An attempt to grow crystals of [Ir(ppy)2(vacac)], (I), from an acetone-d6 solution formed instead crystals of [{Ir(ppy)2}2(μ-oxalato)] acetone solvate, (II), [Ir2(C11H8N)4(C2O4)]·1.974C3H6O, where ppy is the phenylpyridine anion and vacac is vinylacetylacetonate. Each IrIII ion in (II) is in a pseudo-octahedral coordination environment, where the pyridine N atoms are trans to each other and the phenyl C atoms are trans to the O atoms of the oxalate bridging ligand. There are two crystallographically independent dimer molecules, each lying on an inversion centre. It is suggested that the oxalate ligand is formed in a series of steps initiated by the aldol condensation of acetone with vacac.
Supporting information
CCDC reference: 272125
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.040
- wR factor = 0.098
- Data-to-parameter ratio = 21.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact C03C .. C03C .. 2.24 Ang.
| Author Response: ... atom C03 has occupancy 0.23, the adjacent C03 atom
(related by an inversion center) need not be ocupied.
|
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.373 0.493
Tmin and Tmax expected: 0.373 0.568
RR = 1.153
Please check that your absorption correction is appropriate.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.14
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.15
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.10
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C01B
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C01A
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C102
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C01C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.60
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 24.00 Perc.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C23 - C23_a ... 1.54 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C23' - C23'_b ... 1.55 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 30
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C51.92 H43.85 Ir2 N4 O5.97
Atom count from _chemical_formula_moiety:C51.91 H43.82 Ir2 N4 O5.97
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 1.153
Tmax scaled 0.568 Tmin scaled 0.430
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
17 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
8 ALERT type 4 Improvement, methodology, query or suggestion
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.
µ-oxalato-1
κ2O,
O':2
κ2O'',
O'''tetrakis(phenylpyridine-
κ2C,
N)\- diiridium(III)
acetone 1.974 solvate
top
Crystal data top
[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 | |
Data collection top
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 top
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 |
Special details top
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 (Å2) top | 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) |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |