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. 2024 Feb 8;9(Pt 2):x240114. doi: 10.1107/S2414314624001147

Aqua­bis­(2,2′-bi­pyridine-κ2N,N′)(isonicotinamide-κN)ruthenium(II) bis­(trifluoromethanesulfonate)

Liam Faubert a, Hadi D Arman b, Rafael A Adrian a,*
Editor: M Boltec
PMCID: PMC10915547  PMID: 38455113

In the crystal structure of the title compound, the ruthenium(II) metal center is surrounded by two bidentate 2,2′-bi­pyridine, an isonicotinamide ligand, and a water in a distorted octa­hedral geometry. Hydrogen bonding is present between counter-ion and ligand.

Keywords: crystal structure; ruthenium(II); octa­hedral geometry; 2,2′-bi­pyridine; bidentate ligand; isonicotinamide; hydrogen bonding; π–π stacking

Abstract

In the title complex, [Ru(C10H8N2)2(C6H6N2O)(H2O)](CF3SO3)2, the central RuII atom is sixfold coordinated by two bidentate 2,2′-bi­pyridine, an isonic­otinamide ligand, and a water mol­ecule in a distorted octa­hedral environment with tri­fluoro­methane­sulfonate ions completing the outer coordination sphere of the complex. Hydrogen bonding involving the water mol­ecule and weak π–π stacking inter­actions between the pyridyl rings in adjacent mol­ecules contribute to the alignment of the complexes in columns parallel to the c axis.graphic file with name x-09-x240114-scheme1-3D1.jpg

Structure description

Over the last three years, a lot of effort has been directed into studying ruthenium(II) bis­(bi­pyridine) complexes due to their catalytic properties (Griffin et al., 2021 ▸), luminescence (Cuéllar et al., 2021 ▸) and biological activity (Al–Wahaib et al., 2021 ▸; Allison et al., 2021 ▸). Last year, bi­pyridine ruthenium(II) complexes with halogen-substituted salicylates showed promising in vitro anti­proliferative activity against MCF-7 (breast cancer) and U-118 MG (human glioma) cell lines (Schoeller et al., 2023 ▸). Our research group’s inter­est currently lies in synthesizing metal complexes with application as anti­proliferative agents; as part of our research in this area, we describe the synthesis and structure of the title ruthenium(II) complex, Fig. 1 ▸.

Figure 1.

Figure 1

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Asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level; hydrogen bonds shown as dashed lines. The minor occupied sites of the disordered tri­fluoro­methane­sulfonate ion are omitted for clarity.

The asymmetric unit contains the title compound, with four symmetry-related entities inside the unit cell. The ruthenium(II) ion shows a distorted octa­hedral coordination environment defined by two 2,2′-bi­pyridine ligands, one isonicotinamide ligand and a water mol­ecule. Tri­fluoromethane­sulfonate ions sit in the outer coord­ination sphere, balancing the charge of the metal complex. All the Ru—N bond bond lengths are in good agreement with comparable ruthenium(II) bis­(2,2′-bi­pyridine) complexes currently available in the Cambridge Structural Database (CSD, version 5.45, Nov 2023; Groom et al., 2016 ▸; Huang & Ogawa, 2006 ▸, refcode LECFOP; Keniley Jr et al., 2013 ▸, refcode AROJIB01; Yoshikawa et al., 2016 ▸, refcode DACBER; de Souza et al., 2017 ▸, refcode TAWQOA), The N—Ru—N angles found in the bi­pyridine ligands also concur with the values reported in the previously referenced ruthenium(II) bi­pyridine complexes. The Ru—O bond length matches well with the distance in other ruthenium complexes with a coordinating water mol­ecule (Gupta et al., 1992 ▸, refcode KUPBUS; Bonnet et al., 2003 ▸, refcode IPESIF; Ghaderian et al., 2020 ▸, refcode LAGCIJ). All relevant bonds and angles are presented in Table 1 ▸.

Table 1. Selected geometric parameters (Å, °).

Ru1—N3 2.030 (6) Ru1—N2 2.069 (5)
Ru1—N1 2.047 (6) Ru1—N5 2.087 (5)
Ru1—N4 2.050 (6) Ru1—O2 2.145 (5)
       
N3—Ru1—N1 91.1 (2) N4—Ru1—N5 86.8 (2)
N3—Ru1—N4 79.4 (2) N2—Ru1—N5 95.4 (2)
N1—Ru1—N4 99.3 (2) N3—Ru1—O2 171.7 (2)
N3—Ru1—N2 96.3 (2) N1—Ru1—O2 86.9 (2)
N1—Ru1—N2 78.6 (2) N4—Ru1—O2 93.0 (2)
N4—Ru1—N2 175.2 (2) N2—Ru1—O2 91.2 (2)
N3—Ru1—N5 90.7 (2) N5—Ru1—O2 92.1 (2)
N1—Ru1—N5 173.9 (2)    
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The packing diagram reveals the stacking of the asymmetric units in columns observable when looking at the crystal parallel to the caxis (Fig. 2 ▸). Contiguous pyridine rings show weak π–π stacking inter­actions, with a centroid-to-centroid distance (Cg⋯Cg) of 3.791 (4) Å and an offset distance of 1.559 Å, which are responsible for the stacking into columns. Tri­fluoro­methane­sulfonate ions sit in the gap between columns and are held in place by hydrogen bonds between one of the oxygen atoms of the tri­fluoro­methane­sulfonate ion and one of the hydrogen atoms in the water mol­ecule, as well as between the oxygen in the isonicotinamide ligand and the second hydrogen in the water mol­ecule (Table 2 ▸).

Figure 2.

Figure 2

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Perspective view of the crystal packing of the title complex parallel to the c axis; H atoms and the minor occupied sites of the disordered tri­fluoro­methane­sulfonate ion are omitted for clarity.

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2A⋯O1i 0.89 1.73 2.617 (7) 174
O2—H2B⋯O5 0.89 1.90 2.775 (8) 169
N6—H6A⋯O6i 0.88 2.32 3.190 (9) 169
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Symmetry code: (i) Inline graphic.

Synthesis and crystallization

The title compound was synthesized by the reaction of cis-Ru(bpy)2Cl2 (0.100 g, 0.206 mmol) with Ag(CF3SO3) (0.106 g, 0.412 mmol) in 50 ml of EtOH. After heating and stirring for about 1 h at 323.15 K, the solution was filtrated using a PTFE syringe filter to remove AgCl. Isonicotinamide (0.050 g, 0.41 mmol) was then added to the mixture and the resulting solution was heated at 338.15 K until the volume was reduced to about 10 ml. Crystal suitable for X-ray diffraction were grown by vapor diffusion of diethyl ether over a saturated aceto­nitrile solution of the title complex.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. One of the tri­fluoro­methane­sulfonate ions has four atoms disordered over two sets of sites. The site occupation factors of the disordered atoms were set to 0.85 and 0.15, respectively. The displacement parameters of the minor occupied sites were restrained to an isotropic behavior. The C—S distance of the minor occupied sites was restrained to 1.70 (2) Å. H atoms were refined using a riding model with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) or O—H = 0.89 Å and Uiso(H) = 1.5Ueq(O).

Table 3. Experimental details.

Crystal data
Chemical formula [Ru(C10H8N2)2(C6H6N2O(H2O)](CF3SO3)2
M r 851.72
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 9.7878 (1), 26.2103 (3), 12.6443 (1)
β (°) 97.202 (1)
V (Å3) 3218.19 (6)
Z 4
Radiation type Cu Kα
μ (mm−1) 6.02
Crystal size (mm) 0.11 × 0.06 × 0.04
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, HyPix
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2023 ▸)
Tmin, Tmax 0.099, 0.513
No. of measured, independent and observed [I > 2σ(I)] reflections 35289, 5777, 5536
R int 0.072
(sin θ/λ)max (Å−1) 0.599
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.159, 1.06
No. of reflections 5777
No. of parameters 496
No. of restraints 25
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.34, −1.09
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Computer programs: CrysAlis PRO (Rigaku OD, 2023 ▸), SHELXT2018/2 (Sheldrick, 2015a ▸), SHELXL2018/3 (Sheldrick, 2015b ▸), and OLEX2 (Dolomanov et al., 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624001147/bt4147sup1.cif

x-09-x240114-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624001147/bt4147Isup2.hkl

x-09-x240114-Isup2.hkl (459.5KB, hkl)
x-09-x240114-Isup4.mol (4KB, mol)

Supporting information file. DOI: 10.1107/S2414314624001147/bt4147Isup4.mol

CCDC reference: 2330544

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

Acknowledgments

We are thankful for the support of the Department of Chemistry and Biochemistry at the University of the Incarnate Word and the X-ray Diffraction Laboratory at the University of Texas at San Antonio.

full crystallographic data

Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Crystal data

[Ru(C10H8N2)2(C6H6N2O)(H2O)](CF3O3S)2 F(000) = 1712
Mr = 851.72 Dx = 1.758 Mg m−3
Monoclinic, P21/c Cu Kα radiation, λ = 1.54184 Å
a = 9.7878 (1) Å Cell parameters from 24511 reflections
b = 26.2103 (3) Å θ = 3.4–75.8°
c = 12.6443 (1) Å µ = 6.02 mm−1
β = 97.202 (1)° T = 100 K
V = 3218.19 (6) Å3 Plate, clear dark red
Z = 4 0.11 × 0.06 × 0.04 mm
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer 5777 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source 5536 reflections with I > 2σ(I)
Mirror monochromator Rint = 0.072
Detector resolution: 10.0000 pixels mm-1 θmax = 67.5°, θmin = 3.9°
ω scans h = −11→10
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023) k = −26→31
Tmin = 0.099, Tmax = 0.513 l = −15→15
35289 measured reflections
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Refinement

Refinement on F2 Primary atom site location: dual
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.071 H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.010P)2 + 35.P] where P = (Fo2 + 2Fc2)/3
S = 1.06 (Δ/σ)max < 0.001
5777 reflections Δρmax = 1.34 e Å−3
496 parameters Δρmin = −1.09 e Å−3
25 restraints
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Special details

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.
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
Ru1 0.61055 (5) 0.14183 (2) 0.26873 (4) 0.03384 (16)
O1 0.5987 (5) −0.10366 (18) 0.4895 (4) 0.0429 (11)
O2 0.4138 (5) 0.1473 (2) 0.3258 (4) 0.0426 (11)
H2A 0.415425 0.132447 0.389072 0.064*
H2B 0.394335 0.179657 0.338452 0.064*
N1 0.5897 (6) 0.2176 (2) 0.2310 (4) 0.0372 (13)
N2 0.7066 (6) 0.1756 (2) 0.4063 (4) 0.0351 (12)
N3 0.7814 (6) 0.1366 (2) 0.1933 (5) 0.0367 (12)
N4 0.5283 (6) 0.1109 (2) 0.1259 (5) 0.0395 (13)
N5 0.6388 (6) 0.0670 (2) 0.3238 (4) 0.0342 (12)
N6 0.8211 (7) −0.1061 (2) 0.4606 (5) 0.0465 (15)
H6A 0.834866 −0.136811 0.487829 0.056*
H6B 0.889046 −0.089571 0.436429 0.056*
C1 0.5144 (8) 0.2376 (3) 0.1440 (6) 0.0437 (17)
H1 0.468971 0.215078 0.092085 0.052*
C2 0.5013 (8) 0.2896 (3) 0.1277 (7) 0.053 (2)
H2 0.446150 0.302307 0.066209 0.063*
C3 0.5683 (8) 0.3228 (3) 0.2009 (7) 0.053 (2)
H3 0.561552 0.358626 0.189826 0.064*
C4 0.6444 (8) 0.3036 (3) 0.2896 (6) 0.0463 (18)
H4 0.691237 0.325956 0.341113 0.056*
C5 0.6532 (7) 0.2510 (3) 0.3044 (6) 0.0391 (15)
C6 0.7253 (7) 0.2268 (3) 0.3995 (6) 0.0378 (15)
C7 0.8054 (8) 0.2532 (3) 0.4799 (6) 0.0474 (18)
H7 0.818396 0.288929 0.473048 0.057*
C8 0.8655 (8) 0.2284 (3) 0.5686 (6) 0.051 (2)
H8 0.922138 0.246229 0.622999 0.061*
C9 0.8419 (8) 0.1766 (3) 0.5773 (6) 0.0476 (18)
H9 0.880168 0.158475 0.638995 0.057*
C10 0.7622 (7) 0.1516 (3) 0.4956 (5) 0.0376 (15)
H10 0.745896 0.116144 0.502737 0.045*
C11 0.9100 (7) 0.1537 (3) 0.2309 (7) 0.0427 (17)
H11 0.925296 0.167870 0.300561 0.051*
C12 1.0178 (8) 0.1511 (3) 0.1719 (7) 0.0488 (19)
H12 1.106061 0.163383 0.200527 0.059*
C13 0.9978 (8) 0.1306 (3) 0.0709 (7) 0.0491 (19)
H13 1.071896 0.128522 0.029288 0.059*
C14 0.8690 (8) 0.1133 (3) 0.0312 (6) 0.0438 (17)
H14 0.853294 0.099132 −0.038411 0.053*
C15 0.7616 (7) 0.1166 (2) 0.0934 (6) 0.0376 (15)
C16 0.6201 (8) 0.1007 (3) 0.0561 (6) 0.0394 (16)
C17 0.5790 (9) 0.0771 (3) −0.0413 (6) 0.0484 (18)
H17 0.644015 0.070493 −0.089433 0.058*
C18 0.4433 (9) 0.0636 (3) −0.0673 (6) 0.055 (2)
H18 0.413769 0.046924 −0.132983 0.066*
C19 0.3503 (9) 0.0744 (3) 0.0034 (6) 0.0521 (19)
H19 0.255877 0.065725 −0.013631 0.063*
C20 0.3956 (8) 0.0979 (3) 0.0983 (6) 0.0450 (17)
H20 0.330940 0.105272 0.146332 0.054*
C21 0.7662 (7) 0.0492 (3) 0.3579 (6) 0.0402 (16)
H21 0.842514 0.071019 0.352294 0.048*
C22 0.7920 (7) 0.0012 (3) 0.4005 (6) 0.0392 (16)
H22 0.883545 −0.009265 0.424810 0.047*
C23 0.6833 (7) −0.0314 (3) 0.4073 (5) 0.0378 (15)
C24 0.5510 (7) −0.0144 (3) 0.3708 (6) 0.0401 (16)
H24 0.474028 −0.036110 0.374114 0.048*
C25 0.5324 (7) 0.0347 (3) 0.3295 (5) 0.0372 (15)
H25 0.441787 0.045920 0.304487 0.045*
C26 0.6994 (8) −0.0841 (3) 0.4557 (6) 0.0398 (16)
S1 0.2217 (2) 0.25487 (8) 0.41915 (16) 0.0494 (5)
F1 0.2188 (6) 0.3402 (2) 0.3117 (4) 0.0755 (15)
F2 0.1589 (6) 0.2750 (2) 0.2159 (4) 0.0760 (16)
F3 0.0165 (5) 0.3069 (2) 0.3194 (4) 0.0780 (16)
O5 0.3606 (6) 0.2454 (2) 0.3927 (5) 0.0561 (14)
O6 0.1339 (6) 0.2106 (2) 0.4103 (5) 0.0621 (15)
O7 0.2149 (6) 0.2865 (2) 0.5113 (4) 0.0576 (15)
C53 0.1482 (10) 0.2957 (3) 0.3155 (8) 0.065 (3)
S2A 0.1522 (2) −0.03696 (10) 0.29352 (18) 0.0434 (5) 0.85
F5 −0.0471 (6) 0.0206 (2) 0.2038 (4) 0.0841 (19)
F4 0.1073 (7) 0.0024 (2) 0.1044 (4) 0.0848 (19)
O8 0.0628 (5) −0.0594 (2) 0.3648 (4) 0.0503 (13)
O4 0.2389 (6) −0.0727 (2) 0.2487 (5) 0.0636 (16)
C27A 0.0347 (11) −0.0160 (4) 0.1798 (8) 0.050 (2) 0.85
F6A −0.0419 (6) −0.0556 (3) 0.1393 (5) 0.0708 (18) 0.85
O3A 0.2141 (8) 0.0121 (3) 0.3310 (6) 0.068 (2) 0.85
S2B 0.0994 (15) −0.0604 (5) 0.2581 (11) 0.043 (3) 0.15
O3B 0.015 (7) −0.080 (3) 0.185 (5) 0.107 (19) 0.15
C27B 0.110 (5) 0.0032 (10) 0.230 (4) 0.043 (11) 0.15
F6B 0.131 (9) 0.033 (3) 0.283 (6) 0.17 (3) 0.15
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Ru1 0.0356 (3) 0.0340 (3) 0.0319 (3) −0.0025 (2) 0.0042 (2) 0.0010 (2)
O1 0.050 (3) 0.033 (3) 0.047 (3) −0.006 (2) 0.012 (2) 0.003 (2)
O2 0.044 (3) 0.049 (3) 0.037 (3) −0.004 (2) 0.010 (2) 0.000 (2)
N1 0.037 (3) 0.041 (3) 0.035 (3) 0.000 (2) 0.008 (2) 0.006 (2)
N2 0.038 (3) 0.032 (3) 0.035 (3) 0.001 (2) 0.004 (2) 0.001 (2)
N3 0.041 (3) 0.028 (3) 0.042 (3) 0.000 (2) 0.008 (2) 0.008 (2)
N4 0.044 (3) 0.037 (3) 0.038 (3) 0.004 (3) 0.006 (3) 0.004 (3)
N5 0.038 (3) 0.032 (3) 0.033 (3) −0.002 (2) 0.005 (2) 0.001 (2)
N6 0.052 (4) 0.032 (3) 0.057 (4) −0.001 (3) 0.014 (3) 0.005 (3)
C1 0.048 (4) 0.041 (4) 0.041 (4) 0.003 (3) 0.002 (3) 0.008 (3)
C2 0.050 (4) 0.052 (5) 0.054 (5) 0.005 (4) −0.001 (4) 0.023 (4)
C3 0.056 (5) 0.037 (4) 0.067 (5) −0.003 (4) 0.004 (4) 0.011 (4)
C4 0.051 (4) 0.035 (4) 0.052 (4) −0.003 (3) 0.004 (4) 0.006 (3)
C5 0.037 (4) 0.040 (4) 0.042 (4) −0.004 (3) 0.007 (3) 0.000 (3)
C6 0.040 (4) 0.034 (4) 0.041 (4) 0.001 (3) 0.008 (3) 0.003 (3)
C7 0.050 (4) 0.033 (4) 0.058 (5) −0.005 (3) 0.001 (4) −0.010 (3)
C8 0.051 (4) 0.047 (5) 0.051 (5) 0.000 (4) −0.008 (4) −0.017 (4)
C9 0.050 (4) 0.049 (5) 0.040 (4) 0.009 (4) −0.005 (3) −0.007 (3)
C10 0.044 (4) 0.031 (3) 0.038 (4) 0.002 (3) 0.003 (3) 0.000 (3)
C11 0.042 (4) 0.029 (3) 0.058 (5) −0.003 (3) 0.009 (3) 0.003 (3)
C12 0.041 (4) 0.036 (4) 0.072 (5) −0.002 (3) 0.015 (4) 0.004 (4)
C13 0.052 (5) 0.033 (4) 0.067 (5) 0.007 (3) 0.027 (4) 0.007 (4)
C14 0.053 (4) 0.035 (4) 0.045 (4) 0.007 (3) 0.016 (3) 0.008 (3)
C15 0.047 (4) 0.023 (3) 0.044 (4) 0.007 (3) 0.011 (3) 0.004 (3)
C16 0.052 (4) 0.029 (3) 0.038 (4) 0.009 (3) 0.006 (3) 0.005 (3)
C17 0.062 (5) 0.043 (4) 0.040 (4) 0.008 (4) 0.007 (4) 0.000 (3)
C18 0.070 (6) 0.057 (5) 0.036 (4) 0.000 (4) −0.006 (4) −0.006 (4)
C19 0.048 (4) 0.057 (5) 0.049 (5) 0.001 (4) −0.001 (4) −0.003 (4)
C20 0.042 (4) 0.050 (4) 0.042 (4) −0.001 (3) 0.002 (3) −0.003 (3)
C21 0.041 (4) 0.037 (4) 0.044 (4) −0.004 (3) 0.010 (3) −0.003 (3)
C22 0.037 (4) 0.032 (4) 0.049 (4) −0.002 (3) 0.007 (3) −0.002 (3)
C23 0.047 (4) 0.032 (4) 0.035 (4) −0.003 (3) 0.011 (3) 0.000 (3)
C24 0.042 (4) 0.041 (4) 0.039 (4) −0.008 (3) 0.010 (3) −0.001 (3)
C25 0.038 (4) 0.037 (4) 0.036 (4) −0.005 (3) 0.001 (3) −0.003 (3)
C26 0.048 (4) 0.033 (4) 0.038 (4) −0.003 (3) 0.009 (3) −0.006 (3)
S1 0.0465 (10) 0.0490 (11) 0.0523 (11) 0.0038 (8) 0.0047 (8) −0.0023 (9)
F1 0.090 (4) 0.065 (3) 0.068 (3) −0.002 (3) −0.002 (3) 0.013 (3)
F2 0.076 (4) 0.102 (4) 0.047 (3) 0.011 (3) −0.001 (3) −0.011 (3)
F3 0.059 (3) 0.104 (5) 0.068 (3) 0.017 (3) −0.002 (3) 0.007 (3)
O5 0.048 (3) 0.058 (4) 0.064 (4) 0.004 (3) 0.012 (3) −0.005 (3)
O6 0.057 (3) 0.051 (3) 0.079 (4) −0.011 (3) 0.011 (3) −0.005 (3)
O7 0.061 (3) 0.062 (4) 0.049 (3) 0.011 (3) 0.006 (3) −0.012 (3)
C53 0.067 (6) 0.043 (5) 0.076 (6) 0.008 (4) −0.026 (5) −0.015 (4)
S2A 0.0361 (11) 0.0552 (14) 0.0382 (11) 0.0036 (11) 0.0025 (9) 0.0043 (11)
F5 0.097 (4) 0.089 (4) 0.073 (4) 0.056 (3) 0.034 (3) 0.036 (3)
F4 0.106 (4) 0.089 (4) 0.068 (3) 0.036 (4) 0.045 (3) 0.034 (3)
O8 0.047 (3) 0.057 (3) 0.049 (3) 0.013 (3) 0.011 (2) 0.018 (3)
O4 0.057 (3) 0.076 (4) 0.060 (4) 0.029 (3) 0.018 (3) 0.012 (3)
C27A 0.058 (6) 0.046 (5) 0.048 (5) 0.016 (5) 0.011 (5) 0.011 (4)
F6A 0.054 (4) 0.091 (5) 0.062 (4) −0.010 (3) −0.012 (3) −0.011 (4)
O3A 0.058 (4) 0.087 (6) 0.060 (4) −0.028 (4) 0.007 (4) −0.027 (4)
S2B 0.047 (6) 0.034 (5) 0.049 (6) −0.001 (5) 0.009 (5) 0.000 (5)
O3B 0.11 (3) 0.11 (3) 0.10 (2) −0.006 (18) 0.014 (18) 0.021 (18)
C27B 0.044 (14) 0.043 (14) 0.041 (14) −0.002 (10) 0.007 (10) 0.000 (9)
F6B 0.18 (3) 0.15 (3) 0.17 (3) 0.00 (2) 0.02 (2) 0.009 (19)
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Geometric parameters (Å, º)

Ru1—N3 2.030 (6) C13—C14 1.374 (11)
Ru1—N1 2.047 (6) C13—H13 0.9500
Ru1—N4 2.050 (6) C14—C15 1.392 (10)
Ru1—N2 2.069 (5) C14—H14 0.9500
Ru1—N5 2.087 (5) C15—C16 1.467 (10)
Ru1—O2 2.145 (5) C16—C17 1.392 (10)
O1—C26 1.234 (8) C17—C18 1.374 (12)
O2—H2A 0.8881 C17—H17 0.9500
O2—H2B 0.8881 C18—C19 1.383 (12)
N1—C1 1.351 (9) C18—H18 0.9500
N1—C5 1.367 (9) C19—C20 1.372 (11)
N2—C10 1.347 (8) C19—H19 0.9500
N2—C6 1.358 (9) C20—H20 0.9500
N3—C15 1.359 (9) C21—C22 1.381 (10)
N3—C11 1.364 (9) C21—H21 0.9500
N4—C20 1.346 (9) C22—C23 1.375 (9)
N4—C16 1.363 (9) C22—H22 0.9500
N5—C21 1.351 (9) C23—C24 1.392 (10)
N5—C25 1.351 (8) C23—C26 1.511 (10)
N6—C26 1.317 (9) C24—C25 1.393 (10)
N6—H6A 0.8799 C24—H24 0.9500
N6—H6B 0.8799 C25—H25 0.9500
C1—C2 1.382 (11) S1—O7 1.438 (6)
C1—H1 0.9500 S1—O6 1.441 (6)
C2—C3 1.377 (12) S1—O5 1.462 (6)
C2—H2 0.9500 S1—C53 1.773 (9)
C3—C4 1.363 (11) F1—C53 1.361 (10)
C3—H3 0.9500 F2—C53 1.387 (11)
C4—C5 1.392 (10) F3—C53 1.329 (11)
C4—H4 0.9500 S2A—O4 1.428 (6)
C5—C6 1.461 (10) S2A—O8 1.457 (6)
C6—C7 1.389 (10) S2A—O3A 1.474 (8)
C7—C8 1.365 (11) S2A—C27A 1.810 (10)
C7—H7 0.9500 F5—C27A 1.308 (10)
C8—C9 1.383 (11) F5—C27B 1.60 (5)
C8—H8 0.9500 F4—C27A 1.349 (11)
C9—C10 1.379 (10) F4—C27B 1.59 (5)
C9—H9 0.9500 O8—S2B 1.438 (14)
C10—H10 0.9500 O4—S2B 1.423 (14)
C11—C12 1.368 (10) C27A—F6A 1.345 (12)
C11—H11 0.9500 S2B—O3B 1.27 (7)
C12—C13 1.376 (12) S2B—C27B 1.71 (2)
C12—H12 0.9500 C27B—F6B 1.03 (8)
N3—Ru1—N1 91.1 (2) C13—C14—C15 119.7 (7)
N3—Ru1—N4 79.4 (2) C13—C14—H14 120.1
N1—Ru1—N4 99.3 (2) C15—C14—H14 120.1
N3—Ru1—N2 96.3 (2) N3—C15—C14 121.3 (7)
N1—Ru1—N2 78.6 (2) N3—C15—C16 115.3 (6)
N4—Ru1—N2 175.2 (2) C14—C15—C16 123.4 (7)
N3—Ru1—N5 90.7 (2) N4—C16—C17 121.3 (7)
N1—Ru1—N5 173.9 (2) N4—C16—C15 114.1 (6)
N4—Ru1—N5 86.8 (2) C17—C16—C15 124.6 (7)
N2—Ru1—N5 95.4 (2) C18—C17—C16 119.4 (8)
N3—Ru1—O2 171.7 (2) C18—C17—H17 120.3
N1—Ru1—O2 86.9 (2) C16—C17—H17 120.3
N4—Ru1—O2 93.0 (2) C17—C18—C19 119.1 (7)
N2—Ru1—O2 91.2 (2) C17—C18—H18 120.4
N5—Ru1—O2 92.1 (2) C19—C18—H18 120.4
Ru1—O2—H2A 111.0 C20—C19—C18 119.4 (8)
Ru1—O2—H2B 110.2 C20—C19—H19 120.3
H2A—O2—H2B 103.7 C18—C19—H19 120.3
C1—N1—C5 117.4 (6) N4—C20—C19 122.4 (7)
C1—N1—Ru1 126.4 (5) N4—C20—H20 118.8
C5—N1—Ru1 116.1 (4) C19—C20—H20 118.8
C10—N2—C6 118.0 (6) N5—C21—C22 123.8 (7)
C10—N2—Ru1 126.8 (5) N5—C21—H21 118.1
C6—N2—Ru1 114.8 (4) C22—C21—H21 118.1
C15—N3—C11 117.9 (6) C23—C22—C21 119.0 (7)
C15—N3—Ru1 115.6 (5) C23—C22—H22 120.5
C11—N3—Ru1 126.4 (5) C21—C22—H22 120.5
C20—N4—C16 118.4 (6) C22—C23—C24 118.4 (6)
C20—N4—Ru1 126.0 (5) C22—C23—C26 123.3 (7)
C16—N4—Ru1 115.5 (5) C24—C23—C26 118.2 (6)
C21—N5—C25 117.0 (6) C23—C24—C25 119.5 (6)
C21—N5—Ru1 120.6 (5) C23—C24—H24 120.2
C25—N5—Ru1 122.4 (5) C25—C24—H24 120.2
C26—N6—H6A 120.8 N5—C25—C24 122.2 (6)
C26—N6—H6B 119.1 N5—C25—H25 118.9
H6A—N6—H6B 120.0 C24—C25—H25 118.9
N1—C1—C2 122.3 (7) O1—C26—N6 123.9 (7)
N1—C1—H1 118.8 O1—C26—C23 118.2 (6)
C2—C1—H1 118.8 N6—C26—C23 117.9 (6)
C3—C2—C1 119.8 (7) O7—S1—O6 116.1 (4)
C3—C2—H2 120.1 O7—S1—O5 115.0 (4)
C1—C2—H2 120.1 O6—S1—O5 114.1 (4)
C4—C3—C2 119.0 (7) O7—S1—C53 101.3 (4)
C4—C3—H3 120.5 O6—S1—C53 104.3 (4)
C2—C3—H3 120.5 O5—S1—C53 103.7 (4)
C3—C4—C5 119.6 (7) F3—C53—F1 108.2 (7)
C3—C4—H4 120.2 F3—C53—F2 107.7 (7)
C5—C4—H4 120.2 F1—C53—F2 102.0 (8)
N1—C5—C4 121.9 (7) F3—C53—S1 114.3 (8)
N1—C5—C6 114.3 (6) F1—C53—S1 112.5 (6)
C4—C5—C6 123.8 (7) F2—C53—S1 111.4 (6)
N2—C6—C7 121.0 (7) O4—S2A—O8 114.5 (4)
N2—C6—C5 115.2 (6) O4—S2A—O3A 117.3 (4)
C7—C6—C5 123.7 (7) O8—S2A—O3A 114.1 (4)
C8—C7—C6 120.6 (7) O4—S2A—C27A 103.5 (4)
C8—C7—H7 119.7 O8—S2A—C27A 104.0 (4)
C6—C7—H7 119.7 O3A—S2A—C27A 100.7 (5)
C7—C8—C9 118.3 (7) F5—C27A—F6A 109.1 (9)
C7—C8—H8 120.9 F5—C27A—F4 107.1 (7)
C9—C8—H8 120.9 F6A—C27A—F4 108.9 (8)
C10—C9—C8 119.4 (7) F5—C27A—S2A 112.7 (7)
C10—C9—H9 120.3 F6A—C27A—S2A 109.6 (6)
C8—C9—H9 120.3 F4—C27A—S2A 109.4 (7)
N2—C10—C9 122.5 (7) O3B—S2B—O4 113 (3)
N2—C10—H10 118.7 O3B—S2B—O8 118 (3)
C9—C10—H10 118.7 O4—S2B—O8 116.0 (11)
N3—C11—C12 122.3 (7) O3B—S2B—C27B 108 (4)
N3—C11—H11 118.8 O4—S2B—C27B 96.7 (19)
C12—C11—H11 118.8 O8—S2B—C27B 101.7 (19)
C11—C12—C13 119.7 (8) F6B—C27B—F5 91 (6)
C11—C12—H12 120.1 F6B—C27B—F4 129 (5)
C13—C12—H12 120.1 F5—C27B—F4 84 (3)
C14—C13—C12 119.0 (7) F6B—C27B—S2B 129 (6)
C14—C13—H13 120.5 F5—C27B—S2B 104 (2)
C12—C13—H13 120.5 F4—C27B—S2B 101 (2)
C5—N1—C1—C2 0.3 (11) C16—C17—C18—C19 1.1 (12)
Ru1—N1—C1—C2 176.9 (6) C17—C18—C19—C20 −0.8 (13)
N1—C1—C2—C3 1.2 (12) C16—N4—C20—C19 0.6 (11)
C1—C2—C3—C4 −1.4 (13) Ru1—N4—C20—C19 −175.8 (6)
C2—C3—C4—C5 0.1 (12) C18—C19—C20—N4 −0.1 (13)
C1—N1—C5—C4 −1.6 (10) C25—N5—C21—C22 −2.1 (10)
Ru1—N1—C5—C4 −178.5 (6) Ru1—N5—C21—C22 176.5 (5)
C1—N1—C5—C6 176.3 (6) N5—C21—C22—C23 1.4 (11)
Ru1—N1—C5—C6 −0.6 (8) C21—C22—C23—C24 −0.1 (10)
C3—C4—C5—N1 1.4 (12) C21—C22—C23—C26 −178.0 (6)
C3—C4—C5—C6 −176.3 (7) C22—C23—C24—C25 −0.4 (10)
C10—N2—C6—C7 3.3 (10) C26—C23—C24—C25 177.6 (6)
Ru1—N2—C6—C7 −170.7 (6) C21—N5—C25—C24 1.5 (10)
C10—N2—C6—C5 −175.3 (6) Ru1—N5—C25—C24 −177.0 (5)
Ru1—N2—C6—C5 10.7 (8) C23—C24—C25—N5 −0.3 (10)
N1—C5—C6—N2 −6.7 (9) C22—C23—C26—O1 157.0 (7)
C4—C5—C6—N2 171.2 (7) C24—C23—C26—O1 −20.9 (10)
N1—C5—C6—C7 174.8 (7) C22—C23—C26—N6 −22.0 (10)
C4—C5—C6—C7 −7.4 (11) C24—C23—C26—N6 160.1 (7)
N2—C6—C7—C8 −1.1 (12) O7—S1—C53—F3 −64.7 (7)
C5—C6—C7—C8 177.4 (7) O6—S1—C53—F3 56.1 (7)
C6—C7—C8—C9 −1.5 (12) O5—S1—C53—F3 175.8 (6)
C7—C8—C9—C10 1.7 (12) O7—S1—C53—F1 59.1 (8)
C6—N2—C10—C9 −3.1 (10) O6—S1—C53—F1 179.9 (7)
Ru1—N2—C10—C9 170.1 (5) O5—S1—C53—F1 −60.4 (8)
C8—C9—C10—N2 0.6 (12) O7—S1—C53—F2 172.9 (6)
C15—N3—C11—C12 −0.1 (10) O6—S1—C53—F2 −66.3 (8)
Ru1—N3—C11—C12 −176.3 (5) O5—S1—C53—F2 53.4 (7)
N3—C11—C12—C13 −0.1 (11) O4—S2A—C27A—F5 −174.7 (7)
C11—C12—C13—C14 0.2 (11) O8—S2A—C27A—F5 65.3 (8)
C12—C13—C14—C15 −0.1 (11) O3A—S2A—C27A—F5 −53.0 (8)
C11—N3—C15—C14 0.2 (9) O4—S2A—C27A—F6A 63.6 (7)
Ru1—N3—C15—C14 176.8 (5) O8—S2A—C27A—F6A −56.3 (7)
C11—N3—C15—C16 −177.9 (6) O3A—S2A—C27A—F6A −174.7 (6)
Ru1—N3—C15—C16 −1.3 (7) O4—S2A—C27A—F4 −55.7 (8)
C13—C14—C15—N3 −0.1 (10) O8—S2A—C27A—F4 −175.7 (6)
C13—C14—C15—C16 177.8 (6) O3A—S2A—C27A—F4 66.0 (7)
C20—N4—C16—C17 −0.3 (10) O3B—S2B—C27B—F6B 150 (9)
Ru1—N4—C16—C17 176.5 (5) O4—S2B—C27B—F6B −93 (9)
C20—N4—C16—C15 179.6 (6) O8—S2B—C27B—F6B 25 (9)
Ru1—N4—C16—C15 −3.5 (7) O3B—S2B—C27B—F5 47 (4)
N3—C15—C16—N4 3.2 (8) O4—S2B—C27B—F5 164 (2)
C14—C15—C16—N4 −174.9 (6) O8—S2B—C27B—F5 −78 (3)
N3—C15—C16—C17 −176.9 (6) O3B—S2B—C27B—F4 −39 (4)
C14—C15—C16—C17 5.1 (11) O4—S2B—C27B—F4 77 (3)
N4—C16—C17—C18 −0.5 (11) O8—S2B—C27B—F4 −164 (2)
C15—C16—C17—C18 179.5 (7)
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Aquabis(2,2'-bipyridine-κ2N,N')(isonicotinamide-κN)ruthenium(II) bis(trifluoromethanesulfonate) . Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O2—H2A···O1i 0.89 1.73 2.617 (7) 174
O2—H2B···O5 0.89 1.90 2.775 (8) 169
N6—H6A···O6i 0.88 2.32 3.190 (9) 169
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Symmetry code: (i) −x+1, −y, −z+1.

Funding Statement

Funding for this research was provided by: National Science Foundation (award No. 1920059); Welch Foundation (award No. BN0032); University of the Incarnate Word Facuty Endowed Research Award; Constance and Miriam Jauchler Jones Endowed Chair.

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624001147/bt4147sup1.cif

x-09-x240114-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624001147/bt4147Isup2.hkl

x-09-x240114-Isup2.hkl (459.5KB, hkl)
x-09-x240114-Isup4.mol (4KB, mol)

Supporting information file. DOI: 10.1107/S2414314624001147/bt4147Isup4.mol

CCDC reference: 2330544

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

Articles from IUCrData are provided here courtesy of International Union of Crystallography

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