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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1205.
Published online 2008 August 30. doi:  10.1107/S1600536808025452
PMCID: PMC2960588

Chlorido(pyridine-κN)bis­[2-(quinolin-2-yl)phenyl-κ2 C 1,N]iridium(III) mono­hydrate

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-m1205-scheme1.jpg

Experimental

Crystal data

  • [Ir(C15H10N)2Cl(C5H5N)]·H2O
  • M r = 733.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1205-efi1.jpg
  • a = 9.8949 (15) Å
  • b = 17.653 (3) Å
  • c = 16.424 (3) Å
  • β = 98.545 (3)°
  • V = 2837.0 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.83 mm−1
  • T = 273 (2) K
  • 0.16 × 0.12 × 0.08 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.511, T max = 0.684
  • 14857 measured reflections
  • 5027 independent reflections
  • 3702 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.075
  • S = 1.02
  • 5027 reflections
  • 370 parameters
  • 9 restraints
  • H-atom parameters constrained
  • Δρmax = 0.78 e Å−3
  • Δρmin = −0.72 e Å−3

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025452/hy2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025452/hy2145Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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)].

Experimental

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

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.

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

Crystal data

[Ir(C15H10N)2Cl(C5H5N)]·H2OF000 = 1440
Mr = 733.25Dx = 1.717 Mg m3
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 mm1
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

Bruker SMART APEXII CCD area-detector diffractometer5027 independent reflections
Radiation source: fine-focus sealed tube3702 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
T = 273(2) Kθmax = 25.1º
[var phi] 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

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 Å3
370 parametersΔρmin = −0.72 e Å3
9 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2145).

References

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