trans-Di­chlorido­tetra­kis­(pyridine-4-carbo­nitrile-κN)ruthenium(II) toluene hemisolvate

Goodavish, F.S.; Martin, S. A.; Reinheimer, E.W.; Smucker, B.W.

doi:10.1107/S2414314626009375

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 9| September 2026| x260937

https://doi.org/10.1107/S2414314626009375

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trans-Dichloridotetrakis(pyridine-4-carbonitrile-κN)ruthenium(II) toluene hemisolvate

Frank S. Goodavish,^a ‡ Sebastião A. Martin,^a ‡ Eric W. Reinheimer ^b and Bradley W. Smucker ^a ^*

^aAustin College, 900 N Grand Avenue, Sherman, TX 75090, USA, and ^bRigaku Oxford Diffraction, 9009 New Trails Dr., The Woodlands, TX 77381, USA
^*Correspondence e-mail: [email protected]

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 5 August 2026; accepted 7 September 2026; online 25 September 2026)

The title compound, [RuCl₂(C₆H₄N₂)₄]·0.5C₇H₈, resulted from the reaction of four equivalents of pcp (pyridine-4-carbonitrile) with ruthenium(II) chloride to form a propeller-like arrangement, which is positioned along the twofold axis of the C2/c space group. The packing of the complex in the structure, resulting from the overlap at the carbonitrile groups of the complexes, results in a grid-like assembly with Ru⋯Ru diagonal distances of 17.0973 (9) and 20.0289 (5) Å, and a near 50% calculated void volume.

Keywords: crystal structure; ruthenium(II); building block; 4-cyanopyridine; voids.

CCDC reference: 2586520

Structure description

Ruthenium(II) building blocks consisting of four pyridyl-type ligands, such as [Ru(N-methyl-4,4′-bipyridinium)₄Cl₂]⁴⁺ (Cadranel & Hodak, 2015 ), have been utilized to engineer coordination networks including tetrasubstituted pyrazine (Carlucci et al., 2002 ) or 4,4′-bipyridine, which was used to explore new electrochemical devices (Vertova et al., 2007 ). In a course-based undergraduate research experiences (CURE), similar to a recently reported program incorporating X-ray crystallography in education (Abrahams et al., 2023 ), we have been investigating the syntheses and structural characterization of these types of neutral ruthenium(II) chloride building blocks with tetrakis(pyrazine) (Nesterov et al., 2012 ), tetrakis(4-methoxypyridine) (Reinheimer et al., 2023 ), and the disubstituted 4-dimethylaminopyridine and dimethyl sulfoxide (Park et al., 2024 ) ligands. We report herein the tetrasubstituted coordination of pcp (pyridine-4-carbonitrile (Enkelmann et al., 2021 ) with ruthenium(II) chloride. The coordination of a single pcp ligand with Ru^II has been utilized to investigate DNA binding (Singh et al., 2007 ) and organometallic cancer cell cytotoxicity (Wang et al., 2005 ). Other reported propeller-like structures of trans-[M(pcp)₄(NCS)₂] include M = Mn^II (Wellm et al., 2020 ) and M = Ni^II (Clegg & Harrington, 2016 ).

The ruthenium atom, and thereby the title complex, lies on a twofold axis of the C2/c space group. The structure of the complex has the four pcp ligands in a propeller-like arrangement around the ruthenium atom (Fig. 1), which is typical of ruthenium complexes with four pyridyl-based ligands (Małecki et al., 2005 ; Wong & Lau, 1994 ). The tilt angle of the pyridyl rings compared to the plane containing Ru and the four coordinated N atoms is 40.78 (11)° (N1-pyridyl ring) and 55.47 (12)° (N2- pyridyl ring). The ruthenium–pyridyl nitrogen distances are 2.085 (3) and 2.082 (3) Å, which fall in the range of Ru—N distances in other ruthenium(II) complexes with four pyridyl-based ligands: for example, 2.0620 (14) Å for pyrazine (Nesterov et al., 2012), 2.080 (3) Å for pyridine (Coe et al., 1995 ), and 2.137 (5) Å for 4-methoxypyridine (Reinheimer et al., 2023). The Ru—N distance is shorter compared to other ruthenium(II) complexes containing one pcp ligand, many of which utilize larger trans-influence ligands like η⁶-arenes, such as [Ru(η⁶-C₆Me₆)Cl₂(pcp)], 2.136 (6) Å (Singh et al., 2007) or [Ru(η⁶-(p-cymene))I₂(pcp)], 2.119 (6) Å (Torubaev & Skabitsky, 2019 ), or an η³-(allyl) ligand, for example in [Ru(η³:η³-C₁₀H₁₆)Cl₂(pcp)], 2.210 (3) and 2.202 (3) Å (Nand Sahay et al., 2000 ).

Figure 1
The propeller-like arrangement of the two unique pcp ligands in trans-[Ru(pcp)₄Cl₂] (ellipsoids at 50% probability) along with labels of the symmetry-generated (1 − x, y, $[{1\over 2}]$ − x) N1, C1 N2 and C7 atoms.>

The title complex packs in a grid-like assembly resulting from the overlap of the carbonitrile groups of ruthenium-pcp units. The Ru⋯Ru′ distances within a grid are 11.9141 (5) (Ru′ = $[{3\over 2}]$ − x, $[{3\over 2}]$ − y, 1 − z) and 14.3106 (3) Å (Ru′ = − $[{1\over 2}]$ + x, $[{1\over 2}]$ + y, z) and Ru′⋯Ru′′ diagonal distances of 17.0973 (9) (Ru′ = x, y, z and Ru′′ = 1 − x, 2 − y, 1 − z) and 20.0289 (5) Å (Ru′ = − $[{1\over 2}]$ + x, $[{1\over 2}]$ + y, z and Ru′′ = $[{3\over 2}]$ − x, $[{3\over 2}]$ − y, 1 − z) (Fig. 2). The calculated void volume (Macrae et al., 2020 ) is 47.0% (1924.60 Å³) of the unit cell (Fig. 3), which is presumably occupied by disordered solvent molecules. The complexes stack in a staggered pattern along the direction of the Cl—Ru—Cl axes with intermolecular distance between the two chloride ions [Cl1 at x, y, z and symmetry-related Cl1 at 1 − x, 1 − y, 1 − z] of 4.7515 (17) Å. The chloride ions of one complex are near the H1 atoms of neighbouring complexes with the distance between Cl1(1 − x, 1 − y, 1 − z) and H1 being closer to the neighbouring H1 atom (2.82 Å) than the corresponding intramolecular H1 atom (2.93 Å) (Fig. 4).

Figure 2
Representative packing of trans-[Ru(pcp)₄Cl₂] (capped sticks) viewed along the c axis of the grid-like assembly with intermolecular Ru⋯Ru distances (Å) within a unit of the grid.

Figure 3
Calculated voids (yellow surface) in crystal unit cell (axes labelled) with capped stick model.

Figure 4
The staggered stacking of the complexes (capped sticks) showing the longer Cl1⋯H1 intramolecular distance (2.93 Å) and the intermolecular distance of the shorter Cl1(1 − x, 1 − y, 1 − z)⋯H1 (2.82 Å) and Cl1(1 − x, y, 1.5 − z)⋯Cl1(x, 1 − y, $[{1\over 2}]$ + z) (4.752 Å).

Synthesis and crystallization

Following the preparation of other trans-RuCl₂ complexes containing four pyridyl ligands, (Coe et al., 1995; Coe, 2004 ) the title compound was synthesized by mixing, at reflux, a yellow solution containing 100 mg (0.206 mmol) of [Ru(DMSO)₄Cl₂], and 99.6 mg (0.957 mmol) of pyridine-4-carbonitrile in 20 ml of toluene for 2 h under N₂ with light excluded. The resulting dark-red solution slowly cooled and sat undisturbed for one week. The resulting dark red–brown solid was filtered in air and washed with toluene to give 90 mg (74% yield) of product. FT–IR 2921(C—H), 2234(C≡N), 1606, 1485, 1420, 1307, 1219, 1110, 1095, 1017, 936, 833, 732, 716, 683, 564, 426 cm^{−1. 1}H-NMR (acetone-d₆, δ/p.p.m.) 8.69 (dd), 7.62 (dd), 7.2–7.0 (toluene), 2.28 (toluene). Dark-red block-shaped crystals were harvested directly from the product of trans-[Ru(pcp)₄Cl₂] and used for X-ray structural characterization, as well as for FT–IR and NMR spectroscopy analyses.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. A solvent mask was calculated and 92 electrons were found in the void per unit cell (Dolomanov et al., 2009 ). This is consistent with the presence of two toluene molecules per unit cell, which accounts for 100 electrons per unit cell. In the ¹H-NMR using crystals (noted in the Synthesis and crystallization section), we observed an integration of 2 toluene molecules per [Ru(pcp)₄Cl₂], but the electron density over the duration of the 293 K data collection of a single crystal resulted in a toluene hemisolvate.

Table 1
Experimental details

Crystal data
Chemical formula	[RuCl₂(C₆H₄N₂)₄]·0.5C₇H₈
M_r	588.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	19.3087 (5), 21.1269 (6), 10.0865 (2)
β (°)	95.909 (2)
V (Å³)	4092.75 (18)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.54
Crystal size (mm)	0.25 × 0.23 × 0.18

Data collection
Diffractometer	XtaLAB Mini II
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2022 )
T_min, T_max	0.899, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	43912, 3647, 3113
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.01
No. of reflections	3647
No. of parameters	159
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.58
Computer programs: CrysAlis PRO (Rigaku OD, 2022), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020).

Structural data

CCDC reference: 2586520

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626009375/bh4104sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626009375/bh4104Isup2.hkl

checkCIF report

Computing details top

trans-Dichloridotetrakis(pyridine-4-carbonitrile-κN)ruthenium(II) toluene hemisolvate top

Crystal data top

[RuCl₂(C₆H₄N₂)₄]·0.5C₇H₈	F(000) = 1276
M_r = 588.42	D_x = 0.955 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.3087 (5) Å	Cell parameters from 7651 reflections
b = 21.1269 (6) Å	θ = 2.0–22.1°
c = 10.0865 (2) Å	µ = 0.54 mm⁻¹
β = 95.909 (2)°	T = 293 K
V = 4092.75 (18) Å³	Block, red
Z = 4	0.25 × 0.23 × 0.18 mm

Data collection top

XtaLAB Mini II diffractometer	3647 independent reflections
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source	3113 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10.0000 pixels mm^-1	θ_max = 25.2°, θ_min = 2.4°
ω scans	h = −23→23
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2022)	k = −25→25
T_min = 0.899, T_max = 0.929	l = −12→12
43912 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1014P)² + 3.5296P] where P = (F_o² + 2F_c²)/3
3647 reflections	(Δ/σ)_max < 0.001
159 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³
0 constraints

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

	x	y	z	U_iso*/U_eq
Ru1	0.5000	0.61337 (2)	0.2500	0.04687 (18)
Cl1	0.47985 (5)	0.61078 (4)	0.48123 (9)	0.0612 (3)
N1	0.42424 (14)	0.54388 (13)	0.2100 (3)	0.0490 (6)
N2	0.57540 (17)	0.68344 (14)	0.2886 (3)	0.0584 (7)
N3	0.2566 (3)	0.3494 (3)	0.0460 (5)	0.130 (2)
N4	0.7718 (4)	0.8570 (4)	0.4127 (7)	0.184 (4)
C1	0.42393 (18)	0.48927 (17)	0.2810 (3)	0.0532 (8)
H1	0.4545	0.4858	0.3581	0.064*
C2	0.3816 (2)	0.43937 (19)	0.2459 (4)	0.0606 (9)
H2	0.3848	0.4024	0.2961	0.073*
C3	0.3337 (2)	0.4443 (2)	0.1343 (4)	0.0655 (10)
C4	0.3301 (2)	0.5013 (2)	0.0642 (4)	0.0645 (10)
H4	0.2968	0.5071	−0.0083	0.077*
C5	0.37586 (18)	0.54852 (18)	0.1033 (4)	0.0564 (9)
H5	0.3738	0.5858	0.0540	0.068*
C6	0.2899 (3)	0.3921 (3)	0.0871 (5)	0.0898 (16)
C7	0.6328 (2)	0.6852 (2)	0.2254 (4)	0.0753 (12)
H7	0.6386	0.6543	0.1617	0.090*
C8	0.6837 (3)	0.7301 (3)	0.2495 (5)	0.0941 (16)
H8	0.7223	0.7308	0.2014	0.113*
C9	0.6757 (3)	0.7745 (2)	0.3482 (5)	0.0936 (16)
C10	0.6169 (3)	0.7736 (2)	0.4120 (5)	0.0973 (17)
H10	0.6105	0.8037	0.4769	0.117*
C11	0.5674 (2)	0.7283 (2)	0.3804 (5)	0.0759 (12)
H11	0.5271	0.7285	0.4235	0.091*
C12	0.7309 (4)	0.8217 (4)	0.3820 (6)	0.138 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.0492 (3)	0.0439 (3)	0.0466 (3)	0.000	0.00040 (16)	0.000
Cl1	0.0703 (6)	0.0627 (6)	0.0507 (5)	0.0067 (4)	0.0063 (4)	0.0019 (4)
N1	0.0483 (15)	0.0487 (16)	0.0492 (15)	0.0007 (12)	0.0012 (12)	0.0047 (12)
N2	0.0640 (19)	0.0546 (17)	0.0567 (18)	−0.0045 (14)	0.0060 (15)	−0.0052 (14)
N3	0.142 (5)	0.131 (4)	0.111 (4)	−0.073 (4)	−0.008 (3)	−0.014 (3)
N4	0.217 (7)	0.206 (7)	0.126 (5)	−0.152 (7)	0.003 (5)	−0.026 (5)
C1	0.0546 (19)	0.055 (2)	0.0490 (19)	−0.0004 (16)	0.0022 (15)	0.0065 (16)
C2	0.068 (2)	0.060 (2)	0.052 (2)	−0.0116 (18)	0.0035 (17)	0.0045 (17)
C3	0.063 (2)	0.071 (3)	0.063 (2)	−0.016 (2)	0.0067 (18)	−0.0044 (19)
C4	0.053 (2)	0.077 (3)	0.061 (2)	−0.0067 (19)	−0.0062 (17)	0.002 (2)
C5	0.0504 (19)	0.059 (2)	0.059 (2)	0.0030 (16)	−0.0011 (16)	0.0092 (17)
C6	0.095 (4)	0.100 (4)	0.073 (3)	−0.040 (3)	0.004 (3)	−0.002 (3)
C7	0.078 (3)	0.076 (3)	0.072 (3)	−0.028 (2)	0.006 (2)	−0.008 (2)
C8	0.092 (3)	0.112 (4)	0.078 (3)	−0.051 (3)	0.006 (3)	−0.005 (3)
C9	0.116 (4)	0.084 (3)	0.079 (3)	−0.052 (3)	0.000 (3)	−0.002 (3)
C10	0.139 (5)	0.066 (3)	0.088 (3)	−0.033 (3)	0.013 (3)	−0.014 (2)
C11	0.085 (3)	0.061 (2)	0.082 (3)	−0.014 (2)	0.012 (2)	−0.011 (2)
C12	0.174 (6)	0.149 (6)	0.088 (4)	−0.107 (5)	−0.001 (4)	−0.007 (4)

Geometric parameters (Å, º) top

Ru1—Cl1ⁱ	2.4044 (9)	C2—C3	1.386 (5)
Ru1—Cl1	2.4044 (9)	C3—C4	1.395 (6)
Ru1—N1	2.082 (3)	C3—C6	1.441 (6)
Ru1—N1ⁱ	2.082 (3)	C4—H4	0.9300
Ru1—N2	2.085 (3)	C4—C5	1.364 (5)
Ru1—N2ⁱ	2.085 (3)	C5—H5	0.9300
N1—C1	1.358 (4)	C7—H7	0.9300
N1—C5	1.355 (4)	C7—C8	1.368 (6)
N2—C7	1.335 (5)	C8—H8	0.9300
N2—C11	1.345 (5)	C8—C9	1.389 (7)
N3—C6	1.159 (6)	C9—C10	1.361 (7)
N4—C12	1.108 (7)	C9—C12	1.474 (7)
C1—H1	0.9300	C10—H10	0.9300
C1—C2	1.358 (5)	C10—C11	1.368 (6)
C2—H2	0.9300	C11—H11	0.9300

Cl1—Ru1—Cl1ⁱ	177.39 (5)	C2—C3—C4	118.1 (4)
N1—Ru1—Cl1	89.49 (8)	C2—C3—C6	122.1 (4)
N1—Ru1—Cl1ⁱ	88.67 (8)	C4—C3—C6	119.8 (4)
N1ⁱ—Ru1—Cl1ⁱ	89.49 (8)	C3—C4—H4	120.4
N1ⁱ—Ru1—Cl1	88.67 (8)	C5—C4—C3	119.2 (3)
N1—Ru1—N1ⁱ	90.34 (15)	C5—C4—H4	120.4
N1ⁱ—Ru1—N2ⁱ	179.48 (11)	N1—C5—C4	123.4 (3)
N1—Ru1—N2	179.48 (11)	N1—C5—H5	118.3
N1—Ru1—N2ⁱ	90.07 (12)	C4—C5—H5	118.3
N1ⁱ—Ru1—N2	90.07 (12)	N3—C6—C3	177.4 (7)
N2—Ru1—Cl1ⁱ	91.01 (9)	N2—C7—H7	118.3
N2ⁱ—Ru1—Cl1ⁱ	90.84 (9)	N2—C7—C8	123.4 (4)
N2ⁱ—Ru1—Cl1	91.02 (9)	C8—C7—H7	118.3
N2—Ru1—Cl1	90.84 (9)	C7—C8—H8	121.2
N2ⁱ—Ru1—N2	89.51 (17)	C7—C8—C9	117.7 (5)
C1—N1—Ru1	122.6 (2)	C9—C8—H8	121.2
C5—N1—Ru1	121.1 (2)	C8—C9—C12	119.4 (6)
C5—N1—C1	116.1 (3)	C10—C9—C8	119.3 (4)
C7—N2—Ru1	121.9 (3)	C10—C9—C12	121.2 (5)
C7—N2—C11	118.0 (4)	C9—C10—H10	120.1
C11—N2—Ru1	120.1 (3)	C11—C10—C9	119.7 (5)
N1—C1—H1	118.0	C11—C10—H10	120.1
C2—C1—N1	123.9 (3)	N2—C11—C10	121.8 (5)
C2—C1—H1	118.0	N2—C11—H11	119.1
C1—C2—H2	120.4	C10—C11—H11	119.1
C1—C2—C3	119.1 (4)	N4—C12—C9	177.1 (7)
C3—C2—H2	120.4

Ru1—N1—C1—C2	−170.2 (3)	C3—C4—C5—N1	−1.9 (6)
Ru1—N1—C5—C4	172.5 (3)	C5—N1—C1—C2	4.1 (5)
Ru1—N2—C7—C8	−179.2 (4)	C6—C3—C4—C5	−174.4 (4)
Ru1—N2—C11—C10	177.5 (4)	C7—N2—C11—C10	−1.8 (6)
N1—C1—C2—C3	−2.6 (6)	C7—C8—C9—C10	−3.0 (8)
N2—C7—C8—C9	2.2 (8)	C7—C8—C9—C12	176.9 (5)
C1—N1—C5—C4	−1.8 (5)	C8—C9—C10—C11	1.4 (9)
C1—C2—C3—C4	−1.3 (6)	C9—C10—C11—N2	1.0 (8)
C1—C2—C3—C6	176.5 (4)	C11—N2—C7—C8	0.1 (7)
C2—C3—C4—C5	3.4 (6)	C12—C9—C10—C11	−178.5 (5)

Symmetry code: (i) −x+1, y, −z+1/2.

Footnotes

‡These authors contributed equally to this work.

Acknowledgements

The students in Austin College's Advanced Inorganic course: Gabriel J. Graf, Lucas D. Hale, Joshua S. Dengwan, Frederick W. Wilson, Enson A. Flores, Duy-Dan Z. Thai, Vanessa P. Garcia, Stephen T. Estraca, and Anika K. Chand contributed through their co-synthesis and analyses of the title compound.

Funding information

Funding for this research was provided by: Welch Foundation (grant No. AD-0007); Jerry Taylor and Nancy Bryant Foundation (gift to the Austin College Science Division); NSF MRI (grant No. CHE-1725651).

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