(5-Methyl-pyrazine-2-carboxyl-ato-κ(2) N (1),O)bis-[2-(4-methyl-pyridin-2-yl-κN)-3,5-bis-(tri-fluoro-meth-yl)phenyl-κC (1)]iridium(III) chloro-form hemisolvate.

In the title complex, [Ir(C14H8F6N)2(C6H5N2O2)]·0.5CHCl3, the Ir(III) atom adopts a distorted octa-hedral geometry, being coordinated by three N atoms (arranged meridionally), two C atoms and one O atom of three bidentate ligands. The complex mol-ecules pack with no specific inter-molecular inter-actions between them. The SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155] was used to model a disordered chloro-form solvent mol-ecule; the calculated unit-cell data allow for the presence of half of this mol-ecule in the asymmetric unit.

Related literature

For phospho­rescent Ir complexes, see: Chen et al. (2010 ▶). For phospho­rescent Ir complexes in OLED, see: Chang et al. (2013 ▶); Park et al. (2013 ▶); Seo et al. (2010 ▶).

Experimental

Crystal data

[Ir(C14H8F6N)2(C6H5N2O2)]·0.5CHCl3

M = 997.43

Triclinic,

a = 11.0949 (3) Å

b = 12.3669 (4) Å

c = 14.2892 (4) Å

α = 94.399 (3)°

β = 110.888 (1)°

γ = 102.695 (2)°

V = 1760.93 (9) Å3

Z = 2

Mo Kα radiation

μ = 4.01 mm−1

T = 296 K

0.36 × 0.27 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.284, T max = 0.351

46539 measured reflections

8709 independent reflections

8016 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.064

S = 1.04

8709 reflections

481 parameters

H-atom parameters not refined

Δρmax = 1.22 e Å−3

Δρmin = −0.90 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813034727/tk5282sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034727/tk5282Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ir(C14H8F6N)2(C6H5N2O2)]·0.5CHCl3	Z = 2
Mr = 997.43	F(000) = 966
Triclinic, P1	Dx = 1.881 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.0949 (3) Å	Cell parameters from 9024 reflections
b = 12.3669 (4) Å	θ = 2.5–28.3°
c = 14.2892 (4) Å	µ = 4.01 mm−1
α = 94.399 (3)°	T = 296 K
β = 110.888 (1)°	Block, yellow
γ = 102.695 (2)°	0.36 × 0.27 × 0.26 mm
V = 1760.93 (9) Å3

Bruker SMART CCD area-detector diffractometer	8016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→14
Tmin = 0.284, Tmax = 0.351	k = −16→16
46539 measured reflections	l = −19→19
8709 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters not refined
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
8709 reflections	Δρmax = 1.22 e Å−3
481 parameters	Δρmin = −0.90 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.

	x	y	z	Uiso*/Ueq
Ir1	0.03883 (2)	0.25529 (2)	0.20131 (2)	0.02728 (4)
N2	0.1883 (2)	0.40036 (17)	0.26029 (17)	0.0284 (4)
C3	0.1693 (3)	0.5036 (2)	0.2518 (2)	0.0333 (6)
H3	0.0824	0.5112	0.2313	0.04*
C4	0.2723 (3)	0.5980 (2)	0.2721 (2)	0.0387 (6)
H4	0.2554	0.6683	0.2681	0.046*
C5	0.4014 (3)	0.5881 (2)	0.2986 (3)	0.0418 (7)
C6	0.4208 (3)	0.4820 (2)	0.3097 (2)	0.0383 (6)
H6	0.5068	0.473	0.3277	0.046*
C7	0.3165 (3)	0.3897 (2)	0.2949 (2)	0.0290 (5)
C8	0.3232 (3)	0.2723 (2)	0.3049 (2)	0.0290 (5)
C9	0.1971 (3)	0.1931 (2)	0.2568 (2)	0.0297 (5)
C10	0.1925 (3)	0.0790 (2)	0.2549 (2)	0.0358 (6)
H10	0.1109	0.0255	0.2215	0.043*
C11	0.3056 (3)	0.0440 (2)	0.3011 (3)	0.0381 (6)
C12	0.4279 (3)	0.1215 (3)	0.3550 (3)	0.0410 (7)
H12	0.5031	0.0973	0.3891	0.049*
C13	0.4371 (3)	0.2356 (2)	0.3577 (2)	0.0349 (6)
C14	0.5175 (4)	0.6877 (3)	0.3150 (5)	0.0797 (15)
H14A	0.4921	0.7315	0.2621	0.12*
H14B	0.5924	0.6618	0.3137	0.12*
H14C	0.5419	0.7334	0.3798	0.12*
C15	0.2965 (4)	−0.0789 (3)	0.2947 (3)	0.0525 (9)
F16	0.1865 (3)	−0.13855 (19)	0.3003 (3)	0.0883 (9)
F17	0.3047 (5)	−0.1224 (2)	0.2134 (3)	0.1211 (14)
F18	0.3937 (3)	−0.1016 (2)	0.3709 (3)	0.1000 (10)
C19	0.5741 (3)	0.3107 (3)	0.4222 (3)	0.0493 (8)
F20	0.6443 (2)	0.35089 (19)	0.3678 (2)	0.0669 (6)
F21	0.5699 (2)	0.40044 (19)	0.47936 (17)	0.0694 (6)
F22	0.6487 (2)	0.2576 (2)	0.4880 (2)	0.0780 (8)
N23	−0.0887 (2)	0.09914 (19)	0.14990 (18)	0.0316 (5)
C24	−0.1141 (3)	0.0403 (3)	0.0586 (2)	0.0440 (7)
H24	−0.0939	0.0788	0.0104	0.053*
C25	−0.1684 (3)	−0.0741 (3)	0.0334 (3)	0.0475 (8)
H25	−0.1842	−0.1115	−0.0306	0.057*
C26	−0.1994 (3)	−0.1336 (3)	0.1039 (3)	0.0447 (7)
C27	−0.1780 (3)	−0.0718 (2)	0.1968 (3)	0.0411 (7)
H27	−0.1999	−0.1091	0.245	0.049*
C28	−0.1243 (3)	0.0451 (2)	0.2193 (2)	0.0318 (5)
C29	−0.0885 (3)	0.1206 (2)	0.3161 (2)	0.0307 (5)
C30	−0.0002 (3)	0.2272 (2)	0.3244 (2)	0.0284 (5)
C31	0.0482 (3)	0.3046 (2)	0.4146 (2)	0.0339 (6)
H31	0.1077	0.3735	0.4216	0.041*
C32	0.0082 (3)	0.2796 (2)	0.4939 (2)	0.0373 (6)
C33	−0.0821 (3)	0.1794 (3)	0.4843 (2)	0.0390 (6)
H33	−0.1104	0.1649	0.5371	0.047*
C34	−0.1315 (3)	0.0999 (2)	0.3966 (2)	0.0343 (6)
C35	−0.2524 (4)	−0.2593 (3)	0.0832 (4)	0.0676 (11)
H35A	−0.1801	−0.2927	0.1125	0.101*
H35B	−0.2933	−0.2853	0.0111	0.101*
H35C	−0.3176	−0.2803	0.1127	0.101*
C36	0.0617 (4)	0.3628 (3)	0.5896 (3)	0.0562 (9)
F37	0.1506 (5)	0.4477 (3)	0.5970 (3)	0.173 (2)
F38	−0.0266 (4)	0.4019 (5)	0.6057 (4)	0.185 (3)
F39	0.1054 (7)	0.3199 (3)	0.6689 (2)	0.197 (3)
C40	−0.2349 (3)	−0.0040 (3)	0.3935 (3)	0.0456 (7)
F41	−0.34179 (19)	−0.03214 (18)	0.30647 (17)	0.0587 (5)
F42	−0.2824 (2)	0.0087 (2)	0.46604 (18)	0.0708 (7)
F43	−0.1863 (2)	−0.09515 (17)	0.40656 (19)	0.0639 (6)
N44	−0.1189 (2)	0.33246 (19)	0.13102 (18)	0.0319 (5)
C45	−0.2095 (3)	0.3571 (2)	0.1648 (2)	0.0374 (6)
H45	−0.2079	0.34	0.2274	0.045*
C46	−0.3056 (3)	0.4073 (3)	0.1089 (2)	0.0435 (7)
N47	−0.3107 (3)	0.4348 (3)	0.0193 (2)	0.0580 (8)
C48	−0.2181 (4)	0.4116 (4)	−0.0121 (3)	0.0585 (10)
H48	−0.2178	0.4315	−0.0735	0.07*
C49	−0.1226 (3)	0.3600 (3)	0.0412 (2)	0.0397 (6)
C50	−0.4071 (4)	0.4341 (4)	0.1458 (3)	0.0615 (10)
H50A	−0.3628	0.4778	0.213	0.092*
H50B	−0.4663	0.3655	0.1475	0.092*
H50C	−0.4576	0.4763	0.1009	0.092*
C51	−0.0206 (3)	0.3327 (3)	0.0033 (2)	0.0431 (7)
O52	0.0579 (2)	0.28101 (18)	0.05964 (16)	0.0395 (4)
O53	−0.0184 (3)	0.3611 (3)	−0.0767 (2)	0.0648 (7)

	U11	U22	U33	U12	U13	U23
Ir1	0.02945 (6)	0.02304 (6)	0.03234 (6)	0.00983 (4)	0.01330 (4)	0.00644 (4)
N2	0.0359 (11)	0.0205 (9)	0.0327 (11)	0.0110 (8)	0.0149 (9)	0.0077 (8)
C3	0.0389 (14)	0.0251 (12)	0.0409 (15)	0.0156 (11)	0.0162 (12)	0.0088 (11)
C4	0.0483 (16)	0.0229 (12)	0.0493 (17)	0.0149 (12)	0.0201 (14)	0.0088 (12)
C5	0.0453 (16)	0.0235 (13)	0.0612 (19)	0.0071 (11)	0.0263 (15)	0.0099 (12)
C6	0.0369 (14)	0.0271 (13)	0.0560 (18)	0.0100 (11)	0.0222 (13)	0.0093 (12)
C7	0.0353 (13)	0.0233 (11)	0.0343 (13)	0.0112 (10)	0.0178 (11)	0.0069 (10)
C8	0.0340 (13)	0.0240 (11)	0.0355 (13)	0.0107 (10)	0.0185 (11)	0.0081 (10)
C9	0.0336 (13)	0.0249 (12)	0.0361 (14)	0.0117 (10)	0.0168 (11)	0.0088 (10)
C10	0.0370 (14)	0.0227 (12)	0.0522 (17)	0.0102 (10)	0.0209 (13)	0.0079 (11)
C11	0.0422 (15)	0.0260 (13)	0.0557 (18)	0.0140 (11)	0.0255 (14)	0.0138 (12)
C12	0.0397 (15)	0.0357 (15)	0.0559 (19)	0.0194 (12)	0.0201 (14)	0.0181 (13)
C13	0.0361 (14)	0.0310 (13)	0.0416 (15)	0.0125 (11)	0.0165 (12)	0.0113 (11)
C14	0.057 (2)	0.0304 (17)	0.159 (5)	0.0059 (16)	0.053 (3)	0.021 (2)
C15	0.060 (2)	0.0298 (15)	0.085 (3)	0.0231 (14)	0.0397 (19)	0.0184 (16)
F16	0.0793 (17)	0.0376 (11)	0.170 (3)	0.0179 (11)	0.0682 (19)	0.0377 (15)
F17	0.245 (4)	0.0408 (13)	0.141 (3)	0.059 (2)	0.134 (3)	0.0245 (15)
F18	0.098 (2)	0.0503 (14)	0.146 (3)	0.0419 (14)	0.0219 (19)	0.0427 (16)
C19	0.0427 (17)	0.0423 (17)	0.057 (2)	0.0148 (14)	0.0092 (15)	0.0157 (15)
F20	0.0406 (11)	0.0589 (13)	0.1015 (18)	0.0074 (9)	0.0287 (11)	0.0243 (12)
F21	0.0719 (15)	0.0548 (13)	0.0567 (13)	0.0155 (11)	−0.0001 (11)	−0.0062 (10)
F22	0.0555 (13)	0.0632 (14)	0.0864 (17)	0.0184 (11)	−0.0105 (12)	0.0251 (12)
N23	0.0298 (11)	0.0281 (11)	0.0356 (12)	0.0076 (9)	0.0119 (9)	0.0017 (9)
C24	0.0470 (17)	0.0455 (17)	0.0396 (16)	0.0099 (14)	0.0193 (14)	0.0002 (13)
C25	0.0469 (17)	0.0432 (17)	0.0467 (18)	0.0044 (14)	0.0198 (14)	−0.0115 (14)
C26	0.0421 (16)	0.0297 (14)	0.060 (2)	0.0055 (12)	0.0210 (15)	−0.0028 (13)
C27	0.0418 (16)	0.0294 (14)	0.0532 (18)	0.0073 (12)	0.0213 (14)	0.0042 (12)
C28	0.0264 (12)	0.0291 (13)	0.0388 (14)	0.0080 (10)	0.0115 (11)	0.0036 (11)
C29	0.0287 (12)	0.0287 (12)	0.0351 (14)	0.0107 (10)	0.0106 (10)	0.0062 (10)
C30	0.0285 (12)	0.0265 (12)	0.0318 (13)	0.0113 (10)	0.0107 (10)	0.0078 (10)
C31	0.0374 (14)	0.0285 (13)	0.0371 (14)	0.0085 (11)	0.0157 (12)	0.0056 (11)
C32	0.0392 (15)	0.0385 (15)	0.0340 (14)	0.0109 (12)	0.0137 (12)	0.0040 (11)
C33	0.0416 (15)	0.0409 (15)	0.0418 (16)	0.0127 (12)	0.0226 (13)	0.0113 (12)
C34	0.0310 (13)	0.0356 (14)	0.0402 (15)	0.0104 (11)	0.0160 (11)	0.0134 (11)
C35	0.079 (3)	0.0299 (16)	0.091 (3)	0.0001 (17)	0.042 (2)	−0.0109 (17)
C36	0.070 (2)	0.053 (2)	0.0418 (19)	0.0057 (18)	0.0253 (17)	−0.0032 (15)
F37	0.222 (5)	0.134 (3)	0.100 (2)	−0.107 (3)	0.098 (3)	−0.074 (2)
F38	0.127 (3)	0.227 (5)	0.164 (4)	0.057 (3)	0.037 (3)	−0.126 (4)
F39	0.375 (8)	0.101 (3)	0.0358 (15)	0.055 (4)	−0.003 (3)	−0.0066 (16)
C40	0.0473 (17)	0.0408 (16)	0.0519 (19)	0.0063 (13)	0.0257 (15)	0.0100 (14)
F41	0.0373 (10)	0.0578 (12)	0.0718 (14)	−0.0018 (9)	0.0198 (10)	0.0047 (10)
F42	0.0751 (15)	0.0686 (14)	0.0758 (15)	−0.0053 (12)	0.0525 (13)	0.0081 (12)
F43	0.0744 (15)	0.0389 (11)	0.0836 (16)	0.0148 (10)	0.0338 (12)	0.0250 (10)
N44	0.0320 (11)	0.0318 (11)	0.0343 (12)	0.0114 (9)	0.0133 (9)	0.0081 (9)
C45	0.0378 (14)	0.0402 (15)	0.0371 (15)	0.0145 (12)	0.0149 (12)	0.0081 (12)
C46	0.0395 (16)	0.0484 (18)	0.0451 (17)	0.0198 (13)	0.0143 (13)	0.0079 (14)
N47	0.0589 (18)	0.082 (2)	0.0509 (17)	0.0445 (18)	0.0234 (15)	0.0273 (16)
C48	0.064 (2)	0.083 (3)	0.049 (2)	0.044 (2)	0.0262 (18)	0.0326 (19)
C49	0.0426 (16)	0.0434 (16)	0.0371 (15)	0.0166 (13)	0.0158 (13)	0.0119 (12)
C50	0.054 (2)	0.087 (3)	0.059 (2)	0.042 (2)	0.0242 (18)	0.017 (2)
C51	0.0473 (17)	0.0476 (17)	0.0416 (16)	0.0182 (14)	0.0211 (14)	0.0133 (13)
O52	0.0465 (12)	0.0419 (11)	0.0398 (11)	0.0198 (9)	0.0224 (9)	0.0114 (9)
O53	0.0802 (19)	0.094 (2)	0.0504 (14)	0.0460 (16)	0.0411 (14)	0.0379 (14)

Ir1—C30	1.993 (3)	C25—H25	0.93
Ir1—C9	1.999 (3)	C26—C27	1.395 (5)
Ir1—N23	2.028 (2)	C26—C35	1.502 (4)
Ir1—N2	2.035 (2)	C27—C28	1.400 (4)
Ir1—N44	2.147 (2)	C27—H27	0.93
Ir1—O52	2.149 (2)	C28—C29	1.480 (4)
N2—C3	1.347 (3)	C29—C34	1.413 (4)
N2—C7	1.370 (3)	C29—C30	1.427 (4)
C3—C4	1.371 (4)	C30—C31	1.400 (4)
C3—H3	0.93	C31—C32	1.388 (4)
C4—C5	1.381 (4)	C31—H31	0.93
C4—H4	0.93	C32—C33	1.374 (4)
C5—C6	1.388 (4)	C32—C36	1.490 (4)
C5—C14	1.509 (4)	C33—C34	1.388 (4)
C6—C7	1.377 (4)	C33—H33	0.93
C6—H6	0.93	C34—C40	1.508 (4)
C7—C8	1.485 (3)	C35—H35A	0.96
C8—C9	1.414 (4)	C35—H35B	0.96
C8—C13	1.414 (4)	C35—H35C	0.96
C9—C10	1.398 (3)	C36—F37	1.241 (5)
C10—C11	1.376 (4)	C36—F38	1.264 (5)
C10—H10	0.93	C36—F39	1.270 (5)
C11—C12	1.386 (4)	C40—F41	1.332 (4)
C11—C15	1.493 (4)	C40—F42	1.334 (4)
C12—C13	1.389 (4)	C40—F43	1.351 (4)
C12—H12	0.93	N44—C45	1.339 (4)
C13—C19	1.507 (4)	N44—C49	1.342 (4)
C14—H14A	0.96	C45—C46	1.386 (4)
C14—H14B	0.96	C45—H45	0.93
C14—H14C	0.96	C46—N47	1.334 (4)
C15—F17	1.285 (5)	C46—C50	1.489 (5)
C15—F16	1.312 (4)	N47—C48	1.333 (5)
C15—F18	1.330 (5)	C48—C49	1.381 (4)
C19—F20	1.333 (4)	C48—H48	0.93
C19—F22	1.334 (4)	C49—C51	1.504 (4)
C19—F21	1.346 (4)	C50—H50A	0.96
N23—C24	1.347 (4)	C50—H50B	0.96
N23—C28	1.361 (4)	C50—H50C	0.96
C24—C25	1.373 (5)	C51—O53	1.228 (4)
C24—H24	0.93	C51—O52	1.280 (4)
C25—C26	1.387 (5)
C30—Ir1—C9	88.44 (11)	C24—C25—C26	119.6 (3)
C30—Ir1—N23	79.81 (10)	C24—C25—H25	120.2
C9—Ir1—N23	92.01 (10)	C26—C25—H25	120.2
C30—Ir1—N2	99.81 (10)	C25—C26—C27	117.2 (3)
C9—Ir1—N2	79.63 (10)	C25—C26—C35	122.3 (3)
N23—Ir1—N2	171.64 (8)	C27—C26—C35	120.4 (3)
C30—Ir1—N44	97.99 (10)	C26—C27—C28	121.5 (3)
C9—Ir1—N44	173.03 (9)	C26—C27—H27	119.2
N23—Ir1—N44	91.77 (9)	C28—C27—H27	119.2
N2—Ir1—N44	96.54 (9)	N23—C28—C27	119.2 (3)
C30—Ir1—O52	173.79 (9)	N23—C28—C29	112.9 (2)
C9—Ir1—O52	96.65 (9)	C27—C28—C29	127.7 (3)
N23—Ir1—O52	96.41 (9)	C34—C29—C30	118.8 (2)
N2—Ir1—O52	84.65 (9)	C34—C29—C28	128.4 (2)
N44—Ir1—O52	77.10 (8)	C30—C29—C28	112.8 (2)
C3—N2—C7	118.7 (2)	C31—C30—C29	118.9 (2)
C3—N2—Ir1	123.82 (19)	C31—C30—Ir1	125.1 (2)
C7—N2—Ir1	116.56 (16)	C29—C30—Ir1	115.97 (19)
N2—C3—C4	122.8 (3)	C32—C31—C30	120.7 (3)
N2—C3—H3	118.6	C32—C31—H31	119.7
C4—C3—H3	118.6	C30—C31—H31	119.7
C3—C4—C5	119.5 (3)	C33—C32—C31	120.6 (3)
C3—C4—H4	120.2	C33—C32—C36	119.5 (3)
C5—C4—H4	120.2	C31—C32—C36	119.8 (3)
C4—C5—C6	117.3 (3)	C32—C33—C34	120.5 (3)
C4—C5—C14	121.9 (3)	C32—C33—H33	119.7
C6—C5—C14	120.8 (3)	C34—C33—H33	119.7
C7—C6—C5	121.9 (3)	C33—C34—C29	120.3 (3)
C7—C6—H6	119.1	C33—C34—C40	115.4 (3)
C5—C6—H6	119.1	C29—C34—C40	124.3 (3)
N2—C7—C6	119.4 (2)	C26—C35—H35A	109.5
N2—C7—C8	113.0 (2)	C26—C35—H35B	109.5
C6—C7—C8	127.5 (2)	H35A—C35—H35B	109.5
C9—C8—C13	119.7 (2)	C26—C35—H35C	109.5
C9—C8—C7	112.8 (2)	H35A—C35—H35C	109.5
C13—C8—C7	127.4 (2)	H35B—C35—H35C	109.5
C10—C9—C8	117.9 (2)	F37—C36—F38	104.0 (5)
C10—C9—Ir1	125.5 (2)	F37—C36—F39	106.9 (5)
C8—C9—Ir1	116.52 (18)	F38—C36—F39	101.3 (5)
C11—C10—C9	121.6 (3)	F37—C36—C32	116.6 (3)
C11—C10—H10	119.2	F38—C36—C32	113.4 (4)
C9—C10—H10	119.2	F39—C36—C32	113.1 (3)
C10—C11—C12	120.7 (3)	F41—C40—F42	105.4 (3)
C10—C11—C15	119.7 (3)	F41—C40—F43	106.7 (3)
C12—C11—C15	119.6 (3)	F42—C40—F43	105.9 (3)
C11—C12—C13	119.4 (3)	F41—C40—C34	113.2 (3)
C11—C12—H12	120.3	F42—C40—C34	112.4 (3)
C13—C12—H12	120.3	F43—C40—C34	112.8 (3)
C12—C13—C8	120.3 (3)	C45—N44—C49	117.6 (2)
C12—C13—C19	114.0 (3)	C45—N44—Ir1	129.33 (19)
C8—C13—C19	125.7 (2)	C49—N44—Ir1	113.06 (19)
C5—C14—H14A	109.5	N44—C45—C46	121.8 (3)
C5—C14—H14B	109.5	N44—C45—H45	119.1
H14A—C14—H14B	109.5	C46—C45—H45	119.1
C5—C14—H14C	109.5	N47—C46—C45	121.2 (3)
H14A—C14—H14C	109.5	N47—C46—C50	116.8 (3)
H14B—C14—H14C	109.5	C45—C46—C50	121.9 (3)
F17—C15—F16	107.5 (4)	C48—N47—C46	116.1 (3)
F17—C15—F18	105.2 (3)	N47—C48—C49	123.9 (3)
F16—C15—F18	103.8 (3)	N47—C48—H48	118.1
F17—C15—C11	113.1 (3)	C49—C48—H48	118.1
F16—C15—C11	113.5 (3)	N44—C49—C48	119.4 (3)
F18—C15—C11	112.8 (3)	N44—C49—C51	117.7 (3)
F20—C19—F22	106.2 (3)	C48—C49—C51	123.0 (3)
F20—C19—F21	106.5 (3)	C46—C50—H50A	109.5
F22—C19—F21	105.2 (3)	C46—C50—H50B	109.5
F20—C19—C13	113.1 (3)	H50A—C50—H50B	109.5
F22—C19—C13	112.3 (3)	C46—C50—H50C	109.5
F21—C19—C13	112.9 (3)	H50A—C50—H50C	109.5
C24—N23—C28	119.3 (2)	H50B—C50—H50C	109.5
C24—N23—Ir1	122.1 (2)	O53—C51—O52	125.7 (3)
C28—N23—Ir1	116.99 (18)	O53—C51—C49	118.9 (3)
N23—C24—C25	123.0 (3)	O52—C51—C49	115.4 (3)
N23—C24—H24	118.5	C51—O52—Ir1	116.56 (19)
C25—C24—H24	118.5

Table 1

Selected bond lengths (Å)

Ir1—C30	1.993 (3)
Ir1—C9	1.999 (3)
Ir1—N23	2.028 (2)
Ir1—N2	2.035 (2)
Ir1—N44	2.147 (2)
Ir1—O52	2.149 (2)