metal-organic compounds
(1,6,7,12-Tetraazaperylene-κ2N,N′)bis(4,4′,5,5′-tetramethyl-2,2′-bipyridyl-κ2N,N′)ruthenium(II) bis(hexafluoridophosphate) acetonitrile trisolvate
aUniversität Potsdam, Institut für Chemie, Anorganische Chemie, Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam, Germany
*Correspondence e-mail: us@chem.uni-potsdam.de
In the title compound, rac-[Ru(C14H16N2)2(C16H8N4)](PF6)2·3C2H3N, discrete dimers of complex cations, [Ru(tmbpy)2tape]2+, of opposite are formed (tmbpy = tetramethylbipyridine; tape = tetraazaperylene), held together by π–π stacking interactions between the tetraazaperylene moieties with centroid–centroid distances in the range 3.563 (3)–3.837 (3) Å. These interactions exhibit a parallel displaced π–π stacking mode. Additional weak C—H⋯π-ring and C—H⋯N and C—H⋯F interactions are found, leading to a three-dimensional architecture. The RuII atom is coordinated in a distorted octahedral geometry. The counter-charge is provided by two hexafluoridophosphate anions and the is completed by three acetonitrile solvent molecules of crystallization. Four F atoms of one PF6− anion are disordered over three sets of sites with occupancies of 0.517 (3):0.244 (3):0.239 (3). Two acetonitrile solvent molecules are highly disordered and their estimated scattering contribution was subtracted from the observed diffraction data using the SQUEEZE option in PLATON [Spek (2009). Acta Cryst. D65, 148–155].
CCDC reference: 1004679
Related literature
For related RuII complexes with tape and bpy-type ligands, see: Brietzke et al. (2012). For background to the alkaloid eilatin, see: Rudia et al. (1988). For RuII complexes including eilatin-type ligands, see: Gut et al. (2002); Bergman et al. (2004, 2005).
Experimental
Crystal data
|
|
Data collection: X-AREA (Stoe & Cie, 2011); cell X-AREA; data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1004679
10.1107/S1600536814011969/tk5315sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814011969/tk5315Isup2.hkl
The ligand 1,6,7,12-tetraazaperylene (tape) is a D2h-symmetric bis(α,α'-diimine) ligand containing an extended π-heteroaromatic system. Tape is closely related to the well known ligand 2,2'-bipyrimidine (bpym). However, building supramolecular structures by π–π stacking interactions is an additional feature for complexes containing terminal tape ligands. Such behavior was described for RuII and OsII complexes of eilatin (dibenzo-[b,n]-1,6,7,12-tetraazaperylene) (Gut et al., 2002), isoeilatin (dibenzo-[b,k]-1,6,7,12-tetraazaperylene) (Bergman et al., 2005) and dibenzoeilatin (tetrabenzo-[b,e,k,n]-1,6,7,12-tetraazaperylene) (Bergman et al., 2004). Eilatin, an alkaloid first isolated from a Red Sea tunicate (Rudia et al., 1988), isoeilatin and dibenzoeilatin all have a tape core, mainly determining the electronic properties of these large surface ligands (Bergman et al., 2005). The synthesis of tape, as uncoordinated ligand, was first published in 2012 by our workgroup (Brietzke et al., 2012). In the same article, we compared UV-Vis absorption spectra, redox properties as well as structures for RuII complexes of the formula [Ru(L–L)tape]2+ (with L–L = phen, bpy, dmbpy (4,4'-dimethyl-2,2'-bipyridine), dtbbpy (4,4'-di-tert-butyl-2,2'-bipyridine) and tmbpy (4,4'5,5'-tetramethyl-2,2'-bipyridine)). However, we could not present the structures of the RuII complexes with L–L = phen and tmpby in this first report, because there were no crystals suitable for X-ray diffraction. To fill one part of this gap, we present herein the structure of rac-[Ru(tmbpy)2tape](PF6)2·3MeCN, Fig. 1 & Table 1. The key feature in the crystal packing of this compound, and of the analogous complexes mentioned above, is the formation of discrete dimers, Fig. 2a. These are formed by complexes of opposite held together by strong π–π stacking interactions via the planar tetraazaperylene moieties with Cg···Cg distances between 3.563 (3) and 3.837 (3) Å. The root mean square (rms) deviation from planarity for the tape moiety was calculated to be 0.0472 Å. The π–π stacking modes are very similar to earlier observed behavior of analogous complexes (Brietzke et al., 2012). All arene rings of the tape ligand are involved in the π–π stacking, Fig. 2b. The dimer features an interplanar tape separation of 3.33 Å. The Ru—N bond lengths formed by the tape and tmbpy ligands, Table 1, are very close to those of [Ru(L–L)tape]2+ (with L–L = bpy, dmbpy and dtbbpy), reported earlier (Brietzke et al., 2012). The three-dimensional structure is characterized by the parallel lying tape moieties. These are divided by tmbpy moieties. As a consequence large space is available, which is filled with hexafluoridophosphate and acetonitrile. Lots of non-classical hydrogen bonds connect cations, anions and solvent molecules to stabilize the crystal packing, Fig 3. Furthermore, these are supported by weak C—H···π-ring and C—H···N, F interactions (Table 2) .
The title compound was prepared as described earlier (Brietzke et al., 2012). Crystals suitable for X-ray structure analysis were obtained by vapor diffusion of diethyl ether into a saturated acetonitrile solution of [Ru(tmbpy)2tape](PF6)2. Thus, the solution was filled into a test tube, placed into a diethyl ether containing bottle. Dark green crystals began to form at ambient temperature within one week.
All hydrogen atoms were calculated in their expected positions and refined as riding atoms with Uiso(H)=1.2Ueq(C) and C—H distances of 0.93 Å for aromatic H atoms and with Uiso(H)=1.5Ueq(C) and distances of 0.96 Å for methyl hydrogen atoms. After unsuccessful attemps to model a disordered molecule of acetonitrile, the observed structure were modified by PLATON/SQUEEZE (Spek, 2009) to remove its contribution. PLATON/SQUEEZE calculated a solvent-accesible void volume in the
of 305 Å3 (11.3 % of the total cell volume), corresponding to 44 electrons (residual electron density after the last cycle) per This number agrees with two molecules of acetonitrile (2 x 22 = 44). Four fluorines of one hexafluoridophosphate anion (on P1) are disordered over three sets of positions, with occupancies of 0.517 (3):0.244 (3):0.239 (3), respectively.Data collection: X-AREA (Stoe & Cie, 2011); cell
X-AREA (Stoe & Cie, 2011); data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. ORTEP drawing of Λ-[Ru(tmbpy)2(tape)]2+ in rac-[Ru(tmbpy)2(tape)](PF6)2·3MeCN with the atomic numbering scheme and 30% probability displacement ellipsoids. Anions and solvent molecules are omitted for clarity. | |
Fig. 2. a: A side view of the dimer formed by Λ-[Ru(tmbpy)2(tape)]2+ and Δ-[Ru(tmbpy)2(tape)]2+ in rac-[Ru(tmbpy)2(tape)](PF6)2·3MeCN, featuring the stacking interactions via planar tape moieties. b: View along the normal of the tape-given r.m.s. plain, demonstrating the parallel-displaced π–π-stacking between the tape moieties. Anions, solvent molecules and hydrogen atoms are omitted for clarity. | |
Fig. 3. A packing diagram of the title compound is displayed along the c axis. Hydrogen bonds are shown as orange dashed lines. |
[Ru(C14H16N2)2(C16H8N4)](PF6)2·3C2H3N | Z = 2 |
Mr = 1195.01 | F(000) = 1216 |
Triclinic, P1 | Dx = 1.471 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.7485 (5) Å | Cell parameters from 17908 reflections |
b = 13.6973 (7) Å | θ = 1.2–27.1° |
c = 17.3623 (9) Å | µ = 0.44 mm−1 |
α = 105.786 (4)° | T = 210 K |
β = 92.858 (4)° | Prism, dark green |
γ = 110.436 (3)° | 0.55 × 0.40 × 0.25 mm |
V = 2698.3 (2) Å3 |
Stoe IPDS-2 diffractometer | 8918 independent reflections |
Radiation source: fine-focus sealed tube | 6396 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scan | θmax = 25.0°, θmin = 1.7° |
Absorption correction: integration (X-RED; Stoe & Cie, 2011) | h = −15→15 |
Tmin = 0.758, Tmax = 0.955 | k = −16→16 |
17495 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0767P)2] where P = (Fo2 + 2Fc2)/3 |
8918 reflections | (Δ/σ)max = 0.048 |
743 parameters | Δρmax = 0.51 e Å−3 |
363 restraints | Δρmin = −0.54 e Å−3 |
[Ru(C14H16N2)2(C16H8N4)](PF6)2·3C2H3N | γ = 110.436 (3)° |
Mr = 1195.01 | V = 2698.3 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.7485 (5) Å | Mo Kα radiation |
b = 13.6973 (7) Å | µ = 0.44 mm−1 |
c = 17.3623 (9) Å | T = 210 K |
α = 105.786 (4)° | 0.55 × 0.40 × 0.25 mm |
β = 92.858 (4)° |
Stoe IPDS-2 diffractometer | 8918 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2011) | 6396 reflections with I > 2σ(I) |
Tmin = 0.758, Tmax = 0.955 | Rint = 0.044 |
17495 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 363 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.51 e Å−3 |
8918 reflections | Δρmin = −0.54 e Å−3 |
743 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(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 | Occ. (<1) | |
C1 | 0.9535 (4) | 0.5550 (3) | 0.7768 (3) | 0.0491 (10) | |
H1 | 0.9615 | 0.5471 | 0.7227 | 0.059* | |
C2 | 1.0166 (4) | 0.6518 (3) | 0.8328 (3) | 0.0535 (11) | |
H2 | 1.0652 | 0.7083 | 0.8165 | 0.064* | |
C3 | 1.0691 (4) | 0.7631 (4) | 0.9812 (3) | 0.0587 (12) | |
H3 | 1.1193 | 0.8251 | 0.9717 | 0.070* | |
C4 | 1.0525 (5) | 0.7629 (4) | 1.0582 (3) | 0.0651 (13) | |
H4 | 1.0935 | 0.8267 | 1.1002 | 0.078* | |
C5 | 0.7638 (4) | 0.4080 (4) | 1.1288 (3) | 0.0609 (12) | |
H5 | 0.7596 | 0.4113 | 1.1828 | 0.073* | |
C6 | 0.6955 (4) | 0.3138 (4) | 1.0720 (3) | 0.0607 (12) | |
H6 | 0.6458 | 0.2564 | 1.0869 | 0.073* | |
C7 | 0.6375 (4) | 0.2133 (4) | 0.9220 (3) | 0.0607 (12) | |
H7 | 0.5850 | 0.1513 | 0.9301 | 0.073* | |
C8 | 0.6524 (4) | 0.2154 (3) | 0.8455 (3) | 0.0526 (11) | |
H8 | 0.6092 | 0.1540 | 0.8023 | 0.063* | |
C9 | 0.8701 (3) | 0.4816 (3) | 0.8733 (2) | 0.0410 (9) | |
C10 | 0.9343 (4) | 0.5786 (3) | 0.9364 (2) | 0.0432 (9) | |
C11 | 0.9233 (4) | 0.5869 (3) | 1.0184 (2) | 0.0478 (10) | |
C12 | 0.8452 (4) | 0.4914 (3) | 1.0381 (2) | 0.0469 (10) | |
C13 | 0.7788 (4) | 0.3962 (3) | 0.9733 (2) | 0.0445 (9) | |
C14 | 0.7897 (3) | 0.3907 (3) | 0.8918 (2) | 0.0412 (9) | |
C15 | 1.0090 (4) | 0.6679 (3) | 0.9168 (3) | 0.0494 (10) | |
C16 | 0.7017 (4) | 0.3052 (4) | 0.9898 (3) | 0.0515 (10) | |
C17 | 0.5981 (4) | 0.4380 (3) | 0.7574 (3) | 0.0504 (10) | |
H17 | 0.5880 | 0.4096 | 0.8006 | 0.060* | |
C18 | 0.5422 (4) | 0.5060 (4) | 0.7492 (3) | 0.0597 (12) | |
C19 | 0.5588 (4) | 0.5515 (4) | 0.6870 (3) | 0.0592 (12) | |
C20 | 0.6286 (4) | 0.5230 (4) | 0.6332 (3) | 0.0545 (11) | |
H20 | 0.6410 | 0.5517 | 0.5902 | 0.065* | |
C21 | 0.6795 (4) | 0.4524 (3) | 0.6434 (2) | 0.0453 (10) | |
C22 | 0.7530 (3) | 0.4178 (3) | 0.5882 (2) | 0.0418 (9) | |
C23 | 0.7676 (4) | 0.4405 (3) | 0.5163 (2) | 0.0463 (10) | |
H23 | 0.7321 | 0.4832 | 0.5016 | 0.056* | |
C24 | 0.8338 (4) | 0.4018 (3) | 0.4652 (2) | 0.0471 (10) | |
C25 | 0.8860 (3) | 0.3373 (3) | 0.4896 (2) | 0.0438 (9) | |
C26 | 0.8688 (3) | 0.3188 (3) | 0.5624 (2) | 0.0421 (9) | |
H26 | 0.9051 | 0.2780 | 0.5790 | 0.051* | |
C27 | 0.4646 (5) | 0.5281 (5) | 0.8090 (4) | 0.0837 (17) | |
H27A | 0.4665 | 0.4915 | 0.8488 | 0.126* | |
H27B | 0.3885 | 0.5011 | 0.7808 | 0.126* | |
H27C | 0.4895 | 0.6055 | 0.8355 | 0.126* | |
C28 | 0.5044 (6) | 0.6280 (5) | 0.6749 (3) | 0.0866 (19) | |
H28A | 0.5374 | 0.6964 | 0.7176 | 0.130* | |
H28B | 0.4245 | 0.5963 | 0.6756 | 0.130* | |
H28C | 0.5164 | 0.6403 | 0.6236 | 0.130* | |
C29 | 0.8467 (5) | 0.4249 (4) | 0.3863 (3) | 0.0637 (13) | |
H29A | 0.8157 | 0.3573 | 0.3426 | 0.096* | |
H29B | 0.9256 | 0.4610 | 0.3846 | 0.096* | |
H29C | 0.8070 | 0.4713 | 0.3809 | 0.096* | |
C30 | 0.9579 (4) | 0.2884 (4) | 0.4384 (3) | 0.0611 (12) | |
H30A | 0.9115 | 0.2353 | 0.3891 | 0.092* | |
H30B | 0.9910 | 0.2533 | 0.4678 | 0.092* | |
H30C | 1.0169 | 0.3452 | 0.4258 | 0.092* | |
C31 | 0.5323 (3) | 0.1451 (3) | 0.6379 (2) | 0.0432 (9) | |
H31 | 0.5073 | 0.2028 | 0.6455 | 0.052* | |
C32 | 0.4521 (3) | 0.0394 (3) | 0.6086 (2) | 0.0428 (9) | |
C33 | 0.4911 (4) | −0.0465 (3) | 0.5967 (2) | 0.0468 (10) | |
C34 | 0.6065 (4) | −0.0215 (3) | 0.6128 (2) | 0.0470 (10) | |
H34 | 0.6337 | −0.0778 | 0.6035 | 0.056* | |
C35 | 0.6821 (3) | 0.0867 (3) | 0.6427 (2) | 0.0406 (9) | |
C36 | 0.8029 (3) | 0.1188 (3) | 0.6649 (2) | 0.0424 (9) | |
C37 | 0.8613 (4) | 0.0500 (3) | 0.6433 (3) | 0.0508 (10) | |
H37 | 0.8221 | −0.0223 | 0.6114 | 0.061* | |
C38 | 0.9769 (4) | 0.0865 (3) | 0.6681 (3) | 0.0520 (11) | |
C39 | 1.0332 (4) | 0.1945 (3) | 0.7174 (2) | 0.0471 (10) | |
C40 | 0.9713 (4) | 0.2604 (3) | 0.7350 (2) | 0.0434 (9) | |
H40 | 1.0093 | 0.3331 | 0.7665 | 0.052* | |
C41 | 0.3296 (4) | 0.0203 (4) | 0.5928 (3) | 0.0590 (11) | |
H41A | 0.3002 | −0.0190 | 0.5366 | 0.089* | |
H41B | 0.3207 | 0.0895 | 0.6062 | 0.089* | |
H41C | 0.2890 | −0.0217 | 0.6255 | 0.089* | |
C42 | 0.4105 (4) | −0.1637 (3) | 0.5686 (3) | 0.0629 (13) | |
H42A | 0.3631 | −0.1776 | 0.5190 | 0.094* | |
H42B | 0.3642 | −0.1780 | 0.6092 | 0.094* | |
H42C | 0.4526 | −0.2107 | 0.5595 | 0.094* | |
C43 | 1.0396 (5) | 0.0110 (4) | 0.6420 (4) | 0.0752 (15) | |
H43A | 1.0889 | 0.0354 | 0.6053 | 0.113* | |
H43B | 0.9861 | −0.0621 | 0.6153 | 0.113* | |
H43C | 1.0837 | 0.0117 | 0.6887 | 0.113* | |
C44 | 1.1565 (4) | 0.2395 (4) | 0.7511 (3) | 0.0655 (13) | |
H44A | 1.1776 | 0.3125 | 0.7873 | 0.098* | |
H44B | 1.1999 | 0.2410 | 0.7075 | 0.098* | |
H44C | 1.1713 | 0.1939 | 0.7800 | 0.098* | |
P1 | 0.28562 (13) | 0.29009 (10) | 0.53337 (8) | 0.0656 (4) | |
F1A | 0.3747 (3) | 0.4046 (3) | 0.5343 (2) | 0.1070 (13) | |
F2A | 0.1974 (3) | 0.1762 (3) | 0.5305 (2) | 0.1152 (13) | |
F3A | 0.2296 (13) | 0.3494 (9) | 0.5977 (9) | 0.187 (10) | 0.517 (3) |
F4A | 0.2066 (10) | 0.2982 (11) | 0.4647 (8) | 0.100 (5) | 0.517 (3) |
F5A | 0.3413 (12) | 0.2335 (8) | 0.4672 (11) | 0.168 (9) | 0.517 (3) |
F6A | 0.3657 (11) | 0.2851 (10) | 0.6007 (9) | 0.170 (10) | 0.517 (3) |
F3B | 0.3496 (11) | 0.2988 (11) | 0.6149 (6) | 0.052 (6) | 0.244 (3) |
F4B | 0.2101 (12) | 0.3466 (11) | 0.5793 (11) | 0.107 (11) | 0.244 (3) |
F5B | 0.2216 (13) | 0.2815 (13) | 0.4509 (8) | 0.082 (10) | 0.244 (3) |
F6B | 0.3595 (13) | 0.2331 (11) | 0.4864 (9) | 0.144 (15) | 0.244 (3) |
F3C | 0.3232 (18) | 0.3186 (15) | 0.6257 (6) | 0.096 (12) | 0.239 (3) |
F4C | 0.1944 (12) | 0.3408 (11) | 0.550 (2) | 0.150 (18) | 0.239 (3) |
F5C | 0.250 (2) | 0.2632 (16) | 0.4400 (7) | 0.19 (3) | 0.239 (3) |
F6C | 0.3778 (14) | 0.2404 (13) | 0.516 (2) | 0.167 (18) | 0.239 (3) |
P2 | 0.30495 (19) | −0.05892 (15) | 0.82144 (11) | 0.1025 (6) | |
F7 | 0.3074 (8) | 0.0519 (5) | 0.8355 (7) | 0.328 (7) | |
F8 | 0.3046 (7) | −0.1780 (4) | 0.8031 (5) | 0.240 (4) | |
F9 | 0.4063 (5) | −0.0332 (5) | 0.7752 (3) | 0.197 (3) | |
F10 | 0.2122 (6) | −0.0902 (6) | 0.8698 (4) | 0.271 (5) | |
F11 | 0.3925 (6) | −0.0232 (7) | 0.8972 (3) | 0.260 (5) | |
F12 | 0.2236 (6) | −0.1051 (6) | 0.7437 (4) | 0.243 (4) | |
N1 | 0.8782 (3) | 0.4674 (2) | 0.79498 (18) | 0.0410 (7) | |
N2 | 0.9818 (3) | 0.6779 (3) | 1.0784 (2) | 0.0575 (10) | |
N3 | 0.8370 (3) | 0.4969 (3) | 1.1151 (2) | 0.0547 (9) | |
N4 | 0.7285 (3) | 0.3040 (2) | 0.82864 (19) | 0.0417 (7) | |
N5 | 0.6659 (3) | 0.4114 (2) | 0.70604 (19) | 0.0413 (8) | |
N6 | 0.8028 (3) | 0.3555 (2) | 0.61199 (17) | 0.0388 (7) | |
N7 | 0.6437 (3) | 0.1696 (2) | 0.65597 (18) | 0.0411 (8) | |
N8 | 0.8593 (3) | 0.2260 (2) | 0.70947 (18) | 0.0385 (7) | |
Ru1 | 0.76414 (3) | 0.32203 (2) | 0.71845 (2) | 0.03817 (11) | |
C45 | 0.6212 (11) | −0.0934 (9) | 0.9095 (7) | 0.172 (4) | |
H45A | 0.6471 | −0.0405 | 0.9626 | 0.258* | |
H45B | 0.6331 | −0.1586 | 0.9102 | 0.258* | |
H45C | 0.5418 | −0.1109 | 0.8942 | 0.258* | |
C46 | 0.6826 (9) | −0.0492 (7) | 0.8529 (6) | 0.123 (3) | |
N9 | 0.7363 (9) | −0.0128 (7) | 0.8093 (6) | 0.167 (3) | |
C47 | 0.8808 (10) | 0.8156 (10) | 0.7475 (6) | 0.172 (5) | |
H47A | 0.8579 | 0.8733 | 0.7417 | 0.259* | |
H47B | 0.8611 | 0.7587 | 0.6964 | 0.259* | |
H47C | 0.9613 | 0.8442 | 0.7647 | 0.259* | |
C48 | 0.8237 (9) | 0.7712 (9) | 0.8072 (7) | 0.142 (3) | |
N10 | 0.7779 (10) | 0.7379 (9) | 0.8572 (6) | 0.181 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.048 (3) | 0.048 (2) | 0.048 (2) | 0.015 (2) | 0.0124 (19) | 0.0115 (18) |
C2 | 0.050 (3) | 0.043 (2) | 0.062 (3) | 0.008 (2) | 0.011 (2) | 0.019 (2) |
C3 | 0.054 (3) | 0.046 (2) | 0.062 (3) | 0.010 (2) | 0.003 (2) | 0.007 (2) |
C4 | 0.063 (4) | 0.050 (3) | 0.063 (3) | 0.013 (2) | 0.004 (2) | 0.000 (2) |
C5 | 0.064 (4) | 0.085 (3) | 0.046 (2) | 0.037 (3) | 0.025 (2) | 0.026 (2) |
C6 | 0.057 (3) | 0.072 (3) | 0.058 (3) | 0.024 (3) | 0.023 (2) | 0.026 (2) |
C7 | 0.060 (3) | 0.054 (3) | 0.065 (3) | 0.014 (2) | 0.020 (2) | 0.022 (2) |
C8 | 0.049 (3) | 0.049 (2) | 0.055 (2) | 0.014 (2) | 0.014 (2) | 0.0135 (19) |
C9 | 0.037 (3) | 0.0408 (19) | 0.042 (2) | 0.0148 (18) | 0.0106 (17) | 0.0069 (16) |
C10 | 0.038 (3) | 0.042 (2) | 0.043 (2) | 0.0150 (19) | 0.0058 (17) | 0.0043 (16) |
C11 | 0.045 (3) | 0.048 (2) | 0.046 (2) | 0.021 (2) | 0.0094 (18) | 0.0029 (18) |
C12 | 0.043 (3) | 0.055 (2) | 0.043 (2) | 0.023 (2) | 0.0103 (18) | 0.0109 (18) |
C13 | 0.041 (3) | 0.049 (2) | 0.044 (2) | 0.018 (2) | 0.0143 (18) | 0.0118 (17) |
C14 | 0.038 (3) | 0.042 (2) | 0.044 (2) | 0.0167 (19) | 0.0121 (17) | 0.0111 (17) |
C15 | 0.045 (3) | 0.043 (2) | 0.054 (2) | 0.015 (2) | 0.0067 (19) | 0.0073 (18) |
C16 | 0.049 (3) | 0.057 (2) | 0.053 (2) | 0.020 (2) | 0.019 (2) | 0.022 (2) |
C17 | 0.047 (3) | 0.051 (2) | 0.056 (2) | 0.024 (2) | 0.016 (2) | 0.0095 (19) |
C18 | 0.054 (3) | 0.059 (3) | 0.062 (3) | 0.032 (2) | 0.011 (2) | −0.002 (2) |
C19 | 0.058 (3) | 0.058 (3) | 0.061 (3) | 0.034 (2) | 0.002 (2) | 0.002 (2) |
C20 | 0.063 (3) | 0.055 (2) | 0.051 (2) | 0.033 (2) | 0.007 (2) | 0.0107 (19) |
C21 | 0.044 (3) | 0.040 (2) | 0.050 (2) | 0.0174 (19) | 0.0086 (18) | 0.0060 (17) |
C22 | 0.037 (3) | 0.0349 (18) | 0.047 (2) | 0.0114 (18) | 0.0036 (17) | 0.0062 (16) |
C23 | 0.050 (3) | 0.039 (2) | 0.046 (2) | 0.017 (2) | 0.0047 (19) | 0.0070 (17) |
C24 | 0.045 (3) | 0.039 (2) | 0.046 (2) | 0.0083 (19) | 0.0080 (18) | 0.0062 (17) |
C25 | 0.036 (3) | 0.044 (2) | 0.041 (2) | 0.0104 (19) | 0.0050 (17) | 0.0031 (16) |
C26 | 0.033 (3) | 0.045 (2) | 0.044 (2) | 0.0157 (19) | 0.0074 (17) | 0.0063 (16) |
C27 | 0.080 (4) | 0.099 (4) | 0.093 (4) | 0.060 (4) | 0.037 (3) | 0.024 (3) |
C28 | 0.108 (5) | 0.097 (4) | 0.078 (4) | 0.077 (4) | 0.017 (3) | 0.012 (3) |
C29 | 0.075 (4) | 0.067 (3) | 0.049 (2) | 0.025 (3) | 0.018 (2) | 0.019 (2) |
C30 | 0.060 (3) | 0.074 (3) | 0.050 (2) | 0.033 (3) | 0.019 (2) | 0.010 (2) |
C31 | 0.034 (3) | 0.047 (2) | 0.050 (2) | 0.017 (2) | 0.0038 (17) | 0.0143 (17) |
C32 | 0.032 (3) | 0.049 (2) | 0.044 (2) | 0.0112 (19) | 0.0049 (17) | 0.0145 (17) |
C33 | 0.040 (3) | 0.046 (2) | 0.045 (2) | 0.011 (2) | 0.0032 (18) | 0.0077 (17) |
C34 | 0.045 (3) | 0.039 (2) | 0.051 (2) | 0.016 (2) | 0.0014 (18) | 0.0044 (17) |
C35 | 0.035 (3) | 0.043 (2) | 0.040 (2) | 0.0153 (19) | 0.0063 (16) | 0.0075 (16) |
C36 | 0.038 (3) | 0.040 (2) | 0.045 (2) | 0.0142 (19) | 0.0034 (17) | 0.0065 (16) |
C37 | 0.044 (3) | 0.042 (2) | 0.061 (3) | 0.020 (2) | 0.006 (2) | 0.0038 (18) |
C38 | 0.042 (3) | 0.051 (2) | 0.064 (3) | 0.022 (2) | 0.011 (2) | 0.013 (2) |
C39 | 0.036 (3) | 0.058 (2) | 0.046 (2) | 0.019 (2) | 0.0031 (18) | 0.0114 (18) |
C40 | 0.037 (3) | 0.048 (2) | 0.040 (2) | 0.0132 (19) | 0.0027 (17) | 0.0089 (16) |
C41 | 0.042 (3) | 0.061 (3) | 0.077 (3) | 0.017 (2) | 0.011 (2) | 0.028 (2) |
C42 | 0.044 (3) | 0.045 (2) | 0.083 (3) | 0.008 (2) | −0.001 (2) | 0.007 (2) |
C43 | 0.054 (4) | 0.064 (3) | 0.108 (4) | 0.035 (3) | 0.013 (3) | 0.011 (3) |
C44 | 0.048 (3) | 0.075 (3) | 0.068 (3) | 0.027 (3) | 0.001 (2) | 0.009 (2) |
P1 | 0.0775 (11) | 0.0526 (7) | 0.0667 (8) | 0.0315 (7) | −0.0020 (7) | 0.0117 (6) |
F1A | 0.116 (3) | 0.0721 (19) | 0.110 (3) | 0.012 (2) | −0.037 (2) | 0.0338 (18) |
F2A | 0.115 (4) | 0.079 (2) | 0.125 (3) | 0.002 (2) | −0.015 (2) | 0.042 (2) |
F3A | 0.36 (3) | 0.203 (15) | 0.115 (10) | 0.214 (17) | 0.126 (15) | 0.073 (9) |
F4A | 0.073 (7) | 0.140 (10) | 0.102 (9) | 0.040 (8) | 0.001 (8) | 0.065 (8) |
F5A | 0.143 (13) | 0.093 (8) | 0.27 (2) | 0.070 (9) | 0.101 (14) | 0.013 (10) |
F6A | 0.178 (15) | 0.080 (7) | 0.223 (18) | 0.018 (8) | −0.108 (14) | 0.069 (9) |
F3B | 0.059 (12) | 0.089 (12) | 0.038 (7) | 0.055 (11) | 0.023 (7) | 0.025 (7) |
F4B | 0.120 (19) | 0.21 (3) | 0.060 (10) | 0.14 (2) | 0.015 (10) | 0.041 (12) |
F5B | 0.051 (14) | 0.14 (2) | 0.043 (10) | 0.037 (16) | 0.009 (10) | 0.015 (11) |
F6B | 0.23 (3) | 0.23 (3) | 0.041 (9) | 0.19 (3) | 0.013 (11) | 0.022 (11) |
F3C | 0.045 (11) | 0.14 (2) | 0.037 (7) | −0.019 (13) | 0.015 (8) | 0.004 (9) |
F4C | 0.068 (15) | 0.078 (12) | 0.31 (5) | 0.027 (10) | −0.03 (2) | 0.077 (19) |
F5C | 0.23 (5) | 0.16 (3) | 0.047 (12) | −0.09 (3) | −0.02 (2) | 0.025 (15) |
F6C | 0.19 (4) | 0.17 (3) | 0.17 (3) | 0.11 (3) | 0.12 (3) | 0.03 (2) |
P2 | 0.1084 (17) | 0.0854 (11) | 0.0800 (11) | −0.0078 (10) | 0.0051 (10) | 0.0333 (9) |
F7 | 0.346 (13) | 0.100 (4) | 0.573 (18) | 0.103 (6) | 0.239 (13) | 0.106 (7) |
F8 | 0.324 (11) | 0.128 (5) | 0.250 (8) | 0.050 (6) | 0.030 (7) | 0.082 (5) |
F9 | 0.185 (7) | 0.242 (7) | 0.157 (5) | 0.050 (5) | 0.078 (5) | 0.084 (5) |
F10 | 0.237 (9) | 0.240 (7) | 0.196 (6) | −0.064 (6) | 0.122 (6) | 0.039 (5) |
F11 | 0.190 (7) | 0.362 (11) | 0.099 (4) | −0.014 (7) | −0.024 (4) | 0.035 (5) |
F12 | 0.233 (9) | 0.265 (8) | 0.159 (5) | 0.029 (7) | −0.085 (5) | 0.064 (5) |
N1 | 0.040 (2) | 0.0414 (17) | 0.0426 (17) | 0.0152 (16) | 0.0121 (14) | 0.0128 (14) |
N2 | 0.057 (3) | 0.054 (2) | 0.048 (2) | 0.017 (2) | 0.0046 (17) | 0.0003 (17) |
N3 | 0.053 (3) | 0.070 (2) | 0.0403 (18) | 0.027 (2) | 0.0151 (16) | 0.0100 (17) |
N4 | 0.034 (2) | 0.0397 (17) | 0.0462 (18) | 0.0119 (15) | 0.0091 (14) | 0.0082 (14) |
N5 | 0.038 (2) | 0.0381 (16) | 0.0453 (18) | 0.0160 (15) | 0.0135 (15) | 0.0064 (14) |
N6 | 0.037 (2) | 0.0370 (16) | 0.0377 (16) | 0.0159 (15) | 0.0046 (14) | 0.0027 (13) |
N7 | 0.039 (2) | 0.0395 (16) | 0.0421 (17) | 0.0149 (16) | 0.0077 (14) | 0.0077 (13) |
N8 | 0.035 (2) | 0.0394 (16) | 0.0384 (16) | 0.0135 (15) | 0.0054 (14) | 0.0085 (13) |
Ru1 | 0.0355 (2) | 0.03675 (17) | 0.03886 (17) | 0.01383 (14) | 0.00804 (12) | 0.00568 (12) |
C45 | 0.202 (12) | 0.162 (9) | 0.177 (10) | 0.084 (9) | 0.077 (9) | 0.064 (8) |
C46 | 0.144 (9) | 0.107 (6) | 0.124 (7) | 0.054 (6) | 0.043 (6) | 0.033 (5) |
N9 | 0.178 (9) | 0.152 (7) | 0.188 (9) | 0.057 (7) | 0.074 (7) | 0.079 (6) |
C47 | 0.200 (12) | 0.244 (12) | 0.139 (8) | 0.118 (10) | 0.087 (8) | 0.105 (9) |
C48 | 0.124 (9) | 0.152 (8) | 0.149 (9) | 0.073 (7) | 0.009 (7) | 0.019 (7) |
N10 | 0.178 (10) | 0.232 (11) | 0.154 (8) | 0.075 (8) | 0.054 (7) | 0.088 (8) |
C1—C2 | 1.351 (6) | C31—C32 | 1.384 (6) |
C1—N1 | 1.375 (5) | C31—H31 | 0.9300 |
C1—H1 | 0.9300 | C32—C33 | 1.401 (5) |
C2—C15 | 1.428 (6) | C32—C41 | 1.487 (6) |
C2—H2 | 0.9300 | C33—C34 | 1.383 (6) |
C3—C4 | 1.365 (7) | C33—C42 | 1.498 (6) |
C3—C15 | 1.400 (6) | C34—C35 | 1.389 (5) |
C3—H3 | 0.9300 | C34—H34 | 0.9300 |
C4—N2 | 1.347 (6) | C35—N7 | 1.357 (5) |
C4—H4 | 0.9300 | C35—C36 | 1.446 (6) |
C5—N3 | 1.342 (6) | C36—N8 | 1.364 (5) |
C5—C6 | 1.354 (7) | C36—C37 | 1.382 (5) |
C5—H5 | 0.9300 | C37—C38 | 1.383 (6) |
C6—C16 | 1.407 (6) | C37—H37 | 0.9300 |
C6—H6 | 0.9300 | C38—C39 | 1.395 (6) |
C7—C8 | 1.359 (6) | C38—C43 | 1.507 (6) |
C7—C16 | 1.421 (6) | C39—C40 | 1.379 (5) |
C7—H7 | 0.9300 | C39—C44 | 1.493 (6) |
C8—N4 | 1.379 (5) | C40—N8 | 1.346 (5) |
C8—H8 | 0.9300 | C40—H40 | 0.9300 |
C9—N1 | 1.335 (5) | C41—H41A | 0.9600 |
C9—C10 | 1.412 (5) | C41—H41B | 0.9600 |
C9—C14 | 1.437 (6) | C41—H41C | 0.9600 |
C10—C15 | 1.402 (6) | C42—H42A | 0.9600 |
C10—C11 | 1.415 (5) | C42—H42B | 0.9600 |
C11—N2 | 1.327 (5) | C42—H42C | 0.9600 |
C11—C12 | 1.479 (6) | C43—H43A | 0.9600 |
C12—N3 | 1.328 (5) | C43—H43B | 0.9600 |
C12—C13 | 1.421 (6) | C43—H43C | 0.9600 |
C13—C16 | 1.404 (6) | C44—H44A | 0.9600 |
C13—C14 | 1.413 (5) | C44—H44B | 0.9600 |
C14—N4 | 1.334 (5) | C44—H44C | 0.9600 |
C17—N5 | 1.340 (5) | P1—F6A | 1.545 (7) |
C17—C18 | 1.386 (6) | P1—F3C | 1.550 (9) |
C17—H17 | 0.9300 | P1—F5A | 1.551 (8) |
C18—C19 | 1.376 (7) | P1—F6B | 1.550 (9) |
C18—C27 | 1.512 (6) | P1—F3B | 1.551 (8) |
C19—C20 | 1.395 (6) | P1—F4C | 1.552 (9) |
C19—C28 | 1.496 (6) | P1—F3A | 1.552 (7) |
C20—C21 | 1.381 (6) | P1—F6C | 1.554 (9) |
C20—H20 | 0.9300 | P1—F4B | 1.556 (8) |
C21—N5 | 1.347 (5) | P1—F2A | 1.559 (4) |
C21—C22 | 1.475 (5) | P1—F5C | 1.565 (9) |
C22—N6 | 1.359 (5) | P1—F5B | 1.567 (9) |
C22—C23 | 1.372 (6) | P2—F7 | 1.460 (5) |
C23—C24 | 1.382 (6) | P2—F10 | 1.493 (5) |
C23—H23 | 0.9300 | P2—F12 | 1.496 (5) |
C24—C25 | 1.409 (6) | P2—F11 | 1.529 (6) |
C24—C29 | 1.492 (6) | P2—F9 | 1.542 (5) |
C25—C26 | 1.369 (5) | P2—F8 | 1.573 (6) |
C25—C30 | 1.505 (5) | N1—Ru1 | 2.048 (3) |
C26—N6 | 1.354 (5) | N4—Ru1 | 2.047 (3) |
C26—H26 | 0.9300 | N5—Ru1 | 2.074 (3) |
C27—H27A | 0.9600 | N6—Ru1 | 2.065 (3) |
C27—H27B | 0.9600 | N7—Ru1 | 2.063 (3) |
C27—H27C | 0.9600 | N8—Ru1 | 2.061 (3) |
C28—H28A | 0.9600 | C45—C46 | 1.420 (12) |
C28—H28B | 0.9600 | C45—H45A | 0.9600 |
C28—H28C | 0.9600 | C45—H45B | 0.9600 |
C29—H29A | 0.9600 | C45—H45C | 0.9600 |
C29—H29B | 0.9600 | C46—N9 | 1.143 (11) |
C29—H29C | 0.9600 | C47—C48 | 1.444 (14) |
C30—H30A | 0.9600 | C47—H47A | 0.9600 |
C30—H30B | 0.9600 | C47—H47B | 0.9600 |
C30—H30C | 0.9600 | C47—H47C | 0.9600 |
C31—N7 | 1.339 (5) | C48—N10 | 1.176 (13) |
C2—C1—N1 | 123.9 (4) | C37—C38—C39 | 118.2 (4) |
C2—C1—H1 | 118.1 | C37—C38—C43 | 120.5 (4) |
N1—C1—H1 | 118.1 | C39—C38—C43 | 121.4 (4) |
C1—C2—C15 | 120.4 (4) | C40—C39—C38 | 118.0 (4) |
C1—C2—H2 | 119.8 | C40—C39—C44 | 119.9 (4) |
C15—C2—H2 | 119.8 | C38—C39—C44 | 122.1 (4) |
C4—C3—C15 | 118.6 (4) | N8—C40—C39 | 124.0 (4) |
C4—C3—H3 | 120.7 | N8—C40—H40 | 118.0 |
C15—C3—H3 | 120.7 | C39—C40—H40 | 118.0 |
N2—C4—C3 | 125.4 (4) | C32—C41—H41A | 109.5 |
N2—C4—H4 | 117.3 | C32—C41—H41B | 109.5 |
C3—C4—H4 | 117.3 | H41A—C41—H41B | 109.5 |
N3—C5—C6 | 126.4 (4) | C32—C41—H41C | 109.5 |
N3—C5—H5 | 116.8 | H41A—C41—H41C | 109.5 |
C6—C5—H5 | 116.8 | H41B—C41—H41C | 109.5 |
C5—C6—C16 | 118.2 (4) | C33—C42—H42A | 109.5 |
C5—C6—H6 | 120.9 | C33—C42—H42B | 109.5 |
C16—C6—H6 | 120.9 | H42A—C42—H42B | 109.5 |
C8—C7—C16 | 120.4 (4) | C33—C42—H42C | 109.5 |
C8—C7—H7 | 119.8 | H42A—C42—H42C | 109.5 |
C16—C7—H7 | 119.8 | H42B—C42—H42C | 109.5 |
C7—C8—N4 | 123.2 (4) | C38—C43—H43A | 109.5 |
C7—C8—H8 | 118.4 | C38—C43—H43B | 109.5 |
N4—C8—H8 | 118.4 | H43A—C43—H43B | 109.5 |
N1—C9—C10 | 124.1 (4) | C38—C43—H43C | 109.5 |
N1—C9—C14 | 116.0 (3) | H43A—C43—H43C | 109.5 |
C10—C9—C14 | 119.9 (3) | H43B—C43—H43C | 109.5 |
C15—C10—C9 | 119.0 (4) | C39—C44—H44A | 109.5 |
C15—C10—C11 | 120.0 (4) | C39—C44—H44B | 109.5 |
C9—C10—C11 | 121.0 (4) | H44A—C44—H44B | 109.5 |
N2—C11—C10 | 121.9 (4) | C39—C44—H44C | 109.5 |
N2—C11—C12 | 118.9 (4) | H44A—C44—H44C | 109.5 |
C10—C11—C12 | 119.3 (3) | H44B—C44—H44C | 109.5 |
N3—C12—C13 | 121.7 (4) | F6A—P1—F5A | 90.7 (6) |
N3—C12—C11 | 119.8 (4) | F6B—P1—F3B | 90.0 (6) |
C13—C12—C11 | 118.5 (3) | F3C—P1—F4C | 90.5 (7) |
C16—C13—C14 | 118.9 (4) | F6A—P1—F3A | 91.0 (6) |
C16—C13—C12 | 119.9 (4) | F5A—P1—F3A | 177.9 (7) |
C14—C13—C12 | 121.2 (4) | F3C—P1—F6C | 89.6 (7) |
N4—C14—C13 | 123.6 (4) | F4C—P1—F6C | 179.4 (8) |
N4—C14—C9 | 116.4 (3) | F6B—P1—F4B | 179.1 (8) |
C13—C14—C9 | 120.0 (4) | F3B—P1—F4B | 90.8 (6) |
C3—C15—C10 | 117.0 (4) | F6A—P1—F2A | 90.2 (4) |
C3—C15—C2 | 126.7 (4) | F3C—P1—F2A | 90.9 (5) |
C10—C15—C2 | 116.3 (4) | F5A—P1—F2A | 90.3 (4) |
C13—C16—C6 | 116.8 (4) | F6B—P1—F2A | 89.9 (6) |
C13—C16—C7 | 116.8 (4) | F3B—P1—F2A | 90.0 (5) |
C6—C16—C7 | 126.3 (4) | F4C—P1—F2A | 90.1 (5) |
N5—C17—C18 | 123.1 (4) | F3A—P1—F2A | 91.0 (5) |
N5—C17—H17 | 118.5 | F6C—P1—F2A | 90.5 (6) |
C18—C17—H17 | 118.5 | F4B—P1—F2A | 89.8 (5) |
C19—C18—C17 | 119.2 (4) | F3C—P1—F5C | 178.7 (8) |
C19—C18—C27 | 122.0 (4) | F4C—P1—F5C | 90.0 (7) |
C17—C18—C27 | 118.9 (5) | F6C—P1—F5C | 89.9 (7) |
C18—C19—C20 | 117.7 (4) | F2A—P1—F5C | 90.3 (5) |
C18—C19—C28 | 122.8 (4) | F6B—P1—F5B | 89.8 (7) |
C20—C19—C28 | 119.5 (5) | F3B—P1—F5B | 179.7 (8) |
C21—C20—C19 | 120.3 (4) | F4B—P1—F5B | 89.4 (7) |
C21—C20—H20 | 119.8 | F2A—P1—F5B | 90.2 (5) |
C19—C20—H20 | 119.8 | F7—P2—F10 | 94.1 (4) |
N5—C21—C20 | 121.5 (4) | F7—P2—F12 | 93.9 (5) |
N5—C21—C22 | 115.3 (3) | F10—P2—F12 | 92.6 (4) |
C20—C21—C22 | 123.2 (4) | F7—P2—F11 | 92.3 (5) |
N6—C22—C23 | 121.2 (3) | F10—P2—F11 | 89.6 (4) |
N6—C22—C21 | 114.5 (3) | F12—P2—F11 | 173.2 (5) |
C23—C22—C21 | 124.2 (4) | F7—P2—F9 | 90.4 (4) |
C22—C23—C24 | 121.7 (4) | F10—P2—F9 | 174.2 (5) |
C22—C23—H23 | 119.2 | F12—P2—F9 | 90.7 (4) |
C24—C23—H23 | 119.2 | F11—P2—F9 | 86.5 (4) |
C23—C24—C25 | 117.5 (4) | F7—P2—F8 | 177.6 (5) |
C23—C24—C29 | 121.1 (4) | F10—P2—F8 | 88.1 (4) |
C25—C24—C29 | 121.4 (4) | F12—P2—F8 | 85.0 (4) |
C26—C25—C24 | 117.7 (3) | F11—P2—F8 | 88.6 (4) |
C26—C25—C30 | 119.8 (4) | F9—P2—F8 | 87.5 (4) |
C24—C25—C30 | 122.5 (4) | C9—N1—C1 | 116.2 (3) |
N6—C26—C25 | 124.9 (4) | C9—N1—Ru1 | 114.1 (3) |
N6—C26—H26 | 117.6 | C1—N1—Ru1 | 129.3 (3) |
C25—C26—H26 | 117.6 | C11—N2—C4 | 117.2 (4) |
C18—C27—H27A | 109.5 | C12—N3—C5 | 116.9 (4) |
C18—C27—H27B | 109.5 | C14—N4—C8 | 117.0 (3) |
H27A—C27—H27B | 109.5 | C14—N4—Ru1 | 114.0 (3) |
C18—C27—H27C | 109.5 | C8—N4—Ru1 | 128.9 (3) |
H27A—C27—H27C | 109.5 | C17—N5—C21 | 118.1 (3) |
H27B—C27—H27C | 109.5 | C17—N5—Ru1 | 126.1 (3) |
C19—C28—H28A | 109.5 | C21—N5—Ru1 | 115.6 (2) |
C19—C28—H28B | 109.5 | C26—N6—C22 | 117.0 (3) |
H28A—C28—H28B | 109.5 | C26—N6—Ru1 | 127.0 (3) |
C19—C28—H28C | 109.5 | C22—N6—Ru1 | 116.0 (2) |
H28A—C28—H28C | 109.5 | C31—N7—C35 | 118.8 (3) |
H28B—C28—H28C | 109.5 | C31—N7—Ru1 | 126.1 (2) |
C24—C29—H29A | 109.5 | C35—N7—Ru1 | 114.5 (3) |
C24—C29—H29B | 109.5 | C40—N8—C36 | 118.1 (3) |
H29A—C29—H29B | 109.5 | C40—N8—Ru1 | 126.8 (2) |
C24—C29—H29C | 109.5 | C36—N8—Ru1 | 114.7 (3) |
H29A—C29—H29C | 109.5 | N4—Ru1—N1 | 79.34 (13) |
H29B—C29—H29C | 109.5 | N4—Ru1—N8 | 91.00 (12) |
C25—C30—H30A | 109.5 | N1—Ru1—N8 | 100.20 (12) |
C25—C30—H30B | 109.5 | N4—Ru1—N7 | 92.60 (13) |
H30A—C30—H30B | 109.5 | N1—Ru1—N7 | 171.90 (12) |
C25—C30—H30C | 109.5 | N8—Ru1—N7 | 79.05 (13) |
H30A—C30—H30C | 109.5 | N4—Ru1—N6 | 174.66 (12) |
H30B—C30—H30C | 109.5 | N1—Ru1—N6 | 96.31 (12) |
N7—C31—C32 | 124.1 (3) | N8—Ru1—N6 | 92.82 (12) |
N7—C31—H31 | 118.0 | N7—Ru1—N6 | 91.79 (12) |
C32—C31—H31 | 118.0 | N4—Ru1—N5 | 98.07 (12) |
C31—C32—C33 | 117.3 (4) | N1—Ru1—N5 | 85.26 (12) |
C31—C32—C41 | 120.2 (4) | N8—Ru1—N5 | 170.18 (12) |
C33—C32—C41 | 122.5 (4) | N7—Ru1—N5 | 96.70 (13) |
C34—C33—C32 | 118.8 (4) | N6—Ru1—N5 | 78.38 (12) |
C34—C33—C42 | 119.9 (4) | C46—C45—H45A | 109.5 |
C32—C33—C42 | 121.3 (4) | C46—C45—H45B | 109.5 |
C33—C34—C35 | 120.7 (4) | H45A—C45—H45B | 109.5 |
C33—C34—H34 | 119.7 | C46—C45—H45C | 109.5 |
C35—C34—H34 | 119.7 | H45A—C45—H45C | 109.5 |
N7—C35—C34 | 120.3 (4) | H45B—C45—H45C | 109.5 |
N7—C35—C36 | 115.8 (3) | N9—C46—C45 | 177.0 (13) |
C34—C35—C36 | 123.8 (3) | C48—C47—H47A | 109.5 |
N8—C36—C37 | 120.3 (4) | C48—C47—H47B | 109.5 |
N8—C36—C35 | 115.0 (3) | H47A—C47—H47B | 109.5 |
C37—C36—C35 | 124.7 (4) | C48—C47—H47C | 109.5 |
C36—C37—C38 | 121.3 (4) | H47A—C47—H47C | 109.5 |
C36—C37—H37 | 119.4 | H47B—C47—H47C | 109.5 |
C38—C37—H37 | 119.4 | N10—C48—C47 | 178.2 (13) |
N1—C1—C2—C15 | 0.9 (7) | C30—C25—C26—N6 | −177.7 (4) |
C15—C3—C4—N2 | −0.3 (8) | N7—C31—C32—C33 | −0.6 (6) |
N3—C5—C6—C16 | 1.4 (8) | N7—C31—C32—C41 | 178.0 (4) |
C16—C7—C8—N4 | 0.0 (7) | C31—C32—C33—C34 | −1.5 (6) |
N1—C9—C10—C15 | 2.3 (6) | C41—C32—C33—C34 | 179.9 (4) |
C14—C9—C10—C15 | −177.5 (4) | C31—C32—C33—C42 | 177.4 (4) |
N1—C9—C10—C11 | −178.5 (4) | C41—C32—C33—C42 | −1.2 (6) |
C14—C9—C10—C11 | 1.7 (6) | C32—C33—C34—C35 | 2.1 (6) |
C15—C10—C11—N2 | 0.2 (6) | C42—C33—C34—C35 | −176.8 (4) |
C9—C10—C11—N2 | −179.1 (4) | C33—C34—C35—N7 | −0.5 (6) |
C15—C10—C11—C12 | −179.2 (4) | C33—C34—C35—C36 | 176.7 (4) |
C9—C10—C11—C12 | 1.6 (6) | N7—C35—C36—N8 | 11.4 (5) |
N2—C11—C12—N3 | −1.8 (6) | C34—C35—C36—N8 | −165.9 (4) |
C10—C11—C12—N3 | 177.6 (4) | N7—C35—C36—C37 | −167.8 (4) |
N2—C11—C12—C13 | 177.0 (4) | C34—C35—C36—C37 | 14.9 (6) |
C10—C11—C12—C13 | −3.6 (6) | N8—C36—C37—C38 | 2.1 (6) |
N3—C12—C13—C16 | 0.4 (6) | C35—C36—C37—C38 | −178.8 (4) |
C11—C12—C13—C16 | −178.3 (4) | C36—C37—C38—C39 | 1.4 (7) |
N3—C12—C13—C14 | −178.9 (4) | C36—C37—C38—C43 | −178.3 (4) |
C11—C12—C13—C14 | 2.4 (6) | C37—C38—C39—C40 | −3.3 (6) |
C16—C13—C14—N4 | 1.6 (6) | C43—C38—C39—C40 | 176.3 (4) |
C12—C13—C14—N4 | −179.1 (4) | C37—C38—C39—C44 | 176.6 (4) |
C16—C13—C14—C9 | −178.4 (4) | C43—C38—C39—C44 | −3.8 (7) |
C12—C13—C14—C9 | 0.9 (6) | C38—C39—C40—N8 | 2.0 (6) |
N1—C9—C14—N4 | −2.9 (5) | C44—C39—C40—N8 | −177.9 (4) |
C10—C9—C14—N4 | 176.9 (3) | C10—C9—N1—C1 | −1.0 (6) |
N1—C9—C14—C13 | 177.2 (3) | C14—C9—N1—C1 | 178.8 (3) |
C10—C9—C14—C13 | −3.0 (6) | C10—C9—N1—Ru1 | −175.3 (3) |
C4—C3—C15—C10 | 0.6 (7) | C14—C9—N1—Ru1 | 4.5 (4) |
C4—C3—C15—C2 | −178.7 (4) | C2—C1—N1—C9 | −0.7 (6) |
C9—C10—C15—C3 | 178.7 (4) | C2—C1—N1—Ru1 | 172.7 (3) |
C11—C10—C15—C3 | −0.6 (6) | C10—C11—N2—C4 | 0.2 (6) |
C9—C10—C15—C2 | −1.9 (6) | C12—C11—N2—C4 | 179.6 (4) |
C11—C10—C15—C2 | 178.9 (4) | C3—C4—N2—C11 | −0.1 (8) |
C1—C2—C15—C3 | 179.8 (5) | C13—C12—N3—C5 | 0.6 (6) |
C1—C2—C15—C10 | 0.4 (6) | C11—C12—N3—C5 | 179.3 (4) |
C14—C13—C16—C6 | 178.8 (4) | C6—C5—N3—C12 | −1.6 (7) |
C12—C13—C16—C6 | −0.5 (6) | C13—C14—N4—C8 | −1.1 (6) |
C14—C13—C16—C7 | −1.2 (6) | C9—C14—N4—C8 | 178.9 (3) |
C12—C13—C16—C7 | 179.5 (4) | C13—C14—N4—Ru1 | 179.8 (3) |
C5—C6—C16—C13 | −0.3 (6) | C9—C14—N4—Ru1 | −0.2 (4) |
C5—C6—C16—C7 | 179.7 (5) | C7—C8—N4—C14 | 0.3 (6) |
C8—C7—C16—C13 | 0.5 (7) | C7—C8—N4—Ru1 | 179.3 (3) |
C8—C7—C16—C6 | −179.5 (4) | C18—C17—N5—C21 | −0.3 (6) |
N5—C17—C18—C19 | −2.0 (7) | C18—C17—N5—Ru1 | 174.2 (3) |
N5—C17—C18—C27 | 178.1 (5) | C20—C21—N5—C17 | 2.1 (6) |
C17—C18—C19—C20 | 2.4 (7) | C22—C21—N5—C17 | −178.6 (4) |
C27—C18—C19—C20 | −177.7 (5) | C20—C21—N5—Ru1 | −173.0 (3) |
C17—C18—C19—C28 | −178.4 (5) | C22—C21—N5—Ru1 | 6.2 (4) |
C27—C18—C19—C28 | 1.6 (8) | C25—C26—N6—C22 | −2.0 (6) |
C18—C19—C20—C21 | −0.7 (7) | C25—C26—N6—Ru1 | 175.4 (3) |
C28—C19—C20—C21 | −179.9 (5) | C23—C22—N6—C26 | 1.2 (5) |
C19—C20—C21—N5 | −1.7 (7) | C21—C22—N6—C26 | 178.2 (3) |
C19—C20—C21—C22 | 179.2 (4) | C23—C22—N6—Ru1 | −176.5 (3) |
N5—C21—C22—N6 | −4.5 (5) | C21—C22—N6—Ru1 | 0.5 (4) |
C20—C21—C22—N6 | 174.8 (4) | C32—C31—N7—C35 | 2.1 (6) |
N5—C21—C22—C23 | 172.5 (4) | C32—C31—N7—Ru1 | −168.2 (3) |
C20—C21—C22—C23 | −8.3 (7) | C34—C35—N7—C31 | −1.5 (5) |
N6—C22—C23—C24 | −0.3 (6) | C36—C35—N7—C31 | −178.9 (3) |
C21—C22—C23—C24 | −177.1 (4) | C34—C35—N7—Ru1 | 169.9 (3) |
C22—C23—C24—C25 | 0.1 (6) | C36—C35—N7—Ru1 | −7.5 (4) |
C22—C23—C24—C29 | 178.5 (4) | C39—C40—N8—C36 | 1.5 (6) |
C23—C24—C25—C26 | −0.8 (6) | C39—C40—N8—Ru1 | −170.6 (3) |
C29—C24—C25—C26 | −179.2 (4) | C37—C36—N8—C40 | −3.5 (6) |
C23—C24—C25—C30 | 178.7 (4) | C35—C36—N8—C40 | 177.3 (3) |
C29—C24—C25—C30 | 0.3 (6) | C37—C36—N8—Ru1 | 169.6 (3) |
C24—C25—C26—N6 | 1.8 (6) | C35—C36—N8—Ru1 | −9.6 (4) |
Cg1, Cg2 and Cg3 denote the centroids of the N7/C31–C35, N8/C36–C40 and N6/C22–C26 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···F10i | 0.93 | 2.61 | 3.402 (7) | 143 |
C3—H3···F10i | 0.93 | 2.50 | 3.318 (8) | 147 |
C6—H6···F8ii | 0.93 | 2.58 | 3.218 (8) | 126 |
C8—H8···N7 | 0.93 | 2.65 | 3.166 (5) | 116 |
C20—H20···F1Aiii | 0.93 | 2.41 | 3.320 (6) | 166 |
C20—H20···F5Ciii | 0.93 | 2.64 | 3.411 (15) | 141 |
C23—H23···F1Aiii | 0.93 | 2.55 | 3.479 (5) | 177 |
C26—H26···N8 | 0.93 | 2.59 | 3.138 (5) | 118 |
C31—H31···F6A | 0.93 | 2.63 | 3.461 (13) | 150 |
C34—H34···F5Aiv | 0.93 | 2.29 | 3.170 (8) | 158 |
C34—H34···F6Biv | 0.93 | 2.30 | 3.129 (11) | 148 |
C34—H34···F6Civ | 0.93 | 2.55 | 3.295 (19) | 137 |
C45—H45A···F11ii | 0.96 | 2.49 | 3.343 (12) | 148 |
C45—H45C···F11 | 0.96 | 2.58 | 3.388 (15) | 142 |
C47—H47A···N9v | 0.96 | 2.66 | 3.452 (14) | 140 |
C47—H47B···F5Biii | 0.96 | 2.55 | 3.343 (16) | 140 |
C47—H47B···F5Ciii | 0.96 | 2.59 | 3.293 (15) | 131 |
C8—H8···Cg1 | 0.93 | 2.92 | 3.711 (5) | 144 |
C26—H26···Cg2 | 0.93 | 2.90 | 3.708 (4) | 146 |
C42—H42A···Cg3vi | 0.96 | 2.79 | 3.339 (5) | 117 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, −y, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) x, y+1, z; (vi) −x+1, −y+2, −z+1. |
N1—Ru1 | 2.048 (3) | N6—Ru1 | 2.065 (3) |
N4—Ru1 | 2.047 (3) | N7—Ru1 | 2.063 (3) |
N5—Ru1 | 2.074 (3) | N8—Ru1 | 2.061 (3) |
Cg1, Cg2 and Cg3 denote the centroids of the N7/C31–C35, N8/C36–C40 and N6/C22–C26 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···F10i | 0.93 | 2.61 | 3.402 (7) | 143 |
C3—H3···F10i | 0.93 | 2.50 | 3.318 (8) | 147 |
C6—H6···F8ii | 0.93 | 2.58 | 3.218 (8) | 126 |
C8—H8···N7 | 0.93 | 2.65 | 3.166 (5) | 116 |
C20—H20···F1Aiii | 0.93 | 2.41 | 3.320 (6) | 166 |
C20—H20···F5Ciii | 0.93 | 2.64 | 3.411 (15) | 141 |
C23—H23···F1Aiii | 0.93 | 2.55 | 3.479 (5) | 177 |
C26—H26···N8 | 0.93 | 2.59 | 3.138 (5) | 118 |
C31—H31···F6A | 0.93 | 2.63 | 3.461 (13) | 150 |
C34—H34···F5Aiv | 0.93 | 2.29 | 3.170 (8) | 158 |
C34—H34···F6Biv | 0.93 | 2.30 | 3.129 (11) | 148 |
C34—H34···F6Civ | 0.93 | 2.55 | 3.295 (19) | 137 |
C45—H45A···F11ii | 0.96 | 2.49 | 3.343 (12) | 148 |
C45—H45C···F11 | 0.96 | 2.58 | 3.388 (15) | 142 |
C47—H47A···N9v | 0.96 | 2.66 | 3.452 (14) | 140 |
C47—H47B···F5Biii | 0.96 | 2.55 | 3.343 (16) | 140 |
C47—H47B···F5Ciii | 0.96 | 2.59 | 3.293 (15) | 131 |
C8—H8···Cg1 | 0.93 | 2.92 | 3.711 (5) | 144 |
C26—H26···Cg2 | 0.93 | 2.90 | 3.708 (4) | 146 |
C42—H42A···Cg3vi | 0.96 | 2.79 | 3.339 (5) | 117 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, −y, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) x, y+1, z; (vi) −x+1, −y+2, −z+1. |
References
Bergman, S. D., Goldberg, I., Barbieri, A., Barigelletti, F. & Kol, M. (2004). Inorg. Chem. 43, 2355–2367. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bergman, S. D., Goldberg, I., Barbieri, A. & Kol, M. (2005). Inorg. Chem. 44, 2513–2523. Web of Science CSD CrossRef PubMed CAS Google Scholar
Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Brietzke, T., Mickler, W., Kelling, A. & Holdt, H.-J. (2012). Dalton Trans. 41, 2788–2797. Web of Science CSD CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gut, D., Rudi, A., Kopilov, J., Goldberg, I. & Kol, M. (2002). J. Am. Chem. Soc. 124, 5449–5456. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rudia, A., Benayahub, Y., Goldberg, I. & Kasham Eilatin, Y. (1988). Tetrahedron Lett. 29, 6655–6656. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2011). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.