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

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ISSN: 2056-9890

[Bis­(2-pyrid­yl-κN)amine]chlorido(η6-hexa­methyl­benzene)­ruthenium(II) hexa­fluorido­phosphate di­chloro­methane solvate

aDepartment of Chemistry, Kongju National University, 182 Shinkwan, Kongju, Chungnam 314-701, Republic of Korea, and bService Analytique Facultaire, Université de Neuchâtel, Ave de Bellevaux 51, CH-2000 Neuchâtel, Switzerland
*Correspondence e-mail: jkim@kongju.ac.kr

(Received 22 February 2011; accepted 29 March 2011; online 7 April 2011)

In the title half-sandwich complex, [RuCl(η6-C12H18)(C10H9N3)]PF6·CH2Cl2, the ruthenium(II) ion is four-coordinated by a chloro, a hexa­methyl­benzene and a bidentate N,N′-chelating di(pyridin-2-yl)amine ligand. In the crystal, the amino N—H group forms a hydrogen bond with the chloro ligand of a neighbouring complex, thus forming chains along the b axis. Weak inter­molecular C—H⋯F and C—H⋯ Cl contacts are also observed.

Related literature

For related structures with the same N,N′-chelating ligand coordinated to arene ruthenium moieties, see: Romain et al. (2010[Romain, C., Gaillard, S., Elmkaddem, M. K., Toupet, L., Fischmeister, C., Thomas, C. M. & Renaud, J.-L. (2010). Organometallics, 29, 1992-1995.]); Gupta et al. (2011[Gupta, G., Gloria, S., Therrien, B., Das, B. & Mohan Rao, K. (2011). J. Organomet. Chem. 696, 702-708.]); Singh et al. (2004[Singh, A., Chandra, M., Sahay, A. N., Pandey, D. S., Pandey, K. K., Mobin, S. M., Puerta, M. C. & Valerga, P. (2004). J. Organomet. Chem. 689, 1821-1834.]). For the synthesis, see: Romain et al. (2010[Romain, C., Gaillard, S., Elmkaddem, M. K., Toupet, L., Fischmeister, C., Thomas, C. M. & Renaud, J.-L. (2010). Organometallics, 29, 1992-1995.]); Gupta et al. (2010[Gupta, G., Gloria, S., Das, B. & Mohan Rao, K. (2010). J. Mol. Struct. 979, 205-213.]).

[Scheme 1]

Experimental

Crystal data
  • [RuCl(C12H18)(C10H9N3)]PF6·CH2Cl2

  • Mr = 699.88

  • Monoclinic, P 21 /n

  • a = 15.5241 (4) Å

  • b = 9.1644 (2) Å

  • c = 18.9108 (5) Å

  • β = 93.621 (1)°

  • V = 2685.05 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 173 K

  • 0.20 × 0.17 × 0.16 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.738, Tmax = 0.871

  • 31923 measured reflections

  • 9327 independent reflections

  • 7812 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.087

  • S = 1.06

  • 9327 reflections

  • 344 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.78 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯Cl1i 0.85 (3) 2.51 (3) 3.3493 (17) 170 (3)
C3—H3⋯F3ii 0.95 2.52 3.351 (3) 146
C8—H8⋯F5i 0.95 2.55 3.435 (3) 155
C20—H20A⋯Cl3iii 0.98 2.78 3.626 (2) 144
C20—H20B⋯F2iv 0.98 2.54 3.424 (3) 151
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y, -z+2; (iii) x, y+1, z; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART and SAINT (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title complex shows typical three legged piano-stool geometry with the ruthenium(II) atom being coordinated by a hexamethylbenzene ligand occupying one face of the octahedron, a terminal chloro and a bidentate N,N'-chelating ligand, see Fig. 1. The di(pyridin-2-yl)amine ligand acts as a bidentate chelating ligand through its two pyridyl groups, and the Ru-N distances are essentially equivalent at 2.099 (2) and 2.098 (2) Å. The aromatic ring of the hexamethylbenzene is planar and the Ru-centroid distance is 1.690 (2) Å. The Ru-Cl distance is 2.4108 (4) Å, similar to that found in other chloro arene ruthenium complexes (Singh et al., 2004; Gupta et al., 2011).

In the crystal packing, the N-H amino group is involved in a H-bonded interaction with the chloro ligand of a neighbouring complex, thus forming infinite one-dimensional chains along the b axis. Moreover, there are weak intermolecular contacts of the type C—H···F and C—H··· Cl.

Related literature top

For related structures with the same N,N'-chelating ligand coordinated to arene ruthenium moieties, see: Romain et al. (2010); Gupta et al. (2011); Singh et al. (2004). For the synthesis, see: Romain et al. (2010); Gupta et al. (2010).

Experimental top

The synthesis of the title compound has been reported (Romain et al., 2010; Gupta et al., 2011). Yellow-orange crystals for X-ray diffraction analysis were obtained by slow diffusion of hexane into a dichloromethane solution of the title complex.

Refinement top

The H atoms were included in calculated positions and refined using a riding model, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2 (1.5 for methyl) times Ueq(C), except for the H atom of the N—H group which was found in the Fourier difference map and refined isotropically.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of [RuCl(η2-C10H9N3-κ2-N,N')(η6-C12H18)]PF6. Displacement ellipsoids are drawn at the 50% probability level.
[Bis(2-pyridyl-κN)amine]chlorido(η6-hexamethylbenzene)ruthenium(II) hexafluoridophosphate dichloromethane monosolvate top
Crystal data top
[RuCl(C12H18)(C10H9N3)]PF6·CH2Cl2F(000) = 1408
Mr = 699.88Dx = 1.731 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 550 reflections
a = 15.5241 (4) Åθ = 1.7–27.0°
b = 9.1644 (2) ŵ = 1.00 mm1
c = 18.9108 (5) ÅT = 173 K
β = 93.621 (1)°Block, orange
V = 2685.05 (12) Å30.20 × 0.17 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
9327 independent reflections
Radiation source: fine-focus sealed tube7812 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 0 pixels mm-1θmax = 33.9°, θmin = 1.7°
ω scansh = 2224
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1411
Tmin = 0.738, Tmax = 0.871l = 2529
31923 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0383P)2 + 2.053P]
where P = (Fo2 + 2Fc2)/3
9327 reflections(Δ/σ)max = 0.003
344 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.78 e Å3
Crystal data top
[RuCl(C12H18)(C10H9N3)]PF6·CH2Cl2V = 2685.05 (12) Å3
Mr = 699.88Z = 4
Monoclinic, P21/nMo Kα radiation
a = 15.5241 (4) ŵ = 1.00 mm1
b = 9.1644 (2) ÅT = 173 K
c = 18.9108 (5) Å0.20 × 0.17 × 0.16 mm
β = 93.621 (1)°
Data collection top
Bruker SMART CCD
diffractometer
9327 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7812 reflections with I > 2σ(I)
Tmin = 0.738, Tmax = 0.871Rint = 0.030
31923 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.77 e Å3
9327 reflectionsΔρmin = 0.78 e Å3
344 parameters
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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru10.623752 (8)0.316216 (13)0.871467 (6)0.01424 (4)
Cl10.62147 (3)0.05324 (4)0.86885 (2)0.02066 (8)
N10.75701 (10)0.29849 (15)0.86021 (8)0.0181 (3)
N20.74819 (10)0.42939 (17)0.75231 (8)0.0222 (3)
H2A0.7794 (18)0.472 (3)0.7233 (15)0.038 (7)*
N30.61569 (10)0.30532 (15)0.76042 (8)0.0176 (3)
C10.80663 (12)0.2324 (2)0.91254 (10)0.0237 (4)
H10.77900.17760.94720.028*
C20.89516 (13)0.2416 (2)0.91737 (12)0.0306 (4)
H20.92800.19450.95480.037*
C30.93565 (14)0.3209 (2)0.86646 (13)0.0323 (5)
H30.99670.33120.86940.039*
C40.88661 (13)0.3843 (2)0.81186 (11)0.0265 (4)
H40.91330.43830.77640.032*
C50.79686 (12)0.36842 (19)0.80912 (9)0.0196 (3)
C60.67229 (11)0.37280 (19)0.72068 (9)0.0183 (3)
C70.65632 (13)0.3905 (2)0.64760 (9)0.0238 (4)
H70.69730.43850.62050.029*
C80.58096 (14)0.3377 (2)0.61534 (10)0.0300 (4)
H80.56820.35200.56600.036*
C90.52350 (14)0.2629 (3)0.65590 (10)0.0285 (4)
H90.47160.22310.63470.034*
C100.54359 (12)0.2481 (2)0.72714 (9)0.0226 (3)
H100.50510.19500.75460.027*
C110.59093 (13)0.33487 (19)0.98353 (9)0.0215 (3)
C120.64864 (13)0.4479 (2)0.96903 (10)0.0238 (4)
C130.63113 (13)0.54226 (19)0.90926 (10)0.0244 (4)
C140.55431 (14)0.5232 (2)0.86567 (10)0.0253 (4)
C150.49318 (12)0.4121 (2)0.88188 (10)0.0234 (4)
C160.51229 (12)0.31772 (19)0.93991 (10)0.0210 (3)
C170.61053 (17)0.2298 (3)1.04399 (11)0.0362 (5)
H17A0.66430.25891.07020.054*
H17B0.61680.13101.02510.054*
H17C0.56320.23141.07590.054*
C180.73129 (16)0.4720 (3)1.01410 (13)0.0425 (6)
H18A0.72440.55611.04530.064*
H18B0.77860.49070.98340.064*
H18C0.74450.38501.04290.064*
C190.69407 (19)0.6613 (2)0.89334 (15)0.0425 (6)
H19A0.69160.67920.84220.064*
H19B0.75260.63110.90960.064*
H19C0.67890.75090.91800.064*
C200.5372 (2)0.6196 (3)0.80187 (13)0.0474 (7)
H20A0.51790.71580.81710.071*
H20B0.49230.57550.77000.071*
H20C0.59030.63040.77700.071*
C210.40948 (15)0.3991 (3)0.83713 (13)0.0415 (6)
H21A0.38420.30260.84410.062*
H21B0.42070.41160.78710.062*
H21C0.36930.47470.85110.062*
C220.45135 (16)0.1958 (2)0.95564 (14)0.0362 (5)
H22A0.41050.18040.91460.054*
H22B0.41960.22150.99700.054*
H22C0.48430.10600.96550.054*
P10.83358 (3)0.08437 (6)1.08848 (3)0.02634 (11)
F10.80510 (16)0.0740 (2)1.10653 (13)0.0875 (7)
F20.88637 (13)0.0904 (3)1.16249 (9)0.0800 (7)
F30.86296 (14)0.2456 (2)1.06967 (14)0.0859 (7)
F40.78098 (12)0.0793 (2)1.01404 (8)0.0590 (5)
F50.91667 (13)0.0269 (3)1.05393 (10)0.0792 (7)
F60.75213 (14)0.1494 (3)1.12304 (11)0.0860 (8)
Cl20.29778 (4)0.13851 (7)0.69513 (3)0.04174 (14)
Cl30.40491 (4)0.05472 (7)0.78424 (4)0.04606 (15)
C230.30396 (15)0.0338 (3)0.73642 (13)0.0350 (5)
H23A0.29660.11140.70010.042*
H23B0.25690.04350.76910.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01582 (7)0.01321 (6)0.01390 (6)0.00102 (4)0.00260 (5)0.00107 (4)
Cl10.0245 (2)0.01458 (17)0.02333 (19)0.00161 (14)0.00529 (16)0.00003 (13)
N10.0172 (7)0.0176 (6)0.0197 (6)0.0012 (5)0.0017 (5)0.0011 (5)
N20.0209 (7)0.0253 (7)0.0210 (7)0.0042 (6)0.0053 (6)0.0051 (6)
N30.0180 (7)0.0189 (6)0.0162 (6)0.0002 (5)0.0032 (5)0.0019 (5)
C10.0233 (9)0.0225 (8)0.0251 (8)0.0035 (7)0.0018 (7)0.0021 (7)
C20.0235 (10)0.0298 (10)0.0372 (10)0.0042 (8)0.0076 (8)0.0009 (8)
C30.0170 (9)0.0362 (11)0.0432 (12)0.0006 (8)0.0009 (8)0.0040 (9)
C40.0196 (9)0.0266 (9)0.0337 (10)0.0027 (7)0.0050 (7)0.0028 (7)
C50.0192 (8)0.0180 (7)0.0218 (8)0.0011 (6)0.0033 (6)0.0022 (6)
C60.0194 (8)0.0169 (7)0.0188 (7)0.0028 (6)0.0039 (6)0.0025 (6)
C70.0273 (9)0.0263 (8)0.0184 (7)0.0046 (7)0.0054 (7)0.0071 (6)
C80.0308 (11)0.0406 (11)0.0183 (8)0.0056 (9)0.0004 (7)0.0055 (7)
C90.0262 (10)0.0377 (11)0.0211 (8)0.0003 (8)0.0031 (7)0.0007 (8)
C100.0212 (8)0.0259 (9)0.0208 (8)0.0015 (7)0.0017 (7)0.0008 (6)
C110.0304 (10)0.0204 (8)0.0143 (7)0.0036 (7)0.0063 (7)0.0001 (6)
C120.0269 (9)0.0238 (8)0.0210 (8)0.0001 (7)0.0030 (7)0.0068 (6)
C130.0321 (10)0.0142 (7)0.0281 (9)0.0019 (7)0.0114 (8)0.0031 (6)
C140.0335 (10)0.0187 (8)0.0246 (8)0.0107 (7)0.0082 (7)0.0045 (6)
C150.0204 (8)0.0261 (8)0.0239 (8)0.0079 (7)0.0037 (7)0.0028 (7)
C160.0212 (8)0.0190 (7)0.0239 (8)0.0018 (6)0.0099 (7)0.0021 (6)
C170.0536 (14)0.0342 (10)0.0212 (9)0.0055 (10)0.0052 (9)0.0088 (8)
C180.0361 (12)0.0547 (15)0.0356 (11)0.0057 (11)0.0059 (10)0.0177 (11)
C190.0544 (16)0.0222 (10)0.0532 (15)0.0135 (10)0.0228 (12)0.0060 (9)
C200.0685 (18)0.0369 (12)0.0383 (12)0.0245 (12)0.0138 (12)0.0198 (10)
C210.0233 (10)0.0624 (16)0.0381 (12)0.0137 (11)0.0040 (9)0.0082 (11)
C220.0322 (11)0.0302 (10)0.0480 (13)0.0074 (9)0.0171 (10)0.0006 (9)
P10.0245 (2)0.0325 (3)0.0217 (2)0.0028 (2)0.00065 (18)0.00108 (19)
F10.0957 (16)0.0516 (11)0.1124 (18)0.0272 (11)0.0155 (14)0.0377 (12)
F20.0692 (13)0.128 (2)0.0388 (9)0.0203 (13)0.0277 (9)0.0085 (11)
F30.0794 (14)0.0444 (11)0.129 (2)0.0169 (10)0.0326 (13)0.0205 (12)
F40.0668 (11)0.0758 (12)0.0315 (7)0.0028 (9)0.0187 (7)0.0029 (7)
F50.0597 (12)0.1159 (18)0.0652 (12)0.0452 (12)0.0299 (9)0.0266 (12)
F60.0573 (12)0.145 (2)0.0575 (12)0.0489 (13)0.0167 (9)0.0009 (13)
Cl20.0485 (3)0.0372 (3)0.0377 (3)0.0002 (3)0.0113 (2)0.0066 (2)
Cl30.0356 (3)0.0451 (3)0.0571 (4)0.0073 (3)0.0008 (3)0.0181 (3)
C230.0355 (12)0.0315 (10)0.0377 (11)0.0056 (9)0.0006 (9)0.0020 (9)
Geometric parameters (Å, º) top
Ru1—N32.0982 (15)C12—C181.511 (3)
Ru1—N12.0993 (15)C13—C141.417 (3)
Ru1—C142.1808 (18)C13—C191.507 (3)
Ru1—C132.1920 (18)C14—C151.438 (3)
Ru1—C112.2173 (17)C14—C201.506 (3)
Ru1—C122.2178 (18)C15—C161.414 (3)
Ru1—C162.2255 (19)C15—C211.510 (3)
Ru1—C152.2292 (18)C16—C221.506 (3)
Ru1—Cl12.4108 (4)C17—H17A0.9800
N1—C51.343 (2)C17—H17B0.9800
N1—C11.358 (2)C17—H17C0.9800
N2—C61.388 (2)C18—H18A0.9800
N2—C51.391 (2)C18—H18B0.9800
N2—H2A0.85 (3)C18—H18C0.9800
N3—C61.343 (2)C19—H19A0.9800
N3—C101.355 (2)C19—H19B0.9800
C1—C21.374 (3)C19—H19C0.9800
C1—H10.9500C20—H20A0.9800
C2—C31.388 (3)C20—H20B0.9800
C2—H20.9500C20—H20C0.9800
C3—C41.373 (3)C21—H21A0.9800
C3—H30.9500C21—H21B0.9800
C4—C51.399 (3)C21—H21C0.9800
C4—H40.9500C22—H22A0.9800
C6—C71.398 (2)C22—H22B0.9800
C7—C81.373 (3)C22—H22C0.9800
C7—H70.9500P1—F11.5608 (19)
C8—C91.393 (3)P1—F51.5730 (18)
C8—H80.9500P1—F61.5766 (19)
C9—C101.370 (3)P1—F21.5776 (16)
C9—H90.9500P1—F41.5830 (14)
C10—H100.9500P1—F31.593 (2)
C11—C121.408 (3)Cl2—C231.761 (2)
C11—C161.438 (3)Cl3—C231.770 (2)
C11—C171.511 (3)C23—H23A0.9900
C12—C131.436 (3)C23—H23B0.9900
N3—Ru1—N183.79 (6)C11—C12—Ru171.48 (10)
N3—Ru1—C1489.60 (6)C13—C12—Ru170.03 (10)
N1—Ru1—C14123.32 (7)C18—C12—Ru1130.24 (15)
N3—Ru1—C13111.71 (6)C14—C13—C12119.61 (17)
N1—Ru1—C1394.28 (7)C14—C13—C19120.4 (2)
C14—Ru1—C1337.81 (8)C12—C13—C19120.0 (2)
N3—Ru1—C11163.23 (7)C14—C13—Ru170.67 (10)
N1—Ru1—C11112.97 (7)C12—C13—Ru171.98 (10)
C14—Ru1—C1180.69 (7)C19—C13—Ru1129.79 (15)
C13—Ru1—C1168.04 (7)C13—C14—C15120.39 (16)
N3—Ru1—C12148.73 (7)C13—C14—C20119.5 (2)
N1—Ru1—C1290.31 (7)C15—C14—C20120.1 (2)
C14—Ru1—C1268.18 (7)C13—C14—Ru171.52 (10)
C13—Ru1—C1238.00 (7)C15—C14—Ru172.80 (10)
C11—Ru1—C1237.01 (7)C20—C14—Ru1127.76 (15)
N3—Ru1—C16125.66 (7)C16—C15—C14119.30 (17)
N1—Ru1—C16150.10 (7)C16—C15—C21121.2 (2)
C14—Ru1—C1667.90 (7)C14—C15—C21119.49 (19)
C13—Ru1—C1680.27 (7)C16—C15—Ru171.35 (10)
C11—Ru1—C1637.78 (7)C14—C15—Ru169.15 (10)
C12—Ru1—C1667.28 (7)C21—C15—Ru1132.43 (14)
N3—Ru1—C1596.32 (6)C15—C16—C11120.49 (17)
N1—Ru1—C15161.23 (7)C15—C16—C22120.23 (19)
C14—Ru1—C1538.05 (8)C11—C16—C22119.27 (18)
C13—Ru1—C1568.16 (7)C15—C16—Ru171.64 (11)
C11—Ru1—C1567.67 (7)C11—C16—Ru170.80 (10)
C12—Ru1—C1579.85 (7)C22—C16—Ru1129.16 (13)
C16—Ru1—C1537.01 (7)C11—C17—H17A109.5
N3—Ru1—Cl186.10 (4)C11—C17—H17B109.5
N1—Ru1—Cl186.21 (4)H17A—C17—H17B109.5
C14—Ru1—Cl1149.52 (6)C11—C17—H17C109.5
C13—Ru1—Cl1162.15 (5)H17A—C17—H17C109.5
C11—Ru1—Cl195.32 (5)H17B—C17—H17C109.5
C12—Ru1—Cl1124.22 (5)C12—C18—H18A109.5
C16—Ru1—Cl190.41 (5)C12—C18—H18B109.5
C15—Ru1—Cl1112.55 (5)H18A—C18—H18B109.5
C5—N1—C1118.13 (16)C12—C18—H18C109.5
C5—N1—Ru1122.54 (12)H18A—C18—H18C109.5
C1—N1—Ru1118.56 (13)H18B—C18—H18C109.5
C6—N2—C5126.00 (15)C13—C19—H19A109.5
C6—N2—H2A113.3 (18)C13—C19—H19B109.5
C5—N2—H2A112.2 (18)H19A—C19—H19B109.5
C6—N3—C10117.98 (15)C13—C19—H19C109.5
C6—N3—Ru1122.58 (12)H19A—C19—H19C109.5
C10—N3—Ru1118.60 (12)H19B—C19—H19C109.5
N1—C1—C2122.70 (19)C14—C20—H20A109.5
N1—C1—H1118.6C14—C20—H20B109.5
C2—C1—H1118.6H20A—C20—H20B109.5
C1—C2—C3118.73 (19)C14—C20—H20C109.5
C1—C2—H2120.6H20A—C20—H20C109.5
C3—C2—H2120.6H20B—C20—H20C109.5
C4—C3—C2119.31 (19)C15—C21—H21A109.5
C4—C3—H3120.3C15—C21—H21B109.5
C2—C3—H3120.3H21A—C21—H21B109.5
C3—C4—C5119.19 (19)C15—C21—H21C109.5
C3—C4—H4120.4H21A—C21—H21C109.5
C5—C4—H4120.4H21B—C21—H21C109.5
N1—C5—N2119.67 (16)C16—C22—H22A109.5
N1—C5—C4121.75 (17)C16—C22—H22B109.5
N2—C5—C4118.57 (17)H22A—C22—H22B109.5
N3—C6—N2119.91 (15)C16—C22—H22C109.5
N3—C6—C7121.68 (17)H22A—C22—H22C109.5
N2—C6—C7118.40 (16)H22B—C22—H22C109.5
C8—C7—C6119.44 (18)F1—P1—F591.77 (14)
C8—C7—H7120.3F1—P1—F690.87 (15)
C6—C7—H7120.3F5—P1—F6177.30 (15)
C7—C8—C9119.08 (18)F1—P1—F288.70 (13)
C7—C8—H8120.5F5—P1—F289.24 (12)
C9—C8—H8120.5F6—P1—F290.24 (12)
C10—C9—C8118.44 (19)F1—P1—F491.70 (11)
C10—C9—H9120.8F5—P1—F490.64 (11)
C8—C9—H9120.8F6—P1—F489.86 (11)
N3—C10—C9123.26 (18)F2—P1—F4179.59 (14)
N3—C10—H10118.4F1—P1—F3179.65 (17)
C9—C10—H10118.4F5—P1—F387.92 (14)
C12—C11—C16119.76 (16)F6—P1—F389.44 (15)
C12—C11—C17121.06 (19)F2—P1—F391.45 (13)
C16—C11—C17119.18 (18)F4—P1—F388.15 (11)
C12—C11—Ru171.52 (10)Cl2—C23—Cl3110.21 (12)
C16—C11—Ru171.42 (10)Cl2—C23—H23A109.6
C17—C11—Ru1128.81 (14)Cl3—C23—H23A109.6
C11—C12—C13120.36 (17)Cl2—C23—H23B109.6
C11—C12—C18121.75 (19)Cl3—C23—H23B109.6
C13—C12—C18117.87 (19)H23A—C23—H23B108.1
N3—Ru1—N1—C540.39 (14)N1—Ru1—C13—C14143.33 (11)
C14—Ru1—N1—C545.02 (16)C11—Ru1—C13—C14103.61 (12)
C13—Ru1—N1—C571.01 (14)C12—Ru1—C13—C14131.67 (17)
C11—Ru1—N1—C5138.95 (13)C16—Ru1—C13—C1466.32 (11)
C12—Ru1—N1—C5108.84 (14)C15—Ru1—C13—C1429.85 (11)
C16—Ru1—N1—C5148.91 (14)Cl1—Ru1—C13—C14125.76 (17)
C15—Ru1—N1—C551.0 (3)N3—Ru1—C13—C12170.01 (11)
Cl1—Ru1—N1—C5126.88 (14)N1—Ru1—C13—C1285.01 (12)
N3—Ru1—N1—C1149.88 (14)C14—Ru1—C13—C12131.67 (17)
C14—Ru1—N1—C1124.71 (14)C11—Ru1—C13—C1228.06 (11)
C13—Ru1—N1—C198.72 (14)C16—Ru1—C13—C1265.35 (12)
C11—Ru1—N1—C130.78 (15)C15—Ru1—C13—C12101.82 (12)
C12—Ru1—N1—C160.89 (14)Cl1—Ru1—C13—C125.9 (3)
C16—Ru1—N1—C120.8 (2)N3—Ru1—C13—C1955.6 (2)
C15—Ru1—N1—C1118.8 (2)N1—Ru1—C13—C1929.4 (2)
Cl1—Ru1—N1—C163.39 (13)C14—Ru1—C13—C19113.9 (3)
N1—Ru1—N3—C639.46 (13)C11—Ru1—C13—C19142.5 (2)
C14—Ru1—N3—C684.14 (14)C12—Ru1—C13—C19114.4 (3)
C13—Ru1—N3—C652.69 (15)C16—Ru1—C13—C19179.8 (2)
C11—Ru1—N3—C6138.4 (2)C15—Ru1—C13—C19143.7 (2)
C12—Ru1—N3—C640.8 (2)Cl1—Ru1—C13—C19120.3 (2)
C16—Ru1—N3—C6146.23 (13)C12—C13—C14—C151.3 (3)
C15—Ru1—N3—C6121.66 (14)C19—C13—C14—C15178.40 (18)
Cl1—Ru1—N3—C6126.06 (13)Ru1—C13—C14—C1556.12 (16)
N1—Ru1—N3—C10151.27 (14)C12—C13—C14—C20178.35 (18)
C14—Ru1—N3—C1085.14 (14)C19—C13—C14—C201.9 (3)
C13—Ru1—N3—C10116.59 (14)Ru1—C13—C14—C20123.56 (18)
C11—Ru1—N3—C1030.8 (3)C12—C13—C14—Ru154.79 (15)
C12—Ru1—N3—C10128.45 (15)C19—C13—C14—Ru1125.48 (18)
C16—Ru1—N3—C1023.04 (16)N3—Ru1—C14—C13127.75 (11)
C15—Ru1—N3—C1047.61 (14)N1—Ru1—C14—C1345.46 (13)
Cl1—Ru1—N3—C1064.67 (13)C11—Ru1—C14—C1365.98 (11)
C5—N1—C1—C23.9 (3)C12—Ru1—C14—C1329.69 (11)
Ru1—N1—C1—C2166.30 (16)C16—Ru1—C14—C13103.05 (12)
N1—C1—C2—C30.4 (3)C15—Ru1—C14—C13131.44 (16)
C1—C2—C3—C41.8 (3)Cl1—Ru1—C14—C13150.63 (10)
C2—C3—C4—C50.5 (3)N3—Ru1—C14—C15100.80 (11)
C1—N1—C5—N2175.93 (16)N1—Ru1—C14—C15176.91 (10)
Ru1—N1—C5—N214.3 (2)C13—Ru1—C14—C15131.44 (16)
C1—N1—C5—C45.2 (3)C11—Ru1—C14—C1565.46 (11)
Ru1—N1—C5—C4164.55 (14)C12—Ru1—C14—C15101.75 (12)
C6—N2—C5—N134.9 (3)C16—Ru1—C14—C1528.40 (10)
C6—N2—C5—C4146.20 (19)Cl1—Ru1—C14—C1519.19 (17)
C3—C4—C5—N13.1 (3)N3—Ru1—C14—C2014.3 (2)
C3—C4—C5—N2178.03 (18)N1—Ru1—C14—C2068.0 (2)
C10—N3—C6—N2178.17 (16)C13—Ru1—C14—C20113.5 (3)
Ru1—N3—C6—N212.5 (2)C11—Ru1—C14—C20179.5 (2)
C10—N3—C6—C73.0 (3)C12—Ru1—C14—C20143.2 (2)
Ru1—N3—C6—C7166.33 (13)C16—Ru1—C14—C20143.5 (2)
C5—N2—C6—N336.0 (3)C15—Ru1—C14—C20115.1 (3)
C5—N2—C6—C7145.18 (18)Cl1—Ru1—C14—C2095.9 (2)
N3—C6—C7—C80.0 (3)C13—C14—C15—C162.8 (3)
N2—C6—C7—C8178.84 (18)C20—C14—C15—C16176.85 (18)
C6—C7—C8—C92.3 (3)Ru1—C14—C15—C1652.69 (15)
C7—C8—C9—C101.6 (3)C13—C14—C15—C21176.60 (18)
C6—N3—C10—C93.8 (3)C20—C14—C15—C213.7 (3)
Ru1—N3—C10—C9165.96 (16)Ru1—C14—C15—C21127.89 (18)
C8—C9—C10—N31.5 (3)C13—C14—C15—Ru155.51 (15)
N3—Ru1—C11—C12121.3 (2)C20—C14—C15—Ru1124.16 (19)
N1—Ru1—C11—C1256.45 (12)N3—Ru1—C15—C16145.85 (11)
C14—Ru1—C11—C1265.90 (12)N1—Ru1—C15—C16124.88 (19)
C13—Ru1—C11—C1228.76 (11)C14—Ru1—C15—C16132.94 (16)
C16—Ru1—C11—C12131.64 (16)C13—Ru1—C15—C16103.26 (12)
C15—Ru1—C11—C12103.21 (12)C11—Ru1—C15—C1628.99 (10)
Cl1—Ru1—C11—C12144.58 (10)C12—Ru1—C15—C1665.52 (11)
N3—Ru1—C11—C1610.4 (3)Cl1—Ru1—C15—C1657.46 (11)
N1—Ru1—C11—C16171.91 (9)N3—Ru1—C15—C1481.21 (11)
C14—Ru1—C11—C1665.74 (11)N1—Ru1—C15—C148.1 (2)
C13—Ru1—C11—C16102.89 (11)C13—Ru1—C15—C1429.68 (11)
C12—Ru1—C11—C16131.64 (16)C11—Ru1—C15—C14103.96 (12)
C15—Ru1—C11—C1628.43 (10)C12—Ru1—C15—C1467.42 (11)
Cl1—Ru1—C11—C1683.78 (9)C16—Ru1—C15—C14132.94 (16)
N3—Ru1—C11—C17123.3 (2)Cl1—Ru1—C15—C14169.60 (9)
N1—Ru1—C11—C1759.0 (2)N3—Ru1—C15—C2130.2 (2)
C14—Ru1—C11—C17178.7 (2)N1—Ru1—C15—C21119.5 (3)
C13—Ru1—C11—C17144.2 (2)C14—Ru1—C15—C21111.4 (3)
C12—Ru1—C11—C17115.4 (2)C13—Ru1—C15—C21141.1 (2)
C16—Ru1—C11—C17112.9 (2)C11—Ru1—C15—C21144.6 (2)
C15—Ru1—C11—C17141.4 (2)C12—Ru1—C15—C21178.9 (2)
Cl1—Ru1—C11—C1729.2 (2)C16—Ru1—C15—C21115.6 (3)
C16—C11—C12—C132.6 (3)Cl1—Ru1—C15—C2158.2 (2)
C17—C11—C12—C13176.89 (18)C14—C15—C16—C111.6 (3)
Ru1—C11—C12—C1352.13 (15)C21—C15—C16—C11177.77 (18)
C16—C11—C12—C18178.88 (18)Ru1—C15—C16—C1153.32 (15)
C17—C11—C12—C181.7 (3)C14—C15—C16—C22176.89 (18)
Ru1—C11—C12—C18126.43 (19)C21—C15—C16—C223.7 (3)
C16—C11—C12—Ru154.68 (15)Ru1—C15—C16—C22125.22 (17)
C17—C11—C12—Ru1124.76 (18)C14—C15—C16—Ru151.68 (15)
N3—Ru1—C12—C11151.63 (13)C21—C15—C16—Ru1128.92 (18)
N1—Ru1—C12—C11129.88 (11)C12—C11—C16—C151.0 (3)
C14—Ru1—C12—C11103.99 (12)C17—C11—C16—C15178.42 (18)
C13—Ru1—C12—C11133.55 (17)Ru1—C11—C16—C1553.70 (15)
C16—Ru1—C12—C1129.75 (11)C12—C11—C16—C22179.58 (18)
C15—Ru1—C12—C1166.19 (12)C17—C11—C16—C220.1 (3)
Cl1—Ru1—C12—C1144.26 (13)Ru1—C11—C16—C22124.85 (17)
N3—Ru1—C12—C1318.08 (19)C12—C11—C16—Ru154.73 (15)
N1—Ru1—C12—C1396.56 (12)C17—C11—C16—Ru1124.72 (17)
C14—Ru1—C12—C1329.56 (12)N3—Ru1—C16—C1543.37 (13)
C11—Ru1—C12—C13133.55 (17)N1—Ru1—C16—C15148.04 (12)
C16—Ru1—C12—C13103.80 (12)C14—Ru1—C16—C1529.14 (11)
C15—Ru1—C12—C1367.37 (12)C13—Ru1—C16—C1566.44 (12)
Cl1—Ru1—C12—C13177.81 (9)C11—Ru1—C16—C15132.97 (15)
N3—Ru1—C12—C1892.0 (2)C12—Ru1—C16—C15103.78 (12)
N1—Ru1—C12—C1813.6 (2)Cl1—Ru1—C16—C15128.87 (10)
C14—Ru1—C12—C18139.7 (2)N3—Ru1—C16—C11176.34 (9)
C13—Ru1—C12—C18110.1 (2)N1—Ru1—C16—C1115.07 (17)
C11—Ru1—C12—C18116.3 (2)C14—Ru1—C16—C11103.83 (11)
C16—Ru1—C12—C18146.1 (2)C13—Ru1—C16—C1166.53 (11)
C15—Ru1—C12—C18177.5 (2)C12—Ru1—C16—C1129.19 (10)
Cl1—Ru1—C12—C1872.1 (2)C15—Ru1—C16—C11132.97 (15)
C11—C12—C13—C141.4 (3)Cl1—Ru1—C16—C1198.17 (9)
C18—C12—C13—C14180.00 (18)N3—Ru1—C16—C2271.1 (2)
Ru1—C12—C13—C1454.17 (15)N1—Ru1—C16—C2297.5 (2)
C11—C12—C13—C19178.90 (18)C14—Ru1—C16—C22143.6 (2)
C18—C12—C13—C190.3 (3)C13—Ru1—C16—C22179.1 (2)
Ru1—C12—C13—C19126.10 (18)C11—Ru1—C16—C22112.6 (2)
C11—C12—C13—Ru152.79 (16)C12—Ru1—C16—C22141.8 (2)
C18—C12—C13—Ru1125.83 (18)C15—Ru1—C16—C22114.5 (2)
N3—Ru1—C13—C1458.32 (12)Cl1—Ru1—C16—C2214.42 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl1i0.85 (3)2.51 (3)3.3493 (17)170 (3)
C3—H3···F3ii0.952.523.351 (3)146
C8—H8···F5i0.952.553.435 (3)155
C20—H20A···Cl3iii0.982.783.626 (2)144
C20—H20B···F2iv0.982.543.424 (3)151
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+2, y, z+2; (iii) x, y+1, z; (iv) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formula[RuCl(C12H18)(C10H9N3)]PF6·CH2Cl2
Mr699.88
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)15.5241 (4), 9.1644 (2), 18.9108 (5)
β (°) 93.621 (1)
V3)2685.05 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.00
Crystal size (mm)0.20 × 0.17 × 0.16
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.738, 0.871
No. of measured, independent and
observed [I > 2σ(I)] reflections
31923, 9327, 7812
Rint0.030
(sin θ/λ)max1)0.785
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.087, 1.06
No. of reflections9327
No. of parameters344
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.77, 0.78

Computer programs: SMART (Bruker, 1999), SMART and SAINT (Bruker, 1999), SAINT (Bruker, 1999), SIR97 (Altomare et al., 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl1i0.85 (3)2.51 (3)3.3493 (17)170 (3)
C3—H3···F3ii0.952.523.351 (3)146
C8—H8···F5i0.952.553.435 (3)155
C20—H20A···Cl3iii0.982.783.626 (2)144
C20—H20B···F2iv0.982.543.424 (3)151
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+2, y, z+2; (iii) x, y+1, z; (iv) x1/2, y+1/2, z1/2.
 

Acknowledgements

This work was supported by the Korea Research Foundation (KRF 313-2008-2-C00444).

References

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First citationGupta, G., Gloria, S., Das, B. & Mohan Rao, K. (2010). J. Mol. Struct. 979, 205–213.  CrossRef CAS Google Scholar
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First citationRomain, C., Gaillard, S., Elmkaddem, M. K., Toupet, L., Fischmeister, C., Thomas, C. M. & Renaud, J.-L. (2010). Organometallics, 29, 1992–1995.  CrossRef CAS Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, A., Chandra, M., Sahay, A. N., Pandey, D. S., Pandey, K. K., Mobin, S. M., Puerta, M. C. & Valerga, P. (2004). J. Organomet. Chem. 689, 1821–1834.  Web of Science CSD CrossRef CAS Google Scholar

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