Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002462/hg2140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002462/hg2140Isup2.hkl |
CCDC reference: 636672
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: modified SHELXL97.
[Ir(C17H13NOP)ClH(C17H14NOP)]·1.896CHCl3 | F(000) = 1985 |
Mr = 1013.22 | Dx = 1.749 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 77843 reflections |
a = 11.2208 (14) Å | θ = 3.2–30.6° |
b = 14.8301 (15) Å | µ = 4.06 mm−1 |
c = 23.188 (3) Å | T = 120 K |
β = 94.284 (6)° | Prism, yellow |
V = 3847.8 (8) Å3 | 0.60 × 0.30 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID imaging-plate diffractometer | 11703 independent reflections |
Radiation source: normal-focus sealed tube | 10697 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 10.00 pixels mm-1 | θmax = 30.5°, θmin = 3.1° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −21→21 |
Tmin = 0.254, Tmax = 0.481 | l = −33→33 |
94476 measured reflections |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0184P)2 + 12.9527P] where P = (Fo2 + 2Fc2)/3 |
11703 reflections | (Δ/σ)max = 0.004 |
515 parameters | Δρmax = 1.63 e Å−3 |
30 restraints | Δρmin = −1.06 e Å−3 |
Experimental. Indexing was performed from 3 oscillations which were exposed for 1.0 minutes. The camera radius was 127.40 mm. Readout performed in the 0.100 mm pixel mode. #1 Phi=0.0, chi=54.0, omega=0.0 to 180.0 with 2.0deg step #2 Phi=90.0, chi=50.0, omega=0.0 to 180.0 with 2.0deg step #4 Phi=180.0, chi=45.0, omega=0.0 to 90.0 with 2.0deg step A total of 225 images, corresponding to 450.0 °. osillation angles, were collected with 3 different goniometer setting. Exposure time was 2.0 minutes per degree. The camera radius was 127.40 mm. Readout performed in the 0.100 mm pixel mode. |
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 | Occ. (<1) | |
Ir | 0.501290 (8) | 0.754067 (6) | 0.328727 (4) | 0.01315 (3) | |
H0A | 0.597 (4) | 0.717 (3) | 0.3771 (17) | 0.016* | 0.88 |
Cl1A | 0.36580 (6) | 0.79608 (4) | 0.24471 (3) | 0.01407 (12) | 0.88 |
H0B | 0.4034 | 0.7905 | 0.2787 | 0.017* | 0.12 |
Cl1B | 0.6662 (6) | 0.7079 (5) | 0.3944 (3) | 0.0300 (13) | 0.12 |
P1 | 0.58044 (6) | 0.89325 (5) | 0.33549 (3) | 0.01550 (12) | |
P2 | 0.36717 (6) | 0.73192 (4) | 0.39479 (3) | 0.01400 (12) | |
O1 | 0.6774 (2) | 0.63415 (15) | 0.22684 (11) | 0.0284 (5) | |
O2 | 0.5092 (2) | 0.54409 (14) | 0.24884 (10) | 0.0242 (4) | |
H1 | 0.577 (3) | 0.596 (3) | 0.2442 (17) | 0.029* | |
N1 | 0.6488 (2) | 0.76839 (16) | 0.27421 (10) | 0.0175 (4) | |
N2 | 0.4265 (2) | 0.61982 (15) | 0.32267 (10) | 0.0161 (4) | |
C1 | 0.6879 (2) | 0.85489 (19) | 0.28633 (12) | 0.0185 (5) | |
C2 | 0.7875 (3) | 0.8918 (2) | 0.26597 (14) | 0.0256 (6) | |
H2 | 0.8119 | 0.9517 | 0.2754 | 0.031* | |
C3 | 0.8529 (3) | 0.8364 (2) | 0.23001 (16) | 0.0323 (7) | |
H3 | 0.9232 | 0.8589 | 0.2146 | 0.039* | |
C4 | 0.8155 (3) | 0.7511 (2) | 0.21739 (15) | 0.0291 (7) | |
H4 | 0.8600 | 0.7146 | 0.1931 | 0.035* | |
C5 | 0.7108 (3) | 0.7153 (2) | 0.23996 (13) | 0.0218 (5) | |
C6 | 0.5036 (2) | 0.99170 (18) | 0.30469 (13) | 0.0184 (5) | |
C7 | 0.4154 (3) | 1.0314 (2) | 0.33558 (15) | 0.0276 (6) | |
H7 | 0.3976 | 1.0073 | 0.3719 | 0.033* | |
C8 | 0.3537 (3) | 1.1064 (2) | 0.31297 (17) | 0.0329 (7) | |
H8 | 0.2932 | 1.1332 | 0.3339 | 0.040* | |
C9 | 0.3796 (3) | 1.1421 (2) | 0.26065 (16) | 0.0300 (7) | |
H9 | 0.3374 | 1.1934 | 0.2455 | 0.036* | |
C10 | 0.4671 (3) | 1.1029 (2) | 0.23031 (16) | 0.0338 (7) | |
H10 | 0.4857 | 1.1279 | 0.1943 | 0.041* | |
C11 | 0.5284 (3) | 1.0271 (2) | 0.25186 (14) | 0.0274 (6) | |
H11 | 0.5874 | 0.9998 | 0.2302 | 0.033* | |
C12 | 0.6598 (2) | 0.93401 (19) | 0.40098 (12) | 0.0189 (5) | |
C13 | 0.6587 (3) | 0.8844 (2) | 0.45180 (14) | 0.0315 (7) | |
H13 | 0.6157 | 0.8293 | 0.4522 | 0.038* | |
C14 | 0.7203 (4) | 0.9155 (3) | 0.50196 (16) | 0.0403 (9) | |
H14 | 0.7189 | 0.8819 | 0.5367 | 0.048* | |
C15 | 0.7840 (3) | 0.9957 (3) | 0.50148 (15) | 0.0334 (7) | |
H15 | 0.8258 | 1.0171 | 0.5359 | 0.040* | |
C16 | 0.7864 (3) | 1.0442 (2) | 0.45091 (15) | 0.0263 (6) | |
H16 | 0.8311 | 1.0986 | 0.4506 | 0.032* | |
C17 | 0.7247 (3) | 1.01481 (19) | 0.40049 (14) | 0.0219 (5) | |
H17 | 0.7263 | 1.0490 | 0.3659 | 0.026* | |
C18 | 0.3450 (2) | 0.62035 (17) | 0.36379 (11) | 0.0166 (5) | |
C19 | 0.2665 (3) | 0.55191 (19) | 0.37178 (13) | 0.0214 (5) | |
H19 | 0.2111 | 0.5550 | 0.4008 | 0.026* | |
C20 | 0.2712 (3) | 0.47656 (19) | 0.33508 (13) | 0.0222 (6) | |
H20 | 0.2180 | 0.4274 | 0.3387 | 0.027* | |
C21 | 0.3529 (3) | 0.47450 (18) | 0.29415 (13) | 0.0204 (5) | |
H21 | 0.3561 | 0.4234 | 0.2697 | 0.025* | |
C22 | 0.4333 (2) | 0.54768 (18) | 0.28752 (12) | 0.0180 (5) | |
C23 | 0.2233 (2) | 0.78598 (18) | 0.39740 (12) | 0.0163 (5) | |
C24 | 0.1440 (3) | 0.7581 (2) | 0.43755 (14) | 0.0255 (6) | |
H24 | 0.1671 | 0.7125 | 0.4649 | 0.031* | |
C25 | 0.0319 (3) | 0.7969 (3) | 0.43743 (16) | 0.0323 (7) | |
H25 | −0.0217 | 0.7781 | 0.4649 | 0.039* | |
C26 | −0.0025 (3) | 0.8631 (2) | 0.39726 (14) | 0.0294 (7) | |
H26 | −0.0800 | 0.8891 | 0.3971 | 0.035* | |
C27 | 0.0753 (3) | 0.8915 (2) | 0.35760 (13) | 0.0238 (6) | |
H27 | 0.0514 | 0.9370 | 0.3303 | 0.029* | |
C28 | 0.1892 (2) | 0.85332 (19) | 0.35750 (12) | 0.0186 (5) | |
H28 | 0.2430 | 0.8731 | 0.3304 | 0.022* | |
C29 | 0.4230 (2) | 0.71780 (18) | 0.46961 (12) | 0.0173 (5) | |
C30 | 0.4061 (3) | 0.7851 (2) | 0.50994 (13) | 0.0239 (6) | |
H30 | 0.3590 | 0.8365 | 0.4991 | 0.029* | |
C31 | 0.4580 (3) | 0.7776 (3) | 0.56625 (14) | 0.0319 (7) | |
H31 | 0.4462 | 0.8237 | 0.5937 | 0.038* | |
C32 | 0.5265 (4) | 0.7034 (3) | 0.58219 (15) | 0.0365 (8) | |
H32 | 0.5603 | 0.6976 | 0.6208 | 0.044* | |
C33 | 0.5463 (3) | 0.6366 (2) | 0.54152 (16) | 0.0354 (8) | |
H33 | 0.5952 | 0.5862 | 0.5523 | 0.042* | |
C34 | 0.4948 (3) | 0.6437 (2) | 0.48556 (14) | 0.0266 (6) | |
H34 | 0.5083 | 0.5981 | 0.4580 | 0.032* | |
C35 | 0.9721 (4) | 0.7541 (3) | 0.61695 (17) | 0.0489 (11) | |
H35 | 0.9651 | 0.7348 | 0.6579 | 0.059* | |
Cl2 | 0.85909 (15) | 0.69997 (11) | 0.57269 (6) | 0.0755 (5) | |
Cl3 | 1.11432 (12) | 0.72357 (9) | 0.59656 (5) | 0.0553 (3) | |
Cl4 | 0.95374 (10) | 0.87169 (9) | 0.61270 (5) | 0.0516 (3) | |
C36 | 0.8238 (12) | 0.5124 (11) | 0.4116 (7) | 0.002 (3)* | 0.14 |
H36 | 0.8901 | 0.4744 | 0.3984 | 0.002* | 0.14 |
Cl5 | 0.7695 (8) | 0.4702 (6) | 0.4778 (4) | 0.0210 (14)* | 0.14 |
Cl6 | 0.6959 (9) | 0.5128 (7) | 0.3599 (4) | 0.045 (2)* | 0.14 |
Cl7 | 0.8642 (12) | 0.6292 (8) | 0.4163 (5) | 0.078 (3)* | 0.14 |
C37 | 0.8247 (12) | 0.4964 (11) | 0.4033 (7) | 0.028 (5)* | 0.24 |
H37 | 0.8384 | 0.4477 | 0.3747 | 0.034* | 0.24 |
Cl8 | 0.7351 (6) | 0.4603 (4) | 0.4622 (3) | 0.0335 (10)* | 0.24 |
Cl9 | 0.9594 (5) | 0.5301 (4) | 0.4466 (3) | 0.0555 (12)* | 0.24 |
Cl10 | 0.7692 (6) | 0.5975 (5) | 0.3715 (3) | 0.0699 (18)* | 0.24 |
C38 | 0.7865 (18) | 0.5546 (17) | 0.4202 (8) | 0.049 (8)* | 0.15 |
H38 | 0.7471 | 0.6151 | 0.4204 | 0.059* | 0.15 |
Cl11 | 0.7288 (8) | 0.4874 (7) | 0.3594 (3) | 0.052 (2)* | 0.15 |
Cl12 | 0.9456 (8) | 0.5648 (8) | 0.4254 (4) | 0.058 (2)* | 0.15 |
Cl13 | 0.7644 (11) | 0.4941 (8) | 0.4840 (4) | 0.039 (2)* | 0.15 |
C39 | 0.826 (2) | 0.5070 (19) | 0.4133 (9) | 0.09 (2)* | 0.16 |
H39 | 0.8771 | 0.4546 | 0.4045 | 0.104* | 0.16 |
Cl14 | 0.9119 (7) | 0.6062 (5) | 0.4232 (3) | 0.0410 (13)* | 0.16 |
Cl15 | 0.7422 (9) | 0.4834 (9) | 0.4745 (4) | 0.033 (2)* | 0.16 |
Cl16 | 0.7222 (6) | 0.5304 (6) | 0.3545 (2) | 0.0244 (11)* | 0.16 |
C40 | 0.8108 (15) | 0.5425 (17) | 0.4282 (10) | 0.087 (13)* | 0.21 |
H40 | 0.8024 | 0.5938 | 0.4556 | 0.105* | 0.21 |
Cl17 | 0.9635 (6) | 0.5161 (5) | 0.4189 (3) | 0.0615 (16)* | 0.21 |
Cl18 | 0.7150 (6) | 0.4502 (5) | 0.4425 (3) | 0.0538 (17)* | 0.21 |
Cl19 | 0.7464 (6) | 0.5668 (6) | 0.3575 (3) | 0.0458 (12)* | 0.21 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir | 0.01331 (5) | 0.01218 (5) | 0.01417 (5) | 0.00134 (3) | 0.00234 (3) | −0.00184 (3) |
Cl1A | 0.0129 (3) | 0.0147 (3) | 0.0147 (3) | 0.0016 (2) | 0.0017 (2) | 0.0003 (2) |
Cl1B | 0.022 (3) | 0.041 (4) | 0.027 (3) | 0.001 (2) | 0.000 (2) | 0.010 (3) |
P1 | 0.0142 (3) | 0.0148 (3) | 0.0176 (3) | 0.0001 (2) | 0.0024 (2) | −0.0027 (2) |
P2 | 0.0146 (3) | 0.0139 (3) | 0.0137 (3) | 0.0013 (2) | 0.0023 (2) | −0.0002 (2) |
O1 | 0.0251 (11) | 0.0234 (11) | 0.0380 (13) | −0.0015 (8) | 0.0117 (9) | −0.0122 (9) |
O2 | 0.0251 (11) | 0.0207 (10) | 0.0280 (11) | −0.0023 (8) | 0.0100 (9) | −0.0089 (8) |
N1 | 0.0134 (10) | 0.0196 (11) | 0.0199 (11) | 0.0001 (8) | 0.0039 (8) | −0.0035 (8) |
N2 | 0.0159 (10) | 0.0140 (10) | 0.0181 (10) | 0.0017 (8) | 0.0007 (8) | −0.0006 (8) |
C1 | 0.0162 (12) | 0.0188 (12) | 0.0207 (13) | −0.0002 (9) | 0.0035 (10) | −0.0047 (10) |
C2 | 0.0205 (14) | 0.0266 (14) | 0.0306 (16) | −0.0062 (11) | 0.0082 (12) | −0.0085 (12) |
C3 | 0.0189 (14) | 0.0381 (18) | 0.0421 (19) | −0.0080 (13) | 0.0167 (13) | −0.0117 (15) |
C4 | 0.0205 (14) | 0.0336 (17) | 0.0348 (17) | −0.0008 (12) | 0.0129 (12) | −0.0108 (13) |
C5 | 0.0171 (12) | 0.0227 (13) | 0.0264 (14) | 0.0013 (10) | 0.0056 (11) | −0.0070 (11) |
C6 | 0.0160 (12) | 0.0146 (11) | 0.0241 (13) | −0.0005 (9) | −0.0012 (10) | −0.0039 (10) |
C7 | 0.0253 (15) | 0.0257 (15) | 0.0325 (16) | 0.0072 (12) | 0.0074 (13) | −0.0009 (12) |
C8 | 0.0252 (16) | 0.0284 (16) | 0.045 (2) | 0.0103 (12) | 0.0011 (14) | −0.0062 (14) |
C9 | 0.0262 (15) | 0.0216 (14) | 0.0404 (18) | 0.0031 (11) | −0.0096 (13) | −0.0006 (13) |
C10 | 0.0360 (18) | 0.0298 (16) | 0.0350 (18) | 0.0042 (14) | −0.0005 (14) | 0.0092 (14) |
C11 | 0.0270 (15) | 0.0269 (15) | 0.0287 (16) | 0.0041 (12) | 0.0042 (12) | 0.0025 (12) |
C12 | 0.0143 (12) | 0.0202 (12) | 0.0222 (13) | −0.0001 (9) | 0.0011 (10) | −0.0064 (10) |
C13 | 0.0331 (17) | 0.0368 (18) | 0.0239 (15) | −0.0155 (14) | −0.0019 (13) | −0.0001 (13) |
C14 | 0.051 (2) | 0.047 (2) | 0.0222 (16) | −0.0165 (18) | −0.0055 (15) | −0.0002 (15) |
C15 | 0.0352 (18) | 0.0367 (18) | 0.0274 (16) | −0.0062 (14) | −0.0038 (14) | −0.0101 (13) |
C16 | 0.0227 (14) | 0.0233 (14) | 0.0327 (16) | −0.0034 (11) | 0.0010 (12) | −0.0111 (12) |
C17 | 0.0222 (13) | 0.0176 (12) | 0.0259 (14) | 0.0005 (10) | 0.0015 (11) | −0.0058 (10) |
C18 | 0.0194 (12) | 0.0145 (11) | 0.0156 (12) | 0.0013 (9) | −0.0001 (9) | 0.0005 (9) |
C19 | 0.0241 (14) | 0.0205 (13) | 0.0197 (13) | −0.0031 (10) | 0.0025 (11) | 0.0008 (10) |
C20 | 0.0254 (14) | 0.0188 (12) | 0.0221 (13) | −0.0060 (10) | −0.0010 (11) | 0.0009 (10) |
C21 | 0.0251 (14) | 0.0136 (11) | 0.0222 (13) | −0.0017 (10) | −0.0015 (11) | −0.0032 (10) |
C22 | 0.0196 (12) | 0.0145 (11) | 0.0198 (12) | 0.0020 (9) | 0.0000 (10) | −0.0027 (9) |
C23 | 0.0153 (11) | 0.0170 (11) | 0.0167 (12) | 0.0016 (9) | 0.0022 (9) | 0.0000 (9) |
C24 | 0.0201 (13) | 0.0311 (15) | 0.0261 (14) | 0.0039 (11) | 0.0061 (11) | 0.0092 (12) |
C25 | 0.0220 (15) | 0.0440 (19) | 0.0324 (17) | 0.0054 (13) | 0.0117 (13) | 0.0098 (14) |
C26 | 0.0196 (14) | 0.0404 (18) | 0.0284 (16) | 0.0117 (13) | 0.0035 (12) | 0.0009 (13) |
C27 | 0.0245 (14) | 0.0257 (14) | 0.0212 (13) | 0.0093 (11) | 0.0015 (11) | 0.0024 (11) |
C28 | 0.0184 (12) | 0.0209 (12) | 0.0168 (12) | 0.0040 (10) | 0.0033 (10) | 0.0001 (10) |
C29 | 0.0179 (12) | 0.0183 (12) | 0.0158 (12) | −0.0007 (9) | 0.0017 (9) | −0.0001 (9) |
C30 | 0.0284 (15) | 0.0269 (14) | 0.0167 (13) | 0.0068 (11) | 0.0031 (11) | −0.0020 (11) |
C31 | 0.0382 (18) | 0.0403 (18) | 0.0171 (14) | 0.0070 (15) | 0.0011 (13) | −0.0058 (13) |
C32 | 0.043 (2) | 0.044 (2) | 0.0212 (15) | 0.0040 (16) | −0.0070 (14) | 0.0038 (14) |
C33 | 0.041 (2) | 0.0326 (17) | 0.0309 (17) | 0.0078 (15) | −0.0114 (15) | 0.0041 (14) |
C34 | 0.0308 (16) | 0.0224 (14) | 0.0259 (15) | 0.0044 (12) | −0.0034 (12) | 0.0003 (11) |
C35 | 0.055 (3) | 0.068 (3) | 0.0248 (17) | −0.015 (2) | 0.0121 (17) | 0.0065 (18) |
Cl2 | 0.0885 (10) | 0.0834 (10) | 0.0537 (7) | −0.0499 (8) | −0.0010 (7) | 0.0159 (7) |
Cl3 | 0.0713 (8) | 0.0548 (6) | 0.0418 (6) | 0.0104 (6) | 0.0171 (5) | 0.0003 (5) |
Cl4 | 0.0367 (5) | 0.0672 (7) | 0.0513 (6) | 0.0006 (5) | 0.0048 (4) | −0.0121 (5) |
Ir—N2 | 2.161 (2) | C19—C20 | 1.408 (4) |
Ir—N1 | 2.167 (2) | C19—H19 | 0.9500 |
Ir—P1 | 2.2479 (7) | C20—C21 | 1.368 (4) |
Ir—P2 | 2.2503 (7) | C20—H20 | 0.9500 |
Ir—Cl1B | 2.407 (7) | C21—C22 | 1.427 (4) |
Ir—Cl1A | 2.4602 (7) | C21—H21 | 0.9500 |
Ir—H0A | 1.60 (4) | C23—C28 | 1.395 (4) |
Ir—H0B | 1.6292 (2) | C23—C24 | 1.398 (4) |
P1—C12 | 1.806 (3) | C24—C25 | 1.383 (4) |
P1—C1 | 1.812 (3) | C24—H24 | 0.9500 |
P1—C6 | 1.815 (3) | C25—C26 | 1.389 (5) |
P2—C23 | 1.808 (3) | C25—H25 | 0.9500 |
P2—C29 | 1.812 (3) | C26—C27 | 1.380 (4) |
P2—C18 | 1.814 (3) | C26—H26 | 0.9500 |
O1—C5 | 1.290 (4) | C27—C28 | 1.398 (4) |
O1—H1 | 1.35 (4) | C27—H27 | 0.9500 |
O2—C22 | 1.284 (3) | C28—H28 | 0.9500 |
O2—H1 | 1.09 (4) | C29—C30 | 1.391 (4) |
N1—C5 | 1.348 (3) | C29—C34 | 1.396 (4) |
N1—C1 | 1.378 (3) | C30—C31 | 1.394 (4) |
N2—C22 | 1.350 (3) | C30—H30 | 0.9500 |
N2—C18 | 1.370 (3) | C31—C32 | 1.376 (5) |
C1—C2 | 1.361 (4) | C31—H31 | 0.9500 |
C2—C3 | 1.415 (4) | C32—C33 | 1.396 (5) |
C2—H2 | 0.9500 | C32—H32 | 0.9500 |
C3—C4 | 1.358 (5) | C33—C34 | 1.384 (5) |
C3—H3 | 0.9500 | C33—H33 | 0.9500 |
C4—C5 | 1.424 (4) | C34—H34 | 0.9500 |
C4—H4 | 0.9500 | C35—Cl3 | 1.758 (5) |
C6—C11 | 1.380 (4) | C35—Cl4 | 1.758 (5) |
C6—C7 | 1.394 (4) | C35—Cl2 | 1.763 (5) |
C7—C8 | 1.392 (4) | C35—H35 | 1.0000 |
C7—H7 | 0.9500 | C36—Cl7 | 1.792 (15) |
C8—C9 | 1.374 (5) | C36—Cl6 | 1.801 (14) |
C8—H8 | 0.9500 | C36—Cl5 | 1.805 (14) |
C9—C10 | 1.378 (5) | C36—H36 | 1.0000 |
C9—H9 | 0.9500 | C37—Cl10 | 1.764 (14) |
C10—C11 | 1.391 (4) | C37—Cl9 | 1.820 (15) |
C10—H10 | 0.9500 | C37—Cl8 | 1.835 (14) |
C11—H11 | 0.9500 | C37—H37 | 1.0000 |
C12—C13 | 1.390 (4) | C38—Cl13 | 1.762 (18) |
C12—C17 | 1.403 (4) | C38—Cl12 | 1.787 (18) |
C13—C14 | 1.387 (5) | C38—Cl11 | 1.808 (18) |
C13—H13 | 0.9500 | C38—H38 | 1.0000 |
C14—C15 | 1.388 (5) | C39—Cl16 | 1.76 (2) |
C14—H14 | 0.9500 | C39—Cl14 | 1.77 (2) |
C15—C16 | 1.377 (5) | C39—Cl15 | 1.79 (2) |
C15—H15 | 0.9500 | C39—H39 | 1.0000 |
C16—C17 | 1.384 (4) | C40—Cl19 | 1.779 (19) |
C16—H16 | 0.9500 | C40—Cl18 | 1.786 (19) |
C17—H17 | 0.9500 | C40—Cl17 | 1.788 (19) |
C18—C19 | 1.366 (4) | C40—H40 | 1.0000 |
N2—Ir—N1 | 111.23 (9) | C17—C16—H16 | 119.5 |
N2—Ir—P1 | 179.50 (7) | C16—C17—C12 | 119.3 (3) |
N1—Ir—P1 | 68.63 (6) | C16—C17—H17 | 120.4 |
N2—Ir—P2 | 68.51 (6) | C12—C17—H17 | 120.4 |
N1—Ir—P2 | 172.01 (7) | C19—C18—N2 | 124.2 (3) |
P1—Ir—P2 | 111.55 (2) | C19—C18—P2 | 134.0 (2) |
N2—Ir—Cl1B | 93.16 (18) | N2—C18—P2 | 101.66 (18) |
N1—Ir—Cl1B | 79.21 (17) | C18—C19—C20 | 117.0 (3) |
P1—Ir—Cl1B | 86.34 (17) | C18—C19—H19 | 121.5 |
P2—Ir—Cl1B | 92.81 (15) | C20—C19—H19 | 121.5 |
N2—Ir—Cl1A | 88.17 (6) | C21—C20—C19 | 119.7 (3) |
N1—Ir—Cl1A | 88.10 (7) | C21—C20—H20 | 120.2 |
P1—Ir—Cl1A | 92.31 (2) | C19—C20—H20 | 120.2 |
P2—Ir—Cl1A | 99.84 (3) | C20—C21—C22 | 121.3 (3) |
N2—Ir—H0A | 88.0 (14) | C20—C21—H21 | 119.4 |
N1—Ir—H0A | 86.5 (14) | C22—C21—H21 | 119.4 |
P1—Ir—H0A | 91.5 (14) | O2—C22—N2 | 121.6 (3) |
P2—Ir—H0A | 85.5 (14) | O2—C22—C21 | 120.1 (2) |
Cl1A—Ir—H0A | 171.8 (14) | N2—C22—C21 | 118.2 (3) |
N2—Ir—H0B | 91.23 (6) | C28—C23—C24 | 119.8 (3) |
N1—Ir—H0B | 93.19 (7) | C28—C23—P2 | 119.8 (2) |
P1—Ir—H0B | 89.255 (19) | C24—C23—P2 | 120.4 (2) |
P2—Ir—H0B | 94.80 (2) | C25—C24—C23 | 120.0 (3) |
Cl1B—Ir—H0B | 172.20 (15) | C25—C24—H24 | 120.0 |
C12—P1—C1 | 108.93 (13) | C23—C24—H24 | 120.0 |
C12—P1—C6 | 104.58 (13) | C24—C25—C26 | 120.2 (3) |
C1—P1—C6 | 108.91 (13) | C24—C25—H25 | 119.9 |
C12—P1—Ir | 122.23 (10) | C26—C25—H25 | 119.9 |
C1—P1—Ir | 86.89 (9) | C27—C26—C25 | 120.3 (3) |
C6—P1—Ir | 122.52 (9) | C27—C26—H26 | 119.8 |
C23—P2—C29 | 105.36 (13) | C25—C26—H26 | 119.8 |
C23—P2—C18 | 108.75 (13) | C26—C27—C28 | 120.1 (3) |
C29—P2—C18 | 107.54 (12) | C26—C27—H27 | 119.9 |
C23—P2—Ir | 127.04 (9) | C28—C27—H27 | 119.9 |
C29—P2—Ir | 117.89 (9) | C23—C28—C27 | 119.6 (3) |
C18—P2—Ir | 86.69 (9) | C23—C28—H28 | 120.2 |
C5—O1—H1 | 123.9 (17) | C27—C28—H28 | 120.2 |
C22—O2—H1 | 123 (2) | C30—C29—C34 | 119.5 (3) |
C5—N1—C1 | 119.5 (2) | C30—C29—P2 | 120.4 (2) |
C5—N1—Ir | 137.5 (2) | C34—C29—P2 | 119.7 (2) |
C1—N1—Ir | 102.59 (17) | C29—C30—C31 | 120.2 (3) |
C22—N2—C18 | 119.7 (2) | C29—C30—H30 | 119.9 |
C22—N2—Ir | 136.91 (19) | C31—C30—H30 | 119.9 |
C18—N2—Ir | 103.04 (16) | C32—C31—C30 | 120.1 (3) |
C2—C1—N1 | 124.1 (3) | C32—C31—H31 | 119.9 |
C2—C1—P1 | 134.0 (2) | C30—C31—H31 | 119.9 |
N1—C1—P1 | 101.76 (18) | C31—C32—C33 | 119.9 (3) |
C1—C2—C3 | 116.5 (3) | C31—C32—H32 | 120.0 |
C1—C2—H2 | 121.7 | C33—C32—H32 | 120.0 |
C3—C2—H2 | 121.7 | C34—C33—C32 | 120.2 (3) |
C4—C3—C2 | 120.2 (3) | C34—C33—H33 | 119.9 |
C4—C3—H3 | 119.9 | C32—C33—H33 | 119.9 |
C2—C3—H3 | 119.9 | C33—C34—C29 | 120.0 (3) |
C3—C4—C5 | 121.2 (3) | C33—C34—H34 | 120.0 |
C3—C4—H4 | 119.4 | C29—C34—H34 | 120.0 |
C5—C4—H4 | 119.4 | Cl3—C35—Cl4 | 110.2 (2) |
O1—C5—N1 | 122.0 (3) | Cl3—C35—Cl2 | 110.7 (3) |
O1—C5—C4 | 119.6 (3) | Cl4—C35—Cl2 | 110.1 (3) |
N1—C5—C4 | 118.4 (3) | Cl3—C35—H35 | 108.6 |
C11—C6—C7 | 119.6 (3) | Cl4—C35—H35 | 108.6 |
C11—C6—P1 | 122.3 (2) | Cl2—C35—H35 | 108.6 |
C7—C6—P1 | 118.2 (2) | Cl7—C36—Cl6 | 102.9 (9) |
C8—C7—C6 | 119.7 (3) | Cl7—C36—Cl5 | 112.5 (11) |
C8—C7—H7 | 120.1 | Cl6—C36—Cl5 | 105.4 (8) |
C6—C7—H7 | 120.1 | Cl7—C36—H36 | 111.8 |
C9—C8—C7 | 120.5 (3) | Cl6—C36—H36 | 111.8 |
C9—C8—H8 | 119.7 | Cl5—C36—H36 | 111.8 |
C7—C8—H8 | 119.7 | Cl10—C37—Cl9 | 104.5 (9) |
C8—C9—C10 | 119.6 (3) | Cl10—C37—Cl8 | 111.3 (9) |
C8—C9—H9 | 120.2 | Cl9—C37—Cl8 | 98.6 (8) |
C10—C9—H9 | 120.2 | Cl10—C37—H37 | 113.7 |
C9—C10—C11 | 120.6 (3) | Cl9—C37—H37 | 113.7 |
C9—C10—H10 | 119.7 | Cl8—C37—H37 | 113.7 |
C11—C10—H10 | 119.7 | Cl13—C38—Cl12 | 100.9 (11) |
C6—C11—C10 | 119.9 (3) | Cl13—C38—Cl11 | 108.0 (12) |
C6—C11—H11 | 120.0 | Cl12—C38—Cl11 | 113.4 (13) |
C10—C11—H11 | 120.0 | Cl13—C38—H38 | 111.4 |
C13—C12—C17 | 119.8 (3) | Cl12—C38—H38 | 111.4 |
C13—C12—P1 | 120.0 (2) | Cl11—C38—H38 | 111.4 |
C17—C12—P1 | 120.2 (2) | Cl16—C39—Cl14 | 105.1 (13) |
C14—C13—C12 | 120.0 (3) | Cl16—C39—Cl15 | 107.4 (13) |
C14—C13—H13 | 120.0 | Cl14—C39—Cl15 | 111.9 (14) |
C12—C13—H13 | 120.0 | Cl16—C39—H39 | 110.7 |
C13—C14—C15 | 120.2 (3) | Cl14—C39—H39 | 110.7 |
C13—C14—H14 | 119.9 | Cl15—C39—H39 | 110.7 |
C15—C14—H14 | 119.9 | Cl19—C40—Cl18 | 96.7 (10) |
C16—C15—C14 | 119.8 (3) | Cl19—C40—Cl17 | 105.0 (12) |
C16—C15—H15 | 120.1 | Cl18—C40—Cl17 | 116.8 (14) |
C14—C15—H15 | 120.1 | Cl19—C40—H40 | 112.3 |
C15—C16—C17 | 121.0 (3) | Cl18—C40—H40 | 112.3 |
C15—C16—H16 | 119.5 | Cl17—C40—H40 | 112.3 |
N2—Ir—P1—C12 | −39 (8) | C12—P1—C6—C7 | −64.5 (3) |
N1—Ir—P1—C12 | −112.53 (13) | C1—P1—C6—C7 | 179.2 (2) |
P2—Ir—P1—C12 | 58.89 (11) | Ir—P1—C6—C7 | 80.6 (3) |
Cl1B—Ir—P1—C12 | −32.70 (19) | C11—C6—C7—C8 | −0.2 (5) |
Cl1A—Ir—P1—C12 | 160.41 (11) | P1—C6—C7—C8 | −179.3 (3) |
N2—Ir—P1—C1 | 72 (8) | C6—C7—C8—C9 | −0.5 (5) |
N1—Ir—P1—C1 | −2.05 (12) | C7—C8—C9—C10 | 0.2 (5) |
P2—Ir—P1—C1 | 169.36 (9) | C8—C9—C10—C11 | 0.7 (5) |
Cl1B—Ir—P1—C1 | 77.78 (19) | C7—C6—C11—C10 | 1.1 (5) |
Cl1A—Ir—P1—C1 | −89.11 (10) | P1—C6—C11—C10 | −179.8 (3) |
N2—Ir—P1—C6 | −178 (100) | C9—C10—C11—C6 | −1.4 (5) |
N1—Ir—P1—C6 | 108.45 (14) | C1—P1—C12—C13 | −108.0 (3) |
P2—Ir—P1—C6 | −80.13 (12) | C6—P1—C12—C13 | 135.7 (3) |
Cl1B—Ir—P1—C6 | −171.7 (2) | Ir—P1—C12—C13 | −9.5 (3) |
Cl1A—Ir—P1—C6 | 21.40 (12) | C1—P1—C12—C17 | 70.7 (3) |
N2—Ir—P2—C23 | −112.83 (13) | C6—P1—C12—C17 | −45.6 (3) |
N1—Ir—P2—C23 | 157.5 (5) | Ir—P1—C12—C17 | 169.23 (18) |
P1—Ir—P2—C23 | 67.70 (12) | C17—C12—C13—C14 | 0.9 (5) |
Cl1B—Ir—P2—C23 | 154.9 (2) | P1—C12—C13—C14 | 179.6 (3) |
Cl1A—Ir—P2—C23 | −28.75 (12) | C12—C13—C14—C15 | −0.5 (6) |
N2—Ir—P2—C29 | 106.37 (12) | C13—C14—C15—C16 | −0.4 (6) |
N1—Ir—P2—C29 | 16.7 (5) | C14—C15—C16—C17 | 0.9 (5) |
P1—Ir—P2—C29 | −73.10 (11) | C15—C16—C17—C12 | −0.6 (5) |
Cl1B—Ir—P2—C29 | 14.1 (2) | C13—C12—C17—C16 | −0.3 (4) |
Cl1A—Ir—P2—C29 | −169.55 (10) | P1—C12—C17—C16 | −179.0 (2) |
N2—Ir—P2—C18 | −1.75 (11) | C22—N2—C18—C19 | −0.9 (4) |
N1—Ir—P2—C18 | −91.5 (5) | Ir—N2—C18—C19 | 173.1 (2) |
P1—Ir—P2—C18 | 178.78 (9) | C22—N2—C18—P2 | −176.8 (2) |
Cl1B—Ir—P2—C18 | −94.0 (2) | Ir—N2—C18—P2 | −2.80 (17) |
Cl1A—Ir—P2—C18 | 82.33 (9) | C23—P2—C18—C19 | −44.5 (3) |
N2—Ir—N1—C5 | −4.5 (3) | C29—P2—C18—C19 | 69.1 (3) |
P1—Ir—N1—C5 | 175.0 (3) | Ir—P2—C18—C19 | −172.7 (3) |
P2—Ir—N1—C5 | 82.1 (6) | C23—P2—C18—N2 | 130.76 (18) |
Cl1B—Ir—N1—C5 | 84.7 (3) | C29—P2—C18—N2 | −115.62 (18) |
Cl1A—Ir—N1—C5 | −91.8 (3) | Ir—P2—C18—N2 | 2.62 (16) |
N2—Ir—N1—C1 | −176.72 (17) | N2—C18—C19—C20 | 0.2 (4) |
P1—Ir—N1—C1 | 2.76 (16) | P2—C18—C19—C20 | 174.6 (2) |
P2—Ir—N1—C1 | −90.1 (5) | C18—C19—C20—C21 | 0.5 (4) |
Cl1B—Ir—N1—C1 | −87.5 (2) | C19—C20—C21—C22 | −0.4 (4) |
Cl1A—Ir—N1—C1 | 95.98 (17) | C18—N2—C22—O2 | −179.3 (3) |
N1—Ir—N2—C22 | −13.8 (3) | Ir—N2—C22—O2 | 9.3 (4) |
P1—Ir—N2—C22 | −88 (8) | C18—N2—C22—C21 | 0.9 (4) |
P2—Ir—N2—C22 | 174.7 (3) | Ir—N2—C22—C21 | −170.5 (2) |
Cl1B—Ir—N2—C22 | −93.5 (3) | C20—C21—C22—O2 | 179.9 (3) |
Cl1A—Ir—N2—C22 | 73.4 (3) | C20—C21—C22—N2 | −0.3 (4) |
N1—Ir—N2—C18 | 173.80 (16) | C29—P2—C23—C28 | 140.3 (2) |
P1—Ir—N2—C18 | 100 (8) | C18—P2—C23—C28 | −104.6 (2) |
P2—Ir—N2—C18 | 2.37 (15) | Ir—P2—C23—C28 | −4.3 (3) |
Cl1B—Ir—N2—C18 | 94.2 (2) | C29—P2—C23—C24 | −42.4 (3) |
Cl1A—Ir—N2—C18 | −98.95 (16) | C18—P2—C23—C24 | 72.6 (3) |
C5—N1—C1—C2 | −0.3 (5) | Ir—P2—C23—C24 | 173.0 (2) |
Ir—N1—C1—C2 | 173.7 (3) | C28—C23—C24—C25 | 0.3 (5) |
C5—N1—C1—P1 | −177.2 (2) | P2—C23—C24—C25 | −176.9 (3) |
Ir—N1—C1—P1 | −3.26 (18) | C23—C24—C25—C26 | 0.4 (6) |
C12—P1—C1—C2 | −50.3 (4) | C24—C25—C26—C27 | −0.7 (6) |
C6—P1—C1—C2 | 63.2 (4) | C25—C26—C27—C28 | 0.3 (5) |
Ir—P1—C1—C2 | −173.4 (3) | C24—C23—C28—C27 | −0.8 (4) |
C12—P1—C1—N1 | 126.17 (19) | P2—C23—C28—C27 | 176.5 (2) |
C6—P1—C1—N1 | −120.33 (19) | C26—C27—C28—C23 | 0.5 (5) |
Ir—P1—C1—N1 | 3.07 (17) | C23—P2—C29—C30 | −39.5 (3) |
N1—C1—C2—C3 | 0.3 (5) | C18—P2—C29—C30 | −155.4 (2) |
P1—C1—C2—C3 | 176.1 (3) | Ir—P2—C29—C30 | 109.0 (2) |
C1—C2—C3—C4 | 0.0 (5) | C23—P2—C29—C34 | 147.7 (2) |
C2—C3—C4—C5 | −0.2 (6) | C18—P2—C29—C34 | 31.9 (3) |
C1—N1—C5—O1 | −179.4 (3) | Ir—P2—C29—C34 | −63.8 (3) |
Ir—N1—C5—O1 | 9.4 (5) | C34—C29—C30—C31 | −1.6 (5) |
C1—N1—C5—C4 | 0.0 (4) | P2—C29—C30—C31 | −174.4 (3) |
Ir—N1—C5—C4 | −171.2 (2) | C29—C30—C31—C32 | 0.1 (5) |
C3—C4—C5—O1 | 179.6 (3) | C30—C31—C32—C33 | 1.5 (6) |
C3—C4—C5—N1 | 0.2 (5) | C31—C32—C33—C34 | −1.6 (6) |
C12—P1—C6—C11 | 116.5 (3) | C32—C33—C34—C29 | 0.1 (6) |
C1—P1—C6—C11 | 0.2 (3) | C30—C29—C34—C33 | 1.5 (5) |
Ir—P1—C6—C11 | −98.5 (3) | P2—C29—C34—C33 | 174.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 1.09 (4) | 1.35 (4) | 2.398 (3) | 158 (4) |
C28—H28···Cl1A | 0.95 | 2.75 | 3.502 (3) | 137 |