metal-organic compounds
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Chlorido(η6-p-cymene)[2-(5-phenyl-4H-1,2,4-triazol-3-yl-κN2)pyridine-κN]ruthenium(II) chloride
aVolodymyrska 64 Street, Kiev, Ukraine
*Correspondence e-mail: a.a.sikalov@gmail.com
In the title compound, [RuCl(C10H14)(C13H10N4)]Cl, the pyridyltriazole fragment of the bidentate ligand is essentially planar [dihedral angle = 0.8 (1)°], while the phenyl substituent is inclined at 19.4 (1)° to the 1,2,4-triazole ring. In the crystal, the complex cations are packed in sheets with no particularly strong interactions between them. The Cl− anions are bound to the cations by unusually strong N—H⋯Cl hydrogen bonds.
Keywords: crystal structure; ruthenium; p-cymene; coordination chemistry; hydrogen bonding; pyridyltriazoles.
CCDC reference: 1839210
Structure description
Recently, ruthenium(II) π-arene complexes have been of increasing interest – mostly due to their anticancer properties (Süss-Fink, 2010) and their in transfer hydrogenation reactions (Hohloch et al., 2013). Therefore, it is of great importance to know the structural details of these compounds. We have synthesized an example of a ruthenium(II) p-cymene complex with a pyridyl-1,2,4-triazole ligand in the 4H-tautomeric form. The molecular structure of the title compound is shown in Fig. 1. As is traditional for this kind of compounds, the cation exhibits a distorted octahedral piano-stool geometry with p-cymene as a π-bound hexahapto ligand, a chloride anion as a monodentate ligand and the 3-(2-pyridyl)-5-phenyl-1,2,4-triazole as a bidentate chelating N,N-donor ligand. It is interesting that while the pyridyltriazole moiety is virtually planar with a dihedral angle of a mere 0.8 (1)° between the pyridine and triazole rings, the phenyl ring does not lie in this plane and is inclined at 19.4 (1)° to the triazole ring plane, even though there is no apparent to cause this. We surmise that the fact that the 2-(5-phenyl-4H-1,2,4-triazol-3-yl)pyridine ligand is coordinated via N4 arises from unfavourable steric interactions (between the phenyl group and the p-cymene ligand), which would take place in a hypothetical analogue of the title compound where the ligand is coordinated via N7.
As shown in Fig. 2, the title compound features an intriguing hydrogen bond formed between the N—H group of the 1,2,4-triazole ring and the chloride counter-ion (Table 1). The relatively short H⋯Cl distance and an NH⋯Cl angle close to 180° suggest an atypical strength of the bond as compared to other N—H⋯Cl hydrogen bonds, excluding charge-assisted hydrogen bonds (Steed & Atwood, 2009). Unexpectedly, the title compound does not exhibit any significant π-stacking interactions [the shortest centroid–centroid distance is 4.122 Å (offset) and the shortest C—H⋯centroid distance is 3.453 Å].
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It appears that crystal structures of ruthenium(II) p-cymene complexes bearing 3-(2-pyridyl)-1,2,4-triazoles have not been published until now. The two most closely related crystal structures are those of η5-cyclopentadienyl analogues, which also differ from the title compound by variations in the 3-(2-pyridyl)-1,2,4-triazole ligands and by replacement of the chlorido ligand by PPh3 in the inner coordination sphere. The Ru1—N4 and Ru1—N5 bond lengths [2.072 (3) and 2.132 (2) Å, respectively] in the title compound are comparable to those in the related compounds mentioned above [respective bond distances are 2.069 (3) and 2.125 (3) Å (Gupta et al., 2010) and 2.089 (4) and 2.119 (3) Å (Gupta et al., 2012)].
Synthesis and crystallization
The ruthenium(II) p-cymene dichloride dimer (244.8 mg, 0.4 mmol) was dissolved in about 3 ml of methanol. After complete dissolution of the starting compound, 2-(5-phenyl-4H-1,2,4-triazol-3-yl)pyridine (355.2 mg, 0.8 mmol) was added to the clear red solution. Within 30 minutes, the reaction mixture adopted a reddish–orange hue and red prismatic crystals suitable for single-crystal XRD analysis began to form on the bottom and sides of the reaction vessel. Several crystals were harvested, and then the solvent was distilled off with the use of a rotary evaporator. Yield: 93%. Schematic representation of the synthesis is given in Fig. 3.
1H NMR (400 MHz, DMSO-δ6): δ(p.p.m.) 9.43 (d, J = 4.2 Hz, 1H, pyαH), 8.30–8.08 (m, 3H, pyβH, pyβ′H and pyγH), 7.83–7.26 (m, 5H, phenyl), 6.14 (d, J = 5.0 Hz, 1H, p-cymene CH), 6.02 (d, J = 4.9 Hz, 1H, p-cymene CH), 5.93 (d, J = 4.9 Hz, 1H, p-cymene CH), 5.80 (d, J = 5.0 Hz, 1H, p-cymene CH), 2.74–2.63 (m, 1H, CH from iPr), 2.17 (s, 3H, Me from p-cymene), 1.06 (d, J = 6.8 Hz, 3H, Me from iPr), 0.98 (d, J = 6.7 Hz, 3H, Me from iPr).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1839210
https://doi.org/10.1107/S2414314618006259/sj4174sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618006259/sj4174Isup2.hkl
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[RuCl(C10H14)(C13H10N4)]Cl | Z = 1 |
Mr = 528.44 | F(000) = 267.999 |
Triclinic, P1 | Dx = 1.574 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4704 (2) Å | Cell parameters from 8029 reflections |
b = 8.7593 (3) Å | θ = 2–32° |
c = 10.1975 (4) Å | µ = 0.96 mm−1 |
α = 101.425 (3)° | T = 200 K |
β = 97.379 (3)° | Prism, clear intense red |
γ = 95.337 (3)° | 0.35 × 0.20 × 0.20 mm |
V = 557.62 (3) Å3 |
Agilent Xcalibur, Eos with CCD area detector diffractometer | 7220 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 32.7°, θmin = 2.1° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.81, Tmax = 0.83 | k = −13→13 |
13071 measured reflections | l = −15→15 |
7295 independent reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.02P)2 + 0.15P] , where P = (max(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.062 | (Δ/σ)max = 0.001 |
S = 0.98 | Δρmax = 0.56 e Å−3 |
7295 reflections | Δρmin = −0.40 e Å−3 |
276 parameters | Absolute structure: Flack (1983), 3505 Friedel-pairs |
7 restraints | Absolute structure parameter: −0.03 (2) |
Primary atom site location: other |
x | y | z | Uiso*/Ueq | ||
Ru1 | 0.86321 (8) | 0.38802 (6) | 0.54014 (6) | 0.0176 | |
Cl2 | 0.67364 (12) | 0.60046 (10) | 0.49812 (9) | 0.0272 | |
Cl3 | 0.38532 (13) | 0.18193 (12) | −0.10651 (9) | 0.0382 | |
N4 | 0.6317 (4) | 0.2491 (3) | 0.3951 (2) | 0.0217 | |
N5 | 0.9711 (4) | 0.4024 (3) | 0.3535 (2) | 0.0205 | |
N6 | 0.4495 (3) | 0.1562 (3) | 0.3969 (2) | 0.0224 | |
N7 | 0.4792 (3) | 0.1708 (3) | 0.1855 (2) | 0.0220 | |
C8 | 1.0648 (5) | 0.5307 (4) | 0.7248 (3) | 0.0242 | |
C9 | 0.6471 (4) | 0.2555 (3) | 0.2682 (2) | 0.0197 | |
C10 | 0.7853 (5) | 0.3174 (4) | 0.7245 (3) | 0.0269 | |
C11 | 1.1560 (4) | 0.4760 (3) | 0.3399 (3) | 0.0252 | |
C12 | 0.3595 (4) | 0.1103 (3) | 0.2695 (3) | 0.0212 | |
C13 | 0.8319 (4) | 0.3402 (3) | 0.2389 (3) | 0.0217 | |
C14 | 1.1769 (4) | 0.4165 (3) | 0.6582 (3) | 0.0266 | |
C15 | 0.8723 (4) | 0.3530 (3) | 0.1111 (3) | 0.0294 | |
C16 | 0.8650 (4) | 0.4755 (3) | 0.7562 (3) | 0.0269 | |
C17 | 0.1609 (4) | 0.0092 (3) | 0.2237 (3) | 0.0227 | |
C18 | −0.1477 (6) | −0.0882 (5) | 0.0591 (4) | 0.0390 | |
C19 | 1.0659 (4) | 0.4275 (4) | 0.0989 (3) | 0.0318 | |
C20 | 1.2075 (4) | 0.4896 (4) | 0.2144 (3) | 0.0299 | |
C21 | 0.9010 (4) | 0.2016 (3) | 0.6564 (3) | 0.0276 | |
C22 | 1.1445 (4) | 0.7045 (3) | 0.7648 (3) | 0.0300 | |
C23 | 0.0847 (5) | −0.0834 (4) | 0.3077 (3) | 0.0350 | |
C24 | 1.0990 (4) | 0.2552 (4) | 0.6249 (3) | 0.0279 | |
C25 | −0.2238 (5) | −0.1779 (4) | 0.1438 (3) | 0.0421 | |
C26 | 0.0434 (4) | 0.0051 (4) | 0.0982 (3) | 0.0310 | |
C27 | 1.2355 (5) | 0.7703 (4) | 0.6552 (3) | 0.0395 | |
C28 | −0.1071 (5) | −0.1770 (4) | 0.2670 (3) | 0.0433 | |
C29 | 0.8085 (6) | 0.0338 (4) | 0.6203 (4) | 0.0445 | |
C30 | 1.3064 (6) | 0.7305 (4) | 0.8939 (4) | 0.0505 | |
H71 | 0.451 (3) | 0.160 (3) | 0.1007 (18) | 0.0278 (19)* | |
H111 | 1.2519 | 0.5190 | 0.4165 | 0.0292* | |
H141 | 1.3038 | 0.4499 | 0.6226 | 0.0345* | |
H151 | 0.7718 | 0.3117 | 0.0351 | 0.0363* | |
H161 | 0.7756 | 0.5545 | 0.7899 | 0.0341* | |
H181 | −0.2263 | −0.0894 | −0.0232 | 0.0473* | |
H191 | 1.1020 | 0.4339 | 0.0136 | 0.0391* | |
H201 | 1.3382 | 0.5360 | 0.2072 | 0.0359* | |
H221 | 1.0243 | 0.7611 | 0.7874 | 0.0381* | |
H231 | 0.1642 | −0.0822 | 0.3918 | 0.0421* | |
H241 | 1.1754 | 0.1828 | 0.5704 | 0.0352* | |
H251 | −0.3543 | −0.2396 | 0.1181 | 0.0508* | |
H261 | 0.0930 | 0.0653 | 0.0394 | 0.0384* | |
H271 | 1.3590 | 0.7220 | 0.6351 | 0.0610* | |
H272 | 1.2764 | 0.8813 | 0.6860 | 0.0609* | |
H273 | 1.1347 | 0.7520 | 0.5733 | 0.0611* | |
H281 | −0.1561 | −0.2397 | 0.3228 | 0.0532* | |
H291 | 0.8511 | −0.0189 | 0.5382 | 0.0682* | |
H293 | 0.8554 | −0.0149 | 0.6927 | 0.0682* | |
H292 | 0.6578 | 0.0253 | 0.6089 | 0.0680* | |
H301 | 1.2398 | 0.7033 | 0.9668 | 0.0790* | |
H303 | 1.4155 | 0.6662 | 0.8771 | 0.0789* | |
H302 | 1.3657 | 0.8396 | 0.9189 | 0.0788* | |
H101 | 0.6409 | 0.2853 | 0.7369 | 0.0348* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.01437 (7) | 0.02394 (8) | 0.01423 (7) | 0.00019 (5) | 0.00201 (5) | 0.00478 (6) |
Cl2 | 0.0199 (3) | 0.0299 (3) | 0.0327 (4) | 0.0052 (3) | 0.0026 (3) | 0.0090 (3) |
Cl3 | 0.0336 (4) | 0.0593 (5) | 0.0200 (3) | −0.0087 (3) | 0.0005 (3) | 0.0134 (3) |
N4 | 0.0213 (11) | 0.0260 (11) | 0.0172 (12) | −0.0043 (9) | 0.0043 (9) | 0.0054 (9) |
N5 | 0.0156 (10) | 0.0278 (12) | 0.0182 (10) | 0.0016 (9) | 0.0031 (8) | 0.0055 (9) |
N6 | 0.0204 (10) | 0.0244 (10) | 0.0204 (10) | −0.0055 (8) | 0.0013 (8) | 0.0052 (8) |
N7 | 0.0222 (10) | 0.0261 (11) | 0.0165 (10) | −0.0041 (8) | 0.0020 (8) | 0.0052 (8) |
C8 | 0.0198 (13) | 0.0308 (15) | 0.0185 (15) | −0.0021 (11) | −0.0049 (10) | 0.0041 (12) |
C9 | 0.0194 (11) | 0.0237 (12) | 0.0156 (11) | −0.0009 (9) | 0.0022 (8) | 0.0053 (9) |
C10 | 0.0234 (14) | 0.0414 (18) | 0.0177 (12) | −0.0001 (12) | 0.0040 (10) | 0.0121 (13) |
C11 | 0.0186 (11) | 0.0336 (14) | 0.0226 (12) | −0.0014 (10) | 0.0041 (9) | 0.0058 (11) |
C12 | 0.0193 (11) | 0.0235 (12) | 0.0211 (12) | 0.0004 (9) | 0.0043 (9) | 0.0056 (10) |
C13 | 0.0185 (11) | 0.0261 (12) | 0.0198 (12) | −0.0011 (9) | 0.0022 (9) | 0.0055 (10) |
C14 | 0.0184 (11) | 0.0393 (15) | 0.0224 (12) | 0.0025 (10) | −0.0030 (9) | 0.0119 (11) |
C15 | 0.0288 (14) | 0.0392 (15) | 0.0193 (12) | −0.0043 (12) | 0.0043 (10) | 0.0073 (11) |
C16 | 0.0259 (13) | 0.0371 (15) | 0.0159 (11) | 0.0025 (11) | 0.0019 (9) | 0.0030 (11) |
C17 | 0.0212 (11) | 0.0231 (12) | 0.0224 (12) | −0.0026 (9) | 0.0029 (9) | 0.0038 (10) |
C18 | 0.0271 (14) | 0.052 (3) | 0.032 (2) | −0.0112 (16) | −0.0040 (14) | 0.0070 (18) |
C19 | 0.0312 (14) | 0.0440 (17) | 0.0217 (13) | −0.0024 (12) | 0.0088 (11) | 0.0106 (12) |
C20 | 0.0210 (12) | 0.0405 (16) | 0.0293 (14) | −0.0038 (11) | 0.0085 (10) | 0.0103 (12) |
C21 | 0.0326 (14) | 0.0282 (13) | 0.0220 (12) | 0.0020 (11) | −0.0011 (10) | 0.0094 (10) |
C22 | 0.0247 (13) | 0.0341 (15) | 0.0262 (13) | 0.0011 (11) | −0.0008 (10) | −0.0013 (11) |
C23 | 0.0360 (15) | 0.0386 (16) | 0.0280 (14) | −0.0129 (13) | −0.0004 (12) | 0.0127 (12) |
C24 | 0.0260 (14) | 0.0356 (16) | 0.0238 (14) | 0.0114 (12) | 0.0006 (11) | 0.0088 (12) |
C25 | 0.0306 (15) | 0.0471 (19) | 0.0424 (18) | −0.0161 (13) | 0.0014 (13) | 0.0071 (15) |
C26 | 0.0255 (13) | 0.0375 (16) | 0.0279 (14) | −0.0049 (11) | 0.0017 (11) | 0.0073 (12) |
C27 | 0.0418 (17) | 0.0321 (15) | 0.0435 (18) | −0.0019 (13) | 0.0135 (14) | 0.0037 (14) |
C28 | 0.0392 (17) | 0.0482 (19) | 0.0393 (18) | −0.0180 (15) | 0.0049 (14) | 0.0131 (15) |
C29 | 0.051 (2) | 0.0342 (16) | 0.050 (2) | 0.0026 (15) | 0.0041 (16) | 0.0180 (15) |
C30 | 0.051 (2) | 0.048 (2) | 0.0396 (19) | −0.0053 (17) | −0.0179 (16) | −0.0004 (16) |
Ru1—Cl2 | 2.399 (3) | C15—H151 | 0.933 |
Ru1—N4 | 2.072 (3) | C16—H161 | 0.981 |
Ru1—N5 | 2.132 (2) | C17—C23 | 1.394 (4) |
Ru1—C8 | 2.223 (3) | C17—C26 | 1.394 (4) |
Ru1—C10 | 2.195 (3) | C18—C25 | 1.382 (5) |
Ru1—C14 | 2.189 (3) | C18—C26 | 1.383 (5) |
Ru1—C16 | 2.183 (3) | C18—H181 | 0.922 |
Ru1—C21 | 2.213 (3) | C19—C20 | 1.378 (4) |
Ru1—C24 | 2.195 (3) | C19—H191 | 0.940 |
N4—N6 | 1.373 (3) | C20—H201 | 0.922 |
N4—C9 | 1.322 (3) | C21—C24 | 1.421 (4) |
N5—C11 | 1.342 (3) | C21—C29 | 1.490 (4) |
N5—C13 | 1.363 (4) | C22—C27 | 1.513 (4) |
N6—C12 | 1.320 (3) | C22—C30 | 1.538 (4) |
N7—C9 | 1.345 (3) | C22—H221 | 0.988 |
N7—C12 | 1.374 (3) | C23—C28 | 1.388 (4) |
N7—H71 | 0.846 (17) | C23—H231 | 0.939 |
C8—C14 | 1.407 (4) | C24—H241 | 0.972 |
C8—C16 | 1.435 (4) | C25—C28 | 1.379 (5) |
C8—C22 | 1.518 (4) | C25—H251 | 0.936 |
C9—C13 | 1.444 (3) | C26—H261 | 0.940 |
C10—C16 | 1.391 (4) | C27—H271 | 0.964 |
C10—C21 | 1.438 (4) | C27—H272 | 0.961 |
C10—H101 | 0.982 | C27—H273 | 0.967 |
C11—C20 | 1.388 (4) | C28—H281 | 0.930 |
C11—H111 | 0.924 | C29—H291 | 0.959 |
C12—C17 | 1.458 (3) | C29—H293 | 0.955 |
C13—C15 | 1.386 (3) | C29—H292 | 0.961 |
C14—C24 | 1.414 (4) | C30—H301 | 0.963 |
C14—H141 | 0.983 | C30—H303 | 0.955 |
C15—C19 | 1.390 (4) | C30—H302 | 0.967 |
Cl2—Ru1—N4 | 84.77 (8) | Ru1—C14—H141 | 122.1 |
Cl2—Ru1—N5 | 83.97 (7) | C8—C14—H141 | 119.4 |
N4—Ru1—N5 | 76.14 (9) | C24—C14—H141 | 118.0 |
Cl2—Ru1—C8 | 94.13 (9) | C13—C15—C19 | 118.5 (3) |
N4—Ru1—C8 | 168.20 (9) | C13—C15—H151 | 120.5 |
N5—Ru1—C8 | 115.48 (10) | C19—C15—H151 | 121.0 |
Cl2—Ru1—C10 | 109.97 (9) | Ru1—C16—C8 | 72.50 (16) |
N4—Ru1—C10 | 101.13 (11) | Ru1—C16—C10 | 71.95 (16) |
N5—Ru1—C10 | 165.66 (9) | C8—C16—C10 | 122.3 (3) |
C8—Ru1—C10 | 68.16 (12) | Ru1—C16—H161 | 121.8 |
Cl2—Ru1—C14 | 124.65 (8) | C8—C16—H161 | 117.5 |
N4—Ru1—C14 | 148.83 (11) | C10—C16—H161 | 119.7 |
N5—Ru1—C14 | 95.31 (9) | C12—C17—C23 | 119.5 (2) |
C8—Ru1—C14 | 37.19 (11) | C12—C17—C26 | 121.3 (2) |
C10—Ru1—C14 | 79.71 (11) | C23—C17—C26 | 119.2 (2) |
Cl2—Ru1—C16 | 88.32 (8) | C25—C18—C26 | 120.5 (4) |
N4—Ru1—C16 | 130.20 (10) | C25—C18—H181 | 119.6 |
N5—Ru1—C16 | 151.76 (10) | C26—C18—H181 | 119.9 |
C8—Ru1—C16 | 38.00 (11) | C15—C19—C20 | 118.8 (2) |
C10—Ru1—C16 | 37.05 (11) | C15—C19—H191 | 121.1 |
Cl2—Ru1—C21 | 146.94 (8) | C20—C19—H191 | 120.1 |
N4—Ru1—C21 | 93.12 (10) | C11—C20—C19 | 119.9 (2) |
N5—Ru1—C21 | 127.60 (10) | C11—C20—H201 | 120.5 |
C8—Ru1—C21 | 81.38 (11) | C19—C20—H201 | 119.6 |
C10—Ru1—C21 | 38.07 (11) | Ru1—C21—C10 | 70.29 (16) |
Cl2—Ru1—C24 | 161.72 (8) | Ru1—C21—C24 | 70.50 (15) |
N4—Ru1—C24 | 113.51 (12) | C10—C21—C24 | 117.4 (3) |
N5—Ru1—C24 | 100.26 (10) | Ru1—C21—C29 | 129.3 (2) |
C8—Ru1—C24 | 67.92 (12) | C10—C21—C29 | 119.4 (3) |
C10—Ru1—C24 | 67.60 (11) | C24—C21—C29 | 123.3 (3) |
C14—Ru1—C16 | 67.15 (10) | C8—C22—C27 | 114.4 (2) |
C14—Ru1—C21 | 68.15 (10) | C8—C22—C30 | 107.7 (3) |
C16—Ru1—C21 | 68.00 (11) | C27—C22—C30 | 111.2 (3) |
C14—Ru1—C24 | 37.62 (11) | C8—C22—H221 | 107.5 |
C16—Ru1—C24 | 79.57 (11) | C27—C22—H221 | 108.0 |
C21—Ru1—C24 | 37.60 (11) | C30—C22—H221 | 107.9 |
Ru1—N4—N6 | 135.48 (17) | C17—C23—C28 | 120.1 (3) |
Ru1—N4—C9 | 115.74 (18) | C17—C23—H231 | 119.5 |
N6—N4—C9 | 108.6 (2) | C28—C23—H231 | 120.3 |
Ru1—N5—C11 | 125.85 (19) | Ru1—C24—C21 | 71.89 (15) |
Ru1—N5—C13 | 116.14 (17) | Ru1—C24—C14 | 70.97 (15) |
C11—N5—C13 | 117.8 (2) | C21—C24—C14 | 121.0 (3) |
N4—N6—C12 | 106.0 (2) | Ru1—C24—H241 | 123.9 |
C9—N7—C12 | 105.0 (2) | C21—C24—H241 | 120.0 |
C9—N7—H71 | 127.5 (12) | C14—C24—H241 | 118.6 |
C12—N7—H71 | 127.5 (12) | C18—C25—C28 | 120.0 (3) |
Ru1—C8—C14 | 70.11 (16) | C18—C25—H251 | 120.5 |
Ru1—C8—C16 | 69.50 (16) | C28—C25—H251 | 119.5 |
C14—C8—C16 | 116.6 (3) | C17—C26—C18 | 120.0 (3) |
Ru1—C8—C22 | 131.5 (2) | C17—C26—H261 | 120.6 |
C14—C8—C22 | 123.8 (3) | C18—C26—H261 | 119.4 |
C16—C8—C22 | 119.6 (3) | C22—C27—H271 | 109.8 |
N7—C9—N4 | 109.8 (2) | C22—C27—H272 | 109.7 |
N7—C9—C13 | 130.9 (2) | H271—C27—H272 | 108.0 |
N4—C9—C13 | 119.2 (2) | C22—C27—H273 | 111.2 |
Ru1—C10—C16 | 71.00 (16) | H271—C27—H273 | 109.1 |
Ru1—C10—C21 | 71.64 (15) | H272—C27—H273 | 109.0 |
C16—C10—C21 | 120.7 (3) | C23—C28—C25 | 120.2 (3) |
Ru1—C10—H101 | 122.9 | C23—C28—H281 | 119.8 |
C16—C10—H101 | 120.0 | C25—C28—H281 | 120.0 |
C21—C10—H101 | 118.8 | C21—C29—H291 | 110.7 |
N5—C11—C20 | 122.1 (3) | C21—C29—H293 | 108.3 |
N5—C11—H111 | 118.9 | H291—C29—H293 | 109.8 |
C20—C11—H111 | 119.0 | C21—C29—H292 | 110.6 |
N7—C12—N6 | 110.7 (2) | H291—C29—H292 | 109.1 |
N7—C12—C17 | 124.4 (2) | H293—C29—H292 | 108.3 |
N6—C12—C17 | 124.9 (2) | C22—C30—H301 | 110.0 |
C9—C13—N5 | 111.6 (2) | C22—C30—H303 | 109.2 |
C9—C13—C15 | 125.5 (2) | H301—C30—H303 | 109.5 |
N5—C13—C15 | 122.8 (2) | C22—C30—H302 | 109.4 |
Ru1—C14—C8 | 72.71 (16) | H301—C30—H302 | 109.3 |
Ru1—C14—C24 | 71.41 (15) | H303—C30—H302 | 109.5 |
C8—C14—C24 | 122.1 (3) |
References
Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gupta, G., Prasad, K. T., Das, B. & Rao, K. M. (2010). Polyhedron, 29, 904–910. CSD CrossRef CAS Google Scholar
Gupta, G., Therrien, B., Park, S., Lee, S. S. & Kim, J. (2012). J. Coord. Chem. 65, 2523–2534. CSD CrossRef CAS Google Scholar
Hohloch, S., Suntrup, L. & Sarkar, B. (2013). Organometallics, 32, 7376–7385. CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steed, J. W. & Atwood, J. L. (2009). Supramolecular Chemistry. Chichester: John Wiley & Sons. Google Scholar
Süss-Fink, G. (2010). Dalton Trans. 39, 1673–1688. Web of Science PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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