Syntheses and crystal structures of [IrIII{C(CHCO2Et)(dppm)2-κ4 P,C,C′,P′}ClH]Cl·2.75CH2Cl2 and its derivatives, [IrIII{C(CHCO2Et)(dppm)2-κ4 P,C,C′,P′}(CH2CO2Et)Cl]Cl·CH3OH·0.5H2O, [IrIII{C(CHCO2Et)(dppm)2-κ4 P,C,C′,P′}Cl2]Cl·CH3OH·2H2O and [IrIII{C(CHCO2Et)(dppm)2-κ4 P,C,C′,P′}(CH2CO2Et)(CO)]Cl2·2CH2Cl2·1.5H2O

Inge Schlapp-Hackl; Christoph Falschlunger; Kathrin Zauner; Walter Schuh; Holger Kopacka; Klaus Wurst; Paul Peringer

doi:10.1107/S2056989018017024

. 2019 Jan 1;75(Pt 1):12–20. doi: 10.1107/S2056989018017024

Syntheses and crystal structures of [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}ClH]Cl·2.75CH₂Cl₂ and its derivatives, [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}(CH₂CO₂Et)Cl]Cl·CH₃OH·0.5H₂O, [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}Cl₂]Cl·CH₃OH·2H₂O and [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}(CH₂CO₂Et)(CO)]Cl₂·2CH₂Cl₂·1.5H₂O

Inge Schlapp-Hackl ^a,^*, Christoph Falschlunger ^a, Kathrin Zauner ^a, Walter Schuh ^a, Holger Kopacka ^a, Klaus Wurst ^a, Paul Peringer ^a

PMCID: PMC6323871 PMID: 30713725

The common structural feature of the four title Ir^III compounds is the octahedral coordination of the Ir^III atom by a PCP pincer complex, a C atom of a (ethoxyoxoethanylidene)methane group and two variable ligands X (H, CH₂CO₂Et, Cl) and Y (Cl, CO).

Keywords: carbodiphosphorane (CDP), PCP pincer, diazo compounds, cycloaddition, iridium(III), C–C coupling reaction, non-innocent behaviour, alkylidene bridge, carbene intermediate, insertion reaction, crystal structure

Abstract

The common feature of the four iridium(III) salt complexes, (bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴ P,C,C′,P′)chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4), (bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴ P,C,C′,P′)chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5), (bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴ P,C,C′,P′)dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) and (bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴ P,C,C′,P′)carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) or in terms of their formulae [Ir(C₅₅H₅₀O₂P₄)ClH]Cl·2.75CH₂Cl₂ (4), [Ir(C₄H₇O₂)(C₅₅H₅₀O₂P₄)Cl]Cl·CH₃OH·0.5H₂O (5), [Ir(C₅₅H₅₀O₂P₄)Cl₂]Cl·CH₃OH·2H₂O (6) and [Ir(C₄H₇O₂)(C₅₅H₅₀O₂P₄)(CO)]Cl₂·2CH₂Cl₂·1.5H₂O (7) is a central Ir^III atom coordinated in a distorted octahedral fashion by a PCCP ligand system and two additional residues, such as chlorides, a hydride, a carbonyl or an alkyl unit. Thereby, the PCP pincer ligand system and the residue trans to the carbodiphosphorane (CDP) C atom surround the iridium(III) transition metal in the equatorial plane under the formation of two five-membered dissimilar chelate rings [C—C_CDP—P (4, 5, 6 and 7) for the first ring: 120.2 (3), 121.9 (5), 111.2 (3) and 121.7 (2) °; for the second ring: 112.1 (3), 113.5 (5), 120.5 (3) and 108.3 (2)°]. A cyclopropane-like heterocycle is positioned approximately orthogonal (84.21–88.85°) to the equatorial plane, including an alkylidene bridge connecting the Ir^III atom and the coordinating CDP atom of the PCP subunit. In general, the neutral PCCP ligand system coordinates the metal in a tetradentate way via three Lewis acid/base bonds and by an alkylidene unit presenting strengthened interactions. In all the crystal structures, (disordered) solvent molecules are present in the voids of the packed molecules that interact with the positively charged complex and its chloride counter-ion(s) through weak hydrogen bonding.

Chemical context

Carbodiphosphoranes (CDP) in combination with transition metals initialize a huge variety of functionalities. As a result of the presence of two σ-electron-donor groups, preferred in the form of tertiary phosphines, the stabilization of two free-electron pairs with σ- and simultaneously π-symmetry, the establishment of a localized electron octet and further the creation of a zero-valent, naked carbon atom in an excited singlet (¹ D) state is possible (Petz & Frenking, 2010 ▸). The carbodiphosphorane C atom can be considered as a four-electron donor, and accordingly enables the coordination of two Lewis acids, such as protons or different metal cations. Our interests focus on the combination of a carbodiphosphorane pincer ligand system, [CH(dppm)₂]Cl (dppm = 1,1-bis(diphenylphosphino)methane; Reitsamer et al., 2012 ▸), with reactive functionalities to enter new reaction pathways, to create new complexes and to analyse in detail the new properties obtained. In general, C—C coupling reactions can be induced via the use of diazo compounds such as ethyl diazoacetate. As a result of the presence of two nitrogen atoms acting together as an excellent leaving group, and an alkylidene group stabilized by different functionalities, the electrons are delocalized between three atoms and thus a positive and one negative charge theoretically allows by a disregard of the coordinating residuals and chemical conditions four different resonance structures to be gained in total. Therefore, the diazo compound can be regarded as both a nucleophilic and as an electrophilic reaction partner. By the use of this compound, a targeted synthesis of cyclopropanes or rather heterocyclopropanes, consisting of a transition metal, an electron-donor atom and a carbene carbon, is possible and has been reported several times in the literature (e.g. Nomura et al., 2011 ▸; Liu & Yan, 2015 ▸; Malisch et al., 1998 ▸; Strecker et al., 1991 ▸; Zhang et al., 2005 ▸, and references cited therein). An electrophilic reaction partner such as a transition metal establishes a nucleophilic attack of the diazo subunit and, according to the choice of the reaction conditions, the elimination of the nitrogen leaving group is supported. Consequently, the alkylidene carbon atom is stabilized by coordination of an electron-accepting atom and a reactive carbene intermediate complex is formed. The existence of a nucleophilic reaction partner in the vicinity of the carbene atom results in the formation of a ring including an alkylidene bridging subunit. In summary, the reaction of a diazo compound with an electrophilic and additionally a nucleophilic reaction partner initiates a mechanism that can be described as a cheletropic-like process. Inspired by this reaction sequence, we have synthesized a three-membered heterocycle by the combination of an ethyl diazoacetate and an iridium(III) PCP pincer carbodiphosphorane complex.

If the starting materials [CH(dppm)₂]Cl (Reitsamer et al., 2012 ▸) and [IrCl(cod)]₂ are mixed, a reaction sequence is initialized that consists of the following steps: Coordination of the iridium(I) atom, followed by deprotonation of the carbodiphosphorane carbon atom, the generation of a hydrido ligand caused by an oxidation of the iridium(I) atom and the formation of the [Ir{C(dppm)₂-κ³P,C,P‘}ClH(MeCN)]Cl complex 1 (Schlapp-Hackl et al., 2018 ▸; Fig. 1 ▸). In summary, the iridium(III) transition metal is stabilized by the PCP pincer ligand system, and by a chlorido and a hydrido ligand and an acetonitrile solvent molecule. The addition of ethyl diazoacetate causes, via loss of the dinitrogen subunit, the formation of an Ir^III–carbene bond. As a result of the presence of the second free lone-electron pair at the carbodiphosphorane carbon atom, a cyclization and further the creation of an alkylidene bridge is accomplished. The formation of the three-membered Ir—C_CDP—C ring is accompanied by a surprising displacement of the hydrido ligand from a position perpendicular to the plane of the PCP pincer system to a meridional arrangement trans to the carbodiphosphorane carbon atom. Supported by the polar solvent mixture methanol/acetonitrile (v/v 5:1) an [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}H(MeCN)]Cl₂ precursor system (2) is generated in high yields (86%). Moreover, the preparation of complex 2 in a less polar solvent environment like chloroform/acetonitrile or in a solvent mixture of methylene chloride/acetonitrile (v/v 5:1) is not possible and quantitatively results in the substitution of one phosphine moiety of the carbodiphosphorane functionality against the carbene CHCO₂Et subunit. An [Ir{C(CHCO₂Et)(dppm)-κ²P,C}Cl(dppm)H]Cl complex 3 is generated, offering a phosphorus ylide carbon backbone (Schlapp-Hackl et al., 2018 ▸). To a lesser extent (14% yield), this complex is additionally obtained as by-product by the production of complex 2. Heating of complex 2 in methanol/acetonitrile (v/v 5:1) to 333 K for 2 h benefits the ring-opening reaction of the PCCP pincer ligand system. Therefore, a reorganization of the ligand system is supported, resulting in the quantitative formation of complex 3. Furthermore, evaporation of the reaction mixture of complex 2 causes an exchange of the acetonitrile solvent ligand with a chloride counter-ion and the creation of the desired [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}ClH]Cl complex 4.

Scheme (Cambridge Soft, 2001 ▸) for the synthesis and crystallization of the title compounds 4–7.

The stucture of this iridium(III) PCCP complex was completely determined by NMR spectroscopy and X-ray crystallography, but up to now crystallization attempts of the intermediates, 1 and 2, were unsuccessful. With regard to a ruthenium PCP pincer complex, a related cycloaddition was monitored (Zhang et al., 2005 ▸). Thereby, the ruthenium transition metal first stabilizes the phenyldiazomethane by coordination. After the elimination of the dinitrogen molecule, the formation of the corresponding carbene complex and finally a carbon–carbon coupling reaction between the central carbon atom of the phenyl-based PCP ligand and the carbene was detected. As a consequence, the arene backbone of the PCP ligand system is transformed to an arenium moiety. Treatment of complex 4 with an additional equivalent amount of ethyl diazoacetate causes an insertion reaction of the alkylidene to the iridium(III)–hydrido bond and the formation of the [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}(CH₂CO₂Et)Cl]Cl alkyl derivative 5. This reaction procedure is well known, and the mechanism of the intermolecular insertion reaction has been clarified via an intermediate carbene complex (Cohen et al., 2003 ▸). Moreover, treatment of complexes 4 and 5 with hydrochloric acid leads to a ligand substitution at the position trans to the central carbon atom of the PCP pincer ligand system with a chloride ion and to the formation of the [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}Cl₂]Cl complex 6. Besides, a replacement of the chlorido ligand of compound 5 by a carbonyl group is possible and results in the [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}(CH₂CO₂Et)(CO)]Cl₂ complex 7.

Here we report details of the syntheses and crystal structures of complexes 4–7.

Structural commentary

The asymmetric unit of compound 4, [Ir^III{C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′}ClH]Cl, comprises of one formula unit of 4 and additionally of 2.75 molecules of methylene chloride solvent molecules. The central iridium(III) transition metal is surrounded in a distorted octahedral fashion by a PCCP pincer-like ligand system, and anionic chlorido and hydrido ligands (Fig. 2 ▸). The neutral [C(CHCO₂Et)(dppm)₂-κ⁴ P,C,C′,P′] ligand coordinates the Ir^III metal in a tetradentate fashion via two P and two C atoms under formation of two five-membered, dissimilar chelate rings [C4—C1—P3 = 120.2 (3)°, C4—C1—P2 = 112.1 (3)°] and one three membered heterocycle. The PCP ligand exhibits a meridional arrangement with the hydrido ligand completing the equatorial plane trans to the C1 carbodiphosphorane atom. A cyclopropane-like chelate ring is positioned nearly normal (84.21°) to the equatorial plane, and a chlorido ligand is positioned trans to the alkylidene carbon atom C4. The Ir—C1 [2.273 (4) Å] and Ir—C4 [2.072 (5) Å] distances differ significantly and consequently these values substantiate a strengthened interaction between the iridium(III) metal and the alkylidene carbon atom. The C1—C4 separation [1.515 (6) Å] is slightly shorter in comparison to a typical C—C single bond but, in general, very close to that of cyclopropanes. However, in comparison with a cyclopropane molecule the C4—Ir1—C1 [40.5 (2)°], C4—C1—Ir1 [62.6 (2)°] and C1—C4—Ir1 [76.9 (3)°] angles emphasise a significant distortion of the synthesized three-membered heterocycle. All mentioned geometric features of this strained Ir—C1—C4 metallacycle can be associated with the structural results of the Ru—C—C triangle reported by Zhang et al. (2005 ▸). Furthermore, the three-membered ring causes a distortion of the octahedral coordination geometry (Table 1 ▸). The P1—Ir1—P4 [178.4 (1)°] atoms are less affected and show only a slight deviation from linearity. Though, the tetrahedral environment of the carbodiphosphorane C1 atom is strongly influenced and thus distorted, which is reflected by a P3—C1—P2 angle of 124.2 (3)°. Overall, the transition metal and its ligand system present a cationic complex balanced by one chloride.

Molecular structure of the complex cation in 4 and the counter-anion. Displacement ellipsoids are drawn at the 30% probability level. For clarity, only the *ipso* carbon atoms of the phenyl groups are presented and the solvent molecules are omitted.

Table 1. Selected bond lengths (Å) and angles (°) of the compounds 4, 5, 6 and 7 .

	4	5	6	7
Ir1—C1	2.273 (4)	2.279 (6)	2.149 (4)	2.225 (3)
Ir1—C4	2.072 (5)	2.046 (7)	2.076 (4)	2.119 (3)
Ir1—P1	2.290 (1)	2.318 (2)	2.309 (1)	2.339 (1)
Ir1—P4	2.278 (1)	2.306 (2)	2.330 (1)	2.366 (1)
P2—C1	1.791 (5)	1.788 (7)	1.822 (4)	1.837 (3)
Ir1—L _x (L _x= –H, –Cl, –CH₂CO₂Et)	1.62 (2)	2.163 (7)	2.427 (1)	2.177 (3)
Ir1—L _y (L _y = –Cl, –CO)	2.462 (1)	2.461 (2)	2.460 (1)	1.910 (3)
P3—C1	1.788 (5)	1.789 (7)	1.833 (4)	1.791 (3)
C1—C4	1.515 (6)	1.507 (9)	1.513 (5)	1.515 (4)
C4—Ir1—C1	40.5 (2)	40.3 (2)	41.9 (2)	40.72 (11)
C4—C1—Ir1	62.6 (2)	61.5 (3)	66.5 (2)	65.88 (15)
C1—C4—Ir1	76.9 (3)	78.2 (4)	71.6 (2)	73.40 (16)
C4—Ir1—L _y (L _y = –Cl, –CO)	150.3 (1)	152.5 (2)	151.9 (1)	158.8 (1)
C1—Ir1—L _y (L _y = –Cl, –CO)	111.3 (1)	112.8 (2)	111.5 (1)	118.8 (1)
C4—Ir1—L _x (L _x = –H, –Cl, –CH₂CO₂Et)	119.7 (18)	120.8 (3)	116.2 (1)	106.7 (1)
C1—Ir1—L _x (L _x = –H, –Cl, –CH₂CO₂Et)	159.8 (18)	161.1 (3)	158.1 (1)	147.4 (1)
P1—Ir1—P4	178.4 (1)	173.5 (1)	177.6 (1)	176.4 (1)
P1—Ir1—(C1—C4)	84.21	88.85	85.57	84.56

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯Cl2	0.98	2.58	3.488 (5)	154
C3—H3A⋯O1	0.98	2.31	2.892 (7)	117
C3—H3B⋯Cl2ⁱ	0.98	2.83	3.456 (5)	122

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O5ⁱ	0.98	2.22	3.139 (15)	156
C3—H3A⋯Cl2	0.98	2.91	3.693 (8)	137
C3—H3B⋯O1	0.98	2.40	2.895 (10)	111
C102—H102⋯O4	0.94	2.48	3.263 (11)	141
C212—H212⋯O5ⁱ	0.94	2.54	3.445 (18)	163
C306—H306⋯Cl2	0.94	2.57	3.491 (9)	167
C308—H308⋯Cl1	0.94	2.56	3.464 (8)	162
C408—H408⋯O3	0.94	2.23	3.046 (10)	145

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1	0.98	2.33	2.852 (5)	112
C2—H2B⋯O5ⁱ	0.98	2.45	3.320 (8)	148
C3—H3B⋯Cl3	0.98	2.66	3.589 (4)	158
C6—H6A⋯O3ⁱⁱ	0.98	2.40	3.369 (8)	169
C102—H102⋯Cl1	0.94	2.63	3.343 (4)	133
C108—H108⋯Cl1	0.94	2.82	3.671 (5)	151
C206—H206⋯Cl3ⁱ	0.94	2.87	3.742 (5)	156
C208—H208⋯Cl2	0.94	2.64	3.487 (5)	150
C312—H312⋯Cl3	0.94	2.84	3.749 (6)	164
C402—H402⋯Cl1	0.94	2.59	3.398 (6)	144
C406—H406⋯Cl3	0.94	2.88	3.757 (6)	156
C412—H412⋯Cl3	0.94	2.95	3.870 (5)	167

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Cl1	0.98	2.48	3.421 (3)	162
C3—H3A⋯Cl1ⁱ	0.98	2.59	3.488 (3)	152
C3—H3B⋯O1	0.98	2.21	2.968 (4)	134
C102—H102⋯Cl2	0.94	2.61	3.505 (4)	160
C108—H108⋯O2	0.94	2.61	3.313 (4)	132
C112—H112⋯Cl1	0.94	2.80	3.595 (4)	143
C202—H202⋯Cl2	0.94	2.70	3.574 (4)	156
C212—H212⋯Cl1	0.94	2.80	3.733 (5)	173
C306—H306⋯O1	0.94	2.47	3.061 (4)	121
C312—H312⋯Cl1ⁱ	0.94	2.73	3.503 (4)	140
C402—H402⋯O2	0.94	2.47	3.375 (4)	162
C408—H408⋯O3	0.94	2.44	3.326 (5)	156
C412—H412⋯Cl1ⁱ	0.94	2.97	3.866 (4)	161
C13—H13A⋯O5ⁱⁱ	0.98	2.58	3.194 (6)	121
C13—H13A⋯Cl2ⁱⁱ	0.98	2.68	3.500 (7)	141
C14—H14A⋯Cl2ⁱⁱⁱ	0.98	2.65	3.553 (6)	153
C14—H14B⋯O1^iv	0.98	2.37	3.327 (6)	164
C14A—H14C⋯O1^iv	0.98	2.38	3.327 (6)	163
C14A—H14D⋯Cl2ⁱⁱⁱ	0.98	2.59	3.553 (6)	168
O6—H6OA⋯Cl2	0.85 (2)	2.39 (4)	3.178 (5)	154 (7)
O6—H6OB⋯Cl1	0.85 (2)	2.39 (2)	3.239 (6)	178 (6)

	4	5	6	7
Crystal data
Chemical formula	[IrClH(C₅₅H₅₀O₂P₄)]Cl·2.75CH₂Cl₂	[Ir(C₄H₇O₂)Cl(C₅₅H₅₀O₂P₄)]Cl·CH₄O·0.5H₂O	[IrCl₂(C₅₅H₅₀O₂P₄)]Cl·CH₄O·2H₂O	[Ir(C₄H₇O₂)(C₅₅H₅₀O₂P₄)(CO)]Cl₂·2CH₂Cl₂·1.5H₂O
M _r	1364.48	1258.07	1233.45	1441.91
Crystal system, space group	Monoclinic, P2₁/n	Triclinic, P	Triclinic, P	Triclinic, P
Temperature (K)	233	233	233	233
a, b, c (Å)	12.4425 (2), 22.4020 (3), 22.5393 (3)	12.4253 (3), 13.7081 (4), 17.6780 (6)	11.2371 (2), 12.9144 (2), 19.2371 (3)	11.7326 (2), 13.8815 (2), 22.2615 (3)
α, β, γ (°)	90, 94.826 (1), 90	93.152 (2), 97.960 (2), 103.771 (2)	89.439 (1), 77.863 (1), 83.114 (1)	75.477 (1), 86.508 (1), 65.212 (1)
V (Å³)	6260.26 (16)	2884.18 (15)	2709.27 (8)	3182.38 (9)
Z	4	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	2.59	2.57	2.78	2.50
Crystal size (mm)	0.11 × 0.08 × 0.05	0.15 × 0.05 × 0.02	0.11 × 0.05 × 0.03	0.31 × 0.23 × 0.19

Data collection
Diffractometer	Nonius KappaCCD	Nonius KappaCCD	Nonius KappaCCD	Nonius KappaCCD
No. of measured, independent and observed [I > 2σ(I)] reflections	39699, 11006, 8888	13821, 7453, 6326	17984, 9526, 8083	23329, 12496, 11695
R _int	0.045	0.037	0.035	0.024
θ_max (°)	25.0	22.4	25.0	26.0

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.040, 0.112, 1.04	0.044, 0.106, 1.07	0.034, 0.073, 1.05	0.028, 0.070, 1.05
No. of reflections	11006	7453	9526	12496
No. of parameters	711	674	626	751
No. of restraints	2	1	1	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.86	0.90, −0.96	0.75, −1.01	0.97, −1.29

[IrClH(C₅₅H₅₀O₂P₄)]Cl·2.75CH₂Cl₂	F(000) = 2734
M_r = 1364.48	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4425 (2) Å	Cell parameters from 104186 reflections
b = 22.4020 (3) Å	θ = 1.0–25.3°
c = 22.5393 (3) Å	µ = 2.59 mm⁻¹
β = 94.826 (1)°	T = 233 K
V = 6260.26 (16) Å³	Prism, colorless
Z = 4	0.11 × 0.08 × 0.05 mm

Nonius KappaCCD diffractometer	8888 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
phi– and ω–scans	h = −14→14
39699 measured reflections	k = −26→26
11006 independent reflections	l = −26→26

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0606P)² + 10.2768P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
11006 reflections	Δρ_max = 1.03 e Å⁻³
711 parameters	Δρ_min = −0.86 e Å⁻³

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ir1	0.49207 (2)	0.11833 (2)	0.20622 (2)	0.03228 (8)
H1	0.484 (4)	0.1906 (9)	0.209 (2)	0.067 (18)*
P1	0.67637 (10)	0.11984 (5)	0.22113 (6)	0.0370 (3)
P2	0.62189 (10)	−0.01107 (5)	0.22879 (6)	0.0365 (3)
P3	0.36683 (10)	−0.01314 (5)	0.21373 (5)	0.0326 (3)
P4	0.30844 (10)	0.11776 (5)	0.19399 (6)	0.0322 (3)
Cl1	0.52098 (11)	0.12563 (6)	0.09975 (6)	0.0461 (3)
Cl2	0.98655 (13)	0.01266 (9)	0.20289 (13)	0.1081 (9)
O1	0.3419 (3)	0.04012 (18)	0.33389 (18)	0.0627 (11)
O2	0.4452 (4)	0.11608 (16)	0.36960 (17)	0.0579 (11)
C1	0.4926 (4)	0.02169 (19)	0.2370 (2)	0.0323 (10)
C2	0.7115 (4)	0.0439 (2)	0.1997 (2)	0.0424 (12)
H2A	0.7070	0.0410	0.1562	0.051*
H2B	0.7860	0.0352	0.2148	0.051*
C3	0.2600 (4)	0.0420 (2)	0.2099 (2)	0.0396 (11)
H3A	0.2270	0.0425	0.2479	0.048*
H3B	0.2042	0.0304	0.1788	0.048*
C4	0.4981 (4)	0.0697 (2)	0.2846 (2)	0.0360 (11)
H4	0.571 (2)	0.068 (2)	0.3031 (19)	0.036 (13)*
C5	0.4185 (5)	0.0725 (2)	0.3304 (2)	0.0443 (12)
C7	0.3729 (7)	0.1253 (3)	0.4152 (3)	0.076 (2)
H7A	0.3676	0.0890	0.4392	0.091*
H7B	0.3007	0.1357	0.3975	0.091*
C8	0.4203 (8)	0.1761 (4)	0.4533 (4)	0.118 (3)
H8A	0.3744	0.1842	0.4851	0.177*
H8B	0.4918	0.1650	0.4704	0.177*
H8C	0.4252	0.2115	0.4289	0.177*
C101	0.7549 (4)	0.1701 (2)	0.1780 (2)	0.0463 (13)
C102	0.8362 (7)	0.1526 (4)	0.1455 (5)	0.115 (4)
H102	0.8538	0.1119	0.1438	0.138*
C103	0.8944 (8)	0.1940 (5)	0.1145 (6)	0.149 (5)
H103	0.9491	0.1811	0.0911	0.179*
C104	0.8713 (6)	0.2521 (4)	0.1183 (4)	0.095 (3)
H104	0.9105	0.2800	0.0978	0.114*
C105	0.7917 (8)	0.2712 (3)	0.1516 (4)	0.093 (3)
H105	0.7776	0.3123	0.1549	0.112*
C106	0.7311 (7)	0.2298 (3)	0.1808 (3)	0.080 (2)
H106	0.6740	0.2427	0.2024	0.096*
C107	0.7388 (5)	0.1311 (2)	0.2962 (3)	0.0514 (14)
C108	0.8387 (6)	0.1063 (3)	0.3146 (3)	0.073 (2)
H108	0.8762	0.0827	0.2886	0.088*
C109	0.8822 (8)	0.1176 (4)	0.3736 (5)	0.112 (4)
H109	0.9490	0.1009	0.3874	0.134*
C110	0.8274 (11)	0.1528 (5)	0.4107 (4)	0.115 (4)
H110	0.8576	0.1599	0.4497	0.138*
C111	0.7302 (8)	0.1776 (4)	0.3923 (3)	0.091 (3)
H111	0.6938	0.2020	0.4181	0.110*
C112	0.6863 (6)	0.1664 (3)	0.3353 (3)	0.0651 (17)
H112	0.6190	0.1831	0.3225	0.078*
C201	0.6228 (4)	−0.0736 (2)	0.1787 (2)	0.0409 (12)
C202	0.6137 (5)	−0.0644 (3)	0.1167 (2)	0.0499 (14)
H202	0.6052	−0.0255	0.1014	0.060*
C203	0.6174 (6)	−0.1124 (3)	0.0783 (3)	0.0681 (18)
H203	0.6104	−0.1063	0.0369	0.082*
C204	0.6316 (5)	−0.1700 (3)	0.1014 (3)	0.0673 (18)
H204	0.6355	−0.2027	0.0755	0.081*
C205	0.6399 (5)	−0.1793 (3)	0.1620 (3)	0.0648 (17)
H205	0.6478	−0.2183	0.1771	0.078*
C206	0.6368 (4)	−0.1317 (2)	0.2010 (3)	0.0524 (14)
H206	0.6441	−0.1383	0.2423	0.063*
C207	0.6860 (5)	−0.0357 (2)	0.2990 (3)	0.0491 (14)
C208	0.7957 (5)	−0.0481 (3)	0.3027 (3)	0.0682 (18)
H208	0.8347	−0.0441	0.2690	0.082*
C209	0.8477 (8)	−0.0666 (4)	0.3568 (5)	0.100 (3)
H209	0.9219	−0.0752	0.3592	0.120*
C210	0.7930 (10)	−0.0726 (4)	0.4060 (4)	0.106 (4)
H210	0.8299	−0.0842	0.4422	0.127*
C211	0.6813 (9)	−0.0614 (3)	0.4032 (3)	0.096 (3)
H211	0.6435	−0.0664	0.4373	0.116*
C212	0.6259 (6)	−0.0425 (3)	0.3485 (3)	0.0657 (18)
H212	0.5514	−0.0347	0.3457	0.079*
C301	0.3231 (4)	−0.0735 (2)	0.2590 (2)	0.0384 (11)
C302	0.2144 (5)	−0.0820 (3)	0.2652 (3)	0.0572 (15)
H302	0.1637	−0.0544	0.2486	0.069*
C303	0.1802 (6)	−0.1309 (3)	0.2959 (3)	0.077 (2)
H303	0.1062	−0.1366	0.2996	0.092*
C304	0.2540 (7)	−0.1712 (3)	0.3209 (3)	0.078 (2)
H304	0.2303	−0.2040	0.3423	0.094*
C305	0.3607 (6)	−0.1639 (3)	0.3150 (3)	0.0711 (19)
H305	0.4110	−0.1917	0.3319	0.085*
C306	0.3953 (5)	−0.1149 (2)	0.2835 (3)	0.0554 (15)
H306	0.4692	−0.1100	0.2791	0.067*
C307	0.3642 (4)	−0.0446 (2)	0.1398 (2)	0.0356 (11)
C308	0.3715 (5)	−0.0068 (2)	0.0913 (2)	0.0494 (13)
H308	0.3852	0.0341	0.0973	0.059*
C309	0.3585 (6)	−0.0297 (3)	0.0343 (3)	0.0690 (18)
H309	0.3634	−0.0042	0.0015	0.083*
C310	0.3382 (6)	−0.0895 (3)	0.0250 (3)	0.0686 (18)
H310	0.3291	−0.1048	−0.0140	0.082*
C311	0.3314 (6)	−0.1269 (3)	0.0729 (3)	0.0625 (17)
H311	0.3179	−0.1678	0.0667	0.075*
C312	0.3444 (5)	−0.1046 (2)	0.1300 (2)	0.0472 (13)
H312	0.3397	−0.1305	0.1626	0.057*
C401	0.2343 (4)	0.1642 (2)	0.2433 (2)	0.0402 (11)
C402	0.2883 (5)	0.2051 (2)	0.2807 (2)	0.0483 (13)
H402	0.3637	0.2086	0.2817	0.058*
C403	0.2304 (5)	0.2412 (3)	0.3171 (3)	0.0607 (16)
H403	0.2671	0.2690	0.3426	0.073*
C404	0.1209 (5)	0.2365 (3)	0.3161 (3)	0.0636 (17)
H404	0.0827	0.2606	0.3412	0.076*
C405	0.0667 (5)	0.1966 (3)	0.2782 (4)	0.078 (2)
H405	−0.0088	0.1936	0.2772	0.094*
C406	0.1231 (5)	0.1603 (3)	0.2410 (3)	0.0690 (19)
H406	0.0858	0.1334	0.2147	0.083*
C407	0.2442 (4)	0.1381 (2)	0.1209 (2)	0.0421 (12)
C408	0.2823 (5)	0.1899 (2)	0.0957 (2)	0.0507 (14)
H408	0.3416	0.2100	0.1150	0.061*
C409	0.2344 (6)	0.2122 (3)	0.0426 (3)	0.0676 (18)
H409	0.2597	0.2478	0.0268	0.081*
C410	0.1496 (6)	0.1820 (4)	0.0132 (3)	0.080 (2)
H410	0.1162	0.1971	−0.0227	0.096*
C411	0.1144 (7)	0.1301 (4)	0.0363 (4)	0.093 (3)
H411	0.0587	0.1087	0.0151	0.111*
C412	0.1591 (6)	0.1078 (3)	0.0910 (3)	0.0708 (19)
H412	0.1317	0.0728	0.1072	0.085*
C9	0.250 (3)	−0.0515 (13)	0.4305 (9)	0.223 (19)	0.5
Cl3	0.3575 (9)	−0.0543 (4)	0.4754 (3)	0.201 (4)	0.5
Cl4	0.1305 (7)	−0.0182 (4)	0.4559 (3)	0.167 (3)	0.5
C10	0.5629 (8)	0.2613 (4)	0.0386 (4)	0.112 (3)
Cl5	0.4809 (2)	0.31145 (11)	0.07504 (11)	0.1086 (7)
Cl6	0.6123 (3)	0.29238 (12)	−0.02166 (12)	0.1243 (9)
C11	0.9453 (10)	−0.1288 (5)	0.1519 (7)	0.139 (4)
Cl7	0.9402 (6)	−0.1902 (3)	0.1966 (6)	0.197 (4)	0.7
Cl8	1.0617 (3)	−0.1332 (3)	0.1087 (2)	0.1348 (16)	0.7
Cl7A	0.9153 (19)	−0.1694 (9)	0.231 (2)	0.31 (2)	0.3
Cl8A	1.0197 (18)	−0.1825 (9)	0.1312 (12)	0.239 (10)	0.3
C12	0.951 (5)	0.0067 (16)	0.026 (3)	0.16 (2)	0.25
Cl9	1.0704 (12)	−0.0453 (9)	0.0654 (12)	0.238 (11)	0.25
Cl10	0.8652 (16)	0.0098 (9)	0.0607 (12)	0.234 (11)	0.25

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.03166 (12)	0.02717 (12)	0.03855 (12)	0.00054 (7)	0.00623 (8)	0.00117 (8)
P1	0.0320 (7)	0.0297 (7)	0.0491 (8)	−0.0032 (5)	0.0014 (6)	0.0026 (5)
P2	0.0328 (7)	0.0302 (6)	0.0466 (7)	0.0015 (5)	0.0025 (5)	0.0026 (6)
P3	0.0327 (6)	0.0274 (6)	0.0387 (7)	−0.0006 (5)	0.0085 (5)	0.0005 (5)
P4	0.0309 (6)	0.0272 (6)	0.0392 (7)	0.0035 (5)	0.0069 (5)	−0.0008 (5)
Cl1	0.0470 (7)	0.0514 (8)	0.0414 (7)	0.0001 (6)	0.0130 (6)	0.0066 (6)
Cl2	0.0366 (9)	0.0594 (11)	0.229 (3)	−0.0004 (7)	0.0143 (12)	−0.0035 (13)
O1	0.071 (3)	0.059 (3)	0.063 (3)	−0.014 (2)	0.029 (2)	−0.008 (2)
O2	0.082 (3)	0.051 (2)	0.043 (2)	−0.0040 (19)	0.017 (2)	−0.0143 (18)
C1	0.036 (3)	0.026 (2)	0.035 (3)	−0.0005 (19)	0.007 (2)	0.002 (2)
C2	0.030 (3)	0.034 (3)	0.064 (3)	0.000 (2)	0.007 (2)	0.003 (2)
C3	0.032 (3)	0.035 (3)	0.052 (3)	0.001 (2)	0.009 (2)	−0.001 (2)
C4	0.037 (3)	0.029 (3)	0.042 (3)	0.000 (2)	0.004 (2)	0.000 (2)
C5	0.054 (3)	0.039 (3)	0.041 (3)	0.002 (3)	0.011 (2)	0.002 (2)
C7	0.105 (6)	0.079 (5)	0.049 (4)	0.004 (4)	0.034 (4)	−0.014 (3)
C8	0.153 (9)	0.120 (7)	0.087 (6)	−0.003 (6)	0.036 (6)	−0.058 (6)
C101	0.036 (3)	0.045 (3)	0.056 (3)	−0.006 (2)	−0.002 (2)	0.010 (3)
C102	0.087 (6)	0.064 (5)	0.206 (10)	0.008 (4)	0.085 (6)	0.036 (6)
C103	0.112 (8)	0.098 (7)	0.254 (14)	0.014 (6)	0.117 (9)	0.062 (8)
C104	0.063 (5)	0.103 (7)	0.117 (7)	−0.036 (5)	0.000 (5)	0.047 (6)
C105	0.128 (7)	0.047 (4)	0.106 (6)	−0.020 (4)	0.020 (6)	0.022 (4)
C106	0.112 (6)	0.045 (4)	0.089 (5)	−0.006 (4)	0.039 (5)	0.007 (4)
C107	0.050 (3)	0.043 (3)	0.059 (4)	−0.015 (3)	−0.011 (3)	0.008 (3)
C108	0.063 (4)	0.069 (4)	0.084 (5)	−0.009 (3)	−0.025 (4)	0.009 (4)
C109	0.095 (7)	0.098 (7)	0.129 (9)	−0.027 (5)	−0.072 (7)	0.031 (6)
C110	0.149 (10)	0.114 (8)	0.074 (6)	−0.053 (7)	−0.027 (6)	−0.005 (6)
C111	0.115 (7)	0.091 (6)	0.066 (5)	−0.045 (5)	−0.004 (5)	−0.007 (4)
C112	0.076 (4)	0.057 (4)	0.062 (4)	−0.022 (3)	0.002 (3)	−0.009 (3)
C201	0.032 (3)	0.033 (3)	0.059 (3)	0.001 (2)	0.009 (2)	−0.006 (2)
C202	0.057 (4)	0.043 (3)	0.052 (3)	−0.001 (3)	0.018 (3)	−0.001 (3)
C203	0.071 (4)	0.072 (5)	0.064 (4)	−0.007 (3)	0.024 (3)	−0.017 (3)
C204	0.066 (4)	0.051 (4)	0.088 (5)	−0.004 (3)	0.024 (4)	−0.028 (4)
C205	0.058 (4)	0.039 (3)	0.099 (5)	0.003 (3)	0.015 (4)	−0.009 (3)
C206	0.041 (3)	0.039 (3)	0.077 (4)	0.002 (2)	0.008 (3)	−0.001 (3)
C207	0.055 (3)	0.035 (3)	0.054 (3)	0.002 (2)	−0.013 (3)	0.002 (2)
C208	0.055 (4)	0.055 (4)	0.090 (5)	0.005 (3)	−0.020 (3)	0.010 (3)
C209	0.089 (6)	0.074 (5)	0.126 (8)	0.009 (4)	−0.060 (6)	0.015 (5)
C210	0.154 (9)	0.064 (5)	0.086 (6)	0.037 (5)	−0.066 (6)	−0.004 (5)
C211	0.171 (9)	0.064 (5)	0.052 (4)	0.025 (5)	−0.005 (5)	0.002 (3)
C212	0.092 (5)	0.046 (3)	0.057 (4)	0.016 (3)	−0.006 (3)	0.010 (3)
C301	0.047 (3)	0.035 (3)	0.034 (3)	−0.005 (2)	0.011 (2)	−0.002 (2)
C302	0.053 (4)	0.050 (3)	0.071 (4)	−0.005 (3)	0.016 (3)	0.013 (3)
C303	0.076 (5)	0.070 (5)	0.091 (5)	−0.016 (4)	0.034 (4)	0.014 (4)
C304	0.102 (6)	0.056 (4)	0.079 (5)	−0.018 (4)	0.028 (4)	0.022 (4)
C305	0.093 (5)	0.047 (4)	0.073 (4)	0.003 (4)	0.007 (4)	0.017 (3)
C306	0.064 (4)	0.045 (3)	0.059 (4)	0.002 (3)	0.016 (3)	0.012 (3)
C307	0.034 (3)	0.034 (3)	0.040 (3)	0.002 (2)	0.009 (2)	0.000 (2)
C308	0.068 (4)	0.040 (3)	0.042 (3)	−0.002 (3)	0.015 (3)	0.001 (2)
C309	0.103 (5)	0.060 (4)	0.046 (3)	−0.008 (4)	0.017 (3)	0.003 (3)
C310	0.094 (5)	0.070 (4)	0.044 (3)	−0.005 (4)	0.016 (3)	−0.018 (3)
C311	0.082 (5)	0.052 (4)	0.055 (4)	−0.014 (3)	0.017 (3)	−0.022 (3)
C312	0.058 (3)	0.038 (3)	0.048 (3)	−0.003 (2)	0.015 (3)	−0.004 (2)
C401	0.041 (3)	0.034 (3)	0.047 (3)	0.001 (2)	0.013 (2)	−0.002 (2)
C402	0.047 (3)	0.048 (3)	0.050 (3)	0.008 (3)	0.008 (3)	−0.006 (3)
C403	0.064 (4)	0.058 (4)	0.060 (4)	0.013 (3)	0.005 (3)	−0.021 (3)
C404	0.072 (4)	0.045 (3)	0.079 (4)	0.008 (3)	0.035 (4)	−0.011 (3)
C405	0.053 (4)	0.061 (4)	0.127 (6)	−0.003 (3)	0.046 (4)	−0.031 (4)
C406	0.049 (4)	0.057 (4)	0.104 (5)	−0.011 (3)	0.030 (3)	−0.036 (4)
C407	0.039 (3)	0.043 (3)	0.045 (3)	0.010 (2)	0.004 (2)	−0.003 (2)
C408	0.056 (3)	0.046 (3)	0.050 (3)	0.008 (3)	0.003 (3)	0.002 (3)
C409	0.079 (5)	0.062 (4)	0.062 (4)	0.013 (4)	0.006 (4)	0.010 (3)
C410	0.087 (5)	0.092 (6)	0.059 (4)	0.013 (4)	−0.011 (4)	0.010 (4)
C411	0.076 (5)	0.115 (7)	0.080 (5)	−0.014 (5)	−0.034 (4)	−0.003 (5)
C412	0.062 (4)	0.076 (5)	0.070 (4)	−0.010 (3)	−0.021 (3)	0.004 (3)
C9	0.41 (4)	0.20 (2)	0.070 (12)	−0.24 (3)	0.11 (2)	−0.077 (14)
Cl3	0.324 (12)	0.154 (6)	0.121 (5)	0.103 (7)	0.006 (6)	−0.008 (5)
Cl4	0.197 (7)	0.205 (7)	0.099 (4)	−0.039 (6)	0.008 (4)	−0.037 (4)
C10	0.142 (8)	0.072 (5)	0.126 (8)	−0.001 (5)	0.032 (6)	0.029 (5)
Cl5	0.1132 (17)	0.1046 (17)	0.1117 (17)	−0.0339 (13)	0.0310 (14)	−0.0231 (13)
Cl6	0.160 (2)	0.1072 (18)	0.1116 (18)	0.0022 (17)	0.0446 (17)	0.0005 (15)
C11	0.101 (8)	0.117 (9)	0.195 (13)	0.018 (7)	−0.007 (8)	−0.027 (8)
Cl7	0.103 (5)	0.089 (4)	0.393 (14)	−0.018 (3)	−0.010 (6)	0.043 (6)
Cl8	0.088 (3)	0.194 (5)	0.118 (3)	0.029 (3)	−0.020 (2)	−0.020 (3)
Cl7A	0.128 (13)	0.102 (12)	0.69 (7)	0.008 (9)	0.05 (2)	−0.04 (2)
Cl8A	0.201 (19)	0.174 (15)	0.32 (3)	0.048 (14)	−0.098 (18)	−0.041 (16)
C12	0.22 (6)	0.04 (2)	0.22 (6)	−0.08 (3)	0.03 (4)	−0.05 (3)
Cl9	0.120 (11)	0.208 (18)	0.39 (3)	−0.022 (11)	0.010 (14)	−0.15 (2)
Cl10	0.159 (14)	0.213 (19)	0.31 (3)	0.077 (14)	−0.088 (16)	−0.088 (18)

Ir1—C4	2.072 (5)	C207—C208	1.390 (8)
Ir1—C1	2.273 (4)	C207—C212	1.402 (9)
Ir1—P4	2.2783 (12)	C208—C209	1.394 (10)
Ir1—P1	2.2897 (13)	C208—H208	0.9400
Ir1—Cl1	2.4619 (13)	C209—C210	1.355 (13)
Ir1—H1	1.62 (2)	C209—H209	0.9400
P1—C107	1.819 (6)	C210—C211	1.408 (13)
P1—C101	1.824 (5)	C210—H210	0.9400
P1—C2	1.833 (5)	C211—C212	1.426 (9)
P2—C1	1.791 (5)	C211—H211	0.9400
P2—C207	1.798 (5)	C212—H212	0.9400
P2—C201	1.800 (5)	C301—C306	1.374 (8)
P2—C2	1.820 (5)	C301—C302	1.384 (7)
P3—C1	1.788 (5)	C302—C303	1.380 (9)
P3—C301	1.806 (5)	C302—H302	0.9400
P3—C307	1.807 (5)	C303—C304	1.376 (10)
P3—C3	1.811 (5)	C303—H303	0.9400
P4—C407	1.827 (5)	C304—C305	1.356 (10)
P4—C401	1.828 (5)	C304—H304	0.9400
P4—C3	1.846 (5)	C305—C306	1.396 (8)
O1—C5	1.205 (6)	C305—H305	0.9400
O2—C5	1.341 (6)	C306—H306	0.9400
O2—C7	1.437 (7)	C307—C312	1.383 (7)
C1—C4	1.515 (6)	C307—C308	1.391 (7)
C2—H2A	0.9800	C308—C309	1.380 (8)
C2—H2B	0.9800	C308—H308	0.9400
C3—H3A	0.9800	C309—C310	1.376 (9)
C3—H3B	0.9800	C309—H309	0.9400
C4—C5	1.490 (7)	C310—C311	1.375 (9)
C4—H4	0.968 (19)	C310—H310	0.9400
C7—C8	1.516 (10)	C311—C312	1.378 (8)
C7—H7A	0.9800	C311—H311	0.9400
C7—H7B	0.9800	C312—H312	0.9400
C8—H8A	0.9700	C401—C402	1.381 (7)
C8—H8B	0.9700	C401—C406	1.383 (8)
C8—H8C	0.9700	C402—C403	1.395 (8)
C101—C102	1.356 (9)	C402—H402	0.9400
C101—C106	1.371 (8)	C403—C404	1.364 (9)
C102—C103	1.399 (11)	C403—H403	0.9400
C102—H102	0.9400	C404—C405	1.375 (9)

Ir1—C4	2.046 (7)	C304—H304	0.9400
Ir1—C8	2.163 (7)	C305—C306	1.385 (10)
Ir1—C1	2.279 (6)	C305—H305	0.9400
Ir1—P4	2.306 (2)	C306—H306	0.9400
Ir1—P1	2.318 (2)	C307—C312	1.392 (9)
Ir1—Cl1	2.4607 (18)	C307—C308	1.395 (10)
P1—C107	1.831 (7)	C308—C309	1.378 (11)
P1—C101	1.840 (7)	C308—H308	0.9400
P1—C2	1.850 (7)	C309—C310	1.380 (11)
P2—C1	1.788 (7)	C309—H309	0.9400
P2—C2	1.794 (7)	C310—C311	1.385 (11)
P2—C201	1.799 (7)	C310—H310	0.9400
P2—C207	1.823 (7)	C311—C312	1.366 (10)
P3—C1	1.789 (7)	C311—H311	0.9400
P3—C301	1.799 (7)	C312—H312	0.9400
P3—C3	1.800 (7)	C407—C408	1.388 (10)
P3—C307	1.816 (7)	C407—C412	1.404 (11)
P4—C41A	1.80 (2)	C408—C409	1.396 (11)
P4—C407	1.832 (8)	C408—H408	0.9400
P4—C3	1.850 (7)	C409—C410	1.375 (12)
P4—C401	1.871 (18)	C409—H409	0.9400
C1—C4	1.507 (9)	C410—C411	1.385 (13)
C2—H2A	0.9800	C410—H410	0.9400
C2—H2B	0.9800	C411—C412	1.372 (12)
C3—H3A	0.9800	C411—H411	0.9400
C3—H3B	0.9800	C412—H412	0.9400
C101—C102	1.371 (10)	O1—C5	1.203 (8)
C101—C106	1.378 (11)	O2—C5	1.332 (8)
C102—C103	1.364 (11)	O2—C6	1.461 (8)
C102—H102	0.9400	O3—C9	1.199 (10)
C103—C104	1.350 (13)	O4—C9	1.348 (10)
C103—H103	0.9400	O4—C10	1.453 (9)
C104—C105	1.366 (13)	C4—C5	1.488 (10)
C104—H104	0.9400	C4—H4	0.947 (19)
C105—C106	1.382 (12)	C6—C7	1.500 (11)
C105—H105	0.9400	C6—H6A	0.9800
C106—H106	0.9400	C6—H6B	0.9800
C107—C108	1.373 (10)	C7—H7A	0.9700
C107—C112	1.395 (11)	C7—H7B	0.9700
C108—C109	1.380 (10)	C7—H7C	0.9700

	x	y	z	U_iso*/U_eq
Ir1	0.20012 (2)	0.37531 (2)	0.74968 (2)	0.02861 (6)
P1	0.20027 (9)	0.20029 (8)	0.72614 (6)	0.0298 (2)
P2	0.46847 (9)	0.22736 (8)	0.70579 (6)	0.0308 (2)
P3	0.46936 (10)	0.46722 (9)	0.73724 (6)	0.0317 (2)
P4	0.20277 (10)	0.55291 (8)	0.76838 (6)	0.0324 (2)
Cl1	−0.01947 (9)	0.39399 (9)	0.79680 (6)	0.0416 (3)
Cl2	0.16469 (10)	0.43456 (9)	0.63301 (5)	0.0412 (3)
Cl3	0.44061 (18)	0.83094 (12)	0.72218 (9)	0.0876 (5)
O1	0.3698 (3)	0.1714 (3)	0.85456 (16)	0.0483 (8)
O2	0.2473 (3)	0.2825 (2)	0.93555 (14)	0.0423 (7)
C1	0.3924 (4)	0.3490 (3)	0.7501 (2)	0.0316 (9)
C2	0.3590 (4)	0.1363 (3)	0.7100 (2)	0.0347 (10)
H2A	0.3676	0.0870	0.7482	0.042*
H2B	0.3767	0.0966	0.6651	0.042*
C3	0.3579 (4)	0.5712 (3)	0.7202 (2)	0.0351 (10)
H3A	0.3597	0.5738	0.6691	0.042*
H3B	0.3792	0.6379	0.7348	0.042*
C4	0.3107 (4)	0.3481 (3)	0.8234 (2)	0.0306 (9)
H4	0.313 (3)	0.406 (2)	0.8533 (16)	0.021 (9)*
C5	0.3146 (4)	0.2571 (4)	0.8709 (2)	0.0355 (10)
C6	0.2445 (5)	0.2004 (4)	0.9893 (2)	0.0522 (13)
H6A	0.3261	0.1823	0.9996	0.063*
H6B	0.2181	0.1375	0.9721	0.063*
C7	0.1549 (5)	0.2435 (4)	1.0549 (2)	0.0625 (15)
H7A	0.1501	0.1916	1.0918	0.094*
H7B	0.1820	0.3056	1.0712	0.094*
H7C	0.0746	0.2610	1.0438	0.094*
C101	0.1249 (4)	0.1183 (3)	0.7955 (2)	0.0318 (9)
C102	0.0582 (4)	0.1593 (3)	0.8602 (2)	0.0379 (10)
H102	0.0496	0.2317	0.8689	0.046*
C103	0.0044 (4)	0.0949 (4)	0.9122 (2)	0.0486 (12)
H103	−0.0408	0.1236	0.9560	0.058*
C104	0.0168 (5)	−0.0112 (4)	0.9002 (3)	0.0498 (12)
H104	−0.0205	−0.0547	0.9356	0.060*
C105	0.0834 (5)	−0.0537 (4)	0.8366 (3)	0.0516 (13)
H105	0.0928	−0.1262	0.8286	0.062*
C106	0.1362 (4)	0.0110 (3)	0.7848 (3)	0.0434 (11)
H106	0.1809	−0.0181	0.7411	0.052*
C107	0.1414 (4)	0.1673 (3)	0.6485 (2)	0.0378 (10)

Ir1—C4	2.076 (4)	C203—H203	0.9400
Ir1—C1	2.149 (4)	C204—C205	1.369 (7)
Ir1—P1	2.3093 (11)	C204—H204	0.9400
Ir1—P4	2.3298 (11)	C205—C206	1.381 (7)
Ir1—Cl1	2.4268 (10)	C205—H205	0.9400
Ir1—Cl2	2.4597 (10)	C206—H206	0.9400
P1—C101	1.825 (4)	C207—C208	1.389 (6)
P1—C107	1.830 (4)	C207—C212	1.394 (6)
P1—C2	1.838 (4)	C208—C209	1.382 (6)
P2—C2	1.790 (4)	C208—H208	0.9400
P2—C207	1.800 (4)	C209—C210	1.374 (7)
P2—C201	1.801 (4)	C209—H209	0.9400
P2—C1	1.822 (4)	C210—C211	1.376 (7)
P3—C307	1.793 (4)	C210—H210	0.9400
P3—C3	1.800 (4)	C211—C212	1.389 (6)
P3—C301	1.809 (4)	C211—H211	0.9400
P3—C1	1.833 (4)	C212—H212	0.9400
P4—C407	1.821 (4)	C301—C302	1.395 (6)
P4—C401	1.825 (4)	C301—C306	1.397 (6)
P4—C3	1.835 (4)	C302—C303	1.378 (6)
O1—C5	1.213 (5)	C302—H302	0.9400
O2—C5	1.333 (5)	C303—C304	1.378 (7)
O2—C6	1.472 (5)	C303—H303	0.9400
C1—C4	1.513 (5)	C304—C305	1.373 (7)
C2—H2A	0.9800	C304—H304	0.9400
C2—H2B	0.9800	C305—C306	1.392 (6)
C3—H3A	0.9800	C305—H305	0.9400
C3—H3B	0.9800	C306—H306	0.9400
C4—C5	1.483 (6)	C307—C308	1.396 (7)
C4—H4	0.954 (18)	C307—C312	1.397 (7)
C6—C7	1.504 (7)	C308—C309	1.391 (7)
C6—H6A	0.9800	C308—H308	0.9400
C6—H6B	0.9800	C309—C310	1.368 (9)
C7—H7A	0.9700	C309—H309	0.9400
C7—H7B	0.9700	C310—C311	1.371 (9)
C7—H7C	0.9700	C310—H310	0.9400
C101—C102	1.385 (6)	C311—C312	1.394 (7)
C101—C106	1.389 (6)	C311—H311	0.9400
C102—C103	1.382 (6)	C312—H312	0.9400
C102—H102	0.9400	C401—C402	1.364 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl2	0.98	2.58	3.488 (5)	154
C3—H3A···O1	0.98	2.31	2.892 (7)	117
C3—H3B···Cl2ⁱⁱ	0.98	2.83	3.456 (5)	122

[Ir(C₄H₇O₂)Cl(C₅₅H₅₀O₂P₄)]Cl·CH₄O·0.5H₂O	Z = 2
M_r = 1258.07	F(000) = 1274
Triclinic, P1	D_x = 1.449 Mg m⁻³
a = 12.4253 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.7081 (4) Å	Cell parameters from 57775 reflections
c = 17.6780 (6) Å	θ = 1.0–22.5°
α = 93.152 (2)°	µ = 2.57 mm⁻¹
β = 97.960 (2)°	T = 233 K
γ = 103.771 (2)°	Plate, colorless
V = 2884.18 (15) Å³	0.15 × 0.05 × 0.02 mm

Nonius KappaCCD diffractometer	6326 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 22.4°, θ_min = 1.9°
phi– and ω–scans	h = −13→13
13821 measured reflections	k = −14→14
7453 independent reflections	l = −18→18

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.047P)² + 6.9463P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
7453 reflections	Δρ_max = 0.90 e Å⁻³
674 parameters	Δρ_min = −0.96 e Å⁻³

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ir1	−0.16510 (2)	−0.10634 (2)	0.69970 (2)	0.04147 (12)
P1	−0.15686 (15)	−0.26886 (16)	0.72460 (11)	0.0454 (5)
P2	−0.35224 (14)	−0.24371 (15)	0.79978 (10)	0.0416 (5)
P3	−0.35696 (14)	−0.02021 (14)	0.78288 (10)	0.0414 (5)
P4	−0.17014 (15)	0.05959 (16)	0.68972 (11)	0.0474 (5)
Cl1	−0.00070 (14)	−0.05642 (16)	0.80140 (11)	0.0558 (5)
Cl2	−0.3358 (4)	0.3182 (3)	0.8216 (2)	0.1433 (14)
C1	−0.3307 (5)	−0.1353 (5)	0.7465 (4)	0.0389 (16)
C2	−0.2231 (6)	−0.2821 (6)	0.8122 (4)	0.0479 (19)
H2A	−0.2378	−0.3526	0.8242	0.057*
H2B	−0.1716	−0.2407	0.8555	0.057*
C3	−0.2880 (6)	0.0839 (5)	0.7350 (4)	0.053 (2)
H3A	−0.2597	0.1432	0.7722	0.063*
H3B	−0.3433	0.0996	0.6954	0.063*
C101	−0.0247 (6)	−0.3050 (6)	0.7536 (4)	0.053 (2)
C102	0.0243 (7)	−0.3454 (7)	0.6989 (5)	0.073 (3)
H102	−0.0094	−0.3522	0.6473	0.088*
C103	0.1207 (8)	−0.3760 (8)	0.7172 (6)	0.088 (3)
H103	0.1516	−0.4045	0.6785	0.106*
C104	0.1718 (7)	−0.3654 (8)	0.7907 (7)	0.088 (3)
H104	0.2376	−0.3873	0.8034	0.106*
C105	0.1274 (8)	−0.3226 (9)	0.8466 (6)	0.091 (3)
H105	0.1638	−0.3137	0.8977	0.110*
C106	0.0293 (7)	−0.2922 (7)	0.8284 (5)	0.073 (3)
H106	−0.0007	−0.2628	0.8671	0.087*
C107	−0.2385 (6)	−0.3784 (6)	0.6601 (4)	0.0460 (19)
C108	−0.2860 (5)	−0.3683 (6)	0.5870 (4)	0.0445 (18)
H108	−0.2745	−0.3043	0.5684	0.053*
C109	−0.3505 (7)	−0.4520 (7)	0.5407 (5)	0.061 (2)
H109	−0.3840	−0.4444	0.4911	0.073*
C110	−0.3662 (7)	−0.5465 (7)	0.5666 (5)	0.064 (2)
H110	−0.4097	−0.6031	0.5345	0.077*
C111	−0.3188 (8)	−0.5580 (7)	0.6388 (6)	0.069 (2)
H111	−0.3305	−0.6224	0.6568	0.083*
C112	−0.2531 (7)	−0.4745 (7)	0.6857 (5)	0.060 (2)
H112	−0.2185	−0.4827	0.7349	0.072*
C201	−0.3904 (6)	−0.2312 (5)	0.8937 (4)	0.0448 (18)
C202	−0.5033 (6)	−0.2505 (6)	0.9013 (4)	0.053 (2)
H202	−0.5579	−0.2658	0.8570	0.064*
C203	−0.5363 (8)	−0.2477 (6)	0.9718 (5)	0.066 (2)
H203	−0.6129	−0.2602	0.9758	0.079*
C204	−0.4576 (8)	−0.2267 (7)	1.0364 (5)	0.072 (3)
H204	−0.4804	−0.2267	1.0849	0.086*
C205	−0.3439 (9)	−0.2053 (7)	1.0310 (5)	0.074 (3)
H205	−0.2900	−0.1884	1.0756	0.089*
C206	−0.3110 (7)	−0.2089 (6)	0.9600 (4)	0.060 (2)
H206	−0.2342	−0.1963	0.9562	0.073*
C207	−0.4620 (6)	−0.3491 (6)	0.7494 (4)	0.0446 (18)
C208	−0.5408 (5)	−0.3389 (6)	0.6880 (4)	0.0462 (18)
H208	−0.5374	−0.2756	0.6692	0.055*
C209	−0.6234 (6)	−0.4213 (7)	0.6548 (5)	0.056 (2)
H209	−0.6767	−0.4145	0.6135	0.068*
C210	−0.6281 (7)	−0.5149 (7)	0.6825 (5)	0.070 (3)
H210	−0.6844	−0.5713	0.6593	0.083*
C211	−0.5522 (8)	−0.5262 (7)	0.7431 (6)	0.072 (3)
H211	−0.5563	−0.5897	0.7618	0.086*
C212	−0.4681 (7)	−0.4419 (6)	0.7769 (5)	0.058 (2)
H212	−0.4154	−0.4487	0.8186	0.069*
C301	−0.5010 (6)	−0.0138 (6)	0.7748 (4)	0.0418 (17)
C302	−0.5909 (6)	−0.0976 (6)	0.7612 (4)	0.053 (2)
H302	−0.5775	−0.1620	0.7548	0.064*
C303	−0.6999 (6)	−0.0886 (7)	0.7567 (5)	0.062 (2)
H303	−0.7600	−0.1465	0.7481	0.074*
C304	−0.7200 (6)	0.0057 (8)	0.7648 (4)	0.060 (2)
H304	−0.7941	0.0123	0.7614	0.072*
C305	−0.6329 (7)	0.0893 (7)	0.7777 (4)	0.057 (2)
H305	−0.6472	0.1534	0.7824	0.068*
C306	−0.5232 (6)	0.0807 (6)	0.7838 (4)	0.052 (2)
H306	−0.4636	0.1389	0.7941	0.063*
C307	−0.3001 (6)	0.0081 (6)	0.8841 (4)	0.0466 (19)
C308	−0.1853 (6)	0.0207 (7)	0.9072 (5)	0.071 (3)
H308	−0.1390	0.0106	0.8712	0.085*
C309	−0.1405 (7)	0.0481 (8)	0.9833 (5)	0.084 (3)
H309	−0.0630	0.0574	0.9987	0.101*
C310	−0.2066 (7)	0.0621 (7)	1.0376 (5)	0.071 (3)
H310	−0.1753	0.0795	1.0895	0.085*
C311	−0.3204 (6)	0.0499 (6)	1.0135 (4)	0.059 (2)
H311	−0.3664	0.0598	1.0497	0.071*
C312	−0.3670 (6)	0.0239 (6)	0.9383 (4)	0.0493 (19)
H312	−0.4443	0.0167	0.9231	0.059*
C407	−0.1952 (5)	0.1127 (6)	0.5980 (4)	0.0473 (19)
C408	−0.2121 (6)	0.0529 (6)	0.5294 (4)	0.056 (2)
H408	−0.2111	−0.0155	0.5295	0.067*
C409	−0.2304 (8)	0.0951 (8)	0.4601 (5)	0.071 (2)
H409	−0.2410	0.0547	0.4137	0.085*
C410	−0.2332 (8)	0.1947 (8)	0.4586 (6)	0.074 (3)
H410	−0.2464	0.2223	0.4117	0.088*
C411	−0.2163 (7)	0.2534 (7)	0.5275 (7)	0.076 (3)
H411	−0.2176	0.3216	0.5269	0.091*
C412	−0.1977 (7)	0.2145 (7)	0.5966 (5)	0.064 (2)
H412	−0.1866	0.2557	0.6427	0.076*
O1	−0.4427 (5)	−0.0485 (4)	0.6132 (3)	0.0596 (14)
O2	−0.4118 (4)	−0.1706 (4)	0.5351 (3)	0.0514 (13)
O3	−0.1320 (7)	−0.1339 (6)	0.4883 (4)	0.100 (2)
O4	−0.0633 (4)	−0.2499 (4)	0.5440 (3)	0.0587 (14)
C4	−0.3334 (6)	−0.1604 (5)	0.6621 (4)	0.0390 (17)
H4	−0.353 (4)	−0.2318 (16)	0.654 (3)	0.011 (13)*
C5	−0.4024 (5)	−0.1187 (6)	0.6027 (4)	0.0411 (17)
C6	−0.4691 (7)	−0.1344 (7)	0.4686 (4)	0.063 (2)
H6A	−0.4417	−0.0612	0.4685	0.075*
H6B	−0.5502	−0.1509	0.4686	0.075*
C7	−0.4415 (9)	−0.1883 (8)	0.4004 (5)	0.088 (3)
H7A	−0.4771	−0.1677	0.3537	0.131*
H7B	−0.3609	−0.1714	0.4017	0.131*
H7C	−0.4687	−0.2605	0.4018	0.131*
C8	−0.0453 (6)	−0.1001 (6)	0.6211 (4)	0.054 (2)
H8A	−0.0163	−0.0292	0.6126	0.064*
H8B	0.0179	−0.1237	0.6464	0.064*
C9	−0.0851 (7)	−0.1581 (7)	0.5455 (5)	0.059 (2)
C10	−0.0925 (8)	−0.3085 (7)	0.4698 (5)	0.074 (3)
H10A	−0.0483	−0.2737	0.4330	0.088*
H10B	−0.1722	−0.3169	0.4501	0.088*
C11	−0.0689 (8)	−0.4077 (7)	0.4797 (6)	0.093 (3)
H11A	−0.0879	−0.4481	0.4307	0.140*
H11B	0.0102	−0.3986	0.4989	0.140*
H11C	−0.1134	−0.4416	0.5159	0.140*
O5	−0.2422 (14)	0.5220 (9)	0.8989 (9)	0.107 (5)	0.5
C12	−0.190 (5)	0.564 (4)	0.9732 (15)	0.25 (3)	0.5
O6	−0.5573 (15)	0.4914 (9)	1.0173 (8)	0.101 (5)	0.5
C13	−0.665 (6)	0.4857 (18)	0.979 (2)	0.28 (4)	0.5
O7	−0.3475 (17)	0.5078 (11)	1.0734 (10)	0.113 (6)	0.5
C401	−0.0507 (14)	0.1668 (14)	0.7345 (10)	0.039 (5)*	0.5
C402	−0.0572 (18)	0.2344 (16)	0.7933 (12)	0.083 (6)*	0.5
H402	−0.1241	0.2327	0.8130	0.099*	0.5
C403	0.044 (2)	0.3058 (19)	0.8217 (15)	0.108 (7)*	0.5
H403	0.0442	0.3517	0.8633	0.129*	0.5
C404	0.137 (2)	0.3123 (17)	0.7935 (12)	0.085 (6)*	0.5
H404	0.1997	0.3663	0.8120	0.102*	0.5
C405	0.1458 (16)	0.2471 (15)	0.7416 (14)	0.055 (5)*	0.5
H405	0.2133	0.2501	0.7223	0.065*	0.5
C406	0.047 (2)	0.1700 (17)	0.7148 (14)	0.065 (8)*	0.5
H406	0.0528	0.1173	0.6803	0.077*	0.5
C41A	−0.0372 (18)	0.1384 (16)	0.7366 (12)	0.055 (7)*	0.5
C42A	−0.0192 (18)	0.1861 (15)	0.8085 (12)	0.079 (6)*	0.5
H42A	−0.0785	0.1777	0.8373	0.095*	0.5
C43A	0.093 (2)	0.2514 (18)	0.8423 (15)	0.103 (7)*	0.5
H43A	0.1097	0.2786	0.8938	0.123*	0.5
C44A	0.171 (2)	0.2690 (18)	0.7943 (14)	0.083 (6)*	0.5
H44A	0.2410	0.3123	0.8137	0.100*	0.5
C45A	0.1536 (17)	0.2269 (15)	0.7166 (12)	0.062 (6)*	0.5
H45A	0.2095	0.2422	0.6853	0.074*	0.5
C46A	0.0517 (15)	0.1634 (13)	0.6908 (12)	0.037 (5)*	0.5
H46A	0.0380	0.1339	0.6400	0.045*	0.5

[IrCl₂(C₅₅H₅₀O₂P₄)]Cl·CH₄O·2H₂O	Z = 2
M_r = 1233.45	F(000) = 1244
Triclinic, P1	D_x = 1.512 Mg m⁻³
a = 11.2371 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.9144 (2) Å	Cell parameters from 58878 reflections
c = 19.2371 (3) Å	θ = 1.0–25.3°
α = 89.439 (1)°	µ = 2.78 mm⁻¹
β = 77.863 (1)°	T = 233 K
γ = 83.114 (1)°	Prism, light yellow
V = 2709.27 (8) Å³	0.11 × 0.05 × 0.03 mm

Nonius KappaCCD diffractometer	8083 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.0°, θ_min = 1.9°
phi– and ω–scans	h = −13→13
17984 measured reflections	k = −15→15
9526 independent reflections	l = −22→22

[Ir(C₄H₇O₂)(C₅₅H₅₀O₂P₄)(CO)]Cl₂·2CH₂Cl₂·1.5H₂O	Z = 2
M_r = 1441.91	F(000) = 1454
Triclinic, P1	D_x = 1.505 Mg m⁻³
a = 11.7326 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.8815 (2) Å	Cell parameters from 109564 reflections
c = 22.2615 (3) Å	θ = 1.0–27.4°
α = 75.477 (1)°	µ = 2.50 mm⁻¹
β = 86.508 (1)°	T = 233 K
γ = 65.212 (1)°	Prism, yellow
V = 3182.38 (9) Å³	0.31 × 0.23 × 0.19 mm

Nonius KappaCCD diffractometer	11695 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
phi– and ω–scans	h = −14→14
23329 measured reflections	k = −17→16
12496 independent reflections	l = −26→27

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.026P)² + 5.2527P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
12496 reflections	Δρ_max = 0.97 e Å⁻³
751 parameters	Δρ_min = −1.29 e Å⁻³

PERMALINK

Inge Schlapp-Hackl

Christoph Falschlunger

Kathrin Zauner

Walter Schuh

Holger Kopacka

Klaus Wurst

Paul Peringer

Abstract

Chemical context

Figure 1.

Structural commentary

Figure 2.

Table 1. Selected bond lengths (Å) and angles (°) of the compounds 4, 5, 6 and 7 .

Figure 3.

Figure 4.

Figure 5.

Supra­molecular features

Table 2. Hydrogen-bond geometry (Å, °) for 4 .

Table 3. Hydrogen-bond geometry (Å, °) for 5 .

Table 4. Hydrogen-bond geometry (Å, °) for 6 .

Table 5. Hydrogen-bond geometry (Å, °) for 7 .

Figure 6.

Figure 7.

Figure 8.

Figure 9.

Synthesis and crystallization

Refinement

Table 6. Experimental details.

Supplementary Material

supplementary crystallographic information

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Atomic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Hydrogen-bond geometry (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Atomic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Hydrogen-bond geometry (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Atomic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Hydrogen-bond geometry (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Atomic displacement parameters (Å2)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ4P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Hydrogen-bond geometry (Å, º)

References

Associated Data

Supplementary Materials

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Supramolecular features

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Atomic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chloridohydridoiridium(III) chloride methylene chloride 2.75-solvate (4) . Hydrogen-bond geometry (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Atomic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')chlorido(ethoxyoxoethanido)iridium(III) chloride–methanol–water (1/1/0.5) (5) . Hydrogen-bond geometry (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Atomic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')dichloridoiridium(III) chloride–methanol–water (1/1/2) (6) . Hydrogen-bond geometry (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Crystal data

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Data collection

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Refinement

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Special details

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Atomic displacement parameters (Å²)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Geometric parameters (Å, º)

(Bis{[(diphenylphosphanyl)methyl]diphenylphosphanylidene}(ethoxyoxoethanylidene)methane-κ⁴P,C,C',P')carbonyl(ethoxyoxoethanide)iridium(III) dichloride–methylene chloride–water (1/2/1.5) (7) . Hydrogen-bond geometry (Å, º)

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ir1	0.18100 (2)	0.32675 (2)	0.19059 (2)	0.02360 (4)
P1	−0.01647 (7)	0.32287 (7)	0.20407 (4)	0.02798 (16)
P2	0.08519 (8)	0.24968 (7)	0.33707 (4)	0.02951 (17)
P3	0.36173 (7)	0.23582 (6)	0.31877 (3)	0.02553 (16)
P4	0.38428 (7)	0.32406 (6)	0.18358 (3)	0.02485 (15)
O1	0.2405 (2)	0.4989 (2)	0.30318 (12)	0.0441 (6)
O2	0.0747 (2)	0.60098 (18)	0.23599 (11)	0.0398 (6)
O3	0.2584 (3)	0.4317 (3)	0.02412 (12)	0.0555 (7)
O4	0.1299 (3)	0.3486 (2)	0.02816 (11)	0.0512 (7)
O5	0.2606 (3)	0.1321 (2)	0.13439 (14)	0.0542 (7)
C1	0.1994 (3)	0.2948 (2)	0.29337 (13)	0.0258 (6)
C2	0.0016 (3)	0.2266 (3)	0.28035 (14)	0.0322 (7)
H2A	−0.0816	0.2349	0.2950	0.039*
H2B	0.0475	0.1515	0.2761	0.039*
C3	0.4342 (3)	0.3087 (3)	0.26346 (13)	0.0275 (6)
H3A	0.5259	0.2688	0.2690	0.033*
H3B	0.4109	0.3813	0.2707	0.033*
C4	0.1312 (3)	0.4148 (2)	0.26037 (13)	0.0264 (6)
H4	0.0434 (18)	0.441 (3)	0.2635 (15)	0.030 (9)*
C5	0.1589 (3)	0.5053 (3)	0.26978 (15)	0.0320 (7)
C6	0.0842 (4)	0.7004 (3)	0.2418 (2)	0.0530 (10)
H6A	0.1702	0.6939	0.2351	0.064*
H6B	0.0618	0.7123	0.2833	0.064*
C7	−0.0043 (6)	0.7923 (4)	0.1938 (3)	0.093 (2)
H7A	−0.0011	0.8601	0.1960	0.140*
H7B	0.0190	0.7795	0.1530	0.140*
H7C	−0.0889	0.7977	0.2010	0.140*
C8	0.1075 (3)	0.4468 (3)	0.10236 (14)	0.0334 (7)
H8A	0.0184	0.4633	0.0967	0.040*
H8B	0.1127	0.5147	0.1041	0.040*
C9	0.1736 (3)	0.4113 (3)	0.04821 (14)	0.0368 (7)
C10	0.1946 (5)	0.3027 (4)	−0.0222 (2)	0.0668 (13)
H10A	0.2829	0.2543	−0.0095	0.080*
H10B	0.1916	0.3612	−0.0584	0.080*
C11	0.1298 (7)	0.2398 (5)	−0.0379 (3)	0.099 (2)
H11A	0.1708	0.2076	−0.0717	0.149*
H11B	0.1335	0.1821	−0.0018	0.149*
H11C	0.0426	0.2885	−0.0505	0.149*
C12	0.2317 (3)	0.2051 (3)	0.15415 (15)	0.0331 (7)
C101	−0.0676 (3)	0.2706 (3)	0.14917 (15)	0.0335 (7)
C102	−0.0305 (4)	0.1594 (3)	0.15564 (19)	0.0524 (10)
H102	0.0193	0.1079	0.1906	0.063*
C103	−0.0678 (5)	0.1250 (4)	0.1099 (2)	0.0660 (13)
H103	−0.0443	0.0498	0.1144	0.079*
C104	−0.1382 (5)	0.1990 (4)	0.0586 (2)	0.0607 (12)
H104	−0.1625	0.1743	0.0280	0.073*
C105	−0.1736 (4)	0.3080 (4)	0.05112 (18)	0.0506 (10)
H105	−0.2219	0.3583	0.0155	0.061*
C106	−0.1383 (3)	0.3449 (3)	0.09598 (16)	0.0416 (8)
H106	−0.1622	0.4203	0.0906	0.050*
C107	−0.1551 (3)	0.4470 (3)	0.20753 (15)	0.0343 (7)
C108	−0.1557 (3)	0.5505 (3)	0.19268 (16)	0.0397 (8)
H108	−0.0819	0.5588	0.1798	0.048*
C109	−0.2639 (4)	0.6416 (3)	0.1967 (2)	0.0544 (10)
H109	−0.2636	0.7114	0.1869	0.065*
C110	−0.3727 (4)	0.6289 (4)	0.2153 (2)	0.0639 (12)
H110	−0.4463	0.6903	0.2186	0.077*
C111	−0.3735 (4)	0.5262 (4)	0.2292 (2)	0.0586 (11)
H111	−0.4478	0.5183	0.2416	0.070*
C112	−0.2664 (3)	0.4361 (3)	0.22511 (17)	0.0454 (9)
H112	−0.2678	0.3667	0.2341	0.055*
C201	0.1375 (3)	0.1290 (3)	0.40066 (14)	0.0360 (7)
C202	0.1785 (4)	0.0254 (3)	0.39114 (18)	0.0494 (9)
H202	0.1838	0.0162	0.3505	0.059*
C203	0.2117 (5)	−0.0648 (4)	0.4412 (2)	0.0710 (14)
H203	0.2409	−0.1352	0.4344	0.085*
C204	0.2025 (5)	−0.0524 (4)	0.5010 (2)	0.0754 (15)
H204	0.2255	−0.1142	0.5348	0.091*
C205	0.1602 (5)	0.0495 (4)	0.51097 (19)	0.0699 (14)
H205	0.1536	0.0576	0.5519	0.084*
C206	0.1266 (4)	0.1415 (4)	0.46165 (17)	0.0538 (10)
H206	0.0968	0.2116	0.4690	0.065*
C207	−0.0190 (3)	0.3598 (3)	0.36982 (15)	0.0404 (8)
C208	0.0283 (4)	0.4210 (4)	0.39200 (18)	0.0542 (10)
H208	0.1143	0.4053	0.3896	0.065*
C209	−0.0505 (6)	0.5050 (5)	0.4177 (2)	0.0834 (17)
H209	−0.0180	0.5465	0.4327	0.100*
C210	−0.1743 (7)	0.5277 (6)	0.4213 (3)	0.100 (2)
H210	−0.2280	0.5860	0.4379	0.121*
C211	−0.2220 (5)	0.4656 (6)	0.4006 (3)	0.100 (2)
H211	−0.3078	0.4811	0.4043	0.119*
C212	−0.1449 (4)	0.3800 (4)	0.37442 (19)	0.0615 (12)
H212	−0.1773	0.3375	0.3604	0.074*
C301	0.3972 (3)	0.2405 (3)	0.39562 (14)	0.0319 (7)
C302	0.3965 (4)	0.1578 (3)	0.44585 (16)	0.0452 (9)
H302	0.3775	0.1016	0.4394	0.054*
C303	0.4237 (5)	0.1584 (4)	0.50518 (18)	0.0617 (12)
H303	0.4215	0.1033	0.5392	0.074*
C304	0.4536 (5)	0.2385 (4)	0.51477 (18)	0.0635 (13)
H304	0.4723	0.2378	0.5554	0.076*
C305	0.4568 (4)	0.3201 (4)	0.46571 (19)	0.0589 (11)
H305	0.4781	0.3747	0.4727	0.071*
C306	0.4285 (4)	0.3214 (3)	0.40556 (17)	0.0444 (9)
H306	0.4305	0.3770	0.3718	0.053*
C307	0.4396 (3)	0.0935 (2)	0.31728 (14)	0.0294 (6)
C308	0.3872 (3)	0.0411 (3)	0.28949 (16)	0.0382 (8)
H308	0.3039	0.0785	0.2728	0.046*
C309	0.4580 (4)	−0.0664 (3)	0.28642 (19)	0.0503 (9)
H309	0.4217	−0.1023	0.2686	0.060*
C310	0.5809 (4)	−0.1206 (3)	0.3093 (2)	0.0522 (10)
H310	0.6287	−0.1930	0.3063	0.063*
C311	0.6345 (4)	−0.0693 (3)	0.33646 (18)	0.0451 (9)
H311	0.7187	−0.1065	0.3517	0.054*
C312	0.5640 (3)	0.0370 (3)	0.34124 (15)	0.0362 (7)
H312	0.5999	0.0712	0.3607	0.043*
C401	0.4056 (3)	0.4445 (3)	0.13947 (14)	0.0298 (6)
C402	0.3124 (3)	0.5476 (3)	0.13833 (16)	0.0397 (8)
H402	0.2396	0.5549	0.1605	0.048*
C403	0.3264 (4)	0.6402 (3)	0.10452 (19)	0.0488 (9)
H403	0.2632	0.7101	0.1040	0.059*
C404	0.4319 (4)	0.6305 (3)	0.07180 (18)	0.0481 (9)
H404	0.4409	0.6936	0.0491	0.058*
C405	0.5241 (4)	0.5287 (3)	0.07225 (18)	0.0478 (9)
H405	0.5961	0.5221	0.0496	0.057*
C406	0.5115 (3)	0.4355 (3)	0.10599 (16)	0.0394 (8)
H406	0.5752	0.3660	0.1062	0.047*
C407	0.5050 (3)	0.2106 (3)	0.15751 (15)	0.0316 (7)
C408	0.4890 (4)	0.1989 (3)	0.09900 (18)	0.0458 (9)
H408	0.4177	0.2500	0.0735	0.055*
C409	0.5773 (4)	0.1125 (4)	0.0779 (2)	0.0590 (11)
H409	0.5663	0.1051	0.0381	0.071*
C410	0.6809 (5)	0.0375 (4)	0.1154 (2)	0.0652 (13)
H410	0.7395	−0.0225	0.1016	0.078*
C411	0.6996 (4)	0.0494 (4)	0.1723 (2)	0.0665 (13)
H411	0.7718	−0.0017	0.1972	0.080*
C412	0.6133 (4)	0.1358 (3)	0.19386 (18)	0.0474 (9)
H412	0.6276	0.1443	0.2329	0.057*
Cl1	−0.26323 (9)	0.19319 (10)	0.33214 (5)	0.0573 (3)
Cl2	0.17302 (11)	−0.07900 (9)	0.26051 (5)	0.0607 (3)
C13	0.3341 (7)	0.8877 (5)	0.1243 (3)	0.097 (2)
H13A	0.2976	0.9296	0.1555	0.117*
H13B	0.3525	0.8108	0.1435	0.117*
Cl3	0.4728 (3)	0.8992 (2)	0.10094 (13)	0.1458 (8)
Cl4	0.2257 (2)	0.93632 (14)	0.06158 (9)	0.1169 (6)
C14	−0.7130 (7)	0.6657 (5)	0.3733 (3)	0.0917 (19)	0.65
H14A	−0.7622	0.7437	0.3543	0.110*	0.65
H14B	−0.7438	0.6236	0.3546	0.110*	0.65
Cl5	−0.7328 (5)	0.6391 (3)	0.45165 (15)	0.1329 (15)	0.65
Cl6	−0.5546 (6)	0.6307 (7)	0.3585 (4)	0.167 (3)	0.65
C14A	−0.7130 (7)	0.6657 (5)	0.3733 (3)	0.0917 (19)	0.35
H14C	−0.7144	0.6199	0.3465	0.110*	0.35
H14D	−0.7421	0.7406	0.3471	0.110*	0.35
Cl5A	−0.832 (3)	0.6662 (17)	0.4298 (7)	0.355 (14)	0.35
Cl6A	−0.5736 (14)	0.6287 (15)	0.3920 (10)	0.276 (12)	0.35
O6	−0.0892 (5)	−0.0527 (5)	0.3189 (3)	0.1181 (17)
H6OA	−0.013 (3)	−0.063 (6)	0.316 (4)	0.13 (3)*
H6OB	−0.133 (5)	0.012 (2)	0.323 (3)	0.078 (19)*
O7	−1.0377 (12)	0.7546 (9)	0.4039 (6)	0.141 (4)	0.5

Ir1—C12	1.910 (3)	C203—H203	0.9400
Ir1—C4	2.119 (3)	C204—C205	1.361 (7)
Ir1—C8	2.177 (3)	C204—H204	0.9400
Ir1—C1	2.225 (3)	C205—C206	1.385 (6)
Ir1—P1	2.3393 (8)	C205—H205	0.9400
Ir1—P4	2.3658 (8)	C206—H206	0.9400
P1—C101	1.811 (3)	C207—C208	1.382 (6)
P1—C107	1.822 (3)	C207—C212	1.385 (6)
P1—C2	1.839 (3)	C208—C209	1.381 (6)
P2—C201	1.800 (3)	C208—H208	0.9400
P2—C207	1.802 (4)	C209—C210	1.353 (9)
P2—C2	1.810 (3)	C209—H209	0.9400
P2—C1	1.837 (3)	C210—C211	1.380 (10)
P3—C1	1.791 (3)	C210—H210	0.9400
P3—C3	1.798 (3)	C211—C212	1.398 (7)
P3—C307	1.804 (3)	C211—H211	0.9400
P3—C301	1.808 (3)	C212—H212	0.9400
P4—C407	1.820 (3)	C301—C306	1.387 (5)
P4—C401	1.821 (3)	C301—C302	1.390 (5)
P4—C3	1.840 (3)	C302—C303	1.381 (5)
O1—C5	1.208 (4)	C302—H302	0.9400
O2—C5	1.340 (4)	C303—C304	1.364 (7)
O2—C6	1.468 (4)	C303—H303	0.9400
O3—C9	1.205 (4)	C304—C305	1.374 (7)
O4—C9	1.348 (4)	C304—H304	0.9400
O4—C10	1.446 (5)	C305—C306	1.393 (5)
O5—C12	1.120 (4)	C305—H305	0.9400
C1—C4	1.515 (4)	C306—H306	0.9400
C2—H2A	0.9800	C307—C308	1.392 (5)
C2—H2B	0.9800	C307—C312	1.398 (4)
C3—H3A	0.9800	C308—C309	1.388 (5)
C3—H3B	0.9800	C308—H308	0.9400
C4—C5	1.488 (4)	C309—C310	1.376 (6)
C4—H4	0.942 (18)	C309—H309	0.9400
C6—C7	1.479 (6)	C310—C311	1.381 (6)
C6—H6A	0.9800	C310—H310	0.9400
C6—H6B	0.9800	C311—C312	1.384 (5)
C7—H7A	0.9700	C311—H311	0.9400
C7—H7B	0.9700	C312—H312	0.9400
C7—H7C	0.9700	C401—C402	1.385 (5)
C8—C9	1.470 (5)	C401—C406	1.386 (5)
C8—H8A	0.9800	C402—C403	1.386 (5)
C8—H8B	0.9800	C402—H402	0.9400
C10—C11	1.485 (8)	C403—C404	1.371 (6)
C10—H10A	0.9800	C403—H403	0.9400
C10—H10B	0.9800	C404—C405	1.371 (6)
C11—H11A	0.9700	C404—H404	0.9400
C11—H11B	0.9700	C405—C406	1.385 (5)
C11—H11C	0.9700	C405—H405	0.9400
C101—C102	1.388 (5)	C406—H406	0.9400
C101—C106	1.394 (5)	C407—C408	1.385 (5)
C102—C103	1.389 (6)	C407—C412	1.395 (5)
C102—H102	0.9400	C408—C409	1.383 (5)
C103—C104	1.363 (6)	C408—H408	0.9400
C103—H103	0.9400	C409—C410	1.373 (7)
C104—C105	1.359 (6)	C409—H409	0.9400
C104—H104	0.9400	C410—C411	1.359 (7)
C105—C106	1.384 (5)	C410—H410	0.9400
C105—H105	0.9400	C411—C412	1.380 (6)
C106—H106	0.9400	C411—H411	0.9400
C107—C108	1.389 (5)	C412—H412	0.9400
C107—C112	1.398 (5)	C13—Cl3	1.736 (8)
C108—C109	1.383 (5)	C13—Cl4	1.746 (7)
C108—H108	0.9400	C13—H13A	0.9800
C109—C110	1.386 (7)	C13—H13B	0.9800
C109—H109	0.9400	C14—Cl5	1.713 (7)
C110—C111	1.385 (7)	C14—Cl6	1.745 (10)
C110—H110	0.9400	C14—H14A	0.9800
C111—C112	1.370 (6)	C14—H14B	0.9800
C111—H111	0.9400	C14A—Cl6A	1.545 (15)
C112—H112	0.9400	C14A—Cl5A	1.82 (2)
C201—C202	1.381 (5)	C14A—H14C	0.9800
C201—C206	1.403 (5)	C14A—H14D	0.9800
C202—C203	1.380 (5)	O6—H6OA	0.85 (2)
C202—H202	0.9400	O6—H6OB	0.845 (19)
C203—C204	1.377 (7)

C12—Ir1—C4	158.78 (12)	C112—C111—H111	119.9
C12—Ir1—C8	93.36 (13)	C110—C111—H111	119.9
C4—Ir1—C8	106.70 (12)	C111—C112—C107	120.2 (4)
C12—Ir1—C1	118.82 (12)	C111—C112—H112	119.9
C4—Ir1—C1	40.72 (11)	C107—C112—H112	119.9
C8—Ir1—C1	147.39 (12)	C202—C201—C206	119.1 (3)
C12—Ir1—P1	88.65 (10)	C202—C201—P2	121.8 (3)
C4—Ir1—P1	85.11 (9)	C206—C201—P2	118.9 (3)
C8—Ir1—P1	88.50 (9)	C203—C202—C201	120.2 (4)
C1—Ir1—P1	87.22 (8)	C203—C202—H202	119.9
C12—Ir1—P4	91.76 (10)	C201—C202—H202	119.9
C4—Ir1—P4	93.24 (8)	C204—C203—C202	120.5 (5)
C8—Ir1—P4	95.09 (9)	C204—C203—H203	119.7
C1—Ir1—P4	89.41 (8)	C202—C203—H203	119.7
P1—Ir1—P4	176.35 (3)	C205—C204—C203	119.9 (4)
C101—P1—C107	102.78 (15)	C205—C204—H204	120.1
C101—P1—C2	106.38 (15)	C203—C204—H204	120.1
C107—P1—C2	105.77 (15)	C204—C205—C206	120.9 (4)
C101—P1—Ir1	116.72 (11)	C204—C205—H205	119.6
C107—P1—Ir1	120.29 (11)	C206—C205—H205	119.6
C2—P1—Ir1	103.76 (10)	C205—C206—C201	119.4 (4)
C201—P2—C207	105.53 (16)	C205—C206—H206	120.3
C201—P2—C2	107.18 (15)	C201—C206—H206	120.3
C207—P2—C2	110.99 (17)	C208—C207—C212	120.6 (4)
C201—P2—C1	120.40 (15)	C208—C207—P2	119.7 (3)
C207—P2—C1	107.20 (16)	C212—C207—P2	119.7 (3)
C2—P2—C1	105.50 (14)	C209—C208—C207	120.2 (5)
C1—P3—C3	106.12 (14)	C209—C208—H208	119.9
C1—P3—C307	111.84 (14)	C207—C208—H208	119.9
C3—P3—C307	107.34 (14)	C210—C209—C208	120.1 (6)
C1—P3—C301	117.32 (14)	C210—C209—H209	120.0
C3—P3—C301	108.18 (15)	C208—C209—H209	120.0
C307—P3—C301	105.63 (15)	C209—C210—C211	120.3 (5)
C407—P4—C401	104.51 (14)	C209—C210—H210	119.9
C407—P4—C3	105.94 (15)	C211—C210—H210	119.9
C401—P4—C3	103.41 (14)	C210—C211—C212	121.1 (5)
C407—P4—Ir1	116.18 (11)	C210—C211—H211	119.5
C401—P4—Ir1	119.97 (11)	C212—C211—H211	119.5
C3—P4—Ir1	105.34 (10)	C207—C212—C211	117.7 (5)
C5—O2—C6	116.8 (3)	C207—C212—H212	121.1
C9—O4—C10	116.1 (3)	C211—C212—H212	121.1
C4—C1—P3	121.7 (2)	C306—C301—C302	119.5 (3)
C4—C1—P2	108.3 (2)	C306—C301—P3	122.3 (3)
P3—C1—P2	122.16 (16)	C302—C301—P3	118.2 (3)
C4—C1—Ir1	65.88 (15)	C303—C302—C301	119.8 (4)
P3—C1—Ir1	110.27 (14)	C303—C302—H302	120.1
P2—C1—Ir1	115.59 (14)	C301—C302—H302	120.1
P2—C2—P1	111.79 (17)	C304—C303—C302	120.5 (4)
P2—C2—H2A	109.3	C304—C303—H303	119.8
P1—C2—H2A	109.3	C302—C303—H303	119.8
P2—C2—H2B	109.3	C303—C304—C305	120.7 (4)
P1—C2—H2B	109.3	C303—C304—H304	119.6
H2A—C2—H2B	107.9	C305—C304—H304	119.6
P3—C3—P4	110.67 (16)	C304—C305—C306	119.6 (4)
P3—C3—H3A	109.5	C304—C305—H305	120.2
P4—C3—H3A	109.5	C306—C305—H305	120.2
P3—C3—H3B	109.5	C301—C306—C305	119.9 (4)
P4—C3—H3B	109.5	C301—C306—H306	120.1
H3A—C3—H3B	108.1	C305—C306—H306	120.1
C5—C4—C1	125.7 (3)	C308—C307—C312	119.2 (3)
C5—C4—Ir1	131.9 (2)	C308—C307—P3	124.0 (2)
C1—C4—Ir1	73.40 (16)	C312—C307—P3	116.5 (2)
C5—C4—H4	104 (2)	C309—C308—C307	119.9 (3)
C1—C4—H4	112 (2)	C309—C308—H308	120.1
Ir1—C4—H4	108 (2)	C307—C308—H308	120.1
O1—C5—O2	122.8 (3)	C310—C309—C308	120.4 (4)
O1—C5—C4	127.9 (3)	C310—C309—H309	119.8
O2—C5—C4	109.2 (3)	C308—C309—H309	119.8
O2—C6—C7	106.6 (3)	C309—C310—C311	120.3 (4)
O2—C6—H6A	110.4	C309—C310—H310	119.8
C7—C6—H6A	110.4	C311—C310—H310	119.8
O2—C6—H6B	110.4	C310—C311—C312	119.9 (3)
C7—C6—H6B	110.4	C310—C311—H311	120.0
H6A—C6—H6B	108.6	C312—C311—H311	120.0
C6—C7—H7A	109.5	C311—C312—C307	120.2 (3)
C6—C7—H7B	109.5	C311—C312—H312	119.9
H7A—C7—H7B	109.5	C307—C312—H312	119.9
C6—C7—H7C	109.5	C402—C401—C406	119.1 (3)
H7A—C7—H7C	109.5	C402—C401—P4	119.2 (2)
H7B—C7—H7C	109.5	C406—C401—P4	121.7 (3)
C9—C8—Ir1	114.1 (2)	C401—C402—C403	120.0 (3)
C9—C8—H8A	108.7	C401—C402—H402	120.0
Ir1—C8—H8A	108.7	C403—C402—H402	120.0
C9—C8—H8B	108.7	C404—C403—C402	120.4 (4)
Ir1—C8—H8B	108.7	C404—C403—H403	119.8
H8A—C8—H8B	107.6	C402—C403—H403	119.8
O3—C9—O4	122.3 (3)	C405—C404—C403	120.0 (3)
O3—C9—C8	126.2 (3)	C405—C404—H404	120.0
O4—C9—C8	111.5 (3)	C403—C404—H404	120.0
O4—C10—C11	107.2 (5)	C404—C405—C406	120.2 (4)
O4—C10—H10A	110.3	C404—C405—H405	119.9
C11—C10—H10A	110.3	C406—C405—H405	119.9
O4—C10—H10B	110.3	C405—C406—C401	120.3 (3)
C11—C10—H10B	110.3	C405—C406—H406	119.9
H10A—C10—H10B	108.5	C401—C406—H406	119.9
C10—C11—H11A	109.5	C408—C407—C412	118.9 (3)
C10—C11—H11B	109.5	C408—C407—P4	118.6 (3)
H11A—C11—H11B	109.5	C412—C407—P4	122.6 (3)
C10—C11—H11C	109.5	C409—C408—C407	120.4 (4)
H11A—C11—H11C	109.5	C409—C408—H408	119.8
H11B—C11—H11C	109.5	C407—C408—H408	119.8
O5—C12—Ir1	177.9 (3)	C410—C409—C408	119.7 (4)
C102—C101—C106	119.1 (3)	C410—C409—H409	120.2
C102—C101—P1	122.4 (3)	C408—C409—H409	120.2
C106—C101—P1	118.2 (3)	C411—C410—C409	120.6 (4)
C101—C102—C103	119.3 (4)	C411—C410—H410	119.7
C101—C102—H102	120.4	C409—C410—H410	119.7
C103—C102—H102	120.4	C410—C411—C412	120.5 (4)
C104—C103—C102	120.7 (4)	C410—C411—H411	119.7
C104—C103—H103	119.6	C412—C411—H411	119.7
C102—C103—H103	119.6	C411—C412—C407	119.8 (4)
C105—C104—C103	120.7 (4)	C411—C412—H412	120.1
C105—C104—H104	119.7	C407—C412—H412	120.1
C103—C104—H104	119.7	Cl3—C13—Cl4	111.3 (4)
C104—C105—C106	120.0 (4)	Cl3—C13—H13A	109.4
C104—C105—H105	120.0	Cl4—C13—H13A	109.4
C106—C105—H105	120.0	Cl3—C13—H13B	109.4
C105—C106—C101	120.2 (4)	Cl4—C13—H13B	109.4
C105—C106—H106	119.9	H13A—C13—H13B	108.0
C101—C106—H106	119.9	Cl5—C14—Cl6	110.5 (4)
C108—C107—C112	119.1 (3)	Cl5—C14—H14A	109.6
C108—C107—P1	123.4 (3)	Cl6—C14—H14A	109.6
C112—C107—P1	117.5 (3)	Cl5—C14—H14B	109.6
C109—C108—C107	120.7 (4)	Cl6—C14—H14B	109.6
C109—C108—H108	119.7	H14A—C14—H14B	108.1
C107—C108—H108	119.7	Cl6A—C14A—Cl5A	123.0 (11)
C108—C109—C110	119.4 (4)	Cl6A—C14A—H14C	106.6
C108—C109—H109	120.3	Cl5A—C14A—H14C	106.6
C110—C109—H109	120.3	Cl6A—C14A—H14D	106.6
C111—C110—C109	120.3 (4)	Cl5A—C14A—H14D	106.6
C111—C110—H110	119.9	H14C—C14A—H14D	106.5
C109—C110—H110	119.9	H6OA—O6—H6OB	109 (7)
C112—C111—C110	120.3 (4)

C3—P3—C1—C4	−32.3 (3)	C1—P2—C201—C206	101.9 (3)
C307—P3—C1—C4	−149.1 (2)	C206—C201—C202—C203	−1.9 (6)
C301—P3—C1—C4	88.7 (3)	P2—C201—C202—C203	−176.6 (4)
C3—P3—C1—P2	−177.92 (18)	C201—C202—C203—C204	1.0 (8)
C307—P3—C1—P2	65.3 (2)	C202—C203—C204—C205	0.1 (9)
C301—P3—C1—P2	−56.9 (2)	C203—C204—C205—C206	−0.4 (9)
C3—P3—C1—Ir1	41.19 (18)	C204—C205—C206—C201	−0.5 (8)
C307—P3—C1—Ir1	−75.56 (17)	C202—C201—C206—C205	1.6 (6)
C301—P3—C1—Ir1	162.17 (14)	P2—C201—C206—C205	176.5 (4)
C201—P2—C1—C4	−159.6 (2)	C201—P2—C207—C208	91.7 (3)
C207—P2—C1—C4	−39.2 (2)	C2—P2—C207—C208	−152.5 (3)
C2—P2—C1—C4	79.2 (2)	C1—P2—C207—C208	−37.7 (3)
C201—P2—C1—P3	−10.0 (3)	C201—P2—C207—C212	−86.1 (3)
C207—P2—C1—P3	110.4 (2)	C2—P2—C207—C212	29.7 (4)
C2—P2—C1—P3	−131.2 (2)	C1—P2—C207—C212	144.4 (3)
C201—P2—C1—Ir1	128.96 (17)	C212—C207—C208—C209	−1.7 (6)
C207—P2—C1—Ir1	−110.60 (17)	P2—C207—C208—C209	−179.5 (4)
C2—P2—C1—Ir1	7.8 (2)	C207—C208—C209—C210	0.1 (8)
C201—P2—C2—P1	−163.12 (18)	C208—C209—C210—C211	1.4 (10)
C207—P2—C2—P1	82.1 (2)	C209—C210—C211—C212	−1.4 (11)
C1—P2—C2—P1	−33.7 (2)	C208—C207—C212—C211	1.6 (6)
C101—P1—C2—P2	167.17 (18)	P2—C207—C212—C211	179.4 (4)
C107—P1—C2—P2	−84.0 (2)	C210—C211—C212—C207	−0.1 (9)
Ir1—P1—C2—P2	43.49 (19)	C1—P3—C301—C306	−96.7 (3)
C1—P3—C3—P4	−45.4 (2)	C3—P3—C301—C306	23.2 (3)
C307—P3—C3—P4	74.32 (19)	C307—P3—C301—C306	137.9 (3)
C301—P3—C3—P4	−172.12 (15)	C1—P3—C301—C302	85.3 (3)
C407—P4—C3—P3	−94.87 (18)	C3—P3—C301—C302	−154.8 (3)
C401—P4—C3—P3	155.50 (17)	C307—P3—C301—C302	−40.1 (3)
Ir1—P4—C3—P3	28.78 (17)	C306—C301—C302—C303	1.6 (6)
P3—C1—C4—C5	−30.3 (4)	P3—C301—C302—C303	179.7 (3)
P2—C1—C4—C5	119.4 (3)	C301—C302—C303—C304	−1.3 (7)
Ir1—C1—C4—C5	−130.1 (3)	C302—C303—C304—C305	0.2 (8)
P3—C1—C4—Ir1	99.8 (2)	C303—C304—C305—C306	0.4 (7)
P2—C1—C4—Ir1	−110.49 (16)	C302—C301—C306—C305	−1.0 (6)
C6—O2—C5—O1	−0.8 (5)	P3—C301—C306—C305	−179.0 (3)
C6—O2—C5—C4	177.3 (3)	C304—C305—C306—C301	0.0 (6)
C1—C4—C5—O1	2.1 (5)	C1—P3—C307—C308	10.8 (3)
Ir1—C4—C5—O1	−97.9 (4)	C3—P3—C307—C308	−105.2 (3)
C1—C4—C5—O2	−175.9 (3)	C301—P3—C307—C308	139.5 (3)
Ir1—C4—C5—O2	84.2 (3)	C1—P3—C307—C312	−174.7 (2)
C5—O2—C6—C7	171.6 (4)	C3—P3—C307—C312	69.3 (3)
C10—O4—C9—O3	2.9 (5)	C301—P3—C307—C312	−46.0 (3)
C10—O4—C9—C8	−175.7 (3)	C312—C307—C308—C309	0.6 (5)
Ir1—C8—C9—O3	−95.1 (4)	P3—C307—C308—C309	175.0 (3)
Ir1—C8—C9—O4	83.4 (3)	C307—C308—C309—C310	−1.7 (6)
C9—O4—C10—C11	−178.5 (4)	C308—C309—C310—C311	1.1 (6)
C107—P1—C101—C102	−143.3 (3)	C309—C310—C311—C312	0.5 (6)
C2—P1—C101—C102	−32.4 (4)	C310—C311—C312—C307	−1.6 (5)
Ir1—P1—C101—C102	82.8 (3)	C308—C307—C312—C311	1.0 (5)
C107—P1—C101—C106	42.1 (3)	P3—C307—C312—C311	−173.8 (3)
C2—P1—C101—C106	153.0 (3)	C407—P4—C401—C402	166.4 (3)
Ir1—P1—C101—C106	−91.8 (3)	C3—P4—C401—C402	−82.9 (3)
C106—C101—C102—C103	−1.9 (6)	Ir1—P4—C401—C402	34.0 (3)
P1—C101—C102—C103	−176.5 (4)	C407—P4—C401—C406	−12.3 (3)
C101—C102—C103—C104	1.2 (7)	C3—P4—C401—C406	98.4 (3)
C102—C103—C104—C105	−0.1 (8)	Ir1—P4—C401—C406	−144.8 (2)
C103—C104—C105—C106	−0.1 (7)	C406—C401—C402—C403	−0.6 (5)
C104—C105—C106—C101	−0.6 (6)	P4—C401—C402—C403	−179.4 (3)
C102—C101—C106—C105	1.6 (6)	C401—C402—C403—C404	0.3 (6)
P1—C101—C106—C105	176.4 (3)	C402—C403—C404—C405	0.2 (6)
C101—P1—C107—C108	−121.0 (3)	C403—C404—C405—C406	−0.4 (6)
C2—P1—C107—C108	127.6 (3)	C404—C405—C406—C401	0.1 (6)
Ir1—P1—C107—C108	10.8 (3)	C402—C401—C406—C405	0.4 (5)
C101—P1—C107—C112	57.8 (3)	P4—C401—C406—C405	179.1 (3)
C2—P1—C107—C112	−53.6 (3)	C401—P4—C407—C408	−73.7 (3)
Ir1—P1—C107—C112	−170.4 (2)	C3—P4—C407—C408	177.4 (3)
C112—C107—C108—C109	1.7 (5)	Ir1—P4—C407—C408	60.9 (3)
P1—C107—C108—C109	−179.5 (3)	C401—P4—C407—C412	105.6 (3)
C107—C108—C109—C110	−0.5 (6)	C3—P4—C407—C412	−3.3 (3)
C108—C109—C110—C111	−0.6 (7)	Ir1—P4—C407—C412	−119.8 (3)
C109—C110—C111—C112	0.5 (7)	C412—C407—C408—C409	2.0 (6)
C110—C111—C112—C107	0.8 (6)	P4—C407—C408—C409	−178.7 (3)
C108—C107—C112—C111	−1.8 (5)	C407—C408—C409—C410	0.4 (7)
P1—C107—C112—C111	179.3 (3)	C408—C409—C410—C411	−2.1 (7)
C207—P2—C201—C202	155.4 (3)	C409—C410—C411—C412	1.3 (8)
C2—P2—C201—C202	37.0 (3)	C410—C411—C412—C407	1.2 (7)
C1—P2—C201—C202	−83.3 (3)	C408—C407—C412—C411	−2.8 (6)
C207—P2—C201—C206	−19.4 (3)	P4—C407—C412—C411	177.9 (3)
C2—P2—C201—C206	−137.7 (3)