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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1114.
Published online 2010 August 18. doi:  10.1107/S1600536810031727
PMCID: PMC3008037

[(1,2,5,6-η)-1,5-Cyclo­octa­diene](1-isopropyl-3-methyl­imidazolin-2-yl­idene)(triphenyl­phosphine)iridium(I) tetra­fluorido­borate dichloro­methane solvate

Abstract

In the title compound, [Ir(C8H12)(C7H12N2)(C18H15P)]BF4·CH2Cl2, the Ir(I) atom has a square-planar conformation with normal bond lengths. One of the phenyl rings, and the solvent dichloro­methane mol­ecule, were refined using separate two part disorder models, each in an approximately 1:1 ratio.

Related literature

For structure and dynamics of related N-heterocyclic carbene iridium complexes, see: Chianese et al. (2003 [triangle]); Herrmann et al. (2006 [triangle]); Köcher & Herrmann (1997 [triangle]); Nichol et al. (2009 [triangle]). For the isotypic Rh analogue, see: Nichol et al. (2010 [triangle]). For catalytic properties of these complexes, see: Albrecht et al. (2002 [triangle]); Frey et al. (2006 [triangle]); Gnanamgari et al. (2007 [triangle]); Voutchkova et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1114-scheme1.jpg

Experimental

Crystal data

  • [Ir(C8H12)(C7H12N2)(C18H15P)]BF4·CH2Cl2
  • M r = 858.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1114-efi1.jpg
  • a = 36.3039 (16) Å
  • b = 10.4913 (5) Å
  • c = 18.3924 (8) Å
  • β = 103.452 (2)°
  • V = 6813.0 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 4.17 mm−1
  • T = 100 K
  • 0.30 × 0.14 × 0.11 mm

Data collection

  • Bruker Kappa APEXII DUO CCD diffractometer
  • Absorption correction: numerical (SADABS; Sheldrick, 1996 [triangle]) T min = 0.370, T max = 0.652
  • 72041 measured reflections
  • 7834 independent reflections
  • 6800 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.073
  • S = 1.04
  • 7834 reflections
  • 460 parameters
  • 84 restraints
  • H-atom parameters constrained
  • Δρmax = 1.31 e Å−3
  • Δρmin = −0.94 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031727/ng5007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031727/ng5007Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

DS thanks Millersville University’s Neimeyer–Hodgson student research grant. The diffractometer was purchased with funding from NSF grant CHE-0741837.

supplementary crystallographic information

Comment

The title compound, (I), was prepared as part of our ongoing research on Rh and Ir-containing N-heterocyclic carbene complexes (Nichol et al., 2009). The Ir center has an expected square planar conformation and bond distances are unexceptional. One of the phenyl rings, and the solvent dichloromethane molecule, were refined using separate two part disorder models, each in an approximately 1:1 ratio. The structure of the isomorphous Rh analogue has also been reported (Nichol et al., 2010).

Experimental

The title compound, (I), was synthesized by the reaction of [Ir(cod)(C7H12N2)Cl](0.369 mg, 0.80 mmol) and triphenylphosphene (211 mg, 0.80 mmol) in CH2Cl2 (8 ml) with silver tetrafluoroborate (157 m, 0.80 mmol) for 1.5 h. The mixture was filtered through Celite to remove silver chloride and the solvent was removed under reduced pressure. Crystals of the resulting solid of the title compound were obtained by slow diffusion of pentane into dichloromethane solution of the compound.

Refinement

One of the phenyl rings, and the solvent dichloromethane molecule, were refined using separate two part disorder models, each in an approximately 1:1 ratio. Bond distance similarity restraints were applied to the dichloromethane molecule, and approximate isotropic restraints were used on the ellipsoids of the disordered C atoms of both the dichloromethane molecule and the phenyl ring. The largest residual peak is approximately 0.76Å from Ir. H atoms were first located in a difference map and then refined using UisoH = 1.5UeqC for methyl groups and UisoH = 1.2UeqC for all others and constrained C–H distances.

Figures

Fig. 1.
The structure of the Ir complex in (I), with displacement ellipsoids at the 30% probability level and hydrogen atoms omitted.

Crystal data

[Ir(C8H12)(C7H12N2)(C18H15P)]BF4·CH2Cl2F(000) = 3408
Mr = 858.57Dx = 1.674 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9491 reflections
a = 36.3039 (16) Åθ = 2.4–28.3°
b = 10.4913 (5) ŵ = 4.17 mm1
c = 18.3924 (8) ÅT = 100 K
β = 103.452 (2)°Prism, red
V = 6813.0 (5) Å30.30 × 0.14 × 0.11 mm
Z = 8

Data collection

Bruker Kappa APEXII DUO CCD diffractometer7834 independent reflections
Radiation source: fine-focus sealed tube with Miracol optics6800 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: numerical (SADABS; Sheldrick, 1996)h = −47→47
Tmin = 0.370, Tmax = 0.652k = −13→13
72041 measured reflectionsl = −23→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.050P)2 + 5.P] where P = (Fo2 + 2Fc2)/3
7834 reflections(Δ/σ)max = 0.011
460 parametersΔρmax = 1.31 e Å3
84 restraintsΔρmin = −0.94 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Ir0.668273 (3)0.510395 (9)0.563854 (6)0.02420 (5)
Cl10.54347 (6)0.9363 (4)0.70029 (17)0.0471 (7)0.511 (7)
Cl20.57718 (16)1.1103 (5)0.6136 (5)0.137 (2)0.511 (7)
Cl1'0.54270 (8)1.0031 (6)0.71548 (15)0.0579 (11)0.489 (7)
Cl2'0.57231 (13)1.0807 (4)0.58942 (14)0.0553 (9)0.489 (7)
P0.60271 (2)0.52250 (7)0.53810 (5)0.02869 (16)
F10.63097 (6)1.1774 (2)0.28542 (14)0.0718 (7)
F20.68831 (7)1.2144 (3)0.26529 (15)0.0974 (10)
F30.68298 (6)1.1205 (3)0.37193 (13)0.0728 (7)
F40.66639 (8)1.0113 (2)0.2656 (2)0.0865 (10)
N10.67636 (6)0.7514 (2)0.47676 (15)0.0373 (6)
N20.67143 (7)0.5884 (2)0.40379 (14)0.0356 (6)
B0.66725 (11)1.1321 (5)0.2973 (3)0.0557 (11)
C10.67157 (7)0.6230 (3)0.47509 (17)0.0318 (6)
C20.67518 (8)0.6943 (3)0.3618 (2)0.0455 (8)
H20.67560.69480.31040.055*
C30.67807 (8)0.7960 (3)0.4063 (2)0.0488 (9)
H30.68080.88220.39260.059*
C40.67913 (8)0.8306 (3)0.5440 (2)0.0456 (8)
H40.67630.77370.58600.055*
C50.64780 (9)0.9295 (3)0.5322 (3)0.0681 (13)
H5A0.62320.88690.51720.102*
H5B0.65080.98900.49290.102*
H5C0.64920.97650.57880.102*
C60.71784 (8)0.8956 (3)0.5664 (2)0.0525 (9)
H6A0.73780.83240.56720.079*
H6B0.72100.93350.61620.079*
H6C0.71950.96250.53010.079*
C70.66684 (10)0.4574 (3)0.37577 (19)0.0403 (7)
H7A0.65800.40340.41180.060*
H7B0.69120.42540.36910.060*
H7C0.64820.45560.32770.060*
C80.57817 (16)0.6605 (5)0.4981 (5)0.0241 (16)0.556 (18)
C90.55354 (16)0.7332 (5)0.5287 (5)0.0363 (17)0.556 (18)
H90.55050.71490.57760.044*0.556 (18)
C100.53335 (13)0.8325 (4)0.4879 (7)0.047 (2)0.556 (18)
H100.51650.88220.50880.057*0.556 (18)
C110.53780 (13)0.8592 (4)0.4164 (7)0.041 (2)0.556 (18)
H110.52400.92720.38850.049*0.556 (18)
C120.56243 (15)0.7866 (6)0.3857 (5)0.041 (2)0.556 (18)
H120.56550.80490.33690.049*0.556 (18)
C130.58261 (15)0.6873 (5)0.4266 (5)0.0284 (17)0.556 (18)
H130.59940.63760.40560.034*0.556 (18)
C8'0.5794 (2)0.6616 (5)0.4725 (5)0.021 (2)0.444 (18)
C9'0.55502 (19)0.7448 (6)0.4970 (6)0.035 (2)0.444 (18)
H9'0.55090.73630.54590.042*0.444 (18)
C10'0.53665 (19)0.8404 (6)0.4499 (7)0.040 (3)0.444 (18)
H10'0.52000.89730.46660.048*0.444 (18)
C11'0.5426 (2)0.8528 (5)0.3783 (7)0.042 (3)0.444 (18)
H11'0.53010.91820.34610.050*0.444 (18)
C12'0.5670 (2)0.7697 (6)0.3537 (6)0.038 (2)0.444 (18)
H12'0.57110.77810.30480.046*0.444 (18)
C13'0.5854 (2)0.6741 (6)0.4008 (5)0.0260 (19)0.444 (18)
H13'0.60200.61720.38410.031*0.444 (18)
C140.58120 (8)0.5100 (3)0.6183 (2)0.0362 (7)
C150.59156 (8)0.5988 (3)0.6765 (2)0.0471 (9)
H150.60980.66280.67400.057*
C160.57541 (8)0.5937 (4)0.7375 (2)0.0510 (9)
H160.58200.65580.77590.061*
C170.54978 (10)0.4992 (3)0.7431 (2)0.0496 (10)
H170.53910.49510.78560.060*
C180.53965 (8)0.4100 (3)0.68616 (18)0.0429 (7)
H180.52200.34460.68970.052*
C190.55513 (7)0.4160 (3)0.62424 (17)0.0351 (6)
H190.54780.35500.58530.042*
C200.58018 (7)0.3948 (2)0.47589 (14)0.0255 (5)
C210.60049 (8)0.2880 (2)0.46441 (14)0.0265 (5)
H210.62640.28040.48950.032*
C220.58319 (9)0.1918 (3)0.41636 (16)0.0344 (6)
H220.59730.11910.40820.041*
C230.54526 (10)0.2028 (3)0.38053 (17)0.0412 (7)
H230.53330.13700.34810.049*
C240.52498 (9)0.3086 (3)0.39171 (18)0.0432 (8)
H240.49910.31560.36650.052*
C250.54182 (8)0.4050 (3)0.43925 (17)0.0360 (6)
H250.52750.47750.44700.043*
C260.72262 (7)0.4198 (3)0.56404 (17)0.0310 (6)
H260.72870.41800.51370.037*
C270.73017 (8)0.5364 (3)0.60018 (18)0.0333 (6)
H270.74040.60190.57070.040*
C280.74038 (8)0.5601 (4)0.68319 (19)0.0484 (8)
H28A0.76770.54210.70260.058*
H28B0.73620.65130.69250.058*
C290.71816 (11)0.4810 (4)0.7254 (2)0.0515 (10)
H29A0.71770.52450.77290.062*
H29B0.73100.39800.73790.062*
C300.67744 (8)0.4573 (4)0.68168 (17)0.0398 (7)
H300.65780.49140.70670.048*
C310.66613 (8)0.3492 (3)0.63912 (15)0.0335 (6)
H310.63990.32010.63910.040*
C320.69224 (8)0.2436 (3)0.62553 (18)0.0413 (7)
H32A0.69990.19180.67160.050*
H32B0.67810.18740.58540.050*
C330.72751 (9)0.2912 (3)0.60362 (19)0.0421 (7)
H33A0.73530.22750.57040.050*
H33B0.74820.29800.64920.050*
C340.58431 (16)0.9833 (6)0.6744 (3)0.0401 (17)0.511 (7)
H34A0.60371.00680.71980.048*0.511 (7)
H34B0.59420.91050.65050.048*0.511 (7)
C34'0.58224 (16)1.0511 (6)0.6851 (3)0.081 (3)*0.489 (7)
H34C0.60190.98400.69740.097*0.489 (7)
H34D0.59261.12950.71220.097*0.489 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ir0.01353 (7)0.02279 (7)0.03367 (8)0.00024 (3)0.00019 (5)−0.00506 (4)
Cl10.0276 (8)0.0522 (16)0.0600 (13)−0.0038 (8)0.0068 (8)−0.0006 (11)
Cl20.082 (3)0.064 (2)0.293 (7)0.033 (2)0.100 (4)0.095 (4)
Cl1'0.0481 (13)0.087 (3)0.0383 (11)−0.0257 (13)0.0087 (9)0.0051 (12)
Cl2'0.0796 (19)0.0548 (18)0.0410 (14)0.0281 (14)0.0329 (10)0.0115 (9)
P0.0143 (3)0.0221 (3)0.0463 (4)−0.0004 (2)0.0001 (3)−0.0069 (3)
F10.0373 (11)0.0748 (16)0.1002 (18)0.0227 (11)0.0097 (11)0.0172 (14)
F20.0634 (16)0.135 (3)0.0935 (19)−0.0184 (16)0.0181 (14)0.0535 (18)
F30.0535 (13)0.0842 (18)0.0747 (15)0.0031 (12)0.0025 (11)0.0362 (13)
F40.0402 (15)0.085 (2)0.124 (3)0.0264 (11)−0.0033 (15)−0.0120 (15)
N10.0173 (11)0.0250 (12)0.0645 (17)−0.0015 (9)−0.0010 (10)0.0063 (11)
N20.0264 (12)0.0322 (13)0.0443 (14)−0.0048 (10)0.0006 (10)0.0080 (11)
B0.0281 (19)0.069 (3)0.069 (3)0.0096 (18)0.0080 (18)0.022 (2)
C10.0162 (12)0.0253 (13)0.0496 (17)−0.0019 (10)−0.0013 (11)0.0031 (12)
C20.0313 (16)0.0437 (18)0.056 (2)−0.0060 (13)−0.0008 (14)0.0207 (15)
C30.0252 (15)0.0365 (17)0.079 (2)−0.0033 (13)−0.0002 (15)0.0248 (17)
C40.0248 (14)0.0228 (14)0.087 (2)−0.0024 (11)0.0078 (15)−0.0061 (15)
C50.0224 (15)0.0287 (17)0.146 (4)−0.0007 (13)0.0055 (19)−0.014 (2)
C60.0221 (15)0.0325 (16)0.096 (3)−0.0015 (12)−0.0004 (16)−0.0139 (17)
C70.0423 (18)0.0382 (16)0.0394 (17)−0.0084 (15)0.0073 (13)0.0021 (14)
C80.017 (2)0.024 (3)0.029 (4)−0.0035 (19)0.000 (2)0.006 (2)
C90.032 (3)0.028 (3)0.047 (4)0.013 (2)0.006 (3)0.010 (3)
C100.048 (3)0.033 (3)0.063 (6)0.015 (3)0.017 (3)0.013 (3)
C110.039 (3)0.032 (3)0.047 (6)0.007 (2)0.000 (3)0.016 (3)
C120.036 (3)0.039 (4)0.041 (5)−0.010 (3)−0.004 (3)0.014 (3)
C130.022 (3)0.030 (3)0.030 (4)−0.002 (2)0.001 (3)0.001 (3)
C8'0.018 (3)0.020 (3)0.024 (5)−0.001 (2)0.004 (3)−0.001 (3)
C9'0.035 (4)0.029 (4)0.035 (5)0.005 (3)0.000 (3)−0.004 (3)
C10'0.043 (4)0.033 (4)0.040 (6)0.020 (3)0.003 (4)0.003 (4)
C11'0.051 (4)0.023 (3)0.042 (6)0.011 (3)−0.007 (4)0.004 (3)
C12'0.041 (4)0.031 (4)0.036 (5)−0.002 (3)−0.003 (3)0.011 (3)
C13'0.027 (3)0.024 (3)0.025 (4)−0.003 (2)0.003 (3)0.005 (3)
C140.0134 (13)0.0382 (16)0.055 (2)0.0014 (10)0.0038 (13)−0.0189 (13)
C150.0152 (13)0.055 (2)0.070 (2)−0.0043 (12)0.0079 (13)−0.0321 (17)
C160.0195 (14)0.072 (2)0.058 (2)0.0024 (14)0.0016 (13)−0.0355 (18)
C170.0231 (17)0.073 (3)0.051 (2)0.0063 (13)0.0047 (15)−0.0193 (16)
C180.0244 (14)0.0518 (19)0.0511 (19)−0.0001 (13)0.0059 (13)−0.0088 (15)
C190.0183 (12)0.0370 (15)0.0476 (17)0.0010 (11)0.0024 (11)−0.0113 (13)
C200.0203 (12)0.0231 (12)0.0294 (13)−0.0042 (9)−0.0015 (10)0.0005 (10)
C210.0267 (13)0.0236 (12)0.0275 (13)−0.0025 (10)0.0026 (10)0.0048 (10)
C220.0464 (17)0.0208 (13)0.0341 (15)−0.0040 (12)0.0056 (13)0.0003 (11)
C230.0508 (19)0.0295 (15)0.0346 (16)−0.0129 (13)−0.0077 (14)0.0013 (12)
C240.0323 (16)0.0346 (16)0.0497 (18)−0.0103 (12)−0.0171 (13)0.0066 (13)
C250.0242 (14)0.0280 (14)0.0486 (17)−0.0001 (11)−0.0062 (12)0.0005 (12)
C260.0177 (12)0.0316 (14)0.0445 (16)0.0034 (10)0.0090 (11)−0.0012 (12)
C270.0112 (12)0.0369 (15)0.0479 (18)0.0001 (11)−0.0014 (11)−0.0046 (14)
C280.0222 (14)0.065 (2)0.0515 (19)0.0020 (15)−0.0043 (13)−0.0185 (17)
C290.0306 (18)0.084 (3)0.0360 (18)−0.0043 (16)−0.0005 (14)−0.0196 (16)
C300.0221 (14)0.066 (2)0.0291 (15)0.0058 (14)0.0026 (11)−0.0068 (15)
C310.0264 (14)0.0429 (16)0.0302 (14)0.0021 (12)0.0041 (11)0.0076 (12)
C320.0359 (16)0.0404 (17)0.0467 (17)0.0094 (13)0.0074 (13)0.0117 (14)
C330.0360 (16)0.0327 (16)0.058 (2)0.0082 (13)0.0126 (14)0.0022 (14)
C340.034 (3)0.026 (3)0.066 (4)0.004 (2)0.022 (3)−0.002 (3)

Geometric parameters (Å, °)

Ir—P2.3196 (7)C10'—H10'0.950
Ir—C12.041 (3)C10'—C11'1.390
Ir—C262.189 (3)C11'—H11'0.950
Ir—C272.207 (3)C11'—C12'1.390
Ir—C302.187 (3)C12'—H12'0.950
Ir—C312.198 (3)C12'—C13'1.390
Cl1—C341.731 (5)C13'—H13'0.950
Cl2—C341.719 (6)C14—C151.404 (4)
Cl1'—C34'1.732 (5)C14—C191.389 (4)
Cl2'—C34'1.740 (5)C15—H150.950
P—C81.769 (4)C15—C161.382 (5)
P—C8'1.957 (6)C16—H160.950
P—C141.827 (4)C16—C171.380 (5)
P—C201.827 (3)C17—H170.950
F1—B1.369 (4)C17—C181.389 (5)
F2—B1.373 (5)C18—H180.950
F3—B1.364 (5)C18—C191.384 (4)
F4—B1.393 (6)C19—H190.950
N1—C11.358 (3)C20—C211.384 (4)
N1—C31.392 (4)C20—C251.403 (4)
N1—C41.474 (4)C21—H210.950
N2—C11.360 (4)C21—C221.391 (4)
N2—C21.377 (4)C22—H220.950
N2—C71.464 (4)C22—C231.386 (4)
C2—H20.950C23—H230.950
C2—C31.334 (5)C23—C241.373 (5)
C3—H30.950C24—H240.950
C4—H41.000C24—C251.383 (4)
C4—C51.517 (4)C25—H250.950
C4—C61.529 (4)C26—H261.000
C5—H5A0.980C26—C271.388 (4)
C5—H5B0.980C26—C331.524 (4)
C5—H5C0.980C27—H271.000
C6—H6A0.980C27—C281.506 (5)
C6—H6B0.980C28—H28A0.990
C6—H6C0.980C28—H28B0.990
C7—H7A0.980C28—C291.494 (6)
C7—H7B0.980C29—H29A0.990
C7—H7C0.980C29—H29B0.990
C8—C91.390C29—C301.530 (5)
C8—C131.390C30—H301.000
C9—H90.950C30—C311.384 (4)
C9—C101.390C31—H311.000
C10—H100.950C31—C321.516 (4)
C10—C111.390C32—H32A0.990
C11—H110.950C32—H32B0.990
C11—C121.390C32—C331.514 (4)
C12—H120.950C33—H33A0.990
C12—C131.390C33—H33B0.990
C13—H130.950C34—H34A0.990
C8'—C9'1.390C34—H34B0.990
C8'—C13'1.390C34'—H34C0.990
C9'—H9'0.950C34'—H34D0.990
C9'—C10'1.390
P—Ir—C193.05 (7)C11'—C12'—C13'120.0
P—Ir—C26154.91 (8)H12'—C12'—C13'120.0
P—Ir—C27168.25 (9)C8'—C13'—C12'120.0
P—Ir—C3097.40 (8)C8'—C13'—H13'120.0
P—Ir—C3189.18 (8)C12'—C13'—H13'120.0
C1—Ir—C2691.82 (11)P—C14—C15118.7 (2)
C1—Ir—C2785.73 (11)P—C14—C19122.8 (2)
C1—Ir—C30156.42 (12)C15—C14—C19118.5 (3)
C1—Ir—C31165.05 (11)C14—C15—H15119.9
C26—Ir—C2736.81 (11)C14—C15—C16120.3 (3)
C26—Ir—C3087.62 (11)H15—C15—C16119.9
C26—Ir—C3180.16 (11)C15—C16—H16119.7
C27—Ir—C3079.75 (12)C15—C16—C17120.6 (3)
C27—Ir—C3195.00 (12)H16—C16—C17119.7
C30—Ir—C3136.81 (12)C16—C17—H17120.3
Ir—P—C8121.6 (2)C16—C17—C18119.5 (4)
Ir—P—C8'116.3 (3)H17—C17—C18120.3
Ir—P—C14116.25 (11)C17—C18—H18119.9
Ir—P—C20112.12 (9)C17—C18—C19120.2 (3)
C8—P—C8'13.7 (2)H18—C18—C19119.9
C8—P—C1497.2 (3)C14—C19—C18120.8 (3)
C8—P—C20103.3 (3)C14—C19—H19119.6
C8'—P—C14110.3 (3)C18—C19—H19119.6
C8'—P—C2095.4 (3)P—C20—C21120.81 (19)
C14—P—C20103.87 (13)P—C20—C25119.7 (2)
C1—N1—C3110.2 (3)C21—C20—C25119.5 (2)
C1—N1—C4124.2 (3)C20—C21—H21119.8
C3—N1—C4125.6 (3)C20—C21—C22120.4 (2)
C1—N2—C2110.3 (3)H21—C21—C22119.8
C1—N2—C7124.4 (2)C21—C22—H22120.2
C2—N2—C7125.3 (3)C21—C22—C23119.6 (3)
F1—B—F2108.9 (3)H22—C22—C23120.2
F1—B—F3110.7 (4)C22—C23—H23119.9
F1—B—F4108.8 (4)C22—C23—C24120.3 (3)
F2—B—F3110.1 (4)H23—C23—C24119.9
F2—B—F4110.7 (4)C23—C24—H24119.6
F3—B—F4107.7 (4)C23—C24—C25120.8 (3)
Ir—C1—N1125.9 (2)H24—C24—C25119.6
Ir—C1—N2129.0 (2)C20—C25—C24119.4 (3)
N1—C1—N2105.0 (3)C20—C25—H25120.3
N2—C2—H2126.1C24—C25—H25120.3
N2—C2—C3107.8 (3)Ir—C26—H26113.5
H2—C2—C3126.1Ir—C26—C2772.31 (15)
N1—C3—C2106.7 (3)Ir—C26—C33112.95 (18)
N1—C3—H3126.6H26—C26—C27113.5
C2—C3—H3126.6H26—C26—C33113.5
N1—C4—H4108.1C27—C26—C33124.3 (3)
N1—C4—C5111.3 (3)Ir—C27—C2670.88 (15)
N1—C4—C6110.8 (3)Ir—C27—H27113.7
H4—C4—C5108.1Ir—C27—C28108.7 (2)
H4—C4—C6108.1C26—C27—H27113.7
C5—C4—C6110.2 (3)C26—C27—C28127.3 (3)
C4—C5—H5A109.5H27—C27—C28113.7
C4—C5—H5B109.5C27—C28—H28A108.9
C4—C5—H5C109.5C27—C28—H28B108.9
H5A—C5—H5B109.5C27—C28—C29113.6 (3)
H5A—C5—H5C109.5H28A—C28—H28B107.7
H5B—C5—H5C109.5H28A—C28—C29108.9
C4—C6—H6A109.5H28B—C28—C29108.9
C4—C6—H6B109.5C28—C29—H29A109.0
C4—C6—H6C109.5C28—C29—H29B109.0
H6A—C6—H6B109.5C28—C29—C30112.9 (3)
H6A—C6—H6C109.5H29A—C29—H29B107.8
H6B—C6—H6C109.5H29A—C29—C30109.0
N2—C7—H7A109.5H29B—C29—C30109.0
N2—C7—H7B109.5Ir—C30—C29112.7 (2)
N2—C7—H7C109.5Ir—C30—H30113.8
H7A—C7—H7B109.5Ir—C30—C3172.04 (17)
H7A—C7—H7C109.5C29—C30—H30113.8
H7B—C7—H7C109.5C29—C30—C31123.6 (3)
P—C8—C9126.1 (3)H30—C30—C31113.8
P—C8—C13113.6 (3)Ir—C31—C3071.15 (19)
C9—C8—C13120.0Ir—C31—H31114.1
C8—C9—H9120.0Ir—C31—C32110.07 (18)
C8—C9—C10120.0C30—C31—H31114.1
H9—C9—C10120.0C30—C31—C32125.2 (3)
C9—C10—H10120.0H31—C31—C32114.1
C9—C10—C11120.0C31—C32—H32A108.8
H10—C10—C11120.0C31—C32—H32B108.8
C10—C11—H11120.0C31—C32—C33113.8 (3)
C10—C11—C12120.0H32A—C32—H32B107.7
H11—C11—C12120.0H32A—C32—C33108.8
C11—C12—H12120.0H32B—C32—C33108.8
C11—C12—C13120.0C26—C33—C32114.0 (2)
H12—C12—C13120.0C26—C33—H33A108.7
C8—C13—C12120.0C26—C33—H33B108.7
C8—C13—H13120.0C32—C33—H33A108.7
C12—C13—H13120.0C32—C33—H33B108.7
P—C8'—C9'119.0 (3)H33A—C33—H33B107.6
P—C8'—C13'120.9 (3)Cl1—C34—Cl2113.0 (4)
C9'—C8'—C13'120.0Cl1—C34—H34A109.0
C8'—C9'—H9'120.0Cl1—C34—H34B109.0
C8'—C9'—C10'120.0Cl2—C34—H34A109.0
H9'—C9'—C10'120.0Cl2—C34—H34B109.0
C9'—C10'—H10'120.0H34A—C34—H34B107.8
C9'—C10'—C11'120.0Cl1'—C34'—Cl2'112.7 (4)
H10'—C10'—C11'120.0Cl1'—C34'—H34C109.1
C10'—C11'—H11'120.0Cl1'—C34'—H34D109.1
C10'—C11'—C12'120.0Cl2'—C34'—H34C109.1
H11'—C11'—C12'120.0Cl2'—C34'—H34D109.1
C11'—C12'—H12'120.0H34C—C34'—H34D107.8
C1—Ir—P—C8−32.6 (3)C8—P—C14—C19108.2 (3)
C1—Ir—P—C8'−18.0 (3)C8'—P—C14—C15−76.7 (4)
C1—Ir—P—C14−150.47 (13)C8'—P—C14—C19103.6 (4)
C1—Ir—P—C2090.25 (12)C20—P—C14—C15−177.9 (3)
C26—Ir—P—C8−133.5 (4)C20—P—C14—C192.4 (3)
C26—Ir—P—C8'−118.9 (3)P—C14—C15—C16178.9 (3)
C26—Ir—P—C14108.6 (2)C19—C14—C15—C16−1.4 (5)
C26—Ir—P—C20−10.6 (2)C14—C15—C16—C171.9 (5)
C27—Ir—P—C851.2 (6)C15—C16—C17—C18−1.2 (5)
C27—Ir—P—C8'65.7 (5)C16—C17—C18—C19−0.1 (5)
C27—Ir—P—C14−66.7 (5)C17—C18—C19—C140.6 (5)
C27—Ir—P—C20174.0 (4)P—C14—C19—C18179.8 (2)
C30—Ir—P—C8126.3 (3)C15—C14—C19—C180.1 (5)
C30—Ir—P—C8'140.8 (3)Ir—P—C20—C2116.3 (2)
C30—Ir—P—C148.35 (14)Ir—P—C20—C25−163.7 (2)
C30—Ir—P—C20−110.93 (14)C8—P—C20—C21148.9 (3)
C31—Ir—P—C8162.2 (3)C8—P—C20—C25−31.1 (4)
C31—Ir—P—C8'176.7 (3)C8'—P—C20—C21137.6 (3)
C31—Ir—P—C1444.32 (13)C8'—P—C20—C25−42.4 (4)
C31—Ir—P—C20−74.96 (12)C14—P—C20—C21−110.0 (2)
C3—N1—C1—Ir178.82 (19)C14—P—C20—C2570.0 (3)
C3—N1—C1—N21.7 (3)P—C20—C21—C22−179.4 (2)
C4—N1—C1—Ir−1.4 (4)C25—C20—C21—C220.6 (4)
C4—N1—C1—N2−178.5 (2)C20—C21—C22—C23−0.7 (4)
C2—N2—C1—Ir−178.4 (2)C21—C22—C23—C240.7 (5)
C2—N2—C1—N1−1.4 (3)C22—C23—C24—C25−0.6 (5)
C7—N2—C1—Ir3.2 (4)C23—C24—C25—C200.6 (5)
C7—N2—C1—N1−179.8 (2)P—C20—C25—C24179.5 (2)
P—Ir—C1—N192.8 (2)C21—C20—C25—C24−0.5 (4)
P—Ir—C1—N2−90.8 (2)P—Ir—C26—C27−178.43 (16)
C26—Ir—C1—N1−111.9 (2)P—Ir—C26—C33−58.0 (3)
C26—Ir—C1—N264.6 (2)C1—Ir—C26—C2780.4 (2)
C27—Ir—C1—N1−75.5 (2)C1—Ir—C26—C33−159.1 (2)
C27—Ir—C1—N2100.9 (2)C27—Ir—C26—C33120.5 (3)
C30—Ir—C1—N1−23.6 (4)C30—Ir—C26—C27−76.0 (2)
C30—Ir—C1—N2152.8 (3)C30—Ir—C26—C3344.4 (2)
C31—Ir—C1—N1−168.9 (3)C31—Ir—C26—C27−112.3 (2)
C31—Ir—C1—N27.5 (5)C31—Ir—C26—C338.2 (2)
C1—N2—C2—C30.6 (3)Ir—C26—C27—C2899.3 (3)
C7—N2—C2—C3178.9 (3)C33—C26—C27—Ir−106.1 (3)
N2—C2—C3—N10.4 (3)C33—C26—C27—C28−6.8 (4)
C1—N1—C3—C2−1.4 (3)P—Ir—C27—C26176.7 (3)
C4—N1—C3—C2178.9 (3)P—Ir—C27—C2852.7 (6)
C1—N1—C4—C5−119.8 (3)C1—Ir—C27—C26−98.8 (2)
C1—N1—C4—C6117.1 (3)C1—Ir—C27—C28137.2 (3)
C3—N1—C4—C559.9 (4)C26—Ir—C27—C28−124.0 (3)
C3—N1—C4—C6−63.1 (4)C30—Ir—C27—C2699.9 (2)
Ir—P—C8—C9−122.0 (3)C30—Ir—C27—C28−24.1 (2)
Ir—P—C8—C1363.8 (4)C31—Ir—C27—C2666.2 (2)
C8'—P—C8—C9167 (2)C31—Ir—C27—C28−57.8 (2)
C8'—P—C8—C13−7.4 (17)Ir—C27—C28—C2939.1 (4)
C14—P—C8—C94.9 (4)C26—C27—C28—C29−40.7 (4)
C14—P—C8—C13−169.3 (3)C27—C28—C29—C30−34.5 (4)
C20—P—C8—C9111.1 (3)C28—C29—C30—Ir12.4 (4)
C20—P—C8—C13−63.1 (3)C28—C29—C30—C3195.2 (4)
P—C8—C9—C10−173.9 (5)P—Ir—C30—C29−161.7 (2)
C13—C8—C9—C100.0P—Ir—C30—C3178.60 (17)
C8—C9—C10—C110.0C1—Ir—C30—C29−46.1 (4)
C9—C10—C11—C120.0C1—Ir—C30—C31−165.8 (2)
C10—C11—C12—C130.0C26—Ir—C30—C2943.0 (3)
C11—C12—C13—C80.0C26—Ir—C30—C31−76.72 (18)
P—C8—C13—C12174.6 (4)C27—Ir—C30—C296.8 (3)
C9—C8—C13—C120.0C27—Ir—C30—C31−112.94 (19)
Ir—P—C8'—C9'−125.3 (3)C31—Ir—C30—C29119.7 (3)
Ir—P—C8'—C13'58.0 (4)Ir—C30—C31—C32101.7 (3)
C8—P—C8'—C9'−9.4 (16)C29—C30—C31—Ir−105.7 (3)
C8—P—C8'—C13'174 (2)C29—C30—C31—C32−4.0 (5)
C14—P—C8'—C9'9.8 (5)P—Ir—C31—C30−103.54 (17)
C14—P—C8'—C13'−166.9 (3)P—Ir—C31—C32134.9 (2)
C20—P—C8'—C9'116.8 (4)C1—Ir—C31—C30157.7 (3)
C20—P—C8'—C13'−60.0 (4)C1—Ir—C31—C3236.1 (5)
P—C8'—C9'—C10'−176.8 (5)C26—Ir—C31—C3099.28 (18)
C13'—C8'—C9'—C10'0.0C26—Ir—C31—C32−22.3 (2)
C8'—C9'—C10'—C11'0.0C27—Ir—C31—C3065.46 (18)
C9'—C10'—C11'—C12'0.0C27—Ir—C31—C32−56.1 (2)
C10'—C11'—C12'—C13'0.0C30—Ir—C31—C32−121.6 (3)
C11'—C12'—C13'—C8'0.0Ir—C31—C32—C3333.6 (3)
P—C8'—C13'—C12'176.7 (5)C30—C31—C32—C33−47.0 (4)
C9'—C8'—C13'—C12'0.0C31—C32—C33—C26−27.6 (4)
Ir—P—C14—C1558.5 (3)Ir—C26—C33—C327.8 (3)
Ir—P—C14—C19−121.2 (2)C27—C26—C33—C3291.4 (3)
C8—P—C14—C15−72.2 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5007).

References

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