PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m440.
Published online 2009 March 25. doi:  10.1107/S1600536809010204
PMCID: PMC2968936

cis-Bis[2-(1,3-benzothia­zol-2-yl)-1-(4-fluoro­phen­yl)ethen­yl](pentane-2,4-dionato-κ2 O,O′)iridium(III)

Abstract

In the title compound, [Ir(C15H9FNS)2(C5H7O2)], the Ir atom is hexa­coordinated by three chelating ligands, with two cyclo­metalated 2-(1,3-benzothia­zol-2-yl)-1-(4-fluoro­phen­yl)ethenyl ligands showing N,C-bidentate coordination and an O,O′-bidenate pentane-2,4-dionate anion, thereby forming a distorted octa­hedral enviroment.

Related literature

For a related structure, see: Li et al. (2008 [triangle]). For background to possible applications of this class of compound, see: Baldo et al. (1998 [triangle]); Forrest (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m440-scheme1.jpg

Experimental

Crystal data

  • [Ir(C15H9FNS)2(C5H7O2)]
  • M r = 799.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m440-efi1.jpg
  • a = 9.1632 (18) Å
  • b = 17.736 (4) Å
  • c = 18.823 (4) Å
  • β = 93.06 (3)°
  • V = 3054.7 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.56 mm−1
  • T = 113 K
  • 0.16 × 0.14 × 0.10 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.529, T max = 0.659
  • 20289 measured reflections
  • 5373 independent reflections
  • 4792 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.069
  • S = 1.05
  • 5373 reflections
  • 399 parameters
  • H-atom parameters constrained
  • Δρmax = 1.37 e Å−3
  • Δρmin = −2.58 e Å−3

Data collection: CrystalClear (Rigaku, 1999 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010204/hb2924sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010204/hb2924Isup2.hkl

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

supplementary crystallographic information

Comment

Organic triplet-state light-emitting materials (organic phosphorophores) have been one of the most important recent develophments in the field of organic light-emitting diodes (OLEDs) (Baldo et al., 1998; Forrest, 2003). we now report the crystal structure of the title compound, (I), a new iridium(III) complex with benzothiazole and acetylacetonate ligands. The atomic connectivity of (I) was elucidated by extensive spectroscopic analysis, including two-dimensional NMR spectroscopy, and confirmed by single-crystal X-ray diffraction analysis (Fig. 1)

The title compound is a netural mononuclear iridium(III) complex. All the bond lengths and angles fall within their normal ranges. The iridium centre is coordinated by two N atoms and two C atoms from the two 2-(4-fluorostyryl)benzo[d]thiazole anions and two O atoms for the β-diketonate (Table 1). The Ir—C bond lengths [1.988 (4) and 2.000 (4) Å] are found to be shorter than the Ir—N bonds [2.045 (3) and 2.049 Å], as seen in related compounds (Li et al.,2008). The two five-numbered chelate rings are nearly coplanar with the r.m.s. deviations of 0.0549 (3) for C7—C8—C9—N1—Ir1 and 0.0705 (3)Å for C22—C23—C24—N2—Ir1. The dihedral angles between the two benzo[d]thiazoles and two fluorobenzene rings are 59.2 (2) and 84.9 (2)°, respectively, which indicates that two fluorobenzene units are almost perpendicular.

Experimental

The title compound was prepared by the reaction of (E)-2-(4-fluorostyryl)benzothiazole (2.2 mmol) in 2-ethoxyethaol (10 mL) with iridium trichloride hydrate (1.0 mmol) in 3.0 ml of water for 12 h at 353 K. The crude product was purified on a silica gel column using acetic ether and n-hexane as eluent to give the desired red powder of the target compound in 42% yield. Red prisms of (I) were grown by slow evaporation of a solution in methylene chloride/methanol(1:3). Spectroscopic analysis: 1H NMR (500 MHz, CDCl3, p.p.m.): 1.71 (s, 6H), 6.41 (t, 4H), 6.78 (t, 4H), 7.00–7.08 (m, 6H), 7.31 (d, 2H), 7.53 (d, 2H). MS APCI (m/z): 800.9 [M+1]+.

Refinement

All H atoms were positioned geometrically and refined as riding (C—H = 0.93–0.96 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(parent) or 1.5Ueq(parent).

Figures

Fig. 1.
View of the molecule of (I) with displacement ellipsoids drawn at the 35% probability level. The H atoms are omitted for clarity.

Crystal data

[Ir(C15H9FNS)2(C5H7O2)]F(000) = 1568
Mr = 799.89Dx = 1.739 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10390 reflections
a = 9.1632 (18) Åθ = 1.6–27.9°
b = 17.736 (4) ŵ = 4.56 mm1
c = 18.823 (4) ÅT = 113 K
β = 93.06 (3)°Prism, red
V = 3054.7 (11) Å30.16 × 0.14 × 0.10 mm
Z = 4

Data collection

Rigaku Saturn diffractometer5373 independent reflections
Radiation source: rotating anode4792 reflections with I > 2σ(I)
confocalRint = 0.055
ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→9
Tmin = 0.529, Tmax = 0.659k = −21→20
20289 measured reflectionsl = −22→21

Refinement

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) = 0.069H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0328P)2] where P = (Fo2 + 2Fc2)/3
5373 reflections(Δ/σ)max = 0.005
399 parametersΔρmax = 1.37 e Å3
0 restraintsΔρmin = −2.58 e Å3

Special details

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)

xyzUiso*/Ueq
Ir10.914147 (14)0.885461 (7)0.233249 (7)0.01190 (7)
S10.66028 (11)1.04464 (5)0.36383 (6)0.0239 (2)
S21.28983 (11)0.75043 (6)0.16085 (6)0.0256 (3)
F11.5245 (3)1.09581 (13)0.14514 (15)0.0368 (7)
F20.9677 (3)0.84075 (14)0.60215 (13)0.0403 (7)
O10.8070 (3)0.77954 (13)0.21589 (14)0.0151 (6)
O20.7795 (3)0.92998 (13)0.14703 (14)0.0182 (6)
N10.7667 (3)0.93021 (16)0.29937 (16)0.0133 (7)
N21.0741 (3)0.84154 (16)0.17349 (17)0.0158 (7)
C10.5810 (4)0.9564 (2)0.3751 (2)0.0206 (9)
C20.4627 (4)0.9380 (2)0.4159 (2)0.0265 (10)
H20.41410.97490.44050.032*
C30.4204 (4)0.8629 (2)0.4183 (2)0.0290 (11)
H30.34310.84890.44540.035*
C40.4931 (4)0.8086 (2)0.3802 (2)0.0259 (10)
H40.46280.75860.38260.031*
C50.6090 (4)0.8264 (2)0.3390 (2)0.0193 (9)
H50.65590.78940.31370.023*
C60.6529 (4)0.9014 (2)0.3367 (2)0.0159 (9)
C70.7865 (4)1.0049 (2)0.3091 (2)0.0175 (9)
C80.9091 (4)1.0382 (2)0.2803 (2)0.0169 (9)
H80.92851.08960.28360.020*
C90.9980 (4)0.9889 (2)0.2469 (2)0.0149 (8)
C101.1375 (4)1.01596 (19)0.21908 (19)0.0140 (8)
C111.1421 (4)1.0838 (2)0.1814 (2)0.0186 (9)
H111.05701.11190.17370.022*
C121.2707 (5)1.10982 (19)0.1553 (2)0.0233 (10)
H121.27251.15400.12880.028*
C131.3955 (4)1.0689 (2)0.1695 (2)0.0221 (9)
C141.3982 (4)1.0015 (2)0.2060 (2)0.0217 (9)
H141.48450.97440.21370.026*
C151.2674 (4)0.9756 (2)0.2307 (2)0.0174 (9)
H151.26610.93030.25550.021*
C161.2342 (4)0.8054 (2)0.0874 (2)0.0212 (9)
C171.2906 (4)0.8077 (2)0.0208 (2)0.0250 (10)
H171.36760.77640.00980.030*
C181.2303 (4)0.8576 (2)−0.0292 (2)0.0273 (10)
H181.26660.8597−0.07430.033*
C191.1142 (5)0.9049 (2)−0.0119 (2)0.0252 (10)
H191.07520.9386−0.04570.030*
C201.0576 (4)0.9023 (2)0.0542 (2)0.0209 (9)
H200.98080.93390.06500.025*
C211.1164 (4)0.8520 (2)0.1048 (2)0.0167 (9)
C221.1555 (4)0.7908 (2)0.2101 (2)0.0192 (9)
C231.1358 (4)0.7834 (2)0.2839 (2)0.0176 (9)
H231.18670.74860.31270.021*
C241.0345 (4)0.83243 (19)0.3087 (2)0.0175 (9)
C251.0106 (4)0.83624 (19)0.3856 (2)0.0150 (8)
C261.0432 (5)0.9016 (2)0.4245 (2)0.0238 (10)
H261.07470.94450.40130.029*
C271.0292 (5)0.9029 (2)0.4973 (2)0.0272 (10)
H271.05340.94600.52360.033*
C280.9786 (4)0.8394 (2)0.5300 (2)0.0255 (10)
C290.9402 (4)0.7751 (2)0.4934 (2)0.0252 (10)
H290.90220.73370.51650.030*
C300.9599 (4)0.7738 (2)0.4208 (2)0.0205 (9)
H300.93850.72990.39530.025*
C310.6666 (4)0.6829 (2)0.1608 (2)0.0266 (10)
H31A0.74600.64950.17380.040*
H31B0.62840.67090.11370.040*
H31C0.59100.67720.19370.040*
C320.7211 (4)0.7637 (2)0.1626 (2)0.0178 (9)
C330.6716 (4)0.8130 (2)0.1087 (2)0.0200 (9)
H330.61500.79180.07140.024*
C340.6972 (4)0.89059 (19)0.1044 (2)0.0182 (9)
C350.6229 (4)0.9345 (2)0.0443 (2)0.0258 (10)
H35A0.58910.98180.06200.039*
H35B0.54140.90620.02440.039*
H35C0.69100.94360.00820.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ir10.01140 (11)0.01073 (11)0.01329 (12)0.00056 (5)−0.00189 (7)−0.00079 (5)
S10.0190 (6)0.0185 (5)0.0348 (7)0.0027 (4)0.0051 (4)−0.0084 (5)
S20.0216 (6)0.0302 (6)0.0253 (7)0.0104 (5)0.0026 (4)−0.0051 (5)
F10.0272 (15)0.0348 (14)0.0501 (19)−0.0077 (12)0.0173 (12)0.0091 (13)
F20.0611 (19)0.0461 (16)0.0138 (15)0.0079 (13)0.0026 (12)−0.0008 (12)
O10.0159 (15)0.0150 (13)0.0143 (15)−0.0023 (11)−0.0009 (11)0.0011 (11)
O20.0196 (15)0.0139 (14)0.0204 (16)0.0014 (12)−0.0054 (11)−0.0001 (12)
N10.0143 (17)0.0149 (17)0.0107 (17)0.0001 (13)−0.0013 (12)−0.0015 (14)
N20.0152 (17)0.0144 (17)0.0177 (19)−0.0022 (14)−0.0011 (13)−0.0049 (14)
C10.016 (2)0.019 (2)0.026 (3)0.0011 (17)−0.0021 (17)−0.0025 (18)
C20.020 (2)0.031 (2)0.029 (3)0.0056 (19)0.0019 (18)−0.004 (2)
C30.018 (2)0.035 (3)0.034 (3)0.000 (2)0.0039 (19)0.002 (2)
C40.020 (2)0.025 (2)0.032 (3)−0.0017 (19)0.0001 (18)0.000 (2)
C50.017 (2)0.019 (2)0.021 (2)0.0022 (17)−0.0030 (16)−0.0006 (17)
C60.012 (2)0.021 (2)0.014 (2)0.0031 (17)−0.0020 (15)−0.0008 (17)
C70.012 (2)0.022 (2)0.019 (2)0.0040 (17)−0.0044 (15)−0.0051 (18)
C80.018 (2)0.0093 (19)0.023 (2)−0.0016 (16)−0.0021 (16)−0.0011 (17)
C90.017 (2)0.016 (2)0.012 (2)0.0013 (17)−0.0036 (15)0.0020 (16)
C100.019 (2)0.0140 (19)0.009 (2)−0.0043 (16)−0.0004 (15)−0.0023 (16)
C110.021 (2)0.014 (2)0.020 (2)0.0050 (17)−0.0021 (16)0.0002 (17)
C120.033 (3)0.013 (2)0.024 (3)−0.0005 (17)0.005 (2)0.0048 (17)
C130.019 (2)0.026 (2)0.022 (2)−0.0073 (18)0.0077 (17)−0.0017 (19)
C140.014 (2)0.022 (2)0.028 (3)−0.0019 (18)−0.0042 (17)0.000 (2)
C150.017 (2)0.0137 (19)0.021 (2)−0.0018 (17)−0.0030 (16)0.0028 (17)
C160.013 (2)0.025 (2)0.026 (3)−0.0034 (18)0.0031 (17)−0.0086 (19)
C170.019 (2)0.029 (2)0.027 (3)−0.0072 (19)0.0046 (18)−0.011 (2)
C180.028 (3)0.034 (2)0.020 (3)−0.018 (2)0.0068 (18)−0.005 (2)
C190.032 (3)0.020 (2)0.023 (3)−0.011 (2)0.0017 (19)0.0021 (19)
C200.024 (2)0.018 (2)0.020 (2)−0.0042 (18)−0.0023 (17)−0.0009 (19)
C210.018 (2)0.015 (2)0.017 (2)−0.0063 (17)0.0012 (16)−0.0051 (18)
C220.015 (2)0.013 (2)0.030 (3)−0.0002 (17)−0.0009 (17)−0.0014 (18)
C230.019 (2)0.017 (2)0.016 (2)0.0020 (17)−0.0036 (16)−0.0025 (17)
C240.015 (2)0.010 (2)0.027 (3)−0.0047 (16)−0.0021 (16)0.0000 (17)
C250.0101 (19)0.017 (2)0.018 (2)0.0042 (16)−0.0041 (15)−0.0021 (17)
C260.029 (3)0.019 (2)0.024 (3)0.0003 (18)−0.0016 (19)0.0010 (19)
C270.037 (3)0.024 (2)0.020 (3)0.007 (2)−0.0065 (19)−0.010 (2)
C280.030 (3)0.033 (3)0.013 (2)0.011 (2)−0.0030 (17)0.002 (2)
C290.028 (3)0.022 (2)0.025 (3)0.0038 (19)0.0007 (18)0.0072 (19)
C300.022 (2)0.019 (2)0.020 (2)0.0023 (17)−0.0032 (17)0.0005 (18)
C310.025 (2)0.020 (2)0.033 (3)−0.0095 (18)−0.0069 (18)0.001 (2)
C320.013 (2)0.017 (2)0.024 (3)−0.0030 (17)0.0025 (16)−0.0024 (18)
C330.021 (2)0.021 (2)0.018 (2)−0.0076 (17)−0.0081 (16)−0.0038 (18)
C340.017 (2)0.021 (2)0.017 (2)0.0016 (16)−0.0033 (17)0.0028 (17)
C350.027 (2)0.022 (2)0.027 (3)−0.0014 (18)−0.0109 (18)0.0031 (19)

Geometric parameters (Å, °)

Ir1—C92.000 (4)C14—C151.387 (5)
Ir1—C241.988 (4)C14—H140.9300
Ir1—N12.045 (3)C15—H150.9300
Ir1—N22.049 (3)C16—C171.380 (5)
Ir1—O12.137 (2)C16—C211.411 (5)
Ir1—O22.137 (3)C17—C181.385 (6)
S1—C71.739 (4)C17—H170.9300
S1—C11.743 (4)C18—C191.407 (6)
S2—C221.734 (4)C18—H180.9300
S2—C161.746 (4)C19—C201.373 (5)
F1—C131.376 (4)C19—H190.9300
F2—C281.368 (5)C20—C211.393 (6)
O1—C321.273 (5)C20—H200.9300
O2—C341.280 (5)C22—C231.416 (5)
N1—C71.348 (4)C23—C241.372 (5)
N1—C61.386 (5)C23—H230.9300
N2—C221.336 (5)C24—C251.477 (5)
N2—C211.382 (5)C25—C301.384 (5)
C1—C21.399 (5)C25—C261.394 (5)
C1—C61.399 (5)C26—C271.384 (6)
C2—C31.389 (6)C26—H260.9300
C2—H20.9300C27—C281.375 (6)
C3—C41.391 (6)C27—H270.9300
C3—H30.9300C28—C291.369 (6)
C4—C51.385 (5)C29—C301.388 (5)
C4—H40.9300C29—H290.9300
C5—C61.391 (5)C30—H300.9300
C5—H50.9300C31—C321.518 (5)
C7—C81.404 (5)C31—H31A0.9600
C8—C91.371 (5)C31—H31B0.9600
C8—H80.9300C31—H31C0.9600
C9—C101.486 (5)C32—C331.397 (5)
C10—C151.396 (5)C33—C341.399 (5)
C10—C111.399 (5)C33—H330.9300
C11—C121.380 (5)C34—C351.505 (5)
C11—H110.9300C35—H35A0.9600
C12—C131.369 (6)C35—H35B0.9600
C12—H120.9300C35—H35C0.9600
C13—C141.378 (6)
C24—Ir1—C998.48 (15)C14—C15—H15119.3
C24—Ir1—N196.20 (14)C10—C15—H15119.3
C9—Ir1—N180.09 (13)C17—C16—C21121.4 (4)
C24—Ir1—N280.01 (14)C17—C16—S2128.9 (3)
C9—Ir1—N297.92 (13)C21—C16—S2109.7 (3)
N1—Ir1—N2175.46 (12)C16—C17—C18118.7 (4)
C24—Ir1—O2173.43 (12)C16—C17—H17120.6
C9—Ir1—O287.76 (12)C18—C17—H17120.6
N1—Ir1—O286.88 (11)C17—C18—C19120.2 (4)
N2—Ir1—O297.15 (11)C17—C18—H18119.9
C24—Ir1—O185.77 (12)C19—C18—H18119.9
C9—Ir1—O1175.04 (12)C20—C19—C18121.1 (4)
N1—Ir1—O196.96 (10)C20—C19—H19119.4
N2—Ir1—O185.30 (10)C18—C19—H19119.4
O2—Ir1—O188.10 (10)C19—C20—C21119.3 (4)
C7—S1—C190.17 (18)C19—C20—H20120.4
C22—S2—C1690.42 (18)C21—C20—H20120.4
C32—O1—Ir1125.0 (2)N2—C21—C20127.4 (4)
C34—O2—Ir1124.9 (2)N2—C21—C16113.3 (4)
C7—N1—C6113.1 (3)C20—C21—C16119.3 (4)
C7—N1—Ir1112.0 (2)N2—C22—C23118.1 (3)
C6—N1—Ir1134.8 (2)N2—C22—S2113.3 (3)
C22—N2—C21113.3 (3)C23—C22—S2128.1 (3)
C22—N2—Ir1111.7 (3)C24—C23—C22113.6 (4)
C21—N2—Ir1135.0 (3)C24—C23—H23123.2
C2—C1—C6121.4 (4)C22—C23—H23123.2
C2—C1—S1128.0 (3)C23—C24—C25120.1 (4)
C6—C1—S1110.6 (3)C23—C24—Ir1114.6 (3)
C3—C2—C1117.8 (4)C25—C24—Ir1124.9 (3)
C3—C2—H2121.1C30—C25—C26118.8 (4)
C1—C2—H2121.1C30—C25—C24120.3 (3)
C2—C3—C4120.4 (4)C26—C25—C24120.9 (3)
C2—C3—H3119.8C27—C26—C25120.4 (4)
C4—C3—H3119.8C27—C26—H26119.8
C5—C4—C3122.2 (4)C25—C26—H26119.8
C5—C4—H4118.9C28—C27—C26118.7 (4)
C3—C4—H4118.9C28—C27—H27120.7
C4—C5—C6117.9 (4)C26—C27—H27120.7
C4—C5—H5121.1F2—C28—C29118.9 (4)
C6—C5—H5121.1F2—C28—C27118.3 (4)
N1—C6—C5126.5 (3)C29—C28—C27122.8 (4)
N1—C6—C1113.1 (3)C28—C29—C30117.7 (4)
C5—C6—C1120.3 (3)C28—C29—H29121.1
N1—C7—C8117.8 (3)C30—C29—H29121.1
N1—C7—S1112.9 (3)C25—C30—C29121.5 (4)
C8—C7—S1129.0 (3)C25—C30—H30119.2
C9—C8—C7114.6 (3)C29—C30—H30119.2
C9—C8—H8122.7C32—C31—H31A109.5
C7—C8—H8122.7C32—C31—H31B109.5
C8—C9—C10119.9 (3)H31A—C31—H31B109.5
C8—C9—Ir1114.2 (3)C32—C31—H31C109.5
C10—C9—Ir1125.7 (3)H31A—C31—H31C109.5
C15—C10—C11118.2 (3)H31B—C31—H31C109.5
C15—C10—C9121.4 (3)O1—C32—C33126.7 (3)
C11—C10—C9120.4 (3)O1—C32—C31114.5 (3)
C12—C11—C10121.2 (4)C33—C32—C31118.7 (4)
C12—C11—H11119.4C32—C33—C34127.5 (4)
C10—C11—H11119.4C32—C33—H33116.2
C13—C12—C11118.3 (4)C34—C33—H33116.2
C13—C12—H12120.8O2—C34—C33126.5 (4)
C11—C12—H12120.8O2—C34—C35114.6 (3)
C12—C13—F1118.4 (4)C33—C34—C35118.8 (3)
C12—C13—C14123.3 (3)C34—C35—H35A109.5
F1—C13—C14118.3 (4)C34—C35—H35B109.5
C13—C14—C15117.5 (4)H35A—C35—H35B109.5
C13—C14—H14121.2C34—C35—H35C109.5
C15—C14—H14121.2H35A—C35—H35C109.5
C14—C15—C10121.5 (4)H35B—C35—H35C109.5
C24—Ir1—O1—C32−167.6 (3)Ir1—C9—C10—C11130.0 (3)
C9—Ir1—O1—C3243.4 (15)C15—C10—C11—C120.9 (6)
N1—Ir1—O1—C3296.7 (3)C9—C10—C11—C12179.9 (4)
N2—Ir1—O1—C32−87.3 (3)C10—C11—C12—C13−2.3 (6)
O2—Ir1—O1—C3210.0 (3)C11—C12—C13—F1−178.4 (4)
C24—Ir1—O2—C3411.2 (12)C11—C12—C13—C142.7 (6)
C9—Ir1—O2—C34172.9 (3)C12—C13—C14—C15−1.6 (6)
N1—Ir1—O2—C34−106.9 (3)F1—C13—C14—C15179.5 (3)
N2—Ir1—O2—C3475.2 (3)C13—C14—C15—C100.1 (6)
O1—Ir1—O2—C34−9.9 (3)C11—C10—C15—C140.3 (6)
C24—Ir1—N1—C7106.5 (3)C9—C10—C15—C14−178.7 (4)
C9—Ir1—N1—C79.0 (3)C22—S2—C16—C17179.6 (4)
N2—Ir1—N1—C773.3 (14)C22—S2—C16—C210.4 (3)
O2—Ir1—N1—C7−79.3 (3)C21—C16—C17—C180.7 (6)
O1—Ir1—N1—C7−167.0 (2)S2—C16—C17—C18−178.5 (3)
C24—Ir1—N1—C6−72.7 (4)C16—C17—C18—C190.3 (6)
C9—Ir1—N1—C6−170.3 (4)C17—C18—C19—C20−0.7 (6)
N2—Ir1—N1—C6−106.0 (13)C18—C19—C20—C210.1 (6)
O2—Ir1—N1—C6101.4 (4)C22—N2—C21—C20−177.6 (4)
O1—Ir1—N1—C613.7 (4)Ir1—N2—C21—C202.7 (6)
C24—Ir1—N2—C2211.8 (3)C22—N2—C21—C161.5 (5)
C9—Ir1—N2—C22109.1 (3)Ir1—N2—C21—C16−178.2 (3)
N1—Ir1—N2—C2245.4 (15)C19—C20—C21—N2179.9 (4)
O2—Ir1—N2—C22−162.2 (2)C19—C20—C21—C160.8 (6)
O1—Ir1—N2—C22−74.7 (2)C17—C16—C21—N2179.6 (3)
C24—Ir1—N2—C21−168.5 (4)S2—C16—C21—N2−1.1 (4)
C9—Ir1—N2—C21−71.2 (4)C17—C16—C21—C20−1.2 (6)
N1—Ir1—N2—C21−134.9 (13)S2—C16—C21—C20178.1 (3)
O2—Ir1—N2—C2117.5 (3)C21—N2—C22—C23171.1 (3)
O1—Ir1—N2—C21105.0 (3)Ir1—N2—C22—C23−9.1 (4)
C7—S1—C1—C2179.4 (4)C21—N2—C22—S2−1.2 (4)
C7—S1—C1—C6−0.3 (3)Ir1—N2—C22—S2178.58 (16)
C6—C1—C2—C31.2 (6)C16—S2—C22—N20.5 (3)
S1—C1—C2—C3−178.4 (3)C16—S2—C22—C23−170.9 (4)
C1—C2—C3—C4−0.9 (6)N2—C22—C23—C24−1.5 (5)
C2—C3—C4—C50.1 (7)S2—C22—C23—C24169.5 (3)
C3—C4—C5—C60.4 (6)C22—C23—C24—C25−174.8 (3)
C7—N1—C6—C5−178.1 (4)C22—C23—C24—Ir111.9 (4)
Ir1—N1—C6—C51.2 (6)C9—Ir1—C24—C23−109.6 (3)
C7—N1—C6—C11.4 (5)N1—Ir1—C24—C23169.6 (3)
Ir1—N1—C6—C1−179.3 (3)N2—Ir1—C24—C23−13.0 (3)
C4—C5—C6—N1179.3 (4)O2—Ir1—C24—C2351.9 (12)
C4—C5—C6—C1−0.1 (6)O1—Ir1—C24—C2373.0 (3)
C2—C1—C6—N1179.7 (4)C9—Ir1—C24—C2577.5 (3)
S1—C1—C6—N1−0.5 (5)N1—Ir1—C24—C25−3.4 (3)
C2—C1—C6—C5−0.7 (6)N2—Ir1—C24—C25174.1 (3)
S1—C1—C6—C5179.0 (3)O2—Ir1—C24—C25−121.1 (10)
C6—N1—C7—C8172.9 (3)O1—Ir1—C24—C25−99.9 (3)
Ir1—N1—C7—C8−6.6 (4)C23—C24—C25—C30−62.4 (5)
C6—N1—C7—S1−1.7 (4)Ir1—C24—C25—C30110.2 (3)
Ir1—N1—C7—S1178.90 (17)C23—C24—C25—C26115.4 (4)
C1—S1—C7—N11.1 (3)Ir1—C24—C25—C26−72.1 (4)
C1—S1—C7—C8−172.6 (4)C30—C25—C26—C271.9 (6)
N1—C7—C8—C9−1.9 (5)C24—C25—C26—C27−175.9 (4)
S1—C7—C8—C9171.6 (3)C25—C26—C27—C28−1.8 (6)
C7—C8—C9—C10−175.3 (3)C26—C27—C28—F2178.8 (4)
C7—C8—C9—Ir19.7 (5)C26—C27—C28—C29−0.7 (6)
C24—Ir1—C9—C8−105.1 (3)F2—C28—C29—C30−176.5 (3)
N1—Ir1—C9—C8−10.2 (3)C27—C28—C29—C302.9 (6)
N2—Ir1—C9—C8173.9 (3)C26—C25—C30—C290.4 (6)
O2—Ir1—C9—C877.0 (3)C24—C25—C30—C29178.2 (3)
O1—Ir1—C9—C843.7 (16)C28—C29—C30—C25−2.8 (6)
C24—Ir1—C9—C1080.3 (3)Ir1—O1—C32—C33−5.2 (6)
N1—Ir1—C9—C10175.1 (3)Ir1—O1—C32—C31176.5 (2)
N2—Ir1—C9—C10−0.8 (3)O1—C32—C33—C34−4.9 (7)
O2—Ir1—C9—C10−97.7 (3)C31—C32—C33—C34173.4 (4)
O1—Ir1—C9—C10−131.0 (13)Ir1—O2—C34—C334.8 (6)
C8—C9—C10—C15134.5 (4)Ir1—O2—C34—C35−175.1 (2)
Ir1—C9—C10—C15−51.1 (5)C32—C33—C34—O25.1 (7)
C8—C9—C10—C11−44.4 (5)C32—C33—C34—C35−175.0 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2924).

References

  • Baldo, M. A., Obrien, D. F., You, Y., Shoustikov, A., Sibley, S., Thompson, M. E. & Forrest, S. R. (1998). Nature (London), 395, 151–154.
  • Forrest, S. R. (2003). Org. Electron 4, 45-48.
  • Li, W.-Y., Mao, L.-S., Lu, L. & He, H.-W. (2008). Acta Cryst. E64, m490. [PMC free article] [PubMed]
  • Rigaku (1999). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (1996). SADABS University of Go¨ttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography