research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 76| Part 10| October 2020| Pages 1543-1547
https://doi.org/10.1107/S2056989020011603

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

CROSSMARK_Color_square_no_text.svg
Stephen A. Moggach,a Brian W. Skeltona and Daven J. Fosterb*

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: [email protected]

Edited by H. Ishida, Okayama University, Japan (Received 3 July 2020; accepted 25 August 2020; online 4 September 2020)

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 chirality, which could be separated via column chromatography, 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 asymmetric unit, while compound (II) crystallizes in the ortho­rhom­bic system (P212121) with one complex in the asymmetric unit. 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[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]). J. Appl. Cryst. 42, 339–341]. The solvent contribution is not included in the reported chemical formula and other crystal data.

CCDC references: 1963571; 2025278

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1. Chemical context

The use of N-heterocyclic carbenes (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[Lee, S. & Hartwig, J. F. (2001). J. Org. Chem. 66, 3402-3415.]; Arao et al., 2006[Arao, T., Sato, K., Kondo, K. & Aoyama, T. (2006). Chem. Pharm. Bull. 54, 1576-1581.]; Luan et al., 2008[Luan, X., Mariz, R., Robert, C., Gatti, M., Blumentritt, S., Linden, A. & Dorta, R. (2008). Org. Lett. 10, 5569-5572.]; Lai et al., 2009[Laï, R., Daran, J.-C., Heumann, A., Zaragori-Benedetti, A. & Rafii, E. (2009). Inorg. Chim. Acta, 362, 4849-4852.]). Using bulky naphthyl wingtips for the NHCs, axial chirality 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 column chromatography as previously reported for similar Ir–NHC complexes (Gao et al., 2020[Gao, P., Foster, D., Sipos, G., Skelton, B., Sobolev, A. & Dorta, R. (2020). Organometallics, 39, 556-573.]). 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[link]).

[Scheme 1]
[Figure 1]
Figure 1
Reaction scheme for the synthesis of the title compounds.

2. Structural commentary

The mol­ecular structures of the title compounds, (I)[link] and (II)[link], are depicted in Figs. 2[link] and 3[link], 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)[link] crystallizes in the monoclinic system (P21) with two independent complexes and two half-occupied DCM mol­ecules in the asymmetric unit; the solvent DCM mol­ecules were masked in the refinement due to high disordering. Compound (II)[link] crystallizes in the ortho­rhom­bic system (P212121) with one complex in the asymmetric unit.

[Figure 2]
Figure 2
The mol­ecular structures of the title complex (I)[link] with atom labelling. Labelling of selected aliphatic carbons has been omitted for clarity. Ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
[Figure 3]
Figure 3
The mol­ecular structures of the title complex (II)[link] with atom labelling. Labelling of selected aliphatic carbons has been omitted for clarity. Ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

The overall geometry of the complexes is square planar. The cyclo­hexyl rings in the fused N-heterocyclic ring systems of (I)[link] and (II)[link] 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)[link] and −31.5 (7)° for (II)[link]. The Ir—Ccarbene bond lengths are 2.046 (6) and 2.021 (6) Å for (I)[link] and 2.045 (8) Å for (II)[link]. 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[Kelly, R. A. III, Clavier, H., Giudice, S., Scott, N. M., Stevens, E. D., Bordner, J., Samardjiev, I., Hoff, C. D., Cavallo, L. & Nolan, S. P. (2008). Organometallics, 27, 202-210.]), 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[Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L. & Dorta, R. (2016). Chem. Eur. J. 22, 6939-6946.]), 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[Gao, P., Foster, D., Sipos, G., Skelton, B., Sobolev, A. & Dorta, R. (2020). Organometallics, 39, 556-573.]). 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[Ou, A., Wu, L., Salvador, A., Sipos, G., Zhao, G., Skelton, B. W., Sobolev, A. N. & Dorta, R. (2017). Dalton Trans. 46, 3631-3641.]), 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[Gao, P., Foster, D., Sipos, G., Skelton, B., Sobolev, A. & Dorta, R. (2020). Organometallics, 39, 556-573.]]. 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)[link], the complex mol­ecules are stacked in a column along the b axis via weak C—H⋯Cl inter­actions (Table 1[link] and Fig. 4[link]). In comparison, (II)[link] has no obvious inter­actions between mol­ecules.

Table 1
Hydrogen-bond geometry (Å, °) for (I)[link]

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.
[Figure 4]
Figure 4
Mol­ecular packing in the crystal of (I)[link] with C—H⋯Cl inter­actions highlighted in orange.

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[Laï, R., Daran, J.-C., Heumann, A., Zaragori-Benedetti, A. & Rafii, E. (2009). Inorg. Chim. Acta, 362, 4849-4852.]). 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[Lee, H. M., Jiang, T., Stevens, E. D. & Nolan, S. P. (2001). Organometallics, 20, 1255-1258.]), (SIMes)Ir(COD)Cl (QIWPAO), (SIPr)Ir(COD)Cl (QIWPIW) (Kelly et al., 2008[Kelly, R. A. III, Clavier, H., Giudice, S., Scott, N. M., Stevens, E. D., Bordner, J., Samardjiev, I., Hoff, C. D., Cavallo, L. & Nolan, S. P. (2008). Organometallics, 27, 202-210.]), [K](OCO)Ir(COD) [OCO = 1,3-di(2-hy­droxy-5-tert-butyl­phen­yl)imidazolyl; USOZIM; Weinberg et al., 2010[Weinberg, D. R., Hazari, N., Labinger, J. A. & Bercaw, J. E. (2010). Organometallics, 29, 89-100.]], 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[Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L. & Dorta, R. (2016). Chem. Eur. J. 22, 6939-6946.]), (2-SIMorNap)Ir(COD)Cl (XARZUO; Ou et al. 2017[Ou, A., Wu, L., Salvador, A., Sipos, G., Zhao, G., Skelton, B. W., Sobolev, A. N. & Dorta, R. (2017). Dalton Trans. 46, 3631-3641.]) and (anti-2-SICyOctNap)Ir(COD)Cl (POWGAM; Gao et al., 2020[Gao, P., Foster, D., Sipos, G., Skelton, B., Sobolev, A. & Dorta, R. (2020). Organometallics, 39, 556-573.]). 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[Gao, P., Foster, D., Sipos, G., Skelton, B., Sobolev, A. & Dorta, R. (2020). Organometallics, 39, 556-573.]).

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 diastereoisomers were separated via column chromatography (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)[link], 40 mg (11%) for (II)[link] 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)[link] and (II)[link].

(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 refinement details are summarized in Table 2[link]. For (I)[link] the solvent mol­ecule was masked using the smtbx masking tool in OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) 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).

Table 2
Experimental details

  (I) (II)
Crystal data
Chemical formula [Ir(C51H64N2)Cl(C8H12)] [Ir(C51H64N2)Cl(C8H12)]
Mr 1040.86 1040.86
Crystal system, space group Monoclinic, P21 Orthorhombic, P212121
Temperature (K) 102 100
a, b, c (Å) 19.0004 (2), 10.4520 (1), 28.7168 (4) 16.1663 (4), 17.2811 (4), 17.6110 (3)
α, β, γ (°) 90, 107.513 (1), 90 90, 90, 90
V (Å3) 5438.59 (11) 4920.01 (19)
Z 4 4
Radiation type Mo Kα Cu Kα
μ (mm−1) 2.54 6.04
Crystal size (mm) 0.41 × 0.20 × 0.10 0.25 × 0.03 × 0.02
 
Data collection
Diffractometer Oxford Diffraction Xcalibur, Ruby, Gemini ultra Oxford Diffraction Gemini
Absorption correction Multi-scan CrysAlis PRO (Rigaku OD, 2019[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]) Analytical CrysAlis PRO (Rigaku OD, 2019[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.808, 1.000 0.50, 0.90
No. of measured, independent and observed [I > 2σ(I)] reflections 349557, 38134, 32830 26296, 8782, 8164
Rint 0.069 0.056
(sin θ/λ)max (Å−1) 0.762 0.600
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.083, 1.04 0.039, 0.098, 1.04
No. of reflections 38134 8782
No. of parameters 1026 568
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.57, −0.90 2.41, −0.91
Absolute structure Flack x determined using 13600 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]) Flack x determined using 3426 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.074 (4) −0.046 (7)
Computer programs: CrysAlis PRO (Rigaku OD, 2019[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), OLEX2.solve (Bourhis et al., 2015[Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59-75.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 and SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC references: 1963571; 2025278

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S2056989020011603/is5546sup1.cif

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

checkCIF report


Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: 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).

[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 (I) top
Crystal data top
[Ir(C51H64N2)Cl(C8H12)]F(000) = 2152
Mr = 1040.86Dx = 1.271 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 19.0004 (2) ÅCell parameters from 82075 reflections
b = 10.4520 (1) Åθ = 3.3–31.6°
c = 28.7168 (4) ŵ = 2.54 mm−1
β = 107.513 (1)°T = 102 K
V = 5438.59 (11) Å3Block, clear light yellow
Z = 40.41 × 0.20 × 0.10 mm
Data collection top
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
diffractometer		38134 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source32830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 10.4738 pixels mm-1θmax = 32.8°, θmin = 3.2°
ω scansh = −28→27
Absorption correction: multi-scan
CrysAlisPro (Rigaku OD, 2019)		k = −15→15
Tmin = 0.808, Tmax = 1.000l = −43→43
349557 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 1.57 e Å−3
38134 reflectionsΔρmin = −0.90 e Å−3
1026 parametersAbsolute structure: Flack x determined using 13600 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.074 (4)
Primary atom site location: iterative
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir20.24765 (2)0.56306 (2)0.18270 (2)0.01703 (5)
Cl20.34192 (8)0.47528 (14)0.24718 (5)0.0213 (3)
N2120.2086 (2)0.7846 (5)0.24086 (18)0.0157 (9)
N2150.3131 (2)0.8131 (5)0.22408 (18)0.0171 (9)
C2110.2562 (3)0.7306 (6)0.21910 (19)0.0148 (10)
C2130.2441 (3)0.8964 (5)0.2698 (2)0.0174 (9)
H2130.2760270.8641940.3020750.021*
C2140.2935 (3)0.9375 (7)0.2411 (2)0.0197 (10)
H2140.2624070.9844380.2117720.024*
C2160.1974 (3)1.0048 (6)0.2798 (2)0.0237 (12)
H21A0.1653610.9736540.2989410.028*
H21B0.1657541.0415410.2487340.028*
C2170.2519 (3)1.1053 (5)0.3088 (2)0.0245 (12)
H21C0.2778731.0705090.3414990.029*
H21D0.2240961.1820190.3133170.029*
C2180.3092 (3)1.1449 (6)0.2835 (2)0.0213 (12)
H21E0.2837551.1916010.2530620.026*
H21F0.3449641.2043360.3050860.026*
C2190.3513 (3)1.0317 (5)0.2709 (2)0.0213 (10)
H21G0.3835031.0611160.2515820.026*
H21H0.3824320.9903580.3010720.026*
C3010.2809 (3)0.4337 (7)0.1343 (2)0.0326 (5)
H3010.3317880.3989330.1489960.039*
C3020.2287 (4)0.3690 (7)0.1491 (2)0.0326 (5)
H3020.2480500.2965660.1721210.039*
C3030.1382 (4)0.5878 (7)0.1378 (2)0.0326 (5)
H3030.1095620.6508360.1510560.039*
C3040.1855 (4)0.6441 (8)0.1157 (3)0.0326 (5)
H3040.1842280.7397470.1157610.039*
C3050.2073 (4)0.5859 (7)0.0722 (2)0.0326 (5)
H30A0.1645640.5373220.0514540.039*
H30B0.2172290.6568110.0522200.039*
C3060.2714 (4)0.5013 (6)0.0855 (2)0.0326 (5)
H30C0.3162950.5518690.0876110.039*
H30D0.2659000.4362240.0595810.039*
C3070.1493 (3)0.3533 (6)0.1165 (2)0.0326 (5)
H30E0.1295840.2711350.1243650.039*
H30F0.1489940.3494150.0819720.039*
C3080.0981 (4)0.4625 (8)0.1222 (3)0.0326 (5)
H30G0.0591730.4754080.0906990.039*
H30H0.0735410.4371280.1467140.039*
C3200.0765 (3)0.7522 (6)0.2270 (2)0.0185 (11)
C3210.1508 (3)0.7195 (6)0.2540 (2)0.0171 (11)
C3220.1659 (3)0.6387 (6)0.2938 (2)0.0182 (11)
C3230.1056 (3)0.5879 (6)0.3077 (2)0.0218 (11)
H3230.1154140.5330100.3352260.026*
C3240.0339 (4)0.6161 (6)0.2823 (3)0.0257 (13)
H324−0.0051020.5801030.2923450.031*
C3250.0175 (3)0.6978 (6)0.2416 (2)0.0212 (12)
C326−0.0562 (3)0.7260 (6)0.2137 (3)0.0252 (13)
H326−0.0959440.6902310.2230210.030*
C327−0.0704 (3)0.8017 (6)0.1748 (3)0.0252 (13)
H327−0.1202500.8187010.1567670.030*
C328−0.0130 (3)0.8581 (6)0.1594 (2)0.0214 (12)
C3290.0584 (3)0.8335 (6)0.1857 (2)0.0221 (12)
H3290.0970670.8720560.1760200.026*
C331−0.0335 (3)0.9401 (8)0.1143 (2)0.0276 (12)
H331−0.0879820.9317820.0987490.033*
C332−0.0168 (6)1.0809 (11)0.1260 (4)0.0668 (14)
H33A0.0366571.0925620.1423580.080*
H33B−0.0440191.1115340.1483090.080*
C333−0.0413 (6)1.1610 (12)0.0762 (4)0.0668 (14)
H33C−0.0957921.1597540.0628720.080*
H33D−0.0256591.2511650.0832200.080*
C334−0.0095 (6)1.1103 (11)0.0396 (4)0.0668 (14)
H33E−0.0294821.1583490.0087550.080*
H33F0.0446611.1228480.0509620.080*
C335−0.0256 (6)0.9748 (11)0.0306 (4)0.0668 (14)
H33G−0.0032910.9440260.0056200.080*
H33H−0.0797010.9625070.0176570.080*
C3360.0043 (6)0.8972 (11)0.0769 (4)0.0668 (14)
H33I0.0582960.9100380.0903090.080*
H33J−0.0050860.8050910.0697020.080*
C3370.2434 (3)0.6096 (6)0.3265 (2)0.0194 (12)
H3370.2792480.6407930.3097450.023*
C3380.2581 (3)0.6820 (7)0.3750 (2)0.0243 (13)
H33K0.2516860.7749330.3683870.029*
H33L0.2218950.6548750.3916010.029*
C3390.3360 (4)0.6565 (7)0.4083 (3)0.0291 (15)
H33M0.3719700.6935010.3932220.035*
H33N0.3426340.7003270.4398570.035*
C3400.3523 (4)0.5174 (8)0.4175 (3)0.0336 (17)
H34A0.3217120.4829300.4371010.040*
H34B0.4047780.5065540.4366590.040*
C3410.3365 (3)0.4414 (9)0.3696 (2)0.0261 (11)
H34C0.3430040.3488730.3770630.031*
H34D0.3721050.4667280.3522480.031*
C3420.2565 (3)0.4666 (6)0.3363 (2)0.0223 (13)
H34E0.2484310.4207900.3049340.027*
H34F0.2208300.4331520.3522640.027*
C3500.3637 (3)0.8268 (6)0.1541 (2)0.0176 (11)
C3510.3742 (3)0.7975 (5)0.2046 (2)0.0150 (10)
C3520.4427 (3)0.7559 (6)0.2348 (2)0.0173 (11)
C3530.4986 (3)0.7294 (6)0.2127 (2)0.0212 (12)
H3530.5450760.6993860.2326180.025*
C3540.4880 (3)0.7452 (6)0.1640 (2)0.0214 (12)
H3540.5258250.7214790.1502920.026*
C3550.4218 (3)0.7964 (7)0.1339 (2)0.0212 (12)
C3560.4110 (4)0.8240 (8)0.0834 (2)0.0275 (14)
H3560.4476710.7997240.0688170.033*
C3570.3493 (4)0.8843 (7)0.0563 (2)0.0306 (15)
H3570.3447950.9052940.0233130.037*
C3580.2913 (3)0.9169 (7)0.0754 (2)0.0240 (14)
C3590.2997 (3)0.8877 (6)0.1238 (2)0.0201 (11)
H3590.2611520.9092790.1371340.024*
C3610.2239 (4)0.9894 (8)0.0436 (3)0.0315 (16)
H3610.1868860.9956060.0619590.038*
C3620.2448 (4)1.1234 (8)0.0332 (3)0.0377 (17)
H36A0.2856221.1187230.0184110.045*
H36B0.2630951.1707960.0643460.045*
C3630.1799 (6)1.1978 (9)−0.0015 (3)0.047 (2)
H36C0.1967481.283784−0.0079090.056*
H36D0.1402371.2086070.0139940.056*
C3640.1497 (5)1.1238 (9)−0.0502 (3)0.045 (2)
H36E0.1070511.170183−0.0720580.054*
H36F0.1884421.117692−0.0667120.054*
C3650.1258 (4)0.9889 (8)−0.0399 (3)0.0357 (16)
H36G0.0838240.995367−0.0263430.043*
H36H0.1090410.940228−0.0708840.043*
C3660.1880 (4)0.9188 (9)−0.0046 (3)0.0348 (18)
H36I0.2263880.901344−0.0206520.042*
H36J0.1693180.8353220.0028940.042*
C3670.4631 (3)0.7462 (6)0.2898 (2)0.0185 (11)
H3670.4169570.7522500.2996000.022*
C3680.5148 (3)0.8574 (5)0.3138 (2)0.0211 (11)
H36K0.5614800.8500790.3053860.025*
H36L0.4913120.9396320.3006370.025*
C3690.5319 (3)0.8575 (6)0.3689 (2)0.0273 (12)
H36M0.5649080.9301450.3829450.033*
H36N0.4856690.8681680.3776280.033*
C3700.5687 (4)0.7335 (7)0.3898 (2)0.0282 (13)
H37A0.5761800.7322140.4253890.034*
H37B0.6178010.7288050.3845390.034*
C3710.5236 (4)0.6172 (7)0.3666 (2)0.0272 (14)
H37C0.4777870.6141270.3762750.033*
H37D0.5522310.5385700.3789360.033*
C3720.5036 (3)0.6210 (6)0.3107 (2)0.0222 (12)
H37E0.4715820.5470560.2967260.027*
H37F0.5491410.6137330.3009140.027*
Ir10.75763 (2)0.442289 (6)0.31455 (2)0.01599 (5)
Cl10.65873 (8)0.51820 (14)0.25058 (5)0.0196 (3)
N120.6958 (2)0.1776 (4)0.28132 (17)0.0137 (8)
N150.7916 (2)0.2176 (5)0.25652 (18)0.0160 (9)
C110.7485 (3)0.2672 (5)0.2814 (2)0.0152 (10)
C130.6977 (3)0.0714 (6)0.24819 (19)0.0165 (9)
H130.6667070.0967890.2147340.020*
C140.7777 (3)0.0774 (5)0.24884 (19)0.0178 (9)
H140.8080400.0320340.2788320.021*
C160.6759 (3)−0.0611 (5)0.25724 (18)0.0194 (9)
H16A0.623923−0.0632860.2574380.023*
H16B0.707814−0.0934630.2889720.023*
C170.6861 (3)−0.1428 (6)0.2143 (2)0.0200 (12)
H17A0.676466−0.2338180.2197900.024*
H17B0.649442−0.1154340.1834550.024*
C180.7640 (3)−0.1302 (5)0.2091 (2)0.0232 (12)
H18A0.765699−0.1772270.1795350.028*
H18B0.799635−0.1713210.2376260.028*
C190.7884 (3)0.0101 (6)0.2054 (2)0.0239 (13)
H19A0.8408500.0134830.2061780.029*
H19B0.7578750.0500610.1747210.029*
C1010.7843 (3)0.6404 (6)0.3353 (2)0.0279 (4)
H1010.7576920.7025510.3095090.033*
C1020.7402 (3)0.5923 (5)0.3623 (2)0.0279 (4)
H1020.6889580.6275730.3530750.033*
C1030.8192 (4)0.3609 (7)0.3818 (2)0.0279 (4)
H1030.8213750.2653740.3812980.033*
C1040.8667 (4)0.4199 (6)0.3602 (2)0.0279 (4)
H1040.8961290.3579330.3470710.033*
C1050.9076 (3)0.5452 (7)0.3779 (2)0.0279 (4)
H10A0.9159950.5534410.4134840.033*
H10B0.9565110.5420380.3722460.033*
C1060.8665 (3)0.6616 (5)0.3527 (2)0.0279 (4)
H10C0.8777600.7349340.3755710.033*
H10D0.8837920.6835450.3243980.033*
C1070.7722 (3)0.5569 (6)0.4158 (2)0.0279 (4)
H10E0.7348740.5742460.4326900.033*
H10F0.8154620.6121490.4307220.033*
C1080.7964 (4)0.4145 (6)0.4240 (2)0.0279 (4)
H10G0.8383360.4073690.4543380.033*
H10H0.7550820.3631250.4283410.033*
C1200.6444 (3)0.1727 (6)0.3502 (2)0.0166 (10)
C1210.6343 (3)0.2016 (6)0.2999 (2)0.0158 (10)
C1220.5662 (3)0.2416 (5)0.2694 (2)0.0164 (10)
C1230.5090 (3)0.2659 (6)0.2904 (2)0.0195 (11)
H1230.4618110.2910320.2698610.023*
C1240.5198 (3)0.2541 (6)0.3394 (2)0.0213 (12)
H1240.4817660.2788620.3527350.026*
C1250.5871 (3)0.2053 (6)0.3706 (2)0.0181 (11)
C1260.5963 (4)0.1806 (7)0.4203 (2)0.0251 (13)
H1260.5581980.2036170.4338440.030*
C1270.6585 (3)0.1246 (6)0.4493 (2)0.0231 (12)
H1270.6644350.1124520.4830340.028*
C1280.7152 (3)0.0840 (6)0.4294 (2)0.0204 (12)
C1290.7081 (3)0.1103 (6)0.3814 (2)0.0184 (11)
H1290.7466410.0861520.3684460.022*
C1310.7810 (3)0.0144 (6)0.4618 (2)0.0202 (12)
H1310.8184820.0073010.4438120.024*
C1320.8168 (4)0.0867 (7)0.5096 (2)0.0253 (14)
H13A0.7782910.1089870.5250290.030*
H13B0.8384180.1675090.5021920.030*
C1330.8781 (4)0.0075 (8)0.5463 (3)0.0317 (15)
H13C0.920313−0.0031240.5332090.038*
H13D0.8957550.0547030.5775710.038*
C1340.8511 (4)−0.1199 (7)0.5554 (3)0.0303 (15)
H13E0.811455−0.1094000.5709180.036*
H13F0.891970−0.1679860.5783140.036*
C1350.8220 (4)−0.1948 (8)0.5090 (3)0.0309 (16)
H13G0.804220−0.2791330.5163110.037*
H13H0.862370−0.2095030.4943570.037*
C1360.7595 (4)−0.1240 (7)0.4728 (2)0.0249 (13)
H13I0.716941−0.1193820.4858690.030*
H13J0.743763−0.1730300.4418670.030*
C1370.5481 (3)0.2554 (6)0.2145 (2)0.0181 (10)
H1370.5954090.2681880.2066120.022*
C1380.4966 (3)0.3689 (6)0.1929 (2)0.0217 (12)
H13K0.4488620.3569750.1996910.026*
H13L0.5190680.4492190.2088730.026*
C1390.4831 (4)0.3792 (7)0.1384 (3)0.0271 (13)
H13M0.5303980.3979250.1319480.033*
H13N0.4490660.4513400.1255550.033*
C1400.4501 (4)0.2559 (7)0.1116 (3)0.0343 (15)
H14A0.3996380.2433850.1140570.041*
H14B0.4464700.2635550.0766140.041*
C1410.4977 (4)0.1405 (6)0.1335 (2)0.0300 (13)
H14C0.5456040.1470170.1266180.036*
H14D0.4728840.0613980.1179180.036*
C1420.5115 (3)0.1321 (5)0.1889 (2)0.0231 (11)
H14E0.5438820.0580230.2020820.028*
H14F0.4640540.1184370.1958020.028*
C1500.9256 (3)0.2418 (6)0.2704 (2)0.0157 (11)
C1510.8521 (3)0.2766 (6)0.2433 (2)0.0163 (11)
C1520.8374 (3)0.3537 (6)0.2028 (2)0.0177 (11)
C1530.8989 (3)0.3978 (6)0.1882 (2)0.0225 (12)
H1530.8896220.4511700.1601890.027*
C1540.9695 (3)0.3671 (6)0.2124 (2)0.0219 (12)
H1541.0084830.3982630.2011700.026*
C1550.9853 (3)0.2884 (6)0.2544 (2)0.0194 (11)
C1561.0585 (3)0.2584 (6)0.2821 (2)0.0219 (12)
H1561.0983460.2889360.2716540.026*
C1571.0729 (3)0.1853 (6)0.3241 (2)0.0201 (11)
H1571.1225630.1658200.3419970.024*
C1581.0152 (3)0.1396 (6)0.3407 (2)0.0177 (11)
C1590.9426 (3)0.1659 (6)0.3134 (2)0.0146 (10)
H1590.9034110.1321540.3237950.018*
C1611.0328 (3)0.0626 (8)0.3876 (2)0.0219 (11)
H1611.0871670.0704030.4036220.026*
C1620.9954 (4)0.1150 (6)0.4237 (2)0.0249 (11)
H16C0.9412260.1062650.4096870.030*
H16D1.0069040.2072430.4291200.030*
C1631.0206 (4)0.0449 (8)0.4727 (2)0.0358 (15)
H16E1.0740720.0587870.4881540.043*
H16F0.9939400.0790330.4947810.043*
C1641.0049 (4)−0.0978 (8)0.4644 (3)0.0399 (17)
H16G0.950892−0.1115940.4528520.048*
H16H1.024759−0.1435900.4958200.048*
C1651.0394 (4)−0.1538 (7)0.4270 (4)0.051 (2)
H16I1.023792−0.2441450.4205510.061*
H16J1.093797−0.1522710.4407710.061*
C1661.0165 (4)−0.0789 (6)0.3789 (3)0.0310 (13)
H16K1.043491−0.1125870.3569360.037*
H16L0.963020−0.0910470.3626490.037*
C1670.7610 (3)0.3886 (6)0.1711 (2)0.0180 (11)
H1670.7248840.3572100.1875640.022*
C1680.7433 (4)0.3232 (7)0.1212 (2)0.0250 (13)
H16M0.7797000.3507910.1047800.030*
H16N0.7481680.2294430.1260120.030*
C1690.6663 (4)0.3534 (8)0.0883 (3)0.0324 (16)
H16O0.6293690.3169700.1026920.039*
H16P0.6588920.3132540.0559920.039*
C1700.6546 (4)0.4982 (7)0.0821 (3)0.0287 (14)
H17C0.6860520.5322600.0629910.034*
H17D0.6024990.5155760.0634740.034*
C1710.6735 (3)0.5670 (8)0.1313 (2)0.0248 (11)
H17E0.6696170.6605170.1257140.030*
H17F0.6371460.5424390.1482410.030*
C1720.7499 (3)0.5351 (6)0.1634 (2)0.0236 (14)
H17G0.7585040.5772300.1955020.028*
H17H0.7865980.5688400.1483170.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir20.01774 (9)0.01498 (12)0.01705 (10)−0.00075 (8)0.00323 (8)−0.00294 (9)
Cl20.0221 (6)0.0206 (8)0.0192 (6)0.0038 (5)0.0034 (5)0.0006 (5)
N2120.016 (2)0.012 (2)0.020 (2)0.0001 (17)0.0070 (18)−0.0019 (18)
N2150.0160 (19)0.013 (2)0.025 (2)0.0010 (16)0.0098 (18)−0.0027 (17)
C2110.014 (2)0.020 (3)0.009 (2)0.0009 (19)0.0018 (18)0.002 (2)
C2130.017 (2)0.014 (2)0.024 (2)−0.0019 (17)0.0103 (19)−0.0039 (18)
C2140.018 (2)0.015 (2)0.028 (3)−0.002 (2)0.0114 (19)−0.004 (2)
C2160.020 (2)0.017 (3)0.039 (3)−0.003 (2)0.016 (2)−0.008 (2)
C2170.026 (3)0.014 (2)0.039 (3)−0.0016 (19)0.019 (3)−0.008 (2)
C2180.022 (3)0.016 (3)0.027 (3)−0.004 (2)0.009 (2)−0.007 (2)
C2190.020 (2)0.016 (2)0.030 (3)−0.0033 (17)0.011 (2)−0.0051 (19)
C3010.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3020.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3030.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3040.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3050.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3060.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3070.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3080.0349 (11)0.0321 (12)0.0269 (10)0.0001 (10)0.0032 (9)−0.0072 (9)
C3200.019 (2)0.017 (3)0.021 (3)0.002 (2)0.009 (2)−0.003 (2)
C3210.016 (2)0.016 (3)0.022 (3)−0.0013 (19)0.009 (2)−0.003 (2)
C3220.020 (2)0.015 (3)0.022 (3)0.000 (2)0.010 (2)−0.001 (2)
C3230.024 (2)0.017 (3)0.026 (3)0.000 (2)0.009 (2)0.001 (2)
C3240.026 (3)0.023 (3)0.036 (3)−0.007 (2)0.021 (3)−0.004 (2)
C3250.017 (2)0.022 (3)0.029 (3)−0.001 (2)0.013 (2)−0.006 (2)
C3260.016 (2)0.025 (3)0.038 (3)0.000 (2)0.012 (2)−0.002 (3)
C3270.016 (2)0.025 (3)0.036 (3)−0.001 (2)0.008 (2)−0.010 (3)
C3280.019 (3)0.018 (3)0.027 (3)0.001 (2)0.006 (2)−0.003 (2)
C3290.021 (3)0.016 (3)0.033 (3)0.000 (2)0.014 (3)−0.002 (3)
C3310.017 (2)0.025 (3)0.037 (3)−0.004 (3)0.003 (2)0.001 (4)
C3320.061 (3)0.068 (3)0.061 (3)−0.010 (2)0.003 (2)0.024 (2)
C3330.061 (3)0.068 (3)0.061 (3)−0.010 (2)0.003 (2)0.024 (2)
C3340.061 (3)0.068 (3)0.061 (3)−0.010 (2)0.003 (2)0.024 (2)
C3350.061 (3)0.068 (3)0.061 (3)−0.010 (2)0.003 (2)0.024 (2)
C3360.061 (3)0.068 (3)0.061 (3)−0.010 (2)0.003 (2)0.024 (2)
C3370.023 (3)0.018 (3)0.020 (3)−0.002 (2)0.010 (2)−0.001 (2)
C3380.026 (3)0.028 (3)0.022 (3)0.000 (2)0.010 (2)0.002 (3)
C3390.028 (3)0.035 (4)0.025 (3)−0.011 (3)0.009 (3)−0.006 (3)
C3400.028 (3)0.050 (5)0.022 (3)−0.001 (3)0.006 (3)0.002 (3)
C3410.026 (3)0.028 (3)0.023 (3)−0.001 (3)0.007 (2)−0.002 (3)
C3420.027 (3)0.020 (4)0.022 (3)−0.006 (2)0.010 (2)−0.002 (2)
C3500.020 (2)0.015 (3)0.020 (2)−0.004 (2)0.008 (2)−0.002 (2)
C3510.015 (2)0.012 (3)0.019 (2)−0.0049 (18)0.0077 (19)−0.0050 (19)
C3520.016 (2)0.013 (3)0.025 (3)0.0007 (18)0.010 (2)−0.002 (2)
C3530.019 (2)0.019 (3)0.030 (3)0.004 (2)0.013 (2)0.003 (2)
C3540.018 (2)0.022 (3)0.028 (3)−0.001 (2)0.012 (2)−0.008 (2)
C3550.021 (3)0.026 (3)0.019 (3)−0.007 (2)0.011 (2)−0.007 (2)
C3560.023 (3)0.041 (4)0.023 (3)−0.001 (3)0.013 (2)−0.004 (3)
C3570.032 (3)0.044 (4)0.019 (3)−0.011 (3)0.012 (2)−0.005 (3)
C3580.024 (3)0.030 (4)0.019 (3)−0.005 (2)0.008 (2)−0.001 (2)
C3590.019 (2)0.025 (3)0.018 (2)−0.004 (2)0.008 (2)−0.002 (2)
C3610.028 (3)0.044 (4)0.022 (3)−0.008 (3)0.006 (3)−0.004 (3)
C3620.039 (4)0.034 (4)0.030 (3)0.000 (3)−0.004 (3)−0.007 (3)
C3630.063 (5)0.027 (4)0.040 (4)0.000 (4)0.000 (4)−0.008 (3)
C3640.050 (5)0.044 (5)0.033 (4)0.010 (4)0.000 (4)0.006 (4)
C3650.036 (4)0.038 (4)0.028 (3)−0.008 (3)0.002 (3)−0.002 (3)
C3660.035 (3)0.040 (5)0.024 (3)−0.007 (3)0.000 (3)0.002 (3)
C3670.015 (2)0.021 (3)0.021 (3)−0.0001 (19)0.008 (2)0.000 (2)
C3680.021 (2)0.018 (3)0.027 (3)−0.001 (2)0.011 (2)−0.002 (2)
C3690.028 (3)0.027 (3)0.027 (3)−0.003 (2)0.008 (2)−0.008 (2)
C3700.033 (3)0.025 (3)0.026 (3)0.002 (2)0.008 (3)−0.001 (2)
C3710.023 (3)0.029 (4)0.024 (3)−0.002 (2)0.000 (2)0.002 (3)
C3720.023 (3)0.016 (3)0.027 (3)0.001 (2)0.006 (2)0.001 (2)
Ir10.01665 (9)0.01127 (10)0.01773 (10)−0.00002 (8)0.00169 (8)−0.00114 (9)
Cl10.0182 (6)0.0165 (7)0.0216 (6)0.0027 (5)0.0024 (5)0.0001 (5)
N120.0149 (18)0.009 (2)0.018 (2)0.0004 (15)0.0059 (16)0.0004 (16)
N150.0120 (19)0.015 (2)0.021 (2)−0.0045 (17)0.0054 (18)−0.0008 (19)
C110.014 (2)0.009 (2)0.021 (3)0.0026 (18)0.003 (2)0.003 (2)
C130.0161 (19)0.014 (2)0.020 (2)−0.0041 (19)0.0071 (17)−0.005 (2)
C140.0148 (19)0.014 (2)0.028 (2)0.0013 (18)0.0111 (18)−0.002 (2)
C160.019 (2)0.015 (2)0.026 (2)−0.0051 (19)0.0086 (18)−0.001 (2)
C170.022 (3)0.014 (3)0.028 (3)−0.004 (2)0.014 (2)−0.004 (2)
C180.024 (3)0.012 (2)0.040 (3)0.0004 (19)0.019 (2)−0.005 (2)
C190.026 (3)0.020 (3)0.032 (3)−0.004 (2)0.020 (3)−0.007 (2)
C1010.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1020.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1030.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1040.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1050.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1060.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1070.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1080.0309 (10)0.0198 (10)0.0278 (10)0.0019 (8)0.0009 (8)−0.0049 (8)
C1200.016 (2)0.015 (3)0.022 (3)−0.0012 (18)0.009 (2)−0.002 (2)
C1210.014 (2)0.014 (3)0.021 (2)0.0025 (18)0.0070 (19)0.001 (2)
C1220.018 (2)0.011 (2)0.020 (2)−0.0026 (18)0.006 (2)0.0008 (19)
C1230.015 (2)0.014 (3)0.030 (3)0.0000 (19)0.007 (2)−0.003 (2)
C1240.020 (3)0.018 (3)0.032 (3)0.002 (2)0.017 (2)0.001 (2)
C1250.017 (2)0.015 (3)0.024 (3)0.0005 (19)0.008 (2)−0.001 (2)
C1260.031 (3)0.024 (3)0.027 (3)−0.001 (2)0.018 (3)−0.004 (3)
C1270.023 (3)0.028 (3)0.020 (3)0.001 (2)0.008 (2)−0.002 (2)
C1280.022 (2)0.019 (3)0.020 (2)0.000 (2)0.006 (2)0.001 (2)
C1290.015 (2)0.016 (3)0.023 (3)−0.0028 (18)0.003 (2)−0.001 (2)
C1310.022 (3)0.021 (3)0.019 (3)0.003 (2)0.009 (2)0.003 (2)
C1320.032 (3)0.018 (4)0.023 (3)−0.005 (2)0.004 (2)−0.002 (2)
C1330.025 (3)0.043 (4)0.023 (3)0.006 (3)0.001 (2)0.009 (3)
C1340.032 (3)0.032 (4)0.028 (3)0.007 (3)0.011 (3)0.005 (3)
C1350.031 (3)0.029 (4)0.033 (4)0.010 (3)0.010 (3)0.009 (3)
C1360.028 (3)0.021 (3)0.026 (3)−0.001 (2)0.008 (2)0.004 (2)
C1370.018 (2)0.014 (3)0.022 (3)0.0007 (18)0.004 (2)−0.001 (2)
C1380.017 (2)0.022 (3)0.023 (3)0.001 (2)0.001 (2)−0.002 (2)
C1390.023 (3)0.024 (3)0.032 (3)0.002 (2)0.006 (3)0.004 (3)
C1400.035 (3)0.036 (4)0.026 (3)−0.001 (3)0.001 (3)−0.003 (3)
C1410.037 (3)0.024 (3)0.028 (3)−0.005 (3)0.008 (3)−0.005 (2)
C1420.022 (3)0.014 (3)0.031 (3)0.000 (2)0.004 (2)0.001 (2)
C1500.013 (2)0.013 (3)0.022 (3)−0.0020 (18)0.008 (2)−0.003 (2)
C1510.017 (2)0.012 (3)0.022 (3)−0.0062 (19)0.010 (2)−0.005 (2)
C1520.018 (2)0.016 (3)0.020 (3)−0.0024 (19)0.008 (2)−0.003 (2)
C1530.026 (3)0.024 (3)0.023 (3)−0.005 (2)0.014 (2)0.000 (2)
C1540.019 (2)0.027 (3)0.023 (3)−0.004 (2)0.012 (2)0.000 (2)
C1550.019 (2)0.019 (3)0.022 (3)−0.002 (2)0.009 (2)−0.002 (2)
C1560.015 (2)0.027 (3)0.028 (3)−0.002 (2)0.013 (2)−0.004 (2)
C1570.013 (2)0.019 (3)0.029 (3)0.0035 (19)0.009 (2)0.001 (2)
C1580.016 (2)0.014 (3)0.024 (3)0.002 (2)0.008 (2)−0.003 (2)
C1590.015 (2)0.013 (3)0.016 (2)−0.0013 (19)0.004 (2)0.001 (2)
C1610.013 (2)0.023 (3)0.027 (3)−0.002 (3)0.003 (2)0.011 (3)
C1620.029 (3)0.024 (3)0.019 (2)0.005 (2)0.004 (2)0.002 (2)
C1630.032 (3)0.046 (4)0.026 (3)−0.008 (3)0.003 (2)0.009 (3)
C1640.027 (3)0.050 (4)0.036 (3)−0.013 (3)−0.002 (3)0.017 (3)
C1650.033 (3)0.011 (3)0.091 (6)0.005 (2)−0.007 (4)0.013 (3)
C1660.036 (3)0.009 (3)0.043 (3)0.004 (2)0.005 (3)−0.001 (2)
C1670.017 (2)0.017 (3)0.019 (3)−0.003 (2)0.005 (2)0.003 (2)
C1680.031 (3)0.021 (3)0.023 (3)−0.008 (2)0.008 (3)−0.006 (2)
C1690.032 (3)0.040 (5)0.023 (3)−0.006 (3)0.005 (3)−0.004 (3)
C1700.027 (3)0.034 (4)0.019 (3)0.002 (3)−0.001 (2)0.006 (3)
C1710.024 (2)0.025 (3)0.023 (3)0.004 (3)0.005 (2)0.006 (3)
C1720.025 (3)0.023 (4)0.021 (3)0.000 (2)0.004 (2)0.004 (2)
Geometric parameters (Å, º) top
Ir2—Cl22.3415 (15)Ir1—Cl12.3361 (15)
Ir2—C2112.021 (6)Ir1—C112.046 (6)
Ir2—C3012.165 (6)Ir1—C1012.172 (6)
Ir2—C3022.228 (6)Ir1—C1022.173 (6)
Ir2—C3032.106 (7)Ir1—C1032.112 (7)
Ir2—C3042.109 (7)Ir1—C1042.106 (6)
N212—C2111.367 (6)N12—C111.371 (7)
N212—C2131.475 (7)N12—C131.469 (7)
N212—C3211.434 (7)N12—C1211.447 (6)
N215—C2111.357 (7)N15—C111.342 (7)
N215—C2141.476 (8)N15—C141.494 (7)
N215—C3511.439 (6)N15—C1511.452 (6)
C213—H2131.0000C13—H131.0000
C213—C2141.487 (7)C13—C141.516 (6)
C213—C2161.519 (7)C13—C161.490 (8)
C214—H2141.0000C14—H141.0000
C214—C2191.530 (8)C14—C191.498 (7)
C216—H21A0.9900C16—H16A0.9900
C216—H21B0.9900C16—H16B0.9900
C216—C2171.534 (8)C16—C171.560 (7)
C217—H21C0.9900C17—H17A0.9900
C217—H21D0.9900C17—H17B0.9900
C217—C2181.536 (7)C17—C181.537 (7)
C218—H21E0.9900C18—H18A0.9900
C218—H21F0.9900C18—H18B0.9900
C218—C2191.531 (7)C18—C191.552 (8)
C219—H21G0.9900C19—H19A0.9900
C219—H21H0.9900C19—H19B0.9900
C301—H3011.0000C101—H1011.0000
C301—C3021.369 (9)C101—C1021.394 (9)
C301—C3061.530 (9)C101—C1061.507 (8)
C302—H3021.0000C102—H1021.0000
C302—C3071.527 (8)C102—C1071.518 (8)
C303—H3031.0000C103—H1031.0000
C303—C3041.379 (10)C103—C1041.384 (9)
C303—C3081.514 (10)C103—C1081.513 (9)
C304—H3041.0000C104—H1041.0000
C304—C3051.553 (9)C104—C1051.530 (9)
C305—H30A0.9900C105—H10A0.9900
C305—H30B0.9900C105—H10B0.9900
C305—C3061.460 (9)C105—C1061.508 (9)
C306—H30C0.9900C106—H10C0.9900
C306—H30D0.9900C106—H10D0.9900
C307—H30E0.9900C107—H10E0.9900
C307—H30F0.9900C107—H10F0.9900
C307—C3081.541 (9)C107—C1081.554 (9)
C308—H30G0.9900C108—H10G0.9900
C308—H30H0.9900C108—H10H0.9900
C320—C3211.433 (8)C120—C1211.430 (8)
C320—C3251.429 (7)C120—C1251.423 (7)
C320—C3291.413 (9)C120—C1291.428 (8)
C321—C3221.380 (8)C121—C1221.390 (8)
C322—C3231.424 (7)C122—C1231.416 (7)
C322—C3371.519 (9)C122—C1371.516 (8)
C323—H3230.9500C123—H1230.9500
C323—C3241.370 (9)C123—C1241.364 (9)
C324—H3240.9500C124—H1240.9500
C324—C3251.405 (9)C124—C1251.416 (9)
C325—C3261.418 (9)C125—C1261.410 (8)
C326—H3260.9500C126—H1260.9500
C326—C3271.330 (10)C126—C1271.356 (9)
C327—H3270.9500C127—H1270.9500
C327—C3281.422 (8)C127—C1281.428 (8)
C328—C3291.363 (9)C128—C1291.372 (8)
C328—C3311.503 (10)C128—C1311.502 (9)
C329—H3290.9500C129—H1290.9500
C331—H3311.0000C131—H1311.0000
C331—C3321.521 (15)C131—C1321.537 (9)
C331—C3361.528 (13)C131—C1361.562 (9)
C332—H33A0.9900C132—H13A0.9900
C332—H33B0.9900C132—H13B0.9900
C332—C3331.601 (13)C132—C1331.553 (10)
C333—H33C0.9900C133—H13C0.9900
C333—H33D0.9900C133—H13D0.9900
C333—C3341.460 (16)C133—C1341.478 (11)
C334—H33E0.9900C134—H13E0.9900
C334—H33F0.9900C134—H13F0.9900
C334—C3351.456 (15)C134—C1351.501 (11)
C335—H33G0.9900C135—H13G0.9900
C335—H33H0.9900C135—H13H0.9900
C335—C3361.516 (14)C135—C1361.515 (10)
C336—H33I0.9900C136—H13I0.9900
C336—H33J0.9900C136—H13J0.9900
C337—H3371.0000C137—H1371.0000
C337—C3381.535 (9)C137—C1381.544 (8)
C337—C3421.527 (9)C137—C1421.541 (8)
C338—H33K0.9900C138—H13K0.9900
C338—H33L0.9900C138—H13L0.9900
C338—C3391.525 (10)C138—C1391.512 (9)
C339—H33M0.9900C139—H13M0.9900
C339—H33N0.9900C139—H13N0.9900
C339—C3401.493 (11)C139—C1401.536 (10)
C340—H34A0.9900C140—H14A0.9900
C340—H34B0.9900C140—H14B0.9900
C340—C3411.538 (10)C140—C1411.525 (10)
C341—H34C0.9900C141—H14C0.9900
C341—H34D0.9900C141—H14D0.9900
C341—C3421.555 (9)C141—C1421.536 (9)
C342—H34E0.9900C142—H14E0.9900
C342—H34F0.9900C142—H14F0.9900
C350—C3511.437 (8)C150—C1511.427 (8)
C350—C3551.429 (7)C150—C1551.431 (7)
C350—C3591.415 (9)C150—C1591.419 (8)
C351—C3521.398 (8)C151—C1521.373 (8)
C352—C3531.418 (7)C152—C1531.431 (7)
C352—C3671.512 (8)C152—C1671.509 (8)
C353—H3530.9500C153—H1530.9500
C353—C3541.363 (9)C153—C1541.350 (9)
C354—H3540.9500C154—H1540.9500
C354—C3551.400 (9)C154—C1551.418 (9)
C355—C3561.432 (9)C155—C1561.413 (8)
C356—H3560.9500C156—H1560.9500
C356—C3571.353 (10)C156—C1571.385 (9)
C357—H3570.9500C157—H1570.9500
C357—C3581.412 (8)C157—C1581.404 (7)
C358—C3591.385 (8)C158—C1591.394 (8)
C358—C3611.531 (10)C158—C1611.517 (8)
C359—H3590.9500C159—H1590.9500
C361—H3611.0000C161—H1611.0000
C361—C3621.510 (11)C161—C1621.525 (8)
C361—C3661.537 (10)C161—C1661.517 (10)
C362—H36A0.9900C162—H16C0.9900
C362—H36B0.9900C162—H16D0.9900
C362—C3631.542 (12)C162—C1631.528 (9)
C363—H36C0.9900C163—H16E0.9900
C363—H36D0.9900C163—H16F0.9900
C363—C3641.550 (12)C163—C1641.526 (11)
C364—H36E0.9900C164—H16G0.9900
C364—H36F0.9900C164—H16H0.9900
C364—C3651.537 (12)C164—C1651.531 (13)
C365—H36G0.9900C165—H16I0.9900
C365—H36H0.9900C165—H16J0.9900
C365—C3661.496 (11)C165—C1661.533 (11)
C366—H36I0.9900C166—H16K0.9900
C366—H36J0.9900C166—H16L0.9900
C367—H3671.0000C167—H1671.0000
C367—C3681.545 (8)C167—C1681.531 (8)
C367—C3721.545 (9)C167—C1721.551 (9)
C368—H36K0.9900C168—H16M0.9900
C368—H36L0.9900C168—H16N0.9900
C368—C3691.516 (8)C168—C1691.516 (10)
C369—H36M0.9900C169—H16O0.9900
C369—H36N0.9900C169—H16P0.9900
C369—C3701.508 (9)C169—C1701.533 (11)
C370—H37A0.9900C170—H17C0.9900
C370—H37B0.9900C170—H17D0.9900
C370—C3711.520 (10)C170—C1711.530 (10)
C371—H37C0.9900C171—H17E0.9900
C371—H37D0.9900C171—H17F0.9900
C371—C3721.537 (9)C171—C1721.505 (8)
C372—H37E0.9900C172—H17G0.9900
C372—H37F0.9900C172—H17H0.9900
C211—Ir2—Cl290.41 (16)C11—Ir1—Cl190.15 (16)
C211—Ir2—C301151.6 (2)C11—Ir1—C101163.8 (2)
C211—Ir2—C302172.0 (2)C11—Ir1—C102158.7 (2)
C211—Ir2—C30397.0 (3)C11—Ir1—C10390.6 (2)
C211—Ir2—C30493.4 (3)C11—Ir1—C10496.9 (2)
C301—Ir2—Cl287.81 (17)C101—Ir1—Cl187.58 (16)
C301—Ir2—C30236.3 (2)C101—Ir1—C10237.4 (2)
C302—Ir2—Cl288.36 (17)C102—Ir1—Cl190.69 (16)
C303—Ir2—Cl2155.7 (2)C103—Ir1—Cl1161.60 (18)
C303—Ir2—C30196.2 (2)C103—Ir1—C10196.5 (3)
C303—Ir2—C30281.1 (3)C103—Ir1—C10282.0 (2)
C303—Ir2—C30438.2 (3)C104—Ir1—Cl1159.30 (18)
C304—Ir2—Cl2164.58 (19)C104—Ir1—C10180.3 (2)
C304—Ir2—C30181.7 (3)C104—Ir1—C10289.7 (2)
C304—Ir2—C30289.8 (3)C104—Ir1—C10338.3 (3)
C211—N212—C213109.3 (4)C11—N12—C13110.9 (4)
C211—N212—C321126.0 (5)C11—N12—C121123.6 (5)
C321—N212—C213119.0 (4)C121—N12—C13123.3 (4)
C211—N215—C214108.8 (4)C11—N15—C14110.4 (4)
C211—N215—C351126.6 (5)C11—N15—C151129.3 (5)
C351—N215—C214122.8 (4)C151—N15—C14119.8 (4)
N212—C211—Ir2129.3 (4)N12—C11—Ir1124.8 (4)
N215—C211—Ir2122.9 (4)N15—C11—Ir1127.9 (4)
N215—C211—N212107.8 (5)N15—C11—N12107.3 (5)
N212—C213—H213107.6N12—C13—H13107.4
N212—C213—C214100.0 (4)N12—C13—C14100.4 (4)
N212—C213—C216120.1 (4)N12—C13—C16121.8 (4)
C214—C213—H213107.6C14—C13—H13107.4
C214—C213—C216113.0 (5)C16—C13—H13107.4
C216—C213—H213107.6C16—C13—C14111.5 (5)
N215—C214—C213101.2 (5)N15—C14—C13100.1 (4)
N215—C214—H214107.3N15—C14—H14107.9
N215—C214—C219122.8 (4)N15—C14—C19121.4 (4)
C213—C214—H214107.3C13—C14—H14107.9
C213—C214—C219110.0 (4)C19—C14—C13111.0 (4)
C219—C214—H214107.3C19—C14—H14107.9
C213—C216—H21A110.5C13—C16—H16A110.7
C213—C216—H21B110.5C13—C16—H16B110.7
C213—C216—C217106.0 (4)C13—C16—C17105.3 (4)
H21A—C216—H21B108.7H16A—C16—H16B108.8
C217—C216—H21A110.5C17—C16—H16A110.7
C217—C216—H21B110.5C17—C16—H16B110.7
C216—C217—H21C109.0C16—C17—H17A109.1
C216—C217—H21D109.0C16—C17—H17B109.1
C216—C217—C218112.7 (5)H17A—C17—H17B107.8
H21C—C217—H21D107.8C18—C17—C16112.4 (5)
C218—C217—H21C109.0C18—C17—H17A109.1
C218—C217—H21D109.0C18—C17—H17B109.1
C217—C218—H21E108.9C17—C18—H18A108.8
C217—C218—H21F108.9C17—C18—H18B108.8
H21E—C218—H21F107.7C17—C18—C19113.9 (4)
C219—C218—C217113.5 (5)H18A—C18—H18B107.7
C219—C218—H21E108.9C19—C18—H18A108.8
C219—C218—H21F108.9C19—C18—H18B108.8
C214—C219—C218106.9 (4)C14—C19—C18105.5 (4)
C214—C219—H21G110.3C14—C19—H19A110.6
C214—C219—H21H110.3C14—C19—H19B110.6
C218—C219—H21G110.3C18—C19—H19A110.6
C218—C219—H21H110.3C18—C19—H19B110.6
H21G—C219—H21H108.6H19A—C19—H19B108.8
Ir2—C301—H301112.8Ir1—C101—H101113.1
C302—C301—Ir274.4 (4)C102—C101—Ir171.3 (3)
C302—C301—H301112.8C102—C101—H101113.1
C302—C301—C306128.0 (6)C102—C101—C106127.2 (5)
C306—C301—Ir2108.9 (4)C106—C101—Ir1111.3 (4)
C306—C301—H301112.8C106—C101—H101113.1
Ir2—C302—H302115.0Ir1—C102—H102114.8
C301—C302—Ir269.3 (4)C101—C102—Ir171.2 (3)
C301—C302—H302115.0C101—C102—H102114.8
C301—C302—C307122.5 (6)C101—C102—C107121.7 (5)
C307—C302—Ir2111.4 (4)C107—C102—Ir1111.8 (4)
C307—C302—H302115.0C107—C102—H102114.8
Ir2—C303—H303113.5Ir1—C103—H103113.8
C304—C303—Ir271.0 (4)C104—C103—Ir170.6 (4)
C304—C303—H303113.5C104—C103—H103113.8
C304—C303—C308124.9 (6)C104—C103—C108125.2 (6)
C308—C303—Ir2113.1 (5)C108—C103—Ir1111.8 (4)
C308—C303—H303113.5C108—C103—H103113.8
Ir2—C304—H304114.0Ir1—C104—H104113.2
C303—C304—Ir270.8 (4)C103—C104—Ir171.1 (4)
C303—C304—H304114.0C103—C104—H104113.2
C303—C304—C305124.9 (7)C103—C104—C105124.6 (6)
C305—C304—Ir2111.4 (5)C105—C104—Ir1114.7 (4)
C305—C304—H304114.0C105—C104—H104113.2
C304—C305—H30A108.4C104—C105—H10A108.9
C304—C305—H30B108.4C104—C105—H10B108.9
H30A—C305—H30B107.5H10A—C105—H10B107.8
C306—C305—C304115.5 (6)C106—C105—C104113.2 (5)
C306—C305—H30A108.4C106—C105—H10A108.9
C306—C305—H30B108.4C106—C105—H10B108.9
C301—C306—H30C109.2C101—C106—C105112.1 (5)
C301—C306—H30D109.2C101—C106—H10C109.2
C305—C306—C301112.2 (6)C101—C106—H10D109.2
C305—C306—H30C109.2C105—C106—H10C109.2
C305—C306—H30D109.2C105—C106—H10D109.2
H30C—C306—H30D107.9H10C—C106—H10D107.9
C302—C307—H30E108.9C102—C107—H10E108.9
C302—C307—H30F108.9C102—C107—H10F108.9
C302—C307—C308113.2 (5)C102—C107—C108113.4 (5)
H30E—C307—H30F107.7H10E—C107—H10F107.7
C308—C307—H30E108.9C108—C107—H10E108.9
C308—C307—H30F108.9C108—C107—H10F108.9
C303—C308—C307113.2 (5)C103—C108—C107112.0 (5)
C303—C308—H30G108.9C103—C108—H10G109.2
C303—C308—H30H108.9C103—C108—H10H109.2
C307—C308—H30G108.9C107—C108—H10G109.2
C307—C308—H30H108.9C107—C108—H10H109.2
H30G—C308—H30H107.8H10G—C108—H10H107.9
C325—C320—C321118.6 (6)C125—C120—C121118.5 (5)
C329—C320—C321123.3 (5)C125—C120—C129117.5 (5)
C329—C320—C325118.1 (5)C129—C120—C121124.0 (5)
C320—C321—N212116.8 (5)C120—C121—N12117.3 (5)
C322—C321—N212121.5 (5)C122—C121—N12121.4 (5)
C322—C321—C320121.3 (5)C122—C121—C120121.1 (5)
C321—C322—C323118.4 (5)C121—C122—C123118.2 (5)
C321—C322—C337123.8 (5)C121—C122—C137124.2 (5)
C323—C322—C337117.6 (5)C123—C122—C137117.6 (5)
C322—C323—H323119.1C122—C123—H123119.1
C324—C323—C322121.8 (6)C124—C123—C122121.8 (6)
C324—C323—H323119.1C124—C123—H123119.1
C323—C324—H324119.7C123—C124—H124119.6
C323—C324—C325120.6 (5)C123—C124—C125120.7 (5)
C325—C324—H324119.7C125—C124—H124119.6
C324—C325—C320119.3 (5)C124—C125—C120118.9 (5)
C324—C325—C326122.0 (5)C126—C125—C120119.6 (6)
C326—C325—C320118.7 (6)C126—C125—C124121.3 (5)
C325—C326—H326119.6C125—C126—H126119.3
C327—C326—C325120.9 (6)C127—C126—C125121.4 (5)
C327—C326—H326119.6C127—C126—H126119.3
C326—C327—H327119.1C126—C127—H127119.8
C326—C327—C328121.8 (6)C126—C127—C128120.4 (6)
C328—C327—H327119.1C128—C127—H127119.8
C327—C328—C331118.6 (5)C127—C128—C131118.9 (5)
C329—C328—C327118.5 (6)C129—C128—C127119.0 (6)
C329—C328—C331122.8 (5)C129—C128—C131122.1 (5)
C320—C329—H329119.0C120—C129—H129119.0
C328—C329—C320121.9 (5)C128—C129—C120122.0 (5)
C328—C329—H329119.0C128—C129—H129119.0
C328—C331—H331107.6C128—C131—H131107.8
C328—C331—C332112.3 (6)C128—C131—C132112.2 (5)
C328—C331—C336112.5 (7)C128—C131—C136110.7 (5)
C332—C331—H331107.6C132—C131—H131107.8
C332—C331—C336109.1 (7)C132—C131—C136110.3 (5)
C336—C331—H331107.6C136—C131—H131107.8
C331—C332—H33A109.9C131—C132—H13A109.1
C331—C332—H33B109.9C131—C132—H13B109.1
C331—C332—C333108.9 (9)C131—C132—C133112.6 (6)
H33A—C332—H33B108.3H13A—C132—H13B107.8
C333—C332—H33A109.9C133—C132—H13A109.1
C333—C332—H33B109.9C133—C132—H13B109.1
C332—C333—H33C109.1C132—C133—H13C109.3
C332—C333—H33D109.1C132—C133—H13D109.3
H33C—C333—H33D107.9H13C—C133—H13D107.9
C334—C333—C332112.3 (10)C134—C133—C132111.8 (6)
C334—C333—H33C109.1C134—C133—H13C109.3
C334—C333—H33D109.1C134—C133—H13D109.3
C333—C334—H33E109.3C133—C134—H13E109.3
C333—C334—H33F109.3C133—C134—H13F109.3
H33E—C334—H33F107.9C133—C134—C135111.5 (6)
C335—C334—C333111.8 (10)H13E—C134—H13F108.0
C335—C334—H33E109.3C135—C134—H13E109.3
C335—C334—H33F109.3C135—C134—H13F109.3
C334—C335—H33G109.4C134—C135—H13G109.4
C334—C335—H33H109.4C134—C135—H13H109.4
C334—C335—C336111.1 (10)C134—C135—C136111.0 (6)
H33G—C335—H33H108.0H13G—C135—H13H108.0
C336—C335—H33G109.4C136—C135—H13G109.4
C336—C335—H33H109.4C136—C135—H13H109.4
C331—C336—H33I109.8C131—C136—H13I109.0
C331—C336—H33J109.8C131—C136—H13J109.0
C335—C336—C331109.2 (9)C135—C136—C131113.1 (6)
C335—C336—H33I109.8C135—C136—H13I109.0
C335—C336—H33J109.8C135—C136—H13J109.0
H33I—C336—H33J108.3H13I—C136—H13J107.8
C322—C337—H337108.1C122—C137—H137108.1
C322—C337—C338109.9 (5)C122—C137—C138114.1 (5)
C322—C337—C342112.6 (5)C122—C137—C142110.2 (5)
C338—C337—H337108.1C138—C137—H137108.1
C342—C337—H337108.1C142—C137—H137108.1
C342—C337—C338109.9 (5)C142—C137—C138108.1 (5)
C337—C338—H33K109.4C137—C138—H13K109.4
C337—C338—H33L109.4C137—C138—H13L109.4
H33K—C338—H33L108.0H13K—C138—H13L108.0
C339—C338—C337111.1 (5)C139—C138—C137111.1 (5)
C339—C338—H33K109.4C139—C138—H13K109.4
C339—C338—H33L109.4C139—C138—H13L109.4
C338—C339—H33M109.0C138—C139—H13M109.2
C338—C339—H33N109.0C138—C139—H13N109.2
H33M—C339—H33N107.8C138—C139—C140112.0 (6)
C340—C339—C338113.1 (6)H13M—C139—H13N107.9
C340—C339—H33M109.0C140—C139—H13M109.2
C340—C339—H33N109.0C140—C139—H13N109.2
C339—C340—H34A109.3C139—C140—H14A109.5
C339—C340—H34B109.3C139—C140—H14B109.5
C339—C340—C341111.7 (7)H14A—C140—H14B108.1
H34A—C340—H34B107.9C141—C140—C139110.7 (5)
C341—C340—H34A109.3C141—C140—H14A109.5
C341—C340—H34B109.3C141—C140—H14B109.5
C340—C341—H34C109.5C140—C141—H14C109.3
C340—C341—H34D109.5C140—C141—H14D109.3
C340—C341—C342110.8 (6)C140—C141—C142111.6 (5)
H34C—C341—H34D108.1H14C—C141—H14D108.0
C342—C341—H34C109.5C142—C141—H14C109.3
C342—C341—H34D109.5C142—C141—H14D109.3
C337—C342—C341110.8 (6)C137—C142—H14E109.4
C337—C342—H34E109.5C137—C142—H14F109.4
C337—C342—H34F109.5C141—C142—C137111.0 (5)
C341—C342—H34E109.5C141—C142—H14E109.4
C341—C342—H34F109.5C141—C142—H14F109.4
H34E—C342—H34F108.1H14E—C142—H14F108.0
C355—C350—C351118.2 (5)C151—C150—C155118.5 (5)
C359—C350—C351123.4 (5)C159—C150—C151123.1 (5)
C359—C350—C355118.4 (5)C159—C150—C155118.3 (5)
C350—C351—N215118.9 (5)C150—C151—N15118.1 (5)
C352—C351—N215120.3 (5)C152—C151—N15119.8 (5)
C352—C351—C350120.8 (5)C152—C151—C150121.9 (5)
C351—C352—C353117.8 (5)C151—C152—C153117.5 (5)
C351—C352—C367124.4 (4)C151—C152—C167124.5 (5)
C353—C352—C367117.6 (5)C153—C152—C167117.8 (5)
C352—C353—H353118.8C152—C153—H153118.5
C354—C353—C352122.5 (6)C154—C153—C152123.0 (6)
C354—C353—H353118.8C154—C153—H153118.5
C353—C354—H354119.8C153—C154—H154120.0
C353—C354—C355120.4 (5)C153—C154—C155120.0 (5)
C355—C354—H354119.8C155—C154—H154120.0
C350—C355—C356118.3 (6)C154—C155—C150119.1 (5)
C354—C355—C350119.8 (5)C156—C155—C150119.0 (6)
C354—C355—C356121.9 (5)C156—C155—C154121.9 (5)
C355—C356—H356119.6C155—C156—H156119.5
C357—C356—C355120.9 (5)C157—C156—C155121.1 (5)
C357—C356—H356119.6C157—C156—H156119.5
C356—C357—H357119.0C156—C157—H157119.6
C356—C357—C358122.0 (6)C156—C157—C158120.8 (5)
C358—C357—H357119.0C158—C157—H157119.6
C357—C358—C361119.9 (6)C157—C158—C161119.7 (5)
C359—C358—C357118.0 (6)C159—C158—C157119.0 (5)
C359—C358—C361122.0 (5)C159—C158—C161121.3 (5)
C350—C359—H359118.8C150—C159—H159119.1
C358—C359—C350122.3 (5)C158—C159—C150121.8 (5)
C358—C359—H359118.8C158—C159—H159119.1
C358—C361—H361108.3C158—C161—H161106.6
C358—C361—C366111.4 (6)C158—C161—C162113.0 (6)
C362—C361—C358110.8 (6)C162—C161—H161106.6
C362—C361—H361108.3C166—C161—C158113.0 (6)
C362—C361—C366109.8 (6)C166—C161—H161106.6
C366—C361—H361108.3C166—C161—C162110.4 (5)
C361—C362—H36A109.0C161—C162—H16C109.2
C361—C362—H36B109.0C161—C162—H16D109.2
C361—C362—C363112.9 (7)C161—C162—C163111.9 (5)
H36A—C362—H36B107.8H16C—C162—H16D107.9
C363—C362—H36A109.0C163—C162—H16C109.2
C363—C362—H36B109.0C163—C162—H16D109.2
C362—C363—H36C109.7C162—C163—H16E109.8
C362—C363—H36D109.7C162—C163—H16F109.8
C362—C363—C364109.8 (7)H16E—C163—H16F108.2
H36C—C363—H36D108.2C164—C163—C162109.5 (6)
C364—C363—H36C109.7C164—C163—H16E109.8
C364—C363—H36D109.7C164—C163—H16F109.8
C363—C364—H36E109.8C163—C164—H16G109.2
C363—C364—H36F109.8C163—C164—H16H109.2
H36E—C364—H36F108.2C163—C164—C165112.2 (6)
C365—C364—C363109.6 (7)H16G—C164—H16H107.9
C365—C364—H36E109.8C165—C164—H16G109.2
C365—C364—H36F109.8C165—C164—H16H109.2
C364—C365—H36G109.4C164—C165—H16I109.3
C364—C365—H36H109.4C164—C165—H16J109.3
H36G—C365—H36H108.0C164—C165—C166111.8 (6)
C366—C365—C364111.1 (7)H16I—C165—H16J107.9
C366—C365—H36G109.4C166—C165—H16I109.3
C366—C365—H36H109.4C166—C165—H16J109.3
C361—C366—H36I108.5C161—C166—C165111.2 (6)
C361—C366—H36J108.5C161—C166—H16K109.4
C365—C366—C361115.0 (7)C161—C166—H16L109.4
C365—C366—H36I108.5C165—C166—H16K109.4
C365—C366—H36J108.5C165—C166—H16L109.4
H36I—C366—H36J107.5H16K—C166—H16L108.0
C352—C367—H367108.7C152—C167—H167107.9
C352—C367—C368110.2 (5)C152—C167—C168111.0 (5)
C352—C367—C372113.8 (5)C152—C167—C172112.9 (5)
C368—C367—H367108.7C168—C167—H167107.9
C368—C367—C372106.7 (5)C168—C167—C172109.0 (5)
C372—C367—H367108.7C172—C167—H167107.9
C367—C368—H36K109.2C167—C168—H16M109.0
C367—C368—H36L109.2C167—C168—H16N109.0
H36K—C368—H36L107.9H16M—C168—H16N107.8
C369—C368—C367112.0 (5)C169—C168—C167112.9 (5)
C369—C368—H36K109.2C169—C168—H16M109.0
C369—C368—H36L109.2C169—C168—H16N109.0
C368—C369—H36M109.7C168—C169—H16O109.5
C368—C369—H36N109.7C168—C169—H16P109.5
H36M—C369—H36N108.2C168—C169—C170110.9 (6)
C370—C369—C368110.0 (5)H16O—C169—H16P108.0
C370—C369—H36M109.7C170—C169—H16O109.5
C370—C369—H36N109.7C170—C169—H16P109.5
C369—C370—H37A109.1C169—C170—H17C109.3
C369—C370—H37B109.1C169—C170—H17D109.3
C369—C370—C371112.4 (5)H17C—C170—H17D107.9
H37A—C370—H37B107.9C171—C170—C169111.7 (6)
C371—C370—H37A109.1C171—C170—H17C109.3
C371—C370—H37B109.1C171—C170—H17D109.3
C370—C371—H37C109.3C170—C171—H17E109.2
C370—C371—H37D109.3C170—C171—H17F109.2
C370—C371—C372111.4 (6)H17E—C171—H17F107.9
H37C—C371—H37D108.0C172—C171—C170112.1 (6)
C372—C371—H37C109.3C172—C171—H17E109.2
C372—C371—H37D109.3C172—C171—H17F109.2
C367—C372—H37E109.3C167—C172—H17G109.3
C367—C372—H37F109.3C167—C172—H17H109.3
C371—C372—C367111.5 (5)C171—C172—C167111.7 (6)
C371—C372—H37E109.3C171—C172—H17G109.3
C371—C372—H37F109.3C171—C172—H17H109.3
H37E—C372—H37F108.0H17G—C172—H17H107.9
Ir2—C301—C302—C307102.8 (6)Ir1—C101—C102—C107104.6 (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—C305103.2 (7)Ir1—C103—C104—C105107.5 (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—C323173.5 (5)N12—C121—C122—C123−178.6 (5)
N212—C321—C322—C337−1.0 (9)N12—C121—C122—C1374.2 (9)
N215—C214—C219—C218−177.2 (5)N15—C14—C19—C18−176.6 (5)
N215—C351—C352—C353173.6 (5)N15—C151—C152—C153−173.2 (5)
N215—C351—C352—C367−11.0 (9)N15—C151—C152—C1673.2 (9)
C211—N212—C213—C21429.7 (6)C11—N12—C13—C1426.5 (6)
C211—N212—C213—C216153.9 (5)C11—N12—C13—C16150.0 (5)
C211—N212—C321—C320−111.6 (6)C11—N12—C121—C120−91.0 (7)
C211—N212—C321—C32274.6 (8)C11—N12—C121—C12293.9 (7)
C211—N215—C214—C21330.1 (6)C11—N15—C14—C1328.8 (6)
C211—N215—C214—C219153.0 (5)C11—N15—C14—C19151.1 (5)
C211—N215—C351—C35079.9 (8)C11—N15—C151—C150103.9 (7)
C211—N215—C351—C352−100.9 (7)C11—N15—C151—C152−82.2 (8)
C213—N212—C211—Ir2170.6 (4)C13—N12—C11—Ir1171.3 (4)
C213—N212—C211—N215−11.8 (6)C13—N12—C11—N15−9.2 (6)
C213—N212—C321—C32097.9 (6)C13—N12—C121—C120107.3 (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—C21853.1 (7)C13—C16—C17—C1854.0 (6)
C214—N215—C211—Ir2165.8 (4)C14—N15—C11—Ir1166.2 (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—C35296.1 (7)C14—N15—C151—C152107.1 (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—C21965.6 (6)C16—C13—C14—C1969.3 (6)
C216—C217—C218—C219−54.1 (7)C16—C17—C18—C19−53.1 (7)
C217—C218—C219—C21453.9 (7)C17—C18—C19—C1453.4 (7)
C301—C302—C307—C308−89.6 (8)C101—C102—C107—C108−91.5 (7)
C302—C301—C306—C30549.2 (9)C102—C101—C106—C10550.0 (8)
C302—C307—C308—C30327.8 (8)C102—C107—C108—C10328.7 (7)
C303—C304—C305—C306−88.6 (9)C103—C104—C105—C106−92.8 (8)
C304—C303—C308—C30750.6 (10)C104—C103—C108—C10747.9 (9)
C304—C305—C306—C30128.9 (8)C104—C105—C106—C10127.4 (7)
C306—C301—C302—Ir2−102.0 (7)C106—C101—C102—Ir1−103.0 (6)
C306—C301—C302—C3070.8 (10)C106—C101—C102—C1071.5 (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—C1054.0 (11)
C320—C321—C322—C3230.0 (9)C120—C121—C122—C1236.4 (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—Ir217.7 (8)C121—N12—C11—Ir17.6 (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—C3241.2 (9)C121—C120—C125—C1245.6 (9)
C321—C320—C325—C326−177.5 (6)C121—C120—C125—C126−178.6 (6)
C321—C320—C329—C328176.9 (6)C121—C120—C129—C128−179.7 (6)
C321—C322—C323—C3240.7 (9)C121—C122—C123—C1241.7 (9)
C321—C322—C337—C338104.5 (6)C121—C122—C137—C138−144.1 (6)
C321—C322—C337—C342−132.6 (6)C121—C122—C137—C14294.1 (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—C139178.1 (5)
C322—C337—C342—C341179.7 (4)C122—C137—C142—C141−176.0 (5)
C323—C322—C337—C338−70.0 (7)C123—C122—C137—C13838.7 (7)
C323—C322—C337—C34252.9 (7)C123—C122—C137—C142−83.1 (6)
C323—C324—C325—C320−0.5 (9)C123—C124—C125—C1202.1 (9)
C323—C324—C325—C326178.2 (6)C123—C124—C125—C126−173.6 (6)
C324—C325—C326—C327−178.8 (6)C124—C125—C126—C127174.8 (6)
C325—C320—C321—N212−174.7 (5)C125—C120—C121—N12174.8 (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—C1294.5 (10)
C326—C327—C328—C331178.5 (6)C126—C127—C128—C131−175.9 (6)
C327—C328—C329—C3201.2 (10)C127—C128—C129—C120−2.4 (9)
C327—C328—C331—C332110.2 (7)C127—C128—C131—C132−51.6 (8)
C327—C328—C331—C336−126.3 (7)C127—C128—C131—C13672.1 (7)
C328—C331—C332—C333−179.2 (7)C128—C131—C132—C133172.2 (5)
C328—C331—C336—C335173.8 (7)C128—C131—C136—C135−174.9 (5)
C329—C320—C321—N2126.9 (9)C129—C120—C121—N12−6.7 (9)
C329—C320—C321—C322−179.4 (6)C129—C120—C121—C122168.5 (6)
C329—C320—C325—C324179.7 (6)C129—C120—C125—C124−172.9 (6)
C329—C320—C325—C3261.0 (9)C129—C120—C125—C1262.8 (9)
C329—C328—C331—C332−71.1 (9)C129—C128—C131—C132128.0 (6)
C329—C328—C331—C33652.4 (10)C129—C128—C131—C136−108.2 (6)
C331—C328—C329—C320−177.6 (6)C131—C128—C129—C120178.0 (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—C33554.2 (13)C132—C133—C134—C13557.7 (7)
C333—C334—C335—C336−59.2 (13)C133—C134—C135—C136−58.8 (8)
C334—C335—C336—C33162.2 (12)C134—C135—C136—C13155.0 (7)
C336—C331—C332—C33355.3 (9)C136—C131—C132—C13348.3 (7)
C337—C322—C323—C324175.6 (6)C137—C122—C123—C124179.0 (6)
C337—C338—C339—C340−55.3 (7)C137—C138—C139—C14057.6 (7)
C338—C337—C342—C341−57.4 (6)C138—C137—C142—C14158.7 (6)
C338—C339—C340—C34153.7 (7)C138—C139—C140—C141−53.9 (7)
C339—C340—C341—C342−53.5 (8)C139—C140—C141—C14253.4 (7)
C340—C341—C342—C33755.9 (7)C140—C141—C142—C137−57.3 (7)
C342—C337—C338—C33956.5 (7)C142—C137—C138—C139−59.0 (6)
C350—C351—C352—C353−7.3 (9)C150—C151—C152—C1530.5 (9)
C350—C351—C352—C367168.2 (5)C150—C151—C152—C167176.8 (5)
C350—C355—C356—C3573.9 (10)C150—C155—C156—C157−0.1 (9)
C351—N215—C211—Ir20.9 (8)C151—N15—C11—Ir1−5.1 (9)
C351—N215—C211—N212−177.0 (5)C151—N15—C11—N12175.4 (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—C1540.0 (9)
C351—C350—C355—C356179.2 (6)C151—C150—C155—C156177.7 (5)
C351—C350—C359—C358178.9 (6)C151—C150—C159—C158−176.3 (5)
C351—C352—C353—C3541.3 (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—C372135.4 (6)C151—C152—C167—C172127.5 (6)
C352—C353—C354—C3553.8 (10)C152—C153—C154—C155−0.4 (10)
C352—C367—C368—C369175.5 (5)C152—C167—C168—C169178.8 (5)
C352—C367—C372—C371179.4 (5)C152—C167—C172—C171179.5 (4)
C353—C352—C367—C36870.7 (7)C153—C152—C167—C16866.6 (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—C1500.4 (9)
C353—C354—C355—C356174.9 (6)C153—C154—C155—C156−177.2 (6)
C354—C355—C356—C357−173.8 (7)C154—C155—C156—C157177.6 (6)
C355—C350—C351—N215−172.6 (5)C155—C150—C151—N15173.3 (5)
C355—C350—C351—C3528.2 (9)C155—C150—C151—C152−0.4 (9)
C355—C350—C359—C3580.9 (9)C155—C150—C159—C1582.0 (9)
C355—C356—C357—C358−3.2 (11)C155—C156—C157—C158−0.5 (10)
C356—C357—C358—C3591.3 (11)C156—C157—C158—C1591.7 (9)
C356—C357—C358—C361177.8 (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—C162127.4 (6)
C357—C358—C361—C36655.1 (9)C157—C158—C161—C166−106.3 (6)
C358—C361—C362—C363176.3 (6)C158—C161—C162—C163−173.8 (5)
C358—C361—C366—C365−174.7 (6)C158—C161—C166—C165176.6 (5)
C359—C350—C351—N2159.3 (9)C159—C150—C151—N15−8.5 (8)
C359—C350—C351—C352−169.9 (6)C159—C150—C151—C152177.8 (6)
C359—C350—C355—C354175.1 (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—C362109.0 (7)C159—C158—C161—C162−52.7 (8)
C359—C358—C361—C366−128.5 (7)C159—C158—C161—C16673.6 (7)
C361—C358—C359—C350−176.5 (6)C161—C158—C159—C150177.6 (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—C36557.7 (10)C162—C163—C164—C16554.6 (8)
C363—C364—C365—C366−56.1 (9)C163—C164—C165—C166−53.5 (8)
C364—C365—C366—C36154.1 (8)C164—C165—C166—C16153.6 (8)
C366—C361—C362—C36352.9 (9)C166—C161—C162—C16358.5 (7)
C367—C352—C353—C354−174.5 (6)C167—C152—C153—C154−176.6 (6)
C367—C368—C369—C37059.6 (6)C167—C168—C169—C17055.6 (8)
C368—C367—C372—C37157.6 (6)C168—C167—C172—C17155.7 (6)
C368—C369—C370—C371−54.7 (7)C168—C169—C170—C171−53.0 (8)
C369—C370—C371—C37253.1 (7)C169—C170—C171—C17253.8 (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)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···Cl1i0.992.793.773 (6)171
C353—H353···Cl10.952.803.650 (6)149
C372—H37E···Cl20.992.563.422 (6)146
Symmetry code: (i) x, y−1, z.
[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 (II) top
Crystal data top
[Ir(C51H64N2)Cl(C8H12)]F(000) = 2152
Mr = 1040.86Dx = 1.405 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2abCell parameters from 10786 reflections
a = 16.1663 (4) Åθ = 3.6–67.3°
b = 17.2811 (4) ŵ = 6.04 mm−1
c = 17.6110 (3) ÅT = 100 K
V = 4920.01 (19) Å3Needle, yellow
Z = 40.25 × 0.03 × 0.02 mm
Data collection top
Oxford Diffraction Gemini
diffractometer		8782 independent reflections
Radiation source: sealed X-ray tube, Enhance Ultra (Cu) X-ray Source8164 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.056
Detector resolution: 10.4738 pixels mm-1θmax = 67.7°, θmin = 3.6°
ω scansh = −19→17
Absorption correction: analytical
CrysAlisPro (Rigaku OD, 2019)		k = −19→20
Tmin = 0.50, Tmax = 0.90l = −19→20
26296 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 2.41 e Å−3
8782 reflectionsΔρmin = −0.91 e Å−3
568 parametersAbsolute structure: Flack x determined using 3426 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: −0.046 (7)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir10.54235 (2)0.59059 (2)0.39700 (2)0.02181 (11)
Cl10.41450 (11)0.58045 (12)0.46083 (10)0.0271 (4)
C1010.4761 (6)0.6278 (5)0.2922 (4)0.0294 (19)
H1010.4303790.5966790.307050.035*
C1020.4939 (5)0.6920 (5)0.3383 (5)0.0265 (18)
H1020.4576210.7013430.3797290.032*
C1030.6542 (5)0.6303 (5)0.3450 (5)0.0260 (17)
H1030.6768550.6310760.3947370.031*
C1040.6311 (5)0.5567 (5)0.3138 (5)0.0267 (17)
H1040.6424580.5119520.3433420.032*
C1050.5902 (5)0.5451 (5)0.2382 (5)0.0279 (18)
H10A0.5667570.4922620.2362470.033*
H10B0.6327780.5489440.1978890.033*
C1060.5221 (5)0.6028 (5)0.2214 (5)0.0302 (19)
H10C0.4824530.579340.1853180.036*
H10D0.5464810.6489760.1967770.036*
C1070.5648 (6)0.7477 (5)0.3284 (5)0.034 (2)
H10E0.5745120.7753280.3768030.041*
H10F0.5499210.786620.2894650.041*
C1080.6449 (6)0.7066 (5)0.3043 (5)0.0305 (19)
H10G0.6439810.6975510.2487520.037*
H10H0.6929410.7400430.3159850.037*
C110.5961 (5)0.5311 (5)0.4844 (4)0.0213 (16)
N120.6073 (4)0.5585 (4)0.5563 (4)0.0214 (14)
C1210.5956 (5)0.6363 (5)0.5851 (4)0.0215 (16)
C1220.6570 (5)0.6908 (5)0.5780 (4)0.0246 (17)
C1230.6459 (5)0.7638 (5)0.6144 (5)0.0258 (17)
H1230.684780.8039360.6053490.031*
C1240.5811 (5)0.7774 (5)0.6615 (4)0.0256 (16)
H1240.5765180.8259060.6865050.031*
C1250.5207 (5)0.7200 (5)0.6737 (4)0.0247 (17)
C1260.4548 (6)0.7297 (4)0.7271 (4)0.0269 (16)
H1260.4508720.7764720.7551940.032*
C1270.3973 (5)0.6726 (5)0.7384 (4)0.0248 (17)
H1270.3556720.6795230.7758850.03*
C1280.3989 (5)0.6034 (5)0.6952 (5)0.0266 (17)
C1290.4613 (5)0.5939 (5)0.6433 (4)0.0227 (14)
H1290.4621540.5482120.6133280.027*
C1200.5251 (5)0.6499 (4)0.6326 (4)0.0204 (16)
C1610.7386 (5)0.6754 (5)0.5391 (4)0.0233 (16)
H1610.7339870.6248890.5117590.028*
C1620.8085 (5)0.6678 (5)0.5983 (5)0.0273 (16)
H16A0.8162750.7178330.6246840.033*
H16B0.7930180.6284950.6367030.033*
C1630.8895 (5)0.6439 (6)0.5597 (5)0.0329 (19)
H16C0.9343390.642920.5979340.04*
H16D0.8834560.5909440.5389730.04*
C1640.9135 (6)0.6987 (5)0.4957 (5)0.0330 (19)
H16E0.9614110.6768660.4679910.04*
H16F0.9308110.7488780.5177120.04*
C1650.8430 (6)0.7126 (6)0.4397 (5)0.034 (2)
H16G0.8324360.6646790.4104970.041*
H16H0.8590680.7536990.4034690.041*
C1660.7638 (5)0.7368 (5)0.4814 (4)0.0284 (18)
H16I0.7730540.7866370.5077160.034*
H16J0.7185590.7440930.4441790.034*
C1710.3316 (5)0.5443 (5)0.7060 (5)0.0287 (18)
H1710.3166970.544360.7611020.034*
C1720.3565 (5)0.4618 (5)0.6853 (5)0.0299 (18)
H17C0.405510.4466250.7156050.036*
H17D0.3720390.4597510.6310040.036*
C1730.2864 (5)0.4044 (6)0.7001 (5)0.0334 (18)
H17E0.3039110.3518560.6845490.04*
H17F0.273610.4031680.7551080.04*
C1740.2094 (6)0.4279 (6)0.6559 (5)0.038 (2)
H17G0.2208970.4238760.6007860.045*
H17H0.1637910.3917210.6680420.045*
C1750.1828 (6)0.5096 (6)0.6744 (6)0.038 (2)
H17I0.1645340.5121810.7280510.045*
H17J0.1353080.5241680.6419230.045*
C1760.2538 (6)0.5670 (5)0.6618 (6)0.035 (2)
H17K0.2670290.5692440.6069810.042*
H17L0.2358650.6192380.6779520.042*
C130.6188 (5)0.4929 (4)0.6090 (5)0.0236 (15)
H130.5626560.473080.6226370.028*
C140.6579 (5)0.4347 (5)0.5573 (4)0.0214 (16)
H140.7180560.4475350.553290.026*
N150.6182 (4)0.4564 (4)0.4847 (4)0.0223 (14)
C1510.6255 (5)0.4036 (5)0.4216 (4)0.0238 (15)
C1520.5576 (4)0.3625 (4)0.3968 (5)0.0236 (15)
C1530.5708 (5)0.3055 (5)0.3389 (5)0.0282 (18)
H1530.5249440.2766690.3204790.034*
C1540.6476 (6)0.2917 (5)0.3097 (5)0.0296 (18)
H1540.6541640.2531250.2717510.035*
C1550.7167 (5)0.3329 (5)0.3344 (4)0.0260 (17)
C1560.7967 (5)0.3190 (5)0.3058 (5)0.0275 (17)
H1560.8041370.2811270.2673030.033*
C1570.8641 (6)0.3590 (5)0.3324 (5)0.0287 (18)
H1570.9176810.3465930.3138050.034*
C1580.8550 (5)0.4179 (5)0.3865 (4)0.0246 (16)
C1590.7772 (5)0.4340 (5)0.4133 (4)0.0254 (18)
H1590.7705880.4753380.4483690.031*
C1500.7063 (5)0.3917 (4)0.3908 (5)0.0235 (15)
C1810.4720 (5)0.3702 (5)0.4297 (4)0.0262 (17)
H1810.473340.4122840.4686450.031*
C1820.4456 (5)0.2949 (5)0.4694 (5)0.0307 (18)
H18A0.4475690.25170.4325190.037*
H18B0.4850770.2830930.5108130.037*
C1830.3586 (6)0.3007 (6)0.5023 (5)0.036 (2)
H18C0.3577740.3402910.5429170.043*
H18D0.3429370.2504360.5251690.043*
C1840.2955 (6)0.3224 (6)0.4408 (6)0.036 (2)
H18E0.2930290.2809590.4020410.044*
H18F0.2399230.3276640.4637870.044*
C1850.3202 (5)0.3985 (6)0.4032 (5)0.0344 (19)
H18G0.3187760.4406480.4413060.041*
H18H0.2800790.4113150.3626230.041*
C1860.4080 (5)0.3927 (5)0.3689 (5)0.0299 (19)
H18I0.40820.3534150.3279730.036*
H18J0.4235220.4430750.346280.036*
C1910.9290 (6)0.4584 (5)0.4195 (5)0.0297 (19)
H1910.9087220.5047410.4480490.036*
C1920.9725 (6)0.4040 (9)0.4770 (6)0.052 (3)
H19A0.9325090.389050.5168980.063*
H19B0.9899760.3562920.4503080.063*
C1931.0474 (7)0.4407 (8)0.5141 (6)0.058 (3)
H19C1.0746210.4024670.5476380.069*
H19D1.0295340.4850040.5457130.069*
C1941.1091 (6)0.4688 (7)0.4545 (6)0.043 (2)
H19E1.1555840.495540.480070.052*
H19F1.1319150.4237250.4268140.052*
C1951.0687 (5)0.5234 (5)0.3988 (6)0.0344 (18)
H19G1.1091790.538050.3591870.041*
H19H1.0514740.5710680.4256420.041*
C1960.9931 (6)0.4862 (6)0.3613 (5)0.038 (2)
H19I1.0113860.4416610.3302110.045*
H19J0.9668960.5243150.3269020.045*
C160.6671 (5)0.5007 (5)0.6816 (5)0.0276 (17)
H16K0.6404310.5387440.7156980.033*
H16L0.7242380.5180430.6708610.033*
C170.6677 (6)0.4197 (5)0.7185 (4)0.0304 (18)
H17A0.7039860.4209420.7637820.037*
H17B0.6110180.407120.7359270.037*
C180.6974 (5)0.3558 (5)0.6653 (5)0.0273 (17)
H18K0.6904630.3052210.6908720.033*
H18L0.7572090.3631560.6553910.033*
C190.6508 (5)0.3541 (5)0.5886 (4)0.0261 (17)
H19K0.6763830.3161890.5536310.031*
H19L0.5920660.3398940.5963290.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.02523 (16)0.02132 (16)0.01887 (16)0.00163 (14)−0.00061 (13)0.00003 (13)
Cl10.0241 (9)0.0308 (11)0.0264 (9)0.0000 (8)0.0015 (7)0.0006 (8)
C1010.037 (5)0.033 (4)0.018 (4)0.007 (4)−0.006 (3)0.008 (3)
C1020.036 (4)0.016 (4)0.028 (4)0.012 (3)−0.001 (3)0.012 (3)
C1030.024 (4)0.034 (5)0.021 (4)−0.006 (3)0.005 (3)0.003 (3)
C1040.029 (4)0.026 (4)0.026 (4)0.006 (3)0.009 (4)0.002 (3)
C1050.032 (5)0.028 (5)0.023 (4)0.004 (4)0.003 (3)−0.006 (3)
C1060.039 (5)0.029 (5)0.022 (4)−0.004 (4)−0.002 (3)−0.003 (3)
C1070.051 (6)0.027 (5)0.024 (4)0.006 (4)0.000 (3)0.002 (3)
C1080.042 (5)0.028 (5)0.022 (4)−0.002 (4)0.001 (4)0.003 (3)
C110.018 (4)0.024 (4)0.021 (4)0.000 (3)0.000 (3)−0.002 (3)
N120.025 (3)0.023 (3)0.017 (3)−0.002 (3)0.002 (3)−0.002 (3)
C1210.028 (4)0.021 (4)0.016 (4)−0.001 (3)−0.001 (3)−0.001 (3)
C1220.029 (4)0.026 (4)0.019 (4)0.002 (3)−0.001 (3)0.003 (3)
C1230.031 (4)0.020 (4)0.026 (4)−0.002 (3)−0.008 (3)0.002 (3)
C1240.035 (4)0.019 (4)0.022 (4)0.004 (3)−0.004 (3)−0.002 (3)
C1250.032 (4)0.025 (4)0.017 (4)0.010 (3)−0.003 (3)0.000 (3)
C1260.033 (4)0.017 (4)0.031 (4)0.007 (4)−0.002 (4)−0.004 (3)
C1270.028 (4)0.023 (4)0.023 (4)0.005 (3)0.001 (3)−0.002 (3)
C1280.026 (4)0.025 (4)0.029 (4)0.006 (3)−0.004 (3)0.009 (3)
C1290.026 (4)0.022 (3)0.020 (3)0.003 (4)0.000 (3)−0.001 (3)
C1200.022 (4)0.018 (4)0.021 (3)0.003 (3)−0.004 (3)0.002 (3)
C1610.025 (4)0.023 (4)0.021 (4)−0.003 (3)0.002 (3)−0.003 (3)
C1620.028 (4)0.026 (4)0.028 (4)−0.003 (3)−0.001 (4)0.001 (4)
C1630.029 (5)0.033 (5)0.036 (5)−0.003 (4)0.003 (4)−0.002 (4)
C1640.032 (5)0.033 (5)0.034 (5)−0.004 (4)0.008 (4)−0.006 (4)
C1650.038 (5)0.039 (5)0.025 (4)−0.012 (4)0.003 (4)0.002 (4)
C1660.034 (4)0.031 (5)0.020 (4)−0.006 (4)0.000 (3)0.003 (3)
C1710.031 (4)0.029 (5)0.026 (4)−0.001 (4)0.004 (3)−0.002 (3)
C1720.034 (5)0.027 (4)0.029 (4)−0.002 (3)0.001 (4)0.003 (3)
C1730.035 (4)0.027 (4)0.038 (4)−0.001 (4)0.002 (3)0.004 (4)
C1740.034 (5)0.044 (6)0.036 (5)−0.006 (4)0.007 (4)0.000 (4)
C1750.030 (5)0.040 (6)0.044 (5)0.004 (4)−0.002 (4)−0.004 (4)
C1760.031 (5)0.026 (5)0.048 (5)0.004 (3)0.004 (4)0.001 (4)
C130.028 (4)0.019 (4)0.023 (4)0.001 (3)0.002 (3)0.001 (3)
C140.024 (4)0.023 (4)0.017 (4)−0.001 (3)0.000 (3)−0.001 (3)
N150.025 (3)0.020 (3)0.022 (3)−0.001 (3)−0.002 (3)0.000 (3)
C1510.030 (4)0.019 (4)0.022 (3)0.001 (4)−0.001 (3)−0.001 (3)
C1520.026 (4)0.024 (4)0.021 (3)−0.002 (3)−0.001 (3)−0.001 (3)
C1530.032 (4)0.024 (4)0.028 (4)−0.004 (3)0.000 (3)−0.004 (3)
C1540.043 (5)0.023 (4)0.022 (4)0.004 (3)−0.001 (4)−0.005 (3)
C1550.035 (5)0.021 (4)0.022 (4)0.007 (3)0.002 (3)−0.002 (3)
C1560.037 (5)0.023 (4)0.022 (4)0.004 (3)0.005 (3)−0.001 (3)
C1570.035 (5)0.027 (4)0.024 (4)0.010 (4)0.006 (3)0.009 (3)
C1580.029 (4)0.027 (4)0.018 (4)0.002 (3)−0.003 (3)0.006 (3)
C1590.035 (5)0.019 (4)0.022 (4)0.005 (3)0.001 (3)0.000 (3)
C1500.031 (4)0.018 (4)0.022 (4)0.005 (3)0.002 (3)0.002 (3)
C1810.032 (5)0.022 (4)0.025 (4)−0.001 (3)−0.001 (3)−0.006 (3)
C1820.031 (5)0.026 (4)0.035 (4)−0.002 (3)−0.003 (4)0.004 (3)
C1830.043 (5)0.030 (5)0.035 (5)−0.005 (4)0.004 (4)0.000 (4)
C1840.033 (5)0.029 (5)0.047 (5)−0.003 (4)0.004 (4)−0.001 (4)
C1850.026 (4)0.042 (5)0.035 (4)0.000 (4)−0.004 (3)−0.003 (5)
C1860.029 (4)0.031 (5)0.030 (4)0.000 (3)−0.005 (3)0.000 (3)
C1910.034 (5)0.028 (5)0.027 (4)0.001 (3)0.000 (3)−0.005 (3)
C1920.044 (6)0.078 (8)0.035 (5)−0.015 (6)−0.002 (4)0.016 (6)
C1930.038 (5)0.097 (9)0.037 (5)−0.016 (6)−0.011 (5)0.027 (5)
C1940.037 (5)0.052 (6)0.039 (5)−0.003 (4)−0.002 (4)0.008 (5)
C1950.035 (4)0.031 (4)0.038 (4)0.002 (3)0.005 (4)0.007 (4)
C1960.040 (5)0.042 (6)0.031 (4)−0.001 (4)0.002 (4)0.013 (4)
C160.035 (4)0.022 (4)0.026 (4)0.000 (3)−0.005 (3)−0.004 (3)
C170.038 (4)0.029 (5)0.024 (4)0.001 (4)−0.001 (3)0.000 (4)
C180.034 (4)0.018 (4)0.031 (4)0.002 (3)−0.002 (3)0.005 (3)
C190.038 (5)0.020 (4)0.021 (4)0.002 (3)−0.002 (3)−0.004 (3)
Geometric parameters (Å, º) top
Ir1—C112.045 (8)C174—H17H0.99
Ir1—C1042.132 (8)C175—C1761.533 (13)
Ir1—C1032.140 (8)C175—H17I0.99
Ir1—C1022.181 (7)C175—H17J0.99
Ir1—C1012.228 (7)C176—H17K0.99
Ir1—Cl12.3592 (18)C176—H17L0.99
C101—C1021.405 (13)C13—C141.496 (11)
C101—C1061.515 (12)C13—C161.502 (12)
C101—H1010.95C13—H131
C102—C1071.507 (13)C14—N151.479 (10)
C102—H1020.95C14—C191.504 (11)
C103—C1041.435 (12)C14—H141
C103—C1081.508 (12)N15—C1511.443 (10)
C103—H1030.95C151—C1521.377 (11)
C104—C1051.501 (12)C151—C1501.429 (11)
C104—H1040.95C152—C1531.433 (12)
C105—C1061.514 (12)C152—C1811.506 (11)
C105—H10A0.99C153—C1541.366 (13)
C105—H10B0.99C153—H1530.95
C106—H10C0.99C154—C1551.393 (13)
C106—H10D0.99C154—H1540.95
C107—C1081.536 (13)C155—C1561.408 (12)
C107—H10E0.99C155—C1501.431 (11)
C107—H10F0.99C156—C1571.373 (13)
C108—H10G0.99C156—H1560.95
C108—H10H0.99C157—C1581.403 (12)
C11—N151.339 (11)C157—H1570.95
C11—N121.363 (10)C158—C1591.372 (12)
N12—C1211.449 (10)C158—C1911.503 (12)
N12—C131.478 (10)C159—C1501.417 (12)
C121—C1221.374 (12)C159—H1590.95
C121—C1201.433 (11)C181—C1861.538 (12)
C122—C1231.427 (12)C181—C1821.539 (12)
C122—C1611.511 (11)C181—H1811
C123—C1241.356 (12)C182—C1831.524 (13)
C123—H1230.95C182—H18A0.99
C124—C1251.408 (12)C182—H18B0.99
C124—H1240.95C183—C1841.535 (14)
C125—C1201.413 (11)C183—H18C0.99
C125—C1261.430 (12)C183—H18D0.99
C126—C1271.370 (13)C184—C1851.525 (14)
C126—H1260.95C184—H18E0.99
C127—C1281.417 (12)C184—H18F0.99
C127—H1270.95C185—C1861.547 (12)
C128—C1291.372 (11)C185—H18G0.99
C128—C1711.505 (12)C185—H18H0.99
C129—C1201.426 (11)C186—H18I0.99
C129—H1290.95C186—H18J0.99
C161—C1661.524 (11)C191—C1961.535 (13)
C161—C1621.543 (12)C191—C1921.550 (15)
C161—H1611C191—H1911
C162—C1631.532 (12)C192—C1931.515 (15)
C162—H16A0.99C192—H19A0.99
C162—H16B0.99C192—H19B0.99
C163—C1641.522 (13)C193—C1941.526 (15)
C163—H16C0.99C193—H19C0.99
C163—H16D0.99C193—H19D0.99
C164—C1651.526 (13)C194—C1951.510 (14)
C164—H16E0.99C194—H19E0.99
C164—H16F0.99C194—H19F0.99
C165—C1661.534 (13)C195—C1961.529 (14)
C165—H16G0.99C195—H19G0.99
C165—H16H0.99C195—H19H0.99
C166—H16I0.99C196—H19I0.99
C166—H16J0.99C196—H19J0.99
C171—C1721.526 (12)C16—C171.543 (12)
C171—C1761.529 (13)C16—H16K0.99
C171—H1711C16—H16L0.99
C172—C1731.528 (12)C17—C181.525 (12)
C172—H17C0.99C17—H17A0.99
C172—H17D0.99C17—H17B0.99
C173—C1741.523 (13)C18—C191.547 (11)
C173—H17E0.99C18—H18K0.99
C173—H17F0.99C18—H18L0.99
C174—C1751.513 (14)C19—H19K0.99
C174—H17G0.99C19—H19L0.99
C11—Ir1—C10495.4 (3)C175—C174—H17H109.3
C11—Ir1—C10397.2 (3)C173—C174—H17H109.3
C104—Ir1—C10339.3 (3)H17G—C174—H17H107.9
C11—Ir1—C102156.0 (3)C174—C175—C176111.1 (8)
C104—Ir1—C10297.9 (3)C174—C175—H17I109.4
C103—Ir1—C10280.9 (3)C176—C175—H17I109.4
C11—Ir1—C101166.6 (3)C174—C175—H17J109.4
C104—Ir1—C10180.4 (3)C176—C175—H17J109.4
C103—Ir1—C10187.7 (3)H17I—C175—H17J108
C102—Ir1—C10137.2 (3)C171—C176—C175112.1 (8)
C11—Ir1—Cl188.6 (2)C171—C176—H17K109.2
C104—Ir1—Cl1153.7 (2)C175—C176—H17K109.2
C103—Ir1—Cl1165.4 (2)C171—C176—H17L109.2
C102—Ir1—Cl188.3 (2)C175—C176—H17L109.2
C101—Ir1—Cl189.7 (2)H17K—C176—H17L107.9
C102—C101—C106126.8 (8)N12—C13—C14100.7 (6)
C102—C101—Ir169.6 (4)N12—C13—C16122.2 (7)
C106—C101—Ir1111.3 (5)C14—C13—C16111.0 (7)
C102—C101—H101116.6N12—C13—H13107.4
C106—C101—H101116.6C14—C13—H13107.4
Ir1—C101—H10189C16—C13—H13107.4
C101—C102—C107126.4 (8)N15—C14—C13100.0 (6)
C101—C102—Ir173.2 (4)N15—C14—C19121.3 (7)
C107—C102—Ir1107.1 (5)C13—C14—C19111.5 (6)
C101—C102—H102116.8N15—C14—H14107.8
C107—C102—H102116.8C13—C14—H14107.8
Ir1—C102—H10289.6C19—C14—H14107.8
C104—C103—C108124.6 (7)C11—N15—C151129.0 (7)
C104—C103—Ir170.1 (5)C11—N15—C14111.3 (6)
C108—C103—Ir1113.6 (6)C151—N15—C14118.0 (6)
C104—C103—H103117.7C152—C151—C150122.2 (7)
C108—C103—H103117.7C152—C151—N15120.3 (7)
Ir1—C103—H10386.3C150—C151—N15117.2 (7)
C103—C104—C105124.9 (8)C151—C152—C153117.5 (7)
C103—C104—Ir170.7 (5)C151—C152—C181124.4 (7)
C105—C104—Ir1110.6 (6)C153—C152—C181118.0 (7)
C103—C104—H104117.5C154—C153—C152121.5 (8)
C105—C104—H104117.5C154—C153—H153119.2
Ir1—C104—H10488.8C152—C153—H153119.2
C104—C105—C106113.9 (7)C153—C154—C155121.5 (8)
C104—C105—H10A108.8C153—C154—H154119.3
C106—C105—H10A108.8C155—C154—H154119.3
C104—C105—H10B108.8C154—C155—C156122.5 (7)
C106—C105—H10B108.8C154—C155—C150119.0 (8)
H10A—C105—H10B107.7C156—C155—C150118.5 (8)
C105—C106—C101112.6 (7)C157—C156—C155121.4 (8)
C105—C106—H10C109.1C157—C156—H156119.3
C101—C106—H10C109.1C155—C156—H156119.3
C105—C106—H10D109.1C156—C157—C158120.9 (8)
C101—C106—H10D109.1C156—C157—H157119.5
H10C—C106—H10D107.8C158—C157—H157119.5
C102—C107—C108112.2 (7)C159—C158—C157118.5 (8)
C102—C107—H10E109.2C159—C158—C191120.1 (7)
C108—C107—H10E109.2C157—C158—C191121.2 (7)
C102—C107—H10F109.2C158—C159—C150122.8 (7)
C108—C107—H10F109.2C158—C159—H159118.6
H10E—C107—H10F107.9C150—C159—H159118.6
C103—C108—C107110.9 (7)C159—C150—C151124.0 (7)
C103—C108—H10G109.5C159—C150—C155117.7 (7)
C107—C108—H10G109.5C151—C150—C155118.2 (7)
C103—C108—H10H109.5C152—C181—C186111.9 (7)
C107—C108—H10H109.5C152—C181—C182110.8 (7)
H10G—C108—H10H108.1C186—C181—C182110.1 (7)
N15—C11—N12107.2 (7)C152—C181—H181108
N15—C11—Ir1126.9 (6)C186—C181—H181108
N12—C11—Ir1125.5 (6)C182—C181—H181108
C11—N12—C121129.1 (7)C183—C182—C181111.9 (7)
C11—N12—C13109.5 (6)C183—C182—H18A109.2
C121—N12—C13120.5 (6)C181—C182—H18A109.2
C122—C121—C120121.0 (7)C183—C182—H18B109.2
C122—C121—N12120.6 (7)C181—C182—H18B109.2
C120—C121—N12117.4 (7)H18A—C182—H18B107.9
C121—C122—C123118.3 (8)C182—C183—C184111.2 (8)
C121—C122—C161123.5 (7)C182—C183—H18C109.4
C123—C122—C161118.0 (7)C184—C183—H18C109.4
C124—C123—C122121.7 (8)C182—C183—H18D109.4
C124—C123—H123119.2C184—C183—H18D109.4
C122—C123—H123119.2H18C—C183—H18D108
C123—C124—C125120.5 (7)C185—C184—C183110.1 (8)
C123—C124—H124119.8C185—C184—H18E109.6
C125—C124—H124119.8C183—C184—H18E109.6
C124—C125—C120119.3 (7)C185—C184—H18F109.6
C124—C125—C126122.3 (7)C183—C184—H18F109.6
C120—C125—C126118.3 (7)H18E—C184—H18F108.2
C127—C126—C125121.1 (7)C184—C185—C186110.7 (8)
C127—C126—H126119.4C184—C185—H18G109.5
C125—C126—H126119.4C186—C185—H18G109.5
C126—C127—C128121.1 (7)C184—C185—H18H109.5
C126—C127—H127119.4C186—C185—H18H109.5
C128—C127—H127119.4H18G—C185—H18H108.1
C129—C128—C127118.2 (8)C181—C186—C185111.2 (7)
C129—C128—C171122.3 (8)C181—C186—H18I109.4
C127—C128—C171119.5 (7)C185—C186—H18I109.4
C128—C129—C120122.6 (7)C181—C186—H18J109.4
C128—C129—H129118.7C185—C186—H18J109.4
C120—C129—H129118.7H18I—C186—H18J108
C125—C120—C129118.5 (7)C158—C191—C196115.1 (7)
C125—C120—C121118.7 (7)C158—C191—C192109.3 (8)
C129—C120—C121122.7 (7)C196—C191—C192108.6 (8)
C122—C161—C166114.4 (7)C158—C191—H191107.8
C122—C161—C162110.4 (6)C196—C191—H191107.8
C166—C161—C162108.4 (7)C192—C191—H191107.8
C122—C161—H161107.8C193—C192—C191113.0 (10)
C166—C161—H161107.8C193—C192—H19A109
C162—C161—H161107.8C191—C192—H19A109
C163—C162—C161110.4 (7)C193—C192—H19B109
C163—C162—H16A109.6C191—C192—H19B109
C161—C162—H16A109.6H19A—C192—H19B107.8
C163—C162—H16B109.6C192—C193—C194111.1 (8)
C161—C162—H16B109.6C192—C193—H19C109.4
H16A—C162—H16B108.1C194—C193—H19C109.4
C164—C163—C162112.3 (8)C192—C193—H19D109.4
C164—C163—H16C109.1C194—C193—H19D109.4
C162—C163—H16C109.1H19C—C193—H19D108
C164—C163—H16D109.1C195—C194—C193111.2 (9)
C162—C163—H16D109.1C195—C194—H19E109.4
H16C—C163—H16D107.9C193—C194—H19E109.4
C163—C164—C165112.7 (7)C195—C194—H19F109.4
C163—C164—H16E109.1C193—C194—H19F109.4
C165—C164—H16E109.1H19E—C194—H19F108
C163—C164—H16F109.1C194—C195—C196111.4 (8)
C165—C164—H16F109.1C194—C195—H19G109.4
H16E—C164—H16F107.8C196—C195—H19G109.4
C164—C165—C166111.0 (7)C194—C195—H19H109.4
C164—C165—H16G109.4C196—C195—H19H109.4
C166—C165—H16G109.4H19G—C195—H19H108
C164—C165—H16H109.4C195—C196—C191112.5 (8)
C166—C165—H16H109.4C195—C196—H19I109.1
H16G—C165—H16H108C191—C196—H19I109.1
C161—C166—C165110.6 (7)C195—C196—H19J109.1
C161—C166—H16I109.5C191—C196—H19J109.1
C165—C166—H16I109.5H19I—C196—H19J107.8
C161—C166—H16J109.5C13—C16—C17106.3 (7)
C165—C166—H16J109.5C13—C16—H16K110.5
H16I—C166—H16J108.1C17—C16—H16K110.5
C128—C171—C172114.4 (7)C13—C16—H16L110.5
C128—C171—C176110.9 (7)C17—C16—H16L110.5
C172—C171—C176109.6 (7)H16K—C16—H16L108.7
C128—C171—H171107.2C18—C17—C16113.5 (7)
C172—C171—H171107.2C18—C17—H17A108.9
C176—C171—H171107.2C16—C17—H17A108.9
C171—C172—C173111.7 (7)C18—C17—H17B108.9
C171—C172—H17C109.3C16—C17—H17B108.9
C173—C172—H17C109.3H17A—C17—H17B107.7
C171—C172—H17D109.3C17—C18—C19113.4 (7)
C173—C172—H17D109.3C17—C18—H18K108.9
H17C—C172—H17D107.9C19—C18—H18K108.9
C174—C173—C172110.2 (8)C17—C18—H18L108.9
C174—C173—H17E109.6C19—C18—H18L108.9
C172—C173—H17E109.6H18K—C18—H18L107.7
C174—C173—H17F109.6C14—C19—C18105.4 (7)
C172—C173—H17F109.6C14—C19—H19K110.7
H17E—C173—H17F108.1C18—C19—H19K110.7
C175—C174—C173111.7 (8)C14—C19—H19L110.7
C175—C174—H17G109.3C18—C19—H19L110.7
C173—C174—H17G109.3H19K—C19—H19L108.8
C106—C101—C102—C107−2.7 (13)C11—N12—C13—C16153.0 (7)
Ir1—C101—C102—C10799.2 (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—C105102.1 (8)N12—C13—C14—C19−161.0 (6)
C108—C103—C104—Ir1−105.5 (8)C16—C13—C14—C1968.3 (9)
C103—C104—C105—C106−42.6 (12)N12—C11—N15—C151−173.3 (7)
Ir1—C104—C105—C10637.6 (9)Ir1—C11—N15—C15113.5 (12)
C104—C105—C106—C101−32.9 (11)N12—C11—N15—C14−8.7 (9)
C102—C101—C106—C10592.2 (10)Ir1—C11—N15—C14178.0 (5)
Ir1—C101—C106—C10512.3 (9)C13—C14—N15—C1126.6 (8)
C101—C102—C107—C108−39.2 (11)C19—C14—N15—C11149.5 (7)
Ir1—C102—C107—C10842.3 (8)C13—C14—N15—C151−167.0 (6)
C104—C103—C108—C10797.0 (10)C19—C14—N15—C151−44.1 (10)
Ir1—C103—C108—C10715.7 (9)C11—N15—C151—C152−87.1 (11)
C102—C107—C108—C103−39.0 (10)C14—N15—C151—C152109.3 (9)
N15—C11—N12—C121177.3 (7)C11—N15—C151—C15097.8 (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—C1530.9 (12)
Ir1—C11—N12—C13159.5 (5)N15—C151—C152—C153−174.0 (7)
C11—N12—C121—C122−83.8 (11)C150—C151—C152—C181177.1 (7)
C13—N12—C121—C122108.3 (8)N15—C151—C152—C1812.2 (12)
C11—N12—C121—C120107.1 (9)C151—C152—C153—C1540.6 (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—C156179.2 (8)
C120—C121—C122—C161170.1 (7)C153—C154—C155—C150−0.9 (13)
N12—C121—C122—C1611.4 (11)C154—C155—C156—C157−178.3 (8)
C121—C122—C123—C1246.9 (11)C150—C155—C156—C1571.8 (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—C1590.9 (12)
C123—C124—C125—C120−4.1 (11)C156—C157—C158—C191176.1 (8)
C123—C124—C125—C126175.3 (7)C157—C158—C159—C1502.6 (12)
C124—C125—C126—C127−179.3 (8)C191—C158—C159—C150−172.6 (7)
C120—C125—C126—C1270.1 (11)C158—C159—C150—C151175.5 (8)
C125—C126—C127—C128−2.9 (12)C158—C159—C150—C155−3.8 (11)
C126—C127—C128—C1292.1 (12)C152—C151—C150—C159178.3 (8)
C126—C127—C128—C171−176.2 (8)N15—C151—C150—C159−6.6 (11)
C127—C128—C129—C1201.4 (11)C152—C151—C150—C155−2.3 (12)
C171—C128—C129—C120179.7 (7)N15—C151—C150—C155172.7 (7)
C124—C125—C120—C129−177.3 (7)C154—C155—C150—C159−178.3 (8)
C126—C125—C120—C1293.2 (10)C156—C155—C150—C1591.6 (11)
C124—C125—C120—C1216.1 (10)C154—C155—C150—C1512.3 (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—C186122.8 (8)
C128—C129—C120—C121172.4 (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—C125167.5 (7)C153—C152—C181—C18262.3 (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—C166131.4 (8)C181—C182—C183—C18456.4 (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—C18657.5 (10)
C123—C122—C161—C16268.8 (9)C152—C181—C186—C185178.7 (7)
C122—C161—C162—C163174.2 (7)C182—C181—C186—C18555.0 (9)
C166—C161—C162—C163−59.9 (9)C184—C185—C186—C181−57.3 (10)
C161—C162—C163—C16454.9 (9)C159—C158—C191—C196−136.9 (8)
C162—C163—C164—C165−50.8 (10)C157—C158—C191—C19648.0 (11)
C163—C164—C165—C16651.6 (10)C159—C158—C191—C192100.5 (9)
C122—C161—C166—C165−174.7 (7)C157—C158—C191—C192−74.5 (10)
C162—C161—C166—C16561.6 (9)C158—C191—C192—C193−179.2 (9)
C164—C165—C166—C161−57.7 (10)C196—C191—C192—C19354.5 (12)
C129—C128—C171—C17226.9 (11)C191—C192—C193—C194−55.7 (15)
C127—C128—C171—C172−154.8 (7)C192—C193—C194—C19555.3 (14)
C129—C128—C171—C176−97.7 (9)C193—C194—C195—C196−55.6 (12)
C127—C128—C171—C17680.6 (9)C194—C195—C196—C19156.4 (11)
C128—C171—C172—C173178.1 (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—C17457.3 (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—C17654.9 (10)C13—C16—C17—C1852.6 (10)
C128—C171—C176—C175−177.5 (7)C16—C17—C18—C19−52.6 (10)
C172—C171—C176—C17555.2 (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—C1429.7 (8)C17—C18—C19—C1453.5 (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).

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 76| Part 10| October 2020| Pages 1543-1547
https://doi.org/10.1107/S2056989020011603
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