The crystal structure of the title compound, [IrCl2(C10H9N3)2]PF6, contains a monomeric [IrCl2(bpya)2]+ cation (bpya is di-2-pyridylamine) and a hexafluorophosphate anion. The iridium(III) ion is coordinated by four N atoms from two bpya ligands [mean Ir-N distance = 2.049 (6) Å] and two Cl atoms [Ir-Cl = 2.344 (2) Å], forming a distorted octahedral environment.
Supporting information
CCDC reference: 239045
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.012 Å
- R factor = 0.056
- wR factor = 0.128
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.220 0.618
Tmin' and Tmax expected: 0.295 0.618
RR' = 0.747
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.73
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.47
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... P1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13
CL1 -IR1 -N1 -C1 0.00 3.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14
CL1 -IR1 -N1 -C5 -177.00 2.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 27
CL2 -IR1 -N4 -C16 -152.00 4.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 28
CL2 -IR1 -N4 -C20 24.00 4.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 40
N2 -IR1 -N3 -C11 -148.00 3.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 41
N2 -IR1 -N3 -C15 21.00 3.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 49
N3 -IR1 -N2 -C6 -2.00 3.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 50
N3 -IR1 -N2 -C10 -178.00 3.00 1.555 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
F6 P
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
11 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
[IrCl2(C10H9N3)2]PF6 | Z = 2 |
Mr = 750.49 | F(000) = 720 |
Triclinic, P1 | Dx = 2.102 Mg m−3 |
a = 7.6920 (8) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 12.940 (1) Å | Cell parameters from 7910 reflections |
c = 13.229 (1) Å | θ = 2.0–30.5° |
α = 68.958 (3)° | µ = 6.01 mm−1 |
β = 75.775 (4)° | T = 296 K |
γ = 79.760 (6)° | Needle, yellow |
V = 1185.4 (2) Å3 | 0.20 × 0.10 × 0.08 mm |
Data collection top
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 6111 reflections with I > 2.0σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.066 |
ω scans | θmax = 30.5°, θmin = 2.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.220, Tmax = 0.618 | k = −18→18 |
14053 measured reflections | l = −18→18 |
7054 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max = 0.004 |
wR(F2) = 0.128 | Δρmax = 3.70 e Å−3 |
S = 1.72 | Δρmin = −1.50 e Å−3 |
6111 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
325 parameters | Extinction coefficient: 0.0000 |
H-atom parameters constrained | |
Special details top
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ir1 | 0.24177 (3) | 0.22374 (2) | 0.20122 (2) | 0.02817 (9) | |
Cl1 | 0.4511 (3) | 0.0672 (2) | 0.2410 (2) | 0.0512 (4) | |
Cl2 | 0.4647 (2) | 0.3299 (2) | 0.0688 (1) | 0.0417 (4) | |
P1 | −0.3182 (3) | 0.2982 (3) | −0.2953 (2) | 0.0616 (6) | |
F1 | −0.267 (4) | 0.389 (1) | −0.279 (2) | 0.33 (2) | |
F2 | −0.278 (1) | 0.3568 (10) | −0.4262 (7) | 0.137 (4) | |
F3 | −0.505 (1) | 0.345 (2) | −0.299 (1) | 0.26 (1) | |
F4 | −0.347 (4) | 0.212 (1) | −0.332 (2) | 0.33 (2) | |
F5 | −0.360 (2) | 0.237 (2) | −0.1741 (8) | 0.218 (9) | |
F6 | −0.125 (2) | 0.258 (2) | −0.2910 (9) | 0.233 (10) | |
N1 | 0.0644 (7) | 0.3649 (4) | 0.1683 (4) | 0.0277 (10) | |
N2 | 0.1773 (7) | 0.1915 (5) | 0.0740 (5) | 0.032 (1) | |
N3 | 0.2917 (7) | 0.2595 (5) | 0.3296 (5) | 0.033 (1) | |
N4 | 0.0478 (7) | 0.1300 (5) | 0.3120 (4) | 0.031 (1) | |
N5 | −0.0141 (8) | 0.2478 (6) | 0.4202 (5) | 0.041 (1) | |
N6 | −0.1176 (7) | 0.2767 (5) | 0.1105 (5) | 0.034 (1) | |
C1 | 0.0960 (10) | 0.4568 (6) | 0.1857 (6) | 0.038 (1) | |
C2 | −0.027 (1) | 0.5463 (6) | 0.1781 (7) | 0.044 (2) | |
C3 | −0.185 (1) | 0.5481 (6) | 0.1460 (6) | 0.042 (2) | |
C4 | −0.2149 (9) | 0.4593 (6) | 0.1231 (6) | 0.040 (1) | |
C5 | −0.0871 (8) | 0.3680 (5) | 0.1340 (5) | 0.030 (1) | |
C6 | 0.0107 (9) | 0.2155 (6) | 0.0550 (5) | 0.033 (1) | |
C7 | −0.042 (1) | 0.1799 (7) | −0.0207 (7) | 0.046 (2) | |
C8 | 0.086 (1) | 0.1251 (8) | −0.0805 (8) | 0.058 (2) | |
C9 | 0.259 (1) | 0.1032 (7) | −0.0630 (8) | 0.056 (2) | |
C10 | 0.303 (1) | 0.1389 (7) | 0.0123 (6) | 0.043 (2) | |
C11 | 0.4584 (9) | 0.2843 (7) | 0.3268 (6) | 0.043 (2) | |
C12 | 0.490 (1) | 0.3295 (8) | 0.3975 (7) | 0.051 (2) | |
C13 | 0.350 (1) | 0.3534 (8) | 0.4758 (8) | 0.054 (2) | |
C14 | 0.180 (1) | 0.3274 (7) | 0.4820 (6) | 0.047 (2) | |
C15 | 0.1552 (9) | 0.2765 (6) | 0.4108 (6) | 0.035 (1) | |
C16 | −0.0531 (8) | 0.1589 (6) | 0.3979 (5) | 0.033 (1) | |
C17 | −0.1990 (9) | 0.0997 (7) | 0.4673 (6) | 0.045 (2) | |
C18 | −0.2369 (10) | 0.0104 (7) | 0.4464 (7) | 0.048 (2) | |
C19 | −0.130 (1) | −0.0224 (6) | 0.3610 (7) | 0.047 (2) | |
C20 | 0.011 (1) | 0.0376 (6) | 0.2972 (6) | 0.040 (1) | |
H1 | 0.2085 | 0.4571 | 0.2044 | 0.0461* | |
H2 | −0.0058 | 0.6081 | 0.1960 | 0.0541* | |
H3 | −0.2747 | 0.6110 | 0.1406 | 0.0521* | |
H4 | −0.3213 | 0.4603 | 0.0980 | 0.0467* | |
H5 | −0.1647 | 0.1942 | −0.0306 | 0.0553* | |
H6 | 0.0534 | 0.1006 | −0.1330 | 0.0717* | |
H7 | 0.3498 | 0.0637 | −0.1042 | 0.0659* | |
H8 | 0.4258 | 0.1239 | 0.0226 | 0.0493* | |
H9 | −0.2112 | 0.3026 | 0.0689 | 0.0409* | |
H10 | 0.5561 | 0.2670 | 0.2735 | 0.0534* | |
H11 | 0.6089 | 0.3458 | 0.3910 | 0.0599* | |
H12 | 0.3687 | 0.3856 | 0.5266 | 0.0638* | |
H13 | 0.0778 | 0.3419 | 0.5367 | 0.0591* | |
H14 | −0.2724 | 0.1204 | 0.5277 | 0.0524* | |
H15 | −0.3387 | −0.0289 | 0.4931 | 0.0565* | |
H16 | −0.1557 | −0.0845 | 0.3457 | 0.0561* | |
H17 | 0.0900 | 0.0126 | 0.2399 | 0.0478* | |
H18 | −0.0710 | 0.2364 | 0.4956 | 0.0488* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ir1 | 0.0250 (1) | 0.0329 (1) | 0.0265 (1) | −0.00069 (8) | −0.00709 (8) | −0.00934 (9) |
Cl1 | 0.0466 (10) | 0.053 (1) | 0.052 (1) | 0.0162 (8) | −0.0162 (8) | −0.0205 (9) |
Cl2 | 0.0301 (7) | 0.057 (1) | 0.0358 (8) | −0.0110 (7) | −0.0062 (6) | −0.0092 (8) |
P1 | 0.053 (1) | 0.084 (2) | 0.055 (1) | −0.007 (1) | 0.000 (1) | −0.038 (1) |
F1 | 0.52 (4) | 0.15 (1) | 0.45 (3) | −0.05 (2) | −0.35 (3) | −0.09 (2) |
F2 | 0.095 (6) | 0.19 (1) | 0.084 (6) | 0.012 (6) | −0.011 (4) | −0.015 (6) |
F3 | 0.065 (6) | 0.59 (3) | 0.144 (10) | 0.07 (1) | −0.022 (6) | −0.19 (2) |
F4 | 0.75 (5) | 0.13 (1) | 0.20 (2) | −0.11 (2) | −0.19 (2) | −0.05 (1) |
F5 | 0.123 (9) | 0.44 (3) | 0.055 (5) | −0.07 (1) | 0.002 (5) | −0.028 (9) |
F6 | 0.112 (8) | 0.35 (2) | 0.095 (8) | 0.09 (1) | 0.016 (6) | 0.02 (1) |
N1 | 0.028 (2) | 0.028 (2) | 0.026 (2) | −0.005 (2) | −0.006 (2) | −0.006 (2) |
N2 | 0.030 (3) | 0.034 (3) | 0.033 (3) | −0.006 (2) | −0.003 (2) | −0.013 (2) |
N3 | 0.031 (3) | 0.034 (3) | 0.037 (3) | −0.005 (2) | −0.012 (2) | −0.010 (2) |
N4 | 0.034 (3) | 0.032 (3) | 0.023 (2) | −0.005 (2) | −0.006 (2) | −0.004 (2) |
N5 | 0.037 (3) | 0.054 (4) | 0.037 (3) | −0.005 (3) | −0.003 (2) | −0.023 (3) |
N6 | 0.032 (3) | 0.037 (3) | 0.040 (3) | 0.000 (2) | −0.017 (2) | −0.015 (2) |
C1 | 0.043 (4) | 0.033 (3) | 0.036 (3) | −0.006 (3) | −0.011 (3) | −0.005 (3) |
C2 | 0.056 (4) | 0.036 (4) | 0.045 (4) | −0.004 (3) | −0.014 (3) | −0.015 (3) |
C3 | 0.047 (4) | 0.030 (3) | 0.036 (3) | −0.001 (3) | −0.004 (3) | −0.001 (3) |
C4 | 0.031 (3) | 0.046 (4) | 0.042 (4) | 0.000 (3) | −0.009 (3) | −0.016 (3) |
C5 | 0.026 (3) | 0.034 (3) | 0.025 (3) | −0.008 (2) | −0.002 (2) | −0.007 (2) |
C6 | 0.039 (3) | 0.033 (3) | 0.026 (3) | −0.013 (3) | −0.007 (2) | −0.005 (2) |
C7 | 0.053 (4) | 0.047 (4) | 0.049 (4) | −0.012 (3) | −0.019 (3) | −0.021 (4) |
C8 | 0.077 (6) | 0.059 (5) | 0.053 (5) | −0.011 (4) | −0.018 (4) | −0.033 (4) |
C9 | 0.070 (6) | 0.048 (5) | 0.057 (5) | 0.003 (4) | −0.010 (4) | −0.031 (4) |
C10 | 0.044 (4) | 0.054 (4) | 0.030 (3) | 0.001 (3) | −0.003 (3) | −0.020 (3) |
C11 | 0.028 (3) | 0.060 (5) | 0.037 (4) | −0.004 (3) | −0.010 (3) | −0.010 (3) |
C12 | 0.042 (4) | 0.074 (6) | 0.047 (4) | −0.012 (4) | −0.020 (3) | −0.020 (4) |
C13 | 0.060 (5) | 0.066 (6) | 0.053 (5) | −0.011 (4) | −0.025 (4) | −0.028 (4) |
C14 | 0.058 (5) | 0.054 (5) | 0.033 (4) | −0.006 (4) | −0.012 (3) | −0.019 (3) |
C15 | 0.036 (3) | 0.031 (3) | 0.035 (3) | −0.002 (2) | −0.012 (3) | −0.007 (3) |
C16 | 0.034 (3) | 0.038 (3) | 0.023 (3) | 0.004 (2) | −0.011 (2) | −0.006 (2) |
C17 | 0.031 (3) | 0.060 (5) | 0.039 (4) | −0.003 (3) | −0.004 (3) | −0.011 (3) |
C18 | 0.031 (3) | 0.051 (4) | 0.051 (4) | −0.010 (3) | −0.012 (3) | 0.003 (4) |
C19 | 0.053 (4) | 0.036 (4) | 0.047 (4) | −0.011 (3) | −0.014 (3) | −0.001 (3) |
C20 | 0.050 (4) | 0.027 (3) | 0.039 (4) | −0.004 (3) | −0.010 (3) | −0.006 (3) |
Geometric parameters (Å, º) top
Ir1—Cl1 | 2.337 (2) | C2—H2 | 0.961 |
Ir1—Cl2 | 2.351 (2) | C3—C4 | 1.36 (1) |
Ir1—N1 | 2.055 (5) | C3—H3 | 0.961 |
Ir1—N2 | 2.059 (7) | C4—C5 | 1.384 (9) |
Ir1—N3 | 2.049 (7) | C4—H4 | 0.952 |
Ir1—N4 | 2.034 (5) | C6—C7 | 1.41 (1) |
P1—F1 | 1.40 (3) | C7—C8 | 1.37 (1) |
P1—F2 | 1.595 (9) | C7—H5 | 0.961 |
P1—F3 | 1.46 (1) | C8—C9 | 1.37 (2) |
P1—F4 | 1.44 (2) | C8—H6 | 0.957 |
P1—F5 | 1.492 (10) | C9—C10 | 1.37 (2) |
P1—F6 | 1.49 (1) | C9—H7 | 0.964 |
N1—C1 | 1.36 (1) | C10—H8 | 0.960 |
N1—C5 | 1.340 (9) | C11—C12 | 1.35 (2) |
N2—C6 | 1.327 (9) | C11—H10 | 0.952 |
N2—C10 | 1.359 (10) | C12—C13 | 1.37 (1) |
N3—C11 | 1.36 (1) | C12—H11 | 0.951 |
N3—C15 | 1.356 (9) | C13—C14 | 1.39 (1) |
N4—C16 | 1.342 (9) | C13—H12 | 0.956 |
N4—C20 | 1.36 (1) | C14—C15 | 1.39 (1) |
N5—C15 | 1.38 (1) | C14—H13 | 0.969 |
N5—C16 | 1.38 (1) | C16—C17 | 1.408 (9) |
N5—H18 | 0.955 | C17—C18 | 1.37 (1) |
N6—C5 | 1.39 (1) | C17—H14 | 0.953 |
N6—C6 | 1.388 (9) | C18—C19 | 1.38 (1) |
N6—H9 | 0.954 | C18—H15 | 0.965 |
C1—C2 | 1.35 (1) | C19—C20 | 1.37 (1) |
C1—H1 | 0.958 | C19—H16 | 0.960 |
C2—C3 | 1.38 (1) | C20—H17 | 0.963 |
| | | |
Cl1···F4i | 3.54 (2) | F6···C14iv | 3.26 (1) |
Cl2···N6ii | 3.304 (6) | N2···C3iii | 3.573 (8) |
Cl2···C4ii | 3.549 (9) | N4···C18viii | 3.58 (1) |
F1···C2iii | 3.25 (3) | N4···C17viii | 3.594 (9) |
F1···C1iii | 3.28 (3) | N5···C19viii | 3.531 (9) |
F1···C13iii | 3.48 (2) | C2···C7iii | 3.46 (1) |
F2···N5iv | 3.04 (1) | C2···C6iii | 3.485 (9) |
F2···C12v | 3.40 (2) | C3···C6iii | 3.478 (9) |
F2···C13v | 3.43 (2) | C8···C8i | 3.46 (2) |
F2···C14iv | 3.43 (1) | C12···C17ii | 3.46 (1) |
F2···C13iii | 3.53 (2) | C15···C18viii | 3.530 (10) |
F3···C3vi | 3.18 (2) | C15···C19viii | 3.574 (9) |
F3···C13v | 3.40 (2) | C16···C18viii | 3.361 (10) |
F4···C17iv | 3.34 (2) | C16···C19viii | 3.54 (1) |
F4···N5iv | 3.56 (2) | C17···C20viii | 3.50 (1) |
F5···C10vii | 3.19 (1) | C17···C19viii | 3.58 (1) |
F5···C9vii | 3.41 (2) | | |
| | | |
Cl1—Ir1—Cl2 | 91.09 (6) | C2—C3—C4 | 119.2 (7) |
Cl1—Ir1—N1 | 177.5 (2) | C2—C3—H3 | 120.6 |
Cl1—Ir1—N2 | 94.4 (2) | C4—C3—H3 | 120.2 |
Cl1—Ir1—N3 | 88.3 (2) | C3—C4—C5 | 119.5 (7) |
Cl1—Ir1—N4 | 88.7 (1) | C3—C4—H4 | 120.3 |
Cl2—Ir1—N1 | 87.7 (1) | C5—C4—H4 | 120.1 |
Cl2—Ir1—N2 | 87.5 (1) | N1—C5—N6 | 119.2 (5) |
Cl2—Ir1—N3 | 94.1 (2) | N1—C5—C4 | 121.3 (7) |
Cl2—Ir1—N4 | 178.2 (2) | N6—C5—C4 | 119.5 (7) |
N1—Ir1—N2 | 87.7 (2) | N2—C6—N6 | 120.4 (7) |
N1—Ir1—N3 | 89.7 (2) | N2—C6—C7 | 121.7 (7) |
N1—Ir1—N4 | 92.6 (2) | N6—C6—C7 | 117.9 (6) |
N2—Ir1—N3 | 176.9 (2) | C6—C7—C8 | 118.4 (8) |
N2—Ir1—N4 | 90.7 (2) | C6—C7—H5 | 120.9 |
N3—Ir1—N4 | 87.7 (2) | C8—C7—H5 | 120.7 |
F1—P1—F2 | 91 (1) | C7—C8—C9 | 119 (1) |
F1—P1—F3 | 94 (1) | C7—C8—H6 | 120.0 |
F1—P1—F4 | 168 (1) | C9—C8—H6 | 120.3 |
F1—P1—F5 | 92 (1) | C8—C9—C10 | 119.6 (9) |
F1—P1—F6 | 80 (1) | C8—C9—H7 | 120.2 |
F2—P1—F3 | 86.2 (6) | C10—C9—H7 | 120.2 |
F2—P1—F4 | 78.5 (8) | N2—C10—C9 | 121.5 (8) |
F2—P1—F5 | 176.2 (10) | N2—C10—H8 | 120.0 |
F2—P1—F6 | 93.7 (5) | C9—C10—H8 | 118.5 |
F3—P1—F4 | 89 (1) | N3—C11—C12 | 122.9 (7) |
F3—P1—F5 | 93.2 (7) | N3—C11—H10 | 117.7 |
F3—P1—F6 | 175 (1) | C12—C11—H10 | 119.4 |
F4—P1—F5 | 97 (1) | C11—C12—C13 | 119.8 (9) |
F4—P1—F6 | 94 (1) | C11—C12—H11 | 119.1 |
F5—P1—F6 | 87.2 (6) | C13—C12—H11 | 121.1 |
Ir1—N1—C1 | 119.8 (5) | C12—C13—C14 | 118 (1) |
Ir1—N1—C5 | 121.7 (5) | C12—C13—H12 | 121.5 |
C1—N1—C5 | 118.4 (6) | C14—C13—H12 | 119.8 |
Ir1—N2—C6 | 121.0 (5) | C13—C14—C15 | 119.5 (8) |
Ir1—N2—C10 | 120.0 (5) | C13—C14—H13 | 121.3 |
C6—N2—C10 | 118.9 (7) | C15—C14—H13 | 119.2 |
Ir1—N3—C11 | 120.7 (5) | N3—C15—N5 | 119.7 (8) |
Ir1—N3—C15 | 120.9 (5) | N3—C15—C14 | 121.3 (7) |
C11—N3—C15 | 117.6 (8) | N5—C15—C14 | 119.0 (7) |
Ir1—N4—C16 | 122.0 (5) | N4—C16—N5 | 120.0 (6) |
Ir1—N4—C20 | 120.0 (4) | N4—C16—C17 | 121.3 (8) |
C16—N4—C20 | 118.0 (6) | N5—C16—C17 | 118.7 (7) |
C15—N5—C16 | 126.7 (6) | C16—C17—C18 | 118.9 (8) |
C15—N5—H18 | 104.9 | C16—C17—H14 | 121.7 |
C16—N5—H18 | 104.7 | C18—C17—H14 | 119.4 |
C5—N6—C6 | 125.6 (6) | C17—C18—C19 | 120.2 (7) |
C5—N6—H9 | 105.9 | C17—C18—H15 | 118.6 |
C6—N6—H9 | 105.2 | C19—C18—H15 | 121.2 |
N1—C1—C2 | 121.8 (8) | C18—C19—C20 | 118.2 (9) |
N1—C1—H1 | 118.6 | C18—C19—H16 | 120.7 |
C2—C1—H1 | 119.6 | C20—C19—H16 | 121.1 |
C1—C2—C3 | 119.6 (9) | N4—C20—C19 | 123.3 (7) |
C1—C2—H2 | 120.5 | N4—C20—H17 | 118.4 |
C3—C2—H2 | 119.9 | C19—C20—H17 | 118.3 |
| | | |
Ir1—N1—C1—C2 | −171.8 (5) | N3—Ir1—N1—C5 | −143.7 (4) |
Ir1—N1—C5—N6 | −5.8 (7) | N3—Ir1—N2—C6 | −2 (3) |
Ir1—N1—C5—C4 | 173.1 (4) | N3—Ir1—N2—C10 | −178 (3) |
Ir1—N2—C6—N6 | 9.0 (8) | N3—Ir1—N4—C16 | 35.1 (5) |
Ir1—N2—C6—C7 | −170.7 (5) | N3—Ir1—N4—C20 | −148.1 (5) |
Ir1—N2—C10—C9 | 171.3 (6) | N3—C11—C12—C13 | 0 (1) |
Ir1—N3—C11—C12 | 166.6 (6) | N3—C15—N5—C16 | 34.4 (9) |
Ir1—N3—C15—N5 | 13.2 (8) | N3—C15—C14—C13 | −5 (1) |
Ir1—N3—C15—C14 | −163.7 (5) | N4—Ir1—N1—C1 | 121.2 (5) |
Ir1—N4—C16—N5 | −7.1 (8) | N4—Ir1—N1—C5 | −56.0 (5) |
Ir1—N4—C16—C17 | 173.3 (5) | N4—Ir1—N2—C6 | 56.4 (5) |
Ir1—N4—C20—C19 | −172.6 (6) | N4—Ir1—N2—C10 | −119.6 (5) |
Cl1—Ir1—N1—C1 | 0 (3) | N4—Ir1—N3—C11 | 152.5 (5) |
Cl1—Ir1—N1—C5 | −177 (2) | N4—Ir1—N3—C15 | −38.1 (5) |
Cl1—Ir1—N2—C6 | 145.1 (5) | N4—C16—N5—C15 | −38.2 (9) |
Cl1—Ir1—N2—C10 | −30.8 (5) | N4—C16—C17—C18 | 0 (1) |
Cl1—Ir1—N3—C11 | 63.7 (5) | N4—C20—C19—C18 | −1 (1) |
Cl1—Ir1—N3—C15 | −126.8 (5) | N5—C15—N3—C11 | −177.0 (6) |
Cl1—Ir1—N4—C16 | 123.4 (5) | N5—C15—C14—C13 | 177.9 (7) |
Cl1—Ir1—N4—C20 | −59.8 (5) | N5—C16—N4—C20 | 176.1 (6) |
Cl2—Ir1—N1—C1 | −60.6 (4) | N5—C16—C17—C18 | −179.2 (7) |
Cl2—Ir1—N1—C5 | 122.2 (4) | N6—C5—N1—C1 | 176.9 (5) |
Cl2—Ir1—N2—C6 | −124.0 (5) | N6—C5—C4—C3 | 180.0 (6) |
Cl2—Ir1—N2—C10 | 60.1 (5) | N6—C6—N2—C10 | −175.0 (6) |
Cl2—Ir1—N3—C11 | −27.3 (5) | N6—C6—C7—C8 | 176.3 (6) |
Cl2—Ir1—N3—C15 | 142.2 (5) | C1—N1—C5—C4 | −4.2 (8) |
Cl2—Ir1—N4—C16 | −152 (4) | C1—C2—C3—C4 | 0 (1) |
Cl2—Ir1—N4—C20 | 24 (4) | C2—C1—N1—C5 | 5.5 (9) |
N1—Ir1—N2—C6 | −36.2 (5) | C2—C3—C4—C5 | 0 (1) |
N1—Ir1—N2—C10 | 147.8 (5) | C4—C5—N6—C6 | 139.4 (6) |
N1—Ir1—N3—C11 | −114.9 (5) | C5—N6—C6—C7 | −140.4 (7) |
N1—Ir1—N3—C15 | 54.5 (5) | C6—N2—C10—C9 | −4.7 (10) |
N1—Ir1—N4—C16 | −54.5 (5) | C6—C7—C8—C9 | 2 (1) |
N1—Ir1—N4—C20 | 122.4 (5) | C7—C6—N2—C10 | 5.3 (9) |
N1—C1—C2—C3 | −3 (1) | C7—C8—C9—C10 | −1 (1) |
N1—C5—N6—C6 | −41.6 (9) | C11—N3—C15—C14 | 6.1 (9) |
N1—C5—C4—C3 | 1.1 (9) | C11—C12—C13—C14 | 1 (1) |
N2—Ir1—N1—C1 | −148.2 (5) | C12—C11—N3—C15 | −3 (1) |
N2—Ir1—N1—C5 | 34.6 (4) | C12—C13—C14—C15 | 1 (1) |
N2—Ir1—N3—C11 | −148 (3) | C14—C15—N5—C16 | −148.6 (7) |
N2—Ir1—N3—C15 | 21 (3) | C15—N5—C16—C17 | 141.4 (7) |
N2—Ir1—N4—C16 | −142.2 (5) | C16—N4—C20—C19 | 4 (1) |
N2—Ir1—N4—C20 | 34.6 (5) | C16—C17—C18—C19 | 2 (1) |
N2—C6—N6—C5 | 39.9 (9) | C17—C16—N4—C20 | −3.5 (9) |
N2—C6—C7—C8 | −4 (1) | C17—C18—C19—C20 | −1 (1) |
N2—C10—C9—C8 | 2 (1) | C17—C18—C19—C20 | −1 (1) |
N3—Ir1—N1—C1 | 33.6 (5) | | |
Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) −x, −y+1, −z; (iv) x, y, z−1; (v) x−1, y, z−1; (vi) −x−1, −y+1, −z; (vii) x−1, y, z; (viii) −x, −y, −z+1. |
Hydrogen-bond geometry (º) top
D—H···A | D—H···A |
N5—H18···F2ix | 129 |
N5—H18···F4ix | 156 |
N6—H9···Cl2vii | 148 |
Symmetry codes: (vii) x−1, y, z; (ix) x, y, z+1. |