Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008809/wm6056sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008809/wm6056IIsup2.hkl |
CCDC reference: 272125
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Ir(C2O4)(C11H8N)4]·1.974C3H6O | Z = 2 |
Mr = 1203.79 | F(000) = 1170 |
Triclinic, P1 | Dx = 1.683 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9708 (5) Å | Cell parameters from 8192 reflections |
b = 13.0403 (7) Å | θ = 1.7–29.6° |
c = 19.3556 (10) Å | µ = 5.65 mm−1 |
α = 103.383 (1)° | T = 173 K |
β = 99.003 (1)° | Block, gold |
γ = 98.203 (1)° | 0.20 × 0.15 × 0.10 mm |
V = 2375.9 (2) Å3 |
Bruker SMART 1000 CCD area-detector diffractometer | 13184 independent reflections |
Radiation source: fine-focus sealed tube | 9639 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 29.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.430, Tmax = 0.568 | k = −18→18 |
30150 measured reflections | l = −26→26 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.9043P] where P = (Fo2 + 2Fc2)/3 |
13184 reflections | (Δ/σ)max = 0.040 |
602 parameters | Δρmax = 2.37 e Å−3 |
12 restraints | Δρmin = −1.13 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 | Occ. (<1) | |
Ir1 | 0.333434 (7) | 0.133535 (5) | 0.446300 (4) | 0.02833 (2) | |
Ir1' | 0.362785 (7) | 0.627249 (6) | 0.095088 (4) | 0.03433 (2) | |
O1 | 0.51118 (12) | 0.05688 (10) | 0.42742 (7) | 0.0325 (3) | |
O2 | 0.37124 (12) | 0.05975 (10) | 0.53663 (7) | 0.0329 (4) | |
O1' | 0.34793 (13) | 0.46263 (11) | 0.03022 (7) | 0.0375 (4) | |
O2' | 0.54098 (14) | 0.63805 (11) | 0.04149 (7) | 0.0397 (4) | |
N1 | 0.18998 (15) | 0.00040 (12) | 0.39304 (8) | 0.0331 (4) | |
N2 | 0.47597 (15) | 0.27106 (12) | 0.49302 (9) | 0.0340 (4) | |
N1' | 0.49092 (16) | 0.60726 (14) | 0.18067 (9) | 0.0399 (5) | |
N2' | 0.22824 (18) | 0.65759 (13) | 0.01539 (9) | 0.0421 (5) | |
C1 | 0.2177 (2) | −0.08684 (16) | 0.34887 (11) | 0.0400 (6) | |
H1 | 0.3102 | −0.0881 | 0.3428 | 0.048* | |
C2 | 0.1173 (2) | −0.17347 (18) | 0.31264 (14) | 0.0551 (8) | |
H2 | 0.1391 | −0.2338 | 0.2813 | 0.066* | |
C3 | −0.0151 (2) | −0.1718 (2) | 0.32232 (15) | 0.0611 (8) | |
H3 | −0.0863 | −0.2318 | 0.2982 | 0.073* | |
C4 | −0.0458 (2) | −0.08301 (18) | 0.36708 (14) | 0.0526 (7) | |
H4 | −0.1379 | −0.0819 | 0.3739 | 0.063* | |
C5 | 0.05789 (19) | 0.00445 (15) | 0.40197 (11) | 0.0363 (5) | |
C6 | 0.04163 (19) | 0.10710 (15) | 0.44648 (11) | 0.0349 (5) | |
C7 | −0.0838 (2) | 0.13056 (18) | 0.46267 (12) | 0.0453 (6) | |
H7 | −0.1647 | 0.0765 | 0.4465 | 0.054* | |
C8 | −0.0914 (2) | 0.23063 (19) | 0.50161 (13) | 0.0531 (7) | |
H8 | −0.1772 | 0.2464 | 0.5122 | 0.064* | |
C9 | 0.0276 (2) | 0.30909 (18) | 0.52551 (13) | 0.0521 (7) | |
H9 | 0.0225 | 0.3787 | 0.5525 | 0.062* | |
C10 | 0.1528 (2) | 0.28741 (16) | 0.51061 (11) | 0.0383 (6) | |
H10 | 0.2326 | 0.3424 | 0.5276 | 0.046* | |
C11 | 0.16490 (18) | 0.18546 (14) | 0.47069 (10) | 0.0309 (5) | |
C12 | 0.55132 (19) | 0.29571 (17) | 0.56057 (11) | 0.0401 (6) | |
H12 | 0.5320 | 0.2502 | 0.5911 | 0.048* | |
C13 | 0.6552 (2) | 0.38425 (18) | 0.58715 (13) | 0.0491 (7) | |
H13 | 0.7049 | 0.4008 | 0.6356 | 0.059* | |
C14 | 0.6861 (2) | 0.44829 (19) | 0.54261 (15) | 0.0576 (8) | |
H14 | 0.7586 | 0.5092 | 0.5594 | 0.069* | |
C15 | 0.6101 (2) | 0.42279 (18) | 0.47308 (14) | 0.0520 (7) | |
H15 | 0.6314 | 0.4658 | 0.4414 | 0.062* | |
C16 | 0.5021 (2) | 0.33424 (15) | 0.44888 (11) | 0.0380 (6) | |
C17 | 0.4120 (2) | 0.29878 (15) | 0.37732 (11) | 0.0386 (5) | |
C18 | 0.4151 (3) | 0.35527 (18) | 0.32429 (13) | 0.0527 (7) | |
H18 | 0.4777 | 0.4214 | 0.3342 | 0.063* | |
C19 | 0.3283 (3) | 0.31591 (18) | 0.25800 (13) | 0.0538 (7) | |
H19 | 0.3291 | 0.3553 | 0.2224 | 0.065* | |
C20 | 0.2397 (3) | 0.21851 (18) | 0.24332 (13) | 0.0522 (7) | |
H20 | 0.1816 | 0.1900 | 0.1969 | 0.063* | |
C21 | 0.2348 (2) | 0.16169 (17) | 0.29592 (11) | 0.0433 (6) | |
H21 | 0.1719 | 0.0956 | 0.2852 | 0.052* | |
C22 | 0.32132 (18) | 0.20062 (14) | 0.36423 (10) | 0.0327 (5) | |
C23 | 0.46067 (17) | 0.00014 (14) | 0.53137 (9) | 0.0286 (5) | |
C1' | 0.5299 (2) | 0.51368 (18) | 0.18534 (11) | 0.0447 (6) | |
H1' | 0.4928 | 0.4514 | 0.1467 | 0.054* | |
C2' | 0.6216 (2) | 0.5048 (2) | 0.24422 (12) | 0.0498 (7) | |
H2' | 0.6479 | 0.4381 | 0.2459 | 0.060* | |
C3' | 0.6733 (2) | 0.5945 (2) | 0.29992 (12) | 0.0523 (7) | |
H3' | 0.7367 | 0.5904 | 0.3409 | 0.063* | |
C4' | 0.6340 (2) | 0.69079 (19) | 0.29705 (12) | 0.0457 (6) | |
H4' | 0.6691 | 0.7526 | 0.3363 | 0.055* | |
C5' | 0.54292 (19) | 0.69752 (18) | 0.23668 (11) | 0.0414 (6) | |
C6' | 0.4934 (2) | 0.79181 (17) | 0.22350 (11) | 0.0404 (6) | |
C7' | 0.5351 (2) | 0.89533 (19) | 0.27230 (12) | 0.0504 (7) | |
H7' | 0.5974 | 0.9052 | 0.3168 | 0.060* | |
C8' | 0.4855 (3) | 0.98123 (19) | 0.25546 (13) | 0.0562 (8) | |
H8' | 0.5125 | 1.0504 | 0.2884 | 0.067* | |
C9' | 0.3980 (3) | 0.9669 (2) | 0.19161 (14) | 0.0609 (8) | |
H9' | 0.3645 | 1.0270 | 0.1804 | 0.073* | |
C10' | 0.3549 (2) | 0.86603 (18) | 0.14134 (13) | 0.0498 (7) | |
H10' | 0.2929 | 0.8584 | 0.0971 | 0.060* | |
C11' | 0.4039 (2) | 0.77698 (16) | 0.15697 (11) | 0.0390 (6) | |
C12' | 0.2659 (3) | 0.69184 (19) | −0.04096 (13) | 0.0574 (8) | |
H12' | 0.3603 | 0.7006 | −0.0452 | 0.069* | |
C13' | 0.1701 (3) | 0.7143 (2) | −0.09224 (15) | 0.0719 (10) | |
H13' | 0.1973 | 0.7384 | −0.1316 | 0.086* | |
C14' | 0.0341 (3) | 0.7008 (2) | −0.08495 (16) | 0.0737 (10) | |
H14' | −0.0336 | 0.7155 | −0.1198 | 0.088* | |
C15' | −0.0043 (3) | 0.6672 (2) | −0.02925 (15) | 0.0643 (9) | |
H15' | −0.0989 | 0.6571 | −0.0254 | 0.077* | |
C16' | 0.0945 (2) | 0.64706 (17) | 0.02308 (13) | 0.0491 (7) | |
C17' | 0.0713 (2) | 0.61467 (18) | 0.08750 (13) | 0.0485 (7) | |
C18' | −0.0598 (2) | 0.5979 (2) | 0.10718 (15) | 0.0626 (9) | |
H18' | −0.1393 | 0.6079 | 0.0773 | 0.075* | |
C19' | −0.0714 (2) | 0.5674 (2) | 0.16910 (15) | 0.0666 (9) | |
H19' | −0.1591 | 0.5577 | 0.1825 | 0.080* | |
C20' | 0.0423 (2) | 0.5505 (2) | 0.21236 (13) | 0.0599 (8) | |
H20' | 0.0320 | 0.5266 | 0.2544 | 0.072* | |
C21' | 0.1729 (2) | 0.56836 (19) | 0.19464 (12) | 0.0509 (7) | |
H21' | 0.2511 | 0.5581 | 0.2255 | 0.061* | |
C22' | 0.1901 (2) | 0.60126 (16) | 0.13201 (11) | 0.0400 (6) | |
C23' | 0.55548 (18) | 0.54999 (15) | 0.00349 (10) | 0.0328 (5) | |
O101 | 0.8231 (3) | 0.42152 (18) | 0.35311 (15) | 0.1089 (10) | |
C101 | 0.9857 (3) | 0.3143 (3) | 0.3262 (2) | 0.1011 (14) | |
H10A | 1.0502 | 0.3831 | 0.3424 | 0.152* | |
H10B | 0.9886 | 0.2799 | 0.2758 | 0.152* | |
H10C | 1.0121 | 0.2677 | 0.3570 | 0.152* | |
C102 | 0.8491 (3) | 0.3319 (2) | 0.33088 (17) | 0.0722 (10) | |
C103 | 0.7381 (4) | 0.2374 (3) | 0.3079 (2) | 0.0985 (15) | |
H10D | 0.6495 | 0.2598 | 0.3125 | 0.148* | |
H10E | 0.7554 | 0.1886 | 0.3385 | 0.148* | |
H10F | 0.7352 | 0.2006 | 0.2573 | 0.148* | |
C01A | 0.8697 (4) | 0.9800 (3) | 0.1364 (4) | 0.0963 (19) | 0.209 (3) |
C02A | 0.9601 (5) | 0.8988 (4) | 0.1349 (9) | 0.151 (3) | 0.209 (3) |
H02A | 1.0570 | 0.9351 | 0.1500 | 0.227* | 0.209 (3) |
H02B | 0.9450 | 0.8524 | 0.0856 | 0.227* | 0.209 (3) |
H02C | 0.9378 | 0.8553 | 0.1681 | 0.227* | 0.209 (3) |
C03A | 0.7407 (5) | 0.9498 (9) | 0.0808 (4) | 0.151 (3) | 0.209 (3) |
H03A | 0.6884 | 1.0083 | 0.0873 | 0.227* | 0.209 (3) |
H03B | 0.6848 | 0.8847 | 0.0858 | 0.227* | 0.209 (3) |
H03C | 0.7636 | 0.9364 | 0.0325 | 0.227* | 0.209 (3) |
O01A | 0.9169 (10) | 1.0734 (3) | 0.1688 (6) | 0.132 (2) | 0.209 (3) |
C01B | 0.8867 (3) | 0.9744 (2) | 0.1379 (3) | 0.0963 (19) | 0.531 (3) |
C02B | 1.0089 (4) | 0.9277 (4) | 0.1224 (5) | 0.151 (3) | 0.531 (3) |
H02D | 1.0727 | 0.9790 | 0.1076 | 0.227* | 0.531 (3) |
H02E | 0.9794 | 0.8614 | 0.0834 | 0.227* | 0.531 (3) |
H02F | 1.0555 | 0.9117 | 0.1661 | 0.227* | 0.531 (3) |
C03B | 0.7675 (4) | 0.8970 (4) | 0.1427 (4) | 0.151 (3) | 0.531 (3) |
H03D | 0.6953 | 0.9356 | 0.1581 | 0.227* | 0.531 (3) |
H03E | 0.7969 | 0.8577 | 0.1781 | 0.227* | 0.531 (3) |
H03F | 0.7311 | 0.8463 | 0.0952 | 0.227* | 0.531 (3) |
O01B | 0.8909 (5) | 1.0701 (2) | 0.1533 (3) | 0.132 (2) | 0.531 (3) |
C02C | 0.3017 (17) | 0.1852 (14) | 0.0611 (9) | 0.105 (5)* | 0.234 (3) |
H02G | 0.2904 | 0.2531 | 0.0922 | 0.158* | 0.234 (3) |
H02H | 0.2404 | 0.1256 | 0.0697 | 0.158* | 0.234 (3) |
H02I | 0.2782 | 0.1862 | 0.0102 | 0.158* | 0.234 (3) |
O01C | 0.5292 (12) | 0.2218 (9) | 0.1318 (6) | 0.114 (4)* | 0.234 (3) |
C01C | 0.4361 (18) | 0.1723 (14) | 0.0770 (9) | 0.105 (5)* | 0.234 (3) |
C03C | 0.520 (3) | 0.075 (2) | 0.0452 (15) | 0.207 (13)* | 0.234 (3) |
H03G | 0.6172 | 0.0946 | 0.0697 | 0.311* | 0.234 (3) |
H03H | 0.5138 | 0.0654 | −0.0070 | 0.311* | 0.234 (3) |
H03I | 0.4779 | 0.0079 | 0.0542 | 0.311* | 0.234 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.02396 (3) | 0.02515 (3) | 0.03438 (3) | 0.00362 (2) | 0.00467 (2) | 0.00605 (2) |
Ir1' | 0.03068 (3) | 0.03418 (4) | 0.03286 (3) | 0.00177 (3) | 0.00719 (3) | 0.00033 (3) |
O1 | 0.0266 (5) | 0.0334 (6) | 0.0379 (6) | 0.0055 (5) | 0.0094 (5) | 0.0082 (5) |
O2 | 0.0268 (5) | 0.0354 (6) | 0.0368 (6) | 0.0062 (5) | 0.0074 (5) | 0.0091 (5) |
O1' | 0.0319 (6) | 0.0367 (7) | 0.0379 (7) | 0.0000 (5) | 0.0091 (5) | 0.0001 (6) |
O2' | 0.0366 (6) | 0.0360 (7) | 0.0403 (7) | −0.0010 (6) | 0.0076 (6) | 0.0024 (6) |
N1 | 0.0286 (7) | 0.0312 (7) | 0.0393 (8) | 0.0035 (6) | 0.0055 (6) | 0.0110 (6) |
N2 | 0.0282 (7) | 0.0297 (7) | 0.0414 (8) | 0.0046 (6) | 0.0084 (6) | 0.0034 (6) |
N1' | 0.0304 (7) | 0.0468 (9) | 0.0379 (8) | −0.0028 (7) | 0.0119 (6) | 0.0043 (7) |
N2' | 0.0436 (9) | 0.0342 (8) | 0.0396 (9) | 0.0032 (7) | 0.0050 (7) | −0.0037 (7) |
C1 | 0.0365 (9) | 0.0324 (9) | 0.0485 (10) | 0.0025 (8) | 0.0116 (8) | 0.0060 (8) |
C2 | 0.0503 (12) | 0.0359 (11) | 0.0676 (14) | −0.0027 (10) | 0.0145 (11) | −0.0044 (11) |
C3 | 0.0412 (11) | 0.0448 (12) | 0.0789 (16) | −0.0136 (10) | 0.0116 (11) | −0.0070 (12) |
C4 | 0.0345 (10) | 0.0431 (11) | 0.0689 (14) | −0.0035 (9) | 0.0091 (10) | −0.0009 (11) |
C5 | 0.0292 (8) | 0.0335 (8) | 0.0460 (10) | 0.0056 (7) | 0.0059 (7) | 0.0109 (8) |
C6 | 0.0285 (8) | 0.0326 (8) | 0.0434 (10) | 0.0057 (7) | 0.0051 (7) | 0.0109 (7) |
C7 | 0.0277 (8) | 0.0467 (11) | 0.0610 (12) | 0.0038 (8) | 0.0102 (8) | 0.0142 (9) |
C8 | 0.0386 (9) | 0.0592 (12) | 0.0690 (13) | 0.0252 (8) | 0.0217 (9) | 0.0140 (11) |
C9 | 0.0500 (11) | 0.0436 (10) | 0.0632 (13) | 0.0184 (9) | 0.0162 (10) | 0.0060 (10) |
C10 | 0.0352 (9) | 0.0358 (9) | 0.0415 (10) | 0.0062 (8) | 0.0069 (8) | 0.0060 (8) |
C11 | 0.0320 (8) | 0.0292 (8) | 0.0322 (8) | 0.0057 (7) | 0.0046 (7) | 0.0105 (6) |
C12 | 0.0313 (8) | 0.0423 (10) | 0.0407 (10) | 0.0059 (8) | 0.0083 (8) | −0.0014 (8) |
C13 | 0.0379 (10) | 0.0460 (11) | 0.0475 (12) | 0.0020 (9) | −0.0009 (9) | −0.0095 (10) |
C14 | 0.0371 (10) | 0.0396 (11) | 0.0789 (16) | −0.0056 (9) | 0.0076 (11) | −0.0078 (12) |
C15 | 0.0481 (11) | 0.0350 (10) | 0.0648 (13) | −0.0097 (9) | 0.0139 (10) | 0.0059 (10) |
C16 | 0.0323 (8) | 0.0292 (9) | 0.0466 (10) | −0.0012 (7) | 0.0113 (8) | 0.0000 (8) |
C17 | 0.0413 (9) | 0.0308 (8) | 0.0457 (10) | 0.0047 (8) | 0.0150 (8) | 0.0108 (8) |
C18 | 0.0609 (13) | 0.0347 (10) | 0.0655 (13) | 0.0041 (9) | 0.0223 (10) | 0.0156 (9) |
C19 | 0.0686 (14) | 0.0495 (11) | 0.0550 (11) | 0.0168 (10) | 0.0196 (10) | 0.0278 (9) |
C20 | 0.0616 (13) | 0.0487 (11) | 0.0460 (11) | 0.0096 (10) | 0.0059 (10) | 0.0153 (9) |
C21 | 0.0449 (10) | 0.0440 (10) | 0.0410 (10) | 0.0075 (9) | 0.0038 (9) | 0.0143 (8) |
C22 | 0.0303 (8) | 0.0315 (8) | 0.0394 (9) | 0.0094 (7) | 0.0104 (7) | 0.0108 (7) |
C23 | 0.0234 (7) | 0.0272 (8) | 0.0320 (8) | −0.0003 (6) | 0.0022 (6) | 0.0062 (7) |
C1' | 0.0439 (10) | 0.0466 (11) | 0.0421 (10) | 0.0011 (9) | 0.0147 (8) | 0.0089 (9) |
C2' | 0.0425 (10) | 0.0593 (12) | 0.0498 (11) | 0.0047 (10) | 0.0124 (9) | 0.0193 (10) |
C3' | 0.0372 (10) | 0.0781 (15) | 0.0406 (10) | 0.0004 (10) | 0.0051 (9) | 0.0214 (10) |
C4' | 0.0335 (9) | 0.0543 (12) | 0.0420 (10) | −0.0049 (9) | 0.0064 (8) | 0.0070 (9) |
C5' | 0.0289 (8) | 0.0497 (11) | 0.0372 (9) | −0.0063 (8) | 0.0103 (7) | 0.0005 (9) |
C6' | 0.0308 (8) | 0.0475 (11) | 0.0380 (9) | −0.0007 (8) | 0.0125 (7) | 0.0023 (8) |
C7' | 0.0363 (10) | 0.0552 (13) | 0.0474 (11) | −0.0050 (10) | 0.0123 (9) | −0.0058 (10) |
C8' | 0.0598 (13) | 0.0416 (12) | 0.0568 (13) | −0.0038 (10) | 0.0210 (10) | −0.0061 (10) |
C9' | 0.0795 (15) | 0.0417 (12) | 0.0597 (13) | 0.0111 (11) | 0.0240 (12) | 0.0027 (11) |
C10' | 0.0526 (12) | 0.0442 (11) | 0.0482 (11) | 0.0044 (10) | 0.0152 (9) | 0.0027 (10) |
C11' | 0.0351 (9) | 0.0376 (10) | 0.0388 (9) | 0.0023 (8) | 0.0113 (8) | −0.0011 (8) |
C12' | 0.0695 (15) | 0.0490 (12) | 0.0476 (13) | 0.0110 (11) | 0.0031 (12) | 0.0061 (10) |
C13' | 0.094 (2) | 0.0700 (15) | 0.0492 (14) | 0.0200 (14) | −0.0052 (14) | 0.0205 (12) |
C14' | 0.0770 (16) | 0.0614 (14) | 0.0746 (17) | 0.0242 (12) | −0.0166 (14) | 0.0156 (13) |
C15' | 0.0551 (13) | 0.0511 (13) | 0.0734 (17) | 0.0168 (11) | −0.0101 (13) | 0.0006 (12) |
C16' | 0.0423 (11) | 0.0379 (10) | 0.0539 (13) | 0.0052 (9) | 0.0002 (10) | −0.0063 (10) |
C17' | 0.0343 (9) | 0.0377 (10) | 0.0598 (13) | 0.0023 (8) | 0.0049 (9) | −0.0088 (10) |
C18' | 0.0357 (11) | 0.0551 (14) | 0.0786 (17) | 0.0020 (10) | 0.0074 (11) | −0.0125 (13) |
C19' | 0.0437 (11) | 0.0632 (15) | 0.0770 (15) | −0.0098 (11) | 0.0286 (10) | −0.0125 (13) |
C20' | 0.0553 (11) | 0.0543 (14) | 0.0604 (12) | −0.0110 (11) | 0.0312 (9) | −0.0047 (11) |
C21' | 0.0459 (11) | 0.0488 (12) | 0.0498 (11) | −0.0011 (10) | 0.0187 (9) | −0.0032 (10) |
C22' | 0.0390 (9) | 0.0298 (9) | 0.0420 (10) | −0.0012 (8) | 0.0097 (8) | −0.0057 (8) |
C23' | 0.0289 (8) | 0.0359 (9) | 0.0284 (8) | 0.0014 (7) | 0.0029 (7) | 0.0026 (7) |
O101 | 0.1261 (18) | 0.0697 (12) | 0.130 (2) | 0.0374 (12) | 0.0192 (16) | 0.0166 (13) |
C101 | 0.0609 (18) | 0.112 (2) | 0.130 (3) | 0.0122 (18) | 0.0012 (19) | 0.045 (2) |
C102 | 0.0777 (17) | 0.0599 (14) | 0.0788 (18) | 0.0229 (13) | 0.0025 (15) | 0.0196 (13) |
C103 | 0.101 (2) | 0.0619 (18) | 0.121 (3) | 0.0099 (18) | −0.002 (2) | 0.0197 (18) |
C01A | 0.106 (3) | 0.061 (3) | 0.110 (3) | 0.005 (3) | 0.028 (3) | 0.002 (3) |
C02A | 0.120 (4) | 0.095 (4) | 0.234 (6) | −0.007 (3) | 0.085 (4) | 0.015 (4) |
C03A | 0.120 (4) | 0.095 (4) | 0.234 (6) | −0.007 (3) | 0.085 (4) | 0.015 (4) |
O01A | 0.133 (3) | 0.077 (2) | 0.173 (4) | 0.020 (2) | −0.004 (3) | 0.032 (2) |
C01B | 0.106 (3) | 0.061 (3) | 0.110 (3) | 0.005 (3) | 0.028 (3) | 0.002 (3) |
C02B | 0.120 (4) | 0.095 (4) | 0.234 (6) | −0.007 (3) | 0.085 (4) | 0.015 (4) |
C03B | 0.120 (4) | 0.095 (4) | 0.234 (6) | −0.007 (3) | 0.085 (4) | 0.015 (4) |
O01B | 0.133 (3) | 0.077 (2) | 0.173 (4) | 0.020 (2) | −0.004 (3) | 0.032 (2) |
Ir1—C22 | 1.979 (2) | C4'—C5' | 1.392 (3) |
Ir1—C11 | 1.9824 (19) | C4'—H4' | 0.9500 |
Ir1—N1 | 2.0308 (13) | C5'—C6' | 1.449 (3) |
Ir1—N2 | 2.0429 (14) | C6'—C11' | 1.403 (3) |
Ir1—O2 | 2.1911 (14) | C6'—C7' | 1.419 (3) |
Ir1—O1 | 2.1938 (13) | C7'—C8' | 1.372 (4) |
Ir1'—C22' | 1.980 (2) | C7'—H7' | 0.9500 |
Ir1'—C11' | 1.9876 (19) | C8'—C9' | 1.354 (3) |
Ir1'—N1' | 2.0191 (17) | C8'—H8' | 0.9500 |
Ir1'—N2' | 2.0303 (18) | C9'—C10' | 1.406 (3) |
Ir1'—O1' | 2.1931 (13) | C9'—H9' | 0.9500 |
Ir1'—O2' | 2.1969 (15) | C10'—C11' | 1.399 (3) |
O1—C23i | 1.238 (2) | C10'—H10' | 0.9500 |
O2—C23 | 1.265 (2) | C12'—C13' | 1.379 (4) |
O1'—C23'ii | 1.254 (2) | C12'—H12' | 0.9500 |
O2'—C23' | 1.253 (2) | C13'—C14' | 1.376 (5) |
N1—C1 | 1.347 (2) | C13'—H13' | 0.9500 |
N1—C5 | 1.362 (3) | C14'—C15' | 1.342 (5) |
N2—C12 | 1.344 (2) | C14'—H14' | 0.9500 |
N2—C16 | 1.346 (3) | C15'—C16' | 1.397 (4) |
N1'—C1' | 1.350 (3) | C15'—H15' | 0.9500 |
N1'—C5' | 1.374 (2) | C16'—C17' | 1.447 (4) |
N2'—C12' | 1.355 (3) | C17'—C22' | 1.409 (3) |
N2'—C16' | 1.356 (3) | C17'—C18' | 1.419 (3) |
C1—C2 | 1.364 (3) | C18'—C19' | 1.364 (4) |
C1—H1 | 0.9500 | C18'—H18' | 0.9500 |
C2—C3 | 1.365 (4) | C19'—C20' | 1.376 (4) |
C2—H2 | 0.9500 | C19'—H19' | 0.9500 |
C3—C4 | 1.379 (3) | C20'—C21' | 1.400 (3) |
C3—H3 | 0.9500 | C20'—H20' | 0.9500 |
C4—C5 | 1.383 (3) | C21'—C22' | 1.403 (3) |
C4—H4 | 0.9500 | C21'—H21' | 0.9500 |
C5—C6 | 1.460 (3) | C23'—O1'ii | 1.254 (2) |
C6—C7 | 1.394 (3) | C23'—C23'ii | 1.550 (4) |
C6—C11 | 1.419 (2) | O101—C102 | 1.227 (4) |
C7—C8 | 1.367 (3) | C101—C102 | 1.426 (5) |
C7—H7 | 0.9500 | C101—H10A | 0.9800 |
C8—C9 | 1.390 (3) | C101—H10B | 0.9800 |
C8—H8 | 0.9500 | C101—H10C | 0.9800 |
C9—C10 | 1.378 (3) | C102—C103 | 1.464 (4) |
C9—H9 | 0.9500 | C103—H10D | 0.9800 |
C10—C11 | 1.407 (3) | C103—H10E | 0.9800 |
C10—H10 | 0.9500 | C103—H10F | 0.9800 |
C12—C13 | 1.374 (3) | C01A—O01A | 1.219 (5) |
C12—H12 | 0.9500 | C01A—C03A | 1.481 (6) |
C13—C14 | 1.370 (4) | C01A—C02A | 1.483 (6) |
C13—H13 | 0.9500 | C02A—H02A | 0.9800 |
C14—C15 | 1.377 (3) | C02A—H02B | 0.9800 |
C14—H14 | 0.9500 | C02A—H02C | 0.9800 |
C15—C16 | 1.396 (3) | C03A—H03A | 0.9800 |
C15—H15 | 0.9500 | C03A—H03B | 0.9800 |
C16—C17 | 1.461 (3) | C03A—H03C | 0.9800 |
C17—C18 | 1.397 (3) | C01B—O01B | 1.207 (4) |
C17—C22 | 1.403 (3) | C01B—C03B | 1.475 (5) |
C18—C19 | 1.371 (3) | C01B—C02B | 1.479 (5) |
C18—H18 | 0.9500 | C02B—H02D | 0.9800 |
C19—C20 | 1.381 (3) | C02B—H02E | 0.9800 |
C19—H19 | 0.9500 | C02B—H02F | 0.9800 |
C20—C21 | 1.394 (4) | C03B—H03D | 0.9800 |
C20—H20 | 0.9500 | C03B—H03E | 0.9800 |
C21—C22 | 1.399 (3) | C03B—H03F | 0.9800 |
C21—H21 | 0.9500 | C02C—C01C | 1.37 (2) |
C23—O1i | 1.238 (2) | C02C—H02G | 0.9800 |
C23—C23i | 1.545 (4) | C02C—H02H | 0.9800 |
C1'—C2' | 1.383 (3) | C02C—H02I | 0.9800 |
C1'—H1' | 0.9500 | O01C—C01C | 1.268 (18) |
C2'—C3' | 1.366 (3) | C01C—C03C | 1.67 (3) |
C2'—H2' | 0.9500 | C03C—H03G | 0.9800 |
C3'—C4' | 1.378 (4) | C03C—H03H | 0.9800 |
C3'—H3' | 0.9500 | C03C—H03I | 0.9800 |
C22—Ir1—C11 | 89.83 (8) | C2'—C3'—H3' | 119.8 |
C22—Ir1—N1 | 95.20 (7) | C4'—C3'—H3' | 119.8 |
C11—Ir1—N1 | 80.72 (7) | C3'—C4'—C5' | 120.03 (19) |
C22—Ir1—N2 | 80.59 (7) | C3'—C4'—H4' | 120.0 |
C11—Ir1—N2 | 99.37 (7) | C5'—C4'—H4' | 120.0 |
N1—Ir1—N2 | 175.79 (7) | N1'—C5'—C4' | 119.6 (2) |
C22—Ir1—O2 | 173.61 (6) | N1'—C5'—C6' | 112.81 (17) |
C11—Ir1—O2 | 96.13 (7) | C4'—C5'—C6' | 127.63 (18) |
N1—Ir1—O2 | 88.05 (6) | C11'—C6'—C7' | 120.3 (2) |
N2—Ir1—O2 | 96.11 (6) | C11'—C6'—C5' | 116.10 (17) |
C22—Ir1—O1 | 98.03 (7) | C7'—C6'—C5' | 123.55 (19) |
C11—Ir1—O1 | 171.29 (7) | C8'—C7'—C6' | 120.2 (2) |
N1—Ir1—O1 | 94.75 (5) | C8'—C7'—H7' | 119.9 |
N2—Ir1—O1 | 85.70 (5) | C6'—C7'—H7' | 119.9 |
O2—Ir1—O1 | 76.18 (5) | C9'—C8'—C7' | 119.6 (2) |
C22'—Ir1'—C11' | 89.48 (8) | C9'—C8'—H8' | 120.2 |
C22'—Ir1'—N1' | 96.51 (8) | C7'—C8'—H8' | 120.2 |
C11'—Ir1'—N1' | 80.88 (8) | C8'—C9'—C10' | 122.2 (3) |
C22'—Ir1'—N2' | 80.65 (8) | C8'—C9'—H9' | 118.9 |
C11'—Ir1'—N2' | 94.79 (8) | C10'—C9'—H9' | 118.9 |
N1'—Ir1'—N2' | 174.88 (7) | C11'—C10'—C9' | 119.5 (2) |
C22'—Ir1'—O1' | 96.80 (7) | C11'—C10'—H10' | 120.2 |
C11'—Ir1'—O1' | 172.17 (7) | C9'—C10'—H10' | 120.2 |
N1'—Ir1'—O1' | 93.72 (6) | C10'—C11'—C6' | 118.21 (18) |
N2'—Ir1'—O1' | 90.86 (6) | C10'—C11'—Ir1' | 127.65 (15) |
C22'—Ir1'—O2' | 172.30 (6) | C6'—C11'—Ir1' | 114.14 (16) |
C11'—Ir1'—O2' | 97.62 (7) | N2'—C12'—C13' | 121.3 (3) |
N1'—Ir1'—O2' | 87.60 (6) | N2'—C12'—H12' | 119.3 |
N2'—Ir1'—O2' | 95.72 (7) | C13'—C12'—H12' | 119.3 |
O1'—Ir1'—O2' | 76.38 (5) | C14'—C13'—C12' | 118.2 (3) |
C23i—O1—Ir1 | 113.75 (12) | C14'—C13'—H13' | 120.9 |
C23—O2—Ir1 | 113.94 (12) | C12'—C13'—H13' | 120.9 |
C23'ii—O1'—Ir1' | 114.11 (11) | C15'—C14'—C13' | 120.9 (3) |
C23'—O2'—Ir1' | 114.06 (12) | C15'—C14'—H14' | 119.5 |
C1—N1—C5 | 119.93 (15) | C13'—C14'—H14' | 119.5 |
C1—N1—Ir1 | 124.16 (13) | C14'—C15'—C16' | 120.1 (3) |
C5—N1—Ir1 | 115.87 (12) | C14'—C15'—H15' | 120.0 |
C12—N2—C16 | 119.68 (16) | C16'—C15'—H15' | 120.0 |
C12—N2—Ir1 | 124.68 (15) | N2'—C16'—C15' | 119.3 (2) |
C16—N2—Ir1 | 115.34 (12) | N2'—C16'—C17' | 113.7 (2) |
C1'—N1'—C5' | 119.14 (18) | C15'—C16'—C17' | 127.0 (2) |
C1'—N1'—Ir1' | 124.78 (12) | C22'—C17'—C18' | 120.4 (2) |
C5'—N1'—Ir1' | 116.06 (15) | C22'—C17'—C16' | 115.4 (2) |
C12'—N2'—C16' | 120.0 (2) | C18'—C17'—C16' | 124.2 (2) |
C12'—N2'—Ir1' | 124.05 (16) | C19'—C18'—C17' | 119.9 (2) |
C16'—N2'—Ir1' | 115.86 (16) | C19'—C18'—H18' | 120.0 |
N1—C1—C2 | 122.2 (2) | C17'—C18'—H18' | 120.0 |
N1—C1—H1 | 118.9 | C18'—C19'—C20' | 120.8 (2) |
C2—C1—H1 | 118.9 | C18'—C19'—H19' | 119.6 |
C1—C2—C3 | 118.6 (2) | C20'—C19'—H19' | 119.6 |
C1—C2—H2 | 120.7 | C19'—C20'—C21' | 120.2 (3) |
C3—C2—H2 | 120.7 | C19'—C20'—H20' | 119.9 |
C2—C3—C4 | 120.1 (2) | C21'—C20'—H20' | 119.9 |
C2—C3—H3 | 120.0 | C20'—C21'—C22' | 120.9 (2) |
C4—C3—H3 | 120.0 | C20'—C21'—H21' | 119.5 |
C3—C4—C5 | 119.9 (2) | C22'—C21'—H21' | 119.5 |
C3—C4—H4 | 120.1 | C21'—C22'—C17' | 117.6 (2) |
C5—C4—H4 | 120.1 | C21'—C22'—Ir1' | 127.87 (16) |
N1—C5—C4 | 119.25 (18) | C17'—C22'—Ir1' | 114.45 (17) |
N1—C5—C6 | 113.85 (15) | O2'—C23'—O1'ii | 124.65 (17) |
C4—C5—C6 | 126.84 (19) | O2'—C23'—C23'ii | 117.6 (2) |
C7—C6—C11 | 121.19 (17) | O1'ii—C23'—C23'ii | 117.7 (2) |
C7—C6—C5 | 124.29 (16) | C102—C101—H10A | 109.5 |
C11—C6—C5 | 114.47 (17) | C102—C101—H10B | 109.5 |
C8—C7—C6 | 120.62 (18) | H10A—C101—H10B | 109.5 |
C8—C7—H7 | 119.7 | C102—C101—H10C | 109.5 |
C6—C7—H7 | 119.7 | H10A—C101—H10C | 109.5 |
C7—C8—C9 | 119.3 (2) | H10B—C101—H10C | 109.5 |
C7—C8—H8 | 120.3 | O101—C102—C101 | 122.7 (3) |
C9—C8—H8 | 120.3 | O101—C102—C103 | 120.3 (3) |
C10—C9—C8 | 121.0 (2) | C101—C102—C103 | 117.1 (3) |
C10—C9—H9 | 119.5 | C102—C103—H10D | 109.5 |
C8—C9—H9 | 119.5 | C102—C103—H10E | 109.5 |
C9—C10—C11 | 121.36 (17) | H10D—C103—H10E | 109.5 |
C9—C10—H10 | 119.3 | C102—C103—H10F | 109.5 |
C11—C10—H10 | 119.3 | H10D—C103—H10F | 109.5 |
C10—C11—C6 | 116.48 (17) | H10E—C103—H10F | 109.5 |
C10—C11—Ir1 | 128.71 (13) | O01A—C01A—C03A | 121.5 (7) |
C6—C11—Ir1 | 114.76 (13) | O01A—C01A—C02A | 119.6 (6) |
N2—C12—C13 | 122.5 (2) | C03A—C01A—C02A | 116.3 (6) |
N2—C12—H12 | 118.8 | C01A—C02A—H02A | 109.5 |
C13—C12—H12 | 118.8 | C01A—C02A—H02B | 109.5 |
C14—C13—C12 | 118.9 (2) | H02A—C02A—H02B | 109.5 |
C14—C13—H13 | 120.5 | C01A—C02A—H02C | 109.5 |
C12—C13—H13 | 120.5 | H02A—C02A—H02C | 109.5 |
C13—C14—C15 | 118.8 (2) | H02B—C02A—H02C | 109.5 |
C13—C14—H14 | 120.6 | C01A—C03A—H03A | 109.5 |
C15—C14—H14 | 120.6 | C01A—C03A—H03B | 109.5 |
C14—C15—C16 | 120.5 (2) | H03A—C03A—H03B | 109.5 |
C14—C15—H15 | 119.7 | C01A—C03A—H03C | 109.5 |
C16—C15—H15 | 119.7 | H03A—C03A—H03C | 109.5 |
N2—C16—C15 | 119.52 (19) | H03B—C03A—H03C | 109.5 |
N2—C16—C17 | 114.02 (16) | O01B—C01B—C03B | 122.9 (5) |
C15—C16—C17 | 126.4 (2) | O01B—C01B—C02B | 121.7 (4) |
C18—C17—C22 | 121.21 (18) | C03B—C01B—C02B | 114.9 (4) |
C18—C17—C16 | 123.91 (18) | C01B—C02B—H02D | 109.5 |
C22—C17—C16 | 114.87 (19) | C01B—C02B—H02E | 109.5 |
C19—C18—C17 | 120.4 (2) | H02D—C02B—H02E | 109.5 |
C19—C18—H18 | 119.8 | C01B—C02B—H02F | 109.5 |
C17—C18—H18 | 119.8 | H02D—C02B—H02F | 109.5 |
C18—C19—C20 | 119.5 (2) | H02E—C02B—H02F | 109.5 |
C18—C19—H19 | 120.3 | C01B—C03B—H03D | 109.5 |
C20—C19—H19 | 120.3 | C01B—C03B—H03E | 109.5 |
C19—C20—C21 | 120.7 (2) | H03D—C03B—H03E | 109.5 |
C19—C20—H20 | 119.7 | C01B—C03B—H03F | 109.5 |
C21—C20—H20 | 119.7 | H03D—C03B—H03F | 109.5 |
C20—C21—C22 | 120.94 (19) | H03E—C03B—H03F | 109.5 |
C20—C21—H21 | 119.5 | C01C—C02C—H02G | 109.5 |
C22—C21—H21 | 119.5 | C01C—C02C—H02H | 109.5 |
C21—C22—C17 | 117.2 (2) | H02G—C02C—H02H | 109.5 |
C21—C22—Ir1 | 127.91 (15) | C01C—C02C—H02I | 109.5 |
C17—C22—Ir1 | 114.84 (13) | H02G—C02C—H02I | 109.5 |
O1i—C23—O2 | 124.74 (18) | H02H—C02C—H02I | 109.5 |
O1i—C23—C23i | 118.6 (2) | O01C—C01C—C02C | 128.7 (17) |
O2—C23—C23i | 116.7 (2) | O01C—C01C—C03C | 96.8 (15) |
N1'—C1'—C2' | 122.61 (19) | C02C—C01C—C03C | 133.0 (15) |
N1'—C1'—H1' | 118.7 | C01C—C03C—H03G | 109.5 |
C2'—C1'—H1' | 118.7 | C01C—C03C—H03H | 109.5 |
C3'—C2'—C1' | 118.3 (2) | H03G—C03C—H03H | 109.5 |
C3'—C2'—H2' | 120.8 | C01C—C03C—H03I | 109.5 |
C1'—C2'—H2' | 120.8 | H03G—C03C—H03I | 109.5 |
C2'—C3'—C4' | 120.4 (2) | H03H—C03C—H03I | 109.5 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z. |