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Acta Cryst. (2008). E64, m1205    [ doi:10.1107/S1600536808025452 ]

Chlorido(pyridine-[kappa]N)bis[2-(quinolin-2-yl)phenyl-[kappa]2C1,N]iridium(III) monohydrate

C. Li, X.-Q. Dong, Q. Wang, C.-X. Ren and Y.-Q. Ding

Abstract top

In the neutral mononuclear iridium(III) title complex, [Ir(C15H10N)2Cl(C5H5N)]·H2O, the Ir atom is coordinated by two N atoms and two C atoms from two 2-(quinolin-2-yl)phenyl ligands, one N atom from a pyridine ligand and one Cl atom in an octahedral geometry.

Comment top

Since the significant work by Thompson and Forrest (Adachi et al., 2000; Baldo et al., 1998), the chemistry of cyclometalated IrIII complexes has received a great deal of attention. These homoleptic complexes, (CÑ)2Ir(LX), have proven to be very efficient when used in organic light emitting diodes (OLEDs), where CÑ is a general abbreviation used hereafter for a cyclometalating ligand and LX stands for other ligands. (CÑ)2Ir(LX) complexes with different ligands have various emissions (Gao et al., 2002; Lamansky et al., 2001a, b; Liu et al., 2007).

In this paper, we report the crystal structure of the title compound, which is a neutral mononuclear complex. The IrIII atom is coordinated by two N atoms and two C atoms from two 2-phenylquinoline (pq) ligands, one N atom from a pyridine ligand and one Cl atom in an octahedral geometry (Fig. 1). The Ir1—N1 and Ir1—N2 bond lengths are 2.090 (5) and 2.092 (5)Å (Table 1) and agree well with those observed in the related (CÑ)2Ir(LX) complexes (Gao et al., 2002; Lamansky et al., 2001a). The Ir—C bond lengths of 1.990 (6) and 1.992 (6)Å are slightly shorter than the Ir—C bond length [2.003 (9) Å] in the complex [Ir(ppy)2(acac)] (ppy = 2-pyridylphenyl; acac = acetylacetone) (Lamansky et al., 2001a). The N—Ir—C angles of 80.0 (2)° are comparable to that [81.7 (4)°] in [Ir(ppy)2(acac)].

Related literature top

For related literature, see: Adachi et al. (2000); Baldo et al. (1998); Gao et al. (2002); Lamansky et al. (2001a,b); Liu et al. (2007).

Experimental top

A mixture of (pq)2IrCl (0.126 g, 0.2 mmol) and sodium bicarbonate (0.04 g, 0.5 mmol) dissolved in pyridine (12 ml) and dichloromethane (10 ml) was refluxed for 24 h and then cooled to room temperature. The solvent was removed in vacuum. The residue was washed with hexane and hot water. The crude product was separated by chromatography on silica gel with dichloromethane as eluent to give a red solid. Single crystals suitable for X-ray diffraction were obtained by slow diffusion of hexane into the dichloromethane solution.

Refinement top

H atoms bonded on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms of water molecule can not be located in difference Fourier map and they were not included in refinements.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
Chlorido(pyridine-κN)bis[2-(quinolin-2-yl)phenyl- κ2C1,N]iridium(III) monohydrate top
Crystal data top
[Ir(C15H10N)2Cl(C5H5N)]·H2OF000 = 1440
Mr = 733.25Dx = 1.717 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3064 reflections
a = 9.8949 (15) Åθ = 2.5–23.5º
b = 17.653 (3) ŵ = 4.83 mm−1
c = 16.424 (3) ÅT = 273 (2) K
β = 98.545 (3)ºBlock, red
V = 2837.0 (8) Å30.16 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5027 independent reflections
Radiation source: fine-focus sealed tube3702 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
T = 273(2) Kθmax = 25.1º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→10
Tmin = 0.511, Tmax = 0.684k = −20→21
14857 measured reflectionsl = −16→19
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)] = 0.034H-atom parameters constrained
wR(F2) = 0.075  w = 1/[σ2(Fo2) + (0.0276P)2 + 1.7551P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5027 reflectionsΔρmax = 0.78 e Å−3
370 parametersΔρmin = −0.72 e Å−3
9 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ir(C15H10N)2Cl(C5H5N)]·H2OV = 2837.0 (8) Å3
Mr = 733.25Z = 4
Monoclinic, P21/nMo Kα
a = 9.8949 (15) ŵ = 4.83 mm−1
b = 17.653 (3) ÅT = 273 (2) K
c = 16.424 (3) Å0.16 × 0.12 × 0.08 mm
β = 98.545 (3)º
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5027 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3702 reflections with I > 2σ(I)
Tmin = 0.511, Tmax = 0.684Rint = 0.049
14857 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0349 restraints
wR(F2) = 0.075H-atom parameters constrained
S = 1.02Δρmax = 0.78 e Å−3
5027 reflectionsΔρmin = −0.72 e Å−3
370 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir10.09759 (3)0.240147 (11)0.005833 (14)0.03528 (9)
Cl10.20494 (18)0.31961 (8)−0.09466 (10)0.0514 (4)
N10.0132 (5)0.3437 (2)0.0339 (3)0.0410 (13)
N20.1566 (5)0.1294 (3)−0.0176 (3)0.0394 (12)
N30.2997 (5)0.2349 (2)0.0852 (3)0.0382 (11)
O10.4549 (12)0.4379 (6)0.9584 (8)0.245 (5)
C10.0782 (7)0.4038 (3)0.0794 (4)0.0442 (17)
C20.2205 (8)0.4034 (3)0.1040 (4)0.056 (2)
H20.27250.36310.08930.067*
C30.2822 (8)0.4615 (4)0.1490 (5)0.066 (2)
H30.37640.46050.16480.080*
C40.2069 (9)0.5232 (4)0.1724 (5)0.067 (2)
H40.25010.56170.20510.081*
C50.0719 (9)0.5258 (4)0.1467 (4)0.062 (2)
H50.02260.56780.15980.074*
C60.0025 (7)0.4663 (3)0.1002 (4)0.0464 (17)
C7−0.1381 (8)0.4686 (3)0.0732 (4)0.0566 (19)
H7−0.18970.50930.08740.068*
C8−0.1989 (8)0.4119 (3)0.0268 (4)0.0541 (18)
H8−0.29240.41350.00840.065*
C9−0.1209 (7)0.3500 (3)0.0060 (4)0.0432 (16)
C10−0.1786 (7)0.2886 (3)−0.0478 (4)0.0425 (16)
C11−0.0862 (6)0.2318 (3)−0.0616 (3)0.0396 (14)
C12−0.1354 (7)0.1741 (3)−0.1161 (4)0.0469 (17)
H12−0.07580.1362−0.12790.056*
C13−0.2704 (8)0.1716 (4)−0.1532 (4)0.0553 (19)
H13−0.30080.1324−0.18930.066*
C14−0.3594 (8)0.2273 (4)−0.1365 (4)0.065 (2)
H14−0.45070.2250−0.16020.078*
C15−0.3145 (7)0.2865 (4)−0.0848 (4)0.0568 (19)
H15−0.37450.3248−0.07480.068*
C160.2238 (7)0.1046 (3)−0.0807 (4)0.0475 (17)
C170.2191 (8)0.1467 (4)−0.1529 (4)0.064 (2)
H170.16920.1915−0.15910.077*
C180.2872 (10)0.1225 (5)−0.2148 (5)0.086 (3)
H180.28080.1499−0.26360.103*
C190.3657 (10)0.0572 (6)−0.2046 (7)0.098 (3)
H190.41800.0436−0.24490.118*
C200.3677 (10)0.0138 (5)−0.1382 (6)0.093 (3)
H200.4175−0.0311−0.13420.111*
C210.2959 (8)0.0346 (4)−0.0741 (5)0.062 (2)
C220.2865 (9)−0.0103 (4)−0.0068 (6)0.084 (3)
H220.3361−0.05510.00040.100*
C230.2056 (8)0.0103 (4)0.0493 (5)0.070 (2)
H230.1929−0.02260.09160.084*
C240.1409 (7)0.0813 (3)0.0435 (4)0.0439 (16)
C250.0577 (7)0.1094 (3)0.1027 (4)0.0447 (17)
C260.0204 (6)0.1851 (3)0.0943 (4)0.0383 (15)
C27−0.0564 (6)0.2134 (4)0.1515 (4)0.0507 (17)
H27−0.08380.26380.14770.061*
C28−0.0932 (7)0.1694 (5)0.2134 (4)0.060 (2)
H28−0.14190.19080.25190.072*
C29−0.0586 (8)0.0943 (5)0.2190 (5)0.065 (2)
H29−0.08660.06430.26000.078*
C300.0164 (8)0.0637 (4)0.1646 (4)0.061 (2)
H300.04040.01270.16820.073*
C310.4148 (7)0.2258 (3)0.0510 (4)0.0507 (17)
H310.41050.2314−0.00560.061*
C320.5380 (7)0.2085 (4)0.0979 (5)0.062 (2)
H320.61560.20220.07290.075*
C330.5461 (8)0.2007 (4)0.1814 (5)0.068 (2)
H330.62910.18940.21360.082*
C340.4306 (7)0.2098 (4)0.2167 (4)0.0548 (18)
H340.43290.20390.27320.066*
C350.3112 (6)0.2276 (3)0.1669 (4)0.0439 (15)
H350.23350.23520.19150.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.04334 (15)0.03234 (13)0.02941 (13)−0.00102 (12)0.00295 (9)0.00188 (11)
Cl10.0700 (12)0.0461 (9)0.0389 (9)−0.0098 (8)0.0114 (8)0.0051 (7)
N10.055 (4)0.035 (3)0.031 (3)0.003 (2)0.002 (3)0.005 (2)
N20.045 (3)0.037 (3)0.035 (3)0.000 (2)0.004 (2)−0.001 (2)
N30.038 (3)0.039 (3)0.036 (3)0.002 (2)0.002 (2)−0.001 (2)
O10.244 (5)0.245 (5)0.245 (5)0.0004 (10)0.0366 (13)−0.0004 (10)
C10.063 (5)0.034 (3)0.034 (4)−0.001 (3)0.004 (3)0.008 (3)
C20.073 (6)0.038 (4)0.053 (5)−0.002 (3)−0.006 (4)0.001 (3)
C30.082 (6)0.040 (4)0.069 (5)−0.008 (4)−0.016 (4)0.000 (4)
C40.093 (7)0.044 (4)0.059 (5)−0.015 (4)−0.010 (5)−0.011 (4)
C50.106 (7)0.037 (4)0.044 (4)−0.002 (4)0.015 (4)0.001 (3)
C60.068 (5)0.038 (4)0.035 (4)0.001 (3)0.012 (3)0.004 (3)
C70.079 (6)0.038 (4)0.054 (5)0.013 (4)0.015 (4)0.000 (3)
C80.059 (5)0.051 (4)0.052 (4)0.008 (4)0.005 (4)0.004 (3)
C90.058 (5)0.036 (3)0.035 (4)0.004 (3)0.008 (3)0.007 (3)
C100.053 (4)0.038 (3)0.033 (4)0.000 (3)−0.004 (3)0.008 (3)
C110.049 (4)0.038 (3)0.030 (3)0.001 (3)0.000 (3)0.009 (3)
C120.057 (5)0.038 (3)0.043 (4)−0.004 (3)−0.003 (3)0.001 (3)
C130.073 (6)0.048 (4)0.041 (4)−0.011 (4)−0.005 (4)−0.001 (3)
C140.060 (5)0.066 (5)0.061 (5)−0.007 (4)−0.017 (4)0.004 (4)
C150.054 (5)0.058 (4)0.055 (5)0.006 (3)−0.004 (4)0.004 (4)
C160.054 (5)0.042 (4)0.049 (4)−0.004 (3)0.013 (3)−0.015 (3)
C170.095 (6)0.049 (4)0.053 (5)−0.016 (4)0.026 (4)−0.013 (4)
C180.118 (8)0.082 (6)0.068 (6)−0.019 (6)0.049 (6)−0.021 (5)
C190.107 (8)0.101 (8)0.100 (8)−0.004 (6)0.059 (7)−0.029 (6)
C200.111 (8)0.079 (6)0.091 (8)0.023 (6)0.025 (6)−0.034 (6)
C210.067 (5)0.054 (4)0.064 (5)0.005 (4)0.009 (4)−0.017 (4)
C220.105 (8)0.062 (5)0.081 (7)0.036 (5)0.002 (6)−0.007 (5)
C230.092 (7)0.046 (4)0.072 (6)0.014 (4)0.011 (5)0.014 (4)
C240.054 (4)0.032 (3)0.042 (4)−0.002 (3)−0.003 (3)0.002 (3)
C250.052 (4)0.046 (4)0.034 (4)−0.008 (3)−0.001 (3)0.011 (3)
C260.035 (4)0.048 (4)0.030 (3)−0.005 (3)−0.002 (3)0.003 (3)
C270.044 (4)0.067 (4)0.041 (4)0.007 (3)0.005 (3)0.015 (3)
C280.035 (4)0.101 (6)0.043 (4)−0.010 (4)0.008 (3)0.013 (4)
C290.058 (5)0.087 (6)0.050 (5)−0.018 (4)0.007 (4)0.020 (4)
C300.076 (6)0.056 (4)0.048 (5)−0.001 (4)0.003 (4)0.016 (4)
C310.053 (5)0.052 (4)0.047 (4)−0.003 (3)0.007 (3)−0.004 (3)
C320.042 (5)0.075 (5)0.071 (6)0.007 (4)0.011 (4)−0.011 (4)
C330.050 (5)0.087 (6)0.062 (5)0.009 (4)−0.009 (4)−0.002 (4)
C340.058 (5)0.065 (4)0.038 (4)−0.001 (4)−0.003 (4)0.003 (3)
C350.047 (4)0.046 (4)0.038 (4)−0.002 (3)0.005 (3)−0.007 (3)
Geometric parameters (Å, °) top
Ir1—C111.990 (6)C15—H150.9300
Ir1—C261.992 (6)C16—C171.395 (9)
Ir1—N12.090 (5)C16—C211.423 (9)
Ir1—N22.092 (5)C17—C181.368 (10)
Ir1—N32.221 (5)C17—H170.9300
Ir1—Cl12.5182 (16)C18—C191.387 (12)
N1—C91.342 (7)C18—H180.9300
N1—C11.398 (7)C19—C201.331 (12)
N2—C241.340 (7)C19—H190.9300
N2—C161.382 (8)C20—C211.404 (11)
N3—C351.337 (7)C20—H200.9300
N3—C311.351 (8)C21—C221.374 (10)
C1—C61.404 (9)C22—C231.357 (10)
C1—C21.406 (9)C22—H220.9300
C2—C31.357 (8)C23—C241.404 (8)
C2—H20.9300C23—H230.9300
C3—C41.404 (10)C24—C251.452 (9)
C3—H30.9300C25—C261.389 (8)
C4—C51.341 (9)C25—C301.405 (9)
C4—H40.9300C26—C271.386 (8)
C5—C61.415 (9)C27—C281.371 (8)
C5—H50.9300C27—H270.9300
C6—C71.397 (9)C28—C291.370 (9)
C7—C81.345 (9)C28—H280.9300
C7—H70.9300C29—C301.356 (10)
C8—C91.408 (8)C29—H290.9300
C8—H80.9300C30—H300.9300
C9—C101.460 (8)C31—C321.376 (9)
C10—C151.392 (8)C31—H310.9300
C10—C111.398 (8)C32—C331.369 (9)
C11—C121.395 (8)C32—H320.9300
C12—C131.384 (8)C33—C341.366 (9)
C12—H120.9300C33—H330.9300
C13—C141.375 (9)C34—C351.370 (8)
C13—H130.9300C34—H340.9300
C14—C151.378 (9)C35—H350.9300
C14—H140.9300
C11—Ir1—C2687.3 (2)C15—C14—H14119.7
C11—Ir1—N180.0 (2)C14—C15—C10119.4 (7)
C26—Ir1—N193.3 (2)C14—C15—H15120.3
C11—Ir1—N294.9 (2)C10—C15—H15120.3
C26—Ir1—N280.0 (2)N2—C16—C17120.7 (6)
N1—Ir1—N2171.7 (2)N2—C16—C21120.6 (6)
C11—Ir1—N3173.07 (19)C17—C16—C21118.7 (7)
C26—Ir1—N387.8 (2)C18—C17—C16120.6 (8)
N1—Ir1—N3105.16 (18)C18—C17—H17119.7
N2—Ir1—N379.48 (17)C16—C17—H17119.7
C11—Ir1—Cl196.67 (17)C17—C18—C19119.9 (9)
C26—Ir1—Cl1174.02 (16)C17—C18—H18120.0
N1—Ir1—Cl183.02 (14)C19—C18—H18120.0
N2—Ir1—Cl1104.10 (14)C20—C19—C18121.2 (9)
N3—Ir1—Cl188.68 (13)C20—C19—H19119.4
C9—N1—C1118.3 (5)C18—C19—H19119.4
C9—N1—Ir1113.8 (4)C19—C20—C21121.0 (9)
C1—N1—Ir1127.9 (4)C19—C20—H20119.5
C24—N2—C16118.8 (5)C21—C20—H20119.5
C24—N2—Ir1112.8 (4)C22—C21—C20123.7 (8)
C16—N2—Ir1127.7 (4)C22—C21—C16117.9 (7)
C35—N3—C31117.0 (5)C20—C21—C16118.3 (8)
C35—N3—Ir1121.9 (4)C23—C22—C21120.6 (7)
C31—N3—Ir1120.1 (4)C23—C22—H22119.7
N1—C1—C6120.4 (6)C21—C22—H22119.7
N1—C1—C2120.8 (6)C22—C23—C24120.2 (7)
C6—C1—C2118.8 (6)C22—C23—H23119.9
C3—C2—C1120.2 (7)C24—C23—H23119.9
C3—C2—H2119.9N2—C24—C23120.9 (7)
C1—C2—H2119.9N2—C24—C25115.2 (5)
C2—C3—C4121.5 (7)C23—C24—C25123.8 (6)
C2—C3—H3119.3C26—C25—C30121.6 (7)
C4—C3—H3119.3C26—C25—C24115.5 (6)
C5—C4—C3119.0 (6)C30—C25—C24123.0 (6)
C5—C4—H4120.5C27—C26—C25116.3 (6)
C3—C4—H4120.5C27—C26—Ir1128.8 (5)
C4—C5—C6121.7 (7)C25—C26—Ir1114.7 (5)
C4—C5—H5119.1C28—C27—C26122.1 (7)
C6—C5—H5119.1C28—C27—H27118.9
C7—C6—C1119.2 (6)C26—C27—H27118.9
C7—C6—C5122.0 (6)C29—C28—C27120.4 (7)
C1—C6—C5118.8 (7)C29—C28—H28119.8
C8—C7—C6119.9 (6)C27—C28—H28119.8
C8—C7—H7120.1C30—C29—C28119.9 (7)
C6—C7—H7120.1C30—C29—H29120.1
C7—C8—C9120.0 (7)C28—C29—H29120.1
C7—C8—H8120.0C29—C30—C25119.6 (7)
C9—C8—H8120.0C29—C30—H30120.2
N1—C9—C8122.1 (6)C25—C30—H30120.2
N1—C9—C10115.0 (5)N3—C31—C32121.7 (6)
C8—C9—C10122.9 (6)N3—C31—H31119.2
C15—C10—C11121.5 (6)C32—C31—H31119.2
C15—C10—C9123.3 (6)C33—C32—C31119.9 (7)
C11—C10—C9115.2 (5)C33—C32—H32120.1
C12—C11—C10117.0 (6)C31—C32—H32120.1
C12—C11—Ir1127.9 (5)C34—C33—C32119.0 (7)
C10—C11—Ir1114.9 (4)C34—C33—H33120.5
C13—C12—C11121.9 (6)C32—C33—H33120.5
C13—C12—H12119.1C33—C34—C35118.4 (7)
C11—C12—H12119.1C33—C34—H34120.8
C14—C13—C12119.6 (6)C35—C34—H34120.8
C14—C13—H13120.2N3—C35—C34124.0 (6)
C12—C13—H13120.2N3—C35—H35118.0
C13—C14—C15120.6 (7)C34—C35—H35118.0
C13—C14—H14119.7
C11—Ir1—N1—C99.3 (4)Cl1—Ir1—C11—C10−90.5 (4)
C26—Ir1—N1—C9−77.3 (4)C10—C11—C12—C13−1.9 (9)
N3—Ir1—N1—C9−165.9 (4)Ir1—C11—C12—C13173.5 (5)
Cl1—Ir1—N1—C9107.4 (4)C11—C12—C13—C140.1 (10)
C11—Ir1—N1—C1−173.1 (5)C12—C13—C14—C151.7 (10)
C26—Ir1—N1—C1100.3 (5)C13—C14—C15—C10−1.7 (11)
N3—Ir1—N1—C111.7 (5)C11—C10—C15—C14−0.1 (10)
Cl1—Ir1—N1—C1−75.0 (5)C9—C10—C15—C14178.4 (6)
C11—Ir1—N2—C24−98.7 (4)C24—N2—C16—C17167.2 (6)
C26—Ir1—N2—C24−12.3 (4)Ir1—N2—C16—C17−22.6 (9)
N3—Ir1—N2—C2477.2 (4)C24—N2—C16—C21−11.0 (9)
Cl1—Ir1—N2—C24163.2 (4)Ir1—N2—C16—C21159.2 (5)
C11—Ir1—N2—C1690.6 (5)N2—C16—C17—C18179.1 (7)
C26—Ir1—N2—C16176.9 (5)C21—C16—C17—C18−2.6 (11)
N3—Ir1—N2—C16−93.5 (5)C16—C17—C18—C19−2.4 (12)
Cl1—Ir1—N2—C16−7.5 (5)C17—C18—C19—C205.5 (15)
C26—Ir1—N3—C35−24.1 (4)C18—C19—C20—C21−3.4 (16)
N1—Ir1—N3—C3568.6 (4)C19—C20—C21—C22175.4 (9)
N2—Ir1—N3—C35−104.4 (4)C19—C20—C21—C16−1.8 (13)
Cl1—Ir1—N3—C35151.0 (4)N2—C16—C21—C225.6 (10)
C26—Ir1—N3—C31144.4 (5)C17—C16—C21—C22−172.7 (7)
N1—Ir1—N3—C31−122.9 (4)N2—C16—C21—C20−177.0 (7)
N2—Ir1—N3—C3164.1 (4)C17—C16—C21—C204.7 (10)
Cl1—Ir1—N3—C31−40.5 (4)C20—C21—C22—C23−174.1 (8)
C9—N1—C1—C64.5 (8)C16—C21—C22—C233.1 (12)
Ir1—N1—C1—C6−173.0 (4)C21—C22—C23—C24−6.3 (13)
C9—N1—C1—C2−174.3 (6)C16—N2—C24—C237.9 (9)
Ir1—N1—C1—C28.1 (8)Ir1—N2—C24—C23−163.8 (5)
N1—C1—C2—C3−179.2 (6)C16—N2—C24—C25−174.1 (5)
C6—C1—C2—C31.9 (10)Ir1—N2—C24—C2514.2 (6)
C1—C2—C3—C40.0 (11)C22—C23—C24—N20.7 (11)
C2—C3—C4—C5−2.6 (11)C22—C23—C24—C25−177.1 (7)
C3—C4—C5—C63.1 (11)N2—C24—C25—C26−7.9 (8)
N1—C1—C6—C7−1.4 (9)C23—C24—C25—C26170.0 (6)
C2—C1—C6—C7177.5 (6)N2—C24—C25—C30171.9 (6)
N1—C1—C6—C5179.7 (6)C23—C24—C25—C30−10.2 (10)
C2—C1—C6—C5−1.4 (9)C30—C25—C26—C271.7 (9)
C4—C5—C6—C7−180.0 (7)C24—C25—C26—C27−178.5 (5)
C4—C5—C6—C1−1.1 (10)C30—C25—C26—Ir1177.2 (5)
C1—C6—C7—C8−1.1 (10)C24—C25—C26—Ir1−3.0 (7)
C5—C6—C7—C8177.7 (6)C11—Ir1—C26—C27−81.6 (6)
C6—C7—C8—C90.6 (10)N1—Ir1—C26—C27−1.8 (6)
C1—N1—C9—C8−5.2 (9)N2—Ir1—C26—C27−177.1 (6)
Ir1—N1—C9—C8172.7 (5)N3—Ir1—C26—C27103.2 (5)
C1—N1—C9—C10174.1 (5)N1—Ir1—C26—C25−176.8 (4)
Ir1—N1—C9—C10−8.0 (6)N2—Ir1—C26—C258.0 (4)
C7—C8—C9—N12.7 (10)N3—Ir1—C26—C25−71.7 (4)
C7—C8—C9—C10−176.5 (6)C25—C26—C27—C280.4 (9)
N1—C9—C10—C15−177.8 (6)Ir1—C26—C27—C28−174.5 (5)
C8—C9—C10—C151.5 (10)C26—C27—C28—C29−2.3 (10)
N1—C9—C10—C110.8 (8)C27—C28—C29—C302.2 (11)
C8—C9—C10—C11−179.9 (6)C28—C29—C30—C25−0.2 (11)
C15—C10—C11—C121.9 (9)C26—C25—C30—C29−1.8 (10)
C9—C10—C11—C12−176.7 (5)C24—C25—C30—C29178.5 (6)
C15—C10—C11—Ir1−174.1 (5)C35—N3—C31—C321.1 (9)
C9—C10—C11—Ir17.3 (7)Ir1—N3—C31—C32−167.9 (5)
C26—Ir1—C11—C12−90.5 (6)N3—C31—C32—C33−0.5 (10)
N1—Ir1—C11—C12175.7 (6)C31—C32—C33—C340.5 (11)
N2—Ir1—C11—C12−10.8 (6)C32—C33—C34—C35−1.1 (11)
Cl1—Ir1—C11—C1294.1 (5)C31—N3—C35—C34−1.8 (9)
C26—Ir1—C11—C1085.0 (5)Ir1—N3—C35—C34167.0 (5)
N1—Ir1—C11—C10−8.8 (4)C33—C34—C35—N31.9 (10)
N2—Ir1—C11—C10164.7 (4)
Table 1
Selected geometric parameters (Å, °) top
Ir1—C111.990 (6)Ir1—N22.092 (5)
Ir1—C261.992 (6)Ir1—N32.221 (5)
Ir1—N12.090 (5)Ir1—Cl12.5182 (16)
C11—Ir1—C2687.3 (2)N1—Ir1—N3105.16 (18)
C11—Ir1—N180.0 (2)N2—Ir1—N379.48 (17)
C26—Ir1—N193.3 (2)C11—Ir1—Cl196.67 (17)
C11—Ir1—N294.9 (2)C26—Ir1—Cl1174.02 (16)
C26—Ir1—N280.0 (2)N1—Ir1—Cl183.02 (14)
N1—Ir1—N2171.7 (2)N2—Ir1—Cl1104.10 (14)
C11—Ir1—N3173.07 (19)N3—Ir1—Cl188.68 (13)
C26—Ir1—N387.8 (2)
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 20571033) and by the Program for New Century Excellent Talents in Universities (NCET-06–0483).

references
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