Carbon­yl(diethyl­dithio­carbamato)(η⁵-penta­methyl­cyclo­penta­dien­yl)iridium(III) trifluoro­methane­sulfonate

Cations of the title compound, [Ir(C₁₀H₁₅)(C₅H₁₀NS₂)(CO)](CF₃O₃S), contain half-sandwich (η⁵-C₅Me₅)Ir^III fragments. The remaining positions in the octa­hedral Ir^III coordination environment are occupied by the S atoms of the bidentate diethyl­dithio­carbamate ligand and the C atom of the carbonyl ligand.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.025
• wR factor = 0.063
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ir1    -   S2      ..       5.42 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S10
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C10
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         27
            C12 -IR1 -C1  -O1     -7.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            C14 -IR1 -C1  -O1    -18.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            C15 -IR1 -C1  -O1     20.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            C13 -IR1 -C1  -O1    -44.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            C11 -IR1 -C1  -O1     43.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            S1  -IR1 -C1  -O1    143.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            S2  -IR1 -C1  -O1   -145.00 13.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

Carbonyl(diethyldithiocarbamato)(η⁵-pentamethylcyclopentadienyl)iridium(III) trifluoromethanesulfonate

Crystal data

[Ir(C10H15)(C5H10NS2)(CO)](CF3O3S)	Z = 2
Mr = 652.76	F(000) = 636
Triclinic, P1	Dx = 1.818 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.194 (4) Å	Cell parameters from 16 reflections
b = 12.1398 (12) Å	θ = 5.3–12.4°
c = 13.2421 (19) Å	µ = 5.91 mm^−1
α = 112.061 (7)°	T = 292 K
β = 101.245 (17)°	Prism, yellow
γ = 90.470 (15)°	0.46 × 0.44 × 0.33 mm
V = 1192.6 (6) Å^3

Data collection

Siemens P4 diffractometer	3830 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −9→1
Absorption correction: empirical (using intensity measurements) via ψ scans (North et al., 1968)	k = −13→13
Tmin = 0.081, Tmax = 0.145	l = −15→15
5035 measured reflections	3 standard reflections every 97 reflections
4099 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0341P)^2 + 0.7703P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.009
4099 reflections	Δρmax = 0.78 e Å^−3
264 parameters	Δρmin = −0.88 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0089 (5)

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 (Ų)

	x	y	z	Uiso*/Ueq
Ir1	0.200390 (19)	0.093672 (13)	0.833455 (13)	0.04038 (9)
S1	0.25931 (15)	−0.09841 (11)	0.83215 (11)	0.0552 (3)
S2	−0.02910 (14)	−0.04404 (10)	0.71040 (10)	0.0495 (3)
N1	0.0003 (5)	−0.2639 (3)	0.7139 (3)	0.0493 (9)
C2	0.0669 (5)	−0.1538 (4)	0.7457 (4)	0.0444 (9)
C3	0.0898 (7)	−0.3515 (4)	0.7515 (5)	0.0622 (13)
H31	0.0101	−0.4018	0.7642	0.075*
H32	0.1679	−0.3094	0.8217	0.075*
C31	0.1827 (11)	−0.4281 (7)	0.6679 (7)	0.108 (3)
H311	0.2464	−0.4792	0.6977	0.162*
H312	0.2567	−0.3783	0.6516	0.162*
H313	0.1046	−0.4759	0.6007	0.162*
C4	−0.1701 (7)	−0.3015 (5)	0.6450 (4)	0.0614 (13)
H41	−0.1786	−0.3864	0.6002	0.074*
H42	−0.1908	−0.2599	0.5945	0.074*
C41	−0.3023 (7)	−0.2765 (5)	0.7144 (6)	0.0741 (16)
H411	−0.2874	−0.3221	0.7605	0.111*
H412	−0.4111	−0.2984	0.6660	0.111*
H413	−0.2921	−0.1930	0.7607	0.111*
C1	0.0953 (8)	0.1310 (6)	0.9533 (5)	0.0725 (16)
O1	0.0344 (8)	0.1591 (6)	1.0281 (4)	0.136 (3)
C11	0.4561 (6)	0.1426 (4)	0.8207 (5)	0.0553 (12)
C111	0.6106 (7)	0.0813 (6)	0.8438 (7)	0.085 (2)
H111	0.7044	0.1185	0.8314	0.127*
H112	0.5935	−0.0015	0.7948	0.127*
H113	0.6320	0.0878	0.9199	0.127*
C12	0.3441 (7)	0.1113 (4)	0.7153 (5)	0.0577 (13)
C121	0.3589 (11)	0.0154 (6)	0.6065 (6)	0.101 (3)
H121	0.4367	0.0441	0.5745	0.151*
H122	0.2516	−0.0056	0.5563	0.151*
H123	0.3978	−0.0536	0.6193	0.151*
C13	0.2197 (6)	0.1977 (4)	0.7287 (4)	0.0473 (10)
C131	0.0838 (8)	0.2060 (6)	0.6387 (5)	0.0763 (16)
H131	−0.0116	0.2355	0.6693	0.114*
H132	0.0528	0.1284	0.5805	0.114*
H133	0.1230	0.2595	0.6088	0.114*
C14	0.2549 (6)	0.2752 (4)	0.8414 (4)	0.0465 (10)
C141	0.1651 (8)	0.3844 (5)	0.8925 (5)	0.0709 (15)
H141	0.2101	0.4503	0.8801	0.106*
H142	0.1802	0.4040	0.9713	0.106*
H143	0.0481	0.3681	0.8587	0.106*
C15	0.4003 (6)	0.2420 (4)	0.8993 (4)	0.0489 (10)
C151	0.4882 (8)	0.3100 (6)	1.0180 (5)	0.0828 (18)
H151	0.5838	0.3576	1.0199	0.124*
H152	0.5237	0.2551	1.0526	0.124*
H153	0.4133	0.3610	1.0575	0.124*
S10	0.33933 (17)	0.61785 (12)	0.25494 (13)	0.0638 (3)
O11	0.2804 (6)	0.7264 (4)	0.2498 (5)	0.0915 (14)
O12	0.4915 (6)	0.5873 (5)	0.2171 (5)	0.1015 (15)
O13	0.2149 (6)	0.5216 (5)	0.2183 (5)	0.1008 (16)
C10	0.4027 (9)	0.6548 (6)	0.4022 (6)	0.0805 (17)
F11	0.5204 (8)	0.7454 (4)	0.4510 (4)	0.141 (2)
F12	0.2763 (9)	0.6842 (7)	0.4523 (5)	0.159 (3)
F13	0.4650 (7)	0.5644 (4)	0.4261 (4)	0.1174 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.03992 (12)	0.03982 (12)	0.04199 (12)	0.00010 (7)	0.01340 (7)	0.01420 (7)
S1	0.0446 (6)	0.0529 (7)	0.0731 (8)	−0.0051 (5)	−0.0008 (6)	0.0365 (6)
S2	0.0432 (6)	0.0484 (6)	0.0554 (6)	0.0009 (5)	0.0034 (5)	0.0218 (5)
N1	0.049 (2)	0.043 (2)	0.054 (2)	−0.0029 (16)	0.0138 (17)	0.0163 (17)
C2	0.044 (2)	0.044 (2)	0.046 (2)	0.0012 (18)	0.0130 (19)	0.0165 (19)
C3	0.065 (3)	0.045 (3)	0.082 (4)	0.001 (2)	0.018 (3)	0.029 (3)
C31	0.129 (7)	0.091 (5)	0.130 (7)	0.058 (5)	0.064 (6)	0.053 (5)
C4	0.062 (3)	0.048 (3)	0.060 (3)	−0.010 (2)	0.003 (2)	0.010 (2)
C41	0.052 (3)	0.066 (3)	0.101 (4)	−0.002 (3)	0.013 (3)	0.029 (3)
C1	0.071 (4)	0.081 (4)	0.055 (3)	−0.023 (3)	0.025 (3)	0.009 (3)
O1	0.136 (5)	0.171 (6)	0.076 (3)	−0.044 (4)	0.067 (3)	−0.003 (3)
C11	0.039 (2)	0.051 (3)	0.096 (4)	0.007 (2)	0.029 (2)	0.044 (3)
C111	0.053 (3)	0.080 (4)	0.156 (7)	0.021 (3)	0.046 (4)	0.073 (4)
C12	0.070 (3)	0.048 (3)	0.070 (3)	0.007 (2)	0.044 (3)	0.025 (2)
C121	0.153 (7)	0.067 (4)	0.098 (5)	0.017 (4)	0.093 (5)	0.017 (4)
C13	0.054 (3)	0.045 (2)	0.046 (2)	0.0000 (19)	0.015 (2)	0.0189 (19)
C131	0.088 (4)	0.090 (4)	0.059 (3)	0.005 (3)	0.005 (3)	0.043 (3)
C14	0.045 (2)	0.039 (2)	0.057 (3)	0.0066 (18)	0.015 (2)	0.0184 (19)
C141	0.077 (4)	0.050 (3)	0.084 (4)	0.022 (3)	0.023 (3)	0.020 (3)
C15	0.044 (2)	0.042 (2)	0.063 (3)	−0.0019 (19)	0.008 (2)	0.023 (2)
C151	0.079 (4)	0.071 (4)	0.079 (4)	−0.019 (3)	−0.017 (3)	0.024 (3)
S10	0.0569 (7)	0.0605 (7)	0.0832 (9)	−0.0009 (6)	0.0147 (7)	0.0383 (7)
O11	0.084 (3)	0.087 (3)	0.134 (4)	0.017 (2)	0.024 (3)	0.076 (3)
O12	0.091 (3)	0.093 (3)	0.130 (4)	0.016 (3)	0.057 (3)	0.038 (3)
O13	0.084 (3)	0.098 (3)	0.122 (4)	−0.030 (3)	−0.013 (3)	0.061 (3)
C10	0.087 (4)	0.070 (4)	0.085 (4)	0.010 (3)	0.015 (4)	0.032 (3)
F11	0.168 (5)	0.085 (3)	0.125 (4)	−0.021 (3)	−0.039 (4)	0.027 (3)
F12	0.168 (6)	0.234 (7)	0.122 (4)	0.084 (5)	0.081 (4)	0.095 (5)
F13	0.157 (4)	0.089 (3)	0.106 (3)	0.026 (3)	−0.012 (3)	0.058 (2)

Geometric parameters (Å, º)

Ir1—C1	1.862 (5)	C111—H111	0.9600
Ir1—C12	2.202 (4)	C111—H112	0.9600
Ir1—C14	2.204 (4)	C111—H113	0.9600
Ir1—C15	2.214 (4)	C12—C13	1.456 (7)
Ir1—C13	2.223 (4)	C12—C121	1.501 (8)
Ir1—C11	2.228 (4)	C121—H121	0.9600
Ir1—S1	2.3795 (12)	C121—H122	0.9600
Ir1—S2	2.3861 (14)	C121—H123	0.9600
S1—C2	1.717 (5)	C13—C14	1.403 (6)
S2—C2	1.719 (4)	C13—C131	1.498 (7)
N1—C2	1.318 (6)	C131—H131	0.9600
N1—C4	1.473 (6)	C131—H132	0.9600
N1—C3	1.478 (6)	C131—H133	0.9600
C3—C31	1.496 (9)	C14—C15	1.434 (6)
C3—H31	0.9700	C14—C141	1.514 (6)
C3—H32	0.9700	C141—H141	0.9600
C31—H311	0.9600	C141—H142	0.9600
C31—H312	0.9600	C141—H143	0.9600
C31—H313	0.9600	C15—C151	1.498 (7)
C4—C41	1.515 (8)	C151—H151	0.9600
C4—H41	0.9700	C151—H152	0.9600
C4—H42	0.9700	C151—H153	0.9600
C41—H411	0.9600	S10—O13	1.415 (5)
C41—H412	0.9600	S10—O11	1.428 (4)
C41—H413	0.9600	S10—O12	1.433 (5)
C1—O1	1.135 (7)	S10—C10	1.794 (7)
C11—C15	1.415 (7)	C10—F12	1.318 (8)
C11—C12	1.426 (8)	C10—F11	1.328 (8)
C11—C111	1.512 (7)	C10—F13	1.331 (7)
C1—Ir1—C12	161.8 (2)	C11—C111—H111	109.5
C1—Ir1—C14	99.2 (2)	C11—C111—H112	109.5
C12—Ir1—C14	62.92 (17)	H111—C111—H112	109.5
C1—Ir1—C15	101.0 (2)	C11—C111—H113	109.5
C12—Ir1—C15	62.95 (19)	H111—C111—H113	109.5
C14—Ir1—C15	37.86 (17)	H112—C111—H113	109.5
C1—Ir1—C13	128.2 (3)	C11—C12—C13	107.5 (4)
C12—Ir1—C13	38.41 (18)	C11—C12—C121	127.1 (6)
C14—Ir1—C13	36.95 (17)	C13—C12—C121	125.1 (6)
C15—Ir1—C13	62.87 (17)	C11—C12—Ir1	72.2 (3)
C1—Ir1—C11	132.6 (2)	C13—C12—Ir1	71.6 (2)
C12—Ir1—C11	37.5 (2)	C121—C12—Ir1	126.3 (4)
C14—Ir1—C11	62.43 (16)	C12—C121—H121	109.5
C15—Ir1—C11	37.13 (18)	C12—C121—H122	109.5
C13—Ir1—C11	62.94 (18)	H121—C121—H122	109.5
C1—Ir1—S1	93.6 (2)	C12—C121—H123	109.5
C12—Ir1—S1	102.11 (13)	H121—C121—H123	109.5
C14—Ir1—S1	156.98 (12)	H122—C121—H123	109.5
C15—Ir1—S1	120.83 (12)	C14—C13—C12	107.1 (4)
C13—Ir1—S1	137.84 (12)	C14—C13—C131	126.1 (5)
C11—Ir1—S1	94.89 (12)	C12—C13—C131	126.7 (5)
C1—Ir1—S2	91.89 (18)	C14—C13—Ir1	70.8 (2)
C12—Ir1—S2	101.57 (16)	C12—C13—Ir1	70.0 (2)
C14—Ir1—S2	125.57 (12)	C131—C13—Ir1	126.2 (4)
C15—Ir1—S2	160.25 (13)	C13—C131—H131	109.5
C13—Ir1—S2	97.39 (12)	C13—C131—H132	109.5
C11—Ir1—S2	134.99 (16)	H131—C131—H132	109.5
S1—Ir1—S2	72.60 (4)	C13—C131—H133	109.5
C2—S1—Ir1	88.53 (15)	H131—C131—H133	109.5
C2—S2—Ir1	88.27 (16)	H132—C131—H133	109.5
C2—N1—C4	120.9 (4)	C13—C14—C15	109.3 (4)
C2—N1—C3	121.2 (4)	C13—C14—C141	125.8 (4)
C4—N1—C3	117.8 (4)	C15—C14—C141	124.6 (4)
N1—C2—S1	124.7 (3)	C13—C14—Ir1	72.3 (2)
N1—C2—S2	124.9 (4)	C15—C14—Ir1	71.4 (2)
S1—C2—S2	110.4 (2)	C141—C14—Ir1	127.1 (4)
N1—C3—C31	111.9 (5)	C14—C141—H141	109.5
N1—C3—H31	109.2	C14—C141—H142	109.5
C31—C3—H31	109.2	H141—C141—H142	109.5
N1—C3—H32	109.2	C14—C141—H143	109.5
C31—C3—H32	109.2	H141—C141—H143	109.5
H31—C3—H32	107.9	H142—C141—H143	109.5
C3—C31—H311	109.5	C11—C15—C14	107.5 (4)
C3—C31—H312	109.5	C11—C15—C151	126.4 (5)
H311—C31—H312	109.5	C14—C15—C151	125.7 (5)
C3—C31—H313	109.5	C11—C15—Ir1	72.0 (3)
H311—C31—H313	109.5	C14—C15—Ir1	70.7 (3)
H312—C31—H313	109.5	C151—C15—Ir1	128.3 (4)
N1—C4—C41	112.5 (4)	C15—C151—H151	109.5
N1—C4—H41	109.1	C15—C151—H152	109.5
C41—C4—H41	109.1	H151—C151—H152	109.5
N1—C4—H42	109.1	C15—C151—H153	109.5
C41—C4—H42	109.1	H151—C151—H153	109.5
H41—C4—H42	107.8	H152—C151—H153	109.5
C4—C41—H411	109.5	O13—S10—O11	115.1 (3)
C4—C41—H412	109.5	O13—S10—O12	114.9 (3)
H411—C41—H412	109.5	O11—S10—O12	114.9 (3)
C4—C41—H413	109.5	O13—S10—C10	104.1 (3)
H411—C41—H413	109.5	O11—S10—C10	102.6 (3)
H412—C41—H413	109.5	O12—S10—C10	102.7 (4)
O1—C1—Ir1	176.8 (6)	F12—C10—F11	107.5 (7)
C15—C11—C12	108.5 (4)	F12—C10—F13	106.3 (6)
C15—C11—C111	125.8 (5)	F11—C10—F13	106.3 (6)
C12—C11—C111	125.6 (5)	F12—C10—S10	111.7 (5)
C15—C11—Ir1	70.9 (3)	F11—C10—S10	112.2 (5)
C12—C11—Ir1	70.2 (3)	F13—C10—S10	112.5 (5)
C111—C11—Ir1	125.7 (3)
C1—Ir1—S1—C2	87.8 (2)	C15—Ir1—C13—C14	−37.4 (3)
C12—Ir1—S1—C2	−101.6 (2)	C11—Ir1—C13—C14	−79.3 (3)
C14—Ir1—S1—C2	−148.3 (3)	S1—Ir1—C13—C14	−144.4 (2)
C15—Ir1—S1—C2	−167.1 (2)	S2—Ir1—C13—C14	143.4 (2)
C13—Ir1—S1—C2	−84.7 (2)	C1—Ir1—C13—C12	162.4 (3)
C11—Ir1—S1—C2	−138.9 (2)	C14—Ir1—C13—C12	117.2 (4)
S2—Ir1—S1—C2	−3.07 (15)	C15—Ir1—C13—C12	79.8 (3)
C1—Ir1—S2—C2	−90.1 (3)	C11—Ir1—C13—C12	37.9 (3)
C12—Ir1—S2—C2	102.3 (2)	S1—Ir1—C13—C12	−27.1 (4)
C14—Ir1—S2—C2	167.1 (2)	S2—Ir1—C13—C12	−99.3 (3)
C15—Ir1—S2—C2	138.8 (4)	C1—Ir1—C13—C131	−76.1 (5)
C13—Ir1—S2—C2	141.02 (19)	C12—Ir1—C13—C131	121.5 (6)
C11—Ir1—S2—C2	82.3 (2)	C14—Ir1—C13—C131	−121.3 (6)
S1—Ir1—S2—C2	3.06 (15)	C15—Ir1—C13—C131	−158.7 (5)
C4—N1—C2—S1	176.2 (3)	C11—Ir1—C13—C131	159.4 (5)
C3—N1—C2—S1	−0.2 (6)	S1—Ir1—C13—C131	94.4 (5)
C4—N1—C2—S2	−1.5 (6)	S2—Ir1—C13—C131	22.2 (5)
C3—N1—C2—S2	−177.8 (4)	C12—C13—C14—C15	1.3 (5)
Ir1—S1—C2—N1	−173.6 (4)	C131—C13—C14—C15	−176.4 (5)
Ir1—S1—C2—S2	4.3 (2)	Ir1—C13—C14—C15	62.2 (3)
Ir1—S2—C2—N1	173.6 (4)	C12—C13—C14—C141	175.6 (5)
Ir1—S2—C2—S1	−4.3 (2)	C131—C13—C14—C141	−2.1 (8)
C2—N1—C3—C31	−95.8 (6)	Ir1—C13—C14—C141	−123.4 (5)
C4—N1—C3—C31	87.7 (6)	C12—C13—C14—Ir1	−60.9 (3)
C2—N1—C4—C41	−86.9 (6)	C131—C13—C14—Ir1	121.4 (5)
C3—N1—C4—C41	89.6 (5)	C1—Ir1—C14—C13	−145.6 (3)
C12—Ir1—C1—O1	−7 (13)	C12—Ir1—C14—C13	38.3 (3)
C14—Ir1—C1—O1	−18 (13)	C15—Ir1—C14—C13	118.3 (4)
C15—Ir1—C1—O1	20 (13)	C11—Ir1—C14—C13	80.8 (3)
C13—Ir1—C1—O1	−44 (13)	S1—Ir1—C14—C13	91.4 (4)
C11—Ir1—C1—O1	43 (13)	S2—Ir1—C14—C13	−46.6 (3)
S1—Ir1—C1—O1	143 (13)	C1—Ir1—C14—C15	96.1 (3)
S2—Ir1—C1—O1	−145 (13)	C12—Ir1—C14—C15	−79.9 (3)
C1—Ir1—C11—C15	−38.2 (4)	C13—Ir1—C14—C15	−118.3 (4)
C12—Ir1—C11—C15	118.8 (4)	C11—Ir1—C14—C15	−37.5 (3)
C14—Ir1—C11—C15	38.2 (3)	S1—Ir1—C14—C15	−26.9 (5)
C13—Ir1—C11—C15	80.0 (3)	S2—Ir1—C14—C15	−164.9 (2)
S1—Ir1—C11—C15	−137.6 (3)	C1—Ir1—C14—C141	−23.7 (5)
S2—Ir1—C11—C15	152.2 (2)	C12—Ir1—C14—C141	160.2 (5)
C1—Ir1—C11—C12	−157.0 (4)	C15—Ir1—C14—C141	−119.8 (6)
C14—Ir1—C11—C12	−80.6 (3)	C13—Ir1—C14—C141	121.9 (6)
C15—Ir1—C11—C12	−118.8 (4)	C11—Ir1—C14—C141	−157.3 (5)
C13—Ir1—C11—C12	−38.8 (3)	S1—Ir1—C14—C141	−146.7 (4)
S1—Ir1—C11—C12	103.5 (3)	S2—Ir1—C14—C141	75.3 (5)
S2—Ir1—C11—C12	33.3 (3)	C12—C11—C15—C14	−1.7 (5)
C1—Ir1—C11—C111	82.7 (6)	C111—C11—C15—C14	177.0 (4)
C12—Ir1—C11—C111	−120.3 (7)	Ir1—C11—C15—C14	−62.1 (3)
C14—Ir1—C11—C111	159.1 (6)	C12—C11—C15—C151	−174.8 (5)
C15—Ir1—C11—C111	120.9 (7)	C111—C11—C15—C151	3.9 (8)
C13—Ir1—C11—C111	−159.1 (6)	Ir1—C11—C15—C151	124.8 (5)
S1—Ir1—C11—C111	−16.7 (5)	C12—C11—C15—Ir1	60.4 (3)
S2—Ir1—C11—C111	−86.9 (6)	C111—C11—C15—Ir1	−120.8 (5)
C15—C11—C12—C13	2.5 (5)	C13—C14—C15—C11	0.2 (5)
C111—C11—C12—C13	−176.3 (4)	C141—C14—C15—C11	−174.2 (5)
Ir1—C11—C12—C13	63.3 (3)	Ir1—C14—C15—C11	63.0 (3)
C15—C11—C12—C121	176.7 (5)	C13—C14—C15—C151	173.4 (5)
C111—C11—C12—C121	−2.1 (8)	C141—C14—C15—C151	−1.0 (8)
Ir1—C11—C12—C121	−122.5 (5)	Ir1—C14—C15—C151	−123.9 (5)
C15—C11—C12—Ir1	−60.8 (3)	C13—C14—C15—Ir1	−62.7 (3)
C111—C11—C12—Ir1	120.4 (5)	C141—C14—C15—Ir1	122.8 (5)
C1—Ir1—C12—C11	66.6 (9)	C1—Ir1—C15—C11	152.4 (3)
C14—Ir1—C12—C11	79.2 (3)	C12—Ir1—C15—C11	−36.8 (3)
C15—Ir1—C12—C11	36.4 (3)	C14—Ir1—C15—C11	−116.7 (4)
C13—Ir1—C12—C11	116.1 (4)	C13—Ir1—C15—C11	−80.2 (3)
S1—Ir1—C12—C11	−82.2 (3)	S1—Ir1—C15—C11	51.4 (3)
S2—Ir1—C12—C11	−156.6 (2)	S2—Ir1—C15—C11	−77.7 (5)
C1—Ir1—C12—C13	−49.5 (9)	C1—Ir1—C15—C14	−90.9 (3)
C14—Ir1—C12—C13	−36.9 (3)	C12—Ir1—C15—C14	79.9 (3)
C15—Ir1—C12—C13	−79.6 (3)	C13—Ir1—C15—C14	36.5 (3)
C11—Ir1—C12—C13	−116.1 (4)	C11—Ir1—C15—C14	116.7 (4)
S1—Ir1—C12—C13	161.8 (3)	S1—Ir1—C15—C14	168.1 (2)
S2—Ir1—C12—C13	87.3 (3)	S2—Ir1—C15—C14	39.0 (5)
C1—Ir1—C12—C121	−169.9 (8)	C1—Ir1—C15—C151	29.8 (5)
C14—Ir1—C12—C121	−157.4 (7)	C12—Ir1—C15—C151	−159.4 (5)
C15—Ir1—C12—C121	159.9 (7)	C14—Ir1—C15—C151	120.7 (6)
C13—Ir1—C12—C121	−120.5 (7)	C13—Ir1—C15—C151	157.2 (5)
C11—Ir1—C12—C121	123.5 (7)	C11—Ir1—C15—C151	−122.6 (6)
S1—Ir1—C12—C121	41.3 (6)	S1—Ir1—C15—C151	−71.2 (5)
S2—Ir1—C12—C121	−33.2 (6)	S2—Ir1—C15—C151	159.7 (4)
C11—C12—C13—C14	−2.3 (5)	O13—S10—C10—F12	−58.9 (6)
C121—C12—C13—C14	−176.6 (5)	O11—S10—C10—F12	61.4 (6)
Ir1—C12—C13—C14	61.4 (3)	O12—S10—C10—F12	−179.1 (6)
C11—C12—C13—C131	175.4 (5)	O13—S10—C10—F11	−179.7 (5)
C121—C12—C13—C131	1.1 (8)	O11—S10—C10—F11	−59.4 (6)
Ir1—C12—C13—C131	−120.9 (5)	O12—S10—C10—F11	60.2 (6)
C11—C12—C13—Ir1	−63.8 (3)	O13—S10—C10—F13	60.5 (6)
C121—C12—C13—Ir1	121.9 (5)	O11—S10—C10—F13	−179.2 (5)
C1—Ir1—C13—C14	45.2 (4)	O12—S10—C10—F13	−59.6 (6)
C12—Ir1—C13—C14	−117.2 (4)