Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034842/dn2059sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034842/dn2059Isup2.hkl |
CCDC reference: 624203
Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[Ir(C13H19N2O2S)(C10H15)Cl]·CHCl3 | F(000) = 1480 |
Mr = 749.60 | Dx = 1.736 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 15012 reflections |
a = 9.4012 (5) Å | θ = 1.9–25.5° |
b = 12.8491 (7) Å | µ = 5.12 mm−1 |
c = 23.7478 (17) Å | T = 173 K |
V = 2868.7 (3) Å3 | Needle, yellow |
Z = 4 | 0.45 × 0.15 × 0.08 mm |
Stoe IPDS diffractometer | 5576 independent reflections |
Radiation source: fine-focus sealed tube | 4830 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ scans | θmax = 25.9°, θmin = 2.3° |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2003) | h = −11→11 |
Tmin = 0.360, Tmax = 0.557 | k = −15→15 |
15012 measured reflections | l = −29→27 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0306P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max = 0.002 |
5576 reflections | Δρmax = 1.53 e Å−3 |
313 parameters | Δρmin = −1.82 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2413 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.024 (7) |
Experimental. A crystal was mounted at 173 K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using Mo Kα graphite monochromated radiation. Image plate distance 70 mm, φ oscillation scans 0 - 200°, step Δφ = 1.2°, 3 minutes per frame. |
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 | 0.67846 (2) | 0.975962 (17) | 0.284936 (9) | 0.01982 (6) | |
S1 | 0.71822 (14) | 0.79667 (11) | 0.19040 (6) | 0.0220 (3) | |
O1 | 0.7959 (5) | 0.7582 (3) | 0.23804 (17) | 0.0316 (10) | |
N1 | 0.6671 (5) | 0.9139 (3) | 0.20146 (16) | 0.0192 (10) | |
N2 | 0.4944 (5) | 1.0524 (4) | 0.2531 (2) | 0.0267 (12) | |
H2A | 0.4141 | 1.0191 | 0.2660 | 0.032* | |
H2B | 0.4923 | 1.1199 | 0.2660 | 0.032* | |
C11 | 0.4943 (6) | 1.0524 (4) | 0.1911 (3) | 0.0221 (13) | |
H11A | 0.5670 | 1.1033 | 0.1774 | 0.027* | |
C2 | 0.8157 (7) | 0.9480 (4) | 0.3564 (3) | 0.0326 (14) | |
O2 | 0.6050 (4) | 0.7294 (3) | 0.17001 (19) | 0.0306 (10) | |
C17 | 0.8438 (6) | 0.8000 (4) | 0.1343 (2) | 0.0228 (12) | |
C4 | 0.8767 (6) | 1.0584 (5) | 0.2824 (3) | 0.0296 (13) | |
C14 | 0.3986 (7) | 0.9744 (6) | 0.0824 (3) | 0.0402 (15) | |
H14A | 0.3263 | 0.9214 | 0.0923 | 0.048* | |
H14B | 0.4067 | 0.9766 | 0.0408 | 0.048* | |
C1 | 0.7380 (6) | 1.0442 (5) | 0.3632 (3) | 0.0323 (16) | |
C12 | 0.5349 (6) | 0.9447 (4) | 0.1712 (2) | 0.0233 (13) | |
H12A | 0.4576 | 0.8959 | 0.1831 | 0.028* | |
C18 | 0.8924 (6) | 0.7056 (5) | 0.1132 (3) | 0.0269 (13) | |
H18A | 0.8581 | 0.6422 | 0.1286 | 0.032* | |
C13 | 0.5416 (7) | 0.9432 (5) | 0.1076 (3) | 0.0331 (15) | |
H13A | 0.5673 | 0.8725 | 0.0946 | 0.040* | |
H13B | 0.6161 | 0.9920 | 0.0946 | 0.040* | |
C22 | 0.8975 (6) | 0.8926 (5) | 0.1127 (3) | 0.0303 (14) | |
H22A | 0.8671 | 0.9576 | 0.1275 | 0.036* | |
C5 | 0.7789 (6) | 1.1127 (4) | 0.3179 (3) | 0.0267 (14) | |
C21 | 0.9957 (7) | 0.8891 (5) | 0.0693 (3) | 0.0341 (16) | |
H21A | 1.0319 | 0.9525 | 0.0544 | 0.041* | |
C19 | 0.9900 (6) | 0.7039 (5) | 0.0701 (3) | 0.0324 (15) | |
H19A | 1.0218 | 0.6388 | 0.0559 | 0.039* | |
C3 | 0.9020 (6) | 0.9582 (5) | 0.3086 (3) | 0.0355 (17) | |
C7 | 0.8101 (11) | 0.8557 (6) | 0.3946 (4) | 0.070 (3) | |
H7C | 0.8691 | 0.8689 | 0.4279 | 0.083* | |
H7B | 0.8460 | 0.7944 | 0.3747 | 0.083* | |
H7A | 0.7116 | 0.8435 | 0.4063 | 0.083* | |
C20 | 1.0430 (6) | 0.7950 (6) | 0.0469 (3) | 0.0338 (15) | |
C10 | 0.7358 (7) | 1.2238 (5) | 0.3106 (4) | 0.049 (2) | |
H10A | 0.7209 | 1.2383 | 0.2705 | 0.059* | |
H10B | 0.8109 | 1.2692 | 0.3253 | 0.059* | |
H10C | 0.6473 | 1.2366 | 0.3313 | 0.059* | |
C8 | 1.0165 (7) | 0.8843 (6) | 0.2883 (5) | 0.071 (3) | |
H8A | 1.0035 | 0.8162 | 0.3062 | 0.085* | |
H8B | 1.1103 | 0.9121 | 0.2983 | 0.085* | |
H8C | 1.0100 | 0.8767 | 0.2473 | 0.085* | |
C6 | 0.6390 (8) | 1.0717 (8) | 0.4109 (3) | 0.063 (3) | |
H6A | 0.5722 | 1.1255 | 0.3984 | 0.076* | |
H6B | 0.6944 | 1.0979 | 0.4428 | 0.076* | |
H6C | 0.5860 | 1.0096 | 0.4225 | 0.076* | |
C16 | 0.3492 (6) | 1.0829 (5) | 0.1677 (3) | 0.0317 (15) | |
H16A | 0.2762 | 1.0340 | 0.1819 | 0.038* | |
H16B | 0.3242 | 1.1537 | 0.1809 | 0.038* | |
C15 | 0.3503 (8) | 1.0809 (5) | 0.1041 (3) | 0.0386 (17) | |
H15A | 0.4155 | 1.1354 | 0.0898 | 0.046* | |
H15B | 0.2536 | 1.0961 | 0.0897 | 0.046* | |
C23 | 1.1504 (7) | 0.7917 (6) | −0.0003 (3) | 0.0449 (19) | |
H23A | 1.1328 | 0.8496 | −0.0262 | 0.054* | |
H23B | 1.1418 | 0.7256 | −0.0205 | 0.054* | |
H23C | 1.2465 | 0.7979 | 0.0154 | 0.054* | |
C9 | 0.9498 (8) | 1.0991 (7) | 0.2306 (3) | 0.053 (2) | |
H9C | 1.0393 | 1.1327 | 0.2413 | 0.064* | |
H9B | 0.8881 | 1.1498 | 0.2118 | 0.064* | |
H9A | 0.9696 | 1.0412 | 0.2048 | 0.064* | |
Cl3 | 0.1979 (3) | 0.92961 (19) | 0.43475 (11) | 0.0833 (8) | |
Cl2 | 0.2021 (3) | 0.70790 (19) | 0.41831 (13) | 0.0866 (8) | |
C24 | 0.3063 (10) | 0.8185 (6) | 0.4271 (3) | 0.052 (2) | |
H24A | 0.3648 | 0.8277 | 0.3923 | 0.062* | |
Cl4 | 0.4225 (3) | 0.8078 (2) | 0.48421 (10) | 0.0764 (7) | |
Cl1 | 0.50167 (15) | 0.84418 (12) | 0.30971 (7) | 0.0323 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.01598 (8) | 0.01686 (9) | 0.02663 (10) | 0.00012 (10) | −0.00136 (11) | −0.00259 (11) |
S1 | 0.0220 (7) | 0.0157 (7) | 0.0283 (7) | 0.0009 (5) | 0.0031 (6) | −0.0005 (6) |
O1 | 0.038 (3) | 0.025 (2) | 0.031 (2) | 0.008 (2) | 0.0018 (19) | 0.0013 (17) |
N1 | 0.020 (2) | 0.016 (2) | 0.022 (3) | −0.002 (2) | −0.001 (2) | −0.0005 (16) |
N2 | 0.024 (3) | 0.022 (3) | 0.035 (3) | 0.002 (2) | −0.006 (2) | −0.007 (2) |
C11 | 0.021 (3) | 0.011 (3) | 0.034 (3) | 0.002 (2) | −0.006 (2) | −0.004 (2) |
C2 | 0.029 (3) | 0.029 (3) | 0.040 (3) | −0.003 (3) | −0.016 (3) | 0.010 (3) |
O2 | 0.022 (2) | 0.019 (2) | 0.050 (3) | −0.0037 (17) | 0.003 (2) | −0.008 (2) |
C17 | 0.017 (3) | 0.023 (3) | 0.029 (3) | 0.001 (2) | −0.004 (2) | −0.002 (2) |
C4 | 0.020 (2) | 0.032 (3) | 0.037 (3) | −0.010 (2) | −0.007 (3) | −0.007 (3) |
C14 | 0.047 (4) | 0.040 (4) | 0.034 (3) | 0.007 (4) | −0.015 (3) | −0.001 (4) |
C1 | 0.024 (3) | 0.045 (5) | 0.028 (3) | −0.005 (3) | −0.007 (2) | −0.011 (3) |
C12 | 0.022 (3) | 0.018 (3) | 0.030 (3) | −0.002 (2) | −0.007 (2) | 0.003 (2) |
C18 | 0.024 (3) | 0.025 (3) | 0.032 (3) | 0.001 (3) | 0.000 (3) | −0.003 (3) |
C13 | 0.039 (4) | 0.026 (3) | 0.034 (4) | 0.008 (3) | 0.000 (3) | −0.003 (3) |
C22 | 0.029 (3) | 0.025 (3) | 0.038 (4) | −0.001 (3) | 0.003 (3) | −0.003 (3) |
C5 | 0.022 (3) | 0.017 (3) | 0.042 (4) | −0.003 (2) | −0.014 (3) | −0.007 (3) |
C21 | 0.029 (3) | 0.034 (4) | 0.040 (4) | −0.010 (3) | 0.009 (3) | −0.003 (3) |
C19 | 0.023 (3) | 0.038 (4) | 0.036 (4) | 0.008 (3) | −0.004 (3) | −0.008 (3) |
C3 | 0.014 (3) | 0.034 (4) | 0.058 (4) | 0.006 (3) | −0.023 (3) | −0.018 (3) |
C7 | 0.072 (6) | 0.062 (5) | 0.075 (6) | −0.022 (5) | −0.043 (5) | 0.041 (4) |
C20 | 0.021 (3) | 0.051 (4) | 0.029 (4) | 0.001 (3) | −0.003 (3) | −0.003 (3) |
C10 | 0.037 (4) | 0.016 (3) | 0.094 (6) | 0.001 (3) | −0.019 (4) | −0.011 (4) |
C8 | 0.026 (3) | 0.051 (5) | 0.137 (8) | 0.021 (3) | −0.021 (5) | −0.039 (6) |
C6 | 0.049 (5) | 0.102 (7) | 0.038 (4) | −0.017 (4) | 0.006 (3) | −0.032 (4) |
C16 | 0.030 (4) | 0.030 (3) | 0.035 (4) | 0.007 (3) | −0.011 (3) | −0.005 (3) |
C15 | 0.044 (4) | 0.022 (3) | 0.050 (4) | 0.012 (3) | −0.015 (3) | −0.004 (3) |
C23 | 0.029 (4) | 0.072 (5) | 0.034 (4) | 0.001 (3) | 0.006 (3) | −0.011 (4) |
C9 | 0.036 (4) | 0.071 (6) | 0.052 (5) | −0.033 (4) | 0.009 (3) | 0.002 (4) |
Cl3 | 0.100 (2) | 0.0646 (14) | 0.0850 (17) | 0.0328 (15) | −0.0039 (16) | −0.0171 (12) |
Cl2 | 0.0799 (18) | 0.0610 (14) | 0.119 (2) | −0.0069 (14) | 0.0193 (17) | −0.0129 (14) |
C24 | 0.068 (5) | 0.051 (4) | 0.037 (4) | 0.006 (5) | 0.015 (4) | −0.002 (3) |
Cl4 | 0.0771 (16) | 0.098 (2) | 0.0538 (14) | 0.0118 (14) | 0.0010 (12) | 0.0105 (13) |
Cl1 | 0.0284 (8) | 0.0359 (9) | 0.0325 (8) | −0.0119 (7) | 0.0074 (7) | 0.0023 (7) |
Ir1—N2 | 2.129 (5) | C13—H13B | 0.9900 |
Ir1—C1 | 2.130 (6) | C22—C21 | 1.383 (9) |
Ir1—N1 | 2.140 (4) | C22—H22A | 0.9500 |
Ir1—C5 | 2.143 (5) | C5—C10 | 1.493 (8) |
Ir1—C4 | 2.145 (5) | C21—C20 | 1.395 (9) |
Ir1—C2 | 2.162 (6) | C21—H21A | 0.9500 |
Ir1—C3 | 2.188 (5) | C19—C20 | 1.386 (10) |
Ir1—Cl1 | 2.4445 (14) | C19—H19A | 0.9500 |
S1—O1 | 1.435 (4) | C3—C8 | 1.514 (9) |
S1—O2 | 1.454 (4) | C7—H7C | 0.9800 |
S1—N1 | 1.602 (4) | C7—H7B | 0.9800 |
S1—C17 | 1.780 (6) | C7—H7A | 0.9800 |
N1—C12 | 1.489 (7) | C20—C23 | 1.508 (9) |
N2—C11 | 1.472 (7) | C10—H10A | 0.9800 |
N2—H2A | 0.9200 | C10—H10B | 0.9800 |
N2—H2B | 0.9200 | C10—H10C | 0.9800 |
C11—C12 | 1.511 (8) | C8—H8A | 0.9800 |
C11—C16 | 1.524 (8) | C8—H8B | 0.9800 |
C11—H11A | 1.0000 | C8—H8C | 0.9800 |
C2—C3 | 1.402 (10) | C6—H6A | 0.9800 |
C2—C1 | 1.445 (9) | C6—H6B | 0.9800 |
C2—C7 | 1.494 (9) | C6—H6C | 0.9800 |
C17—C18 | 1.390 (8) | C16—C15 | 1.512 (9) |
C17—C22 | 1.391 (8) | C16—H16A | 0.9900 |
C4—C5 | 1.429 (9) | C16—H16B | 0.9900 |
C4—C3 | 1.450 (9) | C15—H15A | 0.9900 |
C4—C9 | 1.503 (10) | C15—H15B | 0.9900 |
C14—C13 | 1.525 (9) | C23—H23A | 0.9800 |
C14—C15 | 1.531 (9) | C23—H23B | 0.9800 |
C14—H14A | 0.9900 | C23—H23C | 0.9800 |
C14—H14B | 0.9900 | C9—H9C | 0.9800 |
C1—C5 | 1.443 (9) | C9—H9B | 0.9800 |
C1—C6 | 1.508 (9) | C9—H9A | 0.9800 |
C12—C13 | 1.512 (8) | Cl3—C24 | 1.764 (8) |
C12—H12A | 1.0000 | Cl2—C24 | 1.738 (9) |
C18—C19 | 1.376 (9) | C24—Cl4 | 1.746 (9) |
C18—H18A | 0.9500 | C24—H24A | 1.0000 |
C13—H13A | 0.9900 | ||
N2—Ir1—C1 | 109.5 (2) | C12—C13—C14 | 110.6 (5) |
N2—Ir1—N1 | 78.58 (18) | C12—C13—H13A | 109.5 |
C1—Ir1—N1 | 167.2 (2) | C14—C13—H13A | 109.5 |
N2—Ir1—C5 | 96.3 (2) | C12—C13—H13B | 109.5 |
C1—Ir1—C5 | 39.5 (2) | C14—C13—H13B | 109.5 |
N1—Ir1—C5 | 131.8 (2) | H13A—C13—H13B | 108.1 |
N2—Ir1—C4 | 117.9 (2) | C21—C22—C17 | 119.3 (6) |
C1—Ir1—C4 | 66.0 (3) | C21—C22—H22A | 120.3 |
N1—Ir1—C4 | 101.6 (2) | C17—C22—H22A | 120.3 |
C5—Ir1—C4 | 38.9 (2) | C4—C5—C1 | 108.3 (5) |
N2—Ir1—C2 | 147.2 (2) | C4—C5—C10 | 125.0 (6) |
C1—Ir1—C2 | 39.3 (2) | C1—C5—C10 | 126.6 (6) |
N1—Ir1—C2 | 134.0 (2) | C4—C5—Ir1 | 70.6 (3) |
C5—Ir1—C2 | 65.6 (2) | C1—C5—Ir1 | 69.8 (3) |
C4—Ir1—C2 | 65.5 (3) | C10—C5—Ir1 | 128.4 (4) |
N2—Ir1—C3 | 157.0 (2) | C22—C21—C20 | 121.7 (6) |
C1—Ir1—C3 | 64.3 (2) | C22—C21—H21A | 119.2 |
N1—Ir1—C3 | 104.3 (2) | C20—C21—H21A | 119.2 |
C5—Ir1—C3 | 64.4 (2) | C18—C19—C20 | 121.5 (6) |
C4—Ir1—C3 | 39.1 (2) | C18—C19—H19A | 119.3 |
C2—Ir1—C3 | 37.6 (3) | C20—C19—H19A | 119.3 |
N2—Ir1—Cl1 | 81.52 (14) | C2—C3—C4 | 109.6 (5) |
C1—Ir1—Cl1 | 104.69 (18) | C2—C3—C8 | 127.7 (7) |
N1—Ir1—Cl1 | 86.04 (12) | C4—C3—C8 | 122.5 (7) |
C5—Ir1—Cl1 | 141.24 (18) | C2—C3—Ir1 | 70.2 (3) |
C4—Ir1—Cl1 | 160.01 (18) | C4—C3—Ir1 | 68.9 (3) |
C2—Ir1—Cl1 | 95.84 (17) | C8—C3—Ir1 | 131.8 (5) |
C3—Ir1—Cl1 | 121.3 (2) | C2—C7—H7C | 109.5 |
O1—S1—O2 | 115.5 (3) | C2—C7—H7B | 109.5 |
O1—S1—N1 | 110.3 (2) | H7C—C7—H7B | 109.5 |
O2—S1—N1 | 113.2 (2) | C2—C7—H7A | 109.5 |
O1—S1—C17 | 105.1 (2) | H7C—C7—H7A | 109.5 |
O2—S1—C17 | 104.5 (3) | H7B—C7—H7A | 109.5 |
N1—S1—C17 | 107.4 (2) | C19—C20—C21 | 117.8 (6) |
C12—N1—S1 | 114.9 (3) | C19—C20—C23 | 120.8 (7) |
C12—N1—Ir1 | 112.9 (3) | C21—C20—C23 | 121.4 (6) |
S1—N1—Ir1 | 119.2 (2) | C5—C10—H10A | 109.5 |
C11—N2—Ir1 | 110.9 (4) | C5—C10—H10B | 109.5 |
C11—N2—H2A | 109.5 | H10A—C10—H10B | 109.5 |
Ir1—N2—H2A | 109.5 | C5—C10—H10C | 109.5 |
C11—N2—H2B | 109.5 | H10A—C10—H10C | 109.5 |
Ir1—N2—H2B | 109.5 | H10B—C10—H10C | 109.5 |
H2A—N2—H2B | 108.1 | C3—C8—H8A | 109.5 |
N2—C11—C12 | 108.2 (5) | C3—C8—H8B | 109.5 |
N2—C11—C16 | 111.4 (5) | H8A—C8—H8B | 109.5 |
C12—C11—C16 | 110.4 (5) | C3—C8—H8C | 109.5 |
N2—C11—H11A | 109.0 | H8A—C8—H8C | 109.5 |
C12—C11—H11A | 109.0 | H8B—C8—H8C | 109.5 |
C16—C11—H11A | 109.0 | C1—C6—H6A | 109.5 |
C3—C2—C1 | 107.7 (5) | C1—C6—H6B | 109.5 |
C3—C2—C7 | 125.9 (7) | H6A—C6—H6B | 109.5 |
C1—C2—C7 | 126.4 (7) | C1—C6—H6C | 109.5 |
C3—C2—Ir1 | 72.2 (3) | H6A—C6—H6C | 109.5 |
C1—C2—Ir1 | 69.1 (3) | H6B—C6—H6C | 109.5 |
C7—C2—Ir1 | 126.0 (5) | C15—C16—C11 | 110.7 (5) |
C18—C17—C22 | 119.6 (5) | C15—C16—H16A | 109.5 |
C18—C17—S1 | 117.8 (4) | C11—C16—H16A | 109.5 |
C22—C17—S1 | 122.6 (5) | C15—C16—H16B | 109.5 |
C5—C4—C3 | 106.6 (6) | C11—C16—H16B | 109.5 |
C5—C4—C9 | 127.3 (6) | H16A—C16—H16B | 108.1 |
C3—C4—C9 | 125.8 (6) | C16—C15—C14 | 110.7 (5) |
C5—C4—Ir1 | 70.5 (3) | C16—C15—H15A | 109.5 |
C3—C4—Ir1 | 72.1 (3) | C14—C15—H15A | 109.5 |
C9—C4—Ir1 | 126.3 (5) | C16—C15—H15B | 109.5 |
C13—C14—C15 | 111.4 (6) | C14—C15—H15B | 109.5 |
C13—C14—H14A | 109.4 | H15A—C15—H15B | 108.1 |
C15—C14—H14A | 109.4 | C20—C23—H23A | 109.5 |
C13—C14—H14B | 109.4 | C20—C23—H23B | 109.5 |
C15—C14—H14B | 109.4 | H23A—C23—H23B | 109.5 |
H14A—C14—H14B | 108.0 | C20—C23—H23C | 109.5 |
C5—C1—C2 | 107.7 (5) | H23A—C23—H23C | 109.5 |
C5—C1—C6 | 125.6 (6) | H23B—C23—H23C | 109.5 |
C2—C1—C6 | 126.7 (7) | C4—C9—H9C | 109.5 |
C5—C1—Ir1 | 70.7 (3) | C4—C9—H9B | 109.5 |
C2—C1—Ir1 | 71.5 (3) | H9C—C9—H9B | 109.5 |
C6—C1—Ir1 | 126.1 (4) | C4—C9—H9A | 109.5 |
N1—C12—C11 | 107.7 (4) | H9C—C9—H9A | 109.5 |
N1—C12—C13 | 116.3 (5) | H9B—C9—H9A | 109.5 |
C11—C12—C13 | 109.5 (5) | Cl2—C24—Cl4 | 112.5 (4) |
N1—C12—H12A | 107.7 | Cl2—C24—Cl3 | 110.4 (5) |
C11—C12—H12A | 107.7 | Cl4—C24—Cl3 | 110.2 (4) |
C13—C12—H12A | 107.7 | Cl2—C24—H24A | 107.9 |
C19—C18—C17 | 120.1 (6) | Cl4—C24—H24A | 107.9 |
C19—C18—H18A | 119.9 | Cl3—C24—H24A | 107.9 |
C17—C18—H18A | 119.9 | ||
O1—S1—N1—C12 | −151.9 (4) | C3—Ir1—C1—C6 | −159.2 (8) |
O2—S1—N1—C12 | −20.8 (5) | Cl1—Ir1—C1—C6 | −41.2 (7) |
C17—S1—N1—C12 | 94.0 (4) | S1—N1—C12—C11 | 174.2 (4) |
O1—S1—N1—Ir1 | −13.3 (4) | Ir1—N1—C12—C11 | 33.0 (5) |
O2—S1—N1—Ir1 | 117.8 (3) | S1—N1—C12—C13 | −62.5 (6) |
C17—S1—N1—Ir1 | −127.3 (3) | Ir1—N1—C12—C13 | 156.3 (4) |
N2—Ir1—N1—C12 | −7.3 (3) | N2—C11—C12—N1 | −50.4 (6) |
C1—Ir1—N1—C12 | −137.7 (9) | C16—C11—C12—N1 | −172.4 (5) |
C5—Ir1—N1—C12 | −95.6 (4) | N2—C11—C12—C13 | −177.7 (5) |
C4—Ir1—N1—C12 | −123.8 (4) | C16—C11—C12—C13 | 60.2 (7) |
C2—Ir1—N1—C12 | 169.1 (3) | C22—C17—C18—C19 | −1.8 (9) |
C3—Ir1—N1—C12 | −163.9 (4) | S1—C17—C18—C19 | −179.7 (4) |
Cl1—Ir1—N1—C12 | 74.8 (3) | N1—C12—C13—C14 | 178.9 (5) |
N2—Ir1—N1—S1 | −146.7 (3) | C11—C12—C13—C14 | −58.7 (7) |
C1—Ir1—N1—S1 | 82.8 (10) | C15—C14—C13—C12 | 56.0 (7) |
C5—Ir1—N1—S1 | 125.0 (3) | C18—C17—C22—C21 | 1.8 (9) |
C4—Ir1—N1—S1 | 96.8 (3) | S1—C17—C22—C21 | 179.5 (5) |
C2—Ir1—N1—S1 | 29.7 (4) | C3—C4—C5—C1 | −3.6 (6) |
C3—Ir1—N1—S1 | 56.7 (3) | C9—C4—C5—C1 | −178.9 (6) |
Cl1—Ir1—N1—S1 | −64.6 (3) | Ir1—C4—C5—C1 | 59.9 (4) |
C1—Ir1—N2—C11 | 148.9 (4) | C3—C4—C5—C10 | 172.6 (6) |
N1—Ir1—N2—C11 | −20.8 (4) | C9—C4—C5—C10 | −2.7 (10) |
C5—Ir1—N2—C11 | 110.6 (4) | Ir1—C4—C5—C10 | −123.9 (6) |
C4—Ir1—N2—C11 | 76.4 (5) | C3—C4—C5—Ir1 | −63.4 (4) |
C2—Ir1—N2—C11 | 163.9 (4) | C9—C4—C5—Ir1 | 121.3 (6) |
C3—Ir1—N2—C11 | 78.9 (7) | C2—C1—C5—C4 | 2.0 (6) |
Cl1—Ir1—N2—C11 | −108.5 (4) | C6—C1—C5—C4 | 178.4 (6) |
Ir1—N2—C11—C12 | 45.0 (5) | Ir1—C1—C5—C4 | −60.4 (4) |
Ir1—N2—C11—C16 | 166.5 (4) | C2—C1—C5—C10 | −174.1 (6) |
N2—Ir1—C2—C3 | −140.3 (4) | C6—C1—C5—C10 | 2.3 (10) |
C1—Ir1—C2—C3 | −117.6 (5) | Ir1—C1—C5—C10 | 123.5 (6) |
N1—Ir1—C2—C3 | 46.1 (4) | C2—C1—C5—Ir1 | 62.4 (4) |
C5—Ir1—C2—C3 | −79.2 (4) | C6—C1—C5—Ir1 | −121.2 (6) |
C4—Ir1—C2—C3 | −36.2 (4) | N2—Ir1—C5—C4 | −127.8 (4) |
Cl1—Ir1—C2—C3 | 136.3 (3) | C1—Ir1—C5—C4 | 118.9 (5) |
N2—Ir1—C2—C1 | −22.7 (6) | N1—Ir1—C5—C4 | −47.5 (5) |
N1—Ir1—C2—C1 | 163.8 (3) | C2—Ir1—C5—C4 | 80.6 (4) |
C5—Ir1—C2—C1 | 38.4 (3) | C3—Ir1—C5—C4 | 39.0 (4) |
C4—Ir1—C2—C1 | 81.4 (4) | Cl1—Ir1—C5—C4 | 147.9 (3) |
C3—Ir1—C2—C1 | 117.6 (5) | N2—Ir1—C5—C1 | 113.2 (3) |
Cl1—Ir1—C2—C1 | −106.1 (3) | N1—Ir1—C5—C1 | −166.5 (3) |
N2—Ir1—C2—C7 | 97.8 (7) | C4—Ir1—C5—C1 | −118.9 (5) |
C1—Ir1—C2—C7 | 120.5 (9) | C2—Ir1—C5—C1 | −38.3 (3) |
N1—Ir1—C2—C7 | −75.7 (8) | C3—Ir1—C5—C1 | −79.9 (4) |
C5—Ir1—C2—C7 | 158.9 (8) | Cl1—Ir1—C5—C1 | 28.9 (4) |
C4—Ir1—C2—C7 | −158.1 (8) | N2—Ir1—C5—C10 | −8.1 (7) |
C3—Ir1—C2—C7 | −121.8 (8) | C1—Ir1—C5—C10 | −121.3 (8) |
Cl1—Ir1—C2—C7 | 14.4 (7) | N1—Ir1—C5—C10 | 72.2 (7) |
O1—S1—C17—C18 | 69.0 (5) | C4—Ir1—C5—C10 | 119.8 (8) |
O2—S1—C17—C18 | −53.0 (5) | C2—Ir1—C5—C10 | −159.6 (7) |
N1—S1—C17—C18 | −173.5 (4) | C3—Ir1—C5—C10 | 158.8 (7) |
O1—S1—C17—C22 | −108.8 (5) | Cl1—Ir1—C5—C10 | −92.3 (7) |
O2—S1—C17—C22 | 129.2 (5) | C17—C22—C21—C20 | −0.3 (10) |
N1—S1—C17—C22 | 8.7 (6) | C17—C18—C19—C20 | 0.4 (9) |
N2—Ir1—C4—C5 | 62.7 (5) | C1—C2—C3—C4 | −2.7 (6) |
C1—Ir1—C4—C5 | −37.5 (4) | C7—C2—C3—C4 | 179.6 (6) |
N1—Ir1—C4—C5 | 145.8 (4) | Ir1—C2—C3—C4 | 57.7 (4) |
C2—Ir1—C4—C5 | −80.8 (4) | C1—C2—C3—C8 | 171.5 (6) |
C3—Ir1—C4—C5 | −115.7 (6) | C7—C2—C3—C8 | −6.2 (11) |
Cl1—Ir1—C4—C5 | −103.2 (5) | Ir1—C2—C3—C8 | −128.1 (6) |
N2—Ir1—C4—C3 | 178.4 (3) | C1—C2—C3—Ir1 | −60.3 (4) |
C1—Ir1—C4—C3 | 78.2 (4) | C7—C2—C3—Ir1 | 122.0 (7) |
N1—Ir1—C4—C3 | −98.4 (4) | C5—C4—C3—C2 | 3.9 (6) |
C5—Ir1—C4—C3 | 115.7 (6) | C9—C4—C3—C2 | 179.3 (6) |
C2—Ir1—C4—C3 | 34.9 (4) | Ir1—C4—C3—C2 | −58.5 (4) |
Cl1—Ir1—C4—C3 | 12.6 (8) | C5—C4—C3—C8 | −170.7 (6) |
N2—Ir1—C4—C9 | −59.8 (6) | C9—C4—C3—C8 | 4.7 (9) |
C1—Ir1—C4—C9 | −160.1 (7) | Ir1—C4—C3—C8 | 127.0 (6) |
N1—Ir1—C4—C9 | 23.3 (6) | C5—C4—C3—Ir1 | 62.4 (4) |
C5—Ir1—C4—C9 | −122.5 (7) | C9—C4—C3—Ir1 | −122.2 (6) |
C2—Ir1—C4—C9 | 156.6 (7) | N2—Ir1—C3—C2 | 117.9 (6) |
C3—Ir1—C4—C9 | 121.7 (7) | C1—Ir1—C3—C2 | 38.5 (4) |
Cl1—Ir1—C4—C9 | 134.3 (6) | N1—Ir1—C3—C2 | −147.7 (3) |
C3—C2—C1—C5 | 0.4 (6) | C5—Ir1—C3—C2 | 82.5 (4) |
C7—C2—C1—C5 | 178.1 (6) | C4—Ir1—C3—C2 | 121.4 (5) |
Ir1—C2—C1—C5 | −61.9 (4) | Cl1—Ir1—C3—C2 | −53.6 (4) |
C3—C2—C1—C6 | −175.9 (6) | N2—Ir1—C3—C4 | −3.6 (8) |
C7—C2—C1—C6 | 1.8 (10) | C1—Ir1—C3—C4 | −82.9 (4) |
Ir1—C2—C1—C6 | 121.8 (6) | N1—Ir1—C3—C4 | 90.9 (4) |
C3—C2—C1—Ir1 | 62.3 (4) | C5—Ir1—C3—C4 | −38.9 (4) |
C7—C2—C1—Ir1 | −120.0 (7) | C2—Ir1—C3—C4 | −121.4 (5) |
N2—Ir1—C1—C5 | −75.7 (3) | Cl1—Ir1—C3—C4 | −175.0 (3) |
N1—Ir1—C1—C5 | 52.0 (11) | N2—Ir1—C3—C8 | −118.8 (8) |
C4—Ir1—C1—C5 | 37.0 (3) | C1—Ir1—C3—C8 | 161.9 (9) |
C2—Ir1—C1—C5 | 117.1 (5) | N1—Ir1—C3—C8 | −24.4 (8) |
C3—Ir1—C1—C5 | 80.3 (4) | C5—Ir1—C3—C8 | −154.1 (9) |
Cl1—Ir1—C1—C5 | −161.8 (3) | C4—Ir1—C3—C8 | −115.3 (10) |
N2—Ir1—C1—C2 | 167.2 (3) | C2—Ir1—C3—C8 | 123.3 (9) |
N1—Ir1—C1—C2 | −65.1 (11) | Cl1—Ir1—C3—C8 | 69.7 (8) |
C5—Ir1—C1—C2 | −117.1 (5) | C18—C19—C20—C21 | 1.0 (9) |
C4—Ir1—C1—C2 | −80.1 (4) | C18—C19—C20—C23 | 179.8 (6) |
C3—Ir1—C1—C2 | −36.8 (4) | C22—C21—C20—C19 | −1.0 (10) |
Cl1—Ir1—C1—C2 | 81.1 (3) | C22—C21—C20—C23 | −179.8 (6) |
N2—Ir1—C1—C6 | 44.8 (7) | N2—C11—C16—C15 | −179.1 (5) |
N1—Ir1—C1—C6 | 172.5 (8) | C12—C11—C16—C15 | −59.0 (7) |
C5—Ir1—C1—C6 | 120.5 (8) | C11—C16—C15—C14 | 55.3 (7) |
C4—Ir1—C1—C6 | 157.6 (7) | C13—C14—C15—C16 | −54.1 (8) |
C2—Ir1—C1—C6 | −122.4 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24A···Cl1 | 1.00 | 2.36 | 3.357 (8) | 178 |
N2—H2A···Cl1 | 0.92 | 2.60 | 2.996 (5) | 106 |
N2—H2B···O2i | 0.92 | 2.26 | 3.063 (7) | 145 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |