(1,2-Dicyano­ethyl­enedithiol­ato-κ²S,S′)(η⁵-penta­methyl­cyclo­penta­dien­yl)iridium(III)

The crystal structure of the title complex, [Ir(C₁₀H₁₅)(C₄N₂S₂)], is composed of distinct [η⁵-Cp*Ir(mnt)] (Cp* is penta­methyl­cyclo­penta­dienyl and mnt is 1,2-dicyano­ethyl­ene­dithiol­ate) molecules separated by normal van der Waals contacts. The asymmetric unit consists of two molecules. The Ir^III atom may be considered penta­coordinate since it is linked to a bidentate dithiol­ate ligand and a formally tridentate η⁵-Cp* ligand. Ir—S distances range from 2.238 (3) to 2.246 (3) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.041
• wR factor = 0.096
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.81
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ir2
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C12    ...       1.46 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13    -   C14    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C25    -   C27    ...       1.46 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C26    -   C28    ...       1.46 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C20
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C21
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C22
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C24
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        147
            C13 -C11 -C12 -N1     16.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        148
            S1  -C11 -C12 -N1      2.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        155
            C11 -C13 -C14 -N2     15.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        156
            S2  -C13 -C14 -N2      3.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        285
            C26 -C25 -C27 -N3     14.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        286
            S4  -C25 -C27 -N3      4.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        287
            C25 -C26 -C28 -N4     13.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        288
            S3  -C26 -C28 -N4      5.00  0.00   1.555   1.555   1.555   1.555

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.812
            Tmax scaled      0.323 Tmin scaled      0.289

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

(1,2-Dicyanoethylenedithiolato-κ²S,S')(η⁵– pentamethylcyclopentadienyl)iridium(III)

Crystal data

[Ir(C10H15)(C4N2S2)]	Z = 4
Mr = 467.60	F(000) = 888
Triclinic, P1	Dx = 1.964 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.891 (9) Å	Cell parameters from 6598 reflections
b = 13.090 (13) Å	θ = 2.0–27.0°
c = 14.548 (14) Å	µ = 8.69 mm^−1
α = 98.347 (13)°	T = 298 K
β = 97.794 (12)°	Block, red
γ = 106.131 (11)°	0.15 × 0.14 × 0.13 mm
V = 1581 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	6598 independent reflections
Radiation source: fine-focus sealed tube	4925 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.356, Tmax = 0.398	k = −16→16
6598 measured reflections	l = 0→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (13.7468P)^2 + 14.5636P] where P = (Fo^2 + 2Fc^2)/3
6598 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 1.41 e Å^−3
0 restraints	Δρmin = −2.28 e Å^−3

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	0.84997 (3)	0.07207 (3)	0.29571 (2)	0.03707 (10)
Ir2	0.71112 (3)	0.42889 (3)	0.79490 (2)	0.03760 (10)
S1	0.9404 (3)	−0.06897 (19)	0.31269 (17)	0.0501 (5)
S2	0.7186 (3)	0.03827 (19)	0.41412 (16)	0.0502 (5)
S3	0.7489 (3)	0.57174 (19)	0.91107 (16)	0.0533 (6)
S4	0.9769 (2)	0.46672 (19)	0.81171 (17)	0.0510 (5)
N1	0.9138 (10)	−0.2958 (7)	0.4416 (7)	0.073 (3)
N2	0.6206 (10)	−0.1505 (8)	0.5792 (7)	0.079 (3)
N3	1.3585 (9)	0.6640 (7)	0.9367 (7)	0.075 (3)
N4	1.0547 (11)	0.8053 (7)	1.0690 (7)	0.084 (3)
C1	0.8117 (10)	0.0954 (8)	0.1493 (6)	0.053 (2)
C2	0.9765 (9)	0.1394 (7)	0.1873 (6)	0.042 (2)
C3	0.9953 (9)	0.2259 (7)	0.2683 (6)	0.0408 (19)
C4	0.8390 (10)	0.2329 (7)	0.2764 (7)	0.050 (2)
C5	0.7259 (9)	0.1531 (8)	0.2058 (6)	0.049 (2)
C6	1.1495 (10)	0.2994 (8)	0.3244 (7)	0.064 (3)
H6A	1.1849	0.3607	0.2951	0.096*
H6B	1.2274	0.2612	0.3270	0.096*
H6C	1.1358	0.3236	0.3873	0.096*
C7	0.8056 (14)	0.3137 (9)	0.3463 (8)	0.082 (3)
H7A	0.8073	0.3773	0.3203	0.123*
H7B	0.8852	0.3328	0.4027	0.123*
H7C	0.7025	0.2836	0.3613	0.123*
C8	0.5459 (10)	0.1332 (10)	0.1867 (8)	0.089 (4)
H8A	0.5202	0.1793	0.1454	0.133*
H8B	0.5110	0.1488	0.2453	0.133*
H8C	0.4933	0.0588	0.1573	0.133*
C9	0.7431 (13)	0.0057 (9)	0.0626 (7)	0.086 (4)
H9A	0.7385	0.0369	0.0069	0.129*
H9B	0.6378	−0.0358	0.0672	0.129*
H9C	0.8097	−0.0407	0.0590	0.129*
C10	1.1081 (11)	0.1056 (9)	0.1494 (8)	0.075 (3)
H10A	1.1425	0.1473	0.1028	0.112*
H10B	1.0698	0.0300	0.1210	0.112*
H10C	1.1960	0.1180	0.2002	0.112*
C11	0.8580 (9)	−0.1208 (7)	0.4022 (6)	0.046 (2)
C12	0.8884 (10)	−0.2187 (8)	0.4259 (6)	0.050 (2)
C13	0.7581 (9)	−0.0742 (7)	0.4473 (6)	0.0424 (19)
C14	0.6832 (10)	−0.1172 (8)	0.5214 (7)	0.051 (2)
C15	0.5861 (12)	0.3600 (9)	0.6512 (6)	0.065 (3)
C16	0.4822 (10)	0.4029 (7)	0.7047 (7)	0.055 (2)
C17	0.4563 (9)	0.3442 (7)	0.7758 (7)	0.050 (2)
C18	0.5442 (9)	0.2661 (7)	0.7692 (6)	0.048 (2)
C19	0.6231 (9)	0.2765 (7)	0.6903 (6)	0.050 (2)
C20	0.6462 (17)	0.4004 (11)	0.5625 (8)	0.127 (6)
H20A	0.5733	0.3583	0.5062	0.191*
H20B	0.7498	0.3924	0.5604	0.191*
H20C	0.6523	0.4754	0.5666	0.191*
C21	0.4098 (13)	0.4912 (9)	0.6867 (10)	0.107 (5)
H21A	0.3091	0.4600	0.6444	0.161*
H21B	0.4801	0.5426	0.6588	0.161*
H21C	0.3943	0.5272	0.7454	0.161*
C22	0.3496 (11)	0.3528 (10)	0.8485 (8)	0.088 (4)
H22A	0.2429	0.3074	0.8223	0.133*
H22B	0.3500	0.4266	0.8648	0.133*
H22C	0.3889	0.3297	0.9041	0.133*
C23	0.5439 (12)	0.1833 (8)	0.8307 (8)	0.080 (4)
H23A	0.4585	0.1181	0.8033	0.121*
H23B	0.5293	0.2111	0.8925	0.121*
H23C	0.6436	0.1676	0.8356	0.121*
C24	0.7196 (12)	0.2075 (10)	0.6559 (9)	0.103 (4)
H24A	0.6517	0.1454	0.6107	0.155*
H24B	0.7692	0.1840	0.7083	0.155*
H24C	0.8003	0.2486	0.6265	0.155*
C25	1.0516 (9)	0.5808 (7)	0.8979 (6)	0.047 (2)
C26	0.9539 (9)	0.6281 (6)	0.9419 (6)	0.0417 (19)
C27	1.2241 (11)	0.6281 (8)	0.9217 (7)	0.059 (3)
C28	1.0131 (11)	0.7263 (8)	1.0145 (7)	0.057 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.03717 (17)	0.0445 (2)	0.03266 (18)	0.01472 (14)	0.00799 (13)	0.01136 (14)
Ir2	0.03918 (17)	0.0396 (2)	0.03427 (18)	0.01249 (14)	0.00678 (14)	0.00682 (14)
S1	0.0562 (12)	0.0581 (15)	0.0517 (13)	0.0302 (11)	0.0227 (11)	0.0232 (11)
S2	0.0621 (13)	0.0584 (15)	0.0461 (13)	0.0306 (11)	0.0270 (11)	0.0203 (11)
S3	0.0492 (12)	0.0549 (15)	0.0500 (13)	0.0121 (11)	0.0119 (11)	−0.0033 (11)
S4	0.0408 (11)	0.0539 (14)	0.0558 (14)	0.0154 (10)	0.0083 (10)	0.0010 (11)
N1	0.095 (6)	0.064 (6)	0.075 (6)	0.041 (5)	0.015 (5)	0.032 (5)
N2	0.073 (5)	0.109 (8)	0.078 (6)	0.034 (5)	0.038 (5)	0.055 (6)
N3	0.055 (5)	0.087 (7)	0.077 (6)	0.011 (5)	0.008 (5)	0.022 (5)
N4	0.101 (7)	0.057 (6)	0.075 (7)	0.009 (5)	0.003 (5)	−0.009 (5)
C1	0.058 (5)	0.066 (6)	0.031 (4)	0.010 (5)	0.001 (4)	0.022 (4)
C2	0.045 (4)	0.053 (5)	0.042 (5)	0.020 (4)	0.021 (4)	0.026 (4)
C3	0.042 (4)	0.051 (5)	0.037 (4)	0.019 (4)	0.010 (4)	0.022 (4)
C4	0.061 (5)	0.057 (6)	0.053 (6)	0.038 (5)	0.024 (5)	0.030 (5)
C5	0.041 (4)	0.079 (7)	0.037 (5)	0.025 (4)	0.009 (4)	0.030 (5)
C6	0.059 (5)	0.059 (6)	0.055 (6)	−0.009 (5)	−0.005 (5)	0.017 (5)
C7	0.113 (9)	0.084 (9)	0.068 (7)	0.050 (7)	0.029 (7)	0.025 (6)
C8	0.040 (5)	0.153 (12)	0.093 (9)	0.034 (6)	0.012 (5)	0.076 (9)
C9	0.090 (8)	0.099 (9)	0.038 (6)	−0.011 (7)	0.014 (6)	−0.005 (5)
C10	0.083 (7)	0.090 (9)	0.076 (7)	0.044 (6)	0.053 (6)	0.028 (6)
C11	0.047 (5)	0.047 (5)	0.044 (5)	0.013 (4)	0.003 (4)	0.013 (4)
C12	0.053 (5)	0.058 (6)	0.046 (5)	0.021 (4)	0.011 (4)	0.016 (5)
C13	0.045 (4)	0.050 (5)	0.037 (4)	0.016 (4)	0.013 (4)	0.015 (4)
C14	0.047 (5)	0.062 (6)	0.049 (5)	0.020 (4)	0.011 (4)	0.019 (5)
C15	0.072 (6)	0.070 (7)	0.031 (5)	−0.006 (5)	0.000 (5)	0.006 (5)
C16	0.057 (5)	0.049 (6)	0.054 (6)	0.020 (4)	−0.008 (5)	0.007 (5)
C17	0.030 (4)	0.048 (5)	0.058 (6)	0.004 (4)	0.005 (4)	−0.013 (4)
C18	0.043 (4)	0.038 (5)	0.054 (6)	0.002 (4)	−0.003 (4)	0.010 (4)
C19	0.039 (4)	0.056 (6)	0.047 (5)	0.015 (4)	0.006 (4)	−0.011 (4)
C20	0.166 (13)	0.123 (12)	0.048 (7)	−0.032 (10)	0.022 (8)	0.021 (7)
C21	0.101 (9)	0.066 (8)	0.143 (13)	0.035 (7)	−0.040 (9)	0.024 (8)
C22	0.052 (6)	0.102 (10)	0.098 (9)	0.013 (6)	0.034 (6)	−0.022 (7)
C23	0.092 (8)	0.049 (7)	0.084 (8)	0.000 (6)	−0.010 (7)	0.030 (6)
C24	0.066 (7)	0.099 (10)	0.126 (11)	0.026 (7)	0.018 (7)	−0.043 (8)
C25	0.043 (4)	0.051 (6)	0.044 (5)	0.010 (4)	0.005 (4)	0.016 (4)
C26	0.048 (4)	0.034 (5)	0.034 (4)	0.002 (4)	−0.001 (4)	0.004 (3)
C27	0.053 (5)	0.063 (7)	0.061 (6)	0.016 (5)	0.003 (5)	0.022 (5)
C28	0.064 (6)	0.058 (7)	0.050 (6)	0.016 (5)	0.013 (5)	0.016 (5)

Geometric parameters (Å, º)

Ir1—C5	2.172 (8)	C8—H8B	0.9600
Ir1—C1	2.190 (8)	C8—H8C	0.9600
Ir1—C4	2.191 (8)	C9—H9A	0.9600
Ir1—C3	2.193 (8)	C9—H9B	0.9600
Ir1—C2	2.205 (7)	C9—H9C	0.9600
Ir1—S2	2.238 (3)	C10—H10A	0.9600
Ir1—S1	2.241 (3)	C10—H10B	0.9600
Ir2—C15	2.164 (9)	C10—H10C	0.9600
Ir2—C18	2.178 (8)	C11—C13	1.391 (11)
Ir2—C16	2.178 (8)	C11—C12	1.459 (11)
Ir2—C17	2.187 (8)	C13—C14	1.444 (11)
Ir2—C19	2.199 (9)	C15—C19	1.398 (13)
Ir2—S4	2.246 (3)	C15—C16	1.460 (14)
Ir2—S3	2.246 (3)	C15—C20	1.568 (13)
S1—C11	1.713 (8)	C16—C17	1.381 (12)
S2—C13	1.724 (8)	C16—C21	1.508 (13)
S3—C26	1.733 (8)	C17—C18	1.450 (12)
S4—C25	1.710 (9)	C17—C22	1.525 (13)
N1—C12	1.140 (11)	C18—C19	1.428 (12)
N2—C14	1.143 (10)	C18—C23	1.502 (11)
N3—C27	1.133 (10)	C19—C24	1.490 (13)
N4—C28	1.143 (12)	C20—H20A	0.9600
C1—C2	1.415 (11)	C20—H20B	0.9600
C1—C5	1.462 (13)	C20—H20C	0.9600
C1—C9	1.518 (13)	C21—H21A	0.9600
C2—C3	1.466 (12)	C21—H21B	0.9600
C2—C10	1.503 (12)	C21—H21C	0.9600
C3—C4	1.437 (11)	C22—H22A	0.9600
C3—C6	1.486 (11)	C22—H22B	0.9600
C4—C5	1.408 (13)	C22—H22C	0.9600
C4—C7	1.479 (14)	C23—H23A	0.9600
C5—C8	1.527 (11)	C23—H23B	0.9600
C6—H6A	0.9600	C23—H23C	0.9600
C6—H6B	0.9600	C24—H24A	0.9600
C6—H6C	0.9600	C24—H24B	0.9600
C7—H7A	0.9600	C24—H24C	0.9600
C7—H7B	0.9600	C25—C26	1.372 (12)
C7—H7C	0.9600	C25—C27	1.456 (11)
C8—H8A	0.9600	C26—C28	1.457 (13)
C5—Ir1—C1	39.2 (3)	C5—C8—H8C	109.5
C5—Ir1—C4	37.7 (3)	H8A—C8—H8C	109.5
C1—Ir1—C4	64.0 (4)	H8B—C8—H8C	109.5
C5—Ir1—C3	64.1 (3)	C1—C9—H9A	109.5
C1—Ir1—C3	64.1 (3)	C1—C9—H9B	109.5
C4—Ir1—C3	38.3 (3)	H9A—C9—H9B	109.5
C5—Ir1—C2	64.4 (3)	C1—C9—H9C	109.5
C1—Ir1—C2	37.6 (3)	H9A—C9—H9C	109.5
C4—Ir1—C2	64.3 (3)	H9B—C9—H9C	109.5
C3—Ir1—C2	38.9 (3)	C2—C10—H10A	109.5
C5—Ir1—S2	108.3 (2)	C2—C10—H10B	109.5
C1—Ir1—S2	141.2 (2)	H10A—C10—H10B	109.5
C4—Ir1—S2	104.1 (2)	C2—C10—H10C	109.5
C3—Ir1—S2	130.2 (2)	H10A—C10—H10C	109.5
C2—Ir1—S2	168.2 (2)	H10B—C10—H10C	109.5
C5—Ir1—S1	149.2 (3)	C13—C11—C12	121.2 (7)
C1—Ir1—S1	113.3 (3)	C13—C11—S1	120.7 (6)
C4—Ir1—S1	162.1 (2)	C12—C11—S1	118.0 (7)
C3—Ir1—S1	123.9 (2)	N1—C12—C11	177.7 (11)
C2—Ir1—S1	102.3 (2)	C11—C13—C14	122.4 (7)
S2—Ir1—S1	88.50 (9)	C11—C13—S2	119.8 (6)
C15—Ir2—C18	62.9 (3)	C14—C13—S2	117.8 (6)
C15—Ir2—C16	39.3 (4)	N2—C14—C13	178.2 (9)
C18—Ir2—C16	63.7 (3)	C19—C15—C16	109.8 (8)
C15—Ir2—C17	63.2 (4)	C19—C15—C20	124.9 (11)
C18—Ir2—C17	38.8 (3)	C16—C15—C20	125.3 (11)
C16—Ir2—C17	36.9 (3)	C19—C15—Ir2	72.7 (5)
C15—Ir2—C19	37.4 (4)	C16—C15—Ir2	70.9 (5)
C18—Ir2—C19	38.1 (3)	C20—C15—Ir2	123.5 (7)
C16—Ir2—C19	64.6 (3)	C17—C16—C15	106.8 (8)
C17—Ir2—C19	64.3 (3)	C17—C16—C21	125.0 (10)
C15—Ir2—S4	113.7 (3)	C15—C16—C21	128.2 (10)
C18—Ir2—S4	124.6 (2)	C17—C16—Ir2	71.9 (5)
C16—Ir2—S4	149.2 (3)	C15—C16—Ir2	69.8 (5)
C17—Ir2—S4	163.4 (3)	C21—C16—Ir2	124.8 (7)
C19—Ir2—S4	102.9 (2)	C16—C17—C18	108.6 (8)
C15—Ir2—S3	141.3 (3)	C16—C17—C22	128.0 (9)
C18—Ir2—S3	130.3 (3)	C18—C17—C22	123.3 (9)
C16—Ir2—S3	107.6 (3)	C16—C17—Ir2	71.2 (5)
C17—Ir2—S3	103.5 (2)	C18—C17—Ir2	70.3 (4)
C19—Ir2—S3	167.4 (2)	C22—C17—Ir2	126.3 (6)
S4—Ir2—S3	88.66 (8)	C19—C18—C17	108.3 (7)
C11—S1—Ir1	105.4 (3)	C19—C18—C23	125.6 (9)
C13—S2—Ir1	105.5 (3)	C17—C18—C23	126.0 (9)
C26—S3—Ir2	104.8 (3)	C19—C18—Ir2	71.8 (5)
C25—S4—Ir2	104.8 (3)	C17—C18—Ir2	70.9 (5)
C2—C1—C5	108.3 (8)	C23—C18—Ir2	126.1 (6)
C2—C1—C9	123.8 (9)	C15—C19—C18	106.5 (8)
C5—C1—C9	127.8 (8)	C15—C19—C24	127.9 (10)
C2—C1—Ir1	71.8 (4)	C18—C19—C24	125.6 (10)
C5—C1—Ir1	69.8 (4)	C15—C19—Ir2	70.0 (6)
C9—C1—Ir1	125.6 (7)	C18—C19—Ir2	70.2 (5)
C1—C2—C3	107.5 (7)	C24—C19—Ir2	126.5 (6)
C1—C2—C10	126.0 (9)	C15—C20—H20A	109.5
C3—C2—C10	126.5 (8)	C15—C20—H20B	109.5
C1—C2—Ir1	70.6 (4)	H20A—C20—H20B	109.5
C3—C2—Ir1	70.1 (4)	C15—C20—H20C	109.5
C10—C2—Ir1	126.1 (6)	H20A—C20—H20C	109.5
C4—C3—C2	107.3 (7)	H20B—C20—H20C	109.5
C4—C3—C6	126.8 (9)	C16—C21—H21A	109.5
C2—C3—C6	125.6 (8)	C16—C21—H21B	109.5
C4—C3—Ir1	70.8 (5)	H21A—C21—H21B	109.5
C2—C3—Ir1	71.0 (4)	C16—C21—H21C	109.5
C6—C3—Ir1	128.3 (5)	H21A—C21—H21C	109.5
C5—C4—C3	109.0 (8)	H21B—C21—H21C	109.5
C5—C4—C7	126.3 (8)	C17—C22—H22A	109.5
C3—C4—C7	124.7 (9)	C17—C22—H22B	109.5
C5—C4—Ir1	70.5 (5)	H22A—C22—H22B	109.5
C3—C4—Ir1	71.0 (4)	C17—C22—H22C	109.5
C7—C4—Ir1	126.1 (6)	H22A—C22—H22C	109.5
C4—C5—C1	107.9 (7)	H22B—C22—H22C	109.5
C4—C5—C8	126.8 (9)	C18—C23—H23A	109.5
C1—C5—C8	125.2 (9)	C18—C23—H23B	109.5
C4—C5—Ir1	71.9 (4)	H23A—C23—H23B	109.5
C1—C5—Ir1	71.1 (4)	C18—C23—H23C	109.5
C8—C5—Ir1	125.2 (6)	H23A—C23—H23C	109.5
C3—C6—H6A	109.5	H23B—C23—H23C	109.5
C3—C6—H6B	109.5	C19—C24—H24A	109.5
H6A—C6—H6B	109.5	C19—C24—H24B	109.5
C3—C6—H6C	109.5	H24A—C24—H24B	109.5
H6A—C6—H6C	109.5	C19—C24—H24C	109.5
H6B—C6—H6C	109.5	H24A—C24—H24C	109.5
C4—C7—H7A	109.5	H24B—C24—H24C	109.5
C4—C7—H7B	109.5	C26—C25—C27	120.8 (8)
H7A—C7—H7B	109.5	C26—C25—S4	121.7 (6)
C4—C7—H7C	109.5	C27—C25—S4	117.5 (7)
H7A—C7—H7C	109.5	C25—C26—C28	123.3 (8)
H7B—C7—H7C	109.5	C25—C26—S3	120.0 (6)
C5—C8—H8A	109.5	C28—C26—S3	116.7 (7)
C5—C8—H8B	109.5	N3—C27—C25	177.3 (11)
H8A—C8—H8B	109.5	N4—C28—C26	176.8 (11)
C5—Ir1—S1—C11	−124.0 (5)	Ir1—S1—C11—C13	−0.1 (8)
C1—Ir1—S1—C11	−146.2 (4)	Ir1—S1—C11—C12	176.4 (6)
C4—Ir1—S1—C11	136.4 (9)	C13—C11—C12—N1	160 (26)
C3—Ir1—S1—C11	140.3 (4)	S1—C11—C12—N1	−16 (26)
C2—Ir1—S1—C11	175.9 (4)	C12—C11—C13—C14	2.0 (13)
S2—Ir1—S1—C11	0.7 (3)	S1—C11—C13—C14	178.4 (7)
C5—Ir1—S2—C13	152.6 (4)	C12—C11—C13—S2	−177.3 (6)
C1—Ir1—S2—C13	125.8 (5)	S1—C11—C13—S2	−0.9 (10)
C4—Ir1—S2—C13	−168.3 (4)	Ir1—S2—C13—C11	1.4 (7)
C3—Ir1—S2—C13	−136.3 (4)	Ir1—S2—C13—C14	−177.9 (6)
C2—Ir1—S2—C13	−157.5 (11)	C11—C13—C14—N2	−145 (38)
S1—Ir1—S2—C13	−1.1 (3)	S2—C13—C14—N2	34 (38)
C15—Ir2—S3—C26	−125.9 (5)	C18—Ir2—C15—C19	−38.2 (5)
C18—Ir2—S3—C26	138.3 (4)	C16—Ir2—C15—C19	−119.0 (8)
C16—Ir2—S3—C26	−151.6 (4)	C17—Ir2—C15—C19	−81.9 (6)
C17—Ir2—S3—C26	170.3 (4)	S4—Ir2—C15—C19	80.0 (5)
C19—Ir2—S3—C26	158.2 (12)	S3—Ir2—C15—C19	−159.6 (4)
S4—Ir2—S3—C26	1.8 (3)	C18—Ir2—C15—C16	80.8 (6)
C15—Ir2—S4—C25	145.7 (4)	C17—Ir2—C15—C16	37.1 (5)
C18—Ir2—S4—C25	−142.0 (4)	C19—Ir2—C15—C16	119.0 (8)
C16—Ir2—S4—C25	121.9 (6)	S4—Ir2—C15—C16	−161.0 (5)
C17—Ir2—S4—C25	−139.0 (9)	S3—Ir2—C15—C16	−40.7 (7)
C19—Ir2—S4—C25	−176.5 (4)	C18—Ir2—C15—C20	−159.0 (12)
S3—Ir2—S4—C25	−1.7 (3)	C16—Ir2—C15—C20	120.2 (13)
C5—Ir1—C1—C2	118.3 (8)	C17—Ir2—C15—C20	157.3 (12)
C4—Ir1—C1—C2	81.0 (6)	C19—Ir2—C15—C20	−120.8 (14)
C3—Ir1—C1—C2	38.2 (5)	S4—Ir2—C15—C20	−40.8 (12)
S2—Ir1—C1—C2	161.0 (4)	S3—Ir2—C15—C20	79.6 (12)
S1—Ir1—C1—C2	−79.6 (5)	C19—C15—C16—C17	−0.3 (11)
C4—Ir1—C1—C5	−37.3 (5)	C20—C15—C16—C17	179.1 (9)
C3—Ir1—C1—C5	−80.1 (5)	Ir2—C15—C16—C17	−62.9 (6)
C2—Ir1—C1—C5	−118.3 (8)	C19—C15—C16—C21	−178.5 (9)
S2—Ir1—C1—C5	42.7 (7)	C20—C15—C16—C21	1.0 (16)
S1—Ir1—C1—C5	162.2 (4)	Ir2—C15—C16—C21	119.0 (10)
C5—Ir1—C1—C9	−122.7 (10)	C19—C15—C16—Ir2	62.6 (7)
C4—Ir1—C1—C9	−160.0 (10)	C20—C15—C16—Ir2	−118.0 (9)
C3—Ir1—C1—C9	157.2 (10)	C15—Ir2—C16—C17	116.3 (8)
C2—Ir1—C1—C9	119.0 (11)	C18—Ir2—C16—C17	37.8 (5)
S2—Ir1—C1—C9	−80.0 (10)	C19—Ir2—C16—C17	80.3 (6)
S1—Ir1—C1—C9	39.5 (9)	S4—Ir2—C16—C17	151.9 (5)
C5—C1—C2—C3	−0.2 (9)	S3—Ir2—C16—C17	−89.0 (5)
C9—C1—C2—C3	178.2 (8)	C18—Ir2—C16—C15	−78.5 (6)
Ir1—C1—C2—C3	−60.7 (5)	C17—Ir2—C16—C15	−116.3 (8)
C5—C1—C2—C10	−178.4 (7)	C19—Ir2—C16—C15	−36.0 (5)
C9—C1—C2—C10	−0.1 (13)	S4—Ir2—C16—C15	35.6 (8)
Ir1—C1—C2—C10	121.1 (8)	S3—Ir2—C16—C15	154.7 (5)
C5—C1—C2—Ir1	60.5 (5)	C15—Ir2—C16—C21	−123.2 (12)
C9—C1—C2—Ir1	−121.1 (9)	C18—Ir2—C16—C21	158.3 (11)
C5—Ir1—C2—C1	−38.1 (6)	C17—Ir2—C16—C21	120.5 (12)
C4—Ir1—C2—C1	−80.1 (6)	C19—Ir2—C16—C21	−159.2 (11)
C3—Ir1—C2—C1	−117.8 (7)	S4—Ir2—C16—C21	−87.5 (11)
S2—Ir1—C2—C1	−91.8 (12)	S3—Ir2—C16—C21	31.5 (10)
S1—Ir1—C2—C1	112.5 (5)	C15—C16—C17—C18	0.9 (10)
C5—Ir1—C2—C3	79.7 (5)	C21—C16—C17—C18	179.1 (9)
C1—Ir1—C2—C3	117.8 (7)	Ir2—C16—C17—C18	−60.6 (6)
C4—Ir1—C2—C3	37.8 (4)	C15—C16—C17—C22	−176.7 (8)
S2—Ir1—C2—C3	26.1 (13)	C21—C16—C17—C22	1.5 (15)
S1—Ir1—C2—C3	−129.7 (4)	Ir2—C16—C17—C22	121.8 (9)
C5—Ir1—C2—C10	−159.1 (10)	C15—C16—C17—Ir2	61.5 (6)
C1—Ir1—C2—C10	−121.0 (11)	C21—C16—C17—Ir2	−120.3 (10)
C4—Ir1—C2—C10	159.0 (9)	C15—Ir2—C17—C16	−39.5 (6)
C3—Ir1—C2—C10	121.2 (10)	C18—Ir2—C17—C16	−118.7 (8)
S2—Ir1—C2—C10	147.3 (8)	C19—Ir2—C17—C16	−81.4 (6)
S1—Ir1—C2—C10	−8.5 (9)	S4—Ir2—C17—C16	−122.6 (9)
C1—C2—C3—C4	−0.7 (8)	S3—Ir2—C17—C16	101.6 (5)
C10—C2—C3—C4	177.5 (8)	C15—Ir2—C17—C18	79.2 (6)
Ir1—C2—C3—C4	−61.8 (5)	C16—Ir2—C17—C18	118.7 (8)
C1—C2—C3—C6	−175.0 (7)	C19—Ir2—C17—C18	37.3 (5)
C10—C2—C3—C6	3.2 (13)	S4—Ir2—C17—C18	−3.9 (12)
Ir1—C2—C3—C6	124.0 (8)	S3—Ir2—C17—C18	−139.8 (5)
C1—C2—C3—Ir1	61.0 (5)	C15—Ir2—C17—C22	−163.4 (10)
C10—C2—C3—Ir1	−120.7 (8)	C18—Ir2—C17—C22	117.5 (11)
C5—Ir1—C3—C4	36.4 (5)	C16—Ir2—C17—C22	−123.9 (11)
C1—Ir1—C3—C4	80.2 (6)	C19—Ir2—C17—C22	154.8 (10)
C2—Ir1—C3—C4	117.0 (7)	S4—Ir2—C17—C22	113.5 (10)
S2—Ir1—C3—C4	−56.2 (6)	S3—Ir2—C17—C22	−22.3 (9)
S1—Ir1—C3—C4	−178.1 (4)	C16—C17—C18—C19	−1.2 (9)
C5—Ir1—C3—C2	−80.6 (5)	C22—C17—C18—C19	176.5 (8)
C1—Ir1—C3—C2	−36.8 (5)	Ir2—C17—C18—C19	−62.4 (6)
C4—Ir1—C3—C2	−117.0 (7)	C16—C17—C18—C23	−177.5 (8)
S2—Ir1—C3—C2	−173.2 (3)	C22—C17—C18—C23	0.3 (13)
S1—Ir1—C3—C2	64.9 (5)	Ir2—C17—C18—C23	121.3 (9)
C5—Ir1—C3—C6	158.6 (10)	C16—C17—C18—Ir2	61.2 (6)
C1—Ir1—C3—C6	−157.6 (10)	C22—C17—C18—Ir2	−121.1 (8)
C4—Ir1—C3—C6	122.2 (11)	C15—Ir2—C18—C19	37.5 (5)
C2—Ir1—C3—C6	−120.8 (10)	C16—Ir2—C18—C19	81.7 (6)
S2—Ir1—C3—C6	66.0 (9)	C17—Ir2—C18—C19	117.7 (7)
S1—Ir1—C3—C6	−55.9 (9)	S4—Ir2—C18—C19	−63.7 (5)
C2—C3—C4—C5	1.4 (9)	S3—Ir2—C18—C19	173.1 (4)
C6—C3—C4—C5	175.6 (7)	C15—Ir2—C18—C17	−80.2 (6)
Ir1—C3—C4—C5	−60.5 (6)	C16—Ir2—C18—C17	−36.0 (5)
C2—C3—C4—C7	−176.8 (8)	C19—Ir2—C18—C17	−117.7 (7)
C6—C3—C4—C7	−2.7 (13)	S4—Ir2—C18—C17	178.6 (4)
Ir1—C3—C4—C7	121.3 (8)	S3—Ir2—C18—C17	55.4 (6)
C2—C3—C4—Ir1	61.9 (5)	C15—Ir2—C18—C23	158.7 (11)
C6—C3—C4—Ir1	−123.9 (8)	C16—Ir2—C18—C23	−157.1 (11)
C1—Ir1—C4—C5	38.8 (5)	C17—Ir2—C18—C23	−121.1 (11)
C3—Ir1—C4—C5	119.2 (7)	C19—Ir2—C18—C23	121.2 (11)
C2—Ir1—C4—C5	80.7 (5)	S4—Ir2—C18—C23	57.5 (10)
S2—Ir1—C4—C5	−101.7 (5)	S3—Ir2—C18—C23	−65.7 (10)
S1—Ir1—C4—C5	124.3 (8)	C16—C15—C19—C18	−0.4 (10)
C5—Ir1—C4—C3	−119.2 (7)	C20—C15—C19—C18	−179.8 (9)
C1—Ir1—C4—C3	−80.4 (5)	Ir2—C15—C19—C18	61.0 (6)
C2—Ir1—C4—C3	−38.4 (5)	C16—C15—C19—C24	177.3 (9)
S2—Ir1—C4—C3	139.1 (5)	C20—C15—C19—C24	−2.1 (16)
S1—Ir1—C4—C3	5.2 (12)	Ir2—C15—C19—C24	−121.3 (10)
C5—Ir1—C4—C7	121.2 (10)	C16—C15—C19—Ir2	−61.5 (6)
C1—Ir1—C4—C7	160.0 (10)	C20—C15—C19—Ir2	119.1 (10)
C3—Ir1—C4—C7	−119.6 (11)	C17—C18—C19—C15	1.0 (9)
C2—Ir1—C4—C7	−158.1 (10)	C23—C18—C19—C15	177.3 (8)
S2—Ir1—C4—C7	19.5 (9)	Ir2—C18—C19—C15	−60.9 (6)
S1—Ir1—C4—C7	−114.4 (9)	C17—C18—C19—C24	−176.8 (8)
C3—C4—C5—C1	−1.5 (9)	C23—C18—C19—C24	−0.5 (14)
C7—C4—C5—C1	176.7 (8)	Ir2—C18—C19—C24	121.3 (9)
Ir1—C4—C5—C1	−62.3 (6)	C17—C18—C19—Ir2	61.9 (6)
C3—C4—C5—C8	−178.4 (7)	C23—C18—C19—Ir2	−121.8 (9)
C7—C4—C5—C8	−0.2 (14)	C18—Ir2—C19—C15	116.9 (7)
Ir1—C4—C5—C8	120.8 (8)	C16—Ir2—C19—C15	37.8 (6)
C3—C4—C5—Ir1	60.8 (5)	C17—Ir2—C19—C15	78.9 (6)
C7—C4—C5—Ir1	−121.0 (9)	S4—Ir2—C19—C15	−112.3 (5)
C2—C1—C5—C4	1.1 (9)	S3—Ir2—C19—C15	92.0 (13)
C9—C1—C5—C4	−177.2 (9)	C15—Ir2—C19—C18	−116.9 (7)
Ir1—C1—C5—C4	62.9 (5)	C16—Ir2—C19—C18	−79.1 (5)
C2—C1—C5—C8	178.0 (7)	C17—Ir2—C19—C18	−38.0 (5)
C9—C1—C5—C8	−0.3 (14)	S4—Ir2—C19—C18	130.8 (4)
Ir1—C1—C5—C8	−120.2 (8)	S3—Ir2—C19—C18	−24.9 (14)
C2—C1—C5—Ir1	−61.8 (5)	C15—Ir2—C19—C24	122.9 (12)
C9—C1—C5—Ir1	119.9 (9)	C18—Ir2—C19—C24	−120.2 (12)
C1—Ir1—C5—C4	−117.0 (7)	C16—Ir2—C19—C24	160.7 (11)
C3—Ir1—C5—C4	−37.0 (5)	C17—Ir2—C19—C24	−158.3 (11)
C2—Ir1—C5—C4	−80.4 (5)	S4—Ir2—C19—C24	10.6 (10)
S2—Ir1—C5—C4	89.6 (5)	S3—Ir2—C19—C24	−145.2 (10)
S1—Ir1—C5—C4	−150.3 (4)	Ir2—S4—C25—C26	1.2 (7)
C4—Ir1—C5—C1	117.0 (7)	Ir2—S4—C25—C27	−177.4 (6)
C3—Ir1—C5—C1	80.0 (5)	C27—C25—C26—C28	−0.4 (13)
C2—Ir1—C5—C1	36.5 (5)	S4—C25—C26—C28	−178.9 (6)
S2—Ir1—C5—C1	−153.4 (4)	C27—C25—C26—S3	178.9 (6)
S1—Ir1—C5—C1	−33.4 (7)	S4—C25—C26—S3	0.4 (10)
C1—Ir1—C5—C8	120.3 (11)	Ir2—S3—C26—C25	−1.7 (7)
C4—Ir1—C5—C8	−122.8 (11)	Ir2—S3—C26—C28	177.7 (6)
C3—Ir1—C5—C8	−159.7 (10)	C26—C25—C27—N3	−140 (23)
C2—Ir1—C5—C8	156.8 (10)	S4—C25—C27—N3	39 (23)
S2—Ir1—C5—C8	−33.2 (10)	C25—C26—C28—N4	129 (20)
S1—Ir1—C5—C8	86.9 (10)	S3—C26—C28—N4	−50 (20)