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The title compound, [Ir(C11H8N)2(C12H12N2)]PF6, an iridium complex with two cyclo­metallated 2-phenyl­pyridine fragments and one 4,4′-dimethyl-2,2′-bipyridine unit, presents a distorted octa­hedral coordination geometry around the Ir atom. Charge balance is achieved through a hexa­fluoridophosphate anion. The coordination geometry of the two 2-phenylpyridine ligands around the IrIII centre retains the cis-C—C and trans-N—N chelate dispositions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059314/bg2132sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059314/bg2132Isup2.hkl
Contains datablock I

CCDC reference: 672738

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.028
  • wR factor = 0.067
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C33 - C34 .. 8.36 su
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.46 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C28 .. 5.84 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C19 .. 6.89 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 5.89 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C29 - C34 .. 5.52 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ir1 - N1 .. 5.47 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ir1 - C34 .. 6.73 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.02 From the CIF: _reflns_number_total 6124 Count of symmetry unique reflns 3461 Completeness (_total/calc) 176.94% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2663 Fraction of Friedel pairs measured 0.769 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Recently, phosphorescent materials have been extensively studied owing to their applications for organic light-emitting diodes (OLEDs) with high performances. Amongst these materials, Iridium(III) complexes containing phenylpyridine are particularly important and have been thoroughly investigated (Graces et al., 1988) because both singlet and triplet excitons can be harvested for light emission in these complexes, leading to the internal quantum efficiency of phosphorescent emitters theoretically approaching 100% (Huo et al., 2006; Wong et al., 2006). In this contribution, we present the synthesis and crystal structure of [Ir(ppy)2(dMbpy)](PF6) (ppy is 2-phenylpyridine and dMbpy is 4,4'-dimethyl-2,2'-bipyridine). The title compound reveals bright green light under excitation of UV radiation, which implies that it is a candidate for a highly efficient phosphorescent emitter in OLEDs.

The overall structural arrangement is similar to several previously reported examples, including the diketonate complex [(ppy)2Ir(acac)] (Lamansky et al.,2001), the diimine complexes such as [Ir(mppz)2(bpy-NH2)](PF6) (Lo et al., 2003). As shown in Fig.1, [Ir(ppy)2(dMbpy)](PF6) has a distorted octahedral coordination geometry with two ppy and one dMbpy around the iridium center, and one hexafluorophosphate (PF6-) anion providing for charge balance. The coordination geometry of the ppy ligands around the cation is such that the carbon atoms C(13) and C(34) are in a cis- orientation, with Ir—C bond lengths of 2.058 (4) Å and 2.055 (4) Å, respectively; on the other side, the nitrogen atoms N(1) and N(2) in ppy reside at trans- locations, with Ir—N bond lengths of 2.026 (5) Å and 2.018 (5) Å, respectively. It is to be noted that the Ir—N3 and Ir- N4 bond lengths in the dMbpy ligand are 2.141 (4)Å and 2.127 (4) Å, values which are slightly longer than those in the ppy ligand. Coordination lengths are listed in Table 1.

Related literature top

For related literature, see: Graces et al. (1988); Huo et al. (2006); Wong et al. (2006); Lo et al. (2003).

For related literature, see: Lamansky et al. (2001).

Experimental top

IrCl3.3H2O (0.1784 g, 0.51 mmol), ppy (0.20 ml, 1.29 mmol), 2-ethoxyethanol (9 ml) and water (3 ml) were heated to 120°C for 24 h under nitrogen atmosphere. After cooling to the room temperature, the precipitate was collected by filtration, washed with water and methanol, and then dried in vacuum. The obtained chloro-bridged dimmer(0.1604 g, 0.15 mmol) was mixed with dMbpy (0.0690 g, 0.375 mmol) in methanol/dichloromethane (30 ml, 1: 1, v:v). The mixture was refluxed under nitrogen atmosphere in the dark for 4 h. The title compound was achieved after metathesis with KPF6 and subsequent recrystalllization from dichloromethane /petroleum ether at room temperature.

Refinement top

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq (C) for aromatic and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular diagram of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
(4,4'-Dimethyl-2,2'-bipyridine-κ2N,N')bis[2-(2-pyridyl)phenyl- κ2N,C]iridium(III) hexafluoridophosphate top
Crystal data top
[Ir(C11H8N)2(C12H12N2)]PF6F(000) = 1624
Mr = 829.77Dx = 1.760 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 5760 reflections
a = 12.5020 (9) Åθ = 1.9–26.0°
b = 13.0490 (9) ŵ = 4.38 mm1
c = 19.1980 (13) ÅT = 293 K
V = 3131.9 (4) Å3Block, orange
Z = 40.40 × 0.30 × 0.25 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
6124 independent reflections
Radiation source: fine-focus sealed tube5760 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1511
Tmin = 0.23, Tmax = 0.33k = 1615
17622 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0242P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
6124 reflectionsΔρmax = 1.23 e Å3
415 parametersΔρmin = 0.76 e Å3
2 restraintsAbsolute structure: Flack (1983), 2663 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.024 (6)
Crystal data top
[Ir(C11H8N)2(C12H12N2)]PF6V = 3131.9 (4) Å3
Mr = 829.77Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.5020 (9) ŵ = 4.38 mm1
b = 13.0490 (9) ÅT = 293 K
c = 19.1980 (13) Å0.40 × 0.30 × 0.25 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
6124 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5760 reflections with I > 2σ(I)
Tmin = 0.23, Tmax = 0.33Rint = 0.091
17622 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.067Δρmax = 1.23 e Å3
S = 1.00Δρmin = 0.76 e Å3
6124 reflectionsAbsolute structure: Flack (1983), 2663 Friedel pairs
415 parametersAbsolute structure parameter: 0.024 (6)
2 restraints
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
xyzUiso*/Ueq
C10.1848 (6)0.2841 (4)0.1679 (3)0.0461 (15)
H1A0.21400.27780.12180.069*
H1B0.11250.30850.16490.069*
H1C0.18560.21840.19030.069*
C20.2504 (5)0.3581 (3)0.2091 (3)0.0320 (11)
C30.3407 (5)0.4050 (3)0.1812 (3)0.0338 (13)
H30.36450.38720.13690.041*
C40.3951 (5)0.4787 (4)0.2197 (2)0.0304 (11)
H40.45250.51250.19920.037*
C50.2253 (4)0.3823 (4)0.2777 (2)0.0316 (10)
H50.16660.35130.29870.038*
C60.2863 (5)0.4520 (3)0.3154 (3)0.0286 (11)
C70.2724 (5)0.4692 (3)0.3914 (2)0.0278 (11)
C80.2012 (5)0.4148 (3)0.4314 (3)0.0333 (12)
H80.15430.36890.41050.040*
C90.1995 (5)0.4285 (4)0.5034 (3)0.0355 (12)
C100.1245 (6)0.3676 (4)0.5485 (3)0.0529 (16)
H10A0.08200.32330.51970.079*
H10B0.07850.41350.57360.079*
H10C0.16500.32730.58080.079*
C110.2697 (5)0.4990 (4)0.5313 (3)0.0329 (12)
H110.27250.50880.57920.039*
C120.3352 (5)0.5546 (4)0.4882 (3)0.0328 (12)
H120.37960.60390.50800.039*
C130.5736 (4)0.5377 (3)0.3615 (2)0.0182 (9)
C140.5925 (5)0.4774 (4)0.4166 (3)0.0341 (12)
H140.54060.47160.45110.041*
C150.6874 (5)0.4234 (4)0.4238 (3)0.0426 (14)
H150.69920.38180.46240.051*
C160.7637 (6)0.4329 (4)0.3725 (3)0.0466 (15)
H160.82750.39660.37580.056*
C170.7454 (5)0.4959 (4)0.3164 (3)0.0418 (14)
H170.79720.50370.28200.050*
C180.6484 (5)0.5480 (3)0.3118 (3)0.0321 (12)
C190.6201 (4)0.6180 (3)0.2552 (2)0.0279 (10)
C200.6786 (4)0.6309 (4)0.1943 (3)0.0356 (11)
H200.74200.59470.18780.043*
C210.6428 (5)0.6974 (4)0.1434 (3)0.0387 (13)
H210.68010.70300.10170.046*
C220.5525 (5)0.7551 (3)0.1539 (3)0.0349 (12)
H220.53080.80130.11980.042*
C230.4933 (5)0.7456 (3)0.2146 (3)0.0334 (12)
H230.43310.78640.22120.040*
C240.5684 (5)0.7350 (3)0.4616 (2)0.0347 (11)
H240.62220.68630.45690.042*
C250.5753 (6)0.8112 (4)0.5126 (3)0.0447 (14)
H250.63330.81120.54290.054*
C260.4980 (6)0.8867 (4)0.5192 (3)0.0516 (16)
H260.50390.93660.55350.062*
C270.4131 (5)0.8868 (4)0.4746 (3)0.0464 (14)
H270.36160.93800.47810.056*
C280.4024 (5)0.8114 (3)0.4238 (3)0.0318 (12)
C290.3096 (5)0.8056 (3)0.3772 (3)0.0322 (12)
C300.2232 (5)0.8739 (4)0.3743 (3)0.0388 (12)
H300.22260.93110.40320.047*
C310.1400 (5)0.8576 (4)0.3299 (3)0.0436 (14)
H310.08240.90270.32880.052*
C320.1422 (5)0.7725 (4)0.2858 (3)0.0388 (13)
H320.08680.76000.25460.047*
C330.2283 (5)0.7078 (4)0.2899 (3)0.0346 (12)
H330.22970.65130.26050.042*
C340.3108 (4)0.7211 (3)0.33388 (19)0.0153 (8)
N10.4759 (5)0.7335 (3)0.4164 (2)0.0429 (12)
N20.5231 (4)0.6748 (3)0.2667 (2)0.0422 (12)
N30.3680 (4)0.5028 (3)0.28533 (19)0.0248 (9)
N40.3385 (4)0.5413 (3)0.4192 (2)0.0288 (10)
F10.4993 (4)0.4697 (2)0.59377 (19)0.0600 (10)
F20.6177 (3)0.3393 (3)0.5834 (2)0.0649 (11)
F30.5000 (4)0.2318 (2)0.6330 (2)0.0630 (11)
F40.3804 (3)0.3588 (2)0.64277 (18)0.0543 (9)
F50.4532 (3)0.3242 (2)0.53746 (18)0.0540 (9)
F60.5454 (3)0.3770 (3)0.68888 (18)0.0674 (10)
P10.49880 (14)0.35010 (11)0.61308 (8)0.0411 (4)
Ir10.436483 (15)0.622344 (12)0.347270 (9)0.02485 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.049 (4)0.042 (3)0.047 (4)0.007 (3)0.006 (3)0.008 (2)
C20.039 (3)0.023 (2)0.035 (3)0.004 (2)0.010 (2)0.0002 (19)
C30.044 (4)0.028 (2)0.029 (2)0.005 (2)0.001 (2)0.0014 (19)
C40.033 (3)0.033 (2)0.025 (2)0.006 (2)0.004 (2)0.000 (2)
C50.034 (3)0.026 (2)0.035 (2)0.002 (2)0.003 (2)0.003 (2)
C60.033 (3)0.022 (2)0.030 (3)0.002 (2)0.001 (2)0.0015 (18)
C70.034 (3)0.023 (2)0.027 (2)0.004 (2)0.001 (2)0.0007 (19)
C80.035 (3)0.029 (2)0.036 (3)0.003 (2)0.009 (3)0.0042 (19)
C90.040 (3)0.035 (2)0.031 (3)0.002 (2)0.008 (3)0.006 (2)
C100.064 (4)0.054 (3)0.041 (3)0.015 (4)0.016 (3)0.001 (3)
C110.037 (3)0.036 (3)0.027 (3)0.007 (2)0.006 (2)0.000 (2)
C120.035 (3)0.031 (2)0.032 (3)0.005 (2)0.001 (2)0.003 (2)
C130.021 (2)0.0129 (16)0.021 (2)0.0011 (17)0.0028 (19)0.0044 (14)
C140.033 (3)0.037 (3)0.033 (3)0.001 (2)0.000 (2)0.000 (2)
C150.045 (4)0.035 (3)0.048 (3)0.009 (3)0.007 (3)0.010 (2)
C160.039 (4)0.049 (3)0.052 (4)0.014 (3)0.002 (3)0.006 (3)
C170.027 (3)0.039 (3)0.059 (4)0.007 (2)0.008 (3)0.001 (3)
C180.034 (3)0.021 (2)0.041 (3)0.002 (2)0.000 (2)0.005 (2)
C190.027 (3)0.026 (2)0.031 (2)0.001 (2)0.001 (2)0.003 (2)
C200.029 (3)0.034 (2)0.044 (3)0.002 (3)0.002 (2)0.002 (2)
C210.042 (3)0.044 (3)0.031 (3)0.011 (2)0.005 (3)0.001 (2)
C220.042 (3)0.032 (2)0.031 (2)0.011 (2)0.001 (3)0.003 (2)
C230.039 (3)0.025 (2)0.036 (3)0.003 (2)0.003 (3)0.002 (2)
C240.037 (3)0.035 (2)0.032 (2)0.007 (3)0.002 (3)0.004 (2)
C250.047 (4)0.047 (3)0.040 (3)0.013 (3)0.009 (3)0.003 (2)
C260.065 (4)0.043 (3)0.047 (3)0.007 (3)0.005 (3)0.018 (3)
C270.051 (4)0.038 (3)0.050 (3)0.003 (3)0.004 (3)0.013 (3)
C280.037 (3)0.020 (2)0.038 (3)0.005 (2)0.002 (2)0.0036 (19)
C290.035 (3)0.029 (2)0.033 (3)0.002 (2)0.006 (3)0.002 (2)
C300.041 (3)0.027 (2)0.049 (3)0.004 (3)0.006 (3)0.005 (2)
C310.044 (3)0.034 (3)0.053 (3)0.013 (2)0.001 (3)0.002 (2)
C320.033 (3)0.043 (3)0.041 (3)0.003 (3)0.005 (3)0.001 (2)
C330.040 (3)0.029 (2)0.034 (3)0.002 (2)0.006 (3)0.003 (2)
C340.017 (2)0.0129 (16)0.016 (2)0.0023 (16)0.0015 (18)0.0001 (14)
N10.040 (3)0.048 (3)0.040 (3)0.011 (2)0.001 (2)0.001 (2)
N20.046 (3)0.045 (2)0.036 (3)0.005 (2)0.005 (2)0.005 (2)
N30.030 (2)0.0235 (18)0.0209 (19)0.0058 (17)0.0023 (18)0.0002 (15)
N40.032 (3)0.028 (2)0.027 (2)0.0002 (18)0.0017 (19)0.0008 (17)
F10.069 (3)0.0475 (18)0.063 (2)0.014 (2)0.014 (2)0.0061 (17)
F20.040 (2)0.092 (3)0.063 (2)0.003 (2)0.001 (2)0.022 (2)
F30.060 (3)0.0452 (18)0.084 (3)0.0122 (19)0.008 (2)0.0185 (18)
F40.042 (2)0.0624 (19)0.059 (2)0.0111 (17)0.0087 (18)0.0111 (18)
F50.058 (3)0.0576 (18)0.0465 (19)0.0029 (18)0.0040 (19)0.0062 (16)
F60.065 (3)0.098 (3)0.0390 (18)0.005 (3)0.0112 (18)0.005 (2)
P10.0371 (9)0.0471 (9)0.0390 (8)0.0008 (7)0.0013 (7)0.0073 (6)
Ir10.02670 (10)0.02314 (9)0.02473 (9)0.00017 (8)0.00159 (8)0.00069 (7)
Geometric parameters (Å, º) top
C1—C21.495 (7)C20—C211.381 (7)
C1—H1A0.9600C20—H200.9300
C1—H1B0.9600C21—C221.372 (8)
C1—H1C0.9600C21—H210.9300
C2—C51.390 (7)C22—C231.388 (8)
C2—C31.390 (8)C22—H220.9300
C3—C41.390 (7)C23—N21.411 (6)
C3—H30.9300C23—H230.9300
C4—N31.342 (6)C24—C251.397 (7)
C4—H40.9300C24—N11.447 (7)
C5—C61.391 (7)C24—H240.9300
C5—H50.9300C25—C261.386 (9)
C6—N31.347 (7)C25—H250.9300
C6—C71.486 (7)C26—C271.364 (9)
C7—N41.361 (6)C26—H260.9300
C7—C81.373 (7)C27—C281.392 (7)
C8—C91.393 (7)C27—H270.9300
C8—H80.9300C28—N11.378 (8)
C9—C111.380 (8)C28—C291.468 (8)
C9—C101.503 (7)C29—C341.380 (6)
C10—H10A0.9600C29—C301.402 (8)
C10—H10B0.9600C30—C311.362 (9)
C10—H10C0.9600C30—H300.9300
C11—C121.372 (7)C31—C321.396 (7)
C11—H110.9300C31—H310.9300
C12—N41.337 (6)C32—C331.369 (8)
C12—H120.9300C32—H320.9300
C13—C141.340 (6)C33—C341.344 (6)
C13—C181.342 (7)C33—H330.9300
C13—Ir12.057 (4)C34—Ir12.049 (4)
C14—C151.386 (8)N1—Ir12.026 (5)
C14—H140.9300N2—Ir12.009 (5)
C15—C161.377 (9)N3—Ir12.140 (4)
C15—H150.9300N4—Ir12.127 (4)
C16—C171.374 (8)F1—P11.604 (4)
C16—H160.9300F2—P11.599 (4)
C17—C181.394 (8)F3—P11.590 (3)
C17—H170.9300F4—P11.590 (4)
C18—C191.463 (7)F5—P11.596 (4)
C19—C201.389 (7)F6—P11.607 (4)
C19—N21.438 (6)
C2—C1—H1A109.5C25—C24—N1118.6 (6)
C2—C1—H1B109.5C25—C24—H24120.7
H1A—C1—H1B109.5N1—C24—H24120.7
C2—C1—H1C109.5C26—C25—C24121.8 (6)
H1A—C1—H1C109.5C26—C25—H25119.1
H1B—C1—H1C109.5C24—C25—H25119.1
C5—C2—C3116.7 (5)C27—C26—C25119.1 (5)
C5—C2—C1121.6 (5)C27—C26—H26120.5
C3—C2—C1121.8 (5)C25—C26—H26120.5
C4—C3—C2119.8 (5)C26—C27—C28120.9 (6)
C4—C3—H3120.1C26—C27—H27119.6
C2—C3—H3120.1C28—C27—H27119.6
N3—C4—C3122.5 (5)N1—C28—C27122.1 (6)
N3—C4—H4118.7N1—C28—C29115.2 (4)
C3—C4—H4118.7C27—C28—C29122.6 (5)
C2—C5—C6121.1 (5)C34—C29—C30119.5 (5)
C2—C5—H5119.4C34—C29—C28113.6 (5)
C6—C5—H5119.4C30—C29—C28126.9 (5)
N3—C6—C5121.0 (4)C31—C30—C29120.9 (5)
N3—C6—C7115.8 (4)C31—C30—H30119.5
C5—C6—C7123.0 (5)C29—C30—H30119.5
N4—C7—C8122.0 (4)C30—C31—C32119.2 (6)
N4—C7—C6114.7 (5)C30—C31—H31120.4
C8—C7—C6123.2 (5)C32—C31—H31120.4
C7—C8—C9120.0 (5)C33—C32—C31118.1 (6)
C7—C8—H8120.0C33—C32—H32121.0
C9—C8—H8120.0C31—C32—H32121.0
C11—C9—C8117.4 (5)C34—C33—C32124.1 (5)
C11—C9—C10121.7 (5)C34—C33—H33118.0
C8—C9—C10120.9 (5)C32—C33—H33118.0
C9—C10—H10A109.5C33—C34—C29118.2 (5)
C9—C10—H10B109.5C33—C34—Ir1125.9 (3)
H10A—C10—H10B109.5C29—C34—Ir1115.8 (4)
C9—C10—H10C109.5C28—N1—C24117.4 (4)
H10A—C10—H10C109.5C28—N1—Ir1115.7 (4)
H10B—C10—H10C109.5C24—N1—Ir1126.7 (4)
C12—C11—C9119.9 (5)C23—N2—C19116.9 (5)
C12—C11—H11120.1C23—N2—Ir1128.7 (4)
C9—C11—H11120.1C19—N2—Ir1113.4 (3)
N4—C12—C11123.2 (5)C4—N3—C6118.6 (4)
N4—C12—H12118.4C4—N3—Ir1126.3 (4)
C11—C12—H12118.4C6—N3—Ir1115.1 (3)
C14—C13—C18119.8 (5)C12—N4—C7117.4 (4)
C14—C13—Ir1124.6 (4)C12—N4—Ir1126.6 (4)
C18—C13—Ir1115.6 (3)C7—N4—Ir1116.0 (3)
C13—C14—C15121.9 (5)F4—P1—F389.6 (2)
C13—C14—H14119.1F4—P1—F590.5 (2)
C15—C14—H14119.1F3—P1—F590.9 (2)
C16—C15—C14118.4 (5)F4—P1—F2179.1 (2)
C16—C15—H15120.8F3—P1—F289.5 (2)
C14—C15—H15120.8F5—P1—F289.4 (2)
C17—C16—C15120.0 (6)F4—P1—F191.0 (2)
C17—C16—H16120.0F3—P1—F1179.0 (3)
C15—C16—H16120.0F5—P1—F189.86 (19)
C16—C17—C18119.1 (6)F2—P1—F190.0 (2)
C16—C17—H17120.4F4—P1—F689.8 (2)
C18—C17—H17120.4F3—P1—F689.5 (2)
C13—C18—C17120.8 (5)F5—P1—F6179.4 (3)
C13—C18—C19115.0 (5)F2—P1—F690.3 (2)
C17—C18—C19124.2 (5)F1—P1—F689.7 (2)
C20—C19—N2120.7 (4)N2—Ir1—N197.43 (19)
C20—C19—C18125.0 (5)N2—Ir1—C3495.89 (17)
N2—C19—C18114.3 (4)N1—Ir1—C3479.54 (19)
C21—C20—C19120.0 (5)N2—Ir1—C1380.55 (18)
C21—C20—H20120.0N1—Ir1—C1395.43 (19)
C19—C20—H20120.0C34—Ir1—C13173.47 (15)
C22—C21—C20120.5 (5)N2—Ir1—N4168.43 (17)
C22—C21—H21119.7N1—Ir1—N494.09 (17)
C20—C21—H21119.7C34—Ir1—N487.28 (16)
C21—C22—C23120.9 (5)C13—Ir1—N497.28 (16)
C21—C22—H22119.6N2—Ir1—N392.06 (17)
C23—C22—H22119.6N1—Ir1—N3169.34 (19)
C22—C23—N2120.9 (5)C34—Ir1—N394.71 (15)
C22—C23—H23119.6C13—Ir1—N390.90 (15)
N2—C23—H23119.6N4—Ir1—N376.57 (15)
C5—C2—C3—C45.4 (7)C18—C19—N2—Ir112.0 (5)
C1—C2—C3—C4175.6 (5)C3—C4—N3—C61.4 (7)
C2—C3—C4—N34.1 (8)C3—C4—N3—Ir1174.7 (4)
C3—C2—C5—C61.6 (7)C5—C6—N3—C45.4 (7)
C1—C2—C5—C6179.4 (5)C7—C6—N3—C4169.9 (4)
C2—C5—C6—N33.9 (7)C5—C6—N3—Ir1171.2 (4)
C2—C5—C6—C7171.0 (5)C7—C6—N3—Ir113.5 (5)
N3—C6—C7—N45.6 (6)C11—C12—N4—C70.4 (8)
C5—C6—C7—N4179.3 (4)C11—C12—N4—Ir1179.9 (4)
N3—C6—C7—C8172.3 (5)C8—C7—N4—C122.9 (7)
C5—C6—C7—C82.8 (8)C6—C7—N4—C12175.1 (4)
N4—C7—C8—C93.7 (8)C8—C7—N4—Ir1176.8 (4)
C6—C7—C8—C9174.1 (5)C6—C7—N4—Ir15.3 (5)
C7—C8—C9—C111.1 (8)C23—N2—Ir1—N188.4 (5)
C7—C8—C9—C10178.2 (5)C19—N2—Ir1—N1103.5 (4)
C8—C9—C11—C122.0 (8)C23—N2—Ir1—C348.2 (4)
C10—C9—C11—C12178.6 (5)C19—N2—Ir1—C34176.3 (3)
C9—C11—C12—N42.9 (8)C23—N2—Ir1—C13177.3 (5)
C18—C13—C14—C150.9 (7)C19—N2—Ir1—C139.2 (3)
Ir1—C13—C14—C15179.0 (4)C23—N2—Ir1—N497.3 (10)
C13—C14—C15—C160.1 (9)C19—N2—Ir1—N470.9 (11)
C14—C15—C16—C171.0 (9)C23—N2—Ir1—N386.8 (4)
C15—C16—C17—C181.3 (9)C19—N2—Ir1—N381.4 (3)
C14—C13—C18—C170.6 (7)C28—N1—Ir1—N298.5 (4)
Ir1—C13—C18—C17178.9 (4)C24—N1—Ir1—N286.4 (4)
C14—C13—C18—C19178.3 (4)C28—N1—Ir1—C343.9 (4)
Ir1—C13—C18—C190.1 (5)C24—N1—Ir1—C34179.0 (4)
C16—C17—C18—C130.4 (8)C28—N1—Ir1—C13179.6 (4)
C16—C17—C18—C19179.3 (5)C24—N1—Ir1—C135.2 (4)
C13—C18—C19—C20171.6 (5)C28—N1—Ir1—N482.6 (4)
C17—C18—C19—C209.5 (8)C24—N1—Ir1—N492.5 (4)
C13—C18—C19—N27.9 (6)C28—N1—Ir1—N354.2 (11)
C17—C18—C19—N2171.0 (5)C24—N1—Ir1—N3120.9 (9)
N2—C19—C20—C211.2 (7)C33—C34—Ir1—N283.9 (4)
C18—C19—C20—C21178.3 (5)C29—C34—Ir1—N299.8 (4)
C19—C20—C21—C223.4 (8)C33—C34—Ir1—N1179.6 (4)
C20—C21—C22—C232.2 (8)C29—C34—Ir1—N13.4 (4)
C21—C22—C23—N21.3 (8)C33—C34—Ir1—N485.0 (4)
N1—C24—C25—C262.2 (8)C29—C34—Ir1—N491.3 (4)
C24—C25—C26—C270.2 (9)C33—C34—Ir1—N38.7 (4)
C25—C26—C27—C281.2 (9)C29—C34—Ir1—N3167.6 (3)
C26—C27—C28—N10.3 (9)C14—C13—Ir1—N2173.0 (4)
C26—C27—C28—C29176.8 (5)C18—C13—Ir1—N25.1 (3)
N1—C28—C29—C340.9 (7)C14—C13—Ir1—N176.4 (4)
C27—C28—C29—C34175.7 (5)C18—C13—Ir1—N1101.8 (3)
N1—C28—C29—C30179.4 (5)C14—C13—Ir1—N418.5 (4)
C27—C28—C29—C302.8 (8)C18—C13—Ir1—N4163.4 (3)
C34—C29—C30—C310.6 (8)C14—C13—Ir1—N395.1 (4)
C28—C29—C30—C31177.8 (5)C18—C13—Ir1—N386.8 (3)
C29—C30—C31—C321.1 (9)C12—N4—Ir1—N2160.3 (8)
C30—C31—C32—C330.7 (8)C7—N4—Ir1—N220.1 (11)
C31—C32—C33—C340.2 (9)C12—N4—Ir1—N114.1 (5)
C32—C33—C34—C290.7 (8)C7—N4—Ir1—N1165.5 (4)
C32—C33—C34—Ir1175.5 (4)C12—N4—Ir1—C3493.4 (4)
C30—C29—C34—C330.3 (7)C7—N4—Ir1—C3486.2 (4)
C28—C29—C34—C33178.9 (4)C12—N4—Ir1—C1381.9 (4)
C30—C29—C34—Ir1176.3 (4)C7—N4—Ir1—C1398.5 (4)
C28—C29—C34—Ir12.3 (5)C12—N4—Ir1—N3171.1 (4)
C27—C28—N1—C242.7 (8)C7—N4—Ir1—N39.3 (4)
C29—C28—N1—C24179.4 (4)C4—N3—Ir1—N26.5 (4)
C27—C28—N1—Ir1172.9 (4)C6—N3—Ir1—N2169.8 (3)
C29—C28—N1—Ir13.8 (6)C4—N3—Ir1—N1159.4 (9)
C25—C24—N1—C283.6 (7)C6—N3—Ir1—N116.9 (11)
C25—C24—N1—Ir1171.5 (4)C4—N3—Ir1—C34102.5 (4)
C22—C23—N2—C193.4 (7)C6—N3—Ir1—C3473.7 (3)
C22—C23—N2—Ir1164.5 (4)C4—N3—Ir1—C1374.1 (4)
C20—C19—N2—C232.1 (7)C6—N3—Ir1—C13109.6 (3)
C18—C19—N2—C23178.4 (4)C4—N3—Ir1—N4171.4 (4)
C20—C19—N2—Ir1167.5 (4)C6—N3—Ir1—N412.3 (3)

Experimental details

Crystal data
Chemical formula[Ir(C11H8N)2(C12H12N2)]PF6
Mr829.77
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)12.5020 (9), 13.0490 (9), 19.1980 (13)
V3)3131.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)4.38
Crystal size (mm)0.40 × 0.30 × 0.25
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.23, 0.33
No. of measured, independent and
observed [I > 2σ(I)] reflections
17622, 6124, 5760
Rint0.091
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.067, 1.00
No. of reflections6124
No. of parameters415
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.23, 0.76
Absolute structureFlack (1983), 2663 Friedel pairs
Absolute structure parameter0.024 (6)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Selected bond lengths (Å) top
C13—Ir12.057 (4)N2—Ir12.009 (5)
C34—Ir12.049 (4)N3—Ir12.140 (4)
N1—Ir12.026 (5)N4—Ir12.127 (4)
 

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