(η6-Benzene)­chlorido­[2-(pyridin-2-yl)quinoline-κ2N,N′]ruthenium(II) tetra­fluorido­borate

Varadhan, M.; Passi, I.; Chinnathangavel, T.; Rajendiran, V.

doi:10.1107/S2414314624012409

metal-organic compounds

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ISSN: 2414-3146

Volume 10| Part 1| January 2025| x241240

https://doi.org/10.1107/S2414314624012409

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(η⁶-Benzene)chlorido[2-(pyridin-2-yl)quinoline-κ²N,N′]ruthenium(II) tetrafluoridoborate

Manikandan Varadhan,^a Ibanpynhunlang Passi,^b Thangaraja Chinnathangavel ^c and Venugopal Rajendiran ^a ^*

^aDepartment of Chemistry, School of Basic and Applied Sciences, Central University of Tamil Nadu, Thiruvarur 610 005, India, ^bDepartment of Chemistry, North Eastern Hill University, Shillong 793 022, India, and ^cDepartment of Chemistry, Anna University Regional Campus, Madurai 625 019, Tamil Nadu, India
^*Correspondence e-mail: rajendiran@cutn.ac.in

Edited by M. Weil, Vienna University of Technology, Austria (Received 13 December 2024; accepted 23 December 2024; online 7 January 2025)

The title compound, [RuCl(C₆H₆)(C₁₄H₁₀N₂)]BF₄ or [Ru(η⁶-benzene)(L)Cl]⁺BF₄⁻ [where L denotes the 2-(pyridin-2-yl)quinoline ligand], crystallizes in the monoclinic space group P2₁/c. The coordination environment around Ru^II is best described as pseudo-octahedral, resembling the familiar half-sandwich ‘three-legged piano-stool’ shape. In the coordination sphere, the η⁶-binding benzene ligand coordinates with the central Ru^II atom occupying the ‘seat’ of the stool with a metal-to-centroid distance of 1.695 (17) Å, while the chelate ligand L coordinates with its N atoms and, together with the Cl ligand, defines the ‘legs’ of the stool. Apart from Coulombic forces, C—H⋯F and C—H⋯Cl hydrogen-bonding interactions consolidate the crystal packing.

Keywords: ruthenium(II); 2-(pyridin-2-yl)quinoline; η⁶-benzene; crystal structure.

CCDC reference: 2407332

Structure description

Ruthenium complexes exhibit a plethora of applications in the domains of medicinal chemistry (Casini & Pöthig, 2024 ; Rajendiran et al., 2012 ; Chan et al., 2017 ; Puckett & Barton, 2007 ), catalysis (Chavarot et al., 2003 ; Ngo & Do, 2020 ; Hamelin et al., 2007 ), and materials chemistry (Ryabov et al., 2005 ; Huisman et al., 2016 ; Vatsa & Padhi, 2021 ). Understanding their structural properties provides new insight into the design of novel ruthenium(II) complexes and predict their structure–activity relationships. In this context, the mononuclear mixed-ligand ruthenium(II) complex, [Ru(η⁶-benzene)(L)Cl]⁺BF₄⁻ [where L is 2-(pyridin-2-yl)quinolone] has been synthesized and characterized by single-crystal X-ray analysis in the present work.

The distinctive half-sandwich, ‘three-legged piano-stool’ geometry of the complex cation of the title compound (Fig. 1) is characteristic of numerous η⁶-binding arene–ruthenium(II) complexes (Khamrang et al., 2016 ; Zamisa et al., 2024 ). The ‘legs’ of the stool are defined by two σ-bonding N atoms from the chelating ligand L and the chlorido ligand, while the ‘seat’ is defined by the π-bonded benzene. The Ru^II-to-benzene(centroid) distance is 1.695 (17) Å and is comparable with other complexes containing N,N′-chelating ligands (Kelani et al., 2023 , 2024 ; Tsolis et al., 2018 ). The Ru1—N1_py bond [2.086 (3) Å] is slightly shorter than the Ru1—N2_qn bond [2.147 (3) Å], revealing the pyridyl (py) N atom more firmly coordinates the central Ru^II atom than the quinolone (qn) N atom. The bidentate ligand has a bite angle of N1—Ru1—N2 = 76.42 (10)°. A similar type of coordination is observed in the crystal structure of [((2,2′-bipyridyl)(η⁶-p-cymene)iodido)ruthenium(II)] hexafluoridophosphate (Kelani et al., 2023). The chlorido ligand bonds to the Ru^II atom with a distance of 2.3840 (9) Å. Except for the Ru—Cl bond, all other bonds are slightly longer than in the structure of the related complex [Ru(η⁶-p-cymene)LCl]⁺(PF₆)⁻ (Tsolis et al., 2018).

Figure 1
The molecular structure of the complex cation of the title compound with displacement ellipsoids at the 50% probability level.

In the crystal, intermolecular C—H⋯F and C—H⋯Cl hydrogen bonding (Table 1) plays a crucial role in the crystal packing (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯F4ⁱ	0.93	2.48	3.375 (5)	162
C16—H16⋯F1	0.93	2.24	3.148 (6)	162
C19—H19⋯Cl1ⁱⁱ	0.93	2.65	3.429 (4)	142
Symmetry codes: (i) ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
The crystal packing of the title compound. The Ru atoms are represented by green spheres, the Cl atoms by yellow spheres, and the F atoms by red spheres of arbitrary radii.

Synthesis and crystallization

[Ru(η⁶-benzene)Cl]₂ (0.12 g, 0.2 mmol) and L (2-(pyridin-2-yl)quinolone) (0.1 g, 0.4 mmol) were suspended in methanol (20 ml) and stirred at room temperature for 2 h. A solution of NaBF₄ (200 mg, 0.60 mmol) in methanol (10 ml) was added to the initially orange solution, which changed color to yellow. After 24 h, the solution was evaporated, and the solid obtained was filtered off. The residue was washed with diethyl ether (40 ml) and dried under vacuum. The obtained product was recrystallized from a DCM:hexane mixture to give orange crystals. Yield: 65%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[RuCl(C₆H₆)(C₁₄H₁₀N₂)]BF₄
M_r	507.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.4191 (3), 23.1476 (9), 9.9079 (3)
β (°)	94.709 (3)
V (Å³)	1924.35 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.00
Crystal size (mm)	0.65 × 0.50 × 0.41

Data collection
Diffractometer	Agilent Xcalibur, Atlas, Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012 )
T_min, T_max	0.507, 0.578
No. of measured, independent and observed [I > 2σ(I)] reflections	8112, 4311, 3815
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.093, 1.13
No. of reflections	4311
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.66
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2407332

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314624012409/wm4225sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624012409/wm4225Isup2.hkl

checkCIF report

Computing details top

(η⁶-Benzene)chlorido[2-(pyridin-2-yl)quinoline-κ²N,N']\ ruthenium(II) tetrafluoridoborate top

Crystal data top

[RuCl(C₆H₆)(C₁₄H₁₀N₂)]BF₄	F(000) = 1008
M_r = 507.68	D_x = 1.752 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4191 (3) Å	Cell parameters from 4311 reflections
b = 23.1476 (9) Å	θ = 3.4–28.7°
c = 9.9079 (3) Å	µ = 1.00 mm⁻¹
β = 94.709 (3)°	T = 293 K
V = 1924.35 (12) Å³	Block, orange
Z = 4	0.65 × 0.50 × 0.41 mm

Data collection top

Agilent Xcalibur, Atlas, Gemini diffractometer	3815 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
ω scans	θ_max = 28.7°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −10→11
T_min = 0.507, T_max = 0.578	k = −29→31
8112 measured reflections	l = −13→7
4311 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0353P)² + 2.2897P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.001
4311 reflections	Δρ_max = 0.92 e Å⁻³
262 parameters	Δρ_min = −0.66 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Ru1	0.36590 (3)	0.35365 (2)	0.55140 (2)	0.03087 (9)
Cl1	0.48682 (11)	0.26281 (4)	0.60853 (11)	0.0510 (2)
F2	0.0921 (4)	0.5390 (2)	0.8475 (3)	0.1168 (14)
F3	0.1988 (4)	0.60983 (16)	0.7391 (5)	0.1201 (14)
F4	0.3426 (3)	0.53126 (16)	0.7890 (3)	0.0961 (10)
F1	0.1343 (5)	0.53076 (17)	0.6300 (3)	0.1116 (13)
C19	0.3184 (6)	0.3211 (2)	0.3438 (4)	0.0585 (11)
H19	0.342384	0.285320	0.307946	0.070*
N2	0.2831 (3)	0.35589 (11)	0.7506 (3)	0.0313 (5)
N1	0.5548 (3)	0.39139 (12)	0.6693 (3)	0.0353 (6)
C14	0.1411 (4)	0.33333 (14)	0.7897 (3)	0.0335 (7)
C18	0.4281 (5)	0.3648 (2)	0.3419 (4)	0.0543 (10)
H18	0.524933	0.358972	0.305041	0.065*
C9	0.0871 (4)	0.34711 (15)	0.9181 (3)	0.0395 (8)
C11	−0.1533 (4)	0.29144 (18)	0.8644 (4)	0.0514 (10)
H11	−0.251959	0.278213	0.887140	0.062*
C20	0.1737 (5)	0.3286 (2)	0.3972 (4)	0.0630 (12)
H20	0.100838	0.298376	0.395571	0.076*
C2	0.8103 (4)	0.43585 (16)	0.6985 (4)	0.0473 (9)
H2	0.905866	0.445181	0.662876	0.057*
C12	−0.0967 (4)	0.27603 (17)	0.7396 (4)	0.0477 (9)
H12	−0.157907	0.251981	0.680845	0.057*
C5	0.5283 (4)	0.40623 (14)	0.7969 (3)	0.0353 (7)
C3	0.7831 (4)	0.45260 (17)	0.8276 (4)	0.0500 (9)
H3	0.858559	0.474045	0.879990	0.060*
C8	0.1852 (5)	0.38125 (18)	1.0081 (4)	0.0493 (9)
H8	0.151892	0.391143	1.092283	0.059*
C1	0.6957 (4)	0.40530 (16)	0.6226 (4)	0.0430 (8)
H1	0.715866	0.393750	0.535760	0.052*
C13	0.0473 (4)	0.29590 (16)	0.7031 (4)	0.0402 (8)
H13	0.083432	0.284658	0.620893	0.048*
C10	−0.0633 (5)	0.32567 (17)	0.9513 (4)	0.0487 (9)
H10	−0.100441	0.335336	1.034212	0.058*
C6	0.3742 (4)	0.38674 (15)	0.8414 (3)	0.0368 (7)
B1	0.1919 (5)	0.5506 (2)	0.7530 (4)	0.0497 (10)
C15	0.1378 (5)	0.3804 (3)	0.4524 (4)	0.0678 (14)
H15	0.041196	0.384661	0.490554	0.081*
C16	0.2430 (7)	0.4273 (2)	0.4530 (4)	0.0717 (15)
H16	0.216515	0.462854	0.488844	0.086*
C7	0.3287 (5)	0.39968 (17)	0.9715 (4)	0.0462 (9)
H7	0.396377	0.420705	1.031986	0.055*
C4	0.6408 (4)	0.43679 (17)	0.8778 (4)	0.0480 (9)
H4	0.620830	0.446693	0.965746	0.058*
C17	0.3906 (6)	0.4190 (2)	0.3973 (4)	0.0636 (12)
H17	0.463368	0.449282	0.397155	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.03032 (14)	0.03298 (15)	0.02952 (14)	0.00145 (11)	0.00382 (9)	−0.00114 (10)
Cl1	0.0498 (5)	0.0383 (5)	0.0662 (6)	0.0080 (4)	0.0128 (4)	0.0086 (4)
F2	0.083 (2)	0.191 (4)	0.082 (2)	−0.038 (2)	0.0366 (18)	−0.001 (2)
F3	0.093 (2)	0.080 (2)	0.189 (4)	−0.005 (2)	0.020 (3)	−0.010 (3)
F4	0.0582 (16)	0.126 (3)	0.104 (2)	0.0188 (18)	0.0070 (16)	0.032 (2)
F1	0.127 (3)	0.142 (3)	0.0637 (18)	0.040 (2)	−0.0099 (18)	−0.036 (2)
C19	0.081 (3)	0.059 (3)	0.0349 (18)	0.000 (2)	0.0039 (19)	−0.0128 (19)
N2	0.0278 (12)	0.0352 (14)	0.0311 (13)	0.0034 (11)	0.0027 (10)	0.0024 (11)
N1	0.0332 (14)	0.0358 (14)	0.0365 (14)	−0.0014 (12)	−0.0003 (11)	0.0022 (12)
C14	0.0297 (15)	0.0352 (16)	0.0363 (16)	0.0080 (13)	0.0057 (12)	0.0051 (13)
C18	0.047 (2)	0.084 (3)	0.0326 (17)	0.001 (2)	0.0095 (16)	0.0049 (19)
C9	0.0412 (18)	0.0405 (18)	0.0382 (17)	0.0108 (15)	0.0110 (14)	0.0080 (15)
C11	0.0379 (19)	0.055 (2)	0.063 (2)	0.0042 (18)	0.0152 (18)	0.014 (2)
C20	0.055 (2)	0.094 (4)	0.038 (2)	−0.020 (3)	−0.0052 (18)	−0.004 (2)
C2	0.0336 (18)	0.044 (2)	0.064 (2)	−0.0069 (16)	0.0032 (16)	0.0088 (18)
C12	0.0335 (17)	0.051 (2)	0.059 (2)	−0.0013 (16)	0.0058 (16)	0.0022 (18)
C5	0.0346 (16)	0.0353 (16)	0.0354 (16)	0.0029 (14)	−0.0009 (13)	0.0014 (13)
C3	0.0398 (19)	0.047 (2)	0.061 (2)	−0.0090 (17)	−0.0110 (17)	0.0007 (18)
C8	0.058 (2)	0.058 (2)	0.0327 (17)	0.005 (2)	0.0105 (16)	−0.0035 (17)
C1	0.0388 (18)	0.045 (2)	0.0455 (19)	−0.0018 (16)	0.0074 (15)	0.0033 (16)
C13	0.0346 (17)	0.0446 (19)	0.0418 (17)	0.0023 (15)	0.0057 (14)	0.0029 (15)
C10	0.048 (2)	0.051 (2)	0.051 (2)	0.0099 (18)	0.0216 (17)	0.0095 (18)
C6	0.0369 (17)	0.0393 (18)	0.0336 (16)	0.0032 (14)	0.0003 (13)	0.0012 (14)
B1	0.042 (2)	0.068 (3)	0.040 (2)	−0.004 (2)	0.0067 (17)	−0.002 (2)
C15	0.041 (2)	0.117 (4)	0.045 (2)	0.025 (3)	0.0020 (17)	0.019 (3)
C16	0.111 (4)	0.060 (3)	0.042 (2)	0.046 (3)	−0.004 (2)	0.008 (2)
C7	0.052 (2)	0.053 (2)	0.0335 (17)	−0.0034 (18)	0.0034 (15)	−0.0065 (16)
C4	0.047 (2)	0.051 (2)	0.0445 (19)	−0.0037 (18)	−0.0065 (16)	−0.0047 (17)
C17	0.086 (3)	0.055 (3)	0.047 (2)	−0.021 (2)	−0.013 (2)	0.020 (2)

Geometric parameters (Å, º) top

Ru1—N1	2.086 (3)	C11—C12	1.407 (5)
Ru1—N2	2.147 (3)	C11—H11	0.9300
Ru1—C17	2.172 (4)	C20—C15	1.361 (8)
Ru1—C15	2.173 (4)	C20—H20	0.9300
Ru1—C16	2.183 (4)	C2—C1	1.371 (5)
Ru1—C19	2.196 (4)	C2—C3	1.373 (6)
Ru1—C18	2.197 (4)	C2—H2	0.9300
Ru1—C20	2.209 (4)	C12—C13	1.373 (5)
Ru1—Cl1	2.3840 (9)	C12—H12	0.9300
F2—B1	1.336 (5)	C5—C4	1.384 (5)
F3—B1	1.381 (6)	C5—C6	1.474 (5)
F4—B1	1.365 (5)	C3—C4	1.384 (5)
F1—B1	1.354 (5)	C3—H3	0.9300
C19—C18	1.371 (6)	C8—C7	1.359 (5)
C19—C20	1.379 (6)	C8—H8	0.9300
C19—H19	0.9300	C1—H1	0.9300
N2—C6	1.340 (4)	C13—H13	0.9300
N2—C14	1.388 (4)	C10—H10	0.9300
N1—C5	1.346 (4)	C6—C7	1.407 (5)
N1—C1	1.347 (4)	C15—C16	1.403 (7)
C14—C13	1.414 (5)	C15—H15	0.9300
C14—C9	1.423 (4)	C16—C17	1.413 (7)
C18—C17	1.416 (6)	C16—H16	0.9300
C18—H18	0.9300	C7—H7	0.9300
C9—C8	1.407 (5)	C4—H4	0.9300
C9—C10	1.423 (5)	C17—H17	0.9300
C11—C10	1.355 (6)

N1—Ru1—N2	76.42 (10)	C15—C20—C19	119.8 (5)
N1—Ru1—C17	89.37 (14)	C15—C20—Ru1	70.5 (2)
N2—Ru1—C17	133.34 (16)	C19—C20—Ru1	71.2 (2)
N1—Ru1—C15	137.61 (19)	C15—C20—H20	120.1
N2—Ru1—C15	93.82 (13)	C19—C20—H20	120.1
C17—Ru1—C15	67.46 (19)	Ru1—C20—H20	130.9
N1—Ru1—C16	103.56 (17)	C1—C2—C3	119.5 (3)
N2—Ru1—C16	102.37 (14)	C1—C2—H2	120.2
C17—Ru1—C16	37.87 (19)	C3—C2—H2	120.2
C15—Ru1—C16	37.6 (2)	C13—C12—C11	121.1 (4)
N1—Ru1—C19	137.72 (15)	C13—C12—H12	119.5
N2—Ru1—C19	145.23 (14)	C11—C12—H12	119.5
C17—Ru1—C19	66.51 (17)	N1—C5—C4	121.0 (3)
C15—Ru1—C19	65.71 (18)	N1—C5—C6	114.9 (3)
C16—Ru1—C19	78.84 (17)	C4—C5—C6	124.1 (3)
N1—Ru1—C18	104.47 (14)	C2—C3—C4	118.4 (3)
N2—Ru1—C18	170.44 (14)	C2—C3—H3	120.8
C17—Ru1—C18	37.83 (17)	C4—C3—H3	120.8
C15—Ru1—C18	79.07 (16)	C7—C8—C9	119.7 (3)
C16—Ru1—C18	68.10 (17)	C7—C8—H8	120.1
C19—Ru1—C18	36.36 (16)	C9—C8—H8	120.1
N1—Ru1—C20	168.06 (15)	N1—C1—C2	122.4 (3)
N2—Ru1—C20	111.55 (14)	N1—C1—H1	118.8
C17—Ru1—C20	78.70 (17)	C2—C1—H1	118.8
C15—Ru1—C20	36.2 (2)	C12—C13—C14	120.5 (3)
C16—Ru1—C20	66.6 (2)	C12—C13—H13	119.8
C19—Ru1—C20	36.47 (17)	C14—C13—H13	119.8
C18—Ru1—C20	66.14 (16)	C11—C10—C9	121.3 (3)
N1—Ru1—Cl1	86.86 (8)	C11—C10—H10	119.4
N2—Ru1—Cl1	88.14 (7)	C9—C10—H10	119.4
C17—Ru1—Cl1	135.88 (15)	N2—C6—C7	123.0 (3)
C15—Ru1—Cl1	134.61 (17)	N2—C6—C5	115.6 (3)
C16—Ru1—Cl1	166.59 (13)	C7—C6—C5	121.4 (3)
C19—Ru1—Cl1	87.78 (13)	F2—B1—F1	111.3 (4)
C18—Ru1—Cl1	101.40 (12)	F2—B1—F4	112.1 (4)
C20—Ru1—Cl1	101.94 (15)	F1—B1—F4	112.4 (4)
C18—C19—C20	122.0 (4)	F2—B1—F3	107.6 (4)
C18—C19—Ru1	71.9 (2)	F1—B1—F3	105.2 (4)
C20—C19—Ru1	72.3 (2)	F4—B1—F3	107.8 (4)
C18—C19—H19	119.0	C20—C15—C16	121.5 (4)
C20—C19—H19	119.0	C20—C15—Ru1	73.4 (3)
Ru1—C19—H19	129.4	C16—C15—Ru1	71.6 (2)
C6—N2—C14	118.2 (3)	C20—C15—H15	119.2
C6—N2—Ru1	114.8 (2)	C16—C15—H15	119.2
C14—N2—Ru1	126.8 (2)	Ru1—C15—H15	128.1
C5—N1—C1	118.7 (3)	C15—C16—C17	117.9 (4)
C5—N1—Ru1	117.1 (2)	C15—C16—Ru1	70.8 (2)
C1—N1—Ru1	124.0 (2)	C17—C16—Ru1	70.6 (2)
N2—C14—C13	120.8 (3)	C15—C16—H16	121.0
N2—C14—C9	120.7 (3)	C17—C16—H16	121.0
C13—C14—C9	118.4 (3)	Ru1—C16—H16	129.8
C19—C18—C17	118.5 (4)	C8—C7—C6	119.5 (3)
C19—C18—Ru1	71.8 (2)	C8—C7—H7	120.2
C17—C18—Ru1	70.1 (2)	C6—C7—H7	120.2
C19—C18—H18	120.8	C3—C4—C5	120.0 (4)
C17—C18—H18	120.8	C3—C4—H4	120.0
Ru1—C18—H18	129.7	C5—C4—H4	120.0
C8—C9—C14	118.6 (3)	C16—C17—C18	120.2 (4)
C8—C9—C10	122.4 (3)	C16—C17—Ru1	71.5 (2)
C14—C9—C10	119.0 (3)	C18—C17—Ru1	72.1 (2)
C10—C11—C12	119.6 (3)	C16—C17—H17	119.9
C10—C11—H11	120.2	C18—C17—H17	119.9
C12—C11—H11	120.2	Ru1—C17—H17	128.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···F4ⁱ	0.93	2.48	3.375 (5)	162
C16—H16···F1	0.93	2.24	3.148 (6)	162
C19—H19···Cl1ⁱⁱ	0.93	2.65	3.429 (4)	142

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

Acknowledgements

We thank Dr Marrappan Velusamy at the Department of Chemistry, North Eastern Hill University, Shillong 793022, India, for collecting the crystal data.

Funding information

The Department of Biotechnology (DBT), New Delhi, provided funding for this research (grant No. BT/PR36476/NNT/28/1723/2020).

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