research communications
E)-2-[(phenylimino)methyl]phenolato-κ2N,O}bis[2-(pyridin-2-yl)phenyl-κ2C1,N]iridium(III) dichloromethane monosolvate
of {(aDepartment of Applied Chemistry, Kumoh National Institute of Technology, Gumi 39177, Republic of Korea, and bResearch institute of Natural Science, Gyeongsang National University, Jinju 52828, Republic of Korea
*Correspondence e-mail: kmpark@gnu.ac.kr, hjk@kumoh.ac.kr
In the title compound, [Ir(C11H8N)2(C13H10NO)]·CH2Cl2, the IrIII ion is six-coordinated by two C,N-bidentate 2-(pyridin-2-yl)phenyl ligands and one N,O-bidentate 2-[(phenylimino)methyl]phenolate anion, giving rise to a distorted octahedral environment. The C,N-bidentate ligands, in which the C and N atoms are statistically disordered over two sites and therefore both pairs of C and N atoms are trans and cis relative to each other, are almost perpendicular to each other [the dihedral angle between the least-square planes is 87.00 (4)°]. An intramolecular C—H⋯O hydrogen bond, as well as intermolecular C—H⋯π interactions and π–π interactions, contribute to the stabilization of the molecular and crystal structure.
Keywords: crystal structure; iridium(III) complex; C2N3O coordination set.
CCDC reference: 1480710
1. Chemical context
Cyclometallated IrIII complexes are of great interest due to their excellent phosphorescent properties and applications. In particular, heteroleptic IrIII complexes with imine-based ancillary ligands exhibit aggregation-induced phosphorescent emission (AIPE), resulting in enhanced phosphorescence phenomena in the solid state (Howarth et al., 2014; You et al., 2008; Zhao et al., 2008). To uncover the origin of the intriguing AIPE, it is crucial to analyse the solid-state structures of relevant IrIII complexes besides undertaking spectroscopic and theoretical investigations. Here we report the of the title compound, [Ir(C11H8N)2(C13H10NO)]·CH2Cl2, a heteroleptic IrIII complex with an ancillary salicylimine ligand.
2. Structural commentary
The molecular components of the title structure are shown in Fig. 1. The consists of one IrIII ion, two 2-(pyridin-2-yl)phenyl ligands, and one 2-[(phenylimino)methyl]phenolate anion. The IrIII ion adopts a distorted octahedral coordination geometry, being N,O-chelated by the 2-[(phenylimino)methyl]phenolate ligand and C,N-chelated by two 2-(pyridin-2-yl)phenyl ligands, in which the C and N atoms are equally disordered over two sites and therefore both pairs of C and N atoms are trans and cis relative to each other. The equatorial plane is formed by N1/O1/N2/C12 atoms, the mean deviation from the least-squares plane being 0.002 Å. The IrIII ion is displaced by 0.0481 (9) Å from the equatorial plane towards the axial imino N3 atom. The C,N-bidentate ligands are nearly perpendicular to each other, with a dihedral angle between the least-squares planes of 87.00 (4)°. Within the C,N-bidentate ligands, the dihedral angles between the aromatic rings are 3.70 (10) (between rings C1–C6 and N1/C7–C11) and 7.67 (16)° (between rings C12–C17 and N2/C18–C22). As shown in Table 1, the Ir—C, Ir—N and Ir—O bond lengths of the title compound are within the ranges reported for similar IrIII compounds, e.g. {(E)-2-[(2,6-diisopropylphenylimino)methyl]phenolato-κ2N,O}bis(2-phenylpyridine-κ2C,N)iridium(III) (Howarth et al., 2014), {(E)-2-[(naphthalene-1-ylimino)methyl]phenolato-κ2N,O}bis(2-phenylpyridine-κ2C,N)iridium(III) (Zhao et al., 2008), or {(E)-2-[(phenylimino)methyl]phenolato-κ2N,O}bis[2-(2,4-difluorophenyl)pyridine-κ2C,N]iridium(III) (You et al., 2008).
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3. Supramolecular features
The molecular structure of the title compound is stabilized by an intramolecular C—H⋯O hydrogen bond and intermolecular C—H⋯π interactions between the dichloromethane solvent molecule and the phenyl rings of the C,N-bidentate ligand (Fig. 1 and Table 2). Additionally, intermolecular C—H⋯π interactions (Table 2) and π–π interactions [Cg1⋯Cg1ii = 3.6231 (12) Å and Cg3⋯Cg4 = 3.8873 (17) Å; Cg1, Cg3 and Cg4 are the centroids of the N1/C7–C11, C12–C17 and C30–C35 rings, respectively; symmetry code: (ii) −x + 1, −y + 2, −z + 1] contribute to the stabilization of the (Fig. 2).
4. Synthesis and crystallization
The title compound was prepared according to a reported procedure (You et al., 2008). Single crystals suitable for X-ray diffraction were grown by slow diffusion of n-hexane into a CH2Cl2 solution of the title compound at room temperature.
5. Refinement
Crystal data, data collection and structure . The positions of the N atoms in the 2-(pyridin-2-yl)phenyl unit could not be discriminated from the difference in the displacement parameters, and free of the N and C atoms revealed a lower and higher electron density, respectively, as expected for full occupancy and without disorder. Therefore, atoms N1 and C1A, C11 and N1A, N2 and C2A, and C22 and N2A were refined at the same sites with site occupancy factors of 0.5 using EXYZ/EADP constrains. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for Csp2—H and 0.99 Å for methylene C—H. For all H atoms, Uiso(H) = 1.2Ueq of the parent atom.
details are summarized in Table 3Supporting information
CCDC reference: 1480710
https://doi.org/10.1107/S2056989016008100/wm5290sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016008100/wm5290Isup2.hkl
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).[Ir(C11H8N)2(C13H10NO)]·CH2Cl2 | Z = 2 |
Mr = 781.71 | F(000) = 768 |
Triclinic, P1 | Dx = 1.708 Mg m−3 |
a = 11.8318 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0638 (4) Å | Cell parameters from 25306 reflections |
c = 12.3169 (2) Å | θ = 1.8–28.3° |
α = 98.260 (1)° | µ = 4.60 mm−1 |
β = 114.283 (1)° | T = 130 K |
γ = 101.418 (1)° | Plate, yellow |
V = 1520.15 (6) Å3 | 0.15 × 0.09 × 0.05 mm |
Bruker APEXII CCD diffractometer | 6973 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.020 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | θmax = 28.3°, θmin = 1.8° |
Tmin = 0.614, Tmax = 0.877 | h = −15→15 |
25306 measured reflections | k = −16→16 |
7425 independent reflections | l = −15→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.019 | H-atom parameters constrained |
wR(F2) = 0.047 | w = 1/[σ2(Fo2) + (0.0286P)2 + 0.6203P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.003 |
7425 reflections | Δρmax = 1.45 e Å−3 |
388 parameters | Δρmin = −1.25 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 | 0.61255 (2) | 0.74630 (2) | 0.71617 (2) | 0.01224 (3) | |
Cl1 | 0.23841 (8) | 0.81561 (9) | 0.92075 (9) | 0.0577 (2) | |
Cl2 | 0.13261 (10) | 0.57002 (9) | 0.79287 (9) | 0.0624 (3) | |
C36 | 0.2462 (3) | 0.7010 (3) | 0.8194 (3) | 0.0384 (7) | |
H36A | 0.2294 | 0.7215 | 0.7402 | 0.046* | |
H36B | 0.3341 | 0.6908 | 0.8553 | 0.046* | |
O1 | 0.62551 (15) | 0.70735 (14) | 0.54724 (15) | 0.0181 (3) | |
N1 | 0.58415 (18) | 0.90242 (16) | 0.68412 (17) | 0.0112 (4) | 0.5 |
C1A | 0.58415 (18) | 0.90242 (16) | 0.68412 (17) | 0.0112 (4) | 0.5 |
N2 | 0.62991 (18) | 0.59058 (16) | 0.75448 (18) | 0.0118 (4) | 0.5 |
C2A | 0.62991 (18) | 0.59058 (16) | 0.75448 (18) | 0.0118 (4) | 0.5 |
N3 | 0.82100 (18) | 0.80078 (16) | 0.80795 (17) | 0.0152 (4) | |
C1 | 0.4191 (2) | 0.69766 (19) | 0.6226 (2) | 0.0212 (4) | 0.5 |
N1A | 0.4191 (2) | 0.69766 (19) | 0.6226 (2) | 0.0212 (4) | 0.5 |
C2 | 0.3326 (2) | 0.5863 (2) | 0.5879 (2) | 0.0195 (5) | |
H2 | 0.3656 | 0.5232 | 0.6112 | 0.023* | |
C3 | 0.1996 (2) | 0.5657 (2) | 0.5204 (2) | 0.0233 (5) | |
H3 | 0.1437 | 0.4889 | 0.4971 | 0.028* | |
C4 | 0.1480 (2) | 0.6570 (2) | 0.4865 (2) | 0.0261 (5) | |
H4 | 0.0572 | 0.6428 | 0.4407 | 0.031* | |
C5 | 0.2310 (2) | 0.7689 (2) | 0.5207 (2) | 0.0226 (5) | |
H5 | 0.1968 | 0.8317 | 0.4986 | 0.027* | |
C6 | 0.3646 (2) | 0.78903 (19) | 0.5875 (2) | 0.0169 (4) | |
C7 | 0.4586 (2) | 0.90398 (19) | 0.6250 (2) | 0.0162 (4) | |
C8 | 0.4294 (2) | 1.0079 (2) | 0.6042 (2) | 0.0209 (5) | |
H8 | 0.3417 | 1.0088 | 0.5654 | 0.025* | |
C9 | 0.5277 (2) | 1.1096 (2) | 0.6400 (2) | 0.0230 (5) | |
H9 | 0.5087 | 1.1804 | 0.6249 | 0.028* | |
C10 | 0.6555 (2) | 1.1059 (2) | 0.6987 (2) | 0.0216 (5) | |
H10 | 0.7250 | 1.1744 | 0.7240 | 0.026* | |
C11 | 0.6799 (2) | 1.00236 (19) | 0.7197 (2) | 0.0186 (4) | |
H11 | 0.7671 | 1.0009 | 0.7606 | 0.022* | |
C12 | 0.5938 (2) | 0.76773 (19) | 0.8711 (2) | 0.0200 (4) | 0.5 |
N12A | 0.5938 (2) | 0.76773 (19) | 0.8711 (2) | 0.0200 (4) | 0.5 |
C13 | 0.5758 (2) | 0.8649 (2) | 0.9321 (2) | 0.0188 (4) | |
H13 | 0.5702 | 0.9308 | 0.8983 | 0.023* | |
C14 | 0.5659 (2) | 0.8671 (2) | 1.0412 (2) | 0.0217 (5) | |
H14 | 0.5557 | 0.9348 | 1.0818 | 0.026* | |
C15 | 0.5709 (2) | 0.7710 (2) | 1.0910 (2) | 0.0239 (5) | |
H15 | 0.5613 | 0.7719 | 1.1640 | 0.029* | |
C16 | 0.5899 (2) | 0.6735 (2) | 1.0337 (2) | 0.0217 (5) | |
H16 | 0.5949 | 0.6081 | 1.0682 | 0.026* | |
C17 | 0.6018 (2) | 0.67162 (19) | 0.9253 (2) | 0.0166 (4) | |
C18 | 0.6277 (2) | 0.57502 (19) | 0.8611 (2) | 0.0161 (4) | |
C19 | 0.6551 (2) | 0.4771 (2) | 0.9021 (2) | 0.0209 (5) | |
H19 | 0.6533 | 0.4661 | 0.9762 | 0.025* | |
C20 | 0.6848 (3) | 0.3963 (2) | 0.8351 (2) | 0.0249 (5) | |
H20 | 0.7057 | 0.3305 | 0.8638 | 0.030* | |
C21 | 0.6838 (3) | 0.4120 (2) | 0.7249 (2) | 0.0246 (5) | |
H21 | 0.7021 | 0.3564 | 0.6764 | 0.029* | |
C22 | 0.6558 (2) | 0.5097 (2) | 0.6875 (2) | 0.0200 (5) | |
H22 | 0.6547 | 0.5205 | 0.6122 | 0.024* | |
C23 | 0.7243 (2) | 0.74819 (19) | 0.5292 (2) | 0.0171 (4) | |
C24 | 0.7062 (2) | 0.7315 (2) | 0.4058 (2) | 0.0219 (5) | |
H24 | 0.6237 | 0.6883 | 0.3408 | 0.026* | |
C25 | 0.8046 (3) | 0.7758 (3) | 0.3775 (2) | 0.0288 (6) | |
H25 | 0.7881 | 0.7644 | 0.2938 | 0.035* | |
C26 | 0.9283 (3) | 0.8375 (3) | 0.4708 (3) | 0.0322 (6) | |
H26 | 0.9950 | 0.8709 | 0.4511 | 0.039* | |
C27 | 0.9517 (2) | 0.8488 (3) | 0.5906 (3) | 0.0283 (6) | |
H27 | 1.0370 | 0.8866 | 0.6538 | 0.034* | |
C28 | 0.8532 (2) | 0.8061 (2) | 0.6238 (2) | 0.0198 (5) | |
C29 | 0.8935 (2) | 0.8164 (2) | 0.7526 (2) | 0.0198 (5) | |
H29 | 0.9842 | 0.8371 | 0.8037 | 0.024* | |
C30 | 0.8861 (2) | 0.7980 (2) | 0.9349 (2) | 0.0191 (5) | |
C31 | 0.9382 (2) | 0.7062 (2) | 0.9630 (2) | 0.0254 (5) | |
H31 | 0.9380 | 0.6505 | 0.9000 | 0.030* | |
C32 | 0.9906 (3) | 0.6962 (3) | 1.0839 (3) | 0.0332 (6) | |
H32 | 1.0255 | 0.6332 | 1.1034 | 0.040* | |
C33 | 0.9920 (3) | 0.7784 (3) | 1.1760 (3) | 0.0371 (7) | |
H33 | 1.0267 | 0.7710 | 1.2583 | 0.044* | |
C34 | 0.9430 (3) | 0.8704 (3) | 1.1480 (2) | 0.0330 (6) | |
H34 | 0.9460 | 0.9274 | 1.2118 | 0.040* | |
C35 | 0.8889 (2) | 0.8813 (2) | 1.0276 (2) | 0.0247 (5) | |
H35 | 0.8545 | 0.9448 | 1.0088 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.01277 (5) | 0.01203 (5) | 0.01265 (5) | 0.00444 (3) | 0.00584 (3) | 0.00369 (3) |
Cl1 | 0.0270 (4) | 0.0682 (6) | 0.0609 (6) | 0.0188 (4) | 0.0103 (4) | −0.0109 (5) |
Cl2 | 0.0591 (6) | 0.0585 (6) | 0.0485 (5) | −0.0171 (4) | 0.0221 (4) | 0.0061 (4) |
C36 | 0.0333 (15) | 0.0408 (17) | 0.0376 (17) | 0.0026 (13) | 0.0178 (13) | 0.0052 (13) |
O1 | 0.0181 (8) | 0.0205 (8) | 0.0157 (8) | 0.0045 (6) | 0.0083 (6) | 0.0042 (6) |
N1 | 0.0127 (9) | 0.0112 (8) | 0.0112 (9) | 0.0054 (7) | 0.0055 (7) | 0.0039 (7) |
C1A | 0.0127 (9) | 0.0112 (8) | 0.0112 (9) | 0.0054 (7) | 0.0055 (7) | 0.0039 (7) |
N2 | 0.0122 (9) | 0.0102 (8) | 0.0125 (9) | 0.0036 (7) | 0.0051 (7) | 0.0022 (7) |
C2A | 0.0122 (9) | 0.0102 (8) | 0.0125 (9) | 0.0036 (7) | 0.0051 (7) | 0.0022 (7) |
N3 | 0.0155 (9) | 0.0155 (9) | 0.0145 (9) | 0.0056 (7) | 0.0059 (7) | 0.0044 (7) |
C1 | 0.0213 (11) | 0.0236 (11) | 0.0182 (11) | 0.0057 (9) | 0.0093 (9) | 0.0040 (9) |
N1A | 0.0213 (11) | 0.0236 (11) | 0.0182 (11) | 0.0057 (9) | 0.0093 (9) | 0.0040 (9) |
C2 | 0.0213 (11) | 0.0186 (11) | 0.0177 (11) | 0.0043 (9) | 0.0091 (9) | 0.0032 (9) |
C3 | 0.0194 (11) | 0.0223 (12) | 0.0234 (12) | −0.0007 (9) | 0.0093 (10) | 0.0028 (10) |
C4 | 0.0157 (11) | 0.0313 (13) | 0.0243 (13) | 0.0025 (10) | 0.0050 (10) | 0.0053 (11) |
C5 | 0.0163 (11) | 0.0250 (12) | 0.0244 (12) | 0.0076 (9) | 0.0063 (10) | 0.0067 (10) |
C6 | 0.0164 (10) | 0.0176 (11) | 0.0158 (11) | 0.0044 (8) | 0.0067 (9) | 0.0038 (9) |
C7 | 0.0162 (10) | 0.0181 (11) | 0.0152 (10) | 0.0060 (8) | 0.0072 (9) | 0.0047 (8) |
C8 | 0.0196 (11) | 0.0219 (11) | 0.0219 (12) | 0.0107 (9) | 0.0075 (9) | 0.0066 (9) |
C9 | 0.0267 (12) | 0.0161 (11) | 0.0283 (13) | 0.0093 (9) | 0.0125 (11) | 0.0076 (10) |
C10 | 0.0211 (11) | 0.0160 (11) | 0.0260 (13) | 0.0043 (9) | 0.0097 (10) | 0.0048 (9) |
C11 | 0.0161 (10) | 0.0172 (11) | 0.0211 (11) | 0.0041 (8) | 0.0074 (9) | 0.0048 (9) |
C12 | 0.0166 (10) | 0.0215 (10) | 0.0196 (11) | 0.0051 (8) | 0.0065 (8) | 0.0039 (9) |
N12A | 0.0166 (10) | 0.0215 (10) | 0.0196 (11) | 0.0051 (8) | 0.0065 (8) | 0.0039 (9) |
C13 | 0.0197 (11) | 0.0191 (11) | 0.0207 (11) | 0.0089 (9) | 0.0102 (9) | 0.0064 (9) |
C14 | 0.0207 (11) | 0.0263 (12) | 0.0196 (12) | 0.0111 (10) | 0.0099 (9) | 0.0016 (10) |
C15 | 0.0241 (12) | 0.0348 (14) | 0.0159 (11) | 0.0102 (10) | 0.0110 (10) | 0.0066 (10) |
C16 | 0.0236 (12) | 0.0253 (12) | 0.0195 (12) | 0.0084 (10) | 0.0111 (10) | 0.0093 (10) |
C17 | 0.0146 (10) | 0.0182 (10) | 0.0173 (11) | 0.0052 (8) | 0.0070 (9) | 0.0051 (9) |
C18 | 0.0142 (10) | 0.0156 (10) | 0.0160 (10) | 0.0018 (8) | 0.0060 (8) | 0.0031 (8) |
C19 | 0.0251 (12) | 0.0196 (11) | 0.0211 (12) | 0.0073 (9) | 0.0117 (10) | 0.0089 (9) |
C20 | 0.0324 (13) | 0.0169 (11) | 0.0293 (13) | 0.0111 (10) | 0.0144 (11) | 0.0103 (10) |
C21 | 0.0315 (13) | 0.0180 (11) | 0.0278 (13) | 0.0105 (10) | 0.0159 (11) | 0.0038 (10) |
C22 | 0.0244 (12) | 0.0170 (11) | 0.0207 (12) | 0.0071 (9) | 0.0120 (10) | 0.0036 (9) |
C23 | 0.0203 (11) | 0.0186 (10) | 0.0182 (11) | 0.0101 (9) | 0.0105 (9) | 0.0092 (9) |
C24 | 0.0233 (12) | 0.0289 (13) | 0.0171 (11) | 0.0125 (10) | 0.0096 (10) | 0.0083 (10) |
C25 | 0.0305 (14) | 0.0472 (16) | 0.0221 (13) | 0.0193 (12) | 0.0182 (11) | 0.0163 (12) |
C26 | 0.0246 (13) | 0.0537 (18) | 0.0297 (14) | 0.0149 (12) | 0.0188 (12) | 0.0184 (13) |
C27 | 0.0192 (12) | 0.0420 (15) | 0.0271 (13) | 0.0104 (11) | 0.0121 (10) | 0.0112 (12) |
C28 | 0.0200 (11) | 0.0230 (11) | 0.0206 (12) | 0.0100 (9) | 0.0108 (9) | 0.0072 (9) |
C29 | 0.0165 (11) | 0.0215 (11) | 0.0205 (12) | 0.0071 (9) | 0.0066 (9) | 0.0061 (9) |
C30 | 0.0115 (10) | 0.0251 (12) | 0.0175 (11) | 0.0021 (9) | 0.0047 (9) | 0.0065 (9) |
C31 | 0.0187 (11) | 0.0314 (13) | 0.0266 (13) | 0.0089 (10) | 0.0085 (10) | 0.0115 (11) |
C32 | 0.0225 (13) | 0.0471 (17) | 0.0296 (15) | 0.0105 (12) | 0.0069 (11) | 0.0234 (13) |
C33 | 0.0225 (13) | 0.061 (2) | 0.0204 (13) | 0.0014 (13) | 0.0053 (11) | 0.0167 (13) |
C34 | 0.0240 (13) | 0.0474 (17) | 0.0177 (12) | −0.0006 (12) | 0.0083 (10) | −0.0019 (12) |
C35 | 0.0202 (12) | 0.0308 (13) | 0.0193 (12) | 0.0033 (10) | 0.0086 (10) | 0.0025 (10) |
Ir1—N12A | 1.997 (2) | C11—H11 | 0.9500 |
Ir1—C12 | 1.997 (2) | C12—C13 | 1.400 (3) |
Ir1—N1A | 2.004 (2) | C12—C17 | 1.418 (3) |
Ir1—C1 | 2.004 (2) | N12A—C13 | 1.400 (3) |
Ir1—N2 | 2.0302 (18) | N12A—C17 | 1.418 (3) |
Ir1—C2A | 2.0302 (18) | C13—C14 | 1.393 (3) |
Ir1—N1 | 2.0424 (18) | C13—H13 | 0.9500 |
Ir1—C1A | 2.0424 (18) | C14—C15 | 1.388 (4) |
Ir1—O1 | 2.1409 (16) | C14—H14 | 0.9500 |
Ir1—N3 | 2.1551 (19) | C15—C16 | 1.389 (4) |
Cl1—C36 | 1.769 (3) | C15—H15 | 0.9500 |
Cl2—C36 | 1.749 (3) | C16—C17 | 1.396 (3) |
C36—H36A | 0.9900 | C16—H16 | 0.9500 |
C36—H36B | 0.9900 | C17—C18 | 1.467 (3) |
O1—C23 | 1.295 (3) | C18—C19 | 1.394 (3) |
N1—C11 | 1.352 (3) | C19—C20 | 1.377 (3) |
N1—C7 | 1.365 (3) | C19—H19 | 0.9500 |
C1A—C11 | 1.352 (3) | C20—C21 | 1.394 (4) |
C1A—C7 | 1.365 (3) | C20—H20 | 0.9500 |
N2—C22 | 1.350 (3) | C21—C22 | 1.377 (3) |
N2—C18 | 1.363 (3) | C21—H21 | 0.9500 |
C2A—C22 | 1.350 (3) | C22—H22 | 0.9500 |
C2A—C18 | 1.363 (3) | C23—C24 | 1.422 (3) |
N3—C29 | 1.300 (3) | C23—C28 | 1.433 (3) |
N3—C30 | 1.440 (3) | C24—C25 | 1.380 (4) |
C1—C2 | 1.403 (3) | C24—H24 | 0.9500 |
C1—C6 | 1.417 (3) | C25—C26 | 1.399 (4) |
N1A—C2 | 1.403 (3) | C25—H25 | 0.9500 |
N1A—C6 | 1.417 (3) | C26—C27 | 1.365 (4) |
C2—C3 | 1.392 (3) | C26—H26 | 0.9500 |
C2—H2 | 0.9500 | C27—C28 | 1.416 (3) |
C3—C4 | 1.396 (4) | C27—H27 | 0.9500 |
C3—H3 | 0.9500 | C28—C29 | 1.435 (3) |
C4—C5 | 1.391 (4) | C29—H29 | 0.9500 |
C4—H4 | 0.9500 | C30—C31 | 1.390 (3) |
C5—C6 | 1.398 (3) | C30—C35 | 1.393 (3) |
C5—H5 | 0.9500 | C31—C32 | 1.392 (4) |
C6—C7 | 1.468 (3) | C31—H31 | 0.9500 |
C7—C8 | 1.395 (3) | C32—C33 | 1.387 (5) |
C8—C9 | 1.382 (3) | C32—H32 | 0.9500 |
C8—H8 | 0.9500 | C33—C34 | 1.374 (4) |
C9—C10 | 1.395 (3) | C33—H33 | 0.9500 |
C9—H9 | 0.9500 | C34—C35 | 1.391 (4) |
C10—C11 | 1.372 (3) | C34—H34 | 0.9500 |
C10—H10 | 0.9500 | C35—H35 | 0.9500 |
N12A—Ir1—N1A | 87.97 (9) | C11—C10—H10 | 120.3 |
C12—Ir1—C1 | 87.97 (9) | C9—C10—H10 | 120.3 |
C12—Ir1—N2 | 80.69 (8) | C1A—C11—C10 | 122.4 (2) |
C1—Ir1—N2 | 96.62 (8) | N1—C11—C10 | 122.4 (2) |
N12A—Ir1—C2A | 80.69 (8) | N1—C11—H11 | 118.8 |
N1A—Ir1—C2A | 96.62 (8) | C10—C11—H11 | 118.8 |
C12—Ir1—N1 | 95.15 (8) | C13—C12—C17 | 117.2 (2) |
C1—Ir1—N1 | 80.42 (8) | C13—C12—Ir1 | 128.28 (17) |
N2—Ir1—N1 | 175.02 (7) | C17—C12—Ir1 | 114.53 (16) |
N12A—Ir1—C1A | 95.15 (8) | C13—N12A—C17 | 117.2 (2) |
N1A—Ir1—C1A | 80.42 (8) | C13—N12A—Ir1 | 128.28 (17) |
C2A—Ir1—C1A | 175.02 (7) | C17—N12A—Ir1 | 114.53 (16) |
N12A—Ir1—O1 | 175.01 (7) | C14—C13—C12 | 121.5 (2) |
C12—Ir1—O1 | 175.01 (7) | C14—C13—N12A | 121.5 (2) |
N1A—Ir1—O1 | 90.14 (8) | C14—C13—H13 | 119.3 |
C1—Ir1—O1 | 90.14 (8) | C12—C13—H13 | 119.3 |
N2—Ir1—O1 | 94.95 (7) | C15—C14—C13 | 120.4 (2) |
C2A—Ir1—O1 | 94.95 (7) | C15—C14—H14 | 119.8 |
N1—Ir1—O1 | 89.08 (7) | C13—C14—H14 | 119.8 |
C1A—Ir1—O1 | 89.08 (7) | C14—C15—C16 | 119.7 (2) |
N12A—Ir1—N3 | 94.96 (8) | C14—C15—H15 | 120.2 |
C12—Ir1—N3 | 94.96 (8) | C16—C15—H15 | 120.2 |
N1A—Ir1—N3 | 176.86 (7) | C15—C16—C17 | 120.1 (2) |
C1—Ir1—N3 | 176.86 (7) | C15—C16—H16 | 120.0 |
N2—Ir1—N3 | 84.99 (7) | C17—C16—H16 | 120.0 |
C2A—Ir1—N3 | 84.99 (7) | C16—C17—C12 | 121.2 (2) |
N1—Ir1—N3 | 98.16 (7) | C16—C17—N12A | 121.2 (2) |
C1A—Ir1—N3 | 98.16 (7) | C16—C17—C18 | 124.0 (2) |
O1—Ir1—N3 | 87.04 (7) | C12—C17—C18 | 114.8 (2) |
Cl2—C36—Cl1 | 110.91 (17) | N12A—C17—C18 | 114.8 (2) |
Cl2—C36—H36A | 109.5 | C2A—C18—C19 | 119.9 (2) |
Cl1—C36—H36A | 109.5 | N2—C18—C19 | 119.9 (2) |
Cl2—C36—H36B | 109.5 | C2A—C18—C17 | 113.50 (19) |
Cl1—C36—H36B | 109.5 | N2—C18—C17 | 113.50 (19) |
H36A—C36—H36B | 108.0 | C19—C18—C17 | 126.5 (2) |
C23—O1—Ir1 | 126.57 (15) | C20—C19—C18 | 120.1 (2) |
C11—N1—C7 | 119.07 (19) | C20—C19—H19 | 120.0 |
C11—N1—Ir1 | 124.65 (15) | C18—C19—H19 | 120.0 |
C7—N1—Ir1 | 116.26 (15) | C19—C20—C21 | 119.3 (2) |
C11—C1A—C7 | 119.07 (19) | C19—C20—H20 | 120.3 |
C11—C1A—Ir1 | 124.65 (15) | C21—C20—H20 | 120.3 |
C7—C1A—Ir1 | 116.26 (15) | C22—C21—C20 | 118.7 (2) |
C22—N2—C18 | 119.81 (19) | C22—C21—H21 | 120.6 |
C22—N2—Ir1 | 123.55 (16) | C20—C21—H21 | 120.6 |
C18—N2—Ir1 | 116.30 (15) | C2A—C22—C21 | 122.1 (2) |
C22—C2A—C18 | 119.81 (19) | N2—C22—C21 | 122.1 (2) |
C22—C2A—Ir1 | 123.55 (16) | N2—C22—H22 | 119.0 |
C18—C2A—Ir1 | 116.30 (15) | C21—C22—H22 | 119.0 |
C29—N3—C30 | 115.83 (19) | O1—C23—C24 | 118.1 (2) |
C29—N3—Ir1 | 124.64 (16) | O1—C23—C28 | 125.5 (2) |
C30—N3—Ir1 | 118.36 (14) | C24—C23—C28 | 116.4 (2) |
C2—C1—C6 | 116.8 (2) | C25—C24—C23 | 122.2 (2) |
C2—C1—Ir1 | 128.52 (17) | C25—C24—H24 | 118.9 |
C6—C1—Ir1 | 114.69 (16) | C23—C24—H24 | 118.9 |
C2—N1A—C6 | 116.8 (2) | C24—C25—C26 | 120.7 (2) |
C2—N1A—Ir1 | 128.52 (17) | C24—C25—H25 | 119.7 |
C6—N1A—Ir1 | 114.69 (16) | C26—C25—H25 | 119.7 |
C3—C2—C1 | 121.8 (2) | C27—C26—C25 | 118.9 (2) |
C3—C2—N1A | 121.8 (2) | C27—C26—H26 | 120.6 |
C3—C2—H2 | 119.1 | C25—C26—H26 | 120.6 |
C1—C2—H2 | 119.1 | C26—C27—C28 | 122.3 (2) |
C2—C3—C4 | 120.5 (2) | C26—C27—H27 | 118.9 |
C2—C3—H3 | 119.8 | C28—C27—H27 | 118.9 |
C4—C3—H3 | 119.8 | C27—C28—C23 | 119.4 (2) |
C5—C4—C3 | 119.3 (2) | C27—C28—C29 | 116.2 (2) |
C5—C4—H4 | 120.4 | C23—C28—C29 | 124.2 (2) |
C3—C4—H4 | 120.4 | N3—C29—C28 | 127.8 (2) |
C4—C5—C6 | 120.1 (2) | N3—C29—H29 | 116.1 |
C4—C5—H5 | 119.9 | C28—C29—H29 | 116.1 |
C6—C5—H5 | 119.9 | C31—C30—C35 | 120.3 (2) |
C5—C6—C1 | 121.6 (2) | C31—C30—N3 | 119.0 (2) |
C5—C6—N1A | 121.6 (2) | C35—C30—N3 | 120.6 (2) |
C5—C6—C7 | 123.4 (2) | C30—C31—C32 | 119.7 (3) |
C1—C6—C7 | 115.01 (19) | C30—C31—H31 | 120.2 |
N1A—C6—C7 | 115.01 (19) | C32—C31—H31 | 120.2 |
C1A—C7—C8 | 120.4 (2) | C33—C32—C31 | 120.1 (3) |
N1—C7—C8 | 120.4 (2) | C33—C32—H32 | 120.0 |
C1A—C7—C6 | 113.51 (19) | C31—C32—H32 | 120.0 |
N1—C7—C6 | 113.51 (19) | C34—C33—C32 | 119.9 (3) |
C8—C7—C6 | 126.0 (2) | C34—C33—H33 | 120.0 |
C9—C8—C7 | 120.2 (2) | C32—C33—H33 | 120.0 |
C9—C8—H8 | 119.9 | C33—C34—C35 | 120.9 (3) |
C7—C8—H8 | 119.9 | C33—C34—H34 | 119.5 |
C8—C9—C10 | 118.5 (2) | C35—C34—H34 | 119.5 |
C8—C9—H9 | 120.7 | C34—C35—C30 | 119.1 (2) |
C10—C9—H9 | 120.7 | C34—C35—H35 | 120.4 |
C11—C10—C9 | 119.4 (2) | C30—C35—H35 | 120.4 |
C6—C1—C2—C3 | 1.1 (3) | C13—N12A—C17—C16 | 1.0 (3) |
Ir1—C1—C2—C3 | −178.72 (18) | Ir1—N12A—C17—C16 | −179.75 (18) |
C6—N1A—C2—C3 | 1.1 (3) | C13—N12A—C17—C18 | −176.82 (19) |
Ir1—N1A—C2—C3 | −178.72 (18) | Ir1—N12A—C17—C18 | 2.4 (2) |
C1—C2—C3—C4 | −1.1 (4) | C22—C2A—C18—C19 | 1.5 (3) |
N1A—C2—C3—C4 | −1.1 (4) | Ir1—C2A—C18—C19 | −172.00 (17) |
C2—C3—C4—C5 | 0.2 (4) | C22—C2A—C18—C17 | 178.4 (2) |
C3—C4—C5—C6 | 0.4 (4) | Ir1—C2A—C18—C17 | 4.9 (2) |
C4—C5—C6—C1 | −0.3 (4) | C22—N2—C18—C19 | 1.5 (3) |
C4—C5—C6—N1A | −0.3 (4) | Ir1—N2—C18—C19 | −172.00 (17) |
C4—C5—C6—C7 | 178.8 (2) | C22—N2—C18—C17 | 178.4 (2) |
C2—C1—C6—C5 | −0.5 (3) | Ir1—N2—C18—C17 | 4.9 (2) |
Ir1—C1—C6—C5 | 179.43 (18) | C16—C17—C18—C2A | 177.5 (2) |
C2—C1—C6—C7 | −179.7 (2) | N12A—C17—C18—C2A | −4.7 (3) |
Ir1—C1—C6—C7 | 0.2 (3) | C16—C17—C18—N2 | 177.5 (2) |
C2—N1A—C6—C5 | −0.5 (3) | C12—C17—C18—N2 | −4.7 (3) |
Ir1—N1A—C6—C5 | 179.43 (18) | C16—C17—C18—C19 | −5.8 (4) |
C2—N1A—C6—C7 | −179.7 (2) | C12—C17—C18—C19 | 171.9 (2) |
Ir1—N1A—C6—C7 | 0.2 (3) | N12A—C17—C18—C19 | 171.9 (2) |
C11—C1A—C7—C8 | −1.6 (3) | C2A—C18—C19—C20 | 0.2 (4) |
Ir1—C1A—C7—C8 | 176.93 (17) | N2—C18—C19—C20 | 0.2 (4) |
C11—C1A—C7—C6 | 177.9 (2) | C17—C18—C19—C20 | −176.3 (2) |
Ir1—C1A—C7—C6 | −3.6 (2) | C18—C19—C20—C21 | −1.6 (4) |
C11—N1—C7—C8 | −1.6 (3) | C19—C20—C21—C22 | 1.4 (4) |
Ir1—N1—C7—C8 | 176.93 (17) | C18—C2A—C22—C21 | −1.7 (3) |
C11—N1—C7—C6 | 177.9 (2) | Ir1—C2A—C22—C21 | 171.25 (19) |
Ir1—N1—C7—C6 | −3.6 (2) | C18—N2—C22—C21 | −1.7 (3) |
C5—C6—C7—C1A | −177.0 (2) | Ir1—N2—C22—C21 | 171.25 (19) |
N1A—C6—C7—C1A | 2.2 (3) | C20—C21—C22—C2A | 0.3 (4) |
C5—C6—C7—N1 | −177.0 (2) | C20—C21—C22—N2 | 0.3 (4) |
C1—C6—C7—N1 | 2.2 (3) | Ir1—O1—C23—C24 | −167.35 (15) |
C5—C6—C7—C8 | 2.4 (4) | Ir1—O1—C23—C28 | 14.9 (3) |
C1—C6—C7—C8 | −178.4 (2) | O1—C23—C24—C25 | 177.4 (2) |
N1A—C6—C7—C8 | −178.4 (2) | C28—C23—C24—C25 | −4.6 (3) |
C1A—C7—C8—C9 | 2.1 (4) | C23—C24—C25—C26 | 1.5 (4) |
N1—C7—C8—C9 | 2.1 (4) | C24—C25—C26—C27 | 2.8 (4) |
C6—C7—C8—C9 | −177.3 (2) | C25—C26—C27—C28 | −3.7 (4) |
C7—C8—C9—C10 | −1.2 (4) | C26—C27—C28—C23 | 0.5 (4) |
C8—C9—C10—C11 | −0.2 (4) | C26—C27—C28—C29 | 175.6 (3) |
C7—C1A—C11—C10 | 0.2 (3) | O1—C23—C28—C27 | −178.6 (2) |
Ir1—C1A—C11—C10 | −178.21 (18) | C24—C23—C28—C27 | 3.6 (3) |
C7—N1—C11—C10 | 0.2 (3) | O1—C23—C28—C29 | 6.7 (4) |
Ir1—N1—C11—C10 | −178.21 (18) | C24—C23—C28—C29 | −171.1 (2) |
C9—C10—C11—C1A | 0.8 (4) | C30—N3—C29—C28 | 170.2 (2) |
C9—C10—C11—N1 | 0.8 (4) | Ir1—N3—C29—C28 | 2.8 (3) |
C17—C12—C13—C14 | −0.1 (3) | C27—C28—C29—N3 | 168.6 (2) |
Ir1—C12—C13—C14 | −179.18 (18) | C23—C28—C29—N3 | −16.6 (4) |
C17—N12A—C13—C14 | −0.1 (3) | C29—N3—C30—C31 | −66.6 (3) |
Ir1—N12A—C13—C14 | −179.18 (18) | Ir1—N3—C30—C31 | 101.6 (2) |
C12—C13—C14—C15 | −1.4 (4) | C29—N3—C30—C35 | 117.9 (2) |
N12A—C13—C14—C15 | −1.4 (4) | Ir1—N3—C30—C35 | −73.9 (2) |
C13—C14—C15—C16 | 2.0 (4) | C35—C30—C31—C32 | 1.5 (4) |
C14—C15—C16—C17 | −1.1 (4) | N3—C30—C31—C32 | −174.0 (2) |
C15—C16—C17—C12 | −0.5 (4) | C30—C31—C32—C33 | −0.7 (4) |
C15—C16—C17—N12A | −0.5 (4) | C31—C32—C33—C34 | −0.8 (4) |
C15—C16—C17—C18 | 177.2 (2) | C32—C33—C34—C35 | 1.5 (4) |
C13—C12—C17—C16 | 1.0 (3) | C33—C34—C35—C30 | −0.6 (4) |
Ir1—C12—C17—C16 | −179.75 (18) | C31—C30—C35—C34 | −0.9 (4) |
C13—C12—C17—C18 | −176.82 (19) | N3—C30—C35—C34 | 174.6 (2) |
Ir1—C12—C17—C18 | 2.4 (2) |
Cg2 and Cg3 are the centroids of the C1–C6 and C12–C17 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O1 | 0.95 | 2.54 | 3.132 (3) | 121 |
C21—H21···Cg2i | 0.95 | 2.90 | 3.658 (3) | 138 |
C36—H36A···Cg2 | 0.99 | 2.62 | 3.444 (4) | 140 |
C36—H36B···Cg3 | 0.99 | 2.59 | 3.498 (4) | 153 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
This work was supported by Kumoh National Institute of Technology.
References
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Howarth, A. J., Patia, R., Davies, D. L., Lelj, F., Wolf, M. O. & Singh, K. (2014). Eur. J. Inorg. Chem. pp. 3657–3664. CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
You, Y., Huh, H. S., Kim, K. S., Lee, S. W., Kim, D. & Park, S. Y. (2008). Chem. Commun. pp. 3998–4000. CSD CrossRef Google Scholar
Zhao, Q., Li, L., Li, F., Yu, M., Liu, Z., Yi, T. & Huang, C. (2008). Chem. Commun. pp. 685–687. CSD CrossRef Google Scholar
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