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The crystal structure of the title complex, (η6-hexamethylbenzene)bis(trifluoromethanesulfonato-O)(2,4,6-trimethylanil­ine-N)ruthenium(II), [Ru(CF3O3S)2(C12H18)(C9H13N)], is described. The complex has the classic three-legged piano-stool structure with a planar arene 1.667 Å from the metal, two monodentate O-bound tri­fluoro­methane­sulfonate ligands [Ru—O 2.169 (2) and 2.174 (2) Å] and one N-bound mesidine ligand [Ru—N 2.198 (2) Å]. The Ru—N distance is relatively long and the average Ru—O distance is relatively short when compared with previously characterized RuII complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001001/da1103sup1.cif
Contains datablocks fjf17, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001001/da1103Isup2.hkl
Contains datablock I

CCDC reference: 146029

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: CARESS (Broach, 1978); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(η6-hexamethylbenzene)bis(trifluoromethanesulfonato-O) (2,4,6-trimethylaniline-N)ruthenium(II) top
Crystal data top
[Ru(C12H18)(CF3O3S)2(C9H13N)]F(000) = 1416
Mr = 696.68Dx = 1.703 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.9497 (13) ÅCell parameters from 35 reflections
b = 14.7055 (15) Åθ = 5.4–14.5°
c = 14.049 (2) ŵ = 0.81 mm1
β = 109.430 (8)°T = 163 K
V = 2717.8 (6) Å3Cuboid, red-orange
Z = 40.27 × 0.27 × 0.17 mm
Data collection top
Siemens P4
diffractometer
5082 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.020
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
2θ/ω scansh = 018
Absorption correction: numerical
(SHELXTL; Sheldrick, 1997)
k = 019
Tmin = 0.811, Tmax = 0.874l = 1817
6422 measured reflections3 standard reflections every 97 reflections
6237 independent reflections intensity decay: <1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030All H-atom parameters refined
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0284P)2 + 2.7894P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.011
6237 reflectionsΔρmax = 0.44 e Å3
477 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00175 (13)
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
Ru10.355069 (14)0.238026 (12)0.619102 (14)0.01366 (6)
S10.24803 (5)0.07454 (4)0.44508 (5)0.01905 (13)
S20.14580 (5)0.18156 (4)0.67532 (5)0.01971 (13)
O10.24463 (13)0.22742 (13)0.69675 (13)0.0217 (4)
O20.15302 (19)0.08771 (14)0.70091 (17)0.0395 (5)
O30.07294 (15)0.20901 (16)0.58050 (14)0.0330 (5)
O40.27823 (13)0.11524 (12)0.54631 (13)0.0209 (4)
O50.33011 (15)0.03670 (14)0.41869 (16)0.0325 (5)
O60.17691 (15)0.12958 (13)0.36936 (14)0.0292 (4)
N10.22796 (16)0.30117 (14)0.50000 (16)0.0174 (4)
C10.46284 (18)0.35217 (17)0.67229 (19)0.0188 (5)
C20.48730 (18)0.30452 (17)0.59470 (19)0.0191 (5)
C30.50180 (18)0.20871 (17)0.59940 (19)0.0202 (5)
C40.49324 (18)0.15914 (18)0.6849 (2)0.0213 (5)
C50.47306 (18)0.20649 (18)0.76404 (19)0.0197 (5)
C60.45365 (18)0.30274 (18)0.75628 (18)0.0198 (5)
C70.4531 (2)0.45410 (19)0.6669 (3)0.0288 (6)
C80.5005 (2)0.3590 (2)0.5087 (2)0.0269 (6)
C90.5287 (3)0.1599 (2)0.5174 (3)0.0322 (7)
C100.4978 (3)0.0566 (2)0.6855 (3)0.0317 (7)
C110.4613 (3)0.1561 (2)0.8531 (2)0.0306 (7)
C120.4209 (2)0.3495 (2)0.8354 (2)0.0272 (6)
C130.22674 (18)0.39365 (16)0.46504 (19)0.0184 (5)
C140.2022 (2)0.46387 (18)0.5198 (2)0.0225 (5)
C150.1999 (2)0.55215 (19)0.4833 (2)0.0281 (6)
C160.2226 (2)0.57194 (19)0.3966 (2)0.0282 (6)
C170.2489 (2)0.5009 (2)0.3458 (2)0.0275 (6)
C180.24977 (19)0.41063 (18)0.37700 (19)0.0212 (5)
C190.1757 (3)0.4448 (2)0.6131 (2)0.0319 (7)
C200.2180 (3)0.6683 (3)0.3582 (4)0.0464 (9)
C210.2703 (3)0.3341 (2)0.3150 (2)0.0300 (6)
C220.1019 (2)0.2347 (2)0.7714 (2)0.0302 (6)
C230.1758 (2)0.02449 (18)0.4620 (2)0.0270 (6)
F10.01326 (14)0.19921 (16)0.76801 (15)0.0507 (5)
F20.08963 (18)0.32287 (14)0.75842 (16)0.0538 (6)
F30.16712 (15)0.22025 (16)0.86327 (13)0.0484 (5)
F40.23397 (16)0.07827 (12)0.53347 (16)0.0484 (5)
F50.14436 (17)0.07148 (13)0.37616 (15)0.0524 (6)
F60.09609 (14)0.00109 (13)0.48601 (15)0.0402 (4)
H10.214 (2)0.262 (2)0.444 (3)0.035 (9)*
H20.181 (2)0.291 (2)0.524 (2)0.024 (8)*
H7A0.412 (3)0.472 (3)0.603 (3)0.058 (12)*
H7B0.426 (3)0.477 (3)0.710 (3)0.054 (11)*
H7C0.521 (3)0.480 (3)0.679 (3)0.052 (11)*
H8A0.501 (3)0.325 (3)0.456 (3)0.055 (11)*
H8B0.441 (3)0.404 (2)0.477 (3)0.043 (10)*
H8C0.558 (3)0.394 (3)0.532 (3)0.051 (11)*
H9A0.529 (3)0.101 (3)0.521 (3)0.072 (14)*
H9B0.485 (4)0.174 (3)0.453 (4)0.080 (15)*
H9C0.594 (4)0.179 (3)0.516 (3)0.077 (14)*
H10A0.473 (3)0.033 (3)0.621 (3)0.062 (12)*
H10B0.564 (3)0.036 (3)0.712 (3)0.064 (12)*
H10C0.461 (3)0.030 (3)0.717 (3)0.062 (13)*
H11A0.487 (3)0.195 (3)0.916 (3)0.052 (11)*
H11B0.504 (3)0.102 (3)0.864 (3)0.053 (11)*
H11C0.404 (3)0.144 (3)0.844 (3)0.050 (12)*
H12A0.474 (3)0.350 (2)0.894 (3)0.041 (10)*
H12B0.393 (3)0.409 (3)0.818 (3)0.042 (10)*
H12C0.372 (3)0.315 (2)0.852 (2)0.036 (9)*
H150.184 (2)0.599 (2)0.519 (2)0.031 (8)*
H170.261 (2)0.512 (2)0.283 (2)0.031 (8)*
H19A0.186 (3)0.498 (3)0.652 (3)0.054 (11)*
H19B0.220 (3)0.407 (3)0.658 (3)0.047 (11)*
H19C0.108 (3)0.420 (2)0.595 (3)0.043 (10)*
H20A0.256 (5)0.705 (5)0.406 (5)0.13 (3)*
H20B0.155 (4)0.687 (4)0.325 (4)0.097 (18)*
H20C0.258 (4)0.676 (4)0.323 (4)0.087 (18)*
H21A0.322 (3)0.289 (2)0.360 (3)0.045 (10)*
H21B0.210 (3)0.305 (2)0.283 (2)0.039 (9)*
H21C0.294 (3)0.355 (3)0.265 (3)0.057 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01329 (9)0.01369 (9)0.01486 (9)0.00034 (7)0.00585 (7)0.00042 (7)
S10.0203 (3)0.0176 (3)0.0198 (3)0.0005 (2)0.0073 (2)0.0024 (2)
S20.0191 (3)0.0233 (3)0.0186 (3)0.0029 (2)0.0088 (2)0.0014 (2)
O10.0178 (9)0.0303 (10)0.0195 (8)0.0026 (7)0.0098 (7)0.0026 (7)
O20.0588 (15)0.0243 (11)0.0446 (13)0.0067 (10)0.0295 (12)0.0043 (9)
O30.0233 (10)0.0519 (13)0.0213 (10)0.0031 (9)0.0040 (8)0.0020 (9)
O40.0236 (9)0.0183 (9)0.0196 (9)0.0016 (7)0.0059 (7)0.0025 (7)
O50.0300 (11)0.0349 (11)0.0386 (12)0.0019 (9)0.0192 (9)0.0094 (9)
O60.0321 (11)0.0272 (10)0.0236 (10)0.0022 (8)0.0028 (8)0.0040 (8)
N10.0195 (11)0.0159 (10)0.0179 (10)0.0011 (8)0.0078 (9)0.0009 (8)
C10.0150 (11)0.0187 (12)0.0220 (12)0.0031 (9)0.0050 (10)0.0016 (10)
C20.0134 (11)0.0221 (13)0.0226 (12)0.0028 (9)0.0071 (10)0.0004 (10)
C30.0137 (12)0.0222 (12)0.0270 (13)0.0009 (10)0.0098 (10)0.0040 (10)
C40.0120 (11)0.0219 (13)0.0281 (13)0.0020 (9)0.0041 (10)0.0021 (10)
C50.0132 (11)0.0231 (12)0.0194 (12)0.0028 (9)0.0007 (9)0.0026 (10)
C60.0150 (12)0.0255 (13)0.0182 (12)0.0043 (10)0.0048 (10)0.0037 (10)
C70.0334 (17)0.0194 (14)0.0366 (17)0.0046 (12)0.0156 (14)0.0013 (12)
C80.0293 (15)0.0285 (15)0.0284 (15)0.0048 (12)0.0171 (12)0.0030 (12)
C90.0299 (16)0.0325 (17)0.0409 (18)0.0038 (13)0.0205 (14)0.0089 (14)
C100.0314 (17)0.0197 (14)0.0430 (19)0.0052 (12)0.0113 (15)0.0037 (13)
C110.0263 (16)0.0367 (17)0.0243 (15)0.0045 (13)0.0026 (12)0.0087 (12)
C120.0278 (15)0.0329 (16)0.0220 (14)0.0049 (12)0.0099 (12)0.0076 (12)
C130.0162 (12)0.0168 (12)0.0201 (12)0.0011 (9)0.0034 (10)0.0029 (9)
C140.0233 (13)0.0193 (13)0.0252 (13)0.0023 (10)0.0084 (11)0.0025 (10)
C150.0304 (15)0.0177 (13)0.0355 (16)0.0033 (11)0.0099 (12)0.0013 (11)
C160.0222 (14)0.0225 (14)0.0345 (15)0.0034 (11)0.0019 (11)0.0092 (12)
C170.0261 (14)0.0328 (15)0.0209 (13)0.0050 (12)0.0045 (11)0.0082 (11)
C180.0195 (12)0.0243 (13)0.0184 (12)0.0019 (10)0.0045 (10)0.0004 (10)
C190.046 (2)0.0258 (15)0.0292 (15)0.0050 (14)0.0199 (14)0.0012 (12)
C200.048 (2)0.0274 (18)0.059 (2)0.0018 (16)0.010 (2)0.0203 (17)
C210.0351 (17)0.0372 (17)0.0199 (13)0.0046 (14)0.0120 (13)0.0046 (12)
C220.0283 (14)0.0403 (16)0.0277 (14)0.0018 (13)0.0169 (12)0.0045 (12)
C230.0324 (15)0.0202 (13)0.0291 (14)0.0046 (11)0.0109 (12)0.0046 (11)
F10.0341 (10)0.0788 (15)0.0521 (12)0.0096 (10)0.0315 (10)0.0023 (11)
F20.0779 (15)0.0387 (11)0.0653 (14)0.0158 (10)0.0514 (12)0.0028 (10)
F30.0422 (11)0.0831 (16)0.0212 (9)0.0094 (10)0.0123 (8)0.0016 (9)
F40.0546 (12)0.0280 (10)0.0611 (13)0.0022 (9)0.0170 (10)0.0180 (9)
F50.0724 (15)0.0421 (11)0.0481 (12)0.0294 (11)0.0272 (11)0.0264 (10)
F60.0349 (10)0.0392 (10)0.0545 (12)0.0111 (8)0.0257 (9)0.0045 (9)
Geometric parameters (Å, º) top
Ru1—O12.1692 (17)C2—C81.511 (4)
Ru1—O42.1739 (17)C3—C41.443 (4)
Ru1—C42.175 (2)C3—C91.506 (4)
Ru1—C62.179 (2)C4—C51.417 (4)
Ru1—C32.197 (2)C4—C101.509 (4)
Ru1—N12.198 (2)C5—C61.438 (4)
Ru1—C52.200 (2)C5—C111.509 (4)
Ru1—C12.211 (2)C6—C121.502 (4)
Ru1—C22.213 (2)C13—C141.396 (3)
Ru1—Cg1.667C13—C181.400 (3)
S1—O51.4284 (19)C14—C151.392 (4)
S1—O61.4383 (19)C14—C191.503 (4)
S1—O41.4696 (18)C15—C161.388 (4)
S1—C231.830 (3)C16—C171.381 (4)
S2—O21.421 (2)C16—C201.510 (4)
S2—O31.439 (2)C17—C181.397 (4)
S2—O11.4731 (18)C18—C211.508 (4)
S2—C221.832 (3)C22—F21.313 (4)
N1—C131.444 (3)C22—F31.326 (3)
C1—C61.428 (3)C22—F11.329 (3)
C1—C21.429 (3)C23—F61.311 (3)
C1—C71.505 (4)C23—F41.323 (3)
C2—C31.422 (4)C23—F51.331 (3)
Cnt—Ru1—O1123.2C2—C1—Ru171.22 (14)
Cnt—Ru1—O4129.1C7—C1—Ru1134.4 (2)
Cnt—Ru1—N1138.9C3—C2—C1121.1 (2)
O1—Ru1—O481.68 (7)C3—C2—C8120.6 (2)
O1—Ru1—C4115.16 (8)C1—C2—C8118.3 (2)
O4—Ru1—C489.17 (8)C3—C2—Ru170.60 (14)
O1—Ru1—C686.07 (8)C1—C2—Ru171.08 (14)
O4—Ru1—C6147.80 (8)C8—C2—Ru1133.44 (19)
C4—Ru1—C669.37 (10)C2—C3—C4119.3 (2)
O1—Ru1—C3153.68 (8)C2—C3—C9120.3 (3)
O4—Ru1—C396.43 (8)C4—C3—C9120.4 (2)
C4—Ru1—C338.55 (9)C2—C3—Ru171.79 (14)
C6—Ru1—C381.77 (9)C4—C3—Ru169.88 (13)
O1—Ru1—N183.41 (8)C9—C3—Ru1132.0 (2)
O4—Ru1—N181.15 (7)C5—C4—C3119.9 (2)
C4—Ru1—N1157.71 (9)C5—C4—C10120.3 (3)
C6—Ru1—N1126.92 (9)C3—C4—C10119.7 (3)
C3—Ru1—N1122.43 (9)C5—C4—Ru172.07 (14)
O1—Ru1—C587.55 (8)C3—C4—Ru171.58 (14)
O4—Ru1—C5111.12 (8)C10—C4—Ru1124.4 (2)
C4—Ru1—C537.80 (10)C4—C5—C6120.4 (2)
C6—Ru1—C538.35 (10)C4—C5—C11121.0 (2)
C3—Ru1—C568.52 (9)C6—C5—C11118.4 (2)
N1—Ru1—C5163.57 (9)C4—C5—Ru170.13 (14)
O1—Ru1—C1113.67 (8)C6—C5—Ru170.03 (14)
O4—Ru1—C1164.36 (8)C11—C5—Ru1128.06 (19)
C4—Ru1—C181.63 (10)C1—C6—C5119.8 (2)
C6—Ru1—C137.95 (9)C1—C6—C12120.8 (2)
C3—Ru1—C168.55 (9)C5—C6—C12119.3 (2)
N1—Ru1—C1102.84 (9)C1—C6—Ru172.25 (14)
C5—Ru1—C168.41 (9)C5—C6—Ru171.63 (14)
O1—Ru1—C2151.37 (8)C12—C6—Ru1126.62 (19)
O4—Ru1—C2126.88 (8)C14—C13—C18121.7 (2)
C4—Ru1—C268.59 (9)C14—C13—N1119.1 (2)
C6—Ru1—C268.33 (9)C18—C13—N1119.2 (2)
C3—Ru1—C237.61 (9)C15—C14—C13117.8 (2)
N1—Ru1—C2101.44 (9)C15—C14—C19120.8 (3)
C5—Ru1—C280.27 (9)C13—C14—C19121.3 (2)
C1—Ru1—C237.70 (9)C16—C15—C14122.3 (3)
O5—S1—O6116.26 (13)C17—C16—C15118.1 (2)
O5—S1—O4114.41 (12)C17—C16—C20120.9 (3)
O6—S1—O4113.06 (11)C15—C16—C20121.0 (3)
O5—S1—C23104.30 (13)C16—C17—C18122.2 (3)
O6—S1—C23105.66 (13)C17—C18—C13117.8 (2)
O4—S1—C23101.03 (12)C17—C18—C21120.8 (2)
O2—S2—O3118.39 (14)C13—C18—C21121.3 (2)
O2—S2—O1114.21 (13)F2—C22—F3108.0 (3)
O3—S2—O1112.68 (12)F2—C22—F1107.8 (2)
O2—S2—C22103.94 (13)F3—C22—F1107.5 (2)
O3—S2—C22104.85 (13)F2—C22—S2112.31 (19)
O1—S2—C2299.99 (12)F3—C22—S2111.1 (2)
S2—O1—Ru1134.68 (11)F1—C22—S2110.0 (2)
S1—O4—Ru1136.99 (11)F6—C23—F4108.7 (2)
C13—N1—Ru1124.89 (16)F6—C23—F5108.5 (2)
C6—C1—C2119.4 (2)F4—C23—F5108.1 (2)
C6—C1—C7121.2 (2)F6—C23—S1112.03 (19)
C2—C1—C7119.3 (2)F5—C23—S1108.98 (19)
C6—C1—Ru169.81 (14)
 

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