metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

(2,2-Bi­pyridine-κ2N,N′)chlorido­[η6-1-methyl-4-(propan-2-yl)benzene]­ruthenium(II) tetra­phenyl­borate

aUniversity of Arkansas, Fayetteville, AR 72701, USA
*Correspondence e-mail: kilyanek@uark.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 1 July 2019; accepted 13 July 2019; online 19 July 2019)

The title complex, [RuCl(C10H14)(C10H8N2)](C24H20B), has monoclinic (P21) symmetry at 100 K. It was prepared by the reaction of the di­chlor­ido[1-methyl-4-(propan-2-yl)benzene]­ruthenium(II) dimer with 2,2′-bi­pyridine, followed by the addition of ammonium tetra­phenyl­borate. The 1-methyl-4-(propan-2-yl)benzene group, the 2,2′-bi­pyridine unit and a chloride ion coordinate the ruthenium(II) atom, with the 1-methyl-4-(propan-2-yl)benzene ring and bi­pyridine moieties trans to each other. In the crystal, the complex cations are linked by C—H⋯Cl hydrogen bonds, forming chains parallel to [010]. These chains are linked by a number of C—H⋯π inter­actions, involving the phenyl rings of the tetra­phenyl­borate anion and a pyridine ring of the bpy ligand, resulting in the formation of layers parallel to (10[\overline{1}]).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

N-Heterocyclic carbenes (NHCs) of ruthenium have been of significant inter­est to the organometallic community for many years, and have a number of applications in homogeneous chemical catalysis (Weskamp et al., 1999[Weskamp, T., Kohl, F. J. & Herrmann, W. A. (1999). J. Organomet. Chem. 582, 362-365.]; Fürstner et al., 2001[Fürstner, A., Ackermann, L., Gabor, B., Goddard, R., Lehmann, C. W., Mynott, R., Stelzer, F. & Thiel, O. R. (2001). Chem. Eur. J. 7, 3236-3253.]; Son et al., 2004[Son, S. U., Park, K. H., Lee, Y.-S., Kim, B. Y., Choi, C. H., Lah, M. S., Jang, Y. H., Jang, D.-J. & Chung, Y. K. (2004). Inorg. Chem. 43, 6896-6898.]; Tudose et al., 2006[Tudose, A., Demonceau, A. & Delaude, L. (2006). J. Organomet. Chem. 691, 5356-5365.]; Gandolfi et al., 2009[Gandolfi, C., Heckenroth, M., Neels, A., Laurenczy, G. & Albrecht, M. (2009). Organometallics, 28, 5112-5121.]); Sanz et al., 2010[Sanz, S., Azua, A. & Peris, E. (2010). Dalton Trans. 39, 6339-6343.]; Fogler et al., 2011[Fogler, E., Balaraman, E., Ben-David, Y., Leitus, G., Shimon, L. J. W. & Milstein, D. (2011). Organometallics, 30, 3826-3833.]; Hackenberg et al., 2013[Hackenberg, F., Müller-Bunz, H., Smith, R., Streciwilk, W., Zhu, X. & Tacke, M. (2013). Organometallics, 32, 5551-5560.]). The catalytic properties of these complexes have also been studied intensively (Fogler et al., 2011[Fogler, E., Balaraman, E., Ben-David, Y., Leitus, G., Shimon, L. J. W. & Milstein, D. (2011). Organometallics, 30, 3826-3833.]; Ortega et al., 2013[Ortega, N., Tang, D. D., Urban, S., Zhao, D. & Glorius, F. (2013). Angew. Chem. Int. Ed. 52, 9500-9503.]; Day & Fogg, 2018[Day, C. S. & Fogg, D. E. (2018). Organometallics, 37, 4551-4555.]). In an effort to access alternative synthetic starting materials for the synthesis of bi­pyridine-substituted complexes of ruthenium that include NHCs, the title complex was synthesized.

Complex 1 is comprised of an RuII metal atom coordinated by an η6 1-methyl-4-(propan-2-yl)benzene (p-cymene) ring, a chloride ion and the bidentate ligand 2,2′-bi­pyridine, with a tetra­phenyl­borate anion as counter ion (Fig. 1[link]). The 1-methyl-4-(propan-2-yl)benzene ring and bi­pyridine moieties are trans to each other. The complex crystallizes in the chiral monoclinic P21 space group with a refined absolute structure Flack parameter of −0.014 (7). The most significant bond lengths and bond angles involving atom Ru1 are given in Table 1[link].

Table 1
Selected geometric parameters (Å, °)

Ru1—Cl1 2.3851 (5) Ru1—C3 2.2123 (16)
Ru1—N1 2.0892 (13) Ru1—C4 2.2391 (16)
Ru1—N2 2.0839 (13) Ru1—C5 2.2005 (16)
Ru1—C1 2.2234 (16) Ru1—C6 2.1626 (16)
Ru1—C2 2.1863 (18)    
       
N2—Ru1—N1 76.98 (5) C4—Ru1—Cl1 87.95 (5)
[Figure 1]
Figure 1
The mol­ecular structure of complex 1, with the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, the complex cations are linked by bifurcated C—(H,H)⋯Cl hydrogen bonds, forming chains propagating parallel to [010]; see Fig. 2[link] and Table 2[link]. The chains are linked by a number of C—H⋯π inter­actions involving the phenyl rings of the tetra­phenyl­borate anion and a pyridine ring of the bpy ligand, resulting in the formation of layers lying parallel to the (10[\overline{1}]) plane; see Fig. 2[link] and Table 2[link].

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C19A–C24A and N2/C16–C20, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯Cl1i 1.00 2.66 3.421 (2) 133
C11—H11⋯Cl1i 0.95 2.62 3.484 (2) 151
C7—H7⋯Cg1ii 1.00 2.67 3.616 (2) 158
C9—H9BCg2iii 0.98 2.91 3.733 (2) 143
C18—H18⋯Cg1 0.95 2.73 3.431 (2) 131
C23A—H23ACg2iv 0.95 2.60 3.461 (2) 151
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) x, y-1, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+1].
[Figure 2]
Figure 2
A view normal to plane (10[\overline{1}]) of the crystal packing of complex 1. The C—H⋯Cl hydrogen bonds and C—H⋯π inter­actions (see Table 2[link]) are shown as dashed lines. For clarity, only the hydrogen atoms involved in these inter­actions have been included.

Synthesis and crystallization

All chemicals were purchased from Sigma–Aldrich and used without further purification under a nitro­gen atmosphere. The di­chlorido­(p-cymene)ruthenium(II) dimer was prepared following the literature protocol of Bennett et al. (2007[Bennett, M. A., Huang, T.-N., Matheson, T. W., Smith, A. K., Ittel, S. & Nickerson, W. (2007). Inorg. Synth. 21, 74-78.]). The reaction scheme is shown in Fig. 3[link]. [Ru(p-cymene)Cl2]2 (100 mg, 163.29 mmol) and 2,2′-bi­pyridine (28 mg, 179.28 mmol) in 5 ml of methanol were refluxed for 16 h. The reaction mixture was cooled to room temperature and then filtered through celite. Ammonium tetra­phenyl­borate (29 mg, 86 mmol) dissolved in 3 ml of MeOH was added to the filtrate. Precipitation proceeded over the next 60 min, at which point a solid yellow product was collected by filtration (110 mg, 147 mmol, 90%). Crystals suitable for X-ray crystallography were grown in CH2Cl2/pentane by slow vapor diffusion. HR FT–ICR MS: Calc. for C20H22ClN2Ru (427.0542); Found m/z (M-BPh4) 427.0515.

[Figure 3]
Figure 3
Synthesis scheme of complex 1

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link].

Table 3
Experimental details

Crystal data
Chemical formula [RuCl(C10H14)(C10H8N2)](C24H20B)
Mr 746.12
Crystal system, space group Monoclinic, P21
Temperature (K) 100
a, b, c (Å) 14.1396 (15), 9.4811 (11), 14.3009 (15)
β (°) 109.013 (4)
V3) 1812.6 (3)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.54
Crystal size (mm) 0.27 × 0.15 × 0.10
 
Data collection
Diffractometer Bruker Photon II cpad
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.391, 0.439
No. of measured, independent and observed [I > 2σ(I)] reflections 57149, 18389, 17627
Rint 0.040
(sin θ/λ)max−1) 0.848
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.062, 1.01
No. of reflections 18389
No. of parameters 446
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.43, −0.60
Absolute structure Flack x determined using 7947 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.014 (7)
Computer programs: APEX3 and SAINT (Bruker, 2018[Bruker (2018). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), SHELXL2018 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(2,2-Bipyridine-κ2N,N')chlorido[η6-1-methyl-4-(propan-2-yl)benzene]ruthenium(II) tetraphenylborate top
Crystal data top
[RuCl(C10H14)(C10H8N2)](C24H20B)F(000) = 772
Mr = 746.12Dx = 1.367 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 14.1396 (15) ÅCell parameters from 9150 reflections
b = 9.4811 (11) Åθ = 4.3–37.1°
c = 14.3009 (15) ŵ = 0.54 mm1
β = 109.013 (4)°T = 100 K
V = 1812.6 (3) Å3Block, orange
Z = 20.27 × 0.15 × 0.10 mm
Data collection top
Bruker Photon II cpad
diffractometer
17627 reflections with I > 2σ(I)
φ and ω scansRint = 0.040
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 37.1°, θmin = 2.5°
Tmin = 0.391, Tmax = 0.439h = 2323
57149 measured reflectionsk = 1616
18389 independent reflectionsl = 2424
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.028P)2 + 0.240P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.062(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.43 e Å3
18389 reflectionsΔρmin = 0.60 e Å3
446 parametersExtinction correction: (SHELXL2018; Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0054 (9)
Primary atom site location: dualAbsolute structure: Flack x determined using 7947 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.014 (7)
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.

Refinement. Hydrogen atoms were included in calculated positions and treated as riding on the parent C atom: C—H = 0.95–1.00 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru10.18068 (2)0.51286 (2)0.07448 (2)0.01075 (3)
Cl10.12759 (4)0.74527 (5)0.01726 (4)0.01957 (8)
N10.09601 (10)0.54459 (14)0.16818 (10)0.0145 (2)
N20.27945 (9)0.61963 (14)0.19404 (10)0.0126 (2)
C10.22538 (12)0.28724 (16)0.09615 (11)0.0146 (2)
C20.12355 (14)0.29922 (19)0.03465 (13)0.0150 (3)
H20.0700930.2633510.0601730.018*
C30.09526 (13)0.38097 (18)0.05258 (11)0.0166 (3)
H30.0227710.4016130.0864610.020*
C40.16818 (13)0.45675 (19)0.08118 (12)0.0182 (3)
C50.26946 (13)0.45044 (19)0.01971 (12)0.0181 (3)
H50.3190340.5180720.0307870.022*
C60.29636 (12)0.36769 (18)0.06801 (12)0.0160 (3)
H60.3649840.3792520.1168690.019*
C70.25764 (13)0.19334 (18)0.18562 (12)0.0179 (3)
H70.3211250.2326420.2323250.022*
C80.18197 (17)0.1836 (3)0.24075 (17)0.0333 (5)
H8A0.1693700.2780720.2619170.050*
H8B0.2086240.1228860.2988700.050*
H8C0.1192770.1436650.1968980.050*
C90.2809 (2)0.0474 (2)0.15284 (17)0.0327 (5)
H9A0.2191800.0044660.1094250.049*
H9B0.3094890.0124670.2111080.049*
H9C0.3290400.0567810.1170020.049*
C100.13714 (16)0.5463 (2)0.17228 (13)0.0259 (4)
H10A0.1377200.4894750.2293290.039*
H10B0.1838400.6253320.1639620.039*
H10C0.0695330.5827600.1832120.039*
C110.00049 (11)0.5078 (3)0.14594 (12)0.0215 (3)
H110.0327890.4616930.0848670.026*
C120.05456 (14)0.5350 (2)0.20943 (15)0.0283 (5)
H120.1227920.5078080.1918930.034*
C130.00786 (15)0.6023 (3)0.29879 (16)0.0278 (4)
H130.0434490.6209280.3434920.033*
C140.09145 (13)0.6420 (2)0.32182 (13)0.0206 (3)
H140.1249270.6884740.3824390.025*
C150.14161 (11)0.61250 (17)0.25445 (11)0.0145 (2)
C160.24499 (11)0.65497 (16)0.26890 (11)0.0128 (2)
C170.30385 (12)0.72922 (17)0.35107 (12)0.0163 (3)
H170.2788600.7519980.4033530.020*
C180.39957 (12)0.76962 (17)0.35571 (13)0.0182 (3)
H180.4410310.8200140.4114250.022*
C190.43407 (12)0.73577 (18)0.27837 (13)0.0186 (3)
H190.4990690.7635430.2797540.022*
C200.37197 (11)0.66058 (17)0.19884 (12)0.0161 (3)
H200.3956440.6371280.1457880.019*
C1A0.23530 (11)0.77267 (17)0.60471 (11)0.0132 (2)
C2A0.23565 (12)0.88711 (16)0.54243 (11)0.0152 (2)
H2A0.2980560.9206290.5398200.018*
C3A0.14809 (14)0.95384 (18)0.48412 (13)0.0196 (3)
H3A0.1520341.0300550.4424260.023*
C4A0.05535 (14)0.9094 (2)0.48677 (13)0.0217 (3)
H4A0.0042690.9548850.4476500.026*
C5A0.05165 (13)0.7970 (2)0.54779 (13)0.0217 (3)
H5A0.0109930.7653670.5509260.026*
C6A0.13943 (12)0.73070 (19)0.60434 (12)0.0181 (3)
H6A0.1345810.6533070.6447250.022*
C7A0.36590 (11)0.75614 (16)0.78984 (11)0.0129 (2)
C8A0.30762 (13)0.8527 (2)0.82111 (12)0.0197 (3)
H8AA0.2471850.8856980.7744080.024*
C9A0.33465 (16)0.9025 (2)0.91823 (14)0.0268 (4)
H9AA0.2931760.9689140.9359990.032*
C10A0.42176 (14)0.8554 (2)0.98886 (13)0.0228 (3)
H10D0.4397000.8874901.0553000.027*
C11A0.48227 (13)0.7604 (2)0.96048 (12)0.0202 (3)
H11A0.5422830.7271211.0077010.024*
C12A0.45494 (12)0.71423 (19)0.86297 (12)0.0173 (3)
H12A0.4984210.6514430.8449190.021*
C13A0.31168 (10)0.5213 (2)0.67714 (9)0.0126 (2)
C14A0.34015 (13)0.43489 (17)0.76138 (12)0.0161 (3)
H14A0.3765680.4758690.8232690.019*
C15A0.31722 (14)0.29086 (19)0.75824 (14)0.0202 (3)
H15A0.3375520.2368450.8174200.024*
C16A0.26504 (14)0.22670 (18)0.66926 (14)0.0212 (3)
H16A0.2492870.1290600.6666350.025*
C17A0.23636 (14)0.3084 (2)0.58416 (14)0.0206 (3)
H17A0.2006000.2663220.5224610.025*
C18A0.25953 (13)0.45161 (18)0.58838 (12)0.0177 (3)
H18A0.2392470.5045470.5287340.021*
C19A0.43290 (11)0.71807 (15)0.63904 (11)0.0122 (2)
C20A0.47654 (11)0.61317 (16)0.59733 (11)0.0140 (2)
H20A0.4494220.5205950.5904720.017*
C21A0.55858 (12)0.63956 (18)0.56539 (12)0.0156 (2)
H21A0.5866100.5651950.5384210.019*
C22A0.59897 (12)0.77414 (18)0.57306 (11)0.0161 (3)
H22A0.6537250.7930640.5502480.019*
C23A0.55809 (12)0.88118 (17)0.61471 (12)0.0158 (3)
H23A0.5849160.9738560.6203060.019*
C24A0.47790 (12)0.85237 (16)0.64813 (12)0.0146 (2)
H24A0.4525540.9260730.6782240.018*
B1A0.33633 (12)0.69173 (18)0.67724 (12)0.0124 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01025 (4)0.01104 (4)0.01128 (4)0.00032 (4)0.00393 (3)0.00047 (4)
Cl10.01740 (17)0.01448 (16)0.02383 (19)0.00399 (13)0.00261 (14)0.00439 (14)
N10.0140 (5)0.0145 (5)0.0164 (5)0.0034 (4)0.0068 (4)0.0035 (4)
N20.0110 (5)0.0118 (5)0.0148 (5)0.0004 (4)0.0038 (4)0.0013 (4)
C10.0170 (6)0.0115 (5)0.0142 (6)0.0018 (5)0.0038 (5)0.0009 (4)
C20.0173 (7)0.0132 (6)0.0130 (6)0.0003 (5)0.0028 (5)0.0014 (5)
C30.0181 (6)0.0178 (6)0.0124 (6)0.0009 (5)0.0030 (5)0.0014 (5)
C40.0217 (7)0.0216 (7)0.0125 (6)0.0042 (6)0.0074 (5)0.0011 (5)
C50.0191 (7)0.0217 (7)0.0166 (6)0.0028 (5)0.0099 (6)0.0014 (5)
C60.0154 (6)0.0169 (6)0.0162 (6)0.0035 (5)0.0057 (5)0.0009 (5)
C70.0206 (7)0.0150 (6)0.0147 (6)0.0003 (5)0.0010 (5)0.0018 (5)
C80.0301 (10)0.0434 (13)0.0271 (9)0.0023 (9)0.0103 (8)0.0167 (9)
C90.0478 (13)0.0140 (7)0.0293 (9)0.0052 (7)0.0030 (9)0.0013 (6)
C100.0283 (8)0.0346 (10)0.0167 (7)0.0058 (7)0.0102 (6)0.0087 (6)
C110.0166 (5)0.0260 (7)0.0241 (6)0.0095 (8)0.0097 (5)0.0094 (9)
C120.0196 (7)0.0391 (14)0.0321 (8)0.0112 (7)0.0167 (7)0.0118 (8)
C130.0237 (8)0.0388 (11)0.0277 (9)0.0077 (8)0.0178 (7)0.0091 (8)
C140.0210 (7)0.0255 (8)0.0186 (7)0.0030 (6)0.0109 (6)0.0058 (6)
C150.0141 (6)0.0152 (6)0.0149 (6)0.0020 (5)0.0058 (5)0.0028 (5)
C160.0127 (5)0.0110 (5)0.0140 (5)0.0001 (4)0.0036 (5)0.0000 (4)
C170.0174 (6)0.0135 (6)0.0156 (6)0.0001 (5)0.0019 (5)0.0016 (5)
C180.0158 (6)0.0135 (6)0.0199 (7)0.0013 (5)0.0015 (5)0.0008 (5)
C190.0129 (6)0.0165 (6)0.0233 (7)0.0027 (5)0.0018 (5)0.0024 (5)
C200.0115 (6)0.0163 (6)0.0206 (7)0.0011 (5)0.0053 (5)0.0018 (5)
C1A0.0143 (6)0.0127 (6)0.0125 (5)0.0005 (5)0.0043 (5)0.0012 (4)
C2A0.0180 (6)0.0122 (6)0.0148 (6)0.0001 (5)0.0047 (5)0.0008 (4)
C3A0.0240 (7)0.0140 (7)0.0179 (7)0.0032 (5)0.0032 (6)0.0009 (5)
C4A0.0194 (7)0.0208 (7)0.0208 (7)0.0063 (6)0.0009 (6)0.0001 (6)
C5A0.0140 (6)0.0276 (8)0.0221 (7)0.0028 (6)0.0040 (6)0.0014 (6)
C6A0.0139 (6)0.0224 (7)0.0177 (6)0.0010 (5)0.0046 (5)0.0043 (5)
C7A0.0127 (6)0.0132 (6)0.0133 (5)0.0013 (4)0.0049 (5)0.0014 (4)
C8A0.0189 (7)0.0225 (7)0.0160 (6)0.0040 (6)0.0034 (5)0.0057 (5)
C9A0.0266 (8)0.0325 (10)0.0205 (8)0.0056 (7)0.0067 (7)0.0106 (7)
C10A0.0239 (8)0.0290 (9)0.0146 (6)0.0043 (7)0.0052 (6)0.0060 (6)
C11A0.0166 (6)0.0271 (8)0.0146 (6)0.0033 (6)0.0021 (5)0.0016 (5)
C12A0.0139 (6)0.0212 (7)0.0156 (6)0.0003 (5)0.0032 (5)0.0017 (5)
C13A0.0123 (4)0.0129 (5)0.0139 (4)0.0005 (6)0.0059 (4)0.0006 (6)
C14A0.0193 (6)0.0147 (6)0.0147 (6)0.0003 (5)0.0064 (5)0.0000 (5)
C15A0.0251 (8)0.0154 (6)0.0218 (7)0.0001 (6)0.0100 (6)0.0023 (5)
C16A0.0237 (8)0.0148 (6)0.0285 (8)0.0044 (6)0.0130 (7)0.0023 (6)
C17A0.0200 (7)0.0184 (7)0.0235 (7)0.0057 (6)0.0071 (6)0.0061 (6)
C18A0.0186 (7)0.0169 (7)0.0165 (6)0.0038 (5)0.0041 (5)0.0015 (5)
C19A0.0120 (5)0.0117 (5)0.0125 (5)0.0003 (4)0.0035 (4)0.0004 (4)
C20A0.0151 (6)0.0117 (5)0.0156 (6)0.0002 (4)0.0056 (5)0.0005 (4)
C21A0.0144 (6)0.0167 (6)0.0170 (6)0.0003 (5)0.0069 (5)0.0019 (5)
C22A0.0130 (6)0.0203 (7)0.0156 (6)0.0015 (5)0.0054 (5)0.0016 (5)
C23A0.0147 (6)0.0143 (6)0.0173 (6)0.0035 (5)0.0035 (5)0.0012 (5)
C24A0.0142 (6)0.0125 (6)0.0171 (6)0.0012 (5)0.0050 (5)0.0015 (5)
B1A0.0125 (6)0.0128 (6)0.0116 (6)0.0009 (5)0.0036 (5)0.0010 (5)
Geometric parameters (Å, º) top
Ru1—Cl12.3851 (5)C19—C201.386 (2)
Ru1—N12.0892 (13)C19—H190.9500
Ru1—N22.0839 (13)C20—H200.9500
Ru1—C12.2234 (16)C1A—C2A1.405 (2)
Ru1—C22.1863 (18)C1A—C6A1.411 (2)
Ru1—C32.2123 (16)C1A—B1A1.655 (2)
Ru1—C42.2391 (16)C2A—C3A1.399 (2)
Ru1—C52.2005 (16)C2A—H2A0.9500
Ru1—C62.1626 (16)C3A—C4A1.390 (3)
N1—C111.3423 (19)C3A—H3A0.9500
N1—C151.354 (2)C4A—C5A1.389 (3)
N2—C201.345 (2)C4A—H4A0.9500
N2—C161.355 (2)C5A—C6A1.391 (2)
C1—C61.419 (2)C5A—H5A0.9500
C1—C21.426 (3)C6A—H6A0.9500
C1—C71.502 (2)C7A—C8A1.399 (2)
C2—C31.411 (2)C7A—C12A1.407 (2)
C2—H21.0000C7A—B1A1.644 (2)
C3—C41.422 (2)C8A—C9A1.397 (2)
C3—H31.0000C8A—H8AA0.9500
C4—C51.417 (2)C9A—C10A1.388 (3)
C4—C101.496 (2)C9A—H9AA0.9500
C5—C61.422 (2)C10A—C11A1.391 (3)
C5—H51.0000C10A—H10D0.9500
C6—H61.0000C11A—C12A1.391 (2)
C7—C81.525 (3)C11A—H11A0.9500
C7—C91.531 (3)C12A—H12A0.9500
C7—H71.0000C13A—C14A1.403 (2)
C8—H8A0.9800C13A—C18A1.408 (2)
C8—H8B0.9800C13A—B1A1.653 (3)
C8—H8C0.9800C14A—C15A1.401 (2)
C9—H9A0.9800C14A—H14A0.9500
C9—H9B0.9800C15A—C16A1.386 (3)
C9—H9C0.9800C15A—H15A0.9500
C10—H10A0.9800C16A—C17A1.387 (3)
C10—H10B0.9800C16A—H16A0.9500
C10—H10C0.9800C17A—C18A1.394 (3)
C11—C121.388 (2)C17A—H17A0.9500
C11—H110.9500C18A—H18A0.9500
C12—C131.388 (3)C19A—C20A1.402 (2)
C12—H120.9500C19A—C24A1.410 (2)
C13—C141.386 (3)C19A—B1A1.647 (2)
C13—H130.9500C20A—C21A1.401 (2)
C14—C151.398 (2)C20A—H20A0.9500
C14—H140.9500C21A—C22A1.388 (2)
C15—C161.465 (2)C21A—H21A0.9500
C16—C171.390 (2)C22A—C23A1.394 (2)
C17—C181.387 (2)C22A—H22A0.9500
C17—H170.9500C23A—C24A1.393 (2)
C18—C191.384 (3)C23A—H23A0.9500
C18—H180.9500C24A—H24A0.9500
N2—Ru1—N176.98 (5)C13—C12—C11119.30 (16)
N2—Ru1—C691.73 (6)C13—C12—H12120.3
N1—Ru1—C6135.94 (6)C11—C12—H12120.3
N2—Ru1—C2139.09 (6)C14—C13—C12119.00 (17)
N1—Ru1—C293.45 (6)C14—C13—H13120.5
C6—Ru1—C267.64 (7)C12—C13—H13120.5
N2—Ru1—C5105.63 (6)C13—C14—C15118.96 (16)
N1—Ru1—C5172.63 (6)C13—C14—H14120.5
C6—Ru1—C538.04 (6)C15—C14—H14120.5
C2—Ru1—C580.06 (7)N1—C15—C14121.67 (14)
N2—Ru1—C3171.53 (6)N1—C15—C16114.60 (13)
N1—Ru1—C3109.54 (6)C14—C15—C16123.70 (14)
C6—Ru1—C379.82 (6)N2—C16—C17121.53 (14)
C2—Ru1—C337.42 (6)N2—C16—C15114.82 (13)
C5—Ru1—C367.23 (7)C17—C16—C15123.62 (14)
N2—Ru1—C1105.60 (5)C18—C17—C16119.10 (15)
N1—Ru1—C1104.21 (6)C18—C17—H17120.5
C6—Ru1—C137.73 (6)C16—C17—H17120.5
C2—Ru1—C137.73 (7)C19—C18—C17119.35 (15)
C5—Ru1—C168.51 (6)C19—C18—H18120.3
C3—Ru1—C167.98 (6)C17—C18—H18120.3
N2—Ru1—C4138.24 (6)C18—C19—C20118.74 (15)
N1—Ru1—C4142.73 (6)C18—C19—H19120.6
C6—Ru1—C467.79 (6)C20—C19—H19120.6
C2—Ru1—C467.55 (7)N2—C20—C19122.40 (16)
C5—Ru1—C437.20 (6)N2—C20—H20118.8
C3—Ru1—C437.25 (6)C19—C20—H20118.8
C1—Ru1—C480.61 (6)C2A—C1A—C6A114.66 (14)
N2—Ru1—Cl183.37 (4)C2A—C1A—B1A125.09 (14)
N1—Ru1—Cl184.55 (4)C6A—C1A—B1A120.23 (14)
C6—Ru1—Cl1136.99 (5)C3A—C2A—C1A122.83 (16)
C2—Ru1—Cl1135.91 (4)C3A—C2A—H2A118.6
C5—Ru1—Cl1102.53 (5)C1A—C2A—H2A118.6
C3—Ru1—Cl1102.34 (5)C4A—C3A—C2A120.43 (16)
C1—Ru1—Cl1168.54 (4)C4A—C3A—H3A119.8
C4—Ru1—Cl187.95 (5)C2A—C3A—H3A119.8
C11—N1—C15119.01 (14)C5A—C4A—C3A118.61 (16)
C11—N1—Ru1124.14 (11)C5A—C4A—H4A120.7
C15—N1—Ru1116.78 (10)C3A—C4A—H4A120.7
C20—N2—C16118.85 (14)C4A—C5A—C6A120.18 (17)
C20—N2—Ru1124.25 (11)C4A—C5A—H5A119.9
C16—N2—Ru1116.82 (10)C6A—C5A—H5A119.9
C6—C1—C2116.57 (14)C5A—C6A—C1A123.28 (16)
C6—C1—C7120.89 (14)C5A—C6A—H6A118.4
C2—C1—C7122.53 (15)C1A—C6A—H6A118.4
C6—C1—Ru168.81 (9)C8A—C7A—C12A115.15 (14)
C2—C1—Ru169.72 (9)C8A—C7A—B1A124.60 (14)
C7—C1—Ru1133.03 (11)C12A—C7A—B1A120.25 (13)
C3—C2—C1121.83 (17)C9A—C8A—C7A122.68 (16)
C3—C2—Ru172.29 (10)C9A—C8A—H8AA118.7
C1—C2—Ru172.55 (9)C7A—C8A—H8AA118.7
C3—C2—H2118.6C10A—C9A—C8A120.37 (18)
C1—C2—H2118.6C10A—C9A—H9AA119.8
Ru1—C2—H2118.6C8A—C9A—H9AA119.8
C2—C3—C4120.56 (15)C9A—C10A—C11A118.70 (16)
C2—C3—Ru170.29 (9)C9A—C10A—H10D120.6
C4—C3—Ru172.40 (9)C11A—C10A—H10D120.6
C2—C3—H3119.1C10A—C11A—C12A120.01 (16)
C4—C3—H3119.1C10A—C11A—H11A120.0
Ru1—C3—H3119.1C12A—C11A—H11A120.0
C5—C4—C3118.77 (15)C11A—C12A—C7A123.05 (16)
C5—C4—C10120.99 (16)C11A—C12A—H12A118.5
C3—C4—C10120.19 (16)C7A—C12A—H12A118.5
C5—C4—Ru169.92 (9)C14A—C13A—C18A114.82 (17)
C3—C4—Ru170.35 (9)C14A—C13A—B1A124.65 (13)
C10—C4—Ru1129.54 (13)C18A—C13A—B1A120.52 (14)
C4—C5—C6119.77 (15)C15A—C14A—C13A122.89 (16)
C4—C5—Ru172.88 (9)C15A—C14A—H14A118.6
C6—C5—Ru169.54 (9)C13A—C14A—H14A118.6
C4—C5—H5119.6C16A—C15A—C14A120.36 (16)
C6—C5—H5119.6C16A—C15A—H15A119.8
Ru1—C5—H5119.6C14A—C15A—H15A119.8
C1—C6—C5122.41 (15)C15A—C16A—C17A118.46 (16)
C1—C6—Ru173.46 (9)C15A—C16A—H16A120.8
C5—C6—Ru172.43 (9)C17A—C16A—H16A120.8
C1—C6—H6118.4C16A—C17A—C18A120.57 (17)
C5—C6—H6118.4C16A—C17A—H17A119.7
Ru1—C6—H6118.4C18A—C17A—H17A119.7
C1—C7—C8113.99 (15)C17A—C18A—C13A122.89 (17)
C1—C7—C9108.11 (15)C17A—C18A—H18A118.6
C8—C7—C9111.16 (18)C13A—C18A—H18A118.6
C1—C7—H7107.8C20A—C19A—C24A115.58 (13)
C8—C7—H7107.8C20A—C19A—B1A124.13 (13)
C9—C7—H7107.8C24A—C19A—B1A120.29 (13)
C7—C8—H8A109.5C21A—C20A—C19A122.55 (14)
C7—C8—H8B109.5C21A—C20A—H20A118.7
H8A—C8—H8B109.5C19A—C20A—H20A118.7
C7—C8—H8C109.5C22A—C21A—C20A120.11 (15)
H8A—C8—H8C109.5C22A—C21A—H21A119.9
H8B—C8—H8C109.5C20A—C21A—H21A119.9
C7—C9—H9A109.5C21A—C22A—C23A119.07 (14)
C7—C9—H9B109.5C21A—C22A—H22A120.5
H9A—C9—H9B109.5C23A—C22A—H22A120.5
C7—C9—H9C109.5C24A—C23A—C22A120.06 (14)
H9A—C9—H9C109.5C24A—C23A—H23A120.0
H9B—C9—H9C109.5C22A—C23A—H23A120.0
C4—C10—H10A109.5C23A—C24A—C19A122.58 (14)
C4—C10—H10B109.5C23A—C24A—H24A118.7
H10A—C10—H10B109.5C19A—C24A—H24A118.7
C4—C10—H10C109.5C7A—B1A—C19A107.15 (12)
H10A—C10—H10C109.5C7A—B1A—C13A110.50 (12)
H10B—C10—H10C109.5C19A—B1A—C13A110.20 (12)
N1—C11—C12122.04 (16)C7A—B1A—C1A109.50 (12)
N1—C11—H11119.0C19A—B1A—C1A111.19 (12)
C12—C11—H11119.0C13A—B1A—C1A108.31 (12)
C6—C1—C2—C33.2 (2)C18—C19—C20—N20.1 (3)
C7—C1—C2—C3175.93 (15)C6A—C1A—C2A—C3A0.4 (2)
Ru1—C1—C2—C355.22 (15)B1A—C1A—C2A—C3A178.56 (15)
C6—C1—C2—Ru152.00 (13)C1A—C2A—C3A—C4A0.9 (3)
C7—C1—C2—Ru1128.85 (15)C2A—C3A—C4A—C5A0.5 (3)
C1—C2—C3—C41.1 (3)C3A—C4A—C5A—C6A0.3 (3)
Ru1—C2—C3—C454.22 (14)C4A—C5A—C6A—C1A0.9 (3)
C1—C2—C3—Ru155.33 (14)C2A—C1A—C6A—C5A0.5 (2)
C2—C3—C4—C51.0 (2)B1A—C1A—C6A—C5A177.80 (16)
Ru1—C3—C4—C552.27 (14)C12A—C7A—C8A—C9A1.0 (3)
C2—C3—C4—C10178.31 (16)B1A—C7A—C8A—C9A178.62 (18)
Ru1—C3—C4—C10125.06 (16)C7A—C8A—C9A—C10A0.8 (3)
C2—C3—C4—Ru153.25 (14)C8A—C9A—C10A—C11A1.3 (3)
C3—C4—C5—C60.8 (2)C9A—C10A—C11A—C12A0.1 (3)
C10—C4—C5—C6178.13 (16)C10A—C11A—C12A—C7A1.8 (3)
Ru1—C4—C5—C653.30 (14)C8A—C7A—C12A—C11A2.3 (3)
C3—C4—C5—Ru152.47 (14)B1A—C7A—C12A—C11A177.37 (16)
C10—C4—C5—Ru1124.83 (16)C18A—C13A—C14A—C15A1.0 (2)
C2—C1—C6—C53.4 (2)B1A—C13A—C14A—C15A179.59 (15)
C7—C1—C6—C5175.78 (15)C13A—C14A—C15A—C16A0.6 (3)
Ru1—C1—C6—C555.84 (14)C14A—C15A—C16A—C17A0.0 (3)
C2—C1—C6—Ru152.45 (13)C15A—C16A—C17A—C18A0.1 (3)
C7—C1—C6—Ru1128.39 (14)C16A—C17A—C18A—C13A0.4 (3)
C4—C5—C6—C11.4 (2)C14A—C13A—C18A—C17A0.9 (2)
Ru1—C5—C6—C156.31 (14)B1A—C13A—C18A—C17A179.66 (15)
C4—C5—C6—Ru154.87 (14)C24A—C19A—C20A—C21A0.8 (2)
C6—C1—C7—C8146.08 (18)B1A—C19A—C20A—C21A179.82 (14)
C2—C1—C7—C834.8 (2)C19A—C20A—C21A—C22A0.9 (2)
Ru1—C1—C7—C857.1 (2)C20A—C21A—C22A—C23A1.3 (2)
C6—C1—C7—C989.8 (2)C21A—C22A—C23A—C24A0.1 (2)
C2—C1—C7—C989.3 (2)C22A—C23A—C24A—C19A2.0 (2)
Ru1—C1—C7—C9178.77 (14)C20A—C19A—C24A—C23A2.3 (2)
C15—N1—C11—C121.1 (3)B1A—C19A—C24A—C23A178.31 (14)
Ru1—N1—C11—C12177.98 (18)C8A—C7A—B1A—C19A127.43 (16)
N1—C11—C12—C130.0 (4)C12A—C7A—B1A—C19A52.97 (18)
C11—C12—C13—C140.7 (4)C8A—C7A—B1A—C13A112.49 (17)
C12—C13—C14—C150.2 (3)C12A—C7A—B1A—C13A67.11 (18)
C11—N1—C15—C141.6 (3)C8A—C7A—B1A—C1A6.7 (2)
Ru1—N1—C15—C14178.68 (14)C12A—C7A—B1A—C1A173.66 (14)
C11—N1—C15—C16176.66 (17)C20A—C19A—B1A—C7A129.97 (15)
Ru1—N1—C15—C160.40 (18)C24A—C19A—B1A—C7A49.35 (18)
C13—C14—C15—N10.9 (3)C20A—C19A—B1A—C13A9.70 (19)
C13—C14—C15—C16177.17 (18)C24A—C19A—B1A—C13A169.62 (13)
C20—N2—C16—C171.6 (2)C20A—C19A—B1A—C1A110.41 (16)
Ru1—N2—C16—C17178.47 (11)C24A—C19A—B1A—C1A70.27 (17)
C20—N2—C16—C15176.78 (14)C14A—C13A—B1A—C7A17.8 (2)
Ru1—N2—C16—C150.12 (17)C18A—C13A—B1A—C7A162.90 (13)
N1—C15—C16—N20.2 (2)C14A—C13A—B1A—C19A100.45 (16)
C14—C15—C16—N2178.42 (16)C18A—C13A—B1A—C19A78.87 (17)
N1—C15—C16—C17178.13 (14)C14A—C13A—B1A—C1A137.72 (14)
C14—C15—C16—C170.1 (3)C18A—C13A—B1A—C1A42.96 (18)
N2—C16—C17—C180.9 (2)C2A—C1A—B1A—C7A96.69 (17)
C15—C16—C17—C18177.30 (15)C6A—C1A—B1A—C7A81.38 (18)
C16—C17—C18—C190.3 (2)C2A—C1A—B1A—C19A21.5 (2)
C17—C18—C19—C200.8 (2)C6A—C1A—B1A—C19A160.42 (14)
C16—N2—C20—C191.1 (2)C2A—C1A—B1A—C13A142.74 (15)
Ru1—N2—C20—C19177.71 (12)C6A—C1A—B1A—C13A39.19 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of rings C19A–C24A and N2/C16–C20, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i1.002.663.421 (2)133
C11—H11···Cl1i0.952.623.484 (2)151
C7—H7···Cg1ii1.002.673.616 (2)158
C9—H9B···Cg2iii0.982.913.733 (2)143
C18—H18···Cg10.952.733.431 (2)131
C23A—H23A···Cg2iv0.952.603.461 (2)151
Symmetry codes: (i) x, y1/2, z; (ii) x+1, y1/2, z+1; (iii) x, y1, z; (iv) x+1, y+1/2, z+1.
 

Acknowledgements

Dr Doug Powell performed the data collection and the refinement of the structure. We are grateful to the University of Arkansas for start-up funding, and for some support for the NMR Facility at the University of Arkansas provided by the Arkansas Biosciences Institute. We also thank the University of Oklahoma for funds to purchase the and computers.

Funding information

We thank the National Science Foundation (grant No. CHE-0130835) for funds to purchase the X-ray diffractometer.

References

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