[2,6-Bis(5-chloro­pyrimidin-2-yl-κN)pyri­dine-κN](2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)ruthenium(II) bis­(hexa­fluoridophosphate) acetonitrile disolvate

Medlycott, E.A.; Wang, J.; Hanan, G.S.

doi:10.1107/S1600536807068602

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m326

doi:10.1107/S1600536807068602

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[2,6-Bis(5-chloropyrimidin-2-yl-κN)pyridine-κN](2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)ruthenium(II) bis(hexafluoridophosphate) acetonitrile disolvate

Elaine A. Medlycott,^a Jianhua Wang ^a and Garry S. Hanan ^a ^*

^aDépartement de Chimie, Université de Montréal, CP 6128, Succ. Centre-ville, Montréal, Québec, Canada H3C 3J7
^*Correspondence e-mail: garry.hanan@umontreal.ca

(Received 22 November 2007; accepted 28 December 2007; online 9 January 2008)

In the title compound, [Ru(C₁₃H₇Cl₂N₅)(C₁₅H₁₁N₃)](PF₆)₂·2CH₃CN, the Ru^II atom is coordinated in a distorted octahedral geometry by a tridentate 2,2′:6′,2′′-terpyridine ligand and a tridentate 2,6-bis(5-chloropyrimidin-2-yl)pyridine ligand. Least-squares mean-plane distortions of only 1.72 (2) and 2.91 (2)° of the pyrimidyl rings with respect to the central pyridine are observed for the bis(pyrimidyl)pyridine-based tridentate ligand, while the distal pyridyl rings of terpyridine twist by 13.43 (7) and 4.68 (9)° away from the central pyridine ring.

Related literature

For related literature, see: Fang et al. (2002 ); Groen et al. (1998 ); Medlycott & Hanan (2005 ); Polson et al. (2004 ); Pyo et al. (1999 ).

Experimental

Crystal data

[Ru(C₁₃H₇Cl₂N₅)(C₁₅H₁₁N₃)](PF₆)₂·2C₂H₃N
M_r = 1010.52
Orthorhombic, F d d 2
a = 16.3846 (2) Å
b = 62.8985 (8) Å
c = 14.5581 (2) Å
V = 15003.1 (3) Å³
Z = 16
Cu Kα radiation
μ = 6.43 mm⁻¹
T = 100 (2) K
0.48 × 0.25 × 0.07 mm

Data collection

Bruker SMART 2K diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.190, T_max = 0.640
45518 measured reflections
7327 independent reflections
7121 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.072
S = 1.08
7327 reflections
534 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ), 3439 Friedel pairs
Flack parameter: 0.052 (5)

Table 1
Selected geometric parameters (Å, °)

Ru1—N1	2.088 (2)
Ru1—N3	1.980 (2)
Ru1—N4	2.069 (2)
Ru1—N6	2.083 (3)
Ru1—N7	2.000 (2)
Ru1—N8	2.068 (3)

N3—Ru1—N7	175.35 (9)
N3—Ru1—N8	100.81 (12)
N7—Ru1—N8	78.90 (12)
N3—Ru1—N4	79.37 (9)
N7—Ru1—N4	96.00 (9)
N8—Ru1—N4	92.69 (10)
N3—Ru1—N6	101.62 (11)
N7—Ru1—N6	78.75 (11)
N8—Ru1—N6	157.58 (9)
N4—Ru1—N6	91.4 (1)
N3—Ru1—N1	79.51 (9)
N7—Ru1—N1	105.12 (9)
N8—Ru1—N1	90.79 (10)
N4—Ru1—N1	158.87 (9)
N6—Ru1—N1	93.3 (1)

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997 ); software used to prepare material for publication: UdMX (local program) and Spek (2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068602/hy2110sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068602/hy2110Isup2.hkl

checkCIF report

Comment top

Ruthenium(II) complexes of tridentate polypyridine ligands have gained much attention in the last few decades due to their interesting photophysical properties. There have been many attempts to try and improve the photophysical properties of these complexes both in the ground state and excited states (Medlycott & Hanan, 2005). Manipulation of the electronic properties of the coordinated ligands can result in an improvement of the photophysical properties of the complex. We have previously employed this strategy by using electron-deficient trazine-based tridenate ligands (Polson et al., 2004) to lower the energy of the ³MLCT emitting state. Herein, we employ a functionalized bis(pyrimidin-2-yl)pyridine tridentate ligand for the synthesis of a ruthenium(II) complex in order to manipulate the energy of the ³MLCT emitting state. A structurally similar ligand, namely bis(pyrimidin-2-yl)pyridine, has previously been employed for the synthesis of palladium(II) complexes in order to study the dynamic behviour of such complexes in solution (Groen et al., 1998). However, the electronic behaviour and solid state structures of these systems were not reported.

The title compound crystalizes in the orthorhombic space group Fdd2 with one complex cation, two PF₆^- anions and two acetonitrile molecules in the asymmetric unit. The complex possesses octahedral geometry with significant distortions due to the tridentate nature of the coordinating ligands as previously observed in the parent complex [Ru(tpy)₂]²⁺ (tpy = 2,2':6',2"-terpyridine) (Pyo et al., 1999). Small variations in the Ru—N bond distances are observed between the two coordinated ligands indicating minimal changes in the electronic (solid state) ground-state properties of the complex compared to [Ru(tpy)₂]²⁺ (Pyo et al., 1999). Similarly, small changes are observed in the N,N,N-tridentate bite angles on the pyrimidyl-substituted ligand 158.87 (9)° compared to the coordinated tpy, 157.58 (9)°, indicating that introducing a pyrimidyl ring has minimal steric effects on the ligand field of the complex.

Comparison of the planarity of the two coordinated ligands in the title compound shows us that the bis(pyrimidin-2-yl)pyridine-based ligand lies planar. Least-square mean plane distortions of only 1.72 (2)° and 2.91 (2)° of the pyrimidyl rings with respect to the central pyridine are observed. However, the distal pyridyl-rings of terpyridine twist by 13.43 (7)° and 4.68 (9)° away from the central pyridine ring. This difference may be explained on considering the uncoordinated pyrimidyl-N atoms forming favourable intramolecular C–H···N interactions with the central pyridine ring. This coplanar effect has previously been shown to dramatically enhance the photophysical properties of such complexes (Fang et al., 2002).

We are currently investigating the consequences of pyrimidyl substitution of tridentate-tpy based ligands on the photophysical properties of their ruthenium(II) complexes.

Related literature top

For related literature, see: Fang et al. (2002); Groen et al. (1998); Medlycott & Hanan (2005); Polson et al. (2004); Pyo et al. (1999); Spek (2003).

Experimental top

The title compound was synthesized following previously established procedures (Polson et al.,2004).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. The PF₆^-counter anions, H atoms and acetonitrile solvent molecules have been omitted for clarity.

[2,6-Bis(5-chloropyrimidin-2-yl)pyridine-κ³N¹,N²,N⁶](2,2':6',2''- terpyridine-κ³N,N',N'')ruthenium(II) bis(hexafluoridophosphate) acetonitrile disolvate top

Crystal data top

[Ru(C₁₃H₇Cl₂N₅)(C₁₅H₁₁N₃)](PF₆)₂·2C₂H₃N	F(000) = 8032
M_r = 1010.52	D_x = 1.789 Mg m⁻³
Orthorhombic, Fdd2	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: F 2 -2d	Cell parameters from 7885 reflections
a = 16.3846 (2) Å	θ = 2.8–72.9°
b = 62.8985 (8) Å	µ = 6.44 mm⁻¹
c = 14.5581 (2) Å	T = 100 K
V = 15003.1 (3) Å³	Block, red
Z = 16	0.48 × 0.25 × 0.07 mm

Data collection top

Bruker SMART 2K diffractometer	7327 independent reflections
Radiation source: X-ray Sealed Tube	7121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 73.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→18
T_min = 0.190, T_max = 0.640	k = −77→77
45518 measured reflections	l = −17→17

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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0495P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.002
7327 reflections	Δρ_max = 0.71 e Å⁻³
534 parameters	Δρ_min = −0.38 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3439 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.052 (5)

Crystal data top

[Ru(C₁₃H₇Cl₂N₅)(C₁₅H₁₁N₃)](PF₆)₂·2C₂H₃N	V = 15003.1 (3) Å³
M_r = 1010.52	Z = 16
Orthorhombic, Fdd2	Cu Kα radiation
a = 16.3846 (2) Å	µ = 6.44 mm⁻¹
b = 62.8985 (8) Å	T = 100 K
c = 14.5581 (2) Å	0.48 × 0.25 × 0.07 mm

Data collection top

Bruker SMART 2K diffractometer	7327 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7121 reflections with I > 2σ(I)
T_min = 0.190, T_max = 0.640	R_int = 0.053
45518 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.072	Δρ_max = 0.71 e Å⁻³
S = 1.08	Δρ_min = −0.38 e Å⁻³
7327 reflections	Absolute structure: Flack (1983), 3439 Friedel pairs
534 parameters	Absolute structure parameter: 0.052 (5)
1 restraint

Special details top

Experimental. X-ray crystallographic data for the title compound were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2 K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu—Kα radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8Å resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ru1	0.290100 (12)	0.172144 (3)	0.184589 (14)	0.01338 (6)
N1	0.16426 (13)	0.16743 (3)	0.17514 (17)	0.0127 (5)
N2	0.06878 (15)	0.13822 (4)	0.16488 (17)	0.0192 (5)
N3	0.28547 (14)	0.14071 (3)	0.1797 (2)	0.0158 (4)
N4	0.41289 (14)	0.16477 (4)	0.19327 (18)	0.0162 (5)
N5	0.50172 (15)	0.13428 (4)	0.19511 (18)	0.0185 (5)
N6	0.30146 (14)	0.17985 (4)	0.04606 (19)	0.0161 (5)
N7	0.30453 (13)	0.20369 (3)	0.1912 (2)	0.0171 (5)
N8	0.28073 (15)	0.17725 (4)	0.32451 (18)	0.0164 (5)
Cl1	−0.05599 (5)	0.191627 (12)	0.18178 (7)	0.03047 (17)
Cl2	0.63956 (5)	0.185785 (12)	0.20297 (6)	0.02663 (17)
C1	0.10321 (18)	0.18085 (4)	0.1752 (2)	0.0187 (6)
H1	0.1139	0.1957	0.1764	0.022*
C2	0.02315 (19)	0.17372 (5)	0.1736 (2)	0.0216 (6)
C3	0.00786 (18)	0.15218 (5)	0.1673 (2)	0.0205 (6)
H3	−0.0469	0.1473	0.1648	0.025*
C4	0.14379 (17)	0.14580 (4)	0.1707 (2)	0.0161 (6)
C5	0.21284 (17)	0.13084 (4)	0.1747 (2)	0.0166 (6)
C6	0.20777 (17)	0.10876 (4)	0.1748 (2)	0.0179 (6)
H6	0.1563	0.1018	0.1723	0.021*
C7	0.27997 (18)	0.09704 (4)	0.1786 (2)	0.0195 (6)
H7	0.2782	0.0819	0.1792	0.023*
C8	0.35412 (17)	0.10751 (4)	0.1814 (2)	0.0184 (5)
H8	0.4036	0.0996	0.1816	0.022*
C9	0.35616 (16)	0.12949 (4)	0.1840 (2)	0.0157 (5)
C10	0.42780 (17)	0.14324 (4)	0.1912 (2)	0.0155 (5)
C11	0.56623 (19)	0.14731 (5)	0.1980 (2)	0.0194 (6)
H11	0.6197	0.1415	0.1991	0.023*
C12	0.55631 (19)	0.16922 (5)	0.1993 (2)	0.0195 (6)
C13	0.47850 (17)	0.17753 (5)	0.1987 (2)	0.0175 (6)
H13	0.4711	0.1925	0.2022	0.021*
C21	0.30071 (18)	0.16651 (5)	−0.0258 (2)	0.0195 (6)
H21	0.2985	0.1516	−0.0147	0.023*
C22	0.3031 (2)	0.17365 (5)	−0.1157 (2)	0.0246 (7)
H22	0.3032	0.1638	−0.1651	0.029*
C23	0.3053 (2)	0.19512 (6)	−0.1327 (2)	0.0264 (7)
H23	0.3035	0.2003	−0.1939	0.032*
C24	0.31023 (19)	0.20912 (5)	−0.0588 (3)	0.0236 (6)
H24	0.3144	0.2240	−0.0690	0.028*
C25	0.30901 (18)	0.20109 (5)	0.0297 (2)	0.0176 (6)
C26	0.31643 (18)	0.21439 (5)	0.1127 (2)	0.0181 (6)
C27	0.3406 (2)	0.23558 (5)	0.1156 (2)	0.0229 (7)
H27	0.3490	0.2434	0.0606	0.028*
C28	0.3523 (2)	0.24505 (5)	0.2008 (2)	0.0283 (7)
H28	0.3690	0.2595	0.2040	0.034*
C29	0.3398 (2)	0.23369 (5)	0.2810 (2)	0.0246 (7)
H29	0.3481	0.2402	0.3392	0.030*
C30	0.31470 (19)	0.21252 (5)	0.2749 (2)	0.0193 (6)
C31	0.29853 (18)	0.19766 (5)	0.3507 (2)	0.0191 (6)
C32	0.3001 (2)	0.20342 (5)	0.4418 (3)	0.0257 (7)
H32	0.3149	0.2175	0.4591	0.031*
C33	0.2797 (2)	0.18839 (6)	0.5089 (2)	0.0262 (7)
H33	0.2806	0.1922	0.5721	0.031*
C34	0.25841 (19)	0.16815 (6)	0.4826 (2)	0.0241 (7)
H34	0.2430	0.1578	0.5270	0.029*
C35	0.25996 (19)	0.16315 (5)	0.3895 (2)	0.0202 (6)
H35	0.2457	0.1491	0.3712	0.024*
P1	0.53369 (4)	0.138455 (11)	−0.06986 (7)	0.01995 (15)
F11	0.55805 (15)	0.15979 (3)	−0.12300 (15)	0.0394 (5)
F12	0.47251 (14)	0.15156 (4)	−0.00468 (16)	0.0489 (6)
F13	0.60507 (12)	0.14221 (4)	0.00174 (15)	0.0395 (5)
F14	0.59497 (16)	0.12565 (4)	−0.13491 (16)	0.0478 (6)
F15	0.46190 (13)	0.13468 (4)	−0.14174 (17)	0.0456 (6)
F16	0.50911 (17)	0.11725 (4)	−0.01669 (18)	0.0514 (7)
P2	0.55212 (6)	0.220273 (12)	0.44248 (8)	0.02989 (19)
F21	0.62202 (18)	0.23668 (4)	0.41314 (18)	0.0620 (8)
F22	0.61423 (13)	0.20103 (4)	0.4277 (2)	0.0494 (6)
F23	0.52253 (16)	0.21836 (4)	0.33806 (17)	0.0481 (6)
F24	0.4896 (2)	0.23943 (4)	0.45789 (19)	0.0691 (9)
F25	0.57961 (18)	0.22231 (4)	0.54775 (16)	0.0499 (6)
F26	0.48287 (14)	0.20363 (4)	0.47239 (17)	0.0412 (5)
C41	0.5921 (3)	0.24842 (7)	0.1749 (4)	0.0671 (15)
H41A	0.5672	0.2485	0.2362	0.101*
H41B	0.6125	0.2341	0.1613	0.101*
H41C	0.5511	0.2524	0.1291	0.101*
C42	0.6591 (3)	0.26342 (6)	0.1723 (3)	0.0385 (9)
N43	0.7112 (2)	0.27540 (5)	0.1708 (3)	0.0412 (9)
C51	0.5307 (3)	0.20455 (7)	−0.0195 (3)	0.0445 (10)
H51A	0.5680	0.2005	0.0302	0.067*
H51B	0.4951	0.1925	−0.0341	0.067*
H51C	0.4974	0.2167	0.0000	0.067*
C52	0.5776 (2)	0.21037 (5)	−0.1004 (3)	0.0301 (8)
N53	0.6152 (2)	0.21498 (5)	−0.1637 (2)	0.0403 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01374 (10)	0.00810 (9)	0.01831 (10)	0.00004 (7)	0.00117 (8)	0.00034 (9)
N1	0.0076 (10)	0.0176 (11)	0.0129 (12)	−0.0043 (8)	−0.0006 (9)	0.0052 (10)
N2	0.0179 (13)	0.0198 (12)	0.0198 (14)	−0.0043 (10)	−0.0001 (10)	0.0000 (10)
N3	0.0191 (11)	0.0120 (10)	0.0164 (11)	0.0004 (8)	−0.0004 (10)	0.0014 (12)
N4	0.0171 (12)	0.0150 (11)	0.0167 (12)	−0.0012 (8)	0.0020 (11)	−0.0005 (11)
N5	0.0189 (12)	0.0146 (11)	0.0220 (13)	0.0035 (8)	0.0033 (11)	0.0011 (10)
N6	0.0139 (12)	0.0110 (12)	0.0233 (14)	−0.0003 (9)	0.0007 (10)	0.0012 (10)
N7	0.0165 (12)	0.0104 (10)	0.0243 (13)	0.0007 (8)	0.0028 (12)	0.0009 (11)
N8	0.0151 (12)	0.0151 (12)	0.0191 (13)	−0.0002 (9)	−0.0001 (9)	−0.0003 (10)
Cl1	0.0194 (3)	0.0265 (4)	0.0456 (5)	0.0084 (3)	0.0040 (4)	0.0037 (4)
Cl2	0.0186 (4)	0.0253 (4)	0.0360 (5)	−0.0046 (3)	0.0018 (3)	−0.0041 (3)
C1	0.0202 (14)	0.0153 (12)	0.0205 (15)	−0.0006 (10)	0.0014 (13)	0.0026 (11)
C2	0.0188 (13)	0.0230 (14)	0.0230 (18)	0.0043 (11)	0.0024 (13)	0.0019 (13)
C3	0.0134 (14)	0.0280 (15)	0.0200 (16)	−0.0011 (11)	−0.0002 (11)	−0.0008 (12)
C4	0.0182 (14)	0.0148 (12)	0.0153 (15)	−0.0016 (10)	0.0032 (11)	−0.0023 (11)
C5	0.0199 (13)	0.0148 (12)	0.0150 (15)	−0.0041 (10)	0.0014 (11)	0.0004 (12)
C6	0.0207 (13)	0.0128 (12)	0.0202 (16)	−0.0050 (10)	0.0020 (12)	−0.0008 (12)
C7	0.0275 (15)	0.0089 (11)	0.0220 (15)	0.0012 (10)	0.0001 (13)	0.0009 (13)
C8	0.0240 (14)	0.0129 (12)	0.0183 (13)	0.0039 (10)	0.0012 (14)	0.0025 (12)
C9	0.0181 (13)	0.0120 (12)	0.0171 (13)	0.0008 (9)	0.0015 (13)	0.0015 (12)
C10	0.0179 (13)	0.0139 (12)	0.0146 (13)	0.0043 (9)	0.0001 (12)	0.0011 (12)
C11	0.0167 (14)	0.0236 (14)	0.0178 (15)	0.0030 (11)	0.0007 (12)	0.0019 (12)
C12	0.0185 (14)	0.0202 (14)	0.0197 (18)	−0.0038 (11)	0.0021 (12)	−0.0029 (12)
C13	0.0176 (14)	0.0164 (13)	0.0184 (15)	−0.0020 (10)	0.0035 (12)	−0.0011 (11)
C21	0.0166 (15)	0.0147 (14)	0.0272 (16)	−0.0008 (11)	−0.0005 (12)	−0.0031 (12)
C22	0.0254 (17)	0.0258 (17)	0.0225 (17)	−0.0011 (13)	0.0016 (13)	−0.0064 (13)
C23	0.0259 (17)	0.0316 (19)	0.0218 (16)	−0.0009 (14)	0.0022 (13)	0.0042 (14)
C24	0.0235 (15)	0.0196 (14)	0.0277 (17)	−0.0016 (11)	0.0048 (15)	0.0047 (14)
C25	0.0160 (14)	0.0130 (14)	0.0237 (15)	−0.0031 (11)	0.0010 (12)	0.0025 (12)
C26	0.0148 (14)	0.0148 (14)	0.0247 (16)	0.0009 (11)	0.0005 (12)	0.0013 (12)
C27	0.0269 (16)	0.0126 (14)	0.0293 (17)	−0.0019 (12)	0.0033 (13)	0.0021 (12)
C28	0.0359 (19)	0.0136 (14)	0.035 (2)	−0.0055 (12)	0.0036 (15)	−0.0036 (13)
C29	0.0305 (17)	0.0147 (14)	0.0287 (17)	−0.0020 (12)	0.0007 (14)	−0.0057 (12)
C30	0.0168 (15)	0.0174 (15)	0.0237 (16)	0.0009 (11)	0.0008 (12)	−0.0040 (12)
C31	0.0157 (15)	0.0159 (15)	0.0258 (17)	0.0005 (11)	0.0024 (12)	−0.0006 (12)
C32	0.0273 (16)	0.0277 (17)	0.0222 (16)	−0.0046 (12)	−0.0017 (14)	−0.0065 (15)
C33	0.0233 (17)	0.034 (2)	0.0213 (16)	−0.0021 (14)	0.0001 (13)	−0.0002 (14)
C34	0.0149 (16)	0.0327 (18)	0.0245 (16)	−0.0007 (13)	−0.0002 (13)	0.0058 (14)
C35	0.0159 (15)	0.0171 (14)	0.0277 (16)	−0.0009 (11)	0.0008 (12)	0.0045 (12)
P1	0.0173 (3)	0.0206 (3)	0.0220 (4)	−0.0014 (3)	−0.0014 (3)	0.0043 (4)
F11	0.0604 (15)	0.0288 (11)	0.0290 (11)	−0.0096 (10)	−0.0010 (10)	0.0081 (9)
F12	0.0412 (13)	0.0762 (18)	0.0295 (12)	0.0268 (12)	0.0053 (10)	0.0076 (12)
F13	0.0272 (11)	0.0636 (15)	0.0277 (11)	−0.0158 (10)	−0.0083 (9)	0.0098 (10)
F14	0.0543 (15)	0.0551 (15)	0.0339 (12)	0.0287 (12)	0.0038 (11)	0.0004 (11)
F15	0.0329 (13)	0.0671 (17)	0.0369 (13)	−0.0200 (11)	−0.0104 (10)	0.0106 (12)
F16	0.0697 (17)	0.0369 (13)	0.0477 (15)	−0.0190 (12)	−0.0112 (13)	0.0209 (11)
P2	0.0418 (5)	0.0167 (3)	0.0312 (5)	−0.0054 (3)	0.0004 (4)	−0.0044 (4)
F21	0.093 (2)	0.0467 (14)	0.0464 (16)	−0.0465 (14)	−0.0020 (14)	0.0039 (12)
F22	0.0305 (11)	0.0396 (12)	0.0783 (18)	−0.0016 (9)	0.0024 (13)	−0.0136 (14)
F23	0.0615 (16)	0.0487 (15)	0.0342 (12)	−0.0094 (12)	−0.0039 (11)	−0.0094 (11)
F24	0.116 (3)	0.0338 (13)	0.0576 (19)	0.0370 (15)	0.0013 (16)	−0.0069 (12)
F25	0.0831 (19)	0.0298 (12)	0.0367 (13)	−0.0235 (12)	−0.0118 (12)	0.0036 (10)
F26	0.0352 (12)	0.0343 (12)	0.0541 (14)	−0.0045 (9)	0.0122 (10)	−0.0061 (10)
C41	0.074 (3)	0.048 (3)	0.080 (4)	−0.016 (2)	−0.032 (3)	0.020 (3)
C42	0.054 (2)	0.0251 (17)	0.036 (2)	0.0097 (16)	−0.0056 (19)	0.0037 (16)
N43	0.050 (2)	0.0265 (15)	0.047 (2)	0.0066 (14)	0.0009 (16)	0.0026 (15)
C51	0.044 (2)	0.044 (2)	0.045 (2)	−0.0034 (18)	0.0125 (19)	0.0020 (19)
C52	0.0322 (19)	0.0219 (16)	0.036 (2)	0.0064 (13)	−0.0042 (15)	−0.0004 (14)
N53	0.053 (2)	0.0313 (17)	0.0368 (18)	0.0028 (14)	0.0104 (16)	0.0072 (14)

Geometric parameters (Å, º) top

Ru1—N1	2.088 (2)	C22—H22	0.95
Ru1—N3	1.980 (2)	C23—C24	1.393 (5)
Ru1—N4	2.069 (2)	C23—H23	0.95
Ru1—N6	2.083 (3)	C24—C25	1.383 (5)
Ru1—N7	2.000 (2)	C24—H24	0.95
Ru1—N8	2.068 (3)	C25—C26	1.475 (4)
N1—C1	1.309 (4)	C26—C27	1.391 (4)
N1—C4	1.403 (3)	C27—C28	1.389 (5)
N2—C4	1.321 (4)	C27—H27	0.95
N2—C3	1.330 (4)	C28—C29	1.384 (5)
N3—C5	1.344 (4)	C28—H28	0.95
N3—C9	1.358 (3)	C29—C30	1.396 (4)
N4—C13	1.344 (4)	C29—H29	0.95
N4—C10	1.376 (3)	C30—C31	1.471 (4)
N5—C10	1.337 (3)	C31—C32	1.375 (5)
N5—C11	1.339 (4)	C32—C33	1.399 (5)
N6—C21	1.342 (4)	C32—H32	0.95
N6—C25	1.363 (4)	C33—C34	1.375 (5)
N7—C26	1.340 (4)	C33—H33	0.95
N7—C30	1.349 (4)	C34—C35	1.392 (4)
N8—C35	1.341 (4)	C34—H34	0.95
N8—C31	1.370 (4)	C35—H35	0.95
Cl1—C2	1.722 (3)	P1—F13	1.584 (2)
Cl2—C12	1.717 (3)	P1—F15	1.592 (2)
C1—C2	1.386 (4)	P1—F16	1.594 (2)
C1—H1	0.95	P1—F14	1.598 (2)
C2—C3	1.381 (4)	P1—F11	1.599 (2)
C3—H3	0.95	P1—F12	1.608 (2)
C4—C5	1.473 (4)	P2—F22	1.596 (2)
C5—C6	1.391 (4)	P2—F24	1.598 (3)
C6—C7	1.395 (4)	P2—F21	1.600 (2)
C6—H6	0.95	P2—F23	1.600 (3)
C7—C8	1.382 (4)	P2—F25	1.602 (2)
C7—H7	0.95	P2—F26	1.604 (2)
C8—C9	1.383 (4)	C41—C42	1.448 (6)
C8—H8	0.95	C41—H41a	0.98
C9—C10	1.462 (4)	C41—H41b	0.98
C11—C12	1.387 (4)	C41—H41c	0.98
C11—H11	0.95	C42—N43	1.140 (5)
C12—C13	1.378 (4)	C51—C52	1.453 (5)
C13—H13	0.95	C51—H51a	0.98
C21—C22	1.383 (5)	C51—H51b	0.98
C21—H21	0.95	C51—H51c	0.98
C22—C23	1.374 (5)	C52—N53	1.145 (5)

N3—Ru1—N7	175.35 (9)	C24—C23—H23	120.5
N3—Ru1—N8	100.81 (12)	C25—C24—C23	119.2 (3)
N7—Ru1—N8	78.90 (12)	C25—C24—H24	120.4
N3—Ru1—N4	79.37 (9)	C23—C24—H24	120.4
N7—Ru1—N4	96.00 (9)	N6—C25—C24	121.5 (3)
N8—Ru1—N4	92.69 (10)	N6—C25—C26	114.8 (3)
N3—Ru1—N6	101.62 (11)	C24—C25—C26	123.7 (3)
N7—Ru1—N6	78.75 (11)	N7—C26—C27	119.8 (3)
N8—Ru1—N6	157.58 (9)	N7—C26—C25	113.7 (3)
N4—Ru1—N6	91.4 (1)	C27—C26—C25	126.3 (3)
N3—Ru1—N1	79.51 (9)	C28—C27—C26	118.5 (3)
N7—Ru1—N1	105.12 (9)	C28—C27—H27	120.7
N8—Ru1—N1	90.79 (10)	C26—C27—H27	120.7
N4—Ru1—N1	158.87 (9)	C29—C28—C27	120.7 (3)
N6—Ru1—N1	93.3 (1)	C29—C28—H28	119.6
C1—N1—C4	116.3 (2)	C27—C28—H28	119.6
C1—N1—RU1	131.55 (19)	C28—C29—C30	118.8 (3)
C4—N1—RU1	112.15 (18)	C28—C29—H29	120.6
C4—N2—C3	117.3 (3)	C30—C29—H29	120.6
C5—N3—C9	121.2 (2)	N7—C30—C29	119.1 (3)
C5—N3—RU1	119.80 (18)	N7—C30—C31	113.2 (3)
C9—N3—RU1	119.00 (18)	C29—C30—C31	127.7 (3)
C13—N4—C10	116.5 (2)	N8—C31—C32	121.3 (3)
C13—N4—RU1	130.4 (2)	N8—C31—C30	115.1 (3)
C10—N4—RU1	113.08 (18)	C32—C31—C30	123.6 (3)
C10—N5—C11	117.3 (2)	C31—C32—C33	119.4 (3)
C21—N6—C25	118.5 (3)	C31—C32—H32	120.3
C21—N6—RU1	127.5 (2)	C33—C32—H32	120.3
C25—N6—RU1	113.9 (2)	C34—C33—C32	119.5 (3)
C26—N7—C30	123.0 (2)	C34—C33—H33	120.3
C26—N7—RU1	118.3 (2)	C32—C33—H33	120.3
C30—N7—RU1	117.8 (2)	C33—C34—C35	118.4 (3)
C35—N8—C31	118.5 (3)	C33—C34—H34	120.8
C35—N8—RU1	127.7 (2)	C35—C34—H34	120.8
C31—N8—RU1	113.8 (2)	N8—C35—C34	122.9 (3)
N1—C1—C2	121.0 (3)	N8—C35—H35	118.6
N1—C1—H1	119.5	C34—C35—H35	118.6
C2—C1—H1	119.5	F13—P1—F15	179.9 (2)
C3—C2—C1	119.3 (3)	F13—P1—F16	89.53 (13)
C3—C2—CL1	120.6 (2)	F15—P1—F16	90.45 (13)
C1—C2—CL1	120.0 (2)	F13—P1—F14	90.07 (13)
N2—C3—C2	120.9 (3)	F15—P1—F14	89.98 (15)
N2—C3—H3	119.6	F16—P1—F14	91.42 (15)
C2—C3—H3	119.6	F13—P1—F11	90.51 (12)
N2—C4—N1	125.1 (3)	F15—P1—F11	89.51 (13)
N2—C4—C5	119.1 (3)	F16—P1—F11	179.77 (18)
N1—C4—C5	115.7 (2)	F14—P1—F11	88.81 (14)
N3—C5—C6	120.9 (3)	F13—P1—F12	89.74 (14)
N3—C5—C4	112.8 (2)	F15—P1—F12	90.21 (13)
C6—C5—C4	126.3 (3)	F16—P1—F12	89.14 (15)
C5—C6—C7	118.5 (3)	F14—P1—F12	179.41 (16)
C5—C6—H6	120.8	F11—P1—F12	90.63 (14)
C7—C6—H6	120.8	F22—P2—F24	179.57 (19)
C8—C7—C6	119.7 (2)	F22—P2—F21	89.79 (15)
C8—C7—H7	120.2	F24—P2—F21	90.59 (18)
C6—C7—H7	120.2	F22—P2—F23	90.44 (15)
C7—C8—C9	119.9 (3)	F24—P2—F23	89.76 (15)
C7—C8—H8	120.1	F21—P2—F23	90.67 (14)
C9—C8—H8	120.1	F22—P2—F25	90.61 (16)
N3—C9—C8	119.8 (2)	F24—P2—F25	89.19 (15)
N3—C9—C10	112.4 (2)	F21—P2—F25	90.15 (13)
C8—C9—C10	127.8 (2)	F23—P2—F25	178.67 (18)
N5—C10—N4	125.1 (3)	F22—P2—F26	89.60 (12)
N5—C10—C9	118.7 (2)	F24—P2—F26	90.02 (16)
N4—C10—C9	116.2 (2)	F21—P2—F26	179.30 (17)
N5—C11—C12	121.1 (3)	F23—P2—F26	89.68 (13)
N5—C11—H11	119.5	F25—P2—F26	89.51 (14)
C12—C11—H11	119.5	C42—C41—H41A	109.5
C13—C12—C11	119.0 (3)	C42—C41—H41B	109.5
C13—C12—CL2	120.3 (2)	H41A—C41—H41B	109.5
C11—C12—CL2	120.7 (2)	C42—C41—H41C	109.5
N4—C13—C12	120.9 (3)	H41A—C41—H41C	109.5
N4—C13—H13	119.5	H41B—C41—H41C	109.5
C12—C13—H13	119.5	N43—C42—C41	179.1 (5)
N6—C21—C22	122.3 (3)	C52—C51—H51A	109.5
N6—C21—H21	118.9	C52—C51—H51B	109.5
C22—C21—H21	118.9	H51A—C51—H51B	109.5
C23—C22—C21	119.4 (3)	C52—C51—H51C	109.5
C23—C22—H22	120.3	H51A—C51—H51C	109.5
C21—C22—H22	120.3	H51B—C51—H51C	109.5
C22—C23—C24	118.9 (3)	N53—C52—C51	179.4 (5)
C22—C23—H23	120.5

N3—RU1—N1—C1	178.0 (3)	N1—C4—C5—N3	−1.7 (4)
N7—RU1—N1—C1	−1.6 (3)	N2—C4—C5—C6	−1.3 (5)
N8—RU1—N1—C1	77.1 (3)	N1—C4—C5—C6	177.6 (3)
N4—RU1—N1—C1	176.7 (3)	N3—C5—C6—C7	−1.1 (5)
N6—RU1—N1—C1	−80.8 (3)	C4—C5—C6—C7	179.7 (3)
N3—RU1—N1—C4	0.1 (2)	C5—C6—C7—C8	−0.5 (6)
N7—RU1—N1—C4	−179.5 (2)	C6—C7—C8—C9	2.5 (6)
N8—RU1—N1—C4	−100.8 (2)	C5—N3—C9—C8	1.3 (5)
N4—RU1—N1—C4	−1.3 (4)	RU1—N3—C9—C8	179.5 (3)
N6—RU1—N1—C4	101.3 (2)	C5—N3—C9—C10	−178.7 (3)
N8—RU1—N3—C5	87.7 (3)	RU1—N3—C9—C10	−0.5 (4)
N4—RU1—N3—C5	178.4 (3)	C7—C8—C9—N3	−2.9 (5)
N6—RU1—N3—C5	−92.3 (3)	C7—C8—C9—C10	177.1 (3)
N1—RU1—N3—C5	−1.1 (3)	C11—N5—C10—N4	−2.5 (5)
N8—RU1—N3—C9	−90.5 (3)	C11—N5—C10—C9	177.4 (3)
N4—RU1—N3—C9	0.2 (3)	C13—N4—C10—N5	0.7 (5)
N6—RU1—N3—C9	89.5 (3)	RU1—N4—C10—N5	179.5 (3)
N1—RU1—N3—C9	−179.3 (3)	C13—N4—C10—C9	−179.2 (3)
N3—RU1—N4—C13	178.7 (3)	RU1—N4—C10—C9	−0.4 (4)
N7—RU1—N4—C13	−1.7 (3)	N3—C9—C10—N5	−179.4 (3)
N8—RU1—N4—C13	−80.8 (3)	C8—C9—C10—N5	0.6 (5)
N6—RU1—N4—C13	77.2 (3)	N3—C9—C10—N4	0.6 (4)
N1—RU1—N4—C13	−179.9 (2)	C8—C9—C10—N4	−179.4 (3)
N3—RU1—N4—C10	0.1 (2)	C10—N5—C11—C12	1.7 (4)
N7—RU1—N4—C10	179.7 (2)	N5—C11—C12—C13	0.7 (5)
N8—RU1—N4—C10	100.6 (2)	N5—C11—C12—CL2	−180.0 (2)
N6—RU1—N4—C10	−101.4 (2)	C10—N4—C13—C12	1.9 (4)
N1—RU1—N4—C10	1.4 (4)	RU1—N4—C13—C12	−176.7 (2)
N3—RU1—N6—C21	3.4 (3)	C11—C12—C13—N4	−2.6 (5)
N7—RU1—N6—C21	178.7 (3)	CL2—C12—C13—N4	178.1 (2)
N8—RU1—N6—C21	−176.7 (2)	C25—N6—C21—C22	−3.4 (5)
N4—RU1—N6—C21	82.9 (3)	RU1—N6—C21—C22	175.4 (2)
N1—RU1—N6—C21	−76.5 (2)	N6—C21—C22—C23	−0.8 (5)
N3—RU1—N6—C25	−177.8 (2)	C21—C22—C23—C24	3.9 (5)
N7—RU1—N6—C25	−2.5 (2)	C22—C23—C24—C25	−2.9 (5)
N8—RU1—N6—C25	2.2 (4)	C21—N6—C25—C24	4.5 (4)
N4—RU1—N6—C25	−98.3 (2)	RU1—N6—C25—C24	−174.5 (2)
N1—RU1—N6—C25	102.3 (2)	C21—N6—C25—C26	−174.9 (3)
N8—RU1—N7—C26	179.8 (2)	RU1—N6—C25—C26	6.1 (3)
N4—RU1—N7—C26	88.3 (2)	C23—C24—C25—N6	−1.3 (5)
N6—RU1—N7—C26	−2.0 (2)	C23—C24—C25—C26	178.0 (3)
N1—RU1—N7—C26	−92.4 (2)	C30—N7—C26—C27	0.2 (4)
N8—RU1—N7—C30	10.2 (2)	RU1—N7—C26—C27	−168.9 (2)
N4—RU1—N7—C30	−81.4 (2)	C30—N7—C26—C25	174.8 (3)
N6—RU1—N7—C30	−171.6 (2)	RU1—N7—C26—C25	5.7 (3)
N1—RU1—N7—C30	98.0 (2)	N6—C25—C26—N7	−7.7 (4)
N3—RU1—N8—C35	−12.3 (3)	C24—C25—C26—N7	172.9 (3)
N7—RU1—N8—C35	172.5 (3)	N6—C25—C26—C27	166.5 (3)
N4—RU1—N8—C35	−91.9 (3)	C24—C25—C26—C27	−12.9 (5)
N6—RU1—N8—C35	167.8 (2)	N7—C26—C27—C28	0.4 (5)
N1—RU1—N8—C35	67.2 (3)	C25—C26—C27—C28	−173.5 (3)
N3—RU1—N8—C31	167.6 (2)	C26—C27—C28—C29	−0.2 (5)
N7—RU1—N8—C31	−7.6 (2)	C27—C28—C29—C30	−0.4 (5)
N4—RU1—N8—C31	87.9 (2)	C26—N7—C30—C29	−0.9 (4)
N6—RU1—N8—C31	−12.3 (4)	RU1—N7—C30—C29	168.3 (2)
N1—RU1—N8—C31	−112.9 (2)	C26—N7—C30—C31	−179.7 (3)
C4—N1—C1—C2	1.8 (4)	RU1—N7—C30—C31	−10.6 (3)
RU1—N1—C1—C2	−176.1 (2)	C28—C29—C30—N7	1.0 (5)
N1—C1—C2—C3	−3.1 (5)	C28—C29—C30—C31	179.6 (3)
N1—C1—C2—CL1	175.5 (3)	C35—N8—C31—C32	3.9 (4)
C4—N2—C3—C2	1.5 (4)	RU1—N8—C31—C32	−176.0 (2)
C1—C2—C3—N2	1.5 (5)	C35—N8—C31—C30	−175.6 (3)
CL1—C2—C3—N2	−177.1 (2)	RU1—N8—C31—C30	4.5 (3)
C3—N2—C4—N1	−3.0 (4)	N7—C30—C31—N8	3.6 (4)
C3—N2—C4—C5	175.8 (3)	C29—C30—C31—N8	−175.1 (3)
C1—N1—C4—N2	1.3 (4)	N7—C30—C31—C32	−175.9 (3)
RU1—N1—C4—N2	179.6 (2)	C29—C30—C31—C32	5.4 (5)
C1—N1—C4—C5	−177.4 (3)	N8—C31—C32—C33	−2.8 (5)
RU1—N1—C4—C5	0.8 (3)	C30—C31—C32—C33	176.7 (3)
C9—N3—C5—C6	0.7 (6)	C31—C32—C33—C34	0.0 (5)
RU1—N3—C5—C6	−177.5 (3)	C32—C33—C34—C35	1.6 (5)
C9—N3—C5—C4	180.0 (3)	C31—N8—C35—C34	−2.3 (5)
RU1—N3—C5—C4	1.8 (4)	RU1—N8—C35—C34	177.6 (2)
N2—C4—C5—N3	179.5 (3)	C33—C34—C35—N8	−0.5 (5)

Experimental details

Crystal data
Chemical formula	[Ru(C₁₃H₇Cl₂N₅)(C₁₅H₁₁N₃)](PF₆)₂·2C₂H₃N
M_r	1010.52
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	100
a, b, c (Å)	16.3846 (2), 62.8985 (8), 14.5581 (2)
V (Å³)	15003.1 (3)
Z	16
Radiation type	Cu Kα
µ (mm⁻¹)	6.44
Crystal size (mm)	0.48 × 0.25 × 0.07

Data collection
Diffractometer	Bruker SMART 2K diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.190, 0.640
No. of measured, independent and observed [I > 2σ(I)] reflections	45518, 7327, 7121
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.072, 1.08
No. of reflections	7327
No. of parameters	534
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.38
Absolute structure	Flack (1983), 3439 Friedel pairs
Absolute structure parameter	0.052 (5)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1997), UdMX (local program).

Selected geometric parameters (Å, º) top

Ru1—N1	2.088 (2)	Ru1—N6	2.083 (3)
Ru1—N3	1.980 (2)	Ru1—N7	2.000 (2)
Ru1—N4	2.069 (2)	Ru1—N8	2.068 (3)

N3—Ru1—N7	175.35 (9)	N8—Ru1—N6	157.58 (9)
N3—Ru1—N8	100.81 (12)	N4—Ru1—N6	91.4 (1)
N7—Ru1—N8	78.90 (12)	N3—Ru1—N1	79.51 (9)
N3—Ru1—N4	79.37 (9)	N7—Ru1—N1	105.12 (9)
N7—Ru1—N4	96.00 (9)	N8—Ru1—N1	90.79 (10)
N8—Ru1—N4	92.69 (10)	N4—Ru1—N1	158.87 (9)
N3—Ru1—N6	101.62 (11)	N6—Ru1—N1	93.3 (1)
N7—Ru1—N6	78.75 (11)

Acknowledgements

We are grateful to the Natural Sciences and Engineering Research Council of Canada and the Ministère de l'Education du Québec for financial support.

References

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