Bis[3,5-difluoro-2-(2-pyrid-yl)phen-yl](picolinato)iridium(III).

The Ir centre in the title complex, [Ir(C(11)H(6)F(2)N)(2)(C(6)H(4)NO(2))], is six-coordinated in a slightly distorted octa-hedral IrC(2)N(3)O 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 = 694.64

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.066

S = 1.06

5410 reflections

343 parameters

H-atom parameters constrained

Δρmax = 2.31 e Å−3

Δρmin = −1.47 e Å−3

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.

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

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

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

[Ir(C11H6F2N)2(C6H4NO2)]	F(000) = 2672
Mr = 694.64	Dx = 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

Rigaku R-AXIS RAPID diffractometer	5410 independent reflections
Radiation source: fine-focus sealed tube	4239 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scan	h = −20→21
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
Tmin = 0.203, Tmax = 0.284	l = −25→25
43036 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.014P)2 + 17.09P] where P = (Fo2 + 2Fc2)/3
5410 reflections	(Δ/σ)max = 0.002
343 parameters	Δρmax = 2.31 e Å−3
0 restraints	Δρmin = −1.47 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.

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
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)

	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)

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)

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)