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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008809/wm6056sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008809/wm6056IIsup2.hkl
Contains datablock II

CCDC reference: 272125

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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-1κ2O,O':2κ2O'',O'''tetrakis(phenylpyridine-κ2C,N)\- diiridium(III) acetone 1.974 solvate top
Crystal data top
[Ir(C2O4)(C11H8N)4]·1.974C3H6OZ = 2
Mr = 1203.79F(000) = 1170
Triclinic, P1Dx = 1.683 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9708 (5) ÅCell parameters from 8192 reflections
b = 13.0403 (7) Åθ = 1.7–29.6°
c = 19.3556 (10) ŵ = 5.65 mm1
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 tube9639 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 29.6°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.430, Tmax = 0.568k = 1818
30150 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-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 parametersΔρmax = 2.37 e Å3
12 restraintsΔρmin = 1.13 e Å3
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
xyzUiso*/UeqOcc. (<1)
Ir10.333434 (7)0.133535 (5)0.446300 (4)0.02833 (2)
Ir1'0.362785 (7)0.627249 (6)0.095088 (4)0.03433 (2)
O10.51118 (12)0.05688 (10)0.42742 (7)0.0325 (3)
O20.37124 (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)
N10.18998 (15)0.00040 (12)0.39304 (8)0.0331 (4)
N20.47597 (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)
C10.2177 (2)0.08684 (16)0.34887 (11)0.0400 (6)
H10.31020.08810.34280.048*
C20.1173 (2)0.17347 (18)0.31264 (14)0.0551 (8)
H20.13910.23380.28130.066*
C30.0151 (2)0.1718 (2)0.32232 (15)0.0611 (8)
H30.08630.23180.29820.073*
C40.0458 (2)0.08301 (18)0.36708 (14)0.0526 (7)
H40.13790.08190.37390.063*
C50.05789 (19)0.00445 (15)0.40197 (11)0.0363 (5)
C60.04163 (19)0.10710 (15)0.44648 (11)0.0349 (5)
C70.0838 (2)0.13056 (18)0.46267 (12)0.0453 (6)
H70.16470.07650.44650.054*
C80.0914 (2)0.23063 (19)0.50161 (13)0.0531 (7)
H80.17720.24640.51220.064*
C90.0276 (2)0.30909 (18)0.52551 (13)0.0521 (7)
H90.02250.37870.55250.062*
C100.1528 (2)0.28741 (16)0.51061 (11)0.0383 (6)
H100.23260.34240.52760.046*
C110.16490 (18)0.18546 (14)0.47069 (10)0.0309 (5)
C120.55132 (19)0.29571 (17)0.56057 (11)0.0401 (6)
H120.53200.25020.59110.048*
C130.6552 (2)0.38425 (18)0.58715 (13)0.0491 (7)
H130.70490.40080.63560.059*
C140.6861 (2)0.44829 (19)0.54261 (15)0.0576 (8)
H140.75860.50920.55940.069*
C150.6101 (2)0.42279 (18)0.47308 (14)0.0520 (7)
H150.63140.46580.44140.062*
C160.5021 (2)0.33424 (15)0.44888 (11)0.0380 (6)
C170.4120 (2)0.29878 (15)0.37732 (11)0.0386 (5)
C180.4151 (3)0.35527 (18)0.32429 (13)0.0527 (7)
H180.47770.42140.33420.063*
C190.3283 (3)0.31591 (18)0.25800 (13)0.0538 (7)
H190.32910.35530.22240.065*
C200.2397 (3)0.21851 (18)0.24332 (13)0.0522 (7)
H200.18160.19000.19690.063*
C210.2348 (2)0.16169 (17)0.29592 (11)0.0433 (6)
H210.17190.09560.28520.052*
C220.32132 (18)0.20062 (14)0.36423 (10)0.0327 (5)
C230.46067 (17)0.00014 (14)0.53137 (9)0.0286 (5)
C1'0.5299 (2)0.51368 (18)0.18534 (11)0.0447 (6)
H1'0.49280.45140.14670.054*
C2'0.6216 (2)0.5048 (2)0.24422 (12)0.0498 (7)
H2'0.64790.43810.24590.060*
C3'0.6733 (2)0.5945 (2)0.29992 (12)0.0523 (7)
H3'0.73670.59040.34090.063*
C4'0.6340 (2)0.69079 (19)0.29705 (12)0.0457 (6)
H4'0.66910.75260.33630.055*
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)
H7'0.59740.90520.31680.060*
C8'0.4855 (3)0.98123 (19)0.25546 (13)0.0562 (8)
H8'0.51251.05040.28840.067*
C9'0.3980 (3)0.9669 (2)0.19161 (14)0.0609 (8)
H9'0.36451.02700.18040.073*
C10'0.3549 (2)0.86603 (18)0.14134 (13)0.0498 (7)
H10'0.29290.85840.09710.060*
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)
H12'0.36030.70060.04520.069*
C13'0.1701 (3)0.7143 (2)0.09224 (15)0.0719 (10)
H13'0.19730.73840.13160.086*
C14'0.0341 (3)0.7008 (2)0.08495 (16)0.0737 (10)
H14'0.03360.71550.11980.088*
C15'0.0043 (3)0.6672 (2)0.02925 (15)0.0643 (9)
H15'0.09890.65710.02540.077*
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)
H18'0.13930.60790.07730.075*
C19'0.0714 (2)0.5674 (2)0.16910 (15)0.0666 (9)
H19'0.15910.55770.18250.080*
C20'0.0423 (2)0.5505 (2)0.21236 (13)0.0599 (8)
H20'0.03200.52660.25440.072*
C21'0.1729 (2)0.56836 (19)0.19464 (12)0.0509 (7)
H21'0.25110.55810.22550.061*
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)
O1010.8231 (3)0.42152 (18)0.35311 (15)0.1089 (10)
C1010.9857 (3)0.3143 (3)0.3262 (2)0.1011 (14)
H10A1.05020.38310.34240.152*
H10B0.98860.27990.27580.152*
H10C1.01210.26770.35700.152*
C1020.8491 (3)0.3319 (2)0.33088 (17)0.0722 (10)
C1030.7381 (4)0.2374 (3)0.3079 (2)0.0985 (15)
H10D0.64950.25980.31250.148*
H10E0.75540.18860.33850.148*
H10F0.73520.20060.25730.148*
C01A0.8697 (4)0.9800 (3)0.1364 (4)0.0963 (19)0.209 (3)
C02A0.9601 (5)0.8988 (4)0.1349 (9)0.151 (3)0.209 (3)
H02A1.05700.93510.15000.227*0.209 (3)
H02B0.94500.85240.08560.227*0.209 (3)
H02C0.93780.85530.16810.227*0.209 (3)
C03A0.7407 (5)0.9498 (9)0.0808 (4)0.151 (3)0.209 (3)
H03A0.68841.00830.08730.227*0.209 (3)
H03B0.68480.88470.08580.227*0.209 (3)
H03C0.76360.93640.03250.227*0.209 (3)
O01A0.9169 (10)1.0734 (3)0.1688 (6)0.132 (2)0.209 (3)
C01B0.8867 (3)0.9744 (2)0.1379 (3)0.0963 (19)0.531 (3)
C02B1.0089 (4)0.9277 (4)0.1224 (5)0.151 (3)0.531 (3)
H02D1.07270.97900.10760.227*0.531 (3)
H02E0.97940.86140.08340.227*0.531 (3)
H02F1.05550.91170.16610.227*0.531 (3)
C03B0.7675 (4)0.8970 (4)0.1427 (4)0.151 (3)0.531 (3)
H03D0.69530.93560.15810.227*0.531 (3)
H03E0.79690.85770.17810.227*0.531 (3)
H03F0.73110.84630.09520.227*0.531 (3)
O01B0.8909 (5)1.0701 (2)0.1533 (3)0.132 (2)0.531 (3)
C02C0.3017 (17)0.1852 (14)0.0611 (9)0.105 (5)*0.234 (3)
H02G0.29040.25310.09220.158*0.234 (3)
H02H0.24040.12560.06970.158*0.234 (3)
H02I0.27820.18620.01020.158*0.234 (3)
O01C0.5292 (12)0.2218 (9)0.1318 (6)0.114 (4)*0.234 (3)
C01C0.4361 (18)0.1723 (14)0.0770 (9)0.105 (5)*0.234 (3)
C03C0.520 (3)0.075 (2)0.0452 (15)0.207 (13)*0.234 (3)
H03G0.61720.09460.06970.311*0.234 (3)
H03H0.51380.06540.00700.311*0.234 (3)
H03I0.47790.00790.05420.311*0.234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.02396 (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)
O10.0266 (5)0.0334 (6)0.0379 (6)0.0055 (5)0.0094 (5)0.0082 (5)
O20.0268 (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)
N10.0286 (7)0.0312 (7)0.0393 (8)0.0035 (6)0.0055 (6)0.0110 (6)
N20.0282 (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)
C10.0365 (9)0.0324 (9)0.0485 (10)0.0025 (8)0.0116 (8)0.0060 (8)
C20.0503 (12)0.0359 (11)0.0676 (14)0.0027 (10)0.0145 (11)0.0044 (11)
C30.0412 (11)0.0448 (12)0.0789 (16)0.0136 (10)0.0116 (11)0.0070 (12)
C40.0345 (10)0.0431 (11)0.0689 (14)0.0035 (9)0.0091 (10)0.0009 (11)
C50.0292 (8)0.0335 (8)0.0460 (10)0.0056 (7)0.0059 (7)0.0109 (8)
C60.0285 (8)0.0326 (8)0.0434 (10)0.0057 (7)0.0051 (7)0.0109 (7)
C70.0277 (8)0.0467 (11)0.0610 (12)0.0038 (8)0.0102 (8)0.0142 (9)
C80.0386 (9)0.0592 (12)0.0690 (13)0.0252 (8)0.0217 (9)0.0140 (11)
C90.0500 (11)0.0436 (10)0.0632 (13)0.0184 (9)0.0162 (10)0.0060 (10)
C100.0352 (9)0.0358 (9)0.0415 (10)0.0062 (8)0.0069 (8)0.0060 (8)
C110.0320 (8)0.0292 (8)0.0322 (8)0.0057 (7)0.0046 (7)0.0105 (6)
C120.0313 (8)0.0423 (10)0.0407 (10)0.0059 (8)0.0083 (8)0.0014 (8)
C130.0379 (10)0.0460 (11)0.0475 (12)0.0020 (9)0.0009 (9)0.0095 (10)
C140.0371 (10)0.0396 (11)0.0789 (16)0.0056 (9)0.0076 (11)0.0078 (12)
C150.0481 (11)0.0350 (10)0.0648 (13)0.0097 (9)0.0139 (10)0.0059 (10)
C160.0323 (8)0.0292 (9)0.0466 (10)0.0012 (7)0.0113 (8)0.0000 (8)
C170.0413 (9)0.0308 (8)0.0457 (10)0.0047 (8)0.0150 (8)0.0108 (8)
C180.0609 (13)0.0347 (10)0.0655 (13)0.0041 (9)0.0223 (10)0.0156 (9)
C190.0686 (14)0.0495 (11)0.0550 (11)0.0168 (10)0.0196 (10)0.0278 (9)
C200.0616 (13)0.0487 (11)0.0460 (11)0.0096 (10)0.0059 (10)0.0153 (9)
C210.0449 (10)0.0440 (10)0.0410 (10)0.0075 (9)0.0038 (9)0.0143 (8)
C220.0303 (8)0.0315 (8)0.0394 (9)0.0094 (7)0.0104 (7)0.0108 (7)
C230.0234 (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)
O1010.1261 (18)0.0697 (12)0.130 (2)0.0374 (12)0.0192 (16)0.0166 (13)
C1010.0609 (18)0.112 (2)0.130 (3)0.0122 (18)0.0012 (19)0.045 (2)
C1020.0777 (17)0.0599 (14)0.0788 (18)0.0229 (13)0.0025 (15)0.0196 (13)
C1030.101 (2)0.0619 (18)0.121 (3)0.0099 (18)0.002 (2)0.0197 (18)
C01A0.106 (3)0.061 (3)0.110 (3)0.005 (3)0.028 (3)0.002 (3)
C02A0.120 (4)0.095 (4)0.234 (6)0.007 (3)0.085 (4)0.015 (4)
C03A0.120 (4)0.095 (4)0.234 (6)0.007 (3)0.085 (4)0.015 (4)
O01A0.133 (3)0.077 (2)0.173 (4)0.020 (2)0.004 (3)0.032 (2)
C01B0.106 (3)0.061 (3)0.110 (3)0.005 (3)0.028 (3)0.002 (3)
C02B0.120 (4)0.095 (4)0.234 (6)0.007 (3)0.085 (4)0.015 (4)
C03B0.120 (4)0.095 (4)0.234 (6)0.007 (3)0.085 (4)0.015 (4)
O01B0.133 (3)0.077 (2)0.173 (4)0.020 (2)0.004 (3)0.032 (2)
Geometric parameters (Å, º) top
Ir1—C221.979 (2)C4'—C5'1.392 (3)
Ir1—C111.9824 (19)C4'—H4'0.9500
Ir1—N12.0308 (13)C5'—C6'1.449 (3)
Ir1—N22.0429 (14)C6'—C11'1.403 (3)
Ir1—O22.1911 (14)C6'—C7'1.419 (3)
Ir1—O12.1938 (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—C23i1.238 (2)C10'—H10'0.9500
O2—C231.265 (2)C12'—C13'1.379 (4)
O1'—C23'ii1.254 (2)C12'—H12'0.9500
O2'—C23'1.253 (2)C13'—C14'1.376 (5)
N1—C11.347 (2)C13'—H13'0.9500
N1—C51.362 (3)C14'—C15'1.342 (5)
N2—C121.344 (2)C14'—H14'0.9500
N2—C161.346 (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—C21.364 (3)C18'—C19'1.364 (4)
C1—H10.9500C18'—H18'0.9500
C2—C31.365 (4)C19'—C20'1.376 (4)
C2—H20.9500C19'—H19'0.9500
C3—C41.379 (3)C20'—C21'1.400 (3)
C3—H30.9500C20'—H20'0.9500
C4—C51.383 (3)C21'—C22'1.403 (3)
C4—H40.9500C21'—H21'0.9500
C5—C61.460 (3)C23'—O1'ii1.254 (2)
C6—C71.394 (3)C23'—C23'ii1.550 (4)
C6—C111.419 (2)O101—C1021.227 (4)
C7—C81.367 (3)C101—C1021.426 (5)
C7—H70.9500C101—H10A0.9800
C8—C91.390 (3)C101—H10B0.9800
C8—H80.9500C101—H10C0.9800
C9—C101.378 (3)C102—C1031.464 (4)
C9—H90.9500C103—H10D0.9800
C10—C111.407 (3)C103—H10E0.9800
C10—H100.9500C103—H10F0.9800
C12—C131.374 (3)C01A—O01A1.219 (5)
C12—H120.9500C01A—C03A1.481 (6)
C13—C141.370 (4)C01A—C02A1.483 (6)
C13—H130.9500C02A—H02A0.9800
C14—C151.377 (3)C02A—H02B0.9800
C14—H140.9500C02A—H02C0.9800
C15—C161.396 (3)C03A—H03A0.9800
C15—H150.9500C03A—H03B0.9800
C16—C171.461 (3)C03A—H03C0.9800
C17—C181.397 (3)C01B—O01B1.207 (4)
C17—C221.403 (3)C01B—C03B1.475 (5)
C18—C191.371 (3)C01B—C02B1.479 (5)
C18—H180.9500C02B—H02D0.9800
C19—C201.381 (3)C02B—H02E0.9800
C19—H190.9500C02B—H02F0.9800
C20—C211.394 (4)C03B—H03D0.9800
C20—H200.9500C03B—H03E0.9800
C21—C221.399 (3)C03B—H03F0.9800
C21—H210.9500C02C—C01C1.37 (2)
C23—O1i1.238 (2)C02C—H02G0.9800
C23—C23i1.545 (4)C02C—H02H0.9800
C1'—C2'1.383 (3)C02C—H02I0.9800
C1'—H1'0.9500O01C—C01C1.268 (18)
C2'—C3'1.366 (3)C01C—C03C1.67 (3)
C2'—H2'0.9500C03C—H03G0.9800
C3'—C4'1.378 (4)C03C—H03H0.9800
C3'—H3'0.9500C03C—H03I0.9800
C22—Ir1—C1189.83 (8)C2'—C3'—H3'119.8
C22—Ir1—N195.20 (7)C4'—C3'—H3'119.8
C11—Ir1—N180.72 (7)C3'—C4'—C5'120.03 (19)
C22—Ir1—N280.59 (7)C3'—C4'—H4'120.0
C11—Ir1—N299.37 (7)C5'—C4'—H4'120.0
N1—Ir1—N2175.79 (7)N1'—C5'—C4'119.6 (2)
C22—Ir1—O2173.61 (6)N1'—C5'—C6'112.81 (17)
C11—Ir1—O296.13 (7)C4'—C5'—C6'127.63 (18)
N1—Ir1—O288.05 (6)C11'—C6'—C7'120.3 (2)
N2—Ir1—O296.11 (6)C11'—C6'—C5'116.10 (17)
C22—Ir1—O198.03 (7)C7'—C6'—C5'123.55 (19)
C11—Ir1—O1171.29 (7)C8'—C7'—C6'120.2 (2)
N1—Ir1—O194.75 (5)C8'—C7'—H7'119.9
N2—Ir1—O185.70 (5)C6'—C7'—H7'119.9
O2—Ir1—O176.18 (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—Ir1113.75 (12)C14'—C13'—H13'120.9
C23—O2—Ir1113.94 (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—C5119.93 (15)C13'—C14'—H14'119.5
C1—N1—Ir1124.16 (13)C14'—C15'—C16'120.1 (3)
C5—N1—Ir1115.87 (12)C14'—C15'—H15'120.0
C12—N2—C16119.68 (16)C16'—C15'—H15'120.0
C12—N2—Ir1124.68 (15)N2'—C16'—C15'119.3 (2)
C16—N2—Ir1115.34 (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—C2122.2 (2)C17'—C18'—H18'120.0
N1—C1—H1118.9C18'—C19'—C20'120.8 (2)
C2—C1—H1118.9C18'—C19'—H19'119.6
C1—C2—C3118.6 (2)C20'—C19'—H19'119.6
C1—C2—H2120.7C19'—C20'—C21'120.2 (3)
C3—C2—H2120.7C19'—C20'—H20'119.9
C2—C3—C4120.1 (2)C21'—C20'—H20'119.9
C2—C3—H3120.0C20'—C21'—C22'120.9 (2)
C4—C3—H3120.0C20'—C21'—H21'119.5
C3—C4—C5119.9 (2)C22'—C21'—H21'119.5
C3—C4—H4120.1C21'—C22'—C17'117.6 (2)
C5—C4—H4120.1C21'—C22'—Ir1'127.87 (16)
N1—C5—C4119.25 (18)C17'—C22'—Ir1'114.45 (17)
N1—C5—C6113.85 (15)O2'—C23'—O1'ii124.65 (17)
C4—C5—C6126.84 (19)O2'—C23'—C23'ii117.6 (2)
C7—C6—C11121.19 (17)O1'ii—C23'—C23'ii117.7 (2)
C7—C6—C5124.29 (16)C102—C101—H10A109.5
C11—C6—C5114.47 (17)C102—C101—H10B109.5
C8—C7—C6120.62 (18)H10A—C101—H10B109.5
C8—C7—H7119.7C102—C101—H10C109.5
C6—C7—H7119.7H10A—C101—H10C109.5
C7—C8—C9119.3 (2)H10B—C101—H10C109.5
C7—C8—H8120.3O101—C102—C101122.7 (3)
C9—C8—H8120.3O101—C102—C103120.3 (3)
C10—C9—C8121.0 (2)C101—C102—C103117.1 (3)
C10—C9—H9119.5C102—C103—H10D109.5
C8—C9—H9119.5C102—C103—H10E109.5
C9—C10—C11121.36 (17)H10D—C103—H10E109.5
C9—C10—H10119.3C102—C103—H10F109.5
C11—C10—H10119.3H10D—C103—H10F109.5
C10—C11—C6116.48 (17)H10E—C103—H10F109.5
C10—C11—Ir1128.71 (13)O01A—C01A—C03A121.5 (7)
C6—C11—Ir1114.76 (13)O01A—C01A—C02A119.6 (6)
N2—C12—C13122.5 (2)C03A—C01A—C02A116.3 (6)
N2—C12—H12118.8C01A—C02A—H02A109.5
C13—C12—H12118.8C01A—C02A—H02B109.5
C14—C13—C12118.9 (2)H02A—C02A—H02B109.5
C14—C13—H13120.5C01A—C02A—H02C109.5
C12—C13—H13120.5H02A—C02A—H02C109.5
C13—C14—C15118.8 (2)H02B—C02A—H02C109.5
C13—C14—H14120.6C01A—C03A—H03A109.5
C15—C14—H14120.6C01A—C03A—H03B109.5
C14—C15—C16120.5 (2)H03A—C03A—H03B109.5
C14—C15—H15119.7C01A—C03A—H03C109.5
C16—C15—H15119.7H03A—C03A—H03C109.5
N2—C16—C15119.52 (19)H03B—C03A—H03C109.5
N2—C16—C17114.02 (16)O01B—C01B—C03B122.9 (5)
C15—C16—C17126.4 (2)O01B—C01B—C02B121.7 (4)
C18—C17—C22121.21 (18)C03B—C01B—C02B114.9 (4)
C18—C17—C16123.91 (18)C01B—C02B—H02D109.5
C22—C17—C16114.87 (19)C01B—C02B—H02E109.5
C19—C18—C17120.4 (2)H02D—C02B—H02E109.5
C19—C18—H18119.8C01B—C02B—H02F109.5
C17—C18—H18119.8H02D—C02B—H02F109.5
C18—C19—C20119.5 (2)H02E—C02B—H02F109.5
C18—C19—H19120.3C01B—C03B—H03D109.5
C20—C19—H19120.3C01B—C03B—H03E109.5
C19—C20—C21120.7 (2)H03D—C03B—H03E109.5
C19—C20—H20119.7C01B—C03B—H03F109.5
C21—C20—H20119.7H03D—C03B—H03F109.5
C20—C21—C22120.94 (19)H03E—C03B—H03F109.5
C20—C21—H21119.5C01C—C02C—H02G109.5
C22—C21—H21119.5C01C—C02C—H02H109.5
C21—C22—C17117.2 (2)H02G—C02C—H02H109.5
C21—C22—Ir1127.91 (15)C01C—C02C—H02I109.5
C17—C22—Ir1114.84 (13)H02G—C02C—H02I109.5
O1i—C23—O2124.74 (18)H02H—C02C—H02I109.5
O1i—C23—C23i118.6 (2)O01C—C01C—C02C128.7 (17)
O2—C23—C23i116.7 (2)O01C—C01C—C03C96.8 (15)
N1'—C1'—C2'122.61 (19)C02C—C01C—C03C133.0 (15)
N1'—C1'—H1'118.7C01C—C03C—H03G109.5
C2'—C1'—H1'118.7C01C—C03C—H03H109.5
C3'—C2'—C1'118.3 (2)H03G—C03C—H03H109.5
C3'—C2'—H2'120.8C01C—C03C—H03I109.5
C1'—C2'—H2'120.8H03G—C03C—H03I109.5
C2'—C3'—C4'120.4 (2)H03H—C03C—H03I109.5
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z.
 

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