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The enanti­omerically pure iridium title complex, [Ir(C13H19N2O2S)(C10H15)Cl]·CHCl3, has the Ir atom in the S configuration, with a distorted octa­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034842/dn2059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034842/dn2059Isup2.hkl
Contains datablock I

CCDC reference: 624203

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.028
  • wR factor = 0.059
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT213_ALERT_2_B Atom C3 has ADP max/min Ratio ............. 4.30 prola
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.19 PLAT213_ALERT_2_C Atom C8 has ADP max/min Ratio ............. 3.40 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
Alert level G 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 1.191 Tmax scaled 0.664 Tmin scaled 0.428 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.94 From the CIF: _reflns_number_total 5576 Count of symmetry unique reflns 3173 Completeness (_total/calc) 175.73% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2403 Fraction of Friedel pairs measured 0.757 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

[(R,R)-2-Amino-1-(p-tolylsulfonylamido)cyclohexane-κ2N,N']chloro(η5– pentamethylcyclopentadienyl)iridium(III) chloroform solvate top
Crystal data top
[Ir(C13H19N2O2S)(C10H15)Cl]·CHCl3F(000) = 1480
Mr = 749.60Dx = 1.736 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 15012 reflections
a = 9.4012 (5) Åθ = 1.9–25.5°
b = 12.8491 (7) ŵ = 5.12 mm1
c = 23.7478 (17) ÅT = 173 K
V = 2868.7 (3) Å3Needle, yellow
Z = 40.45 × 0.15 × 0.08 mm
Data collection top
Stoe IPDS
diffractometer
5576 independent reflections
Radiation source: fine-focus sealed tube4830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ scansθmax = 25.9°, θmin = 2.3°
Absorption correction: multi-scan
(MULABS in PLATON; Spek, 2003)
h = 1111
Tmin = 0.360, Tmax = 0.557k = 1515
15012 measured reflectionsl = 2927
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0306P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.002
5576 reflectionsΔρmax = 1.53 e Å3
313 parametersΔρmin = 1.82 e Å3
0 restraintsAbsolute structure: Flack (1983), 2413 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.024 (7)
Special details top

Experimental. A crystal was mounted at 173 K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using Mo Kα graphite monochromated radiation. Image plate distance 70 mm, φ oscillation scans 0 - 200°, step Δφ = 1.2°, 3 minutes per frame.

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*/Ueq
Ir10.67846 (2)0.975962 (17)0.284936 (9)0.01982 (6)
S10.71822 (14)0.79667 (11)0.19040 (6)0.0220 (3)
O10.7959 (5)0.7582 (3)0.23804 (17)0.0316 (10)
N10.6671 (5)0.9139 (3)0.20146 (16)0.0192 (10)
N20.4944 (5)1.0524 (4)0.2531 (2)0.0267 (12)
H2A0.41411.01910.26600.032*
H2B0.49231.11990.26600.032*
C110.4943 (6)1.0524 (4)0.1911 (3)0.0221 (13)
H11A0.56701.10330.17740.027*
C20.8157 (7)0.9480 (4)0.3564 (3)0.0326 (14)
O20.6050 (4)0.7294 (3)0.17001 (19)0.0306 (10)
C170.8438 (6)0.8000 (4)0.1343 (2)0.0228 (12)
C40.8767 (6)1.0584 (5)0.2824 (3)0.0296 (13)
C140.3986 (7)0.9744 (6)0.0824 (3)0.0402 (15)
H14A0.32630.92140.09230.048*
H14B0.40670.97660.04080.048*
C10.7380 (6)1.0442 (5)0.3632 (3)0.0323 (16)
C120.5349 (6)0.9447 (4)0.1712 (2)0.0233 (13)
H12A0.45760.89590.18310.028*
C180.8924 (6)0.7056 (5)0.1132 (3)0.0269 (13)
H18A0.85810.64220.12860.032*
C130.5416 (7)0.9432 (5)0.1076 (3)0.0331 (15)
H13A0.56730.87250.09460.040*
H13B0.61610.99200.09460.040*
C220.8975 (6)0.8926 (5)0.1127 (3)0.0303 (14)
H22A0.86710.95760.12750.036*
C50.7789 (6)1.1127 (4)0.3179 (3)0.0267 (14)
C210.9957 (7)0.8891 (5)0.0693 (3)0.0341 (16)
H21A1.03190.95250.05440.041*
C190.9900 (6)0.7039 (5)0.0701 (3)0.0324 (15)
H19A1.02180.63880.05590.039*
C30.9020 (6)0.9582 (5)0.3086 (3)0.0355 (17)
C70.8101 (11)0.8557 (6)0.3946 (4)0.070 (3)
H7C0.86910.86890.42790.083*
H7B0.84600.79440.37470.083*
H7A0.71160.84350.40630.083*
C201.0430 (6)0.7950 (6)0.0469 (3)0.0338 (15)
C100.7358 (7)1.2238 (5)0.3106 (4)0.049 (2)
H10A0.72091.23830.27050.059*
H10B0.81091.26920.32530.059*
H10C0.64731.23660.33130.059*
C81.0165 (7)0.8843 (6)0.2883 (5)0.071 (3)
H8A1.00350.81620.30620.085*
H8B1.11030.91210.29830.085*
H8C1.01000.87670.24730.085*
C60.6390 (8)1.0717 (8)0.4109 (3)0.063 (3)
H6A0.57221.12550.39840.076*
H6B0.69441.09790.44280.076*
H6C0.58601.00960.42250.076*
C160.3492 (6)1.0829 (5)0.1677 (3)0.0317 (15)
H16A0.27621.03400.18190.038*
H16B0.32421.15370.18090.038*
C150.3503 (8)1.0809 (5)0.1041 (3)0.0386 (17)
H15A0.41551.13540.08980.046*
H15B0.25361.09610.08970.046*
C231.1504 (7)0.7917 (6)0.0003 (3)0.0449 (19)
H23A1.13280.84960.02620.054*
H23B1.14180.72560.02050.054*
H23C1.24650.79790.01540.054*
C90.9498 (8)1.0991 (7)0.2306 (3)0.053 (2)
H9C1.03931.13270.24130.064*
H9B0.88811.14980.21180.064*
H9A0.96961.04120.20480.064*
Cl30.1979 (3)0.92961 (19)0.43475 (11)0.0833 (8)
Cl20.2021 (3)0.70790 (19)0.41831 (13)0.0866 (8)
C240.3063 (10)0.8185 (6)0.4271 (3)0.052 (2)
H24A0.36480.82770.39230.062*
Cl40.4225 (3)0.8078 (2)0.48421 (10)0.0764 (7)
Cl10.50167 (15)0.84418 (12)0.30971 (7)0.0323 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.01598 (8)0.01686 (9)0.02663 (10)0.00012 (10)0.00136 (11)0.00259 (11)
S10.0220 (7)0.0157 (7)0.0283 (7)0.0009 (5)0.0031 (6)0.0005 (6)
O10.038 (3)0.025 (2)0.031 (2)0.008 (2)0.0018 (19)0.0013 (17)
N10.020 (2)0.016 (2)0.022 (3)0.002 (2)0.001 (2)0.0005 (16)
N20.024 (3)0.022 (3)0.035 (3)0.002 (2)0.006 (2)0.007 (2)
C110.021 (3)0.011 (3)0.034 (3)0.002 (2)0.006 (2)0.004 (2)
C20.029 (3)0.029 (3)0.040 (3)0.003 (3)0.016 (3)0.010 (3)
O20.022 (2)0.019 (2)0.050 (3)0.0037 (17)0.003 (2)0.008 (2)
C170.017 (3)0.023 (3)0.029 (3)0.001 (2)0.004 (2)0.002 (2)
C40.020 (2)0.032 (3)0.037 (3)0.010 (2)0.007 (3)0.007 (3)
C140.047 (4)0.040 (4)0.034 (3)0.007 (4)0.015 (3)0.001 (4)
C10.024 (3)0.045 (5)0.028 (3)0.005 (3)0.007 (2)0.011 (3)
C120.022 (3)0.018 (3)0.030 (3)0.002 (2)0.007 (2)0.003 (2)
C180.024 (3)0.025 (3)0.032 (3)0.001 (3)0.000 (3)0.003 (3)
C130.039 (4)0.026 (3)0.034 (4)0.008 (3)0.000 (3)0.003 (3)
C220.029 (3)0.025 (3)0.038 (4)0.001 (3)0.003 (3)0.003 (3)
C50.022 (3)0.017 (3)0.042 (4)0.003 (2)0.014 (3)0.007 (3)
C210.029 (3)0.034 (4)0.040 (4)0.010 (3)0.009 (3)0.003 (3)
C190.023 (3)0.038 (4)0.036 (4)0.008 (3)0.004 (3)0.008 (3)
C30.014 (3)0.034 (4)0.058 (4)0.006 (3)0.023 (3)0.018 (3)
C70.072 (6)0.062 (5)0.075 (6)0.022 (5)0.043 (5)0.041 (4)
C200.021 (3)0.051 (4)0.029 (4)0.001 (3)0.003 (3)0.003 (3)
C100.037 (4)0.016 (3)0.094 (6)0.001 (3)0.019 (4)0.011 (4)
C80.026 (3)0.051 (5)0.137 (8)0.021 (3)0.021 (5)0.039 (6)
C60.049 (5)0.102 (7)0.038 (4)0.017 (4)0.006 (3)0.032 (4)
C160.030 (4)0.030 (3)0.035 (4)0.007 (3)0.011 (3)0.005 (3)
C150.044 (4)0.022 (3)0.050 (4)0.012 (3)0.015 (3)0.004 (3)
C230.029 (4)0.072 (5)0.034 (4)0.001 (3)0.006 (3)0.011 (4)
C90.036 (4)0.071 (6)0.052 (5)0.033 (4)0.009 (3)0.002 (4)
Cl30.100 (2)0.0646 (14)0.0850 (17)0.0328 (15)0.0039 (16)0.0171 (12)
Cl20.0799 (18)0.0610 (14)0.119 (2)0.0069 (14)0.0193 (17)0.0129 (14)
C240.068 (5)0.051 (4)0.037 (4)0.006 (5)0.015 (4)0.002 (3)
Cl40.0771 (16)0.098 (2)0.0538 (14)0.0118 (14)0.0010 (12)0.0105 (13)
Cl10.0284 (8)0.0359 (9)0.0325 (8)0.0119 (7)0.0074 (7)0.0023 (7)
Geometric parameters (Å, º) top
Ir1—N22.129 (5)C13—H13B0.9900
Ir1—C12.130 (6)C22—C211.383 (9)
Ir1—N12.140 (4)C22—H22A0.9500
Ir1—C52.143 (5)C5—C101.493 (8)
Ir1—C42.145 (5)C21—C201.395 (9)
Ir1—C22.162 (6)C21—H21A0.9500
Ir1—C32.188 (5)C19—C201.386 (10)
Ir1—Cl12.4445 (14)C19—H19A0.9500
S1—O11.435 (4)C3—C81.514 (9)
S1—O21.454 (4)C7—H7C0.9800
S1—N11.602 (4)C7—H7B0.9800
S1—C171.780 (6)C7—H7A0.9800
N1—C121.489 (7)C20—C231.508 (9)
N2—C111.472 (7)C10—H10A0.9800
N2—H2A0.9200C10—H10B0.9800
N2—H2B0.9200C10—H10C0.9800
C11—C121.511 (8)C8—H8A0.9800
C11—C161.524 (8)C8—H8B0.9800
C11—H11A1.0000C8—H8C0.9800
C2—C31.402 (10)C6—H6A0.9800
C2—C11.445 (9)C6—H6B0.9800
C2—C71.494 (9)C6—H6C0.9800
C17—C181.390 (8)C16—C151.512 (9)
C17—C221.391 (8)C16—H16A0.9900
C4—C51.429 (9)C16—H16B0.9900
C4—C31.450 (9)C15—H15A0.9900
C4—C91.503 (10)C15—H15B0.9900
C14—C131.525 (9)C23—H23A0.9800
C14—C151.531 (9)C23—H23B0.9800
C14—H14A0.9900C23—H23C0.9800
C14—H14B0.9900C9—H9C0.9800
C1—C51.443 (9)C9—H9B0.9800
C1—C61.508 (9)C9—H9A0.9800
C12—C131.512 (8)Cl3—C241.764 (8)
C12—H12A1.0000Cl2—C241.738 (9)
C18—C191.376 (9)C24—Cl41.746 (9)
C18—H18A0.9500C24—H24A1.0000
C13—H13A0.9900
N2—Ir1—C1109.5 (2)C12—C13—C14110.6 (5)
N2—Ir1—N178.58 (18)C12—C13—H13A109.5
C1—Ir1—N1167.2 (2)C14—C13—H13A109.5
N2—Ir1—C596.3 (2)C12—C13—H13B109.5
C1—Ir1—C539.5 (2)C14—C13—H13B109.5
N1—Ir1—C5131.8 (2)H13A—C13—H13B108.1
N2—Ir1—C4117.9 (2)C21—C22—C17119.3 (6)
C1—Ir1—C466.0 (3)C21—C22—H22A120.3
N1—Ir1—C4101.6 (2)C17—C22—H22A120.3
C5—Ir1—C438.9 (2)C4—C5—C1108.3 (5)
N2—Ir1—C2147.2 (2)C4—C5—C10125.0 (6)
C1—Ir1—C239.3 (2)C1—C5—C10126.6 (6)
N1—Ir1—C2134.0 (2)C4—C5—Ir170.6 (3)
C5—Ir1—C265.6 (2)C1—C5—Ir169.8 (3)
C4—Ir1—C265.5 (3)C10—C5—Ir1128.4 (4)
N2—Ir1—C3157.0 (2)C22—C21—C20121.7 (6)
C1—Ir1—C364.3 (2)C22—C21—H21A119.2
N1—Ir1—C3104.3 (2)C20—C21—H21A119.2
C5—Ir1—C364.4 (2)C18—C19—C20121.5 (6)
C4—Ir1—C339.1 (2)C18—C19—H19A119.3
C2—Ir1—C337.6 (3)C20—C19—H19A119.3
N2—Ir1—Cl181.52 (14)C2—C3—C4109.6 (5)
C1—Ir1—Cl1104.69 (18)C2—C3—C8127.7 (7)
N1—Ir1—Cl186.04 (12)C4—C3—C8122.5 (7)
C5—Ir1—Cl1141.24 (18)C2—C3—Ir170.2 (3)
C4—Ir1—Cl1160.01 (18)C4—C3—Ir168.9 (3)
C2—Ir1—Cl195.84 (17)C8—C3—Ir1131.8 (5)
C3—Ir1—Cl1121.3 (2)C2—C7—H7C109.5
O1—S1—O2115.5 (3)C2—C7—H7B109.5
O1—S1—N1110.3 (2)H7C—C7—H7B109.5
O2—S1—N1113.2 (2)C2—C7—H7A109.5
O1—S1—C17105.1 (2)H7C—C7—H7A109.5
O2—S1—C17104.5 (3)H7B—C7—H7A109.5
N1—S1—C17107.4 (2)C19—C20—C21117.8 (6)
C12—N1—S1114.9 (3)C19—C20—C23120.8 (7)
C12—N1—Ir1112.9 (3)C21—C20—C23121.4 (6)
S1—N1—Ir1119.2 (2)C5—C10—H10A109.5
C11—N2—Ir1110.9 (4)C5—C10—H10B109.5
C11—N2—H2A109.5H10A—C10—H10B109.5
Ir1—N2—H2A109.5C5—C10—H10C109.5
C11—N2—H2B109.5H10A—C10—H10C109.5
Ir1—N2—H2B109.5H10B—C10—H10C109.5
H2A—N2—H2B108.1C3—C8—H8A109.5
N2—C11—C12108.2 (5)C3—C8—H8B109.5
N2—C11—C16111.4 (5)H8A—C8—H8B109.5
C12—C11—C16110.4 (5)C3—C8—H8C109.5
N2—C11—H11A109.0H8A—C8—H8C109.5
C12—C11—H11A109.0H8B—C8—H8C109.5
C16—C11—H11A109.0C1—C6—H6A109.5
C3—C2—C1107.7 (5)C1—C6—H6B109.5
C3—C2—C7125.9 (7)H6A—C6—H6B109.5
C1—C2—C7126.4 (7)C1—C6—H6C109.5
C3—C2—Ir172.2 (3)H6A—C6—H6C109.5
C1—C2—Ir169.1 (3)H6B—C6—H6C109.5
C7—C2—Ir1126.0 (5)C15—C16—C11110.7 (5)
C18—C17—C22119.6 (5)C15—C16—H16A109.5
C18—C17—S1117.8 (4)C11—C16—H16A109.5
C22—C17—S1122.6 (5)C15—C16—H16B109.5
C5—C4—C3106.6 (6)C11—C16—H16B109.5
C5—C4—C9127.3 (6)H16A—C16—H16B108.1
C3—C4—C9125.8 (6)C16—C15—C14110.7 (5)
C5—C4—Ir170.5 (3)C16—C15—H15A109.5
C3—C4—Ir172.1 (3)C14—C15—H15A109.5
C9—C4—Ir1126.3 (5)C16—C15—H15B109.5
C13—C14—C15111.4 (6)C14—C15—H15B109.5
C13—C14—H14A109.4H15A—C15—H15B108.1
C15—C14—H14A109.4C20—C23—H23A109.5
C13—C14—H14B109.4C20—C23—H23B109.5
C15—C14—H14B109.4H23A—C23—H23B109.5
H14A—C14—H14B108.0C20—C23—H23C109.5
C5—C1—C2107.7 (5)H23A—C23—H23C109.5
C5—C1—C6125.6 (6)H23B—C23—H23C109.5
C2—C1—C6126.7 (7)C4—C9—H9C109.5
C5—C1—Ir170.7 (3)C4—C9—H9B109.5
C2—C1—Ir171.5 (3)H9C—C9—H9B109.5
C6—C1—Ir1126.1 (4)C4—C9—H9A109.5
N1—C12—C11107.7 (4)H9C—C9—H9A109.5
N1—C12—C13116.3 (5)H9B—C9—H9A109.5
C11—C12—C13109.5 (5)Cl2—C24—Cl4112.5 (4)
N1—C12—H12A107.7Cl2—C24—Cl3110.4 (5)
C11—C12—H12A107.7Cl4—C24—Cl3110.2 (4)
C13—C12—H12A107.7Cl2—C24—H24A107.9
C19—C18—C17120.1 (6)Cl4—C24—H24A107.9
C19—C18—H18A119.9Cl3—C24—H24A107.9
C17—C18—H18A119.9
O1—S1—N1—C12151.9 (4)C3—Ir1—C1—C6159.2 (8)
O2—S1—N1—C1220.8 (5)Cl1—Ir1—C1—C641.2 (7)
C17—S1—N1—C1294.0 (4)S1—N1—C12—C11174.2 (4)
O1—S1—N1—Ir113.3 (4)Ir1—N1—C12—C1133.0 (5)
O2—S1—N1—Ir1117.8 (3)S1—N1—C12—C1362.5 (6)
C17—S1—N1—Ir1127.3 (3)Ir1—N1—C12—C13156.3 (4)
N2—Ir1—N1—C127.3 (3)N2—C11—C12—N150.4 (6)
C1—Ir1—N1—C12137.7 (9)C16—C11—C12—N1172.4 (5)
C5—Ir1—N1—C1295.6 (4)N2—C11—C12—C13177.7 (5)
C4—Ir1—N1—C12123.8 (4)C16—C11—C12—C1360.2 (7)
C2—Ir1—N1—C12169.1 (3)C22—C17—C18—C191.8 (9)
C3—Ir1—N1—C12163.9 (4)S1—C17—C18—C19179.7 (4)
Cl1—Ir1—N1—C1274.8 (3)N1—C12—C13—C14178.9 (5)
N2—Ir1—N1—S1146.7 (3)C11—C12—C13—C1458.7 (7)
C1—Ir1—N1—S182.8 (10)C15—C14—C13—C1256.0 (7)
C5—Ir1—N1—S1125.0 (3)C18—C17—C22—C211.8 (9)
C4—Ir1—N1—S196.8 (3)S1—C17—C22—C21179.5 (5)
C2—Ir1—N1—S129.7 (4)C3—C4—C5—C13.6 (6)
C3—Ir1—N1—S156.7 (3)C9—C4—C5—C1178.9 (6)
Cl1—Ir1—N1—S164.6 (3)Ir1—C4—C5—C159.9 (4)
C1—Ir1—N2—C11148.9 (4)C3—C4—C5—C10172.6 (6)
N1—Ir1—N2—C1120.8 (4)C9—C4—C5—C102.7 (10)
C5—Ir1—N2—C11110.6 (4)Ir1—C4—C5—C10123.9 (6)
C4—Ir1—N2—C1176.4 (5)C3—C4—C5—Ir163.4 (4)
C2—Ir1—N2—C11163.9 (4)C9—C4—C5—Ir1121.3 (6)
C3—Ir1—N2—C1178.9 (7)C2—C1—C5—C42.0 (6)
Cl1—Ir1—N2—C11108.5 (4)C6—C1—C5—C4178.4 (6)
Ir1—N2—C11—C1245.0 (5)Ir1—C1—C5—C460.4 (4)
Ir1—N2—C11—C16166.5 (4)C2—C1—C5—C10174.1 (6)
N2—Ir1—C2—C3140.3 (4)C6—C1—C5—C102.3 (10)
C1—Ir1—C2—C3117.6 (5)Ir1—C1—C5—C10123.5 (6)
N1—Ir1—C2—C346.1 (4)C2—C1—C5—Ir162.4 (4)
C5—Ir1—C2—C379.2 (4)C6—C1—C5—Ir1121.2 (6)
C4—Ir1—C2—C336.2 (4)N2—Ir1—C5—C4127.8 (4)
Cl1—Ir1—C2—C3136.3 (3)C1—Ir1—C5—C4118.9 (5)
N2—Ir1—C2—C122.7 (6)N1—Ir1—C5—C447.5 (5)
N1—Ir1—C2—C1163.8 (3)C2—Ir1—C5—C480.6 (4)
C5—Ir1—C2—C138.4 (3)C3—Ir1—C5—C439.0 (4)
C4—Ir1—C2—C181.4 (4)Cl1—Ir1—C5—C4147.9 (3)
C3—Ir1—C2—C1117.6 (5)N2—Ir1—C5—C1113.2 (3)
Cl1—Ir1—C2—C1106.1 (3)N1—Ir1—C5—C1166.5 (3)
N2—Ir1—C2—C797.8 (7)C4—Ir1—C5—C1118.9 (5)
C1—Ir1—C2—C7120.5 (9)C2—Ir1—C5—C138.3 (3)
N1—Ir1—C2—C775.7 (8)C3—Ir1—C5—C179.9 (4)
C5—Ir1—C2—C7158.9 (8)Cl1—Ir1—C5—C128.9 (4)
C4—Ir1—C2—C7158.1 (8)N2—Ir1—C5—C108.1 (7)
C3—Ir1—C2—C7121.8 (8)C1—Ir1—C5—C10121.3 (8)
Cl1—Ir1—C2—C714.4 (7)N1—Ir1—C5—C1072.2 (7)
O1—S1—C17—C1869.0 (5)C4—Ir1—C5—C10119.8 (8)
O2—S1—C17—C1853.0 (5)C2—Ir1—C5—C10159.6 (7)
N1—S1—C17—C18173.5 (4)C3—Ir1—C5—C10158.8 (7)
O1—S1—C17—C22108.8 (5)Cl1—Ir1—C5—C1092.3 (7)
O2—S1—C17—C22129.2 (5)C17—C22—C21—C200.3 (10)
N1—S1—C17—C228.7 (6)C17—C18—C19—C200.4 (9)
N2—Ir1—C4—C562.7 (5)C1—C2—C3—C42.7 (6)
C1—Ir1—C4—C537.5 (4)C7—C2—C3—C4179.6 (6)
N1—Ir1—C4—C5145.8 (4)Ir1—C2—C3—C457.7 (4)
C2—Ir1—C4—C580.8 (4)C1—C2—C3—C8171.5 (6)
C3—Ir1—C4—C5115.7 (6)C7—C2—C3—C86.2 (11)
Cl1—Ir1—C4—C5103.2 (5)Ir1—C2—C3—C8128.1 (6)
N2—Ir1—C4—C3178.4 (3)C1—C2—C3—Ir160.3 (4)
C1—Ir1—C4—C378.2 (4)C7—C2—C3—Ir1122.0 (7)
N1—Ir1—C4—C398.4 (4)C5—C4—C3—C23.9 (6)
C5—Ir1—C4—C3115.7 (6)C9—C4—C3—C2179.3 (6)
C2—Ir1—C4—C334.9 (4)Ir1—C4—C3—C258.5 (4)
Cl1—Ir1—C4—C312.6 (8)C5—C4—C3—C8170.7 (6)
N2—Ir1—C4—C959.8 (6)C9—C4—C3—C84.7 (9)
C1—Ir1—C4—C9160.1 (7)Ir1—C4—C3—C8127.0 (6)
N1—Ir1—C4—C923.3 (6)C5—C4—C3—Ir162.4 (4)
C5—Ir1—C4—C9122.5 (7)C9—C4—C3—Ir1122.2 (6)
C2—Ir1—C4—C9156.6 (7)N2—Ir1—C3—C2117.9 (6)
C3—Ir1—C4—C9121.7 (7)C1—Ir1—C3—C238.5 (4)
Cl1—Ir1—C4—C9134.3 (6)N1—Ir1—C3—C2147.7 (3)
C3—C2—C1—C50.4 (6)C5—Ir1—C3—C282.5 (4)
C7—C2—C1—C5178.1 (6)C4—Ir1—C3—C2121.4 (5)
Ir1—C2—C1—C561.9 (4)Cl1—Ir1—C3—C253.6 (4)
C3—C2—C1—C6175.9 (6)N2—Ir1—C3—C43.6 (8)
C7—C2—C1—C61.8 (10)C1—Ir1—C3—C482.9 (4)
Ir1—C2—C1—C6121.8 (6)N1—Ir1—C3—C490.9 (4)
C3—C2—C1—Ir162.3 (4)C5—Ir1—C3—C438.9 (4)
C7—C2—C1—Ir1120.0 (7)C2—Ir1—C3—C4121.4 (5)
N2—Ir1—C1—C575.7 (3)Cl1—Ir1—C3—C4175.0 (3)
N1—Ir1—C1—C552.0 (11)N2—Ir1—C3—C8118.8 (8)
C4—Ir1—C1—C537.0 (3)C1—Ir1—C3—C8161.9 (9)
C2—Ir1—C1—C5117.1 (5)N1—Ir1—C3—C824.4 (8)
C3—Ir1—C1—C580.3 (4)C5—Ir1—C3—C8154.1 (9)
Cl1—Ir1—C1—C5161.8 (3)C4—Ir1—C3—C8115.3 (10)
N2—Ir1—C1—C2167.2 (3)C2—Ir1—C3—C8123.3 (9)
N1—Ir1—C1—C265.1 (11)Cl1—Ir1—C3—C869.7 (8)
C5—Ir1—C1—C2117.1 (5)C18—C19—C20—C211.0 (9)
C4—Ir1—C1—C280.1 (4)C18—C19—C20—C23179.8 (6)
C3—Ir1—C1—C236.8 (4)C22—C21—C20—C191.0 (10)
Cl1—Ir1—C1—C281.1 (3)C22—C21—C20—C23179.8 (6)
N2—Ir1—C1—C644.8 (7)N2—C11—C16—C15179.1 (5)
N1—Ir1—C1—C6172.5 (8)C12—C11—C16—C1559.0 (7)
C5—Ir1—C1—C6120.5 (8)C11—C16—C15—C1455.3 (7)
C4—Ir1—C1—C6157.6 (7)C13—C14—C15—C1654.1 (8)
C2—Ir1—C1—C6122.4 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24A···Cl11.002.363.357 (8)178
N2—H2A···Cl10.922.602.996 (5)106
N2—H2B···O2i0.922.263.063 (7)145
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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