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The title complex, di-μ-chloro-bis­[chloro­(η6-p-cymene)ruthenium(II)]–9H-carbazole (1/2), [Ru2Cl4(C10H14)2]·2C12H9N, is composed of one [RuCl26-p-cymene)]2 and two 9H-carbazole mol­ecules. There are one-half of a dinuclear complex and one 9H-carbazole mol­ecule per asymmetric unit. In the dinuclear complex, each of the two crystallographically equivalent Ru atoms is in a pseudo-tetra­hedral environment, coordinated by a terminal Cl atom, two bridging Cl atoms and the aromatic hydro­carbon, which is linked in a η6 manner; the Ru...Ru separation is 3.688 (3) Å. The title complex has a crystallographic centre of symmetry located at the mid-point of the Ru...Ru line. Inter­molecular N—H...Cl and π–π stacking inter­actions are observed. These inter­actions form a four-pointed star-shaped ring and one-dimensional linear chains of edge-fused rings running parallel to the [100] direction, which stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106020543/hj3009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106020543/hj3009Isup2.hkl
Contains datablock I

CCDC reference: 618603

Comment top

Arene-ruthenium(II) derivatives are of interest both as reagents in organic chemistry (Pigge & Coniglio, 2001) and as catalysts for a wide range of reactions, including arene hydrogenation (Boxwell et al., 2002), alkene metathesis (Zaja et al., 2003) and Diels-Alder reactions (Davenport et al., 2004). Tetrachlorobis(η6-arene)diruthenium complexes are readily accessible compounds and widely used as starting materials for a wide variety of materials (Bennett, 1997). As a result of their accessibility and propensity to react with nucleophiles, they are often the chosen catalyst precursors for a variety of homogeneous catalytic reactions (Soleimannejad et al., 2003; Özdemir et al., 2001). One of our recent interests involves ketone transfer hydrogenation reactions catalyzed by ruthenium(II) complexes in 2-propanol. In this effort, we have prepared and tested a range of pyridine-diimine complexes of RuII (Çetinkaya et al., 1999; Dayan & Çetinkaya, 2005). As part of this work, we were attempting to use carbazole as an additive in the presence of the µ-chloro-bridged dimer [RuCl2(η6-p-cymene)]2 to improve the catalytic reduction. However, gas chromatography showed that the desired secondery alcohol was not formed in a significant amount, but rather a new adduct between the p-cymene dimer and carbazole in a 1:2 ratio had been isolated. The formulation of the product has been established by 1H and 13C NMR spectroscopy. It is worth noting that the expected multiplets due to the carbazole protons are complicated because of 3-bond couplings.

Crystal engineering of inorganic–organic hybrid materials is based on a modular approach, where discrete building blocks are connected into extended networks. In the search for reliable strategies for crystal synthesis by design, a key goal is the identification and exploitation of robust synthons to control the relative orientation of the molecular component of the solid. Among the usual interactions found to assemble the molecular crystal, hydrogen-bonding interactions have attracted the most attention. In the case of transition metal chloride complexes, the M—Cl units (M is a transition metal) can act as good hydrogen-bond acceptors (Gillon et al., 2000; Lewis & Orpen, 1998; Luque et al., 2002). Complex (I), composed of tetrachlorobis(η6-p-cymene)diruthenium and 9H-carbazole moieties, is an example of such an inorganic–organic hybrid with hydrogen bonding as well as ππ stacking interactions.

The asymmetric unit of (I) contains one-half of the dimeric molecule [RuCl2(η6-p-cymene)]2 and one 9H-carbazole moiety. As shown in Fig. 1, the structure of p-cymene dimer contains a dimetallocyclic Ru2Cl2 core with a crystallographic centre of inversion at the mid-point of the Ru1···Ru1i line [symmetry code: (i) −x + 1, −y + 1, −z]. The Ru1/Cl1/Ru1i/Cl1i ring is strictly planar because of the inversion centre. The environment around the each RuII atom is made up of a terminal Cl atom, two bridging Cl atoms, and the hydrocarbon linked through its π cloud in a typical organometallic η6 bond (see Fig. 1). The rotational orientation of the arene is such that the tripodal ligands are staggered with respect to the arene C atoms, i.e. when viewed along the arene centroid—Ru bond axis, the ligands eclipse the arene C—C bonds rather than the C atoms.

The Ru atom adopts a pseudo-octahedral coordination geometry, with the arene formally occupying three facial coordination sites. However, the geometry around the metal atom may be regarded as a tetrahedron with considerable trigonal distortion, considering the linkage to the hydrocarbon as a single bond. Defining X as the centroid of the aromatic ring, the Ru—X distance is 1.647 (4) Å and the Cl1—Ru1—X, Cl1i—Ru1—X and Cl2—Ru1—X angles are 128.06 (9), 128.61 (10) and 129.73 (9)°, respectively. Many ruthenium-arene complexes have been characterized crystallographically (Aitali et al., 2000; Bown & Bennett, 1999; Feher et al., 2000; Soleimannejad et al., 2005). The Ru—arene distances in these complexes are in the range 1.640–1.671 Å. The Ru—arene distance for (I) is at the lower end of this range. The Cl1—Ru1—Cl2, Cl1—Ru1—Cl1i and Cl1i—Ru1—Cl2 bond angles [mean 84.82 (4)°] are smaller than the ideal tetrahedral angle (109.47°), which is compensated for by the opening of the X—Ru—L (L is Cl1, Cl1i or Cl2) angles [mean 128.80 (10)°]. While there are substantial differences in the C—C [1.398 (5)–1.423 (5) Å] and C—Ru [2.150 (4)–2.193 (3) Å] distances for the arene ring, there is no evidence of the alternating C—C bonds observed in some ruthenium-arene complexes (Begley et al., 1991). Note that the longest Ru—C bond (Ru1—C4; see Table 1) is trans with respect to atoms Cl1 and Cl2, as a result of the strong trans influence of this group.

The two terminal Cl atoms have trans orientations with respect to the planar Ru2Cl2 core. In the dinuclear Ru2Cl2 core, the Ru1—Cl1, Ru1—Cl1i and Ru1—Cl2 bond distances are 2.4459 (9), 2.4445 (8) and 2.3956 (10) Å, respectively, while the Ru1—Cl1—Ru1i and Cl1—Ru1—Cl1i angles are 97.92 (3) and 82.08 (3)°, respectively. The bridging and terminal Ru—Cl distances agree well with those found in other arene-ruthenium complexes possessing µ-Cl ligands (McCormick & Gleason, 1988; Gupta et al., 1997; Therrien et al., 1998; Bown & Bennett, 1999). There is clearly no Ru—Ru bond in the dimer, the Ru···Ru distance of 3.688 (3) Å being too long to include any metal–metal interaction. The carbazole moiety in (I) is planar, the r.m.s. deviation from the plane being 0.022 Å, and the geometric parameters do not deviate from the standard values for the corresponding heterocyclic systems (Allen et al., 1987).

The geometry and packing arrangement in the crystal structure is quite interesting. There are no intermolecular interactions between molecules in the b or c directions. In the construction of the intermolecular connections along the a axis, the carbazole moieties play an active bridging role. Fig. 2 shows that the molecules are translated linearly along the a axis of the unit cell at z = 0, 1/2 and 1, and are related to one another by 21 screw symmetry, in which the 21 screw axes are along (a, 1/2, 1/4) and (a, 1/2, 3/4). There are two carbazole moieties between two adjacent dimeric molecules along the a axis, and these are on a line that is perpendicular to the mid-point of the line linking the centres of inversion of each core of the two adjacent dimeric molecules along the [100] direction, and which is parallel to the [001] direction. In this arrangement, each of the two inversion-related carbazole moieties forms an N1—H1···Cl2 contact with one of the two neighbouring dimeric molecules (Table 2), and ππ stacking interactions between the C17–C22 ring of the carbazole moiety and the arene ring of the adjacent dimeric molecule; the arene ring at (x, y, z) stacks above the C17–C22 ring at (x + 1, y, z), with a distance of 3.574 (6) Å between the ring centroids and a perpendicular distance between the rings of 3.387 (5) Å. This arrangement leads to a four-pointed star-shapped ring between two neighbouring dimeric molecules, translated linearly along the a axis of the unit cell. Propagation of this hydrogen-bonding motif generates one-dimensional linear chains of edge-fused rings running parallel to the [100] direction (Fig. 2).

Experimental top

All manipulations were performed under argon using standard Schlenk techniques. RuCl3·3H2O (Johnson and Mathey), carbazole (Fluka) and ethanol (Merck) were used as received. [RuCl2(p-cymene)]2 was synthesized according to published procedures (Bennett & Smith, 1974). An ethanol solution (30 ml) of carbazole (351 mg, 2.10 mmol) was mixed with [RuCl2(p-cymene)]2 (612 mg, 1.0 mmol). The reaction mixture was heated on a water bath for 3 h and was concentrated (10 ml). The product crystallized from ethanol. After filtration, the brown crystals were washed with cold ethanol (2 × 5 ml) and diethyl ether (2 × 5 ml) and dried in vacuo to give 515 mg (66%) of product (m.p. 440 K). 1H NMR (δ in p.p.m., 400 MHz, J in Hz, CDCl3): 8.35 (s, 2H, NH), 8.06 (d, J = 7.6, 4H, Cz ArH), 7.48 (d, J = 7.4, 4H, Cz ArH), 7.41 (t, J = 7.6, 4H, Cz ArH), 7.23 (t, J = 7.4, 4H, Cz ArH), 5.42 (d, J = 5.6, 4H, p-cymene ArH), 5.28 (d, J = 6, 4H, p-cymene ArH), 2.89 [heptet, J = 6.9, 2H, –CH(CH3)2], 2.12 (s, 6H, CH3), 1.24 [d, J = 7.2, –CH(CH3)2]; 13C NMR (δ in p.p.m., 100 MHz, CDCl3): 139.83, 125.97, 123.52, 120.46, 119.53, 111.08, 101.41, 96.95, 81.51, 80.75, 30.84, 22.34, 19.10.

Refinement top

H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.96, 0.98, 0.93 and 0.86 Å for CH3, CH, CH(aromatic) and NH, respectively. The displacement parameters of the H atoms were constrained as Uiso(H) = 1.2Ueq (1.5Ueq for methyl) of the carrier atom.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. : A view of complex (I), with 40% probability displacement ellipsoids and the atom-numbering scheme. H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) 1 − x, 1 − y, −z.]
[Figure 2] Fig. 2. : Part of the crystal structure of (I), showing the formation of one-dimensional linear chains of star-shaped edge-fused rings along [100]. For clarity, only H atoms involved in hydrogen bonding have been included.
di-µ-chloro-bis[chloro(η6-p-cymene)ruthenium]–9H-carbazole (1/2) top
Crystal data top
[Ru2Cl4(C10H14)2]·2C12H9NF(000) = 1920
Mr = 946.77Dx = 1.544 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 12882 reflections
a = 8.1427 (5) Åθ = 2.2–26.1°
b = 18.3212 (14) ŵ = 1.04 mm1
c = 27.303 (3) ÅT = 296 K
V = 4073.2 (6) Å3Stick, brown
Z = 40.65 × 0.31 × 0.11 mm
Data collection top
Stoe IPDS-2
diffractometer
3964 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2660 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.040
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = 98
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2022
Tmin = 0.803, Tmax = 0.902l = 2833
13233 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0339P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3964 reflectionsΔρmax = 0.35 e Å3
239 parametersΔρmin = 0.42 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00090 (8)
Crystal data top
[Ru2Cl4(C10H14)2]·2C12H9NV = 4073.2 (6) Å3
Mr = 946.77Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 8.1427 (5) ŵ = 1.04 mm1
b = 18.3212 (14) ÅT = 296 K
c = 27.303 (3) Å0.65 × 0.31 × 0.11 mm
Data collection top
Stoe IPDS-2
diffractometer
3964 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
2660 reflections with I > 2σ(I)
Tmin = 0.803, Tmax = 0.902Rint = 0.040
13233 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.01Δρmax = 0.35 e Å3
3964 reflectionsΔρmin = 0.42 e Å3
239 parameters
Special details top

Experimental. Melting points were determined in open capillary tubes on a digital Electrothermal 9100 melting point apparatus. 1H and 13C spectra were obtained on a Varian As 400 MHz s pectrometer operating at 399.883 and 100.561 MHz.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Ru10.44192 (3)0.451931 (12)0.056764 (9)0.04067 (10)
Cl10.43467 (12)0.43226 (4)0.03181 (3)0.0523 (2)
Cl20.71502 (12)0.40348 (6)0.05394 (4)0.0689 (3)
N10.8432 (4)0.52431 (15)0.13937 (11)0.0576 (8)
H10.78390.51030.11510.069*
C10.2594 (5)0.36866 (18)0.07373 (12)0.0508 (9)
C20.1810 (5)0.43404 (18)0.05881 (14)0.0563 (9)
H20.10550.43250.03330.068*
C30.2147 (5)0.50131 (19)0.08167 (15)0.0593 (10)
H30.16060.54320.07120.071*
C40.3295 (5)0.50574 (19)0.12018 (13)0.0566 (9)
C50.4087 (5)0.44171 (19)0.13492 (12)0.0590 (10)
H50.48570.44350.16000.071*
C60.3729 (5)0.37383 (17)0.11196 (12)0.0544 (9)
H60.42640.33190.12260.065*
C70.2246 (5)0.29698 (18)0.04793 (13)0.0606 (10)
H70.20230.30760.01340.073*
C80.0691 (6)0.2648 (2)0.07035 (17)0.0775 (13)
H8A0.08830.25380.10430.116*
H8B0.04020.22080.05320.116*
H8C0.01890.29940.06770.116*
C90.3650 (6)0.2426 (2)0.05030 (19)0.0913 (15)
H9A0.46560.26640.04130.137*
H9B0.34390.20310.02810.137*
H9C0.37430.22390.08300.137*
C100.3741 (6)0.5780 (2)0.14264 (16)0.0754 (13)
H10A0.48250.57510.15640.113*
H10B0.29680.58970.16800.113*
H10C0.37150.61520.11790.113*
C110.8619 (5)0.59600 (19)0.15507 (13)0.0548 (9)
C120.7954 (5)0.6596 (2)0.13563 (16)0.0723 (12)
H120.72760.65870.10820.087*
C130.8348 (7)0.7236 (2)0.15879 (19)0.0821 (13)
H130.79170.76710.14680.098*
C140.9363 (7)0.7257 (2)0.19932 (19)0.0862 (14)
H140.96030.77040.21380.103*
C151.0024 (6)0.6630 (2)0.21870 (16)0.0750 (12)
H151.07010.66470.24610.090*
C160.9650 (5)0.59611 (19)0.19598 (13)0.0568 (9)
C171.0127 (5)0.5214 (2)0.20509 (13)0.0538 (9)
C181.1148 (5)0.4871 (3)0.23865 (14)0.0686 (11)
H181.16720.51410.26290.082*
C191.1379 (6)0.4129 (3)0.23577 (16)0.0746 (12)
H191.20750.38980.25790.089*
C201.0581 (6)0.3724 (2)0.20021 (15)0.0702 (11)
H201.07420.32210.19930.084*
C210.9565 (5)0.40382 (19)0.16640 (14)0.0606 (10)
H210.90390.37600.14260.073*
C220.9347 (5)0.47952 (18)0.16901 (13)0.0519 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.04295 (16)0.04081 (14)0.03827 (14)0.00152 (12)0.00065 (13)0.00027 (11)
Cl10.0671 (6)0.0482 (4)0.0416 (4)0.0164 (4)0.0017 (5)0.0038 (3)
Cl20.0521 (6)0.0783 (6)0.0762 (6)0.0165 (5)0.0070 (5)0.0099 (5)
N10.054 (2)0.0646 (18)0.0540 (18)0.0065 (15)0.0088 (16)0.0062 (14)
C10.053 (2)0.0531 (19)0.0459 (18)0.0139 (16)0.0066 (17)0.0004 (15)
C20.047 (2)0.058 (2)0.063 (2)0.0034 (16)0.005 (2)0.0027 (17)
C30.049 (3)0.052 (2)0.078 (3)0.0020 (17)0.015 (2)0.0012 (18)
C40.062 (3)0.056 (2)0.051 (2)0.0094 (19)0.022 (2)0.0076 (16)
C50.076 (3)0.063 (2)0.0384 (18)0.015 (2)0.0027 (17)0.0024 (15)
C60.076 (3)0.0453 (18)0.0421 (18)0.0061 (16)0.0037 (18)0.0068 (14)
C70.072 (3)0.053 (2)0.057 (2)0.0164 (19)0.004 (2)0.0059 (16)
C80.082 (3)0.051 (2)0.099 (3)0.020 (2)0.005 (3)0.009 (2)
C90.081 (4)0.074 (3)0.119 (4)0.003 (2)0.014 (3)0.038 (3)
C100.090 (4)0.054 (2)0.082 (3)0.015 (2)0.031 (3)0.0227 (19)
C110.048 (2)0.058 (2)0.059 (2)0.0053 (17)0.0047 (18)0.0043 (17)
C120.061 (3)0.073 (3)0.083 (3)0.002 (2)0.001 (2)0.002 (2)
C130.086 (4)0.061 (2)0.099 (4)0.003 (2)0.006 (3)0.002 (2)
C140.103 (4)0.065 (3)0.090 (3)0.012 (3)0.015 (3)0.021 (2)
C150.078 (3)0.083 (3)0.064 (3)0.014 (2)0.004 (2)0.017 (2)
C160.052 (3)0.064 (2)0.055 (2)0.0087 (18)0.0068 (19)0.0091 (17)
C170.044 (2)0.071 (2)0.0460 (19)0.0074 (17)0.0026 (16)0.0070 (17)
C180.062 (3)0.094 (3)0.050 (2)0.009 (2)0.001 (2)0.002 (2)
C190.069 (3)0.095 (3)0.059 (3)0.005 (2)0.007 (2)0.018 (2)
C200.080 (3)0.069 (2)0.061 (2)0.005 (2)0.008 (3)0.0112 (19)
C210.061 (3)0.064 (2)0.056 (2)0.008 (2)0.007 (2)0.0049 (17)
C220.045 (2)0.0635 (19)0.0475 (18)0.0053 (18)0.0026 (18)0.0017 (16)
Geometric parameters (Å, º) top
Ru1—C22.150 (4)C8—H8B0.9600
Ru1—C62.153 (3)C8—H8C0.9600
Ru1—C52.159 (3)C9—H9A0.9600
Ru1—C32.169 (4)C9—H9B0.9600
Ru1—C12.180 (3)C9—H9C0.9600
Ru1—C42.193 (3)C10—H10A0.9600
Ru1—Cl22.3956 (10)C10—H10B0.9600
Ru1—Cl1i2.4445 (8)C10—H10C0.9600
Ru1—Cl12.4459 (9)C11—C121.389 (5)
Cl1—Ru1i2.4445 (8)C11—C161.397 (5)
N1—C221.373 (4)C12—C131.371 (6)
N1—C111.390 (4)C12—H120.9300
N1—H10.8600C13—C141.382 (7)
C1—C61.398 (5)C13—H130.9300
C1—C21.417 (5)C14—C151.375 (7)
C1—C71.517 (4)C14—H140.9300
C2—C31.408 (5)C15—C161.407 (5)
C2—H20.9300C15—H150.9300
C3—C41.409 (5)C16—C171.443 (5)
C3—H30.9300C17—C181.388 (5)
C4—C51.398 (5)C17—C221.401 (5)
C4—C101.503 (5)C18—C191.375 (6)
C5—C61.423 (5)C18—H180.9300
C5—H50.9300C19—C201.384 (6)
C6—H60.9300C19—H190.9300
C7—C91.518 (6)C20—C211.367 (6)
C7—C81.525 (5)C20—H200.9300
C7—H70.9800C21—C221.400 (5)
C8—H8A0.9600C21—H210.9300
C2—Ru1—C667.83 (14)C6—C5—H5119.6
C2—Ru1—C580.64 (15)Ru1—C5—H5129.9
C6—Ru1—C538.53 (12)C1—C6—C5121.6 (3)
C2—Ru1—C338.06 (13)C1—C6—Ru172.23 (19)
C6—Ru1—C380.52 (14)C5—C6—Ru170.98 (18)
C5—Ru1—C367.64 (16)C1—C6—H6119.2
C2—Ru1—C138.20 (13)C5—C6—H6119.2
C6—Ru1—C137.63 (13)Ru1—C6—H6130.3
C5—Ru1—C169.13 (13)C1—C7—C9114.1 (3)
C3—Ru1—C169.12 (14)C1—C7—C8107.7 (3)
C2—Ru1—C468.62 (15)C9—C7—C8110.7 (3)
C6—Ru1—C468.72 (13)C1—C7—H7108.1
C5—Ru1—C437.47 (14)C9—C7—H7108.1
C3—Ru1—C437.70 (14)C8—C7—H7108.1
C1—Ru1—C482.08 (13)C7—C8—H8A109.5
C2—Ru1—Cl2149.48 (9)C7—C8—H8B109.5
C6—Ru1—Cl291.05 (11)H8A—C8—H8B109.5
C5—Ru1—Cl296.65 (11)C7—C8—H8C109.5
C3—Ru1—Cl2163.04 (12)H8A—C8—H8C109.5
C1—Ru1—Cl2112.36 (10)H8B—C8—H8C109.5
C4—Ru1—Cl2125.42 (12)C7—C9—H9A109.5
C2—Ru1—Cl1i123.08 (9)C7—C9—H9B109.5
C6—Ru1—Cl1i151.56 (9)H9A—C9—H9B109.5
C5—Ru1—Cl1i113.72 (9)C7—C9—H9C109.5
C3—Ru1—Cl1i94.36 (10)H9A—C9—H9C109.5
C1—Ru1—Cl1i161.27 (10)H9B—C9—H9C109.5
C4—Ru1—Cl1i90.08 (9)C4—C10—H10A109.5
Cl2—Ru1—Cl1i86.05 (4)C4—C10—H10B109.5
C2—Ru1—Cl188.82 (11)H10A—C10—H10B109.5
C6—Ru1—Cl1126.02 (9)C4—C10—H10C109.5
C5—Ru1—Cl1164.04 (10)H10A—C10—H10C109.5
C3—Ru1—Cl1110.54 (12)H10B—C10—H10C109.5
C1—Ru1—Cl195.20 (9)C12—C11—N1129.2 (4)
C4—Ru1—Cl1146.82 (12)C12—C11—C16122.6 (3)
Cl2—Ru1—Cl186.33 (4)N1—C11—C16108.3 (3)
Cl1i—Ru1—Cl182.08 (3)C13—C12—C11116.8 (4)
Ru1i—Cl1—Ru197.92 (3)C13—C12—H12121.6
C22—N1—C11108.9 (3)C11—C12—H12121.6
C22—N1—H1125.6C12—C13—C14122.2 (4)
C11—N1—H1125.6C12—C13—H13118.9
C6—C1—C2117.1 (3)C14—C13—H13118.9
C6—C1—C7122.0 (3)C15—C14—C13121.3 (4)
C2—C1—C7120.9 (3)C15—C14—H14119.4
C6—C1—Ru170.14 (19)C13—C14—H14119.4
C2—C1—Ru169.8 (2)C14—C15—C16118.3 (4)
C7—C1—Ru1129.4 (2)C14—C15—H15120.9
C3—C2—C1121.7 (4)C16—C15—H15120.9
C3—C2—Ru171.7 (2)C11—C16—C15118.9 (4)
C1—C2—Ru172.0 (2)C11—C16—C17107.3 (3)
C3—C2—H2119.2C15—C16—C17133.7 (4)
C1—C2—H2119.2C18—C17—C22119.2 (4)
Ru1—C2—H2129.7C18—C17—C16134.8 (4)
C2—C3—C4120.7 (3)C22—C17—C16106.0 (3)
C2—C3—Ru170.2 (2)C19—C18—C17119.5 (4)
C4—C3—Ru172.1 (2)C19—C18—H18120.3
C2—C3—H3119.7C17—C18—H18120.3
C4—C3—H3119.7C18—C19—C20120.4 (4)
Ru1—C3—H3130.7C18—C19—H19119.8
C5—C4—C3118.2 (3)C20—C19—H19119.8
C5—C4—C10120.7 (4)C21—C20—C19122.1 (4)
C3—C4—C10121.0 (4)C21—C20—H20118.9
C5—C4—Ru169.96 (19)C19—C20—H20118.9
C3—C4—Ru170.2 (2)C20—C21—C22117.4 (4)
C10—C4—Ru1128.1 (3)C20—C21—H21121.3
C4—C5—C6120.8 (4)C22—C21—H21121.3
C4—C5—Ru172.6 (2)N1—C22—C21129.1 (3)
C6—C5—Ru170.49 (19)N1—C22—C17109.4 (3)
C4—C5—H5119.6C21—C22—C17121.4 (4)
C2—Ru1—Cl1—Ru1i123.64 (9)C2—Ru1—C4—C10143.3 (4)
C6—Ru1—Cl1—Ru1i175.15 (13)C6—Ru1—C4—C10143.1 (4)
C5—Ru1—Cl1—Ru1i172.1 (4)C5—Ru1—C4—C10113.8 (5)
C3—Ru1—Cl1—Ru1i91.71 (10)C3—Ru1—C4—C10114.5 (5)
C1—Ru1—Cl1—Ru1i161.35 (10)C1—Ru1—C4—C10179.6 (4)
C4—Ru1—Cl1—Ru1i77.87 (17)Cl2—Ru1—C4—C1067.8 (4)
Cl2—Ru1—Cl1—Ru1i86.51 (4)Cl1i—Ru1—C4—C1017.4 (4)
Cl1i—Ru1—Cl1—Ru1i0.0Cl1—Ru1—C4—C1093.0 (4)
C2—Ru1—C1—C6130.5 (3)C3—C4—C5—C60.7 (5)
C5—Ru1—C1—C628.8 (2)C10—C4—C5—C6176.7 (3)
C3—Ru1—C1—C6101.9 (2)Ru1—C4—C5—C653.5 (3)
C4—Ru1—C1—C665.2 (2)C3—C4—C5—Ru152.8 (3)
Cl2—Ru1—C1—C659.9 (2)C10—C4—C5—Ru1123.2 (3)
Cl1i—Ru1—C1—C6131.2 (3)C2—Ru1—C5—C466.9 (2)
Cl1—Ru1—C1—C6148.1 (2)C6—Ru1—C5—C4132.9 (4)
C6—Ru1—C1—C2130.5 (3)C3—Ru1—C5—C429.6 (2)
C5—Ru1—C1—C2101.7 (2)C1—Ru1—C5—C4104.8 (3)
C3—Ru1—C1—C228.6 (2)Cl2—Ru1—C5—C4143.8 (2)
C4—Ru1—C1—C265.3 (2)Cl1i—Ru1—C5—C455.2 (2)
Cl2—Ru1—C1—C2169.60 (18)Cl1—Ru1—C5—C4116.2 (4)
Cl1i—Ru1—C1—C20.8 (4)C2—Ru1—C5—C666.0 (2)
Cl1—Ru1—C1—C281.4 (2)C3—Ru1—C5—C6103.3 (2)
C2—Ru1—C1—C7114.0 (4)C1—Ru1—C5—C628.1 (2)
C6—Ru1—C1—C7115.6 (4)C4—Ru1—C5—C6132.9 (4)
C5—Ru1—C1—C7144.3 (4)Cl2—Ru1—C5—C683.3 (2)
C3—Ru1—C1—C7142.6 (4)Cl1i—Ru1—C5—C6171.9 (2)
C4—Ru1—C1—C7179.2 (4)Cl1—Ru1—C5—C616.7 (5)
Cl2—Ru1—C1—C755.6 (3)C2—C1—C6—C50.1 (5)
Cl1i—Ru1—C1—C7113.2 (4)C7—C1—C6—C5178.0 (3)
Cl1—Ru1—C1—C732.5 (3)Ru1—C1—C6—C553.2 (3)
C6—C1—C2—C30.5 (5)C2—C1—C6—Ru153.3 (3)
C7—C1—C2—C3178.6 (3)C7—C1—C6—Ru1124.8 (3)
Ru1—C1—C2—C354.0 (3)C4—C5—C6—C10.7 (5)
C6—C1—C2—Ru153.5 (3)Ru1—C5—C6—C153.8 (3)
C7—C1—C2—Ru1124.6 (3)C4—C5—C6—Ru154.5 (3)
C6—Ru1—C2—C3103.4 (2)C2—Ru1—C6—C130.5 (2)
C5—Ru1—C2—C365.5 (2)C5—Ru1—C6—C1133.8 (3)
C1—Ru1—C2—C3133.5 (3)C3—Ru1—C6—C168.0 (2)
C4—Ru1—C2—C328.5 (2)C4—Ru1—C6—C1105.2 (2)
Cl2—Ru1—C2—C3152.7 (2)Cl2—Ru1—C6—C1126.8 (2)
Cl1i—Ru1—C2—C346.8 (2)Cl1i—Ru1—C6—C1149.55 (19)
Cl1—Ru1—C2—C3126.5 (2)Cl1—Ru1—C6—C140.6 (2)
C6—Ru1—C2—C130.11 (19)C2—Ru1—C6—C5103.3 (3)
C5—Ru1—C2—C168.0 (2)C3—Ru1—C6—C565.8 (2)
C3—Ru1—C2—C1133.5 (3)C1—Ru1—C6—C5133.8 (3)
C4—Ru1—C2—C1105.0 (2)C4—Ru1—C6—C528.6 (2)
Cl2—Ru1—C2—C119.2 (3)Cl2—Ru1—C6—C599.4 (2)
Cl1i—Ru1—C2—C1179.70 (15)Cl1i—Ru1—C6—C515.7 (4)
Cl1—Ru1—C2—C199.94 (19)Cl1—Ru1—C6—C5174.39 (19)
C1—C2—C3—C40.5 (5)C6—C1—C7—C925.2 (5)
Ru1—C2—C3—C453.6 (3)C2—C1—C7—C9152.8 (4)
C1—C2—C3—Ru154.1 (3)Ru1—C1—C7—C964.5 (5)
C6—Ru1—C3—C266.0 (2)C6—C1—C7—C898.2 (4)
C5—Ru1—C3—C2103.9 (2)C2—C1—C7—C883.9 (4)
C1—Ru1—C3—C228.7 (2)Ru1—C1—C7—C8172.2 (3)
C4—Ru1—C3—C2133.3 (3)C22—N1—C11—C12178.6 (4)
Cl2—Ru1—C3—C2127.0 (3)C22—N1—C11—C161.1 (4)
Cl1i—Ru1—C3—C2142.2 (2)N1—C11—C12—C13180.0 (4)
Cl1—Ru1—C3—C259.1 (2)C16—C11—C12—C130.4 (6)
C2—Ru1—C3—C4133.3 (3)C11—C12—C13—C140.4 (7)
C6—Ru1—C3—C467.3 (2)C12—C13—C14—C150.4 (8)
C5—Ru1—C3—C429.41 (19)C13—C14—C15—C160.4 (7)
C1—Ru1—C3—C4104.6 (2)C12—C11—C16—C150.4 (6)
Cl2—Ru1—C3—C46.3 (5)N1—C11—C16—C15179.9 (3)
Cl1i—Ru1—C3—C484.47 (19)C12—C11—C16—C17178.9 (4)
Cl1—Ru1—C3—C4167.64 (17)N1—C11—C16—C170.8 (4)
C2—C3—C4—C50.1 (5)C14—C15—C16—C110.4 (6)
Ru1—C3—C4—C552.7 (3)C14—C15—C16—C17178.7 (4)
C2—C3—C4—C10176.1 (3)C11—C16—C17—C18177.7 (4)
Ru1—C3—C4—C10123.3 (3)C15—C16—C17—C181.5 (8)
C2—C3—C4—Ru152.8 (3)C11—C16—C17—C220.2 (4)
C2—Ru1—C4—C5102.9 (2)C15—C16—C17—C22179.4 (4)
C6—Ru1—C4—C529.3 (2)C22—C17—C18—C190.2 (6)
C3—Ru1—C4—C5131.7 (3)C16—C17—C18—C19177.5 (4)
C1—Ru1—C4—C565.8 (2)C17—C18—C19—C201.0 (6)
Cl2—Ru1—C4—C546.0 (2)C18—C19—C20—C211.0 (7)
Cl1i—Ru1—C4—C5131.2 (2)C19—C20—C21—C220.2 (6)
Cl1—Ru1—C4—C5153.20 (19)C11—N1—C22—C21178.3 (4)
C2—Ru1—C4—C328.8 (2)C11—N1—C22—C170.9 (4)
C6—Ru1—C4—C3102.4 (2)C20—C21—C22—N1178.6 (4)
C5—Ru1—C4—C3131.7 (3)C20—C21—C22—C170.6 (6)
C1—Ru1—C4—C365.9 (2)C18—C17—C22—N1178.7 (3)
Cl2—Ru1—C4—C3177.76 (16)C16—C17—C22—N10.4 (4)
Cl1i—Ru1—C4—C397.04 (19)C18—C17—C22—C210.6 (5)
Cl1—Ru1—C4—C321.5 (3)C16—C17—C22—C21178.9 (3)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl20.862.633.381 (3)146

Experimental details

Crystal data
Chemical formula[Ru2Cl4(C10H14)2]·2C12H9N
Mr946.77
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)8.1427 (5), 18.3212 (14), 27.303 (3)
V3)4073.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.04
Crystal size (mm)0.65 × 0.31 × 0.11
Data collection
DiffractometerStoe IPDS2
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.803, 0.902
No. of measured, independent and
observed [I > 2σ(I)] reflections
13233, 3964, 2660
Rint0.040
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.073, 1.01
No. of reflections3964
No. of parameters239
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.42

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
Ru1—C22.150 (4)N1—C111.390 (4)
Ru1—C62.153 (3)C1—C61.398 (5)
Ru1—C52.159 (3)C1—C21.417 (5)
Ru1—C32.169 (4)C2—C31.408 (5)
Ru1—C12.180 (3)C3—C41.409 (5)
Ru1—C42.193 (3)C4—C51.398 (5)
N1—C221.373 (4)C5—C61.423 (5)
Cl2—Ru1—Cl1i86.05 (4)Cl1i—Ru1—Cl182.08 (3)
Cl2—Ru1—Cl186.33 (4)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl20.862.633.381 (3)146.2
 

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