The cationic cyclometallated iridium(III) complex [Ir(C9H7N2)2(C12H8N2)](PF6) has been synthesized and crystallized by the inter-diffusion method. It contains an unknown number of solvent molecules and has a different space-group symmetry (C2/c) structure than its solvatomorph (P21/c).
Supporting information
CCDC reference: 1856996
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.008 Å
- R factor = 0.039
- wR factor = 0.094
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT260_ALERT_2_C Large Average Ueq of Residue Including P1 0.110 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A ..F6 . 2.57 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 9.831 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.392 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 10 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 5 Note
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 39.62 Why ?
PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of P1 Check
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure 568 A 3
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 34 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 2 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
7 ALERT level G = General information/check it is not something unexpected
1 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
5 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020) and DIAMOND (Brandenburg & Putz, 2016); software used to prepare material for publication: publCIF (Westrip, 2010).
(1,10-Phenanthroline-
κ2N,
N')[2-(1
H-pyrazol-1-yl)phenyl-
κ2N2,
C1]iridium(III)
hexafluoridophosphate
top
Crystal data top
[Ir(C9H7N2)2(C12H8N2)]PF6 | F(000) = 3120 |
Mr = 803.70 | Dx = 1.667 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.976 (3) Å | Cell parameters from 10866 reflections |
b = 22.818 (5) Å | θ = 3.0–26.0° |
c = 18.850 (4) Å | µ = 4.28 mm−1 |
β = 95.98 (3)° | T = 293 K |
V = 6406 (2) Å3 | Block, red |
Z = 8 | 0.25 × 0.22 × 0.20 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5077 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.039 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 26.0°, θmin = 3.0° |
| h = −15→18 |
29484 measured reflections | k = −28→25 |
6280 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0321P)2 + 39.6215P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
6280 reflections | Δρmax = 1.25 e Å−3 |
397 parameters | Δρmin = −0.96 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ir1 | 0.25544 (2) | −0.00046 (2) | 0.00566 (2) | 0.02570 (9) | |
N1 | 0.3343 (3) | 0.06189 (18) | 0.0705 (2) | 0.0289 (10) | |
N2 | 0.1946 (3) | −0.00380 (17) | 0.1030 (2) | 0.0254 (9) | |
N3 | 0.3270 (3) | −0.07374 (19) | 0.0323 (2) | 0.0289 (10) | |
N4 | 0.2938 (3) | −0.12375 (18) | −0.0004 (2) | 0.0317 (10) | |
N5 | 0.1815 (3) | 0.06810 (19) | −0.0356 (2) | 0.0323 (10) | |
N6 | 0.2036 (3) | 0.08734 (19) | −0.1000 (2) | 0.0362 (11) | |
C1 | 0.4018 (4) | 0.0938 (2) | 0.0528 (3) | 0.0362 (13) | |
H1A | 0.4237 | 0.0871 | 0.0091 | 0.043* | |
C2 | 0.4418 (4) | 0.1377 (3) | 0.0976 (3) | 0.0416 (14) | |
H2A | 0.4888 | 0.1598 | 0.0831 | 0.050* | |
C3 | 0.4118 (4) | 0.1478 (2) | 0.1623 (3) | 0.0397 (14) | |
H3A | 0.4386 | 0.1764 | 0.1926 | 0.048* | |
C4 | 0.3391 (4) | 0.1142 (2) | 0.1827 (3) | 0.0348 (12) | |
C5 | 0.3015 (4) | 0.1213 (3) | 0.2491 (3) | 0.0408 (14) | |
H5A | 0.3250 | 0.1498 | 0.2811 | 0.049* | |
C6 | 0.2328 (4) | 0.0877 (2) | 0.2662 (3) | 0.0378 (13) | |
H6A | 0.2101 | 0.0930 | 0.3099 | 0.045* | |
C7 | 0.1946 (3) | 0.0440 (2) | 0.2182 (3) | 0.0296 (11) | |
C8 | 0.1236 (4) | 0.0068 (2) | 0.2333 (3) | 0.0334 (12) | |
H8A | 0.0989 | 0.0101 | 0.2764 | 0.040* | |
C9 | 0.0914 (4) | −0.0341 (2) | 0.1843 (3) | 0.0326 (12) | |
H9A | 0.0450 | −0.0589 | 0.1940 | 0.039* | |
C10 | 0.1287 (3) | −0.0384 (2) | 0.1192 (3) | 0.0300 (11) | |
H10A | 0.1063 | −0.0665 | 0.0863 | 0.036* | |
C11 | 0.2288 (3) | 0.0364 (2) | 0.1529 (2) | 0.0264 (11) | |
C12 | 0.3025 (3) | 0.0718 (2) | 0.1349 (3) | 0.0277 (11) | |
C13 | 0.4046 (4) | −0.0891 (3) | 0.0694 (3) | 0.0367 (13) | |
H13A | 0.4422 | −0.0638 | 0.0973 | 0.044* | |
C14 | 0.4207 (4) | −0.1483 (3) | 0.0602 (3) | 0.0445 (15) | |
H14A | 0.4698 | −0.1697 | 0.0805 | 0.053* | |
C15 | 0.3503 (4) | −0.1691 (3) | 0.0154 (3) | 0.0417 (14) | |
H15A | 0.3426 | −0.2073 | −0.0011 | 0.050* | |
C16 | 0.2090 (4) | −0.1185 (2) | −0.0414 (3) | 0.0302 (12) | |
C17 | 0.1642 (4) | −0.1663 (3) | −0.0724 (3) | 0.0422 (14) | |
H17A | 0.1892 | −0.2036 | −0.0679 | 0.051* | |
C18 | 0.0812 (4) | −0.1576 (3) | −0.1106 (3) | 0.0465 (16) | |
H18A | 0.0498 | −0.1892 | −0.1320 | 0.056* | |
C19 | 0.0454 (4) | −0.1023 (3) | −0.1166 (3) | 0.0426 (14) | |
H19A | −0.0103 | −0.0966 | −0.1424 | 0.051* | |
C20 | 0.0912 (4) | −0.0547 (2) | −0.0845 (3) | 0.0332 (12) | |
H20A | 0.0653 | −0.0176 | −0.0887 | 0.040* | |
C21 | 0.1757 (3) | −0.0614 (2) | −0.0458 (3) | 0.0287 (11) | |
C22 | 0.1125 (4) | 0.0995 (3) | −0.0200 (3) | 0.0428 (14) | |
H22A | 0.0840 | 0.0954 | 0.0213 | 0.051* | |
C23 | 0.0886 (4) | 0.1395 (3) | −0.0738 (4) | 0.0528 (17) | |
H23A | 0.0421 | 0.1666 | −0.0757 | 0.063* | |
C24 | 0.1476 (5) | 0.1307 (3) | −0.1235 (3) | 0.0515 (17) | |
H24A | 0.1487 | 0.1511 | −0.1661 | 0.062* | |
C25 | 0.2783 (4) | 0.0599 (2) | −0.1271 (3) | 0.0358 (13) | |
C26 | 0.3100 (4) | 0.0767 (3) | −0.1898 (3) | 0.0478 (16) | |
H26A | 0.2833 | 0.1077 | −0.2163 | 0.057* | |
C27 | 0.3814 (5) | 0.0474 (3) | −0.2130 (3) | 0.0514 (17) | |
H27A | 0.4039 | 0.0586 | −0.2551 | 0.062* | |
C28 | 0.4198 (5) | 0.0012 (3) | −0.1737 (3) | 0.0514 (17) | |
H28A | 0.4680 | −0.0188 | −0.1896 | 0.062* | |
C29 | 0.3863 (4) | −0.0159 (3) | −0.1097 (3) | 0.0371 (13) | |
H29A | 0.4128 | −0.0472 | −0.0839 | 0.045* | |
C30 | 0.3144 (4) | 0.0132 (2) | −0.0845 (3) | 0.0308 (12) | |
P1 | 0.35528 (11) | 0.28676 (7) | 0.33205 (8) | 0.0404 (4) | |
F1 | 0.3359 (4) | 0.2677 (2) | 0.2511 (2) | 0.105 (2) | |
F2 | 0.3773 (4) | 0.3061 (2) | 0.4122 (2) | 0.0877 (15) | |
F3 | 0.4239 (4) | 0.3339 (2) | 0.3101 (3) | 0.0978 (17) | |
F4 | 0.2835 (5) | 0.2436 (3) | 0.3520 (4) | 0.152 (3) | |
F5 | 0.2829 (4) | 0.3381 (3) | 0.3221 (4) | 0.140 (2) | |
F6 | 0.4276 (5) | 0.2399 (3) | 0.3409 (3) | 0.147 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ir1 | 0.02768 (12) | 0.02890 (14) | 0.02103 (12) | −0.00258 (8) | 0.00499 (8) | 0.00069 (8) |
N1 | 0.029 (2) | 0.029 (2) | 0.028 (2) | −0.0065 (19) | 0.0014 (19) | −0.0035 (18) |
N2 | 0.026 (2) | 0.026 (2) | 0.024 (2) | −0.0003 (17) | 0.0036 (17) | 0.0014 (17) |
N3 | 0.033 (2) | 0.034 (2) | 0.022 (2) | −0.0015 (19) | 0.0107 (19) | −0.0002 (18) |
N4 | 0.042 (3) | 0.029 (2) | 0.025 (2) | −0.001 (2) | 0.008 (2) | 0.0023 (18) |
N5 | 0.036 (3) | 0.029 (2) | 0.031 (2) | −0.005 (2) | 0.002 (2) | −0.0001 (19) |
N6 | 0.042 (3) | 0.037 (3) | 0.029 (2) | −0.006 (2) | 0.000 (2) | 0.010 (2) |
C1 | 0.040 (3) | 0.037 (3) | 0.032 (3) | −0.010 (3) | 0.004 (2) | −0.001 (2) |
C2 | 0.037 (3) | 0.046 (4) | 0.042 (4) | −0.012 (3) | 0.005 (3) | 0.000 (3) |
C3 | 0.040 (3) | 0.042 (3) | 0.035 (3) | −0.010 (3) | −0.005 (3) | −0.008 (3) |
C4 | 0.039 (3) | 0.037 (3) | 0.028 (3) | −0.005 (2) | 0.000 (2) | −0.003 (2) |
C5 | 0.053 (4) | 0.043 (3) | 0.026 (3) | −0.005 (3) | 0.002 (3) | −0.004 (2) |
C6 | 0.043 (3) | 0.046 (3) | 0.026 (3) | −0.004 (3) | 0.008 (2) | −0.003 (2) |
C7 | 0.033 (3) | 0.031 (3) | 0.024 (3) | 0.004 (2) | 0.003 (2) | 0.001 (2) |
C8 | 0.037 (3) | 0.041 (3) | 0.023 (3) | 0.002 (2) | 0.013 (2) | 0.007 (2) |
C9 | 0.035 (3) | 0.037 (3) | 0.027 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C10 | 0.031 (3) | 0.030 (3) | 0.029 (3) | −0.003 (2) | 0.007 (2) | 0.003 (2) |
C11 | 0.031 (3) | 0.029 (3) | 0.019 (2) | 0.000 (2) | 0.000 (2) | −0.001 (2) |
C12 | 0.027 (3) | 0.034 (3) | 0.022 (3) | 0.001 (2) | 0.001 (2) | −0.001 (2) |
C13 | 0.029 (3) | 0.052 (4) | 0.029 (3) | 0.000 (3) | 0.001 (2) | 0.007 (3) |
C14 | 0.047 (4) | 0.045 (4) | 0.042 (4) | 0.014 (3) | 0.008 (3) | 0.014 (3) |
C15 | 0.055 (4) | 0.034 (3) | 0.038 (3) | 0.007 (3) | 0.014 (3) | 0.008 (3) |
C16 | 0.039 (3) | 0.033 (3) | 0.019 (3) | −0.005 (2) | 0.006 (2) | −0.002 (2) |
C17 | 0.065 (4) | 0.035 (3) | 0.027 (3) | −0.008 (3) | 0.009 (3) | 0.000 (2) |
C18 | 0.059 (4) | 0.046 (4) | 0.033 (3) | −0.028 (3) | 0.000 (3) | −0.005 (3) |
C19 | 0.041 (3) | 0.057 (4) | 0.029 (3) | −0.014 (3) | 0.000 (3) | 0.002 (3) |
C20 | 0.034 (3) | 0.043 (3) | 0.022 (3) | −0.008 (2) | 0.005 (2) | 0.001 (2) |
C21 | 0.034 (3) | 0.035 (3) | 0.019 (2) | −0.009 (2) | 0.010 (2) | 0.000 (2) |
C22 | 0.033 (3) | 0.044 (3) | 0.051 (4) | 0.010 (3) | 0.004 (3) | −0.001 (3) |
C23 | 0.042 (4) | 0.051 (4) | 0.063 (5) | 0.007 (3) | −0.009 (3) | 0.011 (3) |
C24 | 0.062 (4) | 0.045 (4) | 0.044 (4) | 0.001 (3) | −0.011 (3) | 0.018 (3) |
C25 | 0.038 (3) | 0.041 (3) | 0.028 (3) | −0.007 (3) | 0.001 (2) | 0.002 (2) |
C26 | 0.061 (4) | 0.047 (4) | 0.035 (3) | −0.019 (3) | 0.004 (3) | 0.011 (3) |
C27 | 0.058 (4) | 0.071 (5) | 0.028 (3) | −0.026 (4) | 0.016 (3) | −0.002 (3) |
C28 | 0.051 (4) | 0.072 (5) | 0.033 (3) | −0.017 (3) | 0.015 (3) | −0.009 (3) |
C29 | 0.038 (3) | 0.050 (3) | 0.025 (3) | −0.008 (3) | 0.012 (2) | −0.005 (2) |
C30 | 0.032 (3) | 0.044 (3) | 0.017 (2) | −0.012 (2) | 0.004 (2) | −0.004 (2) |
P1 | 0.0506 (9) | 0.0377 (8) | 0.0325 (8) | −0.0028 (7) | 0.0030 (7) | 0.0021 (6) |
F1 | 0.163 (5) | 0.105 (4) | 0.041 (3) | −0.067 (4) | −0.014 (3) | 0.005 (2) |
F2 | 0.127 (4) | 0.095 (3) | 0.041 (2) | −0.017 (3) | 0.009 (2) | −0.019 (2) |
F3 | 0.128 (4) | 0.083 (3) | 0.086 (3) | −0.054 (3) | 0.027 (3) | −0.018 (3) |
F4 | 0.198 (7) | 0.158 (6) | 0.116 (5) | −0.125 (5) | 0.084 (5) | −0.035 (4) |
F5 | 0.103 (4) | 0.108 (4) | 0.200 (7) | 0.049 (4) | −0.023 (4) | 0.011 (4) |
F6 | 0.183 (7) | 0.146 (5) | 0.104 (5) | 0.135 (5) | −0.024 (4) | −0.014 (4) |
Geometric parameters (Å, º) top
Ir1—C21 | 2.016 (5) | C11—C12 | 1.437 (7) |
Ir1—C30 | 2.019 (5) | C13—C14 | 1.388 (8) |
Ir1—N3 | 2.021 (4) | C13—H13A | 0.9300 |
Ir1—N5 | 2.025 (4) | C14—C15 | 1.365 (9) |
Ir1—N2 | 2.133 (4) | C14—H14A | 0.9300 |
Ir1—N1 | 2.148 (4) | C15—H15A | 0.9300 |
N1—C1 | 1.317 (7) | C16—C17 | 1.378 (7) |
N1—C12 | 1.367 (6) | C16—C21 | 1.394 (7) |
N2—C10 | 1.324 (6) | C17—C18 | 1.383 (9) |
N2—C11 | 1.374 (6) | C17—H17A | 0.9300 |
N3—C13 | 1.339 (7) | C18—C19 | 1.370 (9) |
N3—N4 | 1.366 (6) | C18—H18A | 0.9300 |
N4—C15 | 1.349 (7) | C19—C20 | 1.390 (8) |
N4—C16 | 1.420 (7) | C19—H19A | 0.9300 |
N5—C22 | 1.315 (7) | C20—C21 | 1.401 (7) |
N5—N6 | 1.364 (6) | C20—H20A | 0.9300 |
N6—C24 | 1.341 (7) | C22—C23 | 1.383 (8) |
N6—C25 | 1.422 (7) | C22—H22A | 0.9300 |
C1—C2 | 1.402 (8) | C23—C24 | 1.369 (9) |
C1—H1A | 0.9300 | C23—H23A | 0.9300 |
C2—C3 | 1.364 (8) | C24—H24A | 0.9300 |
C2—H2A | 0.9300 | C25—C26 | 1.374 (8) |
C3—C4 | 1.418 (8) | C25—C30 | 1.408 (8) |
C3—H3A | 0.9300 | C26—C27 | 1.372 (9) |
C4—C12 | 1.395 (7) | C26—H26A | 0.9300 |
C4—C5 | 1.434 (8) | C27—C28 | 1.378 (9) |
C5—C6 | 1.350 (8) | C27—H27A | 0.9300 |
C5—H5A | 0.9300 | C28—C29 | 1.409 (8) |
C6—C7 | 1.425 (7) | C28—H28A | 0.9300 |
C6—H6A | 0.9300 | C29—C30 | 1.391 (8) |
C7—C11 | 1.393 (7) | C29—H29A | 0.9300 |
C7—C8 | 1.413 (7) | P1—F6 | 1.520 (5) |
C8—C9 | 1.364 (7) | P1—F4 | 1.534 (5) |
C8—H8A | 0.9300 | P1—F3 | 1.572 (5) |
C9—C10 | 1.404 (7) | P1—F2 | 1.575 (4) |
C9—H9A | 0.9300 | P1—F1 | 1.584 (5) |
C10—H10A | 0.9300 | P1—F5 | 1.593 (5) |
| | | |
C21—Ir1—C30 | 89.44 (19) | N3—C13—C14 | 110.0 (5) |
C21—Ir1—N3 | 79.7 (2) | N3—C13—H13A | 125.0 |
C30—Ir1—N3 | 94.0 (2) | C14—C13—H13A | 125.0 |
C21—Ir1—N5 | 94.3 (2) | C15—C14—C13 | 106.3 (5) |
C30—Ir1—N5 | 80.0 (2) | C15—C14—H14A | 126.8 |
N3—Ir1—N5 | 171.64 (16) | C13—C14—H14A | 126.8 |
C21—Ir1—N2 | 96.00 (17) | N4—C15—C14 | 107.3 (5) |
C30—Ir1—N2 | 173.09 (18) | N4—C15—H15A | 126.3 |
N3—Ir1—N2 | 91.16 (15) | C14—C15—H15A | 126.3 |
N5—Ir1—N2 | 95.29 (16) | C17—C16—C21 | 123.9 (5) |
C21—Ir1—N1 | 173.97 (17) | C17—C16—N4 | 122.2 (5) |
C30—Ir1—N1 | 96.56 (18) | C21—C16—N4 | 114.0 (4) |
N3—Ir1—N1 | 99.24 (17) | C16—C17—C18 | 118.6 (6) |
N5—Ir1—N1 | 87.33 (17) | C16—C17—H17A | 120.7 |
N2—Ir1—N1 | 78.06 (15) | C18—C17—H17A | 120.7 |
C1—N1—C12 | 118.8 (4) | C19—C18—C17 | 119.8 (5) |
C1—N1—Ir1 | 127.8 (4) | C19—C18—H18A | 120.1 |
C12—N1—Ir1 | 113.1 (3) | C17—C18—H18A | 120.1 |
C10—N2—C11 | 118.2 (4) | C18—C19—C20 | 120.9 (6) |
C10—N2—Ir1 | 128.0 (3) | C18—C19—H19A | 119.6 |
C11—N2—Ir1 | 113.8 (3) | C20—C19—H19A | 119.6 |
C13—N3—N4 | 105.8 (4) | C19—C20—C21 | 121.2 (5) |
C13—N3—Ir1 | 139.0 (4) | C19—C20—H20A | 119.4 |
N4—N3—Ir1 | 114.8 (3) | C21—C20—H20A | 119.4 |
C15—N4—N3 | 110.5 (5) | C16—C21—C20 | 115.7 (5) |
C15—N4—C16 | 133.6 (5) | C16—C21—Ir1 | 115.2 (4) |
N3—N4—C16 | 116.0 (4) | C20—C21—Ir1 | 129.2 (4) |
C22—N5—N6 | 107.0 (5) | N5—C22—C23 | 110.2 (6) |
C22—N5—Ir1 | 138.2 (4) | N5—C22—H22A | 124.9 |
N6—N5—Ir1 | 114.6 (3) | C23—C22—H22A | 124.9 |
C24—N6—N5 | 109.3 (5) | C24—C23—C22 | 105.6 (6) |
C24—N6—C25 | 133.9 (5) | C24—C23—H23A | 127.2 |
N5—N6—C25 | 116.8 (4) | C22—C23—H23A | 127.2 |
N1—C1—C2 | 122.2 (5) | N6—C24—C23 | 107.9 (5) |
N1—C1—H1A | 118.9 | N6—C24—H24A | 126.0 |
C2—C1—H1A | 118.9 | C23—C24—H24A | 126.0 |
C3—C2—C1 | 120.0 (5) | C26—C25—C30 | 123.7 (6) |
C3—C2—H2A | 120.0 | C26—C25—N6 | 122.8 (5) |
C1—C2—H2A | 120.0 | C30—C25—N6 | 113.4 (5) |
C2—C3—C4 | 119.0 (5) | C27—C26—C25 | 119.2 (6) |
C2—C3—H3A | 120.5 | C27—C26—H26A | 120.4 |
C4—C3—H3A | 120.5 | C25—C26—H26A | 120.4 |
C12—C4—C3 | 117.5 (5) | C26—C27—C28 | 119.9 (6) |
C12—C4—C5 | 118.6 (5) | C26—C27—H27A | 120.1 |
C3—C4—C5 | 123.9 (5) | C28—C27—H27A | 120.1 |
C6—C5—C4 | 121.5 (5) | C27—C28—C29 | 120.4 (6) |
C6—C5—H5A | 119.2 | C27—C28—H28A | 119.8 |
C4—C5—H5A | 119.2 | C29—C28—H28A | 119.8 |
C5—C6—C7 | 120.7 (5) | C30—C29—C28 | 121.1 (6) |
C5—C6—H6A | 119.6 | C30—C29—H29A | 119.4 |
C7—C6—H6A | 119.6 | C28—C29—H29A | 119.4 |
C11—C7—C8 | 117.1 (5) | C29—C30—C25 | 115.6 (5) |
C11—C7—C6 | 119.3 (5) | C29—C30—Ir1 | 129.5 (4) |
C8—C7—C6 | 123.6 (5) | C25—C30—Ir1 | 114.9 (4) |
C9—C8—C7 | 119.7 (5) | F6—P1—F4 | 91.8 (5) |
C9—C8—H8A | 120.2 | F6—P1—F3 | 91.8 (4) |
C7—C8—H8A | 120.2 | F4—P1—F3 | 176.4 (4) |
C8—C9—C10 | 119.6 (5) | F6—P1—F2 | 91.0 (3) |
C8—C9—H9A | 120.2 | F4—P1—F2 | 91.5 (3) |
C10—C9—H9A | 120.2 | F3—P1—F2 | 89.1 (3) |
N2—C10—C9 | 122.3 (5) | F6—P1—F1 | 88.2 (3) |
N2—C10—H10A | 118.9 | F4—P1—F1 | 89.8 (3) |
C9—C10—H10A | 118.9 | F3—P1—F1 | 89.6 (3) |
N2—C11—C7 | 122.9 (5) | F2—P1—F1 | 178.4 (3) |
N2—C11—C12 | 117.0 (4) | F6—P1—F5 | 177.3 (4) |
C7—C11—C12 | 120.0 (4) | F4—P1—F5 | 90.9 (4) |
N1—C12—C4 | 122.5 (5) | F3—P1—F5 | 85.5 (3) |
N1—C12—C11 | 117.7 (4) | F2—P1—F5 | 88.8 (3) |
C4—C12—C11 | 119.8 (4) | F1—P1—F5 | 92.0 (4) |
| | | |
C13—N3—N4—C15 | −0.8 (5) | C7—C11—C12—C4 | −0.5 (7) |
Ir1—N3—N4—C15 | 174.3 (3) | N4—N3—C13—C14 | 0.2 (6) |
C13—N3—N4—C16 | 177.8 (4) | Ir1—N3—C13—C14 | −173.0 (4) |
Ir1—N3—N4—C16 | −7.1 (5) | N3—C13—C14—C15 | 0.4 (6) |
C22—N5—N6—C24 | 0.0 (6) | N3—N4—C15—C14 | 1.0 (6) |
Ir1—N5—N6—C24 | 177.0 (4) | C16—N4—C15—C14 | −177.2 (5) |
C22—N5—N6—C25 | 178.9 (5) | C13—C14—C15—N4 | −0.9 (6) |
Ir1—N5—N6—C25 | −4.1 (6) | C15—N4—C16—C17 | 3.6 (9) |
C12—N1—C1—C2 | −0.2 (8) | N3—N4—C16—C17 | −174.6 (5) |
Ir1—N1—C1—C2 | 173.0 (4) | C15—N4—C16—C21 | −177.5 (5) |
N1—C1—C2—C3 | 0.9 (9) | N3—N4—C16—C21 | 4.3 (6) |
C1—C2—C3—C4 | −1.0 (9) | C21—C16—C17—C18 | 0.2 (8) |
C2—C3—C4—C12 | 0.4 (8) | N4—C16—C17—C18 | 179.0 (5) |
C2—C3—C4—C5 | −179.5 (6) | C16—C17—C18—C19 | −0.1 (8) |
C12—C4—C5—C6 | 0.8 (9) | C17—C18—C19—C20 | −0.3 (9) |
C3—C4—C5—C6 | −179.3 (6) | C18—C19—C20—C21 | 0.8 (8) |
C4—C5—C6—C7 | −0.6 (9) | C17—C16—C21—C20 | 0.3 (7) |
C5—C6—C7—C11 | −0.1 (8) | N4—C16—C21—C20 | −178.6 (4) |
C5—C6—C7—C8 | 179.0 (5) | C17—C16—C21—Ir1 | 179.4 (4) |
C11—C7—C8—C9 | −0.5 (8) | N4—C16—C21—Ir1 | 0.5 (5) |
C6—C7—C8—C9 | −179.6 (5) | C19—C20—C21—C16 | −0.8 (7) |
C7—C8—C9—C10 | −0.5 (8) | C19—C20—C21—Ir1 | −179.8 (4) |
C11—N2—C10—C9 | 1.9 (7) | N6—N5—C22—C23 | 0.1 (7) |
Ir1—N2—C10—C9 | −176.7 (4) | Ir1—N5—C22—C23 | −175.8 (4) |
C8—C9—C10—N2 | −0.2 (8) | N5—C22—C23—C24 | −0.1 (7) |
C10—N2—C11—C7 | −3.0 (7) | N5—N6—C24—C23 | −0.1 (7) |
Ir1—N2—C11—C7 | 175.8 (4) | C25—N6—C24—C23 | −178.8 (6) |
C10—N2—C11—C12 | 177.8 (4) | C22—C23—C24—N6 | 0.1 (7) |
Ir1—N2—C11—C12 | −3.4 (5) | C24—N6—C25—C26 | 1.4 (10) |
C8—C7—C11—N2 | 2.3 (7) | N5—N6—C25—C26 | −177.2 (5) |
C6—C7—C11—N2 | −178.5 (5) | C24—N6—C25—C30 | −176.9 (6) |
C8—C7—C11—C12 | −178.5 (5) | N5—N6—C25—C30 | 4.5 (7) |
C6—C7—C11—C12 | 0.7 (8) | C30—C25—C26—C27 | −0.7 (9) |
C1—N1—C12—C4 | −0.5 (8) | N6—C25—C26—C27 | −178.9 (5) |
Ir1—N1—C12—C4 | −174.6 (4) | C25—C26—C27—C28 | 0.7 (9) |
C1—N1—C12—C11 | 180.0 (5) | C26—C27—C28—C29 | −0.3 (9) |
Ir1—N1—C12—C11 | 5.9 (6) | C27—C28—C29—C30 | −0.2 (9) |
C3—C4—C12—N1 | 0.3 (8) | C28—C29—C30—C25 | 0.2 (8) |
C5—C4—C12—N1 | −179.8 (5) | C28—C29—C30—Ir1 | −178.3 (4) |
C3—C4—C12—C11 | 179.9 (5) | C26—C25—C30—C29 | 0.2 (8) |
C5—C4—C12—C11 | −0.2 (8) | N6—C25—C30—C29 | 178.5 (5) |
N2—C11—C12—N1 | −1.7 (7) | C26—C25—C30—Ir1 | 179.0 (4) |
C7—C11—C12—N1 | 179.1 (5) | N6—C25—C30—Ir1 | −2.7 (6) |
N2—C11—C12—C4 | 178.7 (5) | | |
Hydrogen-bond geometry (Å, º) topCg4 and Cg9 are the centroids of rings N3/N4/C15–C13 and
C16–C21,
respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···F6i | 0.93 | 2.57 | 3.184 (7) | 124 |
C9—H9A···F3ii | 0.93 | 2.49 | 3.024 (7) | 117 |
C17—H17A···F4iii | 0.93 | 2.36 | 2.977 (8) | 124 |
C23—H23A···F2iv | 0.93 | 2.53 | 3.383 (8) | 152 |
C24—H24A···F1v | 0.93 | 2.48 | 3.368 (8) | 161 |
C26—H26A···F5v | 0.93 | 2.47 | 3.348 (9) | 158 |
C6—H6A···Cg9vi | 0.93 | 2.58 | 3.501 (6) | 173 |
C29—H29A···Cg4 | 0.93 | 2.98 | 3.688 (7) | 134 |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, −y, z−1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) −x+1/2, −y+1/2, −z; (vi) −x+1/2, y+1/2, −z+1/2. |