cis-Bis[2-(1,3-benzothia-zol-2-yl)-1-(4-fluoro-phen-yl)ethen-yl](pentane-2,4-dionato-κO,O')iridium(III).

In the title compound, [Ir(C(15)H(9)FNS)(2)(C(5)H(7)O(2))], the Ir atom is hexa-coordinated by three chelating ligands, with two cyclo-metalated 2-(1,3-benzothia-zol-2-yl)-1-(4-fluoro-phen-yl)ethenyl ligands showing N,C-bidentate coordination and an O,O'-bidenate pentane-2,4-dionate anion, thereby forming a distorted octa-hedral 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 = 799.89

Monoclinic,

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[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 ▶); 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.

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

[Ir(C15H9FNS)2(C5H7O2)]	F(000) = 1568
Mr = 799.89	Dx = 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

Rigaku Saturn diffractometer	5373 independent reflections
Radiation source: rotating anode	4792 reflections with I > 2σ(I)
confocal	Rint = 0.055
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.529, Tmax = 0.659	k = −21→20
20289 measured reflections	l = −22→21

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(Fo2) + (0.0328P)2] where P = (Fo2 + 2Fc2)/3
5373 reflections	(Δ/σ)max = 0.005
399 parameters	Δρmax = 1.37 e Å−3
0 restraints	Δρmin = −2.58 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)