Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007952/gs1094sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007952/gs1094Isup2.hkl |
CCDC reference: 150321
The title compound was prepared from the chiral ruthenium porphyrin precursor and eight equivalents of (R)-1-phenylethyl isocyanide, as previously reported for the racemic ligands (Galardon et al., 1999). Crystals suitable for X-ray analysis were obtained by slow evaporation of a CH2Cl2–hexane solution in the presence of a small excess of isocyanide.
In a previous study at room temperature, due to their large thermal expansion, some difficulties were encountered in localizing the dimethyl dioxolane pickets(?). So, in the further refinement calculations, it was necessary to set bond and angle restraints for these groups. This method leads to high values for R and s.u.'s, and a too low r/p ratio. In this situation, the use of the CCD technique at low temperature results in a decrease in the thermal motion and a significant increase in the r/p ratio. Most of the H atoms were found in a difference Fourier map (except for the dimethyl dioxolane pickets). These were treated as riding (using the AFIX x3 command in SHELXL97). It was also possible to confirm unambiguously the absolute configuration using the Friedel pairs and to obtain good geometrical data.
Data collection: KappaCCD Software (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids. |
[Ru(C9H9N)2(C92H108N4O24)] | F(000) = 2128 |
Mr = 2017.24 | Dx = 1.292 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
a = 18.5099 (2) Å | Cell parameters from 157703 reflections |
b = 15.0831 (2) Å | θ = 1.0–27.9° |
c = 18.5766 (2) Å | µ = 0.23 mm−1 |
β = 90.5023 (6)° | T = 110 K |
V = 5186.14 (10) Å3 | Block, purple |
Z = 2 | 0.38 × 0.28 × 0.25 mm |
Enraf-Nonius KappaCCD diffractometer | 24735 independent reflections |
Radiation source: fine-focus sealed tube | 22116 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 19.11 pixels mm-1 | θmax = 27.9°, θmin = 2.1° |
Area–detector scans (see text) | h = −24→24 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965; Alcock, 1970) | k = −19→19 |
Tmin = 0.895, Tmax = 0.932 | l = −24→24 |
82451 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difmap and geom |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0635P)2 + 1.5527P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
24735 reflections | Δρmax = 0.78 e Å−3 |
1270 parameters | Δρmin = −0.78 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.039 (12); 11880 Friedel pairs |
[Ru(C9H9N)2(C92H108N4O24)] | V = 5186.14 (10) Å3 |
Mr = 2017.24 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 18.5099 (2) Å | µ = 0.23 mm−1 |
b = 15.0831 (2) Å | T = 110 K |
c = 18.5766 (2) Å | 0.38 × 0.28 × 0.25 mm |
β = 90.5023 (6)° |
Enraf-Nonius KappaCCD diffractometer | 24735 independent reflections |
Absorption correction: analytical (de Meulenaer & Tompa, 1965; Alcock, 1970) | 22116 reflections with I > 2σ(I) |
Tmin = 0.895, Tmax = 0.932 | Rint = 0.000 |
82451 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.103 | Δρmax = 0.78 e Å−3 |
S = 1.03 | Δρmin = −0.78 e Å−3 |
24735 reflections | Absolute structure: Flack (1983) |
1270 parameters | Absolute structure parameter: −0.039 (12); 11880 Friedel pairs |
1 restraint |
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 | ||
Ru1 | 0.751749 (9) | 0.932404 (14) | 0.745875 (8) | 0.01592 (4) | |
O1 | 0.80517 (9) | 1.02513 (11) | 0.45832 (9) | 0.0266 (4) | |
O2 | 0.79289 (10) | 0.76721 (13) | 0.36453 (10) | 0.0334 (4) | |
O3 | 0.87141 (11) | 0.87271 (14) | 0.32525 (11) | 0.0427 (5) | |
O4 | 0.70496 (10) | 1.23733 (12) | 0.61286 (9) | 0.0271 (4) | |
O5 | 0.50595 (12) | 1.20616 (17) | 0.68425 (11) | 0.0496 (5) | |
O6 | 0.51990 (12) | 1.32027 (16) | 0.60516 (15) | 0.0577 (6) | |
O7 | 0.82490 (10) | 1.19519 (13) | 0.92321 (11) | 0.0313 (4) | |
O8 | 0.66899 (10) | 1.31709 (13) | 0.81340 (10) | 0.0361 (4) | |
O9 | 0.74542 (12) | 1.40873 (13) | 0.87484 (13) | 0.0479 (5) | |
O10 | 1.02369 (9) | 1.05688 (12) | 0.81714 (9) | 0.0273 (4) | |
O11 | 1.06698 (12) | 0.81458 (14) | 0.80523 (10) | 0.0408 (5) | |
O12 | 1.13681 (11) | 0.87915 (14) | 0.89287 (11) | 0.0397 (5) | |
O13 | 0.81075 (11) | 0.64262 (12) | 0.92168 (10) | 0.0305 (4) | |
O14 | 0.99219 (12) | 0.56099 (14) | 0.79536 (11) | 0.0452 (5) | |
O15 | 0.94537 (12) | 0.47732 (14) | 0.88687 (11) | 0.0425 (5) | |
O16 | 0.65073 (10) | 0.85912 (12) | 1.00172 (9) | 0.0311 (4) | |
O17 | 0.65515 (13) | 1.10374 (15) | 1.10142 (12) | 0.0481 (5) | |
O18 | 0.63013 (15) | 0.98279 (14) | 1.16867 (11) | 0.0516 (6) | |
O19 | 0.68324 (10) | 0.65242 (13) | 0.58916 (11) | 0.0324 (4) | |
O20 | 0.84952 (11) | 0.51425 (15) | 0.66895 (11) | 0.0421 (5) | |
O21 | 0.83717 (11) | 0.51898 (14) | 0.54813 (10) | 0.0413 (5) | |
O22 | 0.48064 (9) | 0.81166 (13) | 0.65903 (10) | 0.0319 (4) | |
O23 | 0.35161 (11) | 1.02424 (14) | 0.60975 (10) | 0.0389 (5) | |
O24 | 0.31420 (9) | 0.92625 (15) | 0.69239 (9) | 0.0359 (4) | |
N1 | 0.70220 (8) | 0.93131 (17) | 0.64645 (8) | 0.0163 (3) | |
N2 | 0.80617 (10) | 1.04588 (13) | 0.71884 (9) | 0.0178 (4) | |
N3 | 0.80014 (9) | 0.93353 (17) | 0.84604 (8) | 0.0174 (3) | |
N4 | 0.69776 (10) | 0.81836 (13) | 0.77255 (10) | 0.0182 (4) | |
N5 | 0.89664 (12) | 0.85270 (15) | 0.68610 (11) | 0.0293 (5) | |
N6 | 0.61961 (12) | 1.04122 (15) | 0.80552 (12) | 0.0304 (5) | |
C1 | 0.65203 (12) | 0.87051 (15) | 0.62231 (12) | 0.0188 (4) | |
C2 | 0.62579 (14) | 0.89745 (17) | 0.55176 (13) | 0.0242 (5) | |
H2 | 0.5914 | 0.8681 | 0.5237 | 0.029* | |
C3 | 0.66069 (14) | 0.97329 (18) | 0.53442 (13) | 0.0242 (5) | |
H3 | 0.6547 | 1.0057 | 0.4922 | 0.029* | |
C4 | 0.70912 (12) | 0.99481 (15) | 0.59351 (12) | 0.0186 (4) | |
C5 | 0.75597 (12) | 1.06776 (15) | 0.59667 (11) | 0.0183 (4) | |
C6 | 0.80212 (12) | 1.08928 (16) | 0.65429 (11) | 0.0190 (4) | |
C7 | 0.85284 (13) | 1.16287 (16) | 0.65532 (12) | 0.0215 (5) | |
H7 | 0.8612 | 1.2026 | 0.6180 | 0.026* | |
C8 | 0.88559 (13) | 1.16281 (16) | 0.72048 (12) | 0.0214 (5) | |
H8 | 0.9206 | 1.2026 | 0.7364 | 0.026* | |
C9 | 0.85624 (12) | 1.08960 (16) | 0.76104 (12) | 0.0194 (4) | |
C10 | 0.87507 (12) | 1.06763 (15) | 0.83179 (12) | 0.0198 (4) | |
C11 | 0.84854 (12) | 0.99537 (16) | 0.87107 (12) | 0.0199 (5) | |
C12 | 0.86776 (14) | 0.97419 (17) | 0.94447 (12) | 0.0222 (5) | |
H12 | 0.8997 | 1.0055 | 0.9738 | 0.027* | |
C13 | 0.83086 (14) | 0.90051 (16) | 0.96264 (12) | 0.0221 (5) | |
H13 | 0.8327 | 0.8715 | 1.0068 | 0.027* | |
C14 | 0.78781 (12) | 0.87509 (15) | 0.90057 (11) | 0.0189 (4) | |
C15 | 0.74154 (12) | 0.80193 (16) | 0.89757 (12) | 0.0205 (5) | |
C16 | 0.69989 (12) | 0.77599 (15) | 0.83795 (12) | 0.0182 (4) | |
C17 | 0.65223 (13) | 0.70074 (16) | 0.83603 (13) | 0.0234 (5) | |
H17 | 0.6435 | 0.6615 | 0.8736 | 0.028* | |
C18 | 0.62248 (13) | 0.69774 (16) | 0.76940 (12) | 0.0229 (5) | |
H18 | 0.5901 | 0.6554 | 0.7524 | 0.027* | |
C19 | 0.65012 (12) | 0.77197 (15) | 0.72961 (12) | 0.0196 (4) | |
C20 | 0.62945 (12) | 0.79549 (16) | 0.65957 (12) | 0.0197 (4) | |
C21 | 0.75388 (12) | 1.13169 (16) | 0.53436 (12) | 0.0204 (5) | |
C22 | 0.77841 (12) | 1.10892 (16) | 0.46560 (12) | 0.0227 (5) | |
C23 | 0.77619 (13) | 1.17047 (18) | 0.40931 (12) | 0.0271 (5) | |
H23 | 0.7915 | 1.1543 | 0.3636 | 0.033* | |
C24 | 0.75131 (13) | 1.25490 (18) | 0.42168 (13) | 0.0283 (5) | |
H24 | 0.7512 | 1.2960 | 0.3843 | 0.034* | |
C25 | 0.72640 (13) | 1.27991 (17) | 0.48866 (13) | 0.0282 (5) | |
H25 | 0.7095 | 1.3371 | 0.4965 | 0.034* | |
C26 | 0.72707 (13) | 1.21742 (17) | 0.54456 (12) | 0.0230 (5) | |
C27 | 0.82892 (15) | 0.99981 (19) | 0.38799 (14) | 0.0303 (6) | |
H27A | 0.8718 | 1.0327 | 0.3747 | 0.036* | |
H27B | 0.7914 | 1.0107 | 0.3523 | 0.036* | |
C28 | 0.84509 (15) | 0.90265 (18) | 0.39348 (14) | 0.0295 (6) | |
H28 | 0.8814 | 0.8920 | 0.4312 | 0.035* | |
C29 | 0.77898 (15) | 0.84505 (19) | 0.40623 (15) | 0.0335 (6) | |
H29A | 0.7742 | 0.8306 | 0.4569 | 0.040* | |
H29B | 0.7353 | 0.8745 | 0.3898 | 0.040* | |
C30 | 0.83208 (15) | 0.79575 (19) | 0.30314 (14) | 0.0338 (6) | |
C31 | 0.7808 (2) | 0.8208 (2) | 0.24213 (17) | 0.0512 (8) | |
H31A | 0.8082 | 0.8398 | 0.2013 | 0.061* | |
H31B | 0.7499 | 0.8681 | 0.2575 | 0.061* | |
H31C | 0.7520 | 0.7703 | 0.2291 | 0.061* | |
C32 | 0.88523 (17) | 0.7238 (2) | 0.28268 (16) | 0.0423 (7) | |
H32A | 0.9118 | 0.7421 | 0.2411 | 0.051* | |
H32B | 0.8594 | 0.6701 | 0.2720 | 0.051* | |
H32C | 0.9182 | 0.7135 | 0.3220 | 0.051* | |
C33 | 0.64633 (14) | 1.29806 (18) | 0.62154 (14) | 0.0308 (5) | |
H33A | 0.6569 | 1.3528 | 0.5963 | 0.037* | |
H33B | 0.6407 | 1.3118 | 0.6722 | 0.037* | |
C34 | 0.57663 (15) | 1.2587 (2) | 0.59212 (17) | 0.0375 (6) | |
H34 | 0.5810 | 1.2479 | 0.5403 | 0.045* | |
C35 | 0.55280 (19) | 1.1749 (2) | 0.6298 (2) | 0.0527 (8) | |
H35A | 0.5275 | 1.1356 | 0.5968 | 0.063* | |
H35B | 0.5938 | 1.1437 | 0.6505 | 0.063* | |
C36 | 0.47139 (18) | 1.2806 (3) | 0.65633 (19) | 0.0563 (9) | |
C37 | 0.4604 (5) | 1.3467 (5) | 0.7149 (4) | 0.151 (3) | |
H37A | 0.4365 | 1.3981 | 0.6957 | 0.182* | |
H37B | 0.5064 | 1.3636 | 0.7349 | 0.182* | |
H37C | 0.4312 | 1.3210 | 0.7519 | 0.182* | |
C38 | 0.4034 (2) | 1.2529 (4) | 0.6149 (3) | 0.0963 (19) | |
H38A | 0.3798 | 1.3046 | 0.5960 | 0.116* | |
H38B | 0.3713 | 1.2223 | 0.6467 | 0.116* | |
H38C | 0.4165 | 1.2144 | 0.5760 | 0.116* | |
C39 | 0.92581 (13) | 1.12923 (16) | 0.87089 (12) | 0.0207 (5) | |
C40 | 0.89830 (13) | 1.19600 (17) | 0.91483 (13) | 0.0249 (5) | |
C41 | 0.94493 (15) | 1.25479 (18) | 0.95106 (13) | 0.0291 (5) | |
H41 | 0.9265 | 1.3008 | 0.9788 | 0.035* | |
C42 | 1.01880 (15) | 1.24299 (18) | 0.94471 (13) | 0.0299 (6) | |
H42 | 1.0499 | 1.2807 | 0.9696 | 0.036* | |
C43 | 1.04730 (14) | 1.17692 (17) | 0.90251 (13) | 0.0258 (5) | |
H43 | 1.0971 | 1.1702 | 0.8990 | 0.031* | |
C44 | 1.00090 (13) | 1.12031 (16) | 0.86514 (12) | 0.0208 (5) | |
C45 | 0.78762 (15) | 1.2780 (2) | 0.93237 (15) | 0.0340 (6) | |
H45A | 0.8125 | 1.3135 | 0.9684 | 0.041* | |
H45B | 0.7390 | 1.2668 | 0.9491 | 0.041* | |
C46 | 0.78442 (15) | 1.32804 (18) | 0.86213 (15) | 0.0357 (6) | |
H46 | 0.8332 | 1.3409 | 0.8449 | 0.043* | |
C47 | 0.73958 (16) | 1.2817 (2) | 0.80340 (16) | 0.0382 (6) | |
H47A | 0.7576 | 1.2956 | 0.7559 | 0.046* | |
H47B | 0.7399 | 1.2179 | 0.8099 | 0.046* | |
C48 | 0.68002 (16) | 1.40735 (18) | 0.83336 (16) | 0.0370 (6) | |
C49 | 0.61788 (18) | 1.4346 (3) | 0.88111 (18) | 0.0549 (8) | |
H49A | 0.6239 | 1.4954 | 0.8953 | 0.066* | |
H49B | 0.6172 | 1.3976 | 0.9231 | 0.066* | |
H49C | 0.5732 | 1.4281 | 0.8551 | 0.066* | |
C50 | 0.6879 (2) | 1.4669 (2) | 0.76862 (19) | 0.0510 (8) | |
H50A | 0.6950 | 1.5270 | 0.7843 | 0.061* | |
H50B | 0.6449 | 1.4635 | 0.7394 | 0.061* | |
H50C | 0.7287 | 1.4482 | 0.7409 | 0.061* | |
C51 | 1.08808 (14) | 1.00826 (19) | 0.83257 (15) | 0.0300 (6) | |
H51A | 1.1235 | 1.0472 | 0.8548 | 0.036* | |
H51B | 1.1082 | 0.9859 | 0.7881 | 0.036* | |
C52 | 1.07227 (13) | 0.9307 (2) | 0.88318 (12) | 0.0306 (5) | |
H52 | 1.0545 | 0.9522 | 0.9295 | 0.037* | |
C53 | 1.02099 (16) | 0.86499 (19) | 0.85092 (15) | 0.0362 (6) | |
H53A | 0.9994 | 0.8280 | 0.8876 | 0.043* | |
H53B | 0.9830 | 0.8942 | 0.8235 | 0.043* | |
C54 | 1.13543 (18) | 0.8084 (2) | 0.84080 (15) | 0.0410 (7) | |
C55 | 1.1937 (2) | 0.8196 (3) | 0.7858 (2) | 0.0598 (10) | |
H55A | 1.2401 | 0.8156 | 0.8089 | 0.072* | |
H55B | 1.1888 | 0.8765 | 0.7631 | 0.072* | |
H55C | 1.1894 | 0.7738 | 0.7501 | 0.072* | |
C56 | 1.1410 (2) | 0.7190 (2) | 0.88039 (17) | 0.0517 (8) | |
H56A | 1.1870 | 0.7150 | 0.9045 | 0.062* | |
H56B | 1.1365 | 0.6715 | 0.8463 | 0.062* | |
H56C | 1.1030 | 0.7147 | 0.9151 | 0.062* | |
C57 | 0.73211 (13) | 0.74937 (16) | 0.96532 (12) | 0.0222 (5) | |
C58 | 0.76776 (13) | 0.66943 (17) | 0.97646 (13) | 0.0249 (5) | |
C59 | 0.75841 (14) | 0.62213 (18) | 1.04077 (14) | 0.0299 (5) | |
H59 | 0.7824 | 0.5688 | 1.0485 | 0.036* | |
C60 | 0.71304 (15) | 0.65611 (19) | 1.09219 (13) | 0.0326 (6) | |
H60 | 0.7071 | 0.6248 | 1.1349 | 0.039* | |
C61 | 0.67604 (15) | 0.73482 (19) | 1.08289 (13) | 0.0319 (6) | |
H61 | 0.6457 | 0.7564 | 1.1185 | 0.038* | |
C62 | 0.68543 (13) | 0.78119 (17) | 1.01862 (12) | 0.0251 (5) | |
C63 | 0.85663 (16) | 0.56721 (18) | 0.93646 (15) | 0.0350 (6) | |
H63A | 0.8281 | 0.5175 | 0.9532 | 0.042* | |
H63B | 0.8922 | 0.5819 | 0.9732 | 0.042* | |
C64 | 0.89305 (16) | 0.54426 (19) | 0.86774 (16) | 0.0366 (6) | |
H64 | 0.8580 | 0.5210 | 0.8327 | 0.044* | |
C65 | 0.94026 (17) | 0.6135 (2) | 0.83365 (16) | 0.0414 (7) | |
H65A | 0.9127 | 0.6510 | 0.8011 | 0.050* | |
H65B | 0.9636 | 0.6503 | 0.8698 | 0.050* | |
C66 | 0.99778 (15) | 0.4774 (2) | 0.83113 (14) | 0.0355 (6) | |
C67 | 0.98115 (17) | 0.4029 (2) | 0.77913 (16) | 0.0441 (7) | |
H67A | 1.0163 | 0.4027 | 0.7414 | 0.053* | |
H67B | 0.9338 | 0.4114 | 0.7587 | 0.053* | |
H67C | 0.9828 | 0.3473 | 0.8042 | 0.053* | |
C68 | 1.07179 (18) | 0.4695 (2) | 0.86531 (19) | 0.0503 (8) | |
H68A | 1.1078 | 0.4697 | 0.8284 | 0.060* | |
H68B | 1.0748 | 0.4151 | 0.8920 | 0.060* | |
H68C | 1.0798 | 0.5187 | 0.8972 | 0.060* | |
C69 | 0.61380 (15) | 0.90606 (19) | 1.05763 (14) | 0.0363 (6) | |
H69A | 0.5846 | 0.8650 | 1.0851 | 0.044* | |
H69B | 0.5819 | 0.9501 | 1.0364 | 0.044* | |
C70 | 0.66775 (17) | 0.9509 (2) | 1.10689 (14) | 0.0399 (7) | |
H70 | 0.7057 | 0.9091 | 1.1215 | 0.048* | |
C71 | 0.70140 (18) | 1.0350 (2) | 1.07491 (18) | 0.0449 (7) | |
H71A | 0.7507 | 1.0431 | 1.0917 | 0.054* | |
H71B | 0.7008 | 1.0332 | 1.0227 | 0.054* | |
C72 | 0.63349 (17) | 1.0766 (2) | 1.17161 (16) | 0.0398 (6) | |
C73 | 0.55921 (19) | 1.1119 (3) | 1.1865 (2) | 0.0647 (10) | |
H73A | 0.5447 | 1.0942 | 1.2338 | 0.078* | |
H73B | 0.5257 | 1.0887 | 1.1515 | 0.078* | |
H73C | 0.5598 | 1.1755 | 1.1836 | 0.078* | |
C74 | 0.6878 (2) | 1.1033 (3) | 1.2285 (2) | 0.0609 (10) | |
H74A | 0.6714 | 1.0839 | 1.2748 | 0.073* | |
H74B | 0.6930 | 1.1666 | 1.2286 | 0.073* | |
H74C | 0.7336 | 1.0763 | 1.2183 | 0.073* | |
C75 | 0.58028 (13) | 0.73079 (17) | 0.62228 (12) | 0.0223 (5) | |
C76 | 0.60962 (14) | 0.65535 (18) | 0.58999 (13) | 0.0265 (5) | |
C77 | 0.56599 (15) | 0.5876 (2) | 0.56175 (16) | 0.0352 (6) | |
H77 | 0.5863 | 0.5373 | 0.5412 | 0.042* | |
C78 | 0.49210 (15) | 0.59790 (19) | 0.56529 (15) | 0.0351 (6) | |
H78 | 0.4626 | 0.5537 | 0.5462 | 0.042* | |
C79 | 0.45997 (15) | 0.67152 (19) | 0.59612 (15) | 0.0330 (6) | |
H79 | 0.4099 | 0.6768 | 0.5977 | 0.040* | |
C80 | 0.50500 (13) | 0.73811 (17) | 0.62493 (13) | 0.0241 (5) | |
C81 | 0.71811 (15) | 0.57283 (18) | 0.56808 (15) | 0.0306 (6) | |
H81A | 0.7057 | 0.5576 | 0.5188 | 0.037* | |
H81B | 0.7045 | 0.5241 | 0.5992 | 0.037* | |
C82 | 0.79772 (14) | 0.59273 (18) | 0.57537 (14) | 0.0316 (5) | |
H82 | 0.8097 | 0.6464 | 0.5483 | 0.038* | |
C83 | 0.82375 (16) | 0.6015 (2) | 0.65288 (15) | 0.0380 (6) | |
H83A | 0.8622 | 0.6450 | 0.6571 | 0.046* | |
H83B | 0.7845 | 0.6181 | 0.6844 | 0.046* | |
C84 | 0.88143 (16) | 0.4830 (2) | 0.60483 (16) | 0.0349 (6) | |
C85 | 0.95815 (16) | 0.5139 (3) | 0.59708 (18) | 0.0497 (8) | |
H85A | 0.9776 | 0.4912 | 0.5530 | 0.060* | |
H85B | 0.9865 | 0.4927 | 0.6370 | 0.060* | |
H85C | 0.9594 | 0.5775 | 0.5962 | 0.060* | |
C86 | 0.8731 (2) | 0.3832 (2) | 0.6031 (2) | 0.0535 (9) | |
H86A | 0.8941 | 0.3604 | 0.5598 | 0.064* | |
H86B | 0.8227 | 0.3682 | 0.6041 | 0.064* | |
H86C | 0.8971 | 0.3578 | 0.6442 | 0.064* | |
C87 | 0.40431 (14) | 0.82652 (19) | 0.65648 (15) | 0.0314 (6) | |
H87A | 0.3792 | 0.7808 | 0.6832 | 0.038* | |
H87B | 0.3869 | 0.8258 | 0.6071 | 0.038* | |
C88 | 0.39150 (13) | 0.91597 (18) | 0.68989 (14) | 0.0328 (6) | |
H88 | 0.4129 | 0.9193 | 0.7382 | 0.039* | |
C89 | 0.41659 (16) | 0.9933 (2) | 0.64310 (18) | 0.0405 (7) | |
H89A | 0.4387 | 1.0394 | 0.6723 | 0.049* | |
H89B | 0.4510 | 0.9736 | 0.6074 | 0.049* | |
C90 | 0.29628 (15) | 1.00936 (18) | 0.66027 (14) | 0.0326 (6) | |
C91 | 0.29431 (18) | 1.0800 (2) | 0.71827 (16) | 0.0461 (7) | |
H91A | 0.2558 | 1.0674 | 0.7510 | 0.055* | |
H91B | 0.2864 | 1.1369 | 0.6965 | 0.055* | |
H91C | 0.3395 | 1.0805 | 0.7440 | 0.055* | |
C92 | 0.22475 (16) | 1.0017 (2) | 0.62220 (15) | 0.0417 (7) | |
H92A | 0.1874 | 0.9919 | 0.6568 | 0.050* | |
H92B | 0.2261 | 0.9528 | 0.5891 | 0.050* | |
H92C | 0.2150 | 1.0555 | 0.5962 | 0.050* | |
C93 | 0.83983 (13) | 0.87185 (15) | 0.70733 (11) | 0.0202 (5) | |
C94 | 0.96926 (14) | 0.8555 (2) | 0.65743 (14) | 0.0324 (6) | |
H94 | 1.0029 | 0.8347 | 0.6948 | 0.039* | |
C95 | 0.97579 (13) | 0.79524 (19) | 0.59258 (13) | 0.0302 (5) | |
C96 | 1.04274 (15) | 0.7584 (2) | 0.57695 (15) | 0.0391 (7) | |
H96 | 1.0817 | 0.7687 | 0.6078 | 0.047* | |
C97 | 1.05212 (16) | 0.7066 (2) | 0.51595 (15) | 0.0434 (7) | |
H97 | 1.0972 | 0.6823 | 0.5062 | 0.052* | |
C98 | 0.99486 (16) | 0.6913 (2) | 0.46995 (15) | 0.0373 (6) | |
H98 | 1.0014 | 0.6576 | 0.4286 | 0.045* | |
C99 | 0.92757 (15) | 0.72583 (19) | 0.48536 (14) | 0.0338 (6) | |
H99 | 0.8885 | 0.7143 | 0.4549 | 0.041* | |
C100 | 0.91815 (14) | 0.77820 (19) | 0.54669 (14) | 0.0312 (5) | |
H100 | 0.8729 | 0.8017 | 0.5567 | 0.037* | |
C101 | 0.98705 (19) | 0.9512 (2) | 0.6402 (2) | 0.0522 (9) | |
H10A | 0.9822 | 0.9866 | 0.6829 | 0.063* | |
H10B | 0.9545 | 0.9726 | 0.6037 | 0.063* | |
H10C | 1.0358 | 0.9550 | 0.6232 | 0.063* | |
C102 | 0.66865 (14) | 1.00265 (17) | 0.78342 (13) | 0.0241 (5) | |
C103 | 0.55441 (15) | 1.07346 (19) | 0.83821 (15) | 0.0353 (6) | |
H103 | 0.5267 | 1.1061 | 0.8017 | 0.042* | |
C104 | 0.50877 (15) | 0.9956 (2) | 0.86348 (15) | 0.0335 (6) | |
C105 | 0.53375 (16) | 0.9098 (2) | 0.86944 (16) | 0.0383 (7) | |
H105 | 0.5812 | 0.8970 | 0.8571 | 0.046* | |
C106 | 0.48923 (18) | 0.8422 (2) | 0.89358 (19) | 0.0490 (8) | |
H106 | 0.5070 | 0.7847 | 0.8975 | 0.059* | |
C107 | 0.41818 (18) | 0.8601 (2) | 0.91188 (19) | 0.0513 (8) | |
H107 | 0.3883 | 0.8148 | 0.9279 | 0.062* | |
C108 | 0.39232 (17) | 0.9450 (3) | 0.9062 (2) | 0.0559 (9) | |
H108 | 0.3447 | 0.9572 | 0.9183 | 0.067* | |
C109 | 0.43711 (17) | 1.0132 (2) | 0.88250 (19) | 0.0473 (8) | |
H109 | 0.4193 | 1.0708 | 0.8793 | 0.057* | |
C110 | 0.57418 (19) | 1.1377 (2) | 0.89899 (19) | 0.0501 (8) | |
H11A | 0.6029 | 1.1852 | 0.8801 | 0.060* | |
H11B | 0.6012 | 1.1068 | 0.9355 | 0.060* | |
H11C | 0.5308 | 1.1614 | 0.9195 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.01537 (7) | 0.01588 (7) | 0.01646 (7) | −0.00036 (6) | −0.00208 (5) | −0.00057 (7) |
O1 | 0.0313 (9) | 0.0287 (9) | 0.0200 (8) | 0.0036 (7) | 0.0018 (7) | −0.0025 (7) |
O2 | 0.0332 (10) | 0.0344 (10) | 0.0325 (9) | −0.0033 (8) | 0.0046 (8) | −0.0064 (8) |
O3 | 0.0417 (11) | 0.0411 (12) | 0.0457 (11) | −0.0139 (9) | 0.0183 (9) | −0.0199 (9) |
O4 | 0.0311 (9) | 0.0272 (9) | 0.0231 (8) | 0.0079 (7) | 0.0014 (7) | 0.0001 (7) |
O5 | 0.0422 (12) | 0.0671 (15) | 0.0398 (11) | 0.0058 (11) | 0.0095 (9) | 0.0042 (11) |
O6 | 0.0340 (11) | 0.0513 (14) | 0.0881 (18) | 0.0116 (10) | 0.0162 (11) | 0.0147 (13) |
O7 | 0.0267 (9) | 0.0286 (10) | 0.0387 (10) | 0.0017 (8) | −0.0004 (8) | −0.0070 (8) |
O8 | 0.0385 (10) | 0.0307 (10) | 0.0391 (10) | 0.0041 (8) | −0.0024 (8) | −0.0013 (8) |
O9 | 0.0482 (12) | 0.0296 (11) | 0.0658 (14) | 0.0078 (9) | −0.0116 (10) | −0.0116 (9) |
O10 | 0.0242 (9) | 0.0280 (9) | 0.0294 (9) | 0.0021 (7) | −0.0049 (7) | −0.0047 (7) |
O11 | 0.0519 (12) | 0.0371 (11) | 0.0332 (10) | 0.0070 (9) | −0.0003 (9) | −0.0058 (8) |
O12 | 0.0411 (11) | 0.0384 (11) | 0.0393 (10) | 0.0120 (9) | −0.0074 (8) | 0.0009 (9) |
O13 | 0.0341 (10) | 0.0275 (10) | 0.0299 (9) | 0.0093 (8) | 0.0007 (8) | 0.0024 (8) |
O14 | 0.0566 (13) | 0.0395 (12) | 0.0397 (11) | 0.0105 (10) | 0.0060 (10) | 0.0083 (9) |
O15 | 0.0508 (12) | 0.0352 (11) | 0.0417 (11) | 0.0135 (9) | 0.0116 (9) | 0.0046 (9) |
O16 | 0.0348 (10) | 0.0336 (10) | 0.0249 (8) | 0.0075 (8) | 0.0027 (7) | −0.0002 (7) |
O17 | 0.0548 (13) | 0.0387 (12) | 0.0509 (13) | 0.0056 (10) | 0.0076 (10) | 0.0047 (10) |
O18 | 0.0892 (18) | 0.0324 (12) | 0.0338 (11) | −0.0029 (12) | 0.0213 (11) | −0.0059 (9) |
O19 | 0.0198 (9) | 0.0281 (10) | 0.0493 (12) | −0.0021 (7) | 0.0011 (8) | −0.0147 (8) |
O20 | 0.0425 (12) | 0.0461 (13) | 0.0376 (11) | −0.0001 (10) | −0.0064 (9) | 0.0024 (9) |
O21 | 0.0416 (11) | 0.0471 (12) | 0.0350 (10) | 0.0196 (9) | −0.0097 (8) | −0.0109 (9) |
O22 | 0.0163 (8) | 0.0350 (10) | 0.0444 (10) | 0.0006 (7) | −0.0026 (7) | −0.0088 (8) |
O23 | 0.0450 (11) | 0.0380 (11) | 0.0340 (10) | 0.0057 (9) | 0.0112 (8) | 0.0056 (8) |
O24 | 0.0264 (8) | 0.0392 (10) | 0.0422 (9) | 0.0091 (9) | 0.0078 (7) | 0.0089 (10) |
N1 | 0.0148 (7) | 0.0175 (8) | 0.0166 (7) | −0.0010 (11) | −0.0033 (6) | −0.0008 (10) |
N2 | 0.0161 (9) | 0.0209 (10) | 0.0164 (8) | 0.0005 (8) | 0.0000 (7) | −0.0006 (7) |
N3 | 0.0177 (8) | 0.0172 (8) | 0.0171 (7) | 0.0000 (11) | −0.0006 (6) | −0.0007 (10) |
N4 | 0.0168 (9) | 0.0174 (10) | 0.0205 (9) | 0.0003 (8) | −0.0021 (7) | 0.0003 (7) |
N5 | 0.0274 (11) | 0.0360 (12) | 0.0245 (10) | 0.0067 (9) | 0.0017 (8) | 0.0001 (9) |
N6 | 0.0265 (11) | 0.0322 (12) | 0.0325 (11) | 0.0087 (9) | 0.0025 (9) | −0.0015 (9) |
C1 | 0.0149 (10) | 0.0200 (11) | 0.0214 (10) | 0.0007 (9) | −0.0026 (8) | −0.0029 (8) |
C2 | 0.0212 (12) | 0.0298 (12) | 0.0215 (11) | −0.0042 (10) | −0.0048 (9) | 0.0000 (9) |
C3 | 0.0260 (12) | 0.0278 (12) | 0.0187 (11) | 0.0008 (10) | −0.0078 (10) | 0.0026 (9) |
C4 | 0.0164 (10) | 0.0210 (11) | 0.0183 (10) | 0.0018 (9) | −0.0019 (8) | 0.0008 (8) |
C5 | 0.0175 (10) | 0.0203 (11) | 0.0172 (10) | 0.0009 (9) | 0.0007 (8) | −0.0007 (8) |
C6 | 0.0204 (11) | 0.0190 (11) | 0.0177 (10) | 0.0004 (9) | 0.0005 (8) | 0.0003 (8) |
C7 | 0.0249 (12) | 0.0187 (11) | 0.0209 (10) | −0.0057 (9) | 0.0012 (9) | 0.0011 (9) |
C8 | 0.0223 (11) | 0.0204 (12) | 0.0215 (10) | −0.0031 (9) | −0.0010 (9) | 0.0009 (9) |
C9 | 0.0182 (11) | 0.0198 (11) | 0.0203 (10) | −0.0008 (9) | −0.0003 (8) | −0.0022 (9) |
C10 | 0.0205 (11) | 0.0185 (11) | 0.0202 (10) | −0.0011 (9) | −0.0032 (8) | −0.0037 (8) |
C11 | 0.0195 (11) | 0.0233 (12) | 0.0170 (10) | −0.0021 (9) | −0.0025 (8) | −0.0024 (9) |
C12 | 0.0258 (12) | 0.0230 (12) | 0.0178 (10) | −0.0032 (10) | −0.0051 (9) | 0.0000 (9) |
C13 | 0.0259 (12) | 0.0246 (11) | 0.0159 (10) | −0.0001 (10) | −0.0034 (9) | 0.0017 (8) |
C14 | 0.0189 (11) | 0.0207 (11) | 0.0169 (10) | 0.0015 (9) | −0.0009 (8) | −0.0004 (8) |
C15 | 0.0210 (11) | 0.0195 (11) | 0.0209 (10) | 0.0036 (9) | 0.0006 (9) | 0.0019 (9) |
C16 | 0.0175 (10) | 0.0173 (11) | 0.0196 (10) | −0.0001 (9) | 0.0007 (8) | 0.0007 (8) |
C17 | 0.0237 (12) | 0.0207 (12) | 0.0259 (11) | −0.0010 (10) | −0.0015 (9) | 0.0044 (9) |
C18 | 0.0222 (12) | 0.0202 (12) | 0.0262 (11) | −0.0041 (9) | −0.0014 (9) | −0.0023 (9) |
C19 | 0.0189 (11) | 0.0175 (11) | 0.0224 (10) | 0.0001 (9) | −0.0018 (8) | −0.0023 (8) |
C20 | 0.0162 (10) | 0.0206 (11) | 0.0225 (10) | −0.0003 (9) | −0.0004 (8) | −0.0018 (9) |
C21 | 0.0195 (11) | 0.0238 (12) | 0.0180 (10) | −0.0023 (9) | −0.0017 (8) | 0.0045 (9) |
C22 | 0.0199 (11) | 0.0263 (12) | 0.0219 (10) | −0.0014 (9) | −0.0031 (8) | 0.0011 (9) |
C23 | 0.0241 (12) | 0.0400 (15) | 0.0173 (10) | −0.0032 (11) | −0.0002 (9) | 0.0035 (10) |
C24 | 0.0233 (12) | 0.0352 (14) | 0.0264 (12) | −0.0002 (10) | −0.0023 (9) | 0.0107 (10) |
C25 | 0.0295 (12) | 0.0249 (12) | 0.0302 (12) | 0.0046 (10) | −0.0026 (10) | 0.0065 (10) |
C26 | 0.0215 (11) | 0.0255 (12) | 0.0218 (10) | 0.0008 (9) | 0.0000 (9) | 0.0026 (9) |
C27 | 0.0301 (13) | 0.0357 (15) | 0.0251 (12) | 0.0017 (11) | 0.0049 (10) | −0.0041 (11) |
C28 | 0.0276 (13) | 0.0311 (14) | 0.0300 (12) | −0.0013 (10) | 0.0049 (10) | −0.0056 (10) |
C29 | 0.0297 (13) | 0.0327 (14) | 0.0383 (14) | 0.0001 (11) | 0.0053 (11) | −0.0050 (11) |
C30 | 0.0375 (14) | 0.0333 (14) | 0.0306 (13) | −0.0059 (12) | 0.0021 (11) | −0.0071 (11) |
C31 | 0.059 (2) | 0.055 (2) | 0.0394 (16) | −0.0081 (17) | −0.0052 (14) | 0.0074 (15) |
C32 | 0.0493 (17) | 0.0371 (16) | 0.0407 (15) | −0.0014 (13) | 0.0103 (13) | −0.0079 (13) |
C33 | 0.0338 (13) | 0.0259 (12) | 0.0327 (13) | 0.0049 (11) | 0.0041 (11) | −0.0042 (10) |
C34 | 0.0280 (13) | 0.0410 (16) | 0.0436 (16) | 0.0035 (12) | 0.0051 (12) | −0.0011 (13) |
C35 | 0.0456 (18) | 0.0463 (19) | 0.066 (2) | −0.0066 (15) | 0.0190 (16) | −0.0046 (16) |
C36 | 0.0425 (18) | 0.073 (2) | 0.0534 (19) | 0.0156 (17) | 0.0201 (15) | 0.0119 (18) |
C37 | 0.228 (8) | 0.106 (5) | 0.122 (5) | 0.072 (6) | 0.088 (5) | −0.018 (4) |
C38 | 0.039 (2) | 0.131 (5) | 0.119 (4) | −0.006 (2) | −0.004 (2) | 0.072 (4) |
C39 | 0.0241 (12) | 0.0208 (12) | 0.0172 (10) | −0.0054 (9) | −0.0026 (9) | 0.0015 (9) |
C40 | 0.0266 (12) | 0.0243 (12) | 0.0237 (11) | −0.0023 (10) | −0.0038 (9) | 0.0002 (9) |
C41 | 0.0353 (14) | 0.0258 (13) | 0.0262 (12) | −0.0040 (11) | −0.0041 (10) | −0.0077 (10) |
C42 | 0.0348 (14) | 0.0268 (13) | 0.0278 (12) | −0.0106 (11) | −0.0094 (10) | −0.0011 (10) |
C43 | 0.0249 (12) | 0.0281 (13) | 0.0242 (11) | −0.0065 (10) | −0.0066 (9) | 0.0039 (10) |
C44 | 0.0217 (11) | 0.0216 (11) | 0.0191 (10) | −0.0028 (9) | −0.0031 (8) | 0.0029 (9) |
C45 | 0.0327 (14) | 0.0325 (15) | 0.0369 (14) | 0.0042 (12) | −0.0012 (11) | −0.0122 (12) |
C46 | 0.0346 (14) | 0.0276 (13) | 0.0450 (15) | 0.0012 (11) | 0.0018 (12) | −0.0052 (11) |
C47 | 0.0417 (15) | 0.0334 (15) | 0.0395 (15) | 0.0089 (12) | −0.0011 (12) | −0.0035 (12) |
C48 | 0.0352 (14) | 0.0303 (14) | 0.0456 (15) | 0.0058 (11) | −0.0001 (12) | −0.0029 (11) |
C49 | 0.0547 (18) | 0.0522 (18) | 0.0580 (17) | 0.007 (2) | 0.0140 (15) | −0.005 (2) |
C50 | 0.062 (2) | 0.0365 (16) | 0.0542 (19) | 0.0113 (15) | 0.0124 (16) | 0.0046 (14) |
C51 | 0.0223 (12) | 0.0324 (14) | 0.0354 (13) | 0.0012 (11) | 0.0010 (10) | −0.0023 (11) |
C52 | 0.0339 (12) | 0.0315 (12) | 0.0263 (10) | 0.0076 (13) | 0.0002 (9) | 0.0005 (13) |
C53 | 0.0407 (15) | 0.0308 (14) | 0.0371 (14) | −0.0026 (12) | 0.0052 (12) | −0.0011 (11) |
C54 | 0.0574 (18) | 0.0344 (15) | 0.0314 (14) | 0.0113 (14) | 0.0085 (13) | 0.0028 (11) |
C55 | 0.067 (2) | 0.055 (2) | 0.058 (2) | 0.0202 (18) | 0.0272 (18) | 0.0118 (17) |
C56 | 0.077 (2) | 0.0366 (16) | 0.0416 (16) | 0.0184 (16) | 0.0076 (16) | 0.0077 (13) |
C57 | 0.0244 (12) | 0.0208 (11) | 0.0212 (10) | −0.0047 (9) | −0.0039 (9) | 0.0011 (9) |
C58 | 0.0254 (12) | 0.0254 (12) | 0.0238 (11) | −0.0027 (9) | −0.0030 (9) | 0.0028 (9) |
C59 | 0.0317 (13) | 0.0255 (13) | 0.0323 (13) | −0.0034 (10) | −0.0081 (10) | 0.0073 (10) |
C60 | 0.0337 (14) | 0.0401 (15) | 0.0240 (12) | −0.0110 (12) | −0.0017 (10) | 0.0106 (11) |
C61 | 0.0343 (14) | 0.0388 (15) | 0.0225 (11) | −0.0056 (12) | 0.0021 (10) | 0.0043 (11) |
C62 | 0.0240 (11) | 0.0303 (13) | 0.0211 (11) | −0.0027 (10) | −0.0008 (9) | 0.0019 (9) |
C63 | 0.0397 (15) | 0.0238 (13) | 0.0415 (15) | 0.0064 (11) | −0.0054 (12) | −0.0002 (11) |
C64 | 0.0371 (15) | 0.0305 (14) | 0.0420 (15) | 0.0037 (12) | −0.0049 (12) | −0.0060 (12) |
C65 | 0.0450 (16) | 0.0384 (16) | 0.0406 (15) | 0.0068 (13) | −0.0016 (13) | 0.0030 (12) |
C66 | 0.0375 (15) | 0.0408 (15) | 0.0281 (13) | 0.0058 (12) | 0.0016 (11) | 0.0066 (11) |
C67 | 0.0458 (17) | 0.0492 (18) | 0.0374 (15) | 0.0079 (14) | 0.0032 (13) | −0.0014 (12) |
C68 | 0.0492 (18) | 0.0528 (19) | 0.0487 (18) | −0.0014 (15) | −0.0107 (15) | 0.0075 (15) |
C69 | 0.0352 (14) | 0.0402 (16) | 0.0336 (13) | 0.0064 (11) | 0.0062 (11) | −0.0028 (11) |
C70 | 0.0471 (16) | 0.044 (2) | 0.0283 (12) | 0.0040 (13) | 0.0046 (11) | −0.0048 (12) |
C71 | 0.0455 (17) | 0.0412 (17) | 0.0483 (17) | −0.0015 (14) | 0.0104 (14) | −0.0015 (14) |
C72 | 0.0437 (16) | 0.0342 (15) | 0.0414 (15) | 0.0009 (13) | 0.0032 (13) | −0.0037 (12) |
C73 | 0.0449 (19) | 0.075 (3) | 0.074 (3) | 0.0161 (18) | 0.0067 (17) | −0.001 (2) |
C74 | 0.052 (2) | 0.073 (3) | 0.058 (2) | −0.0031 (19) | −0.0014 (17) | −0.0157 (19) |
C75 | 0.0215 (12) | 0.0254 (13) | 0.0200 (10) | −0.0018 (10) | −0.0046 (9) | 0.0031 (9) |
C76 | 0.0265 (12) | 0.0260 (13) | 0.0270 (12) | −0.0020 (10) | −0.0012 (10) | −0.0050 (10) |
C77 | 0.0310 (14) | 0.0313 (15) | 0.0434 (15) | −0.0026 (11) | −0.0030 (12) | −0.0127 (12) |
C78 | 0.0330 (14) | 0.0290 (14) | 0.0432 (15) | −0.0090 (11) | −0.0076 (12) | −0.0093 (12) |
C79 | 0.0224 (13) | 0.0363 (15) | 0.0400 (14) | −0.0058 (11) | −0.0066 (11) | −0.0043 (12) |
C80 | 0.0225 (12) | 0.0239 (12) | 0.0259 (11) | −0.0018 (10) | −0.0045 (9) | −0.0024 (9) |
C81 | 0.0342 (14) | 0.0255 (13) | 0.0322 (13) | 0.0050 (11) | 0.0002 (11) | −0.0064 (10) |
C82 | 0.0309 (13) | 0.0314 (13) | 0.0324 (13) | 0.0060 (11) | −0.0007 (10) | −0.0029 (11) |
C83 | 0.0366 (15) | 0.0412 (16) | 0.0363 (14) | −0.0012 (12) | −0.0031 (12) | −0.0080 (12) |
C84 | 0.0329 (14) | 0.0352 (16) | 0.0366 (15) | 0.0059 (12) | −0.0039 (12) | 0.0017 (12) |
C85 | 0.0354 (15) | 0.063 (2) | 0.0505 (18) | 0.0017 (15) | −0.0027 (13) | 0.0239 (16) |
C86 | 0.057 (2) | 0.0386 (18) | 0.064 (2) | 0.0058 (16) | −0.0085 (18) | −0.0019 (17) |
C87 | 0.0201 (12) | 0.0341 (15) | 0.0399 (14) | 0.0012 (11) | −0.0004 (10) | 0.0003 (12) |
C88 | 0.0254 (12) | 0.0391 (17) | 0.0341 (12) | 0.0032 (10) | 0.0027 (10) | −0.0009 (11) |
C89 | 0.0367 (15) | 0.0336 (15) | 0.0513 (17) | 0.0009 (12) | 0.0108 (13) | 0.0032 (13) |
C90 | 0.0379 (14) | 0.0333 (14) | 0.0265 (12) | 0.0097 (11) | 0.0030 (10) | 0.0023 (10) |
C91 | 0.0482 (18) | 0.052 (2) | 0.0382 (15) | 0.0088 (15) | −0.0015 (13) | −0.0095 (14) |
C92 | 0.0432 (16) | 0.0509 (18) | 0.0311 (13) | 0.0128 (14) | −0.0004 (12) | −0.0020 (12) |
C93 | 0.0263 (12) | 0.0190 (11) | 0.0152 (10) | 0.0030 (9) | −0.0035 (9) | −0.0014 (8) |
C94 | 0.0219 (12) | 0.0463 (17) | 0.0291 (12) | 0.0049 (11) | 0.0027 (10) | −0.0023 (11) |
C95 | 0.0267 (12) | 0.0390 (15) | 0.0250 (11) | 0.0041 (11) | 0.0034 (10) | 0.0037 (10) |
C96 | 0.0273 (13) | 0.0589 (19) | 0.0311 (13) | 0.0134 (13) | 0.0010 (11) | 0.0015 (13) |
C97 | 0.0346 (15) | 0.059 (2) | 0.0365 (14) | 0.0227 (14) | 0.0087 (12) | 0.0039 (14) |
C98 | 0.0426 (16) | 0.0402 (16) | 0.0293 (12) | 0.0117 (13) | 0.0069 (11) | 0.0006 (11) |
C99 | 0.0341 (14) | 0.0376 (15) | 0.0298 (12) | 0.0042 (12) | 0.0029 (11) | 0.0006 (11) |
C100 | 0.0252 (12) | 0.0383 (14) | 0.0301 (12) | 0.0056 (11) | 0.0038 (10) | 0.0033 (11) |
C101 | 0.0437 (17) | 0.055 (3) | 0.0577 (19) | −0.0137 (15) | 0.0121 (15) | −0.0146 (16) |
C102 | 0.0283 (13) | 0.0219 (12) | 0.0220 (11) | −0.0036 (10) | −0.0035 (10) | −0.0001 (9) |
C103 | 0.0298 (13) | 0.0369 (15) | 0.0394 (14) | 0.0138 (11) | 0.0079 (11) | −0.0014 (12) |
C104 | 0.0306 (14) | 0.0393 (16) | 0.0307 (13) | 0.0092 (12) | 0.0028 (11) | −0.0020 (11) |
C105 | 0.0331 (14) | 0.0381 (18) | 0.0439 (15) | 0.0090 (12) | 0.0070 (12) | −0.0024 (12) |
C106 | 0.0422 (17) | 0.0408 (17) | 0.064 (2) | 0.0049 (14) | 0.0127 (15) | 0.0007 (15) |
C107 | 0.0414 (17) | 0.053 (2) | 0.060 (2) | −0.0055 (15) | 0.0143 (15) | 0.0018 (16) |
C108 | 0.0377 (16) | 0.061 (2) | 0.069 (2) | 0.0084 (16) | 0.0214 (15) | 0.0030 (19) |
C109 | 0.0354 (16) | 0.0472 (18) | 0.060 (2) | 0.0114 (14) | 0.0144 (14) | −0.0022 (15) |
C110 | 0.056 (2) | 0.0392 (17) | 0.0551 (19) | 0.0015 (15) | 0.0212 (16) | −0.0136 (14) |
Ru1—C102 | 1.998 (3) | C43—C44 | 1.392 (3) |
Ru1—C93 | 2.006 (2) | C43—H43 | 0.9300 |
Ru1—N2 | 2.051 (2) | C45—C46 | 1.508 (4) |
Ru1—N4 | 2.0522 (19) | C45—H45A | 0.9700 |
Ru1—N1 | 2.0549 (15) | C45—H45B | 0.9700 |
Ru1—N3 | 2.0581 (15) | C46—C47 | 1.534 (4) |
O1—C22 | 1.363 (3) | C46—H46 | 0.9800 |
O1—C27 | 1.434 (3) | C47—H47A | 0.9700 |
O2—C30 | 1.424 (3) | C47—H47B | 0.9700 |
O2—C29 | 1.431 (3) | C48—C50 | 1.509 (4) |
O3—C30 | 1.429 (3) | C48—C49 | 1.515 (4) |
O3—C28 | 1.435 (3) | C49—H49A | 0.9600 |
O4—C26 | 1.370 (3) | C49—H49B | 0.9600 |
O4—C33 | 1.430 (3) | C49—H49C | 0.9600 |
O5—C36 | 1.390 (4) | C50—H50A | 0.9600 |
O5—C35 | 1.419 (4) | C50—H50B | 0.9600 |
O6—C34 | 1.425 (4) | C50—H50C | 0.9600 |
O6—C36 | 1.443 (4) | C51—C52 | 1.531 (4) |
O7—C40 | 1.369 (3) | C51—H51A | 0.9700 |
O7—C45 | 1.438 (3) | C51—H51B | 0.9700 |
O8—C47 | 1.425 (3) | C52—C53 | 1.494 (4) |
O8—C48 | 1.425 (3) | C52—H52 | 0.9800 |
O9—C48 | 1.429 (4) | C53—H53A | 0.9700 |
O9—C46 | 1.436 (3) | C53—H53B | 0.9700 |
O10—C44 | 1.377 (3) | C54—C55 | 1.502 (4) |
O10—C51 | 1.426 (3) | C54—C56 | 1.538 (4) |
O11—C53 | 1.427 (3) | C55—H55A | 0.9600 |
O11—C54 | 1.427 (4) | C55—H55B | 0.9600 |
O12—C52 | 1.435 (3) | C55—H55C | 0.9600 |
O12—C54 | 1.441 (4) | C56—H56A | 0.9600 |
O13—C58 | 1.359 (3) | C56—H56B | 0.9600 |
O13—C63 | 1.444 (3) | C56—H56C | 0.9600 |
O14—C66 | 1.429 (3) | C57—C58 | 1.389 (4) |
O14—C65 | 1.439 (4) | C57—C62 | 1.404 (3) |
O15—C66 | 1.425 (3) | C58—C59 | 1.404 (3) |
O15—C64 | 1.441 (3) | C59—C60 | 1.376 (4) |
O16—C62 | 1.375 (3) | C59—H59 | 0.9300 |
O16—C69 | 1.435 (3) | C60—C61 | 1.381 (4) |
O17—C72 | 1.427 (4) | C60—H60 | 0.9300 |
O17—C71 | 1.434 (4) | C61—C62 | 1.396 (3) |
O18—C72 | 1.418 (4) | C61—H61 | 0.9300 |
O18—C70 | 1.431 (3) | C63—C64 | 1.490 (4) |
O19—C76 | 1.364 (3) | C63—H63A | 0.9700 |
O19—C81 | 1.420 (3) | C63—H63B | 0.9700 |
O20—C84 | 1.415 (4) | C64—C65 | 1.505 (4) |
O20—C83 | 1.430 (4) | C64—H64 | 0.9800 |
O21—C82 | 1.426 (3) | C65—H65A | 0.9700 |
O21—C84 | 1.435 (3) | C65—H65B | 0.9700 |
O22—C80 | 1.357 (3) | C66—C68 | 1.510 (4) |
O22—C87 | 1.431 (3) | C66—C67 | 1.512 (4) |
O23—C90 | 1.413 (3) | C67—H67A | 0.9600 |
O23—C89 | 1.426 (4) | C67—H67B | 0.9600 |
O24—C90 | 1.426 (3) | C67—H67C | 0.9600 |
O24—C88 | 1.440 (3) | C68—H68A | 0.9600 |
N1—C1 | 1.377 (3) | C68—H68B | 0.9600 |
N1—C4 | 1.380 (3) | C68—H68C | 0.9600 |
N2—C6 | 1.368 (3) | C69—C70 | 1.509 (4) |
N2—C9 | 1.377 (3) | C69—H69A | 0.9700 |
N3—C14 | 1.364 (3) | C69—H69B | 0.9700 |
N3—C11 | 1.372 (3) | C70—C71 | 1.536 (4) |
N4—C16 | 1.373 (3) | C70—H70 | 0.9800 |
N4—C19 | 1.375 (3) | C71—H71A | 0.9700 |
N5—C93 | 1.163 (3) | C71—H71B | 0.9700 |
N5—C94 | 1.451 (3) | C72—C73 | 1.502 (5) |
N6—C102 | 1.157 (3) | C72—C74 | 1.507 (5) |
N6—C103 | 1.440 (3) | C73—H73A | 0.9600 |
C1—C20 | 1.393 (3) | C73—H73B | 0.9600 |
C1—C2 | 1.452 (3) | C73—H73C | 0.9600 |
C2—C3 | 1.354 (4) | C74—H74A | 0.9600 |
C2—H2 | 0.9300 | C74—H74B | 0.9600 |
C3—C4 | 1.448 (3) | C74—H74C | 0.9600 |
C3—H3 | 0.9300 | C75—C76 | 1.398 (4) |
C4—C5 | 1.402 (3) | C75—C80 | 1.399 (3) |
C5—C6 | 1.402 (3) | C76—C77 | 1.401 (4) |
C5—C21 | 1.507 (3) | C77—C78 | 1.378 (4) |
C6—C7 | 1.454 (3) | C77—H77 | 0.9300 |
C7—C8 | 1.349 (3) | C78—C79 | 1.386 (4) |
C7—H7 | 0.9300 | C78—H78 | 0.9300 |
C8—C9 | 1.446 (3) | C79—C80 | 1.408 (4) |
C8—H8 | 0.9300 | C79—H79 | 0.9300 |
C9—C10 | 1.397 (3) | C81—C82 | 1.509 (4) |
C10—C11 | 1.403 (3) | C81—H81A | 0.9700 |
C10—C39 | 1.504 (3) | C81—H81B | 0.9700 |
C11—C12 | 1.442 (3) | C82—C83 | 1.520 (4) |
C12—C13 | 1.349 (3) | C82—H82 | 0.9800 |
C12—H12 | 0.9300 | C83—H83A | 0.9700 |
C13—C14 | 1.448 (3) | C83—H83B | 0.9700 |
C13—H13 | 0.9300 | C84—C85 | 1.502 (4) |
C14—C15 | 1.398 (3) | C84—C86 | 1.514 (4) |
C15—C16 | 1.400 (3) | C85—H85A | 0.9600 |
C15—C57 | 1.499 (3) | C85—H85B | 0.9600 |
C16—C17 | 1.438 (3) | C85—H85C | 0.9600 |
C17—C18 | 1.351 (3) | C86—H86A | 0.9600 |
C17—H17 | 0.9300 | C86—H86B | 0.9600 |
C18—C19 | 1.438 (3) | C86—H86C | 0.9600 |
C18—H18 | 0.9300 | C87—C88 | 1.505 (4) |
C19—C20 | 1.399 (3) | C87—H87A | 0.9700 |
C20—C75 | 1.500 (3) | C87—H87B | 0.9700 |
C21—C26 | 1.398 (3) | C88—C89 | 1.530 (4) |
C21—C22 | 1.402 (3) | C88—H88 | 0.9800 |
C22—C23 | 1.399 (3) | C89—H89A | 0.9700 |
C23—C24 | 1.374 (4) | C89—H89B | 0.9700 |
C23—H23 | 0.9300 | C90—C92 | 1.500 (4) |
C24—C25 | 1.383 (4) | C90—C91 | 1.516 (4) |
C24—H24 | 0.9300 | C91—H91A | 0.9600 |
C25—C26 | 1.402 (3) | C91—H91B | 0.9600 |
C25—H25 | 0.9300 | C91—H91C | 0.9600 |
C27—C28 | 1.499 (4) | C92—H92A | 0.9600 |
C27—H27A | 0.9700 | C92—H92B | 0.9600 |
C27—H27B | 0.9700 | C92—H92C | 0.9600 |
C28—C29 | 1.521 (4) | C94—C101 | 1.516 (5) |
C28—H28 | 0.9800 | C94—C95 | 1.515 (4) |
C29—H29A | 0.9700 | C94—H94 | 0.9800 |
C29—H29B | 0.9700 | C95—C100 | 1.384 (4) |
C30—C32 | 1.516 (4) | C95—C96 | 1.391 (4) |
C30—C31 | 1.519 (4) | C96—C97 | 1.389 (4) |
C31—H31A | 0.9600 | C96—H96 | 0.9300 |
C31—H31B | 0.9600 | C97—C98 | 1.375 (4) |
C31—H31C | 0.9600 | C97—H97 | 0.9300 |
C32—H32A | 0.9600 | C98—C99 | 1.383 (4) |
C32—H32B | 0.9600 | C98—H98 | 0.9300 |
C32—H32C | 0.9600 | C99—C100 | 1.398 (4) |
C33—C34 | 1.518 (4) | C99—H99 | 0.9300 |
C33—H33A | 0.9700 | C100—H100 | 0.9300 |
C33—H33B | 0.9700 | C101—H10A | 0.9600 |
C34—C35 | 1.512 (5) | C101—H10B | 0.9600 |
C34—H34 | 0.9800 | C101—H10C | 0.9600 |
C35—H35A | 0.9700 | C103—C104 | 1.523 (4) |
C35—H35B | 0.9700 | C103—C110 | 1.530 (4) |
C36—C37 | 1.492 (7) | C103—H103 | 0.9800 |
C36—C38 | 1.526 (6) | C104—C105 | 1.379 (4) |
C37—H37A | 0.9600 | C104—C109 | 1.401 (4) |
C37—H37B | 0.9600 | C105—C106 | 1.388 (4) |
C37—H37C | 0.9600 | C105—H105 | 0.9300 |
C38—H38A | 0.9600 | C106—C107 | 1.388 (5) |
C38—H38B | 0.9600 | C106—H106 | 0.9300 |
C38—H38C | 0.9600 | C107—C108 | 1.370 (5) |
C39—C40 | 1.395 (3) | C107—H107 | 0.9300 |
C39—C44 | 1.401 (3) | C108—C109 | 1.395 (5) |
C40—C41 | 1.405 (3) | C108—H108 | 0.9300 |
C41—C42 | 1.385 (4) | C109—H109 | 0.9300 |
C41—H41 | 0.9300 | C110—H11A | 0.9600 |
C42—C43 | 1.376 (4) | C110—H11B | 0.9600 |
C42—H42 | 0.9300 | C110—H11C | 0.9600 |
C102—Ru1—C93 | 175.02 (11) | C51—C52—H52 | 110.8 |
C102—Ru1—N2 | 91.39 (9) | O11—C53—C52 | 102.2 (2) |
C93—Ru1—N2 | 83.69 (9) | O11—C53—H53A | 111.3 |
C102—Ru1—N4 | 88.98 (9) | C52—C53—H53A | 111.3 |
C93—Ru1—N4 | 95.95 (9) | O11—C53—H53B | 111.3 |
N2—Ru1—N4 | 179.62 (9) | C52—C53—H53B | 111.3 |
C102—Ru1—N1 | 88.81 (9) | H53A—C53—H53B | 109.2 |
C93—Ru1—N1 | 91.90 (8) | O11—C54—O12 | 105.8 (2) |
N2—Ru1—N1 | 90.17 (8) | O11—C54—C55 | 108.5 (3) |
N4—Ru1—N1 | 89.76 (8) | O12—C54—C55 | 111.4 (3) |
C102—Ru1—N3 | 90.59 (9) | O11—C54—C56 | 109.5 (3) |
C93—Ru1—N3 | 88.73 (8) | O12—C54—C56 | 109.1 (2) |
N2—Ru1—N3 | 90.21 (8) | C55—C54—C56 | 112.2 (3) |
N4—Ru1—N3 | 89.86 (8) | C54—C55—H55A | 109.5 |
N1—Ru1—N3 | 179.29 (7) | C54—C55—H55B | 109.5 |
C22—O1—C27 | 116.84 (19) | H55A—C55—H55B | 109.5 |
C30—O2—C29 | 106.3 (2) | C54—C55—H55C | 109.5 |
C30—O3—C28 | 109.5 (2) | H55A—C55—H55C | 109.5 |
C26—O4—C33 | 118.55 (19) | H55B—C55—H55C | 109.5 |
C36—O5—C35 | 106.5 (3) | C54—C56—H56A | 109.5 |
C34—O6—C36 | 107.8 (2) | C54—C56—H56B | 109.5 |
C40—O7—C45 | 118.9 (2) | H56A—C56—H56B | 109.5 |
C47—O8—C48 | 105.2 (2) | C54—C56—H56C | 109.5 |
C48—O9—C46 | 108.9 (2) | H56A—C56—H56C | 109.5 |
C44—O10—C51 | 119.17 (19) | H56B—C56—H56C | 109.5 |
C53—O11—C54 | 106.9 (2) | C58—C57—C62 | 119.1 (2) |
C52—O12—C54 | 107.9 (2) | C58—C57—C15 | 121.7 (2) |
C58—O13—C63 | 116.0 (2) | C62—C57—C15 | 119.2 (2) |
C66—O14—C65 | 107.6 (2) | O13—C58—C57 | 115.3 (2) |
C66—O15—C64 | 106.3 (2) | O13—C58—C59 | 124.3 (2) |
C62—O16—C69 | 118.76 (19) | C57—C58—C59 | 120.4 (2) |
C72—O17—C71 | 106.3 (2) | C60—C59—C58 | 118.8 (2) |
C72—O18—C70 | 110.2 (2) | C60—C59—H59 | 120.6 |
C76—O19—C81 | 119.2 (2) | C58—C59—H59 | 120.6 |
C84—O20—C83 | 105.7 (2) | C59—C60—C61 | 122.6 (2) |
C82—O21—C84 | 109.0 (2) | C59—C60—H60 | 118.7 |
C80—O22—C87 | 116.4 (2) | C61—C60—H60 | 118.7 |
C90—O23—C89 | 105.8 (2) | C60—C61—C62 | 118.2 (2) |
C90—O24—C88 | 108.0 (2) | C60—C61—H61 | 120.9 |
C1—N1—C4 | 107.26 (17) | C62—C61—H61 | 120.9 |
C1—N1—Ru1 | 126.32 (16) | O16—C62—C61 | 124.2 (2) |
C4—N1—Ru1 | 126.27 (16) | O16—C62—C57 | 114.9 (2) |
C6—N2—C9 | 107.54 (19) | C61—C62—C57 | 120.9 (2) |
C6—N2—Ru1 | 126.23 (15) | O13—C63—C64 | 106.8 (2) |
C9—N2—Ru1 | 126.16 (15) | O13—C63—H63A | 110.4 |
C14—N3—C11 | 107.50 (17) | C64—C63—H63A | 110.4 |
C14—N3—Ru1 | 126.30 (16) | O13—C63—H63B | 110.4 |
C11—N3—Ru1 | 126.15 (16) | C64—C63—H63B | 110.4 |
C16—N4—C19 | 106.83 (19) | H63A—C63—H63B | 108.6 |
C16—N4—Ru1 | 126.41 (15) | O15—C64—C63 | 105.0 (2) |
C19—N4—Ru1 | 126.70 (15) | O15—C64—C65 | 101.5 (2) |
C93—N5—C94 | 163.9 (3) | C63—C64—C65 | 117.9 (2) |
C102—N6—C103 | 169.3 (3) | O15—C64—H64 | 110.6 |
N1—C1—C20 | 125.7 (2) | C63—C64—H64 | 110.6 |
N1—C1—C2 | 109.1 (2) | C65—C64—H64 | 110.6 |
C20—C1—C2 | 125.2 (2) | O14—C65—C64 | 102.6 (2) |
C3—C2—C1 | 107.1 (2) | O14—C65—H65A | 111.2 |
C3—C2—H2 | 126.4 | C64—C65—H65A | 111.2 |
C1—C2—H2 | 126.4 | O14—C65—H65B | 111.2 |
C2—C3—C4 | 107.6 (2) | C64—C65—H65B | 111.2 |
C2—C3—H3 | 126.2 | H65A—C65—H65B | 109.2 |
C4—C3—H3 | 126.2 | O15—C66—O14 | 107.0 (2) |
N1—C4—C5 | 125.2 (2) | O15—C66—C68 | 108.4 (2) |
N1—C4—C3 | 108.9 (2) | O14—C66—C68 | 109.1 (3) |
C5—C4—C3 | 125.9 (2) | O15—C66—C67 | 109.1 (2) |
C6—C5—C4 | 125.9 (2) | O14—C66—C67 | 110.2 (2) |
C6—C5—C21 | 116.7 (2) | C68—C66—C67 | 112.9 (3) |
C4—C5—C21 | 117.29 (19) | C66—C67—H67A | 109.5 |
N2—C6—C5 | 125.9 (2) | C66—C67—H67B | 109.5 |
N2—C6—C7 | 108.88 (19) | H67A—C67—H67B | 109.5 |
C5—C6—C7 | 125.2 (2) | C66—C67—H67C | 109.5 |
C8—C7—C6 | 107.2 (2) | H67A—C67—H67C | 109.5 |
C8—C7—H7 | 126.4 | H67B—C67—H67C | 109.5 |
C6—C7—H7 | 126.4 | C66—C68—H68A | 109.5 |
C7—C8—C9 | 107.5 (2) | C66—C68—H68B | 109.5 |
C7—C8—H8 | 126.3 | H68A—C68—H68B | 109.5 |
C9—C8—H8 | 126.3 | C66—C68—H68C | 109.5 |
N2—C9—C10 | 125.7 (2) | H68A—C68—H68C | 109.5 |
N2—C9—C8 | 108.86 (19) | H68B—C68—H68C | 109.5 |
C10—C9—C8 | 125.4 (2) | O16—C69—C70 | 110.1 (2) |
C9—C10—C11 | 126.0 (2) | O16—C69—H69A | 109.6 |
C9—C10—C39 | 117.2 (2) | C70—C69—H69A | 109.6 |
C11—C10—C39 | 116.66 (19) | O16—C69—H69B | 109.6 |
N3—C11—C10 | 125.6 (2) | C70—C69—H69B | 109.6 |
N3—C11—C12 | 109.0 (2) | H69A—C69—H69B | 108.2 |
C10—C11—C12 | 125.4 (2) | O18—C70—C69 | 108.2 (2) |
C13—C12—C11 | 107.3 (2) | O18—C70—C71 | 103.6 (2) |
C13—C12—H12 | 126.3 | C69—C70—C71 | 113.9 (3) |
C11—C12—H12 | 126.3 | O18—C70—H70 | 110.3 |
C12—C13—C14 | 107.2 (2) | C69—C70—H70 | 110.3 |
C12—C13—H13 | 126.4 | C71—C70—H70 | 110.3 |
C14—C13—H13 | 126.4 | O17—C71—C70 | 102.6 (2) |
N3—C14—C15 | 126.0 (2) | O17—C71—H71A | 111.2 |
N3—C14—C13 | 109.0 (2) | C70—C71—H71A | 111.2 |
C15—C14—C13 | 125.0 (2) | O17—C71—H71B | 111.2 |
C14—C15—C16 | 125.8 (2) | C70—C71—H71B | 111.2 |
C14—C15—C57 | 117.4 (2) | H71A—C71—H71B | 109.2 |
C16—C15—C57 | 116.7 (2) | O18—C72—O17 | 105.3 (2) |
N4—C16—C15 | 125.5 (2) | O18—C72—C73 | 108.7 (3) |
N4—C16—C17 | 109.43 (19) | O17—C72—C73 | 109.3 (3) |
C15—C16—C17 | 125.0 (2) | O18—C72—C74 | 108.8 (3) |
C18—C17—C16 | 107.1 (2) | O17—C72—C74 | 111.9 (3) |
C18—C17—H17 | 126.4 | C73—C72—C74 | 112.5 (3) |
C16—C17—H17 | 126.4 | C72—C73—H73A | 109.5 |
C17—C18—C19 | 107.5 (2) | C72—C73—H73B | 109.5 |
C17—C18—H18 | 126.2 | H73A—C73—H73B | 109.5 |
C19—C18—H18 | 126.2 | C72—C73—H73C | 109.5 |
N4—C19—C20 | 125.4 (2) | H73A—C73—H73C | 109.5 |
N4—C19—C18 | 109.10 (19) | H73B—C73—H73C | 109.5 |
C20—C19—C18 | 125.4 (2) | C72—C74—H74A | 109.5 |
C1—C20—C19 | 126.0 (2) | C72—C74—H74B | 109.5 |
C1—C20—C75 | 118.9 (2) | H74A—C74—H74B | 109.5 |
C19—C20—C75 | 115.1 (2) | C72—C74—H74C | 109.5 |
C26—C21—C22 | 117.9 (2) | H74A—C74—H74C | 109.5 |
C26—C21—C5 | 119.6 (2) | H74B—C74—H74C | 109.5 |
C22—C21—C5 | 122.5 (2) | C76—C75—C80 | 118.0 (2) |
O1—C22—C23 | 123.3 (2) | C76—C75—C20 | 119.4 (2) |
O1—C22—C21 | 116.0 (2) | C80—C75—C20 | 122.2 (2) |
C23—C22—C21 | 120.7 (2) | O19—C76—C75 | 115.0 (2) |
C24—C23—C22 | 119.9 (2) | O19—C76—C77 | 123.0 (2) |
C24—C23—H23 | 120.1 | C75—C76—C77 | 121.9 (2) |
C22—C23—H23 | 120.1 | C78—C77—C76 | 118.0 (3) |
C23—C24—C25 | 121.2 (2) | C78—C77—H77 | 121.0 |
C23—C24—H24 | 119.4 | C76—C77—H77 | 121.0 |
C25—C24—H24 | 119.4 | C77—C78—C79 | 122.6 (2) |
C24—C25—C26 | 118.8 (2) | C77—C78—H78 | 118.7 |
C24—C25—H25 | 120.6 | C79—C78—H78 | 118.7 |
C26—C25—H25 | 120.6 | C78—C79—C80 | 118.3 (2) |
O4—C26—C21 | 115.9 (2) | C78—C79—H79 | 120.9 |
O4—C26—C25 | 122.5 (2) | C80—C79—H79 | 120.9 |
C21—C26—C25 | 121.5 (2) | O22—C80—C75 | 114.6 (2) |
O1—C27—C28 | 105.1 (2) | O22—C80—C79 | 124.2 (2) |
O1—C27—H27A | 110.7 | C75—C80—C79 | 121.1 (2) |
C28—C27—H27A | 110.7 | O19—C81—C82 | 104.7 (2) |
O1—C27—H27B | 110.7 | O19—C81—H81A | 110.8 |
C28—C27—H27B | 110.7 | C82—C81—H81A | 110.8 |
H27A—C27—H27B | 108.8 | O19—C81—H81B | 110.8 |
O3—C28—C27 | 108.5 (2) | C82—C81—H81B | 110.8 |
O3—C28—C29 | 103.7 (2) | H81A—C81—H81B | 108.9 |
C27—C28—C29 | 114.1 (2) | O21—C82—C81 | 108.4 (2) |
O3—C28—H28 | 110.1 | O21—C82—C83 | 104.2 (2) |
C27—C28—H28 | 110.1 | C81—C82—C83 | 113.8 (2) |
C29—C28—H28 | 110.1 | O21—C82—H82 | 110.1 |
O2—C29—C28 | 103.6 (2) | C81—C82—H82 | 110.1 |
O2—C29—H29A | 111.0 | C83—C82—H82 | 110.1 |
C28—C29—H29A | 111.0 | O20—C83—C82 | 102.7 (2) |
O2—C29—H29B | 111.0 | O20—C83—H83A | 111.2 |
C28—C29—H29B | 111.0 | C82—C83—H83A | 111.2 |
H29A—C29—H29B | 109.0 | O20—C83—H83B | 111.2 |
O2—C30—O3 | 106.1 (2) | C82—C83—H83B | 111.2 |
O2—C30—C32 | 108.7 (2) | H83A—C83—H83B | 109.1 |
O3—C30—C32 | 108.9 (2) | O20—C84—O21 | 104.6 (2) |
O2—C30—C31 | 110.7 (2) | O20—C84—C85 | 112.3 (3) |
O3—C30—C31 | 109.0 (3) | O21—C84—C85 | 110.3 (3) |
C32—C30—C31 | 113.2 (2) | O20—C84—C86 | 107.8 (3) |
C30—C31—H31A | 109.5 | O21—C84—C86 | 107.6 (3) |
C30—C31—H31B | 109.5 | C85—C84—C86 | 113.7 (3) |
H31A—C31—H31B | 109.5 | C84—C85—H85A | 109.5 |
C30—C31—H31C | 109.5 | C84—C85—H85B | 109.5 |
H31A—C31—H31C | 109.5 | H85A—C85—H85B | 109.5 |
H31B—C31—H31C | 109.5 | C84—C85—H85C | 109.5 |
C30—C32—H32A | 109.5 | H85A—C85—H85C | 109.5 |
C30—C32—H32B | 109.5 | H85B—C85—H85C | 109.5 |
H32A—C32—H32B | 109.5 | C84—C86—H86A | 109.5 |
C30—C32—H32C | 109.5 | C84—C86—H86B | 109.5 |
H32A—C32—H32C | 109.5 | H86A—C86—H86B | 109.5 |
H32B—C32—H32C | 109.5 | C84—C86—H86C | 109.5 |
O4—C33—C34 | 110.6 (2) | H86A—C86—H86C | 109.5 |
O4—C33—H33A | 109.5 | H86B—C86—H86C | 109.5 |
C34—C33—H33A | 109.5 | O22—C87—C88 | 106.6 (2) |
O4—C33—H33B | 109.5 | O22—C87—H87A | 110.4 |
C34—C33—H33B | 109.5 | C88—C87—H87A | 110.4 |
H33A—C33—H33B | 108.1 | O22—C87—H87B | 110.4 |
O6—C34—C35 | 104.4 (2) | C88—C87—H87B | 110.4 |
O6—C34—C33 | 108.0 (2) | H87A—C87—H87B | 108.6 |
C35—C34—C33 | 114.3 (3) | O24—C88—C87 | 105.7 (2) |
O6—C34—H34 | 110.0 | O24—C88—C89 | 104.1 (2) |
C35—C34—H34 | 110.0 | C87—C88—C89 | 113.6 (2) |
C33—C34—H34 | 110.0 | O24—C88—H88 | 111.1 |
O5—C35—C34 | 103.6 (3) | C87—C88—H88 | 111.1 |
O5—C35—H35A | 111.0 | C89—C88—H88 | 111.1 |
C34—C35—H35A | 111.0 | O23—C89—C88 | 103.7 (2) |
O5—C35—H35B | 111.0 | O23—C89—H89A | 111.0 |
C34—C35—H35B | 111.0 | C88—C89—H89A | 111.0 |
H35A—C35—H35B | 109.0 | O23—C89—H89B | 111.0 |
O5—C36—O6 | 107.1 (2) | C88—C89—H89B | 111.0 |
O5—C36—C37 | 109.5 (4) | H89A—C89—H89B | 109.0 |
O6—C36—C37 | 107.0 (4) | O23—C90—O24 | 104.5 (2) |
O5—C36—C38 | 110.0 (4) | O23—C90—C92 | 109.9 (2) |
O6—C36—C38 | 107.2 (3) | O24—C90—C92 | 109.3 (2) |
C37—C36—C38 | 115.7 (5) | O23—C90—C91 | 112.5 (3) |
C36—C37—H37A | 109.5 | O24—C90—C91 | 109.1 (2) |
C36—C37—H37B | 109.5 | C92—C90—C91 | 111.3 (2) |
H37A—C37—H37B | 109.5 | C90—C91—H91A | 109.5 |
C36—C37—H37C | 109.5 | C90—C91—H91B | 109.5 |
H37A—C37—H37C | 109.5 | H91A—C91—H91B | 109.5 |
H37B—C37—H37C | 109.5 | C90—C91—H91C | 109.5 |
C36—C38—H38A | 109.5 | H91A—C91—H91C | 109.5 |
C36—C38—H38B | 109.5 | H91B—C91—H91C | 109.5 |
H38A—C38—H38B | 109.5 | C90—C92—H92A | 109.5 |
C36—C38—H38C | 109.5 | C90—C92—H92B | 109.5 |
H38A—C38—H38C | 109.5 | H92A—C92—H92B | 109.5 |
H38B—C38—H38C | 109.5 | C90—C92—H92C | 109.5 |
C40—C39—C44 | 118.8 (2) | H92A—C92—H92C | 109.5 |
C40—C39—C10 | 119.9 (2) | H92B—C92—H92C | 109.5 |
C44—C39—C10 | 121.3 (2) | N5—C93—Ru1 | 167.0 (2) |
O7—C40—C39 | 115.3 (2) | N5—C94—C101 | 108.0 (2) |
O7—C40—C41 | 123.9 (2) | N5—C94—C95 | 110.8 (2) |
C39—C40—C41 | 120.7 (2) | C101—C94—C95 | 112.6 (2) |
C42—C41—C40 | 118.7 (2) | N5—C94—H94 | 108.4 |
C42—C41—H41 | 120.6 | C101—C94—H94 | 108.4 |
C40—C41—H41 | 120.6 | C95—C94—H94 | 108.4 |
C43—C42—C41 | 121.7 (2) | C100—C95—C96 | 118.7 (3) |
C43—C42—H42 | 119.2 | C100—C95—C94 | 122.3 (2) |
C41—C42—H42 | 119.2 | C96—C95—C94 | 118.9 (2) |
C42—C43—C44 | 119.4 (2) | C97—C96—C95 | 120.9 (3) |
C42—C43—H43 | 120.3 | C97—C96—H96 | 119.6 |
C44—C43—H43 | 120.3 | C95—C96—H96 | 119.6 |
O10—C44—C43 | 123.9 (2) | C98—C97—C96 | 120.1 (3) |
O10—C44—C39 | 115.2 (2) | C98—C97—H97 | 120.0 |
C43—C44—C39 | 120.7 (2) | C96—C97—H97 | 120.0 |
O7—C45—C46 | 110.3 (2) | C97—C98—C99 | 119.9 (3) |
O7—C45—H45A | 109.6 | C97—C98—H98 | 120.0 |
C46—C45—H45A | 109.6 | C99—C98—H98 | 120.0 |
O7—C45—H45B | 109.6 | C98—C99—C100 | 120.0 (3) |
C46—C45—H45B | 109.6 | C98—C99—H99 | 120.0 |
H45A—C45—H45B | 108.1 | C100—C99—H99 | 120.0 |
O9—C46—C45 | 107.3 (2) | C95—C100—C99 | 120.4 (2) |
O9—C46—C47 | 103.5 (2) | C95—C100—H100 | 119.8 |
C45—C46—C47 | 113.8 (2) | C99—C100—H100 | 119.8 |
O9—C46—H46 | 110.6 | C94—C101—H10A | 109.5 |
C45—C46—H46 | 110.6 | C94—C101—H10B | 109.5 |
C47—C46—H46 | 110.6 | H10A—C101—H10B | 109.5 |
O8—C47—C46 | 103.1 (2) | C94—C101—H10C | 109.5 |
O8—C47—H47A | 111.1 | H10A—C101—H10C | 109.5 |
C46—C47—H47A | 111.1 | H10B—C101—H10C | 109.5 |
O8—C47—H47B | 111.1 | N6—C102—Ru1 | 178.2 (2) |
C46—C47—H47B | 111.1 | N6—C103—C104 | 109.8 (2) |
H47A—C47—H47B | 109.1 | N6—C103—C110 | 109.2 (2) |
O8—C48—O9 | 105.8 (2) | C104—C103—C110 | 113.0 (2) |
O8—C48—C50 | 112.1 (3) | N6—C103—H103 | 108.2 |
O9—C48—C50 | 109.5 (3) | C104—C103—H103 | 108.2 |
O8—C48—C49 | 107.7 (3) | C110—C103—H103 | 108.2 |
O9—C48—C49 | 108.9 (3) | C105—C104—C109 | 118.4 (3) |
C50—C48—C49 | 112.6 (3) | C105—C104—C103 | 124.2 (2) |
C48—C49—H49A | 109.5 | C109—C104—C103 | 117.4 (3) |
C48—C49—H49B | 109.5 | C104—C105—C106 | 121.1 (3) |
H49A—C49—H49B | 109.5 | C104—C105—H105 | 119.5 |
C48—C49—H49C | 109.5 | C106—C105—H105 | 119.5 |
H49A—C49—H49C | 109.5 | C105—C106—C107 | 120.1 (3) |
H49B—C49—H49C | 109.5 | C105—C106—H106 | 119.9 |
C48—C50—H50A | 109.5 | C107—C106—H106 | 119.9 |
C48—C50—H50B | 109.5 | C108—C107—C106 | 119.7 (3) |
H50A—C50—H50B | 109.5 | C108—C107—H107 | 120.2 |
C48—C50—H50C | 109.5 | C106—C107—H107 | 120.2 |
H50A—C50—H50C | 109.5 | C107—C108—C109 | 120.3 (3) |
H50B—C50—H50C | 109.5 | C107—C108—H108 | 119.8 |
O10—C51—C52 | 110.6 (2) | C109—C108—H108 | 119.8 |
O10—C51—H51A | 109.5 | C108—C109—C104 | 120.4 (3) |
C52—C51—H51A | 109.5 | C108—C109—H109 | 119.8 |
O10—C51—H51B | 109.5 | C104—C109—H109 | 119.8 |
C52—C51—H51B | 109.5 | C103—C110—H11A | 109.5 |
H51A—C51—H51B | 108.1 | C103—C110—H11B | 109.5 |
O12—C52—C53 | 102.5 (2) | H11A—C110—H11B | 109.5 |
O12—C52—C51 | 109.1 (2) | C103—C110—H11C | 109.5 |
C53—C52—C51 | 112.6 (2) | H11A—C110—H11C | 109.5 |
O12—C52—H52 | 110.8 | H11B—C110—H11C | 109.5 |
C53—C52—H52 | 110.8 |
Experimental details
Crystal data | |
Chemical formula | [Ru(C9H9N)2(C92H108N4O24)] |
Mr | 2017.24 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 110 |
a, b, c (Å) | 18.5099 (2), 15.0831 (2), 18.5766 (2) |
β (°) | 90.5023 (6) |
V (Å3) | 5186.14 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.38 × 0.28 × 0.25 |
Data collection | |
Diffractometer | Enraf-Nonius KappaCCD diffractometer |
Absorption correction | Analytical (de Meulenaer & Tompa, 1965; Alcock, 1970) |
Tmin, Tmax | 0.895, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 82451, 24735, 22116 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.103, 1.03 |
No. of reflections | 24735 |
No. of parameters | 1270 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.78, −0.78 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.039 (12); 11880 Friedel pairs |
Computer programs: KappaCCD Software (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1998), SHELXL97.
Ru1—C102 | 1.998 (3) | Ru1—N3 | 2.0581 (15) |
Ru1—C93 | 2.006 (2) | N5—C93 | 1.163 (3) |
Ru1—N2 | 2.051 (2) | N5—C94 | 1.451 (3) |
Ru1—N4 | 2.0522 (19) | N6—C102 | 1.157 (3) |
Ru1—N1 | 2.0549 (15) | N6—C103 | 1.440 (3) |
C102—Ru1—C93 | 175.02 (11) | C102—Ru1—N3 | 90.59 (9) |
C102—Ru1—N2 | 91.39 (9) | C93—Ru1—N3 | 88.73 (8) |
C93—Ru1—N2 | 83.69 (9) | N2—Ru1—N3 | 90.21 (8) |
C102—Ru1—N4 | 88.98 (9) | N4—Ru1—N3 | 89.86 (8) |
C93—Ru1—N4 | 95.95 (9) | N1—Ru1—N3 | 179.29 (7) |
N2—Ru1—N4 | 179.62 (9) | C93—N5—C94 | 163.9 (3) |
C102—Ru1—N1 | 88.81 (9) | C102—N6—C103 | 169.3 (3) |
C93—Ru1—N1 | 91.90 (8) | N5—C93—Ru1 | 167.0 (2) |
N2—Ru1—N1 | 90.17 (8) | N6—C102—Ru1 | 178.2 (2) |
N4—Ru1—N1 | 89.76 (8) |
During the past few years, we have been investigating the use of optically active ruthenium porphyrins in chiral recognition of racemic phosphines (Le Maux et al., 1991) and amino esters (Morice et al., 1998). A few isocyanide derivatives of iron porphyrins (Jameson & Ibers, 1979) and ruthenium porphyrins (Geze et al., 1992) have been described. However, no structural studies on ruthenium porphyrins bearing eight independent chiral pickets have been reported. The title compound, (I), was prepared as part as of a chiral recognition study of racemic isocyanides with metalloporphyrins (Galardon et al., 1999).
The porphyrin ring is nearly planar, with the Ru atom in the centre. The average Ru—Np bond distances [2.054 (2) Å; Np is an N atom of the porphyrin ring] falls within the range of distances reported for chiral porphyrins RuII complexes (Le Maux et al., 1995; Gross et al., 1996; Lo et al., 1997). This planarity is similar to that observed with (TPP)FeII(CNtBu)2 (TPP is triphenylphosphine; Jameson & Ibers, 1979). The Np—Ru—CCN angles vary between 83.7 and 95.9° (CCN is the isocyanide C atom), and the CCN—Ru—CCN angle is non-linear [175.02 (11)°]. A similar situation has been observed previously in (TPP)Fe(CNtBu)2 (Jameson & Ibers, 1979) and was imputed to crystal-packing effects. The Ru—CCN bond [average 2.002 (3) Å] is longer than the Ru—CO [1.77 (2) (Bonnet et al., 1973) and 1.79 (2) Å (Le Maux et al., 1995)] or Ru═C [1.829 (9) Å; Galardon et al., 1998] bonds of porphyrin–ruthenium complexes.
The C—N–R angles [169.3 (3) and 163.9 (3)°] of the isocyanide ligands in the complex are different from the value of 180° expected in the free ligand. This bending is close to that reported for (TPP)Fe(CNtBu)2 (Jameson & Ibers, 1979). The phenyl groups of the isocyanide are nearly perpendicular to one another, probably because of crystal-packing effects.
The rather high values of the displacement parameters of the chiral groups attached to the phenyl ring suggest a large motion of these groups (very large at room temperature, see below), as can also be seen in the crystal structure (Figs. 1 and 2), a relatively large cavity results since the chiral groups extend far above the porphyrin mean plane. Contrary to our expectation, only weak steric effects are present and may also explain the weak chiral recognition (Galardon et al., 1999).