metal-organic compounds
[(1,2,5,6-η)-Cycloocta-1,5-diene](4-isopropyl-1-methyl-1,2,4-triazol-5-ylidene)(tricyclohexylphosphane-κP)iridium(I) tetrafluoridoborate dichloromethane monosolvate
aDepartment of Chemistry, Millersville University, Millersville, PA 17551, USA, and bDepartment of Chemistry and Biochemistry, The University of Arizona, Tuscon, AZ, 85716, USA
*Correspondence e-mail: edward.rajaseelan@millersville.edu
The title compound, [Ir(C8H12)(C6H11N3)(C18H33P)]BF4·CH2Cl2, a triazole-based N-heterocyclic carbene iridium(I) cationic complex with a tetrafluoridoborate counter-anion, crystallizes with one dichloromethane solvent molecule per formula unit. The IrI atom of the cationic complex has a distorted square-planar coordination environment, defined by a bidentate cycloocta-1,5-diene (COD) ligand, an N-heterocyclic carbene, and a tricyclohexylphosphane ligand. The complex crystallizes in a C-centered monoclinic and has an unusually high number of eight formula units.
Keywords: crystal structure; iridium; N-heterocyclic carbenes.
CCDC reference: 2184164
Structure description
N-heterocyclic ; de Frémont et al., 2009; Díez-Gonzáles et al., 2009; Rovis & Nolan, 2013; Ruff et al., 2016; Zuo et al., 2014). Their catalytic activities in the transfer hydrogenation of and have also been studied and reported (Albrecht et al., 2002; Gnanamgari et al., 2007). The NHC ligands can be tuned sterically and electronically by having different substituents on the nitrogen atoms (Gusev, 2009). Many imidazole- and triazole-based NHC rhodium and iridium complexes have been synthesized and structurally characterized (Herrmann et al., 2006; Wang & Lin, 1998; Chianese et al., 2004). As part of our ongoing research, we continue to synthesize new imidazole- and triazole-based NHC complexes of rhodium and iridium to study the effect of different substituents on the NHCs and co-ligands coordinating to the transition metal in transfer hydrogenation reactions (Nichol et al., 2009, 2010, 2011, 2012; Idrees et al., 2017a,b; Rood et al., 2021; Rushlow et al., 2021; Newman et al., 2021; Castaldi et al., 2021).
(NHCs) have emerged as excellent spectator ligands in (Cazin, 2013The molecular structure of the title complex, [Ir(C8H12)(C18H33P)(C6H11N3)][BF4]·CH2Cl2 (4), comprises an IrI cationic complex, a tetrafluoridoborate counter-anion, and a CH2Cl2 solvent molecule, as illustrated in Fig. 1. The coordination sphere around the IrI atom, formed by the bidentate (1,2,5,6-η)-cycloocta-1,5-diene (COD), NHC, and tricyclohexylphosphane ligands, results in a distorted square-planar shape. The N1—C19(NHC)—N3 bond angle in the triazole-based carbene is 102.8 (2)° deviating from the expected 120° for the sp2-hybridized carbon atom. Other selected bond lengths and angles in the structure are: Ir1—C19(NHC) = 2.035 (3) Å, Ir1—P1 = 2.3732 (7) Å, and C19—Ir1—P1 = 94.07 (7)°. The cyclohexyl rings of the tricyclohexylphosphane ligand are all in the expected chair conformation, with the mean planes of the cyclohexyl rings forming dihedral angles of 59.70 (15), 61.77 (14), and 83.20 (15)°. The crystal packing diagram of the title compound is shown in Fig. 2. Several close C—H⋯F contacts stabilizing the orientation of the [BF4]− group with the iridium(I) complex and dichloromethane solvate are reported in Table 1. These non-classical hydrogen-bonds are shown as green dotted lines in Fig. 2.
Synthesis and crystallization
1-Methyl-1,2,4 triazole (1) was purchased from Matrix Scientific. All other compounds used in the syntheses as shown in Fig. 3 were obtained from Sigma-Aldrich and Strem and used as received. All subsequent synthesis procedures were performed under nitrogen using reagent grade solvents, which were used as received without further purification. NMR spectra were recorded at room temperature in CDCl3 on a 400 MHz Varian spectrometer (operating at 162 MHz for 31P) and referenced to the residual solvent peak (δ in ppm).
4-Isopropyl-1-methyl-1,2,4-triazolium bromide (2): 1-methyl-1,2,4-triazole (1) (5.01 g, 60.28 mmol) and isopropyl bromide (10.48 g, 85.2 mmol) were added to toluene (20 ml), and the mixture was refluxed for 48 h. Once cooled, the liquid was decanted, the white solid product that had formed was washed with ether, filtered, and dried. Yield: 2.48 g (20%). 1H NMR: δ 11.79 (s, 1 H, N—C5H—N), 8.97 (s, 1 H, N—C3H—N), 5.83 [m, 1 H, CH(CH3)2], 4.29 (s, 3 H, N—CH3), 1.73 [d, 6 H, CH(CH3)2]. 13C NMR: δ 143.52 (N—CH—N), 142.65 (N—CH—N), 53.32 [CH(CH3)2], 39.62 (N—CH3), 23.21[CH(CH3)2].
[(1,2,5,6-η)-Cycloocta-1,5-diene](4-isopropyl-1-methyl-1,2,4-triazol-5-ylidene) chloroiridium (3): 4-ispopropyl-1-methyl-1,2,4 triazolium bromide (2) (0.061g, 0.300 mmol), Ag2O (0.035 g, 0.149 mmol), and 10 ml of CH2Cl2 were added to an oven-dried flask and stirred under N2 in the dark for 90 min. The mixture was filtered through Celite into [Ir(COD)Cl]2 (0.100 g, 0.149 mmol) and stirred in the dark for 90 min. The resulting mixture was filtered through Celite and the solvent was removed under reduced pressure. The red solid product was washed with pentane and allowed to dry overnight under vacuum. Yield: 0.139 g (100%). 1H NMR: δ 7.91 (s, 1 H, N—C3H—N), 5.52 [m, 1 H, CH(CH3)2], 4.74, 4.76 (m, 4 H, CH of COD) 4.09 (s, 3 H, CH3—N), 2.96, 2.30, 2.17, 1.86 (m, 8 H, CH2 of COD),1.28 [m, 6 H, CH(CH3)2]. 13C NMR: δ 181.21 (Ir—C), 138.79 (N—CH—N), 86.59, 85.96 (CH of COD), 51.73 [CH(CH3)2], 40.52 (N—CH3), 33.72, 33.28, 29.65, 29.24 (CH2 of COD), 24.17, 23.31[CH(CH3)2].
[(1,2,5,6-η)-Cycloocta-1,5-diene](4-isopropyl-1-methyl-1,2,4-triazol-5-ylidene)(tricyclohexylphosphane)iridium(I) tetrafluoridoborate (4): Tricyclohexylphosphane (0.085 g, 0.308 mmol) and AgBF4 (0.059 g 0.308 mmol) were added to an oven-dried flask containing complex 3 (0.140 g, 0.308 mmol) in 10 ml of CH2Cl2, and stirred under N2 in the dark for 90 mins. The mixture was filtered through Celite and the solvent was removed under reduced pressure. The bright-red solid was washed with pentane and dried under vacuum. Yield: 0.214 g (100%). 1H NMR: δ 8.58 (s, 1 H, N—C3H—N), 5.29 [m, 1 H, CH(CH3)2], 4.38, 3.99 (m, 4 H, CH of COD), 4.05 (s, 3 H, CH3—N), 2.27–0.86 CH2 of COD and cyclohexyl, 1.21 [m, 6 H, CH(CH3)2]. 13C NMR: δ 178.26 (Ir—C), 142.01 (N—CH—N), 77.30, 77.19, 76.98, 77.66 (CH of COD), 54.23 [CH(CH3)2], 40.51 (N—CH3), 34.94, 34.10, 30.36, 30.14 (CH2 of COD), 27.79–25.92 (CH2 of cyclohexyl), 24.50, 22.86 [CH(CH3)2]. 31P: δ 39.81.
The title compound (4) was crystallized by slow diffusion of pentane into a CH2Cl2 solution.
Refinement
Crystal data, data collection, and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 2184164
https://doi.org/10.1107/S241431462200685X/wm4168sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462200685X/wm4168Isup2.hkl
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).[Ir(C8H12)(C6H11N3)(C18H33P)]BF4·CH2Cl2 | F(000) = 3552 |
Mr = 877.70 | Dx = 1.631 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 35.832 (5) Å | Cell parameters from 9640 reflections |
b = 10.2608 (15) Å | θ = 2.5–27.1° |
c = 22.034 (3) Å | µ = 3.98 mm−1 |
β = 118.095 (3)° | T = 100 K |
V = 7146.7 (17) Å3 | Plate, clear light pink |
Z = 8 | 0.27 × 0.11 × 0.07 mm |
Bruker APEXII CCD diffractometer | 7086 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.061 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 27.2°, θmin = 1.3° |
Tmin = 0.555, Tmax = 0.746 | h = −45→46 |
151141 measured reflections | k = −13→13 |
7958 independent reflections | l = −28→27 |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.052 | w = 1/[σ2(Fo2) + (0.0234P)2 + 23.3944P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.004 |
7958 reflections | Δρmax = 1.83 e Å−3 |
409 parameters | Δρmin = −0.69 e Å−3 |
1 restraint |
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 | ||
Ir1 | 0.37947 (2) | 0.36533 (2) | 0.66268 (2) | 0.01104 (4) | |
P1 | 0.39296 (2) | 0.44263 (6) | 0.77266 (3) | 0.01133 (12) | |
Cl2S | 0.40895 (2) | 1.15711 (8) | 0.42611 (4) | 0.02888 (16) | |
Cl1S | 0.32454 (3) | 1.06150 (10) | 0.33196 (5) | 0.0487 (2) | |
F4 | 0.33674 (6) | 0.95299 (19) | 0.51922 (11) | 0.0381 (5) | |
N1 | 0.29702 (7) | 0.2187 (2) | 0.62775 (11) | 0.0165 (5) | |
N3 | 0.28433 (7) | 0.4161 (2) | 0.59694 (11) | 0.0148 (4) | |
F2 | 0.34763 (10) | 0.7797 (2) | 0.46717 (12) | 0.0665 (8) | |
F3 | 0.40161 (8) | 0.8615 (2) | 0.56303 (16) | 0.0674 (8) | |
C19 | 0.31703 (8) | 0.3312 (2) | 0.63092 (13) | 0.0140 (5) | |
N2 | 0.25339 (7) | 0.2280 (2) | 0.59297 (12) | 0.0206 (5) | |
F1 | 0.34932 (10) | 0.7542 (3) | 0.56918 (13) | 0.0762 (9) | |
C1 | 0.41482 (8) | 0.6111 (2) | 0.79339 (13) | 0.0133 (5) | |
H1 | 0.409073 | 0.642915 | 0.831081 | 0.016* | |
C7 | 0.43280 (8) | 0.3465 (2) | 0.84639 (13) | 0.0124 (5) | |
H7 | 0.460500 | 0.366415 | 0.847728 | 0.015* | |
C13 | 0.34343 (8) | 0.4505 (2) | 0.78081 (13) | 0.0141 (5) | |
H13 | 0.320559 | 0.472551 | 0.733675 | 0.017* | |
C6 | 0.46335 (8) | 0.6214 (2) | 0.82126 (11) | 0.0148 (5) | |
H6A | 0.478006 | 0.573466 | 0.865319 | 0.018* | |
H6B | 0.471149 | 0.580549 | 0.788106 | 0.018* | |
C12 | 0.42781 (8) | 0.1971 (2) | 0.83749 (13) | 0.0150 (5) | |
H12A | 0.401002 | 0.169971 | 0.836486 | 0.018* | |
H12B | 0.426543 | 0.171706 | 0.793210 | 0.018* | |
C2 | 0.38961 (8) | 0.7009 (2) | 0.73112 (14) | 0.0163 (5) | |
H2A | 0.391499 | 0.666680 | 0.690660 | 0.020* | |
H2B | 0.359446 | 0.700389 | 0.720122 | 0.020* | |
C21 | 0.31663 (9) | 0.0937 (3) | 0.65715 (15) | 0.0221 (6) | |
H21A | 0.310806 | 0.031417 | 0.620001 | 0.033* | |
H21B | 0.304984 | 0.060358 | 0.686421 | 0.033* | |
H21C | 0.347268 | 0.105237 | 0.684765 | 0.033* | |
C25 | 0.44696 (8) | 0.3374 (3) | 0.69905 (14) | 0.0167 (5) | |
H25 | 0.465054 | 0.353427 | 0.749386 | 0.020* | |
C8 | 0.43839 (8) | 0.3886 (3) | 0.91742 (13) | 0.0158 (5) | |
H8A | 0.443145 | 0.483866 | 0.922958 | 0.019* | |
H8B | 0.412273 | 0.368539 | 0.920393 | 0.019* | |
C23 | 0.26856 (9) | 0.5766 (3) | 0.50488 (14) | 0.0224 (6) | |
H23A | 0.237706 | 0.572301 | 0.485058 | 0.034* | |
H23B | 0.278255 | 0.509140 | 0.484080 | 0.034* | |
H23C | 0.276744 | 0.662600 | 0.495709 | 0.034* | |
C11 | 0.46487 (9) | 0.1279 (2) | 0.89647 (13) | 0.0158 (5) | |
H11A | 0.460147 | 0.032577 | 0.891400 | 0.019* | |
H11B | 0.491179 | 0.147151 | 0.893945 | 0.019* | |
C9 | 0.47579 (9) | 0.3179 (3) | 0.97497 (13) | 0.0172 (5) | |
H9A | 0.478191 | 0.343834 | 1.019954 | 0.021* | |
H9B | 0.502223 | 0.343751 | 0.974335 | 0.021* | |
C18 | 0.34015 (9) | 0.5541 (3) | 0.82801 (14) | 0.0193 (6) | |
H18A | 0.346227 | 0.640997 | 0.815137 | 0.023* | |
H18B | 0.361480 | 0.536406 | 0.876193 | 0.023* | |
C20 | 0.24711 (8) | 0.3498 (3) | 0.57501 (14) | 0.0185 (6) | |
H20 | 0.219940 | 0.388176 | 0.549698 | 0.022* | |
C26 | 0.43439 (8) | 0.4508 (3) | 0.65866 (11) | 0.0168 (5) | |
H26 | 0.444608 | 0.531772 | 0.687085 | 0.020* | |
C32 | 0.45361 (9) | 0.2064 (3) | 0.67450 (14) | 0.0192 (6) | |
H32A | 0.452366 | 0.137592 | 0.705011 | 0.023* | |
H32B | 0.482169 | 0.203978 | 0.677949 | 0.023* | |
C4 | 0.45350 (9) | 0.8468 (3) | 0.76842 (15) | 0.0197 (6) | |
H4A | 0.463430 | 0.938160 | 0.778773 | 0.024* | |
H4B | 0.459077 | 0.815192 | 0.731018 | 0.024* | |
C14 | 0.33119 (8) | 0.3160 (3) | 0.79709 (14) | 0.0160 (5) | |
H14A | 0.332548 | 0.250194 | 0.765315 | 0.019* | |
H14B | 0.351701 | 0.290493 | 0.844618 | 0.019* | |
C30 | 0.37730 (9) | 0.2283 (3) | 0.58452 (13) | 0.0177 (5) | |
H30 | 0.355490 | 0.158421 | 0.572558 | 0.021* | |
C10 | 0.47030 (9) | 0.1703 (3) | 0.96657 (14) | 0.0179 (5) | |
H10A | 0.495397 | 0.126619 | 1.003385 | 0.022* | |
H10B | 0.445176 | 0.143510 | 0.971083 | 0.022* | |
C16 | 0.28327 (10) | 0.4211 (3) | 0.83670 (16) | 0.0258 (6) | |
H16A | 0.253819 | 0.424430 | 0.829333 | 0.031* | |
H16B | 0.301900 | 0.397242 | 0.885332 | 0.031* | |
C22 | 0.28870 (9) | 0.5548 (3) | 0.58210 (14) | 0.0174 (5) | |
H22 | 0.319547 | 0.575082 | 0.602327 | 0.021* | |
C15 | 0.28669 (9) | 0.3177 (3) | 0.78991 (16) | 0.0231 (6) | |
H15A | 0.265871 | 0.336313 | 0.741537 | 0.028* | |
H15B | 0.280048 | 0.231093 | 0.802164 | 0.028* | |
C29 | 0.36078 (9) | 0.3470 (3) | 0.55232 (13) | 0.0181 (6) | |
H29 | 0.329489 | 0.346033 | 0.521651 | 0.022* | |
C5 | 0.47773 (9) | 0.7629 (3) | 0.83248 (14) | 0.0187 (6) | |
H5A | 0.508287 | 0.766504 | 0.846153 | 0.022* | |
H5B | 0.473836 | 0.799412 | 0.870709 | 0.022* | |
C31 | 0.42068 (9) | 0.1769 (3) | 0.60030 (14) | 0.0205 (6) | |
H31A | 0.429634 | 0.217383 | 0.568440 | 0.025* | |
H31B | 0.419020 | 0.081538 | 0.592699 | 0.025* | |
C3 | 0.40612 (9) | 0.8415 (3) | 0.74491 (14) | 0.0192 (6) | |
H3A | 0.390892 | 0.893617 | 0.702391 | 0.023* | |
H3B | 0.400367 | 0.880384 | 0.780789 | 0.023* | |
C24 | 0.26977 (9) | 0.6436 (3) | 0.61597 (14) | 0.0218 (6) | |
H24A | 0.275798 | 0.734726 | 0.610367 | 0.033* | |
H24B | 0.282248 | 0.622876 | 0.665071 | 0.033* | |
H24C | 0.239084 | 0.630457 | 0.594223 | 0.033* | |
C28 | 0.38413 (9) | 0.4454 (3) | 0.53192 (14) | 0.0221 (6) | |
H28A | 0.368542 | 0.529057 | 0.520982 | 0.026* | |
H28B | 0.384614 | 0.414669 | 0.489710 | 0.026* | |
C27 | 0.42968 (9) | 0.4688 (3) | 0.58804 (14) | 0.0218 (6) | |
H27A | 0.448791 | 0.407585 | 0.581380 | 0.026* | |
H27B | 0.438268 | 0.558577 | 0.583636 | 0.026* | |
C17 | 0.29586 (10) | 0.5546 (3) | 0.82245 (16) | 0.0252 (6) | |
H17A | 0.295162 | 0.618232 | 0.855678 | 0.030* | |
H17B | 0.275024 | 0.582953 | 0.775659 | 0.030* | |
B1 | 0.35915 (13) | 0.8357 (4) | 0.53007 (19) | 0.0317 (8) | |
C1S | 0.36391 (13) | 1.0744 (5) | 0.4171 (2) | 0.0568 (12) | |
H1SA | 0.372205 | 0.985789 | 0.436656 | 0.068* | |
H1SB | 0.352286 | 1.120661 | 0.443906 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.01177 (5) | 0.01212 (5) | 0.00905 (5) | 0.00001 (4) | 0.00476 (4) | −0.00061 (4) |
P1 | 0.0132 (3) | 0.0105 (3) | 0.0100 (3) | 0.0009 (2) | 0.0053 (3) | 0.0001 (2) |
Cl2S | 0.0298 (4) | 0.0360 (4) | 0.0242 (4) | 0.0020 (3) | 0.0155 (3) | 0.0033 (3) |
Cl1S | 0.0400 (5) | 0.0429 (5) | 0.0466 (5) | −0.0068 (4) | 0.0067 (4) | −0.0053 (4) |
F4 | 0.0372 (11) | 0.0322 (10) | 0.0466 (12) | −0.0052 (9) | 0.0210 (10) | −0.0079 (9) |
N1 | 0.0170 (11) | 0.0167 (11) | 0.0158 (11) | −0.0025 (9) | 0.0077 (9) | 0.0002 (9) |
N3 | 0.0132 (11) | 0.0166 (11) | 0.0140 (11) | 0.0006 (9) | 0.0059 (9) | −0.0001 (9) |
F2 | 0.113 (2) | 0.0406 (13) | 0.0361 (13) | 0.0102 (14) | 0.0270 (14) | −0.0078 (10) |
F3 | 0.0350 (13) | 0.0366 (13) | 0.109 (2) | −0.0045 (10) | 0.0166 (14) | −0.0099 (13) |
C19 | 0.0168 (13) | 0.0161 (12) | 0.0102 (12) | 0.0004 (10) | 0.0072 (10) | −0.0002 (9) |
N2 | 0.0167 (12) | 0.0261 (13) | 0.0190 (12) | −0.0035 (10) | 0.0083 (10) | −0.0009 (10) |
F1 | 0.091 (2) | 0.0757 (19) | 0.0468 (15) | −0.0387 (16) | 0.0203 (14) | 0.0237 (13) |
C1 | 0.0173 (13) | 0.0107 (12) | 0.0120 (12) | −0.0002 (9) | 0.0069 (10) | −0.0010 (9) |
C7 | 0.0117 (12) | 0.0128 (12) | 0.0112 (12) | 0.0013 (9) | 0.0040 (10) | 0.0013 (9) |
C13 | 0.0140 (12) | 0.0164 (12) | 0.0126 (12) | 0.0004 (10) | 0.0068 (10) | −0.0006 (10) |
C6 | 0.0161 (13) | 0.0134 (12) | 0.0142 (12) | 0.0009 (10) | 0.0066 (10) | −0.0009 (9) |
C12 | 0.0186 (13) | 0.0124 (12) | 0.0133 (13) | 0.0024 (10) | 0.0070 (11) | 0.0007 (10) |
C2 | 0.0174 (13) | 0.0136 (12) | 0.0161 (13) | 0.0030 (10) | 0.0064 (11) | 0.0019 (10) |
C21 | 0.0269 (15) | 0.0148 (13) | 0.0214 (14) | −0.0034 (11) | 0.0086 (12) | 0.0014 (11) |
C25 | 0.0150 (13) | 0.0224 (14) | 0.0135 (13) | 0.0005 (10) | 0.0073 (11) | −0.0042 (10) |
C8 | 0.0177 (13) | 0.0162 (13) | 0.0120 (12) | 0.0011 (10) | 0.0059 (11) | −0.0009 (10) |
C23 | 0.0260 (15) | 0.0234 (14) | 0.0151 (14) | 0.0054 (12) | 0.0074 (12) | 0.0033 (11) |
C11 | 0.0201 (13) | 0.0122 (12) | 0.0158 (13) | 0.0034 (10) | 0.0092 (11) | 0.0029 (10) |
C9 | 0.0193 (13) | 0.0198 (13) | 0.0096 (12) | 0.0011 (11) | 0.0043 (11) | 0.0002 (10) |
C18 | 0.0240 (15) | 0.0192 (13) | 0.0173 (14) | 0.0037 (11) | 0.0119 (12) | −0.0006 (10) |
C20 | 0.0116 (12) | 0.0263 (15) | 0.0156 (13) | −0.0013 (11) | 0.0048 (11) | −0.0007 (11) |
C26 | 0.0159 (13) | 0.0194 (13) | 0.0183 (13) | −0.0043 (10) | 0.0107 (11) | −0.0026 (10) |
C32 | 0.0175 (13) | 0.0235 (14) | 0.0169 (13) | 0.0057 (11) | 0.0084 (11) | −0.0011 (11) |
C4 | 0.0243 (15) | 0.0178 (13) | 0.0193 (14) | −0.0028 (11) | 0.0120 (12) | 0.0014 (11) |
C14 | 0.0172 (13) | 0.0171 (12) | 0.0151 (13) | 0.0002 (10) | 0.0086 (11) | 0.0004 (10) |
C30 | 0.0187 (14) | 0.0202 (13) | 0.0131 (13) | −0.0028 (10) | 0.0067 (11) | −0.0080 (10) |
C10 | 0.0213 (14) | 0.0176 (13) | 0.0129 (13) | 0.0043 (11) | 0.0065 (11) | 0.0051 (10) |
C16 | 0.0239 (15) | 0.0332 (16) | 0.0294 (16) | 0.0060 (13) | 0.0200 (13) | 0.0065 (13) |
C22 | 0.0180 (13) | 0.0152 (13) | 0.0174 (13) | 0.0034 (10) | 0.0071 (11) | 0.0031 (10) |
C15 | 0.0162 (14) | 0.0282 (15) | 0.0259 (15) | −0.0001 (11) | 0.0108 (12) | 0.0041 (12) |
C29 | 0.0189 (13) | 0.0272 (15) | 0.0085 (12) | −0.0007 (11) | 0.0068 (11) | −0.0033 (10) |
C5 | 0.0216 (14) | 0.0166 (13) | 0.0175 (14) | −0.0031 (11) | 0.0089 (12) | −0.0017 (10) |
C31 | 0.0244 (15) | 0.0197 (13) | 0.0183 (14) | 0.0015 (11) | 0.0107 (12) | −0.0072 (11) |
C3 | 0.0253 (15) | 0.0140 (13) | 0.0177 (14) | 0.0014 (11) | 0.0097 (12) | 0.0029 (10) |
C24 | 0.0255 (15) | 0.0212 (14) | 0.0143 (13) | 0.0087 (11) | 0.0059 (12) | 0.0024 (11) |
C28 | 0.0255 (15) | 0.0291 (15) | 0.0140 (13) | 0.0020 (12) | 0.0113 (12) | 0.0038 (11) |
C27 | 0.0252 (15) | 0.0256 (15) | 0.0207 (14) | −0.0042 (12) | 0.0160 (13) | 0.0000 (11) |
C17 | 0.0277 (16) | 0.0267 (15) | 0.0283 (16) | 0.0113 (12) | 0.0190 (14) | 0.0037 (12) |
B1 | 0.041 (2) | 0.0238 (18) | 0.0246 (19) | −0.0130 (15) | 0.0110 (17) | 0.0005 (14) |
C1S | 0.048 (2) | 0.096 (4) | 0.034 (2) | −0.021 (2) | 0.0252 (19) | 0.004 (2) |
Ir1—P1 | 2.3732 (7) | C11—H11B | 0.9900 |
Ir1—C19 | 2.035 (3) | C11—C10 | 1.526 (4) |
Ir1—C25 | 2.179 (3) | C9—H9A | 0.9900 |
Ir1—C26 | 2.194 (3) | C9—H9B | 0.9900 |
Ir1—C30 | 2.196 (3) | C9—C10 | 1.528 (4) |
Ir1—C29 | 2.205 (3) | C18—H18A | 0.9900 |
P1—C1 | 1.863 (3) | C18—H18B | 0.9900 |
P1—C7 | 1.862 (3) | C18—C17 | 1.533 (4) |
P1—C13 | 1.868 (3) | C20—H20 | 0.9500 |
Cl2S—C1S | 1.750 (4) | C26—H26 | 1.0000 |
Cl1S—C1S | 1.742 (4) | C26—C27 | 1.496 (3) |
F4—B1 | 1.403 (5) | C32—H32A | 0.9900 |
N1—C19 | 1.343 (3) | C32—H32B | 0.9900 |
N1—N2 | 1.383 (3) | C32—C31 | 1.530 (4) |
N1—C21 | 1.460 (3) | C4—H4A | 0.9900 |
N3—C19 | 1.366 (3) | C4—H4B | 0.9900 |
N3—C20 | 1.367 (3) | C4—C5 | 1.528 (4) |
N3—C22 | 1.484 (3) | C4—C3 | 1.525 (4) |
F2—B1 | 1.372 (4) | C14—H14A | 0.9900 |
F3—B1 | 1.368 (5) | C14—H14B | 0.9900 |
N2—C20 | 1.298 (4) | C14—C15 | 1.527 (4) |
F1—B1 | 1.361 (4) | C30—H30 | 1.0000 |
C1—H1 | 1.0000 | C30—C29 | 1.394 (4) |
C1—C6 | 1.551 (4) | C30—C31 | 1.519 (4) |
C1—C2 | 1.543 (3) | C10—H10A | 0.9900 |
C7—H7 | 1.0000 | C10—H10B | 0.9900 |
C7—C12 | 1.546 (3) | C16—H16A | 0.9900 |
C7—C8 | 1.543 (3) | C16—H16B | 0.9900 |
C13—H13 | 1.0000 | C16—C15 | 1.524 (4) |
C13—C18 | 1.530 (4) | C16—C17 | 1.520 (4) |
C13—C14 | 1.541 (4) | C22—H22 | 1.0000 |
C6—H6A | 0.9900 | C22—C24 | 1.525 (4) |
C6—H6B | 0.9900 | C15—H15A | 0.9900 |
C6—C5 | 1.522 (3) | C15—H15B | 0.9900 |
C12—H12A | 0.9900 | C29—H29 | 1.0000 |
C12—H12B | 0.9900 | C29—C28 | 1.509 (4) |
C12—C11 | 1.527 (3) | C5—H5A | 0.9900 |
C2—H2A | 0.9900 | C5—H5B | 0.9900 |
C2—H2B | 0.9900 | C31—H31A | 0.9900 |
C2—C3 | 1.534 (4) | C31—H31B | 0.9900 |
C21—H21A | 0.9800 | C3—H3A | 0.9900 |
C21—H21B | 0.9800 | C3—H3B | 0.9900 |
C21—H21C | 0.9800 | C24—H24A | 0.9800 |
C25—H25 | 1.0000 | C24—H24B | 0.9800 |
C25—C26 | 1.404 (4) | C24—H24C | 0.9800 |
C25—C32 | 1.510 (4) | C28—H28A | 0.9900 |
C8—H8A | 0.9900 | C28—H28B | 0.9900 |
C8—H8B | 0.9900 | C28—C27 | 1.533 (4) |
C8—C9 | 1.526 (4) | C27—H27A | 0.9900 |
C23—H23A | 0.9800 | C27—H27B | 0.9900 |
C23—H23B | 0.9800 | C17—H17A | 0.9900 |
C23—H23C | 0.9800 | C17—H17B | 0.9900 |
C23—C22 | 1.520 (4) | C1S—H1SA | 0.9900 |
C11—H11A | 0.9900 | C1S—H1SB | 0.9900 |
C19—Ir1—P1 | 94.07 (7) | C25—C26—Ir1 | 70.68 (15) |
C19—Ir1—C25 | 162.50 (10) | C25—C26—H26 | 112.2 |
C19—Ir1—C26 | 156.41 (10) | C25—C26—C27 | 127.4 (2) |
C19—Ir1—C30 | 89.60 (10) | C27—C26—Ir1 | 115.31 (17) |
C19—Ir1—C29 | 83.82 (10) | C27—C26—H26 | 112.2 |
C25—Ir1—P1 | 90.64 (7) | C25—C32—H32A | 109.0 |
C25—Ir1—C26 | 37.45 (10) | C25—C32—H32B | 109.0 |
C25—Ir1—C30 | 80.07 (10) | C25—C32—C31 | 112.7 (2) |
C25—Ir1—C29 | 95.89 (10) | H32A—C32—H32B | 107.8 |
C26—Ir1—P1 | 98.76 (6) | C31—C32—H32A | 109.0 |
C26—Ir1—C30 | 85.73 (9) | C31—C32—H32B | 109.0 |
C26—Ir1—C29 | 78.59 (9) | H4A—C4—H4B | 108.1 |
C30—Ir1—P1 | 158.38 (7) | C5—C4—H4A | 109.5 |
C30—Ir1—C29 | 36.92 (10) | C5—C4—H4B | 109.5 |
C29—Ir1—P1 | 164.70 (7) | C3—C4—H4A | 109.5 |
C1—P1—Ir1 | 114.85 (8) | C3—C4—H4B | 109.5 |
C1—P1—C13 | 104.19 (11) | C3—C4—C5 | 110.6 (2) |
C7—P1—Ir1 | 114.70 (8) | C13—C14—H14A | 109.4 |
C7—P1—C1 | 102.49 (11) | C13—C14—H14B | 109.4 |
C7—P1—C13 | 108.17 (12) | H14A—C14—H14B | 108.0 |
C13—P1—Ir1 | 111.52 (8) | C15—C14—C13 | 111.3 (2) |
C19—N1—N2 | 113.9 (2) | C15—C14—H14A | 109.4 |
C19—N1—C21 | 126.8 (2) | C15—C14—H14B | 109.4 |
N2—N1—C21 | 119.3 (2) | Ir1—C30—H30 | 113.6 |
C19—N3—C20 | 108.6 (2) | C29—C30—Ir1 | 71.89 (15) |
C19—N3—C22 | 125.4 (2) | C29—C30—H30 | 113.6 |
C20—N3—C22 | 125.9 (2) | C29—C30—C31 | 124.3 (3) |
N1—C19—Ir1 | 129.73 (19) | C31—C30—Ir1 | 112.85 (17) |
N1—C19—N3 | 102.8 (2) | C31—C30—H30 | 113.6 |
N3—C19—Ir1 | 126.77 (19) | C11—C10—C9 | 110.7 (2) |
C20—N2—N1 | 103.0 (2) | C11—C10—H10A | 109.5 |
P1—C1—H1 | 106.2 | C11—C10—H10B | 109.5 |
C6—C1—P1 | 115.09 (17) | C9—C10—H10A | 109.5 |
C6—C1—H1 | 106.2 | C9—C10—H10B | 109.5 |
C2—C1—P1 | 109.51 (17) | H10A—C10—H10B | 108.1 |
C2—C1—H1 | 106.2 | H16A—C16—H16B | 108.0 |
C2—C1—C6 | 112.9 (2) | C15—C16—H16A | 109.4 |
P1—C7—H7 | 105.1 | C15—C16—H16B | 109.4 |
C12—C7—P1 | 114.79 (17) | C17—C16—H16A | 109.4 |
C12—C7—H7 | 105.1 | C17—C16—H16B | 109.4 |
C8—C7—P1 | 114.64 (17) | C17—C16—C15 | 111.2 (2) |
C8—C7—H7 | 105.1 | N3—C22—C23 | 110.1 (2) |
C8—C7—C12 | 111.0 (2) | N3—C22—H22 | 108.1 |
P1—C13—H13 | 105.1 | N3—C22—C24 | 110.4 (2) |
C18—C13—P1 | 118.41 (18) | C23—C22—H22 | 108.1 |
C18—C13—H13 | 105.1 | C23—C22—C24 | 111.9 (2) |
C18—C13—C14 | 110.1 (2) | C24—C22—H22 | 108.1 |
C14—C13—P1 | 111.79 (17) | C14—C15—H15A | 109.5 |
C14—C13—H13 | 105.1 | C14—C15—H15B | 109.5 |
C1—C6—H6A | 109.4 | C16—C15—C14 | 110.5 (2) |
C1—C6—H6B | 109.4 | C16—C15—H15A | 109.5 |
H6A—C6—H6B | 108.0 | C16—C15—H15B | 109.5 |
C5—C6—C1 | 111.1 (2) | H15A—C15—H15B | 108.1 |
C5—C6—H6A | 109.4 | Ir1—C29—H29 | 114.1 |
C5—C6—H6B | 109.4 | C30—C29—Ir1 | 71.19 (15) |
C7—C12—H12A | 109.5 | C30—C29—H29 | 114.1 |
C7—C12—H12B | 109.5 | C30—C29—C28 | 125.1 (3) |
H12A—C12—H12B | 108.1 | C28—C29—Ir1 | 110.39 (18) |
C11—C12—C7 | 110.5 (2) | C28—C29—H29 | 114.1 |
C11—C12—H12A | 109.5 | C6—C5—C4 | 112.7 (2) |
C11—C12—H12B | 109.5 | C6—C5—H5A | 109.0 |
C1—C2—H2A | 109.2 | C6—C5—H5B | 109.0 |
C1—C2—H2B | 109.2 | C4—C5—H5A | 109.0 |
H2A—C2—H2B | 107.9 | C4—C5—H5B | 109.0 |
C3—C2—C1 | 112.1 (2) | H5A—C5—H5B | 107.8 |
C3—C2—H2A | 109.2 | C32—C31—H31A | 109.3 |
C3—C2—H2B | 109.2 | C32—C31—H31B | 109.3 |
N1—C21—H21A | 109.5 | C30—C31—C32 | 111.6 (2) |
N1—C21—H21B | 109.5 | C30—C31—H31A | 109.3 |
N1—C21—H21C | 109.5 | C30—C31—H31B | 109.3 |
H21A—C21—H21B | 109.5 | H31A—C31—H31B | 108.0 |
H21A—C21—H21C | 109.5 | C2—C3—H3A | 109.3 |
H21B—C21—H21C | 109.5 | C2—C3—H3B | 109.3 |
Ir1—C25—H25 | 114.5 | C4—C3—C2 | 111.4 (2) |
C26—C25—Ir1 | 71.87 (15) | C4—C3—H3A | 109.3 |
C26—C25—H25 | 114.5 | C4—C3—H3B | 109.3 |
C26—C25—C32 | 124.7 (2) | H3A—C3—H3B | 108.0 |
C32—C25—Ir1 | 108.68 (18) | C22—C24—H24A | 109.5 |
C32—C25—H25 | 114.5 | C22—C24—H24B | 109.5 |
C7—C8—H8A | 109.5 | C22—C24—H24C | 109.5 |
C7—C8—H8B | 109.5 | H24A—C24—H24B | 109.5 |
H8A—C8—H8B | 108.1 | H24A—C24—H24C | 109.5 |
C9—C8—C7 | 110.7 (2) | H24B—C24—H24C | 109.5 |
C9—C8—H8A | 109.5 | C29—C28—H28A | 108.9 |
C9—C8—H8B | 109.5 | C29—C28—H28B | 108.9 |
H23A—C23—H23B | 109.5 | C29—C28—C27 | 113.2 (2) |
H23A—C23—H23C | 109.5 | H28A—C28—H28B | 107.8 |
H23B—C23—H23C | 109.5 | C27—C28—H28A | 108.9 |
C22—C23—H23A | 109.5 | C27—C28—H28B | 108.9 |
C22—C23—H23B | 109.5 | C26—C27—C28 | 112.0 (2) |
C22—C23—H23C | 109.5 | C26—C27—H27A | 109.2 |
C12—C11—H11A | 109.2 | C26—C27—H27B | 109.2 |
C12—C11—H11B | 109.2 | C28—C27—H27A | 109.2 |
H11A—C11—H11B | 107.9 | C28—C27—H27B | 109.2 |
C10—C11—C12 | 112.0 (2) | H27A—C27—H27B | 107.9 |
C10—C11—H11A | 109.2 | C18—C17—H17A | 109.2 |
C10—C11—H11B | 109.2 | C18—C17—H17B | 109.2 |
C8—C9—H9A | 109.4 | C16—C17—C18 | 112.2 (2) |
C8—C9—H9B | 109.4 | C16—C17—H17A | 109.2 |
C8—C9—C10 | 111.0 (2) | C16—C17—H17B | 109.2 |
H9A—C9—H9B | 108.0 | H17A—C17—H17B | 107.9 |
C10—C9—H9A | 109.4 | F2—B1—F4 | 108.1 (3) |
C10—C9—H9B | 109.4 | F3—B1—F4 | 109.2 (3) |
C13—C18—H18A | 109.5 | F3—B1—F2 | 110.3 (4) |
C13—C18—H18B | 109.5 | F1—B1—F4 | 109.7 (3) |
C13—C18—C17 | 110.8 (2) | F1—B1—F2 | 109.8 (3) |
H18A—C18—H18B | 108.1 | F1—B1—F3 | 109.7 (3) |
C17—C18—H18A | 109.5 | Cl2S—C1S—H1SA | 108.9 |
C17—C18—H18B | 109.5 | Cl2S—C1S—H1SB | 108.9 |
N3—C20—H20 | 124.1 | Cl1S—C1S—Cl2S | 113.3 (2) |
N2—C20—N3 | 111.8 (2) | Cl1S—C1S—H1SA | 108.9 |
N2—C20—H20 | 124.1 | Cl1S—C1S—H1SB | 108.9 |
Ir1—C26—H26 | 112.2 | H1SA—C1S—H1SB | 107.7 |
Ir1—P1—C1—C6 | −83.03 (17) | C13—P1—C1—C2 | −76.91 (19) |
Ir1—P1—C1—C2 | 45.38 (19) | C13—P1—C7—C12 | 81.0 (2) |
Ir1—P1—C7—C12 | −44.1 (2) | C13—P1—C7—C8 | −49.2 (2) |
Ir1—P1—C7—C8 | −174.36 (15) | C13—C18—C17—C16 | 55.1 (3) |
Ir1—P1—C13—C18 | −149.88 (17) | C13—C14—C15—C16 | −57.3 (3) |
Ir1—P1—C13—C14 | 80.59 (18) | C6—C1—C2—C3 | −50.3 (3) |
Ir1—C25—C26—C27 | −107.6 (3) | C12—C7—C8—C9 | 56.0 (3) |
Ir1—C25—C32—C31 | 41.4 (3) | C12—C11—C10—C9 | −56.5 (3) |
Ir1—C26—C27—C28 | 10.0 (3) | C2—C1—C6—C5 | 49.8 (3) |
Ir1—C30—C29—C28 | 102.2 (3) | C21—N1—C19—Ir1 | 10.7 (4) |
Ir1—C30—C31—C32 | 13.9 (3) | C21—N1—C19—N3 | −178.9 (2) |
Ir1—C29—C28—C27 | 36.2 (3) | C21—N1—N2—C20 | 179.2 (2) |
P1—C1—C6—C5 | 176.53 (17) | C25—C26—C27—C28 | 94.3 (3) |
P1—C1—C2—C3 | −179.95 (18) | C25—C32—C31—C30 | −36.9 (3) |
P1—C7—C12—C11 | 173.23 (17) | C8—C7—C12—C11 | −54.8 (3) |
P1—C7—C8—C9 | −171.94 (18) | C8—C9—C10—C11 | 57.0 (3) |
P1—C13—C18—C17 | 174.26 (19) | C18—C13—C14—C15 | 57.3 (3) |
P1—C13—C14—C15 | −168.97 (19) | C20—N3—C19—Ir1 | 170.16 (19) |
N1—N2—C20—N3 | −0.2 (3) | C20—N3—C19—N1 | −0.7 (3) |
C19—N1—N2—C20 | −0.2 (3) | C20—N3—C22—C23 | −58.8 (3) |
C19—N3—C20—N2 | 0.6 (3) | C20—N3—C22—C24 | 65.3 (3) |
C19—N3—C22—C23 | 116.4 (3) | C26—C25—C32—C31 | −39.0 (4) |
C19—N3—C22—C24 | −119.5 (3) | C32—C25—C26—Ir1 | 100.6 (3) |
N2—N1—C19—Ir1 | −169.89 (18) | C32—C25—C26—C27 | −7.0 (4) |
N2—N1—C19—N3 | 0.6 (3) | C14—C13—C18—C17 | −55.4 (3) |
C1—P1—C7—C12 | −169.26 (19) | C30—C29—C28—C27 | −44.6 (4) |
C1—P1—C7—C8 | 60.5 (2) | C22—N3—C19—Ir1 | −5.8 (4) |
C1—P1—C13—C18 | −25.4 (2) | C22—N3—C19—N1 | −176.6 (2) |
C1—P1—C13—C14 | −154.96 (18) | C22—N3—C20—N2 | 176.5 (2) |
C1—C6—C5—C4 | −53.7 (3) | C15—C16—C17—C18 | −55.1 (3) |
C1—C2—C3—C4 | 53.8 (3) | C29—C30—C31—C32 | 97.0 (3) |
C7—P1—C1—C6 | 42.0 (2) | C29—C28—C27—C26 | −30.5 (3) |
C7—P1—C1—C2 | 170.42 (17) | C5—C4—C3—C2 | −56.8 (3) |
C7—P1—C13—C18 | 83.1 (2) | C31—C30—C29—Ir1 | −105.8 (2) |
C7—P1—C13—C14 | −46.4 (2) | C31—C30—C29—C28 | −3.6 (4) |
C7—C12—C11—C10 | 55.3 (3) | C3—C4—C5—C6 | 57.6 (3) |
C7—C8—C9—C10 | −57.1 (3) | C17—C16—C15—C14 | 55.7 (3) |
C13—P1—C1—C6 | 154.69 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···F1 | 0.99 | 2.54 | 3.204 (4) | 124 |
C23—H23C···F1 | 0.98 | 2.51 | 3.137 (4) | 122 |
C20—H20···F4i | 0.95 | 2.49 | 3.400 (3) | 161 |
C30—H30···F4ii | 1.00 | 2.35 | 3.192 (3) | 141 |
C16—H16B···F2iii | 0.99 | 2.54 | 3.404 (4) | 146 |
C22—H22···F1 | 1.00 | 2.41 | 3.094 (4) | 125 |
C31—H31B···F3ii | 0.99 | 2.35 | 3.330 (4) | 170 |
C1S—H1SA···F2 | 0.99 | 2.50 | 3.362 (5) | 145 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, y−1, z; (iii) x, −y+1, z+1/2. |
Acknowledgements
JR was supported in this work by the Millersville University Murley Summer Undergraduate Research Fellowship.
References
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