mer-[3-Phenyl-5-(2-pyridyl-κN)-1,2,4-triazol-1-ido-κN]bis-(2-quinolylphenyl-κC,N)iridium(III) deuterochloro-form disolvate.

In the title compound, [Ir(C(13)H(9)N(4))(C(15)H(10)N)(2)]·2CDCl(3), the coordination at iridium is octa-hedral, but with narrow ligand bite angles ranging from 74.85 (8) to 83.99 (8)°. The bond lengths at iridium show the expected trans influence, with Ir-N trans to C being appreciably longer than trans to N. The chelate rings are mutually perpendicular to a reasonable approximation [interplanar angles ranging from 77.79 (6) to 83.93 (7)°]. All ligands are approximately planar; the maximum inter-planar angles within ligands are ca 12°. One CDCl(3) solvent molecule is severly disordered and was excluded from the refinement.

Related literature

For the preparation of iridium complexes, see: Lamansky et al. (2001 ▶); Coppo et al. (2004 ▶). For the photoluminescent properties and color tuning of cyclo­metalated iridium complexes, see: Grushin et al. (2001 ▶); You & Park (2005 ▶); Stagni et al. (2008 ▶). For general background to organic light-emitting diodes (OLEDs), see: Hertel et al. (2005 ▶); Holder et al. (2005 ▶). For two recent related publications from our groups, see: Jones et al. (2010a ▶,b ▶).

Experimental

Crystal data

[Ir(C13H9N4)(C15H10N)2]·2CDCl3

M = 1062.67

Triclinic,

a = 9.1399 (3) Å

b = 12.4430 (5) Å

c = 17.6762 (6) Å

α = 81.493 (4)°

β = 81.509 (4)°

γ = 85.193 (4)°

V = 1962.41 (12) Å3

Z = 2

Mo Kα radiation

μ = 3.86 mm−1

T = 100 K

0.25 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.739, T max = 1.000

78670 measured reflections

9739 independent reflections

8125 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.048

S = 0.93

9739 reflections

487 parameters

134 restraints

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −1.08 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: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038596/bt5363sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038596/bt5363Isup2.hkl

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

[Ir(C13H9N4)(C15H10N)2]·2CDCl3	Z = 2
Mr = 1062.67	F(000) = 1044
Triclinic, P1	Dx = 1.798 Mg m−3
a = 9.1399 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4430 (5) Å	Cell parameters from 26610 reflections
c = 17.6762 (6) Å	θ = 2.2–30.8°
α = 81.493 (4)°	µ = 3.86 mm−1
β = 81.509 (4)°	T = 100 K
γ = 85.193 (4)°	Tablet, orange
V = 1962.41 (12) Å3	0.25 × 0.20 × 0.05 mm

Oxford Diffraction Xcalibur Eos diffractometer	9739 independent reflections
Radiation source: Enhance (Mo) X-ray Source	8125 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 16.1419 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω–scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
Tmin = 0.739, Tmax = 1.000	l = −23→23
78670 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.019P)2] where P = (Fo2 + 2Fc2)/3
9739 reflections	(Δ/σ)max = 0.003
487 parameters	Δρmax = 1.03 e Å−3
134 restraints	Δρmin = −1.07 e Å−3

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)8.0107 (0.0039) x - 5.0559 (0.0100) y + 1.0694 (0.0169) z = 0.3793 (0.0119)* 0.0612 (0.0010) Ir * -0.0747 (0.0014) N1 * 0.0495 (0.0016) C2 * 0.0270 (0.0017) C11 * -0.0630 (0.0014) C12Rms deviation of fitted atoms = 0.05743.5166 (0.0086) x + 11.8000 (0.0045) y + 4.6463 (0.0182) z = 11.4217 (0.0048)Angle to previous plane (with approximate e.s.d.) = 83.93 (0.07)* -0.0639 (0.0011) Ir * 0.0668 (0.0016) C28 * -0.0280 (0.0019) C27 * -0.0526 (0.0019) C18 * 0.0777 (0.0015) N17Rms deviation of fitted atoms = 0.06022.1808 (0.0086) x + 0.5392 (0.0092) y + 17.4903 (0.0021) z = 5.6802 (0.0088)Angle to previous plane (with approximate e.s.d.) = 78.84 (0.08)* -0.0035 (0.0009) Ir * 0.0040 (0.0013) N33 * -0.0019 (0.0016) C37 * -0.0031 (0.0016) C38 * 0.0045 (0.0014) N39Rms deviation of fitted atoms = 0.00358.0107 (0.0039) x - 5.0559 (0.0100) y + 1.0694 (0.0169) z = 0.3793 (0.0119)Angle to previous plane (with approximate e.s.d.) = 78.79 (0.08)* 0.0612 (0.0010) Ir * -0.0747 (0.0014) N1 * 0.0495 (0.0016) C2 * 0.0270 (0.0017) C11 * -0.0630 (0.0014) C12Rms deviation of fitted atoms = 0.05748.1366 (0.0044) x - 4.6169 (0.0120) y + 2.7467 (0.0185) z = 1.1577 (0.0155)Angle to previous plane (with approximate e.s.d.) = 5.58 (0.11)* -0.0062 (0.0018) C11 * 0.0042 (0.0018) C12 * 0.0004 (0.0019) C13 * -0.0031 (0.0020) C14 * 0.0011 (0.0020) C15 * 0.0036 (0.0019) C16Rms deviation of fitted atoms = 0.0036- 7.1556 (0.0029) x + 6.8670 (0.0050) y - 1.5139 (0.0120) z = 1.5526 (0.0051)Angle to previous plane (with approximate e.s.d.) = 11.79 (0.10)* -0.0880 (0.0018) N1 * 0.0273 (0.0020) C2 * 0.0689 (0.0021) C3 * 0.0094 (0.0021) C4 * -0.0354 (0.0024) C5 * -0.0377 (0.0021) C6 * -0.0110 (0.0022) C7 * 0.0624 (0.0021) C8 * 0.0474 (0.0020) C9 * -0.0432 (0.0022) C10Rms deviation of fitted atoms = 0.04913.8481 (0.0098) x + 11.4658 (0.0058) y + 6.3281 (0.0208) z = 11.7536 (0.0044)Angle to previous plane (with approximate e.s.d.) = 77.79 (0.06)* -0.0067 (0.0020) C28 * 0.0001 (0.0020) C29 * 0.0072 (0.0023) C30 * -0.0080 (0.0025) C31 * 0.0013 (0.0023) C32 * 0.0060 (0.0021) C27Rms deviation of fitted atoms = 0.00582.0501 (0.0054) x + 12.1910 (0.0019) y + 5.3371 (0.0154) z = 11.4565 (0.0058)Angle to previous plane (with approximate e.s.d.) = 12.28 (0.08)* -0.0704 (0.0021) N17 * 0.0393 (0.0024) C18 * 0.0498 (0.0028) C19 * -0.0036 (0.0029) C20 * -0.0280 (0.0030) C21 * -0.0253 (0.0030) C22 * 0.0012 (0.0029) C23 * 0.0474 (0.0026) C24 * 0.0300 (0.0024) C25 * -0.0404 (0.0026) C26Rms deviation of fitted atoms = 0.03902.0139 (0.0103) x + 0.5046 (0.0150) y + 17.5147 (0.0030) z = 5.5443 (0.0128)Angle to previous plane (with approximate e.s.d.) = 78.01 (0.09)* 0.0047 (0.0018) C38 * 0.0079 (0.0017) N39 * -0.0141 (0.0019) C40 * 0.0073 (0.0022) C41 * 0.0051 (0.0023) C42 * -0.0109 (0.0020) C43Rms deviation of fitted atoms = 0.00902.2942 (0.0112) x + 0.5668 (0.0154) y + 17.4708 (0.0033) z = 5.7456 (0.0097)Angle to previous plane (with approximate e.s.d.) = 1.81 (0.06)* -0.0023 (0.0014) N33 * 0.0007 (0.0014) N34 * 0.0010 (0.0015) C35 * -0.0024 (0.0015) N36 * 0.0029 (0.0015) C37Rms deviation of fitted atoms = 0.00203.5283 (0.0116) x - 0.8562 (0.0173) y + 16.6404 (0.0084) z = 5.4129 (0.0060)Angle to previous plane (with approximate e.s.d.) = 11.00 (0.10)* -0.0031 (0.0021) C44 * 0.0013 (0.0022) C45 * -0.0006 (0.0025) C46 * 0.0019 (0.0027) C47 * -0.0038 (0.0027) C48 * 0.0044 (0.0024) C49Rms deviation of fitted atoms = 0.0029

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
Ir	0.479659 (11)	0.724128 (9)	0.242431 (7)	0.01435 (3)
N1	0.5063 (2)	0.76795 (18)	0.12298 (13)	0.0164 (5)
C2	0.5821 (3)	0.8582 (2)	0.09770 (16)	0.0183 (6)
C3	0.6254 (3)	0.8918 (2)	0.01826 (17)	0.0241 (7)
H3	0.6797	0.9550	0.0022	0.029*
C4	0.5898 (3)	0.8342 (2)	−0.03560 (17)	0.0250 (7)
H4	0.6227	0.8551	−0.0889	0.030*
C5	0.5035 (3)	0.7430 (2)	−0.01136 (16)	0.0224 (6)
C6	0.4578 (3)	0.6834 (3)	−0.06484 (17)	0.0274 (7)
H6	0.4897	0.7018	−0.1185	0.033*
C7	0.3680 (3)	0.5992 (3)	−0.03966 (18)	0.0283 (7)
H7	0.3403	0.5578	−0.0757	0.034*
C8	0.3166 (3)	0.5737 (2)	0.03924 (17)	0.0253 (7)
H8	0.2504	0.5173	0.0559	0.030*
C9	0.3608 (3)	0.6295 (2)	0.09300 (16)	0.0198 (6)
H9	0.3251	0.6114	0.1463	0.024*
C10	0.4586 (3)	0.7129 (2)	0.06896 (16)	0.0184 (6)
C11	0.6096 (3)	0.9190 (2)	0.15802 (16)	0.0189 (6)
C12	0.5580 (3)	0.8711 (2)	0.23424 (17)	0.0190 (6)
C13	0.5710 (3)	0.9308 (2)	0.29458 (17)	0.0226 (6)
H13	0.5371	0.9019	0.3464	0.027*
C14	0.6325 (3)	1.0308 (2)	0.27935 (19)	0.0284 (7)
H14	0.6397	1.0695	0.3210	0.034*
C15	0.6835 (3)	1.0757 (2)	0.20527 (19)	0.0293 (7)
H15	0.7257	1.1444	0.1961	0.035*
C16	0.6729 (3)	1.0201 (2)	0.14405 (18)	0.0261 (7)
H16	0.7085	1.0504	0.0928	0.031*
N17	0.4354 (3)	0.70179 (19)	0.36314 (13)	0.0239 (6)
C18	0.2901 (3)	0.7236 (3)	0.38966 (19)	0.0348 (8)
C19	0.2355 (5)	0.6990 (3)	0.4688 (2)	0.0534 (11)
H19	0.1330	0.7126	0.4857	0.064*
C20	0.3248 (5)	0.6572 (3)	0.5199 (2)	0.0562 (11)
H20	0.2855	0.6390	0.5727	0.067*
C21	0.4788 (5)	0.6398 (3)	0.49591 (18)	0.0439 (9)
C22	0.5786 (5)	0.6009 (3)	0.5471 (2)	0.0589 (11)
H22	0.5423	0.5823	0.6002	0.071*
C23	0.7259 (5)	0.5885 (3)	0.5236 (2)	0.0557 (11)
H23	0.7916	0.5607	0.5598	0.067*
C24	0.7820 (4)	0.6177 (3)	0.4441 (2)	0.0431 (9)
H24	0.8857	0.6111	0.4275	0.052*
C25	0.6862 (3)	0.6555 (2)	0.39132 (17)	0.0298 (7)
H25	0.7237	0.6753	0.3385	0.036*
C26	0.5336 (4)	0.6647 (2)	0.41575 (17)	0.0290 (7)
C27	0.1995 (3)	0.7753 (3)	0.3323 (2)	0.0338 (8)
C28	0.2731 (3)	0.7910 (2)	0.25696 (19)	0.0266 (7)
C29	0.1941 (3)	0.8497 (2)	0.1998 (2)	0.0354 (8)
H29	0.2412	0.8625	0.1480	0.043*
C30	0.0488 (4)	0.8890 (3)	0.2181 (3)	0.0552 (12)
H30	−0.0021	0.9291	0.1788	0.066*
C31	−0.0228 (4)	0.8707 (3)	0.2923 (3)	0.0645 (14)
H31	−0.1232	0.8965	0.3039	0.077*
C32	0.0508 (4)	0.8153 (3)	0.3494 (3)	0.0541 (11)
H32	0.0019	0.8036	0.4010	0.065*
N33	0.4299 (2)	0.55788 (18)	0.25419 (12)	0.0145 (5)
N34	0.3042 (2)	0.50125 (18)	0.27271 (13)	0.0185 (5)
C35	0.3547 (3)	0.3969 (2)	0.26948 (14)	0.0169 (6)
N36	0.5032 (2)	0.38198 (18)	0.25027 (12)	0.0169 (5)
C37	0.5433 (3)	0.4844 (2)	0.24198 (14)	0.0148 (5)
C38	0.6914 (3)	0.5248 (2)	0.22220 (15)	0.0167 (6)
N39	0.6947 (2)	0.63400 (18)	0.21885 (12)	0.0153 (5)
C40	0.8272 (3)	0.6779 (2)	0.20110 (16)	0.0205 (6)
H40	0.8300	0.7547	0.1968	0.025*
C41	0.9589 (3)	0.6165 (3)	0.18894 (19)	0.0317 (8)
H41	1.0507	0.6500	0.1783	0.038*
C42	0.9549 (3)	0.5056 (3)	0.19247 (19)	0.0334 (8)
H42	1.0443	0.4616	0.1840	0.040*
C43	0.8196 (3)	0.4583 (2)	0.20849 (17)	0.0254 (7)
H43	0.8147	0.3820	0.2100	0.030*
C44	0.2545 (3)	0.3068 (2)	0.28691 (16)	0.0215 (6)
C45	0.3072 (3)	0.2027 (2)	0.27066 (17)	0.0258 (7)
H45	0.4076	0.1904	0.2490	0.031*
C46	0.2140 (4)	0.1174 (3)	0.2859 (2)	0.0387 (8)
H46	0.2504	0.0470	0.2744	0.046*
C47	0.0680 (4)	0.1350 (3)	0.3179 (2)	0.0477 (10)
H47	0.0040	0.0767	0.3288	0.057*
C48	0.0154 (4)	0.2382 (3)	0.3340 (2)	0.0472 (10)
H48	−0.0852	0.2503	0.3554	0.057*
C49	0.1075 (3)	0.3236 (3)	0.31940 (18)	0.0330 (8)
H49	0.0706	0.3936	0.3315	0.040*
C98	0.9808 (4)	1.2544 (3)	0.0450 (2)	0.0480 (10)
H98	0.8770	1.2866	0.0552	0.058*
Cl1	1.03734 (9)	1.19846 (8)	0.13387 (6)	0.0509 (2)
Cl2	0.98185 (9)	1.15510 (8)	−0.01637 (6)	0.0519 (3)
Cl3	1.09404 (12)	1.35913 (7)	0.00000 (6)	0.0619 (3)

	U11	U22	U33	U12	U13	U23
Ir	0.01027 (5)	0.01557 (6)	0.01753 (5)	−0.00124 (4)	0.00080 (4)	−0.00580 (4)
N1	0.0137 (11)	0.0170 (12)	0.0190 (12)	0.0011 (9)	−0.0057 (9)	−0.0016 (10)
C2	0.0145 (14)	0.0177 (15)	0.0219 (15)	0.0030 (11)	−0.0063 (11)	0.0011 (12)
C3	0.0183 (15)	0.0236 (17)	0.0286 (17)	0.0005 (12)	−0.0045 (12)	0.0029 (13)
C4	0.0206 (15)	0.0322 (18)	0.0177 (15)	0.0092 (13)	−0.0024 (12)	0.0046 (13)
C5	0.0157 (14)	0.0289 (17)	0.0224 (15)	0.0077 (12)	−0.0059 (12)	−0.0047 (13)
C6	0.0237 (16)	0.0372 (19)	0.0218 (16)	0.0120 (14)	−0.0072 (12)	−0.0090 (14)
C7	0.0260 (16)	0.0340 (19)	0.0292 (17)	0.0109 (14)	−0.0132 (13)	−0.0161 (15)
C8	0.0193 (15)	0.0284 (17)	0.0321 (17)	0.0038 (13)	−0.0108 (13)	−0.0130 (14)
C9	0.0155 (14)	0.0219 (16)	0.0228 (15)	0.0031 (11)	−0.0061 (11)	−0.0044 (12)
C10	0.0130 (13)	0.0232 (16)	0.0199 (15)	0.0075 (11)	−0.0074 (11)	−0.0057 (12)
C11	0.0114 (13)	0.0179 (15)	0.0274 (16)	0.0023 (11)	−0.0055 (11)	−0.0018 (12)
C12	0.0089 (13)	0.0183 (15)	0.0309 (17)	0.0003 (11)	−0.0028 (11)	−0.0075 (13)
C13	0.0194 (15)	0.0226 (16)	0.0266 (16)	−0.0023 (12)	−0.0029 (12)	−0.0053 (13)
C14	0.0262 (16)	0.0241 (17)	0.0389 (19)	−0.0049 (13)	−0.0101 (14)	−0.0099 (15)
C15	0.0266 (16)	0.0153 (16)	0.048 (2)	−0.0090 (13)	−0.0103 (15)	−0.0008 (14)
C16	0.0210 (15)	0.0228 (16)	0.0330 (18)	−0.0039 (13)	−0.0059 (13)	0.0048 (13)
N17	0.0315 (14)	0.0215 (14)	0.0196 (13)	−0.0124 (11)	0.0068 (10)	−0.0094 (11)
C18	0.0363 (18)	0.0285 (19)	0.0391 (19)	−0.0156 (14)	0.0231 (15)	−0.0230 (15)
C19	0.065 (3)	0.047 (2)	0.046 (2)	−0.025 (2)	0.0348 (19)	−0.027 (2)
C20	0.090 (3)	0.044 (2)	0.031 (2)	−0.031 (2)	0.036 (2)	−0.0190 (18)
C21	0.090 (3)	0.029 (2)	0.0147 (16)	−0.0232 (19)	0.0005 (17)	−0.0069 (15)
C22	0.118 (3)	0.043 (2)	0.0192 (19)	−0.027 (3)	−0.008 (2)	−0.0038 (17)
C23	0.118 (3)	0.031 (2)	0.029 (2)	−0.013 (2)	−0.045 (2)	0.0019 (17)
C24	0.065 (2)	0.036 (2)	0.036 (2)	−0.0128 (18)	−0.0306 (18)	0.0001 (16)
C25	0.049 (2)	0.0257 (17)	0.0184 (16)	−0.0096 (15)	−0.0127 (14)	−0.0035 (13)
C26	0.051 (2)	0.0201 (17)	0.0175 (15)	−0.0127 (15)	0.0003 (14)	−0.0084 (13)
C27	0.0210 (16)	0.0265 (18)	0.057 (2)	−0.0097 (13)	0.0094 (15)	−0.0267 (16)
C28	0.0155 (14)	0.0172 (16)	0.051 (2)	−0.0057 (12)	0.0017 (13)	−0.0216 (15)
C29	0.0188 (15)	0.0224 (17)	0.073 (3)	0.0013 (13)	−0.0158 (16)	−0.0240 (17)
C30	0.0200 (18)	0.036 (2)	0.124 (4)	0.0090 (16)	−0.026 (2)	−0.047 (2)
C31	0.0127 (18)	0.047 (3)	0.145 (4)	0.0018 (16)	−0.002 (2)	−0.062 (3)
C32	0.0250 (18)	0.042 (2)	0.099 (3)	−0.0172 (16)	0.0256 (19)	−0.050 (2)
N33	0.0144 (11)	0.0160 (12)	0.0132 (12)	−0.0018 (9)	0.0017 (9)	−0.0056 (9)
N34	0.0170 (12)	0.0172 (12)	0.0210 (13)	−0.0051 (10)	0.0037 (10)	−0.0062 (10)
C35	0.0227 (14)	0.0170 (14)	0.0109 (13)	−0.0033 (11)	0.0006 (11)	−0.0035 (11)
N36	0.0207 (12)	0.0162 (12)	0.0146 (12)	−0.0002 (9)	−0.0048 (9)	−0.0029 (10)
C37	0.0161 (13)	0.0180 (14)	0.0109 (13)	0.0006 (11)	−0.0036 (10)	−0.0029 (11)
C38	0.0171 (13)	0.0203 (15)	0.0147 (14)	−0.0013 (11)	−0.0057 (11)	−0.0057 (11)
N39	0.0111 (11)	0.0204 (13)	0.0156 (12)	−0.0015 (9)	−0.0023 (9)	−0.0055 (10)
C40	0.0149 (14)	0.0237 (16)	0.0245 (16)	−0.0026 (12)	−0.0010 (12)	−0.0093 (13)
C41	0.0124 (14)	0.0341 (19)	0.051 (2)	−0.0007 (13)	−0.0025 (14)	−0.0148 (17)
C42	0.0149 (15)	0.035 (2)	0.053 (2)	0.0089 (13)	−0.0069 (14)	−0.0177 (17)
C43	0.0198 (15)	0.0235 (17)	0.0356 (18)	0.0044 (12)	−0.0091 (13)	−0.0111 (14)
C44	0.0268 (15)	0.0195 (15)	0.0182 (15)	−0.0054 (12)	−0.0002 (12)	−0.0035 (12)
C45	0.0299 (16)	0.0197 (16)	0.0274 (17)	−0.0029 (13)	−0.0007 (13)	−0.0049 (13)
C46	0.048 (2)	0.0209 (18)	0.046 (2)	−0.0094 (15)	0.0068 (17)	−0.0090 (16)
C47	0.052 (2)	0.029 (2)	0.060 (3)	−0.0240 (17)	0.0233 (19)	−0.0152 (18)
C48	0.045 (2)	0.037 (2)	0.057 (2)	−0.0215 (17)	0.0272 (18)	−0.0181 (19)
C49	0.0357 (18)	0.0235 (17)	0.038 (2)	−0.0119 (14)	0.0150 (15)	−0.0113 (15)
C98	0.0281 (19)	0.041 (2)	0.079 (3)	0.0085 (16)	−0.0137 (19)	−0.021 (2)
Cl1	0.0316 (5)	0.0592 (6)	0.0578 (6)	−0.0033 (4)	0.0045 (4)	−0.0049 (5)
Cl2	0.0398 (5)	0.0402 (6)	0.0808 (8)	−0.0097 (4)	−0.0109 (5)	−0.0188 (5)
Cl3	0.0956 (8)	0.0249 (5)	0.0750 (8)	−0.0077 (5)	−0.0487 (6)	0.0000 (5)

Ir—C28	1.995 (3)	N36—C37	1.336 (3)
Ir—C12	1.997 (3)	C37—C38	1.460 (3)
Ir—N1	2.084 (2)	C38—N39	1.354 (3)
Ir—N17	2.093 (2)	C38—C43	1.389 (4)
Ir—N33	2.129 (2)	N39—C40	1.346 (3)
Ir—N39	2.196 (2)	C40—C41	1.378 (4)
N1—C2	1.353 (3)	C41—C42	1.375 (4)
N1—C10	1.392 (3)	C42—C43	1.388 (4)
C2—C3	1.412 (4)	C44—C49	1.393 (4)
C2—C11	1.457 (4)	C44—C45	1.398 (4)
C3—C4	1.363 (4)	C45—C46	1.387 (4)
C4—C5	1.414 (4)	C46—C47	1.384 (4)
C5—C6	1.413 (4)	C47—C48	1.387 (4)
C5—C10	1.421 (4)	C48—C49	1.381 (4)
C6—C7	1.367 (4)	C98—Cl1	1.753 (4)
C7—C8	1.403 (4)	C98—Cl3	1.755 (4)
C8—C9	1.380 (4)	C98—Cl2	1.760 (3)
C9—C10	1.403 (4)	C3—H3	0.9500
C11—C16	1.402 (4)	C4—H4	0.9500
C11—C12	1.419 (4)	C6—H6	0.9500
C12—C13	1.411 (4)	C7—H7	0.9500
C13—C14	1.382 (4)	C8—H8	0.9500
C14—C15	1.375 (4)	C9—H9	0.9500
C15—C16	1.387 (4)	C13—H13	0.9500
N17—C18	1.361 (4)	C14—H14	0.9500
N17—C26	1.391 (4)	C15—H15	0.9500
C18—C19	1.411 (5)	C16—H16	0.9500
C18—C27	1.447 (5)	C19—H19	0.9500
C19—C20	1.328 (5)	C20—H20	0.9500
C20—C21	1.417 (5)	C22—H22	0.9500
C21—C22	1.387 (5)	C23—H23	0.9500
C21—C26	1.429 (4)	C24—H24	0.9500
C22—C23	1.352 (5)	C25—H25	0.9500
C23—C24	1.428 (5)	C29—H29	0.9500
C24—C25	1.379 (4)	C30—H30	0.9500
C25—C26	1.398 (4)	C31—H31	0.9500
C27—C28	1.394 (4)	C32—H32	0.9500
C27—C32	1.413 (4)	C40—H40	0.9500
C28—C29	1.408 (4)	C41—H41	0.9500
C29—C30	1.386 (4)	C42—H42	0.9500
C30—C31	1.372 (6)	C43—H43	0.9500
C31—C32	1.365 (6)	C45—H45	0.9500
N33—C37	1.339 (3)	C46—H46	0.9500
N33—N34	1.371 (3)	C47—H47	0.9500
N34—C35	1.347 (3)	C48—H48	0.9500
C35—N36	1.354 (3)	C49—H49	0.9500
C35—C44	1.476 (4)	C98—H98	1.0000
C28—Ir—C12	89.81 (10)	N39—C38—C43	122.0 (2)
C28—Ir—N1	93.57 (11)	N39—C38—C37	114.3 (2)
C12—Ir—N1	79.82 (10)	C43—C38—C37	123.7 (3)
C28—Ir—N17	79.82 (12)	C40—N39—C38	118.0 (2)
C12—Ir—N17	95.05 (10)	C40—N39—Ir	125.77 (18)
N1—Ir—N17	171.70 (9)	C38—N39—Ir	116.20 (16)
C28—Ir—N33	98.69 (10)	N39—C40—C41	123.0 (3)
C12—Ir—N33	171.11 (9)	C42—C41—C40	118.7 (3)
N1—Ir—N33	102.08 (8)	C41—C42—C43	119.6 (3)
N17—Ir—N33	83.99 (8)	C42—C43—C38	118.6 (3)
C28—Ir—N39	172.20 (9)	C49—C44—C45	119.2 (3)
C12—Ir—N39	96.86 (9)	C49—C44—C35	121.0 (3)
N1—Ir—N39	83.69 (8)	C45—C44—C35	119.9 (3)
N17—Ir—N39	103.50 (9)	C46—C45—C44	120.6 (3)
N33—Ir—N39	74.85 (8)	C47—C46—C45	119.8 (3)
C2—N1—C10	118.8 (2)	C46—C47—C48	119.7 (3)
C2—N1—Ir	114.28 (18)	C49—C48—C47	120.9 (3)
C10—N1—Ir	126.87 (19)	C48—C49—C44	119.9 (3)
N1—C2—C3	121.6 (3)	Cl1—C98—Cl3	110.20 (18)
N1—C2—C11	115.0 (2)	Cl1—C98—Cl2	111.88 (19)
C3—C2—C11	123.3 (3)	Cl3—C98—Cl2	110.3 (2)
C4—C3—C2	120.4 (3)	C4—C3—H3	119.8
C3—C4—C5	119.4 (3)	C2—C3—H3	119.8
C6—C5—C4	121.7 (3)	C3—C4—H4	120.3
C6—C5—C10	119.5 (3)	C5—C4—H4	120.3
C4—C5—C10	118.8 (3)	C7—C6—H6	119.9
C7—C6—C5	120.2 (3)	C5—C6—H6	119.9
C6—C7—C8	120.2 (3)	C6—C7—H7	119.9
C9—C8—C7	120.9 (3)	C8—C7—H7	119.9
C8—C9—C10	120.0 (3)	C9—C8—H8	119.6
N1—C10—C9	120.3 (2)	C7—C8—H8	119.6
N1—C10—C5	120.6 (3)	C8—C9—H9	120.0
C9—C10—C5	119.0 (3)	C10—C9—H9	120.0
C16—C11—C12	121.1 (3)	C14—C13—H13	119.5
C16—C11—C2	124.3 (3)	C12—C13—H13	119.5
C12—C11—C2	114.5 (2)	C15—C14—H14	119.2
C13—C12—C11	116.9 (3)	C13—C14—H14	119.2
C13—C12—Ir	128.0 (2)	C14—C15—H15	120.2
C11—C12—Ir	115.1 (2)	C16—C15—H15	120.2
C14—C13—C12	120.9 (3)	C15—C16—H16	120.1
C15—C14—C13	121.5 (3)	C11—C16—H16	120.1
C14—C15—C16	119.7 (3)	C20—C19—H19	119.4
C15—C16—C11	119.9 (3)	C18—C19—H19	119.4
C18—N17—C26	119.3 (3)	C19—C20—H20	120.0
C18—N17—Ir	112.8 (2)	C21—C20—H20	120.0
C26—N17—Ir	127.88 (19)	C23—C22—H22	119.0
N17—C18—C19	120.8 (3)	C21—C22—H22	119.0
N17—C18—C27	115.7 (3)	C22—C23—H23	120.2
C19—C18—C27	123.5 (3)	C24—C23—H23	120.2
C20—C19—C18	121.2 (4)	C25—C24—H24	119.9
C19—C20—C21	120.0 (3)	C23—C24—H24	119.9
C22—C21—C20	122.7 (4)	C24—C25—H25	120.1
C22—C21—C26	118.7 (4)	C26—C25—H25	120.1
C20—C21—C26	118.6 (3)	C30—C29—H29	119.5
C23—C22—C21	122.0 (4)	C28—C29—H29	119.5
C22—C23—C24	119.5 (3)	C31—C30—H30	119.6
C25—C24—C23	120.2 (4)	C29—C30—H30	119.6
C24—C25—C26	119.9 (3)	C32—C31—H31	120.1
N17—C26—C25	120.6 (3)	C30—C31—H31	120.1
N17—C26—C21	119.8 (3)	C31—C32—H32	119.9
C25—C26—C21	119.6 (3)	C27—C32—H32	119.9
C28—C27—C32	120.7 (3)	N39—C40—H40	118.5
C28—C27—C18	114.9 (3)	C41—C40—H40	118.5
C32—C27—C18	124.2 (3)	C42—C41—H41	120.7
C27—C28—C29	117.3 (3)	C40—C41—H41	120.7
C27—C28—Ir	115.4 (2)	C41—C42—H42	120.2
C29—C28—Ir	127.3 (2)	C43—C42—H42	120.2
C30—C29—C28	120.9 (4)	C42—C43—H43	120.7
C31—C30—C29	120.9 (4)	C38—C43—H43	120.7
C32—C31—C30	119.8 (3)	C46—C45—H45	119.7
C31—C32—C27	120.3 (4)	C44—C45—H45	119.7
C37—N33—N34	106.6 (2)	C47—C46—H46	120.1
C37—N33—Ir	117.48 (17)	C45—C46—H46	120.1
N34—N33—Ir	135.89 (16)	C46—C47—H47	120.1
C35—N34—N33	103.7 (2)	C48—C47—H47	120.1
N34—C35—N36	114.8 (2)	C49—C48—H48	119.6
N34—C35—C44	121.9 (2)	C47—C48—H48	119.6
N36—C35—C44	123.3 (2)	C48—C49—H49	120.1
C37—N36—C35	100.9 (2)	C44—C49—H49	120.1
N36—C37—N33	113.9 (2)	Cl1—C98—H98	108.1
N36—C37—C38	128.8 (2)	Cl3—C98—H98	108.1
N33—C37—C38	117.2 (2)	Cl2—C98—H98	108.1