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Acta Cryst. (2008). E64, m254-m255    [ doi:10.1107/S1600536807066883 ]

Bis(2-phenyl-4,6-di-2-pyridyl-1,3,5-triazine-[kappa]3N4,N5,N6)ruthenium(II) bis(hexafluoridophosphate)

M. I. J. Polson and G. S. Hanan

Abstract top

The asymmetric unit of the title compound, [Ru(C19H13N5)2](PF6)2, consists of an RuII complex cation and two hexafluoridophosphate anions. The RuII atom is coordinated by three N atoms from the two outer pyridine and the central triazine rings of each of two tridentate ligands in a distorted octahedral environment. The ligands are approximately orthogonal to one another, with a dihedral angle of 88.34 (2)° between planes through the three six-membered rings of the two ligands. The pendant phenyl substituents are almost coplanar with the triazine rings to which they are bound, with dihedral angles of 5.41 (9) and 14.90 (10)°. This is reflected in the previously reported photophysical results with an increased lifetime of the triplet metal to ligand charge transfer (3MLCT) excited state [Fang, Taylor, Hanan, Loiseau, Passalacqua, Campagna, Nierengarten & Van Dorsselaer (2002). J. Am. Chem. Soc. 124, 7912-7913].

Comment top

The structure of the title compound reveals the ruthenium(II) atom to be in a distorted octahedral environment, Table 1. The Ru—N bond lengths to the central triazine ring are significantly shortened when compared to those of the outer pyridine rings. The angles between the coordinating pyridine N atoms also deviate significantly from 180 ° indicating considerable distortion.

Ruthenium complexes of this type have long been known to exhibit surprisingly short lived excited states. This is due to rapid deactivation of the excited state through a low lying metal centred state (Kalyanasundaram, 1991; Barigelletti et al., 1995). By lowering the energy of the triplet metal to ligand charge transfer 3MLCT state, this exchange can be slowed and the lifetime of the excited state is extended (Fang et al., 2002). In the title compound (1) replacement of a the central pyridine ring with a triazine ring in complex with a 4-phenyl substituent allows the pendant phenyl ring to adopt an arrangement in which it is approximately co-planar with the rest of the ligand. This results from the removal of stericically conflicting C—H···H—C interactions and the addition of attractive intramolecular C—H···N interactions. Although the C—H···N angles are acute (approximately 100 °) they are typical of interactions in molecules of this kind (Fitchett et al., 2005) with N···H lengths of 2.47 to 2.52 Å, Table 2. The greater overall planarity of the ligands extends the HOMO orbital (predominately π* in nature) over more of the ligand surface, decreasing the energy of the 3MLCT state (Beley et al., 1991; Polson et al., 2002).

Related literature top

For related synthetic details see: Polson et al. (2002, 2004). For related structures, see: Polson et al. (2002). For general background on the photophysics of ruthenium polypyridyl complexes, see: Kalyanasundaram (1991); Barigelletti et al. (1995). For background on C—H···N interactions in α-diimines, see: Fitchett et al. (2005).

For related literature, see: Beley et al. (1991); Fang et al. (2002).

Experimental top

The complex was prepared as described by Polson et al. (2004). Crystals suitable for X-ray crystallography were prepared by the diffusion of diisopropyl ether into an acetonitrile solution of the complex over a week.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (1), showing displacement ellipsoids at the 50% probability level. All H atoms have been omitted for clarity.
Bis(2-phenyl-4,6-di-2-pyridyl-1,3,5-triazine- κ3N4,N5,N6)ruthenium(II) bis(hexafluoridophosphate) top
Crystal data top
[Ru(C19H13N5)2](PF6)2F000 = 2024
Mr = 1013.70Dx = 1.728 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7650 reflections
a = 9.0995 (3) Åθ = 4.7–53.0º
b = 32.5979 (11) ŵ = 0.59 mm−1
c = 13.1451 (5) ÅT = 93 (2) K
β = 91.774 (2)ºNeedle, red
V = 3897.3 (2) Å30.30 × 0.13 × 0.08 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		8114 independent reflections
Radiation source: sealed tube6511 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
T = 93(2) Kθmax = 26.6º
ω scansθmin = 2.5º
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −11→11
Tmin = 0.822, Tmax = 0.950k = −40→40
75901 measured reflectionsl = −16→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.066  w = 1/[σ2(Fo2) + (0.0562P)2 + 0.5007P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
8114 reflectionsΔρmax = 0.55 e Å−3
568 parametersΔρmin = −0.56 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ru(C19H13N5)2](PF6)2V = 3897.3 (2) Å3
Mr = 1013.70Z = 4
Monoclinic, P21/nMo Kα
a = 9.0995 (3) ŵ = 0.59 mm−1
b = 32.5979 (11) ÅT = 93 (2) K
c = 13.1451 (5) Å0.30 × 0.13 × 0.08 mm
β = 91.774 (2)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		8114 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		6511 reflections with I > 2σ(I)
Tmin = 0.822, Tmax = 0.950Rint = 0.060
75901 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027568 parameters
wR(F2) = 0.066H-atom parameters constrained
S = 0.99Δρmax = 0.55 e Å−3
8114 reflectionsΔρmin = −0.56 e Å−3
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
Ru10.511004 (17)0.118305 (4)0.711838 (12)0.01108 (5)
N100.71581 (17)0.12419 (5)0.64422 (12)0.0136 (4)
C100.8068 (2)0.09472 (6)0.61281 (16)0.0179 (5)
H100.78050.06690.62310.021*
C110.9375 (2)0.10327 (6)0.56596 (17)0.0232 (5)
H110.99780.08150.54330.028*
C120.9798 (2)0.14335 (6)0.55231 (17)0.0240 (5)
H121.07000.14960.52120.029*
C130.8884 (2)0.17461 (6)0.58476 (16)0.0192 (5)
H130.91500.20260.57650.023*
C140.7588 (2)0.16422 (5)0.62909 (15)0.0141 (4)
N200.53678 (17)0.17849 (5)0.70707 (12)0.0123 (3)
N210.67356 (18)0.23500 (5)0.65306 (13)0.0158 (4)
N220.44719 (18)0.24472 (5)0.73807 (12)0.0148 (4)
C200.6545 (2)0.19520 (6)0.66416 (15)0.0137 (4)
C210.5662 (2)0.25871 (6)0.69099 (15)0.0147 (4)
C220.4357 (2)0.20427 (6)0.74240 (15)0.0132 (4)
N300.31752 (18)0.14032 (5)0.77547 (12)0.0130 (3)
C300.2009 (2)0.11839 (6)0.80597 (16)0.0177 (4)
H300.20420.08930.80160.021*
C310.0766 (2)0.13690 (6)0.84348 (17)0.0220 (5)
H31−0.00400.12050.86330.026*
C320.0698 (2)0.17918 (6)0.85204 (17)0.0221 (5)
H32−0.01410.19210.87900.027*
C330.1878 (2)0.20221 (6)0.82050 (15)0.0180 (4)
H330.18580.23130.82470.022*
C340.3083 (2)0.18235 (6)0.78291 (15)0.0133 (4)
C400.5820 (2)0.30342 (6)0.67733 (16)0.0172 (4)
C410.6825 (2)0.31883 (6)0.60975 (17)0.0223 (5)
H410.74510.30070.57470.027*
C420.6911 (3)0.36089 (6)0.59355 (18)0.0268 (5)
H420.75850.37150.54640.032*
C430.6018 (3)0.38746 (6)0.64602 (18)0.0263 (5)
H430.60810.41620.63490.032*
C440.5033 (2)0.37218 (6)0.71460 (18)0.0237 (5)
H440.44330.39050.75130.028*
C450.4920 (2)0.33042 (6)0.72995 (17)0.0207 (5)
H450.42320.32000.77630.025*
N500.40436 (17)0.10703 (5)0.57094 (12)0.0124 (3)
C500.3662 (2)0.13390 (6)0.49749 (15)0.0141 (4)
H500.39030.16200.50730.017*
C510.2932 (2)0.12242 (6)0.40811 (16)0.0162 (4)
H510.26810.14240.35790.019*
C520.2572 (2)0.08161 (6)0.39243 (16)0.0172 (4)
H520.20630.07320.33180.021*
C530.2965 (2)0.05329 (6)0.46646 (15)0.0161 (4)
H530.27320.02510.45720.019*
C540.3700 (2)0.06633 (5)0.55407 (15)0.0120 (4)
N600.48400 (17)0.05829 (5)0.71489 (12)0.0129 (3)
N610.40078 (18)−0.00188 (5)0.63404 (12)0.0143 (4)
N620.51801 (18)−0.00465 (5)0.79959 (13)0.0147 (4)
C600.4180 (2)0.03841 (6)0.63663 (15)0.0137 (4)
C610.4496 (2)−0.02227 (6)0.71801 (15)0.0148 (4)
C620.5347 (2)0.03559 (6)0.79454 (15)0.0143 (4)
N700.61068 (17)0.10207 (5)0.85180 (12)0.0136 (4)
C700.6809 (2)0.12700 (6)0.91947 (15)0.0158 (4)
H700.67980.15570.90760.019*
C710.7543 (2)0.11210 (6)1.00527 (16)0.0187 (4)
H710.80370.13051.05080.022*
C720.7560 (2)0.07045 (6)1.02492 (16)0.0197 (5)
H720.80680.05991.08350.024*
C730.6820 (2)0.04436 (6)0.95750 (16)0.0173 (4)
H730.68030.01560.96950.021*
C740.6111 (2)0.06077 (6)0.87298 (15)0.0145 (4)
C800.4271 (2)−0.06706 (6)0.71991 (15)0.0155 (4)
C810.3459 (2)−0.08622 (6)0.64177 (16)0.0194 (5)
H810.3037−0.07030.58780.023*
C820.3265 (2)−0.12824 (6)0.64252 (18)0.0236 (5)
H820.2722−0.14110.58860.028*
C830.3860 (2)−0.15176 (6)0.72169 (18)0.0237 (5)
H830.3720−0.18060.72210.028*
C840.4651 (2)−0.13302 (6)0.79949 (17)0.0227 (5)
H840.5049−0.14900.85410.027*
C850.4873 (2)−0.09084 (6)0.79877 (16)0.0197 (5)
H850.5435−0.07820.85220.024*
P100.21119 (6)0.252045 (16)0.48554 (4)0.02011 (13)
F100.18421 (15)0.22740 (4)0.58837 (10)0.0386 (4)
F110.26219 (15)0.29172 (4)0.54874 (10)0.0327 (3)
F120.04573 (14)0.26820 (4)0.48256 (10)0.0362 (3)
F130.23965 (14)0.27617 (3)0.38108 (9)0.0250 (3)
F140.16179 (15)0.21244 (4)0.42100 (10)0.0339 (3)
F150.37791 (14)0.23611 (4)0.48793 (11)0.0353 (3)
P200.01052 (6)0.008488 (16)0.76644 (5)0.02301 (14)
F20−0.05493 (16)−0.01201 (4)0.86490 (11)0.0395 (4)
F21−0.04478 (14)0.05249 (3)0.80299 (10)0.0278 (3)
F22−0.14343 (15)0.00207 (4)0.70590 (11)0.0369 (4)
F230.07743 (16)0.02936 (4)0.66771 (11)0.0399 (4)
F240.06484 (16)−0.03543 (4)0.72907 (12)0.0396 (4)
F250.16550 (15)0.01533 (4)0.82574 (13)0.0452 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01126 (9)0.00884 (8)0.01317 (9)−0.00001 (6)0.00056 (6)−0.00003 (6)
N100.0122 (9)0.0126 (8)0.0159 (9)0.0005 (6)−0.0007 (7)0.0005 (7)
C100.0173 (11)0.0149 (10)0.0214 (12)0.0028 (8)−0.0001 (9)0.0018 (8)
C110.0189 (12)0.0222 (11)0.0288 (13)0.0087 (9)0.0053 (10)0.0020 (9)
C120.0129 (11)0.0274 (12)0.0320 (14)0.0020 (9)0.0074 (10)0.0044 (10)
C130.0155 (11)0.0182 (10)0.0240 (12)−0.0028 (8)0.0010 (9)0.0028 (9)
C140.0149 (11)0.0135 (9)0.0135 (11)−0.0004 (8)−0.0032 (8)−0.0011 (8)
N200.0124 (9)0.0125 (8)0.0120 (9)−0.0001 (6)−0.0015 (7)−0.0014 (6)
N210.0170 (9)0.0124 (8)0.0178 (10)−0.0018 (7)−0.0025 (7)−0.0012 (7)
N220.0182 (9)0.0106 (8)0.0153 (9)0.0016 (7)−0.0031 (7)−0.0012 (7)
C200.0127 (10)0.0152 (10)0.0130 (11)−0.0019 (8)−0.0031 (8)−0.0006 (8)
C210.0166 (11)0.0133 (9)0.0140 (11)−0.0020 (8)−0.0047 (8)−0.0014 (8)
C220.0112 (10)0.0144 (9)0.0136 (11)0.0006 (8)−0.0033 (8)−0.0012 (8)
N300.0139 (9)0.0137 (8)0.0114 (9)−0.0001 (7)−0.0002 (7)−0.0005 (6)
C300.0181 (11)0.0163 (10)0.0189 (11)−0.0040 (8)0.0010 (9)−0.0006 (8)
C310.0174 (12)0.0256 (11)0.0234 (13)−0.0048 (9)0.0069 (9)−0.0032 (9)
C320.0176 (11)0.0258 (11)0.0233 (13)0.0045 (9)0.0055 (9)−0.0038 (9)
C330.0198 (11)0.0168 (10)0.0174 (11)0.0017 (8)0.0010 (9)−0.0008 (8)
C340.0149 (10)0.0131 (9)0.0116 (10)−0.0011 (8)−0.0022 (8)0.0004 (8)
C400.0189 (11)0.0118 (9)0.0203 (12)−0.0021 (8)−0.0091 (9)0.0007 (8)
C410.0276 (13)0.0157 (10)0.0233 (13)−0.0021 (9)−0.0030 (10)−0.0006 (9)
C420.0321 (14)0.0194 (11)0.0283 (14)−0.0084 (10)−0.0078 (11)0.0061 (9)
C430.0321 (14)0.0129 (10)0.0329 (14)−0.0011 (9)−0.0184 (11)0.0019 (9)
C440.0225 (12)0.0155 (10)0.0326 (14)0.0019 (9)−0.0093 (10)−0.0031 (9)
C450.0195 (12)0.0162 (10)0.0260 (13)−0.0004 (8)−0.0067 (9)−0.0020 (9)
N500.0096 (8)0.0120 (8)0.0156 (9)0.0008 (6)0.0028 (7)−0.0017 (6)
C500.0124 (10)0.0136 (9)0.0164 (11)0.0022 (8)0.0038 (8)0.0010 (8)
C510.0140 (10)0.0165 (10)0.0182 (11)0.0045 (8)0.0019 (8)0.0029 (8)
C520.0164 (11)0.0210 (10)0.0143 (11)0.0026 (8)0.0006 (9)−0.0026 (8)
C530.0138 (10)0.0142 (9)0.0202 (12)0.0006 (8)0.0016 (9)−0.0032 (8)
C540.0087 (10)0.0133 (9)0.0142 (11)0.0018 (7)0.0041 (8)−0.0002 (8)
N600.0119 (9)0.0139 (8)0.0128 (9)0.0010 (6)0.0019 (7)0.0000 (7)
N610.0152 (9)0.0123 (8)0.0154 (9)0.0002 (7)0.0028 (7)0.0004 (7)
N620.0139 (9)0.0123 (8)0.0180 (10)−0.0002 (6)0.0026 (7)0.0007 (7)
C600.0100 (10)0.0145 (9)0.0168 (11)−0.0007 (8)0.0033 (8)−0.0020 (8)
C610.0127 (10)0.0142 (9)0.0177 (11)0.0010 (8)0.0047 (8)0.0004 (8)
C620.0114 (10)0.0148 (9)0.0171 (11)0.0019 (8)0.0032 (8)0.0028 (8)
N700.0125 (9)0.0119 (8)0.0166 (9)−0.0002 (7)0.0021 (7)−0.0002 (7)
C700.0156 (11)0.0142 (10)0.0177 (11)−0.0022 (8)0.0016 (9)−0.0021 (8)
C710.0185 (11)0.0209 (11)0.0165 (11)−0.0018 (9)−0.0016 (9)−0.0021 (8)
C720.0212 (12)0.0219 (10)0.0160 (12)0.0020 (9)−0.0003 (9)0.0026 (9)
C730.0180 (11)0.0146 (10)0.0194 (12)−0.0006 (8)0.0024 (9)0.0024 (8)
C740.0140 (10)0.0142 (9)0.0154 (11)0.0001 (8)0.0040 (8)0.0005 (8)
C800.0138 (11)0.0124 (9)0.0208 (12)0.0015 (8)0.0069 (9)0.0002 (8)
C810.0175 (11)0.0166 (10)0.0242 (12)0.0018 (8)0.0020 (9)0.0008 (9)
C820.0228 (12)0.0163 (10)0.0318 (14)−0.0018 (9)0.0008 (10)−0.0053 (9)
C830.0224 (12)0.0108 (10)0.0382 (15)−0.0009 (9)0.0062 (10)0.0008 (9)
C840.0247 (13)0.0158 (10)0.0280 (14)0.0038 (9)0.0044 (10)0.0068 (9)
C850.0194 (11)0.0171 (10)0.0228 (13)−0.0001 (9)0.0034 (9)0.0005 (9)
P100.0221 (3)0.0165 (3)0.0213 (3)−0.0062 (2)−0.0066 (2)0.0052 (2)
F100.0444 (9)0.0439 (8)0.0267 (8)−0.0221 (7)−0.0129 (7)0.0191 (6)
F110.0482 (9)0.0203 (6)0.0289 (8)−0.0060 (6)−0.0121 (7)−0.0017 (6)
F120.0238 (8)0.0526 (9)0.0321 (8)0.0031 (6)−0.0023 (6)0.0042 (7)
F130.0325 (8)0.0205 (6)0.0221 (7)−0.0048 (5)−0.0007 (6)0.0061 (5)
F140.0488 (9)0.0168 (6)0.0350 (8)−0.0108 (6)−0.0161 (7)0.0028 (6)
F150.0278 (8)0.0266 (7)0.0510 (9)0.0031 (6)−0.0085 (7)0.0075 (6)
P200.0197 (3)0.0132 (3)0.0362 (4)0.0013 (2)0.0028 (3)0.0045 (2)
F200.0471 (9)0.0261 (7)0.0462 (9)0.0023 (6)0.0159 (7)0.0127 (6)
F210.0287 (7)0.0152 (6)0.0396 (8)−0.0012 (5)0.0023 (6)−0.0028 (5)
F220.0330 (8)0.0214 (7)0.0556 (10)−0.0009 (6)−0.0114 (7)−0.0082 (6)
F230.0446 (9)0.0280 (7)0.0483 (10)0.0128 (6)0.0215 (7)0.0156 (7)
F240.0415 (9)0.0165 (6)0.0616 (10)0.0101 (6)0.0152 (7)0.0042 (6)
F250.0277 (8)0.0321 (8)0.0746 (12)−0.0004 (6)−0.0156 (8)0.0129 (8)
Geometric parameters (Å, °) top
Ru1—N102.0982 (16)C50—H500.9500
Ru1—N201.9773 (15)C51—C521.384 (3)
Ru1—N302.0990 (16)C51—H510.9500
Ru1—N502.0967 (16)C52—C531.380 (3)
Ru1—N601.9723 (15)C52—H520.9500
Ru1—N702.0939 (17)C53—C541.381 (3)
N10—C101.342 (2)C53—H530.9500
N10—C141.378 (2)C54—C601.472 (3)
C10—C111.385 (3)N60—C601.342 (2)
C10—H100.9500N60—C621.351 (2)
C11—C121.375 (3)N61—C601.323 (2)
C11—H110.9500N61—C611.352 (2)
C12—C131.390 (3)N62—C621.323 (2)
C12—H120.9500N62—C611.351 (3)
C13—C141.374 (3)C61—C801.475 (3)
C13—H130.9500C62—C741.475 (3)
C14—C201.470 (3)N70—C701.351 (2)
N20—C221.340 (2)N70—C741.375 (2)
N20—C201.341 (2)C70—C711.381 (3)
N21—C201.318 (2)C70—H700.9500
N21—C211.353 (3)C71—C721.382 (3)
N22—C221.324 (2)C71—H710.9500
N22—C211.344 (3)C72—C731.388 (3)
C21—C401.476 (3)C72—H720.9500
C22—C341.475 (3)C73—C741.376 (3)
N30—C301.351 (2)C73—H730.9500
N30—C341.376 (2)C80—C851.393 (3)
C30—C311.386 (3)C80—C811.394 (3)
C30—H300.9500C81—C821.381 (3)
C31—C321.384 (3)C81—H810.9500
C31—H310.9500C82—C831.389 (3)
C32—C331.385 (3)C82—H820.9500
C32—H320.9500C83—C841.376 (3)
C33—C341.378 (3)C83—H830.9500
C33—H330.9500C84—C851.390 (3)
C40—C411.388 (3)C84—H840.9500
C40—C451.400 (3)C85—H850.9500
C41—C421.390 (3)P10—F121.5943 (14)
C41—H410.9500P10—F101.5980 (13)
C42—C431.386 (3)P10—F111.5981 (13)
C42—H420.9500P10—F141.6015 (13)
C43—C441.383 (3)P10—F151.6029 (14)
C43—H430.9500P10—F131.6104 (13)
C44—C451.380 (3)P20—F201.5887 (14)
C44—H440.9500P20—F241.5970 (13)
C45—H450.9500P20—F211.5988 (13)
N50—C501.341 (2)P20—F231.6022 (14)
N50—C541.380 (2)P20—F221.6033 (15)
C50—C511.383 (3)P20—F251.6056 (15)
N10—Ru1—N30154.76 (6)C52—C51—H51120.3
N60—Ru1—N20179.28 (7)C53—C52—C51118.88 (19)
N70—Ru1—N50155.22 (6)C53—C52—H52120.6
N20—Ru1—N70103.31 (6)C51—C52—H52120.6
N20—Ru1—N50101.42 (6)C52—C53—C54119.35 (18)
N20—Ru1—N1077.77 (6)C52—C53—H53120.3
N20—Ru1—N3077.00 (6)C54—C53—H53120.3
N50—Ru1—N1091.99 (6)N50—C54—C53122.12 (18)
N50—Ru1—N3092.35 (6)N50—C54—C60114.54 (17)
N60—Ru1—N5077.85 (6)C53—C54—C60123.34 (17)
N60—Ru1—N7077.42 (6)C60—N60—C62117.61 (16)
N60—Ru1—N10102.25 (6)C60—N60—Ru1121.10 (13)
N60—Ru1—N30102.98 (6)C62—N60—Ru1121.27 (13)
N70—Ru1—N1091.67 (6)C60—N61—C61115.55 (17)
N70—Ru1—N3094.71 (6)C62—N62—C61115.62 (17)
C10—N10—C14116.93 (17)N61—C60—N60123.30 (18)
C10—N10—Ru1129.03 (13)N61—C60—C54124.22 (18)
C14—N10—Ru1114.03 (12)N60—C60—C54112.47 (16)
N10—C10—C11122.65 (18)N62—C61—N61124.81 (17)
N10—C10—H10118.7N62—C61—C80117.91 (18)
C11—C10—H10118.7N61—C61—C80117.28 (18)
C12—C11—C10119.80 (19)N62—C62—N60123.03 (18)
C12—C11—H11120.1N62—C62—C74124.68 (18)
C10—C11—H11120.1N60—C62—C74112.28 (16)
C11—C12—C13118.93 (19)C70—N70—C74117.23 (17)
C11—C12—H12120.5C70—N70—Ru1127.56 (13)
C13—C12—H12120.5C74—N70—Ru1115.09 (13)
C14—C13—C12118.61 (19)N70—C70—C71122.21 (18)
C14—C13—H13120.7N70—C70—H70118.9
C12—C13—H13120.7C71—C70—H70118.9
C13—C14—N10123.06 (18)C70—C71—C72120.02 (19)
C13—C14—C20122.33 (17)C70—C71—H71120.0
N10—C14—C20114.62 (17)C72—C71—H71120.0
C22—N20—C20117.20 (16)C71—C72—C73118.71 (19)
C22—N20—Ru1121.87 (13)C71—C72—H72120.6
C20—N20—Ru1120.87 (12)C73—C72—H72120.6
C20—N21—C21114.99 (17)C74—C73—C72118.93 (18)
C22—N22—C21115.08 (16)C74—C73—H73120.5
N21—C20—N20123.77 (18)C72—C73—H73120.5
N21—C20—C14123.59 (18)C73—C74—N70122.87 (18)
N20—C20—C14112.63 (16)C73—C74—C62123.19 (17)
N22—C21—N21125.27 (17)N70—C74—C62113.88 (17)
N22—C21—C40118.31 (17)C85—C80—C81119.08 (18)
N21—C21—C40116.42 (18)C85—C80—C61120.80 (19)
N22—C22—N20123.61 (18)C81—C80—C61120.12 (18)
N22—C22—C34124.21 (17)C82—C81—C80120.3 (2)
N20—C22—C34112.13 (16)C82—C81—H81119.9
C30—N30—C34117.11 (16)C80—C81—H81119.9
C30—N30—Ru1127.86 (13)C81—C82—C83120.4 (2)
C34—N30—Ru1114.98 (12)C81—C82—H82119.8
N30—C30—C31122.18 (18)C83—C82—H82119.8
N30—C30—H30118.9C84—C83—C82119.66 (19)
C31—C30—H30118.9C84—C83—H83120.2
C32—C31—C30120.11 (19)C82—C83—H83120.2
C32—C31—H31119.9C83—C84—C85120.5 (2)
C30—C31—H31119.9C83—C84—H84119.8
C33—C32—C31118.56 (19)C85—C84—H84119.8
C33—C32—H32120.7C84—C85—C80120.1 (2)
C31—C32—H32120.7C84—C85—H85119.9
C34—C33—C32119.07 (18)C80—C85—H85119.9
C34—C33—H33120.5F12—P10—F1090.99 (8)
C32—C33—H33120.5F12—P10—F1190.25 (8)
N30—C34—C33122.95 (17)F10—P10—F1190.97 (7)
N30—C34—C22114.00 (16)F12—P10—F1490.22 (8)
C33—C34—C22122.99 (17)F10—P10—F1489.70 (7)
C41—C40—C45119.70 (18)F11—P10—F14179.17 (9)
C41—C40—C21120.25 (18)F12—P10—F15179.52 (9)
C45—C40—C21120.01 (19)F10—P10—F1589.46 (8)
C40—C41—C42119.8 (2)F11—P10—F1589.57 (7)
C40—C41—H41120.1F14—P10—F1589.95 (8)
C42—C41—H41120.1F12—P10—F1389.68 (7)
C43—C42—C41120.2 (2)F10—P10—F13178.99 (8)
C43—C42—H42119.9F11—P10—F1389.79 (7)
C41—C42—H42119.9F14—P10—F1389.53 (7)
C44—C43—C42120.07 (19)F15—P10—F1389.87 (7)
C44—C43—H43120.0F20—P20—F2490.05 (7)
C42—C43—H43120.0F20—P20—F2190.18 (7)
C45—C44—C43120.2 (2)F24—P20—F21179.50 (9)
C45—C44—H44119.9F20—P20—F23179.55 (10)
C43—C44—H44119.9F24—P20—F2390.15 (7)
C44—C45—C40120.0 (2)F21—P20—F2389.63 (7)
C44—C45—H45120.0F20—P20—F2290.33 (8)
C40—C45—H45120.0F24—P20—F2290.25 (8)
C50—N50—C54117.38 (17)F21—P20—F2289.31 (7)
C50—N50—Ru1128.60 (13)F23—P20—F2290.08 (8)
C54—N50—Ru1114.01 (13)F20—P20—F2590.50 (9)
N50—C50—C51122.80 (18)F24—P20—F2589.90 (8)
N50—C50—H50118.6F21—P20—F2590.54 (7)
C51—C50—H50118.6F23—P20—F2589.10 (9)
C50—C51—C52119.45 (19)F22—P20—F25179.16 (9)
C50—C51—H51120.3
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C41—H41···N210.952.472.793 (3)100
C45—H45···N220.952.522.826 (3)99
C81—H81···N610.952.472.797 (2)100
C85—H85···N620.952.502.823 (3)100
Table 1
Selected geometric parameters (Å, °) top
Ru1—N102.0982 (16)Ru1—N502.0967 (16)
Ru1—N201.9773 (15)Ru1—N601.9723 (15)
Ru1—N302.0990 (16)Ru1—N702.0939 (17)
N10—Ru1—N30154.76 (6)N50—Ru1—N3092.35 (6)
N60—Ru1—N20179.28 (7)N60—Ru1—N5077.85 (6)
N70—Ru1—N50155.22 (6)N60—Ru1—N7077.42 (6)
N20—Ru1—N70103.31 (6)N60—Ru1—N10102.25 (6)
N20—Ru1—N50101.42 (6)N60—Ru1—N30102.98 (6)
N20—Ru1—N1077.77 (6)N70—Ru1—N1091.67 (6)
N20—Ru1—N3077.00 (6)N70—Ru1—N3094.71 (6)
N50—Ru1—N1091.99 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C41—H41···N210.952.472.793 (3)100
C45—H45···N220.952.522.826 (3)99
C81—H81···N610.952.472.797 (2)100
C85—H85···N620.952.502.823 (3)100
Acknowledgements top

MIJP thanks the New Zealand Foundation of Research Science and Technology for funding.

references
References top

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