1,3-Bis(2-thienylmeth-yl)-4,5-dihydro-imidazolium trichlorido(η-p-cymene)ruthenate(II).

The asymmetric unit of the title compound, (C(13)H(15)N(2)S(2))[RuCl(3)(C(10)H(14))], contains a 1,3-(2-thienylmeth-yl)-4,5-dihydro-imidazolium cation and a trichlorido(η(6)-p-cymene)ruthenate(II) anion. The thio-phene rings of the cation are disordered by an 180° rotation about the thio-phene-CH(2) bonds with occupancies of 0.847 (5)/0.153 (5) and 0.700 (5)/0.300 (5), respectively. The Ru atom exhibits a distorted octa-hedral coordination with the benzene ring of the p-cymene ligand formally occupying three sites and three Cl atoms occupying the other three sites. The short C-N bond lengths in the imidazoline ring indicate partial electron delocalization within the N-C-N fragment. Cation and anions are connected through five inter-molecular C-H⋯Cl hydrogen bonds and one C-H⋯π hydrogen bond, forming a three-dimensional hydrogen-bonded network.

Related literature

For the synthesis, see: Yaşar et al. (2008 ▶). Özdemir et al. (2008 ▶, 2007 ▶, 2005 ▶). For general background, see: Herrmann et al. (1995 ▶); Herrmann (2002 ▶); Arduengo & Krafczyc (1998 ▶). For related compounds, see: Arslan et al. (2007 ▶, 2005a ▶,b ▶) and references therein; Sonar et al. (2004 ▶, 2005a ▶,b ▶); Wagner et al. (2006a ▶,b ▶); Crundwell et al. (2002 ▶); Linehan et al. (2003 ▶); Liu et al. (2004 ▶); Navarro et al. (2006 ▶); Therrien et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

(C13H15N2S2)[RuCl3(C10H14)]

M = 605.02

Triclinic,

a = 9.910 (2) Å

b = 11.600 (2) Å

c = 12.659 (3) Å

α = 84.95 (3)°

β = 67.05 (3)°

γ = 74.14 (3)°

V = 1288.8 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.10 mm−1

T = 153 (2) K

0.48 × 0.19 × 0.17 mm

Data collection

Rigaku AFC-8S Mercury CCD diffractometer

Absorption correction: multi-scan (REQUAB; Jacobson, 1998 ▶) T min = 0.621, T max = 0.836

11095 measured reflections

4557 independent reflections

4062 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.13

4557 reflections

285 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.68 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000464/hg2465sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000464/hg2465Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C13H15N2S2)[RuCl3(C10H14)]	Z = 2
Mr = 605.02	F(000) = 616
Triclinic, P1	Dx = 1.559 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.910 (2) Å	Cell parameters from 5195 reflections
b = 11.600 (2) Å	θ = 3.3–26.4°
c = 12.659 (3) Å	µ = 1.10 mm−1
α = 84.95 (3)°	T = 153 K
β = 67.05 (3)°	Rod, red
γ = 74.14 (3)°	0.48 × 0.19 × 0.17 mm
V = 1288.8 (6) Å3

Rigaku AFC-8S Mercury CCD diffractometer	4557 independent reflections
Radiation source: Sealed Tube	4062 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.019
Detector resolution: 14.6306 pixels mm-1	θmax = 25.2°, θmin = 3.3°
ω scans	h = −11→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −11→13
Tmin = 0.621, Tmax = 0.836	l = −15→15
11095 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.9404P] where P = (Fo2 + 2Fc2)/3
4557 reflections	(Δ/σ)max = 0.001
285 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ru1	−0.02777 (3)	0.69238 (2)	0.639788 (19)	0.03323 (9)
Cl1	−0.10558 (9)	0.78990 (7)	0.82284 (6)	0.04448 (19)
Cl2	0.08996 (10)	0.51572 (7)	0.72233 (7)	0.04740 (19)
Cl3	−0.26047 (9)	0.62550 (8)	0.71790 (7)	0.0506 (2)
C1	0.1893 (4)	0.7262 (3)	0.5295 (3)	0.0484 (8)
C2	0.1573 (4)	0.6370 (3)	0.4777 (3)	0.0462 (8)
H2	0.2310	0.5610	0.4550	0.055*
C3	0.0226 (4)	0.6570 (4)	0.4593 (3)	0.0512 (8)
H3	0.0058	0.5957	0.4235	0.061*
C4	−0.0892 (4)	0.7679 (4)	0.4935 (3)	0.0534 (9)
C5	−0.0618 (5)	0.8573 (3)	0.5467 (3)	0.0559 (9)
H5	−0.1363	0.9327	0.5705	0.067*
C6	0.0761 (4)	0.8346 (3)	0.5644 (3)	0.0510 (8)
H6	0.0924	0.8953	0.6015	0.061*
C7	0.3370 (5)	0.6951 (5)	0.5491 (4)	0.0721 (12)
H7	0.3489	0.6158	0.5792	0.087*
C8	0.4683 (7)	0.6885 (10)	0.4361 (5)	0.168 (4)
H8A	0.4600	0.7659	0.4019	0.251*
H8B	0.4671	0.6316	0.3860	0.251*
H8C	0.5617	0.6636	0.4484	0.251*
C9	0.3364 (6)	0.7746 (6)	0.6359 (4)	0.0889 (16)
H9A	0.4234	0.7411	0.6554	0.133*
H9B	0.2455	0.7811	0.7034	0.133*
H9C	0.3398	0.8527	0.6046	0.133*
C10	−0.2363 (5)	0.7879 (5)	0.4785 (4)	0.0864 (15)
H10A	−0.2231	0.8116	0.4013	0.130*
H10B	−0.3119	0.8499	0.5311	0.130*
H10C	−0.2683	0.7151	0.4937	0.130*
S1	0.29307 (13)	0.18189 (11)	0.86238 (11)	0.0636 (4)	0.847 (5)
C16'	0.29307 (13)	0.18189 (11)	0.86238 (11)	0.0636 (4)	0.153 (5)
H16'	0.2049	0.2487	0.8803	0.076*	0.153 (5)
S2	0.13328 (18)	0.84868 (10)	0.98665 (14)	0.0673 (5)	0.700 (5)
C21'	0.13328 (18)	0.84868 (10)	0.98665 (14)	0.0673 (5)	0.300 (5)
H21'	0.1475	0.8704	0.9088	0.081*	0.300 (5)
N1	0.4121 (3)	0.3556 (2)	0.9546 (2)	0.0456 (6)
N2	0.2449 (3)	0.5262 (2)	0.9644 (2)	0.0396 (6)
C11	0.2748 (3)	0.4218 (3)	1.0096 (3)	0.0374 (6)
H11	0.2029	0.3959	1.0769	0.045*
C12	0.3763 (4)	0.5391 (3)	0.8622 (3)	0.0561 (9)
H12A	0.4119	0.6054	0.8711	0.067*
H12B	0.3525	0.5501	0.7948	0.067*
C13	0.4936 (5)	0.4194 (3)	0.8565 (3)	0.0631 (10)
H13A	0.5238	0.3766	0.7860	0.076*
H13B	0.5819	0.4315	0.8633	0.076*
C14	0.4669 (4)	0.2283 (3)	0.9737 (3)	0.0473 (8)
H14A	0.4110	0.2105	1.0515	0.057*
H14B	0.5718	0.2112	0.9631	0.057*
C15	0.4510 (4)	0.1486 (3)	0.8940 (3)	0.0438 (7)
S1'	0.5553 (4)	0.0368 (3)	0.8423 (3)	0.0759 (12)	0.153 (5)
C16	0.5553 (4)	0.0368 (3)	0.8423 (3)	0.0759 (12)	0.847 (5)
H16	0.6534	0.0029	0.8456	0.091*	0.847 (5)
C17	0.4850 (6)	−0.0147 (4)	0.7846 (4)	0.0743 (12)
H17	0.5312	−0.0919	0.7467	0.089*
C18	0.3504 (6)	0.0533 (4)	0.7880 (4)	0.0732 (12)
H18	0.2925	0.0307	0.7515	0.088*
C19	0.1011 (4)	0.6183 (3)	1.0051 (3)	0.0409 (7)
H19A	0.0249	0.5844	1.0610	0.049*
H19B	0.0701	0.6438	0.9419	0.049*
C20	0.1103 (3)	0.7249 (3)	1.0576 (3)	0.0407 (7)
S2'	0.0919 (3)	0.7370 (2)	1.18444 (19)	0.0656 (8)	0.300 (5)
C21	0.0919 (3)	0.7370 (2)	1.18444 (19)	0.0656 (8)	0.700 (5)
H21	0.0762	0.6796	1.2445	0.079*	0.700 (5)
C22	0.1046 (5)	0.8587 (6)	1.1876 (5)	0.0860 (17)
H22	0.0993	0.8925	1.2561	0.103*
C23	0.1235 (5)	0.9205 (3)	1.0935 (5)	0.0765 (14)
H23	0.1310	1.0017	1.0887	0.092*

	U11	U22	U33	U12	U13	U23
Ru1	0.04018 (15)	0.03358 (14)	0.03059 (14)	−0.01658 (10)	−0.01405 (10)	0.00217 (9)
Cl1	0.0592 (5)	0.0374 (4)	0.0377 (4)	−0.0148 (3)	−0.0163 (3)	−0.0067 (3)
Cl2	0.0554 (5)	0.0370 (4)	0.0484 (4)	−0.0104 (3)	−0.0204 (4)	0.0055 (3)
Cl3	0.0483 (4)	0.0661 (5)	0.0460 (4)	−0.0327 (4)	−0.0158 (3)	0.0045 (4)
C1	0.0502 (19)	0.064 (2)	0.0352 (16)	−0.0304 (17)	−0.0113 (14)	0.0064 (15)
C2	0.0491 (18)	0.057 (2)	0.0325 (15)	−0.0231 (16)	−0.0090 (13)	−0.0027 (14)
C3	0.063 (2)	0.074 (2)	0.0285 (15)	−0.0371 (19)	−0.0185 (15)	0.0043 (15)
C4	0.059 (2)	0.072 (2)	0.0411 (17)	−0.0304 (19)	−0.0257 (16)	0.0210 (17)
C5	0.077 (3)	0.0430 (18)	0.0461 (19)	−0.0207 (17)	−0.0225 (18)	0.0171 (15)
C6	0.072 (2)	0.0484 (19)	0.0451 (18)	−0.0386 (18)	−0.0222 (17)	0.0124 (15)
C7	0.052 (2)	0.115 (4)	0.059 (2)	−0.040 (2)	−0.0186 (18)	−0.004 (2)
C8	0.075 (4)	0.359 (14)	0.081 (4)	−0.099 (6)	−0.003 (3)	−0.044 (6)
C9	0.079 (3)	0.136 (5)	0.076 (3)	−0.051 (3)	−0.040 (3)	−0.002 (3)
C10	0.072 (3)	0.131 (5)	0.073 (3)	−0.032 (3)	−0.046 (2)	0.026 (3)
S1	0.0542 (7)	0.0669 (8)	0.0728 (8)	−0.0065 (5)	−0.0317 (6)	−0.0088 (6)
C16'	0.0542 (7)	0.0669 (8)	0.0728 (8)	−0.0065 (5)	−0.0317 (6)	−0.0088 (6)
S2	0.1003 (11)	0.0355 (6)	0.0966 (11)	−0.0253 (6)	−0.0681 (9)	0.0179 (6)
C21'	0.1003 (11)	0.0355 (6)	0.0966 (11)	−0.0253 (6)	−0.0681 (9)	0.0179 (6)
N1	0.0445 (15)	0.0354 (14)	0.0491 (15)	−0.0070 (12)	−0.0116 (12)	−0.0012 (12)
N2	0.0473 (14)	0.0315 (13)	0.0384 (13)	−0.0116 (11)	−0.0141 (11)	0.0016 (10)
C11	0.0430 (16)	0.0340 (15)	0.0372 (15)	−0.0124 (13)	−0.0158 (13)	0.0010 (12)
C12	0.060 (2)	0.050 (2)	0.0482 (19)	−0.0202 (17)	−0.0080 (17)	0.0082 (16)
C13	0.060 (2)	0.051 (2)	0.059 (2)	−0.0159 (18)	−0.0004 (18)	−0.0002 (18)
C14	0.0436 (17)	0.0380 (17)	0.0561 (19)	0.0002 (14)	−0.0208 (15)	−0.0042 (15)
C15	0.0430 (17)	0.0376 (16)	0.0485 (18)	−0.0077 (13)	−0.0172 (14)	0.0023 (14)
S1'	0.092 (2)	0.0512 (17)	0.090 (2)	−0.0105 (15)	−0.0439 (19)	−0.0045 (15)
C16	0.092 (2)	0.0512 (17)	0.090 (2)	−0.0105 (15)	−0.0439 (19)	−0.0045 (15)
C17	0.097 (3)	0.053 (2)	0.068 (3)	−0.021 (2)	−0.023 (2)	−0.011 (2)
C18	0.095 (3)	0.075 (3)	0.070 (3)	−0.038 (3)	−0.044 (3)	0.005 (2)
C19	0.0448 (17)	0.0319 (15)	0.0511 (18)	−0.0088 (13)	−0.0242 (14)	−0.0002 (13)
C20	0.0374 (15)	0.0326 (15)	0.0533 (18)	−0.0059 (12)	−0.0197 (14)	−0.0032 (13)
S2'	0.0721 (15)	0.0671 (15)	0.0606 (13)	−0.0293 (11)	−0.0207 (11)	0.0003 (10)
C21	0.0721 (15)	0.0671 (15)	0.0606 (13)	−0.0293 (11)	−0.0207 (11)	0.0003 (10)
C22	0.060 (3)	0.115 (4)	0.082 (3)	−0.020 (3)	−0.015 (2)	−0.053 (3)
C23	0.067 (3)	0.0316 (18)	0.133 (5)	−0.0068 (18)	−0.041 (3)	−0.013 (2)

Ru1—C6	2.140 (3)	C10—H10C	0.9599
Ru1—C2	2.154 (3)	S1—C15	1.700 (3)
Ru1—C5	2.173 (3)	S2—C20	1.647 (3)
Ru1—C1	2.180 (3)	N1—C11	1.307 (4)
Ru1—C3	2.191 (3)	N1—C13	1.458 (5)
Ru1—C4	2.207 (3)	N1—C14	1.462 (4)
Ru1—Cl1	2.4157 (11)	N2—C11	1.302 (4)
Ru1—Cl2	2.4329 (11)	N2—C19	1.460 (4)
Ru1—Cl3	2.4417 (11)	N2—C12	1.466 (4)
C1—C6	1.406 (5)	C11—H11	0.9600
C1—C2	1.435 (5)	C12—C13	1.534 (5)
C1—C7	1.521 (5)	C12—H12A	0.9600
C2—C3	1.398 (5)	C12—H12B	0.9600
C2—H2	0.9600	C13—H13A	0.9600
C3—C4	1.419 (6)	C13—H13B	0.9600
C3—H3	0.9600	C14—C15	1.505 (5)
C4—C5	1.422 (5)	C14—H14A	0.9600
C4—C10	1.495 (5)	C14—H14B	0.9600
C5—C6	1.421 (5)	C15—S1'	1.438 (4)
C5—H5	0.9600	S1'—H16	0.960 (3)
C6—H6	0.9600	C17—C18	1.338 (7)
C7—C9	1.492 (6)	C17—H17	0.9600
C7—C8	1.502 (7)	C18—H18	0.9600
C7—H7	0.9600	C19—C20	1.495 (4)
C8—H8A	0.9599	C19—H19A	0.9600
C8—H8B	0.9599	C19—H19B	0.9600
C8—H8C	0.9599	C20—S2'	1.558 (4)
C9—H9A	0.9599	S2'—H21	0.960 (2)
C9—H9B	0.9599	C22—C23	1.310 (7)
C9—H9C	0.9599	C22—H22	0.9600
C10—H10A	0.9599	C23—H23	0.9600
C10—H10B	0.9599
C6—Ru1—C2	68.59 (14)	Ru1—C6—H6	128.9
C6—Ru1—C5	38.46 (15)	C9—C7—C8	113.3 (5)
C2—Ru1—C5	80.93 (15)	C9—C7—C1	113.7 (4)
C6—Ru1—C1	37.98 (14)	C8—C7—C1	109.7 (4)
C2—Ru1—C1	38.66 (13)	C9—C7—H7	106.5
C5—Ru1—C1	69.25 (15)	C8—C7—H7	106.5
C6—Ru1—C3	81.08 (14)	C1—C7—H7	106.5
C2—Ru1—C3	37.52 (13)	C7—C8—H8A	109.5
C5—Ru1—C3	68.20 (15)	C7—C8—H8B	109.5
C1—Ru1—C3	69.15 (13)	H8A—C8—H8B	109.5
C6—Ru1—C4	68.92 (14)	C7—C8—H8C	109.5
C2—Ru1—C4	68.06 (14)	H8A—C8—H8C	109.5
C5—Ru1—C4	37.88 (15)	H8B—C8—H8C	109.5
C1—Ru1—C4	81.91 (13)	C7—C9—H9A	109.5
C3—Ru1—C4	37.65 (15)	C7—C9—H9B	109.5
C6—Ru1—Cl1	86.77 (10)	H9A—C9—H9B	109.5
C2—Ru1—Cl1	144.83 (9)	C7—C9—H9C	109.5
C5—Ru1—Cl1	95.39 (11)	H9A—C9—H9C	109.5
C1—Ru1—Cl1	107.28 (10)	H9B—C9—H9C	109.5
C3—Ru1—Cl1	163.52 (11)	C4—C10—H10A	109.5
C4—Ru1—Cl1	126.94 (11)	C4—C10—H10B	109.5
C6—Ru1—Cl2	124.11 (11)	H10A—C10—H10B	109.5
C2—Ru1—Cl2	87.76 (11)	C4—C10—H10C	109.5
C5—Ru1—Cl2	162.10 (11)	H10A—C10—H10C	109.5
C1—Ru1—Cl2	93.29 (10)	H10B—C10—H10C	109.5
C3—Ru1—Cl2	110.15 (11)	C11—N1—C13	110.3 (3)
C4—Ru1—Cl2	146.86 (11)	C11—N1—C14	125.0 (3)
Cl1—Ru1—Cl2	85.88 (4)	C13—N1—C14	123.6 (3)
C6—Ru1—Cl3	147.20 (11)	C11—N2—C19	126.2 (3)
C2—Ru1—Cl3	126.23 (9)	C11—N2—C12	110.5 (3)
C5—Ru1—Cl3	110.17 (12)	C19—N2—C12	123.3 (3)
C1—Ru1—Cl3	164.68 (9)	N2—C11—N1	113.6 (3)
C3—Ru1—Cl3	96.15 (10)	N2—C11—H11	123.2
C4—Ru1—Cl3	88.90 (10)	N1—C11—H11	123.2
Cl1—Ru1—Cl3	88.04 (4)	N2—C12—C13	102.5 (3)
Cl2—Ru1—Cl3	87.71 (4)	N2—C12—H12A	111.3
C6—C1—C2	116.7 (3)	C13—C12—H12A	111.3
C6—C1—C7	124.6 (4)	N2—C12—H12B	111.3
C2—C1—C7	118.6 (4)	C13—C12—H12B	111.3
C6—C1—Ru1	69.44 (19)	H12A—C12—H12B	109.2
C2—C1—Ru1	69.67 (19)	N1—C13—C12	103.2 (3)
C7—C1—Ru1	128.6 (3)	N1—C13—H13A	111.1
C3—C2—C1	122.3 (3)	C12—C13—H13A	111.1
C3—C2—Ru1	72.69 (19)	N1—C13—H13B	111.1
C1—C2—Ru1	71.67 (19)	C12—C13—H13B	111.1
C3—C2—H2	118.9	H13A—C13—H13B	109.1
C1—C2—H2	118.9	N1—C14—C15	112.6 (3)
Ru1—C2—H2	129.3	N1—C14—H14A	109.1
C2—C3—C4	120.1 (3)	C15—C14—H14A	109.1
C2—C3—Ru1	69.79 (18)	N1—C14—H14B	109.1
C4—C3—Ru1	71.78 (19)	C15—C14—H14B	109.1
C2—C3—H3	119.9	H14A—C14—H14B	107.8
C4—C3—H3	119.9	S1'—C15—C14	126.7 (3)
Ru1—C3—H3	131.2	S1'—C15—S1	112.4 (3)
C3—C4—C5	118.9 (3)	C14—C15—S1	120.8 (2)
C3—C4—C10	120.4 (4)	C15—S1'—H16	126.4 (3)
C5—C4—C10	120.7 (4)	C18—C17—H17	122.6
C3—C4—Ru1	70.57 (19)	C17—C18—H18	123.4
C5—C4—Ru1	69.77 (19)	N2—C19—C20	112.8 (3)
C10—C4—Ru1	129.5 (3)	N2—C19—H19A	109.0
C6—C5—C4	119.9 (4)	C20—C19—H19A	109.0
C6—C5—Ru1	69.50 (19)	N2—C19—H19B	109.0
C4—C5—Ru1	72.4 (2)	C20—C19—H19B	109.0
C6—C5—H5	120.1	H19A—C19—H19B	107.8
C4—C5—H5	120.1	C19—C20—S2'	125.7 (3)
Ru1—C5—H5	130.7	C19—C20—S2	122.6 (3)
C1—C6—C5	122.1 (3)	S2'—C20—S2	111.7 (2)
C1—C6—Ru1	72.58 (19)	C20—S2'—H21	129.3 (2)
C5—C6—Ru1	72.0 (2)	C23—C22—H22	121.2
C1—C6—H6	119.0	C22—C23—H23	122.8
C5—C6—H6	119.0
C2—Ru1—C1—C6	130.7 (3)	Cl2—Ru1—C4—C5	−150.0 (2)
C5—Ru1—C1—C6	28.9 (2)	Cl3—Ru1—C4—C5	125.9 (2)
C3—Ru1—C1—C6	102.6 (2)	C6—Ru1—C4—C10	−143.0 (5)
C4—Ru1—C1—C6	65.9 (2)	C2—Ru1—C4—C10	142.5 (5)
Cl1—Ru1—C1—C6	−60.4 (2)	C5—Ru1—C4—C10	−113.6 (5)
Cl2—Ru1—C1—C6	−147.07 (19)	C1—Ru1—C4—C10	180.0 (5)
Cl3—Ru1—C1—C6	119.6 (4)	C3—Ru1—C4—C10	113.8 (5)
C6—Ru1—C1—C2	−130.7 (3)	Cl1—Ru1—C4—C10	−74.4 (5)
C5—Ru1—C1—C2	−101.8 (2)	Cl2—Ru1—C4—C10	96.4 (4)
C3—Ru1—C1—C2	−28.1 (2)	Cl3—Ru1—C4—C10	12.3 (4)
C4—Ru1—C1—C2	−64.8 (2)	C3—C4—C5—C6	0.2 (5)
Cl1—Ru1—C1—C2	168.98 (18)	C10—C4—C5—C6	177.4 (3)
Cl2—Ru1—C1—C2	82.3 (2)	Ru1—C4—C5—C6	52.7 (3)
Cl3—Ru1—C1—C2	−11.0 (5)	C3—C4—C5—Ru1	−52.5 (3)
C6—Ru1—C1—C7	118.5 (4)	C10—C4—C5—Ru1	124.7 (3)
C2—Ru1—C1—C7	−110.9 (4)	C2—Ru1—C5—C6	−66.8 (2)
C5—Ru1—C1—C7	147.4 (4)	C1—Ru1—C5—C6	−28.6 (2)
C3—Ru1—C1—C7	−138.9 (4)	C3—Ru1—C5—C6	−103.6 (2)
C4—Ru1—C1—C7	−175.6 (4)	C4—Ru1—C5—C6	−132.6 (3)
Cl1—Ru1—C1—C7	58.1 (4)	Cl1—Ru1—C5—C6	77.9 (2)
Cl2—Ru1—C1—C7	−28.6 (4)	Cl2—Ru1—C5—C6	−15.4 (5)
Cl3—Ru1—C1—C7	−121.9 (4)	Cl3—Ru1—C5—C6	167.78 (19)
C6—C1—C2—C3	1.9 (5)	C6—Ru1—C5—C4	132.6 (3)
C7—C1—C2—C3	178.4 (3)	C2—Ru1—C5—C4	65.7 (2)
Ru1—C1—C2—C3	54.6 (3)	C1—Ru1—C5—C4	104.0 (2)
C6—C1—C2—Ru1	−52.7 (3)	C3—Ru1—C5—C4	29.0 (2)
C7—C1—C2—Ru1	123.8 (3)	Cl1—Ru1—C5—C4	−149.5 (2)
C6—Ru1—C2—C3	−103.7 (2)	Cl2—Ru1—C5—C4	117.2 (3)
C5—Ru1—C2—C3	−65.8 (2)	Cl3—Ru1—C5—C4	−59.6 (2)
C1—Ru1—C2—C3	−133.8 (3)	C2—C1—C6—C5	−1.9 (5)
C4—Ru1—C2—C3	−28.7 (2)	C7—C1—C6—C5	−178.1 (3)
Cl1—Ru1—C2—C3	−152.29 (18)	Ru1—C1—C6—C5	−54.7 (3)
Cl2—Ru1—C2—C3	128.1 (2)	C2—C1—C6—Ru1	52.8 (3)
Cl3—Ru1—C2—C3	42.6 (3)	C7—C1—C6—Ru1	−123.4 (3)
C6—Ru1—C2—C1	30.1 (2)	C4—C5—C6—C1	0.9 (5)
C5—Ru1—C2—C1	68.0 (2)	Ru1—C5—C6—C1	54.9 (3)
C3—Ru1—C2—C1	133.8 (3)	C4—C5—C6—Ru1	−54.0 (3)
C4—Ru1—C2—C1	105.1 (2)	C2—Ru1—C6—C1	−30.6 (2)
Cl1—Ru1—C2—C1	−18.5 (3)	C5—Ru1—C6—C1	−133.4 (3)
Cl2—Ru1—C2—C1	−98.1 (2)	C3—Ru1—C6—C1	−67.4 (2)
Cl3—Ru1—C2—C1	176.40 (17)	C4—Ru1—C6—C1	−104.4 (2)
C1—C2—C3—C4	−0.9 (5)	Cl1—Ru1—C6—C1	123.77 (19)
Ru1—C2—C3—C4	53.2 (3)	Cl2—Ru1—C6—C1	41.0 (2)
C1—C2—C3—Ru1	−54.1 (3)	Cl3—Ru1—C6—C1	−154.91 (17)
C6—Ru1—C3—C2	66.3 (2)	C2—Ru1—C6—C5	102.8 (2)
C5—Ru1—C3—C2	104.0 (2)	C1—Ru1—C6—C5	133.4 (3)
C1—Ru1—C3—C2	28.8 (2)	C3—Ru1—C6—C5	66.0 (2)
C4—Ru1—C3—C2	133.2 (3)	C4—Ru1—C6—C5	29.0 (2)
Cl1—Ru1—C3—C2	109.2 (4)	Cl1—Ru1—C6—C5	−102.8 (2)
Cl2—Ru1—C3—C2	−56.9 (2)	Cl2—Ru1—C6—C5	174.34 (18)
Cl3—Ru1—C3—C2	−146.7 (2)	Cl3—Ru1—C6—C5	−21.5 (3)
C6—Ru1—C3—C4	−66.9 (2)	C6—C1—C7—C9	15.6 (6)
C2—Ru1—C3—C4	−133.2 (3)	C2—C1—C7—C9	−160.6 (4)
C5—Ru1—C3—C4	−29.1 (2)	Ru1—C1—C7—C9	−74.7 (5)
C1—Ru1—C3—C4	−104.3 (2)	C6—C1—C7—C8	−112.5 (6)
Cl1—Ru1—C3—C4	−23.9 (5)	C2—C1—C7—C8	71.4 (6)
Cl2—Ru1—C3—C4	169.95 (18)	Ru1—C1—C7—C8	157.2 (5)
Cl3—Ru1—C3—C4	80.1 (2)	C19—N2—C11—N1	178.8 (3)
C2—C3—C4—C5	−0.2 (5)	C12—N2—C11—N1	0.4 (4)
Ru1—C3—C4—C5	52.1 (3)	C13—N1—C11—N2	0.0 (4)
C2—C3—C4—C10	−177.4 (3)	C14—N1—C11—N2	−168.6 (3)
Ru1—C3—C4—C10	−125.1 (3)	C11—N2—C12—C13	−0.6 (4)
C2—C3—C4—Ru1	−52.3 (3)	C19—N2—C12—C13	−179.1 (3)
C6—Ru1—C4—C3	103.2 (2)	C11—N1—C13—C12	−0.4 (4)
C2—Ru1—C4—C3	28.6 (2)	C14—N1—C13—C12	168.4 (3)
C5—Ru1—C4—C3	132.6 (3)	N2—C12—C13—N1	0.6 (4)
C1—Ru1—C4—C3	66.1 (2)	C11—N1—C14—C15	93.3 (4)
Cl1—Ru1—C4—C3	171.72 (16)	C13—N1—C14—C15	−73.9 (4)
Cl2—Ru1—C4—C3	−17.4 (3)	N1—C14—C15—S1'	143.0 (3)
Cl3—Ru1—C4—C3	−101.6 (2)	N1—C14—C15—S1	−40.9 (4)
C6—Ru1—C4—C5	−29.4 (2)	C11—N2—C19—C20	109.6 (4)
C2—Ru1—C4—C5	−103.9 (2)	C12—N2—C19—C20	−72.2 (4)
C1—Ru1—C4—C5	−66.4 (2)	N2—C19—C20—S2'	−84.8 (4)
C3—Ru1—C4—C5	−132.6 (3)	N2—C19—C20—S2	98.6 (3)
Cl1—Ru1—C4—C5	39.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1i	0.96	2.62	3.450 (4)	144
C14—H14A···Cl1i	0.96	2.82	3.553 (4)	134
C19—H19A···Cl2i	0.96	2.81	3.671 (4)	150
C23—H23···Cl1ii	0.96	2.66	3.549 (4)	154
C14—H14B···Cg2iii	0.96	2.83	3.784 (5)	171
C19—H19B···Cl1	0.96	2.86	3.759 (5)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1i	0.96	2.62	3.450 (4)	144
C14—H14A⋯Cl1i	0.96	2.82	3.553 (4)	134
C19—H19A⋯Cl2i	0.96	2.81	3.671 (4)	150
C23—H23⋯Cl1ii	0.96	2.66	3.549 (4)	154
C14—H14B⋯Cg2iii	0.96	2.83	3.784 (5)	171
C19—H19B⋯Cl1	0.96	2.86	3.759 (5)	157

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the S2,C20–C23 thio­phene ring.