cis-Bis[2-(1,3-benzothia­zol-2-yl)-1-(4-fluoro­phen­yl)ethen­yl](pentane-2,4-dionato-κ2O,O′)iridium(III)

Xiao, G.-Y.; Lei, P.; Chi, H.-J.; Hu, Z.-Z.; Li, X.

doi:10.1107/S1600536809010204

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m440

doi:10.1107/S1600536809010204

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cis-Bis[2-(1,3-benzothiazol-2-yl)-1-(4-fluorophenyl)ethenyl](pentane-2,4-dionato-κ²O,O′)iridium(III)

Guo-Yong Xiao,^a Peng Lei,^a Hai-Jun Chi,^a Zhi-Zhi Hu ^a ^* and Xiao Li ^b

^aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China, and ^bKey Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033, People's Republic of China
^*Correspondence e-mail: xiaoguoyong@sohu.com

(Received 9 March 2009; accepted 19 March 2009; online 25 March 2009)

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 ). For background to possible applications of this class of compound, see: Baldo et al. (1998 ); Forrest (2003 ).

Experimental

Crystal data

[Ir(C₁₅H₉FNS)₂(C₅H₇O₂)]
M_r = 799.89
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.05
5373 reflections
399 parameters
H-atom parameters constrained
Δρ_max = 1.37 e Å⁻³
Δρ_min = −2.58 e Å⁻³

Table 1
Selected bond lengths (Å)

Ir1—C9	2.000 (4)
Ir1—C24	1.988 (4)
Ir1—N1	2.045 (3)
Ir1—N2	2.049 (3)
Ir1—O1	2.137 (2)
Ir1—O2	2.137 (3)

Data collection: CrystalClear (Rigaku, 1999 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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]⁺.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalClear (Rigaku, 1999); 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: SHELXTL (Sheldrick, 2008).

Figures top

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

cis-Bis[2-(1,3-benzothiazol-2-yl)-1-(4-fluorophenyl)ethenyl](pentane- 2,4-dionato-κ²O,O')iridium(III) top

Crystal data top

[Ir(C₁₅H₉FNS)₂(C₅H₇O₂)]	F(000) = 1568
M_r = 799.89	D_x = 1.739 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10390 reflections
a = 9.1632 (18) Å	θ = 1.6–27.9°
b = 17.736 (4) Å	µ = 4.56 mm⁻¹
c = 18.823 (4) Å	T = 113 K
β = 93.06 (3)°	Prism, red
V = 3054.7 (11) Å³	0.16 × 0.14 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	5373 independent reflections
Radiation source: rotating anode	4792 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.055
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.529, T_max = 0.659	k = −21→20
20289 measured reflections	l = −22→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0328P)²] where P = (F_o² + 2F_c²)/3
5373 reflections	(Δ/σ)_max = 0.005
399 parameters	Δρ_max = 1.37 e Å⁻³
0 restraints	Δρ_min = −2.58 e Å⁻³

Crystal data top

[Ir(C₁₅H₉FNS)₂(C₅H₇O₂)]	V = 3054.7 (11) Å³
M_r = 799.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1632 (18) Å	µ = 4.56 mm⁻¹
b = 17.736 (4) Å	T = 113 K
c = 18.823 (4) Å	0.16 × 0.14 × 0.10 mm
β = 93.06 (3)°

Data collection top

Rigaku Saturn diffractometer	5373 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4792 reflections with I > 2σ(I)
T_min = 0.529, T_max = 0.659	R_int = 0.055
20289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	Δρ_max = 1.37 e Å⁻³
5373 reflections	Δρ_min = −2.58 e Å⁻³
399 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

	x	y	z	U_iso*/U_eq
Ir1	0.914147 (14)	0.885461 (7)	0.233249 (7)	0.01190 (7)
S1	0.66028 (11)	1.04464 (5)	0.36383 (6)	0.0239 (2)
S2	1.28983 (11)	0.75043 (6)	0.16085 (6)	0.0256 (3)
F1	1.5245 (3)	1.09581 (13)	0.14514 (15)	0.0368 (7)
F2	0.9677 (3)	0.84075 (14)	0.60215 (13)	0.0403 (7)
O1	0.8070 (3)	0.77954 (13)	0.21589 (14)	0.0151 (6)
O2	0.7795 (3)	0.92998 (13)	0.14703 (14)	0.0182 (6)
N1	0.7667 (3)	0.93021 (16)	0.29937 (16)	0.0133 (7)
N2	1.0741 (3)	0.84154 (16)	0.17349 (17)	0.0158 (7)
C1	0.5810 (4)	0.9564 (2)	0.3751 (2)	0.0206 (9)
C2	0.4627 (4)	0.9380 (2)	0.4159 (2)	0.0265 (10)
H2	0.4141	0.9749	0.4405	0.032*
C3	0.4204 (4)	0.8629 (2)	0.4183 (2)	0.0290 (11)
H3	0.3431	0.8489	0.4454	0.035*
C4	0.4931 (4)	0.8086 (2)	0.3802 (2)	0.0259 (10)
H4	0.4628	0.7586	0.3826	0.031*
C5	0.6090 (4)	0.8264 (2)	0.3390 (2)	0.0193 (9)
H5	0.6559	0.7894	0.3137	0.023*
C6	0.6529 (4)	0.9014 (2)	0.3367 (2)	0.0159 (9)
C7	0.7865 (4)	1.0049 (2)	0.3091 (2)	0.0175 (9)
C8	0.9091 (4)	1.0382 (2)	0.2803 (2)	0.0169 (9)
H8	0.9285	1.0896	0.2836	0.020*
C9	0.9980 (4)	0.9889 (2)	0.2469 (2)	0.0149 (8)
C10	1.1375 (4)	1.01596 (19)	0.21908 (19)	0.0140 (8)
C11	1.1421 (4)	1.0838 (2)	0.1814 (2)	0.0186 (9)
H11	1.0570	1.1119	0.1737	0.022*
C12	1.2707 (5)	1.10982 (19)	0.1553 (2)	0.0233 (10)
H12	1.2725	1.1540	0.1288	0.028*
C13	1.3955 (4)	1.0689 (2)	0.1695 (2)	0.0221 (9)
C14	1.3982 (4)	1.0015 (2)	0.2060 (2)	0.0217 (9)
H14	1.4845	0.9744	0.2137	0.026*
C15	1.2674 (4)	0.9756 (2)	0.2307 (2)	0.0174 (9)
H15	1.2661	0.9303	0.2555	0.021*
C16	1.2342 (4)	0.8054 (2)	0.0874 (2)	0.0212 (9)
C17	1.2906 (4)	0.8077 (2)	0.0208 (2)	0.0250 (10)
H17	1.3676	0.7764	0.0098	0.030*
C18	1.2303 (4)	0.8576 (2)	−0.0292 (2)	0.0273 (10)
H18	1.2666	0.8597	−0.0743	0.033*
C19	1.1142 (5)	0.9049 (2)	−0.0119 (2)	0.0252 (10)
H19	1.0752	0.9386	−0.0457	0.030*
C20	1.0576 (4)	0.9023 (2)	0.0542 (2)	0.0209 (9)
H20	0.9808	0.9339	0.0650	0.025*
C21	1.1164 (4)	0.8520 (2)	0.1048 (2)	0.0167 (9)
C22	1.1555 (4)	0.7908 (2)	0.2101 (2)	0.0192 (9)
C23	1.1358 (4)	0.7834 (2)	0.2839 (2)	0.0176 (9)
H23	1.1867	0.7486	0.3127	0.021*
C24	1.0345 (4)	0.83243 (19)	0.3087 (2)	0.0175 (9)
C25	1.0106 (4)	0.83624 (19)	0.3856 (2)	0.0150 (8)
C26	1.0432 (5)	0.9016 (2)	0.4245 (2)	0.0238 (10)
H26	1.0747	0.9445	0.4013	0.029*
C27	1.0292 (5)	0.9029 (2)	0.4973 (2)	0.0272 (10)
H27	1.0534	0.9460	0.5236	0.033*
C28	0.9786 (4)	0.8394 (2)	0.5300 (2)	0.0255 (10)
C29	0.9402 (4)	0.7751 (2)	0.4934 (2)	0.0252 (10)
H29	0.9022	0.7337	0.5165	0.030*
C30	0.9599 (4)	0.7738 (2)	0.4208 (2)	0.0205 (9)
H30	0.9385	0.7299	0.3953	0.025*
C31	0.6666 (4)	0.6829 (2)	0.1608 (2)	0.0266 (10)
H31A	0.7460	0.6495	0.1738	0.040*
H31B	0.6284	0.6709	0.1137	0.040*
H31C	0.5910	0.6772	0.1937	0.040*
C32	0.7211 (4)	0.7637 (2)	0.1626 (2)	0.0178 (9)
C33	0.6716 (4)	0.8130 (2)	0.1087 (2)	0.0200 (9)
H33	0.6150	0.7918	0.0714	0.024*
C34	0.6972 (4)	0.89059 (19)	0.1044 (2)	0.0182 (9)
C35	0.6229 (4)	0.9345 (2)	0.0443 (2)	0.0258 (10)
H35A	0.5891	0.9818	0.0620	0.039*
H35B	0.5414	0.9062	0.0244	0.039*
H35C	0.6910	0.9436	0.0082	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.01140 (11)	0.01073 (11)	0.01329 (12)	0.00056 (5)	−0.00189 (7)	−0.00079 (5)
S1	0.0190 (6)	0.0185 (5)	0.0348 (7)	0.0027 (4)	0.0051 (4)	−0.0084 (5)
S2	0.0216 (6)	0.0302 (6)	0.0253 (7)	0.0104 (5)	0.0026 (4)	−0.0051 (5)
F1	0.0272 (15)	0.0348 (14)	0.0501 (19)	−0.0077 (12)	0.0173 (12)	0.0091 (13)
F2	0.0611 (19)	0.0461 (16)	0.0138 (15)	0.0079 (13)	0.0026 (12)	−0.0008 (12)
O1	0.0159 (15)	0.0150 (13)	0.0143 (15)	−0.0023 (11)	−0.0009 (11)	0.0011 (11)
O2	0.0196 (15)	0.0139 (14)	0.0204 (16)	0.0014 (12)	−0.0054 (11)	−0.0001 (12)
N1	0.0143 (17)	0.0149 (17)	0.0107 (17)	0.0001 (13)	−0.0013 (12)	−0.0015 (14)
N2	0.0152 (17)	0.0144 (17)	0.0177 (19)	−0.0022 (14)	−0.0011 (13)	−0.0049 (14)
C1	0.016 (2)	0.019 (2)	0.026 (3)	0.0011 (17)	−0.0021 (17)	−0.0025 (18)
C2	0.020 (2)	0.031 (2)	0.029 (3)	0.0056 (19)	0.0019 (18)	−0.004 (2)
C3	0.018 (2)	0.035 (3)	0.034 (3)	0.000 (2)	0.0039 (19)	0.002 (2)
C4	0.020 (2)	0.025 (2)	0.032 (3)	−0.0017 (19)	0.0001 (18)	0.000 (2)
C5	0.017 (2)	0.019 (2)	0.021 (2)	0.0022 (17)	−0.0030 (16)	−0.0006 (17)
C6	0.012 (2)	0.021 (2)	0.014 (2)	0.0031 (17)	−0.0020 (15)	−0.0008 (17)
C7	0.012 (2)	0.022 (2)	0.019 (2)	0.0040 (17)	−0.0044 (15)	−0.0051 (18)
C8	0.018 (2)	0.0093 (19)	0.023 (2)	−0.0016 (16)	−0.0021 (16)	−0.0011 (17)
C9	0.017 (2)	0.016 (2)	0.012 (2)	0.0013 (17)	−0.0036 (15)	0.0020 (16)
C10	0.019 (2)	0.0140 (19)	0.009 (2)	−0.0043 (16)	−0.0004 (15)	−0.0023 (16)
C11	0.021 (2)	0.014 (2)	0.020 (2)	0.0050 (17)	−0.0021 (16)	0.0002 (17)
C12	0.033 (3)	0.013 (2)	0.024 (3)	−0.0005 (17)	0.005 (2)	0.0048 (17)
C13	0.019 (2)	0.026 (2)	0.022 (2)	−0.0073 (18)	0.0077 (17)	−0.0017 (19)
C14	0.014 (2)	0.022 (2)	0.028 (3)	−0.0019 (18)	−0.0042 (17)	0.000 (2)
C15	0.017 (2)	0.0137 (19)	0.021 (2)	−0.0018 (17)	−0.0030 (16)	0.0028 (17)
C16	0.013 (2)	0.025 (2)	0.026 (3)	−0.0034 (18)	0.0031 (17)	−0.0086 (19)
C17	0.019 (2)	0.029 (2)	0.027 (3)	−0.0072 (19)	0.0046 (18)	−0.011 (2)
C18	0.028 (3)	0.034 (2)	0.020 (3)	−0.018 (2)	0.0068 (18)	−0.005 (2)
C19	0.032 (3)	0.020 (2)	0.023 (3)	−0.011 (2)	0.0017 (19)	0.0021 (19)
C20	0.024 (2)	0.018 (2)	0.020 (2)	−0.0042 (18)	−0.0023 (17)	−0.0009 (19)
C21	0.018 (2)	0.015 (2)	0.017 (2)	−0.0063 (17)	0.0012 (16)	−0.0051 (18)
C22	0.015 (2)	0.013 (2)	0.030 (3)	−0.0002 (17)	−0.0009 (17)	−0.0014 (18)
C23	0.019 (2)	0.017 (2)	0.016 (2)	0.0020 (17)	−0.0036 (16)	−0.0025 (17)
C24	0.015 (2)	0.010 (2)	0.027 (3)	−0.0047 (16)	−0.0021 (16)	0.0000 (17)
C25	0.0101 (19)	0.017 (2)	0.018 (2)	0.0042 (16)	−0.0041 (15)	−0.0021 (17)
C26	0.029 (3)	0.019 (2)	0.024 (3)	0.0003 (18)	−0.0016 (19)	0.0010 (19)
C27	0.037 (3)	0.024 (2)	0.020 (3)	0.007 (2)	−0.0065 (19)	−0.010 (2)
C28	0.030 (3)	0.033 (3)	0.013 (2)	0.011 (2)	−0.0030 (17)	0.002 (2)
C29	0.028 (3)	0.022 (2)	0.025 (3)	0.0038 (19)	0.0007 (18)	0.0072 (19)
C30	0.022 (2)	0.019 (2)	0.020 (2)	0.0023 (17)	−0.0032 (17)	0.0005 (18)
C31	0.025 (2)	0.020 (2)	0.033 (3)	−0.0095 (18)	−0.0069 (18)	0.001 (2)
C32	0.013 (2)	0.017 (2)	0.024 (3)	−0.0030 (17)	0.0025 (16)	−0.0024 (18)
C33	0.021 (2)	0.021 (2)	0.018 (2)	−0.0076 (17)	−0.0081 (16)	−0.0038 (18)
C34	0.017 (2)	0.021 (2)	0.017 (2)	0.0016 (16)	−0.0033 (17)	0.0028 (17)
C35	0.027 (2)	0.022 (2)	0.027 (3)	−0.0014 (18)	−0.0109 (18)	0.0031 (19)

Geometric parameters (Å, º) top

Ir1—C9	2.000 (4)	C14—C15	1.387 (5)
Ir1—C24	1.988 (4)	C14—H14	0.9300
Ir1—N1	2.045 (3)	C15—H15	0.9300
Ir1—N2	2.049 (3)	C16—C17	1.380 (5)
Ir1—O1	2.137 (2)	C16—C21	1.411 (5)
Ir1—O2	2.137 (3)	C17—C18	1.385 (6)
S1—C7	1.739 (4)	C17—H17	0.9300
S1—C1	1.743 (4)	C18—C19	1.407 (6)
S2—C22	1.734 (4)	C18—H18	0.9300
S2—C16	1.746 (4)	C19—C20	1.373 (5)
F1—C13	1.376 (4)	C19—H19	0.9300
F2—C28	1.368 (5)	C20—C21	1.393 (6)
O1—C32	1.273 (5)	C20—H20	0.9300
O2—C34	1.280 (5)	C22—C23	1.416 (5)
N1—C7	1.348 (4)	C23—C24	1.372 (5)
N1—C6	1.386 (5)	C23—H23	0.9300
N2—C22	1.336 (5)	C24—C25	1.477 (5)
N2—C21	1.382 (5)	C25—C30	1.384 (5)
C1—C2	1.399 (5)	C25—C26	1.394 (5)
C1—C6	1.399 (5)	C26—C27	1.384 (6)
C2—C3	1.389 (6)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.375 (6)
C3—C4	1.391 (6)	C27—H27	0.9300
C3—H3	0.9300	C28—C29	1.369 (6)
C4—C5	1.385 (5)	C29—C30	1.388 (5)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.391 (5)	C30—H30	0.9300
C5—H5	0.9300	C31—C32	1.518 (5)
C7—C8	1.404 (5)	C31—H31A	0.9600
C8—C9	1.371 (5)	C31—H31B	0.9600
C8—H8	0.9300	C31—H31C	0.9600
C9—C10	1.486 (5)	C32—C33	1.397 (5)
C10—C15	1.396 (5)	C33—C34	1.399 (5)
C10—C11	1.399 (5)	C33—H33	0.9300
C11—C12	1.380 (5)	C34—C35	1.505 (5)
C11—H11	0.9300	C35—H35A	0.9600
C12—C13	1.369 (6)	C35—H35B	0.9600
C12—H12	0.9300	C35—H35C	0.9600
C13—C14	1.378 (6)

C24—Ir1—C9	98.48 (15)	C14—C15—H15	119.3
C24—Ir1—N1	96.20 (14)	C10—C15—H15	119.3
C9—Ir1—N1	80.09 (13)	C17—C16—C21	121.4 (4)
C24—Ir1—N2	80.01 (14)	C17—C16—S2	128.9 (3)
C9—Ir1—N2	97.92 (13)	C21—C16—S2	109.7 (3)
N1—Ir1—N2	175.46 (12)	C16—C17—C18	118.7 (4)
C24—Ir1—O2	173.43 (12)	C16—C17—H17	120.6
C9—Ir1—O2	87.76 (12)	C18—C17—H17	120.6
N1—Ir1—O2	86.88 (11)	C17—C18—C19	120.2 (4)
N2—Ir1—O2	97.15 (11)	C17—C18—H18	119.9
C24—Ir1—O1	85.77 (12)	C19—C18—H18	119.9
C9—Ir1—O1	175.04 (12)	C20—C19—C18	121.1 (4)
N1—Ir1—O1	96.96 (10)	C20—C19—H19	119.4
N2—Ir1—O1	85.30 (10)	C18—C19—H19	119.4
O2—Ir1—O1	88.10 (10)	C19—C20—C21	119.3 (4)
C7—S1—C1	90.17 (18)	C19—C20—H20	120.4
C22—S2—C16	90.42 (18)	C21—C20—H20	120.4
C32—O1—Ir1	125.0 (2)	N2—C21—C20	127.4 (4)
C34—O2—Ir1	124.9 (2)	N2—C21—C16	113.3 (4)
C7—N1—C6	113.1 (3)	C20—C21—C16	119.3 (4)
C7—N1—Ir1	112.0 (2)	N2—C22—C23	118.1 (3)
C6—N1—Ir1	134.8 (2)	N2—C22—S2	113.3 (3)
C22—N2—C21	113.3 (3)	C23—C22—S2	128.1 (3)
C22—N2—Ir1	111.7 (3)	C24—C23—C22	113.6 (4)
C21—N2—Ir1	135.0 (3)	C24—C23—H23	123.2
C2—C1—C6	121.4 (4)	C22—C23—H23	123.2
C2—C1—S1	128.0 (3)	C23—C24—C25	120.1 (4)
C6—C1—S1	110.6 (3)	C23—C24—Ir1	114.6 (3)
C3—C2—C1	117.8 (4)	C25—C24—Ir1	124.9 (3)
C3—C2—H2	121.1	C30—C25—C26	118.8 (4)
C1—C2—H2	121.1	C30—C25—C24	120.3 (3)
C2—C3—C4	120.4 (4)	C26—C25—C24	120.9 (3)
C2—C3—H3	119.8	C27—C26—C25	120.4 (4)
C4—C3—H3	119.8	C27—C26—H26	119.8
C5—C4—C3	122.2 (4)	C25—C26—H26	119.8
C5—C4—H4	118.9	C28—C27—C26	118.7 (4)
C3—C4—H4	118.9	C28—C27—H27	120.7
C4—C5—C6	117.9 (4)	C26—C27—H27	120.7
C4—C5—H5	121.1	F2—C28—C29	118.9 (4)
C6—C5—H5	121.1	F2—C28—C27	118.3 (4)
N1—C6—C5	126.5 (3)	C29—C28—C27	122.8 (4)
N1—C6—C1	113.1 (3)	C28—C29—C30	117.7 (4)
C5—C6—C1	120.3 (3)	C28—C29—H29	121.1
N1—C7—C8	117.8 (3)	C30—C29—H29	121.1
N1—C7—S1	112.9 (3)	C25—C30—C29	121.5 (4)
C8—C7—S1	129.0 (3)	C25—C30—H30	119.2
C9—C8—C7	114.6 (3)	C29—C30—H30	119.2
C9—C8—H8	122.7	C32—C31—H31A	109.5
C7—C8—H8	122.7	C32—C31—H31B	109.5
C8—C9—C10	119.9 (3)	H31A—C31—H31B	109.5
C8—C9—Ir1	114.2 (3)	C32—C31—H31C	109.5
C10—C9—Ir1	125.7 (3)	H31A—C31—H31C	109.5
C15—C10—C11	118.2 (3)	H31B—C31—H31C	109.5
C15—C10—C9	121.4 (3)	O1—C32—C33	126.7 (3)
C11—C10—C9	120.4 (3)	O1—C32—C31	114.5 (3)
C12—C11—C10	121.2 (4)	C33—C32—C31	118.7 (4)
C12—C11—H11	119.4	C32—C33—C34	127.5 (4)
C10—C11—H11	119.4	C32—C33—H33	116.2
C13—C12—C11	118.3 (4)	C34—C33—H33	116.2
C13—C12—H12	120.8	O2—C34—C33	126.5 (4)
C11—C12—H12	120.8	O2—C34—C35	114.6 (3)
C12—C13—F1	118.4 (4)	C33—C34—C35	118.8 (3)
C12—C13—C14	123.3 (3)	C34—C35—H35A	109.5
F1—C13—C14	118.3 (4)	C34—C35—H35B	109.5
C13—C14—C15	117.5 (4)	H35A—C35—H35B	109.5
C13—C14—H14	121.2	C34—C35—H35C	109.5
C15—C14—H14	121.2	H35A—C35—H35C	109.5
C14—C15—C10	121.5 (4)	H35B—C35—H35C	109.5

C24—Ir1—O1—C32	−167.6 (3)	Ir1—C9—C10—C11	130.0 (3)
C9—Ir1—O1—C32	43.4 (15)	C15—C10—C11—C12	0.9 (6)
N1—Ir1—O1—C32	96.7 (3)	C9—C10—C11—C12	179.9 (4)
N2—Ir1—O1—C32	−87.3 (3)	C10—C11—C12—C13	−2.3 (6)
O2—Ir1—O1—C32	10.0 (3)	C11—C12—C13—F1	−178.4 (4)
C24—Ir1—O2—C34	11.2 (12)	C11—C12—C13—C14	2.7 (6)
C9—Ir1—O2—C34	172.9 (3)	C12—C13—C14—C15	−1.6 (6)
N1—Ir1—O2—C34	−106.9 (3)	F1—C13—C14—C15	179.5 (3)
N2—Ir1—O2—C34	75.2 (3)	C13—C14—C15—C10	0.1 (6)
O1—Ir1—O2—C34	−9.9 (3)	C11—C10—C15—C14	0.3 (6)
C24—Ir1—N1—C7	106.5 (3)	C9—C10—C15—C14	−178.7 (4)
C9—Ir1—N1—C7	9.0 (3)	C22—S2—C16—C17	179.6 (4)
N2—Ir1—N1—C7	73.3 (14)	C22—S2—C16—C21	0.4 (3)
O2—Ir1—N1—C7	−79.3 (3)	C21—C16—C17—C18	0.7 (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—C19	0.3 (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—C21	0.1 (6)
O2—Ir1—N1—C6	101.4 (4)	C22—N2—C21—C20	−177.6 (4)
O1—Ir1—N1—C6	13.7 (4)	Ir1—N2—C21—C20	2.7 (6)
C24—Ir1—N2—C22	11.8 (3)	C22—N2—C21—C16	1.5 (5)
C9—Ir1—N2—C22	109.1 (3)	Ir1—N2—C21—C16	−178.2 (3)
N1—Ir1—N2—C22	45.4 (15)	C19—C20—C21—N2	179.9 (4)
O2—Ir1—N2—C22	−162.2 (2)	C19—C20—C21—C16	0.8 (6)
O1—Ir1—N2—C22	−74.7 (2)	C17—C16—C21—N2	179.6 (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—C20	178.1 (3)
O2—Ir1—N2—C21	17.5 (3)	C21—N2—C22—C23	171.1 (3)
O1—Ir1—N2—C21	105.0 (3)	Ir1—N2—C22—C23	−9.1 (4)
C7—S1—C1—C2	179.4 (4)	C21—N2—C22—S2	−1.2 (4)
C7—S1—C1—C6	−0.3 (3)	Ir1—N2—C22—S2	178.58 (16)
C6—C1—C2—C3	1.2 (6)	C16—S2—C22—N2	0.5 (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—C5	0.1 (7)	S2—C22—C23—C24	169.5 (3)
C3—C4—C5—C6	0.4 (6)	C22—C23—C24—C25	−174.8 (3)
C7—N1—C6—C5	−178.1 (4)	C22—C23—C24—Ir1	11.9 (4)
Ir1—N1—C6—C5	1.2 (6)	C9—Ir1—C24—C23	−109.6 (3)
C7—N1—C6—C1	1.4 (5)	N1—Ir1—C24—C23	169.6 (3)
Ir1—N1—C6—C1	−179.3 (3)	N2—Ir1—C24—C23	−13.0 (3)
C4—C5—C6—N1	179.3 (4)	O2—Ir1—C24—C23	51.9 (12)
C4—C5—C6—C1	−0.1 (6)	O1—Ir1—C24—C23	73.0 (3)
C2—C1—C6—N1	179.7 (4)	C9—Ir1—C24—C25	77.5 (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—C25	174.1 (3)
S1—C1—C6—C5	179.0 (3)	O2—Ir1—C24—C25	−121.1 (10)
C6—N1—C7—C8	172.9 (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—C30	110.2 (3)
Ir1—N1—C7—S1	178.90 (17)	C23—C24—C25—C26	115.4 (4)
C1—S1—C7—N1	1.1 (3)	Ir1—C24—C25—C26	−72.1 (4)
C1—S1—C7—C8	−172.6 (4)	C30—C25—C26—C27	1.9 (6)
N1—C7—C8—C9	−1.9 (5)	C24—C25—C26—C27	−175.9 (4)
S1—C7—C8—C9	171.6 (3)	C25—C26—C27—C28	−1.8 (6)
C7—C8—C9—C10	−175.3 (3)	C26—C27—C28—F2	178.8 (4)
C7—C8—C9—Ir1	9.7 (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—C30	2.9 (6)
N2—Ir1—C9—C8	173.9 (3)	C26—C25—C30—C29	0.4 (6)
O2—Ir1—C9—C8	77.0 (3)	C24—C25—C30—C29	178.2 (3)
O1—Ir1—C9—C8	43.7 (16)	C28—C29—C30—C25	−2.8 (6)
C24—Ir1—C9—C10	80.3 (3)	Ir1—O1—C32—C33	−5.2 (6)
N1—Ir1—C9—C10	175.1 (3)	Ir1—O1—C32—C31	176.5 (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—C34	173.4 (4)
O1—Ir1—C9—C10	−131.0 (13)	Ir1—O2—C34—C33	4.8 (6)
C8—C9—C10—C15	134.5 (4)	Ir1—O2—C34—C35	−175.1 (2)
Ir1—C9—C10—C15	−51.1 (5)	C32—C33—C34—O2	5.1 (7)
C8—C9—C10—C11	−44.4 (5)	C32—C33—C34—C35	−175.0 (4)

Experimental details

Crystal data
Chemical formula	[Ir(C₁₅H₉FNS)₂(C₅H₇O₂)]
M_r	799.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	9.1632 (18), 17.736 (4), 18.823 (4)
β (°)	93.06 (3)
V (Å³)	3054.7 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.56
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.529, 0.659
No. of measured, independent and observed [I > 2σ(I)] reflections	20289, 5373, 4792
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.05
No. of reflections	5373
No. of parameters	399
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.37, −2.58

Computer programs: CrystalClear (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ir1—C9	2.000 (4)	Ir1—N2	2.049 (3)
Ir1—C24	1.988 (4)	Ir1—O1	2.137 (2)
Ir1—N1	2.045 (3)	Ir1—O2	2.137 (3)

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. CAS Google Scholar
Forrest, S. R. (2003). Org. Electron. 4, 45-48. Web of Science CrossRef Google Scholar
Li, W.-Y., Mao, L.-S., Lu, L. & He, H.-W. (2008). Acta Cryst. E64, m490. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Go¨ttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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