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

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ISSN: 2056-9890

(Acetyl­acetonato-κ2O,O′)bis­­[2-(naphth[1,2-d][1,3]oxazol-2-yl)phenyl-κ2C1,N]iridium(III)

aDepartment of Environment Engineering and Chemistry, Luoyang Institute of Science and Technology, 471023 Luoyang, People's Republic of China
*Correspondence e-mail: yinguojie000000@yahoo.com.cn

(Received 13 August 2011; accepted 20 August 2011; online 27 August 2011)

In the crystal structure of the title compound, [Ir(C17H10NO)2(C5H7O2)], the IrIII atom is O,O′-chelated by the acetyl­acetonate group and C,N-chelated by the 2-aryl­naphth[1,2-d]oxazole groups. The six-coordinate metal atom displays a distorted octa­hedral geometry.

Related literature

For the synthesis and reactions of some 2-aryl­naphth[1,2-d]oxazole derivatives, see: Abbady (1979[Abbady, M. A. (1979). Indian J. Chem. Sect. B, 17, 450-453.]). For the synthesis and characterization of phospho­rescent cyclo­metalated iridium complexes, see: Lamansky et al. (2001[Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001). Inorg. Chem. 40, 1704-1711.]).

[Scheme 1]

Experimental

Crystal data
  • [Ir(C17H10NO)2(C5H7O2)]

  • Mr = 779.83

  • Monoclinic, C 2/c

  • a = 16.640 (3) Å

  • b = 17.384 (3) Å

  • c = 21.461 (4) Å

  • β = 95.026 (2)°

  • V = 6184.3 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 4.36 mm−1

  • T = 273 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.354, Tmax = 0.476

  • 28178 measured reflections

  • 7558 independent reflections

  • 6091 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.051

  • S = 1.01

  • 7558 reflections

  • 415 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Selected bond lengths (Å)

Ir1—C18 1.995 (3)
Ir1—C1 1.999 (3)
Ir1—N2 2.067 (2)
Ir1—N1 2.091 (2)
Ir1—O4 2.1407 (18)
Ir1—O3 2.1414 (19)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.

Supporting information


Comment top

According to the study of Lamansky's group in 2001 (Lamansky et al., 2001), the luminous wavelength of complexes would change as the the conjugated system of (C—N) changed. Therefore, the arylnaphthoxazoles ligand was choosed to regulate luminous wavelength of phosphorescent materials, leading to get better electrophosphorescent materials.

The title complex (I) is a mononuclear iridium(III) complex (Fig. 1), in which the environment around the IrIII ion is a distorted octahedral coordination geometry, the coordination conformation of the C, N and O atoms of the ligands adopt the cis-, trans- and cis- respectively, which is consistent with the similar reported complexes (Lamansky et al., 2001). It can be illustrated (Fig. 1) that the carbon-metal bond is formed between the IrIII ion and the carbon atom on the benzene ring rather than the C atom on the naphthalene ring. Moreover, there are two five-membered rings formed with (Ir1 C1 C6 C7 N1) and (Ir1 C18 C23 C24 N2), the average deviation of which are 0.0629 Å and 0.0719 Å, and the dihedral angle with their adjacent benzene rings (C1 C2 C3 C4 C5 C6) and (C18 C19 C20 C21 C22 C23) are 6.5 (2)° and 6.9 (1)° respectively, and the dihedral angle with their adjacent oxazole heterocycle (N1 O1 C7–17) and (N2 O2 C24–34) are 9.2 (1)° and 11.4 (1)° respectively. It shows from the Table 1 that the increase of the bond distance from Ir—C to Ir—N and Ir—O is caused by the increase of the covalent component between the coordination atoms from C to N and O of which the electronegativity decreases gradually.

Related literature top

For the synthesis and reactions of some 2-arylnaphth[1,2-d]oxazole derivatives, see: Abbady (1979). For the synthesis and characterization of phosphorescent cyclometalated iridium complexes, see: Lamansky et al. (2001).

Experimental top

The ligand 2-arylnaphth[1,2-d]oxazole was prepared according to the literature (Abbady, 1979). The ligand (0.54 gram, 2.2 mmol) and IrCl3.3H2O (0.35 gram, 1 mmol) were added to 20 ml 2-ethoxyethanol: H2O(3:1, v/v) solution under inert gas atmosphere at 120 °C for 24 h, and then the intermediate product, acetylacetonate(10 ml) and Na2CO3 (1.06 gram, 10 mmol) were refluxed for 12 h. After cooling to room temperature, the colored precipitate was then filtered and washed with ethanol and water. The crude product was flash chromatographed using a silica/dichloromethane column to yield ca. 58% of the pure title compound after solvent evaporation and drying.

Refinement top

H atoms were positioned geometrically and refined using a riding model with C—H =0.93–0.96 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of the title complex. Displacement ellipsoids are drawn at the 30% probability level. H atoms omitted for clarity.
(Acetylacetonato-κ2O,O')bis[2-(naphth[1,2- d][1,3]oxazol-2-yl)phenyl-κ2C1,N]iridium(III) top
Crystal data top
[Ir(C17H10NO)2(C5H7O2)]F(000) = 3072
Mr = 779.83Dx = 1.675 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 16.640 (3) ÅCell parameters from 198 reflections
b = 17.384 (3) Åθ = 2.5–26.0°
c = 21.461 (4) ŵ = 4.36 mm1
β = 95.026 (2)°T = 273 K
V = 6184.3 (19) Å3Prismatic, yellow
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
7558 independent reflections
Radiation source: fine-focus sealed tube6091 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
phi and ω scansθmax = 28.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2222
Tmin = 0.354, Tmax = 0.476k = 2322
28178 measured reflectionsl = 2828
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0233P)2 + 0.650P]
where P = (Fo2 + 2Fc2)/3
7558 reflections(Δ/σ)max = 0.003
415 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Ir(C17H10NO)2(C5H7O2)]V = 6184.3 (19) Å3
Mr = 779.83Z = 8
Monoclinic, C2/cMo Kα radiation
a = 16.640 (3) ŵ = 4.36 mm1
b = 17.384 (3) ÅT = 273 K
c = 21.461 (4) Å0.30 × 0.20 × 0.20 mm
β = 95.026 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7558 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
6091 reflections with I > 2σ(I)
Tmin = 0.354, Tmax = 0.476Rint = 0.031
28178 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.051H-atom parameters constrained
S = 1.01Δρmax = 0.56 e Å3
7558 reflectionsΔρmin = 0.31 e Å3
415 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
Ir10.197297 (6)0.080046 (6)0.624868 (4)0.03071 (4)
C10.11803 (17)0.16584 (16)0.60964 (13)0.0388 (6)
O10.18897 (14)0.19239 (12)0.45599 (10)0.0566 (6)
N10.21509 (14)0.10506 (14)0.53177 (10)0.0375 (5)
N20.16297 (13)0.05731 (12)0.71327 (10)0.0325 (5)
C20.0616 (2)0.19443 (19)0.64860 (17)0.0565 (9)
H2A0.05310.16820.68520.068*
O20.09828 (12)0.02524 (11)0.77095 (8)0.0434 (5)
C30.0187 (2)0.2604 (2)0.6338 (2)0.0770 (11)
H3A0.01750.27850.66100.092*
O30.29032 (12)0.16332 (11)0.64681 (9)0.0441 (5)
C40.0280 (2)0.3008 (2)0.5787 (2)0.0773 (12)
H4A0.00100.34570.56980.093*
O40.28637 (11)0.00711 (11)0.64615 (9)0.0416 (5)
C50.0802 (2)0.27381 (19)0.53807 (17)0.0624 (10)
H5A0.08640.29950.50080.075*
C60.12409 (18)0.20665 (16)0.55357 (14)0.0448 (7)
C70.17719 (18)0.16926 (16)0.51483 (13)0.0419 (7)
C80.2376 (2)0.1358 (2)0.43351 (14)0.0529 (8)
C90.2651 (3)0.1344 (3)0.37428 (16)0.0720 (11)
H9A0.25330.17360.34540.086*
C100.3104 (3)0.0726 (3)0.36111 (17)0.0795 (14)
H10A0.33040.06960.32210.095*
C110.3284 (2)0.0119 (2)0.40499 (16)0.0637 (10)
C120.3728 (3)0.0527 (3)0.3898 (2)0.0865 (13)
H12A0.39260.05510.35060.104*
C130.3878 (3)0.1112 (3)0.4295 (2)0.0875 (13)
H13A0.41820.15290.41800.105*
C140.3575 (2)0.1100 (2)0.48947 (18)0.0706 (10)
H14A0.36680.15140.51660.085*
C150.31459 (19)0.0478 (2)0.50718 (15)0.0550 (8)
H15A0.29490.04700.54640.066*
C160.30009 (18)0.0147 (2)0.46627 (14)0.0486 (8)
C170.25393 (18)0.08108 (18)0.47913 (13)0.0443 (7)
C180.11811 (15)0.00436 (15)0.60453 (12)0.0318 (6)
C190.08870 (17)0.03322 (16)0.54606 (13)0.0402 (7)
H19A0.10140.00800.51000.048*
C200.04120 (19)0.09833 (18)0.54086 (15)0.0486 (8)
H20A0.02280.11630.50130.058*
C210.02032 (19)0.13742 (18)0.59310 (14)0.0498 (8)
H21A0.01140.18150.58860.060*
C220.04648 (18)0.11104 (17)0.65172 (14)0.0448 (7)
H22A0.03240.13660.68730.054*
C230.09442 (16)0.04538 (16)0.65690 (12)0.0352 (6)
C240.12111 (16)0.00633 (16)0.71406 (12)0.0356 (6)
C250.12748 (17)0.03448 (17)0.80972 (13)0.0403 (7)
C260.11666 (19)0.0415 (2)0.87263 (14)0.0523 (8)
H26A0.08910.00480.89400.063*
C270.1491 (2)0.1060 (2)0.90122 (14)0.0536 (8)
H27A0.14540.11240.94390.064*
C280.18800 (19)0.16318 (18)0.86820 (13)0.0455 (7)
C290.2188 (2)0.2304 (2)0.89932 (15)0.0609 (9)
H29A0.21500.23520.94210.073*
C300.2537 (3)0.2877 (2)0.86859 (17)0.0711 (11)
H30A0.27320.33130.89010.085*
C310.2603 (2)0.2809 (2)0.80412 (17)0.0695 (11)
H31A0.28380.32050.78300.083*
C320.2326 (2)0.21693 (17)0.77178 (15)0.0536 (8)
H32A0.23700.21370.72900.064*
C330.19741 (17)0.15592 (16)0.80297 (13)0.0389 (6)
C340.16667 (17)0.08667 (15)0.77478 (12)0.0365 (6)
C350.4142 (2)0.2183 (2)0.68251 (19)0.0828 (13)
H35A0.38340.26400.67260.124*
H35B0.46010.21700.65830.124*
H35C0.43230.21820.72620.124*
C360.3621 (2)0.1482 (2)0.66736 (14)0.0534 (8)
C370.3956 (2)0.0755 (2)0.67846 (18)0.0658 (10)
H37A0.44910.07440.69510.079*
C380.35889 (19)0.0046 (2)0.66777 (14)0.0520 (8)
C390.4084 (2)0.0675 (2)0.6810 (2)0.0802 (13)
H39A0.37520.11190.67180.120*
H39B0.42860.06840.72430.120*
H39C0.45290.06790.65540.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.03189 (6)0.03227 (6)0.02784 (6)0.00094 (5)0.00197 (4)0.00314 (5)
C10.0385 (16)0.0343 (15)0.0421 (16)0.0019 (12)0.0046 (13)0.0013 (12)
O10.0761 (16)0.0517 (14)0.0404 (12)0.0120 (12)0.0034 (11)0.0176 (10)
N10.0408 (13)0.0411 (13)0.0303 (12)0.0056 (11)0.0014 (10)0.0065 (10)
N20.0385 (13)0.0335 (12)0.0258 (11)0.0027 (10)0.0046 (9)0.0005 (9)
C20.054 (2)0.052 (2)0.064 (2)0.0109 (16)0.0053 (17)0.0024 (17)
O20.0557 (13)0.0450 (12)0.0295 (10)0.0139 (10)0.0050 (9)0.0025 (9)
C30.065 (2)0.070 (3)0.094 (3)0.026 (2)0.002 (2)0.008 (2)
O30.0455 (12)0.0467 (12)0.0394 (11)0.0140 (10)0.0004 (9)0.0069 (9)
C40.073 (3)0.053 (2)0.100 (3)0.027 (2)0.023 (2)0.002 (2)
O40.0412 (12)0.0449 (12)0.0385 (11)0.0093 (9)0.0020 (9)0.0021 (9)
C50.074 (2)0.0420 (19)0.066 (2)0.0046 (18)0.0234 (19)0.0066 (17)
C60.0493 (18)0.0336 (16)0.0484 (18)0.0040 (13)0.0136 (14)0.0029 (13)
C70.0508 (18)0.0383 (16)0.0345 (15)0.0122 (14)0.0079 (13)0.0108 (13)
C80.063 (2)0.061 (2)0.0347 (17)0.0193 (18)0.0013 (15)0.0124 (15)
C90.090 (3)0.088 (3)0.039 (2)0.027 (3)0.0094 (19)0.0187 (19)
C100.093 (3)0.109 (4)0.041 (2)0.021 (3)0.027 (2)0.006 (2)
C110.057 (2)0.089 (3)0.047 (2)0.009 (2)0.0195 (17)0.002 (2)
C120.071 (3)0.129 (4)0.064 (3)0.002 (3)0.031 (2)0.015 (3)
C130.072 (3)0.107 (4)0.086 (3)0.024 (3)0.023 (2)0.022 (3)
C140.061 (2)0.089 (3)0.063 (2)0.018 (2)0.0055 (19)0.007 (2)
C150.052 (2)0.070 (2)0.0440 (19)0.0086 (17)0.0074 (15)0.0019 (17)
C160.0417 (17)0.068 (2)0.0368 (17)0.0079 (16)0.0062 (13)0.0025 (15)
C170.0449 (17)0.057 (2)0.0308 (15)0.0135 (15)0.0036 (13)0.0051 (14)
C180.0317 (14)0.0328 (14)0.0311 (14)0.0021 (11)0.0037 (11)0.0008 (11)
C190.0444 (17)0.0457 (18)0.0306 (15)0.0026 (14)0.0035 (12)0.0024 (12)
C200.0502 (19)0.0533 (19)0.0422 (18)0.0090 (15)0.0038 (14)0.0138 (14)
C210.057 (2)0.0437 (18)0.0497 (19)0.0163 (15)0.0097 (16)0.0099 (15)
C220.0516 (18)0.0416 (16)0.0422 (17)0.0082 (15)0.0104 (14)0.0025 (14)
C230.0395 (15)0.0332 (14)0.0330 (15)0.0028 (12)0.0037 (12)0.0024 (12)
C240.0378 (15)0.0380 (15)0.0317 (14)0.0023 (12)0.0076 (12)0.0029 (12)
C250.0449 (17)0.0450 (17)0.0308 (15)0.0050 (14)0.0021 (13)0.0023 (12)
C260.060 (2)0.063 (2)0.0340 (16)0.0106 (17)0.0092 (15)0.0010 (15)
C270.063 (2)0.069 (2)0.0288 (16)0.0030 (18)0.0048 (15)0.0058 (15)
C280.0531 (19)0.0510 (19)0.0321 (15)0.0016 (15)0.0022 (13)0.0078 (13)
C290.078 (2)0.063 (2)0.0411 (18)0.0058 (19)0.0041 (17)0.0151 (17)
C300.091 (3)0.055 (2)0.066 (3)0.010 (2)0.002 (2)0.0232 (19)
C310.101 (3)0.049 (2)0.059 (2)0.025 (2)0.012 (2)0.0079 (17)
C320.074 (2)0.0442 (19)0.0428 (18)0.0115 (17)0.0079 (16)0.0044 (14)
C330.0417 (16)0.0383 (16)0.0366 (15)0.0000 (13)0.0023 (13)0.0052 (12)
C340.0399 (15)0.0401 (16)0.0295 (14)0.0014 (12)0.0033 (12)0.0024 (12)
C350.062 (2)0.089 (3)0.094 (3)0.037 (2)0.013 (2)0.014 (2)
C360.0443 (19)0.072 (2)0.0435 (18)0.0193 (17)0.0001 (15)0.0033 (16)
C370.0383 (18)0.084 (3)0.072 (3)0.0019 (19)0.0118 (17)0.002 (2)
C380.0433 (18)0.072 (2)0.0403 (18)0.0143 (17)0.0003 (14)0.0005 (16)
C390.063 (2)0.086 (3)0.088 (3)0.035 (2)0.015 (2)0.005 (2)
Geometric parameters (Å, º) top
Ir1—C181.995 (3)C15—H15A0.9300
Ir1—C11.999 (3)C16—C171.427 (4)
Ir1—N22.067 (2)C18—C191.399 (4)
Ir1—N12.091 (2)C18—C231.416 (3)
Ir1—O42.1407 (18)C19—C201.379 (4)
Ir1—O32.1414 (19)C19—H19A0.9300
C1—C21.401 (4)C20—C211.381 (4)
C1—C61.408 (4)C20—H20A0.9300
O1—C71.356 (3)C21—C221.374 (4)
O1—C81.387 (4)C21—H21A0.9300
N1—C71.317 (3)C22—C231.391 (4)
N1—C171.413 (4)C22—H22A0.9300
N2—C241.308 (3)C23—C241.438 (4)
N2—C341.412 (3)C25—C341.377 (4)
C2—C31.374 (5)C25—C261.383 (4)
C2—H2A0.9300C26—C271.365 (5)
O2—C241.351 (3)C26—H26A0.9300
O2—C251.391 (3)C27—C281.411 (4)
C3—C41.394 (5)C27—H27A0.9300
C3—H3A0.9300C28—C291.420 (4)
O3—C361.264 (4)C28—C331.428 (4)
C4—C51.366 (5)C29—C301.354 (5)
C4—H4A0.9300C29—H29A0.9300
O4—C381.271 (3)C30—C311.402 (5)
C5—C61.402 (4)C30—H30A0.9300
C5—H5A0.9300C31—C321.369 (4)
C6—C71.422 (4)C31—H31A0.9300
C8—C171.375 (4)C32—C331.409 (4)
C8—C91.388 (4)C32—H32A0.9300
C9—C101.356 (6)C33—C341.422 (4)
C9—H9A0.9300C35—C361.513 (4)
C10—C111.428 (5)C35—H35A0.9600
C10—H10A0.9300C35—H35B0.9600
C11—C121.399 (5)C35—H35C0.9600
C11—C161.436 (4)C36—C371.394 (5)
C12—C131.337 (6)C37—C381.385 (5)
C12—H12A0.9300C37—H37A0.9300
C13—C141.422 (5)C38—C391.513 (4)
C13—H13A0.9300C39—H39A0.9600
C14—C151.367 (5)C39—H39B0.9600
C14—H14A0.9300C39—H39C0.9600
C15—C161.405 (4)
C18—Ir1—C195.70 (11)C8—C17—C16119.9 (3)
C18—Ir1—N280.20 (9)N1—C17—C16133.3 (3)
C1—Ir1—N293.51 (10)C19—C18—C23115.6 (2)
C18—Ir1—N195.17 (10)C19—C18—Ir1129.2 (2)
C1—Ir1—N180.52 (10)C23—C18—Ir1114.92 (19)
N2—Ir1—N1172.10 (8)C20—C19—C18121.3 (3)
C18—Ir1—O487.58 (9)C20—C19—H19A119.3
C1—Ir1—O4176.06 (9)C18—C19—H19A119.3
N2—Ir1—O484.87 (8)C19—C20—C21121.4 (3)
N1—Ir1—O4101.40 (8)C19—C20—H20A119.3
C18—Ir1—O3175.06 (9)C21—C20—H20A119.3
C1—Ir1—O389.17 (10)C22—C21—C20119.8 (3)
N2—Ir1—O3100.37 (8)C22—C21—H21A120.1
N1—Ir1—O384.80 (8)C20—C21—H21A120.1
O4—Ir1—O387.59 (8)C21—C22—C23118.7 (3)
C2—C1—C6115.6 (3)C21—C22—H22A120.6
C2—C1—Ir1129.3 (2)C23—C22—H22A120.6
C6—C1—Ir1114.8 (2)C22—C23—C18123.2 (2)
C7—O1—C8104.5 (2)C22—C23—C24126.0 (2)
C7—N1—C17105.7 (2)C18—C23—C24110.7 (2)
C7—N1—Ir1109.60 (19)N2—C24—O2114.2 (2)
C17—N1—Ir1144.7 (2)N2—C24—C23120.9 (2)
C24—N2—C34105.9 (2)O2—C24—C23124.5 (2)
C24—N2—Ir1111.34 (17)C34—C25—C26125.6 (3)
C34—N2—Ir1142.78 (18)C34—C25—O2108.9 (2)
C3—C2—C1121.3 (3)C26—C25—O2125.5 (3)
C3—C2—H2A119.3C27—C26—C25115.5 (3)
C1—C2—H2A119.3C27—C26—H26A122.2
C24—O2—C25104.3 (2)C25—C26—H26A122.2
C2—C3—C4121.5 (4)C26—C27—C28122.2 (3)
C2—C3—H3A119.3C26—C27—H27A118.9
C4—C3—H3A119.3C28—C27—H27A118.9
C36—O3—Ir1125.4 (2)C27—C28—C29120.5 (3)
C5—C4—C3119.5 (3)C27—C28—C33121.6 (3)
C5—C4—H4A120.2C29—C28—C33117.9 (3)
C3—C4—H4A120.2C30—C29—C28122.0 (3)
C38—O4—Ir1125.6 (2)C30—C29—H29A119.0
C4—C5—C6118.7 (3)C28—C29—H29A119.0
C4—C5—H5A120.6C29—C30—C31119.5 (3)
C6—C5—H5A120.6C29—C30—H30A120.3
C5—C6—C1123.2 (3)C31—C30—H30A120.3
C5—C6—C7125.4 (3)C32—C31—C30121.2 (3)
C1—C6—C7111.3 (3)C32—C31—H31A119.4
N1—C7—O1113.8 (3)C30—C31—H31A119.4
N1—C7—C6122.2 (3)C31—C32—C33120.4 (3)
O1—C7—C6123.8 (3)C31—C32—H32A119.8
C17—C8—O1109.1 (3)C33—C32—H32A119.8
C17—C8—C9125.5 (4)C32—C33—C34125.7 (3)
O1—C8—C9125.4 (3)C32—C33—C28119.0 (3)
C10—C9—C8116.0 (4)C34—C33—C28115.2 (3)
C10—C9—H9A122.0C25—C34—N2106.7 (2)
C8—C9—H9A122.0C25—C34—C33119.7 (3)
C9—C10—C11122.4 (3)N2—C34—C33133.5 (2)
C9—C10—H10A118.8C36—C35—H35A109.5
C11—C10—H10A118.8C36—C35—H35B109.5
C12—C11—C10121.6 (4)H35A—C35—H35B109.5
C12—C11—C16117.6 (4)C36—C35—H35C109.5
C10—C11—C16120.8 (4)H35A—C35—H35C109.5
C13—C12—C11122.4 (4)H35B—C35—H35C109.5
C13—C12—H12A118.8O3—C36—C37126.8 (3)
C11—C12—H12A118.8O3—C36—C35114.5 (3)
C12—C13—C14120.3 (4)C37—C36—C35118.7 (3)
C12—C13—H13A119.9C38—C37—C36128.0 (3)
C14—C13—H13A119.9C38—C37—H37A116.0
C15—C14—C13119.9 (4)C36—C37—H37A116.0
C15—C14—H14A120.0O4—C38—C37126.4 (3)
C13—C14—H14A120.0O4—C38—C39114.8 (3)
C14—C15—C16120.2 (3)C37—C38—C39118.7 (3)
C14—C15—H15A119.9C38—C39—H39A109.5
C16—C15—H15A119.9C38—C39—H39B109.5
C15—C16—C17124.8 (3)H39A—C39—H39B109.5
C15—C16—C11119.6 (3)C38—C39—H39C109.5
C17—C16—C11115.4 (3)H39A—C39—H39C109.5
C8—C17—N1106.8 (3)H39B—C39—H39C109.5
C18—Ir1—C1—C279.9 (3)C9—C8—C17—N1179.5 (3)
N2—Ir1—C1—C20.6 (3)O1—C8—C17—C16177.1 (3)
N1—Ir1—C1—C2174.2 (3)C9—C8—C17—C162.6 (5)
O4—Ir1—C1—C266.3 (15)C7—N1—C17—C81.7 (3)
O3—Ir1—C1—C2101.0 (3)Ir1—N1—C17—C8176.1 (2)
C18—Ir1—C1—C6105.2 (2)C7—N1—C17—C16175.9 (3)
N2—Ir1—C1—C6174.3 (2)Ir1—N1—C17—C166.4 (6)
N1—Ir1—C1—C610.9 (2)C15—C16—C17—C8174.3 (3)
O4—Ir1—C1—C6108.6 (14)C11—C16—C17—C81.7 (4)
O3—Ir1—C1—C673.9 (2)C15—C16—C17—N13.0 (5)
C18—Ir1—N1—C7104.92 (19)C11—C16—C17—N1179.0 (3)
C1—Ir1—N1—C79.99 (19)C1—Ir1—C18—C1981.4 (3)
N2—Ir1—N1—C751.2 (7)N2—Ir1—C18—C19174.0 (3)
O4—Ir1—N1—C7166.51 (18)N1—Ir1—C18—C190.4 (3)
O3—Ir1—N1—C780.04 (19)O4—Ir1—C18—C19100.8 (3)
C18—Ir1—N1—C1777.4 (3)O3—Ir1—C18—C1989.0 (10)
C1—Ir1—N1—C17172.3 (3)C1—Ir1—C18—C23105.3 (2)
N2—Ir1—N1—C17131.1 (6)N2—Ir1—C18—C2312.70 (19)
O4—Ir1—N1—C1711.2 (3)N1—Ir1—C18—C23173.7 (2)
O3—Ir1—N1—C1797.7 (3)O4—Ir1—C18—C2372.5 (2)
C18—Ir1—N2—C2411.46 (19)O3—Ir1—C18—C2384.4 (10)
C1—Ir1—N2—C24106.6 (2)C23—C18—C19—C201.3 (4)
N1—Ir1—N2—C2466.0 (7)Ir1—C18—C19—C20172.0 (2)
O4—Ir1—N2—C2476.97 (19)C18—C19—C20—C210.4 (5)
O3—Ir1—N2—C24163.56 (18)C19—C20—C21—C220.6 (5)
C18—Ir1—N2—C34166.7 (3)C20—C21—C22—C230.6 (5)
C1—Ir1—N2—C3471.5 (3)C21—C22—C23—C180.3 (5)
N1—Ir1—N2—C34112.1 (6)C21—C22—C23—C24174.3 (3)
O4—Ir1—N2—C34104.9 (3)C19—C18—C23—C221.3 (4)
O3—Ir1—N2—C3418.3 (3)Ir1—C18—C23—C22173.0 (2)
C6—C1—C2—C33.2 (5)C19—C18—C23—C24174.1 (2)
Ir1—C1—C2—C3171.6 (3)Ir1—C18—C23—C2411.6 (3)
C1—C2—C3—C41.4 (6)C34—N2—C24—O22.5 (3)
C18—Ir1—O3—C3615.9 (11)Ir1—N2—C24—O2178.68 (17)
C1—Ir1—O3—C36173.7 (2)C34—N2—C24—C23170.1 (2)
N2—Ir1—O3—C3680.3 (2)Ir1—N2—C24—C238.8 (3)
N1—Ir1—O3—C36105.8 (2)C25—O2—C24—N21.7 (3)
O4—Ir1—O3—C364.1 (2)C25—O2—C24—C23170.6 (3)
C2—C3—C4—C50.9 (6)C22—C23—C24—N2176.7 (3)
C18—Ir1—O4—C38175.9 (2)C18—C23—C24—N21.5 (4)
C1—Ir1—O4—C3829.5 (15)C22—C23—C24—O24.9 (5)
N2—Ir1—O4—C3895.5 (2)C18—C23—C24—O2170.3 (2)
N1—Ir1—O4—C3889.4 (2)C24—O2—C25—C340.1 (3)
O3—Ir1—O4—C385.2 (2)C24—O2—C25—C26178.0 (3)
C3—C4—C5—C61.1 (6)C34—C25—C26—C270.7 (5)
C4—C5—C6—C10.9 (5)O2—C25—C26—C27178.5 (3)
C4—C5—C6—C7176.4 (3)C25—C26—C27—C282.6 (5)
C2—C1—C6—C53.0 (4)C26—C27—C28—C29178.2 (3)
Ir1—C1—C6—C5172.6 (2)C26—C27—C28—C331.5 (5)
C2—C1—C6—C7174.6 (3)C27—C28—C29—C30177.4 (3)
Ir1—C1—C6—C79.7 (3)C33—C28—C29—C302.3 (5)
C17—N1—C7—O12.0 (3)C28—C29—C30—C310.3 (6)
Ir1—N1—C7—O1176.59 (18)C29—C30—C31—C320.5 (6)
C17—N1—C7—C6173.3 (3)C30—C31—C32—C330.6 (6)
Ir1—N1—C7—C68.0 (3)C31—C32—C33—C34179.8 (3)
C8—O1—C7—N11.5 (3)C31—C32—C33—C282.6 (5)
C8—O1—C7—C6173.7 (3)C27—C28—C33—C32176.3 (3)
C5—C6—C7—N1178.3 (3)C29—C28—C33—C323.4 (5)
C1—C6—C7—N10.7 (4)C27—C28—C33—C341.5 (4)
C5—C6—C7—O13.4 (5)C29—C28—C33—C34178.8 (3)
C1—C6—C7—O1174.2 (2)C26—C25—C34—N2179.4 (3)
C7—O1—C8—C170.4 (3)O2—C25—C34—N21.3 (3)
C7—O1—C8—C9179.4 (3)C26—C25—C34—C332.3 (5)
C17—C8—C9—C101.4 (6)O2—C25—C34—C33175.8 (2)
O1—C8—C9—C10178.3 (3)C24—N2—C34—C252.3 (3)
C8—C9—C10—C110.5 (6)Ir1—N2—C34—C25179.5 (2)
C9—C10—C11—C12177.8 (4)C24—N2—C34—C33174.3 (3)
C9—C10—C11—C161.2 (6)Ir1—N2—C34—C333.9 (5)
C10—C11—C12—C13177.7 (4)C32—C33—C34—C25174.4 (3)
C16—C11—C12—C131.4 (6)C28—C33—C34—C253.2 (4)
C11—C12—C13—C140.8 (7)C32—C33—C34—N21.8 (5)
C12—C13—C14—C151.7 (7)C28—C33—C34—N2179.4 (3)
C13—C14—C15—C160.2 (6)Ir1—O3—C36—C371.6 (5)
C14—C15—C16—C17177.8 (3)Ir1—O3—C36—C35176.6 (2)
C14—C15—C16—C112.0 (5)O3—C36—C37—C382.2 (6)
C12—C11—C16—C152.8 (5)C35—C36—C37—C38179.7 (4)
C10—C11—C16—C15176.3 (3)Ir1—O4—C38—C373.8 (5)
C12—C11—C16—C17179.0 (3)Ir1—O4—C38—C39177.7 (2)
C10—C11—C16—C170.1 (5)C36—C37—C38—O40.9 (6)
O1—C8—C17—N10.8 (3)C36—C37—C38—C39177.5 (4)

Experimental details

Crystal data
Chemical formula[Ir(C17H10NO)2(C5H7O2)]
Mr779.83
Crystal system, space groupMonoclinic, C2/c
Temperature (K)273
a, b, c (Å)16.640 (3), 17.384 (3), 21.461 (4)
β (°) 95.026 (2)
V3)6184.3 (19)
Z8
Radiation typeMo Kα
µ (mm1)4.36
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.354, 0.476
No. of measured, independent and
observed [I > 2σ(I)] reflections
28178, 7558, 6091
Rint0.031
(sin θ/λ)max1)0.665
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.051, 1.01
No. of reflections7558
No. of parameters415
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.31

Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ir1—C181.995 (3)Ir1—N12.091 (2)
Ir1—C11.999 (3)Ir1—O42.1407 (18)
Ir1—N22.067 (2)Ir1—O32.1414 (19)
 

Acknowledgements

The author gratefully acknowledges financial support by the Natural Science Foundation of China (grant No. 20471054).

References

First citationAbbady, M. A. (1979). Indian J. Chem. Sect. B, 17, 450–453.
First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationLamansky, S., Djurovich, P., Murphy, D., Abdel-Razaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001). Inorg. Chem. 40, 1704–1711.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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