Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050970/si2038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050970/si2038Isup2.hkl |
CCDC reference: 667190
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.024
- wR factor = 0.043
- Data-to-parameter ratio = 23.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.10 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for B1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C44 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 39
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the corresponding solvate-free bis(triphenylphosphine) complex, [Ir(H)2{P(C6H5)3}2{OC(CH3)2}2][BF4], see Crabtree et al. (1984). For data analysis techniques, see Orpen (1980).
Single crystals of the title compound were obtained by protonation of [Ir(H)5{P(C6H11)3}2] with tetrafluoridoboric acid (54% in diethyl ether) in acetone, followed by slow evaporation of the solvent at ambient temperature.
The rotational disorder of the BF4- anion about the B1—F1 axis was modelled using one major and two minor orientations of the remaining BF3 fragment with fluorine site occupancies fixed at 0.65, 1/4, and 0.10, respectively. Standard SADI restraints with subsequent rigid-group refinement were applied for the tetrahedral dimensions of the disordered ion. The two hydride ligands were placed, with Ir—H restrained to 1.55 Å, at the positions calculated by the HYDEX energy-minimizing procedure (Orpen, 1980). Carbon-bound H atoms were positioned geometrically (C—H = 0.96–0.99 Å) and refined using appropriate riding models. All hydrogen Uiso values were fixed at 1.2 times Ueq of the preceding carrier atom.
The cation of the title complex (Fig. 1), adopts a slightly distorted OC-6–13 coordination geometry, where the two monodentate phosphines lie trans to each other [Ir—P = 2.3159 (6) and 2.3267 (6) Å] and the hydrides are opposite to the O-bound acetone groups [Ir—O = 2.238 (1) and 2.276 (1) Å] (Table 1). The tetrafluoridoborate anion exhibts threefold rotational disorder about the B1—F1 axis. The acetone molecule of solvation, by contrast, is located in fully ordered atomic positions.
The ionic components are linked by C—H···F hydrogen-bonding contacts, in which atoms C39 and C40 of the acetone ligands act as donors, via H39B and H40B, to fluorine atoms F4 and F1 with C39···F4(-x + 1, y - 1/2, -z + 1/2) = 3.441 (3) Å and C40···F1(x - 1, -y + 3/2, z - 1/2 + z) = 3.434 (3) Å, respectively. Even though the cation displays several intramolecular C—H···O interactions with C···O distances in the range 3.207 (3)–3.358 (3) Å (Table 2), the oxygen atom of the solvate molecule does not function as a carbon—hydrogen bond acceptor.
In the corresponding solvate-free bis(triphenylphosphine) complex [Ir(H)2{P(C6H5)3}2{OC(CH3)2}2][BF4], the cation also has pseudooctahedral geometry with the two phosphines in mutual trans coordination and the hydrido ligands opposite to the acetone molecules (Crabtree et al., 1984).
For the corresponding solvate-free bis(triphenylphosphine) complex, [Ir(H)2{P(C6H5)3}2{OC(CH3)2}2][BF4], see Crabtree et al. (1984). For data analysis techniques, see Orpen (1980).
Data collection: COLLECT (Bruker, 2002); cell refinement: COLLECT (Bruker, 2002); data reduction: COLLECT (Bruker, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[IrH2(C18H33P)2(C3H6O)2]BF4·C3H6O | F(000) = 2112 |
Mr = 1016.09 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 244 reflections |
a = 10.218 (1) Å | θ = 6–20° |
b = 25.199 (4) Å | µ = 2.82 mm−1 |
c = 19.621 (1) Å | T = 100 K |
β = 102.060 (5)° | Irregular, yellow |
V = 4940.6 (10) Å3 | 0.20 × 0.18 × 0.17 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 12737 independent reflections |
Graphite monochromator | 10353 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.049 |
φ– and ω–rotations with 1.10 ° and 55 sec per frame scans | θmax = 28.7°, θmin = 3.0° |
Absorption correction: integration (Gaussian; Coppens et al., 1965) | h = −13→13 |
Tmin = 0.562, Tmax = 0.687 | k = −34→34 |
111705 measured reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: mixed |
wR(F2) = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0135P)2 + 3.6535P] where P = (Fo2 + 2Fc2)/3 |
12737 reflections | (Δ/σ)max = 0.004 |
544 parameters | Δρmax = 0.54 e Å−3 |
39 restraints | Δρmin = −0.52 e Å−3 |
[IrH2(C18H33P)2(C3H6O)2]BF4·C3H6O | V = 4940.6 (10) Å3 |
Mr = 1016.09 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.218 (1) Å | µ = 2.82 mm−1 |
b = 25.199 (4) Å | T = 100 K |
c = 19.621 (1) Å | 0.20 × 0.18 × 0.17 mm |
β = 102.060 (5)° |
Nonius KappaCCD area-detector diffractometer | 12737 independent reflections |
Absorption correction: integration (Gaussian; Coppens et al., 1965) | 10353 reflections with I > 2σ(I) |
Tmin = 0.562, Tmax = 0.687 | Rint = 0.049 |
111705 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 39 restraints |
wR(F2) = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.54 e Å−3 |
12737 reflections | Δρmin = −0.52 e Å−3 |
544 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ir1 | 0.284245 (8) | 0.460836 (3) | 0.267476 (4) | 0.00798 (2) | |
H1 | 0.2025 (16) | 0.4558 (8) | 0.3224 (9) | 0.010* | |
H2 | 0.4088 (14) | 0.4555 (8) | 0.3262 (9) | 0.010* | |
P1 | 0.28670 (6) | 0.368517 (19) | 0.26606 (3) | 0.00904 (10) | |
P2 | 0.29923 (5) | 0.549912 (19) | 0.29715 (3) | 0.00913 (10) | |
O1 | 0.41473 (14) | 0.46566 (6) | 0.18679 (7) | 0.0136 (3) | |
O2 | 0.11784 (13) | 0.46847 (5) | 0.17367 (7) | 0.0108 (3) | |
C1 | 0.2342 (2) | 0.33866 (8) | 0.34236 (10) | 0.0113 (4) | |
H1A | 0.2436 | 0.2993 | 0.3390 | 0.014* | |
C2 | 0.0868 (2) | 0.35053 (8) | 0.34315 (10) | 0.0141 (4) | |
H2A | 0.0731 | 0.3894 | 0.3430 | 0.017* | |
H2B | 0.0290 | 0.3359 | 0.3005 | 0.017* | |
C3 | 0.0458 (2) | 0.32642 (9) | 0.40740 (10) | 0.0159 (4) | |
H3A | −0.0470 | 0.3372 | 0.4082 | 0.019* | |
H3B | 0.0480 | 0.2872 | 0.4043 | 0.019* | |
C4 | 0.1392 (2) | 0.34446 (9) | 0.47470 (11) | 0.0160 (5) | |
H4A | 0.1309 | 0.3833 | 0.4800 | 0.019* | |
H4B | 0.1128 | 0.3271 | 0.5150 | 0.019* | |
C5 | 0.2838 (2) | 0.33051 (9) | 0.47383 (10) | 0.0150 (4) | |
H5A | 0.2933 | 0.2915 | 0.4710 | 0.018* | |
H5B | 0.3430 | 0.3429 | 0.5175 | 0.018* | |
C6 | 0.3258 (2) | 0.35675 (8) | 0.41109 (10) | 0.0137 (4) | |
H6A | 0.4196 | 0.3472 | 0.4107 | 0.016* | |
H6B | 0.3207 | 0.3958 | 0.4153 | 0.016* | |
C7 | 0.4517 (2) | 0.33716 (8) | 0.26411 (10) | 0.0111 (4) | |
H7 | 0.4538 | 0.3330 | 0.2137 | 0.013* | |
C8 | 0.5737 (2) | 0.37216 (8) | 0.29526 (11) | 0.0131 (4) | |
H8A | 0.5615 | 0.4080 | 0.2741 | 0.016* | |
H8B | 0.5804 | 0.3760 | 0.3461 | 0.016* | |
C9 | 0.7031 (2) | 0.34750 (8) | 0.28166 (11) | 0.0161 (5) | |
H9A | 0.7802 | 0.3696 | 0.3041 | 0.019* | |
H9B | 0.6998 | 0.3472 | 0.2309 | 0.019* | |
C10 | 0.7234 (2) | 0.29056 (8) | 0.30994 (12) | 0.0184 (5) | |
H10A | 0.8034 | 0.2750 | 0.2966 | 0.022* | |
H10B | 0.7392 | 0.2913 | 0.3615 | 0.022* | |
C11 | 0.6014 (2) | 0.25610 (9) | 0.28129 (12) | 0.0178 (5) | |
H11A | 0.6143 | 0.2205 | 0.3031 | 0.021* | |
H11B | 0.5927 | 0.2516 | 0.2304 | 0.021* | |
C12 | 0.4729 (2) | 0.28085 (8) | 0.29554 (11) | 0.0149 (4) | |
H12A | 0.4784 | 0.2827 | 0.3465 | 0.018* | |
H12B | 0.3955 | 0.2582 | 0.2750 | 0.018* | |
C13 | 0.1699 (2) | 0.33971 (8) | 0.18943 (10) | 0.0124 (4) | |
H13 | 0.0807 | 0.3562 | 0.1889 | 0.015* | |
C14 | 0.1472 (2) | 0.27940 (8) | 0.18914 (11) | 0.0180 (5) | |
H14A | 0.2318 | 0.2609 | 0.1872 | 0.022* | |
H14B | 0.1200 | 0.2688 | 0.2327 | 0.022* | |
C15 | 0.0383 (2) | 0.26304 (9) | 0.12626 (12) | 0.0232 (5) | |
H15A | 0.0275 | 0.2240 | 0.1260 | 0.028* | |
H15B | −0.0480 | 0.2793 | 0.1303 | 0.028* | |
C16 | 0.0744 (2) | 0.28069 (9) | 0.05804 (12) | 0.0242 (5) | |
H16A | 0.1555 | 0.2615 | 0.0516 | 0.029* | |
H16B | 0.0004 | 0.2715 | 0.0186 | 0.029* | |
C17 | 0.1001 (2) | 0.34030 (9) | 0.05797 (11) | 0.0202 (5) | |
H17A | 0.0161 | 0.3596 | 0.0592 | 0.024* | |
H17B | 0.1287 | 0.3503 | 0.0145 | 0.024* | |
C18 | 0.2081 (2) | 0.35652 (9) | 0.12081 (10) | 0.0147 (5) | |
H18A | 0.2204 | 0.3955 | 0.1206 | 0.018* | |
H18B | 0.2941 | 0.3397 | 0.1174 | 0.018* | |
C19 | 0.1703 (2) | 0.59093 (8) | 0.23935 (10) | 0.0115 (4) | |
H19 | 0.0854 | 0.5701 | 0.2341 | 0.014* | |
C20 | 0.1990 (2) | 0.59394 (8) | 0.16537 (10) | 0.0144 (4) | |
H20A | 0.2749 | 0.6183 | 0.1653 | 0.017* | |
H20B | 0.2242 | 0.5584 | 0.1510 | 0.017* | |
C21 | 0.0750 (2) | 0.61381 (9) | 0.11372 (11) | 0.0165 (5) | |
H21A | 0.0008 | 0.5882 | 0.1119 | 0.020* | |
H21B | 0.0950 | 0.6161 | 0.0666 | 0.020* | |
C22 | 0.0319 (2) | 0.66848 (9) | 0.13532 (11) | 0.0188 (5) | |
H22A | 0.1011 | 0.6950 | 0.1310 | 0.023* | |
H22B | −0.0527 | 0.6791 | 0.1036 | 0.023* | |
C23 | 0.0118 (2) | 0.66789 (9) | 0.21033 (11) | 0.0199 (5) | |
H23A | −0.0665 | 0.6455 | 0.2129 | 0.024* | |
H23B | −0.0075 | 0.7044 | 0.2241 | 0.024* | |
C24 | 0.1351 (2) | 0.64662 (8) | 0.26185 (11) | 0.0160 (5) | |
H24A | 0.2119 | 0.6708 | 0.2630 | 0.019* | |
H24B | 0.1161 | 0.6451 | 0.3093 | 0.019* | |
C25 | 0.2682 (2) | 0.56519 (8) | 0.38504 (10) | 0.0115 (4) | |
H25 | 0.2741 | 0.6046 | 0.3905 | 0.014* | |
C26 | 0.1266 (2) | 0.54915 (8) | 0.39223 (11) | 0.0157 (5) | |
H26A | 0.0602 | 0.5654 | 0.3539 | 0.019* | |
H26B | 0.1172 | 0.5101 | 0.3880 | 0.019* | |
C27 | 0.0977 (2) | 0.56690 (10) | 0.46231 (11) | 0.0209 (5) | |
H27A | 0.0081 | 0.5540 | 0.4664 | 0.025* | |
H27B | 0.0966 | 0.6062 | 0.4642 | 0.025* | |
C28 | 0.2031 (2) | 0.54562 (10) | 0.52352 (11) | 0.0234 (5) | |
H28A | 0.1864 | 0.5604 | 0.5677 | 0.028* | |
H28B | 0.1955 | 0.5065 | 0.5256 | 0.028* | |
C29 | 0.3438 (2) | 0.56049 (9) | 0.51579 (11) | 0.0173 (5) | |
H29A | 0.4100 | 0.5444 | 0.5544 | 0.021* | |
H29B | 0.3544 | 0.5995 | 0.5190 | 0.021* | |
C30 | 0.3711 (2) | 0.54132 (9) | 0.44602 (10) | 0.0134 (4) | |
H30A | 0.3660 | 0.5021 | 0.4439 | 0.016* | |
H30B | 0.4625 | 0.5520 | 0.4421 | 0.016* | |
C31 | 0.4636 (2) | 0.57988 (8) | 0.29324 (10) | 0.0102 (4) | |
H31 | 0.4598 | 0.5878 | 0.2429 | 0.012* | |
C32 | 0.4943 (2) | 0.63318 (8) | 0.33186 (11) | 0.0146 (4) | |
H32A | 0.4197 | 0.6582 | 0.3154 | 0.018* | |
H32B | 0.5011 | 0.6275 | 0.3824 | 0.018* | |
C33 | 0.6248 (2) | 0.65754 (9) | 0.31986 (12) | 0.0194 (5) | |
H33A | 0.6437 | 0.6906 | 0.3475 | 0.023* | |
H33B | 0.6144 | 0.6669 | 0.2700 | 0.023* | |
C34 | 0.7431 (2) | 0.61922 (9) | 0.34073 (12) | 0.0183 (5) | |
H34A | 0.7610 | 0.6133 | 0.3917 | 0.022* | |
H34B | 0.8242 | 0.6352 | 0.3290 | 0.022* | |
C35 | 0.7132 (2) | 0.56596 (9) | 0.30276 (11) | 0.0162 (5) | |
H35A | 0.7054 | 0.5714 | 0.2521 | 0.019* | |
H35B | 0.7882 | 0.5411 | 0.3192 | 0.019* | |
C36 | 0.58314 (19) | 0.54158 (8) | 0.31571 (10) | 0.0133 (4) | |
H36A | 0.5937 | 0.5332 | 0.3659 | 0.016* | |
H36B | 0.5648 | 0.5080 | 0.2892 | 0.016* | |
C37 | 0.5669 (2) | 0.46118 (11) | 0.11183 (12) | 0.0256 (5) | |
H37A | 0.6069 | 0.4950 | 0.1022 | 0.031* | |
H37B | 0.5582 | 0.4379 | 0.0711 | 0.031* | |
H37C | 0.6242 | 0.4442 | 0.1522 | 0.031* | |
C38 | 0.4313 (2) | 0.47117 (8) | 0.12710 (11) | 0.0144 (4) | |
C39 | 0.3235 (2) | 0.48740 (9) | 0.06649 (11) | 0.0192 (5) | |
H39A | 0.2376 | 0.4890 | 0.0812 | 0.023* | |
H39B | 0.3178 | 0.4614 | 0.0288 | 0.023* | |
H39C | 0.3445 | 0.5224 | 0.0499 | 0.023* | |
C40 | −0.0856 (2) | 0.46968 (9) | 0.08943 (11) | 0.0190 (5) | |
H40A | −0.0248 | 0.4696 | 0.0568 | 0.023* | |
H40B | −0.1409 | 0.5018 | 0.0823 | 0.023* | |
H40C | −0.1433 | 0.4383 | 0.0813 | 0.023* | |
C41 | −0.0053 (2) | 0.46875 (8) | 0.16295 (11) | 0.0131 (4) | |
C42 | −0.0809 (2) | 0.46771 (10) | 0.22023 (11) | 0.0232 (5) | |
H42A | −0.0183 | 0.4717 | 0.2652 | 0.028* | |
H42B | −0.1283 | 0.4338 | 0.2193 | 0.028* | |
H42C | −0.1456 | 0.4969 | 0.2139 | 0.028* | |
O3 | 0.2746 (2) | 0.84436 (9) | 0.41579 (13) | 0.0681 (7) | |
C43 | 0.3208 (3) | 0.80391 (15) | 0.52688 (16) | 0.0534 (9) | |
H43A | 0.2404 | 0.8229 | 0.5331 | 0.064* | |
H43B | 0.3983 | 0.8165 | 0.5614 | 0.064* | |
H43C | 0.3089 | 0.7658 | 0.5332 | 0.064* | |
C44 | 0.3432 (3) | 0.81387 (11) | 0.45587 (14) | 0.0342 (6) | |
C45 | 0.4556 (3) | 0.78411 (16) | 0.43585 (17) | 0.0606 (10) | |
H45A | 0.4384 | 0.7459 | 0.4374 | 0.073* | |
H45B | 0.5394 | 0.7926 | 0.4685 | 0.073* | |
H45C | 0.4629 | 0.7942 | 0.3886 | 0.073* | |
B1 | 0.63333 (11) | 0.88431 (5) | 0.59616 (6) | 0.0282 (6) | |
F1 | 0.74063 (11) | 0.91865 (5) | 0.61781 (7) | 0.0412 (4) | |
F2 | 0.52168 (13) | 0.90752 (10) | 0.61630 (14) | 0.0564 (10) | 0.65 |
F3 | 0.6589 (2) | 0.83624 (6) | 0.62953 (14) | 0.0490 (9) | 0.65 |
F4 | 0.6068 (2) | 0.87863 (10) | 0.52580 (6) | 0.0632 (12) | 0.65 |
F2A | 0.53400 (16) | 0.89281 (10) | 0.63199 (12) | 0.040 (3) | 0.25 |
F3A | 0.6728 (2) | 0.83142 (4) | 0.60168 (16) | 0.047 (3) | 0.25 |
F4A | 0.5812 (2) | 0.89353 (10) | 0.52508 (7) | 0.042 (3) | 0.25 |
F2B | 0.5769 (2) | 0.86477 (11) | 0.64814 (9) | 0.045 (5) | 0.10 |
F3B | 0.6844 (2) | 0.84045 (7) | 0.56388 (15) | 0.061 (6) | 0.10 |
F4B | 0.53435 (17) | 0.90809 (8) | 0.54592 (12) | 0.051 (6) | 0.10 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ir1 | 0.00797 (4) | 0.00727 (3) | 0.00852 (4) | 0.00048 (4) | 0.00131 (2) | −0.00013 (3) |
P1 | 0.0090 (2) | 0.0085 (2) | 0.0092 (2) | 0.0000 (2) | 0.00099 (18) | −0.0004 (2) |
P2 | 0.0093 (2) | 0.0083 (3) | 0.0095 (2) | 0.00102 (19) | 0.00132 (19) | 0.00001 (18) |
O1 | 0.0153 (7) | 0.0139 (7) | 0.0122 (7) | −0.0019 (6) | 0.0046 (6) | −0.0008 (6) |
O2 | 0.0083 (7) | 0.0106 (7) | 0.0129 (7) | 0.0007 (6) | 0.0008 (5) | −0.0003 (5) |
C1 | 0.0118 (10) | 0.0098 (10) | 0.0122 (10) | −0.0011 (8) | 0.0027 (8) | 0.0001 (8) |
C2 | 0.0124 (11) | 0.0166 (11) | 0.0127 (10) | −0.0005 (8) | 0.0009 (8) | 0.0002 (8) |
C3 | 0.0152 (11) | 0.0178 (11) | 0.0156 (11) | −0.0030 (9) | 0.0055 (9) | 0.0013 (8) |
C4 | 0.0177 (12) | 0.0177 (11) | 0.0137 (11) | −0.0019 (9) | 0.0061 (9) | 0.0012 (8) |
C5 | 0.0178 (11) | 0.0170 (11) | 0.0098 (10) | −0.0002 (9) | 0.0021 (8) | 0.0024 (8) |
C6 | 0.0138 (11) | 0.0153 (11) | 0.0122 (10) | −0.0004 (9) | 0.0032 (8) | −0.0010 (8) |
C7 | 0.0104 (10) | 0.0113 (10) | 0.0117 (10) | 0.0023 (8) | 0.0026 (8) | −0.0016 (8) |
C8 | 0.0117 (11) | 0.0129 (10) | 0.0140 (11) | 0.0003 (8) | 0.0014 (8) | −0.0007 (8) |
C9 | 0.0112 (11) | 0.0172 (11) | 0.0193 (11) | 0.0006 (9) | 0.0021 (9) | 0.0014 (9) |
C10 | 0.0124 (11) | 0.0151 (11) | 0.0266 (13) | 0.0041 (9) | 0.0017 (9) | −0.0002 (9) |
C11 | 0.0167 (12) | 0.0136 (11) | 0.0218 (12) | 0.0051 (9) | 0.0009 (9) | −0.0005 (9) |
C12 | 0.0129 (11) | 0.0106 (10) | 0.0197 (11) | 0.0006 (8) | −0.0004 (9) | −0.0013 (8) |
C13 | 0.0100 (10) | 0.0142 (10) | 0.0118 (10) | −0.0016 (8) | −0.0001 (8) | −0.0025 (8) |
C14 | 0.0209 (12) | 0.0141 (11) | 0.0168 (11) | −0.0025 (9) | −0.0011 (9) | −0.0010 (8) |
C15 | 0.0248 (13) | 0.0176 (12) | 0.0239 (13) | −0.0068 (10) | −0.0025 (10) | −0.0051 (9) |
C16 | 0.0279 (14) | 0.0217 (12) | 0.0180 (12) | 0.0010 (10) | −0.0063 (10) | −0.0101 (9) |
C17 | 0.0246 (13) | 0.0206 (12) | 0.0129 (11) | 0.0007 (10) | −0.0019 (9) | −0.0033 (9) |
C18 | 0.0152 (11) | 0.0169 (11) | 0.0113 (10) | 0.0002 (9) | 0.0013 (8) | −0.0018 (8) |
C19 | 0.0096 (10) | 0.0114 (10) | 0.0121 (10) | 0.0012 (8) | −0.0009 (8) | 0.0007 (8) |
C20 | 0.0161 (11) | 0.0147 (11) | 0.0122 (10) | 0.0028 (9) | 0.0024 (8) | 0.0019 (8) |
C21 | 0.0190 (12) | 0.0163 (11) | 0.0126 (11) | 0.0037 (9) | −0.0002 (9) | 0.0003 (8) |
C22 | 0.0200 (12) | 0.0153 (11) | 0.0177 (11) | 0.0045 (9) | −0.0039 (9) | 0.0029 (9) |
C23 | 0.0202 (12) | 0.0167 (11) | 0.0209 (12) | 0.0108 (9) | −0.0001 (9) | −0.0014 (9) |
C24 | 0.0190 (12) | 0.0133 (10) | 0.0141 (11) | 0.0049 (9) | 0.0000 (9) | −0.0015 (8) |
C25 | 0.0137 (11) | 0.0111 (10) | 0.0101 (10) | 0.0014 (8) | 0.0033 (8) | −0.0006 (8) |
C26 | 0.0139 (11) | 0.0176 (12) | 0.0164 (11) | 0.0010 (8) | 0.0050 (8) | −0.0018 (8) |
C27 | 0.0172 (12) | 0.0259 (13) | 0.0224 (12) | −0.0008 (10) | 0.0106 (10) | −0.0046 (10) |
C28 | 0.0282 (13) | 0.0285 (14) | 0.0159 (11) | 0.0005 (11) | 0.0101 (10) | −0.0011 (10) |
C29 | 0.0203 (12) | 0.0194 (11) | 0.0118 (11) | 0.0031 (9) | 0.0023 (9) | −0.0001 (8) |
C30 | 0.0148 (10) | 0.0140 (10) | 0.0117 (10) | 0.0003 (9) | 0.0033 (8) | 0.0017 (8) |
C31 | 0.0100 (10) | 0.0105 (10) | 0.0103 (10) | −0.0006 (8) | 0.0028 (8) | 0.0009 (7) |
C32 | 0.0136 (11) | 0.0107 (10) | 0.0192 (11) | −0.0008 (8) | 0.0028 (9) | −0.0003 (8) |
C33 | 0.0200 (12) | 0.0131 (11) | 0.0250 (12) | −0.0061 (9) | 0.0044 (10) | −0.0011 (9) |
C34 | 0.0138 (11) | 0.0207 (12) | 0.0207 (12) | −0.0052 (9) | 0.0045 (9) | −0.0018 (9) |
C35 | 0.0106 (11) | 0.0206 (12) | 0.0177 (11) | 0.0006 (9) | 0.0036 (9) | −0.0019 (9) |
C36 | 0.0104 (10) | 0.0116 (9) | 0.0176 (10) | 0.0008 (9) | 0.0022 (8) | −0.0006 (9) |
C37 | 0.0163 (11) | 0.0397 (14) | 0.0225 (12) | 0.0032 (12) | 0.0082 (9) | 0.0049 (11) |
C38 | 0.0135 (11) | 0.0119 (11) | 0.0181 (11) | −0.0014 (8) | 0.0043 (8) | 0.0000 (8) |
C39 | 0.0200 (12) | 0.0241 (12) | 0.0141 (11) | 0.0031 (10) | 0.0053 (9) | 0.0017 (9) |
C40 | 0.0141 (11) | 0.0242 (13) | 0.0167 (11) | 0.0025 (9) | −0.0015 (9) | −0.0010 (9) |
C41 | 0.0132 (10) | 0.0074 (10) | 0.0176 (11) | 0.0016 (8) | 0.0010 (8) | −0.0001 (8) |
C42 | 0.0154 (11) | 0.0352 (15) | 0.0190 (12) | 0.0022 (10) | 0.0034 (9) | 0.0022 (10) |
O3 | 0.0511 (15) | 0.0535 (15) | 0.0860 (18) | −0.0109 (12) | −0.0170 (13) | 0.0303 (13) |
C43 | 0.045 (2) | 0.076 (3) | 0.0460 (19) | −0.0144 (18) | 0.0257 (16) | −0.0103 (17) |
C44 | 0.0280 (15) | 0.0336 (15) | 0.0383 (16) | −0.0072 (12) | 0.0011 (12) | 0.0046 (12) |
C45 | 0.054 (2) | 0.089 (3) | 0.044 (2) | −0.001 (2) | 0.0210 (17) | −0.0189 (19) |
B1 | 0.0293 (16) | 0.0300 (16) | 0.0256 (16) | −0.0019 (13) | 0.0059 (13) | 0.0038 (12) |
F1 | 0.0244 (8) | 0.0388 (10) | 0.0593 (11) | −0.0064 (7) | 0.0062 (8) | −0.0015 (8) |
F2 | 0.0292 (19) | 0.0468 (18) | 0.097 (3) | 0.0002 (14) | 0.0225 (18) | −0.0071 (19) |
F3 | 0.048 (2) | 0.0413 (19) | 0.056 (2) | −0.0039 (15) | 0.0060 (15) | 0.0273 (14) |
F4 | 0.111 (3) | 0.055 (2) | 0.025 (2) | −0.029 (2) | 0.0166 (19) | 0.0024 (13) |
F2A | 0.033 (5) | 0.073 (6) | 0.019 (3) | −0.008 (4) | 0.018 (3) | −0.019 (4) |
F3A | 0.047 (5) | 0.033 (4) | 0.057 (6) | 0.000 (3) | 0.000 (4) | 0.023 (3) |
F4A | 0.053 (5) | 0.046 (5) | 0.024 (5) | −0.010 (4) | 0.000 (4) | 0.010 (3) |
F2B | 0.045 (8) | 0.054 (9) | 0.035 (8) | −0.016 (7) | 0.003 (7) | 0.016 (7) |
F3B | 0.052 (9) | 0.067 (9) | 0.063 (9) | 0.013 (7) | 0.009 (7) | −0.026 (8) |
F4B | 0.048 (9) | 0.040 (8) | 0.055 (9) | 0.000 (7) | −0.010 (7) | 0.012 (7) |
Ir1—O2 | 2.2379 (13) | C22—H22B | 0.9900 |
Ir1—O1 | 2.2762 (14) | C23—C24 | 1.537 (3) |
Ir1—P2 | 2.3159 (6) | C23—H23A | 0.9900 |
Ir1—P1 | 2.3267 (6) | C23—H23B | 0.9900 |
Ir1—H1 | 1.501 (14) | C24—H24A | 0.9900 |
Ir1—H2 | 1.534 (14) | C24—H24B | 0.9900 |
P1—C1 | 1.852 (2) | C25—C26 | 1.537 (3) |
P1—C13 | 1.861 (2) | C25—C30 | 1.541 (3) |
P1—C7 | 1.870 (2) | C25—H25 | 1.0000 |
P2—C25 | 1.858 (2) | C26—C27 | 1.532 (3) |
P2—C31 | 1.858 (2) | C26—H26A | 0.9900 |
P2—C19 | 1.862 (2) | C26—H26B | 0.9900 |
O1—C38 | 1.226 (2) | C27—C28 | 1.533 (3) |
O2—C41 | 1.232 (2) | C27—H27A | 0.9900 |
C1—C2 | 1.539 (3) | C27—H27B | 0.9900 |
C1—C6 | 1.541 (3) | C28—C29 | 1.524 (3) |
C1—H1A | 1.0000 | C28—H28A | 0.9900 |
C2—C3 | 1.534 (3) | C28—H28B | 0.9900 |
C2—H2A | 0.9900 | C29—C30 | 1.531 (3) |
C2—H2B | 0.9900 | C29—H29A | 0.9900 |
C3—C4 | 1.528 (3) | C29—H29B | 0.9900 |
C3—H3A | 0.9900 | C30—H30A | 0.9900 |
C3—H3B | 0.9900 | C30—H30B | 0.9900 |
C4—C5 | 1.523 (3) | C31—C32 | 1.542 (3) |
C4—H4A | 0.9900 | C31—C36 | 1.547 (3) |
C4—H4B | 0.9900 | C31—H31 | 1.0000 |
C5—C6 | 1.535 (3) | C32—C33 | 1.531 (3) |
C5—H5A | 0.9900 | C32—H32A | 0.9900 |
C5—H5B | 0.9900 | C32—H32B | 0.9900 |
C6—H6A | 0.9900 | C33—C34 | 1.534 (3) |
C6—H6B | 0.9900 | C33—H33A | 0.9900 |
C7—C12 | 1.544 (3) | C33—H33B | 0.9900 |
C7—C8 | 1.545 (3) | C34—C35 | 1.534 (3) |
C7—H7 | 1.0000 | C34—H34A | 0.9900 |
C8—C9 | 1.533 (3) | C34—H34B | 0.9900 |
C8—H8A | 0.9900 | C35—C36 | 1.532 (3) |
C8—H8B | 0.9900 | C35—H35A | 0.9900 |
C9—C10 | 1.537 (3) | C35—H35B | 0.9900 |
C9—H9A | 0.9900 | C36—H36A | 0.9900 |
C9—H9B | 0.9900 | C36—H36B | 0.9900 |
C10—C11 | 1.527 (3) | C37—C38 | 1.498 (3) |
C10—H10A | 0.9900 | C37—H37A | 0.9800 |
C10—H10B | 0.9900 | C37—H37B | 0.9800 |
C11—C12 | 1.531 (3) | C37—H37C | 0.9800 |
C11—H11A | 0.9900 | C38—C39 | 1.500 (3) |
C11—H11B | 0.9900 | C39—H39A | 0.9800 |
C12—H12A | 0.9900 | C39—H39B | 0.9800 |
C12—H12B | 0.9900 | C39—H39C | 0.9800 |
C13—C14 | 1.537 (3) | C40—C41 | 1.503 (3) |
C13—C18 | 1.538 (3) | C40—H40A | 0.9800 |
C13—H13 | 1.0000 | C40—H40B | 0.9800 |
C14—C15 | 1.535 (3) | C40—H40C | 0.9800 |
C14—H14A | 0.9900 | C41—C42 | 1.491 (3) |
C14—H14B | 0.9900 | C42—H42A | 0.9800 |
C15—C16 | 1.527 (3) | C42—H42B | 0.9800 |
C15—H15A | 0.9900 | C42—H42C | 0.9800 |
C15—H15B | 0.9900 | O3—C44 | 1.212 (3) |
C16—C17 | 1.525 (3) | C43—C44 | 1.480 (4) |
C16—H16A | 0.9900 | C43—H43A | 0.9800 |
C16—H16B | 0.9900 | C43—H43B | 0.9800 |
C17—C18 | 1.529 (3) | C43—H43C | 0.9800 |
C17—H17A | 0.9900 | C44—C45 | 1.491 (4) |
C17—H17B | 0.9900 | C45—H45A | 0.9800 |
C18—H18A | 0.9900 | C45—H45B | 0.9800 |
C18—H18B | 0.9900 | C45—H45C | 0.9800 |
C19—C24 | 1.536 (3) | B1—F4 | 1.3577 |
C19—C20 | 1.542 (3) | B1—F2B | 1.3643 |
C19—H19 | 1.0000 | B1—F2A | 1.3669 |
C20—C21 | 1.532 (3) | B1—F3 | 1.3759 |
C20—H20A | 0.9900 | B1—F3A | 1.3901 |
C20—H20B | 0.9900 | B1—F1 | 1.3917 |
C21—C22 | 1.533 (3) | B1—F4B | 1.3918 |
C21—H21A | 0.9900 | B1—F4A | 1.4045 |
C21—H21B | 0.9900 | B1—F2 | 1.4100 |
C22—C23 | 1.528 (3) | B1—F3B | 1.4257 |
C22—H22A | 0.9900 | ||
O2—Ir1—O1 | 83.00 (5) | H21A—C21—H21B | 108.0 |
O2—Ir1—P2 | 97.03 (4) | C23—C22—C21 | 111.20 (17) |
O1—Ir1—P2 | 96.06 (4) | C23—C22—H22A | 109.4 |
O2—Ir1—P1 | 94.84 (4) | C21—C22—H22A | 109.4 |
O1—Ir1—P1 | 92.05 (4) | C23—C22—H22B | 109.4 |
P2—Ir1—P1 | 166.350 (19) | C21—C22—H22B | 109.4 |
O2—Ir1—H1 | 99.0 (7) | H22A—C22—H22B | 108.0 |
O1—Ir1—H1 | 177.4 (7) | C22—C23—C24 | 112.36 (18) |
P2—Ir1—H1 | 85.3 (8) | C22—C23—H23A | 109.1 |
P1—Ir1—H1 | 86.2 (8) | C24—C23—H23A | 109.1 |
O2—Ir1—H2 | 173.7 (7) | C22—C23—H23B | 109.1 |
O1—Ir1—H2 | 90.7 (7) | C24—C23—H23B | 109.1 |
P2—Ir1—H2 | 84.0 (8) | H23A—C23—H23B | 107.9 |
P1—Ir1—H2 | 84.9 (8) | C19—C24—C23 | 109.76 (17) |
H1—Ir1—H2 | 87.2 (8) | C19—C24—H24A | 109.7 |
C1—P1—C13 | 104.43 (9) | C23—C24—H24A | 109.7 |
C1—P1—C7 | 105.05 (9) | C19—C24—H24B | 109.7 |
C13—P1—C7 | 104.34 (9) | C23—C24—H24B | 109.7 |
C1—P1—Ir1 | 113.01 (7) | H24A—C24—H24B | 108.2 |
C13—P1—Ir1 | 113.14 (7) | C26—C25—C30 | 109.23 (16) |
C7—P1—Ir1 | 115.77 (7) | C26—C25—P2 | 112.17 (14) |
C25—P2—C31 | 106.58 (9) | C30—C25—P2 | 114.74 (14) |
C25—P2—C19 | 102.35 (9) | C26—C25—H25 | 106.7 |
C31—P2—C19 | 106.27 (9) | C30—C25—H25 | 106.7 |
C25—P2—Ir1 | 114.78 (7) | P2—C25—H25 | 106.7 |
C31—P2—Ir1 | 113.35 (6) | C27—C26—C25 | 111.55 (17) |
C19—P2—Ir1 | 112.56 (7) | C27—C26—H26A | 109.3 |
C38—O1—Ir1 | 152.71 (14) | C25—C26—H26A | 109.3 |
C41—O2—Ir1 | 135.60 (13) | C27—C26—H26B | 109.3 |
C2—C1—C6 | 110.51 (17) | C25—C26—H26B | 109.3 |
C2—C1—P1 | 112.25 (14) | H26A—C26—H26B | 108.0 |
C6—C1—P1 | 111.20 (14) | C26—C27—C28 | 111.42 (18) |
C2—C1—H1A | 107.6 | C26—C27—H27A | 109.3 |
C6—C1—H1A | 107.6 | C28—C27—H27A | 109.3 |
P1—C1—H1A | 107.6 | C26—C27—H27B | 109.3 |
C3—C2—C1 | 111.52 (17) | C28—C27—H27B | 109.3 |
C3—C2—H2A | 109.3 | H27A—C27—H27B | 108.0 |
C1—C2—H2A | 109.3 | C29—C28—C27 | 111.06 (18) |
C3—C2—H2B | 109.3 | C29—C28—H28A | 109.4 |
C1—C2—H2B | 109.3 | C27—C28—H28A | 109.4 |
H2A—C2—H2B | 108.0 | C29—C28—H28B | 109.4 |
C4—C3—C2 | 111.36 (17) | C27—C28—H28B | 109.4 |
C4—C3—H3A | 109.4 | H28A—C28—H28B | 108.0 |
C2—C3—H3A | 109.4 | C28—C29—C30 | 111.33 (18) |
C4—C3—H3B | 109.4 | C28—C29—H29A | 109.4 |
C2—C3—H3B | 109.4 | C30—C29—H29A | 109.4 |
H3A—C3—H3B | 108.0 | C28—C29—H29B | 109.4 |
C5—C4—C3 | 110.73 (17) | C30—C29—H29B | 109.4 |
C5—C4—H4A | 109.5 | H29A—C29—H29B | 108.0 |
C3—C4—H4A | 109.5 | C29—C30—C25 | 110.38 (17) |
C5—C4—H4B | 109.5 | C29—C30—H30A | 109.6 |
C3—C4—H4B | 109.5 | C25—C30—H30A | 109.6 |
H4A—C4—H4B | 108.1 | C29—C30—H30B | 109.6 |
C4—C5—C6 | 110.10 (17) | C25—C30—H30B | 109.6 |
C4—C5—H5A | 109.6 | H30A—C30—H30B | 108.1 |
C6—C5—H5A | 109.6 | C32—C31—C36 | 109.65 (16) |
C4—C5—H5B | 109.6 | C32—C31—P2 | 115.24 (14) |
C6—C5—H5B | 109.6 | C36—C31—P2 | 113.67 (14) |
H5A—C5—H5B | 108.2 | C32—C31—H31 | 105.8 |
C5—C6—C1 | 110.74 (17) | C36—C31—H31 | 105.8 |
C5—C6—H6A | 109.5 | P2—C31—H31 | 105.8 |
C1—C6—H6A | 109.5 | C33—C32—C31 | 111.58 (17) |
C5—C6—H6B | 109.5 | C33—C32—H32A | 109.3 |
C1—C6—H6B | 109.5 | C31—C32—H32A | 109.3 |
H6A—C6—H6B | 108.1 | C33—C32—H32B | 109.3 |
C12—C7—C8 | 109.43 (16) | C31—C32—H32B | 109.3 |
C12—C7—P1 | 115.57 (14) | H32A—C32—H32B | 108.0 |
C8—C7—P1 | 114.02 (14) | C32—C33—C34 | 111.71 (18) |
C12—C7—H7 | 105.6 | C32—C33—H33A | 109.3 |
C8—C7—H7 | 105.6 | C34—C33—H33A | 109.3 |
P1—C7—H7 | 105.6 | C32—C33—H33B | 109.3 |
C9—C8—C7 | 110.68 (17) | C34—C33—H33B | 109.3 |
C9—C8—H8A | 109.5 | H33A—C33—H33B | 107.9 |
C7—C8—H8A | 109.5 | C33—C34—C35 | 110.77 (18) |
C9—C8—H8B | 109.5 | C33—C34—H34A | 109.5 |
C7—C8—H8B | 109.5 | C35—C34—H34A | 109.5 |
H8A—C8—H8B | 108.1 | C33—C34—H34B | 109.5 |
C8—C9—C10 | 111.84 (18) | C35—C34—H34B | 109.5 |
C8—C9—H9A | 109.2 | H34A—C34—H34B | 108.1 |
C10—C9—H9A | 109.2 | C36—C35—C34 | 111.23 (17) |
C8—C9—H9B | 109.2 | C36—C35—H35A | 109.4 |
C10—C9—H9B | 109.2 | C34—C35—H35A | 109.4 |
H9A—C9—H9B | 107.9 | C36—C35—H35B | 109.4 |
C11—C10—C9 | 111.07 (17) | C34—C35—H35B | 109.4 |
C11—C10—H10A | 109.4 | H35A—C35—H35B | 108.0 |
C9—C10—H10A | 109.4 | C35—C36—C31 | 111.27 (17) |
C11—C10—H10B | 109.4 | C35—C36—H36A | 109.4 |
C9—C10—H10B | 109.4 | C31—C36—H36A | 109.4 |
H10A—C10—H10B | 108.0 | C35—C36—H36B | 109.4 |
C10—C11—C12 | 111.50 (18) | C31—C36—H36B | 109.4 |
C10—C11—H11A | 109.3 | H36A—C36—H36B | 108.0 |
C12—C11—H11A | 109.3 | C38—C37—H37A | 109.5 |
C10—C11—H11B | 109.3 | C38—C37—H37B | 109.5 |
C12—C11—H11B | 109.3 | H37A—C37—H37B | 109.5 |
H11A—C11—H11B | 108.0 | C38—C37—H37C | 109.5 |
C11—C12—C7 | 110.79 (17) | H37A—C37—H37C | 109.5 |
C11—C12—H12A | 109.5 | H37B—C37—H37C | 109.5 |
C7—C12—H12A | 109.5 | O1—C38—C37 | 119.36 (19) |
C11—C12—H12B | 109.5 | O1—C38—C39 | 124.26 (19) |
C7—C12—H12B | 109.5 | C37—C38—C39 | 116.38 (18) |
H12A—C12—H12B | 108.1 | C38—C39—H39A | 109.5 |
C14—C13—C18 | 109.56 (17) | C38—C39—H39B | 109.5 |
C14—C13—P1 | 117.35 (14) | H39A—C39—H39B | 109.5 |
C18—C13—P1 | 111.25 (14) | C38—C39—H39C | 109.5 |
C14—C13—H13 | 106.0 | H39A—C39—H39C | 109.5 |
C18—C13—H13 | 106.0 | H39B—C39—H39C | 109.5 |
P1—C13—H13 | 106.0 | C41—C40—H40A | 109.5 |
C15—C14—C13 | 110.60 (18) | C41—C40—H40B | 109.5 |
C15—C14—H14A | 109.5 | H40A—C40—H40B | 109.5 |
C13—C14—H14A | 109.5 | C41—C40—H40C | 109.5 |
C15—C14—H14B | 109.5 | H40A—C40—H40C | 109.5 |
C13—C14—H14B | 109.5 | H40B—C40—H40C | 109.5 |
H14A—C14—H14B | 108.1 | O2—C41—C42 | 122.86 (19) |
C16—C15—C14 | 111.05 (19) | O2—C41—C40 | 119.81 (19) |
C16—C15—H15A | 109.4 | C42—C41—C40 | 117.32 (19) |
C14—C15—H15A | 109.4 | C41—C42—H42A | 109.5 |
C16—C15—H15B | 109.4 | C41—C42—H42B | 109.5 |
C14—C15—H15B | 109.4 | H42A—C42—H42B | 109.5 |
H15A—C15—H15B | 108.0 | C41—C42—H42C | 109.5 |
C17—C16—C15 | 111.14 (18) | H42A—C42—H42C | 109.5 |
C17—C16—H16A | 109.4 | H42B—C42—H42C | 109.5 |
C15—C16—H16A | 109.4 | C44—C43—H43A | 109.5 |
C17—C16—H16B | 109.4 | C44—C43—H43B | 109.5 |
C15—C16—H16B | 109.4 | H43A—C43—H43B | 109.5 |
H16A—C16—H16B | 108.0 | C44—C43—H43C | 109.5 |
C16—C17—C18 | 110.96 (19) | H43A—C43—H43C | 109.5 |
C16—C17—H17A | 109.4 | H43B—C43—H43C | 109.5 |
C18—C17—H17A | 109.4 | O3—C44—C43 | 122.4 (3) |
C16—C17—H17B | 109.4 | O3—C44—C45 | 121.4 (3) |
C18—C17—H17B | 109.4 | C43—C44—C45 | 116.2 (3) |
H17A—C17—H17B | 108.0 | C44—C45—H45A | 109.5 |
C17—C18—C13 | 111.08 (18) | C44—C45—H45B | 109.5 |
C17—C18—H18A | 109.4 | H45A—C45—H45B | 109.5 |
C13—C18—H18A | 109.4 | C44—C45—H45C | 109.5 |
C17—C18—H18B | 109.4 | H45A—C45—H45C | 109.5 |
C13—C18—H18B | 109.4 | H45B—C45—H45C | 109.5 |
H18A—C18—H18B | 108.0 | F4—B1—F3 | 111.6 |
C24—C19—C20 | 109.13 (16) | F2A—B1—F3A | 110.2 |
C24—C19—P2 | 120.69 (14) | F4—B1—F1 | 110.7 |
C20—C19—P2 | 110.55 (14) | F2B—B1—F1 | 115.2 |
C24—C19—H19 | 105.0 | F2A—B1—F1 | 111.6 |
C20—C19—H19 | 105.0 | F3—B1—F1 | 110.0 |
P2—C19—H19 | 105.0 | F3A—B1—F1 | 112.0 |
C21—C20—C19 | 110.18 (17) | F2B—B1—F4B | 109.1 |
C21—C20—H20A | 109.6 | F1—B1—F4B | 111.0 |
C19—C20—H20A | 109.6 | F2A—B1—F4A | 108.5 |
C21—C20—H20B | 109.6 | F3A—B1—F4A | 106.2 |
C19—C20—H20B | 109.6 | F1—B1—F4A | 108.1 |
H20A—C20—H20B | 108.1 | F4—B1—F2 | 109.1 |
C20—C21—C22 | 110.89 (17) | F3—B1—F2 | 108.4 |
C20—C21—H21A | 109.5 | F1—B1—F2 | 106.8 |
C22—C21—H21A | 109.5 | F2B—B1—F3B | 107.7 |
C20—C21—H21B | 109.5 | F1—B1—F3B | 106.2 |
C22—C21—H21B | 109.5 | F4B—B1—F3B | 107.4 |
O2—Ir1—P1—C1 | −113.65 (8) | C7—P1—C13—C18 | −64.65 (16) |
O1—Ir1—P1—C1 | 163.20 (8) | Ir1—P1—C13—C18 | 62.02 (16) |
P2—Ir1—P1—C1 | 36.70 (12) | C18—C13—C14—C15 | −57.5 (2) |
O2—Ir1—P1—C13 | 4.77 (8) | P1—C13—C14—C15 | 174.38 (15) |
O1—Ir1—P1—C13 | −78.38 (8) | C13—C14—C15—C16 | 57.1 (3) |
P2—Ir1—P1—C13 | 155.12 (10) | C14—C15—C16—C17 | −55.8 (3) |
O2—Ir1—P1—C7 | 125.13 (8) | C15—C16—C17—C18 | 55.6 (3) |
O1—Ir1—P1—C7 | 41.98 (8) | C16—C17—C18—C13 | −56.9 (3) |
P2—Ir1—P1—C7 | −84.52 (11) | C14—C13—C18—C17 | 57.7 (2) |
O2—Ir1—P2—C25 | 119.70 (8) | P1—C13—C18—C17 | −170.95 (15) |
O1—Ir1—P2—C25 | −156.63 (8) | C25—P2—C19—C24 | 38.12 (19) |
P1—Ir1—P2—C25 | −30.52 (12) | C31—P2—C19—C24 | −73.49 (18) |
O2—Ir1—P2—C31 | −117.50 (8) | Ir1—P2—C19—C24 | 161.87 (15) |
O1—Ir1—P2—C31 | −33.83 (8) | C25—P2—C19—C20 | 167.12 (14) |
P1—Ir1—P2—C31 | 92.28 (11) | C31—P2—C19—C20 | 55.51 (16) |
O2—Ir1—P2—C19 | 3.16 (8) | Ir1—P2—C19—C20 | −69.13 (15) |
O1—Ir1—P2—C19 | 86.82 (8) | C24—C19—C20—C21 | −60.8 (2) |
P1—Ir1—P2—C19 | −147.07 (10) | P2—C19—C20—C21 | 164.19 (14) |
O2—Ir1—O1—C38 | 3.7 (3) | C19—C20—C21—C22 | 58.3 (2) |
P2—Ir1—O1—C38 | −92.7 (3) | C20—C21—C22—C23 | −54.1 (2) |
P1—Ir1—O1—C38 | 98.3 (3) | C21—C22—C23—C24 | 53.6 (3) |
O1—Ir1—O2—C41 | 177.91 (18) | C20—C19—C24—C23 | 59.1 (2) |
P2—Ir1—O2—C41 | −86.80 (18) | P2—C19—C24—C23 | −171.23 (16) |
P1—Ir1—O2—C41 | 86.44 (18) | C22—C23—C24—C19 | −56.3 (2) |
C13—P1—C1—C2 | −58.05 (16) | C31—P2—C25—C26 | 172.35 (14) |
C7—P1—C1—C2 | −167.56 (14) | C19—P2—C25—C26 | 60.98 (16) |
Ir1—P1—C1—C2 | 65.33 (15) | Ir1—P2—C25—C26 | −61.28 (15) |
C13—P1—C1—C6 | 177.58 (15) | C31—P2—C25—C30 | −62.25 (17) |
C7—P1—C1—C6 | 68.06 (16) | C19—P2—C25—C30 | −173.62 (15) |
Ir1—P1—C1—C6 | −59.04 (16) | Ir1—P2—C25—C30 | 64.12 (16) |
C6—C1—C2—C3 | −54.1 (2) | C30—C25—C26—C27 | 57.2 (2) |
P1—C1—C2—C3 | −178.89 (14) | P2—C25—C26—C27 | −174.40 (15) |
C1—C2—C3—C4 | 54.5 (2) | C25—C26—C27—C28 | −55.4 (2) |
C2—C3—C4—C5 | −56.7 (2) | C26—C27—C28—C29 | 53.9 (3) |
C3—C4—C5—C6 | 58.6 (2) | C27—C28—C29—C30 | −55.6 (2) |
C4—C5—C6—C1 | −58.6 (2) | C28—C29—C30—C25 | 58.3 (2) |
C2—C1—C6—C5 | 56.3 (2) | C26—C25—C30—C29 | −58.3 (2) |
P1—C1—C6—C5 | −178.36 (14) | P2—C25—C30—C29 | 174.77 (14) |
C1—P1—C7—C12 | 28.15 (17) | C25—P2—C31—C32 | −35.95 (17) |
C13—P1—C7—C12 | −81.44 (16) | C19—P2—C31—C32 | 72.68 (16) |
Ir1—P1—C7—C12 | 153.54 (12) | Ir1—P2—C31—C32 | −163.16 (12) |
C1—P1—C7—C8 | −99.95 (15) | C25—P2—C31—C36 | 91.82 (15) |
C13—P1—C7—C8 | 150.47 (14) | C19—P2—C31—C36 | −159.55 (14) |
Ir1—P1—C7—C8 | 25.45 (16) | Ir1—P2—C31—C36 | −35.39 (16) |
C12—C7—C8—C9 | 57.5 (2) | C36—C31—C32—C33 | 55.9 (2) |
P1—C7—C8—C9 | −171.33 (14) | P2—C31—C32—C33 | −174.35 (14) |
C7—C8—C9—C10 | −56.1 (2) | C31—C32—C33—C34 | −55.8 (2) |
C8—C9—C10—C11 | 54.2 (2) | C32—C33—C34—C35 | 54.9 (2) |
C9—C10—C11—C12 | −54.6 (2) | C33—C34—C35—C36 | −55.5 (2) |
C10—C11—C12—C7 | 57.3 (2) | C34—C35—C36—C31 | 57.0 (2) |
C8—C7—C12—C11 | −58.2 (2) | C32—C31—C36—C35 | −56.5 (2) |
P1—C7—C12—C11 | 171.50 (14) | P2—C31—C36—C35 | 172.86 (14) |
C1—P1—C13—C14 | −47.42 (18) | Ir1—O1—C38—C37 | −171.0 (2) |
C7—P1—C13—C14 | 62.62 (18) | Ir1—O1—C38—C39 | 8.8 (4) |
Ir1—P1—C13—C14 | −170.71 (14) | Ir1—O2—C41—C42 | 5.3 (3) |
C1—P1—C13—C18 | −174.69 (15) | Ir1—O2—C41—C40 | −174.12 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O1 | 0.99 | 2.49 | 3.358 (3) | 146 |
C18—H18A···O2 | 0.99 | 2.45 | 3.207 (3) | 133 |
C36—H36B···O1 | 0.99 | 2.50 | 3.347 (3) | 144 |
C39—H39A···O2 | 0.98 | 2.45 | 3.304 (3) | 146 |
C39—H39B···F4i | 0.98 | 2.54 | 3.441 (3) | 153 |
C40—H40B···F1ii | 0.98 | 2.51 | 3.434 (3) | 156 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [IrH2(C18H33P)2(C3H6O)2]BF4·C3H6O |
Mr | 1016.09 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 10.218 (1), 25.199 (4), 19.621 (1) |
β (°) | 102.060 (5) |
V (Å3) | 4940.6 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.82 |
Crystal size (mm) | 0.20 × 0.18 × 0.17 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | Integration (Gaussian; Coppens et al., 1965) |
Tmin, Tmax | 0.562, 0.687 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 111705, 12737, 10353 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.676 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.043, 1.04 |
No. of reflections | 12737 |
No. of parameters | 544 |
No. of restraints | 39 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.54, −0.52 |
Computer programs: COLLECT (Bruker, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Ir1—O2 | 2.2379 (13) | Ir1—P2 | 2.3159 (6) |
Ir1—O1 | 2.2762 (14) | Ir1—P1 | 2.3267 (6) |
O2—Ir1—O1 | 83.00 (5) | O2—Ir1—P1 | 94.84 (4) |
O2—Ir1—P2 | 97.03 (4) | O1—Ir1—P1 | 92.05 (4) |
O1—Ir1—P2 | 96.06 (4) | P2—Ir1—P1 | 166.350 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O1 | 0.99 | 2.49 | 3.358 (3) | 145.5 |
C18—H18A···O2 | 0.99 | 2.45 | 3.207 (3) | 132.5 |
C36—H36B···O1 | 0.99 | 2.50 | 3.347 (3) | 143.5 |
C39—H39A···O2 | 0.98 | 2.45 | 3.304 (3) | 145.7 |
C39—H39B···F4i | 0.98 | 2.54 | 3.441 (3) | 153.2 |
C40—H40B···F1ii | 0.98 | 2.51 | 3.434 (3) | 156.2 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, −y+3/2, z−1/2. |
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The cation of the title complex (Fig. 1), adopts a slightly distorted OC-6–13 coordination geometry, where the two monodentate phosphines lie trans to each other [Ir—P = 2.3159 (6) and 2.3267 (6) Å] and the hydrides are opposite to the O-bound acetone groups [Ir—O = 2.238 (1) and 2.276 (1) Å] (Table 1). The tetrafluoridoborate anion exhibts threefold rotational disorder about the B1—F1 axis. The acetone molecule of solvation, by contrast, is located in fully ordered atomic positions.
The ionic components are linked by C—H···F hydrogen-bonding contacts, in which atoms C39 and C40 of the acetone ligands act as donors, via H39B and H40B, to fluorine atoms F4 and F1 with C39···F4(-x + 1, y - 1/2, -z + 1/2) = 3.441 (3) Å and C40···F1(x - 1, -y + 3/2, z - 1/2 + z) = 3.434 (3) Å, respectively. Even though the cation displays several intramolecular C—H···O interactions with C···O distances in the range 3.207 (3)–3.358 (3) Å (Table 2), the oxygen atom of the solvate molecule does not function as a carbon—hydrogen bond acceptor.
In the corresponding solvate-free bis(triphenylphosphine) complex [Ir(H)2{P(C6H5)3}2{OC(CH3)2}2][BF4], the cation also has pseudooctahedral geometry with the two phosphines in mutual trans coordination and the hydrido ligands opposite to the acetone molecules (Crabtree et al., 1984).