Bis[3,5-difluoro-2-(2-pyrid­yl)phen­yl](picolinato)iridium(III)

Xu, M.-L.; Che, G.-B.; Li, X.-Y.; Xiao, Q.

doi:10.1107/S160053680804083X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m28

doi:10.1107/S160053680804083X

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Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III)

Mao-Liang Xu,^a Guang-Bo Che,^b ^* Xiu-Ying Li ^b and Qi Xiao ^a

^aXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China, and ^bDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: guangbochejl@yahoo.com

(Received 30 November 2008; accepted 3 December 2008; online 10 December 2008)

The Ir centre in the title complex, [Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)], is six-coordinated in a slightly distorted octahedral IrC₂N₃O fashion.

Related literature

For background to organic light-emitting diodes (OLEDs), see: Cai et al. (2008 ); Chen et al. (2007 ); Park et al. (2006 ). For the synthesis, see: Lamansky et al. (2001 );

Experimental

Crystal data

[Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)]
M_r = 694.64
Orthorhombic, P b c a
a = 16.469 (3) Å
b = 14.677 (3) Å
c = 19.612 (4) Å
V = 4740.3 (16) Å³
Z = 8
Mo Kα radiation
μ = 5.70 mm⁻¹
T = 292 (2) K
0.30 × 0.26 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.203, T_max = 0.284
43036 measured reflections
5410 independent reflections
4239 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.066
S = 1.06
5410 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 2.31 e Å⁻³
Δρ_min = −1.47 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C11—Ir	1.997 (5)
C22—Ir	1.993 (4)
N1—Ir	2.041 (4)
N2—Ir	2.045 (4)
N3—Ir	2.138 (4)
Ir—O1	2.152 (3)

C22—Ir—C11	88.95 (18)
C11—Ir—N1	81.53 (19)
N1—Ir—N2	175.14 (16)
N1—Ir—N3	93.78 (16)
C11—Ir—O1	95.02 (16)
N2—Ir—O1	93.88 (14)

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804083X/bt2823sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680804083X/bt2823Isup2.hkl

checkCIF report

Comment top

In recent decades, the long-lived excited-state and highly efficient solid-state emissions of d⁶ and d⁸ metal complexes have made them of interest as potential components in organic light-emitting diodes (OLEDs) (Chen et al., 2007). Particularly, phosphorescent materials like Ir³⁺ complexes can significantly improve electroluminescent performance because both singlet and triplet excitons can be harvested for light emission, and usually are used as very promising phosphor dyes in OLEDs (Park et al., 2006). Recently, blue organic phosphor such as F₂Irpic (F = 4,6-difluorophenylpyridinato-N,C-2' and pic = picolinate) (I) as a successful cyclometalated Ir³⁺ complex which has been typically doped into host matrices such as tetra-aryl silanes and short conjugation length carbazole derivatives in OLEDs, showing a good quantum efficiency (Cai et al., 2008). In this contribution, we synthesized and investigated crystal structure of F₂Irpic.

As shown in Fig. 1, each Ir³⁺ cation is in a distorted octahedral coordination geometry, consisting of two chelating cyclometalated F ligands with cis-C—C and trans-N—N dispositions and one pic ligand. The Ir—O distance being 2.152 Å and Ir—C and Ir—N lengths are in the range of 1.993–1.997 Å and 2.041–2.138 Å, respectively.

Related literature top

For background to organic light-emitting diodes (OLEDs), see: Cai et al. (2008); Chen et al. (2007); Park et al. (2006). For the synthesis, see: Lamansky et al. (2001);

Experimental top

The title complex was obtained in two steps using a standard method (Lamansky et al., 2001) (71% yield based on Ir).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound. Displacement ellipsoids are drawn at the 30% probability level (H atoms have been omitted).
	Fig. 2. Partial packing diagram of the title compound.

Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III) top

Crystal data top

[Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)]	F(000) = 2672
M_r = 694.64	D_x = 1.947 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2859 reflections
a = 16.469 (3) Å	θ = 3.0–27.5°
b = 14.677 (3) Å	µ = 5.70 mm⁻¹
c = 19.612 (4) Å	T = 292 K
V = 4740.3 (16) Å³	Block, yellow
Z = 8	0.30 × 0.26 × 0.22 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	5410 independent reflections
Radiation source: fine-focus sealed tube	4239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scan	h = −20→21
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
T_min = 0.203, T_max = 0.284	l = −25→25
43036 measured reflections

Refinement top

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.014P)² + 17.09P] where P = (F_o² + 2F_c²)/3
5410 reflections	(Δ/σ)_max = 0.002
343 parameters	Δρ_max = 2.31 e Å⁻³
0 restraints	Δρ_min = −1.47 e Å⁻³

Crystal data top

[Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)]	V = 4740.3 (16) Å³
M_r = 694.64	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.469 (3) Å	µ = 5.70 mm⁻¹
b = 14.677 (3) Å	T = 292 K
c = 19.612 (4) Å	0.30 × 0.26 × 0.22 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	5410 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4239 reflections with I > 2σ(I)
T_min = 0.203, T_max = 0.284	R_int = 0.047
43036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.014P)² + 17.09P] where P = (F_o² + 2F_c²)/3
5410 reflections	Δρ_max = 2.31 e Å⁻³
343 parameters	Δρ_min = −1.47 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.6207 (4)	0.1101 (4)	0.6853 (3)	0.0499 (13)
H1	0.5661	0.1221	0.6775	0.060*
C2	0.6411 (4)	0.0328 (4)	0.7211 (3)	0.0669 (17)
H2	0.6013	−0.0075	0.7359	0.080*
C3	0.7215 (5)	0.0169 (4)	0.7343 (3)	0.0707 (19)
H3	0.7368	−0.0343	0.7591	0.085*
C4	0.7802 (4)	0.0765 (4)	0.7107 (3)	0.0622 (16)
H4	0.8348	0.0660	0.7200	0.075*
C5	0.7565 (3)	0.1537 (4)	0.6724 (2)	0.0480 (13)
C6	0.8089 (3)	0.2221 (4)	0.6425 (3)	0.0473 (13)
C7	0.8932 (4)	0.2253 (5)	0.6464 (3)	0.0657 (18)
C8	0.9387 (3)	0.2931 (5)	0.6192 (3)	0.0658 (18)
H8	0.9949	0.2938	0.6241	0.079*
C9	0.8993 (4)	0.3605 (5)	0.5842 (3)	0.071 (2)
C10	0.8160 (3)	0.3619 (4)	0.5770 (3)	0.0542 (15)
H10	0.7911	0.4092	0.5534	0.065*
C11	0.7702 (3)	0.2939 (3)	0.6046 (2)	0.0419 (11)
C12	0.6176 (3)	0.4753 (4)	0.5608 (3)	0.0509 (13)
H12	0.6167	0.4868	0.6074	0.061*
C13	0.6061 (4)	0.5465 (4)	0.5168 (3)	0.0661 (17)
H13	0.5978	0.6053	0.5330	0.079*
C14	0.6071 (4)	0.5284 (4)	0.4480 (3)	0.0688 (18)
H14	0.5994	0.5755	0.4169	0.083*
C15	0.6194 (4)	0.4416 (4)	0.4248 (3)	0.0558 (15)
H15	0.6196	0.4297	0.3782	0.067*
C16	0.6316 (3)	0.3711 (3)	0.4712 (2)	0.0385 (11)
C17	0.6479 (3)	0.2753 (3)	0.4558 (2)	0.0383 (10)
C18	0.6517 (3)	0.2361 (4)	0.3914 (3)	0.0472 (12)
C19	0.6645 (3)	0.1461 (4)	0.3795 (3)	0.0518 (14)
H19	0.6669	0.1222	0.3356	0.062*
C20	0.6738 (3)	0.0926 (4)	0.4362 (3)	0.0541 (14)
C21	0.6723 (3)	0.1253 (4)	0.5017 (3)	0.0515 (14)
H21	0.6804	0.0859	0.5382	0.062*
C22	0.6587 (3)	0.2175 (3)	0.5135 (2)	0.0357 (9)
C23	0.4938 (3)	0.3110 (3)	0.6744 (2)	0.0386 (11)
C24	0.4141 (3)	0.3031 (4)	0.6958 (3)	0.0525 (14)
H24	0.3964	0.3333	0.7348	0.063*
C25	0.3613 (4)	0.2499 (4)	0.6585 (3)	0.0628 (17)
H25	0.3079	0.2422	0.6728	0.075*
C26	0.3882 (4)	0.2091 (5)	0.6007 (4)	0.0697 (18)
H26	0.3528	0.1744	0.5744	0.084*
C27	0.4686 (3)	0.2192 (4)	0.5809 (3)	0.0556 (14)
H27	0.4864	0.1913	0.5410	0.067*
C28	0.5564 (3)	0.3678 (3)	0.7132 (2)	0.0430 (12)
N1	0.6763 (3)	0.1695 (3)	0.6610 (2)	0.0417 (10)
N2	0.6303 (2)	0.3893 (3)	0.53947 (19)	0.0365 (9)
N3	0.5214 (2)	0.2683 (3)	0.6182 (2)	0.0391 (9)
F1	0.9340 (2)	0.1567 (3)	0.6813 (2)	0.0938 (13)
F2	0.9423 (2)	0.4287 (3)	0.5565 (2)	0.1009 (15)
F3	0.6422 (2)	0.2901 (3)	0.33525 (15)	0.0727 (10)
F4	0.6870 (3)	0.0019 (2)	0.4263 (2)	0.0847 (12)
Ir	0.649485 (11)	0.281026 (12)	0.603051 (9)	0.03453 (6)
O1	0.6297 (2)	0.3595 (2)	0.69428 (16)	0.0409 (8)
O2	0.5319 (2)	0.4165 (3)	0.7596 (2)	0.0652 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.059 (3)	0.041 (3)	0.050 (3)	−0.002 (2)	0.001 (3)	0.007 (3)
C2	0.091 (5)	0.046 (3)	0.064 (4)	0.003 (3)	0.003 (4)	0.016 (3)
C3	0.094 (5)	0.056 (4)	0.061 (4)	0.026 (4)	−0.010 (4)	0.010 (3)
C4	0.067 (4)	0.060 (4)	0.059 (4)	0.021 (3)	−0.011 (3)	0.004 (3)
C5	0.056 (3)	0.051 (3)	0.036 (3)	0.011 (3)	−0.005 (2)	−0.012 (2)
C6	0.033 (2)	0.060 (3)	0.049 (3)	0.008 (2)	−0.003 (2)	−0.024 (3)
C7	0.050 (3)	0.089 (5)	0.057 (4)	0.010 (4)	−0.004 (3)	−0.019 (4)
C8	0.032 (3)	0.098 (5)	0.068 (4)	−0.003 (3)	0.000 (3)	−0.023 (4)
C9	0.050 (4)	0.093 (5)	0.070 (4)	−0.031 (4)	0.022 (3)	−0.023 (4)
C10	0.042 (3)	0.069 (4)	0.052 (3)	−0.005 (3)	0.002 (3)	−0.017 (3)
C11	0.044 (3)	0.045 (3)	0.037 (2)	−0.001 (2)	0.001 (2)	−0.012 (2)
C12	0.067 (4)	0.034 (3)	0.052 (3)	0.001 (3)	−0.009 (3)	0.003 (2)
C13	0.090 (5)	0.038 (3)	0.070 (4)	0.001 (3)	−0.009 (4)	0.001 (3)
C14	0.091 (5)	0.047 (4)	0.068 (4)	0.004 (3)	−0.011 (4)	0.017 (3)
C15	0.070 (4)	0.055 (4)	0.043 (3)	0.002 (3)	0.001 (3)	0.012 (3)
C16	0.035 (3)	0.043 (3)	0.038 (2)	−0.001 (2)	0.000 (2)	0.004 (2)
C17	0.032 (2)	0.045 (3)	0.038 (2)	−0.001 (2)	0.001 (2)	−0.003 (2)
C18	0.037 (2)	0.064 (4)	0.040 (3)	0.001 (3)	0.003 (2)	0.001 (3)
C19	0.042 (3)	0.073 (4)	0.041 (3)	0.007 (3)	−0.003 (2)	−0.024 (3)
C20	0.057 (3)	0.047 (3)	0.058 (4)	0.009 (3)	−0.006 (3)	−0.019 (3)
C21	0.063 (4)	0.038 (3)	0.054 (3)	0.009 (2)	−0.004 (3)	−0.003 (2)
C22	0.035 (2)	0.036 (2)	0.036 (2)	−0.001 (2)	−0.001 (2)	−0.005 (2)
C23	0.045 (3)	0.035 (3)	0.036 (3)	0.002 (2)	−0.001 (2)	0.010 (2)
C24	0.046 (3)	0.062 (4)	0.050 (3)	0.005 (3)	−0.003 (3)	0.011 (3)
C25	0.047 (3)	0.074 (4)	0.068 (4)	−0.011 (3)	−0.001 (3)	0.018 (3)
C26	0.053 (3)	0.077 (5)	0.079 (5)	−0.021 (3)	−0.012 (3)	−0.002 (4)
C27	0.060 (3)	0.054 (3)	0.052 (3)	−0.008 (3)	−0.010 (3)	−0.005 (3)
C28	0.054 (3)	0.038 (3)	0.037 (3)	0.002 (2)	−0.007 (2)	0.003 (2)
N1	0.046 (2)	0.040 (2)	0.039 (2)	0.0068 (19)	−0.0049 (19)	−0.0004 (19)
N2	0.040 (2)	0.032 (2)	0.038 (2)	−0.0019 (16)	−0.0039 (17)	0.0008 (17)
N3	0.038 (2)	0.039 (2)	0.040 (2)	−0.0031 (17)	−0.0062 (17)	0.0059 (18)
F1	0.054 (2)	0.119 (4)	0.108 (3)	0.028 (2)	−0.021 (2)	−0.010 (3)
F2	0.072 (3)	0.116 (4)	0.116 (3)	−0.041 (3)	0.026 (3)	−0.009 (3)
F3	0.094 (3)	0.089 (3)	0.0345 (16)	0.010 (2)	−0.0010 (17)	0.0034 (17)
F4	0.118 (3)	0.051 (2)	0.086 (3)	0.023 (2)	−0.012 (2)	−0.028 (2)
Ir	0.04007 (10)	0.03117 (9)	0.03235 (9)	0.00048 (8)	−0.00413 (8)	−0.00017 (8)
O1	0.044 (2)	0.0416 (19)	0.0376 (17)	−0.0021 (15)	−0.0060 (15)	−0.0040 (15)
O2	0.061 (3)	0.078 (3)	0.057 (2)	0.009 (2)	0.002 (2)	−0.023 (2)

Geometric parameters (Å, º) top

C1—N1	1.351 (6)	C16—N2	1.366 (6)
C1—C2	1.375 (7)	C16—C17	1.463 (7)
C1—H1	0.9300	C17—C18	1.388 (7)
C2—C3	1.370 (9)	C17—C22	1.426 (7)
C2—H2	0.9300	C18—C19	1.359 (8)
C3—C4	1.383 (9)	C18—F3	1.366 (6)
C3—H3	0.9300	C19—C20	1.370 (8)
C4—C5	1.415 (8)	C19—H19	0.9300
C4—H4	0.9300	C20—F4	1.363 (6)
C5—N1	1.359 (7)	C20—C21	1.371 (7)
C5—C6	1.448 (8)	C21—C22	1.391 (7)
C6—C7	1.391 (7)	C21—H21	0.9300
C6—C11	1.439 (7)	C22—Ir	1.993 (4)
C7—C8	1.355 (9)	C23—N3	1.346 (6)
C7—F1	1.391 (8)	C23—C24	1.383 (7)
C8—C9	1.368 (10)	C23—C28	1.528 (7)
C8—H8	0.9300	C24—C25	1.379 (8)
C9—F2	1.341 (7)	C24—H24	0.9300
C9—C10	1.380 (8)	C25—C26	1.356 (9)
C10—C11	1.362 (7)	C25—H25	0.9300
C10—H10	0.9300	C26—C27	1.388 (8)
C11—Ir	1.997 (5)	C26—H26	0.9300
C12—N2	1.345 (6)	C27—N3	1.347 (6)
C12—C13	1.368 (8)	C27—H27	0.9300
C12—H12	0.9300	C28—O2	1.226 (6)
C13—C14	1.377 (9)	C28—O1	1.269 (6)
C13—H13	0.9300	N1—Ir	2.041 (4)
C14—C15	1.367 (8)	N2—Ir	2.045 (4)
C14—H14	0.9300	N3—Ir	2.138 (4)
C15—C16	1.392 (7)	Ir—O1	2.152 (3)
C15—H15	0.9300

N1—C1—C2	123.2 (6)	C18—C19—H19	122.1
N1—C1—H1	118.4	C20—C19—H19	122.1
C2—C1—H1	118.4	F4—C20—C19	117.5 (5)
C3—C2—C1	118.2 (6)	F4—C20—C21	118.6 (5)
C3—C2—H2	120.9	C19—C20—C21	123.9 (5)
C1—C2—H2	120.9	C20—C21—C22	120.0 (5)
C2—C3—C4	120.3 (6)	C20—C21—H21	120.0
C2—C3—H3	119.9	C22—C21—H21	120.0
C4—C3—H3	119.9	C21—C22—C17	117.8 (4)
C3—C4—C5	119.4 (6)	C21—C22—Ir	127.9 (4)
C3—C4—H4	120.3	C17—C22—Ir	114.3 (3)
C5—C4—H4	120.3	N3—C23—C24	122.0 (5)
N1—C5—C4	119.5 (6)	N3—C23—C28	115.7 (4)
N1—C5—C6	113.3 (5)	C24—C23—C28	122.3 (5)
C4—C5—C6	127.3 (5)	C25—C24—C23	119.0 (6)
C7—C6—C11	116.5 (6)	C25—C24—H24	120.5
C7—C6—C5	126.6 (6)	C23—C24—H24	120.5
C11—C6—C5	116.9 (4)	C26—C25—C24	119.2 (6)
C8—C7—F1	117.3 (6)	C26—C25—H25	120.4
C8—C7—C6	123.7 (7)	C24—C25—H25	120.4
F1—C7—C6	119.0 (7)	C25—C26—C27	119.9 (6)
C7—C8—C9	117.8 (6)	C25—C26—H26	120.1
C7—C8—H8	121.1	C27—C26—H26	120.1
C9—C8—H8	121.1	N3—C27—C26	121.4 (6)
F2—C9—C8	119.5 (6)	N3—C27—H27	119.3
F2—C9—C10	118.2 (7)	C26—C27—H27	119.3
C8—C9—C10	122.3 (6)	O2—C28—O1	125.8 (5)
C11—C10—C9	120.0 (6)	O2—C28—C23	117.8 (5)
C11—C10—H10	120.0	O1—C28—C23	116.4 (4)
C9—C10—H10	120.0	C1—N1—C5	119.3 (5)
C10—C11—C6	119.7 (5)	C1—N1—Ir	124.6 (4)
C10—C11—Ir	127.9 (4)	C5—N1—Ir	116.0 (4)
C6—C11—Ir	112.3 (4)	C12—N2—C16	119.4 (4)
N2—C12—C13	122.9 (5)	C12—N2—Ir	124.3 (3)
N2—C12—H12	118.6	C16—N2—Ir	116.3 (3)
C13—C12—H12	118.6	C23—N3—C27	118.5 (4)
C12—C13—C14	118.0 (6)	C23—N3—Ir	114.0 (3)
C12—C13—H13	121.0	C27—N3—Ir	127.4 (4)
C14—C13—H13	121.0	C22—Ir—C11	88.95 (18)
C15—C14—C13	120.5 (6)	C22—Ir—N1	95.68 (18)
C15—C14—H14	119.8	C11—Ir—N1	81.53 (19)
C13—C14—H14	119.8	C22—Ir—N2	80.69 (18)
C14—C15—C16	119.8 (6)	C11—Ir—N2	95.13 (18)
C14—C15—H15	120.1	N1—Ir—N2	175.14 (16)
C16—C15—H15	120.1	C22—Ir—N3	99.04 (17)
N2—C16—C15	119.5 (5)	C11—Ir—N3	171.13 (17)
N2—C16—C17	113.1 (4)	N1—Ir—N3	93.78 (16)
C15—C16—C17	127.3 (5)	N2—Ir—N3	89.99 (15)
C18—C17—C22	118.1 (4)	C22—Ir—O1	173.55 (16)
C18—C17—C16	126.4 (5)	C11—Ir—O1	95.02 (16)
C22—C17—C16	115.5 (4)	N1—Ir—O1	89.94 (14)
C19—C18—F3	116.3 (5)	N2—Ir—O1	93.88 (14)
C19—C18—C17	124.5 (5)	N3—Ir—O1	77.38 (14)
F3—C18—C17	119.2 (5)	C28—O1—Ir	116.0 (3)
C18—C19—C20	115.8 (5)

Experimental details

Crystal data
Chemical formula	[Ir(C₁₁H₆F₂N)₂(C₆H₄NO₂)]
M_r	694.64
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	16.469 (3), 14.677 (3), 19.612 (4)
V (Å³)	4740.3 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.70
Crystal size (mm)	0.30 × 0.26 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.203, 0.284
No. of measured, independent and observed [I > 2σ(I)] reflections	43036, 5410, 4239
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.066, 1.06
No. of reflections	5410
No. of parameters	343
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.014P)² + 17.09P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.31, −1.47

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

C11—Ir	1.997 (5)	N2—Ir	2.045 (4)
C22—Ir	1.993 (4)	N3—Ir	2.138 (4)
N1—Ir	2.041 (4)	Ir—O1	2.152 (3)

C22—Ir—C11	88.95 (18)	N1—Ir—N3	93.78 (16)
C11—Ir—N1	81.53 (19)	C11—Ir—O1	95.02 (16)
N1—Ir—N2	175.14 (16)	N2—Ir—O1	93.88 (14)

Acknowledgements

The authors thank the Key Programs Foundation for Science and Technology Development of Shanxi Province and the Foundation of Jilin Normal University.

References

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