Literature DB >> 21579961

mer-Bis[3,5-difluoro-2-(2-pyrid-yl)phenyl-κC,N]{5-(2-pyridyl-κN)-3-[3-(4-vinyl-benz-yloxy)phen-yl]-1,2,4-triazol-1-ido}iridium(III) methanol solvate.

Peter G Jones, Marc Debeaux, Andreas Weinkauf, Henning Hopf, Wolfgang Kowalsky, Hans-Hermann Johannes.   

Abstract

In the title compound, [Ir(C(11)H(6)F(2)N)(2)(C(22)H(17)N(4)O)]·CH(3)OH, the coordination at iridium is essentially octa-hedral, but with distortions associated with the bite angles of the ligands [76.25 (9)-80.71 (12)°] and the differing trans influences of C and N ligands [Ir-N = 2.04 Å (average) trans to N but 2.14 Å trans to C]. All three bidentate ligands have coordinating ring systems that are almost coplanar [inter-planar angles = 1.7 (1)-3.8 (2)°]. The vinyl-benzyl group is disordered over two positions with occupations of 0.653 (4) and 0.347 (4). The methanol solvent mol-ecule is involved in a classical O-H⋯N hydrogen bond to a triazole N atom.

Entities:  

Year:  2009        PMID： 21579961      PMCID： PMC2980050          DOI： 10.1107/S1600536809052726

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to organic light-emitting diodes (OLEDs), see: Adachi et al. (2001 ▶); Baldo et al. (1998 ▶); Burroughes et al. (1990 ▶); Chang et al. (2007 ▶); Coppo et al. (2004 ▶); Dedeian et al. (1991 ▶); Dixon et al. (2000 ▶); Gong et al. (2002 ▶); Grushin et al. (2001 ▶); Lamansky et al. (2001 ▶); Schütz et al. (2008 ▶); Suzuki et al. (2005 ▶); Tang & VanSlyke (1987 ▶); You & Park (2005 ▶).

Experimental

Crystal data

[Ir(C11H6F2N)2(C22H17N4O)]·CH4O M = 957.97 Triclinic, a = 9.8934 (1) Å b = 12.3039 (2) Å c = 16.8933 (3) Å α = 81.7429 (14)° β = 83.2858 (11)° γ = 69.9647 (14)° V = 1906.82 (5) Å3 Z = 2 Mo Kα radiation μ = 3.57 mm−1 T = 100 K 0.20 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.848, T max = 1.000 53102 measured reflections 10448 independent reflections 8442 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029 wR(F 2) = 0.064 S = 0.93 10448 reflections 538 parameters 69 restraints H-atom parameters constrained Δρmax = 2.18 e Å−3 Δρmin = −0.84 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052726/tk2595sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052726/tk2595Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ir(C11H6F2N)2(C22H17N4O)]·CH4OZ = 2
Mr = 957.97F(000) = 948
Triclinic, P1Dx = 1.668 Mg m−3
Hall symbol: -P 1Melting point: 560 K
a = 9.8934 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3039 (2) ÅCell parameters from 25891 reflections
c = 16.8933 (3) Åθ = 2.0–30.7°
α = 81.7429 (14)°µ = 3.57 mm−1
β = 83.2858 (11)°T = 100 K
γ = 69.9647 (14)°Prism, yellow
V = 1906.82 (5) Å30.20 × 0.15 × 0.10 mm
Oxford Diffraction Xcalibur E diffractometer10448 independent reflections
Radiation source: Enhance (Mo) X-ray Source8442 reflections with I > 2σ(I)
graphiteRint = 0.034
Detector resolution: 16.1419 pixels mm-1θmax = 29.6°, θmin = 2.0°
ω scanh = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −17→17
Tmin = 0.848, Tmax = 1.000l = −23→23
53102 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 0.93w = 1/[σ2(Fo2) + (0.0374P)2] where P = (Fo2 + 2Fc2)/3
10448 reflections(Δ/σ)max = 0.028
538 parametersΔρmax = 2.18 e Å−3
69 restraintsΔρmin = −0.84 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)3.2255 (0.0106) x + 5.5173 (0.0081) y + 15.8973 (0.0047) z = 8.4546 (0.0089)* -0.0191 (0.0010) Ir * 0.0215 (0.0015) N3 * 0.0244 (0.0015) N4 * -0.0109 (0.0018) C23 * -0.0159 (0.0018) C28Rms deviation of fitted atoms = 0.0190- 5.0032 (0.0075) x + 7.5842 (0.0079) y - 2.6742 (0.0193) z = 0.8875 (0.0113)Angle to previous plane (with approximate e.s.d.) = 88.07 (0.08)* -0.0017 (0.0011) Ir * -0.0003 (0.0016) N1 * 0.0030 (0.0019) C1 * -0.0050 (0.0018) C6 * 0.0041 (0.0015) C11Rms deviation of fitted atoms = 0.00338.0059 (0.0047) x + 7.0413 (0.0123) y - 6.0961 (0.0152) z = 9.2723 (0.0097)Angle to previous plane (with approximate e.s.d.) = 87.21 (0.07)* -0.0001 (0.0011) Ir * 0.0052 (0.0015) N2 * -0.0092 (0.0018) C12 * 0.0091 (0.0019) C17 * -0.0051 (0.0016) C22Rms deviation of fitted atoms = 0.0066- 4.9239 (0.0124) x + 7.5102 (0.0143) y - 3.5667 (0.0238) z = 0.6667 (0.0227)Angle to previous plane (with approximate e.s.d.) = 88.93 (0.09)* -0.0051 (0.0020) N1 * 0.0097 (0.0022) C1 * -0.0065 (0.0026) C2 * -0.0011 (0.0029) C3 * 0.0057 (0.0026) C4 * -0.0027 (0.0022) C5Rms deviation of fitted atoms = 0.0058- 5.0855 (0.0105) x + 7.5155 (0.0121) y - 2.5377 (0.0215) z = 0.7805 (0.0195)Angle to previous plane (with approximate e.s.d.) = 3.74 (0.23)* -0.0030 (0.0020) C6 * -0.0032 (0.0024) C7 * 0.0061 (0.0024) C8 * -0.0028 (0.0023) C9 * -0.0034 (0.0021) C10 * 0.0063 (0.0019) C11Rms deviation of fitted atoms = 0.00447.8608 (0.0075) x + 6.9324 (0.0128) y - 6.5592 (0.0188) z = 9.0941 (0.0078)Angle to previous plane (with approximate e.s.d.) = 87.00 (0.09)* -0.0057 (0.0019) N2 * 0.0051 (0.0020) C12 * -0.0006 (0.0023) C13 * -0.0035 (0.0023) C14 * 0.0030 (0.0022) C15 * 0.0016 (0.0021) C16Rms deviation of fitted atoms = 0.00378.1881 (0.0069) x + 6.6251 (0.0132) y - 6.0523 (0.0203) z = 9.0428 (0.0130)Angle to previous plane (with approximate e.s.d.) = 3.41 (0.18)* 0.0009 (0.0020) C17 * 0.0004 (0.0022) C18 * -0.0039 (0.0023) C19 * 0.0060 (0.0024) C20 * -0.0045 (0.0022) C21 * 0.0010 (0.0021) C22Rms deviation of fitted atoms = 0.00353.1752 (0.0118) x + 5.2258 (0.0137) y + 16.0284 (0.0067) z = 8.3218 (0.0125)Angle to previous plane (with approximate e.s.d.) = 85.49 (0.09)* -0.0036 (0.0019) N3 * -0.0039 (0.0020) C23 * 0.0076 (0.0022) C24 * -0.0040 (0.0023) C25 * -0.0033 (0.0022) C26 * 0.0073 (0.0020) C27Rms deviation of fitted atoms = 0.00533.4499 (0.0143) x + 5.2695 (0.0146) y + 15.9354 (0.0080) z = 8.4866 (0.0099)Angle to previous plane (with approximate e.s.d.) = 1.70 (0.14)* -0.0012 (0.0016) N4 * -0.0019 (0.0016) N5 * -0.0046 (0.0016) N6 * 0.0036 (0.0016) C28 * 0.0040 (0.0017) C29Rms deviation of fitted atoms = 0.0033
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.
xyzUiso*/UeqOcc. (<1)
Ir0.714159 (11)0.644989 (9)0.161874 (7)0.02659 (4)
N10.7504 (3)0.7041 (2)0.26105 (15)0.0309 (5)
N20.6692 (2)0.6055 (2)0.05631 (14)0.0297 (5)
N30.8732 (2)0.4767 (2)0.19058 (14)0.0278 (5)
N40.5913 (2)0.5443 (2)0.22449 (14)0.0290 (5)
N50.4497 (3)0.5607 (2)0.24969 (15)0.0313 (5)
N60.5827 (3)0.3722 (2)0.28304 (14)0.0305 (5)
F11.0571 (2)0.8804 (2)0.19271 (14)0.0637 (6)
F21.0605 (2)0.7954 (2)−0.06767 (12)0.0556 (5)
F30.3418 (2)0.9040 (2)−0.04453 (13)0.0608 (6)
F40.3587 (2)1.08740 (17)0.17490 (17)0.0701 (7)
O0.2211 (3)0.1772 (2)0.41368 (14)0.0503 (6)
C10.8454 (3)0.7639 (3)0.25172 (19)0.0363 (7)
C20.8715 (4)0.8095 (3)0.3164 (2)0.0513 (9)
H20.93970.84940.31010.062*
C30.7979 (5)0.7970 (4)0.3901 (2)0.0625 (11)
H30.81470.82900.43440.075*
C40.7006 (4)0.7383 (3)0.3989 (2)0.0521 (10)
H40.64890.72960.44910.063*
C50.6797 (3)0.6927 (3)0.33407 (19)0.0386 (7)
H50.61300.65140.34030.046*
C60.9075 (3)0.7745 (2)0.16876 (18)0.0319 (6)
C71.0059 (4)0.8317 (3)0.1408 (2)0.0425 (8)
C81.0578 (4)0.8414 (3)0.0622 (2)0.0434 (8)
H81.12400.88190.04450.052*
C91.0087 (3)0.7895 (3)0.0103 (2)0.0400 (8)
C100.9111 (3)0.7311 (3)0.03312 (18)0.0323 (7)
H100.88070.6967−0.00520.039*
C110.8574 (3)0.7232 (2)0.11339 (18)0.0280 (6)
C120.5624 (3)0.6896 (3)0.01559 (19)0.0351 (7)
C130.5223 (4)0.6677 (3)−0.0547 (2)0.0455 (9)
H130.44750.7260−0.08250.055*
C140.5895 (4)0.5627 (4)−0.0848 (2)0.0479 (9)
H140.56140.5480−0.13300.058*
C150.6979 (4)0.4792 (3)−0.04409 (19)0.0416 (8)
H150.74640.4062−0.06390.050*
C160.7347 (3)0.5033 (3)0.02574 (18)0.0347 (7)
H160.80960.44550.05370.042*
C170.5012 (3)0.7966 (3)0.05579 (19)0.0356 (7)
C180.3976 (3)0.8979 (3)0.0267 (2)0.0442 (9)
C190.3463 (3)0.9952 (3)0.0644 (3)0.0518 (10)
H190.27431.06330.04310.062*
C200.4042 (4)0.9899 (3)0.1353 (3)0.0510 (10)
C210.5066 (3)0.8936 (3)0.1702 (2)0.0406 (8)
H210.54150.89440.22010.049*
C220.5573 (3)0.7946 (2)0.12954 (19)0.0329 (7)
C230.8215 (3)0.3924 (2)0.22827 (16)0.0276 (6)
C240.9108 (3)0.2797 (3)0.24803 (19)0.0346 (7)
H240.87220.22260.27530.042*
C251.0571 (3)0.2515 (3)0.2275 (2)0.0390 (8)
H251.12010.17420.23970.047*
C261.1106 (3)0.3365 (3)0.18928 (19)0.0354 (7)
H261.21090.31850.17480.042*
C271.0169 (3)0.4480 (3)0.17215 (17)0.0314 (6)
H271.05470.50650.14650.038*
C280.6655 (3)0.4329 (2)0.24554 (16)0.0273 (6)
C290.4508 (3)0.4553 (3)0.28467 (17)0.0308 (6)
C300.3195 (3)0.4309 (3)0.32093 (18)0.0336 (7)
C310.3315 (4)0.3168 (3)0.35168 (18)0.0379 (7)
H310.42260.25690.34860.045*
C320.2111 (4)0.2905 (3)0.38664 (19)0.0432 (8)
C330.0807 (4)0.3776 (3)0.3946 (2)0.0469 (9)
H33−0.00070.36050.42150.056*
C340.0688 (4)0.4897 (3)0.3636 (2)0.0487 (9)
H34−0.02190.54960.36840.058*
C350.1860 (3)0.5171 (3)0.3254 (2)0.0429 (8)
H350.17510.59450.30230.052*
C360.3592 (7)0.0866 (5)0.4007 (4)0.071 (2)0.653 (4)
H36A0.42990.09180.43570.085*0.653 (4)
H36B0.39730.09540.34420.085*0.653 (4)
C370.3348 (5)−0.0286 (3)0.4204 (2)0.0622 (19)0.653 (4)
C380.3438 (5)−0.0840 (3)0.49835 (19)0.072 (2)0.653 (4)
H380.3633−0.04820.53990.086*0.653 (4)
C390.3242 (6)−0.1918 (3)0.51547 (16)0.0604 (19)0.653 (4)
H390.3303−0.22960.56870.072*0.653 (4)
C400.2956 (6)−0.2442 (3)0.4547 (2)0.0362 (13)0.653 (4)
C410.2867 (6)−0.1888 (3)0.37680 (19)0.0527 (18)0.653 (4)
H410.2672−0.22460.33530.063*0.653 (4)
C420.3063 (5)−0.0810 (3)0.35967 (17)0.0585 (16)0.653 (4)
H420.3002−0.04320.30640.070*0.653 (4)
C430.2863 (11)−0.3593 (5)0.4678 (4)0.0501 (18)0.653 (4)
H430.2594−0.38600.42400.060*0.653 (4)
C440.311 (2)−0.4304 (10)0.5326 (6)0.080 (4)0.653 (4)
H44A0.3378−0.40820.57820.096*0.653 (4)
H44B0.3011−0.50510.53460.096*0.653 (4)
C36'0.0909 (11)0.1407 (8)0.4352 (7)0.049 (3)*0.347 (4)
H36C0.04320.16760.48710.059*0.347 (4)
H36D0.02100.17470.39360.059*0.347 (4)
C37'0.1405 (9)0.0112 (6)0.4411 (5)0.049 (3)*0.347 (4)
C38'0.1309 (12)−0.0504 (9)0.5161 (5)0.143 (8)*0.347 (4)
H38'0.0859−0.00990.56110.172*0.347 (4)
C39'0.1870 (14)−0.1713 (9)0.5251 (6)0.103 (6)*0.347 (4)
H39'0.1804−0.21340.57630.124*0.347 (4)
C40'0.2528 (13)−0.2305 (6)0.4592 (8)0.073 (5)*0.347 (4)
C41'0.2625 (12)−0.1689 (8)0.3843 (6)0.076 (5)*0.347 (4)
H41'0.3074−0.20940.33930.091*0.347 (4)
C42'0.2063 (10)−0.0480 (8)0.3753 (4)0.078 (4)*0.347 (4)
H42'0.2129−0.00590.32400.093*0.347 (4)
C43'0.325 (3)−0.3545 (13)0.4677 (15)0.087 (7)*0.347 (4)
H43'0.3818−0.38680.42200.105*0.347 (4)
C44'0.321 (5)−0.427 (3)0.5311 (19)0.115 (11)*0.347 (4)
H44C0.2657−0.39910.57850.137*0.347 (4)
H44D0.3729−0.50740.53020.137*0.347 (4)
O990.6874 (3)0.1238 (2)0.30300 (14)0.0464 (6)
H990.65000.19560.30650.070*
C990.6872 (4)0.1023 (3)0.2235 (2)0.0543 (10)
H99A0.58920.13730.20570.081*
H99B0.72000.01810.22070.081*
H99C0.75210.13630.18870.081*
U11U22U33U12U13U23
Ir0.02141 (6)0.02302 (6)0.02931 (6)−0.00108 (4)0.00057 (4)−0.00128 (4)
N10.0286 (13)0.0270 (12)0.0314 (13)−0.0031 (10)0.0062 (10)−0.0068 (10)
N20.0231 (12)0.0330 (13)0.0301 (13)−0.0088 (10)−0.0002 (10)0.0029 (10)
N30.0265 (12)0.0274 (12)0.0243 (12)−0.0014 (10)−0.0016 (10)−0.0058 (10)
N40.0239 (12)0.0281 (12)0.0303 (13)−0.0033 (10)0.0020 (10)−0.0047 (10)
N50.0249 (12)0.0309 (13)0.0327 (13)−0.0040 (10)0.0049 (10)−0.0045 (11)
N60.0328 (13)0.0285 (13)0.0276 (13)−0.0063 (11)0.0008 (10)−0.0063 (10)
F10.0689 (15)0.0842 (17)0.0595 (14)−0.0496 (13)0.0101 (11)−0.0284 (12)
F20.0598 (13)0.0782 (15)0.0380 (11)−0.0407 (12)0.0111 (9)−0.0034 (10)
F30.0347 (11)0.0685 (15)0.0649 (14)−0.0097 (10)−0.0156 (10)0.0293 (12)
F40.0377 (12)0.0281 (10)0.130 (2)0.0050 (9)0.0069 (12)−0.0134 (12)
O0.0573 (16)0.0502 (15)0.0440 (14)−0.0271 (13)0.0128 (12)0.0028 (12)
C10.0388 (17)0.0300 (16)0.0372 (17)−0.0073 (14)0.0014 (14)−0.0077 (13)
C20.069 (3)0.048 (2)0.044 (2)−0.0274 (19)0.0065 (18)−0.0164 (17)
C30.096 (3)0.057 (2)0.043 (2)−0.033 (2)0.010 (2)−0.0255 (19)
C40.071 (3)0.042 (2)0.0359 (19)−0.0122 (19)0.0165 (18)−0.0122 (16)
C50.0410 (18)0.0311 (16)0.0369 (18)−0.0055 (14)0.0063 (14)−0.0054 (14)
C60.0295 (15)0.0282 (15)0.0336 (16)−0.0035 (12)−0.0008 (12)−0.0059 (12)
C70.0404 (18)0.0448 (19)0.047 (2)−0.0172 (15)0.0001 (15)−0.0161 (16)
C80.0368 (18)0.048 (2)0.050 (2)−0.0239 (16)0.0080 (15)−0.0068 (16)
C90.0335 (17)0.0463 (19)0.0365 (18)−0.0123 (15)0.0043 (14)−0.0009 (15)
C100.0277 (15)0.0326 (16)0.0318 (16)−0.0048 (13)−0.0027 (12)−0.0010 (13)
C110.0180 (13)0.0250 (14)0.0345 (16)0.0005 (11)−0.0019 (11)−0.0009 (12)
C120.0235 (14)0.0431 (18)0.0361 (17)−0.0141 (13)0.0002 (12)0.0097 (14)
C130.0363 (18)0.066 (2)0.0328 (18)−0.0220 (17)−0.0084 (14)0.0149 (17)
C140.046 (2)0.078 (3)0.0270 (17)−0.032 (2)0.0020 (15)−0.0029 (17)
C150.0393 (18)0.057 (2)0.0326 (17)−0.0235 (17)0.0059 (14)−0.0073 (15)
C160.0341 (16)0.0377 (17)0.0314 (16)−0.0122 (14)0.0007 (13)−0.0031 (13)
C170.0204 (14)0.0355 (16)0.0441 (18)−0.0086 (12)−0.0003 (13)0.0146 (14)
C180.0219 (15)0.046 (2)0.056 (2)−0.0112 (14)−0.0027 (14)0.0210 (17)
C190.0171 (15)0.0383 (19)0.085 (3)−0.0022 (14)−0.0017 (17)0.0209 (19)
C200.0277 (17)0.0284 (17)0.088 (3)−0.0052 (14)0.0141 (18)−0.0027 (18)
C210.0200 (14)0.0293 (16)0.065 (2)−0.0011 (12)0.0024 (14)−0.0042 (15)
C220.0217 (14)0.0242 (14)0.0462 (18)−0.0054 (12)0.0058 (13)0.0048 (13)
C230.0273 (14)0.0277 (14)0.0245 (14)−0.0049 (12)0.0012 (11)−0.0055 (11)
C240.0350 (17)0.0254 (15)0.0373 (17)−0.0033 (13)0.0004 (13)−0.0032 (13)
C250.0361 (17)0.0276 (15)0.0423 (19)0.0033 (13)−0.0005 (14)−0.0056 (14)
C260.0261 (15)0.0337 (16)0.0366 (17)0.0019 (13)0.0016 (13)−0.0057 (13)
C270.0278 (15)0.0331 (16)0.0302 (16)−0.0060 (13)0.0006 (12)−0.0056 (12)
C280.0309 (15)0.0255 (14)0.0230 (14)−0.0057 (12)0.0013 (11)−0.0063 (11)
C290.0295 (15)0.0316 (15)0.0279 (15)−0.0062 (13)0.0018 (12)−0.0056 (12)
C300.0331 (16)0.0379 (17)0.0293 (16)−0.0115 (14)0.0016 (13)−0.0059 (13)
C310.0436 (18)0.0378 (17)0.0288 (16)−0.0116 (14)0.0020 (13)−0.0011 (13)
C320.056 (2)0.046 (2)0.0288 (17)−0.0224 (18)0.0034 (15)−0.0023 (15)
C330.050 (2)0.058 (2)0.0375 (19)−0.0283 (19)0.0085 (16)−0.0067 (17)
C340.0362 (19)0.049 (2)0.056 (2)−0.0108 (16)0.0059 (16)−0.0080 (18)
C350.0360 (18)0.0375 (18)0.052 (2)−0.0119 (15)0.0064 (15)−0.0042 (16)
C360.102 (5)0.037 (3)0.062 (4)−0.024 (3)0.041 (4)−0.008 (3)
C370.099 (5)0.034 (3)0.046 (3)−0.021 (3)0.027 (3)−0.008 (2)
C380.141 (7)0.052 (4)0.034 (3)−0.052 (4)0.011 (4)−0.011 (3)
C390.122 (6)0.042 (3)0.022 (3)−0.035 (3)−0.007 (3)0.002 (2)
C400.053 (4)0.033 (3)0.025 (3)−0.017 (2)0.000 (2)−0.0018 (18)
C410.072 (4)0.045 (3)0.029 (3)−0.005 (3)0.000 (3)−0.004 (2)
C420.070 (4)0.040 (3)0.046 (3)0.003 (3)0.005 (3)−0.001 (2)
C430.077 (6)0.050 (3)0.035 (3)−0.031 (3)−0.011 (3)−0.009 (2)
C440.170 (11)0.059 (5)0.039 (4)−0.079 (6)−0.002 (4)0.002 (3)
O990.0594 (16)0.0366 (13)0.0406 (13)−0.0142 (12)−0.0046 (11)0.0005 (10)
C990.073 (3)0.044 (2)0.050 (2)−0.0206 (19)−0.0161 (19)−0.0038 (17)
Ir—C112.010 (3)C24—C251.381 (4)
Ir—C222.012 (3)C24—H240.9500
Ir—N12.033 (2)C25—C261.377 (5)
Ir—N22.049 (2)C25—H250.9500
Ir—N42.118 (2)C26—C271.379 (4)
Ir—N32.158 (2)C26—H260.9500
N1—C51.359 (4)C27—H270.9500
N1—C11.361 (4)C29—C301.476 (4)
N2—C161.348 (4)C30—C351.384 (4)
N2—C121.370 (4)C30—C311.395 (4)
N3—C271.352 (4)C31—C321.385 (5)
N3—C231.356 (4)C31—H310.9500
N4—C281.332 (3)C32—C331.373 (5)
N4—N51.370 (3)C33—C341.373 (5)
N5—C291.342 (4)C33—H330.9500
N6—C281.339 (4)C34—C351.380 (5)
N6—C291.355 (4)C34—H340.9500
F1—C71.359 (4)C35—H350.9500
F2—C91.357 (4)C36—C371.503 (6)
F3—C181.363 (4)C36—H36A0.9900
F4—C201.371 (4)C36—H36B0.9900
O—C321.375 (4)C37—C381.3900
O—C361.454 (6)C37—C421.3900
O—C36'1.495 (11)C38—C391.3900
C1—C21.385 (5)C38—H380.9500
C1—C61.469 (4)C39—C401.3900
C2—C31.383 (5)C39—H390.9500
C2—H20.9500C40—C411.3900
C3—C41.372 (6)C40—C431.435 (6)
C3—H30.9500C41—C421.3900
C4—C51.367 (5)C41—H410.9500
C4—H40.9500C42—H420.9500
C5—H50.9500C43—C441.290 (9)
C6—C71.390 (4)C43—H430.9500
C6—C111.418 (4)C44—H44A0.9500
C7—C81.371 (5)C44—H44B0.9500
C8—C91.373 (5)C36'—C37'1.490 (10)
C8—H80.9500C36'—H36C0.9900
C9—C101.381 (4)C36'—H36D0.9900
C10—C111.400 (4)C37'—C38'1.3900
C10—H100.9500C37'—C42'1.3900
C12—C131.383 (5)C38'—C39'1.3900
C12—C171.475 (5)C38'—H38'0.9500
C13—C141.376 (5)C39'—C40'1.3900
C13—H130.9500C39'—H39'0.9500
C14—C151.376 (5)C40'—C41'1.3900
C14—H140.9500C40'—C43'1.439 (14)
C15—C161.374 (4)C41'—C42'1.3900
C15—H150.9500C41'—H41'0.9500
C16—H160.9500C42'—H42'0.9500
C17—C181.382 (4)C43'—C44'1.296 (16)
C17—C221.416 (5)C43'—H43'0.9500
C18—C191.351 (5)C44'—H44C0.9500
C19—C201.370 (6)C44'—H44D0.9500
C19—H190.9500O99—C991.406 (4)
C20—C211.377 (5)O99—H990.8400
C21—C221.395 (4)C99—H99A0.9800
C21—H210.9500C99—H99B0.9800
C23—C241.382 (4)C99—H99C0.9800
C23—C281.457 (4)
C11—Ir—C2287.62 (11)C25—C24—H24120.5
C11—Ir—N180.20 (11)C23—C24—H24120.5
C22—Ir—N193.29 (12)C26—C25—C24119.3 (3)
C11—Ir—N296.44 (11)C26—C25—H25120.3
C22—Ir—N280.71 (12)C24—C25—H25120.3
N1—Ir—N2173.28 (9)C25—C26—C27119.3 (3)
C11—Ir—N4170.49 (10)C25—C26—H26120.3
C22—Ir—N4101.08 (10)C27—C26—H26120.3
N1—Ir—N495.35 (10)N3—C27—C26122.2 (3)
N2—Ir—N488.81 (9)N3—C27—H27118.9
C11—Ir—N395.37 (10)C26—C27—H27118.9
C22—Ir—N3174.78 (11)N4—C28—N6113.2 (2)
N1—Ir—N391.44 (9)N4—C28—C23118.7 (3)
N2—Ir—N394.68 (9)N6—C28—C23128.1 (3)
N4—Ir—N376.25 (9)N5—C29—N6114.3 (3)
C5—N1—C1118.9 (3)N5—C29—C30123.2 (3)
C5—N1—Ir123.7 (2)N6—C29—C30122.5 (3)
C1—N1—Ir117.3 (2)C35—C30—C31119.2 (3)
C16—N2—C12118.7 (3)C35—C30—C29122.3 (3)
C16—N2—Ir124.8 (2)C31—C30—C29118.5 (3)
C12—N2—Ir116.5 (2)C32—C31—C30120.2 (3)
C27—N3—C23118.1 (2)C32—C31—H31119.9
C27—N3—Ir125.9 (2)C30—C31—H31119.9
C23—N3—Ir115.98 (18)C33—C32—O119.6 (3)
C28—N4—N5107.2 (2)C33—C32—C31120.0 (3)
C28—N4—Ir115.38 (18)O—C32—C31120.4 (3)
N5—N4—Ir137.37 (18)C32—C33—C34119.6 (3)
C29—N5—N4103.8 (2)C32—C33—H33120.2
C28—N6—C29101.5 (2)C34—C33—H33120.2
C32—O—C36118.1 (3)C33—C34—C35121.3 (3)
C32—O—C36'122.2 (4)C33—C34—H34119.3
C36—O—C36'117.7 (5)C35—C34—H34119.3
N1—C1—C2120.2 (3)C30—C35—C34119.5 (3)
N1—C1—C6112.8 (3)C30—C35—H35120.3
C2—C1—C6127.0 (3)C34—C35—H35120.3
C3—C2—C1119.8 (4)O—C36—C37107.5 (4)
C3—C2—H2120.1O—C36—H36A110.2
C1—C2—H2120.1C37—C36—H36A110.2
C4—C3—C2119.8 (4)O—C36—H36B110.2
C4—C3—H3120.1C37—C36—H36B110.2
C2—C3—H3120.1H36A—C36—H36B108.5
C5—C4—C3118.6 (3)C38—C37—C42120.0
C5—C4—H4120.7C38—C37—C36120.6 (4)
C3—C4—H4120.7C42—C37—C36119.4 (4)
N1—C5—C4122.6 (3)C37—C38—C39120.0
N1—C5—H5118.7C37—C38—H38120.0
C4—C5—H5118.7C39—C38—H38120.0
C7—C6—C11118.7 (3)C40—C39—C38120.0
C7—C6—C1126.0 (3)C40—C39—H39120.0
C11—C6—C1115.4 (3)C38—C39—H39120.0
F1—C7—C8116.5 (3)C39—C40—C41120.0
F1—C7—C6120.0 (3)C39—C40—C43122.2 (3)
C8—C7—C6123.5 (3)C41—C40—C43117.6 (3)
C7—C8—C9116.4 (3)C42—C41—C40120.0
C7—C8—H8121.8C42—C41—H41120.0
C9—C8—H8121.8C40—C41—H41120.0
F2—C9—C8117.8 (3)C41—C42—C37120.0
F2—C9—C10118.5 (3)C41—C42—H42120.0
C8—C9—C10123.7 (3)C37—C42—H42120.0
C9—C10—C11119.4 (3)C44—C43—C40127.1 (7)
C9—C10—H10120.3C44—C43—H43116.5
C11—C10—H10120.3C40—C43—H43116.5
C10—C11—C6118.3 (3)C43—C44—H44A120.0
C10—C11—Ir127.3 (2)C43—C44—H44B120.0
C6—C11—Ir114.3 (2)H44A—C44—H44B120.0
N2—C12—C13119.8 (3)C37'—C36'—O107.3 (7)
N2—C12—C17112.7 (3)C37'—C36'—H36C110.2
C13—C12—C17127.5 (3)O—C36'—H36C110.2
C14—C13—C12120.8 (3)C37'—C36'—H36D110.2
C14—C13—H13119.6O—C36'—H36D110.2
C12—C13—H13119.6H36C—C36'—H36D108.5
C15—C14—C13119.0 (3)C38'—C37'—C42'120.0
C15—C14—H14120.5C38'—C37'—C36'118.3 (7)
C13—C14—H14120.5C42'—C37'—C36'121.4 (7)
C16—C15—C14118.8 (3)C37'—C38'—C39'120.0
C16—C15—H15120.6C37'—C38'—H38'120.0
C14—C15—H15120.6C39'—C38'—H38'120.0
N2—C16—C15122.9 (3)C40'—C39'—C38'120.0
N2—C16—H16118.6C40'—C39'—H39'120.0
C15—C16—H16118.6C38'—C39'—H39'120.0
C18—C17—C22118.1 (3)C39'—C40'—C41'120.0
C18—C17—C12125.6 (3)C39'—C40'—C43'121.5 (11)
C22—C17—C12116.2 (3)C41'—C40'—C43'118.2 (11)
C19—C18—F3115.9 (3)C42'—C41'—C40'120.0
C19—C18—C17124.0 (4)C42'—C41'—H41'120.0
F3—C18—C17120.1 (3)C40'—C41'—H41'120.0
C18—C19—C20116.0 (3)C41'—C42'—C37'120.0
C18—C19—H19122.0C41'—C42'—H42'120.0
C20—C19—H19122.0C37'—C42'—H42'120.0
C19—C20—F4118.3 (3)C44'—C43'—C40'127 (3)
C19—C20—C21125.0 (4)C44'—C43'—H43'116.5
F4—C20—C21116.7 (4)C40'—C43'—H43'116.6
C20—C21—C22117.5 (4)C43'—C44'—H44C119.9
C20—C21—H21121.2C43'—C44'—H44D120.1
C22—C21—H21121.2H44C—C44'—H44D120.0
C21—C22—C17119.4 (3)C99—O99—H99109.5
C21—C22—Ir126.6 (3)O99—C99—H99A109.5
C17—C22—Ir113.9 (2)O99—C99—H99B109.5
N3—C23—C24122.1 (3)H99A—C99—H99B109.5
N3—C23—C28113.5 (2)O99—C99—H99C109.5
C24—C23—C28124.4 (3)H99A—C99—H99C109.5
C25—C24—C23119.0 (3)H99B—C99—H99C109.5
C11—Ir—N1—C5176.2 (2)C18—C19—C20—F4178.2 (3)
C22—Ir—N1—C589.2 (2)C18—C19—C20—C21−1.2 (5)
N4—Ir—N1—C5−12.3 (2)C19—C20—C21—C221.3 (5)
N3—Ir—N1—C5−88.6 (2)F4—C20—C21—C22−178.2 (3)
C11—Ir—N1—C10.0 (2)C20—C21—C22—C17−0.7 (4)
C22—Ir—N1—C1−87.0 (2)C20—C21—C22—Ir176.1 (2)
N4—Ir—N1—C1171.5 (2)C18—C17—C22—C210.2 (4)
N3—Ir—N1—C195.2 (2)C12—C17—C22—C21178.7 (3)
C11—Ir—N2—C1694.2 (2)C18—C17—C22—Ir−177.0 (2)
C22—Ir—N2—C16−179.3 (2)C12—C17—C22—Ir1.5 (3)
N4—Ir—N2—C16−77.9 (2)C11—Ir—C22—C21−80.6 (3)
N3—Ir—N2—C16−1.8 (2)N1—Ir—C22—C21−0.6 (3)
C11—Ir—N2—C12−87.1 (2)N2—Ir—C22—C21−177.5 (3)
C22—Ir—N2—C12−0.6 (2)N4—Ir—C22—C2195.6 (3)
N4—Ir—N2—C12100.8 (2)C11—Ir—C22—C1796.4 (2)
N3—Ir—N2—C12176.9 (2)N1—Ir—C22—C17176.4 (2)
C11—Ir—N3—C27−3.8 (2)N2—Ir—C22—C17−0.5 (2)
N1—Ir—N3—C27−84.0 (2)N4—Ir—C22—C17−87.5 (2)
N2—Ir—N3—C2793.2 (2)C27—N3—C23—C240.1 (4)
N4—Ir—N3—C27−179.2 (2)Ir—N3—C23—C24178.0 (2)
C11—Ir—N3—C23178.4 (2)C27—N3—C23—C28179.8 (2)
N1—Ir—N3—C2398.2 (2)Ir—N3—C23—C28−2.3 (3)
N2—Ir—N3—C23−84.6 (2)N3—C23—C24—C25−1.1 (5)
N4—Ir—N3—C233.00 (19)C28—C23—C24—C25179.2 (3)
C22—Ir—N4—C28172.1 (2)C23—C24—C25—C261.1 (5)
N1—Ir—N4—C28−93.5 (2)C24—C25—C26—C27−0.1 (5)
N2—Ir—N4—C2891.8 (2)C23—N3—C27—C261.0 (4)
N3—Ir—N4—C28−3.30 (19)Ir—N3—C27—C26−176.7 (2)
C22—Ir—N4—N5−6.3 (3)C25—C26—C27—N3−1.0 (5)
N1—Ir—N4—N588.2 (3)N5—N4—C28—N60.5 (3)
N2—Ir—N4—N5−86.5 (3)Ir—N4—C28—N6−178.33 (18)
N3—Ir—N4—N5178.3 (3)N5—N4—C28—C23−177.9 (2)
C28—N4—N5—C290.1 (3)Ir—N4—C28—C233.3 (3)
Ir—N4—N5—C29178.5 (2)C29—N6—C28—N4−0.8 (3)
C5—N1—C1—C21.6 (4)C29—N6—C28—C23177.4 (3)
Ir—N1—C1—C2178.0 (2)N3—C23—C28—N4−0.7 (4)
C5—N1—C1—C6−176.8 (2)C24—C23—C28—N4179.0 (3)
Ir—N1—C1—C6−0.4 (3)N3—C23—C28—N6−178.8 (3)
N1—C1—C2—C3−1.7 (5)C24—C23—C28—N60.9 (5)
C6—C1—C2—C3176.4 (3)N4—N5—C29—N6−0.6 (3)
C1—C2—C3—C40.7 (6)N4—N5—C29—C30−179.8 (3)
C2—C3—C4—C50.5 (6)C28—N6—C29—N50.9 (3)
C1—N1—C5—C4−0.4 (5)C28—N6—C29—C30−180.0 (3)
Ir—N1—C5—C4−176.6 (2)N5—C29—C30—C35−3.6 (5)
C3—C4—C5—N1−0.6 (5)N6—C29—C30—C35177.3 (3)
N1—C1—C6—C7179.3 (3)N5—C29—C30—C31176.4 (3)
C2—C1—C6—C71.0 (5)N6—C29—C30—C31−2.7 (4)
N1—C1—C6—C110.8 (4)C35—C30—C31—C32−0.4 (5)
C2—C1—C6—C11−177.5 (3)C29—C30—C31—C32179.6 (3)
C11—C6—C7—F1−179.2 (3)C36—O—C32—C33177.1 (4)
C1—C6—C7—F12.5 (5)C36'—O—C32—C3313.7 (7)
C11—C6—C7—C80.1 (5)C36—O—C32—C31−3.1 (6)
C1—C6—C7—C8−178.3 (3)C36'—O—C32—C31−166.5 (5)
F1—C7—C8—C9178.4 (3)C30—C31—C32—C33−3.2 (5)
C6—C7—C8—C9−0.9 (5)C30—C31—C32—O177.0 (3)
C7—C8—C9—F2−178.5 (3)O—C32—C33—C34−176.3 (3)
C7—C8—C9—C100.8 (5)C31—C32—C33—C343.9 (5)
F2—C9—C10—C11179.4 (3)C32—C33—C34—C35−1.0 (6)
C8—C9—C10—C110.0 (5)C31—C30—C35—C343.2 (5)
C9—C10—C11—C6−0.9 (4)C29—C30—C35—C34−176.8 (3)
C9—C10—C11—Ir179.4 (2)C33—C34—C35—C30−2.5 (6)
C7—C6—C11—C100.8 (4)C32—O—C36—C37−169.1 (3)
C1—C6—C11—C10179.4 (3)C36'—O—C36—C37−5.0 (8)
C7—C6—C11—Ir−179.4 (2)O—C36—C37—C38−88.2 (5)
C1—C6—C11—Ir−0.9 (3)O—C36—C37—C4293.2 (5)
C22—Ir—C11—C10−86.0 (3)C42—C37—C38—C390.0
N1—Ir—C11—C10−179.8 (3)C36—C37—C38—C39−178.6 (4)
N2—Ir—C11—C10−5.7 (3)C37—C38—C39—C400.0
N3—Ir—C11—C1089.7 (2)C38—C39—C40—C410.0
C22—Ir—C11—C694.2 (2)C38—C39—C40—C43174.8 (7)
N1—Ir—C11—C60.49 (19)C39—C40—C41—C420.0
N2—Ir—C11—C6174.6 (2)C43—C40—C41—C42−175.0 (6)
N3—Ir—C11—C6−90.0 (2)C40—C41—C42—C370.0
C16—N2—C12—C131.1 (4)C38—C37—C42—C410.0
Ir—N2—C12—C13−177.7 (2)C36—C37—C42—C41178.6 (4)
C16—N2—C12—C17−179.7 (2)C39—C40—C43—C44−4.5 (17)
Ir—N2—C12—C171.5 (3)C41—C40—C43—C44170.4 (13)
N2—C12—C13—C14−0.7 (5)C32—O—C36'—C37'165.6 (5)
C17—C12—C13—C14−179.7 (3)C36—O—C36'—C37'2.1 (9)
C12—C13—C14—C15−0.2 (5)O—C36'—C37'—C38'112.4 (7)
C13—C14—C15—C160.5 (5)O—C36'—C37'—C42'−62.2 (10)
C12—N2—C16—C15−0.8 (4)C42'—C37'—C38'—C39'0.0
Ir—N2—C16—C15177.9 (2)C36'—C37'—C38'—C39'−174.7 (9)
C14—C15—C16—N20.0 (5)C37'—C38'—C39'—C40'0.0
N2—C12—C17—C18176.4 (3)C38'—C39'—C40'—C41'0.0
C13—C12—C17—C18−4.5 (5)C38'—C39'—C40'—C43'173.5 (15)
N2—C12—C17—C22−1.9 (4)C39'—C40'—C41'—C42'0.0
C13—C12—C17—C22177.1 (3)C43'—C40'—C41'—C42'−173.8 (14)
C22—C17—C18—C19−0.2 (5)C40'—C41'—C42'—C37'0.0
C12—C17—C18—C19−178.5 (3)C38'—C37'—C42'—C41'0.0
C22—C17—C18—F3179.3 (3)C36'—C37'—C42'—C41'174.5 (9)
C12—C17—C18—F31.0 (5)C39'—C40'—C43'—C44'11 (4)
F3—C18—C19—C20−178.9 (3)C41'—C40'—C43'—C44'−175 (3)
C17—C18—C19—C200.7 (5)
D—H···AD—HH···AD···AD—H···A
O99—H99···N60.842.042.853 (3)164
C24—H24···O990.952.493.368 (4)154
C31—H31···O990.952.663.587 (4)164
C8—H8···F3i0.952.553.412 (4)151
C25—H25···F4ii0.952.433.088 (4)126
C3—H3···Oiii0.952.543.353 (5)143
C14—H14···N5iv0.952.573.475 (5)160
C39—H39···O99v0.952.643.272 (4)124
Table 1

Selected bond lengths (Å)

Ir—C112.010 (3)
Ir—C222.012 (3)
Ir—N12.033 (2)
Ir—N22.049 (2)
Ir—N42.118 (2)
Ir—N32.158 (2)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O99—H99⋯N60.842.042.853 (3)164
C24—H24⋯O990.952.493.368 (4)154
C31—H31⋯O990.952.663.587 (4)164
  5 in total

1.  Inter-ligand energy transfer and related emission change in the cyclometalated heteroleptic iridium complex: facile and efficient color tuning over the whole visible range by the ancillary ligand structure.

Authors:  Youngmin You; Soo Young Park
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes.

Authors:  S Lamansky; P Djurovich; D Murphy; F Abdel-Razzaq; H E Lee; C Adachi; P E Burrows; S R Forrest; M E Thompson
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

4.  Tuning iridium(III) phenylpyridine complexes in the "almost blue" region.

Authors:  Paolo Coppo; Edward A Plummer; Luisa De Cola
Journal:  Chem Commun (Camb)       Date:  2004-06-30       Impact factor: 6.222

5.  Color tuning associated with heteroleptic cyclometalated Ir(III) complexes: influence of the ancillary ligand.

Authors:  Chau-Jiun Chang; Cheng-Han Yang; Kellen Chen; Yun Chi; Ching-Fong Shu; Mei-Lin Ho; Yu-Shan Yeh; Pi-Tai Chou
Journal:  Dalton Trans       Date:  2007-05-21       Impact factor: 4.390
  5 in total

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