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The novel title ruthenium(II) complex, [RuCl(C10H14)(C10H10N3OS)], was synthesized from the reaction of 1,2,4-triazepine, a new class of bidentate ligands, with [Ru(p-cymene)Cl2]2. The 1,2,4-triazepine ligand is coordinated to the metal centre through the N-4 and S atoms, forming a four-membered chelate ring. This is the first structural example of a transition metal complex containing a 1,2,4-triazepine ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008891/qa0323sup1.cif
Contains datablocks II, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008891/qa0323IIsup2.hkl
Contains datablock II

CCDC reference: 150372

Comment top

Heterocylic compounds have found widespread application in both pharmacology as active drugs (Pauwels et al., 1990; Koop et al., 1991) and chemistry as useful reaction intermediates in organic synthesis (Anderson & Raju, 1989; Steinmeyer & Neef, 1992). They are also good ligands which coordinate readily with transition metals to provide versatile and useful complexes (Ghosh et al., 1998; Wills, 1998; Shi et al., 1999). However, the preparation of transition metal complexes with 1,2,4-tiazepines as ligands is not well documented. This can probably be ascribed to the difficulty of synthesis of these heterocycles and to the triazepine nucleus instability (Ait Itto et al., 1997).

In the course of our research on transition metal complexes (El Firdoussi et al., 1993, 1997; Abouhamza et al., 1999), we report here the crystal structure of a new triazepine based ruthenium(II) complex, namely Chloro(η6-p-cymene)(2-methyl-5-oxo-7-phenyl-5,6-dihydro-2H-1,2,4-triazepin- 3-thiolato-κ2N4,S)ruthenium(II), (II). This kind of complex which has a great conformational rigidity could lead to catalysts of high selectivity. The title compound was prepared by reaction in 2-propanol of the 1,2,4-triazepine (I) with [Ru(p-cymene)Cl2]2 in the presence of triethylamine. Crystals were isolated and characterized by X-ray diffraction. Various complexes of the type [Ru(arene)(heteroatomic ligand)Cl] have been crystallographically characterized (Nishiyama et al., 1989; Suzuki et al., 1996).

Complex (II) is, to the best of our knowledge, the first structural example of a transition metal complex containing a 1,2,4-triazepine ligand. The latter acts as a bidentate ligand (through N1 and S1), forming a four-membered chelate ring. The p-cymene and Cl ligands complete the coordination sphere of the RuII atom.

The crystal structure has two similar molecules in its asymmetric unit pseudo-centrosymmetrically arranged, but no additional crystallographic symmetry was found (Le Page, 1987, 1988). Both molecules have the same arrangement and have very close geometries. Average distances involving ruthenium coordination: Ru—N 2.097 (8), Ru—Cl 2.404 (2), Ru—S 2.438 (3) and Ru–centroid 1.67 (1) Å. Average angles involving ruthenium coordination: N—Ru—Cl 85.9 (2), Cl—Ru—S 82.08 (9), N—Ru—S 66.8 (2), N—Ru—centroid 133.0 (3), S—Ru—centroid 135.3 (3) and Cl—Ru—centroid 128.3 (3)°.

Experimental top

Complex (II) was prepared by reaction of [Ru(p-cymene)Cl2]2, 1,2,4-triazepine (I) and triethyamine (molar ratio 1:4:8) in 2-propanol at 353 K. The resulting solid was filtered off and recrystallized from CHCl3.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL (Otwinowski & Minor, 1997); data reduction: HKL; program(s) used to solve structure: DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1992); software used to prepare material for publication: SHELXL97.

Chloro(η6-p-cymene)(2-methyl-5-oxo-7-phenyl-5,6-dihydro-2H-1,2,4-triazepin- 3-thiolato-κ2N4,S)ruthenium top
Crystal data top
[RuCl(C10H14)(C10H11N3OS)]F(000) = 2048
Mr = 503.01Dx = 1.592 Mg m3
Monoclinic, CcCu Kα radiation, λ = 1.54184 Å
a = 20.647 (2) ÅCell parameters from 8671 reflections
b = 11.835 (1) Åθ = 4.3–68.2°
c = 17.275 (2) ŵ = 8.28 mm1
β = 96.253 (5)°T = 293 K
V = 4196.2 (7) Å3Prismatic, colourless
Z = 80.7 × 0.2 × 0.2 mm
Data collection top
Nonius KappaCCD
diffractometer
5007 independent reflections
Radiation source: fine-focus sealed tube4791 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 9.43 pixels mm-1θmax = 68.2°, θmin = 4.3°
ω scansh = 2423
Absorption correction: empirical (using intensity measurements)
(using ΔF; Parkin et al., 1995)
k = 014
Tmin = 0.050, Tmax = 0.189l = 2020
8671 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)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119Calculated w = 1/[σ2(Fo2) + (0.0718P)2 + 9.2057P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5007 reflectionsΔρmax = 0.95 e Å3
584 parametersΔρmin = 0.80 e Å3
2 restraintsAbsolute structure: Flack (1983), Friedel pairs merged
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.467 (14)
Crystal data top
[RuCl(C10H14)(C10H11N3OS)]V = 4196.2 (7) Å3
Mr = 503.01Z = 8
Monoclinic, CcCu Kα radiation
a = 20.647 (2) ŵ = 8.28 mm1
b = 11.835 (1) ÅT = 293 K
c = 17.275 (2) Å0.7 × 0.2 × 0.2 mm
β = 96.253 (5)°
Data collection top
Nonius KappaCCD
diffractometer
5007 independent reflections
Absorption correction: empirical (using intensity measurements)
(using ΔF; Parkin et al., 1995)
4791 reflections with I > 2σ(I)
Tmin = 0.050, Tmax = 0.189Rint = 0.052
8671 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119Δρmax = 0.95 e Å3
S = 1.03Δρmin = 0.80 e Å3
5007 reflectionsAbsolute structure: Flack (1983), Friedel pairs merged
584 parametersAbsolute structure parameter: 0.467 (14)
2 restraints
Special details top

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
Ru10.50133 (3)0.33202 (5)0.49972 (4)0.0267 (2)
Cl10.41055 (12)0.2478 (3)0.42157 (16)0.0529 (7)
S10.45099 (11)0.25636 (19)0.61058 (15)0.0352 (6)
O10.4188 (4)0.5740 (6)0.4445 (4)0.0504 (19)
N10.4322 (4)0.4410 (7)0.5401 (5)0.0298 (18)
N20.3796 (4)0.4311 (7)0.6584 (5)0.042 (2)
N30.3766 (4)0.5476 (7)0.6740 (5)0.0357 (19)
C10.4149 (5)0.3884 (8)0.6036 (6)0.028 (2)
C20.3602 (4)0.6116 (7)0.6172 (6)0.030 (2)
C30.3393 (5)0.5683 (9)0.5373 (6)0.039 (2)
H310.31560.62380.50400.073 (7)*
H320.31130.50320.54150.073 (7)*
C40.3998 (4)0.5286 (8)0.5021 (6)0.034 (2)
C50.3667 (4)0.7351 (9)0.6349 (6)0.033 (2)
C60.3658 (5)0.8144 (9)0.5742 (7)0.039 (3)
H60.36050.79100.52260.02 (2)*
C70.3732 (5)0.9289 (10)0.5927 (7)0.045 (3)
H70.37290.98170.55280.04 (3)*
C80.3806 (5)0.9640 (9)0.6671 (8)0.049 (3)
H80.38461.04080.67800.04 (3)*
C90.3824 (6)0.8884 (10)0.7269 (8)0.047 (3)
H90.388 (5)0.904 (8)0.783 (7)0.04 (3)*
C100.3746 (5)0.7731 (10)0.7108 (7)0.042 (3)
H100.375 (7)0.737 (13)0.743 (8)0.073 (7)*
C110.3645 (6)0.3589 (11)0.7235 (8)0.055 (3)
H1110.32500.35940.72620.073 (7)*
H1120.38650.38740.77130.073 (7)*
H1130.37840.28280.71550.073 (7)*
C120.6004 (5)0.3370 (7)0.5571 (6)0.028 (2)
C130.5937 (4)0.2431 (8)0.5065 (6)0.030 (2)
H130.610 (7)0.186 (11)0.534 (8)0.073 (7)*
C140.5701 (5)0.2546 (9)0.4290 (7)0.037 (2)
H140.56170.22210.37990.05 (3)*
C150.5529 (5)0.3660 (10)0.3963 (7)0.040 (2)
C160.5609 (5)0.4553 (10)0.4461 (6)0.041 (3)
H160.55420.51850.41410.07 (4)*
C170.5813 (5)0.4423 (10)0.5276 (7)0.040 (3)
H170.58930.51540.54600.073 (7)*
C180.6256 (5)0.3143 (10)0.6420 (6)0.040 (3)
H180.59730.25380.65740.04 (3)*
C190.6998 (5)0.3028 (12)0.6462 (7)0.058 (3)
H1910.71470.35560.62300.073 (7)*
H1920.71020.23270.62240.073 (7)*
H1930.71830.30320.69970.073 (7)*
C200.6073 (6)0.4073 (10)0.6964 (7)0.058 (3)
H2010.57400.43900.67710.073 (7)*
H2020.64230.46100.70320.073 (7)*
H2030.60000.37630.74610.073 (7)*
C210.5247 (7)0.3805 (12)0.3124 (7)0.059 (3)
H2110.49090.41730.31070.10 (6)*
H2120.51540.30750.28970.11 (6)*
H2130.55520.41930.28370.13 (7)*
Ru20.39153 (3)0.09821 (5)0.04224 (3)0.0262 (2)
Cl20.29934 (12)0.0401 (3)0.13026 (17)0.0600 (8)
S20.33700 (12)0.0103 (2)0.05997 (15)0.0374 (6)
O20.3221 (4)0.3533 (6)0.0808 (4)0.0482 (18)
N210.3269 (4)0.2078 (7)0.0056 (5)0.0278 (17)
N220.2641 (4)0.1774 (6)0.1137 (5)0.034 (2)
N230.2616 (4)0.2893 (7)0.1375 (5)0.0343 (19)
C310.3042 (5)0.1443 (8)0.0587 (6)0.029 (2)
C320.2502 (4)0.3664 (9)0.0853 (5)0.035 (2)
C330.2357 (5)0.3394 (8)0.0008 (6)0.036 (2)
H3310.20960.27250.01190.02 (2)*
H3320.22000.39940.03460.05 (3)*
C340.2970 (4)0.3052 (8)0.0298 (6)0.033 (2)
C350.2544 (4)0.4866 (8)0.1106 (6)0.034 (2)
C360.2631 (5)0.5740 (10)0.0608 (7)0.045 (3)
H360.26400.56240.00770.08 (4)*
C370.2694 (5)0.6847 (11)0.0881 (10)0.056 (4)
H370.28860.70660.04420.16 (10)*
C380.2675 (6)0.7076 (12)0.1650 (9)0.062 (4)
H380.27880.77800.18620.073 (7)*
C390.2572 (6)0.6224 (11)0.2162 (8)0.054 (3)
H390.26430.65580.26510.06 (3)*
C400.2513 (5)0.5113 (10)0.1917 (6)0.046 (3)
H400.25080.45480.22900.03 (2)*
C410.2441 (7)0.0992 (11)0.1707 (8)0.061 (4)
H4110.22510.14020.21050.073 (7)*
H4120.28130.05790.19370.073 (7)*
H4130.21260.04740.14580.073 (7)*
C420.4880 (5)0.1199 (10)0.0234 (6)0.032 (2)
C430.4680 (5)0.0066 (9)0.0972 (7)0.040 (3)
H430.46100.05710.12850.04 (3)*
C440.4862 (4)0.0135 (9)0.0163 (6)0.036 (2)
H440.49300.05690.00710.073 (7)*
C450.4505 (5)0.1044 (8)0.1422 (6)0.037 (3)
C460.4716 (5)0.2171 (8)0.0207 (6)0.036 (2)
H460.47110.28700.00370.073 (7)*
C470.4536 (5)0.2095 (11)0.1040 (7)0.044 (3)
H470.43690.27100.13320.06 (4)*
C480.5075 (5)0.1226 (9)0.1103 (6)0.040 (2)
H480.50150.04680.13110.073 (7)*
C490.5824 (5)0.1299 (11)0.1259 (7)0.057 (3)
H4910.59780.19140.09660.073 (7)*
H4920.60130.06050.11040.073 (7)*
H4930.59470.14250.18040.073 (7)*
C500.4772 (6)0.2195 (12)0.1507 (7)0.065 (3)
H5010.43260.22840.12940.073 (7)*
H5020.50070.28790.14280.073 (7)*
H5030.47910.20400.20540.073 (7)*
C510.4297 (7)0.0938 (12)0.2274 (7)0.060 (4)
H5110.38390.10870.23740.08 (5)*
H5120.43860.01860.24430.20 (11)*
H5130.45330.14720.25540.14 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0262 (3)0.0247 (4)0.0291 (4)0.0012 (3)0.0028 (3)0.0014 (3)
Cl10.0382 (13)0.076 (2)0.0432 (16)0.0151 (12)0.0005 (11)0.0119 (13)
S10.0377 (12)0.0289 (13)0.0401 (15)0.0047 (9)0.0086 (11)0.0075 (10)
O10.066 (5)0.047 (5)0.041 (5)0.021 (4)0.018 (4)0.018 (4)
N10.038 (4)0.025 (4)0.029 (5)0.002 (3)0.013 (4)0.001 (3)
N20.046 (5)0.033 (5)0.046 (6)0.004 (4)0.007 (5)0.010 (4)
N30.036 (4)0.039 (5)0.032 (5)0.007 (4)0.007 (3)0.001 (4)
C10.033 (5)0.031 (6)0.021 (5)0.004 (4)0.004 (4)0.003 (4)
C20.029 (4)0.032 (5)0.031 (5)0.011 (4)0.010 (4)0.001 (4)
C30.039 (5)0.035 (6)0.041 (6)0.008 (4)0.008 (4)0.006 (4)
C40.036 (5)0.037 (6)0.027 (6)0.012 (4)0.003 (4)0.002 (4)
C50.027 (4)0.044 (6)0.030 (6)0.013 (4)0.001 (4)0.002 (4)
C60.031 (5)0.045 (7)0.041 (7)0.005 (4)0.002 (5)0.008 (5)
C70.031 (5)0.038 (7)0.068 (9)0.011 (4)0.016 (5)0.009 (6)
C80.046 (6)0.031 (7)0.071 (9)0.003 (5)0.006 (6)0.005 (5)
C90.056 (7)0.045 (7)0.041 (8)0.001 (5)0.012 (6)0.005 (5)
C100.034 (5)0.043 (7)0.049 (8)0.002 (5)0.003 (5)0.008 (5)
C110.069 (8)0.048 (7)0.055 (8)0.020 (6)0.038 (6)0.020 (6)
C120.024 (4)0.028 (6)0.033 (6)0.001 (4)0.002 (4)0.005 (4)
C130.023 (4)0.025 (5)0.042 (6)0.003 (4)0.008 (4)0.003 (4)
C140.041 (5)0.031 (6)0.037 (6)0.005 (4)0.001 (5)0.002 (5)
C150.043 (6)0.034 (6)0.043 (7)0.002 (5)0.008 (5)0.005 (5)
C160.044 (6)0.040 (7)0.039 (7)0.003 (5)0.001 (5)0.010 (5)
C170.026 (5)0.044 (7)0.052 (8)0.012 (5)0.010 (5)0.002 (5)
C180.036 (5)0.051 (7)0.035 (6)0.012 (5)0.004 (5)0.003 (5)
C190.046 (6)0.086 (9)0.038 (7)0.010 (6)0.011 (5)0.005 (6)
C200.062 (8)0.072 (9)0.039 (7)0.003 (6)0.003 (6)0.017 (5)
C210.060 (8)0.070 (9)0.047 (8)0.006 (7)0.002 (6)0.013 (6)
Ru20.0265 (3)0.0255 (4)0.0269 (4)0.0008 (3)0.0037 (3)0.0019 (3)
Cl20.0378 (13)0.091 (2)0.0508 (18)0.0139 (14)0.0010 (12)0.0214 (15)
S20.0424 (13)0.0289 (13)0.0432 (16)0.0053 (10)0.0148 (12)0.0066 (10)
O20.054 (4)0.051 (5)0.040 (4)0.008 (4)0.010 (4)0.014 (4)
N210.031 (4)0.028 (4)0.025 (4)0.003 (3)0.006 (3)0.003 (3)
N220.035 (4)0.033 (5)0.036 (5)0.005 (3)0.014 (4)0.005 (4)
N230.043 (4)0.035 (5)0.026 (5)0.009 (4)0.011 (3)0.000 (3)
C310.030 (5)0.025 (5)0.033 (6)0.003 (4)0.009 (5)0.005 (4)
C320.028 (5)0.047 (6)0.028 (6)0.008 (4)0.000 (4)0.003 (4)
C330.035 (5)0.028 (6)0.042 (7)0.001 (4)0.005 (4)0.011 (4)
C340.037 (5)0.030 (5)0.030 (6)0.007 (4)0.003 (5)0.000 (4)
C350.027 (4)0.038 (6)0.037 (6)0.013 (4)0.003 (4)0.003 (4)
C360.035 (5)0.054 (7)0.046 (8)0.006 (5)0.006 (5)0.000 (6)
C370.034 (6)0.045 (8)0.089 (12)0.007 (5)0.011 (7)0.007 (7)
C380.041 (6)0.059 (9)0.084 (12)0.006 (6)0.006 (6)0.014 (8)
C390.058 (7)0.058 (8)0.043 (8)0.009 (6)0.002 (6)0.012 (6)
C400.053 (6)0.049 (7)0.035 (7)0.020 (5)0.006 (5)0.010 (5)
C410.065 (8)0.078 (10)0.045 (8)0.022 (6)0.038 (7)0.017 (6)
C420.024 (5)0.049 (6)0.025 (6)0.007 (4)0.010 (4)0.002 (4)
C430.039 (5)0.034 (6)0.048 (7)0.004 (4)0.015 (5)0.011 (5)
C440.031 (5)0.035 (6)0.038 (6)0.002 (4)0.013 (4)0.002 (4)
C450.034 (5)0.043 (7)0.031 (6)0.005 (4)0.006 (4)0.008 (4)
C460.040 (5)0.024 (6)0.043 (7)0.001 (4)0.003 (5)0.011 (4)
C470.034 (5)0.045 (7)0.054 (8)0.007 (5)0.014 (5)0.008 (6)
C480.051 (6)0.034 (6)0.037 (6)0.008 (5)0.003 (5)0.001 (5)
C490.048 (6)0.067 (8)0.052 (8)0.004 (6)0.015 (6)0.003 (6)
C500.072 (8)0.091 (10)0.029 (7)0.001 (7)0.001 (6)0.020 (6)
C510.068 (8)0.090 (11)0.020 (6)0.002 (7)0.004 (6)0.008 (6)
Geometric parameters (Å, º) top
Ru1—N12.099 (8)Ru2—N212.095 (8)
Ru1—C172.119 (10)Ru2—C462.171 (9)
Ru1—C132.171 (9)Ru2—C472.194 (11)
Ru1—C142.174 (12)Ru2—C422.196 (10)
Ru1—C122.174 (9)Ru2—C442.199 (9)
Ru1—C162.180 (11)Ru2—C432.213 (11)
Ru1—C152.214 (12)Ru2—C452.219 (12)
Ru1—Cl12.404 (2)Ru2—Cl22.404 (2)
Ru1—S12.446 (3)Ru2—S22.429 (3)
S1—C11.731 (10)S2—C311.724 (10)
O1—C41.230 (12)O2—C341.212 (12)
N1—C11.342 (13)N21—C311.310 (13)
N1—C41.364 (12)N21—C341.415 (12)
N2—C11.354 (14)N22—C311.383 (14)
N2—N31.406 (12)N22—N231.391 (11)
N2—C111.473 (14)N22—C411.444 (14)
N3—C21.257 (12)N23—C321.287 (12)
C2—C31.492 (14)C32—C351.488 (14)
C2—C51.496 (14)C32—C331.492 (14)
C3—C41.522 (14)C33—C341.481 (14)
C3—H310.9697C33—H3310.9688
C3—H320.9702C33—H3320.9694
C5—C101.378 (16)C35—C361.371 (16)
C5—C61.406 (14)C35—C401.438 (15)
C6—C71.396 (15)C36—C371.394 (17)
C6—H60.9300C36—H360.9300
C7—C81.344 (16)C37—C381.36 (2)
C7—H70.9300C37—H370.9305
C8—C91.364 (17)C38—C391.37 (2)
C8—H80.9300C38—H380.9299
C9—C101.398 (17)C39—C401.383 (16)
C9—H90.98 (11)C39—H390.9301
C10—H100.70 (14)C40—H400.9300
C11—H1110.8200C41—H4110.9600
C11—H1120.9600C41—H4120.9600
C11—H1130.9600C41—H4130.9600
C12—C171.387 (15)C42—C461.401 (15)
C12—C131.412 (13)C42—C441.432 (15)
C12—C181.525 (16)C42—C481.512 (16)
C13—C141.381 (15)C43—C441.410 (15)
C13—H130.87 (13)C43—C451.419 (15)
C14—C151.463 (15)C43—H430.9299
C14—H140.9303C44—H440.9298
C15—C161.361 (16)C45—C471.406 (16)
C15—C211.511 (16)C45—C511.494 (16)
C16—C171.434 (16)C46—C471.448 (16)
C16—H160.9302C46—H460.9301
C17—H170.9300C47—H470.9297
C18—C201.522 (16)C48—C501.513 (17)
C18—C191.532 (15)C48—C491.543 (15)
C18—H180.9798C48—H480.9794
C19—H1910.8200C49—H4910.9600
C19—H1920.9600C49—H4920.9600
C19—H1930.9600C49—H4930.9600
C20—H2010.8200C50—H5010.9600
C20—H2020.9600C50—H5020.9600
C20—H2030.9599C50—H5030.9600
C21—H2110.8200C51—H5110.9600
C21—H2120.9601C51—H5120.9600
C21—H2130.9599C51—H5130.9600
N1—Ru1—C1795.0 (4)N21—Ru2—C4692.1 (3)
N1—Ru1—C13154.9 (3)N21—Ru2—C47104.6 (4)
C17—Ru1—C1368.2 (4)C46—Ru2—C4738.8 (4)
N1—Ru1—C14162.8 (3)N21—Ru2—C42107.7 (3)
C17—Ru1—C1481.2 (4)C46—Ru2—C4237.4 (4)
C13—Ru1—C1437.1 (4)C47—Ru2—C4268.7 (4)
N1—Ru1—C12118.1 (3)N21—Ru2—C44142.4 (3)
C17—Ru1—C1237.7 (4)C46—Ru2—C4467.5 (4)
C13—Ru1—C1237.9 (3)C47—Ru2—C4479.6 (4)
C14—Ru1—C1268.2 (4)C42—Ru2—C4438.0 (4)
N1—Ru1—C1699.6 (3)N21—Ru2—C43171.1 (4)
C17—Ru1—C1638.9 (4)C46—Ru2—C4379.9 (4)
C13—Ru1—C1679.3 (4)C47—Ru2—C4366.6 (5)
C14—Ru1—C1667.0 (4)C42—Ru2—C4368.3 (4)
C12—Ru1—C1668.2 (4)C44—Ru2—C4337.3 (4)
N1—Ru1—C15124.1 (4)N21—Ru2—C45135.5 (3)
C17—Ru1—C1568.9 (4)C46—Ru2—C4568.9 (4)
C13—Ru1—C1568.6 (4)C47—Ru2—C4537.1 (4)
C14—Ru1—C1538.9 (4)C42—Ru2—C4581.6 (4)
C12—Ru1—C1581.5 (4)C44—Ru2—C4567.9 (4)
C16—Ru1—C1536.1 (4)C43—Ru2—C4537.3 (4)
N1—Ru1—Cl185.7 (2)N21—Ru2—Cl286.1 (2)
C17—Ru1—Cl1157.5 (3)C46—Ru2—Cl2146.0 (3)
C13—Ru1—Cl1117.1 (3)C47—Ru2—Cl2109.2 (3)
C14—Ru1—Cl191.5 (3)C42—Ru2—Cl2166.1 (3)
C12—Ru1—Cl1154.8 (2)C44—Ru2—Cl2128.6 (3)
C16—Ru1—Cl1118.7 (3)C43—Ru2—Cl298.1 (3)
C15—Ru1—Cl192.1 (3)C45—Ru2—Cl288.9 (3)
N1—Ru1—S166.5 (2)N21—Ru2—S267.2 (2)
C17—Ru1—S1115.8 (3)C46—Ru2—S2123.9 (3)
C13—Ru1—S1103.1 (3)C47—Ru2—S2162.2 (3)
C14—Ru1—S1130.2 (3)C42—Ru2—S298.1 (3)
C12—Ru1—S196.4 (3)C44—Ru2—S297.4 (3)
C16—Ru1—S1152.3 (3)C43—Ru2—S2120.7 (3)
C15—Ru1—S1168.8 (3)C45—Ru2—S2156.4 (3)
Cl1—Ru1—S185.19 (9)Cl2—Ru2—S286.53 (10)
C1—S1—Ru180.3 (4)C31—S2—Ru279.0 (3)
C1—N1—C4125.9 (8)C31—N21—C34126.7 (8)
C1—N1—Ru1103.8 (6)C31—N21—Ru2102.3 (6)
C4—N1—Ru1128.5 (7)C34—N21—Ru2126.9 (7)
C1—N2—N3122.5 (8)C31—N22—N23121.1 (8)
C1—N2—C11119.5 (9)C31—N22—C41121.6 (8)
N3—N2—C11113.9 (9)N23—N22—C41112.7 (9)
C2—N3—N2117.1 (8)C32—N23—N22118.5 (8)
N1—C1—N2127.6 (8)N21—C31—N22127.2 (9)
N1—C1—S1108.9 (7)N21—C31—S2111.5 (7)
N2—C1—S1123.3 (7)N22—C31—S2121.0 (7)
N3—C2—C3122.7 (9)N23—C32—C35118.1 (9)
N3—C2—C5114.8 (8)N23—C32—C33122.4 (9)
C3—C2—C5122.4 (8)C35—C32—C33119.5 (8)
C2—C3—C4108.0 (7)C34—C33—C32108.6 (7)
C2—C3—H31113.1C34—C33—H33199.9
C4—C3—H31110.8C32—C33—H331116.4
C2—C3—H32108.6C34—C33—H332102.5
C4—C3—H32107.9C32—C33—H332118.5
H31—C3—H32108.4H331—C33—H332108.4
O1—C4—N1122.7 (9)O2—C34—N21119.8 (9)
O1—C4—C3122.4 (8)O2—C34—C33125.6 (9)
N1—C4—C3114.9 (9)N21—C34—C33114.7 (8)
C10—C5—C6118.8 (10)C36—C35—C40118.7 (10)
C10—C5—C2120.8 (9)C36—C35—C32123.0 (10)
C6—C5—C2120.4 (9)C40—C35—C32118.3 (10)
C7—C6—C5119.0 (11)C35—C36—C37120.7 (12)
C7—C6—H6120.5C35—C36—H36121.8
C5—C6—H6120.5C37—C36—H36117.5
C8—C7—C6121.1 (11)C38—C37—C36120.4 (14)
C8—C7—H7119.5C38—C37—H37143.3
C6—C7—H7119.5C36—C37—H3791.0
C7—C8—C9120.8 (11)C37—C38—C39120.4 (13)
C7—C8—H8119.6C37—C38—H38122.0
C9—C8—H8119.6C39—C38—H38117.1
C8—C9—C10119.8 (11)C38—C39—C40121.1 (13)
C8—C9—H9128 (5)C38—C39—H39104.7
C10—C9—H9112 (5)C40—C39—H39133.0
C5—C10—C9120.4 (10)C39—C40—C35118.7 (12)
C5—C10—H10123 (10)C39—C40—H40118.6
C9—C10—H10116 (10)C35—C40—H40122.2
N2—C11—H111109.5N22—C41—H411109.5
N2—C11—H112109.4N22—C41—H412109.5
H111—C11—H112109.2H411—C41—H412109.5
N2—C11—H113110.0N22—C41—H413109.5
H111—C11—H113109.3H411—C41—H413109.5
H112—C11—H113109.5H412—C41—H413109.5
C17—C12—C13118.3 (10)C46—C42—C44118.0 (9)
C17—C12—C18124.5 (9)C46—C42—C48123.1 (10)
C13—C12—C18117.2 (8)C44—C42—C48118.9 (9)
C17—C12—Ru169.0 (6)C46—C42—Ru270.3 (6)
C13—C12—Ru170.9 (5)C44—C42—Ru271.1 (5)
C18—C12—Ru1129.8 (7)C48—C42—Ru2130.1 (7)
C14—C13—C12121.6 (9)C44—C43—C45121.3 (9)
C14—C13—Ru171.6 (6)C44—C43—Ru270.8 (6)
C12—C13—Ru171.2 (5)C45—C43—Ru271.5 (6)
C14—C13—H13133 (9)C44—C43—H43129.2
C12—C13—H13106 (9)C45—C43—H43109.2
Ru1—C13—H13134 (9)Ru2—C43—H43124.9
C13—C14—C15120.6 (9)C43—C44—C42121.0 (9)
C13—C14—Ru171.3 (6)C43—C44—Ru271.9 (5)
C15—C14—Ru172.0 (6)C42—C44—Ru270.9 (5)
C13—C14—H14148.7C43—C44—H44112.9
C15—C14—H1490.4C42—C44—H44125.8
Ru1—C14—H14128.2Ru2—C44—H44125.9
C16—C15—C14116.6 (10)C47—C45—C43118.0 (11)
C16—C15—C21121.7 (11)C47—C45—C51122.0 (11)
C14—C15—C21121.6 (11)C43—C45—C51120.0 (10)
C16—C15—Ru170.6 (7)C47—C45—Ru270.5 (7)
C14—C15—Ru169.1 (6)C43—C45—Ru271.1 (7)
C21—C15—Ru1128.7 (8)C51—C45—Ru2129.9 (8)
C15—C16—C17122.7 (10)C42—C46—C47120.7 (10)
C15—C16—Ru173.3 (7)C42—C46—Ru272.3 (6)
C17—C16—Ru168.2 (6)C47—C46—Ru271.5 (6)
C15—C16—H16104.4C42—C46—H46119.8
C17—C16—H16132.7C47—C46—H46119.5
Ru1—C16—H16137.3Ru2—C46—H46127.5
C12—C17—C16119.9 (11)C45—C47—C46120.9 (11)
C12—C17—Ru173.3 (6)C45—C47—Ru272.4 (7)
C16—C17—Ru172.8 (6)C46—C47—Ru269.8 (6)
C12—C17—H17132.6C45—C47—H47116.3
C16—C17—H17104.9C46—C47—H47122.0
Ru1—C17—H17139.0Ru2—C47—H47122.1
C20—C18—C12112.6 (9)C42—C48—C50113.3 (9)
C20—C18—C19110.5 (9)C42—C48—C49109.2 (9)
C12—C18—C19107.3 (9)C50—C48—C49109.5 (9)
C20—C18—H1899.4C42—C48—H48108.3
C12—C18—H18103.7C50—C48—H48116.8
C19—C18—H18123.1C49—C48—H4898.7
C18—C19—H191109.5C48—C49—H491109.5
C18—C19—H192108.9C48—C49—H492109.5
H191—C19—H192109.7H491—C49—H492109.5
C18—C19—H193109.6C48—C49—H493109.5
H191—C19—H193109.7H491—C49—H493109.5
H192—C19—H193109.5H492—C49—H493109.5
C18—C20—H201109.5C48—C50—H501109.5
C18—C20—H202108.6C48—C50—H502109.5
H201—C20—H202109.4H501—C50—H502109.5
C18—C20—H203110.5C48—C50—H503109.5
H201—C20—H203109.4H501—C50—H503109.5
H202—C20—H203109.5H502—C50—H503109.5
C15—C21—H211109.5C45—C51—H511109.5
C15—C21—H212109.2C45—C51—H512109.5
H211—C21—H212109.3H511—C51—H512109.5
C15—C21—H213110.1C45—C51—H513109.5
H211—C21—H213109.2H511—C51—H513109.5
H212—C21—H213109.5H512—C51—H513109.5

Experimental details

Crystal data
Chemical formula[RuCl(C10H14)(C10H11N3OS)]
Mr503.01
Crystal system, space groupMonoclinic, Cc
Temperature (K)293
a, b, c (Å)20.647 (2), 11.835 (1), 17.275 (2)
β (°) 96.253 (5)
V3)4196.2 (7)
Z8
Radiation typeCu Kα
µ (mm1)8.28
Crystal size (mm)0.7 × 0.2 × 0.2
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(using ΔF; Parkin et al., 1995)
Tmin, Tmax0.050, 0.189
No. of measured, independent and
observed [I > 2σ(I)] reflections
8671, 5007, 4791
Rint0.052
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.119, 1.03
No. of reflections5007
No. of parameters584
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.95, 0.80
Absolute structureFlack (1983), Friedel pairs merged
Absolute structure parameter0.467 (14)

Computer programs: COLLECT (Nonius, 1998), HKL (Otwinowski & Minor, 1997), HKL, DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1992), SHELXL97.

 

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