(3-Benzoyl-1,7,7-trimethyl-bicyclo-[2.2.1]heptan-2-olato-κO,O)bis-[2-(2-pyrid-yl)phenyl-κC,N]iridium(III).

The title compound, [Ir(C(11)H(8)N)(2)(C(17)H(19)O(2))], has an octa-hedral coordination geometry around the Ir(III) atom, retaining the cis-C,C,trans-N,N chelate disposition of the two 2-phenyl-pyridine ligands. The chelate rings are nearly mutually perpendicular [the inter-planar angles range from 85.48 (17) to 89.17 (19)°]. The two 2-(2-pyrid-yl)phenyl ligands are approximately planar, with the plane of the phenyl ring being inclined to that of the pyridine ring by 2.3 (3) and 5.1 (3)° in the two ligands. The inter-planar angle between the phenyl ring in 3-benzoyl-camphor and the IrO(2)C(3) chelate ring is 35.5 (2)°.

Related literature

For general background and for related structures, see: Ulbricht et al. (2009 ▶); Lamansky et al. (2001a ▶); Jones et al. (2010 ▶). For the synthesis of 3-benzoyl-camphor and the title complex, see: Tamiaki et al. (2003 ▶); Lamansky et al. (2001b ▶); Luo et al. (2011 ▶).

Experimental

Crystal data

[Ir(C11H8N)2(C17H19O2)]

M = 755.89

Monoclinic,

a = 10.4569 (6) Å

b = 15.0979 (9) Å

c = 19.9110 (11) Å

β = 101.755 (6)°

V = 3077.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.38 mm−1

T = 296 K

0.36 × 0.32 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.302, T max = 0.433

12765 measured reflections

6233 independent reflections

4631 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.076

S = 0.97

6233 reflections

400 parameters

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −1.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039262/su2315sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039262/su2315Isup2.hkl

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

[Ir(C11H8N)2(C17H19O2)]	F(000) = 1504
Mr = 755.89	Dx = 1.631 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6379 reflections
a = 10.4569 (6) Å	θ = 2.9–28.5°
b = 15.0979 (9) Å	µ = 4.38 mm−1
c = 19.9110 (11) Å	T = 296 K
β = 101.755 (6)°	Block, yellow
V = 3077.6 (3) Å3	0.36 × 0.32 × 0.23 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	6233 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4631 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→18
Tmin = 0.302, Tmax = 0.433	l = −22→24
12765 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max = 0.002
S = 0.97	Δρmax = 1.21 e Å−3
6233 reflections	Δρmin = −1.31 e Å−3
400 parameters

Experimental. (CrysAlis PRO; Oxford Diffraction, 2010). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
Ir1	0.011297 (17)	0.240633 (12)	0.384356 (9)	0.03589 (7)
O1	0.1844 (3)	0.1580 (2)	0.39631 (15)	0.0355 (7)
O2	0.0088 (3)	0.2488 (2)	0.27613 (16)	0.0410 (8)
N1	−0.0946 (4)	0.1267 (3)	0.3756 (2)	0.0411 (10)
N2	0.1116 (4)	0.3565 (3)	0.40134 (18)	0.0354 (9)
C1	−0.1432 (5)	0.0837 (4)	0.3165 (3)	0.0483 (13)
H1	−0.1273	0.1073	0.2758	0.058*
C2	−0.2153 (5)	0.0065 (4)	0.3132 (3)	0.0551 (14)
H2	−0.2492	−0.0206	0.2715	0.066*
C3	−0.2354 (5)	−0.0293 (4)	0.3753 (3)	0.0571 (16)
H3	−0.2805	−0.0823	0.3758	0.069*
C4	−0.1876 (5)	0.0151 (4)	0.4351 (3)	0.0536 (14)
H4	−0.2033	−0.0078	0.4760	0.064*
C5	−0.1169 (4)	0.0924 (3)	0.4370 (3)	0.0431 (12)
C6	−0.0578 (4)	0.1448 (3)	0.4969 (2)	0.0397 (12)
C7	−0.0643 (5)	0.1208 (4)	0.5638 (3)	0.0518 (14)
H7	−0.1059	0.0685	0.5718	0.062*
C8	−0.0086 (5)	0.1750 (4)	0.6182 (3)	0.0574 (15)
H8	−0.0134	0.1596	0.6629	0.069*
C9	0.0532 (6)	0.2509 (4)	0.6057 (3)	0.0551 (15)
H9	0.0917	0.2871	0.6420	0.066*
C10	0.0588 (5)	0.2743 (4)	0.5394 (3)	0.0502 (13)
H10	0.1004	0.3268	0.5321	0.060*
C11	0.0050 (5)	0.2227 (3)	0.4832 (2)	0.0423 (12)
C12	0.2430 (5)	0.3628 (4)	0.4152 (3)	0.0501 (14)
H12	0.2923	0.3123	0.4121	0.060*
C13	0.3068 (6)	0.4420 (5)	0.4339 (3)	0.0630 (16)
H13	0.3975	0.4450	0.4425	0.076*
C14	0.2339 (7)	0.5162 (4)	0.4394 (3)	0.0696 (18)
H14	0.2742	0.5700	0.4529	0.083*
C15	0.0998 (6)	0.5094 (4)	0.4245 (3)	0.0545 (14)
H15	0.0492	0.5593	0.4275	0.065*
C16	0.0404 (5)	0.4308 (4)	0.4054 (2)	0.0467 (13)
C17	−0.1026 (5)	0.4141 (3)	0.3877 (2)	0.0450 (13)
C18	−0.1962 (6)	0.4818 (4)	0.3824 (3)	0.0619 (16)
H18	−0.1709	0.5406	0.3900	0.074*
C19	−0.3295 (6)	0.4585 (5)	0.3653 (3)	0.0695 (18)
H19	−0.3933	0.5021	0.3623	0.083*
C20	−0.3647 (6)	0.3725 (4)	0.3531 (3)	0.0688 (18)
H20	−0.4527	0.3576	0.3420	0.083*
C21	−0.2731 (5)	0.3079 (4)	0.3569 (3)	0.0592 (16)
H21	−0.3009	0.2499	0.3475	0.071*
C22	−0.1386 (5)	0.3247 (3)	0.3746 (2)	0.0399 (12)
C23	0.0909 (4)	0.2123 (3)	0.2447 (2)	0.0330 (10)
C24	0.0621 (4)	0.2298 (3)	0.1683 (2)	0.0365 (11)
C25	0.1607 (5)	0.2425 (3)	0.1319 (2)	0.0413 (11)
H25	0.2478	0.2387	0.1541	0.050*
C26	0.1288 (6)	0.2608 (3)	0.0621 (3)	0.0556 (14)
H26	0.1952	0.2686	0.0379	0.067*
C27	0.0046 (6)	0.2674 (4)	0.0291 (3)	0.0634 (17)
H27	−0.0148	0.2773	−0.0180	0.076*
C28	−0.0949 (6)	0.2597 (4)	0.0646 (3)	0.0647 (17)
H28	−0.1812	0.2677	0.0421	0.078*
C29	−0.0658 (5)	0.2400 (4)	0.1336 (3)	0.0523 (14)
H29	−0.1333	0.2334	0.1572	0.063*
C30	0.1920 (4)	0.1572 (3)	0.2748 (2)	0.0337 (10)
C31	0.2301 (4)	0.1346 (3)	0.3445 (2)	0.0311 (10)
C32	0.3490 (4)	0.0745 (3)	0.3523 (2)	0.0349 (11)
C33	0.3151 (4)	0.0220 (3)	0.2842 (2)	0.0377 (11)
C34	0.2894 (4)	0.1080 (3)	0.2407 (2)	0.0377 (11)
H34	0.2600	0.0984	0.1913	0.045*
C35	0.4212 (5)	0.1555 (4)	0.2612 (2)	0.0477 (13)
H35A	0.4851	0.1311	0.2372	0.057*
H35B	0.4124	0.2186	0.2519	0.057*
C36	0.4591 (5)	0.1375 (3)	0.3380 (2)	0.0444 (12)
H36A	0.4615	0.1919	0.3640	0.053*
H36B	0.5439	0.1090	0.3496	0.053*
C37	0.1943 (5)	−0.0362 (4)	0.2786 (3)	0.0520 (14)
H37A	0.1649	−0.0544	0.2318	0.078*
H37B	0.1264	−0.0033	0.2933	0.078*
H37C	0.2156	−0.0875	0.3072	0.078*
C38	0.4259 (5)	−0.0355 (4)	0.2702 (3)	0.0526 (14)
H38A	0.4493	−0.0782	0.3063	0.079*
H38B	0.5002	0.0011	0.2682	0.079*
H38C	0.3984	−0.0656	0.2272	0.079*
C39	0.3849 (5)	0.0237 (3)	0.4182 (2)	0.0449 (12)
H39A	0.3237	−0.0236	0.4183	0.067*
H39B	0.3830	0.0626	0.4561	0.067*
H39C	0.4712	−0.0004	0.4224	0.067*

	U11	U22	U33	U12	U13	U23
Ir1	0.03940 (11)	0.03886 (12)	0.03298 (10)	0.00425 (9)	0.01573 (7)	0.00030 (9)
O1	0.0318 (18)	0.049 (2)	0.0268 (17)	0.0043 (14)	0.0096 (14)	−0.0017 (14)
O2	0.0458 (18)	0.043 (2)	0.0357 (17)	0.0114 (15)	0.0133 (14)	0.0069 (15)
N1	0.042 (2)	0.040 (2)	0.045 (3)	0.0126 (19)	0.017 (2)	0.0055 (19)
N2	0.038 (2)	0.039 (2)	0.031 (2)	−0.0003 (18)	0.0096 (17)	0.0057 (17)
C1	0.049 (3)	0.056 (4)	0.041 (3)	0.004 (3)	0.013 (3)	−0.005 (3)
C2	0.046 (3)	0.054 (4)	0.064 (4)	0.003 (3)	0.012 (3)	−0.011 (3)
C3	0.042 (3)	0.049 (4)	0.081 (5)	0.001 (3)	0.013 (3)	0.002 (3)
C4	0.050 (3)	0.052 (4)	0.064 (4)	0.002 (3)	0.022 (3)	0.013 (3)
C5	0.037 (3)	0.043 (3)	0.052 (3)	0.007 (2)	0.018 (2)	0.008 (2)
C6	0.038 (3)	0.044 (3)	0.042 (3)	0.009 (2)	0.019 (2)	0.006 (2)
C7	0.052 (3)	0.061 (4)	0.047 (3)	0.001 (3)	0.024 (3)	0.009 (3)
C8	0.058 (3)	0.075 (4)	0.046 (3)	0.016 (3)	0.026 (3)	0.012 (3)
C9	0.063 (4)	0.063 (4)	0.044 (3)	0.016 (3)	0.022 (3)	−0.006 (3)
C10	0.052 (3)	0.057 (4)	0.046 (3)	0.006 (3)	0.023 (3)	−0.001 (3)
C11	0.044 (3)	0.045 (3)	0.043 (3)	0.010 (2)	0.020 (2)	0.002 (2)
C12	0.051 (3)	0.060 (4)	0.042 (3)	−0.002 (3)	0.015 (3)	0.000 (3)
C13	0.056 (4)	0.077 (5)	0.055 (4)	−0.012 (3)	0.007 (3)	0.007 (3)
C14	0.110 (5)	0.053 (4)	0.044 (3)	−0.027 (4)	0.011 (4)	−0.001 (3)
C15	0.073 (4)	0.043 (3)	0.049 (3)	0.005 (3)	0.017 (3)	−0.005 (3)
C16	0.069 (4)	0.047 (3)	0.027 (3)	0.000 (3)	0.018 (2)	0.006 (2)
C17	0.059 (3)	0.045 (3)	0.036 (3)	0.015 (3)	0.020 (3)	0.001 (2)
C18	0.088 (5)	0.049 (4)	0.052 (4)	0.019 (3)	0.020 (3)	0.000 (3)
C19	0.059 (4)	0.088 (6)	0.062 (4)	0.027 (4)	0.015 (3)	0.009 (4)
C20	0.051 (4)	0.066 (5)	0.091 (5)	0.018 (3)	0.017 (3)	0.004 (4)
C21	0.049 (3)	0.058 (4)	0.073 (4)	0.010 (3)	0.017 (3)	0.005 (3)
C22	0.045 (3)	0.042 (3)	0.036 (3)	0.010 (2)	0.018 (2)	−0.002 (2)
C23	0.035 (2)	0.037 (3)	0.029 (2)	0.002 (2)	0.012 (2)	0.002 (2)
C24	0.042 (3)	0.034 (3)	0.032 (2)	0.002 (2)	0.004 (2)	0.001 (2)
C25	0.051 (3)	0.041 (3)	0.033 (2)	−0.003 (2)	0.011 (2)	0.006 (2)
C26	0.076 (4)	0.055 (4)	0.039 (3)	−0.003 (3)	0.017 (3)	0.011 (3)
C27	0.078 (4)	0.080 (5)	0.027 (3)	−0.001 (3)	0.000 (3)	0.013 (3)
C28	0.056 (3)	0.084 (5)	0.046 (3)	0.012 (3)	−0.008 (3)	0.002 (3)
C29	0.044 (3)	0.069 (4)	0.044 (3)	0.005 (3)	0.008 (2)	0.006 (3)
C30	0.038 (3)	0.039 (3)	0.024 (2)	0.000 (2)	0.008 (2)	0.002 (2)
C31	0.033 (2)	0.035 (3)	0.027 (2)	−0.0026 (19)	0.0097 (19)	−0.001 (2)
C32	0.037 (3)	0.040 (3)	0.029 (2)	0.002 (2)	0.009 (2)	0.002 (2)
C33	0.041 (3)	0.041 (3)	0.032 (3)	0.003 (2)	0.009 (2)	0.001 (2)
C34	0.045 (3)	0.044 (3)	0.025 (2)	0.007 (2)	0.009 (2)	0.001 (2)
C35	0.051 (3)	0.054 (3)	0.044 (3)	0.000 (2)	0.025 (3)	0.007 (2)
C36	0.039 (3)	0.054 (3)	0.040 (3)	−0.004 (2)	0.007 (2)	−0.002 (2)
C37	0.055 (3)	0.051 (3)	0.049 (3)	−0.011 (3)	0.007 (3)	0.002 (3)
C38	0.064 (3)	0.051 (3)	0.042 (3)	0.020 (3)	0.009 (3)	−0.002 (3)
C39	0.041 (3)	0.055 (3)	0.038 (3)	0.004 (2)	0.005 (2)	0.008 (2)

Ir1—O1	2.171 (3)	C19—H19	0.9300
Ir1—O2	2.153 (3)	C19—C20	1.358 (9)
Ir1—N1	2.033 (4)	C20—H20	0.9300
Ir1—N2	2.032 (4)	C20—C21	1.358 (7)
Ir1—C11	2.001 (5)	C21—H21	0.9300
Ir1—C22	1.996 (5)	C21—C22	1.402 (6)
O1—C31	1.272 (5)	C23—C24	1.512 (6)
O2—C23	1.285 (5)	C23—C30	1.382 (6)
N1—C1	1.349 (6)	C24—C25	1.390 (6)
N1—C5	1.392 (6)	C24—C29	1.384 (7)
N2—C12	1.349 (6)	C25—H25	0.9300
N2—C16	1.358 (6)	C25—C26	1.388 (7)
C1—H1	0.9300	C26—H26	0.9300
C1—C2	1.383 (7)	C26—C27	1.334 (8)
C2—H2	0.9300	C27—H27	0.9300
C2—C3	1.404 (7)	C27—C28	1.376 (8)
C3—H3	0.9300	C28—H28	0.9300
C3—C4	1.368 (8)	C28—C29	1.377 (7)
C4—H4	0.9300	C29—H29	0.9300
C4—C5	1.377 (7)	C30—C31	1.406 (6)
C5—C6	1.459 (7)	C30—C34	1.526 (6)
C6—C7	1.396 (6)	C31—C32	1.522 (6)
C6—C11	1.401 (6)	C32—C33	1.549 (6)
C7—H7	0.9300	C32—C36	1.564 (6)
C7—C8	1.388 (8)	C32—C39	1.500 (6)
C8—H8	0.9300	C33—C34	1.553 (6)
C8—C9	1.364 (8)	C33—C37	1.524 (6)
C9—H9	0.9300	C33—C38	1.518 (6)
C9—C10	1.380 (7)	C34—H34	0.9800
C10—H10	0.9300	C34—C35	1.534 (6)
C10—C11	1.384 (7)	C35—H35A	0.9700
C12—H12	0.9300	C35—H35B	0.9700
C12—C13	1.383 (8)	C35—C36	1.523 (6)
C13—H13	0.9300	C36—H36A	0.9700
C13—C14	1.371 (8)	C36—H36B	0.9700
C14—H14	0.9300	C37—H37A	0.9600
C14—C15	1.377 (8)	C37—H37B	0.9600
C15—H15	0.9300	C37—H37C	0.9600
C15—C16	1.356 (7)	C38—H38A	0.9600
C16—C17	1.487 (7)	C38—H38B	0.9600
C17—C18	1.404 (7)	C38—H38C	0.9600
C17—C22	1.411 (7)	C39—H39A	0.9600
C18—H18	0.9300	C39—H39B	0.9600
C18—C19	1.410 (8)	C39—H39C	0.9600
?···?	?
O2—Ir1—O1	88.99 (11)	C21—C20—H20	119.5
N1—Ir1—O1	87.18 (13)	C20—C21—H21	118.5
N1—Ir1—O2	93.82 (14)	C20—C21—C22	122.9 (6)
N2—Ir1—O1	94.93 (14)	C22—C21—H21	118.5
N2—Ir1—O2	91.04 (13)	C17—C22—Ir1	114.5 (4)
N2—Ir1—N1	174.74 (14)	C21—C22—Ir1	129.6 (4)
C11—Ir1—O1	90.47 (15)	C21—C22—C17	115.9 (5)
C11—Ir1—O2	174.84 (17)	O2—C23—C24	113.5 (4)
C11—Ir1—N1	81.03 (19)	O2—C23—C30	125.1 (4)
C11—Ir1—N2	94.12 (18)	C30—C23—C24	121.3 (4)
C22—Ir1—O1	175.56 (16)	C25—C24—C23	122.2 (4)
C22—Ir1—O2	90.97 (15)	C29—C24—C23	119.8 (4)
C22—Ir1—N1	97.25 (18)	C29—C24—C25	117.9 (4)
C22—Ir1—N2	80.63 (19)	C24—C25—H25	120.1
C22—Ir1—C11	89.96 (19)	C26—C25—C24	119.8 (5)
C31—O1—Ir1	120.9 (3)	C26—C25—H25	120.1
C23—O2—Ir1	126.1 (3)	C25—C26—H26	119.4
C1—N1—Ir1	125.7 (3)	C27—C26—C25	121.2 (5)
C1—N1—C5	119.1 (4)	C27—C26—H26	119.4
C5—N1—Ir1	115.2 (3)	C26—C27—H27	119.9
C12—N2—Ir1	124.4 (3)	C26—C27—C28	120.2 (5)
C12—N2—C16	118.5 (5)	C28—C27—H27	119.9
C16—N2—Ir1	116.8 (3)	C27—C28—H28	120.2
N1—C1—H1	118.3	C27—C28—C29	119.5 (5)
N1—C1—C2	123.5 (5)	C29—C28—H28	120.2
C2—C1—H1	118.3	C24—C29—H29	119.4
C1—C2—H2	121.3	C28—C29—C24	121.2 (5)
C1—C2—C3	117.5 (5)	C28—C29—H29	119.4
C3—C2—H2	121.3	C23—C30—C31	127.7 (4)
C2—C3—H3	120.5	C23—C30—C34	128.4 (4)
C4—C3—C2	118.9 (5)	C31—C30—C34	104.0 (4)
C4—C3—H3	120.5	O1—C31—C30	131.0 (4)
C3—C4—H4	118.7	O1—C31—C32	121.1 (4)
C3—C4—C5	122.6 (5)	C30—C31—C32	107.8 (4)
C5—C4—H4	118.7	C31—C32—C33	100.3 (4)
N1—C5—C6	113.4 (4)	C31—C32—C36	103.6 (4)
C4—C5—N1	118.4 (5)	C33—C32—C36	101.3 (3)
C4—C5—C6	128.2 (5)	C39—C32—C31	116.6 (4)
C7—C6—C5	122.9 (5)	C39—C32—C33	118.5 (4)
C7—C6—C11	121.3 (5)	C39—C32—C36	114.1 (4)
C11—C6—C5	115.8 (4)	C32—C33—C34	92.5 (4)
C6—C7—H7	120.1	C37—C33—C32	113.4 (3)
C8—C7—C6	119.8 (5)	C37—C33—C34	113.2 (4)
C8—C7—H7	120.1	C38—C33—C32	113.9 (4)
C7—C8—H8	120.3	C38—C33—C34	115.3 (4)
C9—C8—C7	119.5 (5)	C38—C33—C37	108.0 (4)
C9—C8—H8	120.3	C30—C34—C33	102.4 (3)
C8—C9—H9	119.9	C30—C34—H34	114.7
C8—C9—C10	120.3 (6)	C30—C34—C35	107.4 (4)
C10—C9—H9	119.9	C33—C34—H34	114.7
C9—C10—H10	118.7	C35—C34—C33	101.4 (4)
C9—C10—C11	122.7 (5)	C35—C34—H34	114.7
C11—C10—H10	118.7	C34—C35—H35A	111.2
C6—C11—Ir1	114.5 (4)	C34—C35—H35B	111.2
C10—C11—Ir1	129.0 (4)	H35A—C35—H35B	109.1
C10—C11—C6	116.4 (4)	C36—C35—C34	102.7 (4)
N2—C12—H12	118.9	C36—C35—H35A	111.2
N2—C12—C13	122.1 (5)	C36—C35—H35B	111.2
C13—C12—H12	118.9	C32—C36—H36A	111.0
C12—C13—H13	120.6	C32—C36—H36B	111.0
C14—C13—C12	118.8 (6)	C35—C36—C32	104.0 (4)
C14—C13—H13	120.6	C35—C36—H36A	111.0
C13—C14—H14	120.6	C35—C36—H36B	111.0
C13—C14—C15	118.7 (6)	H36A—C36—H36B	109.0
C15—C14—H14	120.6	C33—C37—H37A	109.5
C14—C15—H15	119.5	C33—C37—H37B	109.5
C16—C15—C14	120.9 (6)	C33—C37—H37C	109.5
C16—C15—H15	119.5	H37A—C37—H37B	109.5
N2—C16—C17	112.5 (5)	H37A—C37—H37C	109.5
C15—C16—N2	120.9 (5)	H37B—C37—H37C	109.5
C15—C16—C17	126.6 (5)	C33—C38—H38A	109.5
C18—C17—C16	123.1 (5)	C33—C38—H38B	109.5
C18—C17—C22	121.8 (5)	C33—C38—H38C	109.5
C22—C17—C16	115.1 (4)	H38A—C38—H38B	109.5
C17—C18—H18	120.8	H38A—C38—H38C	109.5
C17—C18—C19	118.4 (6)	H38B—C38—H38C	109.5
C19—C18—H18	120.8	C32—C39—H39A	109.5
C18—C19—H19	120.0	C32—C39—H39B	109.5
C20—C19—C18	120.0 (6)	C32—C39—H39C	109.5
C20—C19—H19	120.0	H39A—C39—H39B	109.5
C19—C20—H20	119.5	H39A—C39—H39C	109.5
C21—C20—C19	121.0 (6)	H39B—C39—H39C	109.5
Ir1—O1—C31—C30	4.1 (7)	C11—Ir1—N1—C5	−1.2 (3)
Ir1—O1—C31—C32	−178.1 (3)	C11—Ir1—N2—C12	90.3 (4)
Ir1—O2—C23—C24	179.6 (3)	C11—Ir1—N2—C16	−83.1 (3)
Ir1—O2—C23—C30	3.6 (7)	C11—Ir1—C22—C17	90.6 (4)
Ir1—N1—C1—C2	−179.7 (4)	C11—Ir1—C22—C21	−89.3 (5)
Ir1—N1—C5—C4	−179.7 (4)	C11—C6—C7—C8	0.5 (7)
Ir1—N1—C5—C6	−0.8 (5)	C12—N2—C16—C15	−1.5 (7)
Ir1—N2—C12—C13	−172.6 (4)	C12—N2—C16—C17	179.0 (4)
Ir1—N2—C16—C15	172.3 (4)	C12—C13—C14—C15	−1.5 (8)
Ir1—N2—C16—C17	−7.2 (5)	C13—C14—C15—C16	0.7 (8)
O1—Ir1—O2—C23	−0.2 (4)	C14—C15—C16—N2	0.9 (8)
O1—Ir1—N1—C1	−90.4 (4)	C14—C15—C16—C17	−179.7 (5)
O1—Ir1—N1—C5	89.7 (3)	C15—C16—C17—C18	6.2 (8)
O1—Ir1—N2—C12	−0.5 (4)	C15—C16—C17—C22	−175.4 (5)
O1—Ir1—N2—C16	−173.9 (3)	C16—N2—C12—C13	0.6 (7)
O1—Ir1—C11—C6	−84.1 (4)	C16—C17—C18—C19	−179.9 (5)
O1—Ir1—C11—C10	92.7 (5)	C16—C17—C22—Ir1	0.9 (5)
O1—Ir1—C22—C17	−5(2)	C16—C17—C22—C21	−179.2 (4)
O1—Ir1—C22—C21	175.2 (16)	C17—C18—C19—C20	−1.2 (9)
O1—C31—C32—C33	146.6 (4)	C18—C17—C22—Ir1	179.4 (4)
O1—C31—C32—C36	−109.0 (4)	C18—C17—C22—C21	−0.8 (7)
O1—C31—C32—C39	17.2 (6)	C18—C19—C20—C21	−0.2 (10)
O2—Ir1—O1—C31	−3.3 (3)	C19—C20—C21—C22	1.2 (9)
O2—Ir1—N1—C1	−1.6 (4)	C20—C21—C22—Ir1	179.2 (5)
O2—Ir1—N1—C5	178.5 (3)	C20—C21—C22—C17	−0.7 (8)
O2—Ir1—N2—C12	−89.6 (4)	C22—Ir1—O1—C31	−92.8 (19)
O2—Ir1—N2—C16	97.0 (3)	C22—Ir1—O2—C23	175.3 (4)
O2—Ir1—C11—C6	−0.1 (19)	C22—Ir1—N1—C1	89.9 (4)
O2—Ir1—C11—C10	176.7 (14)	C22—Ir1—N1—C5	−90.0 (3)
O2—Ir1—C22—C17	−94.5 (4)	C22—Ir1—N2—C12	179.6 (4)
O2—Ir1—C22—C21	85.7 (4)	C22—Ir1—N2—C16	6.2 (3)
O2—C23—C24—C25	143.4 (4)	C22—Ir1—C11—C6	100.3 (4)
O2—C23—C24—C29	−31.9 (6)	C22—Ir1—C11—C10	−82.8 (5)
O2—C23—C30—C31	−4.2 (8)	C22—C17—C18—C19	1.7 (8)
O2—C23—C30—C34	176.9 (4)	C23—C24—C25—C26	−178.2 (4)
N1—Ir1—O1—C31	90.6 (3)	C23—C24—C29—C28	177.3 (5)
N1—Ir1—O2—C23	−87.3 (4)	C23—C30—C31—O1	−0.3 (8)
N1—Ir1—N2—C12	112.9 (16)	C23—C30—C31—C32	−178.2 (5)
N1—Ir1—N2—C16	−60.5 (17)	C23—C30—C34—C33	−146.9 (5)
N1—Ir1—C11—C6	3.0 (3)	C23—C30—C34—C35	106.7 (5)
N1—Ir1—C11—C10	179.8 (5)	C24—C23—C30—C31	−179.9 (4)
N1—Ir1—C22—C17	171.5 (3)	C24—C23—C30—C34	1.2 (8)
N1—Ir1—C22—C21	−8.3 (5)	C24—C25—C26—C27	0.6 (8)
N1—C1—C2—C3	−1.6 (8)	C25—C24—C29—C28	1.7 (8)
N1—C5—C6—C7	−177.8 (4)	C25—C26—C27—C28	2.7 (9)
N1—C5—C6—C11	3.3 (6)	C26—C27—C28—C29	−3.7 (9)
N2—Ir1—O1—C31	−94.2 (3)	C27—C28—C29—C24	1.5 (9)
N2—Ir1—O2—C23	94.7 (4)	C29—C24—C25—C26	−2.8 (7)
N2—Ir1—N1—C1	155.9 (15)	C30—C23—C24—C25	−40.4 (7)
N2—Ir1—N1—C5	−24.0 (18)	C30—C23—C24—C29	144.2 (5)
N2—Ir1—C11—C6	−179.0 (3)	C30—C31—C32—C33	−35.2 (4)
N2—Ir1—C11—C10	−2.2 (5)	C30—C31—C32—C36	69.2 (4)
N2—Ir1—C22—C17	−3.6 (3)	C30—C31—C32—C39	−164.6 (4)
N2—Ir1—C22—C21	176.6 (5)	C30—C34—C35—C36	67.0 (5)
N2—C12—C13—C14	0.9 (8)	C31—C30—C34—C33	34.0 (5)
N2—C16—C17—C18	−174.3 (4)	C31—C30—C34—C35	−72.4 (4)
N2—C16—C17—C22	4.1 (6)	C31—C32—C33—C34	51.7 (4)
C1—N1—C5—C4	0.4 (7)	C31—C32—C33—C37	−65.0 (5)
C1—N1—C5—C6	179.3 (4)	C31—C32—C33—C38	170.9 (4)
C1—C2—C3—C4	2.4 (8)	C31—C32—C36—C35	−71.1 (4)
C2—C3—C4—C5	−1.9 (8)	C32—C33—C34—C30	−52.6 (4)
C3—C4—C5—N1	0.5 (8)	C32—C33—C34—C35	58.3 (4)
C3—C4—C5—C6	−178.2 (5)	C33—C32—C36—C35	32.6 (5)
C4—C5—C6—C7	1.0 (8)	C33—C34—C35—C36	−40.0 (4)
C4—C5—C6—C11	−177.8 (5)	C34—C30—C31—O1	178.8 (5)
C5—N1—C1—C2	0.2 (7)	C34—C30—C31—C32	0.8 (5)
C5—C6—C7—C8	−178.4 (4)	C34—C35—C36—C32	4.4 (5)
C5—C6—C11—Ir1	−4.3 (5)	C36—C32—C33—C34	−54.5 (4)
C5—C6—C11—C10	178.4 (4)	C36—C32—C33—C37	−171.2 (4)
C6—C7—C8—C9	−0.6 (8)	C36—C32—C33—C38	64.7 (5)
C7—C6—C11—Ir1	176.8 (4)	C37—C33—C34—C30	64.3 (5)
C7—C6—C11—C10	−0.5 (7)	C37—C33—C34—C35	175.2 (4)
C7—C8—C9—C10	0.8 (8)	C38—C33—C34—C30	−170.6 (4)
C8—C9—C10—C11	−0.9 (8)	C38—C33—C34—C35	−59.7 (5)
C9—C10—C11—Ir1	−176.1 (4)	C39—C32—C33—C34	179.8 (4)
C9—C10—C11—C6	0.7 (7)	C39—C32—C33—C37	63.1 (5)
C11—Ir1—O1—C31	171.6 (3)	C39—C32—C33—C38	−61.0 (5)
C11—Ir1—O2—C23	−84.2 (17)	C39—C32—C36—C35	161.1 (4)
C11—Ir1—N1—C1	178.7 (4)