research communications
Crystal structures of [μ2-(Ra,Sa,3aR,7aR)-1,3-bis(2,7-dicyclohexylnaphthalen-1-yl)octahydro-1H-benzo[d]imidazolidin-2-ylidene]chlorido(η4-1,5-cyclooctadiene)iridium dichloromethane monosolvate and [μ2-(Sa,Sa,3aR,7aR)-1,3-bis(2,7-dicyclohexylnaphthalen-1-yl)octahydro-1H-benzo[d]imidazolidin-2-ylidene]chlorido(η4-1,5-cyclooctadiene)iridium
aCentre for Microscopy, Characterisation and Analysis, University of Western Australia, 35 Stirling Highway, 6009 Perth, Western Australia, Australia, and bDepartment of Chemistry, School of Molecular Sciences, University of Western Australia, M310, 35 Stirling Highway, 6009 Perth, Western Australia, Australia
*Correspondence e-mail: daven.foster@research.uwa.edu.au
The title compounds, [Ir(C51H64N2)Cl(C8H12)]·CH2Cl2, (I), and [Ir(C51H64N2)Cl(C8H12)], (II), represent the first two examples of hexahydrobenzoimidazole-based N-heterocyclic carbene (NHC) iridium complexes. The diastereomeric complexes differing only in their axial which could be separated via show noticeable differences in their 1H NMR spectra. Compound (I) crystallizes in the monoclinic system (P21) with two independent complexes and two half-occupied dichloromethane molecules in the while compound (II) crystallizes in the orthorhombic system (P212121) with one complex in the The fused five-membered N-heterocycles of NHCs show unusually high backbone torsion angles of −34.1 (5) and −30.9 (5)° for (I) and −31.5 (7)° for (II), but the Ir—Ccarbene bond lengths of 2.046 (6) and 2.021 (6) Å for (I) and 2.045 (8) Å for (II) present typical NHC—Ir bond lengths. The solvent molecule in the crystal of (I) was found to be highly disordered and its contribution to the scattering was masked using the solvent-masking routine smtbx.mask in OLEX2 [Dolomanov et al. (2009). J. Appl. Cryst. 42, 339–341]. The solvent contribution is not included in the reported chemical formula and other crystal data.
Keywords: crystal structure; N-heterocyclic carbene; iridium; naphthyl; cyclooctadiene.
1. Chemical context
The use of N-heterocyclic (NHCs) as ancillary ligands for various metal complexes has been implemented extensively, resulting in the synthesis of many successful catalytic species. When enantiopure catalysts are used, asymmetric transformations can be performed that result in enantio-enriched synthetic products. In terms of chiral NHC ligand design, substituents on the NHC that are too distal to the coordination sphere of the metal centre generally result in low enantio-selectivities for such catalysts. Some NHCs featuring a fused, chiral cyclohexyl backbone (modelled on the salen-type or Trost-type ligands) have been reported and studied, but the catalytic capabilities of such complexes resulted in disappointing enantio-selection (Lee & Hartwig, 2001; Arao et al., 2006; Luan et al., 2008; Lai et al., 2009). Using bulky naphthyl wingtips for the NHCs, axial is generated due to hindrance of rotation around the C—N bonds. With implementation of an enantiopure cyclohexyl backbone, three isomers are present in the mixture and are isolable via as previously reported for similar Ir–NHC complexes (Gao et al., 2020). Herein we report a new NHC ligand that uses bulky 2,7-dicyclohexyl naphthyl wingtips on the NHC in the hope that it will result in iridium precatalysts that can successfully perform catalytic transformations with high enantio-selectivity (Fig. 1).
2. Structural commentary
The molecular structures of the title compounds, (I) and (II), are depicted in Figs. 2 and 3, respectively. The two compounds crystallized under the same conditions, where the complexes were dissolved in a minimum amount of dichloromethane (DCM) under an inert atmosphere and layered with pentane, which then slowly diffused into the DCM solution overnight resulting in the formation of yellow crystals. Compound (I) crystallizes in the monoclinic system (P21) with two independent complexes and two half-occupied DCM molecules in the the solvent DCM molecules were masked in the due to high disordering. Compound (II) crystallizes in the orthorhombic system (P212121) with one complex in the asymmetric unit.
The overall geometry of the complexes is square planar. The cyclohexyl rings in the fused N-heterocyclic ring systems of (I) and (II) adopt a chair conformation, which lead to the distortion of the 5-membered imidazolidine ring. The torsion angles corresponding to N12—C13—C14—N15 are −34.1 (5) and −30.9 (5)° for (I) and −31.5 (7)° for (II). The Ir—Ccarbene bond lengths are 2.046 (6) and 2.021 (6) Å for (I) and 2.045 (8) Å for (II). With respect to other complexes of general formula (NHC)Ir(COD)Cl, where COD is cyclooctadiene, these bond lengths are quite similar to 2.041 (3) Å in (SIMes)Ir(COD)Cl, 2.049 (5) Å in (SIPr)Ir(COD)Cl (Kelly et al., 2008), 2.034 (1) Å in (anti-2-SICyNap)Ir(COD)Cl, 2.052 (5) Å in (anti-2,7-SICyNap)Ir(COD)Cl (Sipos et al., 2016), 2.034 (3) Å in (anti-2-SICyOctNap)Ir(COD)Cl and 2.053 (5) Å [(Ra,Ra,S,S)-DiPh-2,7-SICyNap]Ir(COD)Cl (Gao et al., 2020). Whilst being shorter than the values of 2.072 (6) and 2.055 (6) Å for two independent molecules of (2-SIMorNap)Ir(COD)Cl (Ou et al., 2017), the bonds in the title compounds are slightly longer than in [(Ra,Sa,S,S)-DiPh-2-SICyNap]Ir(COD)Cl [2.028 (7) Å; Gao et al., 2020]. DiPh (di-phenyl) and FuCy (fused cyclohexyl) refer to the backbone of the NHC, and SI (saturated imidazolium) refers to the NHC type. Mes (2,4,6-trimethyl phenyl), Pr (2,6-diisopropyl phenyl), CyNap (cyclohexyl 1-naphthalene), CyOctNaph (cyclooctyl 1-naphthalene) and MorNap (morpholinyl 1-naphthalene) refer to the side-chain substitution.
Saturated achiral or racemic NHC–Ir–COD complexes without a fused second ring appear to have a greater degree of flexibility and show clearly smaller distortions within the five-membered N-heterocycle, with backbone torsion angles ranging from 1.6° for (anti-2-SICyNap)Ir(COD)Cl to 19.5° for (SIPr)Ir(COD)Cl. For enantiopure complexes, [(Ra,Ra,S,S)-DiPh-2-SICyNap]Ir(COD)Cl has a torsion angle of 9.4° and [(Ra,Ra,S,S)-DiPh-2,7-SICyNap]Ir(COD)Cl has 11.9°, with a small range in angles of different molecules in the same crystal (Δ0.3°), revealing that increased bulk on the backbone appears to increase the rigidity of the NHC ring.
3. Supramolecular features
In the crystal of (I), the complex molecules are stacked in a column along the b axis via weak C—H⋯Cl interactions (Table 1 and Fig. 4). In comparison, (II) has no obvious interactions between molecules.
4. Database survey
The only other report of a crystallographically characterized fused cyclohexyl NHC complex is (FuCySIMes)Rh(COD)Cl (CSD Refcode BUNRIM; Lai et al., 2009). The backbone torsion angle in the NHC was 32.0° (average of two independent molecules), slightly larger than those found in the title complexes. Selected examples of other crystallographically characterized saturated NHC-iridium-COD complexes with aromatic wingtips include (see Structural commentary for abbreviations) (SIMes)Ir(COD)py[PF6] (XIDLAX; Lee, Jiang et al., 2001), (SIMes)Ir(COD)Cl (QIWPAO), (SIPr)Ir(COD)Cl (QIWPIW) (Kelly et al., 2008), [K](OCO)Ir(COD) [OCO = 1,3-di(2-hydroxy-5-tert-butylphenyl)imidazolyl; USOZIM; Weinberg et al., 2010], chiral (anti-2-SICyNap)Ir(COD)Cl (UMEGEA), (anti-2,7-SICyNap)Ir(COD)Cl (UMEGIE), (anti-2,7SICyNap)Ir(COD)[PF6] (UMEHIF) (Sipos et al., 2016), (2-SIMorNap)Ir(COD)Cl (XARZUO; Ou et al. 2017) and (anti-2-SICyOctNap)Ir(COD)Cl (POWGAM; Gao et al., 2020). Enantiopure versions include [(Ra,Ra,S,S)-DiPh-2-SICyNap]Ir(COD)Cl (XUKYUA), [(Ra,Ra,S,S)-DiPh-2-SICyNap]Ir(COD)[PF6] (XUKYAG) and [(Ra,Ra,S,S)-DiPh-2,7-SICyNap]Ir(COD)Cl (XUKZIP) (Gao et al., 2020).
5. Synthesis and crystallization
2,7-FuCySICyNap·HBF4 (300 mg, 0.38 mmol) was added to a solution of [Ir(COD)Cl]2 (138 mg, 0.18 mmol) in THF (8 mL) in a glovebox and was stirred at room temperature. KOtBu (42 mg, 0.38 mmol) was then added and the yellow solution was stirred for 3 h. The yellow–brown solution was evaporated to dryness and the three were separated via (1.5 kg SiO2, diameter 5cm, 1:20 diethyl ether:hexane) to afford the products as yellow powders after evaporation of the respective fractions under vacuum: yield 78 mg (21%) for (I), 40 mg (11%) for (II) and 101 mg (27%) for [(Ra,Ra,R,R)-2,7-FuCySICyNap]Ir(COD)Cl. The respective yellow powders were dissolved in DCM and layered with pentane to obtain yellow crystals of two of the three isomers, (I) and (II).
(I) 1H NMR (600 MHz, CD2Cl2): δ 7.97 (s, 1H, H8), 7.92–7.83 (m, 4H), 7.58 (dd, Ja = 8.6 Hz, Jb = 1.1 Hz, 2H), 7.50 (s, 1H, H8), 7.49–7.43 (m, 2H), 4.30–4.23 (m, 1H), 3.86–3.72 (m, 2H), 3.65–3.59 (m, 1H), 3.53–3.46 (m, 1H), 3.31–3.25 (m, 1H), 3.09–3.04 (m, 1H), 2.93–2.71 (m, 3H), 2.64 (d, J = 12.1 Hz, 1H), 2.48 (d, J = 11.6 Hz, 1H), 2.15–0.76 (m, 52H), 0.75–0.68 (m, 1H), 0.56–0.47 (m, 1H) ppm. 13C NMR (151 MHz, CD2Cl2): δ 214.2 (carbene), 146.4, 145.8, 145.5. 145.4, 133.5, 132.8, 132.2, 132.08, 132.05, 131.9, 128.9, 128.8, 128.7, 128.3, 125.5, 125.0, 124.6, 124.4, 122.3, 122.2, 84.7, 82.3, 71.6, 71.4, 54.5, 52.7, 46.2, 45.8, 40.7, 38.5, 37.8, 37.2, 35.7, 35.1, 34.3, 34.03, 34.01, 29.2, 29.1, 27.9, 27.80, 27.78, 27.4, 27.3, 27.2, 27.02, 27.00, 26.96, 26.9, 26.83, 26.79, 26.58, 26.55, 24.8, 24.5 ppm. Elemental analysis (%) calculated for C59H76N2IrCl: C 68.06, H 7.36, N 2.69. Found: C 68.21, H 7.56, N 2.82.
(II): 1H NMR (500 MHz, CD2Cl2): δ 8.22 (s, 1H), 7.89 (d, J = 8.7 Hz, 1H), 7.853 (d, J = 8.3 Hz, 1H), 7.848 (d, J = 8.3 Hz, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.61 (d, J = 8.7 Hz, 1H), 7.52 (d, J = 8.7 Hz, 1H), 7.44 (s, 1H), 7.43 (d, J = 8.2 Hz), 7.38 (dd, Ja = 8.3 Hz; Jb = 1.5 Hz, 1H), 4.21–4.11 (m, 1H), 4.10–3.98 (m, 2H), 3.78–3.64 (m, 2H), 3.36–3.23 (m, 2H), 2.90–2.73 (m, 3H), 2.49 (d, J = 11.9 Hz, 1H), 2.25 (d, J = 13.0 Hz, 1H), 2.12 (d, J = 12.6 Hz, 1H), 2.05–1.01 (m, 74H), 0.93–0.80 (m, 2H), 0.74–0.64 (m, 1H) ppm. 13C NMR (126 MHz, CD2Cl2): δ 212.1 (carbene), 146.41, 146.39, 144.6, 144.0, 132.8, 132.5, 132.1, 132.0, 131.89, 131.0, 129.0, 128.9, 128.5, 127.4, 126.6, 125., 125.7, 124.7, 124.3, 121.9 (aromatic carbons), 85.2, 74.1, 71.8, 70.1 (olefinic carbons), 50.0, 46.2, 45.9, 40.4, 39.0, 37.1, 36.8, 35.3, 34.7, 33.69, 33.68, 33.5, 33.3, 33.2, 29.9, 29.8, 28.9, 28.5, 27.9, 27.7, 27.6, 27.3, 27.2, 27.1, 26.9, 26.80, 26.79, 26.6, 26.4, 24.7, 24.6 ppm. Elemental analysis (%) calculated for C59H76N2IrCl: C 68.06, H 7.36, N 2.69. Found: C 68.55, H 7.61, N 2.54.
6. Refinement
Crystal data, data collection and structure . For (I) the solvent molecule was masked using the smtbx masking tool in OLEX2 (Dolomanov et al., 2009) due to diffuse electron density that could not be fitted using an atomistic model. The mask gave two void positions, of 428 and 414 Å3, and with 76.2 and 74.7 electrons, respectively. This equates to two half-occupied DCM molecules. Hydrogen atoms were positioned geometrically (C—H = 0.95–1.00 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 2Supporting information
https://doi.org/10.1107/S2056989020011603/is5546sup1.cif
contains datablocks I, II, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020011603/is5546Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020011603/is5546IIsup3.hkl
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell
CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019). Program(s) used to solve structure: OLEX2.solve (Bourhis et al., 2015) for (I); SHELXT (Sheldrick, 2015a) for (II). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b) for (I); SHELXL2014 (Sheldrick, 2015b) for (II). For both structures, molecular graphics: DIAMOND (Brandenburg, 1999). Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for (I); WinGX (Farrugia, 2012) for (II).[Ir(C51H64N2)Cl(C8H12)] | F(000) = 2152 |
Mr = 1040.86 | Dx = 1.271 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 19.0004 (2) Å | Cell parameters from 82075 reflections |
b = 10.4520 (1) Å | θ = 3.3–31.6° |
c = 28.7168 (4) Å | µ = 2.54 mm−1 |
β = 107.513 (1)° | T = 102 K |
V = 5438.59 (11) Å3 | Block, clear light yellow |
Z = 4 | 0.41 × 0.20 × 0.10 mm |
Oxford Diffraction Xcalibur, Ruby, Gemini ultra diffractometer | 38134 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 32830 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 10.4738 pixels mm-1 | θmax = 32.8°, θmin = 3.2° |
ω scans | h = −28→27 |
Absorption correction: multi-scan CrysAlisPro (Rigaku OD, 2019) | k = −15→15 |
Tmin = 0.808, Tmax = 1.000 | l = −43→43 |
349557 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0273P)2 + 10.0086P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.083 | (Δ/σ)max = 0.003 |
S = 1.04 | Δρmax = 1.57 e Å−3 |
38134 reflections | Δρmin = −0.90 e Å−3 |
1026 parameters | Absolute structure: Flack x determined using 13600 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.074 (4) |
Primary atom site location: iterative |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. A solvent mask was calculated and 151 electrons were found in a volume of 927Å3 in 6 voids per unit cell. This is consistent with the presence of two 0.5[CH2Cl2]occupied DCM molecules per Formula Unit which account for 168 electrons per unit cell. |
x | y | z | Uiso*/Ueq | ||
Ir2 | 0.24765 (2) | 0.56306 (2) | 0.18270 (2) | 0.01703 (5) | |
Cl2 | 0.34192 (8) | 0.47528 (14) | 0.24718 (5) | 0.0213 (3) | |
N212 | 0.2086 (2) | 0.7846 (5) | 0.24086 (18) | 0.0157 (9) | |
N215 | 0.3131 (2) | 0.8131 (5) | 0.22408 (18) | 0.0171 (9) | |
C211 | 0.2562 (3) | 0.7306 (6) | 0.21910 (19) | 0.0148 (10) | |
C213 | 0.2441 (3) | 0.8964 (5) | 0.2698 (2) | 0.0174 (9) | |
H213 | 0.276027 | 0.864194 | 0.302075 | 0.021* | |
C214 | 0.2935 (3) | 0.9375 (7) | 0.2411 (2) | 0.0197 (10) | |
H214 | 0.262407 | 0.984438 | 0.211772 | 0.024* | |
C216 | 0.1974 (3) | 1.0048 (6) | 0.2798 (2) | 0.0237 (12) | |
H21A | 0.165361 | 0.973654 | 0.298941 | 0.028* | |
H21B | 0.165754 | 1.041541 | 0.248734 | 0.028* | |
C217 | 0.2519 (3) | 1.1053 (5) | 0.3088 (2) | 0.0245 (12) | |
H21C | 0.277873 | 1.070509 | 0.341499 | 0.029* | |
H21D | 0.224096 | 1.182019 | 0.313317 | 0.029* | |
C218 | 0.3092 (3) | 1.1449 (6) | 0.2835 (2) | 0.0213 (12) | |
H21E | 0.283755 | 1.191601 | 0.253062 | 0.026* | |
H21F | 0.344964 | 1.204336 | 0.305086 | 0.026* | |
C219 | 0.3513 (3) | 1.0317 (5) | 0.2709 (2) | 0.0213 (10) | |
H21G | 0.383503 | 1.061116 | 0.251582 | 0.026* | |
H21H | 0.382432 | 0.990358 | 0.301072 | 0.026* | |
C301 | 0.2809 (3) | 0.4337 (7) | 0.1343 (2) | 0.0326 (5) | |
H301 | 0.331788 | 0.398933 | 0.148996 | 0.039* | |
C302 | 0.2287 (4) | 0.3690 (7) | 0.1491 (2) | 0.0326 (5) | |
H302 | 0.248050 | 0.296566 | 0.172121 | 0.039* | |
C303 | 0.1382 (4) | 0.5878 (7) | 0.1378 (2) | 0.0326 (5) | |
H303 | 0.109562 | 0.650836 | 0.151056 | 0.039* | |
C304 | 0.1855 (4) | 0.6441 (8) | 0.1157 (3) | 0.0326 (5) | |
H304 | 0.184228 | 0.739747 | 0.115761 | 0.039* | |
C305 | 0.2073 (4) | 0.5859 (7) | 0.0722 (2) | 0.0326 (5) | |
H30A | 0.164564 | 0.537322 | 0.051454 | 0.039* | |
H30B | 0.217229 | 0.656811 | 0.052220 | 0.039* | |
C306 | 0.2714 (4) | 0.5013 (6) | 0.0855 (2) | 0.0326 (5) | |
H30C | 0.316295 | 0.551869 | 0.087611 | 0.039* | |
H30D | 0.265900 | 0.436224 | 0.059581 | 0.039* | |
C307 | 0.1493 (3) | 0.3533 (6) | 0.1165 (2) | 0.0326 (5) | |
H30E | 0.129584 | 0.271135 | 0.124365 | 0.039* | |
H30F | 0.148994 | 0.349415 | 0.081972 | 0.039* | |
C308 | 0.0981 (4) | 0.4625 (8) | 0.1222 (3) | 0.0326 (5) | |
H30G | 0.059173 | 0.475408 | 0.090699 | 0.039* | |
H30H | 0.073541 | 0.437128 | 0.146714 | 0.039* | |
C320 | 0.0765 (3) | 0.7522 (6) | 0.2270 (2) | 0.0185 (11) | |
C321 | 0.1508 (3) | 0.7195 (6) | 0.2540 (2) | 0.0171 (11) | |
C322 | 0.1659 (3) | 0.6387 (6) | 0.2938 (2) | 0.0182 (11) | |
C323 | 0.1056 (3) | 0.5879 (6) | 0.3077 (2) | 0.0218 (11) | |
H323 | 0.115414 | 0.533010 | 0.335226 | 0.026* | |
C324 | 0.0339 (4) | 0.6161 (6) | 0.2823 (3) | 0.0257 (13) | |
H324 | −0.005102 | 0.580103 | 0.292345 | 0.031* | |
C325 | 0.0175 (3) | 0.6978 (6) | 0.2416 (2) | 0.0212 (12) | |
C326 | −0.0562 (3) | 0.7260 (6) | 0.2137 (3) | 0.0252 (13) | |
H326 | −0.095944 | 0.690231 | 0.223021 | 0.030* | |
C327 | −0.0704 (3) | 0.8017 (6) | 0.1748 (3) | 0.0252 (13) | |
H327 | −0.120250 | 0.818701 | 0.156767 | 0.030* | |
C328 | −0.0130 (3) | 0.8581 (6) | 0.1594 (2) | 0.0214 (12) | |
C329 | 0.0584 (3) | 0.8335 (6) | 0.1857 (2) | 0.0221 (12) | |
H329 | 0.097067 | 0.872056 | 0.176020 | 0.026* | |
C331 | −0.0335 (3) | 0.9401 (8) | 0.1143 (2) | 0.0276 (12) | |
H331 | −0.087982 | 0.931782 | 0.098749 | 0.033* | |
C332 | −0.0168 (6) | 1.0809 (11) | 0.1260 (4) | 0.0668 (14) | |
H33A | 0.036657 | 1.092562 | 0.142358 | 0.080* | |
H33B | −0.044019 | 1.111534 | 0.148309 | 0.080* | |
C333 | −0.0413 (6) | 1.1610 (12) | 0.0762 (4) | 0.0668 (14) | |
H33C | −0.095792 | 1.159754 | 0.062872 | 0.080* | |
H33D | −0.025659 | 1.251165 | 0.083220 | 0.080* | |
C334 | −0.0095 (6) | 1.1103 (11) | 0.0396 (4) | 0.0668 (14) | |
H33E | −0.029482 | 1.158349 | 0.008755 | 0.080* | |
H33F | 0.044661 | 1.122848 | 0.050962 | 0.080* | |
C335 | −0.0256 (6) | 0.9748 (11) | 0.0306 (4) | 0.0668 (14) | |
H33G | −0.003291 | 0.944026 | 0.005620 | 0.080* | |
H33H | −0.079701 | 0.962507 | 0.017657 | 0.080* | |
C336 | 0.0043 (6) | 0.8972 (11) | 0.0769 (4) | 0.0668 (14) | |
H33I | 0.058296 | 0.910038 | 0.090309 | 0.080* | |
H33J | −0.005086 | 0.805091 | 0.069702 | 0.080* | |
C337 | 0.2434 (3) | 0.6096 (6) | 0.3265 (2) | 0.0194 (12) | |
H337 | 0.279248 | 0.640793 | 0.309745 | 0.023* | |
C338 | 0.2581 (3) | 0.6820 (7) | 0.3750 (2) | 0.0243 (13) | |
H33K | 0.251686 | 0.774933 | 0.368387 | 0.029* | |
H33L | 0.221895 | 0.654875 | 0.391601 | 0.029* | |
C339 | 0.3360 (4) | 0.6565 (7) | 0.4083 (3) | 0.0291 (15) | |
H33M | 0.371970 | 0.693501 | 0.393222 | 0.035* | |
H33N | 0.342634 | 0.700327 | 0.439857 | 0.035* | |
C340 | 0.3523 (4) | 0.5174 (8) | 0.4175 (3) | 0.0336 (17) | |
H34A | 0.321712 | 0.482930 | 0.437101 | 0.040* | |
H34B | 0.404778 | 0.506554 | 0.436659 | 0.040* | |
C341 | 0.3365 (3) | 0.4414 (9) | 0.3696 (2) | 0.0261 (11) | |
H34C | 0.343004 | 0.348873 | 0.377063 | 0.031* | |
H34D | 0.372105 | 0.466728 | 0.352248 | 0.031* | |
C342 | 0.2565 (3) | 0.4666 (6) | 0.3363 (2) | 0.0223 (13) | |
H34E | 0.248431 | 0.420790 | 0.304934 | 0.027* | |
H34F | 0.220830 | 0.433152 | 0.352264 | 0.027* | |
C350 | 0.3637 (3) | 0.8268 (6) | 0.1541 (2) | 0.0176 (11) | |
C351 | 0.3742 (3) | 0.7975 (5) | 0.2046 (2) | 0.0150 (10) | |
C352 | 0.4427 (3) | 0.7559 (6) | 0.2348 (2) | 0.0173 (11) | |
C353 | 0.4986 (3) | 0.7294 (6) | 0.2127 (2) | 0.0212 (12) | |
H353 | 0.545076 | 0.699386 | 0.232618 | 0.025* | |
C354 | 0.4880 (3) | 0.7452 (6) | 0.1640 (2) | 0.0214 (12) | |
H354 | 0.525825 | 0.721479 | 0.150292 | 0.026* | |
C355 | 0.4218 (3) | 0.7964 (7) | 0.1339 (2) | 0.0212 (12) | |
C356 | 0.4110 (4) | 0.8240 (8) | 0.0834 (2) | 0.0275 (14) | |
H356 | 0.447671 | 0.799724 | 0.068817 | 0.033* | |
C357 | 0.3493 (4) | 0.8843 (7) | 0.0563 (2) | 0.0306 (15) | |
H357 | 0.344795 | 0.905294 | 0.023313 | 0.037* | |
C358 | 0.2913 (3) | 0.9169 (7) | 0.0754 (2) | 0.0240 (14) | |
C359 | 0.2997 (3) | 0.8877 (6) | 0.1238 (2) | 0.0201 (11) | |
H359 | 0.261152 | 0.909279 | 0.137134 | 0.024* | |
C361 | 0.2239 (4) | 0.9894 (8) | 0.0436 (3) | 0.0315 (16) | |
H361 | 0.186886 | 0.995606 | 0.061959 | 0.038* | |
C362 | 0.2448 (4) | 1.1234 (8) | 0.0332 (3) | 0.0377 (17) | |
H36A | 0.285622 | 1.118723 | 0.018411 | 0.045* | |
H36B | 0.263095 | 1.170796 | 0.064346 | 0.045* | |
C363 | 0.1799 (6) | 1.1978 (9) | −0.0015 (3) | 0.047 (2) | |
H36C | 0.196748 | 1.283784 | −0.007909 | 0.056* | |
H36D | 0.140237 | 1.208607 | 0.013994 | 0.056* | |
C364 | 0.1497 (5) | 1.1238 (9) | −0.0502 (3) | 0.045 (2) | |
H36E | 0.107051 | 1.170183 | −0.072058 | 0.054* | |
H36F | 0.188442 | 1.117692 | −0.066712 | 0.054* | |
C365 | 0.1258 (4) | 0.9889 (8) | −0.0399 (3) | 0.0357 (16) | |
H36G | 0.083824 | 0.995367 | −0.026343 | 0.043* | |
H36H | 0.109041 | 0.940228 | −0.070884 | 0.043* | |
C366 | 0.1880 (4) | 0.9188 (9) | −0.0046 (3) | 0.0348 (18) | |
H36I | 0.226388 | 0.901344 | −0.020652 | 0.042* | |
H36J | 0.169318 | 0.835322 | 0.002894 | 0.042* | |
C367 | 0.4631 (3) | 0.7462 (6) | 0.2898 (2) | 0.0185 (11) | |
H367 | 0.416957 | 0.752250 | 0.299600 | 0.022* | |
C368 | 0.5148 (3) | 0.8574 (5) | 0.3138 (2) | 0.0211 (11) | |
H36K | 0.561480 | 0.850079 | 0.305386 | 0.025* | |
H36L | 0.491312 | 0.939632 | 0.300637 | 0.025* | |
C369 | 0.5319 (3) | 0.8575 (6) | 0.3689 (2) | 0.0273 (12) | |
H36M | 0.564908 | 0.930145 | 0.382945 | 0.033* | |
H36N | 0.485669 | 0.868168 | 0.377628 | 0.033* | |
C370 | 0.5687 (4) | 0.7335 (7) | 0.3898 (2) | 0.0282 (13) | |
H37A | 0.576180 | 0.732214 | 0.425389 | 0.034* | |
H37B | 0.617801 | 0.728805 | 0.384539 | 0.034* | |
C371 | 0.5236 (4) | 0.6172 (7) | 0.3666 (2) | 0.0272 (14) | |
H37C | 0.477787 | 0.614127 | 0.376275 | 0.033* | |
H37D | 0.552231 | 0.538570 | 0.378936 | 0.033* | |
C372 | 0.5036 (3) | 0.6210 (6) | 0.3107 (2) | 0.0222 (12) | |
H37E | 0.471582 | 0.547056 | 0.296726 | 0.027* | |
H37F | 0.549141 | 0.613733 | 0.300914 | 0.027* | |
Ir1 | 0.75763 (2) | 0.442289 (6) | 0.31455 (2) | 0.01599 (5) | |
Cl1 | 0.65873 (8) | 0.51820 (14) | 0.25058 (5) | 0.0196 (3) | |
N12 | 0.6958 (2) | 0.1776 (4) | 0.28132 (17) | 0.0137 (8) | |
N15 | 0.7916 (2) | 0.2176 (5) | 0.25652 (18) | 0.0160 (9) | |
C11 | 0.7485 (3) | 0.2672 (5) | 0.2814 (2) | 0.0152 (10) | |
C13 | 0.6977 (3) | 0.0714 (6) | 0.24819 (19) | 0.0165 (9) | |
H13 | 0.666707 | 0.096789 | 0.214734 | 0.020* | |
C14 | 0.7777 (3) | 0.0774 (5) | 0.24884 (19) | 0.0178 (9) | |
H14 | 0.808040 | 0.032034 | 0.278832 | 0.021* | |
C16 | 0.6759 (3) | −0.0611 (5) | 0.25724 (18) | 0.0194 (9) | |
H16A | 0.623923 | −0.063286 | 0.257438 | 0.023* | |
H16B | 0.707814 | −0.093463 | 0.288972 | 0.023* | |
C17 | 0.6861 (3) | −0.1428 (6) | 0.2143 (2) | 0.0200 (12) | |
H17A | 0.676466 | −0.233818 | 0.219790 | 0.024* | |
H17B | 0.649442 | −0.115434 | 0.183455 | 0.024* | |
C18 | 0.7640 (3) | −0.1302 (5) | 0.2091 (2) | 0.0232 (12) | |
H18A | 0.765699 | −0.177227 | 0.179535 | 0.028* | |
H18B | 0.799635 | −0.171321 | 0.237626 | 0.028* | |
C19 | 0.7884 (3) | 0.0101 (6) | 0.2054 (2) | 0.0239 (13) | |
H19A | 0.840850 | 0.013483 | 0.206178 | 0.029* | |
H19B | 0.757875 | 0.050061 | 0.174721 | 0.029* | |
C101 | 0.7843 (3) | 0.6404 (6) | 0.3353 (2) | 0.0279 (4) | |
H101 | 0.757692 | 0.702551 | 0.309509 | 0.033* | |
C102 | 0.7402 (3) | 0.5923 (5) | 0.3623 (2) | 0.0279 (4) | |
H102 | 0.688958 | 0.627573 | 0.353075 | 0.033* | |
C103 | 0.8192 (4) | 0.3609 (7) | 0.3818 (2) | 0.0279 (4) | |
H103 | 0.821375 | 0.265374 | 0.381298 | 0.033* | |
C104 | 0.8667 (4) | 0.4199 (6) | 0.3602 (2) | 0.0279 (4) | |
H104 | 0.896129 | 0.357933 | 0.347071 | 0.033* | |
C105 | 0.9076 (3) | 0.5452 (7) | 0.3779 (2) | 0.0279 (4) | |
H10A | 0.915995 | 0.553441 | 0.413484 | 0.033* | |
H10B | 0.956511 | 0.542038 | 0.372246 | 0.033* | |
C106 | 0.8665 (3) | 0.6616 (5) | 0.3527 (2) | 0.0279 (4) | |
H10C | 0.877760 | 0.734934 | 0.375571 | 0.033* | |
H10D | 0.883792 | 0.683545 | 0.324398 | 0.033* | |
C107 | 0.7722 (3) | 0.5569 (6) | 0.4158 (2) | 0.0279 (4) | |
H10E | 0.734874 | 0.574246 | 0.432690 | 0.033* | |
H10F | 0.815462 | 0.612149 | 0.430722 | 0.033* | |
C108 | 0.7964 (4) | 0.4145 (6) | 0.4240 (2) | 0.0279 (4) | |
H10G | 0.838336 | 0.407369 | 0.454338 | 0.033* | |
H10H | 0.755082 | 0.363125 | 0.428341 | 0.033* | |
C120 | 0.6444 (3) | 0.1727 (6) | 0.3502 (2) | 0.0166 (10) | |
C121 | 0.6343 (3) | 0.2016 (6) | 0.2999 (2) | 0.0158 (10) | |
C122 | 0.5662 (3) | 0.2416 (5) | 0.2694 (2) | 0.0164 (10) | |
C123 | 0.5090 (3) | 0.2659 (6) | 0.2904 (2) | 0.0195 (11) | |
H123 | 0.461811 | 0.291032 | 0.269861 | 0.023* | |
C124 | 0.5198 (3) | 0.2541 (6) | 0.3394 (2) | 0.0213 (12) | |
H124 | 0.481766 | 0.278862 | 0.352735 | 0.026* | |
C125 | 0.5871 (3) | 0.2053 (6) | 0.3706 (2) | 0.0181 (11) | |
C126 | 0.5963 (4) | 0.1806 (7) | 0.4203 (2) | 0.0251 (13) | |
H126 | 0.558198 | 0.203617 | 0.433844 | 0.030* | |
C127 | 0.6585 (3) | 0.1246 (6) | 0.4493 (2) | 0.0231 (12) | |
H127 | 0.664435 | 0.112452 | 0.483034 | 0.028* | |
C128 | 0.7152 (3) | 0.0840 (6) | 0.4294 (2) | 0.0204 (12) | |
C129 | 0.7081 (3) | 0.1103 (6) | 0.3814 (2) | 0.0184 (11) | |
H129 | 0.746641 | 0.086152 | 0.368446 | 0.022* | |
C131 | 0.7810 (3) | 0.0144 (6) | 0.4618 (2) | 0.0202 (12) | |
H131 | 0.818482 | 0.007301 | 0.443812 | 0.024* | |
C132 | 0.8168 (4) | 0.0867 (7) | 0.5096 (2) | 0.0253 (14) | |
H13A | 0.778291 | 0.108987 | 0.525029 | 0.030* | |
H13B | 0.838418 | 0.167509 | 0.502192 | 0.030* | |
C133 | 0.8781 (4) | 0.0075 (8) | 0.5463 (3) | 0.0317 (15) | |
H13C | 0.920313 | −0.003124 | 0.533209 | 0.038* | |
H13D | 0.895755 | 0.054703 | 0.577571 | 0.038* | |
C134 | 0.8511 (4) | −0.1199 (7) | 0.5554 (3) | 0.0303 (15) | |
H13E | 0.811455 | −0.109400 | 0.570918 | 0.036* | |
H13F | 0.891970 | −0.167986 | 0.578314 | 0.036* | |
C135 | 0.8220 (4) | −0.1948 (8) | 0.5090 (3) | 0.0309 (16) | |
H13G | 0.804220 | −0.279133 | 0.516311 | 0.037* | |
H13H | 0.862370 | −0.209503 | 0.494357 | 0.037* | |
C136 | 0.7595 (4) | −0.1240 (7) | 0.4728 (2) | 0.0249 (13) | |
H13I | 0.716941 | −0.119382 | 0.485869 | 0.030* | |
H13J | 0.743763 | −0.173030 | 0.441867 | 0.030* | |
C137 | 0.5481 (3) | 0.2554 (6) | 0.2145 (2) | 0.0181 (10) | |
H137 | 0.595409 | 0.268188 | 0.206612 | 0.022* | |
C138 | 0.4966 (3) | 0.3689 (6) | 0.1929 (2) | 0.0217 (12) | |
H13K | 0.448862 | 0.356975 | 0.199691 | 0.026* | |
H13L | 0.519068 | 0.449219 | 0.208873 | 0.026* | |
C139 | 0.4831 (4) | 0.3792 (7) | 0.1384 (3) | 0.0271 (13) | |
H13M | 0.530398 | 0.397925 | 0.131948 | 0.033* | |
H13N | 0.449066 | 0.451340 | 0.125555 | 0.033* | |
C140 | 0.4501 (4) | 0.2559 (7) | 0.1116 (3) | 0.0343 (15) | |
H14A | 0.399638 | 0.243385 | 0.114057 | 0.041* | |
H14B | 0.446470 | 0.263555 | 0.076614 | 0.041* | |
C141 | 0.4977 (4) | 0.1405 (6) | 0.1335 (2) | 0.0300 (13) | |
H14C | 0.545604 | 0.147017 | 0.126618 | 0.036* | |
H14D | 0.472884 | 0.061398 | 0.117918 | 0.036* | |
C142 | 0.5115 (3) | 0.1321 (5) | 0.1889 (2) | 0.0231 (11) | |
H14E | 0.543882 | 0.058023 | 0.202082 | 0.028* | |
H14F | 0.464054 | 0.118437 | 0.195802 | 0.028* | |
C150 | 0.9256 (3) | 0.2418 (6) | 0.2704 (2) | 0.0157 (11) | |
C151 | 0.8521 (3) | 0.2766 (6) | 0.2433 (2) | 0.0163 (11) | |
C152 | 0.8374 (3) | 0.3537 (6) | 0.2028 (2) | 0.0177 (11) | |
C153 | 0.8989 (3) | 0.3978 (6) | 0.1882 (2) | 0.0225 (12) | |
H153 | 0.889622 | 0.451170 | 0.160189 | 0.027* | |
C154 | 0.9695 (3) | 0.3671 (6) | 0.2124 (2) | 0.0219 (12) | |
H154 | 1.008483 | 0.398263 | 0.201170 | 0.026* | |
C155 | 0.9853 (3) | 0.2884 (6) | 0.2544 (2) | 0.0194 (11) | |
C156 | 1.0585 (3) | 0.2584 (6) | 0.2821 (2) | 0.0219 (12) | |
H156 | 1.098346 | 0.288936 | 0.271654 | 0.026* | |
C157 | 1.0729 (3) | 0.1853 (6) | 0.3241 (2) | 0.0201 (11) | |
H157 | 1.122563 | 0.165820 | 0.341997 | 0.024* | |
C158 | 1.0152 (3) | 0.1396 (6) | 0.3407 (2) | 0.0177 (11) | |
C159 | 0.9426 (3) | 0.1659 (6) | 0.3134 (2) | 0.0146 (10) | |
H159 | 0.903411 | 0.132154 | 0.323795 | 0.018* | |
C161 | 1.0328 (3) | 0.0626 (8) | 0.3876 (2) | 0.0219 (11) | |
H161 | 1.087167 | 0.070403 | 0.403622 | 0.026* | |
C162 | 0.9954 (4) | 0.1150 (6) | 0.4237 (2) | 0.0249 (11) | |
H16C | 0.941226 | 0.106265 | 0.409687 | 0.030* | |
H16D | 1.006904 | 0.207243 | 0.429120 | 0.030* | |
C163 | 1.0206 (4) | 0.0449 (8) | 0.4727 (2) | 0.0358 (15) | |
H16E | 1.074072 | 0.058787 | 0.488154 | 0.043* | |
H16F | 0.993940 | 0.079033 | 0.494781 | 0.043* | |
C164 | 1.0049 (4) | −0.0978 (8) | 0.4644 (3) | 0.0399 (17) | |
H16G | 0.950892 | −0.111594 | 0.452852 | 0.048* | |
H16H | 1.024759 | −0.143590 | 0.495820 | 0.048* | |
C165 | 1.0394 (4) | −0.1538 (7) | 0.4270 (4) | 0.051 (2) | |
H16I | 1.023792 | −0.244145 | 0.420551 | 0.061* | |
H16J | 1.093797 | −0.152271 | 0.440771 | 0.061* | |
C166 | 1.0165 (4) | −0.0789 (6) | 0.3789 (3) | 0.0310 (13) | |
H16K | 1.043491 | −0.112587 | 0.356936 | 0.037* | |
H16L | 0.963020 | −0.091047 | 0.362649 | 0.037* | |
C167 | 0.7610 (3) | 0.3886 (6) | 0.1711 (2) | 0.0180 (11) | |
H167 | 0.724884 | 0.357210 | 0.187564 | 0.022* | |
C168 | 0.7433 (4) | 0.3232 (7) | 0.1212 (2) | 0.0250 (13) | |
H16M | 0.779700 | 0.350791 | 0.104780 | 0.030* | |
H16N | 0.748168 | 0.229443 | 0.126012 | 0.030* | |
C169 | 0.6663 (4) | 0.3534 (8) | 0.0883 (3) | 0.0324 (16) | |
H16O | 0.629369 | 0.316970 | 0.102692 | 0.039* | |
H16P | 0.658892 | 0.313254 | 0.055992 | 0.039* | |
C170 | 0.6546 (4) | 0.4982 (7) | 0.0821 (3) | 0.0287 (14) | |
H17C | 0.686052 | 0.532260 | 0.062991 | 0.034* | |
H17D | 0.602499 | 0.515576 | 0.063474 | 0.034* | |
C171 | 0.6735 (3) | 0.5670 (8) | 0.1313 (2) | 0.0248 (11) | |
H17E | 0.669617 | 0.660517 | 0.125714 | 0.030* | |
H17F | 0.637146 | 0.542439 | 0.148241 | 0.030* | |
C172 | 0.7499 (3) | 0.5351 (6) | 0.1634 (2) | 0.0236 (14) | |
H17G | 0.758504 | 0.577230 | 0.195502 | 0.028* | |
H17H | 0.786598 | 0.568840 | 0.148317 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir2 | 0.01774 (9) | 0.01498 (12) | 0.01705 (10) | −0.00075 (8) | 0.00323 (8) | −0.00294 (9) |
Cl2 | 0.0221 (6) | 0.0206 (8) | 0.0192 (6) | 0.0038 (5) | 0.0034 (5) | 0.0006 (5) |
N212 | 0.016 (2) | 0.012 (2) | 0.020 (2) | 0.0001 (17) | 0.0070 (18) | −0.0019 (18) |
N215 | 0.0160 (19) | 0.013 (2) | 0.025 (2) | 0.0010 (16) | 0.0098 (18) | −0.0027 (17) |
C211 | 0.014 (2) | 0.020 (3) | 0.009 (2) | 0.0009 (19) | 0.0018 (18) | 0.002 (2) |
C213 | 0.017 (2) | 0.014 (2) | 0.024 (2) | −0.0019 (17) | 0.0103 (19) | −0.0039 (18) |
C214 | 0.018 (2) | 0.015 (2) | 0.028 (3) | −0.002 (2) | 0.0114 (19) | −0.004 (2) |
C216 | 0.020 (2) | 0.017 (3) | 0.039 (3) | −0.003 (2) | 0.016 (2) | −0.008 (2) |
C217 | 0.026 (3) | 0.014 (2) | 0.039 (3) | −0.0016 (19) | 0.019 (3) | −0.008 (2) |
C218 | 0.022 (3) | 0.016 (3) | 0.027 (3) | −0.004 (2) | 0.009 (2) | −0.007 (2) |
C219 | 0.020 (2) | 0.016 (2) | 0.030 (3) | −0.0033 (17) | 0.011 (2) | −0.0051 (19) |
C301 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C302 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C303 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C304 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C305 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C306 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C307 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C308 | 0.0349 (11) | 0.0321 (12) | 0.0269 (10) | 0.0001 (10) | 0.0032 (9) | −0.0072 (9) |
C320 | 0.019 (2) | 0.017 (3) | 0.021 (3) | 0.002 (2) | 0.009 (2) | −0.003 (2) |
C321 | 0.016 (2) | 0.016 (3) | 0.022 (3) | −0.0013 (19) | 0.009 (2) | −0.003 (2) |
C322 | 0.020 (2) | 0.015 (3) | 0.022 (3) | 0.000 (2) | 0.010 (2) | −0.001 (2) |
C323 | 0.024 (2) | 0.017 (3) | 0.026 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C324 | 0.026 (3) | 0.023 (3) | 0.036 (3) | −0.007 (2) | 0.021 (3) | −0.004 (2) |
C325 | 0.017 (2) | 0.022 (3) | 0.029 (3) | −0.001 (2) | 0.013 (2) | −0.006 (2) |
C326 | 0.016 (2) | 0.025 (3) | 0.038 (3) | 0.000 (2) | 0.012 (2) | −0.002 (3) |
C327 | 0.016 (2) | 0.025 (3) | 0.036 (3) | −0.001 (2) | 0.008 (2) | −0.010 (3) |
C328 | 0.019 (3) | 0.018 (3) | 0.027 (3) | 0.001 (2) | 0.006 (2) | −0.003 (2) |
C329 | 0.021 (3) | 0.016 (3) | 0.033 (3) | 0.000 (2) | 0.014 (3) | −0.002 (3) |
C331 | 0.017 (2) | 0.025 (3) | 0.037 (3) | −0.004 (3) | 0.003 (2) | 0.001 (4) |
C332 | 0.061 (3) | 0.068 (3) | 0.061 (3) | −0.010 (2) | 0.003 (2) | 0.024 (2) |
C333 | 0.061 (3) | 0.068 (3) | 0.061 (3) | −0.010 (2) | 0.003 (2) | 0.024 (2) |
C334 | 0.061 (3) | 0.068 (3) | 0.061 (3) | −0.010 (2) | 0.003 (2) | 0.024 (2) |
C335 | 0.061 (3) | 0.068 (3) | 0.061 (3) | −0.010 (2) | 0.003 (2) | 0.024 (2) |
C336 | 0.061 (3) | 0.068 (3) | 0.061 (3) | −0.010 (2) | 0.003 (2) | 0.024 (2) |
C337 | 0.023 (3) | 0.018 (3) | 0.020 (3) | −0.002 (2) | 0.010 (2) | −0.001 (2) |
C338 | 0.026 (3) | 0.028 (3) | 0.022 (3) | 0.000 (2) | 0.010 (2) | 0.002 (3) |
C339 | 0.028 (3) | 0.035 (4) | 0.025 (3) | −0.011 (3) | 0.009 (3) | −0.006 (3) |
C340 | 0.028 (3) | 0.050 (5) | 0.022 (3) | −0.001 (3) | 0.006 (3) | 0.002 (3) |
C341 | 0.026 (3) | 0.028 (3) | 0.023 (3) | −0.001 (3) | 0.007 (2) | −0.002 (3) |
C342 | 0.027 (3) | 0.020 (4) | 0.022 (3) | −0.006 (2) | 0.010 (2) | −0.002 (2) |
C350 | 0.020 (2) | 0.015 (3) | 0.020 (2) | −0.004 (2) | 0.008 (2) | −0.002 (2) |
C351 | 0.015 (2) | 0.012 (3) | 0.019 (2) | −0.0049 (18) | 0.0077 (19) | −0.0050 (19) |
C352 | 0.016 (2) | 0.013 (3) | 0.025 (3) | 0.0007 (18) | 0.010 (2) | −0.002 (2) |
C353 | 0.019 (2) | 0.019 (3) | 0.030 (3) | 0.004 (2) | 0.013 (2) | 0.003 (2) |
C354 | 0.018 (2) | 0.022 (3) | 0.028 (3) | −0.001 (2) | 0.012 (2) | −0.008 (2) |
C355 | 0.021 (3) | 0.026 (3) | 0.019 (3) | −0.007 (2) | 0.011 (2) | −0.007 (2) |
C356 | 0.023 (3) | 0.041 (4) | 0.023 (3) | −0.001 (3) | 0.013 (2) | −0.004 (3) |
C357 | 0.032 (3) | 0.044 (4) | 0.019 (3) | −0.011 (3) | 0.012 (2) | −0.005 (3) |
C358 | 0.024 (3) | 0.030 (4) | 0.019 (3) | −0.005 (2) | 0.008 (2) | −0.001 (2) |
C359 | 0.019 (2) | 0.025 (3) | 0.018 (2) | −0.004 (2) | 0.008 (2) | −0.002 (2) |
C361 | 0.028 (3) | 0.044 (4) | 0.022 (3) | −0.008 (3) | 0.006 (3) | −0.004 (3) |
C362 | 0.039 (4) | 0.034 (4) | 0.030 (3) | 0.000 (3) | −0.004 (3) | −0.007 (3) |
C363 | 0.063 (5) | 0.027 (4) | 0.040 (4) | 0.000 (4) | 0.000 (4) | −0.008 (3) |
C364 | 0.050 (5) | 0.044 (5) | 0.033 (4) | 0.010 (4) | 0.000 (4) | 0.006 (4) |
C365 | 0.036 (4) | 0.038 (4) | 0.028 (3) | −0.008 (3) | 0.002 (3) | −0.002 (3) |
C366 | 0.035 (3) | 0.040 (5) | 0.024 (3) | −0.007 (3) | 0.000 (3) | 0.002 (3) |
C367 | 0.015 (2) | 0.021 (3) | 0.021 (3) | −0.0001 (19) | 0.008 (2) | 0.000 (2) |
C368 | 0.021 (2) | 0.018 (3) | 0.027 (3) | −0.001 (2) | 0.011 (2) | −0.002 (2) |
C369 | 0.028 (3) | 0.027 (3) | 0.027 (3) | −0.003 (2) | 0.008 (2) | −0.008 (2) |
C370 | 0.033 (3) | 0.025 (3) | 0.026 (3) | 0.002 (2) | 0.008 (3) | −0.001 (2) |
C371 | 0.023 (3) | 0.029 (4) | 0.024 (3) | −0.002 (2) | 0.000 (2) | 0.002 (3) |
C372 | 0.023 (3) | 0.016 (3) | 0.027 (3) | 0.001 (2) | 0.006 (2) | 0.001 (2) |
Ir1 | 0.01665 (9) | 0.01127 (10) | 0.01773 (10) | −0.00002 (8) | 0.00169 (8) | −0.00114 (9) |
Cl1 | 0.0182 (6) | 0.0165 (7) | 0.0216 (6) | 0.0027 (5) | 0.0024 (5) | 0.0001 (5) |
N12 | 0.0149 (18) | 0.009 (2) | 0.018 (2) | 0.0004 (15) | 0.0059 (16) | 0.0004 (16) |
N15 | 0.0120 (19) | 0.015 (2) | 0.021 (2) | −0.0045 (17) | 0.0054 (18) | −0.0008 (19) |
C11 | 0.014 (2) | 0.009 (2) | 0.021 (3) | 0.0026 (18) | 0.003 (2) | 0.003 (2) |
C13 | 0.0161 (19) | 0.014 (2) | 0.020 (2) | −0.0041 (19) | 0.0071 (17) | −0.005 (2) |
C14 | 0.0148 (19) | 0.014 (2) | 0.028 (2) | 0.0013 (18) | 0.0111 (18) | −0.002 (2) |
C16 | 0.019 (2) | 0.015 (2) | 0.026 (2) | −0.0051 (19) | 0.0086 (18) | −0.001 (2) |
C17 | 0.022 (3) | 0.014 (3) | 0.028 (3) | −0.004 (2) | 0.014 (2) | −0.004 (2) |
C18 | 0.024 (3) | 0.012 (2) | 0.040 (3) | 0.0004 (19) | 0.019 (2) | −0.005 (2) |
C19 | 0.026 (3) | 0.020 (3) | 0.032 (3) | −0.004 (2) | 0.020 (3) | −0.007 (2) |
C101 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C102 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C103 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C104 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C105 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C106 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C107 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C108 | 0.0309 (10) | 0.0198 (10) | 0.0278 (10) | 0.0019 (8) | 0.0009 (8) | −0.0049 (8) |
C120 | 0.016 (2) | 0.015 (3) | 0.022 (3) | −0.0012 (18) | 0.009 (2) | −0.002 (2) |
C121 | 0.014 (2) | 0.014 (3) | 0.021 (2) | 0.0025 (18) | 0.0070 (19) | 0.001 (2) |
C122 | 0.018 (2) | 0.011 (2) | 0.020 (2) | −0.0026 (18) | 0.006 (2) | 0.0008 (19) |
C123 | 0.015 (2) | 0.014 (3) | 0.030 (3) | 0.0000 (19) | 0.007 (2) | −0.003 (2) |
C124 | 0.020 (3) | 0.018 (3) | 0.032 (3) | 0.002 (2) | 0.017 (2) | 0.001 (2) |
C125 | 0.017 (2) | 0.015 (3) | 0.024 (3) | 0.0005 (19) | 0.008 (2) | −0.001 (2) |
C126 | 0.031 (3) | 0.024 (3) | 0.027 (3) | −0.001 (2) | 0.018 (3) | −0.004 (3) |
C127 | 0.023 (3) | 0.028 (3) | 0.020 (3) | 0.001 (2) | 0.008 (2) | −0.002 (2) |
C128 | 0.022 (2) | 0.019 (3) | 0.020 (2) | 0.000 (2) | 0.006 (2) | 0.001 (2) |
C129 | 0.015 (2) | 0.016 (3) | 0.023 (3) | −0.0028 (18) | 0.003 (2) | −0.001 (2) |
C131 | 0.022 (3) | 0.021 (3) | 0.019 (3) | 0.003 (2) | 0.009 (2) | 0.003 (2) |
C132 | 0.032 (3) | 0.018 (4) | 0.023 (3) | −0.005 (2) | 0.004 (2) | −0.002 (2) |
C133 | 0.025 (3) | 0.043 (4) | 0.023 (3) | 0.006 (3) | 0.001 (2) | 0.009 (3) |
C134 | 0.032 (3) | 0.032 (4) | 0.028 (3) | 0.007 (3) | 0.011 (3) | 0.005 (3) |
C135 | 0.031 (3) | 0.029 (4) | 0.033 (4) | 0.010 (3) | 0.010 (3) | 0.009 (3) |
C136 | 0.028 (3) | 0.021 (3) | 0.026 (3) | −0.001 (2) | 0.008 (2) | 0.004 (2) |
C137 | 0.018 (2) | 0.014 (3) | 0.022 (3) | 0.0007 (18) | 0.004 (2) | −0.001 (2) |
C138 | 0.017 (2) | 0.022 (3) | 0.023 (3) | 0.001 (2) | 0.001 (2) | −0.002 (2) |
C139 | 0.023 (3) | 0.024 (3) | 0.032 (3) | 0.002 (2) | 0.006 (3) | 0.004 (3) |
C140 | 0.035 (3) | 0.036 (4) | 0.026 (3) | −0.001 (3) | 0.001 (3) | −0.003 (3) |
C141 | 0.037 (3) | 0.024 (3) | 0.028 (3) | −0.005 (3) | 0.008 (3) | −0.005 (2) |
C142 | 0.022 (3) | 0.014 (3) | 0.031 (3) | 0.000 (2) | 0.004 (2) | 0.001 (2) |
C150 | 0.013 (2) | 0.013 (3) | 0.022 (3) | −0.0020 (18) | 0.008 (2) | −0.003 (2) |
C151 | 0.017 (2) | 0.012 (3) | 0.022 (3) | −0.0062 (19) | 0.010 (2) | −0.005 (2) |
C152 | 0.018 (2) | 0.016 (3) | 0.020 (3) | −0.0024 (19) | 0.008 (2) | −0.003 (2) |
C153 | 0.026 (3) | 0.024 (3) | 0.023 (3) | −0.005 (2) | 0.014 (2) | 0.000 (2) |
C154 | 0.019 (2) | 0.027 (3) | 0.023 (3) | −0.004 (2) | 0.012 (2) | 0.000 (2) |
C155 | 0.019 (2) | 0.019 (3) | 0.022 (3) | −0.002 (2) | 0.009 (2) | −0.002 (2) |
C156 | 0.015 (2) | 0.027 (3) | 0.028 (3) | −0.002 (2) | 0.013 (2) | −0.004 (2) |
C157 | 0.013 (2) | 0.019 (3) | 0.029 (3) | 0.0035 (19) | 0.009 (2) | 0.001 (2) |
C158 | 0.016 (2) | 0.014 (3) | 0.024 (3) | 0.002 (2) | 0.008 (2) | −0.003 (2) |
C159 | 0.015 (2) | 0.013 (3) | 0.016 (2) | −0.0013 (19) | 0.004 (2) | 0.001 (2) |
C161 | 0.013 (2) | 0.023 (3) | 0.027 (3) | −0.002 (3) | 0.003 (2) | 0.011 (3) |
C162 | 0.029 (3) | 0.024 (3) | 0.019 (2) | 0.005 (2) | 0.004 (2) | 0.002 (2) |
C163 | 0.032 (3) | 0.046 (4) | 0.026 (3) | −0.008 (3) | 0.003 (2) | 0.009 (3) |
C164 | 0.027 (3) | 0.050 (4) | 0.036 (3) | −0.013 (3) | −0.002 (3) | 0.017 (3) |
C165 | 0.033 (3) | 0.011 (3) | 0.091 (6) | 0.005 (2) | −0.007 (4) | 0.013 (3) |
C166 | 0.036 (3) | 0.009 (3) | 0.043 (3) | 0.004 (2) | 0.005 (3) | −0.001 (2) |
C167 | 0.017 (2) | 0.017 (3) | 0.019 (3) | −0.003 (2) | 0.005 (2) | 0.003 (2) |
C168 | 0.031 (3) | 0.021 (3) | 0.023 (3) | −0.008 (2) | 0.008 (3) | −0.006 (2) |
C169 | 0.032 (3) | 0.040 (5) | 0.023 (3) | −0.006 (3) | 0.005 (3) | −0.004 (3) |
C170 | 0.027 (3) | 0.034 (4) | 0.019 (3) | 0.002 (3) | −0.001 (2) | 0.006 (3) |
C171 | 0.024 (2) | 0.025 (3) | 0.023 (3) | 0.004 (3) | 0.005 (2) | 0.006 (3) |
C172 | 0.025 (3) | 0.023 (4) | 0.021 (3) | 0.000 (2) | 0.004 (2) | 0.004 (2) |
Ir2—Cl2 | 2.3415 (15) | Ir1—Cl1 | 2.3361 (15) |
Ir2—C211 | 2.021 (6) | Ir1—C11 | 2.046 (6) |
Ir2—C301 | 2.165 (6) | Ir1—C101 | 2.172 (6) |
Ir2—C302 | 2.228 (6) | Ir1—C102 | 2.173 (6) |
Ir2—C303 | 2.106 (7) | Ir1—C103 | 2.112 (7) |
Ir2—C304 | 2.109 (7) | Ir1—C104 | 2.106 (6) |
N212—C211 | 1.367 (6) | N12—C11 | 1.371 (7) |
N212—C213 | 1.475 (7) | N12—C13 | 1.469 (7) |
N212—C321 | 1.434 (7) | N12—C121 | 1.447 (6) |
N215—C211 | 1.357 (7) | N15—C11 | 1.342 (7) |
N215—C214 | 1.476 (8) | N15—C14 | 1.494 (7) |
N215—C351 | 1.439 (6) | N15—C151 | 1.452 (6) |
C213—H213 | 1.0000 | C13—H13 | 1.0000 |
C213—C214 | 1.487 (7) | C13—C14 | 1.516 (6) |
C213—C216 | 1.519 (7) | C13—C16 | 1.490 (8) |
C214—H214 | 1.0000 | C14—H14 | 1.0000 |
C214—C219 | 1.530 (8) | C14—C19 | 1.498 (7) |
C216—H21A | 0.9900 | C16—H16A | 0.9900 |
C216—H21B | 0.9900 | C16—H16B | 0.9900 |
C216—C217 | 1.534 (8) | C16—C17 | 1.560 (7) |
C217—H21C | 0.9900 | C17—H17A | 0.9900 |
C217—H21D | 0.9900 | C17—H17B | 0.9900 |
C217—C218 | 1.536 (7) | C17—C18 | 1.537 (7) |
C218—H21E | 0.9900 | C18—H18A | 0.9900 |
C218—H21F | 0.9900 | C18—H18B | 0.9900 |
C218—C219 | 1.531 (7) | C18—C19 | 1.552 (8) |
C219—H21G | 0.9900 | C19—H19A | 0.9900 |
C219—H21H | 0.9900 | C19—H19B | 0.9900 |
C301—H301 | 1.0000 | C101—H101 | 1.0000 |
C301—C302 | 1.369 (9) | C101—C102 | 1.394 (9) |
C301—C306 | 1.530 (9) | C101—C106 | 1.507 (8) |
C302—H302 | 1.0000 | C102—H102 | 1.0000 |
C302—C307 | 1.527 (8) | C102—C107 | 1.518 (8) |
C303—H303 | 1.0000 | C103—H103 | 1.0000 |
C303—C304 | 1.379 (10) | C103—C104 | 1.384 (9) |
C303—C308 | 1.514 (10) | C103—C108 | 1.513 (9) |
C304—H304 | 1.0000 | C104—H104 | 1.0000 |
C304—C305 | 1.553 (9) | C104—C105 | 1.530 (9) |
C305—H30A | 0.9900 | C105—H10A | 0.9900 |
C305—H30B | 0.9900 | C105—H10B | 0.9900 |
C305—C306 | 1.460 (9) | C105—C106 | 1.508 (9) |
C306—H30C | 0.9900 | C106—H10C | 0.9900 |
C306—H30D | 0.9900 | C106—H10D | 0.9900 |
C307—H30E | 0.9900 | C107—H10E | 0.9900 |
C307—H30F | 0.9900 | C107—H10F | 0.9900 |
C307—C308 | 1.541 (9) | C107—C108 | 1.554 (9) |
C308—H30G | 0.9900 | C108—H10G | 0.9900 |
C308—H30H | 0.9900 | C108—H10H | 0.9900 |
C320—C321 | 1.433 (8) | C120—C121 | 1.430 (8) |
C320—C325 | 1.429 (7) | C120—C125 | 1.423 (7) |
C320—C329 | 1.413 (9) | C120—C129 | 1.428 (8) |
C321—C322 | 1.380 (8) | C121—C122 | 1.390 (8) |
C322—C323 | 1.424 (7) | C122—C123 | 1.416 (7) |
C322—C337 | 1.519 (9) | C122—C137 | 1.516 (8) |
C323—H323 | 0.9500 | C123—H123 | 0.9500 |
C323—C324 | 1.370 (9) | C123—C124 | 1.364 (9) |
C324—H324 | 0.9500 | C124—H124 | 0.9500 |
C324—C325 | 1.405 (9) | C124—C125 | 1.416 (9) |
C325—C326 | 1.418 (9) | C125—C126 | 1.410 (8) |
C326—H326 | 0.9500 | C126—H126 | 0.9500 |
C326—C327 | 1.330 (10) | C126—C127 | 1.356 (9) |
C327—H327 | 0.9500 | C127—H127 | 0.9500 |
C327—C328 | 1.422 (8) | C127—C128 | 1.428 (8) |
C328—C329 | 1.363 (9) | C128—C129 | 1.372 (8) |
C328—C331 | 1.503 (10) | C128—C131 | 1.502 (9) |
C329—H329 | 0.9500 | C129—H129 | 0.9500 |
C331—H331 | 1.0000 | C131—H131 | 1.0000 |
C331—C332 | 1.521 (15) | C131—C132 | 1.537 (9) |
C331—C336 | 1.528 (13) | C131—C136 | 1.562 (9) |
C332—H33A | 0.9900 | C132—H13A | 0.9900 |
C332—H33B | 0.9900 | C132—H13B | 0.9900 |
C332—C333 | 1.601 (13) | C132—C133 | 1.553 (10) |
C333—H33C | 0.9900 | C133—H13C | 0.9900 |
C333—H33D | 0.9900 | C133—H13D | 0.9900 |
C333—C334 | 1.460 (16) | C133—C134 | 1.478 (11) |
C334—H33E | 0.9900 | C134—H13E | 0.9900 |
C334—H33F | 0.9900 | C134—H13F | 0.9900 |
C334—C335 | 1.456 (15) | C134—C135 | 1.501 (11) |
C335—H33G | 0.9900 | C135—H13G | 0.9900 |
C335—H33H | 0.9900 | C135—H13H | 0.9900 |
C335—C336 | 1.516 (14) | C135—C136 | 1.515 (10) |
C336—H33I | 0.9900 | C136—H13I | 0.9900 |
C336—H33J | 0.9900 | C136—H13J | 0.9900 |
C337—H337 | 1.0000 | C137—H137 | 1.0000 |
C337—C338 | 1.535 (9) | C137—C138 | 1.544 (8) |
C337—C342 | 1.527 (9) | C137—C142 | 1.541 (8) |
C338—H33K | 0.9900 | C138—H13K | 0.9900 |
C338—H33L | 0.9900 | C138—H13L | 0.9900 |
C338—C339 | 1.525 (10) | C138—C139 | 1.512 (9) |
C339—H33M | 0.9900 | C139—H13M | 0.9900 |
C339—H33N | 0.9900 | C139—H13N | 0.9900 |
C339—C340 | 1.493 (11) | C139—C140 | 1.536 (10) |
C340—H34A | 0.9900 | C140—H14A | 0.9900 |
C340—H34B | 0.9900 | C140—H14B | 0.9900 |
C340—C341 | 1.538 (10) | C140—C141 | 1.525 (10) |
C341—H34C | 0.9900 | C141—H14C | 0.9900 |
C341—H34D | 0.9900 | C141—H14D | 0.9900 |
C341—C342 | 1.555 (9) | C141—C142 | 1.536 (9) |
C342—H34E | 0.9900 | C142—H14E | 0.9900 |
C342—H34F | 0.9900 | C142—H14F | 0.9900 |
C350—C351 | 1.437 (8) | C150—C151 | 1.427 (8) |
C350—C355 | 1.429 (7) | C150—C155 | 1.431 (7) |
C350—C359 | 1.415 (9) | C150—C159 | 1.419 (8) |
C351—C352 | 1.398 (8) | C151—C152 | 1.373 (8) |
C352—C353 | 1.418 (7) | C152—C153 | 1.431 (7) |
C352—C367 | 1.512 (8) | C152—C167 | 1.509 (8) |
C353—H353 | 0.9500 | C153—H153 | 0.9500 |
C353—C354 | 1.363 (9) | C153—C154 | 1.350 (9) |
C354—H354 | 0.9500 | C154—H154 | 0.9500 |
C354—C355 | 1.400 (9) | C154—C155 | 1.418 (9) |
C355—C356 | 1.432 (9) | C155—C156 | 1.413 (8) |
C356—H356 | 0.9500 | C156—H156 | 0.9500 |
C356—C357 | 1.353 (10) | C156—C157 | 1.385 (9) |
C357—H357 | 0.9500 | C157—H157 | 0.9500 |
C357—C358 | 1.412 (8) | C157—C158 | 1.404 (7) |
C358—C359 | 1.385 (8) | C158—C159 | 1.394 (8) |
C358—C361 | 1.531 (10) | C158—C161 | 1.517 (8) |
C359—H359 | 0.9500 | C159—H159 | 0.9500 |
C361—H361 | 1.0000 | C161—H161 | 1.0000 |
C361—C362 | 1.510 (11) | C161—C162 | 1.525 (8) |
C361—C366 | 1.537 (10) | C161—C166 | 1.517 (10) |
C362—H36A | 0.9900 | C162—H16C | 0.9900 |
C362—H36B | 0.9900 | C162—H16D | 0.9900 |
C362—C363 | 1.542 (12) | C162—C163 | 1.528 (9) |
C363—H36C | 0.9900 | C163—H16E | 0.9900 |
C363—H36D | 0.9900 | C163—H16F | 0.9900 |
C363—C364 | 1.550 (12) | C163—C164 | 1.526 (11) |
C364—H36E | 0.9900 | C164—H16G | 0.9900 |
C364—H36F | 0.9900 | C164—H16H | 0.9900 |
C364—C365 | 1.537 (12) | C164—C165 | 1.531 (13) |
C365—H36G | 0.9900 | C165—H16I | 0.9900 |
C365—H36H | 0.9900 | C165—H16J | 0.9900 |
C365—C366 | 1.496 (11) | C165—C166 | 1.533 (11) |
C366—H36I | 0.9900 | C166—H16K | 0.9900 |
C366—H36J | 0.9900 | C166—H16L | 0.9900 |
C367—H367 | 1.0000 | C167—H167 | 1.0000 |
C367—C368 | 1.545 (8) | C167—C168 | 1.531 (8) |
C367—C372 | 1.545 (9) | C167—C172 | 1.551 (9) |
C368—H36K | 0.9900 | C168—H16M | 0.9900 |
C368—H36L | 0.9900 | C168—H16N | 0.9900 |
C368—C369 | 1.516 (8) | C168—C169 | 1.516 (10) |
C369—H36M | 0.9900 | C169—H16O | 0.9900 |
C369—H36N | 0.9900 | C169—H16P | 0.9900 |
C369—C370 | 1.508 (9) | C169—C170 | 1.533 (11) |
C370—H37A | 0.9900 | C170—H17C | 0.9900 |
C370—H37B | 0.9900 | C170—H17D | 0.9900 |
C370—C371 | 1.520 (10) | C170—C171 | 1.530 (10) |
C371—H37C | 0.9900 | C171—H17E | 0.9900 |
C371—H37D | 0.9900 | C171—H17F | 0.9900 |
C371—C372 | 1.537 (9) | C171—C172 | 1.505 (8) |
C372—H37E | 0.9900 | C172—H17G | 0.9900 |
C372—H37F | 0.9900 | C172—H17H | 0.9900 |
C211—Ir2—Cl2 | 90.41 (16) | C11—Ir1—Cl1 | 90.15 (16) |
C211—Ir2—C301 | 151.6 (2) | C11—Ir1—C101 | 163.8 (2) |
C211—Ir2—C302 | 172.0 (2) | C11—Ir1—C102 | 158.7 (2) |
C211—Ir2—C303 | 97.0 (3) | C11—Ir1—C103 | 90.6 (2) |
C211—Ir2—C304 | 93.4 (3) | C11—Ir1—C104 | 96.9 (2) |
C301—Ir2—Cl2 | 87.81 (17) | C101—Ir1—Cl1 | 87.58 (16) |
C301—Ir2—C302 | 36.3 (2) | C101—Ir1—C102 | 37.4 (2) |
C302—Ir2—Cl2 | 88.36 (17) | C102—Ir1—Cl1 | 90.69 (16) |
C303—Ir2—Cl2 | 155.7 (2) | C103—Ir1—Cl1 | 161.60 (18) |
C303—Ir2—C301 | 96.2 (2) | C103—Ir1—C101 | 96.5 (3) |
C303—Ir2—C302 | 81.1 (3) | C103—Ir1—C102 | 82.0 (2) |
C303—Ir2—C304 | 38.2 (3) | C104—Ir1—Cl1 | 159.30 (18) |
C304—Ir2—Cl2 | 164.58 (19) | C104—Ir1—C101 | 80.3 (2) |
C304—Ir2—C301 | 81.7 (3) | C104—Ir1—C102 | 89.7 (2) |
C304—Ir2—C302 | 89.8 (3) | C104—Ir1—C103 | 38.3 (3) |
C211—N212—C213 | 109.3 (4) | C11—N12—C13 | 110.9 (4) |
C211—N212—C321 | 126.0 (5) | C11—N12—C121 | 123.6 (5) |
C321—N212—C213 | 119.0 (4) | C121—N12—C13 | 123.3 (4) |
C211—N215—C214 | 108.8 (4) | C11—N15—C14 | 110.4 (4) |
C211—N215—C351 | 126.6 (5) | C11—N15—C151 | 129.3 (5) |
C351—N215—C214 | 122.8 (4) | C151—N15—C14 | 119.8 (4) |
N212—C211—Ir2 | 129.3 (4) | N12—C11—Ir1 | 124.8 (4) |
N215—C211—Ir2 | 122.9 (4) | N15—C11—Ir1 | 127.9 (4) |
N215—C211—N212 | 107.8 (5) | N15—C11—N12 | 107.3 (5) |
N212—C213—H213 | 107.6 | N12—C13—H13 | 107.4 |
N212—C213—C214 | 100.0 (4) | N12—C13—C14 | 100.4 (4) |
N212—C213—C216 | 120.1 (4) | N12—C13—C16 | 121.8 (4) |
C214—C213—H213 | 107.6 | C14—C13—H13 | 107.4 |
C214—C213—C216 | 113.0 (5) | C16—C13—H13 | 107.4 |
C216—C213—H213 | 107.6 | C16—C13—C14 | 111.5 (5) |
N215—C214—C213 | 101.2 (5) | N15—C14—C13 | 100.1 (4) |
N215—C214—H214 | 107.3 | N15—C14—H14 | 107.9 |
N215—C214—C219 | 122.8 (4) | N15—C14—C19 | 121.4 (4) |
C213—C214—H214 | 107.3 | C13—C14—H14 | 107.9 |
C213—C214—C219 | 110.0 (4) | C19—C14—C13 | 111.0 (4) |
C219—C214—H214 | 107.3 | C19—C14—H14 | 107.9 |
C213—C216—H21A | 110.5 | C13—C16—H16A | 110.7 |
C213—C216—H21B | 110.5 | C13—C16—H16B | 110.7 |
C213—C216—C217 | 106.0 (4) | C13—C16—C17 | 105.3 (4) |
H21A—C216—H21B | 108.7 | H16A—C16—H16B | 108.8 |
C217—C216—H21A | 110.5 | C17—C16—H16A | 110.7 |
C217—C216—H21B | 110.5 | C17—C16—H16B | 110.7 |
C216—C217—H21C | 109.0 | C16—C17—H17A | 109.1 |
C216—C217—H21D | 109.0 | C16—C17—H17B | 109.1 |
C216—C217—C218 | 112.7 (5) | H17A—C17—H17B | 107.8 |
H21C—C217—H21D | 107.8 | C18—C17—C16 | 112.4 (5) |
C218—C217—H21C | 109.0 | C18—C17—H17A | 109.1 |
C218—C217—H21D | 109.0 | C18—C17—H17B | 109.1 |
C217—C218—H21E | 108.9 | C17—C18—H18A | 108.8 |
C217—C218—H21F | 108.9 | C17—C18—H18B | 108.8 |
H21E—C218—H21F | 107.7 | C17—C18—C19 | 113.9 (4) |
C219—C218—C217 | 113.5 (5) | H18A—C18—H18B | 107.7 |
C219—C218—H21E | 108.9 | C19—C18—H18A | 108.8 |
C219—C218—H21F | 108.9 | C19—C18—H18B | 108.8 |
C214—C219—C218 | 106.9 (4) | C14—C19—C18 | 105.5 (4) |
C214—C219—H21G | 110.3 | C14—C19—H19A | 110.6 |
C214—C219—H21H | 110.3 | C14—C19—H19B | 110.6 |
C218—C219—H21G | 110.3 | C18—C19—H19A | 110.6 |
C218—C219—H21H | 110.3 | C18—C19—H19B | 110.6 |
H21G—C219—H21H | 108.6 | H19A—C19—H19B | 108.8 |
Ir2—C301—H301 | 112.8 | Ir1—C101—H101 | 113.1 |
C302—C301—Ir2 | 74.4 (4) | C102—C101—Ir1 | 71.3 (3) |
C302—C301—H301 | 112.8 | C102—C101—H101 | 113.1 |
C302—C301—C306 | 128.0 (6) | C102—C101—C106 | 127.2 (5) |
C306—C301—Ir2 | 108.9 (4) | C106—C101—Ir1 | 111.3 (4) |
C306—C301—H301 | 112.8 | C106—C101—H101 | 113.1 |
Ir2—C302—H302 | 115.0 | Ir1—C102—H102 | 114.8 |
C301—C302—Ir2 | 69.3 (4) | C101—C102—Ir1 | 71.2 (3) |
C301—C302—H302 | 115.0 | C101—C102—H102 | 114.8 |
C301—C302—C307 | 122.5 (6) | C101—C102—C107 | 121.7 (5) |
C307—C302—Ir2 | 111.4 (4) | C107—C102—Ir1 | 111.8 (4) |
C307—C302—H302 | 115.0 | C107—C102—H102 | 114.8 |
Ir2—C303—H303 | 113.5 | Ir1—C103—H103 | 113.8 |
C304—C303—Ir2 | 71.0 (4) | C104—C103—Ir1 | 70.6 (4) |
C304—C303—H303 | 113.5 | C104—C103—H103 | 113.8 |
C304—C303—C308 | 124.9 (6) | C104—C103—C108 | 125.2 (6) |
C308—C303—Ir2 | 113.1 (5) | C108—C103—Ir1 | 111.8 (4) |
C308—C303—H303 | 113.5 | C108—C103—H103 | 113.8 |
Ir2—C304—H304 | 114.0 | Ir1—C104—H104 | 113.2 |
C303—C304—Ir2 | 70.8 (4) | C103—C104—Ir1 | 71.1 (4) |
C303—C304—H304 | 114.0 | C103—C104—H104 | 113.2 |
C303—C304—C305 | 124.9 (7) | C103—C104—C105 | 124.6 (6) |
C305—C304—Ir2 | 111.4 (5) | C105—C104—Ir1 | 114.7 (4) |
C305—C304—H304 | 114.0 | C105—C104—H104 | 113.2 |
C304—C305—H30A | 108.4 | C104—C105—H10A | 108.9 |
C304—C305—H30B | 108.4 | C104—C105—H10B | 108.9 |
H30A—C305—H30B | 107.5 | H10A—C105—H10B | 107.8 |
C306—C305—C304 | 115.5 (6) | C106—C105—C104 | 113.2 (5) |
C306—C305—H30A | 108.4 | C106—C105—H10A | 108.9 |
C306—C305—H30B | 108.4 | C106—C105—H10B | 108.9 |
C301—C306—H30C | 109.2 | C101—C106—C105 | 112.1 (5) |
C301—C306—H30D | 109.2 | C101—C106—H10C | 109.2 |
C305—C306—C301 | 112.2 (6) | C101—C106—H10D | 109.2 |
C305—C306—H30C | 109.2 | C105—C106—H10C | 109.2 |
C305—C306—H30D | 109.2 | C105—C106—H10D | 109.2 |
H30C—C306—H30D | 107.9 | H10C—C106—H10D | 107.9 |
C302—C307—H30E | 108.9 | C102—C107—H10E | 108.9 |
C302—C307—H30F | 108.9 | C102—C107—H10F | 108.9 |
C302—C307—C308 | 113.2 (5) | C102—C107—C108 | 113.4 (5) |
H30E—C307—H30F | 107.7 | H10E—C107—H10F | 107.7 |
C308—C307—H30E | 108.9 | C108—C107—H10E | 108.9 |
C308—C307—H30F | 108.9 | C108—C107—H10F | 108.9 |
C303—C308—C307 | 113.2 (5) | C103—C108—C107 | 112.0 (5) |
C303—C308—H30G | 108.9 | C103—C108—H10G | 109.2 |
C303—C308—H30H | 108.9 | C103—C108—H10H | 109.2 |
C307—C308—H30G | 108.9 | C107—C108—H10G | 109.2 |
C307—C308—H30H | 108.9 | C107—C108—H10H | 109.2 |
H30G—C308—H30H | 107.8 | H10G—C108—H10H | 107.9 |
C325—C320—C321 | 118.6 (6) | C125—C120—C121 | 118.5 (5) |
C329—C320—C321 | 123.3 (5) | C125—C120—C129 | 117.5 (5) |
C329—C320—C325 | 118.1 (5) | C129—C120—C121 | 124.0 (5) |
C320—C321—N212 | 116.8 (5) | C120—C121—N12 | 117.3 (5) |
C322—C321—N212 | 121.5 (5) | C122—C121—N12 | 121.4 (5) |
C322—C321—C320 | 121.3 (5) | C122—C121—C120 | 121.1 (5) |
C321—C322—C323 | 118.4 (5) | C121—C122—C123 | 118.2 (5) |
C321—C322—C337 | 123.8 (5) | C121—C122—C137 | 124.2 (5) |
C323—C322—C337 | 117.6 (5) | C123—C122—C137 | 117.6 (5) |
C322—C323—H323 | 119.1 | C122—C123—H123 | 119.1 |
C324—C323—C322 | 121.8 (6) | C124—C123—C122 | 121.8 (6) |
C324—C323—H323 | 119.1 | C124—C123—H123 | 119.1 |
C323—C324—H324 | 119.7 | C123—C124—H124 | 119.6 |
C323—C324—C325 | 120.6 (5) | C123—C124—C125 | 120.7 (5) |
C325—C324—H324 | 119.7 | C125—C124—H124 | 119.6 |
C324—C325—C320 | 119.3 (5) | C124—C125—C120 | 118.9 (5) |
C324—C325—C326 | 122.0 (5) | C126—C125—C120 | 119.6 (6) |
C326—C325—C320 | 118.7 (6) | C126—C125—C124 | 121.3 (5) |
C325—C326—H326 | 119.6 | C125—C126—H126 | 119.3 |
C327—C326—C325 | 120.9 (6) | C127—C126—C125 | 121.4 (5) |
C327—C326—H326 | 119.6 | C127—C126—H126 | 119.3 |
C326—C327—H327 | 119.1 | C126—C127—H127 | 119.8 |
C326—C327—C328 | 121.8 (6) | C126—C127—C128 | 120.4 (6) |
C328—C327—H327 | 119.1 | C128—C127—H127 | 119.8 |
C327—C328—C331 | 118.6 (5) | C127—C128—C131 | 118.9 (5) |
C329—C328—C327 | 118.5 (6) | C129—C128—C127 | 119.0 (6) |
C329—C328—C331 | 122.8 (5) | C129—C128—C131 | 122.1 (5) |
C320—C329—H329 | 119.0 | C120—C129—H129 | 119.0 |
C328—C329—C320 | 121.9 (5) | C128—C129—C120 | 122.0 (5) |
C328—C329—H329 | 119.0 | C128—C129—H129 | 119.0 |
C328—C331—H331 | 107.6 | C128—C131—H131 | 107.8 |
C328—C331—C332 | 112.3 (6) | C128—C131—C132 | 112.2 (5) |
C328—C331—C336 | 112.5 (7) | C128—C131—C136 | 110.7 (5) |
C332—C331—H331 | 107.6 | C132—C131—H131 | 107.8 |
C332—C331—C336 | 109.1 (7) | C132—C131—C136 | 110.3 (5) |
C336—C331—H331 | 107.6 | C136—C131—H131 | 107.8 |
C331—C332—H33A | 109.9 | C131—C132—H13A | 109.1 |
C331—C332—H33B | 109.9 | C131—C132—H13B | 109.1 |
C331—C332—C333 | 108.9 (9) | C131—C132—C133 | 112.6 (6) |
H33A—C332—H33B | 108.3 | H13A—C132—H13B | 107.8 |
C333—C332—H33A | 109.9 | C133—C132—H13A | 109.1 |
C333—C332—H33B | 109.9 | C133—C132—H13B | 109.1 |
C332—C333—H33C | 109.1 | C132—C133—H13C | 109.3 |
C332—C333—H33D | 109.1 | C132—C133—H13D | 109.3 |
H33C—C333—H33D | 107.9 | H13C—C133—H13D | 107.9 |
C334—C333—C332 | 112.3 (10) | C134—C133—C132 | 111.8 (6) |
C334—C333—H33C | 109.1 | C134—C133—H13C | 109.3 |
C334—C333—H33D | 109.1 | C134—C133—H13D | 109.3 |
C333—C334—H33E | 109.3 | C133—C134—H13E | 109.3 |
C333—C334—H33F | 109.3 | C133—C134—H13F | 109.3 |
H33E—C334—H33F | 107.9 | C133—C134—C135 | 111.5 (6) |
C335—C334—C333 | 111.8 (10) | H13E—C134—H13F | 108.0 |
C335—C334—H33E | 109.3 | C135—C134—H13E | 109.3 |
C335—C334—H33F | 109.3 | C135—C134—H13F | 109.3 |
C334—C335—H33G | 109.4 | C134—C135—H13G | 109.4 |
C334—C335—H33H | 109.4 | C134—C135—H13H | 109.4 |
C334—C335—C336 | 111.1 (10) | C134—C135—C136 | 111.0 (6) |
H33G—C335—H33H | 108.0 | H13G—C135—H13H | 108.0 |
C336—C335—H33G | 109.4 | C136—C135—H13G | 109.4 |
C336—C335—H33H | 109.4 | C136—C135—H13H | 109.4 |
C331—C336—H33I | 109.8 | C131—C136—H13I | 109.0 |
C331—C336—H33J | 109.8 | C131—C136—H13J | 109.0 |
C335—C336—C331 | 109.2 (9) | C135—C136—C131 | 113.1 (6) |
C335—C336—H33I | 109.8 | C135—C136—H13I | 109.0 |
C335—C336—H33J | 109.8 | C135—C136—H13J | 109.0 |
H33I—C336—H33J | 108.3 | H13I—C136—H13J | 107.8 |
C322—C337—H337 | 108.1 | C122—C137—H137 | 108.1 |
C322—C337—C338 | 109.9 (5) | C122—C137—C138 | 114.1 (5) |
C322—C337—C342 | 112.6 (5) | C122—C137—C142 | 110.2 (5) |
C338—C337—H337 | 108.1 | C138—C137—H137 | 108.1 |
C342—C337—H337 | 108.1 | C142—C137—H137 | 108.1 |
C342—C337—C338 | 109.9 (5) | C142—C137—C138 | 108.1 (5) |
C337—C338—H33K | 109.4 | C137—C138—H13K | 109.4 |
C337—C338—H33L | 109.4 | C137—C138—H13L | 109.4 |
H33K—C338—H33L | 108.0 | H13K—C138—H13L | 108.0 |
C339—C338—C337 | 111.1 (5) | C139—C138—C137 | 111.1 (5) |
C339—C338—H33K | 109.4 | C139—C138—H13K | 109.4 |
C339—C338—H33L | 109.4 | C139—C138—H13L | 109.4 |
C338—C339—H33M | 109.0 | C138—C139—H13M | 109.2 |
C338—C339—H33N | 109.0 | C138—C139—H13N | 109.2 |
H33M—C339—H33N | 107.8 | C138—C139—C140 | 112.0 (6) |
C340—C339—C338 | 113.1 (6) | H13M—C139—H13N | 107.9 |
C340—C339—H33M | 109.0 | C140—C139—H13M | 109.2 |
C340—C339—H33N | 109.0 | C140—C139—H13N | 109.2 |
C339—C340—H34A | 109.3 | C139—C140—H14A | 109.5 |
C339—C340—H34B | 109.3 | C139—C140—H14B | 109.5 |
C339—C340—C341 | 111.7 (7) | H14A—C140—H14B | 108.1 |
H34A—C340—H34B | 107.9 | C141—C140—C139 | 110.7 (5) |
C341—C340—H34A | 109.3 | C141—C140—H14A | 109.5 |
C341—C340—H34B | 109.3 | C141—C140—H14B | 109.5 |
C340—C341—H34C | 109.5 | C140—C141—H14C | 109.3 |
C340—C341—H34D | 109.5 | C140—C141—H14D | 109.3 |
C340—C341—C342 | 110.8 (6) | C140—C141—C142 | 111.6 (5) |
H34C—C341—H34D | 108.1 | H14C—C141—H14D | 108.0 |
C342—C341—H34C | 109.5 | C142—C141—H14C | 109.3 |
C342—C341—H34D | 109.5 | C142—C141—H14D | 109.3 |
C337—C342—C341 | 110.8 (6) | C137—C142—H14E | 109.4 |
C337—C342—H34E | 109.5 | C137—C142—H14F | 109.4 |
C337—C342—H34F | 109.5 | C141—C142—C137 | 111.0 (5) |
C341—C342—H34E | 109.5 | C141—C142—H14E | 109.4 |
C341—C342—H34F | 109.5 | C141—C142—H14F | 109.4 |
H34E—C342—H34F | 108.1 | H14E—C142—H14F | 108.0 |
C355—C350—C351 | 118.2 (5) | C151—C150—C155 | 118.5 (5) |
C359—C350—C351 | 123.4 (5) | C159—C150—C151 | 123.1 (5) |
C359—C350—C355 | 118.4 (5) | C159—C150—C155 | 118.3 (5) |
C350—C351—N215 | 118.9 (5) | C150—C151—N15 | 118.1 (5) |
C352—C351—N215 | 120.3 (5) | C152—C151—N15 | 119.8 (5) |
C352—C351—C350 | 120.8 (5) | C152—C151—C150 | 121.9 (5) |
C351—C352—C353 | 117.8 (5) | C151—C152—C153 | 117.5 (5) |
C351—C352—C367 | 124.4 (4) | C151—C152—C167 | 124.5 (5) |
C353—C352—C367 | 117.6 (5) | C153—C152—C167 | 117.8 (5) |
C352—C353—H353 | 118.8 | C152—C153—H153 | 118.5 |
C354—C353—C352 | 122.5 (6) | C154—C153—C152 | 123.0 (6) |
C354—C353—H353 | 118.8 | C154—C153—H153 | 118.5 |
C353—C354—H354 | 119.8 | C153—C154—H154 | 120.0 |
C353—C354—C355 | 120.4 (5) | C153—C154—C155 | 120.0 (5) |
C355—C354—H354 | 119.8 | C155—C154—H154 | 120.0 |
C350—C355—C356 | 118.3 (6) | C154—C155—C150 | 119.1 (5) |
C354—C355—C350 | 119.8 (5) | C156—C155—C150 | 119.0 (6) |
C354—C355—C356 | 121.9 (5) | C156—C155—C154 | 121.9 (5) |
C355—C356—H356 | 119.6 | C155—C156—H156 | 119.5 |
C357—C356—C355 | 120.9 (5) | C157—C156—C155 | 121.1 (5) |
C357—C356—H356 | 119.6 | C157—C156—H156 | 119.5 |
C356—C357—H357 | 119.0 | C156—C157—H157 | 119.6 |
C356—C357—C358 | 122.0 (6) | C156—C157—C158 | 120.8 (5) |
C358—C357—H357 | 119.0 | C158—C157—H157 | 119.6 |
C357—C358—C361 | 119.9 (6) | C157—C158—C161 | 119.7 (5) |
C359—C358—C357 | 118.0 (6) | C159—C158—C157 | 119.0 (5) |
C359—C358—C361 | 122.0 (5) | C159—C158—C161 | 121.3 (5) |
C350—C359—H359 | 118.8 | C150—C159—H159 | 119.1 |
C358—C359—C350 | 122.3 (5) | C158—C159—C150 | 121.8 (5) |
C358—C359—H359 | 118.8 | C158—C159—H159 | 119.1 |
C358—C361—H361 | 108.3 | C158—C161—H161 | 106.6 |
C358—C361—C366 | 111.4 (6) | C158—C161—C162 | 113.0 (6) |
C362—C361—C358 | 110.8 (6) | C162—C161—H161 | 106.6 |
C362—C361—H361 | 108.3 | C166—C161—C158 | 113.0 (6) |
C362—C361—C366 | 109.8 (6) | C166—C161—H161 | 106.6 |
C366—C361—H361 | 108.3 | C166—C161—C162 | 110.4 (5) |
C361—C362—H36A | 109.0 | C161—C162—H16C | 109.2 |
C361—C362—H36B | 109.0 | C161—C162—H16D | 109.2 |
C361—C362—C363 | 112.9 (7) | C161—C162—C163 | 111.9 (5) |
H36A—C362—H36B | 107.8 | H16C—C162—H16D | 107.9 |
C363—C362—H36A | 109.0 | C163—C162—H16C | 109.2 |
C363—C362—H36B | 109.0 | C163—C162—H16D | 109.2 |
C362—C363—H36C | 109.7 | C162—C163—H16E | 109.8 |
C362—C363—H36D | 109.7 | C162—C163—H16F | 109.8 |
C362—C363—C364 | 109.8 (7) | H16E—C163—H16F | 108.2 |
H36C—C363—H36D | 108.2 | C164—C163—C162 | 109.5 (6) |
C364—C363—H36C | 109.7 | C164—C163—H16E | 109.8 |
C364—C363—H36D | 109.7 | C164—C163—H16F | 109.8 |
C363—C364—H36E | 109.8 | C163—C164—H16G | 109.2 |
C363—C364—H36F | 109.8 | C163—C164—H16H | 109.2 |
H36E—C364—H36F | 108.2 | C163—C164—C165 | 112.2 (6) |
C365—C364—C363 | 109.6 (7) | H16G—C164—H16H | 107.9 |
C365—C364—H36E | 109.8 | C165—C164—H16G | 109.2 |
C365—C364—H36F | 109.8 | C165—C164—H16H | 109.2 |
C364—C365—H36G | 109.4 | C164—C165—H16I | 109.3 |
C364—C365—H36H | 109.4 | C164—C165—H16J | 109.3 |
H36G—C365—H36H | 108.0 | C164—C165—C166 | 111.8 (6) |
C366—C365—C364 | 111.1 (7) | H16I—C165—H16J | 107.9 |
C366—C365—H36G | 109.4 | C166—C165—H16I | 109.3 |
C366—C365—H36H | 109.4 | C166—C165—H16J | 109.3 |
C361—C366—H36I | 108.5 | C161—C166—C165 | 111.2 (6) |
C361—C366—H36J | 108.5 | C161—C166—H16K | 109.4 |
C365—C366—C361 | 115.0 (7) | C161—C166—H16L | 109.4 |
C365—C366—H36I | 108.5 | C165—C166—H16K | 109.4 |
C365—C366—H36J | 108.5 | C165—C166—H16L | 109.4 |
H36I—C366—H36J | 107.5 | H16K—C166—H16L | 108.0 |
C352—C367—H367 | 108.7 | C152—C167—H167 | 107.9 |
C352—C367—C368 | 110.2 (5) | C152—C167—C168 | 111.0 (5) |
C352—C367—C372 | 113.8 (5) | C152—C167—C172 | 112.9 (5) |
C368—C367—H367 | 108.7 | C168—C167—H167 | 107.9 |
C368—C367—C372 | 106.7 (5) | C168—C167—C172 | 109.0 (5) |
C372—C367—H367 | 108.7 | C172—C167—H167 | 107.9 |
C367—C368—H36K | 109.2 | C167—C168—H16M | 109.0 |
C367—C368—H36L | 109.2 | C167—C168—H16N | 109.0 |
H36K—C368—H36L | 107.9 | H16M—C168—H16N | 107.8 |
C369—C368—C367 | 112.0 (5) | C169—C168—C167 | 112.9 (5) |
C369—C368—H36K | 109.2 | C169—C168—H16M | 109.0 |
C369—C368—H36L | 109.2 | C169—C168—H16N | 109.0 |
C368—C369—H36M | 109.7 | C168—C169—H16O | 109.5 |
C368—C369—H36N | 109.7 | C168—C169—H16P | 109.5 |
H36M—C369—H36N | 108.2 | C168—C169—C170 | 110.9 (6) |
C370—C369—C368 | 110.0 (5) | H16O—C169—H16P | 108.0 |
C370—C369—H36M | 109.7 | C170—C169—H16O | 109.5 |
C370—C369—H36N | 109.7 | C170—C169—H16P | 109.5 |
C369—C370—H37A | 109.1 | C169—C170—H17C | 109.3 |
C369—C370—H37B | 109.1 | C169—C170—H17D | 109.3 |
C369—C370—C371 | 112.4 (5) | H17C—C170—H17D | 107.9 |
H37A—C370—H37B | 107.9 | C171—C170—C169 | 111.7 (6) |
C371—C370—H37A | 109.1 | C171—C170—H17C | 109.3 |
C371—C370—H37B | 109.1 | C171—C170—H17D | 109.3 |
C370—C371—H37C | 109.3 | C170—C171—H17E | 109.2 |
C370—C371—H37D | 109.3 | C170—C171—H17F | 109.2 |
C370—C371—C372 | 111.4 (6) | H17E—C171—H17F | 107.9 |
H37C—C371—H37D | 108.0 | C172—C171—C170 | 112.1 (6) |
C372—C371—H37C | 109.3 | C172—C171—H17E | 109.2 |
C372—C371—H37D | 109.3 | C172—C171—H17F | 109.2 |
C367—C372—H37E | 109.3 | C167—C172—H17G | 109.3 |
C367—C372—H37F | 109.3 | C167—C172—H17H | 109.3 |
C371—C372—C367 | 111.5 (5) | C171—C172—C167 | 111.7 (6) |
C371—C372—H37E | 109.3 | C171—C172—H17G | 109.3 |
C371—C372—H37F | 109.3 | C171—C172—H17H | 109.3 |
H37E—C372—H37F | 108.0 | H17G—C172—H17H | 107.9 |
Ir2—C301—C302—C307 | 102.8 (6) | Ir1—C101—C102—C107 | 104.6 (5) |
Ir2—C301—C306—C305 | −35.4 (6) | Ir1—C101—C106—C105 | −32.2 (6) |
Ir2—C302—C307—C308 | −11.1 (7) | Ir1—C102—C107—C108 | −10.7 (6) |
Ir2—C303—C304—C305 | 103.2 (7) | Ir1—C103—C104—C105 | 107.5 (6) |
Ir2—C303—C308—C307 | −31.8 (7) | Ir1—C103—C108—C107 | −33.2 (7) |
Ir2—C304—C305—C306 | −7.7 (8) | Ir1—C104—C105—C106 | −9.5 (7) |
N212—C213—C214—N215 | −34.1 (5) | N12—C13—C14—N15 | −30.9 (5) |
N212—C213—C214—C219 | −165.4 (5) | N12—C13—C14—C19 | −160.3 (5) |
N212—C213—C216—C217 | −177.9 (5) | N12—C13—C16—C17 | −179.8 (5) |
N212—C321—C322—C323 | 173.5 (5) | N12—C121—C122—C123 | −178.6 (5) |
N212—C321—C322—C337 | −1.0 (9) | N12—C121—C122—C137 | 4.2 (9) |
N215—C214—C219—C218 | −177.2 (5) | N15—C14—C19—C18 | −176.6 (5) |
N215—C351—C352—C353 | 173.6 (5) | N15—C151—C152—C153 | −173.2 (5) |
N215—C351—C352—C367 | −11.0 (9) | N15—C151—C152—C167 | 3.2 (9) |
C211—N212—C213—C214 | 29.7 (6) | C11—N12—C13—C14 | 26.5 (6) |
C211—N212—C213—C216 | 153.9 (5) | C11—N12—C13—C16 | 150.0 (5) |
C211—N212—C321—C320 | −111.6 (6) | C11—N12—C121—C120 | −91.0 (7) |
C211—N212—C321—C322 | 74.6 (8) | C11—N12—C121—C122 | 93.9 (7) |
C211—N215—C214—C213 | 30.1 (6) | C11—N15—C14—C13 | 28.8 (6) |
C211—N215—C214—C219 | 153.0 (5) | C11—N15—C14—C19 | 151.1 (5) |
C211—N215—C351—C350 | 79.9 (8) | C11—N15—C151—C150 | 103.9 (7) |
C211—N215—C351—C352 | −100.9 (7) | C11—N15—C151—C152 | −82.2 (8) |
C213—N212—C211—Ir2 | 170.6 (4) | C13—N12—C11—Ir1 | 171.3 (4) |
C213—N212—C211—N215 | −11.8 (6) | C13—N12—C11—N15 | −9.2 (6) |
C213—N212—C321—C320 | 97.9 (6) | C13—N12—C121—C120 | 107.3 (6) |
C213—N212—C321—C322 | −75.9 (7) | C13—N12—C121—C122 | −67.9 (7) |
C213—C214—C219—C218 | −58.5 (6) | C13—C14—C19—C18 | −59.7 (6) |
C213—C216—C217—C218 | 53.1 (7) | C13—C16—C17—C18 | 54.0 (6) |
C214—N215—C211—Ir2 | 165.8 (4) | C14—N15—C11—Ir1 | 166.2 (4) |
C214—N215—C211—N212 | −12.0 (6) | C14—N15—C11—N12 | −13.2 (6) |
C214—N215—C351—C350 | −83.1 (7) | C14—N15—C151—C150 | −66.7 (7) |
C214—N215—C351—C352 | 96.1 (7) | C14—N15—C151—C152 | 107.1 (6) |
C214—C213—C216—C217 | −60.2 (6) | C14—C13—C16—C17 | −61.6 (5) |
C216—C213—C214—N215 | −163.1 (5) | C16—C13—C14—N15 | −161.3 (4) |
C216—C213—C214—C219 | 65.6 (6) | C16—C13—C14—C19 | 69.3 (6) |
C216—C217—C218—C219 | −54.1 (7) | C16—C17—C18—C19 | −53.1 (7) |
C217—C218—C219—C214 | 53.9 (7) | C17—C18—C19—C14 | 53.4 (7) |
C301—C302—C307—C308 | −89.6 (8) | C101—C102—C107—C108 | −91.5 (7) |
C302—C301—C306—C305 | 49.2 (9) | C102—C101—C106—C105 | 50.0 (8) |
C302—C307—C308—C303 | 27.8 (8) | C102—C107—C108—C103 | 28.7 (7) |
C303—C304—C305—C306 | −88.6 (9) | C103—C104—C105—C106 | −92.8 (8) |
C304—C303—C308—C307 | 50.6 (10) | C104—C103—C108—C107 | 47.9 (9) |
C304—C305—C306—C301 | 28.9 (8) | C104—C105—C106—C101 | 27.4 (7) |
C306—C301—C302—Ir2 | −102.0 (7) | C106—C101—C102—Ir1 | −103.0 (6) |
C306—C301—C302—C307 | 0.8 (10) | C106—C101—C102—C107 | 1.5 (9) |
C308—C303—C304—Ir2 | −105.4 (7) | C108—C103—C104—Ir1 | −103.5 (7) |
C308—C303—C304—C305 | −2.2 (12) | C108—C103—C104—C105 | 4.0 (11) |
C320—C321—C322—C323 | 0.0 (9) | C120—C121—C122—C123 | 6.4 (9) |
C320—C321—C322—C337 | −174.5 (5) | C120—C121—C122—C137 | −170.8 (5) |
C320—C325—C326—C327 | −0.1 (10) | C120—C125—C126—C127 | −0.9 (10) |
C321—N212—C211—Ir2 | 17.7 (8) | C121—N12—C11—Ir1 | 7.6 (8) |
C321—N212—C211—N215 | −164.6 (5) | C121—N12—C11—N15 | −172.9 (5) |
C321—N212—C213—C214 | −175.3 (5) | C121—N12—C13—C14 | −169.7 (5) |
C321—N212—C213—C216 | −51.1 (7) | C121—N12—C13—C16 | −46.2 (7) |
C321—C320—C325—C324 | 1.2 (9) | C121—C120—C125—C124 | 5.6 (9) |
C321—C320—C325—C326 | −177.5 (6) | C121—C120—C125—C126 | −178.6 (6) |
C321—C320—C329—C328 | 176.9 (6) | C121—C120—C129—C128 | −179.7 (6) |
C321—C322—C323—C324 | 0.7 (9) | C121—C122—C123—C124 | 1.7 (9) |
C321—C322—C337—C338 | 104.5 (6) | C121—C122—C137—C138 | −144.1 (6) |
C321—C322—C337—C342 | −132.6 (6) | C121—C122—C137—C142 | 94.1 (6) |
C322—C323—C324—C325 | −0.5 (10) | C122—C123—C124—C125 | −6.0 (10) |
C322—C337—C338—C339 | −179.0 (5) | C122—C137—C138—C139 | 178.1 (5) |
C322—C337—C342—C341 | 179.7 (4) | C122—C137—C142—C141 | −176.0 (5) |
C323—C322—C337—C338 | −70.0 (7) | C123—C122—C137—C138 | 38.7 (7) |
C323—C322—C337—C342 | 52.9 (7) | C123—C122—C137—C142 | −83.1 (6) |
C323—C324—C325—C320 | −0.5 (9) | C123—C124—C125—C120 | 2.1 (9) |
C323—C324—C325—C326 | 178.2 (6) | C123—C124—C125—C126 | −173.6 (6) |
C324—C325—C326—C327 | −178.8 (6) | C124—C125—C126—C127 | 174.8 (6) |
C325—C320—C321—N212 | −174.7 (5) | C125—C120—C121—N12 | 174.8 (5) |
C325—C320—C321—C322 | −1.0 (9) | C125—C120—C121—C122 | −10.0 (9) |
C325—C320—C329—C328 | −1.5 (9) | C125—C120—C129—C128 | −1.2 (9) |
C325—C326—C327—C328 | −0.3 (10) | C125—C126—C127—C128 | −2.8 (10) |
C326—C327—C328—C329 | −0.2 (10) | C126—C127—C128—C129 | 4.5 (10) |
C326—C327—C328—C331 | 178.5 (6) | C126—C127—C128—C131 | −175.9 (6) |
C327—C328—C329—C320 | 1.2 (10) | C127—C128—C129—C120 | −2.4 (9) |
C327—C328—C331—C332 | 110.2 (7) | C127—C128—C131—C132 | −51.6 (8) |
C327—C328—C331—C336 | −126.3 (7) | C127—C128—C131—C136 | 72.1 (7) |
C328—C331—C332—C333 | −179.2 (7) | C128—C131—C132—C133 | 172.2 (5) |
C328—C331—C336—C335 | 173.8 (7) | C128—C131—C136—C135 | −174.9 (5) |
C329—C320—C321—N212 | 6.9 (9) | C129—C120—C121—N12 | −6.7 (9) |
C329—C320—C321—C322 | −179.4 (6) | C129—C120—C121—C122 | 168.5 (6) |
C329—C320—C325—C324 | 179.7 (6) | C129—C120—C125—C124 | −172.9 (6) |
C329—C320—C325—C326 | 1.0 (9) | C129—C120—C125—C126 | 2.8 (9) |
C329—C328—C331—C332 | −71.1 (9) | C129—C128—C131—C132 | 128.0 (6) |
C329—C328—C331—C336 | 52.4 (10) | C129—C128—C131—C136 | −108.2 (6) |
C331—C328—C329—C320 | −177.6 (6) | C131—C128—C129—C120 | 178.0 (6) |
C331—C332—C333—C334 | −52.8 (11) | C131—C132—C133—C134 | −53.4 (7) |
C332—C331—C336—C335 | −61.0 (10) | C132—C131—C136—C135 | −50.0 (7) |
C332—C333—C334—C335 | 54.2 (13) | C132—C133—C134—C135 | 57.7 (7) |
C333—C334—C335—C336 | −59.2 (13) | C133—C134—C135—C136 | −58.8 (8) |
C334—C335—C336—C331 | 62.2 (12) | C134—C135—C136—C131 | 55.0 (7) |
C336—C331—C332—C333 | 55.3 (9) | C136—C131—C132—C133 | 48.3 (7) |
C337—C322—C323—C324 | 175.6 (6) | C137—C122—C123—C124 | 179.0 (6) |
C337—C338—C339—C340 | −55.3 (7) | C137—C138—C139—C140 | 57.6 (7) |
C338—C337—C342—C341 | −57.4 (6) | C138—C137—C142—C141 | 58.7 (6) |
C338—C339—C340—C341 | 53.7 (7) | C138—C139—C140—C141 | −53.9 (7) |
C339—C340—C341—C342 | −53.5 (8) | C139—C140—C141—C142 | 53.4 (7) |
C340—C341—C342—C337 | 55.9 (7) | C140—C141—C142—C137 | −57.3 (7) |
C342—C337—C338—C339 | 56.5 (7) | C142—C137—C138—C139 | −59.0 (6) |
C350—C351—C352—C353 | −7.3 (9) | C150—C151—C152—C153 | 0.5 (9) |
C350—C351—C352—C367 | 168.2 (5) | C150—C151—C152—C167 | 176.8 (5) |
C350—C355—C356—C357 | 3.9 (10) | C150—C155—C156—C157 | −0.1 (9) |
C351—N215—C211—Ir2 | 0.9 (8) | C151—N15—C11—Ir1 | −5.1 (9) |
C351—N215—C211—N212 | −177.0 (5) | C151—N15—C11—N12 | 175.4 (5) |
C351—N215—C214—C213 | −164.2 (5) | C151—N15—C14—C13 | −158.9 (5) |
C351—N215—C214—C219 | −41.4 (8) | C151—N15—C14—C19 | −36.6 (7) |
C351—C350—C355—C354 | −3.1 (9) | C151—C150—C155—C154 | 0.0 (9) |
C351—C350—C355—C356 | 179.2 (6) | C151—C150—C155—C156 | 177.7 (5) |
C351—C350—C359—C358 | 178.9 (6) | C151—C150—C159—C158 | −176.3 (5) |
C351—C352—C353—C354 | 1.3 (9) | C151—C152—C153—C154 | −0.1 (9) |
C351—C352—C367—C368 | −104.7 (6) | C151—C152—C167—C168 | −109.7 (6) |
C351—C352—C367—C372 | 135.4 (6) | C151—C152—C167—C172 | 127.5 (6) |
C352—C353—C354—C355 | 3.8 (10) | C152—C153—C154—C155 | −0.4 (10) |
C352—C367—C368—C369 | 175.5 (5) | C152—C167—C168—C169 | 178.8 (5) |
C352—C367—C372—C371 | 179.4 (5) | C152—C167—C172—C171 | 179.5 (4) |
C353—C352—C367—C368 | 70.7 (7) | C153—C152—C167—C168 | 66.6 (7) |
C353—C352—C367—C372 | −49.1 (7) | C153—C152—C167—C172 | −56.2 (7) |
C353—C354—C355—C350 | −2.8 (10) | C153—C154—C155—C150 | 0.4 (9) |
C353—C354—C355—C356 | 174.9 (6) | C153—C154—C155—C156 | −177.2 (6) |
C354—C355—C356—C357 | −173.8 (7) | C154—C155—C156—C157 | 177.6 (6) |
C355—C350—C351—N215 | −172.6 (5) | C155—C150—C151—N15 | 173.3 (5) |
C355—C350—C351—C352 | 8.2 (9) | C155—C150—C151—C152 | −0.4 (9) |
C355—C350—C359—C358 | 0.9 (9) | C155—C150—C159—C158 | 2.0 (9) |
C355—C356—C357—C358 | −3.2 (11) | C155—C156—C157—C158 | −0.5 (10) |
C356—C357—C358—C359 | 1.3 (11) | C156—C157—C158—C159 | 1.7 (9) |
C356—C357—C358—C361 | 177.8 (7) | C156—C157—C158—C161 | −178.4 (6) |
C357—C358—C359—C350 | −0.1 (10) | C157—C158—C159—C150 | −2.5 (9) |
C357—C358—C361—C362 | −67.3 (8) | C157—C158—C161—C162 | 127.4 (6) |
C357—C358—C361—C366 | 55.1 (9) | C157—C158—C161—C166 | −106.3 (6) |
C358—C361—C362—C363 | 176.3 (6) | C158—C161—C162—C163 | −173.8 (5) |
C358—C361—C366—C365 | −174.7 (6) | C158—C161—C166—C165 | 176.6 (5) |
C359—C350—C351—N215 | 9.3 (9) | C159—C150—C151—N15 | −8.5 (8) |
C359—C350—C351—C352 | −169.9 (6) | C159—C150—C151—C152 | 177.8 (6) |
C359—C350—C355—C354 | 175.1 (6) | C159—C150—C155—C154 | −178.3 (5) |
C359—C350—C355—C356 | −2.7 (9) | C159—C150—C155—C156 | −0.6 (9) |
C359—C358—C361—C362 | 109.0 (7) | C159—C158—C161—C162 | −52.7 (8) |
C359—C358—C361—C366 | −128.5 (7) | C159—C158—C161—C166 | 73.6 (7) |
C361—C358—C359—C350 | −176.5 (6) | C161—C158—C159—C150 | 177.6 (6) |
C361—C362—C363—C364 | −57.8 (10) | C161—C162—C163—C164 | −57.3 (8) |
C362—C361—C366—C365 | −51.6 (8) | C162—C161—C166—C165 | −55.7 (7) |
C362—C363—C364—C365 | 57.7 (10) | C162—C163—C164—C165 | 54.6 (8) |
C363—C364—C365—C366 | −56.1 (9) | C163—C164—C165—C166 | −53.5 (8) |
C364—C365—C366—C361 | 54.1 (8) | C164—C165—C166—C161 | 53.6 (8) |
C366—C361—C362—C363 | 52.9 (9) | C166—C161—C162—C163 | 58.5 (7) |
C367—C352—C353—C354 | −174.5 (6) | C167—C152—C153—C154 | −176.6 (6) |
C367—C368—C369—C370 | 59.6 (6) | C167—C168—C169—C170 | 55.6 (8) |
C368—C367—C372—C371 | 57.6 (6) | C168—C167—C172—C171 | 55.7 (6) |
C368—C369—C370—C371 | −54.7 (7) | C168—C169—C170—C171 | −53.0 (8) |
C369—C370—C371—C372 | 53.1 (7) | C169—C170—C171—C172 | 53.8 (8) |
C370—C371—C372—C367 | −55.4 (7) | C170—C171—C172—C167 | −55.5 (7) |
C372—C367—C368—C369 | −60.4 (6) | C172—C167—C168—C169 | −56.2 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17A···Cl1i | 0.99 | 2.79 | 3.773 (6) | 171 |
C353—H353···Cl1 | 0.95 | 2.80 | 3.650 (6) | 149 |
C372—H37E···Cl2 | 0.99 | 2.56 | 3.422 (6) | 146 |
Symmetry code: (i) x, y−1, z. |
[Ir(C51H64N2)Cl(C8H12)] | F(000) = 2152 |
Mr = 1040.86 | Dx = 1.405 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 10786 reflections |
a = 16.1663 (4) Å | θ = 3.6–67.3° |
b = 17.2811 (4) Å | µ = 6.04 mm−1 |
c = 17.6110 (3) Å | T = 100 K |
V = 4920.01 (19) Å3 | Needle, yellow |
Z = 4 | 0.25 × 0.03 × 0.02 mm |
Oxford Diffraction Gemini diffractometer | 8782 independent reflections |
Radiation source: sealed X-ray tube, Enhance Ultra (Cu) X-ray Source | 8164 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.056 |
Detector resolution: 10.4738 pixels mm-1 | θmax = 67.7°, θmin = 3.6° |
ω scans | h = −19→17 |
Absorption correction: analytical CrysAlisPro (Rigaku OD, 2019) | k = −19→20 |
Tmin = 0.50, Tmax = 0.90 | l = −19→20 |
26296 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0588P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.098 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 2.41 e Å−3 |
8782 reflections | Δρmin = −0.91 e Å−3 |
568 parameters | Absolute structure: Flack x determined using 3426 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.046 (7) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. One reflection with poor agreement was omitted from the refinement. |
x | y | z | Uiso*/Ueq | ||
Ir1 | 0.54235 (2) | 0.59059 (2) | 0.39700 (2) | 0.02181 (11) | |
Cl1 | 0.41450 (11) | 0.58045 (12) | 0.46083 (10) | 0.0271 (4) | |
C101 | 0.4761 (6) | 0.6278 (5) | 0.2922 (4) | 0.0294 (19) | |
H101 | 0.430379 | 0.596679 | 0.30705 | 0.035* | |
C102 | 0.4939 (5) | 0.6920 (5) | 0.3383 (5) | 0.0265 (18) | |
H102 | 0.457621 | 0.701343 | 0.379729 | 0.032* | |
C103 | 0.6542 (5) | 0.6303 (5) | 0.3450 (5) | 0.0260 (17) | |
H103 | 0.676855 | 0.631076 | 0.394737 | 0.031* | |
C104 | 0.6311 (5) | 0.5567 (5) | 0.3138 (5) | 0.0267 (17) | |
H104 | 0.642458 | 0.511952 | 0.343342 | 0.032* | |
C105 | 0.5902 (5) | 0.5451 (5) | 0.2382 (5) | 0.0279 (18) | |
H10A | 0.566757 | 0.492262 | 0.236247 | 0.033* | |
H10B | 0.632778 | 0.548944 | 0.197889 | 0.033* | |
C106 | 0.5221 (5) | 0.6028 (5) | 0.2214 (5) | 0.0302 (19) | |
H10C | 0.482453 | 0.57934 | 0.185318 | 0.036* | |
H10D | 0.546481 | 0.648976 | 0.196777 | 0.036* | |
C107 | 0.5648 (6) | 0.7477 (5) | 0.3284 (5) | 0.034 (2) | |
H10E | 0.574512 | 0.775328 | 0.376803 | 0.041* | |
H10F | 0.549921 | 0.78662 | 0.289465 | 0.041* | |
C108 | 0.6449 (6) | 0.7066 (5) | 0.3043 (5) | 0.0305 (19) | |
H10G | 0.643981 | 0.697551 | 0.248752 | 0.037* | |
H10H | 0.692941 | 0.740043 | 0.315985 | 0.037* | |
C11 | 0.5961 (5) | 0.5311 (5) | 0.4844 (4) | 0.0213 (16) | |
N12 | 0.6073 (4) | 0.5585 (4) | 0.5563 (4) | 0.0214 (14) | |
C121 | 0.5956 (5) | 0.6363 (5) | 0.5851 (4) | 0.0215 (16) | |
C122 | 0.6570 (5) | 0.6908 (5) | 0.5780 (4) | 0.0246 (17) | |
C123 | 0.6459 (5) | 0.7638 (5) | 0.6144 (5) | 0.0258 (17) | |
H123 | 0.68478 | 0.803936 | 0.605349 | 0.031* | |
C124 | 0.5811 (5) | 0.7774 (5) | 0.6615 (4) | 0.0256 (16) | |
H124 | 0.576518 | 0.825906 | 0.686505 | 0.031* | |
C125 | 0.5207 (5) | 0.7200 (5) | 0.6737 (4) | 0.0247 (17) | |
C126 | 0.4548 (6) | 0.7297 (4) | 0.7271 (4) | 0.0269 (16) | |
H126 | 0.450872 | 0.776472 | 0.755194 | 0.032* | |
C127 | 0.3973 (5) | 0.6726 (5) | 0.7384 (4) | 0.0248 (17) | |
H127 | 0.355672 | 0.679523 | 0.775885 | 0.03* | |
C128 | 0.3989 (5) | 0.6034 (5) | 0.6952 (5) | 0.0266 (17) | |
C129 | 0.4613 (5) | 0.5939 (5) | 0.6433 (4) | 0.0227 (14) | |
H129 | 0.462154 | 0.548212 | 0.613328 | 0.027* | |
C120 | 0.5251 (5) | 0.6499 (4) | 0.6326 (4) | 0.0204 (16) | |
C161 | 0.7386 (5) | 0.6754 (5) | 0.5391 (4) | 0.0233 (16) | |
H161 | 0.733987 | 0.624889 | 0.511759 | 0.028* | |
C162 | 0.8085 (5) | 0.6678 (5) | 0.5983 (5) | 0.0273 (16) | |
H16A | 0.816275 | 0.717833 | 0.624684 | 0.033* | |
H16B | 0.793018 | 0.628495 | 0.636703 | 0.033* | |
C163 | 0.8895 (5) | 0.6439 (6) | 0.5597 (5) | 0.0329 (19) | |
H16C | 0.934339 | 0.64292 | 0.597934 | 0.04* | |
H16D | 0.883456 | 0.590944 | 0.538973 | 0.04* | |
C164 | 0.9135 (6) | 0.6987 (5) | 0.4957 (5) | 0.0330 (19) | |
H16E | 0.961411 | 0.676866 | 0.467991 | 0.04* | |
H16F | 0.930811 | 0.748878 | 0.517712 | 0.04* | |
C165 | 0.8430 (6) | 0.7126 (6) | 0.4397 (5) | 0.034 (2) | |
H16G | 0.832436 | 0.664679 | 0.410497 | 0.041* | |
H16H | 0.859068 | 0.753699 | 0.403469 | 0.041* | |
C166 | 0.7638 (5) | 0.7368 (5) | 0.4814 (4) | 0.0284 (18) | |
H16I | 0.773054 | 0.786637 | 0.507716 | 0.034* | |
H16J | 0.718559 | 0.744093 | 0.444179 | 0.034* | |
C171 | 0.3316 (5) | 0.5443 (5) | 0.7060 (5) | 0.0287 (18) | |
H171 | 0.316697 | 0.54436 | 0.761102 | 0.034* | |
C172 | 0.3565 (5) | 0.4618 (5) | 0.6853 (5) | 0.0299 (18) | |
H17C | 0.40551 | 0.446625 | 0.715605 | 0.036* | |
H17D | 0.372039 | 0.459751 | 0.631004 | 0.036* | |
C173 | 0.2864 (5) | 0.4044 (6) | 0.7001 (5) | 0.0334 (18) | |
H17E | 0.303911 | 0.351856 | 0.684549 | 0.04* | |
H17F | 0.27361 | 0.403168 | 0.755108 | 0.04* | |
C174 | 0.2094 (6) | 0.4279 (6) | 0.6559 (5) | 0.038 (2) | |
H17G | 0.220897 | 0.423876 | 0.600786 | 0.045* | |
H17H | 0.163791 | 0.391721 | 0.668042 | 0.045* | |
C175 | 0.1828 (6) | 0.5096 (6) | 0.6744 (6) | 0.038 (2) | |
H17I | 0.164534 | 0.512181 | 0.728051 | 0.045* | |
H17J | 0.135308 | 0.524168 | 0.641923 | 0.045* | |
C176 | 0.2538 (6) | 0.5670 (5) | 0.6618 (6) | 0.035 (2) | |
H17K | 0.267029 | 0.569244 | 0.606981 | 0.042* | |
H17L | 0.235865 | 0.619238 | 0.677952 | 0.042* | |
C13 | 0.6188 (5) | 0.4929 (4) | 0.6090 (5) | 0.0236 (15) | |
H13 | 0.562656 | 0.47308 | 0.622637 | 0.028* | |
C14 | 0.6579 (5) | 0.4347 (5) | 0.5573 (4) | 0.0214 (16) | |
H14 | 0.718056 | 0.447535 | 0.55329 | 0.026* | |
N15 | 0.6182 (4) | 0.4564 (4) | 0.4847 (4) | 0.0223 (14) | |
C151 | 0.6255 (5) | 0.4036 (5) | 0.4216 (4) | 0.0238 (15) | |
C152 | 0.5576 (4) | 0.3625 (4) | 0.3968 (5) | 0.0236 (15) | |
C153 | 0.5708 (5) | 0.3055 (5) | 0.3389 (5) | 0.0282 (18) | |
H153 | 0.524944 | 0.276669 | 0.320479 | 0.034* | |
C154 | 0.6476 (6) | 0.2917 (5) | 0.3097 (5) | 0.0296 (18) | |
H154 | 0.654164 | 0.253125 | 0.271751 | 0.035* | |
C155 | 0.7167 (5) | 0.3329 (5) | 0.3344 (4) | 0.0260 (17) | |
C156 | 0.7967 (5) | 0.3190 (5) | 0.3058 (5) | 0.0275 (17) | |
H156 | 0.804137 | 0.281127 | 0.267303 | 0.033* | |
C157 | 0.8641 (6) | 0.3590 (5) | 0.3324 (5) | 0.0287 (18) | |
H157 | 0.917681 | 0.346593 | 0.313805 | 0.034* | |
C158 | 0.8550 (5) | 0.4179 (5) | 0.3865 (4) | 0.0246 (16) | |
C159 | 0.7772 (5) | 0.4340 (5) | 0.4133 (4) | 0.0254 (18) | |
H159 | 0.770588 | 0.475338 | 0.448369 | 0.031* | |
C150 | 0.7063 (5) | 0.3917 (4) | 0.3908 (5) | 0.0235 (15) | |
C181 | 0.4720 (5) | 0.3702 (5) | 0.4297 (4) | 0.0262 (17) | |
H181 | 0.47334 | 0.412284 | 0.468645 | 0.031* | |
C182 | 0.4456 (5) | 0.2949 (5) | 0.4694 (5) | 0.0307 (18) | |
H18A | 0.447569 | 0.2517 | 0.432519 | 0.037* | |
H18B | 0.485077 | 0.283093 | 0.510813 | 0.037* | |
C183 | 0.3586 (6) | 0.3007 (6) | 0.5023 (5) | 0.036 (2) | |
H18C | 0.357774 | 0.340291 | 0.542917 | 0.043* | |
H18D | 0.342937 | 0.250436 | 0.525169 | 0.043* | |
C184 | 0.2955 (6) | 0.3224 (6) | 0.4408 (6) | 0.036 (2) | |
H18E | 0.293029 | 0.280959 | 0.402041 | 0.044* | |
H18F | 0.239923 | 0.327664 | 0.463787 | 0.044* | |
C185 | 0.3202 (5) | 0.3985 (6) | 0.4032 (5) | 0.0344 (19) | |
H18G | 0.318776 | 0.440648 | 0.441306 | 0.041* | |
H18H | 0.280079 | 0.411315 | 0.362623 | 0.041* | |
C186 | 0.4080 (5) | 0.3927 (5) | 0.3689 (5) | 0.0299 (19) | |
H18I | 0.4082 | 0.353415 | 0.327973 | 0.036* | |
H18J | 0.423522 | 0.443075 | 0.34628 | 0.036* | |
C191 | 0.9290 (6) | 0.4584 (5) | 0.4195 (5) | 0.0297 (19) | |
H191 | 0.908722 | 0.504741 | 0.448049 | 0.036* | |
C192 | 0.9725 (6) | 0.4040 (9) | 0.4770 (6) | 0.052 (3) | |
H19A | 0.932509 | 0.38905 | 0.516898 | 0.063* | |
H19B | 0.989976 | 0.356292 | 0.450308 | 0.063* | |
C193 | 1.0474 (7) | 0.4407 (8) | 0.5141 (6) | 0.058 (3) | |
H19C | 1.074621 | 0.402467 | 0.547638 | 0.069* | |
H19D | 1.029534 | 0.485004 | 0.545713 | 0.069* | |
C194 | 1.1091 (6) | 0.4688 (7) | 0.4545 (6) | 0.043 (2) | |
H19E | 1.155584 | 0.49554 | 0.48007 | 0.052* | |
H19F | 1.131915 | 0.423725 | 0.426814 | 0.052* | |
C195 | 1.0687 (5) | 0.5234 (5) | 0.3988 (6) | 0.0344 (18) | |
H19G | 1.109179 | 0.53805 | 0.359187 | 0.041* | |
H19H | 1.051474 | 0.571068 | 0.425642 | 0.041* | |
C196 | 0.9931 (6) | 0.4862 (6) | 0.3613 (5) | 0.038 (2) | |
H19I | 1.011386 | 0.441661 | 0.330211 | 0.045* | |
H19J | 0.966896 | 0.524315 | 0.326902 | 0.045* | |
C16 | 0.6671 (5) | 0.5007 (5) | 0.6816 (5) | 0.0276 (17) | |
H16K | 0.640431 | 0.538744 | 0.715698 | 0.033* | |
H16L | 0.724238 | 0.518043 | 0.670861 | 0.033* | |
C17 | 0.6677 (6) | 0.4197 (5) | 0.7185 (4) | 0.0304 (18) | |
H17A | 0.703986 | 0.420942 | 0.763782 | 0.037* | |
H17B | 0.611018 | 0.40712 | 0.735927 | 0.037* | |
C18 | 0.6974 (5) | 0.3558 (5) | 0.6653 (5) | 0.0273 (17) | |
H18K | 0.690463 | 0.305221 | 0.690872 | 0.033* | |
H18L | 0.757209 | 0.363156 | 0.655391 | 0.033* | |
C19 | 0.6508 (5) | 0.3541 (5) | 0.5886 (4) | 0.0261 (17) | |
H19K | 0.676383 | 0.316189 | 0.553631 | 0.031* | |
H19L | 0.592066 | 0.339894 | 0.596329 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.02523 (16) | 0.02132 (16) | 0.01887 (16) | 0.00163 (14) | −0.00061 (13) | 0.00003 (13) |
Cl1 | 0.0241 (9) | 0.0308 (11) | 0.0264 (9) | 0.0000 (8) | 0.0015 (7) | 0.0006 (8) |
C101 | 0.037 (5) | 0.033 (4) | 0.018 (4) | 0.007 (4) | −0.006 (3) | 0.008 (3) |
C102 | 0.036 (4) | 0.016 (4) | 0.028 (4) | 0.012 (3) | −0.001 (3) | 0.012 (3) |
C103 | 0.024 (4) | 0.034 (5) | 0.021 (4) | −0.006 (3) | 0.005 (3) | 0.003 (3) |
C104 | 0.029 (4) | 0.026 (4) | 0.026 (4) | 0.006 (3) | 0.009 (4) | 0.002 (3) |
C105 | 0.032 (5) | 0.028 (5) | 0.023 (4) | 0.004 (4) | 0.003 (3) | −0.006 (3) |
C106 | 0.039 (5) | 0.029 (5) | 0.022 (4) | −0.004 (4) | −0.002 (3) | −0.003 (3) |
C107 | 0.051 (6) | 0.027 (5) | 0.024 (4) | 0.006 (4) | 0.000 (3) | 0.002 (3) |
C108 | 0.042 (5) | 0.028 (5) | 0.022 (4) | −0.002 (4) | 0.001 (4) | 0.003 (3) |
C11 | 0.018 (4) | 0.024 (4) | 0.021 (4) | 0.000 (3) | 0.000 (3) | −0.002 (3) |
N12 | 0.025 (3) | 0.023 (3) | 0.017 (3) | −0.002 (3) | 0.002 (3) | −0.002 (3) |
C121 | 0.028 (4) | 0.021 (4) | 0.016 (4) | −0.001 (3) | −0.001 (3) | −0.001 (3) |
C122 | 0.029 (4) | 0.026 (4) | 0.019 (4) | 0.002 (3) | −0.001 (3) | 0.003 (3) |
C123 | 0.031 (4) | 0.020 (4) | 0.026 (4) | −0.002 (3) | −0.008 (3) | 0.002 (3) |
C124 | 0.035 (4) | 0.019 (4) | 0.022 (4) | 0.004 (3) | −0.004 (3) | −0.002 (3) |
C125 | 0.032 (4) | 0.025 (4) | 0.017 (4) | 0.010 (3) | −0.003 (3) | 0.000 (3) |
C126 | 0.033 (4) | 0.017 (4) | 0.031 (4) | 0.007 (4) | −0.002 (4) | −0.004 (3) |
C127 | 0.028 (4) | 0.023 (4) | 0.023 (4) | 0.005 (3) | 0.001 (3) | −0.002 (3) |
C128 | 0.026 (4) | 0.025 (4) | 0.029 (4) | 0.006 (3) | −0.004 (3) | 0.009 (3) |
C129 | 0.026 (4) | 0.022 (3) | 0.020 (3) | 0.003 (4) | 0.000 (3) | −0.001 (3) |
C120 | 0.022 (4) | 0.018 (4) | 0.021 (3) | 0.003 (3) | −0.004 (3) | 0.002 (3) |
C161 | 0.025 (4) | 0.023 (4) | 0.021 (4) | −0.003 (3) | 0.002 (3) | −0.003 (3) |
C162 | 0.028 (4) | 0.026 (4) | 0.028 (4) | −0.003 (3) | −0.001 (4) | 0.001 (4) |
C163 | 0.029 (5) | 0.033 (5) | 0.036 (5) | −0.003 (4) | 0.003 (4) | −0.002 (4) |
C164 | 0.032 (5) | 0.033 (5) | 0.034 (5) | −0.004 (4) | 0.008 (4) | −0.006 (4) |
C165 | 0.038 (5) | 0.039 (5) | 0.025 (4) | −0.012 (4) | 0.003 (4) | 0.002 (4) |
C166 | 0.034 (4) | 0.031 (5) | 0.020 (4) | −0.006 (4) | 0.000 (3) | 0.003 (3) |
C171 | 0.031 (4) | 0.029 (5) | 0.026 (4) | −0.001 (4) | 0.004 (3) | −0.002 (3) |
C172 | 0.034 (5) | 0.027 (4) | 0.029 (4) | −0.002 (3) | 0.001 (4) | 0.003 (3) |
C173 | 0.035 (4) | 0.027 (4) | 0.038 (4) | −0.001 (4) | 0.002 (3) | 0.004 (4) |
C174 | 0.034 (5) | 0.044 (6) | 0.036 (5) | −0.006 (4) | 0.007 (4) | 0.000 (4) |
C175 | 0.030 (5) | 0.040 (6) | 0.044 (5) | 0.004 (4) | −0.002 (4) | −0.004 (4) |
C176 | 0.031 (5) | 0.026 (5) | 0.048 (5) | 0.004 (3) | 0.004 (4) | 0.001 (4) |
C13 | 0.028 (4) | 0.019 (4) | 0.023 (4) | 0.001 (3) | 0.002 (3) | 0.001 (3) |
C14 | 0.024 (4) | 0.023 (4) | 0.017 (4) | −0.001 (3) | 0.000 (3) | −0.001 (3) |
N15 | 0.025 (3) | 0.020 (3) | 0.022 (3) | −0.001 (3) | −0.002 (3) | 0.000 (3) |
C151 | 0.030 (4) | 0.019 (4) | 0.022 (3) | 0.001 (4) | −0.001 (3) | −0.001 (3) |
C152 | 0.026 (4) | 0.024 (4) | 0.021 (3) | −0.002 (3) | −0.001 (3) | −0.001 (3) |
C153 | 0.032 (4) | 0.024 (4) | 0.028 (4) | −0.004 (3) | 0.000 (3) | −0.004 (3) |
C154 | 0.043 (5) | 0.023 (4) | 0.022 (4) | 0.004 (3) | −0.001 (4) | −0.005 (3) |
C155 | 0.035 (5) | 0.021 (4) | 0.022 (4) | 0.007 (3) | 0.002 (3) | −0.002 (3) |
C156 | 0.037 (5) | 0.023 (4) | 0.022 (4) | 0.004 (3) | 0.005 (3) | −0.001 (3) |
C157 | 0.035 (5) | 0.027 (4) | 0.024 (4) | 0.010 (4) | 0.006 (3) | 0.009 (3) |
C158 | 0.029 (4) | 0.027 (4) | 0.018 (4) | 0.002 (3) | −0.003 (3) | 0.006 (3) |
C159 | 0.035 (5) | 0.019 (4) | 0.022 (4) | 0.005 (3) | 0.001 (3) | 0.000 (3) |
C150 | 0.031 (4) | 0.018 (4) | 0.022 (4) | 0.005 (3) | 0.002 (3) | 0.002 (3) |
C181 | 0.032 (5) | 0.022 (4) | 0.025 (4) | −0.001 (3) | −0.001 (3) | −0.006 (3) |
C182 | 0.031 (5) | 0.026 (4) | 0.035 (4) | −0.002 (3) | −0.003 (4) | 0.004 (3) |
C183 | 0.043 (5) | 0.030 (5) | 0.035 (5) | −0.005 (4) | 0.004 (4) | 0.000 (4) |
C184 | 0.033 (5) | 0.029 (5) | 0.047 (5) | −0.003 (4) | 0.004 (4) | −0.001 (4) |
C185 | 0.026 (4) | 0.042 (5) | 0.035 (4) | 0.000 (4) | −0.004 (3) | −0.003 (5) |
C186 | 0.029 (4) | 0.031 (5) | 0.030 (4) | 0.000 (3) | −0.005 (3) | 0.000 (3) |
C191 | 0.034 (5) | 0.028 (5) | 0.027 (4) | 0.001 (3) | 0.000 (3) | −0.005 (3) |
C192 | 0.044 (6) | 0.078 (8) | 0.035 (5) | −0.015 (6) | −0.002 (4) | 0.016 (6) |
C193 | 0.038 (5) | 0.097 (9) | 0.037 (5) | −0.016 (6) | −0.011 (5) | 0.027 (5) |
C194 | 0.037 (5) | 0.052 (6) | 0.039 (5) | −0.003 (4) | −0.002 (4) | 0.008 (5) |
C195 | 0.035 (4) | 0.031 (4) | 0.038 (4) | 0.002 (3) | 0.005 (4) | 0.007 (4) |
C196 | 0.040 (5) | 0.042 (6) | 0.031 (4) | −0.001 (4) | 0.002 (4) | 0.013 (4) |
C16 | 0.035 (4) | 0.022 (4) | 0.026 (4) | 0.000 (3) | −0.005 (3) | −0.004 (3) |
C17 | 0.038 (4) | 0.029 (5) | 0.024 (4) | 0.001 (4) | −0.001 (3) | 0.000 (4) |
C18 | 0.034 (4) | 0.018 (4) | 0.031 (4) | 0.002 (3) | −0.002 (3) | 0.005 (3) |
C19 | 0.038 (5) | 0.020 (4) | 0.021 (4) | 0.002 (3) | −0.002 (3) | −0.004 (3) |
Ir1—C11 | 2.045 (8) | C174—H17H | 0.99 |
Ir1—C104 | 2.132 (8) | C175—C176 | 1.533 (13) |
Ir1—C103 | 2.140 (8) | C175—H17I | 0.99 |
Ir1—C102 | 2.181 (7) | C175—H17J | 0.99 |
Ir1—C101 | 2.228 (7) | C176—H17K | 0.99 |
Ir1—Cl1 | 2.3592 (18) | C176—H17L | 0.99 |
C101—C102 | 1.405 (13) | C13—C14 | 1.496 (11) |
C101—C106 | 1.515 (12) | C13—C16 | 1.502 (12) |
C101—H101 | 0.95 | C13—H13 | 1 |
C102—C107 | 1.507 (13) | C14—N15 | 1.479 (10) |
C102—H102 | 0.95 | C14—C19 | 1.504 (11) |
C103—C104 | 1.435 (12) | C14—H14 | 1 |
C103—C108 | 1.508 (12) | N15—C151 | 1.443 (10) |
C103—H103 | 0.95 | C151—C152 | 1.377 (11) |
C104—C105 | 1.501 (12) | C151—C150 | 1.429 (11) |
C104—H104 | 0.95 | C152—C153 | 1.433 (12) |
C105—C106 | 1.514 (12) | C152—C181 | 1.506 (11) |
C105—H10A | 0.99 | C153—C154 | 1.366 (13) |
C105—H10B | 0.99 | C153—H153 | 0.95 |
C106—H10C | 0.99 | C154—C155 | 1.393 (13) |
C106—H10D | 0.99 | C154—H154 | 0.95 |
C107—C108 | 1.536 (13) | C155—C156 | 1.408 (12) |
C107—H10E | 0.99 | C155—C150 | 1.431 (11) |
C107—H10F | 0.99 | C156—C157 | 1.373 (13) |
C108—H10G | 0.99 | C156—H156 | 0.95 |
C108—H10H | 0.99 | C157—C158 | 1.403 (12) |
C11—N15 | 1.339 (11) | C157—H157 | 0.95 |
C11—N12 | 1.363 (10) | C158—C159 | 1.372 (12) |
N12—C121 | 1.449 (10) | C158—C191 | 1.503 (12) |
N12—C13 | 1.478 (10) | C159—C150 | 1.417 (12) |
C121—C122 | 1.374 (12) | C159—H159 | 0.95 |
C121—C120 | 1.433 (11) | C181—C186 | 1.538 (12) |
C122—C123 | 1.427 (12) | C181—C182 | 1.539 (12) |
C122—C161 | 1.511 (11) | C181—H181 | 1 |
C123—C124 | 1.356 (12) | C182—C183 | 1.524 (13) |
C123—H123 | 0.95 | C182—H18A | 0.99 |
C124—C125 | 1.408 (12) | C182—H18B | 0.99 |
C124—H124 | 0.95 | C183—C184 | 1.535 (14) |
C125—C120 | 1.413 (11) | C183—H18C | 0.99 |
C125—C126 | 1.430 (12) | C183—H18D | 0.99 |
C126—C127 | 1.370 (13) | C184—C185 | 1.525 (14) |
C126—H126 | 0.95 | C184—H18E | 0.99 |
C127—C128 | 1.417 (12) | C184—H18F | 0.99 |
C127—H127 | 0.95 | C185—C186 | 1.547 (12) |
C128—C129 | 1.372 (11) | C185—H18G | 0.99 |
C128—C171 | 1.505 (12) | C185—H18H | 0.99 |
C129—C120 | 1.426 (11) | C186—H18I | 0.99 |
C129—H129 | 0.95 | C186—H18J | 0.99 |
C161—C166 | 1.524 (11) | C191—C196 | 1.535 (13) |
C161—C162 | 1.543 (12) | C191—C192 | 1.550 (15) |
C161—H161 | 1 | C191—H191 | 1 |
C162—C163 | 1.532 (12) | C192—C193 | 1.515 (15) |
C162—H16A | 0.99 | C192—H19A | 0.99 |
C162—H16B | 0.99 | C192—H19B | 0.99 |
C163—C164 | 1.522 (13) | C193—C194 | 1.526 (15) |
C163—H16C | 0.99 | C193—H19C | 0.99 |
C163—H16D | 0.99 | C193—H19D | 0.99 |
C164—C165 | 1.526 (13) | C194—C195 | 1.510 (14) |
C164—H16E | 0.99 | C194—H19E | 0.99 |
C164—H16F | 0.99 | C194—H19F | 0.99 |
C165—C166 | 1.534 (13) | C195—C196 | 1.529 (14) |
C165—H16G | 0.99 | C195—H19G | 0.99 |
C165—H16H | 0.99 | C195—H19H | 0.99 |
C166—H16I | 0.99 | C196—H19I | 0.99 |
C166—H16J | 0.99 | C196—H19J | 0.99 |
C171—C172 | 1.526 (12) | C16—C17 | 1.543 (12) |
C171—C176 | 1.529 (13) | C16—H16K | 0.99 |
C171—H171 | 1 | C16—H16L | 0.99 |
C172—C173 | 1.528 (12) | C17—C18 | 1.525 (12) |
C172—H17C | 0.99 | C17—H17A | 0.99 |
C172—H17D | 0.99 | C17—H17B | 0.99 |
C173—C174 | 1.523 (13) | C18—C19 | 1.547 (11) |
C173—H17E | 0.99 | C18—H18K | 0.99 |
C173—H17F | 0.99 | C18—H18L | 0.99 |
C174—C175 | 1.513 (14) | C19—H19K | 0.99 |
C174—H17G | 0.99 | C19—H19L | 0.99 |
C11—Ir1—C104 | 95.4 (3) | C175—C174—H17H | 109.3 |
C11—Ir1—C103 | 97.2 (3) | C173—C174—H17H | 109.3 |
C104—Ir1—C103 | 39.3 (3) | H17G—C174—H17H | 107.9 |
C11—Ir1—C102 | 156.0 (3) | C174—C175—C176 | 111.1 (8) |
C104—Ir1—C102 | 97.9 (3) | C174—C175—H17I | 109.4 |
C103—Ir1—C102 | 80.9 (3) | C176—C175—H17I | 109.4 |
C11—Ir1—C101 | 166.6 (3) | C174—C175—H17J | 109.4 |
C104—Ir1—C101 | 80.4 (3) | C176—C175—H17J | 109.4 |
C103—Ir1—C101 | 87.7 (3) | H17I—C175—H17J | 108 |
C102—Ir1—C101 | 37.2 (3) | C171—C176—C175 | 112.1 (8) |
C11—Ir1—Cl1 | 88.6 (2) | C171—C176—H17K | 109.2 |
C104—Ir1—Cl1 | 153.7 (2) | C175—C176—H17K | 109.2 |
C103—Ir1—Cl1 | 165.4 (2) | C171—C176—H17L | 109.2 |
C102—Ir1—Cl1 | 88.3 (2) | C175—C176—H17L | 109.2 |
C101—Ir1—Cl1 | 89.7 (2) | H17K—C176—H17L | 107.9 |
C102—C101—C106 | 126.8 (8) | N12—C13—C14 | 100.7 (6) |
C102—C101—Ir1 | 69.6 (4) | N12—C13—C16 | 122.2 (7) |
C106—C101—Ir1 | 111.3 (5) | C14—C13—C16 | 111.0 (7) |
C102—C101—H101 | 116.6 | N12—C13—H13 | 107.4 |
C106—C101—H101 | 116.6 | C14—C13—H13 | 107.4 |
Ir1—C101—H101 | 89 | C16—C13—H13 | 107.4 |
C101—C102—C107 | 126.4 (8) | N15—C14—C13 | 100.0 (6) |
C101—C102—Ir1 | 73.2 (4) | N15—C14—C19 | 121.3 (7) |
C107—C102—Ir1 | 107.1 (5) | C13—C14—C19 | 111.5 (6) |
C101—C102—H102 | 116.8 | N15—C14—H14 | 107.8 |
C107—C102—H102 | 116.8 | C13—C14—H14 | 107.8 |
Ir1—C102—H102 | 89.6 | C19—C14—H14 | 107.8 |
C104—C103—C108 | 124.6 (7) | C11—N15—C151 | 129.0 (7) |
C104—C103—Ir1 | 70.1 (5) | C11—N15—C14 | 111.3 (6) |
C108—C103—Ir1 | 113.6 (6) | C151—N15—C14 | 118.0 (6) |
C104—C103—H103 | 117.7 | C152—C151—C150 | 122.2 (7) |
C108—C103—H103 | 117.7 | C152—C151—N15 | 120.3 (7) |
Ir1—C103—H103 | 86.3 | C150—C151—N15 | 117.2 (7) |
C103—C104—C105 | 124.9 (8) | C151—C152—C153 | 117.5 (7) |
C103—C104—Ir1 | 70.7 (5) | C151—C152—C181 | 124.4 (7) |
C105—C104—Ir1 | 110.6 (6) | C153—C152—C181 | 118.0 (7) |
C103—C104—H104 | 117.5 | C154—C153—C152 | 121.5 (8) |
C105—C104—H104 | 117.5 | C154—C153—H153 | 119.2 |
Ir1—C104—H104 | 88.8 | C152—C153—H153 | 119.2 |
C104—C105—C106 | 113.9 (7) | C153—C154—C155 | 121.5 (8) |
C104—C105—H10A | 108.8 | C153—C154—H154 | 119.3 |
C106—C105—H10A | 108.8 | C155—C154—H154 | 119.3 |
C104—C105—H10B | 108.8 | C154—C155—C156 | 122.5 (7) |
C106—C105—H10B | 108.8 | C154—C155—C150 | 119.0 (8) |
H10A—C105—H10B | 107.7 | C156—C155—C150 | 118.5 (8) |
C105—C106—C101 | 112.6 (7) | C157—C156—C155 | 121.4 (8) |
C105—C106—H10C | 109.1 | C157—C156—H156 | 119.3 |
C101—C106—H10C | 109.1 | C155—C156—H156 | 119.3 |
C105—C106—H10D | 109.1 | C156—C157—C158 | 120.9 (8) |
C101—C106—H10D | 109.1 | C156—C157—H157 | 119.5 |
H10C—C106—H10D | 107.8 | C158—C157—H157 | 119.5 |
C102—C107—C108 | 112.2 (7) | C159—C158—C157 | 118.5 (8) |
C102—C107—H10E | 109.2 | C159—C158—C191 | 120.1 (7) |
C108—C107—H10E | 109.2 | C157—C158—C191 | 121.2 (7) |
C102—C107—H10F | 109.2 | C158—C159—C150 | 122.8 (7) |
C108—C107—H10F | 109.2 | C158—C159—H159 | 118.6 |
H10E—C107—H10F | 107.9 | C150—C159—H159 | 118.6 |
C103—C108—C107 | 110.9 (7) | C159—C150—C151 | 124.0 (7) |
C103—C108—H10G | 109.5 | C159—C150—C155 | 117.7 (7) |
C107—C108—H10G | 109.5 | C151—C150—C155 | 118.2 (7) |
C103—C108—H10H | 109.5 | C152—C181—C186 | 111.9 (7) |
C107—C108—H10H | 109.5 | C152—C181—C182 | 110.8 (7) |
H10G—C108—H10H | 108.1 | C186—C181—C182 | 110.1 (7) |
N15—C11—N12 | 107.2 (7) | C152—C181—H181 | 108 |
N15—C11—Ir1 | 126.9 (6) | C186—C181—H181 | 108 |
N12—C11—Ir1 | 125.5 (6) | C182—C181—H181 | 108 |
C11—N12—C121 | 129.1 (7) | C183—C182—C181 | 111.9 (7) |
C11—N12—C13 | 109.5 (6) | C183—C182—H18A | 109.2 |
C121—N12—C13 | 120.5 (6) | C181—C182—H18A | 109.2 |
C122—C121—C120 | 121.0 (7) | C183—C182—H18B | 109.2 |
C122—C121—N12 | 120.6 (7) | C181—C182—H18B | 109.2 |
C120—C121—N12 | 117.4 (7) | H18A—C182—H18B | 107.9 |
C121—C122—C123 | 118.3 (8) | C182—C183—C184 | 111.2 (8) |
C121—C122—C161 | 123.5 (7) | C182—C183—H18C | 109.4 |
C123—C122—C161 | 118.0 (7) | C184—C183—H18C | 109.4 |
C124—C123—C122 | 121.7 (8) | C182—C183—H18D | 109.4 |
C124—C123—H123 | 119.2 | C184—C183—H18D | 109.4 |
C122—C123—H123 | 119.2 | H18C—C183—H18D | 108 |
C123—C124—C125 | 120.5 (7) | C185—C184—C183 | 110.1 (8) |
C123—C124—H124 | 119.8 | C185—C184—H18E | 109.6 |
C125—C124—H124 | 119.8 | C183—C184—H18E | 109.6 |
C124—C125—C120 | 119.3 (7) | C185—C184—H18F | 109.6 |
C124—C125—C126 | 122.3 (7) | C183—C184—H18F | 109.6 |
C120—C125—C126 | 118.3 (7) | H18E—C184—H18F | 108.2 |
C127—C126—C125 | 121.1 (7) | C184—C185—C186 | 110.7 (8) |
C127—C126—H126 | 119.4 | C184—C185—H18G | 109.5 |
C125—C126—H126 | 119.4 | C186—C185—H18G | 109.5 |
C126—C127—C128 | 121.1 (7) | C184—C185—H18H | 109.5 |
C126—C127—H127 | 119.4 | C186—C185—H18H | 109.5 |
C128—C127—H127 | 119.4 | H18G—C185—H18H | 108.1 |
C129—C128—C127 | 118.2 (8) | C181—C186—C185 | 111.2 (7) |
C129—C128—C171 | 122.3 (8) | C181—C186—H18I | 109.4 |
C127—C128—C171 | 119.5 (7) | C185—C186—H18I | 109.4 |
C128—C129—C120 | 122.6 (7) | C181—C186—H18J | 109.4 |
C128—C129—H129 | 118.7 | C185—C186—H18J | 109.4 |
C120—C129—H129 | 118.7 | H18I—C186—H18J | 108 |
C125—C120—C129 | 118.5 (7) | C158—C191—C196 | 115.1 (7) |
C125—C120—C121 | 118.7 (7) | C158—C191—C192 | 109.3 (8) |
C129—C120—C121 | 122.7 (7) | C196—C191—C192 | 108.6 (8) |
C122—C161—C166 | 114.4 (7) | C158—C191—H191 | 107.8 |
C122—C161—C162 | 110.4 (6) | C196—C191—H191 | 107.8 |
C166—C161—C162 | 108.4 (7) | C192—C191—H191 | 107.8 |
C122—C161—H161 | 107.8 | C193—C192—C191 | 113.0 (10) |
C166—C161—H161 | 107.8 | C193—C192—H19A | 109 |
C162—C161—H161 | 107.8 | C191—C192—H19A | 109 |
C163—C162—C161 | 110.4 (7) | C193—C192—H19B | 109 |
C163—C162—H16A | 109.6 | C191—C192—H19B | 109 |
C161—C162—H16A | 109.6 | H19A—C192—H19B | 107.8 |
C163—C162—H16B | 109.6 | C192—C193—C194 | 111.1 (8) |
C161—C162—H16B | 109.6 | C192—C193—H19C | 109.4 |
H16A—C162—H16B | 108.1 | C194—C193—H19C | 109.4 |
C164—C163—C162 | 112.3 (8) | C192—C193—H19D | 109.4 |
C164—C163—H16C | 109.1 | C194—C193—H19D | 109.4 |
C162—C163—H16C | 109.1 | H19C—C193—H19D | 108 |
C164—C163—H16D | 109.1 | C195—C194—C193 | 111.2 (9) |
C162—C163—H16D | 109.1 | C195—C194—H19E | 109.4 |
H16C—C163—H16D | 107.9 | C193—C194—H19E | 109.4 |
C163—C164—C165 | 112.7 (7) | C195—C194—H19F | 109.4 |
C163—C164—H16E | 109.1 | C193—C194—H19F | 109.4 |
C165—C164—H16E | 109.1 | H19E—C194—H19F | 108 |
C163—C164—H16F | 109.1 | C194—C195—C196 | 111.4 (8) |
C165—C164—H16F | 109.1 | C194—C195—H19G | 109.4 |
H16E—C164—H16F | 107.8 | C196—C195—H19G | 109.4 |
C164—C165—C166 | 111.0 (7) | C194—C195—H19H | 109.4 |
C164—C165—H16G | 109.4 | C196—C195—H19H | 109.4 |
C166—C165—H16G | 109.4 | H19G—C195—H19H | 108 |
C164—C165—H16H | 109.4 | C195—C196—C191 | 112.5 (8) |
C166—C165—H16H | 109.4 | C195—C196—H19I | 109.1 |
H16G—C165—H16H | 108 | C191—C196—H19I | 109.1 |
C161—C166—C165 | 110.6 (7) | C195—C196—H19J | 109.1 |
C161—C166—H16I | 109.5 | C191—C196—H19J | 109.1 |
C165—C166—H16I | 109.5 | H19I—C196—H19J | 107.8 |
C161—C166—H16J | 109.5 | C13—C16—C17 | 106.3 (7) |
C165—C166—H16J | 109.5 | C13—C16—H16K | 110.5 |
H16I—C166—H16J | 108.1 | C17—C16—H16K | 110.5 |
C128—C171—C172 | 114.4 (7) | C13—C16—H16L | 110.5 |
C128—C171—C176 | 110.9 (7) | C17—C16—H16L | 110.5 |
C172—C171—C176 | 109.6 (7) | H16K—C16—H16L | 108.7 |
C128—C171—H171 | 107.2 | C18—C17—C16 | 113.5 (7) |
C172—C171—H171 | 107.2 | C18—C17—H17A | 108.9 |
C176—C171—H171 | 107.2 | C16—C17—H17A | 108.9 |
C171—C172—C173 | 111.7 (7) | C18—C17—H17B | 108.9 |
C171—C172—H17C | 109.3 | C16—C17—H17B | 108.9 |
C173—C172—H17C | 109.3 | H17A—C17—H17B | 107.7 |
C171—C172—H17D | 109.3 | C17—C18—C19 | 113.4 (7) |
C173—C172—H17D | 109.3 | C17—C18—H18K | 108.9 |
H17C—C172—H17D | 107.9 | C19—C18—H18K | 108.9 |
C174—C173—C172 | 110.2 (8) | C17—C18—H18L | 108.9 |
C174—C173—H17E | 109.6 | C19—C18—H18L | 108.9 |
C172—C173—H17E | 109.6 | H18K—C18—H18L | 107.7 |
C174—C173—H17F | 109.6 | C14—C19—C18 | 105.4 (7) |
C172—C173—H17F | 109.6 | C14—C19—H19K | 110.7 |
H17E—C173—H17F | 108.1 | C18—C19—H19K | 110.7 |
C175—C174—C173 | 111.7 (8) | C14—C19—H19L | 110.7 |
C175—C174—H17G | 109.3 | C18—C19—H19L | 110.7 |
C173—C174—H17G | 109.3 | H19K—C19—H19L | 108.8 |
C106—C101—C102—C107 | −2.7 (13) | C11—N12—C13—C16 | 153.0 (7) |
Ir1—C101—C102—C107 | 99.2 (8) | C121—N12—C13—C16 | −37.0 (11) |
C106—C101—C102—Ir1 | −101.9 (8) | N12—C13—C14—N15 | −31.5 (7) |
C108—C103—C104—C105 | −3.5 (13) | C16—C13—C14—N15 | −162.2 (6) |
Ir1—C103—C104—C105 | 102.1 (8) | N12—C13—C14—C19 | −161.0 (6) |
C108—C103—C104—Ir1 | −105.5 (8) | C16—C13—C14—C19 | 68.3 (9) |
C103—C104—C105—C106 | −42.6 (12) | N12—C11—N15—C151 | −173.3 (7) |
Ir1—C104—C105—C106 | 37.6 (9) | Ir1—C11—N15—C151 | 13.5 (12) |
C104—C105—C106—C101 | −32.9 (11) | N12—C11—N15—C14 | −8.7 (9) |
C102—C101—C106—C105 | 92.2 (10) | Ir1—C11—N15—C14 | 178.0 (5) |
Ir1—C101—C106—C105 | 12.3 (9) | C13—C14—N15—C11 | 26.6 (8) |
C101—C102—C107—C108 | −39.2 (11) | C19—C14—N15—C11 | 149.5 (7) |
Ir1—C102—C107—C108 | 42.3 (8) | C13—C14—N15—C151 | −167.0 (6) |
C104—C103—C108—C107 | 97.0 (10) | C19—C14—N15—C151 | −44.1 (10) |
Ir1—C103—C108—C107 | 15.7 (9) | C11—N15—C151—C152 | −87.1 (11) |
C102—C107—C108—C103 | −39.0 (10) | C14—N15—C151—C152 | 109.3 (9) |
N15—C11—N12—C121 | 177.3 (7) | C11—N15—C151—C150 | 97.8 (10) |
Ir1—C11—N12—C121 | −9.3 (12) | C14—N15—C151—C150 | −65.9 (9) |
N15—C11—N12—C13 | −13.8 (9) | C150—C151—C152—C153 | 0.9 (12) |
Ir1—C11—N12—C13 | 159.5 (5) | N15—C151—C152—C153 | −174.0 (7) |
C11—N12—C121—C122 | −83.8 (11) | C150—C151—C152—C181 | 177.1 (7) |
C13—N12—C121—C122 | 108.3 (8) | N15—C151—C152—C181 | 2.2 (12) |
C11—N12—C121—C120 | 107.1 (9) | C151—C152—C153—C154 | 0.6 (12) |
C13—N12—C121—C120 | −60.8 (10) | C181—C152—C153—C154 | −175.9 (8) |
C120—C121—C122—C123 | −4.7 (11) | C152—C153—C154—C155 | −0.6 (13) |
N12—C121—C122—C123 | −173.5 (7) | C153—C154—C155—C156 | 179.2 (8) |
C120—C121—C122—C161 | 170.1 (7) | C153—C154—C155—C150 | −0.9 (13) |
N12—C121—C122—C161 | 1.4 (11) | C154—C155—C156—C157 | −178.3 (8) |
C121—C122—C123—C124 | 6.9 (11) | C150—C155—C156—C157 | 1.8 (12) |
C161—C122—C123—C124 | −168.2 (7) | C155—C156—C157—C158 | −3.1 (12) |
C122—C123—C124—C125 | −2.5 (12) | C156—C157—C158—C159 | 0.9 (12) |
C123—C124—C125—C120 | −4.1 (11) | C156—C157—C158—C191 | 176.1 (8) |
C123—C124—C125—C126 | 175.3 (7) | C157—C158—C159—C150 | 2.6 (12) |
C124—C125—C126—C127 | −179.3 (8) | C191—C158—C159—C150 | −172.6 (7) |
C120—C125—C126—C127 | 0.1 (11) | C158—C159—C150—C151 | 175.5 (8) |
C125—C126—C127—C128 | −2.9 (12) | C158—C159—C150—C155 | −3.8 (11) |
C126—C127—C128—C129 | 2.1 (12) | C152—C151—C150—C159 | 178.3 (8) |
C126—C127—C128—C171 | −176.2 (8) | N15—C151—C150—C159 | −6.6 (11) |
C127—C128—C129—C120 | 1.4 (11) | C152—C151—C150—C155 | −2.3 (12) |
C171—C128—C129—C120 | 179.7 (7) | N15—C151—C150—C155 | 172.7 (7) |
C124—C125—C120—C129 | −177.3 (7) | C154—C155—C150—C159 | −178.3 (8) |
C126—C125—C120—C129 | 3.2 (10) | C156—C155—C150—C159 | 1.6 (11) |
C124—C125—C120—C121 | 6.1 (10) | C154—C155—C150—C151 | 2.3 (11) |
C126—C125—C120—C121 | −173.4 (7) | C156—C155—C150—C151 | −177.8 (7) |
C128—C129—C120—C125 | −4.0 (11) | C151—C152—C181—C186 | 122.8 (8) |
C128—C129—C120—C121 | 172.4 (7) | C153—C152—C181—C186 | −61.0 (10) |
C122—C121—C120—C125 | −1.6 (11) | C151—C152—C181—C182 | −113.9 (9) |
N12—C121—C120—C125 | 167.5 (7) | C153—C152—C181—C182 | 62.3 (9) |
C122—C121—C120—C129 | −178.0 (7) | C152—C181—C182—C183 | −179.2 (7) |
N12—C121—C120—C129 | −9.0 (10) | C186—C181—C182—C183 | −54.9 (9) |
C121—C122—C161—C166 | 131.4 (8) | C181—C182—C183—C184 | 56.4 (10) |
C123—C122—C161—C166 | −53.7 (10) | C182—C183—C184—C185 | −57.3 (10) |
C121—C122—C161—C162 | −106.0 (8) | C183—C184—C185—C186 | 57.5 (10) |
C123—C122—C161—C162 | 68.8 (9) | C152—C181—C186—C185 | 178.7 (7) |
C122—C161—C162—C163 | 174.2 (7) | C182—C181—C186—C185 | 55.0 (9) |
C166—C161—C162—C163 | −59.9 (9) | C184—C185—C186—C181 | −57.3 (10) |
C161—C162—C163—C164 | 54.9 (9) | C159—C158—C191—C196 | −136.9 (8) |
C162—C163—C164—C165 | −50.8 (10) | C157—C158—C191—C196 | 48.0 (11) |
C163—C164—C165—C166 | 51.6 (10) | C159—C158—C191—C192 | 100.5 (9) |
C122—C161—C166—C165 | −174.7 (7) | C157—C158—C191—C192 | −74.5 (10) |
C162—C161—C166—C165 | 61.6 (9) | C158—C191—C192—C193 | −179.2 (9) |
C164—C165—C166—C161 | −57.7 (10) | C196—C191—C192—C193 | 54.5 (12) |
C129—C128—C171—C172 | 26.9 (11) | C191—C192—C193—C194 | −55.7 (15) |
C127—C128—C171—C172 | −154.8 (7) | C192—C193—C194—C195 | 55.3 (14) |
C129—C128—C171—C176 | −97.7 (9) | C193—C194—C195—C196 | −55.6 (12) |
C127—C128—C171—C176 | 80.6 (9) | C194—C195—C196—C191 | 56.4 (11) |
C128—C171—C172—C173 | 178.1 (7) | C158—C191—C196—C195 | −177.2 (8) |
C176—C171—C172—C173 | −56.7 (9) | C192—C191—C196—C195 | −54.3 (11) |
C171—C172—C173—C174 | 57.3 (10) | N12—C13—C16—C17 | −177.9 (7) |
C172—C173—C174—C175 | −56.1 (10) | C14—C13—C16—C17 | −59.4 (9) |
C173—C174—C175—C176 | 54.9 (10) | C13—C16—C17—C18 | 52.6 (10) |
C128—C171—C176—C175 | −177.5 (7) | C16—C17—C18—C19 | −52.6 (10) |
C172—C171—C176—C175 | 55.2 (10) | N15—C14—C19—C18 | −178.1 (7) |
C174—C175—C176—C171 | −54.8 (11) | C13—C14—C19—C18 | −60.9 (9) |
C11—N12—C13—C14 | 29.7 (8) | C17—C18—C19—C14 | 53.5 (9) |
C121—N12—C13—C14 | −160.3 (7) |
Acknowledgements
We are thankful to Reto Dorta for guidance and advice in the synthesis of these unique NHC salts and their corresponding complexes.
Funding information
Funding for this research was provided by: The University of Western Australia (scholarship to Daven J. Foster).
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