5)
C14—C15	1.391 (5)	C59—H59A	0.9500
C14—H14A	0.9500	C60—H60A	0.9500
C15—C16	1.367 (5)	C61—C66	1.385 (4)
C15—H15A	0.9500	C61—C62	1.398 (4)
C16—C17	1.381 (5)	C62—C63	1.381 (5)
C16—H16A	0.9500	C62—H62A	0.9500
C17—C18	1.389 (5)	C63—C64	1.381 (5)
C17—H17A	0.9500	C63—H63A	0.9500
C18—H18A	0.9500	C64—C65	1.382 (5)
C19—C20	1.390 (4)	C64—H64A	0.9500
C19—C24	1.392 (4)	C65—C66	1.390 (4)
C20—C21	1.383 (5)	C65—H65A	0.9500
C20—H20A	0.9500	C66—H66A	0.9500
C21—C22	1.389 (5)	C67—C72	1.377 (5)
C21—H21A	0.9500	C67—C68	1.406 (5)
C22—C23	1.378 (5)	C68—C69	1.379 (5)
C22—H22A	0.9500	C68—H68A	0.9500
C23—C24	1.385 (5)	C69—C70	1.366 (6)
C23—H23A	0.9500	C69—H69A	0.9500
C24—H24A	0.9500	C70—C71	1.374 (6)
C25—C26	1.386 (5)	C70—H70A	0.9500
C25—C30	1.405 (4)	C71—C72	1.399 (5)
C26—C27	1.395 (5)	C71—H71A	0.9500
C26—H26A	0.9500	C72—H72A	0.9500
C27—C28	1.383 (6)	B1—F14	1.378 (5)
C27—H27A	0.9500	B1—F11	1.384 (5)
C28—C29	1.376 (6)	B1—F13	1.385 (5)
C28—H28A	0.9500	B1—F12	1.391 (5)
C29—C30	1.376 (6)	C100—Cl12	1.738 (4)
C29—H29A	0.9500	C100—Cl11	1.756 (4)
C30—H30A	0.9500	C100—H10B	0.9900
C31—C32	1.386 (5)	C100—H10C	0.9900
C31—C36	1.394 (5)	C200—Cl22	1.725 (6)
C32—C33	1.393 (5)	C200—Cl21	1.757 (5)
C32—H32A	0.9500	C200—H20B	0.9900
C33—C34	1.365 (7)	C200—H20C	0.9900
P1—Ir1—P2	92.35 (3)	C25—C30—H30A	119.9
P1—Ir1—Cl3	95.11 (3)	C32—C31—C36	119.5 (3)
P2—Ir1—Cl3	167.70 (3)	C32—C31—P2	120.7 (3)
P1—Ir1—Cl2	174.05 (3)	C36—C31—P2	119.4 (3)
P2—Ir1—Cl2	93.52 (3)	C31—C32—C33	119.6 (4)
Cl3—Ir1—Cl2	79.29 (3)	C31—C32—H32A	120.2
P1—Ir1—Cl1	98.28 (3)	C33—C32—H32A	120.2
P2—Ir1—Cl1	108.34 (3)	C34—C33—C32	120.7 (4)
Cl3—Ir1—Cl1	80.26 (2)	C34—C33—H33A	119.7
Cl2—Ir1—Cl1	78.91 (2)	C32—C33—H33A	119.7
P1—Ir1—H1	88.2 (14)	C33—C34—C35	120.5 (4)
P2—Ir1—H1	79.3 (13)	C33—C34—H34A	119.8
Cl3—Ir1—H1	91.2 (13)	C35—C34—H34A	119.8
Cl2—Ir1—H1	93.8 (13)	C34—C35—C36	119.6 (4)
Cl1—Ir1—H1	169.6 (13)	C34—C35—H35A	120.2
P3—Ir2—P4	93.80 (3)	C36—C35—H35A	120.2
P3—Ir2—Cl2	95.58 (3)	C35—C36—C31	120.2 (4)
P4—Ir2—Cl2	167.55 (3)	C35—C36—H36A	119.9
P3—Ir2—Cl3	174.60 (3)	C31—C36—H36A	119.9
P4—Ir2—Cl3	91.50 (3)	C38—C37—C42	119.4 (3)
Cl2—Ir2—Cl3	79.33 (3)	C38—C37—P3	120.6 (2)
P3—Ir2—Cl1	97.83 (3)	C42—C37—P3	119.9 (2)
P4—Ir2—Cl1	107.55 (3)	C39—C38—C37	120.4 (3)
Cl2—Ir2—Cl1	79.27 (2)	C39—C38—H38A	119.8
Cl3—Ir2—Cl1	79.53 (3)	C37—C38—H38A	119.8
P3—Ir2—H2	88.1 (13)	C38—C39—C40	121.0 (3)
P4—Ir2—H2	81.1 (13)	C38—C39—H39A	119.5
Cl2—Ir2—H2	91.1 (13)	C40—C39—H39A	119.5
Cl3—Ir2—H2	93.7 (13)	C41—C40—C39	118.9 (3)
Cl1—Ir2—H2	169.1 (13)	C41—C40—H40A	120.5
Ir1—Cl1—Ir2	82.56 (2)	C39—C40—H40A	120.5
Ir2—Cl2—Ir1	85.85 (2)	C40—C41—C42	121.8 (3)
Ir1—Cl3—Ir2	86.28 (2)	C40—C41—H41A	119.1
C19—P1—C1	108.54 (14)	C42—C41—H41A	119.1
C19—P1—C13	100.68 (14)	C41—C42—C37	118.5 (3)
C1—P1—C13	103.28 (14)	C41—C42—C43	117.0 (3)
C19—P1—Ir1	114.03 (10)	C37—C42—C43	124.5 (3)
C1—P1—Ir1	111.59 (10)	C44—C43—C48	118.9 (3)
C13—P1—Ir1	117.60 (11)	C44—C43—C42	116.9 (3)
C25—P2—C31	104.13 (16)	C48—C43—C42	124.0 (3)
C25—P2—C12	101.49 (15)	C45—C44—C43	121.3 (3)
C31—P2—C12	106.06 (15)	C45—C44—H44A	119.4
C25—P2—Ir1	121.92 (11)	C43—C44—H44A	119.4
C31—P2—Ir1	107.60 (11)	C46—C45—C44	119.5 (3)
C12—P2—Ir1	114.27 (11)	C46—C45—H45A	120.2
C55—P3—C37	103.64 (14)	C44—C45—H45A	120.2
C55—P3—C49	102.05 (15)	C45—C46—C47	120.1 (3)
C37—P3—C49	108.81 (14)	C45—C46—H46A	119.9
C55—P3—Ir2	118.97 (11)	C47—C46—H46A	119.9
C37—P3—Ir2	111.08 (10)	C46—C47—C48	121.0 (3)
C49—P3—Ir2	111.48 (11)	C46—C47—H47A	119.5
C61—P4—C67	104.80 (15)	C48—C47—H47A	119.5
C61—P4—C48	101.26 (14)	C47—C48—C43	119.1 (3)
C67—P4—C48	105.77 (14)	C47—C48—P4	121.2 (2)
C61—P4—Ir2	122.08 (11)	C43—C48—P4	119.7 (2)
C67—P4—Ir2	106.56 (10)	C54—C49—C50	118.5 (3)
C48—P4—Ir2	114.99 (11)	C54—C49—P3	120.0 (3)
C2—C1—C6	119.2 (3)	C50—C49—P3	121.1 (3)
C2—C1—P1	117.3 (2)	C51—C50—C49	120.7 (3)
C6—C1—P1	123.3 (2)	C51—C50—H50A	119.6
C3—C2—C1	120.7 (3)	C49—C50—H50A	119.6
C3—C2—H2A	119.6	C52—C51—C50	120.1 (3)
C1—C2—H2A	119.6	C52—C51—H51A	119.9
C4—C3—C2	120.2 (3)	C50—C51—H51A	119.9
C4—C3—H3A	119.9	C53—C52—C51	119.6 (3)
C2—C3—H3A	119.9	C53—C52—H52A	120.2
C3—C4—C5	119.8 (3)	C51—C52—H52A	120.2
C3—C4—H4A	120.1	C52—C53—C54	120.6 (4)
C5—C4—H4A	120.1	C52—C53—H53A	119.7
C4—C5—C6	121.5 (3)	C54—C53—H53A	119.7
C4—C5—H5A	119.2	C53—C54—C49	120.3 (3)
C6—C5—H5A	119.2	C53—C54—H54A	119.8
C5—C6—C1	118.4 (3)	C49—C54—H54A	119.8
C5—C6—C7	117.0 (3)	C60—C55—C56	119.0 (3)
C1—C6—C7	124.6 (3)	C60—C55—P3	122.9 (3)
C8—C7—C12	119.3 (3)	C56—C55—P3	117.9 (2)
C8—C7—C6	118.1 (3)	C57—C56—C55	120.3 (3)
C12—C7—C6	122.5 (3)	C57—C56—H56A	119.8
C9—C8—C7	121.1 (3)	C55—C56—H56A	119.8
C9—C8—H8A	119.4	C58—C57—C56	120.4 (4)
C7—C8—H8A	119.4	C58—C57—H57A	119.8
C8—C9—C10	119.8 (3)	C56—C57—H57A	119.8
C8—C9—H9A	120.1	C59—C58—C57	119.8 (3)
C10—C9—H9A	120.1	C59—C58—H58A	120.1
C9—C10—C11	120.1 (3)	C57—C58—H58A	120.1
C9—C10—H10A	119.9	C58—C59—C60	120.3 (4)
C11—C10—H10A	119.9	C58—C59—H59A	119.8
C10—C11—C12	121.1 (3)	C60—C59—H59A	119.8
C10—C11—H11A	119.4	C55—C60—C59	120.2 (4)
C12—C11—H11A	119.4	C55—C60—H60A	119.9
C11—C12—C7	118.5 (3)	C59—C60—H60A	119.9
C11—C12—P2	121.6 (3)	C66—C61—C62	119.4 (3)
C7—C12—P2	119.8 (2)	C66—C61—P4	121.9 (2)
C14—C13—C18	118.2 (3)	C62—C61—P4	118.7 (2)
C14—C13—P1	123.9 (3)	C63—C62—C61	120.0 (3)
C18—C13—P1	117.9 (3)	C63—C62—H62A	120.0
C13—C14—C15	120.7 (3)	C61—C62—H62A	120.0
C13—C14—H14A	119.7	C64—C63—C62	120.2 (3)
C15—C14—H14A	119.7	C64—C63—H63A	119.9
C16—C15—C14	120.8 (3)	C62—C63—H63A	119.9
C16—C15—H15A	119.6	C63—C64—C65	120.4 (3)
C14—C15—H15A	119.6	C63—C64—H64A	119.8
C15—C16—C17	119.3 (3)	C65—C64—H64A	119.8
C15—C16—H16A	120.3	C64—C65—C66	119.6 (3)
C17—C16—H16A	120.3	C64—C65—H65A	120.2
C16—C17—C18	120.2 (4)	C66—C65—H65A	120.2
C16—C17—H17A	119.9	C61—C66—C65	120.4 (3)
C18—C17—H17A	119.9	C61—C66—H66A	119.8
C17—C18—C13	120.8 (4)	C65—C66—H66A	119.8
C17—C18—H18A	119.6	C72—C67—C68	118.5 (3)
C13—C18—H18A	119.6	C72—C67—P4	121.8 (3)
C20—C19—C24	119.0 (3)	C68—C67—P4	119.1 (3)
C20—C19—P1	117.6 (2)	C69—C68—C67	120.7 (4)
C24—C19—P1	123.1 (2)	C69—C68—H68A	119.6
C21—C20—C19	120.5 (3)	C67—C68—H68A	119.6
C21—C20—H20A	119.8	C70—C69—C68	119.9 (4)
C19—C20—H20A	119.8	C70—C69—H69A	120.0
C20—C21—C22	119.9 (3)	C68—C69—H69A	120.0
C20—C21—H21A	120.1	C69—C70—C71	120.7 (4)
C22—C21—H21A	120.1	C69—C70—H70A	119.7
C23—C22—C21	120.1 (3)	C71—C70—H70A	119.7
C23—C22—H22A	119.9	C70—C71—C72	119.8 (4)
C21—C22—H22A	119.9	C70—C71—H71A	120.1
C22—C23—C24	119.9 (3)	C72—C71—H71A	120.1
C22—C23—H23A	120.0	C67—C72—C71	120.3 (4)
C24—C23—H23A	120.0	C67—C72—H72A	119.8
C23—C24—C19	120.6 (3)	C71—C72—H72A	119.8
C23—C24—H24A	119.7	F14—B1—F11	109.3 (4)
C19—C24—H24A	119.7	F14—B1—F13	110.2 (3)
C26—C25—C30	119.3 (3)	F11—B1—F13	109.3 (3)
C26—C25—P2	122.1 (2)	F14—B1—F12	109.8 (3)
C30—C25—P2	118.6 (3)	F11—B1—F12	109.7 (3)
C25—C26—C27	119.8 (3)	F13—B1—F12	108.5 (4)
C25—C26—H26A	120.1	Cl12—C100—Cl11	112.5 (2)
C27—C26—H26A	120.1	Cl12—C100—H10B	109.1
C28—C27—C26	120.2 (4)	Cl11—C100—H10B	109.1
C28—C27—H27A	119.9	Cl12—C100—H10C	109.1
C26—C27—H27A	119.9	Cl11—C100—H10C	109.1
C29—C28—C27	120.2 (4)	H10B—C100—H10C	107.8
C29—C28—H28A	119.9	Cl22—C200—Cl21	111.7 (3)
C27—C28—H28A	119.9	Cl22—C200—H20B	109.3
C30—C29—C28	120.3 (4)	Cl21—C200—H20B	109.3
C30—C29—H29A	119.9	Cl22—C200—H20C	109.3
C28—C29—H29A	119.9	Cl21—C200—H20C	109.3
C29—C30—C25	120.3 (4)	H20B—C200—H20C	107.9
C29—C30—H30A	119.9