Tetra-μ-acetato-O:O′-bis­(quinoline-N)­diruthenium(II,III) hexa­fluoro­phosphate quinoline solvate

Gilfoy, H.J.; Robertson, K.N.; Cameron, T.S.; Aquino, M.A.S.

doi:10.1107/S1600536801016063

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Tetra-μ-acetato-O:O′-bis(quinoline-N)diruthenium(II,III) hexafluorophosphate quinoline solvate

H. J. Gilfoy, K. N. Robertson, T. S. Cameron and M. A. S. Aquino

The title complex, [Ru₂(O₂CCH₃)₄(C₉H₇N)₂]PF₆·C₉H₇N, shows a binuclear cage structure having an inversion center. There are weak intramolecular C—H

O interactions between the quinoline ligands and the bridging acetate O atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016063/ci6061sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016063/ci6061Isup2.hkl Contains datablock I

CCDC reference: 175968

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
Disorder in solvent or counter-ion
R factor = 0.043
wR factor = 0.131
Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



CELLV_02  Alert C The supplied cell volume s.u. differs from that
          calculated from the cell parameter s.u.'s by > 2
          Calculated cell volume su =       7.12
          Cell volume su given      =      11.00

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5872

PLAT_301  Alert C Main Residue Disorder ........................       7.00 Perc.

PLAT_302  Alert C Anion/Solvent Disorder .......................      50.00 Perc.

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.104
          Tmax scaled      0.104 Tmin scaled      0.046


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

Comment top

Only a few N-donor heterocycle axial diadducts of diruthenium(II,III) tetracarboxylate, [Ru₂(O₂CR)₄(N-heterocycle)₂]X (R = alkyl or aryl, X = counter-ion), have been structurally characterized. Most of these involve pyridine or pyridine derivatives (Cotton et al., 1998; Vamvounis et al., 2000) and one example of biological relevance employing 2-methylimidazole as the axial ligand (Sudha & Chakravarty, 1998). This latter complex displayed a weak intermolecular hydrogen bonding interaction between the non-bound nitrogen and an oxygen on the perchlorate counterion.

As Ru₂(O₂CR)₄Cl (R = CH₃ and CH₂CH₃) complexes have shown small but significant antitumor activity (Keppler et al., 1989), we sought to investigate the binding of various nucleoside bases to the diruthenium(II,III) tetracarboxylate core and focus on the structural aspects of this binding, in particular, any intramolcular hydrogen bonding. In addition to looking at nucleoside base adducts, we wanted to study similar and simpler diadducts that were soluble in non-aqueous media. Molecule (I) is one such complex. While it contains typical Ru—Ru, Ru—O and Ru—N bond lengths and angles (Table 1), it displays trans-oriented axially bound quinoline rings with weak intramolecular interactions between the acetate O atoms and C—H bonds of bound quinolines. Four of these are given in Table 2, the strongest of which is C12—H12···O3.

Experimental top

Quinoline (0.64 mmol) was added dropwise to a 5 ml solution of [Ru₂(O₂CCH₃)₄(H₂O)₂]PF₆ (0.16 mmol) in 2-propanol. The solution was stirred for 5 min and the gold–brown product filtered and dried. Crystals could be grown by slow evaporation from dichloromethane.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN for Windows; software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 50% probability level. The quinoline molecule of solvation and the heaxafluorophosphate counterion have been omitted.

tetra-mu-acetato-O:O'-bis(quinoline-N)diruthenium(II,III)hexafluorophosphate quinoline solvate top

Crystal data top

[Ru(C₂H₃O₂)₄(C₉H₇N)₂]PF₆·C₉H₇N	Z = 1
M_r = 970.75	F(000) = 485
Triclinic, P1	D_x = 1.689 Mg m⁻³
a = 12.180 (7) Å	Cu Kα radiation, λ = 1.5418 Å
b = 10.980 (3) Å	Cell parameters from 25 reflections
c = 7.729 (3) Å	θ = 39.5–40.0°
α = 99.75 (1)°	µ = 7.54 mm⁻¹
β = 108.70 (2)°	T = 293 K
γ = 79.0 (3)°	Block, red–brown
V = 954.6 (11) Å³	0.55 × 0.35 × 0.30 mm

Data collection top

Rigaku AFC-5R diffractometer	2555 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	R_int = 0.078
Graphite monochromator	θ_max = 64.9°, θ_min = 3.9°
ω–2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.446, T_max = 1.000	l = −8→8
3253 measured reflections	3 standard reflections every 150 reflections
3089 independent reflections	intensity decay: 8.4%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0655P)² + 3.3237P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3089 reflections	Δρ_max = 1.10 e Å⁻³
260 parameters	Δρ_min = −0.71 e Å⁻³
61 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (3)

Crystal data top

[Ru(C₂H₃O₂)₄(C₉H₇N)₂]PF₆·C₉H₇N	γ = 79.0 (3)°
M_r = 970.75	V = 954.6 (11) Å³
Triclinic, P1	Z = 1
a = 12.180 (7) Å	Cu Kα radiation
b = 10.980 (3) Å	µ = 7.54 mm⁻¹
c = 7.729 (3) Å	T = 293 K
α = 99.75 (1)°	0.55 × 0.35 × 0.30 mm
β = 108.70 (2)°

Data collection top

Rigaku AFC-5R diffractometer	2555 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.078
T_min = 0.446, T_max = 1.000	3 standard reflections every 150 reflections
3253 measured reflections	intensity decay: 8.4%
3089 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	61 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.05	Δρ_max = 1.10 e Å⁻³
3089 reflections	Δρ_min = −0.71 e Å⁻³
260 parameters

Special details top

Experimental. The scan width was (1.73 + 0.35tanθ)° with an ω scan speed of 16° per minute (up to 7 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ru1	0.48727 (4)	0.09331 (4)	0.44470 (6)	0.0378 (2)
P1A	1.0000	0.0000	0.5000	0.0850 (11)	0.50
F1A	0.943 (2)	0.0298 (16)	0.2958 (19)	0.143 (5)	0.50
F2A	1.1261 (14)	0.013 (2)	0.487 (4)	0.157 (7)	0.50
F3A	0.984 (2)	0.1451 (15)	0.568 (3)	0.195 (9)	0.50
P1B	1.0000	0.0000	0.5000	0.0850 (11)	0.50
F1B	0.967 (2)	−0.0372 (14)	0.2858 (19)	0.143 (5)	0.50
F2B	1.1313 (14)	−0.0506 (19)	0.523 (4)	0.157 (7)	0.50
F3B	1.015 (2)	0.1332 (14)	0.483 (3)	0.195 (9)	0.50
O1	0.3916 (4)	0.1713 (4)	0.6166 (6)	0.0464 (10)
O2	0.3397 (4)	0.0487 (4)	0.2505 (6)	0.0501 (11)
O3	0.5811 (4)	0.0102 (4)	0.2723 (6)	0.0459 (10)
O4	0.6330 (4)	0.1352 (4)	0.6462 (6)	0.0485 (10)
N1	0.4585 (4)	0.2862 (5)	0.3388 (7)	0.0406 (11)
C1	0.3767 (6)	0.1058 (6)	0.7253 (8)	0.0461 (14)
C2	0.3067 (8)	0.1655 (8)	0.8497 (12)	0.072 (2)
H2A	0.3027	0.1053	0.9234	0.108*	0.50
H2B	0.2290	0.1965	0.7783	0.108*	0.50
H2C	0.3428	0.2336	0.9282	0.108*	0.50
H2D	0.2803	0.2516	0.8299	0.108*	0.50
H2E	0.3540	0.1604	0.9750	0.108*	0.50
H2F	0.2402	0.1233	0.8251	0.108*	0.50
C3	0.3088 (6)	−0.0586 (7)	0.2436 (8)	0.0478 (15)
C4	0.2026 (7)	−0.0911 (8)	0.0983 (10)	0.068 (2)
H4A	0.1683	−0.0230	0.0256	0.102*	0.50
H4B	0.1473	−0.1071	0.1535	0.102*	0.50
H4C	0.2229	−0.1645	0.0211	0.102*	0.50
H4D	0.1907	−0.1734	0.1078	0.102*	0.50
H4E	0.2118	−0.0893	−0.0200	0.102*	0.50
H4F	0.1361	−0.0319	0.1124	0.102*	0.50
C5	0.3515 (5)	0.3478 (6)	0.3135 (9)	0.0477 (15)
H5	0.2953	0.3080	0.3301	0.057*
C6	0.3174 (5)	0.4674 (6)	0.2640 (9)	0.0534 (17)
H6	0.2409	0.5070	0.2499	0.064*
C7	0.3984 (5)	0.5264 (6)	0.2362 (9)	0.0526 (16)
H7	0.3773	0.6068	0.2020	0.063*
C8	0.5129 (5)	0.4655 (5)	0.2592 (8)	0.0435 (14)
C9	0.5993 (6)	0.5233 (7)	0.2324 (10)	0.0586 (18)
H9	0.5806	0.6032	0.1963	0.070*
C10	0.7116 (6)	0.4601 (6)	0.2604 (11)	0.064 (2)
H10	0.7692	0.4984	0.2455	0.077*
C11	0.7399 (6)	0.3397 (6)	0.3108 (10)	0.0586 (18)
H11	0.8159	0.2981	0.3277	0.070*
C12	0.6567 (5)	0.2817 (6)	0.3357 (9)	0.0495 (15)
H12	0.6765	0.2009	0.3688	0.059*
C13	0.5424 (5)	0.3437 (5)	0.3116 (7)	0.0372 (13)
C14	1.0363 (12)	0.3005 (18)	1.133 (3)	0.161 (7)
H14	1.0489	0.2175	1.1548	0.194*
C16	1.0042 (9)	0.4505 (10)	0.9312 (14)	0.111 (3)
C18	0.9694 (14)	0.6052 (18)	0.724 (3)	0.166 (7)
H18	0.9583	0.6235	0.6057	0.199*
C17	0.9918 (10)	0.4850 (16)	0.7636 (19)	0.137 (4)	0.75
H17	0.9991	0.4218	0.6696	0.164*	0.75
C15	1.0236 (10)	0.3275 (13)	0.961 (2)	0.140 (4)	0.75
H15	1.0281	0.2640	0.8659	0.168*	0.75
N2A	0.9918 (10)	0.4850 (16)	0.7636 (19)	0.137 (4)	0.25
N2B	1.0236 (10)	0.3275 (13)	0.961 (2)	0.140 (4)	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.0416 (3)	0.0422 (3)	0.0304 (3)	−0.01320 (19)	0.00602 (19)	0.00727 (18)
P1A	0.076 (2)	0.095 (2)	0.0535 (17)	0.0136 (18)	−0.0057 (15)	0.0055 (16)
F1A	0.153 (12)	0.161 (16)	0.066 (4)	0.017 (13)	−0.012 (5)	0.013 (8)
F2A	0.099 (6)	0.23 (2)	0.133 (12)	0.004 (10)	0.026 (6)	0.034 (13)
F3A	0.256 (19)	0.118 (8)	0.155 (19)	−0.012 (9)	−0.002 (14)	0.002 (10)
P1B	0.076 (2)	0.095 (2)	0.0535 (17)	0.0136 (18)	−0.0057 (15)	0.0055 (16)
F1B	0.153 (12)	0.161 (16)	0.066 (4)	0.017 (13)	−0.012 (5)	0.013 (8)
F2B	0.099 (6)	0.23 (2)	0.133 (12)	0.004 (10)	0.026 (6)	0.034 (13)
F3B	0.256 (19)	0.118 (8)	0.155 (19)	−0.012 (9)	−0.002 (14)	0.002 (10)
O1	0.056 (3)	0.048 (2)	0.043 (2)	−0.015 (2)	0.020 (2)	0.0053 (19)
O2	0.049 (2)	0.057 (3)	0.041 (2)	−0.014 (2)	0.0031 (19)	0.010 (2)
O3	0.055 (3)	0.052 (3)	0.037 (2)	−0.016 (2)	0.0187 (19)	0.0051 (19)
O4	0.049 (2)	0.054 (3)	0.044 (2)	−0.019 (2)	0.007 (2)	0.009 (2)
N1	0.037 (3)	0.044 (3)	0.037 (3)	−0.009 (2)	0.005 (2)	0.003 (2)
C1	0.051 (4)	0.050 (4)	0.039 (3)	−0.016 (3)	0.012 (3)	0.000 (3)
C2	0.094 (6)	0.069 (5)	0.064 (5)	−0.020 (4)	0.041 (5)	−0.007 (4)
C3	0.047 (4)	0.063 (4)	0.034 (3)	−0.020 (3)	0.006 (3)	0.002 (3)
C4	0.063 (5)	0.078 (5)	0.051 (4)	−0.035 (4)	−0.016 (4)	0.012 (4)
C5	0.035 (3)	0.061 (4)	0.043 (3)	−0.010 (3)	0.000 (3)	0.012 (3)
C6	0.037 (3)	0.058 (4)	0.056 (4)	0.000 (3)	−0.001 (3)	0.019 (3)
C7	0.054 (4)	0.046 (4)	0.047 (4)	−0.001 (3)	0.000 (3)	0.016 (3)
C8	0.051 (4)	0.046 (3)	0.030 (3)	−0.012 (3)	0.004 (3)	0.004 (3)
C9	0.067 (5)	0.058 (4)	0.055 (4)	−0.019 (4)	0.015 (4)	0.015 (3)
C10	0.065 (5)	0.072 (5)	0.072 (5)	−0.031 (4)	0.028 (4)	0.014 (4)
C11	0.049 (4)	0.070 (5)	0.070 (5)	−0.012 (3)	0.031 (4)	0.015 (4)
C12	0.044 (4)	0.054 (4)	0.051 (4)	−0.007 (3)	0.013 (3)	0.008 (3)
C13	0.042 (3)	0.042 (3)	0.027 (3)	−0.013 (3)	0.004 (2)	0.006 (2)
C14	0.063 (7)	0.192 (16)	0.223 (15)	−0.056 (9)	0.010 (12)	0.030 (13)
C16	0.049 (4)	0.151 (7)	0.118 (6)	−0.027 (5)	0.024 (5)	−0.040 (5)
C18	0.082 (10)	0.261 (18)	0.167 (15)	−0.051 (14)	0.036 (10)	0.030 (14)
C17	0.057 (6)	0.225 (13)	0.121 (8)	−0.043 (9)	0.028 (7)	−0.031 (8)
C15	0.063 (7)	0.156 (8)	0.181 (11)	−0.033 (8)	0.029 (9)	−0.041 (8)
N2A	0.057 (6)	0.225 (13)	0.121 (8)	−0.043 (9)	0.028 (7)	−0.031 (8)
N2B	0.063 (7)	0.156 (8)	0.181 (11)	−0.033 (8)	0.029 (9)	−0.041 (8)

Geometric parameters (Å, º) top

Ru1—O2	2.020 (5)	C4—H4D	0.96
Ru1—O3	2.020 (5)	C4—H4E	0.96
Ru1—O1	2.020 (5)	C4—H4F	0.96
Ru1—O4	2.021 (5)	C5—C6	1.379 (7)
Ru1—Ru1ⁱ	2.2816 (17)	C5—H5	0.93
Ru1—N1	2.323 (5)	C6—C7	1.366 (7)
P1A—F1Aⁱⁱ	1.570 (14)	C6—H6	0.93
P1A—F1A	1.570 (14)	C7—C8	1.395 (8)
P1A—F3Aⁱⁱ	1.586 (15)	C7—H7	0.93
P1A—F3A	1.586 (15)	C8—C13	1.409 (7)
P1A—F2Aⁱⁱ	1.605 (15)	C8—C9	1.413 (7)
P1A—F2A	1.605 (15)	C9—C10	1.377 (8)
O1—C1	1.269 (8)	C9—H9	0.93
O2—C3	1.292 (8)	C10—C11	1.389 (8)
O3—C1ⁱ	1.280 (8)	C10—H10	0.93
O4—C3ⁱ	1.250 (8)	C11—C12	1.372 (7)
N1—C5	1.319 (8)	C11—H11	0.93
N1—C13	1.385 (8)	C12—C13	1.397 (7)
C1—O3ⁱ	1.280 (8)	C12—H12	0.93
C1—C2	1.476 (10)	C14—C15	1.366 (9)
C2—H2A	0.96	C14—C18ⁱⁱⁱ	1.39 (3)
C2—H2B	0.96	C14—H14	0.93
C2—H2C	0.96	C16—C17	1.365 (9)
C2—H2D	0.96	C16—C15	1.372 (9)
C2—H2E	0.96	C16—C16ⁱⁱⁱ	1.399 (10)
C2—H2F	0.96	C18—C17	1.363 (9)
C3—O4ⁱ	1.250 (8)	C18—C14ⁱⁱⁱ	1.39 (3)
C3—C4	1.474 (9)	C18—H18	0.93
C4—H4A	0.96	C17—H17	0.93
C4—H4B	0.96	C15—H15	0.93
C4—H4C	0.96

O2—Ru1—O3	89.5 (2)	C3—C4—H4A	109.5
O2—Ru1—O1	89.6 (2)	C3—C4—H4B	109.5
O3—Ru1—O1	178.2 (4)	H4A—C4—H4B	109.5
O2—Ru1—O4	177.8 (4)	C3—C4—H4C	109.5
O3—Ru1—O4	92.0 (2)	H4A—C4—H4C	109.5
O1—Ru1—O4	88.9 (2)	H4B—C4—H4C	109.5
O2—Ru1—Ru1ⁱ	89.6 (2)	C3—C4—H4D	109.5
O3—Ru1—Ru1ⁱ	89.1 (2)	H4A—C4—H4D	141.1
O1—Ru1—Ru1ⁱ	89.4 (2)	H4B—C4—H4D	56.3
O4—Ru1—Ru1ⁱ	88.7 (2)	H4C—C4—H4D	56.3
O2—Ru1—N1	90.5 (3)	C3—C4—H4E	109.5
O3—Ru1—N1	92.6 (2)	H4A—C4—H4E	56.3
O1—Ru1—N1	88.9 (2)	H4B—C4—H4E	141.1
O4—Ru1—N1	91.1 (3)	H4C—C4—H4E	56.3
Ru1ⁱ—Ru1—N1	178.24 (13)	H4D—C4—H4E	109.5
F1Aⁱⁱ—P1A—F1A	180.000 (1)	C3—C4—H4F	109.5
F1Aⁱⁱ—P1A—F3Aⁱⁱ	89.5 (9)	H4A—C4—H4F	56.3
F1A—P1A—F3Aⁱⁱ	90.5 (9)	H4B—C4—H4F	56.3
F1Aⁱⁱ—P1A—F3A	90.5 (9)	H4C—C4—H4F	141.1
F1A—P1A—F3A	89.5 (9)	H4D—C4—H4F	109.5
F3Aⁱⁱ—P1A—F3A	180.000 (2)	H4E—C4—H4F	109.5
F1Aⁱⁱ—P1A—F2Aⁱⁱ	89.6 (9)	N1—C5—C6	124.3 (6)
F1A—P1A—F2Aⁱⁱ	90.4 (9)	N1—C5—H5	117.9
F3Aⁱⁱ—P1A—F2Aⁱⁱ	88.0 (10)	C6—C5—H5	117.9
F3A—P1A—F2Aⁱⁱ	92.0 (10)	C7—C6—C5	118.6 (6)
F1Aⁱⁱ—P1A—F2A	90.4 (9)	C7—C6—H6	120.7
F1A—P1A—F2A	89.6 (9)	C5—C6—H6	120.7
F3Aⁱⁱ—P1A—F2A	92.0 (10)	C6—C7—C8	119.8 (6)
F3A—P1A—F2A	88.0 (10)	C6—C7—H7	120.1
F2Aⁱⁱ—P1A—F2A	180.000 (2)	C8—C7—H7	120.1
C1—O1—Ru1	119.8 (4)	C7—C8—C13	118.9 (6)
C3—O2—Ru1	118.8 (4)	C7—C8—C9	121.5 (5)
C1ⁱ—O3—Ru1	119.8 (4)	C13—C8—C9	119.6 (6)
C3ⁱ—O4—Ru1	120.7 (4)	C10—C9—C8	119.2 (6)
C5—N1—C13	118.4 (5)	C10—C9—H9	120.4
C5—N1—Ru1	114.6 (5)	C8—C9—H9	120.4
C13—N1—Ru1	126.9 (4)	C9—C10—C11	120.9 (6)
O1—C1—O3ⁱ	121.9 (6)	C9—C10—H10	119.6
O1—C1—C2	118.6 (6)	C11—C10—H10	119.6
O3ⁱ—C1—C2	119.5 (6)	C12—C11—C10	120.7 (6)
C1—C2—H2A	109.5	C12—C11—H11	119.7
C1—C2—H2B	109.5	C10—C11—H11	119.7
H2A—C2—H2B	109.5	C11—C12—C13	120.1 (6)
C1—C2—H2C	109.5	C11—C12—H12	120.0
H2A—C2—H2C	109.5	C13—C12—H12	120.0
H2B—C2—H2C	109.5	N1—C13—C12	120.3 (5)
C1—C2—H2D	109.5	N1—C13—C8	120.1 (5)
H2A—C2—H2D	141.1	C12—C13—C8	119.6 (6)
H2B—C2—H2D	56.3	C15—C14—C18ⁱⁱⁱ	121.3 (18)
H2C—C2—H2D	56.3	C15—C14—H14	119.4
C1—C2—H2E	109.5	C18ⁱⁱⁱ—C14—H14	119.4
H2A—C2—H2E	56.3	C17—C16—C15	121.9 (10)
H2B—C2—H2E	141.1	C17—C16—C16ⁱⁱⁱ	115.1 (15)
H2C—C2—H2E	56.3	C15—C16—C16ⁱⁱⁱ	123.0 (16)
H2D—C2—H2E	109.5	C17—C18—C14ⁱⁱⁱ	117.3 (18)
C1—C2—H2F	109.5	C17—C18—H18	121.3
H2A—C2—H2F	56.3	C14ⁱⁱⁱ—C18—H18	121.3
H2B—C2—H2F	56.3	C18—C17—C16	124.8 (16)
H2C—C2—H2F	141.1	C18—C17—H17	117.6
H2D—C2—H2F	109.5	C16—C17—H17	117.6
H2E—C2—H2F	109.5	C14—C15—C16	118.4 (16)
O4ⁱ—C3—O2	122.1 (6)	C14—C15—H15	120.8
O4ⁱ—C3—C4	119.7 (6)	C16—C15—H15	120.8
O2—C3—C4	118.2 (6)

O2—Ru1—O1—C1	91.1 (5)	C13—N1—C5—C6	−1.0 (9)
O4—Ru1—O1—C1	−87.3 (5)	Ru1—N1—C5—C6	175.2 (5)
Ru1ⁱ—Ru1—O1—C1	1.5 (4)	N1—C5—C6—C7	1.1 (10)
N1—Ru1—O1—C1	−178.3 (5)	C5—C6—C7—C8	−0.4 (10)
O3—Ru1—O2—C3	87.6 (5)	C6—C7—C8—C13	−0.2 (9)
O1—Ru1—O2—C3	−90.9 (5)	C6—C7—C8—C9	−179.8 (6)
Ru1ⁱ—Ru1—O2—C3	−1.5 (5)	C7—C8—C9—C10	178.7 (7)
N1—Ru1—O2—C3	−179.8 (5)	C13—C8—C9—C10	−0.8 (10)
O2—Ru1—O3—C1ⁱ	−90.4 (5)	C8—C9—C10—C11	1.3 (12)
O4—Ru1—O3—C1ⁱ	88.0 (5)	C9—C10—C11—C12	−0.7 (12)
Ru1ⁱ—Ru1—O3—C1ⁱ	−0.7 (4)	C10—C11—C12—C13	−0.3 (11)
N1—Ru1—O3—C1ⁱ	179.1 (5)	C5—N1—C13—C12	−179.6 (6)
O3—Ru1—O4—C3ⁱ	−87.1 (5)	Ru1—N1—C13—C12	4.7 (8)
O1—Ru1—O4—C3ⁱ	91.4 (5)	C5—N1—C13—C8	0.4 (8)
Ru1ⁱ—Ru1—O4—C3ⁱ	2.0 (5)	Ru1—N1—C13—C8	−175.3 (4)
N1—Ru1—O4—C3ⁱ	−179.7 (5)	C11—C12—C13—N1	−179.2 (6)
O2—Ru1—N1—C5	48.0 (4)	C11—C12—C13—C8	0.8 (9)
O3—Ru1—N1—C5	137.5 (4)	C7—C8—C13—N1	0.2 (8)
O1—Ru1—N1—C5	−41.6 (5)	C9—C8—C13—N1	179.8 (6)
O4—Ru1—N1—C5	−130.5 (4)	C7—C8—C13—C12	−179.8 (6)
O2—Ru1—N1—C13	−136.2 (5)	C9—C8—C13—C12	−0.2 (9)
O3—Ru1—N1—C13	−46.7 (5)	C14ⁱⁱⁱ—C18—C17—C16	3 (2)
O1—Ru1—N1—C13	134.2 (5)	C15—C16—C17—C18	178.2 (13)
O4—Ru1—N1—C13	45.4 (5)	C16ⁱⁱⁱ—C16—C17—C18	−2 (2)
Ru1—O1—C1—O3ⁱ	−1.3 (8)	C18ⁱⁱⁱ—C14—C15—C16	−1 (2)
Ru1—O1—C1—C2	179.8 (5)	C17—C16—C15—C14	179.4 (11)
Ru1—O2—C3—O4ⁱ	0.4 (9)	C16ⁱⁱⁱ—C16—C15—C14	−1 (2)
Ru1—O2—C3—C4	−178.5 (5)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.71	3.150 (7)	110
C5—H5···O2	0.93	2.79	3.261 (8)	112
C12—H12···O3	0.93	2.48	3.199 (9)	135
C12—H12···O4	0.93	2.61	3.218 (8)	124

Experimental details

Crystal data
Chemical formula	[Ru(C₂H₃O₂)₄(C₉H₇N)₂]PF₆·C₉H₇N
M_r	970.75
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	12.180 (7), 10.980 (3), 7.729 (3)
α, β, γ (°)	99.75 (1), 108.70 (2), 79.0 (3)
V (Å³)	954.6 (11)
Z	1
Radiation type	Cu Kα
µ (mm⁻¹)	7.54
Crystal size (mm)	0.55 × 0.35 × 0.30

Data collection
Diffractometer	Rigaku AFC-5R diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.446, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3253, 3089, 2555
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.587

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.131, 1.05
No. of reflections	3089
No. of parameters	260
No. of restraints	61
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.10, −0.71

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1997-1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), TEXSAN for Windows, SHELXL97.

Selected geometric parameters (Å, º) top

Ru1—O2	2.020 (5)	Ru1—O4	2.021 (5)
Ru1—O3	2.020 (5)	Ru1—Ru1ⁱ	2.2816 (17)
Ru1—O1	2.020 (5)	Ru1—N1	2.323 (5)

O2—Ru1—O3	89.5 (2)	Ru1ⁱ—Ru1—N1	178.24 (13)
O3—Ru1—O1	178.2 (4)	C1—O1—Ru1	119.8 (4)
O3—Ru1—O4	92.0 (2)	C1ⁱ—O3—Ru1	119.8 (4)
O2—Ru1—Ru1ⁱ	89.6 (2)	C5—N1—C13	118.4 (5)
O1—Ru1—Ru1ⁱ	89.4 (2)	C5—N1—Ru1	114.6 (5)
O2—Ru1—N1	90.5 (3)	C13—N1—Ru1	126.9 (4)
O1—Ru1—N1	88.9 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.71	3.150 (7)	110.2
C5—H5···O2	0.93	2.79	3.261 (8)	112.2
C12—H12···O3	0.93	2.48	3.199 (9)	134.6
C12—H12···O4	0.93	2.61	3.218 (8)	123.8

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