μ-1,6,7,12-Tetra-aza-perylene-κ(4) N (1),N (12):N (6),N (7)-bis-[chlorido-(η(6)-p-cymene)ruthenium(II)] bis-(hexa-fluorido-phosphate) acetone disolvate.

In the title compound, [Ru2(C10H14)2Cl2(C16H8N4)](PF6)2·2C3H6O, the binuclear Ru(II) complex dication, [{RuCl(η(6)-cym)}2(μ-tape)](2+), built up by a planar 1,6,7,12-tetra-aza-perylene (tape) bridge, two η(6)-bound cymene (cym) ligands and two chloride ligands, includes an inversion center. The Ru(II) atom shows the typical piano-stool motif for arene coordination. The counter-charge is provided by a hexa-fluorido-phosphate anion and the asymmetric unit is completed by an acetone mol-ecule of crystallization. The components of the structure are connected into a three-dimensional architecture by C-H⋯O/F/Cl inter-actions.

Related literature

For related RuII–arene complexes, see: Bennett & Smith (1974 ▶); Robertson et al. (1980 ▶); Govindaswamy et al. (2007 ▶); Betanzos-Lara et al. (2012 ▶). For tetra­aza­perylene-bridged RuII complexes, see: Brietzke, Mickler, Kelling & Holdt (2012 ▶); Brietzke, Mickler, Kelling, Schilde et al. (2012 ▶).

Experimental

Crystal data

[Ru2(C10H14)2Cl2(C16H8N4)](PF6)2·2C3H6O

M = 1203.82

Triclinic,

a = 8.6289 (5) Å

b = 11.9346 (7) Å

c = 12.7785 (7) Å

α = 66.099 (4)°

β = 83.536 (4)°

γ = 77.572 (4)°

V = 1174.45 (12) Å3

Z = 1

Mo Kα radiation

μ = 0.91 mm−1

T = 293 K

1.50 × 0.62 × 0.17 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2011 ▶) T min = 0.614, T max = 0.860

15353 measured reflections

4133 independent reflections

3971 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.01

4133 reflections

302 parameters

H-atom parameters constrained

Δρmax = 1.17 e Å−3

Δρmin = −0.67 e Å−3

Data collection: X-AREA (Stoe & Cie, 2011 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400035X/tk5277sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400035X/tk5277Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ru2(C10H14)2Cl2(C16H8N4)](PF6)2·2C3H6O	Z = 1
Mr = 1203.82	F(000) = 604
Triclinic, P1	Dx = 1.702 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6289 (5) Å	Cell parameters from 20121 reflections
b = 11.9346 (7) Å	θ = 1.7–29.8°
c = 12.7785 (7) Å	µ = 0.91 mm−1
α = 66.099 (4)°	T = 293 K
β = 83.536 (4)°	Needle, black
γ = 77.572 (4)°	1.50 × 0.62 × 0.17 mm
V = 1174.45 (12) Å3

Stoe IPDS-2 diffractometer	4133 independent reflections
Radiation source: sealed X-ray tube	3971 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.047
ω scan	θmax = 25.0°, θmin = 1.7°
Absorption correction: integration (X-RED; Stoe & Cie, 2011)	h = −9→10
Tmin = 0.614, Tmax = 0.860	k = −14→14
15353 measured reflections	l = −15→15

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.045P)2 + 1.286P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.003
4133 reflections	Δρmax = 1.17 e Å−3
302 parameters	Δρmin = −0.67 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (8)

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
C1	0.5372 (3)	0.7198 (2)	0.1198 (2)	0.0278 (5)
H1	0.5127	0.7695	0.1619	0.033*
C2	0.6772 (3)	0.7223 (2)	0.0576 (2)	0.0282 (5)
H2	0.7457	0.7720	0.0592	0.034*
C3	0.1439 (3)	0.3571 (2)	0.0791 (2)	0.0288 (5)
H3	0.0679	0.3099	0.0853	0.035*
C4	0.1221 (3)	0.4332 (2)	0.1380 (2)	0.0293 (5)
H4	0.0302	0.4364	0.1831	0.035*
C5	0.3591 (3)	0.5000 (2)	0.0674 (2)	0.0237 (5)
C6	0.4691 (3)	0.5778 (2)	0.0619 (2)	0.0231 (5)
C7	0.3911 (3)	0.4242 (2)	0.0050 (2)	0.0231 (5)
C8	0.7183 (3)	0.6500 (2)	−0.0090 (2)	0.0250 (5)
C9	0.1106 (3)	0.7601 (3)	0.2988 (2)	0.0302 (6)
C10	−0.0022 (3)	0.6859 (3)	0.3042 (2)	0.0313 (6)
H10	−0.1038	0.7252	0.2778	0.038*
C11	0.0364 (3)	0.5555 (3)	0.3479 (2)	0.0312 (6)
H11	−0.0400	0.5097	0.3515	0.037*
C12	0.1928 (3)	0.4922 (2)	0.3873 (2)	0.0314 (6)
C13	0.3041 (3)	0.5644 (3)	0.3818 (2)	0.0307 (6)
H13	0.4067	0.5251	0.4062	0.037*
C14	0.2629 (3)	0.6972 (2)	0.3395 (2)	0.0292 (5)
H14	0.3380	0.7428	0.3389	0.035*
C15	0.0633 (4)	0.9007 (3)	0.2507 (3)	0.0383 (7)
H15	−0.0254	0.9237	0.1999	0.046*
C16	0.0016 (5)	0.9403 (3)	0.3501 (3)	0.0629 (11)
H16A	0.0839	0.9136	0.4044	0.094*
H16B	−0.0883	0.9027	0.3868	0.094*
H16C	−0.0294	1.0295	0.3213	0.094*
C17	0.1938 (4)	0.9683 (3)	0.1810 (3)	0.0527 (8)
H17A	0.2254	0.9444	0.1174	0.079*
H17B	0.2834	0.9467	0.2283	0.079*
H17C	0.1555	1.0567	0.1532	0.079*
C18	0.2359 (4)	0.3522 (3)	0.4299 (3)	0.0396 (7)
H18A	0.1643	0.3221	0.3997	0.059*
H18B	0.2284	0.3167	0.5120	0.059*
H18C	0.3426	0.3287	0.4051	0.059*
C19	0.5166 (6)	0.9785 (4)	0.3738 (4)	0.0748 (12)
H19A	0.4216	1.0407	0.3534	0.112*
H19B	0.5910	1.0067	0.4036	0.112*
H19C	0.4914	0.9021	0.4310	0.112*
C20	0.5881 (4)	0.9566 (3)	0.2701 (3)	0.0446 (7)
C21	0.6172 (6)	1.0667 (5)	0.1694 (4)	0.0792 (13)
H21A	0.6894	1.1064	0.1881	0.119*
H21B	0.5188	1.1241	0.1458	0.119*
H21C	0.6625	1.0419	0.1082	0.119*
Cl1	0.09547 (8)	0.78153 (6)	0.03483 (5)	0.03517 (17)
F1	0.5627 (2)	0.3410 (2)	0.26787 (17)	0.0589 (5)
F2	0.8898 (2)	0.3000 (2)	0.3836 (2)	0.0675 (6)
F3	0.7334 (4)	0.4617 (2)	0.2626 (3)	0.0938 (10)
F4	0.7241 (3)	0.1753 (2)	0.3893 (3)	0.0811 (8)
F5	0.6323 (3)	0.3400 (3)	0.4315 (2)	0.0837 (8)
F6	0.8209 (3)	0.2954 (4)	0.2213 (3)	0.1058 (11)
N1	0.4310 (2)	0.64737 (19)	0.12313 (17)	0.0247 (4)
N2	0.2288 (2)	0.50461 (19)	0.13364 (17)	0.0253 (4)
O1	0.6209 (3)	0.8519 (2)	0.2737 (2)	0.0611 (7)
P1	0.72700 (9)	0.31873 (7)	0.32587 (7)	0.03586 (18)
Ru1	0.20978 (2)	0.63314 (2)	0.21078 (2)	0.02344 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0287 (13)	0.0305 (12)	0.0306 (12)	−0.0114 (11)	0.0015 (11)	−0.0163 (10)
C2	0.0275 (13)	0.0300 (12)	0.0326 (13)	−0.0140 (11)	0.0003 (11)	−0.0139 (11)
C3	0.0250 (12)	0.0325 (13)	0.0336 (13)	−0.0145 (11)	0.0032 (11)	−0.0141 (11)
C4	0.0233 (12)	0.0356 (13)	0.0336 (13)	−0.0125 (11)	0.0061 (11)	−0.0166 (11)
C5	0.0224 (11)	0.0265 (11)	0.0231 (11)	−0.0090 (10)	0.0017 (9)	−0.0092 (9)
C6	0.0232 (12)	0.0268 (11)	0.0217 (11)	−0.0091 (10)	0.0007 (9)	−0.0103 (9)
C7	0.0225 (12)	0.0254 (11)	0.0231 (11)	−0.0091 (10)	−0.0010 (10)	−0.0088 (9)
C8	0.0241 (12)	0.0267 (12)	0.0258 (12)	−0.0098 (10)	−0.0007 (10)	−0.0094 (10)
C9	0.0299 (13)	0.0352 (14)	0.0296 (13)	−0.0034 (11)	0.0049 (11)	−0.0197 (11)
C10	0.0230 (12)	0.0410 (14)	0.0325 (13)	−0.0035 (11)	0.0058 (11)	−0.0199 (12)
C11	0.0277 (13)	0.0392 (14)	0.0308 (13)	−0.0126 (11)	0.0100 (11)	−0.0176 (11)
C12	0.0349 (14)	0.0333 (13)	0.0241 (12)	−0.0078 (12)	0.0068 (11)	−0.0107 (10)
C13	0.0303 (13)	0.0366 (14)	0.0239 (12)	−0.0040 (11)	0.0004 (10)	−0.0120 (11)
C14	0.0306 (13)	0.0370 (14)	0.0268 (12)	−0.0086 (11)	0.0011 (10)	−0.0186 (11)
C15	0.0356 (15)	0.0341 (14)	0.0459 (16)	−0.0002 (12)	−0.0046 (13)	−0.0186 (13)
C16	0.079 (3)	0.0439 (18)	0.068 (2)	0.0035 (18)	0.009 (2)	−0.0350 (18)
C17	0.0503 (19)	0.0348 (16)	0.067 (2)	−0.0084 (14)	−0.0035 (17)	−0.0128 (15)
C18	0.0425 (16)	0.0319 (14)	0.0383 (15)	−0.0088 (13)	0.0075 (13)	−0.0090 (12)
C19	0.088 (3)	0.084 (3)	0.073 (3)	−0.039 (3)	0.021 (2)	−0.046 (2)
C20	0.0364 (16)	0.0520 (19)	0.0522 (18)	−0.0107 (14)	−0.0066 (14)	−0.0248 (15)
C21	0.076 (3)	0.085 (3)	0.057 (2)	−0.024 (3)	−0.001 (2)	−0.005 (2)
Cl1	0.0354 (3)	0.0383 (3)	0.0310 (3)	−0.0088 (3)	−0.0050 (3)	−0.0108 (3)
F1	0.0433 (11)	0.0809 (14)	0.0505 (11)	−0.0207 (10)	−0.0098 (9)	−0.0170 (10)
F2	0.0412 (11)	0.0592 (12)	0.0888 (16)	−0.0176 (10)	−0.0221 (11)	−0.0062 (11)
F3	0.104 (2)	0.0417 (12)	0.116 (2)	−0.0260 (13)	−0.0552 (18)	0.0085 (13)
F4	0.0662 (15)	0.0428 (11)	0.124 (2)	−0.0188 (11)	−0.0134 (15)	−0.0148 (13)
F5	0.0653 (15)	0.138 (2)	0.0661 (14)	−0.0051 (15)	−0.0010 (12)	−0.0656 (16)
F6	0.0733 (17)	0.181 (3)	0.103 (2)	−0.053 (2)	0.0486 (16)	−0.094 (2)
N1	0.0239 (10)	0.0284 (10)	0.0254 (10)	−0.0091 (9)	0.0016 (8)	−0.0128 (8)
N2	0.0240 (10)	0.0289 (10)	0.0265 (10)	−0.0100 (9)	0.0037 (9)	−0.0128 (9)
O1	0.0586 (15)	0.0611 (16)	0.0792 (18)	−0.0093 (13)	−0.0124 (14)	−0.0416 (14)
P1	0.0298 (4)	0.0372 (4)	0.0405 (4)	−0.0110 (3)	0.0007 (3)	−0.0131 (3)
Ru1	0.02053 (13)	0.02803 (14)	0.02507 (14)	−0.00703 (9)	0.00287 (9)	−0.01342 (9)

C1—C2	1.368 (4)	C13—H13	0.9300
C1—N1	1.376 (3)	C14—Ru1	2.200 (3)
C1—H1	0.9300	C14—H14	0.9300
C2—C8	1.411 (4)	C15—C17	1.515 (5)
C2—H2	0.9300	C15—C16	1.531 (4)
C3—C4	1.369 (4)	C15—H15	0.9800
C3—C8i	1.415 (4)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—N2	1.366 (3)	C16—H16C	0.9600
C4—H4	0.9300	C17—H17A	0.9600
C5—N2	1.335 (3)	C17—H17B	0.9600
C5—C7	1.399 (3)	C17—H17C	0.9600
C5—C6	1.442 (3)	C18—H18A	0.9600
C6—N1	1.327 (3)	C18—H18B	0.9600
C6—C7i	1.400 (3)	C18—H18C	0.9600
C7—C6i	1.400 (3)	C19—C20	1.493 (5)
C7—C8i	1.410 (3)	C19—H19A	0.9600
C8—C7i	1.410 (3)	C19—H19B	0.9600
C8—C3i	1.415 (4)	C19—H19C	0.9600
C9—C14	1.405 (4)	C20—O1	1.203 (4)
C9—C10	1.430 (4)	C20—C21	1.465 (5)
C9—C15	1.512 (4)	C21—H21A	0.9600
C9—Ru1	2.214 (2)	C21—H21B	0.9600
C10—C11	1.399 (4)	C21—H21C	0.9600
C10—Ru1	2.188 (2)	Cl1—Ru1	2.3844 (7)
C10—H10	0.9300	F1—P1	1.595 (2)
C11—C12	1.432 (4)	F2—P1	1.592 (2)
C11—Ru1	2.204 (3)	F3—P1	1.575 (2)
C11—H11	0.9300	F4—P1	1.574 (2)
C12—C13	1.401 (4)	F5—P1	1.579 (2)
C12—C18	1.506 (4)	F6—P1	1.574 (3)
C12—Ru1	2.212 (3)	N1—Ru1	2.105 (2)
C13—C14	1.427 (4)	N2—Ru1	2.105 (2)
C13—Ru1	2.185 (3)
C2—C1—N1	123.2 (2)	C12—C18—H18A	109.5
C2—C1—H1	118.4	C12—C18—H18B	109.5
N1—C1—H1	118.4	H18A—C18—H18B	109.5
C1—C2—C8	120.4 (2)	C12—C18—H18C	109.5
C1—C2—H2	119.8	H18A—C18—H18C	109.5
C8—C2—H2	119.8	H18B—C18—H18C	109.5
C4—C3—C8i	120.2 (2)	C20—C19—H19A	109.5
C4—C3—H3	119.9	C20—C19—H19B	109.5
C8i—C3—H3	119.9	H19A—C19—H19B	109.5
N2—C4—C3	123.2 (2)	C20—C19—H19C	109.5
N2—C4—H4	118.4	H19A—C19—H19C	109.5
C3—C4—H4	118.4	H19B—C19—H19C	109.5
N2—C5—C7	122.9 (2)	O1—C20—C21	123.9 (4)
N2—C5—C6	117.0 (2)	O1—C20—C19	119.5 (4)
C7—C5—C6	120.2 (2)	C21—C20—C19	116.6 (4)
N1—C6—C7i	123.5 (2)	C20—C21—H21A	109.5
N1—C6—C5	116.9 (2)	C20—C21—H21B	109.5
C7i—C6—C5	119.7 (2)	H21A—C21—H21B	109.5
C6i—C7—C5	120.2 (2)	C20—C21—H21C	109.5
C6i—C7—C8i	119.9 (2)	H21A—C21—H21C	109.5
C5—C7—C8i	119.9 (2)	H21B—C21—H21C	109.5
C2—C8—C7i	116.0 (2)	C6—N1—C1	117.0 (2)
C2—C8—C3i	127.8 (2)	C6—N1—Ru1	114.24 (17)
C7i—C8—C3i	116.2 (2)	C1—N1—Ru1	128.77 (17)
C14—C9—C10	117.4 (2)	C5—N2—C4	117.6 (2)
C14—C9—C15	122.8 (3)	C5—N2—Ru1	113.90 (17)
C10—C9—C15	119.8 (2)	C4—N2—Ru1	128.38 (16)
C14—C9—Ru1	70.90 (14)	F6—P1—F4	90.27 (19)
C10—C9—Ru1	70.05 (14)	F6—P1—F3	89.3 (2)
C15—C9—Ru1	130.05 (19)	F4—P1—F3	178.93 (15)
C11—C10—C9	121.8 (3)	F6—P1—F5	179.13 (19)
C11—C10—Ru1	72.07 (14)	F4—P1—F5	88.87 (16)
C9—C10—Ru1	72.03 (14)	F3—P1—F5	91.57 (18)
C11—C10—H10	119.1	F6—P1—F2	90.33 (16)
C9—C10—H10	119.1	F4—P1—F2	90.70 (13)
Ru1—C10—H10	129.3	F3—P1—F2	88.33 (13)
C10—C11—C12	120.4 (3)	F5—P1—F2	89.85 (14)
C10—C11—Ru1	70.78 (15)	F6—P1—F1	90.38 (15)
C12—C11—Ru1	71.39 (15)	F4—P1—F1	90.59 (13)
C10—C11—H11	119.8	F3—P1—F1	90.39 (13)
C12—C11—H11	119.8	F5—P1—F1	89.46 (13)
Ru1—C11—H11	130.7	F2—P1—F1	178.53 (13)
C13—C12—C11	118.1 (2)	N1—Ru1—N2	77.91 (8)
C13—C12—C18	121.5 (3)	N1—Ru1—C13	95.62 (9)
C11—C12—C18	120.3 (3)	N2—Ru1—C13	117.75 (9)
C13—C12—Ru1	70.36 (15)	N1—Ru1—C10	157.21 (10)
C11—C12—Ru1	70.77 (15)	N2—Ru1—C10	124.11 (10)
C18—C12—Ru1	128.85 (18)	C13—Ru1—C10	79.68 (10)
C12—C13—C14	121.1 (3)	N1—Ru1—C14	95.53 (9)
C12—C13—Ru1	72.49 (15)	N2—Ru1—C14	154.82 (9)
C14—C13—Ru1	71.58 (14)	C13—Ru1—C14	37.97 (10)
C12—C13—H13	119.4	C10—Ru1—C14	67.02 (10)
C14—C13—H13	119.4	N1—Ru1—C11	158.10 (9)
Ru1—C13—H13	128.9	N2—Ru1—C11	97.57 (9)
C9—C14—C13	121.2 (3)	C13—Ru1—C11	67.23 (10)
C9—C14—Ru1	71.98 (15)	C10—Ru1—C11	37.15 (10)
C13—C14—Ru1	70.45 (15)	C14—Ru1—C11	79.41 (10)
C9—C14—H14	119.4	N1—Ru1—C12	120.53 (9)
C13—C14—H14	119.4	N2—Ru1—C12	94.32 (9)
Ru1—C14—H14	130.9	C13—Ru1—C12	37.15 (11)
C9—C15—C17	114.1 (2)	C10—Ru1—C12	67.90 (10)
C9—C15—C16	108.1 (2)	C14—Ru1—C12	67.84 (10)
C17—C15—C16	112.0 (3)	C11—Ru1—C12	37.84 (10)
C9—C15—H15	107.5	N1—Ru1—C9	119.65 (9)
C17—C15—H15	107.5	N2—Ru1—C9	161.77 (10)
C16—C15—H15	107.5	C13—Ru1—C9	68.20 (10)
C15—C16—H16A	109.5	C10—Ru1—C9	37.92 (11)
C15—C16—H16B	109.5	C14—Ru1—C9	37.11 (10)
H16A—C16—H16B	109.5	C11—Ru1—C9	68.03 (10)
C15—C16—H16C	109.5	C12—Ru1—C9	81.09 (10)
H16A—C16—H16C	109.5	N1—Ru1—Cl1	86.45 (6)
H16B—C16—H16C	109.5	N2—Ru1—Cl1	84.46 (6)
C15—C17—H17A	109.5	C13—Ru1—Cl1	157.67 (7)
C15—C17—H17B	109.5	C10—Ru1—Cl1	89.80 (7)
H17A—C17—H17B	109.5	C14—Ru1—Cl1	119.71 (7)
C15—C17—H17C	109.5	C11—Ru1—Cl1	114.67 (8)
H17A—C17—H17C	109.5	C12—Ru1—Cl1	152.21 (8)
H17B—C17—H17C	109.5	C9—Ru1—Cl1	91.43 (7)
N1—C1—C2—C8	1.0 (4)	C11—C12—C13—Ru1	−54.0 (2)
C8i—C3—C4—N2	−0.3 (4)	C18—C12—C13—Ru1	124.2 (2)
N2—C5—C6—N1	−0.1 (3)	C10—C9—C14—C13	1.5 (4)
C7—C5—C6—N1	179.9 (2)	C15—C9—C14—C13	−178.5 (2)
N2—C5—C6—C7i	179.2 (2)	Ru1—C9—C14—C13	−52.6 (2)
C7—C5—C6—C7i	−0.8 (4)	C10—C9—C14—Ru1	54.1 (2)
N2—C5—C7—C6i	−179.2 (2)	C15—C9—C14—Ru1	−125.9 (2)
C6—C5—C7—C6i	0.8 (4)	C12—C13—C14—C9	−1.9 (4)
N2—C5—C7—C8i	1.2 (4)	Ru1—C13—C14—C9	53.3 (2)
C6—C5—C7—C8i	−178.8 (2)	C12—C13—C14—Ru1	−55.2 (2)
C1—C2—C8—C7i	−1.0 (4)	C14—C9—C15—C17	37.2 (4)
C1—C2—C8—C3i	179.1 (2)	C10—C9—C15—C17	−142.9 (3)
C14—C9—C10—C11	−0.1 (4)	Ru1—C9—C15—C17	−54.7 (4)
C15—C9—C10—C11	180.0 (2)	C14—C9—C15—C16	−88.1 (3)
Ru1—C9—C10—C11	54.5 (2)	C10—C9—C15—C16	91.9 (3)
C14—C9—C10—Ru1	−54.5 (2)	Ru1—C9—C15—C16	−180.0 (3)
C15—C9—C10—Ru1	125.5 (2)	C7i—C6—N1—C1	−0.5 (4)
C9—C10—C11—C12	−1.1 (4)	C5—C6—N1—C1	178.8 (2)
Ru1—C10—C11—C12	53.4 (2)	C7i—C6—N1—Ru1	178.40 (18)
C9—C10—C11—Ru1	−54.4 (2)	C5—C6—N1—Ru1	−2.4 (3)
C10—C11—C12—C13	0.8 (4)	C2—C1—N1—C6	−0.2 (4)
Ru1—C11—C12—C13	53.8 (2)	C2—C1—N1—Ru1	−178.90 (19)
C10—C11—C12—C18	−177.5 (2)	C7—C5—N2—C4	−1.2 (4)
Ru1—C11—C12—C18	−124.4 (2)	C6—C5—N2—C4	178.8 (2)
C10—C11—C12—Ru1	−53.1 (2)	C7—C5—N2—Ru1	−177.53 (18)
C11—C12—C13—C14	0.7 (4)	C6—C5—N2—Ru1	2.5 (3)
C18—C12—C13—C14	179.0 (2)	C3—C4—N2—C5	0.8 (4)
Ru1—C12—C13—C14	54.7 (2)	C3—C4—N2—Ru1	176.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.39	3.194 (4)	145
C3—H3···Cl1ii	0.93	2.84	3.637 (3)	145
C3—H3···F6iii	0.93	2.58	3.205 (4)	125
C4—H4···F6iii	0.93	2.60	3.223 (4)	125
C19—H19B···F4iv	0.96	2.46	3.321 (5)	149

Table 1

Selected bond lengths (Å)

C9—Ru1	2.214 (2)
C10—Ru1	2.188 (2)
C11—Ru1	2.204 (3)
C12—Ru1	2.212 (3)
C13—Ru1	2.185 (3)
C14—Ru1	2.200 (3)
Cl1—Ru1	2.3844 (7)
N1—Ru1	2.105 (2)
N2—Ru1	2.105 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.93	2.39	3.194 (4)	145
C3—H3⋯Cl1i	0.93	2.84	3.637 (3)	145
C3—H3⋯F6ii	0.93	2.58	3.205 (4)	125
C4—H4⋯F6ii	0.93	2.60	3.223 (4)	125
C19—H19B⋯F4iii	0.96	2.46	3.321 (5)	149

Symmetry codes: (i) ; (ii) ; (iii) .