Literature DB >> 21578690

Di-μ(2)-bromido-bis-[bromido(η-1,2,4,5-tetra-methyl-benzene)ruthenium(II)].

Noel Espinosa-Jalapa1, Simón Hernández-Ortega, Ronan Le Lagadec, David Morales-Morales.   

Abstract

The asymmetric unit of the title compound, [Ru(2)Br(4)(C(10)H(14))(2)], contains one half of the centrosymmetric mol-ecule. Each Ru center is coordinated by tetra-methyl-benzene ring in a η(6)-coordination mode, and one terminal and two bridging bromine atoms. The aromatic rings and the Ru(2)Br(2) four-membered ring form a dihedral angle of 55.99 (8)°. In the crystal structure, weak inter-molecular C-H⋯Br inter-actions link mol-ecules into chains propagated in [001].

Entities:  

Year:  2009        PMID： 21578690      PMCID： PMC2972084          DOI： 10.1107/S1600536809049642

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For our work on the synthesis and catalytic applications of ruthenium–arene complexes, see: Cerón-Camacho et al. (2006 ▶); Díaz Camacho et al. (2008 ▶). For related structures, see: González-Torres et al. (2009 ▶) and references therein. For details of the synthesis, see: Bennett et al. (1982 ▶).

Experimental

Crystal data

[Ru2Br4(C10H14)2] M = 790.20 Triclinic, a = 7.8866 (13) Å b = 8.2873 (14) Å c = 9.8627 (17) Å α = 88.335 (2)° β = 74.508 (2)° γ = 69.648 (2)° V = 580.96 (17) Å3 Z = 1 Mo Kα radiation μ = 8.18 mm−1 T = 298 K 0.35 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: face indexed-numerical (SHELXTL>; Sheldrick, 2008 ▶) T min = 0.139, T max = 0.478 4786 measured reflections 2108 independent reflections 1878 reflections with I > 2σ(I) R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.060 S = 1.00 2108 reflections 122 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.65 e Å−3 Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049642/cv2636sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049642/cv2636Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ru2Br4(C10H14)2]Z = 1
Mr = 790.20F(000) = 376
Triclinic, P1Dx = 2.259 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8866 (13) ÅCell parameters from 3668 reflections
b = 8.2873 (14) Åθ = 2.6–25.4°
c = 9.8627 (17) ŵ = 8.18 mm−1
α = 88.335 (2)°T = 298 K
β = 74.508 (2)°Prism, red
γ = 69.648 (2)°0.35 × 0.15 × 0.12 mm
V = 580.96 (17) Å3
Bruker SMART CCD area-detector diffractometer2108 independent reflections
Radiation source: fine-focus sealed tube1878 reflections with I > 2σ(I)
graphiteRint = 0.063
Detector resolution: 0.83 pixels mm-1θmax = 25.4°, θmin = 2.2°
ω scansh = −9→9
Absorption correction: face indexed-numerical (SHELXTL; Sheldrick, 2008)k = −9→9
Tmin = 0.139, Tmax = 0.478l = −11→11
4786 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0227P)2] where P = (Fo2 + 2Fc2)/3
2108 reflections(Δ/σ)max = 0.001
122 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.65 e Å−3
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.
xyzUiso*/Ueq
Ru0.63750 (4)0.49125 (3)0.30491 (3)0.02810 (10)
Br10.64758 (5)0.29795 (4)0.51434 (4)0.04089 (12)
Br20.41130 (6)0.36687 (6)0.24801 (4)0.05137 (14)
C10.8371 (5)0.3925 (4)0.0980 (4)0.0367 (8)
C20.9352 (5)0.3568 (4)0.2017 (4)0.0379 (8)
C30.9134 (5)0.4943 (4)0.2952 (4)0.0377 (8)
H30.97890.46990.36340.045*
C40.7972 (5)0.6654 (4)0.2891 (4)0.0407 (9)
C50.6944 (5)0.7014 (4)0.1860 (4)0.0396 (9)
C60.7172 (5)0.5650 (5)0.0931 (4)0.0389 (8)
H60.65070.58880.02550.047*
C70.8478 (6)0.2543 (5)−0.0040 (4)0.0546 (11)
H7A0.77340.3062−0.06720.082*
H7B0.80060.17170.04750.082*
H7C0.97620.1974−0.05720.082*
C81.0565 (6)0.1754 (5)0.2196 (5)0.0557 (11)
H8A1.17640.14500.15050.084*
H8B0.99590.09670.20730.084*
H8C1.07440.16920.31240.084*
C90.7843 (7)0.8028 (5)0.3909 (5)0.0620 (12)
H9A0.85140.75060.45840.093*
H9B0.65470.86390.43920.093*
H9C0.83850.88180.34050.093*
C100.5588 (7)0.8778 (5)0.1774 (5)0.0629 (13)
H10A0.48300.87070.11760.094*
H10B0.62710.95200.13890.094*
H10C0.47920.92360.27000.094*
U11U22U33U12U13U23
Ru0.02570 (16)0.02940 (16)0.02784 (16)−0.01036 (12)−0.00439 (11)0.00292 (10)
Br10.0380 (2)0.0341 (2)0.0370 (2)−0.00366 (16)−0.00100 (16)0.00683 (15)
Br20.0483 (3)0.0736 (3)0.0462 (2)−0.0382 (2)−0.0134 (2)0.00497 (19)
C10.0333 (19)0.0419 (19)0.0313 (18)−0.0173 (16)0.0031 (15)−0.0009 (15)
C20.0252 (17)0.0367 (19)0.045 (2)−0.0104 (15)0.0003 (15)0.0011 (15)
C30.0300 (19)0.045 (2)0.042 (2)−0.0177 (16)−0.0095 (16)0.0051 (16)
C40.045 (2)0.0378 (19)0.040 (2)−0.0241 (17)−0.0011 (17)0.0014 (15)
C50.039 (2)0.0362 (18)0.040 (2)−0.0169 (17)−0.0010 (16)0.0090 (15)
C60.041 (2)0.049 (2)0.0294 (17)−0.0213 (18)−0.0081 (16)0.0099 (15)
C70.056 (3)0.060 (3)0.047 (2)−0.029 (2)0.001 (2)−0.013 (2)
C80.038 (2)0.046 (2)0.069 (3)−0.0035 (19)−0.007 (2)0.002 (2)
C90.084 (3)0.057 (2)0.056 (3)−0.045 (3)−0.008 (2)−0.006 (2)
C100.066 (3)0.043 (2)0.065 (3)−0.013 (2)−0.006 (2)0.021 (2)
Ru—C62.150 (3)C4—C51.427 (5)
Ru—C32.161 (4)C4—C91.498 (5)
Ru—C52.180 (4)C5—C61.408 (5)
Ru—C22.182 (3)C5—C101.497 (5)
Ru—C12.191 (3)C6—H60.9300
Ru—C42.200 (4)C7—H7A0.9600
Ru—Br22.5313 (6)C7—H7B0.9600
Ru—Br1i2.5676 (5)C7—H7C0.9600
Ru—Br12.5780 (5)C8—H8A0.9600
Br1—Rui2.5676 (5)C8—H8B0.9600
C1—C21.407 (5)C8—H8C0.9600
C1—C61.421 (5)C9—H9A0.9600
C1—C71.511 (5)C9—H9B0.9600
C2—C31.421 (5)C9—H9C0.9600
C2—C81.510 (5)C10—H10A0.9600
C3—C41.406 (5)C10—H10B0.9600
C3—H30.9300C10—H10C0.9600
C6—Ru—C379.89 (15)C4—C3—C2122.8 (3)
C6—Ru—C537.93 (13)C4—C3—Ru72.7 (2)
C3—Ru—C568.14 (14)C2—C3—Ru71.7 (2)
C6—Ru—C268.16 (14)C4—C3—H3118.6
C3—Ru—C238.18 (13)C2—C3—H3118.6
C5—Ru—C281.73 (14)Ru—C3—H3129.7
C6—Ru—C138.21 (14)C3—C4—C5118.3 (3)
C3—Ru—C168.06 (13)C3—C4—C9119.3 (4)
C5—Ru—C169.31 (13)C5—C4—C9122.4 (3)
C2—Ru—C137.53 (14)C3—C4—Ru69.7 (2)
C6—Ru—C468.13 (14)C5—C4—Ru70.2 (2)
C3—Ru—C437.60 (13)C9—C4—Ru131.5 (3)
C5—Ru—C438.01 (14)C6—C5—C4118.6 (3)
C2—Ru—C469.00 (13)C6—C5—C10119.3 (4)
C1—Ru—C481.45 (13)C4—C5—C10122.0 (4)
C6—Ru—Br292.41 (11)C6—C5—Ru69.9 (2)
C3—Ru—Br2154.25 (9)C4—C5—Ru71.7 (2)
C5—Ru—Br2119.06 (11)C10—C5—Ru128.2 (3)
C2—Ru—Br2116.19 (10)C5—C6—C1122.9 (3)
C1—Ru—Br290.67 (10)C5—C6—Ru72.2 (2)
C4—Ru—Br2157.03 (10)C1—C6—Ru72.4 (2)
C6—Ru—Br1i119.11 (10)C5—C6—H6118.5
C3—Ru—Br1i118.25 (9)C1—C6—H6118.5
C5—Ru—Br1i92.02 (9)Ru—C6—H6129.5
C2—Ru—Br1i156.13 (10)C1—C7—H7A109.5
C1—Ru—Br1i157.12 (10)C1—C7—H7B109.5
C4—Ru—Br1i91.93 (9)H7A—C7—H7B109.5
Br2—Ru—Br1i87.02 (2)C1—C7—H7C109.5
C6—Ru—Br1158.03 (10)H7A—C7—H7C109.5
C3—Ru—Br190.73 (10)H7B—C7—H7C109.5
C5—Ru—Br1152.74 (10)C2—C8—H8A109.5
C2—Ru—Br192.20 (10)C2—C8—H8B109.5
C1—Ru—Br1119.82 (10)H8A—C8—H8B109.5
C4—Ru—Br1115.15 (10)C2—C8—H8C109.5
Br2—Ru—Br187.508 (18)H8A—C8—H8C109.5
Br1i—Ru—Br182.838 (17)H8B—C8—H8C109.5
Rui—Br1—Ru97.162 (17)C4—C9—H9A109.5
C2—C1—C6118.3 (3)C4—C9—H9B109.5
C2—C1—C7122.8 (3)H9A—C9—H9B109.5
C6—C1—C7118.8 (3)C4—C9—H9C109.5
C2—C1—Ru70.89 (19)H9A—C9—H9C109.5
C6—C1—Ru69.36 (18)H9B—C9—H9C109.5
C7—C1—Ru129.3 (3)C5—C10—H10A109.5
C1—C2—C3119.0 (3)C5—C10—H10B109.5
C1—C2—C8121.6 (3)H10A—C10—H10B109.5
C3—C2—C8119.3 (3)C5—C10—H10C109.5
C1—C2—Ru71.58 (19)H10A—C10—H10C109.5
C3—C2—Ru70.13 (19)H10B—C10—H10C109.5
C8—C2—Ru128.1 (3)
C6—Ru—Br1—Rui−177.6 (3)Ru—C3—C4—C5−52.5 (3)
C3—Ru—Br1—Rui118.39 (9)C2—C3—C4—C9−179.3 (4)
C5—Ru—Br1—Rui80.4 (2)Ru—C3—C4—C9127.1 (4)
C2—Ru—Br1—Rui156.56 (10)C2—C3—C4—Ru53.6 (3)
C1—Ru—Br1—Rui−176.65 (12)C6—Ru—C4—C3−102.2 (2)
C4—Ru—Br1—Rui88.77 (10)C5—Ru—C4—C3−132.1 (3)
Br2—Ru—Br1—Rui−87.31 (2)C2—Ru—C4—C3−28.2 (2)
Br1i—Ru—Br1—Rui0.0C1—Ru—C4—C3−64.9 (2)
C6—Ru—C1—C2131.8 (3)Br2—Ru—C4—C3−136.0 (2)
C3—Ru—C1—C229.9 (2)Br1i—Ru—C4—C3137.1 (2)
C5—Ru—C1—C2103.8 (2)Br1—Ru—C4—C354.1 (2)
C4—Ru—C1—C266.5 (2)C6—Ru—C4—C529.92 (19)
Br2—Ru—C1—C2−135.2 (2)C3—Ru—C4—C5132.1 (3)
Br1i—Ru—C1—C2140.9 (2)C2—Ru—C4—C5103.9 (2)
Br1—Ru—C1—C2−47.7 (2)C1—Ru—C4—C567.2 (2)
C3—Ru—C1—C6−101.9 (2)Br2—Ru—C4—C5−3.9 (4)
C5—Ru—C1—C6−27.9 (2)Br1i—Ru—C4—C5−90.81 (19)
C2—Ru—C1—C6−131.8 (3)Br1—Ru—C4—C5−173.80 (16)
C4—Ru—C1—C6−65.3 (2)C6—Ru—C4—C9146.2 (4)
Br2—Ru—C1—C693.0 (2)C3—Ru—C4—C9−111.6 (5)
Br1i—Ru—C1—C69.1 (4)C5—Ru—C4—C9116.3 (5)
Br1—Ru—C1—C6−179.45 (18)C2—Ru—C4—C9−139.8 (4)
C6—Ru—C1—C7−111.0 (4)C1—Ru—C4—C9−176.5 (4)
C3—Ru—C1—C7147.2 (4)Br2—Ru—C4—C9112.4 (4)
C5—Ru—C1—C7−138.9 (4)Br1i—Ru—C4—C925.5 (4)
C2—Ru—C1—C7117.2 (4)Br1—Ru—C4—C9−57.5 (4)
C4—Ru—C1—C7−176.3 (4)C3—C4—C5—C6−1.4 (5)
Br2—Ru—C1—C7−17.9 (3)C9—C4—C5—C6179.0 (3)
Br1i—Ru—C1—C7−101.9 (4)Ru—C4—C5—C6−53.7 (3)
Br1—Ru—C1—C769.6 (4)C3—C4—C5—C10176.4 (4)
C6—C1—C2—C3−1.2 (5)C9—C4—C5—C10−3.2 (6)
C7—C1—C2—C3−178.6 (3)Ru—C4—C5—C10124.1 (4)
Ru—C1—C2—C3−53.6 (3)C3—C4—C5—Ru52.3 (3)
C6—C1—C2—C8176.3 (4)C9—C4—C5—Ru−127.3 (4)
C7—C1—C2—C8−1.1 (6)C3—Ru—C5—C6102.0 (2)
Ru—C1—C2—C8123.9 (4)C2—Ru—C5—C664.8 (2)
C6—C1—C2—Ru52.4 (3)C1—Ru—C5—C628.1 (2)
C7—C1—C2—Ru−125.0 (4)C4—Ru—C5—C6131.1 (3)
C6—Ru—C2—C1−29.8 (2)Br2—Ru—C5—C6−50.6 (2)
C3—Ru—C2—C1−131.6 (3)Br1i—Ru—C5—C6−138.3 (2)
C5—Ru—C2—C1−66.6 (2)Br1—Ru—C5—C6143.5 (2)
C4—Ru—C2—C1−103.8 (2)C6—Ru—C5—C4−131.1 (3)
Br2—Ru—C2—C151.8 (2)C3—Ru—C5—C4−29.2 (2)
Br1i—Ru—C2—C1−142.7 (2)C2—Ru—C5—C4−66.3 (2)
Br1—Ru—C2—C1140.1 (2)C1—Ru—C5—C4−103.0 (2)
C6—Ru—C2—C3101.8 (2)Br2—Ru—C5—C4178.27 (16)
C5—Ru—C2—C364.9 (2)Br1i—Ru—C5—C490.55 (19)
C1—Ru—C2—C3131.6 (3)Br1—Ru—C5—C412.3 (3)
C4—Ru—C2—C327.8 (2)C6—Ru—C5—C10112.1 (5)
Br2—Ru—C2—C3−176.69 (17)C3—Ru—C5—C10−146.0 (4)
Br1i—Ru—C2—C3−11.2 (4)C2—Ru—C5—C10176.9 (4)
Br1—Ru—C2—C3−88.4 (2)C1—Ru—C5—C10140.2 (4)
C6—Ru—C2—C8−146.0 (4)C4—Ru—C5—C10−116.8 (4)
C3—Ru—C2—C8112.3 (4)Br2—Ru—C5—C1061.5 (4)
C5—Ru—C2—C8177.2 (4)Br1i—Ru—C5—C10−26.2 (4)
C1—Ru—C2—C8−116.2 (4)Br1—Ru—C5—C10−104.5 (4)
C4—Ru—C2—C8140.0 (4)C4—C5—C6—C10.4 (5)
Br2—Ru—C2—C8−64.4 (4)C10—C5—C6—C1−177.4 (4)
Br1i—Ru—C2—C8101.1 (4)Ru—C5—C6—C1−54.1 (3)
Br1—Ru—C2—C823.9 (3)C4—C5—C6—Ru54.6 (3)
C1—C2—C3—C40.2 (5)C10—C5—C6—Ru−123.3 (4)
C8—C2—C3—C4−177.4 (4)C2—C1—C6—C50.9 (5)
Ru—C2—C3—C4−54.1 (3)C7—C1—C6—C5178.4 (3)
C1—C2—C3—Ru54.3 (3)Ru—C1—C6—C554.0 (3)
C8—C2—C3—Ru−123.3 (3)C2—C1—C6—Ru−53.1 (3)
C6—Ru—C3—C467.1 (2)C7—C1—C6—Ru124.4 (3)
C5—Ru—C3—C429.5 (2)C3—Ru—C6—C5−67.3 (2)
C2—Ru—C3—C4134.5 (3)C2—Ru—C6—C5−105.2 (2)
C1—Ru—C3—C4105.1 (2)C1—Ru—C6—C5−134.5 (3)
Br2—Ru—C3—C4141.4 (2)C4—Ru—C6—C5−30.0 (2)
Br1i—Ru—C3—C4−50.6 (2)Br2—Ru—C6—C5137.5 (2)
Br1—Ru—C3—C4−132.8 (2)Br1i—Ru—C6—C549.5 (2)
C6—Ru—C3—C2−67.4 (2)Br1—Ru—C6—C5−133.2 (2)
C5—Ru—C3—C2−105.0 (2)C3—Ru—C6—C167.2 (2)
C1—Ru—C3—C2−29.4 (2)C5—Ru—C6—C1134.5 (3)
C4—Ru—C3—C2−134.5 (3)C2—Ru—C6—C129.3 (2)
Br2—Ru—C3—C26.9 (4)C4—Ru—C6—C1104.5 (2)
Br1i—Ru—C3—C2174.90 (17)Br2—Ru—C6—C1−88.0 (2)
Br1—Ru—C3—C292.6 (2)Br1i—Ru—C6—C1−175.95 (18)
C2—C3—C4—C51.1 (5)Br1—Ru—C6—C11.3 (4)
D—H···AD—HH···AD···AD—H···A
C6—H6···Br2ii0.932.863.739 (4)158
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C6—H6⋯Br2i 0.932.863.739 (4)158

Symmetry code: (i) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Di-μ(2)-chlorido-bis-[chlorido(η-hexa-methyl-benzene)ruthenium(II)].

Authors:  Yunuem González-Torres; Noel Espinosa-Jalapa; Simón Hernández-Ortega; Ronan Le Lagadec; David Morales-Morales
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-17
  2 in total

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