Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102022461/tr1046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102022461/tr1046Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102022461/tr1046IIsup3.hkl |
CCDC references: 205289; 205290
For (I), a solution of [Ru(ttp)(CO)(EtOH)] in tetrahydrofuran was irradiated with a 100 W high-pressure mercury lamp under N2 for 6 h. An equimolar quantity of N2═C(COPh)2 was added and the resulting solution refluxed for 6 h. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel and eluted with CH2Cl2/hexane (2:1), to afford [Ru(ttp){C(COPh)2}], (I'). Addition of an excess amount of pyridine to a CH2Cl2 solution of (I') and evaporation gave compound (I) as a dark-red solid. Compound (II) was prepared according to a procedure similar to that of Kawai et al. (2002). The detailed procedure will be published elsewhere (Wada et al., 2002). Crystals of (I) and (II) were prepared by recrystallization from CH2Cl2/cyclohexane (1:1) and CH2Cl2/pyridine (1:1) solutions, respectively.
All H atoms were placed in geometrically idealized positions, with Csp2—H = 0.93 Å or Csp3—H = 0.96 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).
For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku Corporation, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[Ru(C48H36N4)(C15H10O2)(C5H5N)] | F(000) = 2216 |
Mr = 1071.21 | Dx = 1.319 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 15.806 (2) Å | θ = 10.8–13.7° |
b = 16.6172 (18) Å | µ = 0.34 mm−1 |
c = 20.644 (2) Å | T = 296 K |
β = 95.872 (10)° | Needle, dark red |
V = 5393.7 (10) Å3 | 0.20 × 0.12 × 0.10 mm |
Z = 4 |
Rigaku AFC-7R diffractometer | Rint = 0.048 |
Radiation source: rotating Mo anticathode | θmax = 27.5°, θmin = 2.6° |
Graphite monochromator | h = 0→20 |
ω/2θ scans | k = 0→21 |
6419 measured reflections | l = −26→26 |
6197 independent reflections | 3 standard reflections every 150 reflections |
2792 reflections with I > 2σ(I) | intensity decay: 1.5% |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0752P)2] where P = (Fo2 + 2Fc2)/3 |
6197 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
[Ru(C48H36N4)(C15H10O2)(C5H5N)] | V = 5393.7 (10) Å3 |
Mr = 1071.21 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.806 (2) Å | µ = 0.34 mm−1 |
b = 16.6172 (18) Å | T = 296 K |
c = 20.644 (2) Å | 0.20 × 0.12 × 0.10 mm |
β = 95.872 (10)° |
Rigaku AFC-7R diffractometer | Rint = 0.048 |
6419 measured reflections | 3 standard reflections every 150 reflections |
6197 independent reflections | intensity decay: 1.5% |
2792 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.64 e Å−3 |
6197 reflections | Δρmin = −0.51 e Å−3 |
345 parameters |
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 | ||
Ru | 0.5000 | 0.63899 (4) | 0.2500 | 0.0426 (2) | |
O | 0.5512 (3) | 0.8122 (3) | 0.15859 (19) | 0.0658 (11) | |
N1 | 0.3831 (3) | 0.6273 (3) | 0.28244 (19) | 0.0447 (10) | |
N2 | 0.4442 (3) | 0.6359 (3) | 0.15594 (19) | 0.0461 (10) | |
N3 | 0.5000 | 0.4988 (4) | 0.2500 | 0.0548 (17) | |
C1 | 0.3664 (3) | 0.6281 (3) | 0.3473 (3) | 0.0502 (14) | |
C2 | 0.2762 (4) | 0.6202 (4) | 0.3491 (3) | 0.0620 (18) | |
H1 | 0.2477 | 0.6183 | 0.3863 | 0.074* | |
C3 | 0.2402 (4) | 0.6161 (4) | 0.2871 (3) | 0.0627 (17) | |
H2 | 0.1825 | 0.6104 | 0.2741 | 0.075* | |
C4 | 0.3058 (3) | 0.6219 (3) | 0.2452 (3) | 0.0504 (14) | |
C5 | 0.2946 (3) | 0.6247 (3) | 0.1767 (3) | 0.0521 (14) | |
C6 | 0.3586 (3) | 0.6339 (3) | 0.1358 (2) | 0.0476 (12) | |
C7 | 0.3464 (4) | 0.6390 (4) | 0.0660 (3) | 0.0621 (15) | |
H3 | 0.2945 | 0.6400 | 0.0403 | 0.074* | |
C8 | 0.4237 (4) | 0.6419 (4) | 0.0447 (3) | 0.0585 (14) | |
H4 | 0.4349 | 0.6454 | 0.0014 | 0.070* | |
C9 | 0.4866 (3) | 0.6387 (4) | 0.1003 (2) | 0.0503 (12) | |
C10 | 0.5739 (3) | 0.6348 (3) | 0.0990 (2) | 0.0491 (12) | |
C11 | 0.2044 (4) | 0.6154 (3) | 0.1448 (3) | 0.0529 (15) | |
C12 | 0.1617 (4) | 0.6767 (4) | 0.1099 (3) | 0.0675 (17) | |
H5 | 0.1884 | 0.7260 | 0.1055 | 0.081* | |
C13 | 0.0796 (4) | 0.6652 (4) | 0.0814 (4) | 0.083 (2) | |
H6 | 0.0521 | 0.7069 | 0.0578 | 0.100* | |
C14 | 0.0377 (4) | 0.5932 (4) | 0.0871 (4) | 0.078 (2) | |
C15 | 0.0797 (5) | 0.5337 (4) | 0.1224 (4) | 0.092 (2) | |
H7 | 0.0522 | 0.4850 | 0.1274 | 0.110* | |
C16 | 0.1611 (4) | 0.5433 (4) | 0.1506 (3) | 0.0741 (19) | |
H8 | 0.1879 | 0.5011 | 0.1739 | 0.089* | |
C17 | −0.0516 (5) | 0.5811 (5) | 0.0537 (5) | 0.121 (3) | |
H9 | −0.0707 | 0.6298 | 0.0318 | 0.145* | |
H10 | −0.0894 | 0.5675 | 0.0856 | 0.145* | |
H11 | −0.0512 | 0.5382 | 0.0225 | 0.145* | |
C18 | 0.6085 (3) | 0.6388 (4) | 0.0340 (3) | 0.0529 (13) | |
C19 | 0.6268 (5) | 0.7110 (4) | 0.0080 (3) | 0.084 (2) | |
H12 | 0.6163 | 0.7582 | 0.0300 | 0.101* | |
C20 | 0.6611 (5) | 0.7148 (4) | −0.0512 (4) | 0.095 (3) | |
H13 | 0.6733 | 0.7651 | −0.0678 | 0.114* | |
C21 | 0.6774 (4) | 0.6491 (5) | −0.0856 (3) | 0.0698 (18) | |
C22 | 0.6562 (6) | 0.5782 (5) | −0.0601 (4) | 0.103 (3) | |
H14 | 0.6649 | 0.5314 | −0.0832 | 0.123* | |
C23 | 0.6218 (6) | 0.5715 (4) | −0.0012 (3) | 0.095 (3) | |
H15 | 0.6078 | 0.5212 | 0.0142 | 0.114* | |
C24 | 0.7157 (5) | 0.6553 (5) | −0.1496 (3) | 0.099 (3) | |
H16 | 0.7224 | 0.6023 | −0.1670 | 0.118* | |
H17 | 0.7702 | 0.6811 | −0.1427 | 0.118* | |
H18 | 0.6787 | 0.6863 | −0.1798 | 0.118* | |
C25 | 0.5000 | 0.7519 (5) | 0.2500 | 0.0441 (18) | |
C26 | 0.4888 (4) | 0.7992 (3) | 0.1879 (2) | 0.0493 (14) | |
C27 | 0.4045 (4) | 0.8323 (3) | 0.1641 (3) | 0.0513 (14) | |
C28 | 0.3933 (4) | 0.8643 (4) | 0.1022 (3) | 0.0746 (18) | |
H19 | 0.4373 | 0.8629 | 0.0755 | 0.089* | |
C29 | 0.3153 (6) | 0.8989 (5) | 0.0800 (4) | 0.101 (3) | |
H20 | 0.3076 | 0.9216 | 0.0386 | 0.121* | |
C30 | 0.2501 (6) | 0.8996 (5) | 0.1184 (5) | 0.094 (3) | |
H21 | 0.1985 | 0.9233 | 0.1033 | 0.112* | |
C31 | 0.2601 (5) | 0.8661 (5) | 0.1785 (4) | 0.085 (2) | |
H22 | 0.2153 | 0.8665 | 0.2045 | 0.102* | |
C32 | 0.3371 (4) | 0.8311 (4) | 0.2014 (3) | 0.0652 (17) | |
H23 | 0.3433 | 0.8068 | 0.2422 | 0.078* | |
C33 | 0.5149 (4) | 0.4568 (4) | 0.1979 (3) | 0.0721 (19) | |
H24 | 0.5253 | 0.4849 | 0.1606 | 0.087* | |
C34 | 0.5160 (5) | 0.3752 (4) | 0.1958 (4) | 0.096 (2) | |
H25 | 0.5274 | 0.3485 | 0.1580 | 0.115* | |
C35 | 0.5000 | 0.3327 (7) | 0.2500 | 0.100 (4) | |
H26 | 0.5000 | 0.2767 | 0.2500 | 0.120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru | 0.0424 (4) | 0.0448 (4) | 0.0412 (3) | 0.000 | 0.0076 (3) | 0.000 |
O | 0.069 (3) | 0.070 (3) | 0.061 (3) | −0.010 (2) | 0.018 (2) | 0.010 (2) |
N1 | 0.046 (2) | 0.053 (3) | 0.035 (2) | −0.001 (2) | 0.0068 (19) | 0.004 (2) |
N2 | 0.046 (2) | 0.048 (2) | 0.044 (2) | −0.003 (2) | 0.0068 (19) | −0.007 (2) |
N3 | 0.048 (4) | 0.052 (4) | 0.065 (5) | 0.000 | 0.007 (3) | 0.000 |
C1 | 0.048 (3) | 0.042 (3) | 0.062 (3) | 0.002 (3) | 0.017 (3) | −0.003 (3) |
C2 | 0.057 (4) | 0.075 (5) | 0.058 (4) | 0.001 (3) | 0.020 (3) | −0.002 (3) |
C3 | 0.042 (3) | 0.078 (5) | 0.069 (4) | −0.001 (3) | 0.012 (3) | 0.002 (3) |
C4 | 0.044 (3) | 0.050 (4) | 0.058 (3) | 0.000 (2) | 0.007 (3) | 0.001 (3) |
C5 | 0.045 (3) | 0.050 (4) | 0.061 (3) | −0.005 (3) | 0.001 (3) | −0.003 (3) |
C6 | 0.047 (3) | 0.046 (3) | 0.047 (3) | −0.002 (3) | −0.003 (2) | −0.004 (3) |
C7 | 0.055 (3) | 0.080 (4) | 0.049 (3) | −0.009 (4) | −0.004 (3) | −0.001 (4) |
C8 | 0.069 (4) | 0.064 (4) | 0.041 (3) | −0.011 (4) | 0.003 (3) | −0.013 (3) |
C9 | 0.060 (3) | 0.046 (3) | 0.045 (3) | −0.007 (3) | 0.009 (2) | −0.003 (3) |
C10 | 0.058 (3) | 0.046 (3) | 0.045 (3) | −0.005 (3) | 0.012 (2) | −0.003 (3) |
C11 | 0.047 (3) | 0.054 (4) | 0.057 (3) | −0.003 (3) | 0.000 (3) | −0.008 (3) |
C12 | 0.062 (4) | 0.061 (4) | 0.076 (4) | −0.014 (3) | −0.007 (3) | 0.004 (3) |
C13 | 0.064 (4) | 0.067 (5) | 0.113 (6) | 0.000 (4) | −0.020 (4) | 0.008 (4) |
C14 | 0.053 (4) | 0.070 (5) | 0.106 (6) | −0.011 (4) | −0.010 (4) | 0.002 (4) |
C15 | 0.066 (5) | 0.060 (5) | 0.143 (7) | −0.017 (4) | −0.020 (5) | 0.015 (5) |
C16 | 0.055 (4) | 0.060 (4) | 0.101 (5) | −0.009 (3) | −0.019 (4) | 0.007 (4) |
C17 | 0.060 (5) | 0.105 (7) | 0.187 (10) | −0.020 (5) | −0.033 (5) | 0.012 (7) |
C18 | 0.053 (3) | 0.053 (3) | 0.055 (3) | 0.001 (3) | 0.014 (3) | 0.001 (3) |
C19 | 0.134 (7) | 0.052 (4) | 0.075 (5) | 0.000 (4) | 0.057 (5) | −0.006 (3) |
C20 | 0.149 (8) | 0.051 (4) | 0.098 (6) | −0.005 (4) | 0.074 (6) | 0.005 (4) |
C21 | 0.086 (5) | 0.079 (5) | 0.049 (3) | 0.009 (4) | 0.026 (3) | 0.002 (4) |
C22 | 0.183 (9) | 0.069 (5) | 0.066 (5) | 0.012 (5) | 0.058 (5) | −0.009 (4) |
C23 | 0.167 (8) | 0.057 (4) | 0.069 (5) | −0.009 (5) | 0.056 (5) | −0.005 (4) |
C24 | 0.132 (7) | 0.103 (6) | 0.070 (4) | 0.006 (5) | 0.056 (5) | 0.007 (4) |
C25 | 0.036 (4) | 0.055 (5) | 0.041 (4) | 0.000 | 0.001 (3) | 0.000 |
C26 | 0.066 (4) | 0.041 (3) | 0.041 (3) | −0.007 (3) | 0.010 (3) | −0.002 (2) |
C27 | 0.059 (4) | 0.042 (3) | 0.051 (3) | −0.001 (3) | −0.004 (3) | 0.008 (2) |
C28 | 0.084 (5) | 0.085 (5) | 0.052 (3) | −0.022 (4) | −0.012 (3) | 0.008 (4) |
C29 | 0.110 (7) | 0.093 (6) | 0.089 (6) | −0.033 (5) | −0.043 (5) | 0.037 (5) |
C30 | 0.082 (6) | 0.080 (5) | 0.109 (7) | 0.013 (5) | −0.036 (5) | 0.012 (5) |
C31 | 0.075 (5) | 0.096 (6) | 0.080 (5) | 0.023 (5) | −0.008 (4) | −0.007 (5) |
C32 | 0.064 (4) | 0.076 (4) | 0.055 (4) | 0.014 (3) | 0.001 (3) | 0.001 (3) |
C33 | 0.076 (5) | 0.061 (4) | 0.081 (5) | −0.001 (4) | 0.012 (4) | −0.013 (4) |
C34 | 0.111 (6) | 0.064 (6) | 0.112 (7) | 0.002 (4) | 0.010 (5) | −0.021 (4) |
C35 | 0.114 (10) | 0.051 (6) | 0.132 (11) | 0.000 | 0.004 (9) | 0.000 |
Ru—N1 | 2.038 (4) | C25—C26 | 1.498 (6) |
Ru—N2 | 2.049 (4) | C26—C27 | 1.479 (8) |
Ru—N3 | 2.329 (7) | C27—C32 | 1.377 (8) |
Ru—C25 | 1.877 (8) | C27—C28 | 1.378 (8) |
O—C26 | 1.228 (6) | C28—C29 | 1.394 (11) |
N1—C1 | 1.392 (6) | C29—C30 | 1.362 (12) |
N1—C4 | 1.379 (7) | C30—C31 | 1.354 (10) |
N2—C6 | 1.374 (6) | C31—C32 | 1.388 (9) |
N2—C9 | 1.387 (6) | C33—C34 | 1.358 (9) |
N3—C33 | 1.323 (7) | C34—C35 | 1.369 (9) |
C1—C2 | 1.436 (8) | C2—H1 | 0.9300 |
C2—C3 | 1.347 (8) | C3—H2 | 0.9300 |
C3—C4 | 1.420 (8) | C7—H3 | 0.9300 |
C4—C5 | 1.407 (8) | C8—H4 | 0.9300 |
C5—C6 | 1.391 (7) | C12—H5 | 0.9300 |
C6—C7 | 1.437 (7) | C13—H6 | 0.9300 |
C7—C8 | 1.342 (8) | C15—H7 | 0.9300 |
C8—C9 | 1.440 (7) | C16—H8 | 0.9300 |
C9—C10 | 1.385 (7) | C17—H9 | 0.9600 |
C10—C1i | 1.384 (7) | C17—H10 | 0.9600 |
C5—C11 | 1.515 (8) | C17—H11 | 0.9600 |
C11—C12 | 1.383 (8) | C19—H12 | 0.9300 |
C12—C13 | 1.382 (9) | C20—H13 | 0.9300 |
C13—C14 | 1.378 (9) | C22—H14 | 0.9300 |
C14—C15 | 1.360 (9) | C23—H15 | 0.9300 |
C15—C16 | 1.366 (9) | C24—H16 | 0.9600 |
C16—C11 | 1.390 (8) | C24—H17 | 0.9600 |
C14—C17 | 1.520 (9) | C24—H18 | 0.9600 |
C10—C18 | 1.501 (7) | C28—H19 | 0.9300 |
C18—C19 | 1.357 (8) | C29—H20 | 0.9300 |
C19—C20 | 1.388 (8) | C30—H21 | 0.9300 |
C20—C21 | 1.342 (9) | C31—H22 | 0.9300 |
C21—C22 | 1.347 (9) | C32—H23 | 0.9300 |
C22—C23 | 1.386 (9) | C33—H24 | 0.9300 |
C23—C18 | 1.361 (8) | C34—H25 | 0.9300 |
C21—C24 | 1.512 (8) | C35—H26 | 0.9300 |
N1—Ru—N1i | 169.1 (2) | C27—C26—C25 | 120.2 (4) |
N1—Ru—N2 | 89.57 (15) | C32—C27—C28 | 119.4 (6) |
N1—Ru—N2i | 90.16 (15) | C32—C27—C26 | 122.0 (5) |
N1—Ru—N3 | 84.55 (12) | C28—C27—C26 | 118.6 (6) |
N2i—Ru—N2 | 177.1 (3) | C27—C28—C29 | 119.3 (7) |
N2—Ru—N3 | 88.57 (13) | C30—C29—C28 | 120.5 (7) |
N1—Ru—C25 | 95.45 (12) | C31—C30—C29 | 120.4 (7) |
N2—Ru—C25 | 91.43 (13) | C30—C31—C32 | 120.0 (7) |
N3—Ru—C25 | 180 | C27—C32—C31 | 120.4 (6) |
C4—N1—C1 | 107.1 (4) | N3—C33—C34 | 123.9 (8) |
C4—N1—Ru | 127.2 (3) | C33—C34—C35 | 119.0 (9) |
C1—N1—Ru | 125.6 (3) | C34—C35—C34i | 117.9 (11) |
C6—N2—C9 | 107.1 (4) | C3—C2—H1 | 126.1 |
C6—N2—Ru | 127.0 (3) | C1—C2—H1 | 126.1 |
C9—N2—Ru | 125.9 (3) | C2—C3—H2 | 125.9 |
C33—N3—C33i | 116.4 (9) | C4—C3—H2 | 125.9 |
C33—N3—Ru | 121.8 (4) | C8—C7—H3 | 126.4 |
C33i—N3—Ru | 121.8 (4) | C6—C7—H3 | 126.4 |
C10i—C1—N1 | 126.3 (5) | C7—C8—H4 | 125.8 |
C10i—C1—C2 | 125.7 (5) | C9—C8—H4 | 125.8 |
N1—C1—C2 | 108.0 (5) | C13—C12—H5 | 119.8 |
C3—C2—C1 | 107.7 (5) | C11—C12—H5 | 119.8 |
C2—C3—C4 | 108.2 (5) | C14—C13—H6 | 119.3 |
N1—C4—C5 | 124.9 (5) | C12—C13—H6 | 119.3 |
N1—C4—C3 | 108.9 (5) | C14—C15—H7 | 119.0 |
C5—C4—C3 | 126.2 (5) | C16—C15—H7 | 119.0 |
C6—C5—C4 | 126.0 (5) | C15—C16—H8 | 119.5 |
C6—C5—C11 | 117.3 (5) | C11—C16—H8 | 119.5 |
C4—C5—C11 | 116.7 (5) | C14—C17—H9 | 109.5 |
N2—C6—C5 | 125.1 (5) | C14—C17—H10 | 109.5 |
N2—C6—C7 | 109.2 (5) | H9—C17—H10 | 109.5 |
C5—C6—C7 | 125.6 (5) | C14—C17—H11 | 109.5 |
C8—C7—C6 | 107.2 (5) | H9—C17—H11 | 109.5 |
C7—C8—C9 | 108.4 (5) | H10—C17—H11 | 109.5 |
C10—C9—N2 | 125.5 (5) | C18—C19—H12 | 119.8 |
C10—C9—C8 | 126.4 (5) | C20—C19—H12 | 119.8 |
N2—C9—C8 | 108.0 (5) | C21—C20—H13 | 118.6 |
C1i—C10—C9 | 125.9 (5) | C19—C20—H13 | 118.6 |
C1i—C10—C18 | 116.0 (5) | C21—C22—H14 | 118.4 |
C9—C10—C18 | 118.1 (5) | C23—C22—H14 | 118.4 |
C12—C11—C16 | 117.4 (6) | C18—C23—H15 | 120.1 |
C12—C11—C5 | 122.6 (5) | C22—C23—H15 | 120.1 |
C16—C11—C5 | 120.0 (5) | C21—C24—H16 | 109.5 |
C13—C12—C11 | 120.5 (6) | C21—C24—H17 | 109.5 |
C14—C13—C12 | 121.5 (7) | H16—C24—H17 | 109.5 |
C15—C14—C13 | 117.7 (6) | C21—C24—H18 | 109.5 |
C15—C14—C17 | 121.7 (7) | H16—C24—H18 | 109.5 |
C13—C14—C17 | 120.6 (7) | H17—C24—H18 | 109.5 |
C14—C15—C16 | 122.0 (7) | C27—C28—H19 | 120.4 |
C15—C16—C11 | 121.0 (6) | C29—C28—H19 | 120.4 |
C19—C18—C23 | 117.6 (5) | C30—C29—H20 | 119.7 |
C19—C18—C10 | 120.3 (5) | C28—C29—H20 | 119.7 |
C23—C18—C10 | 122.0 (6) | C31—C30—H21 | 119.8 |
C18—C19—C20 | 120.5 (6) | C29—C30—H21 | 119.8 |
C21—C20—C19 | 122.8 (6) | C30—C31—H22 | 120.0 |
C20—C21—C22 | 115.8 (5) | C32—C31—H22 | 120.0 |
C20—C21—C24 | 121.5 (7) | C27—C32—H23 | 119.8 |
C22—C21—C24 | 122.6 (7) | C31—C32—H23 | 119.8 |
C21—C22—C23 | 123.3 (6) | N3—C33—H24 | 118.1 |
C18—C23—C22 | 119.9 (6) | C34—C33—H24 | 118.1 |
C26—C25—C26i | 116.8 (6) | C33—C34—H25 | 120.5 |
Ru—C25—C26 | 121.6 (3) | C35—C34—H25 | 120.5 |
O—C26—C27 | 120.8 (5) | C34—C35—H26 | 121.1 |
O—C26—C25 | 118.9 (5) | ||
N1—Ru—N3—C33 | 127.1 (4) | C26i—C25—C26—C27 | −81.6 (5) |
N2—Ru—N3—C33 | 37.4 (4) | Ru—C25—C26—C27 | 98.4 (5) |
N1—Ru—C25—C26 | −107.1 (3) | O—C26—C27—C32 | −168.2 (5) |
N2—Ru—C25—C26 | −17.4 (3) | C25—C26—C27—C32 | 9.3 (8) |
C26i—C25—C26—O | 95.9 (5) | O—C26—C27—C28 | 12.6 (8) |
Ru—C25—C26—O | −84.1 (5) | C25—C26—C27—C28 | −170.0 (6) |
Symmetry code: (i) −x+1, y, −z+1/2. |
[Ru(C48H36N4)(C15H8F6)(C5H5N)] | F(000) = 2360 |
Mr = 1151.19 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 12.4428 (17) Å | θ = 14.9–15.0° |
b = 17.3768 (19) Å | µ = 0.36 mm−1 |
c = 25.1794 (17) Å | T = 296 K |
β = 99.436 (9)° | Prism, dark red |
V = 5370.5 (10) Å3 | 0.50 × 0.40 × 0.20 mm |
Z = 4 |
Rigaku AFC-7R diffractometer | 8702 reflections with I > 2σ(I) |
Radiation source: rotating Mo anticathode | Rint = 0.018 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
ω scans | h = 0→16 |
Absorption correction: ψ scan (North et al., 1968) | k = −22→0 |
Tmin = 0.840, Tmax = 0.930 | l = −32→32 |
12882 measured reflections | 3 standard reflections every 150 reflections |
12323 independent reflections | intensity decay: 0.5% |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0488P)2 + 1.7405P] where P = (Fo2 + 2Fc2)/3 |
12323 reflections | (Δ/σ)max = 0.001 |
721 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
[Ru(C48H36N4)(C15H8F6)(C5H5N)] | V = 5370.5 (10) Å3 |
Mr = 1151.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4428 (17) Å | µ = 0.36 mm−1 |
b = 17.3768 (19) Å | T = 296 K |
c = 25.1794 (17) Å | 0.50 × 0.40 × 0.20 mm |
β = 99.436 (9)° |
Rigaku AFC-7R diffractometer | 8702 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.018 |
Tmin = 0.840, Tmax = 0.930 | 3 standard reflections every 150 reflections |
12882 measured reflections | intensity decay: 0.5% |
12323 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.32 e Å−3 |
12323 reflections | Δρmin = −0.30 e Å−3 |
721 parameters |
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 | ||
Ru | 0.099529 (15) | 0.276037 (12) | 0.112533 (8) | 0.03681 (6) | |
F1 | 0.1755 (3) | −0.02171 (17) | 0.32508 (10) | 0.1254 (10) | |
F2 | 0.3033 (2) | 0.0438 (2) | 0.30258 (10) | 0.1422 (13) | |
F3 | 0.1773 (3) | 0.09841 (19) | 0.33376 (10) | 0.1470 (13) | |
F4 | 0.3295 (2) | −0.01272 (15) | −0.04399 (10) | 0.1109 (8) | |
F5 | 0.1622 (2) | 0.00427 (17) | −0.03831 (10) | 0.1122 (9) | |
F6 | 0.2485 (3) | 0.09030 (15) | −0.07310 (9) | 0.1177 (9) | |
N1 | −0.05825 (16) | 0.24049 (13) | 0.08965 (8) | 0.0410 (5) | |
N2 | 0.07158 (16) | 0.28449 (12) | 0.19014 (8) | 0.0407 (5) | |
N3 | 0.25141 (16) | 0.32371 (12) | 0.13378 (8) | 0.0400 (5) | |
N4 | 0.12282 (16) | 0.27647 (12) | 0.03356 (8) | 0.0402 (4) | |
N5 | 0.03744 (18) | 0.40103 (13) | 0.09832 (9) | 0.0470 (5) | |
C1 | −0.1032 (2) | 0.21636 (15) | 0.03845 (10) | 0.0434 (6) | |
C2 | −0.2102 (2) | 0.18622 (17) | 0.04027 (11) | 0.0495 (6) | |
H1 | −0.2584 | 0.1667 | 0.0112 | 0.059* | |
C3 | −0.2281 (2) | 0.19124 (18) | 0.09123 (11) | 0.0511 (7) | |
H2 | −0.2907 | 0.1754 | 0.1039 | 0.061* | |
C4 | −0.1332 (2) | 0.22545 (16) | 0.12274 (10) | 0.0435 (6) | |
C5 | −0.1176 (2) | 0.23684 (16) | 0.17851 (10) | 0.0437 (6) | |
C6 | −0.0225 (2) | 0.26538 (16) | 0.20932 (10) | 0.0433 (6) | |
C7 | −0.0056 (2) | 0.27736 (18) | 0.26690 (11) | 0.0541 (7) | |
H3 | −0.0567 | 0.2697 | 0.2895 | 0.065* | |
C8 | 0.0976 (2) | 0.30171 (18) | 0.28176 (11) | 0.0520 (7) | |
H4 | 0.1309 | 0.3136 | 0.3166 | 0.062* | |
C9 | 0.1472 (2) | 0.30601 (16) | 0.23391 (10) | 0.0433 (6) | |
C10 | 0.2538 (2) | 0.32930 (15) | 0.23234 (10) | 0.0422 (6) | |
C11 | 0.3008 (2) | 0.33989 (15) | 0.18582 (10) | 0.0431 (6) | |
C12 | 0.4076 (2) | 0.37039 (17) | 0.18433 (11) | 0.0514 (7) | |
H5 | 0.4582 | 0.3855 | 0.2139 | 0.062* | |
C13 | 0.4212 (2) | 0.37315 (17) | 0.13228 (11) | 0.0517 (7) | |
H6 | 0.4822 | 0.3918 | 0.1195 | 0.062* | |
C14 | 0.3247 (2) | 0.34220 (15) | 0.10003 (10) | 0.0436 (6) | |
C15 | 0.3093 (2) | 0.32987 (15) | 0.04438 (10) | 0.0439 (6) | |
C16 | 0.2162 (2) | 0.29682 (15) | 0.01416 (10) | 0.0424 (6) | |
C17 | 0.2036 (2) | 0.27733 (16) | −0.04219 (11) | 0.0490 (6) | |
H7 | 0.2552 | 0.2845 | −0.0646 | 0.059* | |
C18 | 0.1038 (2) | 0.24695 (17) | −0.05628 (11) | 0.0488 (6) | |
H8 | 0.0735 | 0.2293 | −0.0903 | 0.059* | |
C19 | 0.0521 (2) | 0.24668 (15) | −0.00914 (10) | 0.0423 (6) | |
C20 | −0.0525 (2) | 0.21902 (15) | −0.00729 (10) | 0.0423 (6) | |
C21 | −0.2073 (2) | 0.20829 (16) | 0.20679 (10) | 0.0461 (6) | |
C22 | −0.1905 (2) | 0.14399 (18) | 0.23965 (11) | 0.0513 (7) | |
H9 | −0.1211 | 0.1226 | 0.2474 | 0.062* | |
C23 | −0.2751 (2) | 0.11093 (18) | 0.26127 (12) | 0.0560 (7) | |
H10 | −0.2616 | 0.0676 | 0.2830 | 0.067* | |
C24 | −0.3792 (2) | 0.14130 (19) | 0.25103 (12) | 0.0568 (7) | |
C25 | −0.3950 (2) | 0.2070 (2) | 0.21953 (12) | 0.0584 (8) | |
H11 | −0.4637 | 0.2295 | 0.2129 | 0.070* | |
C26 | −0.3106 (2) | 0.24026 (18) | 0.19759 (12) | 0.0522 (7) | |
H12 | −0.3236 | 0.2843 | 0.1766 | 0.063* | |
C27 | −0.4726 (3) | 0.1042 (2) | 0.27239 (16) | 0.0828 (11) | |
H13 | −0.5205 | 0.0803 | 0.2433 | 0.099* | |
H14 | −0.5119 | 0.1427 | 0.2888 | 0.099* | |
H15 | −0.4450 | 0.0660 | 0.2987 | 0.099* | |
C28 | 0.3276 (2) | 0.33959 (16) | 0.28545 (10) | 0.0450 (6) | |
C29 | 0.3615 (3) | 0.27619 (18) | 0.31649 (12) | 0.0594 (8) | |
H16 | 0.3352 | 0.2279 | 0.3049 | 0.071* | |
C30 | 0.4333 (3) | 0.2822 (2) | 0.36432 (13) | 0.0651 (8) | |
H17 | 0.4552 | 0.2382 | 0.3842 | 0.078* | |
C31 | 0.4728 (2) | 0.3529 (2) | 0.38276 (11) | 0.0583 (8) | |
C32 | 0.4381 (3) | 0.4163 (2) | 0.35279 (12) | 0.0642 (8) | |
H18 | 0.4638 | 0.4646 | 0.3647 | 0.077* | |
C33 | 0.3647 (3) | 0.41023 (18) | 0.30450 (12) | 0.0591 (8) | |
H19 | 0.3409 | 0.4544 | 0.2852 | 0.071* | |
C34 | 0.5538 (3) | 0.3587 (3) | 0.43448 (13) | 0.0837 (12) | |
H20 | 0.5442 | 0.3159 | 0.4573 | 0.100* | |
H21 | 0.5420 | 0.4059 | 0.4526 | 0.100* | |
H22 | 0.6265 | 0.3581 | 0.4263 | 0.100* | |
C35 | 0.3998 (2) | 0.35308 (16) | 0.01488 (11) | 0.0463 (6) | |
C36 | 0.5029 (2) | 0.32118 (19) | 0.02690 (13) | 0.0598 (8) | |
H23 | 0.5167 | 0.2837 | 0.0535 | 0.072* | |
C37 | 0.5858 (2) | 0.34432 (19) | −0.00010 (14) | 0.0631 (8) | |
H24 | 0.6546 | 0.3226 | 0.0092 | 0.076* | |
C38 | 0.5690 (2) | 0.39871 (19) | −0.04031 (12) | 0.0568 (7) | |
C39 | 0.4658 (3) | 0.42957 (18) | −0.05300 (12) | 0.0582 (7) | |
H25 | 0.4517 | 0.4659 | −0.0804 | 0.070* | |
C40 | 0.3825 (2) | 0.40745 (17) | −0.02564 (12) | 0.0536 (7) | |
H26 | 0.3140 | 0.4296 | −0.0348 | 0.064* | |
C41 | 0.6594 (3) | 0.4239 (2) | −0.06927 (16) | 0.0825 (11) | |
H27 | 0.6375 | 0.4169 | −0.1073 | 0.099* | |
H28 | 0.7233 | 0.3937 | −0.0571 | 0.099* | |
H29 | 0.6753 | 0.4773 | −0.0618 | 0.099* | |
C42 | −0.1179 (2) | 0.18966 (16) | −0.05901 (10) | 0.0428 (6) | |
C43 | −0.1274 (3) | 0.11240 (18) | −0.06961 (12) | 0.0599 (8) | |
H30 | −0.0915 | 0.0775 | −0.0449 | 0.072* | |
C44 | −0.1897 (3) | 0.08560 (18) | −0.11658 (12) | 0.0616 (8) | |
H31 | −0.1954 | 0.0329 | −0.1227 | 0.074* | |
C45 | −0.2432 (2) | 0.13562 (18) | −0.15431 (10) | 0.0502 (7) | |
C46 | −0.2329 (3) | 0.21277 (18) | −0.14392 (11) | 0.0585 (8) | |
H32 | −0.2684 | 0.2477 | −0.1688 | 0.070* | |
C47 | −0.1705 (2) | 0.23992 (17) | −0.09700 (11) | 0.0531 (7) | |
H33 | −0.1640 | 0.2927 | −0.0911 | 0.064* | |
C48 | −0.3125 (3) | 0.1058 (2) | −0.20524 (13) | 0.0747 (10) | |
H34 | −0.3816 | 0.0888 | −0.1973 | 0.090* | |
H35 | −0.2760 | 0.0635 | −0.2191 | 0.090* | |
H36 | −0.3239 | 0.1462 | −0.2316 | 0.090* | |
C49 | 0.15061 (19) | 0.17531 (15) | 0.12378 (9) | 0.0399 (5) | |
C50 | 0.1107 (2) | 0.11845 (15) | 0.16059 (11) | 0.0448 (6) | |
C51 | 0.1672 (2) | 0.10765 (17) | 0.21242 (11) | 0.0527 (7) | |
H37 | 0.2275 | 0.1382 | 0.2248 | 0.063* | |
C52 | 0.1348 (3) | 0.05184 (19) | 0.24593 (12) | 0.0604 (8) | |
C53 | 0.0457 (3) | 0.00593 (19) | 0.22824 (15) | 0.0685 (9) | |
H38 | 0.0245 | −0.0319 | 0.2505 | 0.082* | |
C54 | −0.0116 (3) | 0.01678 (19) | 0.17714 (16) | 0.0692 (9) | |
H39 | −0.0718 | −0.0140 | 0.1650 | 0.083* | |
C55 | 0.0195 (2) | 0.07307 (17) | 0.14366 (13) | 0.0568 (7) | |
H40 | −0.0210 | 0.0805 | 0.1096 | 0.068* | |
C56 | 0.1981 (4) | 0.0427 (3) | 0.30129 (15) | 0.0860 (12) | |
C57 | 0.2377 (2) | 0.14355 (15) | 0.09600 (11) | 0.0432 (6) | |
C58 | 0.2099 (2) | 0.10557 (16) | 0.04724 (11) | 0.0499 (6) | |
H41 | 0.1369 | 0.0998 | 0.0322 | 0.060* | |
C59 | 0.2903 (3) | 0.07613 (17) | 0.02087 (13) | 0.0585 (8) | |
C60 | 0.3989 (3) | 0.0830 (2) | 0.04397 (16) | 0.0719 (10) | |
H42 | 0.4530 | 0.0628 | 0.0266 | 0.086* | |
C61 | 0.4264 (3) | 0.1196 (2) | 0.09246 (16) | 0.0736 (10) | |
H43 | 0.4993 | 0.1239 | 0.1080 | 0.088* | |
C62 | 0.3474 (2) | 0.14995 (18) | 0.11813 (13) | 0.0583 (7) | |
H44 | 0.3672 | 0.1752 | 0.1508 | 0.070* | |
C63 | 0.2578 (4) | 0.0400 (2) | −0.03295 (16) | 0.0779 (10) | |
C64 | 0.0862 (3) | 0.45997 (19) | 0.12564 (15) | 0.0674 (9) | |
H45 | 0.1448 | 0.4499 | 0.1527 | 0.081* | |
C65 | 0.0549 (3) | 0.5351 (2) | 0.11612 (18) | 0.0832 (11) | |
H46 | 0.0911 | 0.5746 | 0.1367 | 0.100* | |
C66 | −0.0297 (3) | 0.5511 (2) | 0.07625 (16) | 0.0786 (10) | |
H47 | −0.0520 | 0.6016 | 0.0687 | 0.094* | |
C67 | −0.0806 (3) | 0.4918 (2) | 0.04790 (15) | 0.0812 (11) | |
H48 | −0.1387 | 0.5010 | 0.0204 | 0.097* | |
C68 | −0.0458 (3) | 0.41744 (19) | 0.05997 (13) | 0.0663 (9) | |
H49 | −0.0822 | 0.3772 | 0.0404 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru | 0.03286 (10) | 0.04300 (11) | 0.03268 (10) | 0.00014 (9) | −0.00027 (7) | 0.00060 (9) |
F1 | 0.165 (3) | 0.125 (2) | 0.0840 (16) | −0.0253 (19) | 0.0128 (16) | 0.0513 (16) |
F2 | 0.0933 (19) | 0.254 (4) | 0.0722 (16) | −0.027 (2) | −0.0091 (14) | 0.057 (2) |
F3 | 0.241 (4) | 0.133 (2) | 0.0640 (15) | −0.002 (2) | 0.018 (2) | −0.0082 (16) |
F4 | 0.137 (2) | 0.0966 (18) | 0.1071 (18) | 0.0351 (16) | 0.0434 (16) | −0.0270 (14) |
F5 | 0.119 (2) | 0.136 (2) | 0.0863 (16) | −0.0295 (18) | 0.0292 (14) | −0.0496 (15) |
F6 | 0.191 (3) | 0.1004 (19) | 0.0668 (14) | 0.0263 (19) | 0.0363 (16) | 0.0059 (13) |
N1 | 0.0351 (10) | 0.0504 (13) | 0.0355 (10) | 0.0015 (9) | −0.0007 (8) | −0.0008 (9) |
N2 | 0.0354 (10) | 0.0503 (13) | 0.0343 (10) | 0.0004 (9) | −0.0008 (8) | −0.0030 (9) |
N3 | 0.0356 (10) | 0.0452 (12) | 0.0372 (10) | −0.0014 (9) | 0.0001 (8) | 0.0021 (9) |
N4 | 0.0382 (10) | 0.0450 (11) | 0.0362 (10) | 0.0005 (9) | 0.0023 (8) | 0.0018 (9) |
N5 | 0.0448 (12) | 0.0497 (13) | 0.0452 (12) | 0.0057 (10) | 0.0033 (10) | 0.0024 (10) |
C1 | 0.0373 (12) | 0.0529 (16) | 0.0366 (12) | 0.0013 (11) | −0.0041 (10) | 0.0013 (11) |
C2 | 0.0378 (13) | 0.0641 (18) | 0.0428 (14) | −0.0042 (12) | −0.0046 (11) | −0.0045 (13) |
C3 | 0.0362 (13) | 0.0687 (18) | 0.0461 (15) | −0.0051 (13) | 0.0002 (11) | −0.0031 (14) |
C4 | 0.0339 (12) | 0.0541 (15) | 0.0413 (13) | 0.0015 (11) | 0.0026 (10) | −0.0019 (12) |
C5 | 0.0350 (12) | 0.0529 (16) | 0.0424 (13) | 0.0026 (11) | 0.0039 (10) | −0.0029 (11) |
C6 | 0.0364 (12) | 0.0533 (16) | 0.0398 (13) | 0.0022 (11) | 0.0052 (10) | −0.0031 (11) |
C7 | 0.0460 (15) | 0.077 (2) | 0.0394 (14) | −0.0039 (14) | 0.0071 (11) | −0.0070 (14) |
C8 | 0.0468 (15) | 0.0727 (19) | 0.0347 (13) | −0.0021 (13) | 0.0013 (11) | −0.0075 (13) |
C9 | 0.0417 (13) | 0.0507 (15) | 0.0348 (12) | −0.0004 (11) | −0.0015 (10) | −0.0033 (11) |
C10 | 0.0387 (12) | 0.0455 (14) | 0.0389 (13) | −0.0003 (11) | −0.0034 (10) | −0.0028 (11) |
C11 | 0.0376 (12) | 0.0467 (15) | 0.0415 (13) | −0.0005 (11) | −0.0033 (10) | 0.0029 (11) |
C12 | 0.0410 (14) | 0.0594 (17) | 0.0494 (15) | −0.0081 (12) | −0.0055 (12) | 0.0011 (13) |
C13 | 0.0420 (14) | 0.0581 (17) | 0.0524 (16) | −0.0089 (13) | 0.0000 (12) | 0.0057 (13) |
C14 | 0.0385 (13) | 0.0455 (15) | 0.0447 (14) | −0.0029 (11) | 0.0004 (10) | 0.0046 (11) |
C15 | 0.0404 (13) | 0.0439 (14) | 0.0462 (14) | 0.0027 (11) | 0.0037 (11) | 0.0083 (11) |
C16 | 0.0427 (13) | 0.0423 (14) | 0.0413 (13) | 0.0022 (11) | 0.0045 (11) | 0.0044 (11) |
C17 | 0.0518 (15) | 0.0555 (16) | 0.0408 (14) | 0.0010 (13) | 0.0105 (11) | 0.0043 (12) |
C18 | 0.0546 (16) | 0.0548 (16) | 0.0359 (13) | 0.0013 (13) | 0.0042 (12) | −0.0001 (12) |
C19 | 0.0441 (14) | 0.0446 (14) | 0.0359 (12) | 0.0033 (11) | −0.0010 (10) | 0.0020 (10) |
C20 | 0.0430 (13) | 0.0463 (14) | 0.0345 (12) | 0.0033 (11) | −0.0027 (10) | 0.0021 (11) |
C21 | 0.0373 (13) | 0.0614 (18) | 0.0387 (13) | −0.0013 (12) | 0.0040 (10) | −0.0054 (12) |
C22 | 0.0400 (14) | 0.0650 (19) | 0.0488 (15) | 0.0061 (13) | 0.0071 (12) | −0.0011 (13) |
C23 | 0.0579 (17) | 0.0563 (18) | 0.0535 (17) | 0.0002 (14) | 0.0083 (14) | 0.0011 (14) |
C24 | 0.0481 (16) | 0.069 (2) | 0.0545 (17) | −0.0120 (14) | 0.0114 (13) | −0.0113 (15) |
C25 | 0.0353 (14) | 0.080 (2) | 0.0587 (17) | 0.0032 (14) | 0.0050 (12) | −0.0100 (16) |
C26 | 0.0425 (14) | 0.0620 (18) | 0.0509 (16) | 0.0032 (13) | 0.0037 (12) | −0.0004 (13) |
C27 | 0.061 (2) | 0.099 (3) | 0.092 (3) | −0.014 (2) | 0.0233 (19) | 0.005 (2) |
C28 | 0.0378 (13) | 0.0569 (16) | 0.0378 (13) | −0.0028 (12) | −0.0014 (10) | −0.0013 (12) |
C29 | 0.0632 (18) | 0.0551 (17) | 0.0525 (16) | −0.0013 (15) | −0.0123 (14) | −0.0001 (14) |
C30 | 0.0636 (19) | 0.073 (2) | 0.0519 (17) | 0.0071 (17) | −0.0120 (14) | 0.0051 (16) |
C31 | 0.0438 (15) | 0.090 (2) | 0.0385 (14) | −0.0006 (15) | −0.0002 (12) | −0.0071 (15) |
C32 | 0.068 (2) | 0.068 (2) | 0.0523 (17) | −0.0153 (16) | −0.0038 (15) | −0.0139 (15) |
C33 | 0.0686 (19) | 0.0535 (18) | 0.0507 (16) | −0.0047 (15) | −0.0037 (14) | −0.0001 (14) |
C34 | 0.060 (2) | 0.139 (4) | 0.0456 (18) | −0.006 (2) | −0.0105 (15) | −0.010 (2) |
C35 | 0.0424 (14) | 0.0509 (16) | 0.0454 (14) | −0.0022 (12) | 0.0062 (11) | 0.0043 (12) |
C36 | 0.0511 (16) | 0.063 (2) | 0.0654 (19) | 0.0079 (14) | 0.0114 (14) | 0.0171 (16) |
C37 | 0.0437 (15) | 0.070 (2) | 0.077 (2) | 0.0100 (15) | 0.0147 (15) | 0.0049 (17) |
C38 | 0.0519 (17) | 0.0621 (19) | 0.0594 (18) | −0.0056 (14) | 0.0177 (14) | −0.0032 (15) |
C39 | 0.0605 (18) | 0.0587 (18) | 0.0562 (17) | −0.0047 (15) | 0.0115 (14) | 0.0128 (14) |
C40 | 0.0466 (15) | 0.0564 (17) | 0.0576 (17) | 0.0058 (13) | 0.0084 (13) | 0.0114 (14) |
C41 | 0.068 (2) | 0.094 (3) | 0.092 (3) | −0.010 (2) | 0.034 (2) | 0.003 (2) |
C42 | 0.0395 (13) | 0.0535 (15) | 0.0332 (12) | −0.0001 (11) | −0.0007 (10) | 0.0007 (11) |
C43 | 0.0683 (19) | 0.0545 (18) | 0.0495 (16) | 0.0107 (15) | −0.0117 (14) | 0.0004 (13) |
C44 | 0.074 (2) | 0.0494 (17) | 0.0550 (17) | 0.0077 (15) | −0.0074 (15) | −0.0110 (14) |
C45 | 0.0458 (14) | 0.0672 (19) | 0.0360 (13) | −0.0027 (13) | 0.0018 (11) | −0.0051 (12) |
C46 | 0.0634 (18) | 0.064 (2) | 0.0416 (15) | 0.0024 (15) | −0.0093 (13) | 0.0121 (13) |
C47 | 0.0638 (18) | 0.0452 (16) | 0.0462 (15) | −0.0008 (13) | −0.0032 (13) | 0.0056 (12) |
C48 | 0.077 (2) | 0.092 (3) | 0.0481 (17) | −0.005 (2) | −0.0081 (16) | −0.0104 (17) |
C49 | 0.0361 (12) | 0.0438 (14) | 0.0370 (12) | −0.0012 (11) | −0.0021 (10) | −0.0008 (10) |
C50 | 0.0439 (14) | 0.0434 (14) | 0.0479 (14) | 0.0006 (11) | 0.0095 (11) | 0.0011 (11) |
C51 | 0.0538 (16) | 0.0574 (17) | 0.0471 (15) | −0.0079 (13) | 0.0090 (13) | 0.0024 (13) |
C52 | 0.0663 (19) | 0.064 (2) | 0.0546 (17) | 0.0023 (16) | 0.0203 (15) | 0.0112 (15) |
C53 | 0.072 (2) | 0.0575 (19) | 0.083 (2) | −0.0083 (16) | 0.0317 (19) | 0.0135 (17) |
C54 | 0.0554 (18) | 0.0569 (19) | 0.096 (3) | −0.0153 (15) | 0.0159 (18) | 0.0043 (18) |
C55 | 0.0470 (16) | 0.0545 (18) | 0.0679 (19) | −0.0045 (13) | 0.0063 (14) | 0.0008 (15) |
C56 | 0.108 (3) | 0.099 (3) | 0.054 (2) | −0.012 (3) | 0.022 (2) | 0.015 (2) |
C57 | 0.0422 (13) | 0.0390 (13) | 0.0485 (14) | 0.0013 (11) | 0.0078 (11) | 0.0070 (11) |
C58 | 0.0486 (15) | 0.0481 (16) | 0.0536 (16) | 0.0021 (12) | 0.0104 (12) | 0.0040 (13) |
C59 | 0.069 (2) | 0.0481 (17) | 0.0644 (19) | 0.0068 (14) | 0.0272 (16) | 0.0036 (14) |
C60 | 0.060 (2) | 0.064 (2) | 0.101 (3) | 0.0096 (16) | 0.039 (2) | 0.006 (2) |
C61 | 0.0420 (16) | 0.074 (2) | 0.105 (3) | 0.0040 (15) | 0.0127 (18) | −0.002 (2) |
C62 | 0.0431 (15) | 0.0601 (19) | 0.0693 (19) | 0.0021 (13) | 0.0023 (14) | −0.0007 (15) |
C63 | 0.101 (3) | 0.065 (2) | 0.076 (2) | 0.005 (2) | 0.038 (2) | −0.0052 (19) |
C64 | 0.0604 (19) | 0.0540 (19) | 0.081 (2) | 0.0046 (15) | −0.0078 (16) | −0.0046 (16) |
C65 | 0.082 (3) | 0.052 (2) | 0.110 (3) | 0.0036 (18) | 0.000 (2) | −0.006 (2) |
C66 | 0.095 (3) | 0.052 (2) | 0.089 (3) | 0.0221 (19) | 0.015 (2) | 0.0097 (19) |
C67 | 0.086 (3) | 0.077 (3) | 0.073 (2) | 0.029 (2) | −0.0115 (19) | 0.0038 (19) |
C68 | 0.071 (2) | 0.061 (2) | 0.0607 (19) | 0.0152 (16) | −0.0086 (16) | −0.0021 (15) |
Ru—N1 | 2.049 (2) | C47—C42 | 1.379 (4) |
Ru—N2 | 2.046 (2) | C45—C48 | 1.514 (4) |
Ru—N3 | 2.052 (2) | C49—C50 | 1.494 (4) |
Ru—N4 | 2.056 (2) | C49—C57 | 1.489 (3) |
Ru—N5 | 2.313 (2) | C50—C51 | 1.390 (4) |
Ru—C49 | 1.868 (3) | C51—C52 | 1.388 (4) |
F1—C56 | 1.321 (4) | C52—C53 | 1.379 (5) |
F2—C56 | 1.304 (5) | C53—C54 | 1.378 (5) |
F3—C56 | 1.321 (5) | C54—C55 | 1.387 (4) |
F4—C63 | 1.340 (4) | C55—C50 | 1.390 (4) |
F5—C63 | 1.329 (4) | C52—C56 | 1.493 (5) |
F6—C63 | 1.327 (4) | C57—C58 | 1.387 (4) |
N1—C1 | 1.383 (3) | C58—C59 | 1.386 (4) |
N1—C4 | 1.374 (3) | C59—C60 | 1.387 (5) |
N2—C6 | 1.378 (3) | C60—C61 | 1.369 (5) |
N2—C9 | 1.378 (3) | C61—C62 | 1.368 (4) |
N3—C11 | 1.382 (3) | C62—C57 | 1.391 (4) |
N3—C14 | 1.383 (3) | C59—C63 | 1.488 (5) |
N4—C16 | 1.378 (3) | C64—C65 | 1.373 (5) |
N4—C19 | 1.374 (3) | C65—C66 | 1.359 (5) |
N5—C64 | 1.324 (4) | C66—C67 | 1.351 (5) |
N5—C68 | 1.326 (3) | C67—C68 | 1.380 (5) |
C1—C2 | 1.439 (4) | C2—H1 | 0.9300 |
C2—C3 | 1.341 (4) | C3—H2 | 0.9300 |
C3—C4 | 1.439 (3) | C7—H3 | 0.9300 |
C4—C5 | 1.400 (3) | C8—H4 | 0.9300 |
C5—C6 | 1.395 (3) | C12—H5 | 0.9300 |
C6—C7 | 1.446 (4) | C13—H6 | 0.9300 |
C7—C8 | 1.345 (4) | C17—H7 | 0.9300 |
C8—C9 | 1.443 (4) | C18—H8 | 0.9300 |
C9—C10 | 1.394 (3) | C22—H9 | 0.9300 |
C10—C11 | 1.404 (4) | C23—H10 | 0.9300 |
C11—C12 | 1.437 (4) | C25—H11 | 0.9300 |
C12—C13 | 1.350 (4) | C26—H12 | 0.9300 |
C13—C14 | 1.439 (3) | C27—H13 | 0.9600 |
C14—C15 | 1.399 (4) | C27—H14 | 0.9600 |
C15—C16 | 1.401 (4) | C27—H15 | 0.9600 |
C16—C17 | 1.442 (4) | C29—H16 | 0.9300 |
C17—C18 | 1.343 (4) | C30—H17 | 0.9300 |
C18—C19 | 1.440 (4) | C32—H18 | 0.9300 |
C19—C20 | 1.396 (4) | C33—H19 | 0.9300 |
C20—C1 | 1.401 (4) | C34—H20 | 0.9600 |
C5—C21 | 1.504 (4) | C34—H21 | 0.9600 |
C21—C22 | 1.386 (4) | C34—H22 | 0.9600 |
C22—C23 | 1.387 (4) | C36—H23 | 0.9300 |
C23—C24 | 1.384 (4) | C37—H24 | 0.9300 |
C24—C25 | 1.386 (4) | C39—H25 | 0.9300 |
C25—C26 | 1.389 (4) | C40—H26 | 0.9300 |
C26—C21 | 1.384 (4) | C41—H27 | 0.9600 |
C24—C27 | 1.503 (4) | C41—H28 | 0.9600 |
C10—C28 | 1.504 (3) | C41—H29 | 0.9600 |
C28—C29 | 1.376 (4) | C43—H30 | 0.9300 |
C29—C30 | 1.381 (4) | C44—H31 | 0.9300 |
C30—C31 | 1.375 (5) | C46—H32 | 0.9300 |
C31—C32 | 1.365 (5) | C47—H33 | 0.9300 |
C32—C33 | 1.400 (4) | C48—H34 | 0.9600 |
C33—C28 | 1.370 (4) | C48—H35 | 0.9600 |
C31—C34 | 1.514 (4) | C48—H36 | 0.9600 |
C15—C35 | 1.502 (4) | C51—H37 | 0.9300 |
C35—C36 | 1.385 (4) | C53—H38 | 0.9300 |
C36—C37 | 1.385 (4) | C54—H39 | 0.9300 |
C37—C38 | 1.376 (4) | C55—H40 | 0.9300 |
C38—C39 | 1.380 (4) | C58—H41 | 0.9300 |
C39—C40 | 1.389 (4) | C60—H42 | 0.9300 |
C40—C35 | 1.381 (4) | C61—H43 | 0.9300 |
C38—C41 | 1.503 (4) | C62—H44 | 0.9300 |
C20—C42 | 1.507 (3) | C64—H45 | 0.9300 |
C42—C43 | 1.370 (4) | C65—H46 | 0.9300 |
C43—C44 | 1.384 (4) | C66—H47 | 0.9300 |
C44—C45 | 1.376 (4) | C67—H48 | 0.9300 |
C45—C46 | 1.368 (4) | C68—H49 | 0.9300 |
C46—C47 | 1.386 (4) | ||
N1—Ru—N2 | 89.15 (8) | C54—C55—C50 | 120.6 (3) |
N1—Ru—N3 | 173.72 (8) | F2—C56—F3 | 105.8 (4) |
N1—Ru—N4 | 90.55 (8) | F2—C56—F1 | 106.8 (4) |
N2—Ru—N3 | 90.89 (8) | F3—C56—F1 | 105.2 (3) |
N2—Ru—N4 | 175.36 (8) | F2—C56—C52 | 113.3 (3) |
N3—Ru—N4 | 88.90 (8) | F3—C56—C52 | 111.9 (4) |
N1—Ru—N5 | 87.66 (8) | F1—C56—C52 | 113.3 (4) |
N2—Ru—N5 | 88.60 (8) | C58—C57—C62 | 118.6 (3) |
N3—Ru—N5 | 86.06 (8) | C58—C57—C49 | 119.8 (2) |
N4—Ru—N5 | 86.75 (8) | C62—C57—C49 | 121.6 (2) |
C49—Ru—N1 | 92.68 (10) | C59—C58—C57 | 120.3 (3) |
C49—Ru—N2 | 91.69 (10) | C58—C59—C60 | 119.9 (3) |
C49—Ru—N3 | 93.60 (9) | C58—C59—C63 | 118.8 (3) |
C49—Ru—N4 | 92.96 (10) | C60—C59—C63 | 121.3 (3) |
C49—Ru—N5 | 179.56 (10) | C61—C60—C59 | 119.9 (3) |
C4—N1—C1 | 107.3 (2) | C62—C61—C60 | 120.4 (3) |
C4—N1—Ru | 126.97 (16) | C61—C62—C57 | 120.9 (3) |
C1—N1—Ru | 125.14 (17) | F6—C63—F5 | 105.4 (4) |
C6—N2—C9 | 107.0 (2) | F6—C63—F4 | 105.7 (3) |
C6—N2—Ru | 127.21 (16) | F5—C63—F4 | 105.9 (3) |
C9—N2—Ru | 125.65 (17) | F6—C63—C59 | 113.2 (3) |
C11—N3—C14 | 107.5 (2) | F5—C63—C59 | 113.3 (3) |
C11—N3—Ru | 125.21 (16) | F4—C63—C59 | 112.7 (3) |
C14—N3—Ru | 127.28 (16) | N5—C64—C65 | 123.5 (3) |
C19—N4—C16 | 106.8 (2) | C66—C65—C64 | 119.1 (4) |
C19—N4—Ru | 125.58 (17) | C67—C66—C65 | 118.2 (3) |
C16—N4—Ru | 127.18 (16) | C66—C67—C68 | 119.7 (3) |
C64—N5—C68 | 116.7 (3) | N5—C68—C67 | 122.7 (3) |
C64—N5—Ru | 122.20 (19) | C1—C2—H1 | 126.1 |
C68—N5—Ru | 121.0 (2) | C3—C2—H1 | 126.1 |
N1—C1—C20 | 126.1 (2) | C2—C3—H2 | 126.1 |
N1—C1—C2 | 108.4 (2) | C4—C3—H2 | 126.1 |
C20—C1—C2 | 125.6 (2) | C8—C7—H3 | 126.3 |
C3—C2—C1 | 107.9 (2) | C6—C7—H3 | 126.3 |
C2—C3—C4 | 107.7 (2) | C7—C8—H4 | 126.2 |
N1—C4—C5 | 125.8 (2) | C9—C8—H4 | 126.2 |
N1—C4—C3 | 108.8 (2) | C13—C12—H5 | 126.2 |
C5—C4—C3 | 125.4 (2) | C11—C12—H5 | 126.2 |
C6—C5—C4 | 125.0 (2) | C12—C13—H6 | 126.0 |
C6—C5—C21 | 118.8 (2) | C14—C13—H6 | 126.0 |
C4—C5—C21 | 115.9 (2) | C18—C17—H7 | 126.3 |
N2—C6—C5 | 125.6 (2) | C16—C17—H7 | 126.3 |
N2—C6—C7 | 108.9 (2) | C17—C18—H8 | 126.2 |
C5—C6—C7 | 125.4 (2) | C19—C18—H8 | 126.2 |
C8—C7—C6 | 107.4 (2) | C21—C22—H9 | 119.4 |
C7—C8—C9 | 107.6 (2) | C23—C22—H9 | 119.4 |
N2—C9—C10 | 125.7 (2) | C24—C23—H10 | 119.4 |
N2—C9—C8 | 108.9 (2) | C22—C23—H10 | 119.4 |
C10—C9—C8 | 125.3 (2) | C24—C25—H11 | 119.2 |
C9—C10—C11 | 126.2 (2) | C26—C25—H11 | 119.2 |
C9—C10—C28 | 117.1 (2) | C21—C26—H12 | 119.7 |
C11—C10—C28 | 116.7 (2) | C25—C26—H12 | 119.7 |
N3—C11—C10 | 125.7 (2) | C24—C27—H13 | 109.5 |
N3—C11—C12 | 108.6 (2) | C24—C27—H14 | 109.5 |
C10—C11—C12 | 125.7 (2) | H13—C27—H14 | 109.5 |
C13—C12—C11 | 107.6 (2) | C24—C27—H15 | 109.5 |
C12—C13—C14 | 108.0 (2) | H13—C27—H15 | 109.5 |
N3—C14—C15 | 125.7 (2) | H14—C27—H15 | 109.5 |
N3—C14—C13 | 108.3 (2) | C28—C29—H16 | 119.1 |
C15—C14—C13 | 125.9 (2) | C30—C29—H16 | 119.1 |
C14—C15—C16 | 124.9 (2) | C31—C30—H17 | 119.8 |
C14—C15—C35 | 117.6 (2) | C29—C30—H17 | 119.8 |
C16—C15—C35 | 117.5 (2) | C31—C32—H18 | 119.3 |
N4—C16—C15 | 125.7 (2) | C33—C32—H18 | 119.3 |
N4—C16—C17 | 109.1 (2) | C28—C33—H19 | 119.8 |
C15—C16—C17 | 125.3 (2) | C32—C33—H19 | 119.8 |
C18—C17—C16 | 107.4 (2) | C31—C34—H20 | 109.5 |
C17—C18—C19 | 107.6 (2) | C31—C34—H21 | 109.5 |
N4—C19—C20 | 125.8 (2) | H20—C34—H21 | 109.5 |
N4—C19—C18 | 109.2 (2) | C31—C34—H22 | 109.5 |
C20—C19—C18 | 125.0 (2) | H20—C34—H22 | 109.5 |
C19—C20—C1 | 125.9 (2) | H21—C34—H22 | 109.5 |
C19—C20—C42 | 117.5 (2) | C37—C36—H23 | 119.5 |
C1—C20—C42 | 116.6 (2) | C35—C36—H23 | 119.5 |
C26—C21—C22 | 118.0 (3) | C38—C37—H24 | 119.2 |
C26—C21—C5 | 122.0 (3) | C36—C37—H24 | 119.2 |
C22—C21—C5 | 119.8 (2) | C38—C39—H25 | 119.4 |
C21—C22—C23 | 121.2 (3) | C40—C39—H25 | 119.4 |
C24—C23—C22 | 121.1 (3) | C35—C40—H26 | 119.4 |
C23—C24—C25 | 117.5 (3) | C39—C40—H26 | 119.4 |
C23—C24—C27 | 121.7 (3) | C38—C41—H27 | 109.5 |
C25—C24—C27 | 120.9 (3) | C38—C41—H28 | 109.5 |
C24—C25—C26 | 121.6 (3) | H27—C41—H28 | 109.5 |
C21—C26—C25 | 120.5 (3) | C38—C41—H29 | 109.5 |
C33—C28—C29 | 117.7 (2) | H27—C41—H29 | 109.5 |
C33—C28—C10 | 122.6 (3) | H28—C41—H29 | 109.5 |
C29—C28—C10 | 119.7 (2) | C42—C43—H30 | 119.5 |
C28—C29—C30 | 121.9 (3) | C44—C43—H30 | 119.5 |
C31—C30—C29 | 120.5 (3) | C45—C44—H31 | 119.4 |
C32—C31—C30 | 118.1 (3) | C43—C44—H31 | 119.4 |
C32—C31—C34 | 121.8 (3) | C45—C46—H32 | 119.4 |
C30—C31—C34 | 120.0 (3) | C47—C46—H32 | 119.4 |
C31—C32—C33 | 121.4 (3) | C42—C47—H33 | 119.6 |
C28—C33—C32 | 120.4 (3) | C46—C47—H33 | 119.6 |
C40—C35—C36 | 117.5 (3) | C45—C48—H34 | 109.5 |
C40—C35—C15 | 120.7 (2) | C45—C48—H35 | 109.5 |
C36—C35—C15 | 121.8 (2) | H34—C48—H35 | 109.5 |
C37—C36—C35 | 121.0 (3) | C45—C48—H36 | 109.5 |
C38—C37—C36 | 121.7 (3) | H34—C48—H36 | 109.5 |
C37—C38—C39 | 117.5 (3) | H35—C48—H36 | 109.5 |
C37—C38—C41 | 121.4 (3) | C52—C51—H37 | 119.6 |
C39—C38—C41 | 121.1 (3) | C50—C51—H37 | 119.6 |
C38—C39—C40 | 121.3 (3) | C54—C53—H38 | 120.4 |
C35—C40—C39 | 121.2 (3) | C52—C53—H38 | 120.4 |
C43—C42—C47 | 118.0 (2) | C53—C54—H39 | 119.6 |
C43—C42—C20 | 121.1 (2) | C55—C54—H39 | 119.6 |
C47—C42—C20 | 120.8 (3) | C54—C55—H40 | 119.7 |
C42—C43—C44 | 121.0 (3) | C50—C55—H40 | 119.7 |
C45—C44—C43 | 121.2 (3) | C59—C58—H41 | 119.8 |
C46—C45—C44 | 117.8 (3) | C57—C58—H41 | 119.8 |
C46—C45—C48 | 121.3 (3) | C61—C60—H42 | 120.1 |
C44—C45—C48 | 120.8 (3) | C59—C60—H42 | 120.1 |
C45—C46—C47 | 121.3 (3) | C62—C61—H43 | 119.8 |
C42—C47—C46 | 120.8 (3) | C60—C61—H43 | 119.8 |
C50—C49—C57 | 112.8 (2) | C61—C62—H44 | 119.5 |
Ru—C49—C50 | 125.04 (18) | C57—C62—H44 | 119.5 |
Ru—C49—C57 | 122.13 (18) | N5—C64—H45 | 118.2 |
C55—C50—C51 | 118.2 (3) | C65—C64—H45 | 118.2 |
C55—C50—C49 | 121.5 (2) | C66—C65—H46 | 120.4 |
C51—C50—C49 | 120.2 (2) | C64—C65—H46 | 120.4 |
C52—C51—C50 | 120.8 (3) | C67—C66—H47 | 120.9 |
C53—C52—C51 | 120.4 (3) | C65—C66—H47 | 120.9 |
C53—C52—C56 | 120.9 (3) | C66—C67—H48 | 120.2 |
C51—C52—C56 | 118.7 (3) | C68—C67—H48 | 120.2 |
C54—C53—C52 | 119.2 (3) | N5—C68—H49 | 118.6 |
C53—C54—C55 | 120.7 (3) | C67—C68—H49 | 118.6 |
C49—Ru—N1—C4 | 86.4 (2) | C14—C15—C35—C40 | −119.7 (3) |
N5—Ru—N1—C4 | −93.9 (2) | C16—C15—C35—C40 | 60.9 (4) |
C49—Ru—N1—C1 | −83.4 (2) | C19—C20—C42—C43 | 100.9 (3) |
N5—Ru—N1—C1 | 96.3 (2) | C1—C20—C42—C43 | −79.5 (3) |
C49—Ru—N2—C6 | −89.3 (2) | C19—C20—C42—C47 | −79.5 (3) |
N5—Ru—N2—C6 | 91.0 (2) | C1—C20—C42—C47 | 100.2 (3) |
C49—Ru—N2—C9 | 86.1 (2) | N1—Ru—C49—C57 | 123.7 (2) |
N5—Ru—N2—C9 | −93.5 (2) | N2—Ru—C49—C57 | −147.1 (2) |
C49—Ru—N3—C11 | −84.6 (2) | N3—Ru—C49—C57 | −56.1 (2) |
N5—Ru—N3—C11 | 95.7 (2) | N4—Ru—C49—C57 | 33.0 (2) |
C49—Ru—N3—C14 | 92.2 (2) | N1—Ru—C49—C50 | −56.4 (2) |
N5—Ru—N3—C14 | −87.5 (2) | N2—Ru—C49—C50 | 32.8 (2) |
C49—Ru—N4—C16 | −88.4 (2) | N3—Ru—C49—C50 | 123.8 (2) |
N5—Ru—N4—C16 | 91.3 (2) | N4—Ru—C49—C50 | −147.1 (2) |
C49—Ru—N4—C19 | 82.5 (2) | C57—C49—C50—C51 | 82.8 (3) |
N5—Ru—N4—C19 | −97.9 (2) | Ru—C49—C50—C51 | −97.1 (3) |
N1—Ru—N5—C64 | 150.7 (3) | C57—C49—C50—C55 | −94.6 (3) |
N2—Ru—N5—C64 | 61.5 (3) | Ru—C49—C50—C55 | 85.5 (3) |
N3—Ru—N5—C64 | −29.5 (3) | C51—C52—C56—F1 | −166.2 (3) |
N4—Ru—N5—C64 | −118.6 (3) | C53—C52—C56—F1 | 13.9 (6) |
N1—Ru—N5—C68 | −33.1 (2) | C51—C52—C56—F2 | −44.3 (5) |
N2—Ru—N5—C68 | −122.3 (2) | C53—C52—C56—F2 | 135.7 (4) |
N3—Ru—N5—C68 | 146.7 (2) | C51—C52—C56—F3 | 75.1 (5) |
N4—Ru—N5—C68 | 57.6 (2) | C53—C52—C56—F3 | −104.8 (4) |
C4—C5—C21—C22 | 108.7 (3) | C50—C49—C57—C58 | 88.7 (3) |
C6—C5—C21—C22 | −65.4 (4) | Ru—C49—C57—C58 | −91.4 (3) |
C4—C5—C21—C26 | −65.6 (4) | C50—C49—C57—C62 | −90.4 (3) |
C6—C5—C21—C26 | 120.3 (3) | Ru—C49—C57—C62 | 89.5 (3) |
C5—C21—C22—C23 | −172.4 (3) | C58—C59—C63—F4 | −153.5 (3) |
C5—C21—C26—C25 | 172.6 (3) | C60—C59—C63—F4 | 28.7 (5) |
C9—C10—C28—C29 | 69.6 (4) | C58—C59—C63—F5 | −33.3 (5) |
C11—C10—C28—C29 | −106.9 (3) | C60—C59—C63—F5 | 149.0 (3) |
C9—C10—C28—C33 | −111.2 (3) | C58—C59—C63—F6 | 86.7 (4) |
C11—C10—C28—C33 | 72.2 (4) | C60—C59—C63—F6 | −91.1 (4) |
C14—C15—C35—C36 | 60.4 (4) | Ru—N5—C64—C65 | 176.4 (3) |
C16—C15—C35—C36 | −119.0 (3) | Ru—N5—C68—C67 | −175.6 (3) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | [Ru(C48H36N4)(C15H10O2)(C5H5N)] | [Ru(C48H36N4)(C15H8F6)(C5H5N)] |
Mr | 1071.21 | 1151.19 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, P21/c |
Temperature (K) | 296 | 296 |
a, b, c (Å) | 15.806 (2), 16.6172 (18), 20.644 (2) | 12.4428 (17), 17.3768 (19), 25.1794 (17) |
β (°) | 95.872 (10) | 99.436 (9) |
V (Å3) | 5393.7 (10) | 5370.5 (10) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.34 | 0.36 |
Crystal size (mm) | 0.20 × 0.12 × 0.10 | 0.50 × 0.40 × 0.20 |
Data collection | ||
Diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – | ψ scan (North et al., 1968) |
Tmin, Tmax | – | 0.840, 0.930 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6419, 6197, 2792 | 12882, 12323, 8702 |
Rint | 0.048 | 0.018 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.182, 0.97 | 0.038, 0.108, 1.02 |
No. of reflections | 6197 | 12323 |
No. of parameters | 345 | 721 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.51 | 0.32, −0.30 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, CrystalStructure (Molecular Structure Corporation & Rigaku Corporation, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Ru—N1 | 2.038 (4) | O—C26 | 1.228 (6) |
Ru—N2 | 2.049 (4) | C25—C26 | 1.498 (6) |
Ru—N3 | 2.329 (7) | C26—C27 | 1.479 (8) |
Ru—C25 | 1.877 (8) | ||
N1—Ru—N1i | 169.1 (2) | N1—Ru—C25 | 95.45 (12) |
N1—Ru—N2 | 89.57 (15) | N2—Ru—C25 | 91.43 (13) |
N1—Ru—N2i | 90.16 (15) | N3—Ru—C25 | 180 |
N1—Ru—N3 | 84.55 (12) | C26—C25—C26i | 116.8 (6) |
N2i—Ru—N2 | 177.1 (3) | Ru—C25—C26 | 121.6 (3) |
N2—Ru—N3 | 88.57 (13) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Ru—N1 | 2.049 (2) | Ru—N4 | 2.056 (2) |
Ru—N2 | 2.046 (2) | Ru—N5 | 2.313 (2) |
Ru—N3 | 2.052 (2) | Ru—C49 | 1.868 (3) |
N1—Ru—N2 | 89.15 (8) | N4—Ru—N5 | 86.75 (8) |
N1—Ru—N3 | 173.72 (8) | C49—Ru—N1 | 92.68 (10) |
N1—Ru—N4 | 90.55 (8) | C49—Ru—N2 | 91.69 (10) |
N2—Ru—N3 | 90.89 (8) | C49—Ru—N3 | 93.60 (9) |
N2—Ru—N4 | 175.36 (8) | C49—Ru—N4 | 92.96 (10) |
N3—Ru—N4 | 88.90 (8) | C49—Ru—N5 | 179.56 (10) |
N1—Ru—N5 | 87.66 (8) | C50—C49—C57 | 112.8 (2) |
N2—Ru—N5 | 88.60 (8) | Ru—C49—C50 | 125.04 (18) |
N3—Ru—N5 | 86.06 (8) | Ru—C49—C57 | 122.13 (18) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
Ruthenium(II) porphyrin carbene complexes have been reported as effective catalysts for the production of olefins or cyclopropanes from diazo compounds (Che & Huang, 2002). Assuming that the catalytic reaction would take place at the position trans to the carbene ligand, the ligand-exchange reaction should play an important role in the study of such catalytic reactions. A large amount of Lewis base, PPh3, pyridine or CO, causes dissociation of the carbene ligand, and the exchange reaction of the axial ligand trans to carbene has been examined using UV-vis spectroscopy in CH2Cl2 solution (Galardon et al., 1998). We have synthesized two (porphyrinato)ruthenium(II) carbene complexes coordinated by a pyridine ligand, [Ru(ttp){C(COPh)2}(py)], (I) and [Ru(ttp){C(3—C6H4CF3)2}(py)], (II) (where H2ttp is 5,10,15,20-tetra-p-tolylporphyrin and py is pyridine), and have investigated the trans influence of the axial ligands on the molecular structures in the crystalline state. \sch
The molecular structures of (I) and (II) are shown in Figs. 1 and 2, respectively. The geometry about the Ru atoms is distorted octahedral in both complexes, and the equatorial Ru—N(porphyrin) bond lengths in (I) and (II) are as expected for ruthenium(II) porphyrin complexes. The Ru—C bond length in (II) is longer than that in the five-coordinate derivative [Ru(ttp){C(3—C6H4CF3)2}] [1.842 (6) Å; Wada et al., 2002]. Compared with analogous ruthenium(II) tetra-p-tolylporphyrin and tetraphenylporphyrin (H2tpp) carbene complexes, the Ru—C bond trans to the N-donor ligand in (I) and (II) is obviously longer than that trans to an O-donor; an Ru—C bond length of 1.829 (9) Å was observed in [Ru(tpp){C(CO2Et)2}(CH3OH)]·H2O (Galardon et al., 1998), and a value of 1.845 (3) Å was observed in [Ru(ttp)(CPh2)(CH3OH)]·CH3OH (Kawai et al., 2002). Thus, the N-donor ligand seems to have a larger trans influence than the O-donor ligand in ruthenium(II) porphyrin carbene complexes. In addition, the Ru—N bond trans to the carbene in (I) and (II) is much longer than that trans to a carbonyl group; an Ru—N distance of 2.193 (4) Å was observed in [Ru(tpp)(CO)(py)].1.5(toluene) (Little & Ibers, 1973). Therefore, the trans influence of the carbene ligand is apparently stronger than that of the carbonyl ligand for (porphyrinato)ruthenium(II) complexes. The Ru—C—C angle about the carbene C atom in (I) is closer to 120° than in (II). The pairs of benzoyl [(I)] and 3-trifluoromethylphenyl [(II)] groups assume a face-to-face arrangement in an anti conformation.
The porphyrin rings in these two compounds are slightly distorted into saddle conformations. The largest deviations from the C20N4 least-squares planes are −0.235 (6) and 0.194 (6) Å at C3 and C8, respectively, for (I), and 0.148 (3) and −0.107 (3) Å at C10 and C13, respectively, for (II). The Ru atoms are displaced out of the least-squares planes toward the carbene ligands by 0.1460 (17) and 0.0603 (6) Å for (I) and (II), respectively. The Ru displacement in (II) is the smallest among ruthenium(II) porphyrin carbene complexes reported to date.