metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[2-(Phenyl­diazen­yl)pyrrolato]bis­(2-pyridylphen­yl)iridium(III)

aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China
*Correspondence e-mail: lulong@mail.sioc.ac.cn

(Received 23 January 2008; accepted 14 February 2008; online 20 February 2008)

In the title compound, [Ir(C10H8N3)(C11H8N)2], the Ir center is octa­hedrally coordinated by the three chelating ligands, with two cyclo­metalated 2-pyridylphenyl ligands [Ir—N = 2.049 (5) and 2.030 (5) Å; Ir—C = 2.016 (6) and 2.012 (6) Å] and a bidentate 2-(phenyl­diazen­yl)pyrrolate ligand [Ir—N = 2.204 (5) and 2.079 (5) Å]. The Ir—N(diazen­yl) bond is longer than the Ir—N(pyrrolate) bond. The structure is stabilized by aromatic ππ stacking, the shortest parallel distance between ring centroids being 3.426 (8) Å..

Related literature

For phospho­rescence properties of cyclo­metalated iridium complexes, see: Baldo et al. (2000[Baldo, M. A., Thompson, M. E. & Forrest, S. R. (2000). Nature (London), 403, 750-753.]); Pomestcheako et al. (2003[Pomestcheako, I. E., Luman, C. R., Hissler, M. E., Ziessel, R. & Castellano, F. N. (2003). Inorg. Chem. 42, 1394-1396.]); Chen et al. (2003[Chen, X., Liao, J. L., Liang, Y. M., Ahmed, M. O., Tseng, H. E. & Chen, S. A. (2003). J. Am. Chem. Soc. 125, 636-637.]). For the preparation of iridium complexes, see: Lamansky et al. (2001[Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Lee, H.-E., Adachi, C., Burrows, P. E., Forrest, S. R. & Thompson, M. E. (2001). J. Am. Chem. Soc. 123, 4304-4312.]); Davies et al. (2006[Davies, D. L., Donald, S. M. A., Al-Duaij, O., Fawcett, J., Little, C. & Macgregor, S. A. (2006). Organometallics, 25, 5976-5978.]). For reference structural data, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Chin et al. (1995[Chin, K.-F., Cheung, K.-K., Yip, H.-K., Mak, T. C. W. & Che, C. M. (1995). J. Chem. Soc. Dalton Trans. pp. 657-665.]).

[Scheme 1]

Experimental

Crystal data
  • [Ir(C10H8N3)(C11H8N)2]

  • Mr = 670.76

  • Monoclinic, C 2/c

  • a = 17.5606 (14) Å

  • b = 11.0213 (9) Å

  • c = 26.673 (2) Å

  • β = 93.282 (1)°

  • V = 5153.9 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 5.21 mm−1

  • T = 293 (2) K

  • 0.22 × 0.14 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.754, Tmax = 1.000 (expected range = 0.549–0.728)

  • 14220 measured reflections

  • 5327 independent reflections

  • 4228 reflections with I > 2σ(I)

  • Rint = 0.140

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.107

  • S = 0.97

  • 5327 reflections

  • 343 parameters

  • H-atom parameters constrained

  • Δρmax = 4.15 e Å−3

  • Δρmin = −2.38 e Å−3

Table 1
Selected geometric parameters (Å, °)

Ir—C22 2.012 (6)
Ir—C21 2.016 (6)
Ir—N5 2.030 (5)
Ir—N4 2.049 (5)
Ir—N3 2.079 (5)
Ir—N1 2.204 (5)
C22—Ir—C21 85.1 (2)
C22—Ir—N5 79.7 (2)
C21—Ir—N5 96.0 (2)
C22—Ir—N4 94.9 (2)
C21—Ir—N4 79.4 (2)
N5—Ir—N4 173.2 (2)
C22—Ir—N3 96.8 (2)
C21—Ir—N3 174.5 (2)
N5—Ir—N3 89.5 (2)
N4—Ir—N3 95.3 (2)
C22—Ir—N1 170.6 (2)
C21—Ir—N1 104.0 (2)
N5—Ir—N1 97.2 (2)
N4—Ir—N1 88.74 (19)
N3—Ir—N1 74.2 (2)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART (Version 5.628) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART (Version 5.628) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Transition-metal (Ir) complexes that display intense phosphorescence from metal-to-ligand charge transfer (MLCT) excited states have been widely investigated (Baldo et al., 2000; Pomestcheako et al., 2003; Chen et al., 2003). These Ir complexes with long excited-stated lifetimes and high luminescent efficiencies can be used in a variety of photonic applications such as photocatalysis and organic light-emitting diodes (Chin et al., 1995). We report here the molecular structure of (I), (Fig. 1).

In the title compound (I), all the bond lengths and angles fall within normal ranges. Moreover, the Ir—C bond lengths are found to be shorter than the Ir—N bond lengths. In comparison with bis(2-pyridylphenyl)(acetylacetonate) iridium (Ir(ppy)2(acac)) which was reported in the literature (Lamansky et al., 2001), this title complex displays longer Ir—N bond with the same cis-C, C trans-N, N chelate disposition. The dihedral angles between rings in the two ppy ligands are 5.2 (4)° [between rings N4/C11–C15 and C16–C21] and 5.5 (6)° [(between rings N5/C28–C32 and C22–C27].

Related literature top

For phosphorescence properties of cyclometalated iridium complexes, see: Baldo et al. (2000); Pomestcheako et al. (2003); Chen et al. (2003). For the preparation of iridium complexes, see: Lamansky et al. (2001); Davies et al. (2006). For reference structural data, see: Allen (2002); Allen et al. (1987); Chin et al. (1995).

Experimental top

To a stirring solution of 2-(2-phenylazo)-1H-pyrrole (60 mg,0.35 mmol) in dichloromethane (15 ml), sodium acetate (23 mg, 0.28 mmol) and [IrCl(ppy)2]2 (150 mg, 0.14 mmol) were added. The mixture was allowed to stir under an argon atmosphere at room temperature for 12 h. Then, the mixture was diluted with water and extracted thrice with 10 ml of dichloromethane. The organic extracts were combined and dried over anhydrous magnesium sulfate. After the solvent was removed in vacuo, the resulting residue was subjected to flash chromatography on silica gel using dichloromethane to afford the title compound (yield 75%). Red crystals of (I) suitable for X-ray structure analysis were grown from the mixture of dichloromethane and petroleum ether (v/v, 1:6).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å and Uiso = 1.2Ueq (C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Version 5.0; Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Version 5.0; Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[2-(Phenyldiazenyl)pyrrolato]bis(2-pyridylphenyl)iridium(III) top
Crystal data top
[Ir(C10H8N3)(C11H8N)2]F(000) = 2624
Mr = 670.76Dx = 1.729 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4482 reflections
a = 17.5606 (14) Åθ = 4.6–52.7°
b = 11.0213 (9) ŵ = 5.21 mm1
c = 26.673 (2) ÅT = 293 K
β = 93.282 (1)°Prism, red
V = 5153.9 (7) Å30.22 × 0.14 × 0.06 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5327 independent reflections
Radiation source: fine-focus sealed tube4228 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.140
ϕ and ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 2122
Tmin = 0.754, Tmax = 1.000k = 136
14220 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0284P)2]
where P = (Fo2 + 2Fc2)/3
5327 reflections(Δ/σ)max = 0.002
343 parametersΔρmax = 4.15 e Å3
0 restraintsΔρmin = 2.38 e Å3
Crystal data top
[Ir(C10H8N3)(C11H8N)2]V = 5153.9 (7) Å3
Mr = 670.76Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.5606 (14) ŵ = 5.21 mm1
b = 11.0213 (9) ÅT = 293 K
c = 26.673 (2) Å0.22 × 0.14 × 0.06 mm
β = 93.282 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5327 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
4228 reflections with I > 2σ(I)
Tmin = 0.754, Tmax = 1.000Rint = 0.140
14220 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 0.97Δρmax = 4.15 e Å3
5327 reflectionsΔρmin = 2.38 e Å3
343 parameters
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
Ir0.118518 (14)0.76861 (2)0.384282 (9)0.02997 (11)
N10.0029 (3)0.6954 (5)0.3915 (2)0.0339 (12)
N20.0012 (3)0.5952 (5)0.4165 (2)0.0366 (13)
N30.1331 (3)0.6047 (5)0.42223 (18)0.0332 (12)
N40.1050 (3)0.8704 (5)0.44743 (17)0.0312 (12)
N50.1403 (3)0.6834 (5)0.31918 (18)0.0358 (12)
C10.0655 (4)0.5480 (6)0.4316 (3)0.0392 (16)
C20.0800 (4)0.4391 (6)0.4596 (3)0.0487 (19)
H20.04420.38540.47120.058*
C30.1589 (5)0.4304 (7)0.4660 (3)0.052 (2)
H30.18660.36890.48250.063*
C40.1888 (4)0.5342 (7)0.4422 (3)0.0485 (19)
H40.24050.55090.44080.058*
C50.0713 (4)0.7448 (6)0.3781 (3)0.0353 (16)
C60.1359 (4)0.7030 (7)0.3983 (3)0.0497 (19)
H60.13270.64020.42160.060*
C70.2066 (5)0.7536 (8)0.3844 (4)0.065 (3)
H70.25030.72270.39780.079*
C80.2124 (4)0.8471 (8)0.3516 (3)0.060 (2)
H80.25970.88200.34340.072*
C90.1483 (4)0.8905 (8)0.3305 (3)0.059 (2)
H90.15230.95490.30800.071*
C100.0775 (4)0.8385 (7)0.3426 (2)0.0458 (18)
H100.03450.86580.32730.055*
C110.1086 (4)0.8273 (7)0.4944 (2)0.0412 (16)
H110.11470.74420.49920.049*
C120.1037 (4)0.8995 (7)0.5356 (2)0.0483 (19)
H120.10460.86550.56760.058*
C130.0976 (4)1.0214 (8)0.5296 (3)0.054 (2)
H130.09581.07240.55730.065*
C140.0939 (4)1.0684 (7)0.4814 (3)0.0498 (19)
H140.08871.15170.47660.060*
C150.0978 (4)0.9916 (6)0.4402 (2)0.0360 (15)
C160.0931 (4)1.0276 (6)0.3870 (2)0.0372 (15)
C170.0809 (4)1.1486 (7)0.3711 (3)0.054 (2)
H170.07701.21020.39460.065*
C180.0749 (5)1.1744 (8)0.3212 (4)0.065 (2)
H180.06611.25360.31030.078*
C190.0820 (4)1.0820 (8)0.2866 (3)0.055 (2)
H190.07851.09970.25250.066*
C200.0940 (4)0.9656 (7)0.3021 (3)0.0435 (17)
H200.09800.90500.27810.052*
C210.1005 (3)0.9341 (6)0.3536 (2)0.0328 (14)
C220.2299 (4)0.8077 (6)0.3802 (2)0.0330 (14)
C230.2771 (4)0.8709 (6)0.4162 (2)0.0388 (16)
H230.25680.90120.44520.047*
C240.3538 (4)0.8875 (6)0.4080 (3)0.0417 (17)
H240.38390.93100.43150.050*
C250.3867 (4)0.8421 (7)0.3667 (3)0.0475 (18)
H250.43840.85340.36250.057*
C260.3418 (4)0.7792 (6)0.3312 (3)0.0440 (18)
H260.36300.74920.30250.053*
C270.2634 (4)0.7606 (6)0.3388 (3)0.0361 (16)
C280.2131 (4)0.6904 (6)0.3034 (2)0.0350 (15)
C290.2321 (4)0.6370 (7)0.2595 (3)0.0487 (18)
H290.28060.64850.24810.058*
C300.1803 (5)0.5667 (7)0.2323 (3)0.056 (2)
H300.19380.52940.20290.067*
C310.1093 (4)0.5521 (8)0.2487 (3)0.055 (2)
H310.07390.50270.23130.067*
C320.0902 (4)0.6121 (7)0.2918 (3)0.051 (2)
H320.04100.60320.30260.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir0.02407 (15)0.03860 (17)0.02744 (14)0.00330 (11)0.00326 (9)0.00461 (11)
N10.027 (3)0.035 (3)0.040 (3)0.008 (3)0.004 (2)0.004 (3)
N20.031 (3)0.035 (3)0.044 (3)0.006 (3)0.010 (2)0.009 (3)
N30.039 (3)0.034 (3)0.027 (3)0.001 (3)0.006 (2)0.007 (2)
N40.021 (3)0.048 (3)0.025 (3)0.001 (3)0.006 (2)0.006 (2)
N50.029 (3)0.052 (3)0.027 (3)0.009 (3)0.002 (2)0.002 (3)
C10.028 (4)0.044 (4)0.046 (4)0.001 (3)0.006 (3)0.009 (3)
C20.046 (5)0.041 (4)0.060 (5)0.003 (4)0.014 (4)0.007 (4)
C30.053 (5)0.047 (4)0.057 (5)0.010 (4)0.001 (4)0.004 (4)
C40.030 (4)0.056 (5)0.060 (5)0.008 (4)0.004 (3)0.005 (4)
C50.024 (4)0.044 (4)0.038 (4)0.001 (3)0.006 (3)0.009 (3)
C60.039 (4)0.043 (4)0.068 (5)0.000 (4)0.016 (4)0.005 (4)
C70.027 (4)0.079 (6)0.091 (7)0.004 (4)0.012 (4)0.001 (5)
C80.038 (4)0.080 (6)0.062 (5)0.014 (5)0.003 (4)0.005 (5)
C90.040 (4)0.088 (6)0.049 (5)0.007 (5)0.001 (4)0.017 (4)
C100.029 (4)0.068 (5)0.041 (4)0.002 (4)0.006 (3)0.001 (4)
C110.036 (4)0.051 (4)0.037 (4)0.001 (4)0.003 (3)0.001 (3)
C120.044 (4)0.074 (6)0.027 (4)0.002 (4)0.006 (3)0.011 (4)
C130.047 (5)0.077 (6)0.038 (4)0.000 (4)0.000 (3)0.023 (4)
C140.047 (5)0.052 (5)0.050 (4)0.007 (4)0.001 (4)0.011 (4)
C150.024 (3)0.046 (4)0.039 (4)0.002 (3)0.004 (3)0.007 (3)
C160.028 (3)0.045 (4)0.039 (4)0.002 (3)0.003 (3)0.004 (3)
C170.048 (5)0.049 (5)0.067 (5)0.003 (4)0.007 (4)0.005 (4)
C180.047 (5)0.058 (5)0.091 (7)0.005 (5)0.004 (5)0.032 (5)
C190.037 (4)0.077 (6)0.052 (5)0.001 (4)0.007 (3)0.021 (4)
C200.035 (4)0.056 (5)0.039 (4)0.006 (4)0.005 (3)0.005 (3)
C210.026 (3)0.029 (3)0.045 (4)0.002 (3)0.013 (3)0.003 (3)
C220.030 (4)0.036 (3)0.033 (3)0.004 (3)0.001 (3)0.007 (3)
C230.030 (4)0.047 (4)0.040 (4)0.004 (3)0.001 (3)0.008 (3)
C240.030 (4)0.046 (4)0.048 (4)0.005 (3)0.008 (3)0.004 (3)
C250.021 (3)0.062 (5)0.059 (5)0.003 (4)0.001 (3)0.003 (4)
C260.032 (4)0.048 (4)0.053 (4)0.001 (3)0.016 (3)0.004 (3)
C270.033 (4)0.035 (4)0.041 (4)0.002 (3)0.006 (3)0.003 (3)
C280.029 (3)0.046 (4)0.031 (3)0.004 (3)0.006 (3)0.002 (3)
C290.046 (4)0.058 (5)0.044 (4)0.002 (4)0.015 (3)0.005 (4)
C300.059 (5)0.068 (5)0.040 (4)0.018 (5)0.002 (4)0.020 (4)
C310.045 (5)0.082 (6)0.038 (4)0.007 (4)0.010 (3)0.029 (4)
C320.037 (4)0.063 (5)0.054 (5)0.003 (4)0.004 (3)0.025 (4)
Geometric parameters (Å, º) top
Ir—C222.012 (6)C12—H120.9300
Ir—C212.016 (6)C13—C141.383 (10)
Ir—N52.030 (5)C13—H130.9300
Ir—N42.049 (5)C14—C151.394 (9)
Ir—N32.079 (5)C14—H140.9300
Ir—N12.204 (5)C15—C161.469 (9)
N1—N21.293 (7)C16—C211.374 (9)
N1—C51.438 (9)C16—C171.411 (10)
N2—C11.324 (8)C17—C181.361 (11)
N3—C41.336 (8)C17—H170.9300
N3—C11.377 (8)C18—C191.384 (12)
N4—C111.339 (8)C18—H180.9300
N4—C151.355 (9)C19—C201.360 (10)
N5—C321.362 (8)C19—H190.9300
N5—C281.370 (8)C20—C211.417 (9)
C1—C21.429 (9)C20—H200.9300
C2—C31.389 (11)C22—C271.383 (10)
C2—H20.9300C22—C231.415 (8)
C3—C41.423 (10)C23—C241.389 (9)
C3—H30.9300C23—H230.9300
C4—H40.9300C24—C251.368 (9)
C5—C61.364 (10)C24—H240.9300
C5—C101.400 (10)C25—C261.382 (10)
C6—C71.392 (11)C25—H250.9300
C6—H60.9300C26—C271.418 (11)
C7—C81.352 (12)C26—H260.9300
C7—H70.9300C27—C281.474 (9)
C8—C91.373 (11)C28—C291.369 (9)
C8—H80.9300C29—C301.371 (10)
C9—C101.390 (9)C29—H290.9300
C9—H90.9300C30—C311.355 (11)
C10—H100.9300C30—H300.9300
C11—C121.364 (9)C31—C321.384 (9)
C11—H110.9300C31—H310.9300
C12—C131.357 (11)C32—H320.9300
C22—Ir—C2185.1 (2)C13—C12—H12120.3
C22—Ir—N579.7 (2)C11—C12—H12120.3
C21—Ir—N596.0 (2)C12—C13—C14118.7 (7)
C22—Ir—N494.9 (2)C12—C13—H13120.6
C21—Ir—N479.4 (2)C14—C13—H13120.6
N5—Ir—N4173.2 (2)C13—C14—C15120.3 (7)
C22—Ir—N396.8 (2)C13—C14—H14119.9
C21—Ir—N3174.5 (2)C15—C14—H14119.9
N5—Ir—N389.5 (2)N4—C15—C14119.6 (6)
N4—Ir—N395.3 (2)N4—C15—C16113.8 (6)
C22—Ir—N1170.6 (2)C14—C15—C16126.5 (7)
C21—Ir—N1104.0 (2)C21—C16—C17122.1 (6)
N5—Ir—N197.2 (2)C21—C16—C15114.9 (6)
N4—Ir—N188.74 (19)C17—C16—C15123.0 (7)
N3—Ir—N174.2 (2)C18—C17—C16119.6 (8)
N2—N1—C5112.0 (5)C18—C17—H17120.2
N2—N1—Ir115.9 (4)C16—C17—H17120.2
C5—N1—Ir131.7 (4)C17—C18—C19119.6 (8)
N1—N2—C1114.7 (6)C17—C18—H18120.2
C4—N3—C1106.4 (6)C19—C18—H18120.2
C4—N3—Ir140.1 (5)C20—C19—C18120.7 (7)
C1—N3—Ir113.5 (4)C20—C19—H19119.6
C11—N4—C15118.9 (6)C18—C19—H19119.6
C11—N4—Ir125.1 (5)C19—C20—C21121.8 (7)
C15—N4—Ir115.9 (4)C19—C20—H20119.1
C32—N5—C28117.0 (6)C21—C20—H20119.1
C32—N5—Ir125.3 (5)C16—C21—C20116.1 (6)
C28—N5—Ir117.5 (4)C16—C21—Ir115.7 (5)
N2—C1—N3121.5 (6)C20—C21—Ir128.1 (5)
N2—C1—C2128.1 (7)C27—C22—C23117.9 (6)
N3—C1—C2110.3 (6)C27—C22—Ir115.0 (5)
C3—C2—C1105.6 (7)C23—C22—Ir127.0 (5)
C3—C2—H2127.2C24—C23—C22119.6 (6)
C1—C2—H2127.2C24—C23—H23120.2
C2—C3—C4106.3 (6)C22—C23—H23120.2
C2—C3—H3126.9C25—C24—C23122.4 (6)
C4—C3—H3126.9C25—C24—H24118.8
N3—C4—C3111.4 (6)C23—C24—H24118.8
N3—C4—H4124.3C24—C25—C26119.0 (6)
C3—C4—H4124.3C24—C25—H25120.5
C6—C5—C10118.8 (7)C26—C25—H25120.5
C6—C5—N1122.3 (6)C25—C26—C27119.6 (7)
C10—C5—N1118.8 (6)C25—C26—H26120.2
C5—C6—C7120.5 (8)C27—C26—H26120.2
C5—C6—H6119.8C22—C27—C26121.4 (6)
C7—C6—H6119.8C22—C27—C28116.2 (6)
C8—C7—C6120.8 (9)C26—C27—C28122.4 (7)
C8—C7—H7119.6N5—C28—C29121.0 (6)
C6—C7—H7119.6N5—C28—C27111.6 (6)
C7—C8—C9119.8 (8)C29—C28—C27127.3 (7)
C7—C8—H8120.1C28—C29—C30120.6 (7)
C9—C8—H8120.1C28—C29—H29119.7
C8—C9—C10120.3 (8)C30—C29—H29119.7
C8—C9—H9119.9C31—C30—C29119.5 (7)
C10—C9—H9119.9C31—C30—H30120.3
C9—C10—C5119.7 (7)C29—C30—H30120.3
C9—C10—H10120.1C30—C31—C32118.9 (7)
C5—C10—H10120.1C30—C31—H31120.6
N4—C11—C12123.1 (7)C32—C31—H31120.6
N4—C11—H11118.5N5—C32—C31122.7 (7)
C12—C11—H11118.5N5—C32—H32118.6
C13—C12—C11119.4 (7)C31—C32—H32118.6
C21—Ir—N1—N2171.3 (4)C11—N4—C15—C140.4 (9)
N5—Ir—N1—N290.7 (4)Ir—N4—C15—C14175.4 (5)
N4—Ir—N1—N292.6 (4)C11—N4—C15—C16178.9 (6)
N3—Ir—N1—N23.3 (4)Ir—N4—C15—C166.0 (7)
C21—Ir—N1—C51.0 (6)C13—C14—C15—N40.2 (11)
N5—Ir—N1—C597.1 (6)C13—C14—C15—C16178.6 (7)
N4—Ir—N1—C579.7 (6)N4—C15—C16—C213.1 (9)
N3—Ir—N1—C5175.5 (6)C14—C15—C16—C21178.4 (7)
C5—N1—N2—C1177.5 (5)N4—C15—C16—C17176.2 (6)
Ir—N1—N2—C13.7 (7)C14—C15—C16—C172.3 (12)
C22—Ir—N3—C42.4 (7)C21—C16—C17—C181.2 (12)
N5—Ir—N3—C482.0 (7)C15—C16—C17—C18178.1 (7)
N4—Ir—N3—C493.2 (7)C16—C17—C18—C191.0 (12)
N1—Ir—N3—C4179.6 (7)C17—C18—C19—C200.8 (12)
C22—Ir—N3—C1179.4 (4)C18—C19—C20—C210.7 (12)
N5—Ir—N3—C199.8 (4)C17—C16—C21—C201.0 (10)
N4—Ir—N3—C185.0 (4)C15—C16—C21—C20178.3 (6)
N1—Ir—N3—C12.2 (4)C17—C16—C21—Ir179.4 (6)
C22—Ir—N4—C1195.9 (5)C15—C16—C21—Ir1.3 (8)
C21—Ir—N4—C11180.0 (5)C19—C20—C21—C160.8 (10)
N3—Ir—N4—C111.5 (5)C19—C20—C21—Ir179.7 (5)
N1—Ir—N4—C1175.5 (5)C22—Ir—C21—C1692.5 (5)
C22—Ir—N4—C1578.9 (5)N5—Ir—C21—C16171.6 (5)
C21—Ir—N4—C155.2 (4)N4—Ir—C21—C163.4 (5)
N3—Ir—N4—C15176.2 (4)N1—Ir—C21—C1689.4 (5)
N1—Ir—N4—C15109.8 (5)C22—Ir—C21—C2088.0 (6)
C22—Ir—N5—C32174.5 (6)N5—Ir—C21—C208.9 (6)
C21—Ir—N5—C32101.6 (6)N4—Ir—C21—C20176.1 (6)
N3—Ir—N5—C3277.4 (6)N1—Ir—C21—C2090.1 (6)
N1—Ir—N5—C323.4 (6)C21—Ir—C22—C2797.3 (5)
C22—Ir—N5—C280.1 (5)N5—Ir—C22—C270.3 (5)
C21—Ir—N5—C2883.8 (5)N4—Ir—C22—C27176.2 (5)
N3—Ir—N5—C2897.2 (5)N3—Ir—C22—C2787.9 (5)
N1—Ir—N5—C28171.2 (5)C21—Ir—C22—C2386.6 (6)
N1—N2—C1—N31.8 (9)N5—Ir—C22—C23176.4 (6)
N1—N2—C1—C2179.9 (6)N4—Ir—C22—C237.8 (6)
C4—N3—C1—N2179.9 (6)N3—Ir—C22—C2388.2 (6)
Ir—N3—C1—N21.1 (8)C27—C22—C23—C242.4 (10)
C4—N3—C1—C21.4 (7)Ir—C22—C23—C24178.3 (5)
Ir—N3—C1—C2177.4 (4)C22—C23—C24—C251.7 (11)
N2—C1—C2—C3179.7 (7)C23—C24—C25—C261.1 (11)
N3—C1—C2—C31.3 (8)C24—C25—C26—C271.4 (11)
C1—C2—C3—C40.6 (8)C23—C22—C27—C262.7 (10)
C1—N3—C4—C31.0 (8)Ir—C22—C27—C26179.1 (5)
Ir—N3—C4—C3177.3 (5)C23—C22—C27—C28177.1 (6)
C2—C3—C4—N30.2 (8)Ir—C22—C27—C280.7 (8)
N2—N1—C5—C612.3 (9)C25—C26—C27—C222.2 (11)
Ir—N1—C5—C6160.2 (5)C25—C26—C27—C28177.6 (7)
N2—N1—C5—C10167.2 (6)C32—N5—C28—C296.0 (10)
Ir—N1—C5—C1020.3 (9)Ir—N5—C28—C29179.0 (5)
C10—C5—C6—C70.7 (12)C32—N5—C28—C27174.5 (6)
N1—C5—C6—C7179.8 (7)Ir—N5—C28—C270.5 (8)
C5—C6—C7—C81.8 (14)C22—C27—C28—N50.8 (9)
C6—C7—C8—C92.1 (14)C26—C27—C28—N5179.0 (6)
C7—C8—C9—C100.1 (13)C22—C27—C28—C29178.7 (7)
C8—C9—C10—C52.6 (12)C26—C27—C28—C291.5 (11)
C6—C5—C10—C92.8 (11)N5—C28—C29—C305.4 (11)
N1—C5—C10—C9177.7 (6)C27—C28—C29—C30175.2 (7)
C15—N4—C11—C121.5 (10)C28—C29—C30—C311.2 (12)
Ir—N4—C11—C12176.0 (5)C29—C30—C31—C322.1 (13)
N4—C11—C12—C132.4 (11)C28—N5—C32—C312.6 (11)
C11—C12—C13—C142.1 (11)Ir—N5—C32—C31177.2 (6)
C12—C13—C14—C151.1 (12)C30—C31—C32—N51.4 (13)

Experimental details

Crystal data
Chemical formula[Ir(C10H8N3)(C11H8N)2]
Mr670.76
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)17.5606 (14), 11.0213 (9), 26.673 (2)
β (°) 93.282 (1)
V3)5153.9 (7)
Z8
Radiation typeMo Kα
µ (mm1)5.21
Crystal size (mm)0.22 × 0.14 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.754, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14220, 5327, 4228
Rint0.140
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.107, 0.97
No. of reflections5327
No. of parameters343
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)4.15, 2.38

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Version 5.0; Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Ir—C222.012 (6)Ir—N42.049 (5)
Ir—C212.016 (6)Ir—N32.079 (5)
Ir—N52.030 (5)Ir—N12.204 (5)
C22—Ir—C2185.1 (2)N5—Ir—N389.5 (2)
C22—Ir—N579.7 (2)N4—Ir—N395.3 (2)
C21—Ir—N596.0 (2)C22—Ir—N1170.6 (2)
C22—Ir—N494.9 (2)C21—Ir—N1104.0 (2)
C21—Ir—N479.4 (2)N5—Ir—N197.2 (2)
N5—Ir—N4173.2 (2)N4—Ir—N188.74 (19)
C22—Ir—N396.8 (2)N3—Ir—N174.2 (2)
C21—Ir—N3174.5 (2)
 

Acknowledgements

The authors thank Professor J. S. for fruitful advice.

References

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