research communications
mer-tris{2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl-κN]pyridin-4-yl-κC4}iridium(III) dichloromethane hemisolvate n-hexane hemisolvate
ofaDivision of Science Education & Department of Chemistry, Kangwon National University, Chuncheon 24341, Republic of Korea, and bResearch Institute of Natural Science, Gyeongsang National University, Jinju 52828, Republic of Korea
*Correspondence e-mail: kmpark@gnu.ac.kr, jinhok@kangwon.ac.kr
The 17H11F2N2)3]·0.5CH3(CH2)4CH3·0.5CH2Cl2, comprises one IrIII atom, three 2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl]pyridin-4-yl ligands and half each of an n-hexane and a dichloromethane solvent molecule located about crystallographic inversion centres. The IrIII atom displays a distorted octahedral coordination geometry, having three C,N-chelating 2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl]pyridin-4-yl ligands arranged in a meridional manner. The IrIII ion lies almost in the equatorial plane [deviation = 0.0069 (15) Å]. The average distance [2.041 (3) Å] of Ir—C bonds is slightly shorter than that [2.076 (3) Å] of Ir—N bonds. A variety of intra- and intermolecular C—H⋯F and C—H⋯π hydrogen bonds, as well as intermolecular C—F⋯π interactions, contribute to the stabilization of the molecular and crystal structures, and result in the formation of a two-dimensional network parallel to the ab plane. No interactions between n-hexane solvent molecules and the other components in the title compound are observed.
of the title compound, [Ir(CKeywords: crystal structure; iridium(III) complex; C,N-chelating ligand; mer-C3N3 coordination set; hydrogen bonds; C—F⋯π interactions.
CCDC reference: 1586829
1. Chemical context
Phosphorescent iridium(III) complexes are considered to be excellent candidates for triplet emitters in phosphorescent organic light-emitting diodes (PHOLEDs) because of their high efficiency and high stability (Cho et al., 2016). In particular, iridium(III) complexes with C,N-chelating 2,3′-bipyridine ligands have recently attracted much attention because of their deep-blue emission and easy tuning emission energy upon ligand substitution (Kim et al., 2017). However, many studies of the crystal structures of bipyridine-based iridium(III) derivatives are focused on the different substituents of the C-coordinating pyridine ring (Lee et al., 2014). Examples of iridium(III) complexes with substituents on the N-coordinating pyridine ring are relatively rare compared to those of C-coordination pyridine-functionalized iridium(III) complexes (Lee et al., 2016; Oh et al., 2013). Herein, we report the result of our investigation of the of an iridium(III) complex with an o-tolyl group on the N-coordinating pyridine ring.
2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. The consists of one IrIII atom, three 2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl]pyridin-4-yl ligands, and half each of the n-hexane and dichloromethane solvent molecules located about crystallographic inversion centres. The IrIII atom is six-coordinated by three C,N-chelating 2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl]pyridin-4-yl ligands, forming a distorted octahedral coordination sphere due to narrow ligand bite angles, which range from 78.49 (12) to 80.32 (12)° (Table 1). The pyridyl N atoms of the three ligands are arranged in a mer-configuration around the octahedral IrIII ion (Fig. 1). The equatorial plane is defined by the N1/C1/N5/C18 atoms, the mean deviation from the least-squares plane being 0.0585 (14) Å. The IrIII ion lies almost in the equatorial plane with a deviation of 0.0069 (15) Å. As listed in Table 1, the Ir—C and Ir—N bond lengths in the title compound are within the ranges reported for similar IrIII compounds, for example, mer-[tris[2′,6′-difluoro-2,3′-bipyridinato-k2C4′,N]iridium(III)] (Jung et al., 2012). The average length [2.041 (3) Å] of the Ir—C bonds is slightly shorter than that [2.076 (3) Å] of the Ir—N bonds because of back bonding between the metal and an anionic C atom of the ligand. Within the ligands, the terminal pyridine rings are tilted slightly by 7.2 (2), 6.74 (19), and 6.29 (18)°, respectively, to the N1-, N3-, and N5-containing central pyridine rings, indicating that effective π conjugations of the two pyridine rings occur in the ligands. The terminal phenyl rings, however, are tilted by 51.79 (13), 46.74 (11), and 40.50 (12)° with respect to N1-, N3-, and N5-containing central pyridine rings, respectively. The molecular structure of the IrIII complex is stabilized by weak intramolecular C—H⋯F and C—H⋯N hydrogen bonds (Table 2, shown as dashed lines in Fig. 1).
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3. Supramolecular features
Intermolecular C—H⋯F hydrogen bonds (Table 2, yellow dashed lines in Fig. 2) between adjacent IrIII complexes lead to the formation of one-dimensional chains propagating along the [110] direction. These chains are further interlinked by C13—H⋯π interactions (Table 2, black dashed lines in Fig. 2), resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane. In addition, weak intermolecular C—F⋯π interactions [F2⋯Cg1i = 3.268 (3) Å; F4⋯Cg1iii = 3.411 (3) Å; F4⋯Cg2iii = 3.387 (3) Å; F6⋯Cg5iv = 3.291 (3) Å; Cg1, Cg2, and Cg5 are the centroids of the N1/C6–C10, N3/C23–C27, and N6/C35–C39 rings, respectively; symmetry codes: (i) −x + 2, −y + 1, −z + 1; (iii) −x + 2, −y + 2, −z + 1; (iv) −x + 1, −y + 1, −z + 1] contribute to the stabilization of the Intermolecular C55—H⋯π interactions (Table 2) between the IrIII complexes and the disordered dichloromethane solvent molecules also occur in the of the title compound (not shown in Fig. 2).
No interactions between the n-hexane solvent molecules and the other components of the title compound are observed.
4. Synthesis and crystallization
The title complex was synthesized according to a previous report (Lee et al., 2017). Slow evaporation from a dichloromethane/hexane solution afforded yellow crystals suitable for X-ray crystallography analysis. 1H NMR(400 MHz, CD2Cl2): δ 8.89 (dd, J = 6.2, 1.4 Hz, 1H), 8.30 (dd, J = 8.8, 1.0 Hz, 1H), 8.27–8.21 (m, 2H), 8.01 (d, J = 2.0 Hz, 1H), 7.91 (d, J = 1.2 Hz, 1H), 7.76–7.70 (m, 3H), 7.59 (d, J = 1.6 Hz, 1H), 7.2–6.95 (m, 12H), 6.31 (t, J = 3.2 Hz, 1H), 5.94 (t, J = 2.4 Hz, 1H), 5.83 (t, J = 2.0 Hz, 1H), 1.94 (s, 3H), 1.93 (s, 3H), 1.79 (s, 3H).
5. Refinement
Crystal data, data collection and structure . The dichloromethane molecule is disordered over two sets of sites about an inversion centre with equal occupancy. The C—Cl bond lengths were restrained using the DFIX instructions in SHELXL2014/7 (Sheldrick, 2015). The anisotropic displacement ellipsoid of a chloride atom (Cl1) in the disordered dichloromethane solvent molecule was very elongated and therefore an ISOR restraint was applied for this atom (McArdle, 1995; Sheldrick, 2008). All H atoms were positioned geometrically and refined as riding: C—H = 0.95 Å for Csp2—H, 0.99 Å for methylene C—H, and 0.98 Å for methyl C—H, with Uiso(H) = 1.2–1.5Ueq(C).
details are summarized in Table 3
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Supporting information
CCDC reference: 1586829
https://doi.org/10.1107/S2056989017016759/hg5501sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017016759/hg5501Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).[Ir(C17H11F2N2)3]·0.5C6H14·0.5CH2Cl2 | Z = 2 |
Mr = 1121.58 | F(000) = 1116 |
Triclinic, P1 | Dx = 1.640 Mg m−3 |
a = 12.5753 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.4054 (3) Å | Cell parameters from 9893 reflections |
c = 14.8668 (3) Å | θ = 2.3–28.2° |
α = 117.0678 (5)° | µ = 3.07 mm−1 |
β = 101.9336 (6)° | T = 173 K |
γ = 97.2102 (6)° | Block, yellow |
V = 2270.58 (8) Å3 | 0.42 × 0.23 × 0.21 mm |
Bruker APEXII CCD diffractometer | 10233 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.035 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 28.3°, θmin = 1.6° |
Tmin = 0.532, Tmax = 0.746 | h = −16→16 |
40374 measured reflections | k = −19→19 |
11187 independent reflections | l = −18→19 |
Refinement on F2 | 16 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.047P)2 + 1.7767P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
11187 reflections | Δρmax = 2.38 e Å−3 |
625 parameters | Δρmin = −2.06 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ir1 | 0.80627 (2) | 0.75047 (2) | 0.53831 (2) | 0.01827 (4) | |
F1 | 0.8673 (2) | 0.6415 (2) | 0.8511 (2) | 0.0543 (7) | |
F2 | 1.12093 (19) | 0.59363 (19) | 0.6739 (2) | 0.0429 (6) | |
N1 | 0.9274 (2) | 0.6888 (2) | 0.4727 (2) | 0.0208 (5) | |
N2 | 0.9932 (3) | 0.6203 (2) | 0.7616 (3) | 0.0340 (7) | |
C1 | 0.8725 (2) | 0.6929 (2) | 0.6358 (3) | 0.0212 (6) | |
C2 | 0.8363 (3) | 0.6866 (3) | 0.7161 (3) | 0.0276 (7) | |
H2 | 0.7702 | 0.7072 | 0.7304 | 0.033* | |
C3 | 0.8993 (3) | 0.6498 (3) | 0.7734 (3) | 0.0341 (8) | |
C4 | 1.0248 (3) | 0.6251 (3) | 0.6851 (3) | 0.0298 (7) | |
C5 | 0.9706 (3) | 0.6581 (2) | 0.6176 (3) | 0.0232 (6) | |
C6 | 1.0025 (2) | 0.6582 (2) | 0.5291 (3) | 0.0229 (6) | |
C7 | 1.0955 (3) | 0.6311 (3) | 0.4960 (3) | 0.0303 (7) | |
H7 | 1.1495 | 0.6127 | 0.5356 | 0.036* | |
C8 | 1.1101 (3) | 0.6307 (3) | 0.4064 (3) | 0.0330 (8) | |
H8 | 1.1749 | 0.6136 | 0.3859 | 0.040* | |
C9 | 1.0306 (3) | 0.6551 (3) | 0.3459 (3) | 0.0300 (7) | |
C10 | 0.9416 (3) | 0.6851 (2) | 0.3839 (3) | 0.0252 (7) | |
H10 | 0.8873 | 0.7041 | 0.3450 | 0.030* | |
C11 | 1.0395 (3) | 0.6562 (3) | 0.2480 (3) | 0.0339 (8) | |
C12 | 1.1385 (4) | 0.7141 (4) | 0.2506 (4) | 0.0489 (11) | |
H12 | 1.2007 | 0.7477 | 0.3130 | 0.059* | |
C13 | 1.1479 (5) | 0.7235 (4) | 0.1634 (5) | 0.0611 (14) | |
H13 | 1.2159 | 0.7634 | 0.1662 | 0.073* | |
C14 | 1.0573 (5) | 0.6742 (4) | 0.0724 (4) | 0.0597 (14) | |
H14 | 1.0625 | 0.6816 | 0.0131 | 0.072* | |
C15 | 0.9605 (5) | 0.6148 (4) | 0.0677 (4) | 0.0510 (11) | |
H15 | 0.8996 | 0.5801 | 0.0042 | 0.061* | |
C16 | 0.9490 (4) | 0.6041 (3) | 0.1545 (3) | 0.0388 (9) | |
C17 | 0.8413 (4) | 0.5336 (4) | 0.1405 (4) | 0.0510 (11) | |
H17A | 0.8564 | 0.4994 | 0.1840 | 0.077* | |
H17B | 0.8090 | 0.4780 | 0.0659 | 0.077* | |
H17C | 0.7882 | 0.5775 | 0.1625 | 0.077* | |
F3 | 0.5772 (3) | 0.7962 (2) | 0.2111 (2) | 0.0757 (10) | |
F4 | 0.8327 (2) | 1.08740 (18) | 0.4761 (2) | 0.0466 (6) | |
N3 | 0.9257 (2) | 0.9044 (2) | 0.6254 (2) | 0.0202 (5) | |
N4 | 0.7040 (3) | 0.9417 (3) | 0.3469 (3) | 0.0402 (8) | |
C18 | 0.7582 (3) | 0.8195 (3) | 0.4460 (3) | 0.0242 (6) | |
C19 | 0.6756 (3) | 0.7747 (3) | 0.3490 (3) | 0.0350 (8) | |
H19 | 0.6349 | 0.7013 | 0.3136 | 0.042* | |
C20 | 0.6547 (4) | 0.8392 (4) | 0.3060 (3) | 0.0440 (10) | |
C21 | 0.7826 (3) | 0.9830 (3) | 0.4368 (3) | 0.0321 (8) | |
C22 | 0.8172 (3) | 0.9295 (3) | 0.4913 (3) | 0.0236 (6) | |
C23 | 0.9103 (3) | 0.9743 (2) | 0.5882 (3) | 0.0229 (6) | |
C24 | 0.9824 (3) | 1.0773 (3) | 0.6421 (3) | 0.0299 (7) | |
H24 | 0.9710 | 1.1270 | 0.6179 | 0.036* | |
C25 | 1.0702 (3) | 1.1068 (3) | 0.7304 (3) | 0.0307 (7) | |
H25 | 1.1189 | 1.1771 | 0.7667 | 0.037* | |
C26 | 1.0887 (3) | 1.0351 (3) | 0.7673 (3) | 0.0241 (6) | |
C27 | 1.0117 (2) | 0.9351 (2) | 0.7118 (3) | 0.0212 (6) | |
H27 | 1.0204 | 0.8854 | 0.7365 | 0.025* | |
C28 | 1.1851 (3) | 1.0651 (3) | 0.8603 (3) | 0.0259 (7) | |
C29 | 1.2073 (3) | 1.1663 (3) | 0.9495 (3) | 0.0377 (8) | |
H29 | 1.1586 | 1.2118 | 0.9500 | 0.045* | |
C30 | 1.2990 (4) | 1.2017 (3) | 1.0375 (3) | 0.0457 (10) | |
H30 | 1.3132 | 1.2709 | 1.0976 | 0.055* | |
C31 | 1.3691 (3) | 1.1359 (4) | 1.0369 (3) | 0.0459 (11) | |
H31 | 1.4327 | 1.1599 | 1.0964 | 0.055* | |
C32 | 1.3476 (3) | 1.0351 (3) | 0.9502 (3) | 0.0380 (9) | |
H32 | 1.3965 | 0.9903 | 0.9516 | 0.046* | |
C33 | 1.2560 (3) | 0.9967 (3) | 0.8603 (3) | 0.0293 (7) | |
C34 | 1.2406 (3) | 0.8875 (3) | 0.7682 (3) | 0.0349 (8) | |
H34A | 1.2296 | 0.8922 | 0.7033 | 0.052* | |
H34B | 1.1748 | 0.8377 | 0.7613 | 0.052* | |
H34C | 1.3075 | 0.8611 | 0.7796 | 0.052* | |
F5 | 0.5676 (2) | 0.34823 (18) | 0.2318 (2) | 0.0532 (7) | |
F6 | 0.38409 (17) | 0.55554 (19) | 0.4386 (2) | 0.0466 (6) | |
N5 | 0.6894 (2) | 0.8035 (2) | 0.6117 (2) | 0.0210 (5) | |
N6 | 0.4774 (3) | 0.4534 (3) | 0.3367 (3) | 0.0386 (8) | |
C35 | 0.6786 (3) | 0.6197 (3) | 0.4518 (3) | 0.0232 (6) | |
C36 | 0.6739 (3) | 0.5210 (3) | 0.3648 (3) | 0.0298 (7) | |
H36 | 0.7383 | 0.5075 | 0.3418 | 0.036* | |
C37 | 0.5732 (3) | 0.4448 (3) | 0.3142 (3) | 0.0356 (8) | |
C38 | 0.4829 (3) | 0.5465 (3) | 0.4172 (3) | 0.0324 (8) | |
C39 | 0.5777 (3) | 0.6319 (3) | 0.4795 (3) | 0.0255 (7) | |
C40 | 0.5854 (3) | 0.7342 (3) | 0.5712 (3) | 0.0246 (6) | |
C41 | 0.5035 (3) | 0.7659 (3) | 0.6217 (3) | 0.0325 (8) | |
H41 | 0.4299 | 0.7199 | 0.5929 | 0.039* | |
C42 | 0.5293 (3) | 0.8633 (3) | 0.7127 (3) | 0.0339 (8) | |
H42 | 0.4734 | 0.8836 | 0.7469 | 0.041* | |
C43 | 0.6366 (3) | 0.9335 (3) | 0.7561 (3) | 0.0256 (7) | |
C44 | 0.7122 (3) | 0.8998 (3) | 0.6997 (3) | 0.0243 (6) | |
H44 | 0.7842 | 0.9473 | 0.7245 | 0.029* | |
C45 | 0.6669 (3) | 1.0390 (3) | 0.8546 (3) | 0.0288 (7) | |
C46 | 0.5870 (3) | 1.0993 (3) | 0.8704 (3) | 0.0356 (8) | |
H46 | 0.5167 | 1.0726 | 0.8173 | 0.043* | |
C47 | 0.6081 (4) | 1.1971 (3) | 0.9618 (3) | 0.0428 (9) | |
H47 | 0.5525 | 1.2367 | 0.9713 | 0.051* | |
C48 | 0.7093 (4) | 1.2364 (3) | 1.0383 (3) | 0.0456 (10) | |
H48 | 0.7247 | 1.3038 | 1.1009 | 0.055* | |
C49 | 0.7893 (3) | 1.1773 (3) | 1.0239 (3) | 0.0385 (9) | |
H49 | 0.8592 | 1.2055 | 1.0778 | 0.046* | |
C50 | 0.7712 (3) | 1.0787 (3) | 0.9339 (3) | 0.0311 (7) | |
C51 | 0.8620 (3) | 1.0185 (4) | 0.9291 (3) | 0.0417 (9) | |
H51A | 0.8275 | 0.9409 | 0.8916 | 0.063* | |
H51B | 0.9071 | 1.0410 | 1.0011 | 0.063* | |
H51C | 0.9104 | 1.0347 | 0.8915 | 0.063* | |
C52 | 0.3642 (9) | 0.5534 (10) | 0.1629 (11) | 0.164 (5) | |
H52A | 0.3244 | 0.5125 | 0.1889 | 0.246* | |
H52B | 0.4233 | 0.6141 | 0.2223 | 0.246* | |
H52C | 0.3111 | 0.5806 | 0.1289 | 0.246* | |
C53 | 0.4179 (10) | 0.4784 (9) | 0.0806 (10) | 0.143 (4) | |
H53A | 0.4697 | 0.4498 | 0.1153 | 0.171* | |
H53B | 0.3576 | 0.4164 | 0.0220 | 0.171* | |
C54 | 0.4771 (10) | 0.5289 (7) | 0.0381 (9) | 0.140 (4) | |
H54A | 0.4255 | 0.5619 | 0.0091 | 0.168* | |
H54C | 0.5386 | 0.5887 | 0.0977 | 0.168* | |
C55 | 0.4858 (8) | 1.0429 (5) | 0.4679 (6) | 0.070 (3) | 0.5 |
H55A | 0.5258 | 1.0535 | 0.4212 | 0.084* | 0.5 |
H55B | 0.4281 | 1.0844 | 0.4747 | 0.084* | 0.5 |
Cl1 | 0.4193 (4) | 0.9067 (4) | 0.4086 (4) | 0.245 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.01779 (6) | 0.01590 (6) | 0.02123 (7) | 0.00411 (4) | 0.00436 (4) | 0.00994 (5) |
F1 | 0.0766 (18) | 0.0687 (17) | 0.0456 (15) | 0.0301 (14) | 0.0258 (14) | 0.0449 (14) |
F2 | 0.0406 (12) | 0.0478 (13) | 0.0472 (14) | 0.0263 (10) | 0.0083 (10) | 0.0272 (12) |
N1 | 0.0205 (12) | 0.0147 (12) | 0.0255 (14) | 0.0042 (9) | 0.0059 (10) | 0.0090 (11) |
N2 | 0.0455 (17) | 0.0254 (15) | 0.0286 (16) | 0.0110 (13) | 0.0018 (14) | 0.0147 (13) |
C1 | 0.0210 (13) | 0.0137 (13) | 0.0243 (16) | −0.0001 (11) | 0.0012 (12) | 0.0092 (12) |
C2 | 0.0326 (17) | 0.0247 (16) | 0.0260 (17) | 0.0048 (13) | 0.0065 (14) | 0.0144 (15) |
C3 | 0.049 (2) | 0.0285 (18) | 0.0264 (18) | 0.0083 (16) | 0.0070 (16) | 0.0173 (16) |
C4 | 0.0316 (17) | 0.0196 (15) | 0.0303 (18) | 0.0082 (13) | −0.0005 (14) | 0.0096 (14) |
C5 | 0.0233 (14) | 0.0149 (14) | 0.0267 (16) | 0.0040 (11) | 0.0009 (12) | 0.0096 (13) |
C6 | 0.0216 (14) | 0.0151 (14) | 0.0260 (16) | 0.0038 (11) | 0.0032 (12) | 0.0071 (13) |
C7 | 0.0259 (15) | 0.0233 (16) | 0.036 (2) | 0.0095 (13) | 0.0059 (14) | 0.0102 (15) |
C8 | 0.0266 (16) | 0.0265 (17) | 0.041 (2) | 0.0090 (13) | 0.0154 (15) | 0.0103 (16) |
C9 | 0.0368 (18) | 0.0184 (15) | 0.0346 (19) | 0.0066 (13) | 0.0173 (15) | 0.0103 (15) |
C10 | 0.0331 (16) | 0.0166 (14) | 0.0278 (17) | 0.0061 (12) | 0.0122 (14) | 0.0114 (13) |
C11 | 0.050 (2) | 0.0235 (16) | 0.040 (2) | 0.0162 (15) | 0.0278 (18) | 0.0172 (16) |
C12 | 0.057 (3) | 0.042 (2) | 0.053 (3) | 0.009 (2) | 0.032 (2) | 0.022 (2) |
C13 | 0.071 (3) | 0.057 (3) | 0.083 (4) | 0.018 (3) | 0.053 (3) | 0.044 (3) |
C14 | 0.092 (4) | 0.056 (3) | 0.061 (3) | 0.035 (3) | 0.051 (3) | 0.038 (3) |
C15 | 0.079 (3) | 0.048 (3) | 0.047 (3) | 0.029 (2) | 0.034 (2) | 0.030 (2) |
C16 | 0.057 (2) | 0.0300 (19) | 0.040 (2) | 0.0194 (17) | 0.0244 (19) | 0.0198 (18) |
C17 | 0.062 (3) | 0.052 (3) | 0.040 (2) | 0.010 (2) | 0.013 (2) | 0.026 (2) |
F3 | 0.092 (2) | 0.0570 (17) | 0.0537 (18) | 0.0057 (16) | −0.0304 (16) | 0.0328 (15) |
F4 | 0.0643 (15) | 0.0293 (11) | 0.0506 (15) | 0.0084 (10) | 0.0053 (12) | 0.0290 (11) |
N3 | 0.0202 (11) | 0.0174 (12) | 0.0256 (14) | 0.0064 (9) | 0.0090 (10) | 0.0115 (11) |
N4 | 0.0490 (19) | 0.0394 (18) | 0.0415 (19) | 0.0159 (15) | 0.0069 (16) | 0.0291 (17) |
C18 | 0.0242 (15) | 0.0263 (16) | 0.0272 (17) | 0.0100 (12) | 0.0090 (13) | 0.0159 (14) |
C19 | 0.0382 (19) | 0.0275 (18) | 0.0309 (19) | 0.0045 (14) | −0.0030 (15) | 0.0142 (16) |
C20 | 0.051 (2) | 0.044 (2) | 0.034 (2) | 0.0133 (18) | −0.0040 (18) | 0.0230 (19) |
C21 | 0.0415 (19) | 0.0271 (17) | 0.036 (2) | 0.0128 (15) | 0.0114 (16) | 0.0215 (16) |
C22 | 0.0267 (15) | 0.0240 (15) | 0.0264 (17) | 0.0110 (12) | 0.0096 (13) | 0.0156 (14) |
C23 | 0.0246 (14) | 0.0194 (14) | 0.0286 (17) | 0.0084 (12) | 0.0109 (13) | 0.0132 (14) |
C24 | 0.0330 (17) | 0.0217 (16) | 0.039 (2) | 0.0084 (13) | 0.0110 (15) | 0.0181 (16) |
C25 | 0.0341 (17) | 0.0158 (15) | 0.035 (2) | 0.0017 (13) | 0.0069 (15) | 0.0095 (15) |
C26 | 0.0235 (14) | 0.0197 (15) | 0.0266 (17) | 0.0031 (12) | 0.0092 (13) | 0.0093 (14) |
C27 | 0.0184 (13) | 0.0195 (14) | 0.0249 (16) | 0.0033 (11) | 0.0063 (12) | 0.0108 (13) |
C28 | 0.0231 (14) | 0.0242 (16) | 0.0265 (17) | −0.0021 (12) | 0.0050 (13) | 0.0125 (14) |
C29 | 0.041 (2) | 0.0283 (18) | 0.033 (2) | −0.0028 (15) | 0.0063 (16) | 0.0110 (17) |
C30 | 0.049 (2) | 0.037 (2) | 0.030 (2) | −0.0120 (18) | 0.0022 (18) | 0.0100 (18) |
C31 | 0.037 (2) | 0.052 (3) | 0.038 (2) | −0.0142 (18) | −0.0050 (17) | 0.027 (2) |
C32 | 0.0257 (16) | 0.044 (2) | 0.042 (2) | −0.0016 (15) | 0.0002 (16) | 0.027 (2) |
C33 | 0.0223 (15) | 0.0310 (18) | 0.0323 (19) | −0.0002 (13) | 0.0052 (14) | 0.0167 (16) |
C34 | 0.0271 (16) | 0.0335 (19) | 0.041 (2) | 0.0092 (14) | 0.0068 (15) | 0.0174 (18) |
F5 | 0.0495 (14) | 0.0276 (12) | 0.0478 (15) | −0.0026 (10) | 0.0112 (12) | −0.0048 (11) |
F6 | 0.0240 (10) | 0.0421 (13) | 0.0539 (15) | −0.0029 (9) | 0.0100 (10) | 0.0113 (12) |
N5 | 0.0172 (11) | 0.0211 (13) | 0.0258 (14) | 0.0053 (9) | 0.0044 (10) | 0.0131 (11) |
N6 | 0.0332 (16) | 0.0273 (16) | 0.0378 (18) | −0.0041 (12) | 0.0028 (14) | 0.0082 (14) |
C35 | 0.0220 (14) | 0.0212 (15) | 0.0263 (16) | 0.0028 (11) | 0.0032 (12) | 0.0139 (14) |
C36 | 0.0281 (16) | 0.0230 (16) | 0.0315 (18) | 0.0040 (13) | 0.0058 (14) | 0.0098 (15) |
C37 | 0.0369 (19) | 0.0219 (17) | 0.034 (2) | 0.0007 (14) | 0.0062 (16) | 0.0063 (16) |
C38 | 0.0230 (15) | 0.0324 (18) | 0.038 (2) | 0.0016 (13) | 0.0072 (14) | 0.0162 (17) |
C39 | 0.0247 (15) | 0.0232 (16) | 0.0270 (17) | 0.0042 (12) | 0.0065 (13) | 0.0120 (14) |
C40 | 0.0197 (14) | 0.0234 (15) | 0.0288 (17) | 0.0038 (12) | 0.0054 (13) | 0.0124 (14) |
C41 | 0.0215 (15) | 0.0345 (19) | 0.036 (2) | 0.0012 (13) | 0.0090 (14) | 0.0140 (17) |
C42 | 0.0262 (16) | 0.038 (2) | 0.038 (2) | 0.0101 (14) | 0.0149 (15) | 0.0172 (18) |
C43 | 0.0255 (15) | 0.0276 (16) | 0.0273 (17) | 0.0091 (13) | 0.0081 (13) | 0.0157 (15) |
C44 | 0.0226 (14) | 0.0244 (16) | 0.0284 (17) | 0.0069 (12) | 0.0090 (13) | 0.0143 (14) |
C45 | 0.0320 (16) | 0.0278 (17) | 0.0304 (18) | 0.0093 (13) | 0.0150 (14) | 0.0146 (15) |
C46 | 0.0383 (19) | 0.037 (2) | 0.036 (2) | 0.0157 (16) | 0.0150 (16) | 0.0181 (17) |
C47 | 0.054 (2) | 0.039 (2) | 0.042 (2) | 0.0218 (19) | 0.026 (2) | 0.0185 (19) |
C48 | 0.066 (3) | 0.030 (2) | 0.034 (2) | 0.0056 (19) | 0.024 (2) | 0.0084 (18) |
C49 | 0.040 (2) | 0.037 (2) | 0.0301 (19) | −0.0029 (16) | 0.0104 (16) | 0.0135 (17) |
C50 | 0.0311 (17) | 0.0330 (18) | 0.0300 (18) | 0.0037 (14) | 0.0116 (15) | 0.0164 (16) |
C51 | 0.0281 (18) | 0.056 (3) | 0.036 (2) | 0.0114 (17) | 0.0069 (16) | 0.019 (2) |
C52 | 0.114 (8) | 0.181 (12) | 0.207 (14) | 0.014 (8) | 0.007 (8) | 0.126 (11) |
C53 | 0.183 (11) | 0.123 (8) | 0.161 (11) | 0.051 (8) | 0.048 (9) | 0.100 (8) |
C54 | 0.172 (10) | 0.068 (6) | 0.172 (12) | 0.019 (6) | 0.064 (8) | 0.050 (7) |
C55 | 0.070 (3) | 0.071 (3) | 0.071 (3) | 0.020 (2) | 0.023 (2) | 0.035 (2) |
Cl1 | 0.210 (2) | 0.257 (3) | 0.244 (3) | 0.0489 (18) | 0.0950 (19) | 0.0951 (18) |
Ir1—C35 | 1.991 (3) | C29—C30 | 1.387 (6) |
Ir1—N5 | 2.030 (3) | C29—H29 | 0.9500 |
Ir1—N1 | 2.056 (3) | C30—C31 | 1.372 (7) |
Ir1—C1 | 2.061 (3) | C30—H30 | 0.9500 |
Ir1—C18 | 2.070 (3) | C31—C32 | 1.378 (6) |
Ir1—N3 | 2.143 (3) | C31—H31 | 0.9500 |
F1—C3 | 1.349 (4) | C32—C33 | 1.396 (5) |
F2—C4 | 1.359 (4) | C32—H32 | 0.9500 |
N1—C10 | 1.346 (4) | C33—C34 | 1.496 (5) |
N1—C6 | 1.378 (4) | C34—H34A | 0.9800 |
N2—C4 | 1.307 (5) | C34—H34B | 0.9800 |
N2—C3 | 1.323 (5) | C34—H34C | 0.9800 |
C1—C2 | 1.397 (5) | F5—C37 | 1.352 (4) |
C1—C5 | 1.421 (4) | F6—C38 | 1.352 (4) |
C2—C3 | 1.369 (5) | N5—C44 | 1.346 (4) |
C2—H2 | 0.9500 | N5—C40 | 1.367 (4) |
C4—C5 | 1.389 (5) | N6—C38 | 1.310 (5) |
C5—C6 | 1.453 (5) | N6—C37 | 1.322 (5) |
C6—C7 | 1.393 (5) | C35—C36 | 1.405 (5) |
C7—C8 | 1.378 (5) | C35—C39 | 1.420 (4) |
C7—H7 | 0.9500 | C36—C37 | 1.371 (5) |
C8—C9 | 1.392 (5) | C36—H36 | 0.9500 |
C8—H8 | 0.9500 | C38—C39 | 1.389 (5) |
C9—C10 | 1.386 (5) | C39—C40 | 1.456 (5) |
C9—C11 | 1.490 (5) | C40—C41 | 1.400 (5) |
C10—H10 | 0.9500 | C41—C42 | 1.372 (5) |
C11—C12 | 1.392 (5) | C41—H41 | 0.9500 |
C11—C16 | 1.404 (6) | C42—C43 | 1.401 (5) |
C12—C13 | 1.390 (7) | C42—H42 | 0.9500 |
C12—H12 | 0.9500 | C43—C44 | 1.384 (5) |
C13—C14 | 1.385 (8) | C43—C45 | 1.483 (5) |
C13—H13 | 0.9500 | C44—H44 | 0.9500 |
C14—C15 | 1.366 (7) | C45—C46 | 1.396 (5) |
C14—H14 | 0.9500 | C45—C50 | 1.413 (5) |
C15—C16 | 1.401 (6) | C46—C47 | 1.384 (6) |
C15—H15 | 0.9500 | C46—H46 | 0.9500 |
C16—C17 | 1.502 (6) | C47—C48 | 1.367 (6) |
C17—H17A | 0.9800 | C47—H47 | 0.9500 |
C17—H17B | 0.9800 | C48—C49 | 1.385 (6) |
C17—H17C | 0.9800 | C48—H48 | 0.9500 |
F3—C20 | 1.345 (5) | C49—C50 | 1.386 (5) |
F4—C21 | 1.346 (4) | C49—H49 | 0.9500 |
N3—C27 | 1.343 (4) | C50—C51 | 1.513 (5) |
N3—C23 | 1.367 (4) | C51—H51A | 0.9800 |
N4—C21 | 1.305 (5) | C51—H51B | 0.9800 |
N4—C20 | 1.316 (5) | C51—H51C | 0.9800 |
C18—C19 | 1.392 (5) | C52—C53 | 1.562 (14) |
C18—C22 | 1.429 (4) | C52—H52A | 0.9800 |
C19—C20 | 1.369 (5) | C52—H52B | 0.9800 |
C19—H19 | 0.9500 | C52—H52C | 0.9800 |
C21—C22 | 1.394 (5) | C53—C54 | 1.400 (13) |
C22—C23 | 1.460 (5) | C53—H53A | 0.9900 |
C23—C24 | 1.395 (4) | C53—H53B | 0.9900 |
C24—C25 | 1.377 (5) | C54—C54i | 1.358 (18) |
C24—H24 | 0.9500 | C54—H54A | 0.9900 |
C25—C26 | 1.396 (5) | C54—H54C | 0.9900 |
C25—H25 | 0.9500 | C55—Cl1ii | 1.727 (3) |
C26—C27 | 1.389 (4) | C55—Cl1 | 1.741 (3) |
C26—C28 | 1.483 (5) | C55—H55A | 0.9900 |
C27—H27 | 0.9500 | C55—H55B | 0.9900 |
C28—C29 | 1.395 (5) | Cl1—C55ii | 1.727 (4) |
C28—C33 | 1.410 (5) | ||
C35—Ir1—N5 | 80.32 (12) | C29—C28—C33 | 119.4 (3) |
C35—Ir1—N1 | 98.62 (12) | C29—C28—C26 | 118.1 (3) |
N5—Ir1—N1 | 174.15 (10) | C33—C28—C26 | 122.4 (3) |
C35—Ir1—C1 | 92.12 (12) | C30—C29—C28 | 121.3 (4) |
N5—Ir1—C1 | 94.75 (12) | C30—C29—H29 | 119.4 |
N1—Ir1—C1 | 79.51 (12) | C28—C29—H29 | 119.4 |
C35—Ir1—C18 | 94.00 (13) | C31—C30—C29 | 119.3 (4) |
N5—Ir1—C18 | 88.72 (11) | C31—C30—H30 | 120.3 |
N1—Ir1—C18 | 97.10 (12) | C29—C30—H30 | 120.3 |
C1—Ir1—C18 | 173.39 (11) | C30—C31—C32 | 120.2 (4) |
C35—Ir1—N3 | 170.98 (11) | C30—C31—H31 | 119.9 |
N5—Ir1—N3 | 94.39 (10) | C32—C31—H31 | 119.9 |
N1—Ir1—N3 | 87.37 (10) | C31—C32—C33 | 122.0 (4) |
C1—Ir1—N3 | 95.61 (11) | C31—C32—H32 | 119.0 |
C18—Ir1—N3 | 78.49 (12) | C33—C32—H32 | 119.0 |
C10—N1—C6 | 119.6 (3) | C32—C33—C28 | 117.7 (3) |
C10—N1—Ir1 | 123.6 (2) | C32—C33—C34 | 118.6 (3) |
C6—N1—Ir1 | 116.6 (2) | C28—C33—C34 | 123.6 (3) |
C4—N2—C3 | 114.9 (3) | C33—C34—H34A | 109.5 |
C2—C1—C5 | 117.7 (3) | C33—C34—H34B | 109.5 |
C2—C1—Ir1 | 129.4 (2) | H34A—C34—H34B | 109.5 |
C5—C1—Ir1 | 112.8 (2) | C33—C34—H34C | 109.5 |
C3—C2—C1 | 117.8 (3) | H34A—C34—H34C | 109.5 |
C3—C2—H2 | 121.1 | H34B—C34—H34C | 109.5 |
C1—C2—H2 | 121.1 | C44—N5—C40 | 120.0 (3) |
N2—C3—F1 | 113.6 (3) | C44—N5—Ir1 | 122.9 (2) |
N2—C3—C2 | 126.4 (4) | C40—N5—Ir1 | 117.0 (2) |
F1—C3—C2 | 120.0 (4) | C38—N6—C37 | 114.1 (3) |
N2—C4—F2 | 113.9 (3) | C36—C35—C39 | 116.7 (3) |
N2—C4—C5 | 126.7 (3) | C36—C35—Ir1 | 128.7 (2) |
F2—C4—C5 | 119.4 (3) | C39—C35—Ir1 | 114.4 (2) |
C4—C5—C1 | 116.4 (3) | C37—C36—C35 | 117.6 (3) |
C4—C5—C6 | 126.8 (3) | C37—C36—H36 | 121.2 |
C1—C5—C6 | 116.8 (3) | C35—C36—H36 | 121.2 |
N1—C6—C7 | 118.6 (3) | N6—C37—F5 | 113.9 (3) |
N1—C6—C5 | 112.9 (3) | N6—C37—C36 | 127.4 (4) |
C7—C6—C5 | 128.5 (3) | F5—C37—C36 | 118.6 (3) |
C8—C7—C6 | 120.9 (3) | N6—C38—F6 | 113.8 (3) |
C8—C7—H7 | 119.6 | N6—C38—C39 | 126.6 (3) |
C6—C7—H7 | 119.6 | F6—C38—C39 | 119.5 (3) |
C7—C8—C9 | 120.5 (3) | C38—C39—C35 | 117.4 (3) |
C7—C8—H8 | 119.8 | C38—C39—C40 | 127.0 (3) |
C9—C8—H8 | 119.8 | C35—C39—C40 | 115.6 (3) |
C10—C9—C8 | 116.5 (3) | N5—C40—C41 | 118.9 (3) |
C10—C9—C11 | 119.3 (3) | N5—C40—C39 | 112.5 (3) |
C8—C9—C11 | 124.1 (3) | C41—C40—C39 | 128.6 (3) |
N1—C10—C9 | 123.8 (3) | C42—C41—C40 | 120.1 (3) |
N1—C10—H10 | 118.1 | C42—C41—H41 | 120.0 |
C9—C10—H10 | 118.1 | C40—C41—H41 | 120.0 |
C12—C11—C16 | 119.2 (4) | C41—C42—C43 | 121.2 (3) |
C12—C11—C9 | 119.0 (4) | C41—C42—H42 | 119.4 |
C16—C11—C9 | 121.7 (3) | C43—C42—H42 | 119.4 |
C13—C12—C11 | 121.1 (5) | C44—C43—C42 | 115.9 (3) |
C13—C12—H12 | 119.5 | C44—C43—C45 | 121.8 (3) |
C11—C12—H12 | 119.5 | C42—C43—C45 | 122.3 (3) |
C14—C13—C12 | 119.4 (4) | N5—C44—C43 | 123.7 (3) |
C14—C13—H13 | 120.3 | N5—C44—H44 | 118.1 |
C12—C13—H13 | 120.3 | C43—C44—H44 | 118.1 |
C15—C14—C13 | 120.3 (5) | C46—C45—C50 | 119.1 (3) |
C15—C14—H14 | 119.9 | C46—C45—C43 | 118.1 (3) |
C13—C14—H14 | 119.9 | C50—C45—C43 | 122.7 (3) |
C14—C15—C16 | 121.4 (5) | C47—C46—C45 | 121.4 (4) |
C14—C15—H15 | 119.3 | C47—C46—H46 | 119.3 |
C16—C15—H15 | 119.3 | C45—C46—H46 | 119.3 |
C15—C16—C11 | 118.7 (4) | C48—C47—C46 | 119.7 (4) |
C15—C16—C17 | 117.6 (4) | C48—C47—H47 | 120.2 |
C11—C16—C17 | 123.6 (4) | C46—C47—H47 | 120.2 |
C16—C17—H17A | 109.5 | C47—C48—C49 | 119.6 (4) |
C16—C17—H17B | 109.5 | C47—C48—H48 | 120.2 |
H17A—C17—H17B | 109.5 | C49—C48—H48 | 120.2 |
C16—C17—H17C | 109.5 | C48—C49—C50 | 122.5 (4) |
H17A—C17—H17C | 109.5 | C48—C49—H49 | 118.8 |
H17B—C17—H17C | 109.5 | C50—C49—H49 | 118.8 |
C27—N3—C23 | 119.4 (3) | C49—C50—C45 | 117.7 (3) |
C27—N3—Ir1 | 124.7 (2) | C49—C50—C51 | 118.0 (3) |
C23—N3—Ir1 | 115.9 (2) | C45—C50—C51 | 124.3 (3) |
C21—N4—C20 | 114.6 (3) | C50—C51—H51A | 109.5 |
C19—C18—C22 | 116.7 (3) | C50—C51—H51B | 109.5 |
C19—C18—Ir1 | 129.1 (3) | H51A—C51—H51B | 109.5 |
C22—C18—Ir1 | 114.1 (2) | C50—C51—H51C | 109.5 |
C20—C19—C18 | 118.2 (3) | H51A—C51—H51C | 109.5 |
C20—C19—H19 | 120.9 | H51B—C51—H51C | 109.5 |
C18—C19—H19 | 120.9 | C53—C52—H52A | 109.5 |
N4—C20—F3 | 114.1 (3) | C53—C52—H52B | 109.5 |
N4—C20—C19 | 127.1 (4) | H52A—C52—H52B | 109.5 |
F3—C20—C19 | 118.8 (4) | C53—C52—H52C | 109.5 |
N4—C21—F4 | 113.4 (3) | H52A—C52—H52C | 109.5 |
N4—C21—C22 | 126.5 (3) | H52B—C52—H52C | 109.5 |
F4—C21—C22 | 120.1 (3) | C54—C53—C52 | 114.3 (9) |
C21—C22—C18 | 116.9 (3) | C54—C53—H53A | 108.7 |
C21—C22—C23 | 126.1 (3) | C52—C53—H53A | 108.7 |
C18—C22—C23 | 117.0 (3) | C54—C53—H53B | 108.7 |
N3—C23—C24 | 119.5 (3) | C52—C53—H53B | 108.7 |
N3—C23—C22 | 114.0 (3) | H53A—C53—H53B | 107.6 |
C24—C23—C22 | 126.4 (3) | C54i—C54—C53 | 120.0 (12) |
C25—C24—C23 | 119.9 (3) | C54i—C54—H54A | 107.3 |
C25—C24—H24 | 120.0 | C53—C54—H54A | 107.3 |
C23—C24—H24 | 120.0 | C54i—C54—H54C | 107.3 |
C24—C25—C26 | 121.1 (3) | C53—C54—H54C | 107.3 |
C24—C25—H25 | 119.5 | H54A—C54—H54C | 106.9 |
C26—C25—H25 | 119.5 | Cl1ii—C55—Cl1 | 113.6 (6) |
C27—C26—C25 | 115.9 (3) | Cl1ii—C55—H55A | 108.8 |
C27—C26—C28 | 122.8 (3) | Cl1—C55—H55A | 108.8 |
C25—C26—C28 | 121.4 (3) | Cl1ii—C55—H55B | 108.8 |
N3—C27—C26 | 124.1 (3) | Cl1—C55—H55B | 108.8 |
N3—C27—H27 | 117.9 | H55A—C55—H55B | 107.7 |
C26—C27—H27 | 117.9 | C55ii—Cl1—C55 | 66.4 (6) |
C5—C1—C2—C3 | 1.5 (5) | C22—C23—C24—C25 | −177.0 (3) |
Ir1—C1—C2—C3 | −176.6 (3) | C23—C24—C25—C26 | 0.1 (5) |
C4—N2—C3—F1 | 178.4 (3) | C24—C25—C26—C27 | −2.0 (5) |
C4—N2—C3—C2 | −1.9 (6) | C24—C25—C26—C28 | 178.1 (3) |
C1—C2—C3—N2 | 0.9 (6) | C23—N3—C27—C26 | −0.5 (5) |
C1—C2—C3—F1 | −179.5 (3) | Ir1—N3—C27—C26 | 179.8 (2) |
C3—N2—C4—F2 | −179.5 (3) | C25—C26—C27—N3 | 2.2 (5) |
C3—N2—C4—C5 | 0.4 (5) | C28—C26—C27—N3 | −177.8 (3) |
N2—C4—C5—C1 | 1.9 (5) | C27—C26—C28—C29 | −134.7 (4) |
F2—C4—C5—C1 | −178.2 (3) | C25—C26—C28—C29 | 45.2 (5) |
N2—C4—C5—C6 | −176.6 (3) | C27—C26—C28—C33 | 47.1 (5) |
F2—C4—C5—C6 | 3.4 (5) | C25—C26—C28—C33 | −133.0 (4) |
C2—C1—C5—C4 | −2.7 (4) | C33—C28—C29—C30 | 1.2 (6) |
Ir1—C1—C5—C4 | 175.7 (2) | C26—C28—C29—C30 | −177.0 (3) |
C2—C1—C5—C6 | 175.8 (3) | C28—C29—C30—C31 | −0.2 (6) |
Ir1—C1—C5—C6 | −5.7 (3) | C29—C30—C31—C32 | −0.8 (6) |
C10—N1—C6—C7 | 4.3 (4) | C30—C31—C32—C33 | 0.8 (6) |
Ir1—N1—C6—C7 | −170.7 (2) | C31—C32—C33—C28 | 0.2 (6) |
C10—N1—C6—C5 | −175.1 (3) | C31—C32—C33—C34 | 178.2 (4) |
Ir1—N1—C6—C5 | 9.9 (3) | C29—C28—C33—C32 | −1.2 (5) |
C4—C5—C6—N1 | 175.8 (3) | C26—C28—C33—C32 | 176.9 (3) |
C1—C5—C6—N1 | −2.6 (4) | C29—C28—C33—C34 | −179.0 (3) |
C4—C5—C6—C7 | −3.5 (5) | C26—C28—C33—C34 | −0.9 (5) |
C1—C5—C6—C7 | 178.1 (3) | C39—C35—C36—C37 | −0.2 (5) |
N1—C6—C7—C8 | −2.5 (5) | Ir1—C35—C36—C37 | −176.3 (3) |
C5—C6—C7—C8 | 176.8 (3) | C38—N6—C37—F5 | 179.3 (3) |
C6—C7—C8—C9 | −1.4 (5) | C38—N6—C37—C36 | −0.3 (6) |
C7—C8—C9—C10 | 3.5 (5) | C35—C36—C37—N6 | 1.1 (6) |
C7—C8—C9—C11 | −179.8 (3) | C35—C36—C37—F5 | −178.5 (3) |
C6—N1—C10—C9 | −2.2 (5) | C37—N6—C38—F6 | 178.9 (3) |
Ir1—N1—C10—C9 | 172.4 (2) | C37—N6—C38—C39 | −1.6 (6) |
C8—C9—C10—N1 | −1.7 (5) | N6—C38—C39—C35 | 2.4 (6) |
C11—C9—C10—N1 | −178.6 (3) | F6—C38—C39—C35 | −178.1 (3) |
C10—C9—C11—C12 | 126.0 (4) | N6—C38—C39—C40 | −177.8 (4) |
C8—C9—C11—C12 | −50.7 (5) | F6—C38—C39—C40 | 1.8 (6) |
C10—C9—C11—C16 | −51.4 (5) | C36—C35—C39—C38 | −1.3 (5) |
C8—C9—C11—C16 | 131.9 (4) | Ir1—C35—C39—C38 | 175.4 (3) |
C16—C11—C12—C13 | 1.8 (6) | C36—C35—C39—C40 | 178.8 (3) |
C9—C11—C12—C13 | −175.6 (4) | Ir1—C35—C39—C40 | −4.5 (4) |
C11—C12—C13—C14 | −0.2 (7) | C44—N5—C40—C41 | 1.0 (5) |
C12—C13—C14—C15 | −1.5 (7) | Ir1—N5—C40—C41 | 177.7 (3) |
C13—C14—C15—C16 | 1.5 (7) | C44—N5—C40—C39 | −177.0 (3) |
C14—C15—C16—C11 | 0.2 (6) | Ir1—N5—C40—C39 | −0.3 (4) |
C14—C15—C16—C17 | −177.5 (4) | C38—C39—C40—N5 | −176.8 (3) |
C12—C11—C16—C15 | −1.8 (5) | C35—C39—C40—N5 | 3.1 (4) |
C9—C11—C16—C15 | 175.5 (3) | C38—C39—C40—C41 | 5.5 (6) |
C12—C11—C16—C17 | 175.8 (4) | C35—C39—C40—C41 | −174.6 (3) |
C9—C11—C16—C17 | −6.9 (6) | N5—C40—C41—C42 | −2.6 (5) |
C22—C18—C19—C20 | −1.9 (5) | C39—C40—C41—C42 | 175.0 (4) |
Ir1—C18—C19—C20 | 176.1 (3) | C40—C41—C42—C43 | 1.0 (6) |
C21—N4—C20—F3 | −177.2 (4) | C41—C42—C43—C44 | 2.1 (5) |
C21—N4—C20—C19 | 1.7 (7) | C41—C42—C43—C45 | −179.7 (3) |
C18—C19—C20—N4 | −0.6 (7) | C40—N5—C44—C43 | 2.3 (5) |
C18—C19—C20—F3 | 178.3 (4) | Ir1—N5—C44—C43 | −174.2 (2) |
C20—N4—C21—F4 | 179.1 (4) | C42—C43—C44—N5 | −3.8 (5) |
C20—N4—C21—C22 | −0.2 (6) | C45—C43—C44—N5 | 178.0 (3) |
N4—C21—C22—C18 | −2.2 (6) | C44—C43—C45—C46 | 139.1 (4) |
F4—C21—C22—C18 | 178.5 (3) | C42—C43—C45—C46 | −39.0 (5) |
N4—C21—C22—C23 | 175.5 (4) | C44—C43—C45—C50 | −43.0 (5) |
F4—C21—C22—C23 | −3.7 (6) | C42—C43—C45—C50 | 138.8 (4) |
C19—C18—C22—C21 | 3.2 (5) | C50—C45—C46—C47 | 0.2 (6) |
Ir1—C18—C22—C21 | −175.2 (3) | C43—C45—C46—C47 | 178.2 (4) |
C19—C18—C22—C23 | −174.8 (3) | C45—C46—C47—C48 | 0.4 (6) |
Ir1—C18—C22—C23 | 6.8 (4) | C46—C47—C48—C49 | −0.6 (6) |
C27—N3—C23—C24 | −1.6 (5) | C47—C48—C49—C50 | 0.2 (6) |
Ir1—N3—C23—C24 | 178.2 (2) | C48—C49—C50—C45 | 0.5 (6) |
C27—N3—C23—C22 | 177.4 (3) | C48—C49—C50—C51 | −176.9 (4) |
Ir1—N3—C23—C22 | −2.9 (3) | C46—C45—C50—C49 | −0.7 (5) |
C21—C22—C23—N3 | 179.7 (3) | C43—C45—C50—C49 | −178.5 (3) |
C18—C22—C23—N3 | −2.5 (4) | C46—C45—C50—C51 | 176.5 (4) |
C21—C22—C23—C24 | −1.5 (6) | C43—C45—C50—C51 | −1.3 (6) |
C18—C22—C23—C24 | 176.3 (3) | C52—C53—C54—C54i | −176.7 (15) |
N3—C23—C24—C25 | 1.8 (5) | Cl1ii—C55—Cl1—C55ii | 0.000 (1) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z+1. |
Cg3, Cg4 and Cg6 are the centroids of the N4/C18–C21, N5/C40–C44, and C45–C50 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···F2 | 0.95 | 2.29 | 2.895 (5) | 121 |
C24—H24···F4 | 0.95 | 2.22 | 2.851 (4) | 123 |
C36—H36···F2iii | 0.95 | 2.41 | 3.245 (4) | 146 |
C41—H41···F6 | 0.95 | 2.32 | 2.917 (4) | 121 |
C44—H44···N3 | 0.95 | 2.50 | 3.112 (4) | 122 |
C46—H46···F3ii | 0.95 | 2.50 | 3.067 (5) | 119 |
C13—H13···Cg6iv | 0.95 | 2.98 | 3.777 (7) | 142 |
C55—H55A···Cg4ii | 0.99 | 2.96 | 3.326 (9) | 103 |
C55—H55B···Cg3ii | 0.99 | 3.00 | 3.718 (10) | 131 |
C55—H55B···Cg4ii | 0.99 | 2.78 | 3.326 (10) | 116 |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+2, −z+1. |
Funding information
This study was supported by a 2017 Research Grant from Kangwon National University (No. 520170523).
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