Chlorido(6-diphenyl­phosphino-2-pyridonato-κ²P,N)(6-diphenyl­phosphino-2-hydroxypyridine-κ²P,N)hydridoiridium(III) chloro­form 1.896-solvate

The title complex, [Ir(C₁₇H₁₃NOP)ClH(C₁₇H₁₄NOP)]·1.896CHCl₃, contains hydride, chloride, 6-diphenyl­phosphino-2-hydroxy­pyridine (pyphosH) and 6-diphenyl­phosphino-2-pyridonate (pyphos) ligands coordinated to an Ir^III metal centre to give a distorted octa­hedral coordination geometry. The two P and two N atoms of the pyphosH and pyphos ligands lie with a cis coordination in the equatorial plane. An intra­molecular O—H...O hydrogen bond is observed between the pyphosH and pyphos ligands.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.030
• wR factor = 0.066
• Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...      10.00 Ratio

Author Response: Two sites of chloroform solvate were found in the electron density maps. One chloroform solvate was successfully refined. The other chloroform solvate was poorly defined, and five positions (occupancy factor: 0.14314, 0.23924, 0.15039, 0.15787, 0.20548) could be assigned for chloroform solvate on a difference Fourier map. Atoms of the disordered chloroform solvate were isotropically refined. The Cl---C and Cl...Cl bonds for the disordered chloroform solvate were restrained to 1.761(29) and 2.889(20) \%A, respectively. The ratio (>52.5) is a value from ambiguous C40(Uiso) and C36(Uiso) in the disordered chloroform solvate, so it is large.

 Large Non-Solvent   Cl     Ueq(max)/Ueq(min) ...       5.54 Ratio
 RESPONSE: Uiso(max) is a value (0.078(3)) of the chlorine atom (Cl7)
  Uiso(max) is a value (0.078(3)) of the chlorine atom (Cl7)
 in disordered chloroform solvate. Ueq(min) is a value (0.014(1)) of
 chloride ligand (Cl1A).

PLAT220_ALERT_2_A Large Non-Solvent   Cl     Ueq(max)/Ueq(min) ...       5.54 Ratio

Author Response: Two sites of chloroform solvate were found in the electron density maps. One chloroform solvate was successfully refined. The other chloroform solvate was poorly defined, and five positions (occupancy factor: 0.14314, 0.23924, 0.15039, 0.15787, 0.20548) could be assigned for chloroform solvate on a difference Fourier map. Atoms of the disordered chloroform solvate were isotropically refined. The Cl---C and Cl...Cl bonds for the disordered chloroform solvate were restrained to 1.761(29) and 2.889(20) \%A, respectively. The ratio (>52.5) is a value from ambiguous C40(Uiso) and C36(Uiso) in the disordered chloroform solvate, so it is large.

 Large Non-Solvent   Cl     Ueq(max)/Ueq(min) ...       5.54 Ratio
 RESPONSE: Uiso(max) is a value (0.078(3)) of the chlorine atom (Cl7)
  Uiso(max) is a value (0.078(3)) of the chlorine atom (Cl7)
 in disordered chloroform solvate. Ueq(min) is a value (0.014(1)) of
 chloride ligand (Cl1A).

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...      10.00 Ratio

Author Response: Uiso(max) is a value (0.105) of the methine H-atom (H40) in disordered chloroform solvate. The value (0.002) of Uiso(min) is H36 of disordered chloroform solvate. Therefore, the ratio is large.

PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C39

Author Response: The C39 atom (Uiso: 0.09) is included in the disordered chloroform solvate (occupancy factor: 0.15787).

PLAT431_ALERT_2_A Short Inter HL..A Contact  Cl9    ..  Cl9     ..       2.72 Ang.

Author Response: The Cl9 atom is included in the disordered chloroform solvate (occupancy factor: 0.23924), so it actually does not have any short contacts to Cl9 atoms generated by the symmetry operation.

PLAT772_ALERT_2_A Suspect O-H Bond in CIF:      O1     -H1      ..       1.35 Ang.

Author Response: .Proton of hydroxy group was located in a difference Fourier map and refined isotropically with <i>U</i>~iso~(H1) = 1.2<i>U</i>~eq~(O2). The intramolecular hydrogen bond (O2...H1---O1) of the title compound is almost symmetrical with O2---H1 = 1.09(4) and H1---O1 = 1.35(4) \%A, The O...O distance (2.398(3) \%A) is accordance with strong hydrogen bond between pyphosH and pyphos.

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       Cl10

Author Response: The C39 atom (Uiso: 0.09) is included in the disordered chloroform solvate (occupancy factor: 0.15787).

PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C40

Author Response: The C39 atom (Uiso: 0.09) is included in the disordered chloroform solvate (occupancy factor: 0.15787).

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C36
PLAT432_ALERT_2_B Short Inter X...Y Contact  C3     ..  Cl11    ..       3.14 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C25    ..  Cl7     ..       3.13 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C25    ..  Cl14    ..       3.14 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C37
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C2     ..  Cl11    ..       3.23 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N2  -IR  -P1  -C12   -39.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N2  -IR  -P1  -C1     72.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            N2  -IR  -P1  -C6     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N1  -IR  -P2  -C23   157.50  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            N1  -IR  -P2  -C29    16.70  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         27
            N1  -IR  -P2  -C18   -91.50  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            P2  -IR  -N1  -C5     82.10  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         38
            P2  -IR  -N1  -C1    -90.10  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         42
            P1  -IR  -N2  -C22   -88.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         47
            P1  -IR  -N2  -C18   100.00  8.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C35.896 H29.896 Cl6.688 Ir1 N2
            Atom count from the _atom_site data:  C35.9 H29.9 Cl6.7 Ir1 N2 O2 P2
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      0.924
            Tmax scaled      0.444 Tmin scaled      0.234
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C35.896 H29.896 Cl6.688 Ir N2 O2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        143.58    143.60   -0.02
           H        119.58    119.60   -0.02
           Cl        26.75     26.80   -0.05
           Ir         4.00      4.00    0.00
           N          8.00      8.00    0.00
           O          8.00      8.00    0.00
           P          8.00      8.00    0.00

   6 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  18 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 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
  12 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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.

Chlorido(6-diphenylphosphino-2-pyridonato-κ²P,N)(6-diphenylphosphino- 2-hydroxypyridine-κ²P,N)hydridoiridium(III) chloroform 1.896-solvate

Crystal data

[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) Å^3	0.60 × 0.30 × 0.20 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0184P)^2 + 12.9527P] where P = (Fo^2 + 2Fc^2)/3
11703 reflections	(Δ/σ)max = 0.004
515 parameters	Δρmax = 1.63 e Å^−3
30 restraints	Δρmin = −1.06 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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