(3-Allyl­oxypicolinato-κ2N,O2)bis­[3,5-difluoro-2-(2-pyrid­yl)phenyl-κ2C1,N]iridium(III)

Zhao, Y.-L.; Meng, J.

doi:10.1107/S1600536809046479

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1546-m1547

doi:10.1107/S1600536809046479

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(3-Allyloxypicolinato-κ²N,O²)bis[3,5-difluoro-2-(2-pyridyl)phenyl-κ²C¹,N]iridium(III)

Yu-Ling Zhao ^a ^* and Jing Meng ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: ytz823@hotmail.com

(Received 1 November 2009; accepted 4 November 2009; online 11 November 2009)

The title complex, [Ir(C₁₁H₆F₂N)₂(C₉H₈NO₃)], consists of one Ir^III ion, two C,N-bidentate 3,5-difluoro-2-(2-pyridyl)phenyl (F₂ppy) ligands and one N,O-bidentate 3-allyloxypicolinate (pic-3-Oall) ligand. The Ir^III ion is hexacoordinated by two C atoms and two N atoms from the F₂ppy ligands and one N atom and one carboxylate O atom from the pic-3-Oall ligand, displaying a distorted octahedral geometry. In the crystal structure, weak intermolecular C—H⋯F and C—H⋯O hydrogen bonds link the complex molecules into a three-dimensional supramolecular structure.

Related literature

For general background to phosphorescent materials, see: Baldo et al. (1998 , 2000 ); Liang et al. (2006 ); Thompson (2007 ); Tsuboyama et al. (2003 ). For bond lengths in organic compounds, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ir(C₁₁H₆F₂N)₂(C₉H₈NO₃)]
M_r = 750.70
Monoclinic, C 2/c
a = 33.429 (4) Å
b = 9.9117 (12) Å
c = 16.0265 (19) Å
β = 94.107 (2)°
V = 5296.5 (11) Å³
Z = 8
Mo Kα radiation
μ = 5.11 mm⁻¹
T = 185 K
0.31 × 0.23 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.305, T_max = 0.862
14169 measured reflections
5087 independent reflections
4364 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.05
5087 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 1.72 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Ir1—C7	1.983 (4)
Ir1—C18	2.002 (4)
Ir1—N1	2.045 (3)
Ir1—N2	2.051 (4)
Ir1—N3	2.132 (3)
Ir1—O1	2.135 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯F1ⁱ	0.95	2.60	2.997 (6)	106
C28—H28⋯F2ⁱⁱ	0.95	2.55	3.280 (6)	134
C10—H10⋯F3ⁱⁱⁱ	0.95	2.50	3.299 (6)	142
C12—H12⋯F4^iv	0.95	2.56	3.130 (6)	119
C26—H26⋯O1^v	0.95	2.63	3.519 (5)	155
C14—H14⋯O2^vi	0.95	2.54	3.275 (6)	134
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ ; (v) $[x, -y, z-{\script{1\over 2}}]$ ; (vi) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046479/hy2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046479/hy2251Isup2.hkl

checkCIF report

Comment top

Since Forrest and co-workers (Baldo et al., 1998) successfully utilized the phosphorescent material PtOEP to fabricate light-emitting devices, many heavy-metal complexes have been extensively investigated in highly efficient electrophosphorescent organic light-emitting diodes (Baldo et al., 2000; Liang et al., 2006; Thompson, 2007). Among the complexes, the cyclometalated iridium complexes are the most valuable emitting materials due to the results in higher efficiency and brightness (Liang et al., 2006; Tsuboyama et al., 2003). Recently, we synthesized a mixed-ligand iridium complex, [Ir(F₂ppy)₂(pic-3-Oall)] (F₂ppy = 3,5-difluoro-2-(2-pyridyl)phenyl; pic-3-Oall = 3-allyloxypicolinate), which exhibits bright blue light.

The molecular structure of the title complex is shown in Fig. 1. The mononuclear iridium(III) complex has an approximately octahedral coordination geometry. The Ir^III ion is hexa-coordinated by two C atoms and two N atoms from two C,N-bidentate F₂ppy ligands, which exhibit cis-C,C and trans-N,N chelate dispositions, and one N atom and one carboxylate O atom from one N,O-bidentate pic-3-Oall ligand. All the bond lengths and angles of the molecule are within normal ranges (Allen et al., 1987). For the F₂ppy ligands, the Ir—C bonds [1.983 (4) and 2.002 (4) Å] are shorter than the Ir—N bonds [2.045 (4) and 2.051 (4) Å] (Table 1). Due to steric interactions, the difluorophenyl groups are not coplanar with the pyridine groups; the dihedral angles between the substituted phenyl rings and pyridines are 7.60 (1) and 6.05 (3)°, respectively. For the pic-3-Oall ligand, the bond lengths of Ir—N and Ir—O are 2.132 (3) and 2.135 (3) Å, respectively. In the crystal structure, the complex molecules are connected by weak intermolecular C—H···F and C—H···O hydrogen bonds (Table 2 and Fig. 2), forming a three-dimensional supramolecular structure.

Related literature top

For general background to phosphorescent materials, see: Baldo et al. (1998, 2000); Liang et al. (2006); Thompson (2007); Tsuboyama et al. (2003). For bond lengths in organic compounds, see: Allen et al. (1987).

Experimental top

The title complex was prepared as following. First, a cyclometalated Ir^III µ-chlorobridged dimer, [(C₁₁H₆F₂N)₂Ir(µ-Cl)]₂, was synthesized by reacting IrCl₃.nH₂O (3.0 mmol) and 2-(2,4-difluorophenyl)pyridine (7.5 mmol). Then, the dimer (0.2 mmol) was reacted with 3-hydroxypicolinic acid (0.44 mmol) in 2-methoxyethanol (25 ml), affording bis[2-(2,4-difluorophenyl)pyridine](3-hydroxypicolinate)iridium(III), which (0.2 mmol) was reacted with 3-bromopropene (0.24 mmol) in the present of anhydrous K₂CO₃ (1 mmol) to give the title complex. Yellow plate single crystals of the complex were obtained by slow evaporation of the chloroform solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Intermolecular C—H···F and C—H···O hydrogen bonds in the title complex, viewed along the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity. [Colour codes: pale-green F; grey C; red O; white H.]

(3-Allyloxypicolinato-κ²N,O²)bis[3,5-difluoro-2-(2- pyridyl)phenyl-κ²C¹,N]iridium(III) top

Crystal data top

[Ir(C₁₁H₆F₂N)₂(C₉H₈NO₃)]	F(000) = 2912
M_r = 750.70	D_x = 1.883 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7056 reflections
a = 33.429 (4) Å	θ = 2.4–25.8°
b = 9.9117 (12) Å	µ = 5.11 mm⁻¹
c = 16.0265 (19) Å	T = 185 K
β = 94.107 (2)°	Plate, yellow
V = 5296.5 (11) Å³	0.31 × 0.23 × 0.03 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	5087 independent reflections
Radiation source: sealed tube	4364 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.8°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −40→36
T_min = 0.305, T_max = 0.862	k = −12→12
14169 measured reflections	l = −11→19

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0425P)²] where P = (F_o² + 2F_c²)/3
5087 reflections	(Δ/σ)_max = 0.002
379 parameters	Δρ_max = 1.72 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ir(C₁₁H₆F₂N)₂(C₉H₈NO₃)]	V = 5296.5 (11) Å³
M_r = 750.70	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.429 (4) Å	µ = 5.11 mm⁻¹
b = 9.9117 (12) Å	T = 185 K
c = 16.0265 (19) Å	0.31 × 0.23 × 0.03 mm
β = 94.107 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	5087 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4364 reflections with I > 2σ(I)
T_min = 0.305, T_max = 0.862	R_int = 0.039
14169 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	Δρ_max = 1.72 e Å⁻³
5087 reflections	Δρ_min = −0.59 e Å⁻³
379 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ir1	0.365597 (4)	0.187358 (14)	0.693663 (9)	0.03540 (8)
N1	0.32777 (11)	0.0250 (3)	0.6890 (2)	0.0416 (8)
N2	0.39933 (11)	0.3598 (4)	0.7072 (2)	0.0426 (8)
N3	0.38322 (11)	0.1393 (3)	0.5719 (2)	0.0401 (8)
O1	0.41710 (9)	0.0620 (3)	0.71739 (17)	0.0441 (7)
O2	0.45390 (11)	−0.0942 (4)	0.6590 (2)	0.0706 (10)
O3	0.45584 (9)	−0.0840 (3)	0.4921 (2)	0.0564 (8)
C1	0.33883 (15)	−0.1008 (4)	0.7107 (3)	0.0485 (11)
H1	0.3663	−0.1186	0.7259	0.058*
C2	0.31159 (19)	−0.2054 (5)	0.7119 (4)	0.0617 (14)
H2	0.3203	−0.2935	0.7280	0.074*
C3	0.2721 (2)	−0.1808 (5)	0.6897 (4)	0.0640 (16)
H3	0.2531	−0.2520	0.6897	0.077*
C4	0.25994 (15)	−0.0520 (5)	0.6672 (3)	0.0585 (12)
H4	0.2324	−0.0342	0.6521	0.070*
C5	0.28811 (13)	0.0521 (4)	0.6665 (3)	0.0441 (10)
C6	0.28083 (15)	0.1936 (4)	0.6436 (3)	0.0453 (11)
C7	0.31502 (13)	0.2809 (4)	0.6563 (3)	0.0409 (10)
C8	0.30985 (14)	0.4155 (4)	0.6320 (3)	0.0503 (11)
H8	0.3314	0.4776	0.6405	0.060*
C9	0.27359 (16)	0.4575 (5)	0.5961 (3)	0.0582 (12)
C10	0.24033 (16)	0.3774 (5)	0.5840 (3)	0.0613 (14)
H10	0.2156	0.4105	0.5592	0.074*
C11	0.24501 (13)	0.2484 (5)	0.6095 (3)	0.0536 (12)
C12	0.41786 (14)	0.4204 (4)	0.6459 (3)	0.0521 (11)
H12	0.4174	0.3770	0.5930	0.062*
C13	0.43741 (16)	0.5417 (5)	0.6554 (4)	0.0663 (14)
H13	0.4494	0.5824	0.6097	0.080*
C14	0.43921 (18)	0.6028 (5)	0.7324 (4)	0.0722 (16)
H14	0.4527	0.6865	0.7409	0.087*
C15	0.42135 (16)	0.5422 (5)	0.7969 (3)	0.0639 (14)
H15	0.4229	0.5834	0.8505	0.077*
C16	0.40075 (13)	0.4197 (4)	0.7843 (3)	0.0458 (10)
C17	0.37829 (14)	0.3462 (4)	0.8450 (3)	0.0446 (10)
C18	0.35732 (12)	0.2308 (4)	0.8132 (3)	0.0378 (9)
C19	0.33531 (14)	0.1565 (4)	0.8687 (3)	0.0434 (10)
H19	0.3199	0.0808	0.8492	0.052*
C20	0.33618 (17)	0.1936 (4)	0.9511 (3)	0.0525 (13)
C21	0.35735 (19)	0.3014 (5)	0.9836 (4)	0.0683 (16)
H21	0.3583	0.3225	1.0416	0.082*
C22	0.37700 (17)	0.3773 (5)	0.9289 (3)	0.0649 (14)
C23	0.43021 (13)	−0.0015 (4)	0.6533 (3)	0.0446 (10)
C24	0.41319 (12)	0.0496 (4)	0.5690 (3)	0.0383 (9)
C25	0.42684 (13)	0.0104 (4)	0.4908 (3)	0.0437 (10)
C26	0.41040 (14)	0.0726 (5)	0.4191 (3)	0.0542 (12)
H26	0.4201	0.0518	0.3663	0.065*
C27	0.38003 (17)	0.1647 (5)	0.4247 (3)	0.0535 (13)
H27	0.3682	0.2063	0.3756	0.064*
C28	0.36687 (15)	0.1963 (4)	0.5008 (3)	0.0458 (11)
H28	0.3457	0.2598	0.5040	0.055*
C29	0.46854 (15)	−0.1295 (6)	0.4130 (3)	0.0619 (13)
H29A	0.4832	−0.0568	0.3858	0.074*
H29B	0.4450	−0.1555	0.3754	0.074*
C30	0.49507 (17)	−0.2473 (7)	0.4297 (5)	0.0751 (17)
H30	0.5047	−0.2911	0.3824	0.090*
C31	0.5065 (2)	−0.2967 (5)	0.5026 (5)	0.080 (2)
H31A	0.4976	−0.2565	0.5518	0.097*
H31B	0.5237	−0.3731	0.5067	0.097*
F1	0.27033 (10)	0.5876 (3)	0.5693 (2)	0.0866 (10)
F2	0.21199 (9)	0.1647 (3)	0.5980 (2)	0.0759 (9)
F3	0.31653 (10)	0.1165 (3)	1.00528 (17)	0.0748 (9)
F4	0.39817 (14)	0.4857 (3)	0.9610 (2)	0.1073 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.03972 (12)	0.03992 (11)	0.02690 (11)	−0.00128 (6)	0.00483 (8)	−0.00145 (6)
N1	0.051 (2)	0.0460 (19)	0.0293 (19)	−0.0108 (16)	0.0137 (16)	−0.0091 (15)
N2	0.045 (2)	0.0455 (18)	0.038 (2)	−0.0053 (17)	0.0091 (17)	0.0043 (17)
N3	0.047 (2)	0.0424 (17)	0.0316 (19)	0.0009 (16)	0.0072 (16)	−0.0010 (16)
O1	0.0496 (17)	0.0548 (16)	0.0270 (15)	0.0049 (14)	−0.0033 (13)	0.0029 (14)
O2	0.085 (3)	0.074 (2)	0.053 (2)	0.038 (2)	0.0088 (19)	0.0119 (18)
O3	0.0536 (19)	0.0692 (19)	0.0477 (19)	0.0164 (16)	0.0118 (16)	−0.0069 (16)
C1	0.064 (3)	0.049 (2)	0.034 (2)	−0.008 (2)	0.009 (2)	−0.0010 (19)
C2	0.087 (4)	0.055 (3)	0.045 (3)	−0.016 (3)	0.013 (3)	−0.004 (2)
C3	0.078 (4)	0.065 (3)	0.051 (3)	−0.026 (3)	0.019 (3)	−0.009 (2)
C4	0.053 (3)	0.074 (3)	0.049 (3)	−0.019 (3)	0.009 (2)	−0.010 (3)
C5	0.046 (2)	0.058 (2)	0.030 (2)	−0.010 (2)	0.0149 (19)	−0.009 (2)
C6	0.042 (3)	0.061 (3)	0.034 (3)	0.002 (2)	0.008 (2)	−0.012 (2)
C7	0.045 (2)	0.051 (2)	0.028 (2)	0.0021 (19)	0.0061 (19)	−0.0085 (18)
C8	0.050 (3)	0.053 (2)	0.048 (3)	0.005 (2)	0.004 (2)	−0.009 (2)
C9	0.065 (3)	0.055 (3)	0.055 (3)	0.018 (2)	0.004 (3)	−0.011 (2)
C10	0.055 (3)	0.076 (3)	0.052 (3)	0.024 (3)	0.002 (2)	−0.016 (3)
C11	0.040 (3)	0.074 (3)	0.047 (3)	0.003 (2)	0.008 (2)	−0.015 (3)
C12	0.057 (3)	0.057 (3)	0.044 (3)	−0.010 (2)	0.015 (2)	0.008 (2)
C13	0.074 (4)	0.067 (3)	0.060 (3)	−0.021 (3)	0.016 (3)	0.013 (3)
C14	0.082 (4)	0.054 (3)	0.082 (4)	−0.025 (3)	0.011 (3)	0.003 (3)
C15	0.082 (4)	0.052 (3)	0.058 (3)	−0.022 (3)	0.010 (3)	−0.006 (2)
C16	0.055 (3)	0.042 (2)	0.040 (2)	−0.003 (2)	0.003 (2)	−0.0020 (19)
C17	0.056 (3)	0.045 (2)	0.034 (2)	−0.005 (2)	0.008 (2)	−0.0061 (19)
C18	0.042 (2)	0.0404 (19)	0.031 (2)	0.0027 (18)	0.0018 (18)	−0.0042 (18)
C19	0.050 (3)	0.049 (2)	0.032 (2)	−0.006 (2)	0.011 (2)	−0.0047 (19)
C20	0.067 (3)	0.055 (3)	0.038 (3)	−0.007 (2)	0.020 (3)	−0.003 (2)
C21	0.089 (4)	0.077 (4)	0.041 (3)	−0.016 (3)	0.019 (3)	−0.013 (3)
C22	0.097 (4)	0.055 (3)	0.044 (3)	−0.022 (3)	0.012 (3)	−0.020 (2)
C23	0.047 (3)	0.048 (2)	0.040 (3)	0.003 (2)	0.011 (2)	0.002 (2)
C24	0.042 (2)	0.0396 (19)	0.034 (2)	−0.0034 (18)	0.0066 (18)	−0.0004 (18)
C25	0.041 (2)	0.048 (2)	0.042 (3)	−0.0038 (19)	0.010 (2)	−0.005 (2)
C26	0.057 (3)	0.068 (3)	0.039 (3)	−0.006 (2)	0.013 (2)	−0.006 (2)
C27	0.062 (3)	0.071 (3)	0.027 (2)	0.007 (2)	0.000 (2)	0.003 (2)
C28	0.053 (3)	0.052 (2)	0.033 (2)	0.0068 (19)	0.004 (2)	−0.0005 (19)
C29	0.058 (3)	0.077 (3)	0.053 (3)	0.008 (3)	0.015 (3)	−0.021 (3)
C30	0.059 (3)	0.081 (4)	0.087 (5)	0.011 (3)	0.017 (3)	−0.022 (4)
C31	0.071 (4)	0.063 (3)	0.110 (6)	0.009 (3)	0.025 (4)	0.000 (3)
F1	0.090 (2)	0.0581 (16)	0.109 (3)	0.0262 (16)	−0.015 (2)	−0.0043 (17)
F2	0.0428 (16)	0.101 (2)	0.082 (3)	−0.0054 (15)	−0.0077 (16)	−0.0100 (18)
F3	0.100 (2)	0.087 (2)	0.0399 (16)	−0.0301 (18)	0.0257 (16)	−0.0026 (15)
F4	0.177 (4)	0.092 (2)	0.055 (2)	−0.071 (2)	0.024 (2)	−0.0337 (18)

Geometric parameters (Å, º) top

Ir1—C7	1.983 (4)	C12—C13	1.371 (6)
Ir1—C18	2.002 (4)	C12—H12	0.9500
Ir1—N1	2.045 (3)	C13—C14	1.373 (8)
Ir1—N2	2.051 (4)	C13—H13	0.9500
Ir1—N3	2.132 (3)	C14—C15	1.368 (7)
Ir1—O1	2.135 (3)	C14—H14	0.9500
N1—C1	1.339 (5)	C15—C16	1.404 (6)
N1—C5	1.375 (6)	C15—H15	0.9500
N2—C12	1.341 (5)	C16—C17	1.465 (6)
N2—C16	1.367 (6)	C17—C22	1.384 (6)
N3—C24	1.343 (5)	C17—C18	1.417 (6)
N3—C28	1.352 (6)	C18—C19	1.404 (6)
O1—C23	1.307 (5)	C19—C20	1.369 (7)
O2—C23	1.212 (5)	C19—H19	0.9500
O3—C25	1.346 (5)	C20—F3	1.361 (5)
O3—C29	1.438 (6)	C20—C21	1.365 (7)
C1—C2	1.381 (7)	C21—C22	1.359 (7)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.364 (9)	C22—F4	1.367 (5)
C2—H2	0.9500	C23—C24	1.514 (6)
C3—C4	1.380 (7)	C24—C25	1.419 (6)
C3—H3	0.9500	C25—C26	1.383 (6)
C4—C5	1.398 (6)	C26—C27	1.373 (7)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.465 (6)	C27—C28	1.362 (7)
C6—C11	1.391 (7)	C27—H27	0.9500
C6—C7	1.436 (6)	C28—H28	0.9500
C7—C8	1.397 (6)	C29—C30	1.479 (8)
C8—C9	1.369 (7)	C29—H29A	0.9900
C8—H8	0.9500	C29—H29B	0.9900
C9—F1	1.360 (5)	C30—C31	1.299 (10)
C9—C10	1.369 (7)	C30—H30	0.9500
C10—C11	1.349 (8)	C31—H31A	0.9500
C10—H10	0.9500	C31—H31B	0.9500
C11—F2	1.382 (5)

C7—Ir1—C18	90.86 (17)	C13—C12—H12	118.2
C7—Ir1—N1	81.10 (16)	C12—C13—C14	118.5 (5)
C18—Ir1—N1	94.43 (15)	C12—C13—H13	120.7
C7—Ir1—N2	95.32 (15)	C14—C13—H13	120.7
C18—Ir1—N2	80.32 (16)	C15—C14—C13	119.4 (5)
N1—Ir1—N2	173.64 (13)	C15—C14—H14	120.3
C7—Ir1—N3	96.53 (15)	C13—C14—H14	120.3
C18—Ir1—N3	171.88 (15)	C14—C15—C16	120.5 (5)
N1—Ir1—N3	90.06 (13)	C14—C15—H15	119.7
N2—Ir1—N3	95.59 (14)	C16—C15—H15	119.7
C7—Ir1—O1	170.11 (14)	N2—C16—C15	119.3 (4)
C18—Ir1—O1	96.88 (14)	N2—C16—C17	113.4 (3)
N1—Ir1—O1	92.13 (13)	C15—C16—C17	127.2 (4)
N2—Ir1—O1	92.06 (13)	C22—C17—C18	118.7 (4)
N3—Ir1—O1	76.16 (12)	C22—C17—C16	126.0 (4)
C1—N1—C5	119.6 (4)	C18—C17—C16	115.2 (4)
C1—N1—Ir1	124.4 (3)	C19—C18—C17	117.6 (4)
C5—N1—Ir1	116.0 (3)	C19—C18—Ir1	127.5 (3)
C12—N2—C16	118.7 (4)	C17—C18—Ir1	114.8 (3)
C12—N2—Ir1	125.1 (3)	C20—C19—C18	119.7 (4)
C16—N2—Ir1	116.1 (3)	C20—C19—H19	120.2
C24—N3—C28	120.4 (4)	C18—C19—H19	120.2
C24—N3—Ir1	115.8 (3)	F3—C20—C21	117.2 (5)
C28—N3—Ir1	123.8 (3)	F3—C20—C19	119.1 (4)
C23—O1—Ir1	116.9 (3)	C21—C20—C19	123.6 (5)
C25—O3—C29	117.5 (4)	C22—C21—C20	116.6 (5)
N1—C1—C2	122.2 (5)	C22—C21—H21	121.7
N1—C1—H1	118.9	C20—C21—H21	121.7
C2—C1—H1	118.9	C21—C22—F4	117.0 (5)
C3—C2—C1	119.3 (5)	C21—C22—C17	123.7 (4)
C3—C2—H2	120.4	F4—C22—C17	119.3 (5)
C1—C2—H2	120.4	O2—C23—O1	124.1 (4)
C2—C3—C4	119.7 (5)	O2—C23—C24	121.4 (4)
C2—C3—H3	120.2	O1—C23—C24	114.5 (4)
C4—C3—H3	120.2	N3—C24—C25	120.0 (4)
C3—C4—C5	119.9 (5)	N3—C24—C23	115.1 (4)
C3—C4—H4	120.0	C25—C24—C23	124.9 (4)
C5—C4—H4	120.0	O3—C25—C26	124.4 (4)
N1—C5—C4	119.4 (4)	O3—C25—C24	117.0 (4)
N1—C5—C6	113.1 (4)	C26—C25—C24	118.6 (4)
C4—C5—C6	127.5 (4)	C27—C26—C25	119.6 (4)
C11—C6—C7	118.3 (4)	C27—C26—H26	120.2
C11—C6—C5	126.5 (4)	C25—C26—H26	120.2
C7—C6—C5	115.2 (4)	C28—C27—C26	120.0 (5)
C8—C7—C6	117.0 (4)	C28—C27—H27	120.0
C8—C7—Ir1	128.1 (3)	C26—C27—H27	120.0
C6—C7—Ir1	114.4 (3)	N3—C28—C27	121.4 (4)
C9—C8—C7	119.8 (4)	N3—C28—H28	119.3
C9—C8—H8	120.1	C27—C28—H28	119.3
C7—C8—H8	120.1	O3—C29—C30	107.4 (5)
F1—C9—C8	118.0 (5)	O3—C29—H29A	110.2
F1—C9—C10	117.3 (4)	C30—C29—H29A	110.2
C8—C9—C10	124.6 (5)	O3—C29—H29B	110.2
C11—C10—C9	115.6 (4)	C30—C29—H29B	110.2
C11—C10—H10	122.2	H29A—C29—H29B	108.5
C9—C10—H10	122.2	C31—C30—C29	126.5 (6)
C10—C11—F2	117.0 (4)	C31—C30—H30	116.7
C10—C11—C6	124.6 (5)	C29—C30—H30	116.7
F2—C11—C6	118.4 (5)	C30—C31—H31A	120.0
N2—C12—C13	123.5 (5)	C30—C31—H31B	120.0
N2—C12—H12	118.2	H31A—C31—H31B	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F1ⁱ	0.95	2.60	2.997 (6)	106
C28—H28···F2ⁱⁱ	0.95	2.55	3.280 (6)	134
C10—H10···F3ⁱⁱⁱ	0.95	2.50	3.299 (6)	142
C12—H12···F4^iv	0.95	2.56	3.130 (6)	119
C26—H26···O1^v	0.95	2.63	3.519 (5)	155
C14—H14···O2^vi	0.95	2.54	3.275 (6)	134

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x, −y+1, z−1/2; (v) x, −y, z−1/2; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ir(C₁₁H₆F₂N)₂(C₉H₈NO₃)]
M_r	750.70
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	185
a, b, c (Å)	33.429 (4), 9.9117 (12), 16.0265 (19)
β (°)	94.107 (2)
V (Å³)	5296.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.11
Crystal size (mm)	0.31 × 0.23 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.305, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	14169, 5087, 4364
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.05
No. of reflections	5087
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.72, −0.59

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ir1—C7	1.983 (4)	Ir1—N2	2.051 (4)
Ir1—C18	2.002 (4)	Ir1—N3	2.132 (3)
Ir1—N1	2.045 (3)	Ir1—O1	2.135 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F1ⁱ	0.95	2.60	2.997 (6)	106
C28—H28···F2ⁱⁱ	0.95	2.55	3.280 (6)	134
C10—H10···F3ⁱⁱⁱ	0.95	2.50	3.299 (6)	142
C12—H12···F4^iv	0.95	2.56	3.130 (6)	119
C26—H26···O1^v	0.95	2.63	3.519 (5)	155
C14—H14···O2^vi	0.95	2.54	3.275 (6)	134

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x, −y+1, z−1/2; (v) x, −y, z−1/2; (vi) x, y+1, z.

Acknowledgements

This work was supported by the Natural Science Foundation of Gansu Province (096RJZA086) and the `Qing Lan' Talent Engineering Funds (QL-05–23 A) of Lanzhou Jiaotong University.

References

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