metal-organic compounds
Hydrido(prolinato-κ2N,O)tris(trimethylphosphane-κP)iridium(III) hexafluoridophosphate
aDepartment of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA, and bDepartment of Chemistry, Duke University, Durham, NC 27708, USA
*Correspondence e-mail: jmerola@vt.edu
The title complex, [Ir(C5H8NO2)H(C3H9P)3]PF6, has two independent anion–cation pairs in the The geometry about each IrIII atom is pseudo-octahedral with a meridional arrangement of the P(CH3)3 ligands, N,O-bidentate coordination of prolinate and a hydride ligand trans to the prolinate N atom. The independent IrIII moieties are joined by N—H⋯O hydrogen bonds and the N—H⋯O bonding motif continues throughout the structure, creating an extended chain parallel to the c-axis direction. The methyl groups of one P(CH3)3 ligand are rotationally disordered over two sets of sites in a 0.62 (2):0.38 (2) ratio.
CCDC reference: 983575
Related literature
For the valine structure analogous to the proline structure described herein, see: Roy et al. (2006). For a Cp*Ir complex with proline and a t-butylethynl ligand, see: Carmona et al. (2000). For a Cp*Ir complex with proline and a chloride ligand, see: Carmona et al. (2012). For the preparation of [Ir(COD)(PMe3)3]Cl, see: Frazier & Merola (1992). For a selection of amino acid complexes in general, their structures and their extended lattice features, see: Urban et al. (1996); Shimazaki et al. (2009). For a description of the Cambridge Structural Database, see: Allen (2002).
Experimental
Crystal data
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Data collection: XSCANS (Siemens, 1996); cell XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 983575
10.1107/S1600536814001834/pk2511sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001834/pk2511Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001834/pk2511Isup3.mol
[Ir(COD)(PMe3)3]Cl was synthesized as reported previously (Frazier & Merola, 1992). L-proline was purchased from Aldrich Chemical and used as received. Water was deionized/distilled.
A 100 mL flask equipped with a stir bar and septum was charged with 117.5 mg (1.02 mmol) of L-proline. The flask was then charged with 250 mg (0.443 mmol) of [Ir(COD)(PMe3)3]Cl under N2 in a drybox. The flask was then connected to a double manifold (vacuum/nitrogen) Schlenk line and 20 mL of distilled water was added to the flask via syringe. The solution was stirred magnetically and heated to reflux. After 18 hours at reflux the reaction mixture was allowed to cool and solvent was removed in vacuo. The white solid residue was treated with distilled methylene chloride (3 x 10 mL) to extract the product from the excess amino acid. The solution was filtered from the solid using cannula techniques. The methylene chloride was removed in vacuo and the solids were dried under reduced pressure to yield 150 mg (0.263 mmol, 60.7% yield based on the amount of Ir(COD)(PMe3)3]Cl) of [Ir(L-pro)(H)(PMe3)3]Cl C,H analysis: Calculated for C14H36NO2P3IrCl:C, 29.4% H,6.3% Found: C, 29.17%; H, 6.2% An aqueous solution of the chloride salt was treated with an aqueous solution of K[PF6] to precipitate [Ir(L-pro)(H)(PMe3)3][PF6]. Crystals suitable for X-ray diffraction were grown from dichloromethane/diethylether.
Hydrogen atoms were treated with a combination of
(i.e. for the Ir—H hydrogens) and constrained riding models. Values of Uiso(H) were set to either 1.2Ueq or 1.5Ueq of the parent atom. Crystal data, data collection and structure details are summarized in Table 1.The chemistry of amino acid complexes of transition metals has a long history (Shimazaki et al., 2009). A search of the CSD data base (Allen, 2002) reveals over 1400 hits for compounds with bidentate N,O coordination of amino acids to transition metals. Restricting the search to the specific amino acid proline, yields over 140 hits. Finally, restricting the search to iridium compounds, there are 6 CSD structures with proline coordinated to iridium. We reported on the η5-Pentamethyl-cyclopentadienyl)-(t-butylethynyl)-(L-prolinato-N,O)-ιridium (CSD:20010919) (Carmona et al., 2000), but when the t-butylethynyl group is replaced by chloride (CSD: 19911024) (Carmona et al., 2012), the motif changes to alternating N—H···O and N—H···Cl bonding to generate the full lattice.
of [hydrido-valinato-tris(trimethylphosphine)iridium][hexafluorophosphate] (CSD:20060907) (Roy et al., 2006) in the P43, which has very strong intermolecular N—H···O hydrogen bonding that results in a 43 helical arrangement of the iridium complexes. In this report, the title proline complex has a "flatter" intermolecular motif with the N—H···O hydrogen bonding resulting in a one-dimenional chain motif with the chain parallel to the c-axis. Hydrogen bonding parameters are listed Table 1. A similar motif has been reported for ([Ir(COD)(PMe3)3]Cl was synthesized as reported previously (Frazier & Merola, 1992). L-proline was purchased from Aldrich Chemical and used as received. Water was deionized/distilled.
The chemistry of amino acid complexes of transition metals has a long history (Shimazaki et al., 2009). A search of the CSD data base (Allen, 2002) reveals over 1400 hits for compounds with bidentate N,O coordination of amino acids to transition metals. Restricting the search to the specific amino acid proline, yields over 140 hits. Finally, restricting the search to iridium compounds, there are 6 CSD structures with proline coordinated to iridium. We reported on the η5-Pentamethyl-cyclopentadienyl)-(t-butylethynyl)-(L-prolinato-N,O)-ιridium (CSD:20010919) (Carmona et al., 2000), but when the t-butylethynyl group is replaced by chloride (CSD: 19911024) (Carmona et al., 2012), the motif changes to alternating N—H···O and N—H···Cl bonding to generate the full lattice.
of [hydrido-valinato-tris(trimethylphosphine)iridium][hexafluorophosphate] (CSD:20060907) (Roy et al., 2006) in the P43, which has very strong intermolecular N—H···O hydrogen bonding that results in a 43 helical arrangement of the iridium complexes. In this report, the title proline complex has a "flatter" intermolecular motif with the N—H···O hydrogen bonding resulting in a one-dimenional chain motif with the chain parallel to the c-axis. Hydrogen bonding parameters are listed Table 1. A similar motif has been reported for (For the valine structure analogous to the proline structure described herein, see: Roy et al. (2006). For a Cp*Ir complex with proline and a t-butylethynl ligand, see: Carmona et al. (2000). For a Cp*Ir complex with proline and a chloride ligand ,see: Carmona et al. (2012). For the preparation of [Ir(COD)(PMe3)3]Cl, see: Frazier & Merola (1992). For a selection of amino acid complexes in general, their structures and their extended lattice features, see: Urban et al. (1996); Shimazaki et al. (2009). For a description of the Cambridge Structural Database, see: Allen (2002).
A 100 mL flask equipped with a stir bar and septum was charged with 117.5 mg (1.02 mmol) of L-proline. The flask was then charged with 250 mg (0.443 mmol) of [Ir(COD)(PMe3)3]Cl under N2 in a drybox. The flask was then connected to a double manifold (vacuum/nitrogen) Schlenk line and 20 mL of distilled water was added to the flask via syringe. The solution was stirred magnetically and heated to reflux. After 18 hours at reflux the reaction mixture was allowed to cool and solvent was removed in vacuo. The white solid residue was treated with distilled methylene chloride (3 x 10 mL) to extract the product from the excess amino acid. The solution was filtered from the solid using cannula techniques. The methylene chloride was removed in vacuo and the solids were dried under reduced pressure to yield 150 mg (0.263 mmol, 60.7% yield based on the amount of Ir(COD)(PMe3)3]Cl) of [Ir(L-pro)(H)(PMe3)3]Cl C,H analysis: Calculated for C14H36NO2P3IrCl:C, 29.4% H,6.3% Found: C, 29.17%; H, 6.2% An aqueous solution of the chloride salt was treated with an aqueous solution of K[PF6] to precipitate [Ir(L-pro)(H)(PMe3)3][PF6]. Crystals suitable for X-ray diffraction were grown from dichloromethane/diethylether.
detailsHydrogen atoms were treated with a combination of
(i.e. for the Ir—H hydrogens) and constrained riding models. Values of Uiso(H) were set to either 1.2Ueq or 1.5Ueq of the parent atom. Crystal data, data collection and structure details are summarized in Table 1.Data collection: XSCANS (Siemens, 1996); cell
XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[Ir(C5H8NO2)H(C3H9P)3]PF6 | F(000) = 1336 |
Mr = 680.52 | Dx = 1.764 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.824 (2) Å | Cell parameters from 25 reflections |
b = 20.021 (4) Å | θ = 2–22° |
c = 11.826 (2) Å | µ = 5.51 mm−1 |
β = 91.15 (1)° | T = 293 K |
V = 2562.3 (8) Å3 | Prism, clear colourless |
Z = 4 | 0.5 × 0.4 × 0.4 mm |
Siemens P4 diffractometer | 5587 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
ω–scans | h = 0→14 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→26 |
Tmin = 0.618, Tmax = 1.000 | l = −15→15 |
6363 measured reflections | 3 standard reflections every 300 reflections |
6055 independent reflections | intensity decay: 0(1) |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0445P)2 + 1.0877P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 1.02 e Å−3 |
6055 reflections | Δρmin = −0.93 e Å−3 |
522 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.00105 (12) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.001 (8) |
[Ir(C5H8NO2)H(C3H9P)3]PF6 | V = 2562.3 (8) Å3 |
Mr = 680.52 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.824 (2) Å | µ = 5.51 mm−1 |
b = 20.021 (4) Å | T = 293 K |
c = 11.826 (2) Å | 0.5 × 0.4 × 0.4 mm |
β = 91.15 (1)° |
Siemens P4 diffractometer | 5587 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.020 |
Tmin = 0.618, Tmax = 1.000 | 3 standard reflections every 300 reflections |
6363 measured reflections | intensity decay: 0(1) |
6055 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | Δρmax = 1.02 e Å−3 |
S = 1.06 | Δρmin = −0.93 e Å−3 |
6055 reflections | Absolute structure: Flack (1983) |
522 parameters | Absolute structure parameter: 0.001 (8) |
4 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ir2 | −0.08795 (2) | −0.490281 (13) | −0.05567 (2) | 0.03453 (8) | |
H | 0.014 (7) | −0.486 (5) | 0.021 (6) | 0.041* | |
P4 | −0.0431 (2) | −0.38225 (14) | −0.1162 (2) | 0.0514 (5) | |
P5 | 0.0256 (2) | −0.54315 (14) | −0.18575 (19) | 0.0491 (6) | |
P6 | −0.0981 (2) | −0.58276 (13) | 0.0664 (2) | 0.0500 (6) | |
O3 | −0.2047 (6) | −0.4449 (3) | 0.0633 (5) | 0.0438 (13) | |
O4 | −0.3980 (6) | −0.4334 (4) | 0.1118 (5) | 0.0622 (18) | |
N2 | −0.2684 (5) | −0.4939 (4) | −0.1474 (4) | 0.0336 (12) | |
H2A | −0.2590 | −0.4713 | −0.2134 | 0.040* | |
C6 | −0.3219 (8) | −0.4439 (4) | 0.0432 (7) | 0.0428 (18) | |
C7 | −0.3627 (8) | −0.4555 (5) | −0.0791 (7) | 0.048 (2) | |
H7 | −0.3721 | −0.4115 | −0.1145 | 0.057* | |
C8 | −0.4842 (9) | −0.4914 (9) | −0.0947 (10) | 0.082 (4) | |
H8A | −0.5049 | −0.5156 | −0.0266 | 0.099* | |
H8B | −0.5501 | −0.4600 | −0.1123 | 0.099* | |
C9 | −0.4661 (9) | −0.5386 (6) | −0.1910 (9) | 0.065 (3) | |
H9A | −0.4811 | −0.5167 | −0.2632 | 0.078* | |
H9B | −0.5198 | −0.5772 | −0.1854 | 0.078* | |
C10 | −0.3311 (10) | −0.5583 (5) | −0.1762 (9) | 0.055 (2) | |
H10A | −0.3202 | −0.5905 | −0.1156 | 0.066* | |
H10B | −0.2993 | −0.5770 | −0.2454 | 0.066* | |
C41 | −0.1356 (14) | −0.3456 (7) | −0.2278 (11) | 0.092 (5) | |
H41A | −0.1286 | −0.3719 | −0.2952 | 0.137* | |
H41B | −0.1071 | −0.3010 | −0.2421 | 0.137* | |
H41C | −0.2204 | −0.3442 | −0.2057 | 0.137* | |
C42 | −0.0602 (14) | −0.3248 (6) | 0.0002 (10) | 0.081 (4) | |
H42A | −0.1433 | −0.3268 | 0.0268 | 0.121* | |
H42B | −0.0425 | −0.2802 | −0.0247 | 0.121* | |
H42C | −0.0037 | −0.3368 | 0.0605 | 0.121* | |
C43 | 0.1141 (11) | −0.3655 (7) | −0.1608 (14) | 0.096 (5) | |
H43A | 0.1710 | −0.3748 | −0.0995 | 0.144* | |
H43B | 0.1212 | −0.3194 | −0.1823 | 0.144* | |
H43C | 0.1330 | −0.3934 | −0.2241 | 0.144* | |
C51 | 0.0109 (11) | −0.5114 (8) | −0.3276 (8) | 0.081 (4) | |
H51A | −0.0735 | −0.5153 | −0.3534 | 0.121* | |
H51B | 0.0631 | −0.5366 | −0.3764 | 0.121* | |
H51C | 0.0351 | −0.4653 | −0.3286 | 0.121* | |
C52 | −0.0078 (14) | −0.6317 (6) | −0.2063 (10) | 0.081 (4) | |
H52A | 0.0053 | −0.6550 | −0.1361 | 0.122* | |
H52B | 0.0460 | −0.6496 | −0.2623 | 0.122* | |
H52C | −0.0922 | −0.6370 | −0.2311 | 0.122* | |
C53 | 0.1922 (9) | −0.5445 (8) | −0.1651 (11) | 0.081 (4) | |
H53A | 0.2231 | −0.4996 | −0.1634 | 0.122* | |
H53B | 0.2291 | −0.5684 | −0.2262 | 0.122* | |
H53C | 0.2126 | −0.5663 | −0.0949 | 0.122* | |
C61 | −0.1468 (18) | −0.5558 (9) | 0.2034 (10) | 0.130 (8) | |
H61A | −0.0897 | −0.5232 | 0.2329 | 0.196* | |
H61B | −0.1491 | −0.5935 | 0.2535 | 0.196* | |
H61C | −0.2277 | −0.5364 | 0.1968 | 0.196* | |
C62 | −0.1973 (14) | −0.6552 (8) | 0.0456 (15) | 0.112 (6) | |
H62A | −0.2823 | −0.6415 | 0.0466 | 0.168* | |
H62B | −0.1818 | −0.6869 | 0.1051 | 0.168* | |
H62C | −0.1803 | −0.6755 | −0.0260 | 0.168* | |
C63 | 0.0501 (11) | −0.6209 (6) | 0.0953 (9) | 0.066 (3) | |
H63A | 0.0845 | −0.6363 | 0.0258 | 0.099* | |
H63B | 0.0400 | −0.6579 | 0.1457 | 0.099* | |
H63C | 0.1047 | −0.5886 | 0.1297 | 0.099* | |
Ir1 | 0.42609 (3) | −0.385828 (17) | 0.42830 (3) | 0.04158 (10) | |
HA | 0.291 (8) | −0.387 (5) | 0.497 (7) | 0.050* | |
P1 | 0.4533 (3) | −0.29798 (17) | 0.5578 (3) | 0.0643 (8) | |
P2 | 0.3190 (2) | −0.32928 (16) | 0.2955 (2) | 0.0585 (7) | |
P3 | 0.3672 (3) | −0.49222 (17) | 0.3689 (2) | 0.0656 (7) | |
O1 | 0.5350 (6) | −0.4376 (4) | 0.5512 (5) | 0.0592 (18) | |
O2 | 0.7238 (7) | −0.4649 (4) | 0.6036 (6) | 0.068 (2) | |
N1 | 0.6065 (6) | −0.3865 (4) | 0.3446 (5) | 0.0421 (14) | |
H1 | 0.5944 | −0.4097 | 0.2791 | 0.051* | |
C1 | 0.6479 (10) | −0.4445 (5) | 0.5318 (8) | 0.057 (2) | |
C2 | 0.6963 (8) | −0.4281 (5) | 0.4158 (8) | 0.048 (2) | |
H2 | 0.7082 | −0.4705 | 0.3761 | 0.057* | |
C3 | 0.8210 (10) | −0.3902 (8) | 0.4148 (8) | 0.072 (3) | |
H3A | 0.8336 | −0.3646 | 0.4837 | 0.087* | |
H3B | 0.8896 | −0.4209 | 0.4062 | 0.087* | |
C4 | 0.8077 (9) | −0.3443 (7) | 0.3123 (9) | 0.076 (3) | |
H4A | 0.8602 | −0.3053 | 0.3203 | 0.092* | |
H4B | 0.8279 | −0.3676 | 0.2431 | 0.092* | |
C5 | 0.6716 (9) | −0.3252 (6) | 0.3132 (9) | 0.061 (3) | |
H5A | 0.6574 | −0.2901 | 0.3680 | 0.073* | |
H5B | 0.6440 | −0.3098 | 0.2392 | 0.073* | |
C11 | 0.331 (3) | −0.243 (2) | 0.585 (3) | 0.23 (3) | 0.62 (2) |
H11A | 0.2543 | −0.2672 | 0.5831 | 0.339* | 0.62 (2) |
H11B | 0.3284 | −0.2084 | 0.5291 | 0.339* | 0.62 (2) |
H11C | 0.3430 | −0.2235 | 0.6588 | 0.339* | 0.62 (2) |
C12 | 0.448 (4) | −0.3406 (14) | 0.7038 (19) | 0.169 (17) | 0.62 (2) |
H12A | 0.3827 | −0.3731 | 0.7037 | 0.253* | 0.62 (2) |
H12B | 0.4331 | −0.3077 | 0.7609 | 0.253* | 0.62 (2) |
H12C | 0.5254 | −0.3624 | 0.7196 | 0.253* | 0.62 (2) |
C13 | 0.582 (3) | −0.252 (3) | 0.579 (3) | 0.23 (3) | 0.62 (2) |
H13A | 0.6524 | −0.2772 | 0.5561 | 0.351* | 0.62 (2) |
H13B | 0.5899 | −0.2407 | 0.6574 | 0.351* | 0.62 (2) |
H13C | 0.5757 | −0.2118 | 0.5346 | 0.351* | 0.62 (2) |
C11' | 0.595 (4) | −0.281 (4) | 0.620 (5) | 0.23 (3) | 0.38 (2) |
H11D | 0.6517 | −0.2680 | 0.5624 | 0.339* | 0.38 (2) |
H11E | 0.6253 | −0.3202 | 0.6577 | 0.339* | 0.38 (2) |
H11F | 0.5865 | −0.2454 | 0.6732 | 0.339* | 0.38 (2) |
C12' | 0.439 (7) | −0.204 (2) | 0.497 (3) | 0.169 (17) | 0.38 (2) |
H12D | 0.4875 | −0.2004 | 0.4302 | 0.253* | 0.38 (2) |
H12E | 0.4690 | −0.1735 | 0.5532 | 0.253* | 0.38 (2) |
H12F | 0.3542 | −0.1948 | 0.4788 | 0.253* | 0.38 (2) |
C13' | 0.349 (5) | −0.296 (4) | 0.648 (5) | 0.23 (3) | 0.38 (2) |
H13D | 0.2712 | −0.3078 | 0.6125 | 0.351* | 0.38 (2) |
H13E | 0.3435 | −0.2520 | 0.6792 | 0.351* | 0.38 (2) |
H13F | 0.3679 | −0.3275 | 0.7072 | 0.351* | 0.38 (2) |
C21 | 0.3609 (18) | −0.2415 (7) | 0.2790 (16) | 0.115 (6) | |
H21A | 0.3479 | −0.2183 | 0.3488 | 0.173* | |
H21B | 0.3105 | −0.2218 | 0.2202 | 0.173* | |
H21C | 0.4463 | −0.2382 | 0.2594 | 0.173* | |
C22 | 0.1528 (11) | −0.3273 (10) | 0.3072 (12) | 0.102 (6) | |
H22A | 0.1212 | −0.3721 | 0.3058 | 0.154* | |
H22B | 0.1175 | −0.3025 | 0.2450 | 0.154* | |
H22C | 0.1314 | −0.3062 | 0.3770 | 0.154* | |
C23 | 0.3395 (14) | −0.3606 (10) | 0.1514 (10) | 0.104 (6) | |
H23A | 0.4253 | −0.3583 | 0.1327 | 0.156* | |
H23B | 0.2920 | −0.3338 | 0.0992 | 0.156* | |
H23C | 0.3119 | −0.4061 | 0.1468 | 0.156* | |
C31 | 0.220 (2) | −0.5030 (10) | 0.303 (2) | 0.194 (13) | |
H31A | 0.1568 | −0.4896 | 0.3546 | 0.291* | |
H31B | 0.2083 | −0.5491 | 0.2835 | 0.291* | |
H31C | 0.2142 | −0.4761 | 0.2362 | 0.291* | |
C32 | 0.465 (2) | −0.5422 (10) | 0.2820 (17) | 0.177 (12) | |
H32A | 0.4793 | −0.5192 | 0.2124 | 0.265* | |
H32B | 0.4246 | −0.5841 | 0.2661 | 0.265* | |
H32C | 0.5417 | −0.5502 | 0.3210 | 0.265* | |
C33 | 0.3521 (18) | −0.5449 (8) | 0.4876 (13) | 0.116 (6) | |
H33A | 0.4302 | −0.5481 | 0.5272 | 0.173* | |
H33B | 0.3265 | −0.5885 | 0.4630 | 0.173* | |
H33C | 0.2916 | −0.5267 | 0.5372 | 0.173* | |
P2F | 0.9668 (3) | −0.18818 (16) | 0.5529 (2) | 0.0642 (7) | |
F7 | 0.8585 (9) | −0.1880 (7) | 0.6377 (7) | 0.125 (4) | |
F8 | 1.0611 (9) | −0.1994 (5) | 0.6545 (7) | 0.107 (3) | |
F9 | 0.9816 (11) | −0.1118 (4) | 0.5672 (10) | 0.119 (3) | |
F10 | 0.8701 (9) | −0.1759 (7) | 0.4529 (6) | 0.126 (4) | |
F11 | 0.9558 (16) | −0.2645 (5) | 0.5403 (9) | 0.171 (6) | |
F12 | 1.0760 (9) | −0.1859 (7) | 0.4653 (8) | 0.134 (4) | |
P1F | 0.5916 (3) | −0.20678 (17) | −0.0328 (3) | 0.0726 (8) | |
F1 | 0.4971 (14) | −0.1944 (10) | 0.0534 (13) | 0.206 (8) | |
F2 | 0.6848 (16) | −0.2087 (9) | 0.0641 (13) | 0.218 (8) | |
F3 | 0.6158 (16) | −0.1305 (6) | −0.0336 (11) | 0.178 (6) | |
F4 | 0.4963 (12) | −0.1990 (8) | −0.1305 (11) | 0.184 (6) | |
F5 | 0.5793 (17) | −0.2797 (6) | −0.0332 (18) | 0.229 (8) | |
F6 | 0.6855 (13) | −0.2143 (11) | −0.1255 (12) | 0.214 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir2 | 0.03230 (13) | 0.04134 (16) | 0.02985 (13) | 0.00099 (14) | −0.00191 (10) | −0.00124 (14) |
P4 | 0.0558 (12) | 0.0494 (13) | 0.0487 (11) | −0.0107 (12) | −0.0023 (10) | 0.0037 (12) |
P5 | 0.0391 (11) | 0.0700 (16) | 0.0382 (11) | 0.0085 (11) | 0.0049 (9) | −0.0037 (11) |
P6 | 0.0521 (12) | 0.0526 (14) | 0.0453 (12) | 0.0123 (11) | 0.0035 (10) | 0.0121 (10) |
O3 | 0.051 (3) | 0.050 (3) | 0.031 (3) | 0.009 (3) | −0.005 (2) | −0.002 (2) |
O4 | 0.059 (4) | 0.090 (5) | 0.038 (3) | 0.011 (4) | 0.011 (3) | −0.008 (3) |
N2 | 0.041 (3) | 0.039 (3) | 0.022 (2) | −0.002 (3) | 0.000 (2) | 0.006 (3) |
C6 | 0.045 (4) | 0.041 (4) | 0.043 (4) | 0.007 (3) | 0.009 (4) | −0.002 (4) |
C7 | 0.038 (4) | 0.062 (6) | 0.044 (5) | 0.010 (4) | 0.000 (3) | 0.004 (4) |
C8 | 0.043 (5) | 0.133 (11) | 0.072 (7) | −0.017 (7) | 0.010 (5) | −0.019 (9) |
C9 | 0.056 (6) | 0.076 (7) | 0.064 (6) | −0.018 (5) | −0.013 (5) | 0.000 (6) |
C10 | 0.058 (6) | 0.051 (5) | 0.056 (5) | −0.011 (4) | −0.017 (5) | −0.007 (4) |
C41 | 0.127 (12) | 0.070 (8) | 0.076 (8) | −0.018 (8) | −0.038 (8) | 0.036 (7) |
C42 | 0.135 (11) | 0.043 (6) | 0.065 (7) | −0.025 (7) | −0.001 (7) | −0.003 (5) |
C43 | 0.065 (7) | 0.079 (9) | 0.145 (13) | −0.028 (6) | 0.021 (8) | 0.004 (8) |
C51 | 0.070 (7) | 0.132 (12) | 0.040 (5) | 0.021 (7) | 0.005 (5) | −0.003 (6) |
C52 | 0.108 (10) | 0.069 (7) | 0.066 (7) | 0.024 (7) | 0.009 (7) | −0.014 (6) |
C53 | 0.036 (5) | 0.124 (11) | 0.084 (8) | 0.017 (6) | 0.007 (5) | 0.005 (8) |
C61 | 0.22 (2) | 0.124 (13) | 0.049 (7) | 0.087 (14) | 0.053 (10) | 0.039 (8) |
C62 | 0.084 (9) | 0.095 (11) | 0.156 (15) | −0.020 (8) | −0.030 (10) | 0.064 (11) |
C63 | 0.079 (7) | 0.062 (6) | 0.057 (6) | 0.014 (6) | −0.014 (5) | 0.014 (5) |
Ir1 | 0.03547 (15) | 0.0540 (2) | 0.03524 (15) | −0.00449 (15) | 0.00001 (12) | −0.00367 (15) |
P1 | 0.0485 (13) | 0.080 (2) | 0.0641 (16) | 0.0015 (13) | 0.0004 (12) | −0.0302 (15) |
P2 | 0.0446 (12) | 0.0774 (18) | 0.0532 (14) | 0.0142 (13) | −0.0031 (11) | 0.0018 (13) |
P3 | 0.0754 (16) | 0.0640 (16) | 0.0574 (14) | −0.0267 (16) | −0.0038 (12) | −0.0042 (15) |
O1 | 0.047 (4) | 0.090 (5) | 0.040 (3) | 0.004 (4) | 0.003 (3) | 0.013 (3) |
O2 | 0.061 (4) | 0.090 (5) | 0.053 (4) | 0.015 (4) | −0.008 (3) | 0.014 (4) |
N1 | 0.048 (3) | 0.052 (4) | 0.026 (3) | −0.006 (4) | 0.002 (2) | −0.001 (3) |
C1 | 0.074 (7) | 0.060 (6) | 0.036 (4) | 0.010 (5) | −0.008 (4) | −0.002 (4) |
C2 | 0.041 (4) | 0.058 (5) | 0.043 (5) | −0.001 (4) | −0.001 (4) | −0.004 (4) |
C3 | 0.054 (5) | 0.119 (10) | 0.044 (5) | 0.002 (7) | −0.003 (4) | −0.006 (7) |
C4 | 0.050 (5) | 0.121 (10) | 0.058 (6) | −0.024 (6) | 0.003 (5) | −0.004 (7) |
C5 | 0.050 (5) | 0.080 (8) | 0.054 (6) | −0.004 (5) | 0.010 (4) | 0.006 (5) |
C11 | 0.18 (3) | 0.33 (5) | 0.17 (3) | 0.20 (4) | −0.11 (3) | −0.18 (4) |
C12 | 0.36 (5) | 0.094 (17) | 0.052 (11) | −0.04 (3) | 0.02 (2) | −0.037 (11) |
C13 | 0.14 (2) | 0.38 (6) | 0.18 (3) | −0.20 (4) | 0.12 (3) | −0.21 (4) |
C11' | 0.18 (3) | 0.33 (5) | 0.17 (3) | 0.20 (4) | −0.11 (3) | −0.18 (4) |
C12' | 0.36 (5) | 0.094 (17) | 0.052 (11) | −0.04 (3) | 0.02 (2) | −0.037 (11) |
C13' | 0.14 (2) | 0.38 (6) | 0.18 (3) | −0.20 (4) | 0.12 (3) | −0.21 (4) |
C21 | 0.150 (16) | 0.074 (9) | 0.121 (13) | 0.011 (10) | 0.003 (12) | 0.026 (9) |
C22 | 0.048 (6) | 0.174 (17) | 0.085 (9) | 0.020 (9) | −0.004 (6) | 0.000 (10) |
C23 | 0.091 (9) | 0.171 (17) | 0.050 (6) | 0.040 (10) | −0.002 (6) | −0.011 (8) |
C31 | 0.21 (2) | 0.122 (16) | 0.24 (3) | −0.112 (16) | −0.14 (2) | 0.047 (16) |
C32 | 0.28 (3) | 0.100 (13) | 0.154 (17) | −0.047 (16) | 0.146 (19) | −0.062 (13) |
C33 | 0.175 (17) | 0.086 (10) | 0.087 (10) | −0.052 (12) | 0.031 (11) | 0.000 (8) |
P2F | 0.088 (2) | 0.0630 (17) | 0.0421 (13) | −0.0072 (15) | 0.0048 (13) | −0.0013 (12) |
F7 | 0.109 (6) | 0.198 (11) | 0.068 (5) | −0.021 (7) | 0.022 (4) | 0.017 (6) |
F8 | 0.127 (7) | 0.121 (7) | 0.072 (5) | 0.039 (6) | −0.018 (5) | −0.018 (5) |
F9 | 0.146 (9) | 0.072 (6) | 0.140 (9) | −0.009 (5) | 0.003 (7) | −0.001 (5) |
F10 | 0.122 (7) | 0.193 (11) | 0.061 (4) | −0.004 (8) | −0.023 (5) | 0.004 (6) |
F11 | 0.333 (19) | 0.079 (6) | 0.101 (7) | −0.045 (9) | 0.018 (9) | −0.022 (5) |
F12 | 0.118 (7) | 0.211 (12) | 0.075 (5) | 0.047 (8) | 0.031 (5) | 0.026 (7) |
P1F | 0.078 (2) | 0.072 (2) | 0.0678 (18) | 0.0101 (16) | 0.0070 (16) | −0.0079 (15) |
F1 | 0.171 (12) | 0.28 (2) | 0.167 (12) | 0.026 (14) | 0.099 (11) | −0.041 (13) |
F2 | 0.253 (18) | 0.223 (18) | 0.174 (13) | 0.044 (14) | −0.115 (13) | −0.024 (12) |
F3 | 0.300 (18) | 0.090 (7) | 0.144 (10) | −0.004 (9) | −0.012 (11) | −0.020 (7) |
F4 | 0.150 (10) | 0.220 (15) | 0.180 (12) | 0.042 (10) | −0.080 (9) | −0.062 (11) |
F5 | 0.30 (2) | 0.072 (7) | 0.32 (2) | −0.035 (11) | 0.055 (17) | −0.006 (11) |
F6 | 0.152 (11) | 0.34 (2) | 0.148 (11) | 0.029 (13) | 0.051 (9) | −0.060 (13) |
Ir2—H | 1.42 (8) | P2—C21 | 1.827 (15) |
Ir2—P4 | 2.332 (3) | P2—C22 | 1.807 (12) |
Ir2—P5 | 2.252 (2) | P2—C23 | 1.833 (12) |
Ir2—P6 | 2.352 (2) | P3—C31 | 1.774 (17) |
Ir2—O3 | 2.114 (6) | P3—C32 | 1.792 (16) |
Ir2—N2 | 2.216 (6) | P3—C33 | 1.766 (15) |
P4—C41 | 1.798 (12) | O1—C1 | 1.256 (13) |
P4—C42 | 1.807 (12) | O2—C1 | 1.238 (11) |
P4—C43 | 1.823 (11) | N1—H1 | 0.9100 |
P5—C51 | 1.798 (11) | N1—C2 | 1.520 (11) |
P5—C52 | 1.824 (13) | N1—C5 | 1.467 (13) |
P5—C53 | 1.816 (10) | C1—C2 | 1.515 (13) |
P6—C61 | 1.796 (12) | C2—H2 | 0.9800 |
P6—C62 | 1.819 (15) | C2—C3 | 1.548 (14) |
P6—C63 | 1.802 (11) | C3—H3A | 0.9700 |
O3—C6 | 1.287 (10) | C3—H3B | 0.9700 |
O4—C6 | 1.186 (10) | C3—C4 | 1.525 (17) |
N2—H2A | 0.9100 | C4—H4A | 0.9700 |
N2—C7 | 1.521 (10) | C4—H4B | 0.9700 |
N2—C10 | 1.493 (12) | C4—C5 | 1.522 (14) |
C6—C7 | 1.522 (12) | C5—H5A | 0.9700 |
C7—H7 | 0.9800 | C5—H5B | 0.9700 |
C7—C8 | 1.507 (14) | C11—H11A | 0.9600 |
C8—H8A | 0.9700 | C11—H11B | 0.9600 |
C8—H8B | 0.9700 | C11—H11C | 0.9600 |
C8—C9 | 1.496 (17) | C12—H12A | 0.9600 |
C9—H9A | 0.9700 | C12—H12B | 0.9600 |
C9—H9B | 0.9700 | C12—H12C | 0.9600 |
C9—C10 | 1.520 (15) | C13—H13A | 0.9600 |
C10—H10A | 0.9700 | C13—H13B | 0.9600 |
C10—H10B | 0.9700 | C13—H13C | 0.9600 |
C41—H41A | 0.9600 | C11'—H11D | 0.9600 |
C41—H41B | 0.9600 | C11'—H11E | 0.9600 |
C41—H41C | 0.9600 | C11'—H11F | 0.9600 |
C42—H42A | 0.9600 | C12'—H12D | 0.9600 |
C42—H42B | 0.9600 | C12'—H12E | 0.9600 |
C42—H42C | 0.9600 | C12'—H12F | 0.9600 |
C43—H43A | 0.9600 | C13'—H13D | 0.9600 |
C43—H43B | 0.9600 | C13'—H13E | 0.9600 |
C43—H43C | 0.9600 | C13'—H13F | 0.9600 |
C51—H51A | 0.9600 | C21—H21A | 0.9600 |
C51—H51B | 0.9600 | C21—H21B | 0.9600 |
C51—H51C | 0.9600 | C21—H21C | 0.9600 |
C52—H52A | 0.9600 | C22—H22A | 0.9600 |
C52—H52B | 0.9600 | C22—H22B | 0.9600 |
C52—H52C | 0.9600 | C22—H22C | 0.9600 |
C53—H53A | 0.9600 | C23—H23A | 0.9600 |
C53—H53B | 0.9600 | C23—H23B | 0.9600 |
C53—H53C | 0.9600 | C23—H23C | 0.9600 |
C61—H61A | 0.9600 | C31—H31A | 0.9600 |
C61—H61B | 0.9600 | C31—H31B | 0.9600 |
C61—H61C | 0.9600 | C31—H31C | 0.9600 |
C62—H62A | 0.9600 | C32—H32A | 0.9600 |
C62—H62B | 0.9600 | C32—H32B | 0.9600 |
C62—H62C | 0.9600 | C32—H32C | 0.9600 |
C63—H63A | 0.9600 | C33—H33A | 0.9600 |
C63—H63B | 0.9600 | C33—H33B | 0.9600 |
C63—H63C | 0.9600 | C33—H33C | 0.9600 |
Ir1—HA | 1.69 (8) | P2F—F7 | 1.559 (8) |
Ir1—P1 | 2.346 (3) | P2F—F8 | 1.577 (8) |
Ir1—P2 | 2.241 (3) | P2F—F9 | 1.545 (9) |
Ir1—P3 | 2.328 (3) | P2F—F10 | 1.583 (8) |
Ir1—O1 | 2.123 (7) | P2F—F11 | 1.539 (10) |
Ir1—N1 | 2.206 (6) | P2F—F12 | 1.588 (9) |
P1—C11 | 1.76 (2) | P1F—F1 | 1.480 (11) |
P1—C12 | 1.93 (3) | P1F—F2 | 1.512 (13) |
P1—C13 | 1.68 (2) | P1F—F3 | 1.550 (13) |
P1—C11' | 1.72 (5) | P1F—F4 | 1.540 (11) |
P1—C12' | 2.01 (4) | P1F—F5 | 1.466 (12) |
P1—C13' | 1.57 (4) | P1F—F6 | 1.517 (12) |
P4—Ir2—H | 89 (4) | C13'—P1—C12 | 51 (3) |
P4—Ir2—P6 | 158.58 (9) | C13'—P1—C13 | 119.4 (17) |
P5—Ir2—H | 92 (3) | C13'—P1—C11' | 111 (2) |
P5—Ir2—P4 | 96.12 (10) | C13'—P1—C12' | 100 (3) |
P5—Ir2—P6 | 94.71 (9) | C21—P2—Ir1 | 115.8 (6) |
P6—Ir2—H | 72 (4) | C21—P2—C23 | 101.3 (9) |
O3—Ir2—H | 91 (3) | C22—P2—Ir1 | 117.3 (5) |
O3—Ir2—P4 | 86.36 (18) | C22—P2—C21 | 103.7 (9) |
O3—Ir2—P5 | 176.11 (18) | C22—P2—C23 | 102.6 (7) |
O3—Ir2—P6 | 83.91 (17) | C23—P2—Ir1 | 114.1 (5) |
O3—Ir2—N2 | 78.9 (2) | C31—P3—Ir1 | 118.8 (7) |
N2—Ir2—H | 169 (3) | C31—P3—C32 | 102.5 (12) |
N2—Ir2—P4 | 93.83 (19) | C32—P3—Ir1 | 121.6 (7) |
N2—Ir2—P5 | 97.94 (17) | C33—P3—Ir1 | 109.6 (5) |
N2—Ir2—P6 | 102.91 (18) | C33—P3—C31 | 100.3 (9) |
C41—P4—Ir2 | 119.2 (4) | C33—P3—C32 | 100.8 (10) |
C41—P4—C42 | 103.6 (7) | C1—O1—Ir1 | 117.2 (6) |
C41—P4—C43 | 102.8 (7) | Ir1—N1—H1 | 105.8 |
C42—P4—Ir2 | 109.4 (4) | C2—N1—Ir1 | 108.5 (5) |
C42—P4—C43 | 102.4 (7) | C2—N1—H1 | 105.8 |
C43—P4—Ir2 | 117.4 (5) | C5—N1—Ir1 | 122.8 (6) |
C51—P5—Ir2 | 115.6 (4) | C5—N1—H1 | 105.8 |
C51—P5—C52 | 101.9 (6) | C5—N1—C2 | 107.0 (7) |
C51—P5—C53 | 101.5 (6) | O1—C1—C2 | 119.8 (8) |
C52—P5—Ir2 | 116.0 (4) | O2—C1—O1 | 123.1 (9) |
C53—P5—Ir2 | 118.0 (5) | O2—C1—C2 | 117.1 (10) |
C53—P5—C52 | 101.3 (7) | N1—C2—H2 | 107.3 |
C61—P6—Ir2 | 109.6 (5) | N1—C2—C3 | 106.0 (8) |
C61—P6—C62 | 100.3 (9) | C1—C2—N1 | 113.0 (7) |
C61—P6—C63 | 103.4 (7) | C1—C2—H2 | 107.3 |
C62—P6—Ir2 | 125.4 (5) | C1—C2—C3 | 115.5 (8) |
C63—P6—Ir2 | 113.4 (4) | C3—C2—H2 | 107.3 |
C63—P6—C62 | 102.1 (6) | C2—C3—H3A | 111.1 |
C6—O3—Ir2 | 119.0 (5) | C2—C3—H3B | 111.1 |
Ir2—N2—H2A | 106.9 | H3A—C3—H3B | 109.0 |
C7—N2—Ir2 | 108.5 (4) | C4—C3—C2 | 103.4 (8) |
C7—N2—H2A | 106.9 | C4—C3—H3A | 111.1 |
C10—N2—Ir2 | 122.1 (6) | C4—C3—H3B | 111.1 |
C10—N2—H2A | 106.9 | C3—C4—H4A | 111.2 |
C10—N2—C7 | 104.5 (7) | C3—C4—H4B | 111.2 |
O3—C6—C7 | 116.0 (7) | H4A—C4—H4B | 109.1 |
O4—C6—O3 | 125.0 (9) | C5—C4—C3 | 102.8 (8) |
O4—C6—C7 | 119.0 (8) | C5—C4—H4A | 111.2 |
N2—C7—C6 | 113.4 (6) | C5—C4—H4B | 111.2 |
N2—C7—H7 | 107.1 | N1—C5—C4 | 105.1 (9) |
C6—C7—H7 | 107.1 | N1—C5—H5A | 110.7 |
C8—C7—N2 | 106.7 (8) | N1—C5—H5B | 110.7 |
C8—C7—C6 | 115.1 (8) | C4—C5—H5A | 110.7 |
C8—C7—H7 | 107.1 | C4—C5—H5B | 110.7 |
C7—C8—H8A | 110.7 | H5A—C5—H5B | 108.8 |
C7—C8—H8B | 110.7 | P1—C11—H11A | 109.5 |
H8A—C8—H8B | 108.8 | P1—C11—H11B | 109.5 |
C9—C8—C7 | 105.4 (8) | P1—C11—H11C | 109.5 |
C9—C8—H8A | 110.7 | H11A—C11—H11B | 109.5 |
C9—C8—H8B | 110.7 | H11A—C11—H11C | 109.5 |
C8—C9—H9A | 111.3 | H11B—C11—H11C | 109.5 |
C8—C9—H9B | 111.3 | P1—C12—H12A | 109.5 |
C8—C9—C10 | 102.5 (8) | P1—C12—H12B | 109.5 |
H9A—C9—H9B | 109.2 | P1—C12—H12C | 109.5 |
C10—C9—H9A | 111.3 | H12A—C12—H12B | 109.5 |
C10—C9—H9B | 111.3 | H12A—C12—H12C | 109.5 |
N2—C10—C9 | 103.5 (8) | H12B—C12—H12C | 109.5 |
N2—C10—H10A | 111.1 | P1—C13—H13A | 109.5 |
N2—C10—H10B | 111.1 | P1—C13—H13B | 109.5 |
C9—C10—H10A | 111.1 | P1—C13—H13C | 109.5 |
C9—C10—H10B | 111.1 | H13A—C13—H13B | 109.5 |
H10A—C10—H10B | 109.0 | H13A—C13—H13C | 109.5 |
P4—C41—H41A | 109.5 | H13B—C13—H13C | 109.5 |
P4—C41—H41B | 109.5 | P1—C11'—H11D | 109.5 |
P4—C41—H41C | 109.5 | P1—C11'—H11E | 109.5 |
H41A—C41—H41B | 109.5 | P1—C11'—H11F | 109.5 |
H41A—C41—H41C | 109.5 | H11D—C11'—H11E | 109.5 |
H41B—C41—H41C | 109.5 | H11D—C11'—H11F | 109.5 |
P4—C42—H42A | 109.5 | H11E—C11'—H11F | 109.5 |
P4—C42—H42B | 109.5 | P1—C12'—H12D | 109.5 |
P4—C42—H42C | 109.5 | P1—C12'—H12E | 109.5 |
H42A—C42—H42B | 109.5 | P1—C12'—H12F | 109.5 |
H42A—C42—H42C | 109.5 | H12D—C12'—H12E | 109.5 |
H42B—C42—H42C | 109.5 | H12D—C12'—H12F | 109.5 |
P4—C43—H43A | 109.5 | H12E—C12'—H12F | 109.5 |
P4—C43—H43B | 109.5 | P1—C13'—H13D | 109.5 |
P4—C43—H43C | 109.5 | P1—C13'—H13E | 109.5 |
H43A—C43—H43B | 109.5 | P1—C13'—H13F | 109.5 |
H43A—C43—H43C | 109.5 | H13D—C13'—H13E | 109.5 |
H43B—C43—H43C | 109.5 | H13D—C13'—H13F | 109.5 |
P5—C51—H51A | 109.5 | H13E—C13'—H13F | 109.5 |
P5—C51—H51B | 109.5 | P2—C21—H21A | 109.5 |
P5—C51—H51C | 109.5 | P2—C21—H21B | 109.5 |
H51A—C51—H51B | 109.5 | P2—C21—H21C | 109.5 |
H51A—C51—H51C | 109.5 | H21A—C21—H21B | 109.5 |
H51B—C51—H51C | 109.5 | H21A—C21—H21C | 109.5 |
P5—C52—H52A | 109.5 | H21B—C21—H21C | 109.5 |
P5—C52—H52B | 109.5 | P2—C22—H22A | 109.5 |
P5—C52—H52C | 109.5 | P2—C22—H22B | 109.5 |
H52A—C52—H52B | 109.5 | P2—C22—H22C | 109.5 |
H52A—C52—H52C | 109.5 | H22A—C22—H22B | 109.5 |
H52B—C52—H52C | 109.5 | H22A—C22—H22C | 109.5 |
P5—C53—H53A | 109.5 | H22B—C22—H22C | 109.5 |
P5—C53—H53B | 109.5 | P2—C23—H23A | 109.5 |
P5—C53—H53C | 109.5 | P2—C23—H23B | 109.5 |
H53A—C53—H53B | 109.5 | P2—C23—H23C | 109.5 |
H53A—C53—H53C | 109.5 | H23A—C23—H23B | 109.5 |
H53B—C53—H53C | 109.5 | H23A—C23—H23C | 109.5 |
P6—C61—H61A | 109.5 | H23B—C23—H23C | 109.5 |
P6—C61—H61B | 109.5 | P3—C31—H31A | 109.5 |
P6—C61—H61C | 109.5 | P3—C31—H31B | 109.5 |
H61A—C61—H61B | 109.5 | P3—C31—H31C | 109.5 |
H61A—C61—H61C | 109.5 | H31A—C31—H31B | 109.5 |
H61B—C61—H61C | 109.5 | H31A—C31—H31C | 109.5 |
P6—C62—H62A | 109.5 | H31B—C31—H31C | 109.5 |
P6—C62—H62B | 109.5 | P3—C32—H32A | 109.5 |
P6—C62—H62C | 109.5 | P3—C32—H32B | 109.5 |
H62A—C62—H62B | 109.5 | P3—C32—H32C | 109.5 |
H62A—C62—H62C | 109.5 | H32A—C32—H32B | 109.5 |
H62B—C62—H62C | 109.5 | H32A—C32—H32C | 109.5 |
P6—C63—H63A | 109.5 | H32B—C32—H32C | 109.5 |
P6—C63—H63B | 109.5 | P3—C33—H33A | 109.5 |
P6—C63—H63C | 109.5 | P3—C33—H33B | 109.5 |
H63A—C63—H63B | 109.5 | P3—C33—H33C | 109.5 |
H63A—C63—H63C | 109.5 | H33A—C33—H33B | 109.5 |
H63B—C63—H63C | 109.5 | H33A—C33—H33C | 109.5 |
P1—Ir1—HA | 78 (3) | H33B—C33—H33C | 109.5 |
P2—Ir1—HA | 84 (3) | F7—P2F—F8 | 89.6 (5) |
P2—Ir1—P1 | 97.77 (12) | F7—P2F—F10 | 89.2 (5) |
P2—Ir1—P3 | 96.65 (11) | F7—P2F—F12 | 178.1 (7) |
P3—Ir1—HA | 84 (3) | F8—P2F—F10 | 178.6 (6) |
P3—Ir1—P1 | 155.90 (11) | F8—P2F—F12 | 91.3 (5) |
O1—Ir1—HA | 98 (3) | F9—P2F—F7 | 90.3 (7) |
O1—Ir1—P1 | 81.9 (2) | F9—P2F—F8 | 89.6 (6) |
O1—Ir1—P2 | 177.4 (2) | F9—P2F—F10 | 89.7 (7) |
O1—Ir1—P3 | 84.5 (2) | F9—P2F—F12 | 88.0 (7) |
O1—Ir1—N1 | 79.6 (2) | F10—P2F—F12 | 89.9 (5) |
N1—Ir1—HA | 178 (3) | F11—P2F—F7 | 90.4 (7) |
N1—Ir1—P1 | 101.4 (2) | F11—P2F—F8 | 88.8 (7) |
N1—Ir1—P2 | 97.99 (18) | F11—P2F—F9 | 178.3 (8) |
N1—Ir1—P3 | 95.6 (2) | F11—P2F—F10 | 91.9 (8) |
C11—P1—Ir1 | 120.3 (11) | F11—P2F—F12 | 91.3 (8) |
C11—P1—C12 | 94.3 (17) | F1—P1F—F2 | 86.6 (10) |
C11—P1—C12' | 55 (2) | F1—P1F—F3 | 87.6 (9) |
C12—P1—Ir1 | 104.3 (8) | F1—P1F—F4 | 92.2 (9) |
C12—P1—C12' | 136.8 (13) | F1—P1F—F6 | 175.5 (11) |
C13—P1—Ir1 | 126.8 (11) | F2—P1F—F3 | 85.3 (9) |
C13—P1—C11 | 105 (2) | F2—P1F—F4 | 175.6 (9) |
C13—P1—C12 | 98.6 (17) | F2—P1F—F6 | 95.7 (10) |
C13—P1—C12' | 66 (2) | F4—P1F—F3 | 90.4 (8) |
C11'—P1—Ir1 | 121.7 (15) | F5—P1F—F1 | 96.0 (11) |
C11'—P1—C11 | 117.8 (18) | F5—P1F—F2 | 92.1 (11) |
C11'—P1—C12 | 75 (3) | F5—P1F—F3 | 175.5 (10) |
C11'—P1—C12' | 92 (2) | F5—P1F—F4 | 92.2 (10) |
C12'—P1—Ir1 | 117.2 (11) | F5—P1F—F6 | 87.8 (11) |
C13'—P1—Ir1 | 112.2 (17) | F6—P1F—F3 | 88.8 (10) |
C13'—P1—C11 | 46 (3) | F6—P1F—F4 | 85.3 (8) |
Ir2—O3—C6—O4 | 162.9 (8) | P1—Ir1—P2—C22 | −88.9 (7) |
Ir2—O3—C6—C7 | −18.6 (10) | P1—Ir1—P2—C23 | 151.1 (7) |
Ir2—N2—C7—C6 | −17.1 (9) | P1—Ir1—P3—C31 | 95.9 (10) |
Ir2—N2—C7—C8 | −144.8 (7) | P1—Ir1—P3—C32 | −135.3 (10) |
Ir2—N2—C10—C9 | 157.3 (6) | P1—Ir1—P3—C33 | −18.5 (8) |
P4—Ir2—P5—C51 | −44.0 (5) | P1—Ir1—O1—C1 | −100.2 (8) |
P4—Ir2—P5—C52 | −163.2 (5) | P1—Ir1—N1—C2 | 84.8 (5) |
P4—Ir2—P5—C53 | 76.3 (6) | P1—Ir1—N1—C5 | −40.8 (7) |
P4—Ir2—P6—C61 | 44.0 (8) | P2—Ir1—P1—C11 | 42 (2) |
P4—Ir2—P6—C62 | 163.1 (8) | P2—Ir1—P1—C12 | 145.8 (15) |
P4—Ir2—P6—C63 | −71.0 (5) | P2—Ir1—P1—C13 | −102 (3) |
P4—Ir2—O3—C6 | 101.2 (6) | P2—Ir1—P1—C11' | −133 (3) |
P4—Ir2—N2—C7 | −79.0 (5) | P2—Ir1—P1—C12' | −22 (2) |
P4—Ir2—N2—C10 | 159.5 (6) | P2—Ir1—P1—C13' | 93 (4) |
P5—Ir2—P4—C41 | 86.2 (6) | P2—Ir1—P3—C31 | −30.6 (10) |
P5—Ir2—P4—C42 | −155.0 (5) | P2—Ir1—P3—C32 | 98.3 (10) |
P5—Ir2—P4—C43 | −39.0 (6) | P2—Ir1—P3—C33 | −144.9 (7) |
P5—Ir2—P6—C61 | 164.2 (7) | P2—Ir1—N1—C2 | −175.6 (5) |
P5—Ir2—P6—C62 | −76.8 (8) | P2—Ir1—N1—C5 | 58.8 (7) |
P5—Ir2—P6—C63 | 49.2 (4) | P3—Ir1—P1—C11 | −84 (2) |
P5—Ir2—N2—C7 | −175.7 (5) | P3—Ir1—P1—C12 | 19.5 (15) |
P5—Ir2—N2—C10 | 62.8 (6) | P3—Ir1—P1—C13 | 132 (3) |
P6—Ir2—P4—C41 | −153.9 (6) | P3—Ir1—P1—C11' | 101 (3) |
P6—Ir2—P4—C42 | −35.0 (6) | P3—Ir1—P1—C12' | −148 (2) |
P6—Ir2—P4—C43 | 80.9 (6) | P3—Ir1—P1—C13' | −34 (4) |
P6—Ir2—P5—C51 | 154.5 (5) | P3—Ir1—P2—C21 | −165.2 (7) |
P6—Ir2—P5—C52 | 35.3 (5) | P3—Ir1—P2—C22 | 71.7 (7) |
P6—Ir2—P5—C53 | −85.2 (6) | P3—Ir1—P2—C23 | −48.3 (7) |
P6—Ir2—O3—C6 | −97.9 (6) | P3—Ir1—O1—C1 | 99.7 (7) |
P6—Ir2—N2—C7 | 87.6 (5) | P3—Ir1—N1—C2 | −78.0 (5) |
P6—Ir2—N2—C10 | −33.9 (6) | P3—Ir1—N1—C5 | 156.3 (6) |
O3—Ir2—P4—C41 | −90.8 (7) | O1—Ir1—P1—C11 | −141 (2) |
O3—Ir2—P4—C42 | 28.0 (6) | O1—Ir1—P1—C12 | −36.8 (15) |
O3—Ir2—P4—C43 | 144.0 (6) | O1—Ir1—P1—C13 | 76 (3) |
O3—Ir2—P6—C61 | −19.4 (7) | O1—Ir1—P1—C11' | 45 (3) |
O3—Ir2—P6—C62 | 99.6 (8) | O1—Ir1—P1—C12' | 156 (2) |
O3—Ir2—P6—C63 | −134.5 (5) | O1—Ir1—P1—C13' | −90 (4) |
O3—Ir2—N2—C7 | 6.5 (5) | O1—Ir1—P3—C31 | 151.7 (10) |
O3—Ir2—N2—C10 | −115.0 (6) | O1—Ir1—P3—C32 | −79.5 (10) |
O3—C6—C7—N2 | 23.9 (11) | O1—Ir1—P3—C33 | 37.4 (7) |
O3—C6—C7—C8 | 147.2 (10) | O1—Ir1—N1—C2 | 5.4 (5) |
O4—C6—C7—N2 | −157.5 (8) | O1—Ir1—N1—C5 | −120.3 (7) |
O4—C6—C7—C8 | −34.2 (14) | O1—C1—C2—N1 | 16.0 (13) |
N2—Ir2—P4—C41 | −12.3 (7) | O1—C1—C2—C3 | 138.4 (11) |
N2—Ir2—P4—C42 | 106.6 (6) | O2—C1—C2—N1 | −164.5 (9) |
N2—Ir2—P4—C43 | −137.4 (6) | O2—C1—C2—C3 | −42.1 (14) |
N2—Ir2—P5—C51 | 50.8 (6) | N1—Ir1—P1—C11 | 142 (2) |
N2—Ir2—P5—C52 | −68.4 (5) | N1—Ir1—P1—C12 | −114.4 (15) |
N2—Ir2—P5—C53 | 171.1 (6) | N1—Ir1—P1—C13 | −2 (3) |
N2—Ir2—P6—C61 | −96.5 (7) | N1—Ir1—P1—C11' | −33 (3) |
N2—Ir2—P6—C62 | 22.5 (8) | N1—Ir1—P1—C12' | 78 (2) |
N2—Ir2—P6—C63 | 148.5 (5) | N1—Ir1—P1—C13' | −167 (4) |
N2—Ir2—O3—C6 | 6.6 (6) | N1—Ir1—P2—C21 | −68.6 (7) |
N2—C7—C8—C9 | −13.1 (13) | N1—Ir1—P2—C22 | 168.4 (7) |
C6—C7—C8—C9 | −139.9 (10) | N1—Ir1—P2—C23 | 48.4 (7) |
C7—N2—C10—C9 | 33.9 (9) | N1—Ir1—P3—C31 | −129.3 (10) |
C7—C8—C9—C10 | 33.7 (13) | N1—Ir1—P3—C32 | −0.5 (10) |
C8—C9—C10—N2 | −42.1 (11) | N1—Ir1—P3—C33 | 116.4 (7) |
C10—N2—C7—C6 | 114.7 (8) | N1—Ir1—O1—C1 | 3.0 (7) |
C10—N2—C7—C8 | −13.1 (10) | N1—C2—C3—C4 | −19.3 (11) |
Ir1—O1—C1—O2 | 169.2 (8) | C1—C2—C3—C4 | −145.3 (9) |
Ir1—O1—C1—C2 | −11.3 (12) | C2—N1—C5—C4 | 27.6 (10) |
Ir1—N1—C2—C1 | −11.9 (9) | C2—C3—C4—C5 | 35.5 (12) |
Ir1—N1—C2—C3 | −139.4 (6) | C3—C4—C5—N1 | −39.7 (11) |
Ir1—N1—C5—C4 | 153.9 (6) | C5—N1—C2—C1 | 122.5 (8) |
P1—Ir1—P2—C21 | 34.1 (7) | C5—N1—C2—C3 | −5.0 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.91 | 2.04 | 2.909 (9) | 160 |
Symmetry code: (i) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.91 | 2.04 | 2.909 (9) | 159.7 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
Financial support for this work was provided by ACS–PRF (grant #23961-C1) and by the National Science Foundation (CHE-902244). The Virginia Tech Subvention Fund is gratefully acknowledged for covering the open-access fee.
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