Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004469/ci6016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004469/ci6016Isup2.hkl |
CCDC reference: 162803
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.009 Å
- R factor = 0.047
- wR factor = 0.133
- Data-to-parameter ratio = 13.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.83 From the CIF: _reflns_number_total 7148 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 7694 Completeness (_total/calc) 92.90% Alert C: < 95% complete RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.141 PLAT_420 Alert C D-H Without Acceptor N(1) - H(99B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Ag[BF4] (26.8 mg, 0.138 mmol) was added to a solution of benzylamine (15 µL, 0.138 mmol) and [Ru(Cp)Cl(PPh3)2] (100 mg, 0.138 mmol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere. The color changed immediately to yellow and an off-white solid precipitated. The mixture was stirred at room temperature for 30 min and filtered over celite. The solvent was removed under reduced pressure and the residue redissolved in dichloromethane and precipitated with hexanes. The yellow solid was washed with hexanes (2 × 10 ml) and dried under vacuum to afford 104 mg (85%) of the title compound.
The NH2 and the CH2 H atoms were located by Fourier syntheses and their parameters were refined [N—H = 0.84 (4) and 1.00 (8) Å, and C—H = 0.96 (4) and 1.08 (5) Å]. All the other H-atom positions were calculated and refined riding on their parent atoms (C—H = 0.93 Å).
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: EUCLID (Spek, 1982); software used to prepare material for publication: SHELXL97.
[Ru(C5H5)(C7H9N)(C18H15P)2]BF4 | Dx = 1.445 Mg m−3 |
Mr = 884.66 | Cu Kα radiation, λ = 1.54179 Å |
Orthorhombic, Pbca | Cell parameters from 22652 reflections |
a = 13.4255 (3) Å | θ = 1.5–70.1° |
b = 21.1335 (6) Å | µ = 4.31 mm−1 |
c = 28.6552 (8) Å | T = 200 K |
V = 8130.3 (4) Å3 | Block, yellow |
Z = 8 | 0.08 × 0.05 × 0.03 mm |
F(000) = 3632 |
KappaCCD diffractometer | 7148 independent reflections |
Radiation source: fine-focus sealed tube | 3839 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.141 |
Detector resolution: 9.0 pixels mm-1 | θmax = 69.8°, θmin = 3.1° |
CCD scans | h = 0→16 |
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995) | k = 0→24 |
Tmin = 0.701, Tmax = 0.898 | l = 0→34 |
54625 measured reflections |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0449P)2 + ] where P = (Fo2 + 2Fc2)/3 |
7148 reflections | (Δ/σ)max < 0.001 |
530 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −0.59 e Å−3 |
[Ru(C5H5)(C7H9N)(C18H15P)2]BF4 | V = 8130.3 (4) Å3 |
Mr = 884.66 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 13.4255 (3) Å | µ = 4.31 mm−1 |
b = 21.1335 (6) Å | T = 200 K |
c = 28.6552 (8) Å | 0.08 × 0.05 × 0.03 mm |
KappaCCD diffractometer | 7148 independent reflections |
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995) | 3839 reflections with I > 2σ(I) |
Tmin = 0.701, Tmax = 0.898 | Rint = 0.141 |
54625 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.86 e Å−3 |
7148 reflections | Δρmin = −0.59 e Å−3 |
530 parameters |
Experimental. Anal. and spectroscopic data: Calcd for C48H44BF4NP2Ru (884.66): C, 65.17; H, 5.01; N, 1.58. Found: C, 64.96; H, 4.89; N, 1.50. 1H NMR (CD2Cl2): δ 7.53–7.03 (m, 35 H, Ph), 6.55 (s, br, 2 H, NH2), 4.55 (s, 5 H, Cp), 2.54 (s, br, 2 H, CH2) p.p.m.. 31P NMR (CD2Cl2): δ 44.48 (s) p.p.m.. 19F NMR (CD2Cl2): δ -152.23 (s) p.p.m.. |
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 | ||
C1 | 0.2292 (4) | 0.2018 (3) | 0.01116 (18) | 0.0382 (16) | |
H1 | 0.2570 | 0.1634 | 0.0021 | 0.046* | |
C2 | 0.1254 (4) | 0.2147 (3) | 0.02001 (18) | 0.0365 (15) | |
H2 | 0.0735 | 0.1859 | 0.0170 | 0.044* | |
C3 | 0.1160 (4) | 0.2779 (3) | 0.03387 (19) | 0.0379 (16) | |
H3 | 0.0568 | 0.2978 | 0.0420 | 0.046* | |
C4 | 0.2113 (4) | 0.3064 (3) | 0.03359 (19) | 0.0412 (16) | |
H4 | 0.2258 | 0.3481 | 0.0414 | 0.049* | |
C5 | 0.2806 (4) | 0.2597 (3) | 0.01917 (18) | 0.0375 (15) | |
H5 | 0.3487 | 0.2659 | 0.0155 | 0.045* | |
C6 | 0.1960 (5) | 0.3456 (3) | 0.1543 (2) | 0.0431 (17) | |
C101 | 0.1579 (4) | 0.3765 (3) | 0.1983 (2) | 0.0419 (16) | |
C102 | 0.0915 (4) | 0.4260 (3) | 0.1969 (2) | 0.0516 (19) | |
H102 | 0.0681 | 0.4403 | 0.1683 | 0.062* | |
C103 | 0.0592 (5) | 0.4548 (4) | 0.2372 (3) | 0.073 (2) | |
H103 | 0.0148 | 0.4885 | 0.2357 | 0.087* | |
C104 | 0.0935 (6) | 0.4331 (4) | 0.2805 (3) | 0.069 (2) | |
H104 | 0.0714 | 0.4519 | 0.3080 | 0.083* | |
C105 | 0.1589 (5) | 0.3847 (4) | 0.2819 (2) | 0.060 (2) | |
H105 | 0.1824 | 0.3705 | 0.3106 | 0.071* | |
C106 | 0.1911 (5) | 0.3561 (3) | 0.2417 (2) | 0.0528 (18) | |
H106 | 0.2359 | 0.3226 | 0.2435 | 0.063* | |
C201 | 0.1490 (4) | 0.1016 (3) | 0.16953 (19) | 0.0350 (15) | |
C202 | 0.1086 (4) | 0.1404 (3) | 0.2043 (2) | 0.0444 (17) | |
H202 | 0.0776 | 0.1781 | 0.1961 | 0.053* | |
C203 | 0.1141 (4) | 0.1230 (3) | 0.2508 (2) | 0.0494 (18) | |
H203 | 0.0879 | 0.1495 | 0.2736 | 0.059* | |
C204 | 0.1583 (5) | 0.0665 (4) | 0.2636 (2) | 0.054 (2) | |
H204 | 0.1632 | 0.0554 | 0.2949 | 0.065* | |
C205 | 0.1951 (5) | 0.0270 (3) | 0.2295 (2) | 0.056 (2) | |
H205 | 0.2240 | −0.0115 | 0.2377 | 0.068* | |
C206 | 0.1890 (4) | 0.0443 (3) | 0.1832 (2) | 0.0460 (17) | |
H206 | 0.2125 | 0.0166 | 0.1605 | 0.055* | |
C301 | 0.1740 (4) | 0.0677 (3) | 0.0715 (2) | 0.0306 (14) | |
C302 | 0.2648 (4) | 0.0382 (3) | 0.0759 (2) | 0.0410 (16) | |
H302 | 0.3076 | 0.0502 | 0.0998 | 0.049* | |
C303 | 0.2938 (4) | −0.0095 (3) | 0.0451 (2) | 0.0398 (16) | |
H303 | 0.3540 | −0.0304 | 0.0494 | 0.048* | |
C304 | 0.2324 (4) | −0.0256 (3) | 0.0080 (2) | 0.0389 (16) | |
H304 | 0.2520 | −0.0566 | −0.0131 | 0.047* | |
C305 | 0.1436 (4) | 0.0043 (3) | 0.0027 (2) | 0.0380 (15) | |
H305 | 0.1027 | −0.0061 | −0.0223 | 0.046* | |
C306 | 0.1128 (4) | 0.0506 (3) | 0.0346 (2) | 0.0349 (15) | |
H306 | 0.0511 | 0.0699 | 0.0310 | 0.042* | |
C401 | 0.0016 (4) | 0.1296 (3) | 0.10744 (19) | 0.0308 (14) | |
C402 | −0.0487 (4) | 0.0738 (3) | 0.1190 (2) | 0.0387 (16) | |
H402 | −0.0119 | 0.0382 | 0.1271 | 0.046* | |
C403 | −0.1502 (4) | 0.0698 (3) | 0.1187 (2) | 0.0432 (17) | |
H403 | −0.1816 | 0.0321 | 0.1267 | 0.052* | |
C404 | −0.2064 (4) | 0.1224 (3) | 0.1063 (2) | 0.0412 (16) | |
H404 | −0.2756 | 0.1199 | 0.1058 | 0.049* | |
C405 | −0.1599 (4) | 0.1779 (3) | 0.0950 (2) | 0.0433 (17) | |
H405 | −0.1974 | 0.2132 | 0.0869 | 0.052* | |
C406 | −0.0562 (4) | 0.1815 (3) | 0.09562 (18) | 0.0353 (15) | |
H406 | −0.0252 | 0.2195 | 0.0880 | 0.042* | |
C501 | 0.3856 (4) | 0.2273 (3) | 0.18252 (19) | 0.0330 (14) | |
C502 | 0.3480 (4) | 0.1803 (3) | 0.2120 (2) | 0.0439 (17) | |
H502 | 0.3184 | 0.1445 | 0.1991 | 0.053* | |
C503 | 0.3542 (4) | 0.1861 (3) | 0.2597 (2) | 0.0482 (18) | |
H503 | 0.3300 | 0.1540 | 0.2788 | 0.058* | |
C504 | 0.3958 (4) | 0.2388 (3) | 0.2792 (2) | 0.0477 (18) | |
H504 | 0.3981 | 0.2429 | 0.3115 | 0.057* | |
C505 | 0.4337 (4) | 0.2850 (3) | 0.2516 (2) | 0.0464 (17) | |
H505 | 0.4625 | 0.3208 | 0.2649 | 0.056* | |
C506 | 0.4291 (4) | 0.2787 (3) | 0.2038 (2) | 0.0407 (16) | |
H506 | 0.4565 | 0.3103 | 0.1852 | 0.049* | |
C601 | 0.4622 (4) | 0.2808 (3) | 0.10145 (18) | 0.0307 (14) | |
C602 | 0.5645 (4) | 0.2695 (3) | 0.10628 (19) | 0.0385 (15) | |
H602 | 0.5868 | 0.2293 | 0.1144 | 0.046* | |
C603 | 0.6329 (5) | 0.3177 (3) | 0.0990 (2) | 0.0441 (17) | |
H603 | 0.7006 | 0.3095 | 0.1022 | 0.053* | |
C604 | 0.6011 (5) | 0.3779 (3) | 0.08687 (19) | 0.0448 (17) | |
H604 | 0.6470 | 0.4103 | 0.0825 | 0.054* | |
C605 | 0.5017 (5) | 0.3891 (3) | 0.0814 (2) | 0.0441 (17) | |
H605 | 0.4801 | 0.4291 | 0.0725 | 0.053* | |
C606 | 0.4327 (4) | 0.3416 (3) | 0.08905 (19) | 0.0388 (15) | |
H606 | 0.3652 | 0.3505 | 0.0858 | 0.047* | |
C701 | 0.4420 (4) | 0.1484 (3) | 0.1025 (2) | 0.0319 (15) | |
C702 | 0.4809 (4) | 0.1053 (3) | 0.1335 (2) | 0.0347 (15) | |
H702 | 0.4728 | 0.1111 | 0.1655 | 0.042* | |
C703 | 0.5327 (4) | 0.0528 (3) | 0.1167 (2) | 0.0420 (16) | |
H703 | 0.5577 | 0.0231 | 0.1375 | 0.050* | |
C704 | 0.5470 (4) | 0.0447 (3) | 0.0697 (2) | 0.0416 (16) | |
H704 | 0.5816 | 0.0095 | 0.0589 | 0.050* | |
C705 | 0.5103 (4) | 0.0888 (3) | 0.0384 (2) | 0.0412 (16) | |
H705 | 0.5209 | 0.0839 | 0.0065 | 0.049* | |
C706 | 0.4580 (4) | 0.1398 (3) | 0.0550 (2) | 0.0388 (16) | |
H706 | 0.4327 | 0.1693 | 0.0340 | 0.047* | |
B1 | −0.0797 (6) | 0.1300 (4) | 0.5999 (3) | 0.046 (2) | |
F1 | −0.0521 (3) | 0.17286 (18) | 0.63475 (13) | 0.0697 (11) | |
F2 | −0.1162 (2) | 0.1655 (2) | 0.56299 (13) | 0.0726 (12) | |
F3 | −0.1481 (3) | 0.08874 (19) | 0.61643 (15) | 0.0820 (13) | |
F4 | 0.0061 (2) | 0.09946 (16) | 0.58534 (12) | 0.0528 (10) | |
N1 | 0.1617 (4) | 0.2799 (3) | 0.14729 (19) | 0.0349 (13) | |
P1 | 0.13861 (10) | 0.13308 (7) | 0.11007 (5) | 0.0309 (4) | |
P2 | 0.37115 (11) | 0.22016 (7) | 0.11873 (5) | 0.0309 (4) | |
Ru1 | 0.21194 (3) | 0.22838 (2) | 0.085300 (14) | 0.02903 (16) | |
H6A | 0.276 (4) | 0.341 (3) | 0.1557 (18) | 0.052 (18)* | |
H6B | 0.173 (3) | 0.372 (2) | 0.1289 (16) | 0.020 (14)* | |
H99A | 0.099 (3) | 0.279 (2) | 0.1487 (15) | 0.006 (14)* | |
H99B | 0.179 (6) | 0.255 (4) | 0.176 (3) | 0.14 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.052 (4) | 0.041 (4) | 0.022 (3) | 0.006 (3) | 0.001 (3) | −0.002 (3) |
C2 | 0.036 (4) | 0.046 (4) | 0.028 (4) | 0.002 (3) | −0.008 (3) | −0.002 (3) |
C3 | 0.035 (4) | 0.044 (4) | 0.035 (4) | 0.007 (3) | −0.007 (3) | 0.004 (3) |
C4 | 0.057 (4) | 0.033 (4) | 0.034 (4) | −0.001 (4) | −0.004 (3) | 0.006 (3) |
C5 | 0.039 (4) | 0.045 (4) | 0.029 (4) | −0.003 (3) | 0.002 (3) | 0.008 (3) |
C6 | 0.054 (5) | 0.036 (4) | 0.039 (4) | 0.005 (4) | −0.002 (4) | −0.003 (3) |
C101 | 0.039 (4) | 0.046 (4) | 0.041 (4) | 0.002 (3) | −0.001 (3) | −0.015 (3) |
C102 | 0.043 (4) | 0.058 (5) | 0.053 (5) | 0.010 (4) | −0.006 (4) | −0.009 (4) |
C103 | 0.056 (5) | 0.066 (6) | 0.097 (7) | 0.019 (4) | 0.012 (5) | −0.027 (5) |
C104 | 0.076 (6) | 0.070 (6) | 0.062 (6) | −0.012 (5) | 0.030 (5) | −0.032 (5) |
C105 | 0.071 (5) | 0.069 (6) | 0.039 (5) | −0.007 (5) | 0.006 (4) | 0.002 (4) |
C106 | 0.061 (5) | 0.050 (5) | 0.048 (5) | 0.007 (4) | 0.001 (4) | −0.008 (4) |
C201 | 0.032 (4) | 0.042 (4) | 0.031 (4) | −0.002 (3) | 0.001 (3) | −0.003 (3) |
C202 | 0.041 (4) | 0.044 (4) | 0.048 (4) | 0.000 (3) | 0.010 (3) | 0.010 (4) |
C203 | 0.044 (4) | 0.070 (5) | 0.034 (4) | −0.010 (4) | 0.014 (3) | −0.006 (4) |
C204 | 0.049 (4) | 0.079 (6) | 0.035 (4) | −0.006 (4) | 0.002 (4) | 0.019 (4) |
C205 | 0.063 (5) | 0.057 (5) | 0.049 (5) | 0.012 (4) | −0.004 (4) | 0.018 (4) |
C206 | 0.054 (4) | 0.040 (4) | 0.044 (4) | 0.001 (3) | 0.001 (4) | 0.003 (3) |
C301 | 0.029 (3) | 0.029 (4) | 0.034 (4) | −0.004 (3) | 0.001 (3) | −0.003 (3) |
C302 | 0.039 (4) | 0.035 (4) | 0.049 (4) | 0.000 (3) | −0.004 (3) | −0.007 (3) |
C303 | 0.033 (3) | 0.031 (4) | 0.055 (4) | 0.003 (3) | 0.002 (3) | 0.000 (3) |
C304 | 0.042 (4) | 0.034 (4) | 0.040 (4) | 0.007 (3) | 0.008 (3) | −0.005 (3) |
C305 | 0.040 (4) | 0.035 (4) | 0.039 (4) | −0.006 (3) | −0.005 (3) | −0.007 (3) |
C306 | 0.034 (4) | 0.034 (4) | 0.036 (4) | 0.002 (3) | −0.002 (3) | 0.004 (3) |
C401 | 0.021 (3) | 0.036 (4) | 0.036 (4) | −0.002 (3) | 0.000 (3) | −0.003 (3) |
C402 | 0.030 (4) | 0.037 (4) | 0.049 (4) | 0.004 (3) | 0.003 (3) | 0.001 (3) |
C403 | 0.038 (4) | 0.045 (4) | 0.047 (4) | −0.012 (3) | 0.010 (3) | 0.000 (3) |
C404 | 0.028 (3) | 0.048 (5) | 0.048 (4) | −0.005 (3) | −0.002 (3) | −0.004 (3) |
C405 | 0.037 (4) | 0.047 (4) | 0.045 (4) | 0.013 (3) | −0.002 (3) | −0.004 (3) |
C406 | 0.027 (3) | 0.039 (4) | 0.040 (4) | −0.002 (3) | 0.004 (3) | −0.009 (3) |
C501 | 0.030 (3) | 0.038 (4) | 0.031 (4) | −0.001 (3) | 0.003 (3) | 0.002 (3) |
C502 | 0.034 (4) | 0.059 (5) | 0.038 (4) | −0.009 (3) | −0.004 (3) | −0.002 (4) |
C503 | 0.042 (4) | 0.069 (5) | 0.033 (4) | −0.010 (4) | −0.004 (3) | 0.013 (4) |
C504 | 0.035 (4) | 0.070 (5) | 0.038 (4) | 0.003 (4) | −0.004 (3) | −0.009 (4) |
C505 | 0.044 (4) | 0.059 (5) | 0.036 (4) | −0.003 (3) | −0.006 (3) | −0.007 (4) |
C506 | 0.045 (4) | 0.038 (4) | 0.039 (4) | −0.007 (3) | 0.000 (3) | −0.004 (3) |
C601 | 0.033 (4) | 0.035 (4) | 0.024 (3) | −0.004 (3) | 0.004 (3) | 0.001 (3) |
C602 | 0.036 (4) | 0.037 (4) | 0.042 (4) | 0.000 (3) | 0.006 (3) | −0.005 (3) |
C603 | 0.035 (4) | 0.046 (5) | 0.051 (4) | −0.004 (3) | 0.002 (3) | 0.000 (3) |
C604 | 0.054 (4) | 0.045 (5) | 0.035 (4) | −0.018 (4) | 0.002 (3) | −0.006 (3) |
C605 | 0.050 (4) | 0.038 (4) | 0.044 (4) | −0.007 (3) | 0.000 (3) | 0.009 (3) |
C606 | 0.034 (3) | 0.041 (4) | 0.041 (4) | −0.003 (3) | −0.001 (3) | 0.000 (3) |
C701 | 0.021 (3) | 0.038 (4) | 0.036 (4) | −0.003 (3) | 0.001 (3) | −0.004 (3) |
C702 | 0.034 (4) | 0.030 (4) | 0.040 (4) | −0.005 (3) | −0.008 (3) | −0.004 (3) |
C703 | 0.035 (4) | 0.040 (4) | 0.050 (5) | −0.008 (3) | −0.013 (3) | 0.007 (3) |
C704 | 0.033 (4) | 0.027 (4) | 0.065 (5) | −0.005 (3) | 0.007 (4) | −0.005 (3) |
C705 | 0.039 (4) | 0.042 (4) | 0.042 (4) | 0.002 (3) | 0.011 (3) | −0.001 (3) |
C706 | 0.038 (4) | 0.034 (4) | 0.044 (4) | 0.009 (3) | 0.004 (3) | 0.006 (3) |
B1 | 0.047 (5) | 0.041 (5) | 0.050 (5) | 0.002 (4) | −0.005 (4) | −0.003 (4) |
F1 | 0.079 (3) | 0.066 (3) | 0.064 (3) | 0.007 (2) | −0.001 (2) | −0.018 (2) |
F2 | 0.058 (2) | 0.093 (3) | 0.067 (3) | 0.014 (2) | −0.018 (2) | 0.011 (2) |
F3 | 0.055 (3) | 0.060 (3) | 0.131 (4) | −0.010 (2) | 0.028 (3) | 0.003 (3) |
F4 | 0.042 (2) | 0.052 (2) | 0.064 (3) | 0.0091 (18) | 0.0008 (19) | −0.005 (2) |
N1 | 0.027 (3) | 0.037 (4) | 0.041 (4) | 0.001 (3) | 0.002 (3) | 0.003 (3) |
P1 | 0.0286 (8) | 0.0286 (9) | 0.0355 (9) | 0.0002 (7) | −0.0001 (7) | 0.0006 (7) |
P2 | 0.0292 (9) | 0.0321 (9) | 0.0314 (9) | −0.0007 (7) | 0.0018 (7) | 0.0004 (7) |
Ru1 | 0.0292 (3) | 0.0285 (3) | 0.0294 (3) | 0.0006 (2) | −0.0001 (2) | 0.0000 (2) |
C1—C5 | 1.422 (7) | C401—P1 | 1.843 (5) |
C1—C2 | 1.442 (7) | C402—C403 | 1.365 (7) |
C1—Ru1 | 2.210 (5) | C402—H402 | 0.9300 |
C1—H1 | 0.9300 | C403—C404 | 1.389 (8) |
C2—C3 | 1.398 (8) | C403—H403 | 0.9300 |
C2—Ru1 | 2.221 (5) | C404—C405 | 1.368 (8) |
C2—H2 | 0.9300 | C404—H404 | 0.9300 |
C3—C4 | 1.414 (7) | C405—C406 | 1.395 (7) |
C3—Ru1 | 2.219 (5) | C405—H405 | 0.9300 |
C3—H3 | 0.9300 | C406—H406 | 0.9300 |
C4—C5 | 1.418 (7) | C501—C506 | 1.376 (7) |
C4—Ru1 | 2.217 (6) | C501—C502 | 1.397 (8) |
C4—H4 | 0.9300 | C501—P2 | 1.844 (6) |
C5—Ru1 | 2.208 (5) | C502—C503 | 1.377 (7) |
C5—H5 | 0.9300 | C502—H502 | 0.9300 |
C6—N1 | 1.477 (8) | C503—C504 | 1.365 (8) |
C6—C101 | 1.511 (8) | C503—H503 | 0.9300 |
C6—H6A | 1.08 (5) | C504—C505 | 1.357 (8) |
C6—H6B | 0.96 (4) | C504—H504 | 0.9300 |
C101—C102 | 1.375 (8) | C505—C506 | 1.379 (7) |
C101—C106 | 1.390 (8) | C505—H505 | 0.9300 |
C102—C103 | 1.374 (9) | C506—H506 | 0.9300 |
C102—H102 | 0.9300 | C601—C606 | 1.389 (7) |
C103—C104 | 1.400 (10) | C601—C602 | 1.402 (7) |
C103—H103 | 0.9300 | C601—P2 | 1.840 (6) |
C104—C105 | 1.349 (9) | C602—C603 | 1.387 (7) |
C104—H104 | 0.9300 | C602—H602 | 0.9300 |
C105—C106 | 1.371 (8) | C603—C604 | 1.386 (8) |
C105—H105 | 0.9300 | C603—H603 | 0.9300 |
C106—H106 | 0.9300 | C604—C605 | 1.364 (7) |
C201—C206 | 1.381 (8) | C604—H604 | 0.9300 |
C201—C202 | 1.399 (7) | C605—C606 | 1.384 (7) |
C201—P1 | 1.834 (6) | C605—H605 | 0.9300 |
C202—C203 | 1.385 (8) | C606—H606 | 0.9300 |
C202—H202 | 0.9300 | C701—C702 | 1.378 (7) |
C203—C204 | 1.381 (8) | C701—C706 | 1.390 (7) |
C203—H203 | 0.9300 | C701—P2 | 1.849 (6) |
C204—C205 | 1.378 (8) | C702—C703 | 1.394 (7) |
C204—H204 | 0.9300 | C702—H702 | 0.9300 |
C205—C206 | 1.378 (8) | C703—C704 | 1.370 (8) |
C205—H205 | 0.9300 | C703—H703 | 0.9300 |
C206—H206 | 0.9300 | C704—C705 | 1.385 (8) |
C301—C302 | 1.374 (7) | C704—H704 | 0.9300 |
C301—C306 | 1.388 (7) | C705—C706 | 1.371 (7) |
C301—P1 | 1.831 (6) | C705—H705 | 0.9300 |
C302—C303 | 1.395 (7) | C706—H706 | 0.9300 |
C302—H302 | 0.9300 | B1—F3 | 1.351 (8) |
C303—C304 | 1.387 (7) | B1—F4 | 1.384 (8) |
C303—H303 | 0.9300 | B1—F2 | 1.387 (8) |
C304—C305 | 1.357 (7) | B1—F1 | 1.398 (8) |
C304—H304 | 0.9300 | N1—Ru1 | 2.190 (5) |
C305—C306 | 1.401 (7) | N1—H99A | 0.84 (4) |
C305—H305 | 0.9300 | N1—H99B | 1.00 (8) |
C306—H306 | 0.9300 | P1—Ru1 | 2.3514 (15) |
C401—C406 | 1.386 (7) | P2—Ru1 | 2.3487 (15) |
C401—C402 | 1.399 (7) | ||
C5—C1—C2 | 106.1 (5) | C405—C406—H406 | 119.4 |
C5—C1—Ru1 | 71.2 (3) | C506—C501—C502 | 116.5 (5) |
C2—C1—Ru1 | 71.4 (3) | C506—C501—P2 | 123.2 (5) |
C5—C1—H1 | 127.0 | C502—C501—P2 | 120.2 (5) |
C2—C1—H1 | 127.0 | C503—C502—C501 | 121.0 (6) |
Ru1—C1—H1 | 122.2 | C503—C502—H502 | 119.5 |
C3—C2—C1 | 108.5 (5) | C501—C502—H502 | 119.5 |
C3—C2—Ru1 | 71.6 (3) | C504—C503—C502 | 120.3 (6) |
C1—C2—Ru1 | 70.6 (3) | C504—C503—H503 | 119.8 |
C3—C2—H2 | 125.7 | C502—C503—H503 | 119.8 |
C1—C2—H2 | 125.7 | C505—C504—C503 | 120.1 (6) |
Ru1—C2—H2 | 123.7 | C505—C504—H504 | 119.9 |
C2—C3—C4 | 108.9 (5) | C503—C504—H504 | 119.9 |
C2—C3—Ru1 | 71.7 (3) | C504—C505—C506 | 119.5 (6) |
C4—C3—Ru1 | 71.3 (3) | C504—C505—H505 | 120.2 |
C2—C3—H3 | 125.5 | C506—C505—H505 | 120.2 |
C4—C3—H3 | 125.5 | C501—C506—C505 | 122.5 (6) |
Ru1—C3—H3 | 123.0 | C501—C506—H506 | 118.8 |
C3—C4—C5 | 107.3 (5) | C505—C506—H506 | 118.8 |
C3—C4—Ru1 | 71.5 (3) | C606—C601—C602 | 117.6 (5) |
C5—C4—Ru1 | 71.0 (3) | C606—C601—P2 | 121.6 (4) |
C3—C4—H4 | 126.3 | C602—C601—P2 | 120.4 (5) |
C5—C4—H4 | 126.3 | C603—C602—C601 | 120.6 (6) |
Ru1—C4—H4 | 122.9 | C603—C602—H602 | 119.7 |
C4—C5—C1 | 109.1 (5) | C601—C602—H602 | 119.7 |
C4—C5—Ru1 | 71.6 (3) | C604—C603—C602 | 120.5 (6) |
C1—C5—Ru1 | 71.3 (3) | C604—C603—H603 | 119.8 |
C4—C5—H5 | 125.4 | C602—C603—H603 | 119.8 |
C1—C5—H5 | 125.4 | C605—C604—C603 | 119.3 (6) |
Ru1—C5—H5 | 123.3 | C605—C604—H604 | 120.3 |
N1—C6—C101 | 114.4 (5) | C603—C604—H604 | 120.3 |
N1—C6—H6A | 103 (3) | C604—C605—C606 | 120.7 (6) |
C101—C6—H6A | 110 (3) | C604—C605—H605 | 119.6 |
N1—C6—H6B | 109 (3) | C606—C605—H605 | 119.6 |
C101—C6—H6B | 106 (3) | C605—C606—C601 | 121.3 (5) |
H6A—C6—H6B | 114 (4) | C605—C606—H606 | 119.3 |
C102—C101—C106 | 118.0 (6) | C601—C606—H606 | 119.3 |
C102—C101—C6 | 121.6 (6) | C702—C701—C706 | 119.1 (5) |
C106—C101—C6 | 120.3 (6) | C702—C701—P2 | 125.1 (5) |
C103—C102—C101 | 121.1 (7) | C706—C701—P2 | 115.7 (4) |
C103—C102—H102 | 119.4 | C701—C702—C703 | 119.5 (6) |
C101—C102—H102 | 119.4 | C701—C702—H702 | 120.3 |
C102—C103—C104 | 119.7 (7) | C703—C702—H702 | 120.3 |
C102—C103—H103 | 120.2 | C704—C703—C702 | 120.6 (6) |
C104—C103—H103 | 120.2 | C704—C703—H703 | 119.7 |
C105—C104—C103 | 119.3 (7) | C702—C703—H703 | 119.7 |
C105—C104—H104 | 120.4 | C703—C704—C705 | 120.2 (6) |
C103—C104—H104 | 120.4 | C703—C704—H704 | 119.9 |
C104—C105—C106 | 121.0 (7) | C705—C704—H704 | 119.9 |
C104—C105—H105 | 119.5 | C706—C705—C704 | 119.2 (6) |
C106—C105—H105 | 119.5 | C706—C705—H705 | 120.4 |
C105—C106—C101 | 120.9 (7) | C704—C705—H705 | 120.4 |
C105—C106—H106 | 119.5 | C705—C706—C701 | 121.4 (6) |
C101—C106—H106 | 119.5 | C705—C706—H706 | 119.3 |
C206—C201—C202 | 117.5 (6) | C701—C706—H706 | 119.3 |
C206—C201—P1 | 127.7 (5) | F3—B1—F4 | 111.8 (6) |
C202—C201—P1 | 114.8 (5) | F3—B1—F2 | 112.1 (6) |
C203—C202—C201 | 120.6 (6) | F4—B1—F2 | 108.4 (6) |
C203—C202—H202 | 119.7 | F3—B1—F1 | 110.3 (6) |
C201—C202—H202 | 119.7 | F4—B1—F1 | 107.3 (6) |
C204—C203—C202 | 120.5 (6) | F2—B1—F1 | 106.7 (6) |
C204—C203—H203 | 119.7 | C6—N1—Ru1 | 118.8 (4) |
C202—C203—H203 | 119.7 | C6—N1—H99A | 110 (3) |
C205—C204—C203 | 119.3 (6) | Ru1—N1—H99A | 109 (3) |
C205—C204—H204 | 120.4 | C6—N1—H99B | 109 (5) |
C203—C204—H204 | 120.4 | Ru1—N1—H99B | 109 (5) |
C206—C205—C204 | 120.0 (6) | H99A—N1—H99B | 100 (5) |
C206—C205—H205 | 120.0 | C301—P1—C201 | 105.5 (3) |
C204—C205—H205 | 120.0 | C301—P1—C401 | 101.8 (3) |
C205—C206—C201 | 122.0 (6) | C201—P1—C401 | 95.7 (3) |
C205—C206—H206 | 119.0 | C301—P1—Ru1 | 110.79 (18) |
C201—C206—H206 | 119.0 | C201—P1—Ru1 | 123.98 (19) |
C302—C301—C306 | 118.4 (5) | C401—P1—Ru1 | 116.1 (2) |
C302—C301—P1 | 121.2 (4) | C601—P2—C501 | 98.1 (3) |
C306—C301—P1 | 120.2 (4) | C601—P2—C701 | 99.3 (3) |
C301—C302—C303 | 121.2 (6) | C501—P2—C701 | 105.2 (3) |
C301—C302—H302 | 119.4 | C601—P2—Ru1 | 116.31 (19) |
C303—C302—H302 | 119.4 | C501—P2—Ru1 | 119.61 (17) |
C304—C303—C302 | 119.7 (6) | C701—P2—Ru1 | 115.19 (18) |
C304—C303—H303 | 120.1 | N1—Ru1—C5 | 132.5 (2) |
C302—C303—H303 | 120.1 | N1—Ru1—C1 | 159.8 (2) |
C305—C304—C303 | 119.6 (6) | C5—Ru1—C1 | 37.56 (19) |
C305—C304—H304 | 120.2 | N1—Ru1—C4 | 99.8 (2) |
C303—C304—H304 | 120.2 | C5—Ru1—C4 | 37.38 (19) |
C304—C305—C306 | 120.7 (6) | C1—Ru1—C4 | 63.1 (2) |
C304—C305—H305 | 119.6 | N1—Ru1—C3 | 97.2 (2) |
C306—C305—H305 | 119.6 | C5—Ru1—C3 | 62.0 (2) |
C301—C306—C305 | 120.3 (5) | C1—Ru1—C3 | 62.7 (2) |
C301—C306—H306 | 119.9 | C4—Ru1—C3 | 37.18 (18) |
C305—C306—H306 | 119.9 | N1—Ru1—C2 | 125.9 (2) |
C406—C401—C402 | 117.1 (5) | C5—Ru1—C2 | 62.2 (2) |
C406—C401—P1 | 122.5 (4) | C1—Ru1—C2 | 38.00 (18) |
C402—C401—P1 | 120.4 (4) | C4—Ru1—C2 | 62.1 (2) |
C403—C402—C401 | 122.1 (6) | C3—Ru1—C2 | 36.70 (19) |
C403—C402—H402 | 118.9 | N1—Ru1—P2 | 89.22 (15) |
C401—C402—H402 | 118.9 | C5—Ru1—P2 | 89.58 (15) |
C402—C403—C404 | 119.7 (6) | C1—Ru1—P2 | 106.13 (15) |
C402—C403—H403 | 120.2 | C4—Ru1—P2 | 109.35 (16) |
C404—C403—H403 | 120.2 | C3—Ru1—P2 | 146.50 (16) |
C405—C404—C403 | 119.9 (5) | C2—Ru1—P2 | 144.09 (15) |
C405—C404—H404 | 120.1 | N1—Ru1—P1 | 93.00 (14) |
C403—C404—H404 | 120.1 | C5—Ru1—P1 | 133.65 (17) |
C404—C405—C406 | 120.0 (6) | C1—Ru1—P1 | 96.70 (17) |
C404—C405—H405 | 120.0 | C4—Ru1—P1 | 146.84 (16) |
C406—C405—H405 | 120.0 | C3—Ru1—P1 | 111.17 (16) |
C401—C406—C405 | 121.2 (6) | C2—Ru1—P1 | 85.65 (16) |
C401—C406—H406 | 119.4 | P2—Ru1—P1 | 101.22 (5) |
C5—C1—C2—C3 | −1.3 (6) | C6—N1—Ru1—C5 | −16.2 (6) |
Ru1—C1—C2—C3 | 61.9 (4) | C6—N1—Ru1—C1 | −67.6 (8) |
C5—C1—C2—Ru1 | −63.2 (4) | C6—N1—Ru1—C4 | −37.0 (5) |
C1—C2—C3—C4 | 0.8 (6) | C6—N1—Ru1—C3 | −74.5 (5) |
Ru1—C2—C3—C4 | 62.0 (4) | C6—N1—Ru1—C2 | −99.5 (5) |
C1—C2—C3—Ru1 | −61.2 (4) | C6—N1—Ru1—P2 | 72.5 (5) |
C2—C3—C4—C5 | 0.1 (6) | C6—N1—Ru1—P1 | 173.7 (5) |
Ru1—C3—C4—C5 | 62.3 (4) | C4—C5—Ru1—N1 | −35.2 (5) |
C2—C3—C4—Ru1 | −62.3 (4) | C1—C5—Ru1—N1 | −153.7 (3) |
C3—C4—C5—C1 | −0.9 (6) | C4—C5—Ru1—C1 | 118.5 (5) |
Ru1—C4—C5—C1 | 61.7 (4) | C1—C5—Ru1—C4 | −118.5 (5) |
C3—C4—C5—Ru1 | −62.7 (4) | C4—C5—Ru1—C3 | 37.7 (3) |
C2—C1—C5—C4 | 1.4 (6) | C1—C5—Ru1—C3 | −80.8 (4) |
Ru1—C1—C5—C4 | −62.0 (4) | C4—C5—Ru1—C2 | 79.5 (4) |
C2—C1—C5—Ru1 | 63.4 (4) | C1—C5—Ru1—C2 | −39.1 (3) |
N1—C6—C101—C102 | −112.2 (7) | C4—C5—Ru1—P2 | −123.7 (3) |
N1—C6—C101—C106 | 69.2 (8) | C1—C5—Ru1—P2 | 117.7 (3) |
C106—C101—C102—C103 | 0.2 (10) | C4—C5—Ru1—P1 | 131.1 (3) |
C6—C101—C102—C103 | −178.4 (6) | C1—C5—Ru1—P1 | 12.6 (4) |
C101—C102—C103—C104 | −0.6 (11) | C5—C1—Ru1—N1 | 71.0 (7) |
C102—C103—C104—C105 | 0.9 (11) | C2—C1—Ru1—N1 | −44.1 (8) |
C103—C104—C105—C106 | −0.8 (11) | C2—C1—Ru1—C5 | −115.0 (5) |
C104—C105—C106—C101 | 0.5 (10) | C5—C1—Ru1—C4 | 36.8 (3) |
C102—C101—C106—C105 | −0.2 (10) | C2—C1—Ru1—C4 | −78.3 (4) |
C6—C101—C106—C105 | 178.5 (6) | C5—C1—Ru1—C3 | 78.7 (4) |
C206—C201—C202—C203 | 3.6 (9) | C2—C1—Ru1—C3 | −36.3 (3) |
P1—C201—C202—C203 | −178.1 (4) | C5—C1—Ru1—C2 | 115.0 (5) |
C201—C202—C203—C204 | −1.0 (9) | C5—C1—Ru1—P2 | −67.1 (3) |
C202—C203—C204—C205 | −1.4 (10) | C2—C1—Ru1—P2 | 177.8 (3) |
C203—C204—C205—C206 | 1.1 (10) | C5—C1—Ru1—P1 | −170.9 (3) |
C204—C205—C206—C201 | 1.7 (10) | C2—C1—Ru1—P1 | 74.1 (3) |
C202—C201—C206—C205 | −4.0 (9) | C3—C4—Ru1—N1 | −89.0 (4) |
P1—C201—C206—C205 | 178.0 (5) | C5—C4—Ru1—N1 | 154.4 (3) |
C306—C301—C302—C303 | −2.2 (9) | C3—C4—Ru1—C5 | 116.6 (5) |
P1—C301—C302—C303 | −176.8 (5) | C3—C4—Ru1—C1 | 79.6 (4) |
C301—C302—C303—C304 | 3.1 (9) | C5—C4—Ru1—C1 | −36.9 (3) |
C302—C303—C304—C305 | −1.6 (9) | C5—C4—Ru1—C3 | −116.6 (5) |
C303—C304—C305—C306 | −0.7 (9) | C3—C4—Ru1—C2 | 36.6 (3) |
C302—C301—C306—C305 | −0.1 (8) | C5—C4—Ru1—C2 | −80.0 (4) |
P1—C301—C306—C305 | 174.6 (4) | C3—C4—Ru1—P2 | 178.4 (3) |
C304—C305—C306—C301 | 1.6 (9) | C5—C4—Ru1—P2 | 61.8 (3) |
C406—C401—C402—C403 | 0.1 (9) | C3—C4—Ru1—P1 | 22.2 (5) |
P1—C401—C402—C403 | 178.2 (4) | C5—C4—Ru1—P1 | −94.3 (4) |
C401—C402—C403—C404 | 0.4 (9) | C2—C3—Ru1—N1 | −145.1 (3) |
C402—C403—C404—C405 | −0.6 (9) | C4—C3—Ru1—N1 | 96.8 (4) |
C403—C404—C405—C406 | 0.3 (9) | C2—C3—Ru1—C5 | 80.2 (4) |
C402—C401—C406—C405 | −0.4 (8) | C4—C3—Ru1—C5 | −37.9 (3) |
P1—C401—C406—C405 | −178.4 (4) | C2—C3—Ru1—C1 | 37.6 (3) |
C404—C405—C406—C401 | 0.2 (9) | C4—C3—Ru1—C1 | −80.5 (4) |
C506—C501—C502—C503 | 0.4 (9) | C2—C3—Ru1—C4 | 118.2 (5) |
P2—C501—C502—C503 | −177.1 (4) | C4—C3—Ru1—C2 | −118.2 (5) |
C501—C502—C503—C504 | 1.3 (9) | C2—C3—Ru1—P2 | 115.4 (4) |
C502—C503—C504—C505 | −1.8 (9) | C4—C3—Ru1—P2 | −2.8 (5) |
C503—C504—C505—C506 | 0.6 (9) | C2—C3—Ru1—P1 | −49.0 (4) |
C502—C501—C506—C505 | −1.7 (9) | C4—C3—Ru1—P1 | −167.2 (3) |
P2—C501—C506—C505 | 175.8 (4) | C3—C2—Ru1—N1 | 44.5 (4) |
C504—C505—C506—C501 | 1.2 (9) | C1—C2—Ru1—N1 | 162.7 (3) |
C606—C601—C602—C603 | 0.2 (8) | C3—C2—Ru1—C5 | −79.6 (4) |
P2—C601—C602—C603 | −171.8 (4) | C1—C2—Ru1—C5 | 38.6 (3) |
C601—C602—C603—C604 | 0.1 (9) | C3—C2—Ru1—C1 | −118.2 (5) |
C602—C603—C604—C605 | −1.1 (9) | C3—C2—Ru1—C4 | −37.1 (3) |
C603—C604—C605—C606 | 1.7 (9) | C1—C2—Ru1—C4 | 81.1 (4) |
C604—C605—C606—C601 | −1.3 (9) | C1—C2—Ru1—C3 | 118.2 (5) |
C602—C601—C606—C605 | 0.4 (8) | C3—C2—Ru1—P2 | −121.8 (3) |
P2—C601—C606—C605 | 172.3 (4) | C1—C2—Ru1—P2 | −3.5 (5) |
C706—C701—C702—C703 | −2.1 (8) | C3—C2—Ru1—P1 | 135.1 (3) |
P2—C701—C702—C703 | 179.8 (4) | C1—C2—Ru1—P1 | −106.7 (3) |
C701—C702—C703—C704 | 1.5 (8) | C601—P2—Ru1—N1 | −95.3 (2) |
C702—C703—C704—C705 | 0.1 (8) | C501—P2—Ru1—N1 | 22.2 (3) |
C703—C704—C705—C706 | −1.2 (9) | C701—P2—Ru1—N1 | 149.1 (2) |
C704—C705—C706—C701 | 0.6 (9) | C601—P2—Ru1—C5 | 37.2 (3) |
C702—C701—C706—C705 | 1.1 (8) | C501—P2—Ru1—C5 | 154.7 (3) |
P2—C701—C706—C705 | 179.4 (4) | C701—P2—Ru1—C5 | −78.4 (3) |
C101—C6—N1—Ru1 | −179.4 (4) | C601—P2—Ru1—C1 | 71.4 (3) |
C302—C301—P1—C201 | −56.5 (5) | C501—P2—Ru1—C1 | −171.2 (3) |
C306—C301—P1—C201 | 129.0 (5) | C701—P2—Ru1—C1 | −44.2 (3) |
C302—C301—P1—C401 | −155.9 (5) | C601—P2—Ru1—C4 | 4.9 (3) |
C306—C301—P1—C401 | 29.6 (5) | C501—P2—Ru1—C4 | 122.3 (3) |
C302—C301—P1—Ru1 | 80.0 (5) | C701—P2—Ru1—C4 | −110.7 (3) |
C306—C301—P1—Ru1 | −94.5 (4) | C601—P2—Ru1—C3 | 6.7 (4) |
C206—C201—P1—C301 | 8.7 (6) | C501—P2—Ru1—C3 | 124.1 (4) |
C202—C201—P1—C301 | −169.3 (4) | C701—P2—Ru1—C3 | −109.0 (4) |
C206—C201—P1—C401 | 112.7 (6) | C601—P2—Ru1—C2 | 73.7 (3) |
C202—C201—P1—C401 | −65.3 (5) | C501—P2—Ru1—C2 | −168.9 (3) |
C206—C201—P1—Ru1 | −120.4 (5) | C701—P2—Ru1—C2 | −42.0 (4) |
C202—C201—P1—Ru1 | 61.6 (5) | C601—P2—Ru1—P1 | 171.8 (2) |
C406—C401—P1—C301 | −126.0 (5) | C501—P2—Ru1—P1 | −70.7 (2) |
C402—C401—P1—C301 | 56.0 (5) | C701—P2—Ru1—P1 | 56.2 (2) |
C406—C401—P1—C201 | 126.8 (5) | C301—P1—Ru1—N1 | −172.6 (3) |
C402—C401—P1—C201 | −51.1 (5) | C201—P1—Ru1—N1 | −45.7 (3) |
C406—C401—P1—Ru1 | −5.6 (5) | C401—P1—Ru1—N1 | 72.0 (2) |
C402—C401—P1—Ru1 | 176.4 (4) | C301—P1—Ru1—C5 | 17.5 (3) |
C606—C601—P2—C501 | −99.2 (5) | C201—P1—Ru1—C5 | 144.4 (3) |
C602—C601—P2—C501 | 72.4 (5) | C401—P1—Ru1—C5 | −97.9 (3) |
C606—C601—P2—C701 | 153.8 (5) | C301—P1—Ru1—C1 | 25.2 (2) |
C602—C601—P2—C701 | −34.5 (5) | C201—P1—Ru1—C1 | 152.1 (3) |
C606—C601—P2—Ru1 | 29.6 (5) | C401—P1—Ru1—C1 | −90.3 (2) |
C602—C601—P2—Ru1 | −158.8 (4) | C301—P1—Ru1—C4 | 74.3 (4) |
C506—C501—P2—C601 | 17.4 (5) | C201—P1—Ru1—C4 | −158.8 (4) |
C502—C501—P2—C601 | −165.2 (5) | C401—P1—Ru1—C4 | −41.1 (4) |
C506—C501—P2—C701 | 119.5 (5) | C301—P1—Ru1—C3 | 88.5 (3) |
C502—C501—P2—C701 | −63.2 (5) | C201—P1—Ru1—C3 | −144.6 (3) |
C506—C501—P2—Ru1 | −109.1 (5) | C401—P1—Ru1—C3 | −26.9 (3) |
C502—C501—P2—Ru1 | 68.3 (5) | C301—P1—Ru1—C2 | 61.6 (2) |
C702—C701—P2—C601 | 111.1 (5) | C201—P1—Ru1—C2 | −171.5 (3) |
C706—C701—P2—C601 | −67.1 (5) | C401—P1—Ru1—C2 | −53.8 (2) |
C702—C701—P2—C501 | 10.0 (5) | C301—P1—Ru1—P2 | −82.8 (2) |
C706—C701—P2—C501 | −168.2 (4) | C201—P1—Ru1—P2 | 44.1 (2) |
C702—C701—P2—Ru1 | −123.9 (4) | C401—P1—Ru1—P2 | 161.8 (2) |
C706—C701—P2—Ru1 | 57.9 (5) |
Experimental details
Crystal data | |
Chemical formula | [Ru(C5H5)(C7H9N)(C18H15P)2]BF4 |
Mr | 884.66 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 200 |
a, b, c (Å) | 13.4255 (3), 21.1335 (6), 28.6552 (8) |
V (Å3) | 8130.3 (4) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 4.31 |
Crystal size (mm) | 0.08 × 0.05 × 0.03 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (XABS2; Parkin et al., 1995) |
Tmin, Tmax | 0.701, 0.898 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 54625, 7148, 3839 |
Rint | 0.141 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.133, 0.90 |
No. of reflections | 7148 |
No. of parameters | 530 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.86, −0.59 |
Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, DIRDIF (Beurskens et al., 1992), SHELXL97 (Sheldrick, 1997), EUCLID (Spek, 1982), SHELXL97.
Hydroamination of alkenes and alkynes, which constitutes the formal addition of an N—H bond across a carbon–carbon multiple bond, represents an attractive route to numerous classes of organonitrogen molecules, such as alkylated amines, enamines or imines (Müller & Beller, 1998). Recent advances in catalytic aminations are based on early-transition-metal and f-element complexes (Schaverien, 1994). However, catalytic additions of amines H—NR2 to non-activated double or triple bonds mediated by late-transition-metal complexes are still rare (Schaverien, 1994). In this context, we have synthesized the RuII complex [(Cp)Ru(H2NCH2Ph)(PPh3)2][BF4], (I), to use as a catalyst precursor for amination reactions. The synthesis and crystal structure reported herein is part of this study.