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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 9| Part 9| September 2024| x240941
https://doi.org/10.1107/S2414314624009416

[(1,2,5,6-η)-Cyclo­octa-1,5-diene](1-ethyl-4-iso­butyl-1,2,4-triazol-5-yl­­idene)(tri­phenyl­phosphane)iridium(I) tetra­fluorido­borate di­chloro­methane hemisolvate

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Timothy G. Lerch,a Michael Gau,b Daniel R. Alberta and Edward Rajaseelana*

aDepartment of Chemistry, Millersville University, Millersville, PA 17551, USA, and bDepartment of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA
*Correspondence e-mail: edward.rajaseelan@millersville.edu

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 23 September 2024; accepted 24 September 2024; online 30 September 2024)

A new triazole-based N-heterocyclic carbene IrI cationic complex with a tetra­fluorido­borate counter-anion and hemi-solvating di­chloro­methane, [Ir(C8H12)(C8H15N3)(C18H15P)]BF4·0.5CH2Cl2, has been synthesized and structurally characterized. There are two independent ion pairs in the asymmetric unit and one di­chloro­methane solvent mol­ecule per two ion pairs. The cationic complex exhibits a distorted square-planar conformation around the IrI atom, formed by a bidentate cyclo­octa-1,5,diene (COD) ligand, a tri­phenyl­phosphane ligand, and an N-heterocyclic carbene (NHC). There are several close non-standard H⋯F hydrogen-bonding inter­actions that orient the tetra­fluorido­borate anions with respect to the IrI complex mol­ecules. The complex shows promising catalytic activity in transfer hydrogenation reactions. The structure was refined as a non-merohedral twin, and one of the COD mol­ecules is statistically disordered.

CCDC reference: 2386332

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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

N-heterocyclic carbenes (NHCs) have been considered alternatives to phosphanes as spectator ligands in homogeneous catalysis and can be tuned sterically and electronically by having different substituent groups on the nitro­gen atoms (Cazin, 2013[Cazin, C. S. J. (2013). Dalton Trans. 42, 7254.]; Diez-González et al., 2009[Díez-González, S., Marion, N. & Nolan, S. P. (2009). Chem. Rev. 109, 3612-3676.]; Rovis & Nolan, 2013[Rovis, T. & Nolan, S. (2013). Synlett, 24, 1188-1189.]; Ruff et al., 2016[Ruff, A., Kirby, C., Chan, B. C. & O'Connor, A. R. (2016). Organometallics, 35, 327-335.]; Zuo et al., 2014[Zuo, W., Tauer, S., Prokopchuk, D. E. & Morris, R. H. (2014). Organometallics, 33, 5791-5801.]; Diez-González & Nolan, 2007[Díez-González, S. & Nolan, S. P. (2007). Coord. Chem. Rev. 251, 874-883.]; Gusev, 2009[Gusev, D. G. (2009). Organometallics, 28, 6458-6461.]). Their catalytic activity in the transfer hydrogenation of ketones and imines has also been reported (Albrecht et al., 2002[Albrecht, M., Miecznikowski, J. R., Samuel, A., Faller, J. W. & Crabtree, R. H. (2002). Organometallics, 21, 3596-3604.]; Gnanamgari et al., 2007[Gnanamgari, D., Moores, A., Rajaseelan, E. & Crabtree, R. H. (2007). Organometallics, 26, 1226-1230.]). Many imidazole- and triazole-based NHC rhodium and iridium complexes have been synthesized and structurally characterized (Herrmann et al., 2006[Herrmann, W. A., Schütz, J., Frey, G. D. & Herdtweck, E. (2006). Organometallics, 25, 2437-2448.]; Wang & Lin 1998[Wang, H. M. J. & Lin, I. J. B. (1998). Organometallics, 17, 972-975.]; Chianese et al., 2004[Chianese, A. R., Kovacevic, A., Zeglis, B. M., Faller, J. W. & Crabtree, R. H. (2004). Organometallics, 23, 2461-2468.]). We continue to synthesize new imidazole- and triazole-based NHC complexes of rhodium and iridium, to study the effect of different substituents on the NHCs and the other ligands coordinated to the metal in transfer hydrogenation reactions (Nichol et al., 2009[Nichol, G. S., Rajaseelan, J., Anna, L. J. & Rajaseelan, E. (2009). Eur. J. Inorg. Chem. pp, 4320-4328.], 2010[Nichol, G. S., Stasiw, D., Anna, L. J. & Rajaseelan, E. (2010). Acta Cryst. E66, m1114.], 2011[Nichol, G. S., Rajaseelan, J., Walton, D. P. & Rajaseelan, E. (2011). Acta Cryst. E67, m1860-m1861.], 2012[Nichol, G. S., Walton, D. P., Anna, L. J. & Rajaseelan, E. (2012). Acta Cryst. E68, m158-m159.]; Idrees et al., 2017a[Idrees, K. B., Rutledge, W. J., Roberts, S. A. & Rajaseelan, E. (2017a). IUCrData, 2, x171411.],b[Idrees, K. B., Astashkin, A. V. & Rajaseelan, E. (2017b). IUCrData, 2, x171081.]; Rood et al., 2021[Rood, J., Subedi, C. B., Risell, J. P., Astashkin, A. V. & Rajaseelan, E. (2021). IUCrData, 6, x210597.]; Rushlow et al., 2021[Rushlow, J., Astashkin, A. V., Albert, D. R. & Rajaseelan, E. (2021). IUCrData, 6, x210811.]; Newman et al., 2021[Newman, E. B., Astashkin, A. V., Albert, D. R. & Rajaseelan, E. (2021). IUCrData, 6, x210836.]; Castaldi et al., 2021[Castaldi, K. T., Astashkin, A. V., Albert, D. R. & Rajaseelan, E. (2021). IUCrData, 6, x211142.]; Maynard et al., 2023[Maynard, A., Gau, M., Albert, D. R. & Rajaseelan, E. (2023). IUCrData, 8, x230903.]; Lerch et al., 2024a[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024a). IUCrData, 9, x240501.],b[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024b). IUCrData, 9, x240060.],c[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024c). IUCrData, 9, x240704.],d[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024d). IUCrData, 9, x240745.]). The asymmetric unit of the title complex, [Ir(C8H12)(C18H15P)(C8H15N3)][BF4] (3), comprises two independent IrI complex cations (A containing Ir1 and B containing Ir1′) and two independent tetra­fluorido­borate counter-anions, Fig. 1[link]. One di­chloro­methane solvent mol­ecule per two ion pairs was also found in the crystal, Fig. 1[link].

[Figure 1]
Figure 1
Mol­ecular entities of the title compound (3) showing the atom-labeling scheme and with displacement ellipsoids drawn at the 50% probability level.

The coordination sphere around the IrI ion is formed by the bidentate (1,2,5,6-η)-cyclo­octa-1,5-diene (COD), NHC, and tri­phenyl­phosphane ligands, resulting in a distorted square-planar geometry. The distorted square-planar geometry around the IrI atoms is characterized by CNHC— Ir—P bond angles of 93.5 (5)° for cation A and 93.4 (4)° for cation B. The N—C—N bond angles of the NHC ligand are 103.9 (10) and 103.7 (10)° for cations A and B, respectively. Other selected bond lengths in cations A and B are Ir—CNHC = 2.035 (13) and 2.029 (12) Å, and Ir—P = 2.323 (4) and 2.329 (4) Å. The wing tip substituents in the carbene ligand are anti with respect to one another as shown in Fig. 2[link]. Fig. 3[link] shows several close F⋯H contacts (likely, non-standard hydrogen bonds) shown as dotted orange lines stabilizing the orientation of [BF4−], Table 1[link]. Notably, the incorporated di­chloro­methane solvate does not exhibit hydrogen-bonding inter­actions with the cationic complex.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯F8i 0.95 2.32 3.18 (2) 149
C19—H19⋯F1ii 0.95 2.50 3.380 (19) 154
C2′—H2′⋯F5iii 0.95 2.26 3.171 (18) 161
C13′—H13′⋯F2iii 0.95 2.56 3.38 (2) 144
C18′—H18′⋯F8 0.95 2.52 3.319 (16) 142
C33"—H33B⋯F3ii 0.99 2.24 3.08 (3) 143
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x-1, y, z]; (iii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z].
[Figure 2]
Figure 2
In the title compound (3), ethyl (C3 and C4) and isobutyl (C5–C7) wingtips exhibit an anti configuration with regards to the NHC.
[Figure 3]
Figure 3
Mol­ecular packing diagram showing hydrogen-bonding inter­actions as dotted orange lines.

Synthesis and crystallization

The synthesis of 1-ethyl-4-isobutyl-1,2,4-triazolium bromide (1) has been published previously (Lerch et al., 2024c[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024c). IUCrData, 9, x240704.]). All other compounds used in the syntheses, shown in Fig. 4[link], were obtained from Sigma-Aldrich and Strem, and used as received; all syntheses were performed under a nitro­gen atmosphere. NMR spectra were recorded at room temperature in CDCl3 on a 400 MHz (operating at 100 MHz for 13C, and 162 MHz for 31P) Varian spectrometer and referenced to the residual solvent peak (δ in p.p.m.). The title compound (3) was crystallized by slow diffusion of pentane into a CH2Cl2 solution.

[Figure 4]
Figure 4
Reaction scheme for the synthesis of the title compound (3).

Chloro­[(1,2,5,6-η)-cyclo­octa-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-yl­idene)iridium(I) (2): Triazolium bromide (1) (0.070 g, 0.298 mmol) and Ag2O (0.035 g, 0.149 mmol) were stirred at room temperature in the dark for 1 h in CH2Cl2 (10 ml). The mixture was then filtered through Celite into [Ir(cod)Cl]2 (0.100 g, 0.149 mmol), and stirred again in the dark for 1.5 h. The resulting solution was filtered through Celite and the solvent was removed under reduced pressure in a rotavapor. The yellow–orange solid product (2) was dried under vacuum. Yield: 0.129 g (88.5%). 1H NMR: δ 7.83 (s, 1H, N—C3H—N), 4.73 (q, 2H, N—CH2 of eth­yl), 4.64 (d, 2H, N—CH2 of isobut­yl), 4.58 (m, 2H, CH of COD), 4.20 (m, 2H, CH of COD), 3.01, 2.84(m, 4H, CH2 of COD), 2.48, 2.27 (m, 4H, CH2 of COD), 1.88 (m, 1H, CH of isobut­yl), 1.54 (t, 3H, CH3 of eth­yl), 1.04 (d, 6H, CH3 of isobut­yl). 13C NMR: δ 182.54, 142.17 (N—C3H—N), 86.33, 85.66 (CH of COD), 55.94 (N—CH2 of isobut­yl), 47.78 (N—CH2 of eth­yl), 33.99, 33.00, 30.06, 29.03 (CH2 of COD), 28.91 (CH of isobut­yl), 20.28 (CH3 of isobut­yl), 15.36 (CH3 of eth­yl).

[(1,2,5,6-η)-Cyclo­octa-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-yl­idene)(tri­phenyl­phosphane)iridium(I) tetra­fluor­ido­borate (3): Tri­phenyl­phosphane (0.069 g, 0.264 mmol) and AgBF4 (0.051 g, 0.264 mmol) were added to (2) (0.129 g, 0.264 mmol) in CH2Cl2 (15 ml). The solution was stirred in the dark for 1.5 h. The resulting mixture was filtered through Celite and the solvent was removed under reduced pressure. The bright orange–red solid product (3) was dried under vacuum. Yield: 0.212 g (100%). 1H NMR: δ 8.08 (s, 1H, N—C3H—N), 7.48-7.25 (m, 15H, aromatic-H), 4.72 (q, 2H, N—CH2 of eth­yl), 4.47 (d, 2H, N—CH2 of isobut­yl), 4.24 (m, 2H, CH of COD), 4.08 (m, 2H, CH of COD), 2.60 (m, 4H, CH2 of COD), 2.48 (m, 2H, CH2 of COD), 2.23 (m, 2H, CH2 of COD), 2.06 (m, 1H, CH of isobut­yl), 1.23 (t, 3H, CH3 of eth­yl), 0.92 (d, 6H, CH3 of isobut­yl). 13C NMR: δ 178.03, 143.94 (N—C3H—N), 133.65–129.07 (Caromatic), 87.80, 87.69, 85.49, 85.37 (CH of COD), 55.66 (N—CH2 of isobut­yl), 47.90 (N—CH2 of eth­yl), 31.68, 31.67, 31.20, 31.16 (CH2 of COD), 28.09 (CH of isobut­yl), 19.95 (CH3 of isobut­yl), 13.83 (CH3 of eth­yl).31P NMR: δ 17.44.

Refinement

Crystal data and refinement details are summarized in Table 2[link]. The crystal grew as a non-merohedral twin. This was evident due to the double spots in the diffraction pattern and only a partial fit of all spots to the determined unit cell. Due to the large number of overlaps and almost pseudo-merohedral nature of the twinning, TWINROTMAT (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]) was utilized to determine the twin matrix (−1 0 0 0 −1 0 0.146 0 1) after initial solution. Rotation frames were integrated using CrysAlis PRO (Rigaku OD, 2024[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), producing a listing of unaveraged F2 and σ(F2) values. All carbon atoms of the COD ligand of cation B are disordered over adjacent sites in a 0.50:0.50 ratio. The maximum and minimum electron density peaks of 1.91 and 1.42 e Å−3, respectively, are located 1.04 and 1.11 Å from the H32′ and H4′C atoms, respectively.

Table 2
Experimental details

Crystal data
Chemical formula [Ir(C8H12)(C8H15N3)(C18H15P)]BF4·0.5CH2Cl2
Mr 845.17
Crystal system, space group Monoclinic, Cc
Temperature (K) 100
a, b, c (Å) 13.19118 (17), 13.5580 (2), 38.8216 (7)
β (°) 91.4236 (14)
V (Å3) 6940.96 (18)
Z 8
Radiation type Mo Kα
μ (mm−1) 4.02
Crystal size (mm) 0.17 × 0.11 × 0.02 × 0.81 (radius)
 
Data collection
Diffractometer Rigaku XtaLAB Synergy-S
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2024[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.072, 0.097
No. of measured, independent and observed [I > 2σ(I)] reflections 71611, 16962, 16233
Rint 0.056
(sin θ/λ)max (Å−1) 0.667
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.133, 1.08
No. of reflections 16962
No. of parameters 889
No. of restraints 558
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.91, −1.42
Absolute structure Twinning involves inversion, so Flack parameter cannot be determined
Computer programs: CrysAlis PRO (Rigaku OD, 2024[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), 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 publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 2386332

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624009416/tk4109sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624009416/tk4109Isup2.hkl

checkCIF report


Computing details top

[(1,2,5,6-η)-Cycloocta-1,5-diene](1-ethyl-4-isobutyl-1,2,4-triazol-5-ylidene)(triphenylphosphane)iridium(I) tetrafluoridoborate dichloromethane hemisolvate top
Crystal data top
[Ir(C8H12)(C8H15N3)(C18H15P)]BF4·0.5CH2Cl2F(000) = 3368
Mr = 845.17Dx = 1.618 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 13.19118 (17) ÅCell parameters from 42032 reflections
b = 13.5580 (2) Åθ = 2.1–28.2°
c = 38.8216 (7) ŵ = 4.02 mm−1
β = 91.4236 (14)°T = 100 K
V = 6940.96 (18) Å3Plate, red
Z = 80.17 × 0.11 × 0.02 × 0.81 (radius) mm
Data collection top
Rigaku XtaLAB Synergy-S
diffractometer		16233 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm-1Rint = 0.056
ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2024)		h = −16→17
Tmin = 0.072, Tmax = 0.097k = −17→18
71611 measured reflectionsl = −51→51
16962 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0699P)2 + 71.6254P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133(Δ/σ)max < 0.001
S = 1.08Δρmax = 1.91 e Å−3
16962 reflectionsΔρmin = −1.42 e Å−3
889 parametersAbsolute structure: Twinning involves inversion, so Flack parameter cannot be determined
558 restraints
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. Refined as a 4-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ir10.12659 (3)0.60645 (4)0.29374 (2)0.02226 (12)
P10.0178 (3)0.4738 (3)0.28445 (10)0.0200 (7)
N1−0.0280 (10)0.7663 (8)0.2806 (3)0.025 (2)
N2−0.0786 (11)0.8231 (10)0.2561 (3)0.033 (3)
N30.0287 (10)0.7215 (9)0.2317 (3)0.027 (3)
C10.0370 (11)0.7016 (10)0.2662 (3)0.026 (3)
C2−0.0430 (13)0.7942 (11)0.2273 (4)0.036 (4)
H2−0.0638780.8200100.2055330.043*
C3−0.0482 (11)0.7760 (11)0.3170 (3)0.029 (3)
H3A−0.0432680.8462800.3238480.035*
H3B0.0032720.7386230.3306790.035*
C4−0.1546 (13)0.7367 (14)0.3248 (5)0.046 (5)
H4A−0.2054630.7742530.3114130.068*
H4B−0.1672140.7440300.3494070.068*
H4C−0.1589260.6668900.3184030.068*
C50.0804 (15)0.6657 (12)0.2052 (4)0.039 (4)
H5A0.0326350.6167150.1951170.047*
H5B0.1376230.6290900.2161480.047*
C60.1211 (15)0.7302 (13)0.1763 (4)0.049 (5)
H60.0635740.7685410.1656690.059*
C70.2020 (17)0.8026 (18)0.1900 (6)0.060 (6)
H7A0.1722940.8460750.2071490.090*
H7B0.2269900.8422400.1708370.090*
H7C0.2584620.7656260.2005830.090*
C80.166 (2)0.6631 (16)0.1488 (6)0.067 (8)
H8A0.2251010.6283110.1585880.100*
H8B0.1867950.7031880.1291760.100*
H8C0.1148870.6150610.1410360.100*
C90.0541 (9)0.4071 (9)0.2458 (3)0.021 (3)
C100.1512 (11)0.4195 (11)0.2325 (4)0.033 (3)
H100.1978900.4639630.2431600.040*
C110.1784 (13)0.3665 (13)0.2036 (4)0.037 (4)
H110.2443400.3749000.1947000.045*
C120.1115 (12)0.3014 (13)0.1873 (4)0.041 (4)
H120.1306420.2661070.1674000.049*
C130.0159 (12)0.2891 (13)0.2009 (4)0.040 (4)
H13−0.0298120.2431650.1905760.048*
C14−0.0142 (12)0.3431 (12)0.2296 (4)0.033 (4)
H14−0.0808600.3361110.2379490.040*
C15−0.1178 (10)0.4993 (10)0.2758 (3)0.021 (3)
C16−0.1438 (10)0.5503 (10)0.2457 (3)0.024 (3)
H16−0.0916240.5672760.2303480.029*
C17−0.2428 (10)0.5776 (12)0.2372 (4)0.034 (4)
H17−0.2584230.6117380.2163760.041*
C18−0.3187 (11)0.5533 (12)0.2603 (4)0.034 (4)
H18−0.3866440.5732590.2555250.040*
C19−0.2954 (10)0.5002 (12)0.2900 (4)0.031 (3)
H19−0.3476430.4825380.3052640.037*
C20−0.1948 (8)0.4726 (11)0.2976 (4)0.024 (3)
H20−0.1792760.4354240.3178070.029*
C210.0219 (11)0.3790 (9)0.3183 (3)0.024 (2)
C22−0.0174 (12)0.4027 (10)0.3503 (3)0.026 (2)
H22−0.0482270.4650120.3539770.032*
C23−0.0107 (11)0.3333 (9)0.3770 (4)0.029 (2)
H23−0.0377860.3486460.3988020.035*
C240.0347 (11)0.2427 (10)0.3720 (4)0.029 (2)
H240.0391520.1964530.3903790.035*
C250.0740 (11)0.2193 (10)0.3402 (3)0.027 (2)
H250.1051860.1570880.3366350.032*
C260.0673 (11)0.2875 (8)0.3135 (4)0.024 (2)
H260.0941570.2714520.2917310.029*
C270.2489 (11)0.5091 (12)0.3141 (4)0.031 (3)
H270.2364420.4372730.3100550.037*
C280.1966 (12)0.5479 (10)0.3413 (4)0.031 (2)
H280.1534930.4984410.3532000.037*
C290.2301 (13)0.6338 (10)0.3643 (4)0.035 (3)
H29E0.2809050.6097490.3814710.041*
H29F0.1708050.6580960.3769370.041*
C300.2759 (13)0.7200 (12)0.3442 (4)0.036 (3)
H30E0.3486910.7068640.3406670.043*
H30F0.2706540.7811270.3580300.043*
C310.2222 (12)0.7357 (13)0.3090 (4)0.038 (3)
H310.1873670.8009360.3064410.045*
C320.2560 (12)0.6968 (12)0.2788 (4)0.037 (3)
H320.2427380.7391680.2581040.045*
C330.3472 (13)0.6270 (12)0.2757 (5)0.040 (3)
H33E0.3442020.5960740.2525580.048*
H33F0.4102060.6665690.2772790.048*
C340.3535 (11)0.5449 (11)0.3029 (4)0.036 (3)
H34E0.3913850.4883710.2935450.043*
H34F0.3918360.5696510.3234160.043*
Ir1'−0.01715 (3)0.52789 (4)0.48110 (2)0.02538 (13)
P1'0.1221 (3)0.4294 (3)0.49566 (10)0.0213 (7)
N1'−0.1804 (9)0.3761 (9)0.4955 (3)0.027 (2)
N2'−0.2398 (10)0.3379 (10)0.5211 (3)0.030 (2)
N3'−0.1352 (9)0.4473 (10)0.5432 (3)0.027 (2)
C1'−0.1142 (10)0.4454 (10)0.5088 (3)0.026 (2)
C2'−0.2114 (12)0.3794 (12)0.5492 (4)0.030 (2)
H2'−0.2384960.3657320.5711060.037*
C3'−0.1921 (13)0.3438 (10)0.4603 (3)0.030 (3)
H3'A−0.1547800.3894430.4452320.036*
H3'B−0.2646990.3465700.4533040.036*
C4'−0.1526 (13)0.2384 (10)0.4550 (4)0.034 (4)
H4'A−0.1529850.2232210.4302920.051*
H4'B−0.1964300.1916610.4668040.051*
H4'C−0.0832570.2331950.4644390.051*
C5'−0.0792 (11)0.5054 (13)0.5686 (4)0.032 (3)
H5'A−0.0386420.5554070.5565000.038*
H5'B−0.0312560.4614580.5812770.038*
C6'−0.1455 (13)0.5580 (14)0.5948 (4)0.044 (4)
H6'−0.1909530.5081280.6053910.052*
C7'−0.2117 (18)0.6360 (17)0.5766 (6)0.064 (7)
H7'A−0.1705370.6735260.5605460.097*
H7'B−0.2393460.6808410.5938240.097*
H7'C−0.2674390.6035020.5639440.097*
C8'−0.0759 (17)0.601 (2)0.6231 (6)0.061 (6)
H8'A−0.0333690.5484730.6330630.092*
H8'B−0.1171600.6300350.6411780.092*
H8'C−0.0326770.6520740.6133160.092*
C9'0.0980 (11)0.3001 (9)0.5057 (3)0.027 (2)
C10'0.0410 (11)0.2791 (9)0.5344 (4)0.028 (2)
H10'0.0205210.3318590.5487320.033*
C11'0.0132 (12)0.1838 (9)0.5428 (4)0.031 (2)
H11'−0.0228720.1718620.5633070.037*
C12'0.0377 (11)0.1063 (10)0.5216 (4)0.031 (2)
H12'0.0149610.0412750.5263520.037*
C13'0.0965 (12)0.1254 (10)0.4930 (4)0.031 (2)
H13'0.1173280.0722060.4788980.037*
C14'0.1252 (11)0.2211 (8)0.4847 (4)0.030 (2)
H14'0.1635570.2328280.4647120.036*
C15'0.1889 (8)0.4708 (7)0.5348 (2)0.030 (2)
C16'0.1769 (8)0.5668 (7)0.5466 (3)0.033 (3)
H16'0.1314110.6103970.5349450.040*
C17'0.2313 (9)0.5988 (6)0.5756 (3)0.038 (3)
H17'0.2231100.6643520.5837590.046*
C18'0.2978 (9)0.5349 (9)0.5928 (3)0.043 (3)
H18'0.3350590.5568510.6125870.052*
C19'0.3099 (9)0.4390 (8)0.5809 (3)0.042 (3)
H19'0.3553110.3953930.5926020.050*
C20'0.2554 (9)0.4070 (6)0.5519 (3)0.036 (3)
H20'0.2636130.3414360.5437880.043*
C21'0.2197 (9)0.4283 (10)0.4638 (3)0.023 (2)
C22'0.3140 (9)0.4729 (11)0.4687 (4)0.026 (2)
H22'0.3314990.5012100.4904450.032*
C23'0.3829 (11)0.4764 (12)0.4422 (3)0.032 (2)
H23'0.4467550.5075470.4458940.038*
C24'0.3587 (11)0.4348 (11)0.4105 (4)0.031 (2)
H24'0.4063350.4366420.3925150.037*
C25'0.2650 (10)0.3904 (11)0.4048 (4)0.030 (2)
H25'0.2481140.3607030.3832860.037*
C26'0.1964 (11)0.3904 (11)0.4313 (3)0.027 (2)
H26'0.1308000.3633050.4271090.033*
C27"0.044 (3)0.593 (3)0.4333 (10)0.026 (3)0.5
H27"0.0948190.5510530.4211950.031*0.5
C27'0.058 (3)0.604 (3)0.4385 (9)0.026 (3)0.5
H27'0.1169100.5666590.4290580.031*0.5
C28"0.082 (3)0.642 (3)0.4619 (10)0.026 (3)0.5
H28"0.1556910.6314680.4671040.032*0.5
C28'0.083 (3)0.658 (3)0.4676 (10)0.026 (3)0.5
H28'0.1548700.6507930.4757420.031*0.5
C29"0.039 (2)0.740 (3)0.4755 (13)0.028 (3)0.5
H29A0.0652590.7944560.4611250.033*0.5
H29B0.0664500.7504350.4992660.033*0.5
C29'0.033 (3)0.756 (3)0.4776 (12)0.028 (3)0.5
H29C0.0845660.7986200.4890270.034*0.5
H29D0.0093570.7902670.4562420.034*0.5
C30"−0.0776 (19)0.7476 (18)0.4760 (9)0.027 (3)0.5
H30A−0.0978940.7916050.4949990.033*0.5
H30B−0.1034190.7762780.4540330.033*0.5
C30'−0.058 (2)0.7451 (18)0.5016 (8)0.028 (3)0.5
H30C−0.0332250.7432250.5258970.033*0.5
H30D−0.1039380.8022770.4987480.033*0.5
C31"−0.124 (2)0.6450 (18)0.4810 (8)0.025 (3)0.5
H31"−0.1704450.6419160.5008410.030*0.5
C31'−0.116 (3)0.649 (2)0.4928 (8)0.026 (3)0.5
H31'−0.1620710.6310980.5117840.031*0.5
C32"−0.155 (3)0.588 (2)0.4535 (6)0.026 (3)0.5
H32"−0.2187440.5493000.4575430.031*0.5
C32'−0.150 (3)0.611 (2)0.4618 (6)0.026 (3)0.5
H32'−0.2166700.5752590.4624330.031*0.5
C33"−0.1362 (18)0.611 (2)0.4155 (7)0.026 (3)0.5
H33A−0.1867970.6594260.4071140.031*0.5
H33B−0.1459130.5495430.4017630.031*0.5
C33'−0.127 (2)0.661 (2)0.4274 (7)0.027 (3)0.5
H33C−0.1837830.6501390.4107550.033*0.5
H33D−0.1202510.7333660.4310490.033*0.5
C34"−0.0288 (19)0.651 (2)0.4095 (9)0.027 (3)0.5
H34A−0.0105140.6425050.3851590.032*0.5
H34B−0.0258720.7223830.4151800.032*0.5
C34'−0.0283 (19)0.622 (2)0.4120 (8)0.027 (3)0.5
H34C−0.0435140.5587160.4000710.032*0.5
H34D−0.0048110.6690950.3945470.032*0.5
Cl10.5771 (7)0.5278 (8)0.6159 (3)0.102 (3)
Cl20.4852 (9)0.4734 (6)0.6780 (3)0.106 (3)
C350.586 (3)0.462 (3)0.6547 (11)0.106 (6)
H35A0.5974670.3916250.6496420.127*
H35B0.6459950.4863890.6682520.127*
F10.5708 (10)0.4784 (10)0.3628 (3)0.053 (3)
F20.6253 (10)0.5096 (16)0.4169 (4)0.088 (6)
F30.7346 (10)0.4513 (11)0.3786 (4)0.062 (4)
F40.6099 (13)0.3549 (12)0.3985 (4)0.085 (6)
B10.635 (2)0.450 (2)0.3893 (6)0.052 (7)
F50.2490 (9)0.8110 (9)0.6258 (3)0.046 (3)
F60.4174 (9)0.8114 (8)0.6123 (3)0.046 (3)
F70.3683 (15)0.8643 (12)0.6646 (4)0.087 (6)
F80.3589 (11)0.7035 (11)0.6517 (3)0.057 (3)
B20.348 (2)0.7976 (18)0.6386 (6)0.051 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.0198 (2)0.0156 (2)0.0313 (2)−0.0022 (2)−0.00146 (19)0.0036 (2)
P10.0198 (18)0.0155 (16)0.0247 (17)−0.0010 (13)0.0018 (13)0.0004 (13)
N10.033 (7)0.016 (6)0.026 (6)0.001 (5)0.000 (5)−0.003 (4)
N20.042 (8)0.023 (6)0.034 (7)0.012 (6)−0.005 (6)−0.003 (5)
N30.029 (7)0.025 (6)0.028 (6)0.005 (5)0.002 (5)0.006 (5)
C10.025 (7)0.023 (7)0.030 (7)0.001 (6)0.003 (6)−0.001 (6)
C20.043 (10)0.026 (8)0.039 (9)0.006 (7)−0.001 (7)0.011 (6)
C30.039 (9)0.021 (7)0.028 (7)0.007 (6)−0.003 (6)−0.004 (5)
C40.055 (12)0.038 (10)0.045 (11)0.013 (9)0.028 (9)0.006 (8)
C50.044 (10)0.042 (10)0.033 (8)−0.006 (8)0.012 (7)0.003 (7)
C60.056 (12)0.051 (11)0.042 (10)0.008 (10)0.010 (9)0.017 (9)
C70.055 (14)0.062 (15)0.063 (14)−0.009 (12)0.012 (11)0.019 (11)
C80.091 (19)0.053 (14)0.059 (14)0.002 (13)0.043 (14)0.019 (11)
C90.027 (7)0.016 (6)0.021 (6)0.004 (5)0.003 (5)0.004 (5)
C100.027 (8)0.031 (8)0.042 (9)0.007 (6)0.006 (7)0.007 (6)
C110.030 (9)0.039 (10)0.043 (10)0.012 (8)0.010 (7)0.000 (8)
C120.048 (11)0.046 (10)0.029 (8)0.019 (9)0.006 (8)−0.006 (7)
C130.048 (11)0.030 (8)0.042 (10)0.007 (8)−0.014 (8)−0.012 (7)
C140.032 (9)0.036 (9)0.033 (8)−0.001 (7)−0.001 (6)−0.005 (6)
C150.027 (7)0.014 (6)0.023 (7)−0.007 (5)−0.005 (5)−0.003 (5)
C160.029 (8)0.017 (6)0.028 (7)0.001 (5)0.005 (6)0.005 (5)
C170.036 (9)0.031 (8)0.036 (9)−0.004 (7)0.001 (7)0.007 (7)
C180.023 (8)0.032 (8)0.046 (9)−0.002 (6)−0.006 (7)0.000 (7)
C190.014 (6)0.035 (8)0.043 (9)0.003 (6)0.003 (6)0.004 (7)
C200.011 (6)0.030 (7)0.031 (7)−0.007 (5)−0.001 (5)0.001 (6)
C210.026 (5)0.015 (4)0.029 (5)−0.005 (4)−0.004 (4)−0.003 (4)
C220.026 (5)0.022 (5)0.031 (5)−0.003 (4)0.002 (4)−0.001 (4)
C230.026 (5)0.029 (5)0.031 (5)−0.005 (4)0.000 (4)0.001 (4)
C240.025 (5)0.028 (5)0.034 (5)−0.005 (4)−0.005 (4)0.005 (4)
C250.025 (5)0.022 (5)0.034 (5)−0.003 (4)−0.003 (4)0.006 (4)
C260.024 (5)0.017 (5)0.032 (5)−0.004 (4)0.001 (4)0.000 (4)
C270.027 (5)0.020 (5)0.045 (6)−0.004 (4)−0.005 (5)0.000 (5)
C280.027 (5)0.020 (5)0.044 (6)−0.008 (4)−0.006 (5)0.001 (5)
C290.029 (5)0.028 (5)0.046 (6)−0.006 (5)−0.005 (5)−0.002 (5)
C300.026 (5)0.030 (5)0.052 (6)−0.005 (5)−0.006 (5)0.002 (5)
C310.029 (5)0.028 (5)0.056 (6)−0.009 (5)−0.009 (5)0.005 (5)
C320.025 (5)0.033 (6)0.053 (6)−0.008 (5)−0.005 (5)0.009 (5)
C330.033 (5)0.033 (6)0.055 (6)−0.004 (5)−0.001 (5)0.003 (5)
C340.033 (5)0.024 (5)0.050 (6)−0.002 (5)0.001 (5)0.000 (5)
Ir1'0.0153 (2)0.0190 (2)0.0422 (3)0.0032 (2)0.0069 (2)0.0088 (2)
P1'0.0140 (17)0.0199 (17)0.0301 (18)0.0021 (14)0.0028 (13)0.0029 (14)
N1'0.022 (4)0.025 (5)0.036 (5)−0.007 (4)0.008 (4)0.006 (4)
N2'0.024 (5)0.032 (5)0.036 (5)−0.007 (4)0.006 (4)0.008 (4)
N3'0.020 (4)0.028 (5)0.034 (5)0.000 (4)0.004 (4)−0.001 (4)
C1'0.020 (5)0.024 (5)0.033 (5)0.001 (4)0.009 (4)0.002 (4)
C2'0.023 (5)0.033 (5)0.036 (5)−0.002 (4)0.005 (4)0.006 (4)
C3'0.034 (9)0.023 (7)0.033 (8)0.004 (7)0.000 (7)0.009 (6)
C4'0.038 (9)0.029 (8)0.034 (8)−0.007 (7)−0.004 (7)0.001 (7)
C5'0.026 (8)0.036 (9)0.032 (8)0.000 (7)−0.004 (6)−0.005 (7)
C6'0.038 (10)0.043 (11)0.049 (11)0.011 (8)0.008 (8)−0.006 (8)
C7'0.048 (13)0.064 (15)0.081 (17)0.029 (12)−0.006 (12)−0.020 (12)
C8'0.050 (13)0.066 (16)0.068 (15)0.008 (12)0.002 (11)−0.010 (12)
C9'0.019 (5)0.017 (5)0.045 (5)0.000 (4)−0.001 (4)0.005 (4)
C10'0.022 (5)0.016 (5)0.044 (6)0.003 (4)0.001 (4)0.004 (4)
C11'0.023 (5)0.022 (5)0.049 (6)0.002 (4)0.006 (5)0.008 (5)
C12'0.024 (5)0.018 (5)0.051 (6)0.000 (4)0.003 (5)0.008 (5)
C13'0.024 (5)0.018 (5)0.052 (6)0.004 (4)0.002 (5)0.002 (4)
C14'0.021 (5)0.019 (5)0.050 (6)−0.004 (4)0.000 (5)0.000 (4)
C15'0.031 (5)0.029 (5)0.031 (5)0.000 (5)0.004 (5)0.002 (4)
C16'0.034 (5)0.029 (5)0.037 (5)0.000 (5)0.003 (5)0.001 (5)
C17'0.040 (6)0.036 (6)0.039 (6)−0.004 (5)0.002 (5)−0.003 (5)
C18'0.046 (6)0.046 (6)0.038 (6)0.000 (5)0.001 (5)−0.009 (5)
C19'0.044 (6)0.043 (6)0.038 (6)0.001 (5)0.000 (5)0.001 (5)
C20'0.042 (6)0.034 (6)0.032 (5)0.000 (5)−0.001 (5)0.004 (5)
C21'0.019 (5)0.017 (4)0.034 (5)0.009 (4)−0.003 (4)−0.001 (4)
C22'0.020 (5)0.024 (5)0.035 (5)0.006 (4)0.003 (4)0.006 (4)
C23'0.025 (5)0.029 (5)0.041 (5)0.007 (4)0.006 (5)0.007 (5)
C24'0.029 (5)0.026 (5)0.037 (5)0.012 (4)0.005 (5)0.007 (5)
C25'0.032 (5)0.025 (5)0.035 (5)0.010 (4)0.001 (4)0.004 (4)
C26'0.028 (5)0.021 (5)0.033 (5)0.010 (4)−0.004 (4)0.002 (4)
C27"0.022 (5)0.017 (6)0.040 (6)0.005 (5)0.003 (4)0.006 (5)
C27'0.022 (5)0.017 (6)0.040 (6)0.005 (5)0.003 (5)0.006 (5)
C28"0.022 (5)0.017 (6)0.040 (6)0.003 (5)0.003 (5)0.006 (5)
C28'0.022 (5)0.016 (6)0.039 (6)0.004 (5)0.002 (5)0.005 (5)
C29"0.023 (4)0.018 (6)0.041 (6)0.004 (5)0.000 (5)0.004 (5)
C29'0.024 (4)0.020 (6)0.041 (6)0.003 (5)0.000 (5)0.003 (5)
C30"0.021 (5)0.020 (5)0.041 (6)0.003 (5)−0.001 (5)0.003 (5)
C30'0.022 (5)0.020 (5)0.041 (6)0.004 (4)0.000 (5)0.004 (5)
C31"0.018 (5)0.017 (5)0.041 (6)0.006 (4)0.001 (5)0.004 (5)
C31'0.019 (5)0.017 (5)0.042 (6)0.004 (4)0.001 (5)0.003 (5)
C32"0.019 (5)0.017 (6)0.041 (6)0.006 (5)0.001 (5)0.004 (5)
C32'0.019 (5)0.017 (6)0.041 (6)0.006 (5)0.001 (5)0.004 (5)
C33"0.021 (5)0.017 (6)0.040 (6)0.007 (5)0.003 (5)0.005 (5)
C33'0.022 (5)0.018 (6)0.042 (6)0.005 (5)0.001 (5)0.005 (5)
C34"0.022 (5)0.018 (6)0.040 (6)0.005 (5)0.003 (5)0.006 (5)
C34'0.023 (5)0.017 (6)0.041 (6)0.006 (5)0.003 (4)0.005 (5)
Cl10.076 (5)0.133 (8)0.097 (6)0.013 (5)0.004 (4)0.030 (5)
Cl20.152 (8)0.063 (4)0.104 (6)0.023 (5)0.019 (6)0.012 (4)
C350.111 (11)0.095 (10)0.110 (10)0.015 (10)0.004 (10)0.026 (10)
F10.064 (8)0.057 (8)0.040 (6)0.002 (6)0.003 (5)0.021 (5)
F20.031 (7)0.159 (17)0.073 (9)0.009 (9)0.010 (6)−0.052 (10)
F30.057 (8)0.062 (8)0.070 (9)0.015 (6)0.044 (7)0.005 (7)
F40.078 (10)0.071 (10)0.108 (12)0.031 (8)0.041 (9)0.064 (9)
B10.055 (14)0.064 (15)0.039 (11)0.035 (13)0.017 (10)0.020 (10)
F50.049 (7)0.051 (7)0.039 (6)−0.012 (6)0.012 (5)0.001 (5)
F60.053 (7)0.040 (6)0.045 (6)−0.009 (5)0.011 (5)0.005 (5)
F70.128 (15)0.065 (10)0.069 (9)−0.057 (10)0.009 (9)−0.023 (8)
F80.078 (9)0.062 (8)0.032 (6)−0.009 (7)0.004 (6)0.002 (5)
B20.087 (19)0.039 (12)0.027 (10)−0.022 (12)0.014 (11)0.007 (8)
Geometric parameters (Å, º) top
Ir1—P12.323 (4)N3'—C2'1.387 (19)
Ir1—C12.035 (13)N3'—C5'1.451 (12)
Ir1—C272.215 (17)C2'—H2'0.9500
Ir1—C282.192 (16)C3'—H3'A0.9900
Ir1—C312.231 (17)C3'—H3'B0.9900
Ir1—C322.191 (17)C3'—C4'1.536 (12)
P1—C91.828 (13)C4'—H4'A0.9800
P1—C151.845 (14)C4'—H4'B0.9800
P1—C211.839 (14)C4'—H4'C0.9800
N1—N21.384 (11)C5'—H5'A0.9900
N1—C11.357 (12)C5'—H5'B0.9900
N1—C31.450 (11)C5'—C6'1.533 (13)
N2—C21.284 (12)C6'—H6'1.0000
N3—C11.370 (12)C6'—C7'1.531 (13)
N3—C21.373 (12)C6'—C8'1.531 (13)
N3—C51.459 (12)C7'—H7'A0.9800
C2—H20.9500C7'—H7'B0.9800
C3—H3A0.9900C7'—H7'C0.9800
C3—H3B0.9900C8'—H8'A0.9800
C3—C41.538 (13)C8'—H8'B0.9800
C4—H4A0.9800C8'—H8'C0.9800
C4—H4B0.9800C9'—C10'1.390 (12)
C4—H4C0.9800C9'—C14'1.397 (12)
C5—H5A0.9900C10'—H10'0.9500
C5—H5B0.9900C10'—C11'1.384 (12)
C5—C61.531 (13)C11'—H11'0.9500
C6—H61.0000C11'—C12'1.380 (12)
C6—C71.535 (14)C12'—H12'0.9500
C6—C81.533 (13)C12'—C13'1.396 (12)
C7—H7A0.9800C13'—H13'0.9500
C7—H7B0.9800C13'—C14'1.392 (12)
C7—H7C0.9800C14'—H14'0.9500
C8—H8A0.9800C15'—C16'1.3900
C8—H8B0.9800C15'—C20'1.3900
C8—H8C0.9800C16'—H16'0.9500
C9—C101.402 (12)C16'—C17'1.3900
C9—C141.389 (12)C17'—H17'0.9500
C10—H100.9500C17'—C18'1.3900
C10—C111.387 (12)C18'—H18'0.9500
C11—H110.9500C18'—C19'1.3900
C11—C121.388 (13)C19'—H19'0.9500
C12—H120.9500C19'—C20'1.3900
C12—C131.389 (13)C20'—H20'0.9500
C13—H130.9500C21'—C22'1.391 (12)
C13—C141.397 (12)C21'—C26'1.390 (12)
C14—H140.9500C22'—H22'0.9500
C15—C161.392 (12)C22'—C23'1.390 (12)
C15—C201.387 (12)C23'—H23'0.9500
C16—H160.9500C23'—C24'1.386 (13)
C16—C171.388 (12)C24'—H24'0.9500
C17—H170.9500C24'—C25'1.387 (12)
C17—C181.399 (12)C25'—H25'0.9500
C18—H180.9500C25'—C26'1.387 (12)
C18—C191.390 (12)C26'—H26'0.9500
C19—H190.9500C27"—H27"1.0000
C19—C201.403 (12)C27"—C28"1.378 (14)
C20—H200.9500C27"—C34"1.537 (14)
C21—C221.396 (12)C27'—H27'1.0000
C21—C261.393 (12)C27'—C28'1.376 (14)
C22—H220.9500C27'—C34'1.536 (14)
C22—C231.400 (12)C28"—H28"1.0000
C23—H230.9500C28"—C29"1.539 (14)
C23—C241.382 (12)C28'—H28'1.0000
C24—H240.9500C28'—C29'1.544 (14)
C24—C251.389 (12)C29"—H29A0.9900
C25—H250.9500C29"—H29B0.9900
C25—C261.388 (12)C29"—C30"1.548 (14)
C26—H260.9500C29'—H29C0.9900
C27—H271.0000C29'—H29D0.9900
C27—C281.378 (13)C29'—C30'1.543 (14)
C27—C341.535 (12)C30"—H30A0.9900
C28—H281.0000C30"—H30B0.9900
C28—C291.527 (12)C30"—C31"1.532 (14)
C29—H29E0.9900C30'—H30C0.9900
C29—H29F0.9900C30'—H30D0.9900
C29—C301.537 (13)C30'—C31'1.540 (14)
C30—H30E0.9900C31"—H31"1.0000
C30—H30F0.9900C31"—C32"1.378 (14)
C30—C311.537 (13)C31'—H31'1.0000
C31—H311.0000C31'—C32'1.380 (14)
C31—C321.372 (13)C32"—H32"1.0000
C32—H321.0000C32"—C33"1.537 (14)
C32—C331.538 (13)C32'—H32'1.0000
C33—H33E0.9900C32'—C33'1.540 (14)
C33—H33F0.9900C33"—H33A0.9900
C33—C341.537 (13)C33"—H33B0.9900
C34—H34E0.9900C33"—C34"1.542 (14)
C34—H34F0.9900C33'—H33C0.9900
Ir1'—P1'2.329 (4)C33'—H33D0.9900
Ir1'—C1'2.029 (12)C33'—C34'1.540 (14)
Ir1'—C27"2.23 (5)C34"—H34A0.9900
Ir1'—C27'2.21 (5)C34"—H34B0.9900
Ir1'—C28"2.17 (5)C34'—H34C0.9900
Ir1'—C28'2.27 (5)C34'—H34D0.9900
Ir1'—C31"2.12 (3)Cl1—C351.75 (4)
Ir1'—C31'2.15 (3)Cl2—C351.64 (4)
Ir1'—C32"2.24 (3)C35—H35A0.9900
Ir1'—C32'2.20 (3)C35—H35B0.9900
P1'—C9'1.824 (14)F1—B11.37 (3)
P1'—C15'1.825 (9)F2—B11.35 (3)
P1'—C21'1.807 (14)F3—B11.39 (3)
N1'—N2'1.379 (9)F4—B11.38 (3)
N1'—C1'1.374 (12)F5—B21.40 (3)
N1'—C3'1.442 (12)F6—B21.40 (3)
N2'—C2'1.276 (12)F7—B21.38 (3)
N3'—C1'1.370 (12)F8—B21.38 (3)
C1—Ir1—P193.5 (5)C1'—N3'—C5'124.2 (12)
C1—Ir1—C27166.9 (5)C2'—N3'—C5'127.2 (12)
C1—Ir1—C28154.0 (5)N1'—C1'—Ir1'125.6 (9)
C1—Ir1—C3187.6 (6)N3'—C1'—Ir1'130.6 (9)
C1—Ir1—C3287.3 (6)N3'—C1'—N1'103.7 (10)
C27—Ir1—P192.1 (4)N2'—C2'—N3'110.4 (13)
C27—Ir1—C3188.3 (6)N2'—C2'—H2'124.8
C28—Ir1—P195.5 (4)N3'—C2'—H2'124.8
C28—Ir1—C2736.4 (4)N1'—C3'—H3'A109.1
C28—Ir1—C3180.6 (5)N1'—C3'—H3'B109.1
C31—Ir1—P1172.9 (4)N1'—C3'—C4'112.4 (12)
C32—Ir1—P1150.9 (4)H3'A—C3'—H3'B107.9
C32—Ir1—C2782.1 (6)C4'—C3'—H3'A109.1
C32—Ir1—C2896.3 (6)C4'—C3'—H3'B109.1
C32—Ir1—C3136.1 (4)C3'—C4'—H4'A109.5
C9—P1—Ir1109.7 (4)C3'—C4'—H4'B109.5
C9—P1—C15102.4 (6)C3'—C4'—H4'C109.5
C9—P1—C21103.7 (6)H4'A—C4'—H4'B109.5
C15—P1—Ir1118.4 (4)H4'A—C4'—H4'C109.5
C21—P1—Ir1115.0 (5)H4'B—C4'—H4'C109.5
C21—P1—C15105.8 (6)N3'—C5'—H5'A108.6
N2—N1—C3121.6 (11)N3'—C5'—H5'B108.6
C1—N1—N2112.0 (10)N3'—C5'—C6'114.5 (13)
C1—N1—C3126.4 (11)H5'A—C5'—H5'B107.6
C2—N2—N1104.4 (11)C6'—C5'—H5'A108.6
C1—N3—C2107.4 (11)C6'—C5'—H5'B108.6
C1—N3—C5124.1 (11)C5'—C6'—H6'108.4
C2—N3—C5128.2 (12)C7'—C6'—C5'110.2 (15)
N1—C1—Ir1124.0 (9)C7'—C6'—H6'108.4
N1—C1—N3103.9 (10)C7'—C6'—C8'113.1 (18)
N3—C1—Ir1132.0 (9)C8'—C6'—C5'108.2 (14)
N2—C2—N3112.2 (12)C8'—C6'—H6'108.4
N2—C2—H2123.9C6'—C7'—H7'A109.5
N3—C2—H2123.9C6'—C7'—H7'B109.5
N1—C3—H3A109.6C6'—C7'—H7'C109.5
N1—C3—H3B109.6H7'A—C7'—H7'B109.5
N1—C3—C4110.4 (12)H7'A—C7'—H7'C109.5
H3A—C3—H3B108.1H7'B—C7'—H7'C109.5
C4—C3—H3A109.6C6'—C8'—H8'A109.5
C4—C3—H3B109.6C6'—C8'—H8'B109.5
C3—C4—H4A109.5C6'—C8'—H8'C109.5
C3—C4—H4B109.5H8'A—C8'—H8'B109.5
C3—C4—H4C109.5H8'A—C8'—H8'C109.5
H4A—C4—H4B109.5H8'B—C8'—H8'C109.5
H4A—C4—H4C109.5C10'—C9'—P1'117.9 (9)
H4B—C4—H4C109.5C10'—C9'—C14'117.5 (13)
N3—C5—H5A108.9C14'—C9'—P1'124.3 (10)
N3—C5—H5B108.9C9'—C10'—H10'118.9
N3—C5—C6113.5 (13)C11'—C10'—C9'122.2 (13)
H5A—C5—H5B107.7C11'—C10'—H10'118.9
C6—C5—H5A108.9C10'—C11'—H11'119.9
C6—C5—H5B108.9C12'—C11'—C10'120.2 (14)
C5—C6—H6108.9C12'—C11'—H11'119.9
C5—C6—C7111.4 (16)C11'—C12'—H12'120.8
C5—C6—C8108.7 (13)C11'—C12'—C13'118.5 (13)
C7—C6—H6108.9C13'—C12'—H12'120.8
C8—C6—H6108.9C12'—C13'—H13'119.4
C8—C6—C7110 (2)C14'—C13'—C12'121.2 (14)
C6—C7—H7A109.5C14'—C13'—H13'119.4
C6—C7—H7B109.5C9'—C14'—H14'119.8
C6—C7—H7C109.5C13'—C14'—C9'120.3 (14)
H7A—C7—H7B109.5C13'—C14'—H14'119.8
H7A—C7—H7C109.5C16'—C15'—P1'120.5 (6)
H7B—C7—H7C109.5C16'—C15'—C20'120.0
C6—C8—H8A109.5C20'—C15'—P1'119.5 (6)
C6—C8—H8B109.5C15'—C16'—H16'120.0
C6—C8—H8C109.5C17'—C16'—C15'120.0
H8A—C8—H8B109.5C17'—C16'—H16'120.0
H8A—C8—H8C109.5C16'—C17'—H17'120.0
H8B—C8—H8C109.5C18'—C17'—C16'120.0
C10—C9—P1120.2 (10)C18'—C17'—H17'120.0
C14—C9—P1120.0 (10)C17'—C18'—H18'120.0
C14—C9—C10119.8 (13)C17'—C18'—C19'120.0
C9—C10—H10120.3C19'—C18'—H18'120.0
C11—C10—C9119.5 (14)C18'—C19'—H19'120.0
C11—C10—H10120.3C18'—C19'—C20'120.0
C10—C11—H11119.3C20'—C19'—H19'120.0
C10—C11—C12121.4 (15)C15'—C20'—H20'120.0
C12—C11—H11119.3C19'—C20'—C15'120.0
C11—C12—H12120.8C19'—C20'—H20'120.0
C11—C12—C13118.5 (15)C22'—C21'—P1'123.6 (10)
C13—C12—H12120.8C26'—C21'—P1'118.5 (10)
C12—C13—H13119.4C26'—C21'—C22'117.5 (13)
C12—C13—C14121.2 (15)C21'—C22'—H22'119.6
C14—C13—H13119.4C23'—C22'—C21'120.8 (14)
C9—C14—C13119.5 (14)C23'—C22'—H22'119.6
C9—C14—H14120.2C22'—C23'—H23'119.9
C13—C14—H14120.2C24'—C23'—C22'120.3 (14)
C16—C15—P1117.6 (9)C24'—C23'—H23'119.9
C20—C15—P1124.1 (9)C23'—C24'—H24'120.0
C20—C15—C16118.2 (13)C23'—C24'—C25'120.1 (14)
C15—C16—H16118.6C25'—C24'—H24'120.0
C17—C16—C15122.8 (13)C24'—C25'—H25'120.7
C17—C16—H16118.6C26'—C25'—C24'118.6 (14)
C16—C17—H17121.0C26'—C25'—H25'120.7
C16—C17—C18118.0 (14)C21'—C26'—H26'118.7
C18—C17—H17121.0C25'—C26'—C21'122.6 (14)
C17—C18—H18119.8C25'—C26'—H26'118.7
C19—C18—C17120.5 (14)Ir1'—C27"—H27"115.2
C19—C18—H18119.8C28"—C27"—Ir1'70 (3)
C18—C19—H19120.0C28"—C27"—H27"115.2
C18—C19—C20120.1 (13)C28"—C27"—C34"116 (3)
C20—C19—H19120.0C34"—C27"—Ir1'118 (3)
C15—C20—C19120.3 (13)C34"—C27"—H27"115.2
C15—C20—H20119.8Ir1'—C27'—H27'113.8
C19—C20—H20119.8C28'—C27'—Ir1'74 (3)
C22—C21—P1118.1 (9)C28'—C27'—H27'113.8
C26—C21—P1122.2 (9)C28'—C27'—C34'128 (4)
C26—C21—C22119.6 (13)C34'—C27'—Ir1'103 (2)
C21—C22—H22120.5C34'—C27'—H27'113.8
C21—C22—C23119.1 (13)Ir1'—C28"—H28"114.7
C23—C22—H22120.5C27"—C28"—Ir1'74 (3)
C22—C23—H23119.6C27"—C28"—H28"114.7
C24—C23—C22120.9 (13)C27"—C28"—C29"125 (4)
C24—C23—H23119.6C29"—C28"—Ir1'106 (3)
C23—C24—H24120.0C29"—C28"—H28"114.7
C23—C24—C25120.0 (13)Ir1'—C28'—H28'114.2
C25—C24—H24120.0C27'—C28'—Ir1'70 (2)
C24—C25—H25120.2C27'—C28'—H28'114.2
C26—C25—C24119.6 (13)C27'—C28'—C29'125 (4)
C26—C25—H25120.2C29'—C28'—Ir1'111 (3)
C21—C26—H26119.6C29'—C28'—H28'114.2
C25—C26—C21120.9 (13)C28"—C29"—H29A108.4
C25—C26—H26119.6C28"—C29"—H29B108.4
Ir1—C27—H27114.1C28"—C29"—C30"116 (3)
C28—C27—Ir170.9 (10)H29A—C29"—H29B107.4
C28—C27—H27114.1C30"—C29"—H29A108.4
C28—C27—C34124.5 (15)C30"—C29"—H29B108.4
C34—C27—Ir1111.3 (11)C28'—C29'—H29C108.7
C34—C27—H27114.1C28'—C29'—H29D108.7
Ir1—C28—H28113.6H29C—C29'—H29D107.6
C27—C28—Ir172.7 (10)C30'—C29'—C28'114 (3)
C27—C28—H28113.6C30'—C29'—H29C108.7
C27—C28—C29126.5 (14)C30'—C29'—H29D108.7
C29—C28—Ir1109.0 (10)C29"—C30"—H30A109.7
C29—C28—H28113.6C29"—C30"—H30B109.7
C28—C29—H29E108.9H30A—C30"—H30B108.2
C28—C29—H29F108.9C31"—C30"—C29"110 (3)
C28—C29—C30113.3 (13)C31"—C30"—H30A109.7
H29E—C29—H29F107.7C31"—C30"—H30B109.7
C30—C29—H29E108.9C29'—C30'—H30C109.8
C30—C29—H29F108.9C29'—C30'—H30D109.8
C29—C30—H30E109.2H30C—C30'—H30D108.2
C29—C30—H30F109.2C31'—C30'—C29'110 (3)
C29—C30—C31112.2 (13)C31'—C30'—H30C109.8
H30E—C30—H30F107.9C31'—C30'—H30D109.8
C31—C30—H30E109.2Ir1'—C31"—H31"113.0
C31—C30—H30F109.2C30"—C31"—Ir1'115 (2)
Ir1—C31—H31114.4C30"—C31"—H31"113.0
C30—C31—Ir1111.9 (11)C32"—C31"—Ir1'76.5 (19)
C30—C31—H31114.4C32"—C31"—C30"122 (3)
C32—C31—Ir170.3 (10)C32"—C31"—H31"113.0
C32—C31—C30123.6 (16)Ir1'—C31'—H31'110.7
C32—C31—H31114.4C30'—C31'—Ir1'113 (2)
Ir1—C32—H32114.3C30'—C31'—H31'110.7
C31—C32—Ir173.5 (10)C32'—C31'—Ir1'73.7 (19)
C31—C32—H32114.3C32'—C31'—C30'131 (3)
C31—C32—C33125.2 (16)C32'—C31'—H31'110.7
C33—C32—Ir1107.1 (11)Ir1'—C32"—H32"114.4
C33—C32—H32114.3C31"—C32"—Ir1'66.8 (18)
C32—C33—H33E108.6C31"—C32"—H32"114.4
C32—C33—H33F108.6C31"—C32"—C33"125 (3)
H33E—C33—H33F107.5C33"—C32"—Ir1'112 (2)
C34—C33—C32114.8 (14)C33"—C32"—H32"114.4
C34—C33—H33E108.6Ir1'—C32'—H32'115.6
C34—C33—H33F108.6C31'—C32'—Ir1'69.4 (19)
C27—C34—C33113.0 (14)C31'—C32'—H32'115.6
C27—C34—H34E109.0C31'—C32'—C33'121 (3)
C27—C34—H34F109.0C33'—C32'—Ir1'110 (2)
C33—C34—H34E109.0C33'—C32'—H32'115.6
C33—C34—H34F109.0C32"—C33"—H33A109.0
H34E—C34—H34F107.8C32"—C33"—H33B109.0
C1'—Ir1'—P1'93.4 (4)C32"—C33"—C34"113 (3)
C1'—Ir1'—C27"155.3 (9)H33A—C33"—H33B107.8
C1'—Ir1'—C27'163.2 (8)C34"—C33"—H33A109.0
C1'—Ir1'—C28"165.6 (9)C34"—C33"—H33B109.0
C1'—Ir1'—C28'158.2 (9)C32'—C33'—H33C109.2
C1'—Ir1'—C31"89.3 (9)C32'—C33'—H33D109.2
C1'—Ir1'—C31'85.3 (9)H33C—C33'—H33D107.9
C1'—Ir1'—C32"86.3 (9)C34'—C33'—C32'112 (2)
C1'—Ir1'—C32'87.4 (9)C34'—C33'—H33C109.2
C27"—Ir1'—P1'97.3 (9)C34'—C33'—H33D109.2
C27"—Ir1'—C32"76.6 (11)C27"—C34"—C33"107 (2)
C27'—Ir1'—P1'94.7 (10)C27"—C34"—H34A110.3
C27'—Ir1'—C28'35.8 (7)C27"—C34"—H34B110.3
C28"—Ir1'—P1'90.9 (10)C33"—C34"—H34A110.3
C28"—Ir1'—C27"36.5 (7)C33"—C34"—H34B110.3
C28"—Ir1'—C32"93.9 (13)H34A—C34"—H34B108.6
C28'—Ir1'—P1'92.4 (10)C27'—C34'—C33'115 (3)
C31"—Ir1'—P1'161.5 (7)C27'—C34'—H34C108.6
C31"—Ir1'—C27"87.6 (12)C27'—C34'—H34D108.6
C31"—Ir1'—C28"82.4 (12)C33'—C34'—H34C108.6
C31"—Ir1'—C32"36.7 (5)C33'—C34'—H34D108.6
C31'—Ir1'—P1'149.7 (7)H34C—C34'—H34D107.6
C31'—Ir1'—C27'95.0 (13)Cl1—C35—H35A109.0
C31'—Ir1'—C28'79.2 (11)Cl1—C35—H35B109.0
C31'—Ir1'—C32'36.9 (5)Cl2—C35—Cl1113 (2)
C32"—Ir1'—P1'161.8 (7)Cl2—C35—H35A109.0
C32'—Ir1'—P1'173.4 (7)Cl2—C35—H35B109.0
C32'—Ir1'—C27'82.9 (11)H35A—C35—H35B107.8
C32'—Ir1'—C28'89.3 (12)F1—B1—F3110.0 (17)
C9'—P1'—Ir1'117.5 (5)F1—B1—F4108 (2)
C9'—P1'—C15'101.7 (6)F2—B1—F1110.9 (18)
C15'—P1'—Ir1'112.7 (4)F2—B1—F3110 (2)
C21'—P1'—Ir1'114.2 (5)F2—B1—F4109.1 (19)
C21'—P1'—C9'105.6 (6)F4—B1—F3109.1 (18)
C21'—P1'—C15'103.5 (6)F6—B2—F5110.2 (18)
N2'—N1'—C3'121.2 (11)F7—B2—F5109 (2)
C1'—N1'—N2'110.8 (10)F7—B2—F6109.4 (19)
C1'—N1'—C3'128.0 (11)F7—B2—F8108.7 (19)
C2'—N2'—N1'106.7 (12)F8—B2—F5109.6 (19)
C1'—N3'—C2'108.4 (11)F8—B2—F6109 (2)
Ir1—P1—C9—C1018.4 (13)Ir1'—C27'—C28'—C29'−102 (4)
Ir1—P1—C9—C14−162.1 (11)Ir1'—C27'—C34'—C33'45 (3)
Ir1—P1—C15—C1664.3 (12)Ir1'—C28"—C29"—C30"−38 (4)
Ir1—P1—C15—C20−114.2 (12)Ir1'—C28'—C29'—C30'14 (4)
Ir1—P1—C21—C2269.9 (12)Ir1'—C31"—C32"—C33"−102 (3)
Ir1—P1—C21—C26−106.6 (11)Ir1'—C31'—C32'—C33'−102 (3)
Ir1—C27—C28—C29−101.2 (17)Ir1'—C32"—C33"—C34"−36 (3)
Ir1—C27—C34—C33−10.0 (18)Ir1'—C32'—C33'—C34'13 (3)
Ir1—C28—C29—C30−39.7 (16)P1'—C9'—C10'—C11'175.7 (13)
Ir1—C31—C32—C33−99.5 (17)P1'—C9'—C14'—C13'−174.7 (13)
Ir1—C32—C33—C34−38.3 (18)P1'—C15'—C16'—C17'−177.3 (9)
P1—C9—C10—C11178.4 (13)P1'—C15'—C20'—C19'177.3 (9)
P1—C9—C14—C13−177.1 (13)P1'—C21'—C22'—C23'−174.8 (12)
P1—C15—C16—C17−177.0 (13)P1'—C21'—C26'—C25'177.1 (12)
P1—C15—C20—C19176.0 (12)N1'—N2'—C2'—N3'1.5 (18)
P1—C21—C22—C23−177.0 (11)N2'—N1'—C1'—Ir1'−176.2 (11)
P1—C21—C26—C25176.6 (11)N2'—N1'—C1'—N3'0.3 (17)
N1—N2—C2—N30 (2)N2'—N1'—C3'—C4'−71.5 (19)
N2—N1—C1—Ir1179.2 (11)N3'—C5'—C6'—C7'−65 (2)
N2—N1—C1—N32.1 (17)N3'—C5'—C6'—C8'170.5 (17)
N2—N1—C3—C469.3 (18)C1'—N1'—N2'—C2'−1.2 (18)
N3—C5—C6—C763 (2)C1'—N1'—C3'—C4'109.0 (18)
N3—C5—C6—C8−175.6 (19)C1'—N3'—C2'—N2'−1.4 (19)
C1—N1—N2—C2−1.2 (19)C1'—N3'—C5'—C6'137.4 (16)
C1—N1—C3—C4−108.4 (17)C2'—N3'—C1'—Ir1'176.9 (12)
C1—N3—C2—N22 (2)C2'—N3'—C1'—N1'0.6 (17)
C1—N3—C5—C6−140.6 (17)C2'—N3'—C5'—C6'−49 (2)
C2—N3—C1—Ir1−178.9 (13)C3'—N1'—N2'—C2'179.2 (14)
C2—N3—C1—N1−2.1 (17)C3'—N1'—C1'—Ir1'3 (2)
C2—N3—C5—C647 (3)C3'—N1'—C1'—N3'179.9 (14)
C3—N1—N2—C2−179.2 (15)C5'—N3'—C1'—Ir1'−8 (2)
C3—N1—C1—Ir1−3 (2)C5'—N3'—C1'—N1'175.7 (14)
C3—N1—C1—N3180.0 (14)C5'—N3'—C2'—N2'−176.3 (15)
C5—N3—C1—Ir17 (2)C9'—P1'—C15'—C16'−146.5 (7)
C5—N3—C1—N1−176.0 (14)C9'—P1'—C15'—C20'36.2 (8)
C5—N3—C2—N2175.2 (16)C9'—P1'—C21'—C22'−119.8 (13)
C9—P1—C15—C16−56.5 (12)C9'—P1'—C21'—C26'67.3 (13)
C9—P1—C15—C20125.0 (13)C9'—C10'—C11'—C12'−3 (3)
C9—P1—C21—C22−170.2 (11)C10'—C9'—C14'—C13'−1 (2)
C9—P1—C21—C2613.3 (13)C10'—C11'—C12'—C13'4 (2)
C9—C10—C11—C120 (3)C11'—C12'—C13'—C14'−4 (2)
C10—C9—C14—C132 (2)C12'—C13'—C14'—C9'2 (2)
C10—C11—C12—C13−1 (3)C14'—C9'—C10'—C11'1 (2)
C11—C12—C13—C142 (3)C15'—P1'—C9'—C10'59.5 (13)
C12—C13—C14—C9−3 (3)C15'—P1'—C9'—C14'−126.5 (14)
C14—C9—C10—C11−1 (2)C15'—P1'—C21'—C22'−13.4 (14)
C15—P1—C9—C10145.1 (12)C15'—P1'—C21'—C26'173.7 (11)
C15—P1—C9—C14−35.5 (14)C15'—C16'—C17'—C18'0.0
C15—P1—C21—C22−62.8 (13)C16'—C15'—C20'—C19'0.0
C15—P1—C21—C26120.7 (12)C16'—C17'—C18'—C19'0.0
C15—C16—C17—C181 (2)C17'—C18'—C19'—C20'0.0
C16—C15—C20—C19−2 (2)C18'—C19'—C20'—C15'0.0
C16—C17—C18—C19−2 (3)C20'—C15'—C16'—C17'0.0
C17—C18—C19—C202 (3)C21'—P1'—C9'—C10'167.3 (12)
C18—C19—C20—C151 (2)C21'—P1'—C9'—C14'−18.7 (15)
C20—C15—C16—C172 (2)C21'—P1'—C15'—C16'104.1 (8)
C21—P1—C9—C10−105.0 (12)C21'—P1'—C15'—C20'−73.2 (8)
C21—P1—C9—C1474.5 (14)C21'—C22'—C23'—C24'0 (2)
C21—P1—C15—C16−164.8 (11)C22'—C21'—C26'—C25'4 (2)
C21—P1—C15—C2016.6 (14)C22'—C23'—C24'—C25'1 (2)
C21—C22—C23—C241 (2)C23'—C24'—C25'—C26'1 (2)
C22—C21—C26—C250 (2)C24'—C25'—C26'—C21'−3 (2)
C22—C23—C24—C250 (2)C26'—C21'—C22'—C23'−2 (2)
C23—C24—C25—C260 (2)C27"—C28"—C29"—C30"43 (6)
C24—C25—C26—C210 (2)C27'—C28'—C29'—C30'94 (5)
C26—C21—C22—C230 (2)C28"—C27"—C34"—C33"−106 (4)
C27—C28—C29—C3042 (2)C28"—C29"—C30"—C31"29 (5)
C28—C27—C34—C33−91 (2)C28'—C27'—C34'—C33'−35 (6)
C28—C29—C30—C3137 (2)C28'—C29'—C30'—C31'−34 (4)
C29—C30—C31—Ir1−15.1 (18)C29"—C30"—C31"—Ir1'−5 (4)
C29—C30—C31—C32−95 (2)C29"—C30"—C31"—C32"−94 (4)
C30—C31—C32—Ir1103.7 (16)C29'—C30'—C31'—Ir1'40 (3)
C30—C31—C32—C334 (3)C29'—C30'—C31'—C32'−49 (5)
C31—C32—C33—C3443 (2)C30"—C31"—C32"—Ir1'111 (3)
C32—C33—C34—C2733 (2)C30"—C31"—C32"—C33"9 (5)
C34—C27—C28—Ir1103.1 (16)C30'—C31'—C32'—Ir1'107 (4)
C34—C27—C28—C292 (3)C30'—C31'—C32'—C33'5 (6)
Ir1'—P1'—C9'—C10'−64.1 (13)C31"—C32"—C33"—C34"40 (4)
Ir1'—P1'—C9'—C14'110.0 (13)C31'—C32'—C33'—C34'91 (4)
Ir1'—P1'—C15'—C16'−19.7 (8)C32"—C33"—C34"—C27"40 (4)
Ir1'—P1'—C15'—C20'162.9 (5)C32'—C33'—C34'—C27'−41 (4)
Ir1'—P1'—C21'—C22'109.6 (12)C34"—C27"—C28"—Ir1'112 (3)
Ir1'—P1'—C21'—C26'−63.4 (12)C34"—C27"—C28"—C29"13 (6)
Ir1'—C27"—C28"—C29"−98 (4)C34'—C27'—C28'—Ir1'95 (4)
Ir1'—C27"—C34"—C33"−26 (4)C34'—C27'—C28'—C29'−8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···F8i0.952.323.18 (2)149
C19—H19···F1ii0.952.503.380 (19)154
C2′—H2′···F5iii0.952.263.171 (18)161
C13′—H13′···F2iii0.952.563.38 (2)144
C18′—H18′···F80.952.523.319 (16)142
C33"—H33B···F3ii0.992.243.08 (3)143
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) x−1/2, y−1/2, z.
 

Acknowledgements

This work was supported by a Murley Research Fellowship grant.

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Journal logoIUCrDATA
ISSN: 2414-3146
Volume 9| Part 9| September 2024| x240941
https://doi.org/10.1107/S2414314624009416