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The geometry about the Ru atom in the title compound, [Ru(C9H9N)2(C92H108N4O24)], is approximately tetragonal and the porphyrin ring is nearly planar, while 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007952/gs1094sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007952/gs1094Isup2.hkl
Contains datablock I

CCDC reference: 150321

Comment top

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 RuC [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).

Experimental top

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.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids.
(I) top
Crystal data top
[Ru(C9H9N)2(C92H108N4O24)]F(000) = 2128
Mr = 2017.24Dx = 1.292 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71069 Å
a = 18.5099 (2) ÅCell parameters from 157703 reflections
b = 15.0831 (2) Åθ = 1.0–27.9°
c = 18.5766 (2) ŵ = 0.23 mm1
β = 90.5023 (6)°T = 110 K
V = 5186.14 (10) Å3Block, purple
Z = 20.38 × 0.28 × 0.25 mm
Data collection top
Enraf-Nonius KappaCCD
diffractometer
24735 independent reflections
Radiation source: fine-focus sealed tube22116 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 19.11 pixels mm-1θmax = 27.9°, θmin = 2.1°
Area–detector scans (see text)h = 2424
Absorption correction: analytical
(de Meulenaer & Tompa, 1965; Alcock, 1970)
k = 1919
Tmin = 0.895, Tmax = 0.932l = 2424
82451 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.039H-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 reflectionsΔρmax = 0.78 e Å3
1270 parametersΔρmin = 0.78 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.039 (12); 11880 Friedel pairs
Crystal data top
[Ru(C9H9N)2(C92H108N4O24)]V = 5186.14 (10) Å3
Mr = 2017.24Z = 2
Monoclinic, P21Mo Kα radiation
a = 18.5099 (2) ŵ = 0.23 mm1
b = 15.0831 (2) ÅT = 110 K
c = 18.5766 (2) Å0.38 × 0.28 × 0.25 mm
β = 90.5023 (6)°
Data collection top
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 = 0.932Rint = 0.000
82451 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.103Δρmax = 0.78 e Å3
S = 1.03Δρmin = 0.78 e Å3
24735 reflectionsAbsolute structure: Flack (1983)
1270 parametersAbsolute structure parameter: 0.039 (12); 11880 Friedel pairs
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru10.751749 (9)0.932404 (14)0.745875 (8)0.01592 (4)
O10.80517 (9)1.02513 (11)0.45832 (9)0.0266 (4)
O20.79289 (10)0.76721 (13)0.36453 (10)0.0334 (4)
O30.87141 (11)0.87271 (14)0.32525 (11)0.0427 (5)
O40.70496 (10)1.23733 (12)0.61286 (9)0.0271 (4)
O50.50595 (12)1.20616 (17)0.68425 (11)0.0496 (5)
O60.51990 (12)1.32027 (16)0.60516 (15)0.0577 (6)
O70.82490 (10)1.19519 (13)0.92321 (11)0.0313 (4)
O80.66899 (10)1.31709 (13)0.81340 (10)0.0361 (4)
O90.74542 (12)1.40873 (13)0.87484 (13)0.0479 (5)
O101.02369 (9)1.05688 (12)0.81714 (9)0.0273 (4)
O111.06698 (12)0.81458 (14)0.80523 (10)0.0408 (5)
O121.13681 (11)0.87915 (14)0.89287 (11)0.0397 (5)
O130.81075 (11)0.64262 (12)0.92168 (10)0.0305 (4)
O140.99219 (12)0.56099 (14)0.79536 (11)0.0452 (5)
O150.94537 (12)0.47732 (14)0.88687 (11)0.0425 (5)
O160.65073 (10)0.85912 (12)1.00172 (9)0.0311 (4)
O170.65515 (13)1.10374 (15)1.10142 (12)0.0481 (5)
O180.63013 (15)0.98279 (14)1.16867 (11)0.0516 (6)
O190.68324 (10)0.65242 (13)0.58916 (11)0.0324 (4)
O200.84952 (11)0.51425 (15)0.66895 (11)0.0421 (5)
O210.83717 (11)0.51898 (14)0.54813 (10)0.0413 (5)
O220.48064 (9)0.81166 (13)0.65903 (10)0.0319 (4)
O230.35161 (11)1.02424 (14)0.60975 (10)0.0389 (5)
O240.31420 (9)0.92625 (15)0.69239 (9)0.0359 (4)
N10.70220 (8)0.93131 (17)0.64645 (8)0.0163 (3)
N20.80617 (10)1.04588 (13)0.71884 (9)0.0178 (4)
N30.80014 (9)0.93353 (17)0.84604 (8)0.0174 (3)
N40.69776 (10)0.81836 (13)0.77255 (10)0.0182 (4)
N50.89664 (12)0.85270 (15)0.68610 (11)0.0293 (5)
N60.61961 (12)1.04122 (15)0.80552 (12)0.0304 (5)
C10.65203 (12)0.87051 (15)0.62231 (12)0.0188 (4)
C20.62579 (14)0.89745 (17)0.55176 (13)0.0242 (5)
H20.59140.86810.52370.029*
C30.66069 (14)0.97329 (18)0.53442 (13)0.0242 (5)
H30.65471.00570.49220.029*
C40.70912 (12)0.99481 (15)0.59351 (12)0.0186 (4)
C50.75597 (12)1.06776 (15)0.59667 (11)0.0183 (4)
C60.80212 (12)1.08928 (16)0.65429 (11)0.0190 (4)
C70.85284 (13)1.16287 (16)0.65532 (12)0.0215 (5)
H70.86121.20260.61800.026*
C80.88559 (13)1.16281 (16)0.72048 (12)0.0214 (5)
H80.92061.20260.73640.026*
C90.85624 (12)1.08960 (16)0.76104 (12)0.0194 (4)
C100.87507 (12)1.06763 (15)0.83179 (12)0.0198 (4)
C110.84854 (12)0.99537 (16)0.87107 (12)0.0199 (5)
C120.86776 (14)0.97419 (17)0.94447 (12)0.0222 (5)
H120.89971.00550.97380.027*
C130.83086 (14)0.90051 (16)0.96264 (12)0.0221 (5)
H130.83270.87151.00680.027*
C140.78781 (12)0.87509 (15)0.90057 (11)0.0189 (4)
C150.74154 (12)0.80193 (16)0.89757 (12)0.0205 (5)
C160.69989 (12)0.77599 (15)0.83795 (12)0.0182 (4)
C170.65223 (13)0.70074 (16)0.83603 (13)0.0234 (5)
H170.64350.66150.87360.028*
C180.62248 (13)0.69774 (16)0.76940 (12)0.0229 (5)
H180.59010.65540.75240.027*
C190.65012 (12)0.77197 (15)0.72961 (12)0.0196 (4)
C200.62945 (12)0.79549 (16)0.65957 (12)0.0197 (4)
C210.75388 (12)1.13169 (16)0.53436 (12)0.0204 (5)
C220.77841 (12)1.10892 (16)0.46560 (12)0.0227 (5)
C230.77619 (13)1.17047 (18)0.40931 (12)0.0271 (5)
H230.79151.15430.36360.033*
C240.75131 (13)1.25490 (18)0.42168 (13)0.0283 (5)
H240.75121.29600.38430.034*
C250.72640 (13)1.27991 (17)0.48866 (13)0.0282 (5)
H250.70951.33710.49650.034*
C260.72707 (13)1.21742 (17)0.54456 (12)0.0230 (5)
C270.82892 (15)0.99981 (19)0.38799 (14)0.0303 (6)
H27A0.87181.03270.37470.036*
H27B0.79141.01070.35230.036*
C280.84509 (15)0.90265 (18)0.39348 (14)0.0295 (6)
H280.88140.89200.43120.035*
C290.77898 (15)0.84505 (19)0.40623 (15)0.0335 (6)
H29A0.77420.83060.45690.040*
H29B0.73530.87450.38980.040*
C300.83208 (15)0.79575 (19)0.30314 (14)0.0338 (6)
C310.7808 (2)0.8208 (2)0.24213 (17)0.0512 (8)
H31A0.80820.83980.20130.061*
H31B0.74990.86810.25750.061*
H31C0.75200.77030.22910.061*
C320.88523 (17)0.7238 (2)0.28268 (16)0.0423 (7)
H32A0.91180.74210.24110.051*
H32B0.85940.67010.27200.051*
H32C0.91820.71350.32200.051*
C330.64633 (14)1.29806 (18)0.62154 (14)0.0308 (5)
H33A0.65691.35280.59630.037*
H33B0.64071.31180.67220.037*
C340.57663 (15)1.2587 (2)0.59212 (17)0.0375 (6)
H340.58101.24790.54030.045*
C350.55280 (19)1.1749 (2)0.6298 (2)0.0527 (8)
H35A0.52751.13560.59680.063*
H35B0.59381.14370.65050.063*
C360.47139 (18)1.2806 (3)0.65633 (19)0.0563 (9)
C370.4604 (5)1.3467 (5)0.7149 (4)0.151 (3)
H37A0.43651.39810.69570.182*
H37B0.50641.36360.73490.182*
H37C0.43121.32100.75190.182*
C380.4034 (2)1.2529 (4)0.6149 (3)0.0963 (19)
H38A0.37981.30460.59600.116*
H38B0.37131.22230.64670.116*
H38C0.41651.21440.57600.116*
C390.92581 (13)1.12923 (16)0.87089 (12)0.0207 (5)
C400.89830 (13)1.19600 (17)0.91483 (13)0.0249 (5)
C410.94493 (15)1.25479 (18)0.95106 (13)0.0291 (5)
H410.92651.30080.97880.035*
C421.01880 (15)1.24299 (18)0.94471 (13)0.0299 (6)
H421.04991.28070.96960.036*
C431.04730 (14)1.17692 (17)0.90251 (13)0.0258 (5)
H431.09711.17020.89900.031*
C441.00090 (13)1.12031 (16)0.86514 (12)0.0208 (5)
C450.78762 (15)1.2780 (2)0.93237 (15)0.0340 (6)
H45A0.81251.31350.96840.041*
H45B0.73901.26680.94910.041*
C460.78442 (15)1.32804 (18)0.86213 (15)0.0357 (6)
H460.83321.34090.84490.043*
C470.73958 (16)1.2817 (2)0.80340 (16)0.0382 (6)
H47A0.75761.29560.75590.046*
H47B0.73991.21790.80990.046*
C480.68002 (16)1.40735 (18)0.83336 (16)0.0370 (6)
C490.61788 (18)1.4346 (3)0.88111 (18)0.0549 (8)
H49A0.62391.49540.89530.066*
H49B0.61721.39760.92310.066*
H49C0.57321.42810.85510.066*
C500.6879 (2)1.4669 (2)0.76862 (19)0.0510 (8)
H50A0.69501.52700.78430.061*
H50B0.64491.46350.73940.061*
H50C0.72871.44820.74090.061*
C511.08808 (14)1.00826 (19)0.83257 (15)0.0300 (6)
H51A1.12351.04720.85480.036*
H51B1.10820.98590.78810.036*
C521.07227 (13)0.9307 (2)0.88318 (12)0.0306 (5)
H521.05450.95220.92950.037*
C531.02099 (16)0.86499 (19)0.85092 (15)0.0362 (6)
H53A0.99940.82800.88760.043*
H53B0.98300.89420.82350.043*
C541.13543 (18)0.8084 (2)0.84080 (15)0.0410 (7)
C551.1937 (2)0.8196 (3)0.7858 (2)0.0598 (10)
H55A1.24010.81560.80890.072*
H55B1.18880.87650.76310.072*
H55C1.18940.77380.75010.072*
C561.1410 (2)0.7190 (2)0.88039 (17)0.0517 (8)
H56A1.18700.71500.90450.062*
H56B1.13650.67150.84630.062*
H56C1.10300.71470.91510.062*
C570.73211 (13)0.74937 (16)0.96532 (12)0.0222 (5)
C580.76776 (13)0.66943 (17)0.97646 (13)0.0249 (5)
C590.75841 (14)0.62213 (18)1.04077 (14)0.0299 (5)
H590.78240.56881.04850.036*
C600.71304 (15)0.65611 (19)1.09219 (13)0.0326 (6)
H600.70710.62481.13490.039*
C610.67604 (15)0.73482 (19)1.08289 (13)0.0319 (6)
H610.64570.75641.11850.038*
C620.68543 (13)0.78119 (17)1.01862 (12)0.0251 (5)
C630.85663 (16)0.56721 (18)0.93646 (15)0.0350 (6)
H63A0.82810.51750.95320.042*
H63B0.89220.58190.97320.042*
C640.89305 (16)0.54426 (19)0.86774 (16)0.0366 (6)
H640.85800.52100.83270.044*
C650.94026 (17)0.6135 (2)0.83365 (16)0.0414 (7)
H65A0.91270.65100.80110.050*
H65B0.96360.65030.86980.050*
C660.99778 (15)0.4774 (2)0.83113 (14)0.0355 (6)
C670.98115 (17)0.4029 (2)0.77913 (16)0.0441 (7)
H67A1.01630.40270.74140.053*
H67B0.93380.41140.75870.053*
H67C0.98280.34730.80420.053*
C681.07179 (18)0.4695 (2)0.86531 (19)0.0503 (8)
H68A1.10780.46970.82840.060*
H68B1.07480.41510.89200.060*
H68C1.07980.51870.89720.060*
C690.61380 (15)0.90606 (19)1.05763 (14)0.0363 (6)
H69A0.58460.86501.08510.044*
H69B0.58190.95011.03640.044*
C700.66775 (17)0.9509 (2)1.10689 (14)0.0399 (7)
H700.70570.90911.12150.048*
C710.70140 (18)1.0350 (2)1.07491 (18)0.0449 (7)
H71A0.75071.04311.09170.054*
H71B0.70081.03321.02270.054*
C720.63349 (17)1.0766 (2)1.17161 (16)0.0398 (6)
C730.55921 (19)1.1119 (3)1.1865 (2)0.0647 (10)
H73A0.54471.09421.23380.078*
H73B0.52571.08871.15150.078*
H73C0.55981.17551.18360.078*
C740.6878 (2)1.1033 (3)1.2285 (2)0.0609 (10)
H74A0.67141.08391.27480.073*
H74B0.69301.16661.22860.073*
H74C0.73361.07631.21830.073*
C750.58028 (13)0.73079 (17)0.62228 (12)0.0223 (5)
C760.60962 (14)0.65535 (18)0.58999 (13)0.0265 (5)
C770.56599 (15)0.5876 (2)0.56175 (16)0.0352 (6)
H770.58630.53730.54120.042*
C780.49210 (15)0.59790 (19)0.56529 (15)0.0351 (6)
H780.46260.55370.54620.042*
C790.45997 (15)0.67152 (19)0.59612 (15)0.0330 (6)
H790.40990.67680.59770.040*
C800.50500 (13)0.73811 (17)0.62493 (13)0.0241 (5)
C810.71811 (15)0.57283 (18)0.56808 (15)0.0306 (6)
H81A0.70570.55760.51880.037*
H81B0.70450.52410.59920.037*
C820.79772 (14)0.59273 (18)0.57537 (14)0.0316 (5)
H820.80970.64640.54830.038*
C830.82375 (16)0.6015 (2)0.65288 (15)0.0380 (6)
H83A0.86220.64500.65710.046*
H83B0.78450.61810.68440.046*
C840.88143 (16)0.4830 (2)0.60483 (16)0.0349 (6)
C850.95815 (16)0.5139 (3)0.59708 (18)0.0497 (8)
H85A0.97760.49120.55300.060*
H85B0.98650.49270.63700.060*
H85C0.95940.57750.59620.060*
C860.8731 (2)0.3832 (2)0.6031 (2)0.0535 (9)
H86A0.89410.36040.55980.064*
H86B0.82270.36820.60410.064*
H86C0.89710.35780.64420.064*
C870.40431 (14)0.82652 (19)0.65648 (15)0.0314 (6)
H87A0.37920.78080.68320.038*
H87B0.38690.82580.60710.038*
C880.39150 (13)0.91597 (18)0.68989 (14)0.0328 (6)
H880.41290.91930.73820.039*
C890.41659 (16)0.9933 (2)0.64310 (18)0.0405 (7)
H89A0.43871.03940.67230.049*
H89B0.45100.97360.60740.049*
C900.29628 (15)1.00936 (18)0.66027 (14)0.0326 (6)
C910.29431 (18)1.0800 (2)0.71827 (16)0.0461 (7)
H91A0.25581.06740.75100.055*
H91B0.28641.13690.69650.055*
H91C0.33951.08050.74400.055*
C920.22475 (16)1.0017 (2)0.62220 (15)0.0417 (7)
H92A0.18740.99190.65680.050*
H92B0.22610.95280.58910.050*
H92C0.21501.05550.59620.050*
C930.83983 (13)0.87185 (15)0.70733 (11)0.0202 (5)
C940.96926 (14)0.8555 (2)0.65743 (14)0.0324 (6)
H941.00290.83470.69480.039*
C950.97579 (13)0.79524 (19)0.59258 (13)0.0302 (5)
C961.04274 (15)0.7584 (2)0.57695 (15)0.0391 (7)
H961.08170.76870.60780.047*
C971.05212 (16)0.7066 (2)0.51595 (15)0.0434 (7)
H971.09720.68230.50620.052*
C980.99486 (16)0.6913 (2)0.46995 (15)0.0373 (6)
H981.00140.65760.42860.045*
C990.92757 (15)0.72583 (19)0.48536 (14)0.0338 (6)
H990.88850.71430.45490.041*
C1000.91815 (14)0.77820 (19)0.54669 (14)0.0312 (5)
H1000.87290.80170.55670.037*
C1010.98705 (19)0.9512 (2)0.6402 (2)0.0522 (9)
H10A0.98220.98660.68290.063*
H10B0.95450.97260.60370.063*
H10C1.03580.95500.62320.063*
C1020.66865 (14)1.00265 (17)0.78342 (13)0.0241 (5)
C1030.55441 (15)1.07346 (19)0.83821 (15)0.0353 (6)
H1030.52671.10610.80170.042*
C1040.50877 (15)0.9956 (2)0.86348 (15)0.0335 (6)
C1050.53375 (16)0.9098 (2)0.86944 (16)0.0383 (7)
H1050.58120.89700.85710.046*
C1060.48923 (18)0.8422 (2)0.89358 (19)0.0490 (8)
H1060.50700.78470.89750.059*
C1070.41818 (18)0.8601 (2)0.91188 (19)0.0513 (8)
H1070.38830.81480.92790.062*
C1080.39232 (17)0.9450 (3)0.9062 (2)0.0559 (9)
H1080.34470.95720.91830.067*
C1090.43711 (17)1.0132 (2)0.88250 (19)0.0473 (8)
H1090.41931.07080.87930.057*
C1100.57418 (19)1.1377 (2)0.89899 (19)0.0501 (8)
H11A0.60291.18520.88010.060*
H11B0.60121.10680.93550.060*
H11C0.53081.16140.91950.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01537 (7)0.01588 (7)0.01646 (7)0.00036 (6)0.00208 (5)0.00057 (7)
O10.0313 (9)0.0287 (9)0.0200 (8)0.0036 (7)0.0018 (7)0.0025 (7)
O20.0332 (10)0.0344 (10)0.0325 (9)0.0033 (8)0.0046 (8)0.0064 (8)
O30.0417 (11)0.0411 (12)0.0457 (11)0.0139 (9)0.0183 (9)0.0199 (9)
O40.0311 (9)0.0272 (9)0.0231 (8)0.0079 (7)0.0014 (7)0.0001 (7)
O50.0422 (12)0.0671 (15)0.0398 (11)0.0058 (11)0.0095 (9)0.0042 (11)
O60.0340 (11)0.0513 (14)0.0881 (18)0.0116 (10)0.0162 (11)0.0147 (13)
O70.0267 (9)0.0286 (10)0.0387 (10)0.0017 (8)0.0004 (8)0.0070 (8)
O80.0385 (10)0.0307 (10)0.0391 (10)0.0041 (8)0.0024 (8)0.0013 (8)
O90.0482 (12)0.0296 (11)0.0658 (14)0.0078 (9)0.0116 (10)0.0116 (9)
O100.0242 (9)0.0280 (9)0.0294 (9)0.0021 (7)0.0049 (7)0.0047 (7)
O110.0519 (12)0.0371 (11)0.0332 (10)0.0070 (9)0.0003 (9)0.0058 (8)
O120.0411 (11)0.0384 (11)0.0393 (10)0.0120 (9)0.0074 (8)0.0009 (9)
O130.0341 (10)0.0275 (10)0.0299 (9)0.0093 (8)0.0007 (8)0.0024 (8)
O140.0566 (13)0.0395 (12)0.0397 (11)0.0105 (10)0.0060 (10)0.0083 (9)
O150.0508 (12)0.0352 (11)0.0417 (11)0.0135 (9)0.0116 (9)0.0046 (9)
O160.0348 (10)0.0336 (10)0.0249 (8)0.0075 (8)0.0027 (7)0.0002 (7)
O170.0548 (13)0.0387 (12)0.0509 (13)0.0056 (10)0.0076 (10)0.0047 (10)
O180.0892 (18)0.0324 (12)0.0338 (11)0.0029 (12)0.0213 (11)0.0059 (9)
O190.0198 (9)0.0281 (10)0.0493 (12)0.0021 (7)0.0011 (8)0.0147 (8)
O200.0425 (12)0.0461 (13)0.0376 (11)0.0001 (10)0.0064 (9)0.0024 (9)
O210.0416 (11)0.0471 (12)0.0350 (10)0.0196 (9)0.0097 (8)0.0109 (9)
O220.0163 (8)0.0350 (10)0.0444 (10)0.0006 (7)0.0026 (7)0.0088 (8)
O230.0450 (11)0.0380 (11)0.0340 (10)0.0057 (9)0.0112 (8)0.0056 (8)
O240.0264 (8)0.0392 (10)0.0422 (9)0.0091 (9)0.0078 (7)0.0089 (10)
N10.0148 (7)0.0175 (8)0.0166 (7)0.0010 (11)0.0033 (6)0.0008 (10)
N20.0161 (9)0.0209 (10)0.0164 (8)0.0005 (8)0.0000 (7)0.0006 (7)
N30.0177 (8)0.0172 (8)0.0171 (7)0.0000 (11)0.0006 (6)0.0007 (10)
N40.0168 (9)0.0174 (10)0.0205 (9)0.0003 (8)0.0021 (7)0.0003 (7)
N50.0274 (11)0.0360 (12)0.0245 (10)0.0067 (9)0.0017 (8)0.0001 (9)
N60.0265 (11)0.0322 (12)0.0325 (11)0.0087 (9)0.0025 (9)0.0015 (9)
C10.0149 (10)0.0200 (11)0.0214 (10)0.0007 (9)0.0026 (8)0.0029 (8)
C20.0212 (12)0.0298 (12)0.0215 (11)0.0042 (10)0.0048 (9)0.0000 (9)
C30.0260 (12)0.0278 (12)0.0187 (11)0.0008 (10)0.0078 (10)0.0026 (9)
C40.0164 (10)0.0210 (11)0.0183 (10)0.0018 (9)0.0019 (8)0.0008 (8)
C50.0175 (10)0.0203 (11)0.0172 (10)0.0009 (9)0.0007 (8)0.0007 (8)
C60.0204 (11)0.0190 (11)0.0177 (10)0.0004 (9)0.0005 (8)0.0003 (8)
C70.0249 (12)0.0187 (11)0.0209 (10)0.0057 (9)0.0012 (9)0.0011 (9)
C80.0223 (11)0.0204 (12)0.0215 (10)0.0031 (9)0.0010 (9)0.0009 (9)
C90.0182 (11)0.0198 (11)0.0203 (10)0.0008 (9)0.0003 (8)0.0022 (9)
C100.0205 (11)0.0185 (11)0.0202 (10)0.0011 (9)0.0032 (8)0.0037 (8)
C110.0195 (11)0.0233 (12)0.0170 (10)0.0021 (9)0.0025 (8)0.0024 (9)
C120.0258 (12)0.0230 (12)0.0178 (10)0.0032 (10)0.0051 (9)0.0000 (9)
C130.0259 (12)0.0246 (11)0.0159 (10)0.0001 (10)0.0034 (9)0.0017 (8)
C140.0189 (11)0.0207 (11)0.0169 (10)0.0015 (9)0.0009 (8)0.0004 (8)
C150.0210 (11)0.0195 (11)0.0209 (10)0.0036 (9)0.0006 (9)0.0019 (9)
C160.0175 (10)0.0173 (11)0.0196 (10)0.0001 (9)0.0007 (8)0.0007 (8)
C170.0237 (12)0.0207 (12)0.0259 (11)0.0010 (10)0.0015 (9)0.0044 (9)
C180.0222 (12)0.0202 (12)0.0262 (11)0.0041 (9)0.0014 (9)0.0023 (9)
C190.0189 (11)0.0175 (11)0.0224 (10)0.0001 (9)0.0018 (8)0.0023 (8)
C200.0162 (10)0.0206 (11)0.0225 (10)0.0003 (9)0.0004 (8)0.0018 (9)
C210.0195 (11)0.0238 (12)0.0180 (10)0.0023 (9)0.0017 (8)0.0045 (9)
C220.0199 (11)0.0263 (12)0.0219 (10)0.0014 (9)0.0031 (8)0.0011 (9)
C230.0241 (12)0.0400 (15)0.0173 (10)0.0032 (11)0.0002 (9)0.0035 (10)
C240.0233 (12)0.0352 (14)0.0264 (12)0.0002 (10)0.0023 (9)0.0107 (10)
C250.0295 (12)0.0249 (12)0.0302 (12)0.0046 (10)0.0026 (10)0.0065 (10)
C260.0215 (11)0.0255 (12)0.0218 (10)0.0008 (9)0.0000 (9)0.0026 (9)
C270.0301 (13)0.0357 (15)0.0251 (12)0.0017 (11)0.0049 (10)0.0041 (11)
C280.0276 (13)0.0311 (14)0.0300 (12)0.0013 (10)0.0049 (10)0.0056 (10)
C290.0297 (13)0.0327 (14)0.0383 (14)0.0001 (11)0.0053 (11)0.0050 (11)
C300.0375 (14)0.0333 (14)0.0306 (13)0.0059 (12)0.0021 (11)0.0071 (11)
C310.059 (2)0.055 (2)0.0394 (16)0.0081 (17)0.0052 (14)0.0074 (15)
C320.0493 (17)0.0371 (16)0.0407 (15)0.0014 (13)0.0103 (13)0.0079 (13)
C330.0338 (13)0.0259 (12)0.0327 (13)0.0049 (11)0.0041 (11)0.0042 (10)
C340.0280 (13)0.0410 (16)0.0436 (16)0.0035 (12)0.0051 (12)0.0011 (13)
C350.0456 (18)0.0463 (19)0.066 (2)0.0066 (15)0.0190 (16)0.0046 (16)
C360.0425 (18)0.073 (2)0.0534 (19)0.0156 (17)0.0201 (15)0.0119 (18)
C370.228 (8)0.106 (5)0.122 (5)0.072 (6)0.088 (5)0.018 (4)
C380.039 (2)0.131 (5)0.119 (4)0.006 (2)0.004 (2)0.072 (4)
C390.0241 (12)0.0208 (12)0.0172 (10)0.0054 (9)0.0026 (9)0.0015 (9)
C400.0266 (12)0.0243 (12)0.0237 (11)0.0023 (10)0.0038 (9)0.0002 (9)
C410.0353 (14)0.0258 (13)0.0262 (12)0.0040 (11)0.0041 (10)0.0077 (10)
C420.0348 (14)0.0268 (13)0.0278 (12)0.0106 (11)0.0094 (10)0.0011 (10)
C430.0249 (12)0.0281 (13)0.0242 (11)0.0065 (10)0.0066 (9)0.0039 (10)
C440.0217 (11)0.0216 (11)0.0191 (10)0.0028 (9)0.0031 (8)0.0029 (9)
C450.0327 (14)0.0325 (15)0.0369 (14)0.0042 (12)0.0012 (11)0.0122 (12)
C460.0346 (14)0.0276 (13)0.0450 (15)0.0012 (11)0.0018 (12)0.0052 (11)
C470.0417 (15)0.0334 (15)0.0395 (15)0.0089 (12)0.0011 (12)0.0035 (12)
C480.0352 (14)0.0303 (14)0.0456 (15)0.0058 (11)0.0001 (12)0.0029 (11)
C490.0547 (18)0.0522 (18)0.0580 (17)0.007 (2)0.0140 (15)0.005 (2)
C500.062 (2)0.0365 (16)0.0542 (19)0.0113 (15)0.0124 (16)0.0046 (14)
C510.0223 (12)0.0324 (14)0.0354 (13)0.0012 (11)0.0010 (10)0.0023 (11)
C520.0339 (12)0.0315 (12)0.0263 (10)0.0076 (13)0.0002 (9)0.0005 (13)
C530.0407 (15)0.0308 (14)0.0371 (14)0.0026 (12)0.0052 (12)0.0011 (11)
C540.0574 (18)0.0344 (15)0.0314 (14)0.0113 (14)0.0085 (13)0.0028 (11)
C550.067 (2)0.055 (2)0.058 (2)0.0202 (18)0.0272 (18)0.0118 (17)
C560.077 (2)0.0366 (16)0.0416 (16)0.0184 (16)0.0076 (16)0.0077 (13)
C570.0244 (12)0.0208 (11)0.0212 (10)0.0047 (9)0.0039 (9)0.0011 (9)
C580.0254 (12)0.0254 (12)0.0238 (11)0.0027 (9)0.0030 (9)0.0028 (9)
C590.0317 (13)0.0255 (13)0.0323 (13)0.0034 (10)0.0081 (10)0.0073 (10)
C600.0337 (14)0.0401 (15)0.0240 (12)0.0110 (12)0.0017 (10)0.0106 (11)
C610.0343 (14)0.0388 (15)0.0225 (11)0.0056 (12)0.0021 (10)0.0043 (11)
C620.0240 (11)0.0303 (13)0.0211 (11)0.0027 (10)0.0008 (9)0.0019 (9)
C630.0397 (15)0.0238 (13)0.0415 (15)0.0064 (11)0.0054 (12)0.0002 (11)
C640.0371 (15)0.0305 (14)0.0420 (15)0.0037 (12)0.0049 (12)0.0060 (12)
C650.0450 (16)0.0384 (16)0.0406 (15)0.0068 (13)0.0016 (13)0.0030 (12)
C660.0375 (15)0.0408 (15)0.0281 (13)0.0058 (12)0.0016 (11)0.0066 (11)
C670.0458 (17)0.0492 (18)0.0374 (15)0.0079 (14)0.0032 (13)0.0014 (12)
C680.0492 (18)0.0528 (19)0.0487 (18)0.0014 (15)0.0107 (15)0.0075 (15)
C690.0352 (14)0.0402 (16)0.0336 (13)0.0064 (11)0.0062 (11)0.0028 (11)
C700.0471 (16)0.044 (2)0.0283 (12)0.0040 (13)0.0046 (11)0.0048 (12)
C710.0455 (17)0.0412 (17)0.0483 (17)0.0015 (14)0.0104 (14)0.0015 (14)
C720.0437 (16)0.0342 (15)0.0414 (15)0.0009 (13)0.0032 (13)0.0037 (12)
C730.0449 (19)0.075 (3)0.074 (3)0.0161 (18)0.0067 (17)0.001 (2)
C740.052 (2)0.073 (3)0.058 (2)0.0031 (19)0.0014 (17)0.0157 (19)
C750.0215 (12)0.0254 (13)0.0200 (10)0.0018 (10)0.0046 (9)0.0031 (9)
C760.0265 (12)0.0260 (13)0.0270 (12)0.0020 (10)0.0012 (10)0.0050 (10)
C770.0310 (14)0.0313 (15)0.0434 (15)0.0026 (11)0.0030 (12)0.0127 (12)
C780.0330 (14)0.0290 (14)0.0432 (15)0.0090 (11)0.0076 (12)0.0093 (12)
C790.0224 (13)0.0363 (15)0.0400 (14)0.0058 (11)0.0066 (11)0.0043 (12)
C800.0225 (12)0.0239 (12)0.0259 (11)0.0018 (10)0.0045 (9)0.0024 (9)
C810.0342 (14)0.0255 (13)0.0322 (13)0.0050 (11)0.0002 (11)0.0064 (10)
C820.0309 (13)0.0314 (13)0.0324 (13)0.0060 (11)0.0007 (10)0.0029 (11)
C830.0366 (15)0.0412 (16)0.0363 (14)0.0012 (12)0.0031 (12)0.0080 (12)
C840.0329 (14)0.0352 (16)0.0366 (15)0.0059 (12)0.0039 (12)0.0017 (12)
C850.0354 (15)0.063 (2)0.0505 (18)0.0017 (15)0.0027 (13)0.0239 (16)
C860.057 (2)0.0386 (18)0.064 (2)0.0058 (16)0.0085 (18)0.0019 (17)
C870.0201 (12)0.0341 (15)0.0399 (14)0.0012 (11)0.0004 (10)0.0003 (12)
C880.0254 (12)0.0391 (17)0.0341 (12)0.0032 (10)0.0027 (10)0.0009 (11)
C890.0367 (15)0.0336 (15)0.0513 (17)0.0009 (12)0.0108 (13)0.0032 (13)
C900.0379 (14)0.0333 (14)0.0265 (12)0.0097 (11)0.0030 (10)0.0023 (10)
C910.0482 (18)0.052 (2)0.0382 (15)0.0088 (15)0.0015 (13)0.0095 (14)
C920.0432 (16)0.0509 (18)0.0311 (13)0.0128 (14)0.0004 (12)0.0020 (12)
C930.0263 (12)0.0190 (11)0.0152 (10)0.0030 (9)0.0035 (9)0.0014 (8)
C940.0219 (12)0.0463 (17)0.0291 (12)0.0049 (11)0.0027 (10)0.0023 (11)
C950.0267 (12)0.0390 (15)0.0250 (11)0.0041 (11)0.0034 (10)0.0037 (10)
C960.0273 (13)0.0589 (19)0.0311 (13)0.0134 (13)0.0010 (11)0.0015 (13)
C970.0346 (15)0.059 (2)0.0365 (14)0.0227 (14)0.0087 (12)0.0039 (14)
C980.0426 (16)0.0402 (16)0.0293 (12)0.0117 (13)0.0069 (11)0.0006 (11)
C990.0341 (14)0.0376 (15)0.0298 (12)0.0042 (12)0.0029 (11)0.0006 (11)
C1000.0252 (12)0.0383 (14)0.0301 (12)0.0056 (11)0.0038 (10)0.0033 (11)
C1010.0437 (17)0.055 (3)0.0577 (19)0.0137 (15)0.0121 (15)0.0146 (16)
C1020.0283 (13)0.0219 (12)0.0220 (11)0.0036 (10)0.0035 (10)0.0001 (9)
C1030.0298 (13)0.0369 (15)0.0394 (14)0.0138 (11)0.0079 (11)0.0014 (12)
C1040.0306 (14)0.0393 (16)0.0307 (13)0.0092 (12)0.0028 (11)0.0020 (11)
C1050.0331 (14)0.0381 (18)0.0439 (15)0.0090 (12)0.0070 (12)0.0024 (12)
C1060.0422 (17)0.0408 (17)0.064 (2)0.0049 (14)0.0127 (15)0.0007 (15)
C1070.0414 (17)0.053 (2)0.060 (2)0.0055 (15)0.0143 (15)0.0018 (16)
C1080.0377 (16)0.061 (2)0.069 (2)0.0084 (16)0.0214 (15)0.0030 (19)
C1090.0354 (16)0.0472 (18)0.060 (2)0.0114 (14)0.0144 (14)0.0022 (15)
C1100.056 (2)0.0392 (17)0.0551 (19)0.0015 (15)0.0212 (16)0.0136 (14)
Geometric parameters (Å, º) top
Ru1—C1021.998 (3)C43—C441.392 (3)
Ru1—C932.006 (2)C43—H430.9300
Ru1—N22.051 (2)C45—C461.508 (4)
Ru1—N42.0522 (19)C45—H45A0.9700
Ru1—N12.0549 (15)C45—H45B0.9700
Ru1—N32.0581 (15)C46—C471.534 (4)
O1—C221.363 (3)C46—H460.9800
O1—C271.434 (3)C47—H47A0.9700
O2—C301.424 (3)C47—H47B0.9700
O2—C291.431 (3)C48—C501.509 (4)
O3—C301.429 (3)C48—C491.515 (4)
O3—C281.435 (3)C49—H49A0.9600
O4—C261.370 (3)C49—H49B0.9600
O4—C331.430 (3)C49—H49C0.9600
O5—C361.390 (4)C50—H50A0.9600
O5—C351.419 (4)C50—H50B0.9600
O6—C341.425 (4)C50—H50C0.9600
O6—C361.443 (4)C51—C521.531 (4)
O7—C401.369 (3)C51—H51A0.9700
O7—C451.438 (3)C51—H51B0.9700
O8—C471.425 (3)C52—C531.494 (4)
O8—C481.425 (3)C52—H520.9800
O9—C481.429 (4)C53—H53A0.9700
O9—C461.436 (3)C53—H53B0.9700
O10—C441.377 (3)C54—C551.502 (4)
O10—C511.426 (3)C54—C561.538 (4)
O11—C531.427 (3)C55—H55A0.9600
O11—C541.427 (4)C55—H55B0.9600
O12—C521.435 (3)C55—H55C0.9600
O12—C541.441 (4)C56—H56A0.9600
O13—C581.359 (3)C56—H56B0.9600
O13—C631.444 (3)C56—H56C0.9600
O14—C661.429 (3)C57—C581.389 (4)
O14—C651.439 (4)C57—C621.404 (3)
O15—C661.425 (3)C58—C591.404 (3)
O15—C641.441 (3)C59—C601.376 (4)
O16—C621.375 (3)C59—H590.9300
O16—C691.435 (3)C60—C611.381 (4)
O17—C721.427 (4)C60—H600.9300
O17—C711.434 (4)C61—C621.396 (3)
O18—C721.418 (4)C61—H610.9300
O18—C701.431 (3)C63—C641.490 (4)
O19—C761.364 (3)C63—H63A0.9700
O19—C811.420 (3)C63—H63B0.9700
O20—C841.415 (4)C64—C651.505 (4)
O20—C831.430 (4)C64—H640.9800
O21—C821.426 (3)C65—H65A0.9700
O21—C841.435 (3)C65—H65B0.9700
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O22—C871.431 (3)C66—C671.512 (4)
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N1—C11.377 (3)C68—H68B0.9600
N1—C41.380 (3)C68—H68C0.9600
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N2—C91.377 (3)C69—H69A0.9700
N3—C141.364 (3)C69—H69B0.9700
N3—C111.372 (3)C70—C711.536 (4)
N4—C161.373 (3)C70—H700.9800
N4—C191.375 (3)C71—H71A0.9700
N5—C931.163 (3)C71—H71B0.9700
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N6—C1021.157 (3)C72—C741.507 (5)
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C1—C201.393 (3)C73—H73B0.9600
C1—C21.452 (3)C73—H73C0.9600
C2—C31.354 (4)C74—H74A0.9600
C2—H20.9300C74—H74B0.9600
C3—C41.448 (3)C74—H74C0.9600
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C4—C51.402 (3)C75—C801.399 (3)
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C7—H70.9300C78—H780.9300
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C10—C391.504 (3)C81—H81B0.9700
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C12—H120.9300C83—H83A0.9700
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C23—C241.374 (4)C89—H89B0.9700
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C25—C261.402 (3)C91—H91B0.9600
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C27—H27A0.9700C92—H92B0.9600
C27—H27B0.9700C92—H92C0.9600
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C28—H280.9800C94—C951.515 (4)
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C31—H31B0.9600C97—C981.375 (4)
C31—H31C0.9600C97—H970.9300
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C32—H32B0.9600C98—H980.9300
C32—H32C0.9600C99—C1001.398 (4)
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C33—H33B0.9700C101—H10A0.9600
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C35—H35B0.9700C103—C1101.530 (4)
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C38—H38B0.9600C106—H1060.9300
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C102—Ru1—N488.98 (9)C52—C53—H53A111.3
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N2—Ru1—N4179.62 (9)C52—C53—H53B111.3
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N1—Ru1—N3179.29 (7)C54—C55—H55B109.5
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C30—O3—C28109.5 (2)H55A—C55—H55C109.5
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C36—O5—C35106.5 (3)C54—C56—H56A109.5
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C48—O9—C46108.9 (2)H56A—C56—H56C109.5
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C28—C27—H27B110.7C82—C81—H81A110.8
H27A—C27—H27B108.8O19—C81—H81B110.8
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C27—C28—H28110.1C81—C82—C83113.8 (2)
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C28—C29—H29B111.0C82—C83—H83A111.2
H29A—C29—H29B109.0O20—C83—H83B111.2
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C30—C31—H31C109.5C84—C85—H85B109.5
H31A—C31—H31C109.5H85A—C85—H85B109.5
H31B—C31—H31C109.5C84—C85—H85C109.5
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C34—C33—H33B109.5C88—C87—H87A110.4
H33A—C33—H33B108.1O22—C87—H87B110.4
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C35—C34—H34110.0C87—C88—C89113.6 (2)
C33—C34—H34110.0O24—C88—H88111.1
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O5—C35—H35A111.0C89—C88—H88111.1
C34—C35—H35A111.0O23—C89—C88103.7 (2)
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C34—C35—H35B111.0C88—C89—H89A111.0
H35A—C35—H35B109.0O23—C89—H89B111.0
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O6—C36—C37107.0 (4)O23—C90—O24104.5 (2)
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O6—C36—C38107.2 (3)O24—C90—C92109.3 (2)
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C36—C37—H37A109.5O24—C90—C91109.1 (2)
C36—C37—H37B109.5C92—C90—C91111.3 (2)
H37A—C37—H37B109.5C90—C91—H91A109.5
C36—C37—H37C109.5C90—C91—H91B109.5
H37A—C37—H37C109.5H91A—C91—H91B109.5
H37B—C37—H37C109.5C90—C91—H91C109.5
C36—C38—H38A109.5H91A—C91—H91C109.5
C36—C38—H38B109.5H91B—C91—H91C109.5
H38A—C38—H38B109.5C90—C92—H92A109.5
C36—C38—H38C109.5C90—C92—H92B109.5
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H38B—C38—H38C109.5C90—C92—H92C109.5
C40—C39—C44118.8 (2)H92A—C92—H92C109.5
C40—C39—C10119.9 (2)H92B—C92—H92C109.5
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C42—C41—C40118.7 (2)N5—C94—H94108.4
C42—C41—H41120.6C101—C94—H94108.4
C40—C41—H41120.6C95—C94—H94108.4
C43—C42—C41121.7 (2)C100—C95—C96118.7 (3)
C43—C42—H42119.2C100—C95—C94122.3 (2)
C41—C42—H42119.2C96—C95—C94118.9 (2)
C42—C43—C44119.4 (2)C97—C96—C95120.9 (3)
C42—C43—H43120.3C97—C96—H96119.6
C44—C43—H43120.3C95—C96—H96119.6
O10—C44—C43123.9 (2)C98—C97—C96120.1 (3)
O10—C44—C39115.2 (2)C98—C97—H97120.0
C43—C44—C39120.7 (2)C96—C97—H97120.0
O7—C45—C46110.3 (2)C97—C98—C99119.9 (3)
O7—C45—H45A109.6C97—C98—H98120.0
C46—C45—H45A109.6C99—C98—H98120.0
O7—C45—H45B109.6C98—C99—C100120.0 (3)
C46—C45—H45B109.6C98—C99—H99120.0
H45A—C45—H45B108.1C100—C99—H99120.0
O9—C46—C45107.3 (2)C95—C100—C99120.4 (2)
O9—C46—C47103.5 (2)C95—C100—H100119.8
C45—C46—C47113.8 (2)C99—C100—H100119.8
O9—C46—H46110.6C94—C101—H10A109.5
C45—C46—H46110.6C94—C101—H10B109.5
C47—C46—H46110.6H10A—C101—H10B109.5
O8—C47—C46103.1 (2)C94—C101—H10C109.5
O8—C47—H47A111.1H10A—C101—H10C109.5
C46—C47—H47A111.1H10B—C101—H10C109.5
O8—C47—H47B111.1N6—C102—Ru1178.2 (2)
C46—C47—H47B111.1N6—C103—C104109.8 (2)
H47A—C47—H47B109.1N6—C103—C110109.2 (2)
O8—C48—O9105.8 (2)C104—C103—C110113.0 (2)
O8—C48—C50112.1 (3)N6—C103—H103108.2
O9—C48—C50109.5 (3)C104—C103—H103108.2
O8—C48—C49107.7 (3)C110—C103—H103108.2
O9—C48—C49108.9 (3)C105—C104—C109118.4 (3)
C50—C48—C49112.6 (3)C105—C104—C103124.2 (2)
C48—C49—H49A109.5C109—C104—C103117.4 (3)
C48—C49—H49B109.5C104—C105—C106121.1 (3)
H49A—C49—H49B109.5C104—C105—H105119.5
C48—C49—H49C109.5C106—C105—H105119.5
H49A—C49—H49C109.5C105—C106—C107120.1 (3)
H49B—C49—H49C109.5C105—C106—H106119.9
C48—C50—H50A109.5C107—C106—H106119.9
C48—C50—H50B109.5C108—C107—C106119.7 (3)
H50A—C50—H50B109.5C108—C107—H107120.2
C48—C50—H50C109.5C106—C107—H107120.2
H50A—C50—H50C109.5C107—C108—C109120.3 (3)
H50B—C50—H50C109.5C107—C108—H108119.8
O10—C51—C52110.6 (2)C109—C108—H108119.8
O10—C51—H51A109.5C108—C109—C104120.4 (3)
C52—C51—H51A109.5C108—C109—H109119.8
O10—C51—H51B109.5C104—C109—H109119.8
C52—C51—H51B109.5C103—C110—H11A109.5
H51A—C51—H51B108.1C103—C110—H11B109.5
O12—C52—C53102.5 (2)H11A—C110—H11B109.5
O12—C52—C51109.1 (2)C103—C110—H11C109.5
C53—C52—C51112.6 (2)H11A—C110—H11C109.5
O12—C52—H52110.8H11B—C110—H11C109.5
C53—C52—H52110.8

Experimental details

Crystal data
Chemical formula[Ru(C9H9N)2(C92H108N4O24)]
Mr2017.24
Crystal system, space groupMonoclinic, P21
Temperature (K)110
a, b, c (Å)18.5099 (2), 15.0831 (2), 18.5766 (2)
β (°) 90.5023 (6)
V3)5186.14 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.38 × 0.28 × 0.25
Data collection
DiffractometerEnraf-Nonius KappaCCD
diffractometer
Absorption correctionAnalytical
(de Meulenaer & Tompa, 1965; Alcock, 1970)
Tmin, Tmax0.895, 0.932
No. of measured, independent and
observed [I > 2σ(I)] reflections
82451, 24735, 22116
Rint0.000
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.103, 1.03
No. of reflections24735
No. of parameters1270
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.78, 0.78
Absolute structureFlack (1983)
Absolute structure parameter0.039 (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.

Selected geometric parameters (Å, º) top
Ru1—C1021.998 (3)Ru1—N32.0581 (15)
Ru1—C932.006 (2)N5—C931.163 (3)
Ru1—N22.051 (2)N5—C941.451 (3)
Ru1—N42.0522 (19)N6—C1021.157 (3)
Ru1—N12.0549 (15)N6—C1031.440 (3)
C102—Ru1—C93175.02 (11)C102—Ru1—N390.59 (9)
C102—Ru1—N291.39 (9)C93—Ru1—N388.73 (8)
C93—Ru1—N283.69 (9)N2—Ru1—N390.21 (8)
C102—Ru1—N488.98 (9)N4—Ru1—N389.86 (8)
C93—Ru1—N495.95 (9)N1—Ru1—N3179.29 (7)
N2—Ru1—N4179.62 (9)C93—N5—C94163.9 (3)
C102—Ru1—N188.81 (9)C102—N6—C103169.3 (3)
C93—Ru1—N191.90 (8)N5—C93—Ru1167.0 (2)
N2—Ru1—N190.17 (8)N6—C102—Ru1178.2 (2)
N4—Ru1—N189.76 (8)
 

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