(η⁶-Hexamethylbenzene)(mesidine)­ditriflatoruthenium(II)

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 Ru^II complexes.

Computing details

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)

Crystal data

[Ru(C12H18)(CF3O3S)2(C9H13N)]	F(000) = 1416
Mr = 696.68	Dx = 1.703 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.9497 (13) Å	Cell parameters from 35 reflections
b = 14.7055 (15) Å	θ = 5.4–14.5°
c = 14.049 (2) Å	µ = 0.81 mm^−1
β = 109.430 (8)°	T = 163 K
V = 2717.8 (6) Å^3	Cuboid, red-orange
Z = 4	0.27 × 0.27 × 0.17 mm

Data collection

Siemens P4 diffractometer	5082 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.020
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
2θ/ω scans	h = 0→18
Absorption correction: numerical (SHELXTL; Sheldrick, 1997)	k = 0→19
Tmin = 0.811, Tmax = 0.874	l = −18→17
6422 measured reflections	3 standard reflections every 97 reflections
6237 independent reflections	intensity decay: <1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	All H-atom parameters refined
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0284P)^2 + 2.7894P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.011
6237 reflections	Δρmax = 0.44 e Å^−3
477 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00175 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ru1	0.355069 (14)	0.238026 (12)	0.619102 (14)	0.01366 (6)
S1	0.24803 (5)	0.07454 (4)	0.44508 (5)	0.01905 (13)
S2	0.14580 (5)	0.18156 (4)	0.67532 (5)	0.01971 (13)
O1	0.24463 (13)	0.22742 (13)	0.69675 (13)	0.0217 (4)
O2	0.15302 (19)	0.08771 (14)	0.70091 (17)	0.0395 (5)
O3	0.07294 (15)	0.20901 (16)	0.58050 (14)	0.0330 (5)
O4	0.27823 (13)	0.11524 (12)	0.54631 (13)	0.0209 (4)
O5	0.33011 (15)	0.03670 (14)	0.41869 (16)	0.0325 (5)
O6	0.17691 (15)	0.12958 (13)	0.36936 (14)	0.0292 (4)
N1	0.22796 (16)	0.30117 (14)	0.50000 (16)	0.0174 (4)
C1	0.46284 (18)	0.35217 (17)	0.67229 (19)	0.0188 (5)
C2	0.48730 (18)	0.30452 (17)	0.59470 (19)	0.0191 (5)
C3	0.50180 (18)	0.20871 (17)	0.59940 (19)	0.0202 (5)
C4	0.49324 (18)	0.15914 (18)	0.6849 (2)	0.0213 (5)
C5	0.47306 (18)	0.20649 (18)	0.76404 (19)	0.0197 (5)
C6	0.45365 (18)	0.30274 (18)	0.75628 (18)	0.0198 (5)
C7	0.4531 (2)	0.45410 (19)	0.6669 (3)	0.0288 (6)
C8	0.5005 (2)	0.3590 (2)	0.5087 (2)	0.0269 (6)
C9	0.5287 (3)	0.1599 (2)	0.5174 (3)	0.0322 (7)
C10	0.4978 (3)	0.0566 (2)	0.6855 (3)	0.0317 (7)
C11	0.4613 (3)	0.1561 (2)	0.8531 (2)	0.0306 (7)
C12	0.4209 (2)	0.3495 (2)	0.8354 (2)	0.0272 (6)
C13	0.22674 (18)	0.39365 (16)	0.46504 (19)	0.0184 (5)
C14	0.2022 (2)	0.46387 (18)	0.5198 (2)	0.0225 (5)
C15	0.1999 (2)	0.55215 (19)	0.4833 (2)	0.0281 (6)
C16	0.2226 (2)	0.57194 (19)	0.3966 (2)	0.0282 (6)
C17	0.2489 (2)	0.5009 (2)	0.3458 (2)	0.0275 (6)
C18	0.24977 (19)	0.41063 (18)	0.37700 (19)	0.0212 (5)
C19	0.1757 (3)	0.4448 (2)	0.6131 (2)	0.0319 (7)
C20	0.2180 (3)	0.6683 (3)	0.3582 (4)	0.0464 (9)
C21	0.2703 (3)	0.3341 (2)	0.3150 (2)	0.0300 (6)
C22	0.1019 (2)	0.2347 (2)	0.7714 (2)	0.0302 (6)
C23	0.1758 (2)	−0.02449 (18)	0.4620 (2)	0.0270 (6)
F1	0.01326 (14)	0.19921 (16)	0.76801 (15)	0.0507 (5)
F2	0.08963 (18)	0.32287 (14)	0.75842 (16)	0.0538 (6)
F3	0.16712 (15)	0.22025 (16)	0.86327 (13)	0.0484 (5)
F4	0.23397 (16)	−0.07827 (12)	0.53347 (16)	0.0484 (5)
F5	0.14436 (17)	−0.07148 (13)	0.37616 (15)	0.0524 (6)
F6	0.09609 (14)	−0.00109 (13)	0.48601 (15)	0.0402 (4)
H1	0.214 (2)	0.262 (2)	0.444 (3)	0.035 (9)*
H2	0.181 (2)	0.291 (2)	0.524 (2)	0.024 (8)*
H7A	0.412 (3)	0.472 (3)	0.603 (3)	0.058 (12)*
H7B	0.426 (3)	0.477 (3)	0.710 (3)	0.054 (11)*
H7C	0.521 (3)	0.480 (3)	0.679 (3)	0.052 (11)*
H8A	0.501 (3)	0.325 (3)	0.456 (3)	0.055 (11)*
H8B	0.441 (3)	0.404 (2)	0.477 (3)	0.043 (10)*
H8C	0.558 (3)	0.394 (3)	0.532 (3)	0.051 (11)*
H9A	0.529 (3)	0.101 (3)	0.521 (3)	0.072 (14)*
H9B	0.485 (4)	0.174 (3)	0.453 (4)	0.080 (15)*
H9C	0.594 (4)	0.179 (3)	0.516 (3)	0.077 (14)*
H10A	0.473 (3)	0.033 (3)	0.621 (3)	0.062 (12)*
H10B	0.564 (3)	0.036 (3)	0.712 (3)	0.064 (12)*
H10C	0.461 (3)	0.030 (3)	0.717 (3)	0.062 (13)*
H11A	0.487 (3)	0.195 (3)	0.916 (3)	0.052 (11)*
H11B	0.504 (3)	0.102 (3)	0.864 (3)	0.053 (11)*
H11C	0.404 (3)	0.144 (3)	0.844 (3)	0.050 (12)*
H12A	0.474 (3)	0.350 (2)	0.894 (3)	0.041 (10)*
H12B	0.393 (3)	0.409 (3)	0.818 (3)	0.042 (10)*
H12C	0.372 (3)	0.315 (2)	0.852 (2)	0.036 (9)*
H15	0.184 (2)	0.599 (2)	0.519 (2)	0.031 (8)*
H17	0.261 (2)	0.512 (2)	0.283 (2)	0.031 (8)*
H19A	0.186 (3)	0.498 (3)	0.652 (3)	0.054 (11)*
H19B	0.220 (3)	0.407 (3)	0.658 (3)	0.047 (11)*
H19C	0.108 (3)	0.420 (2)	0.595 (3)	0.043 (10)*
H20A	0.256 (5)	0.705 (5)	0.406 (5)	0.13 (3)*
H20B	0.155 (4)	0.687 (4)	0.325 (4)	0.097 (18)*
H20C	0.258 (4)	0.676 (4)	0.323 (4)	0.087 (18)*
H21A	0.322 (3)	0.289 (2)	0.360 (3)	0.045 (10)*
H21B	0.210 (3)	0.305 (2)	0.283 (2)	0.039 (9)*
H21C	0.294 (3)	0.355 (3)	0.265 (3)	0.057 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.01329 (9)	0.01369 (9)	0.01486 (9)	0.00034 (7)	0.00585 (7)	−0.00042 (7)
S1	0.0203 (3)	0.0176 (3)	0.0198 (3)	−0.0005 (2)	0.0073 (2)	−0.0024 (2)
S2	0.0191 (3)	0.0233 (3)	0.0186 (3)	−0.0029 (2)	0.0088 (2)	0.0014 (2)
O1	0.0178 (9)	0.0303 (10)	0.0195 (8)	−0.0026 (7)	0.0098 (7)	−0.0026 (7)
O2	0.0588 (15)	0.0243 (11)	0.0446 (13)	−0.0067 (10)	0.0295 (12)	0.0043 (9)
O3	0.0233 (10)	0.0519 (13)	0.0213 (10)	−0.0031 (9)	0.0040 (8)	0.0020 (9)
O4	0.0236 (9)	0.0183 (9)	0.0196 (9)	−0.0016 (7)	0.0059 (7)	−0.0025 (7)
O5	0.0300 (11)	0.0349 (11)	0.0386 (12)	0.0019 (9)	0.0192 (9)	−0.0094 (9)
O6	0.0321 (11)	0.0272 (10)	0.0236 (10)	0.0022 (8)	0.0028 (8)	0.0040 (8)
N1	0.0195 (11)	0.0159 (10)	0.0179 (10)	0.0011 (8)	0.0078 (9)	0.0009 (8)
C1	0.0150 (11)	0.0187 (12)	0.0220 (12)	−0.0031 (9)	0.0050 (10)	−0.0016 (10)
C2	0.0134 (11)	0.0221 (13)	0.0226 (12)	−0.0028 (9)	0.0071 (10)	0.0004 (10)
C3	0.0137 (12)	0.0222 (12)	0.0270 (13)	−0.0009 (10)	0.0098 (10)	−0.0040 (10)
C4	0.0120 (11)	0.0219 (13)	0.0281 (13)	0.0020 (9)	0.0041 (10)	0.0021 (10)
C5	0.0132 (11)	0.0231 (12)	0.0194 (12)	−0.0028 (9)	0.0007 (9)	0.0026 (10)
C6	0.0150 (12)	0.0255 (13)	0.0182 (12)	−0.0043 (10)	0.0048 (10)	−0.0037 (10)
C7	0.0334 (17)	0.0194 (14)	0.0366 (17)	−0.0046 (12)	0.0156 (14)	−0.0013 (12)
C8	0.0293 (15)	0.0285 (15)	0.0284 (15)	−0.0048 (12)	0.0171 (12)	0.0030 (12)
C9	0.0299 (16)	0.0325 (17)	0.0409 (18)	0.0038 (13)	0.0205 (14)	−0.0089 (14)
C10	0.0314 (17)	0.0197 (14)	0.0430 (19)	0.0052 (12)	0.0113 (15)	0.0037 (13)
C11	0.0263 (16)	0.0367 (17)	0.0243 (15)	−0.0045 (13)	0.0026 (12)	0.0087 (12)
C12	0.0278 (15)	0.0329 (16)	0.0220 (14)	−0.0049 (12)	0.0099 (12)	−0.0076 (12)
C13	0.0162 (12)	0.0168 (12)	0.0201 (12)	0.0011 (9)	0.0034 (10)	0.0029 (9)
C14	0.0233 (13)	0.0193 (13)	0.0252 (13)	0.0023 (10)	0.0084 (11)	0.0025 (10)
C15	0.0304 (15)	0.0177 (13)	0.0355 (16)	0.0033 (11)	0.0099 (12)	0.0013 (11)
C16	0.0222 (14)	0.0225 (14)	0.0345 (15)	−0.0034 (11)	0.0019 (11)	0.0092 (12)
C17	0.0261 (14)	0.0328 (15)	0.0209 (13)	−0.0050 (12)	0.0045 (11)	0.0082 (11)
C18	0.0195 (12)	0.0243 (13)	0.0184 (12)	−0.0019 (10)	0.0045 (10)	0.0004 (10)
C19	0.046 (2)	0.0258 (15)	0.0292 (15)	0.0050 (14)	0.0199 (14)	−0.0012 (12)
C20	0.048 (2)	0.0274 (18)	0.059 (2)	−0.0018 (16)	0.010 (2)	0.0203 (17)
C21	0.0351 (17)	0.0372 (17)	0.0199 (13)	−0.0046 (14)	0.0120 (13)	−0.0046 (12)
C22	0.0283 (14)	0.0403 (16)	0.0277 (14)	0.0018 (13)	0.0169 (12)	0.0045 (12)
C23	0.0324 (15)	0.0202 (13)	0.0291 (14)	−0.0046 (11)	0.0109 (12)	−0.0046 (11)
F1	0.0341 (10)	0.0788 (15)	0.0521 (12)	−0.0096 (10)	0.0315 (10)	−0.0023 (11)
F2	0.0779 (15)	0.0387 (11)	0.0653 (14)	0.0158 (10)	0.0514 (12)	0.0028 (10)
F3	0.0422 (11)	0.0831 (16)	0.0212 (9)	0.0094 (10)	0.0123 (8)	−0.0016 (9)
F4	0.0546 (12)	0.0280 (10)	0.0611 (13)	0.0022 (9)	0.0170 (10)	0.0180 (9)
F5	0.0724 (15)	0.0421 (11)	0.0481 (12)	−0.0294 (11)	0.0272 (11)	−0.0264 (10)
F6	0.0349 (10)	0.0392 (10)	0.0545 (12)	−0.0111 (8)	0.0257 (9)	−0.0045 (9)

Geometric parameters (Å, º)

Ru1—O1	2.1692 (17)	C2—C8	1.511 (4)
Ru1—O4	2.1739 (17)	C3—C4	1.443 (4)
Ru1—C4	2.175 (2)	C3—C9	1.506 (4)
Ru1—C6	2.179 (2)	C4—C5	1.417 (4)
Ru1—C3	2.197 (2)	C4—C10	1.509 (4)
Ru1—N1	2.198 (2)	C5—C6	1.438 (4)
Ru1—C5	2.200 (2)	C5—C11	1.509 (4)
Ru1—C1	2.211 (2)	C6—C12	1.502 (4)
Ru1—C2	2.213 (2)	C13—C14	1.396 (3)
Ru1—Cg	1.667	C13—C18	1.400 (3)
S1—O5	1.4284 (19)	C14—C15	1.392 (4)
S1—O6	1.4383 (19)	C14—C19	1.503 (4)
S1—O4	1.4696 (18)	C15—C16	1.388 (4)
S1—C23	1.830 (3)	C16—C17	1.381 (4)
S2—O2	1.421 (2)	C16—C20	1.510 (4)
S2—O3	1.439 (2)	C17—C18	1.397 (4)
S2—O1	1.4731 (18)	C18—C21	1.508 (4)
S2—C22	1.832 (3)	C22—F2	1.313 (4)
N1—C13	1.444 (3)	C22—F3	1.326 (3)
C1—C6	1.428 (3)	C22—F1	1.329 (3)
C1—C2	1.429 (3)	C23—F6	1.311 (3)
C1—C7	1.505 (4)	C23—F4	1.323 (3)
C2—C3	1.422 (4)	C23—F5	1.331 (3)
Cnt—Ru1—O1	123.2	C2—C1—Ru1	71.22 (14)
Cnt—Ru1—O4	129.1	C7—C1—Ru1	134.4 (2)
Cnt—Ru1—N1	138.9	C3—C2—C1	121.1 (2)
O1—Ru1—O4	81.68 (7)	C3—C2—C8	120.6 (2)
O1—Ru1—C4	115.16 (8)	C1—C2—C8	118.3 (2)
O4—Ru1—C4	89.17 (8)	C3—C2—Ru1	70.60 (14)
O1—Ru1—C6	86.07 (8)	C1—C2—Ru1	71.08 (14)
O4—Ru1—C6	147.80 (8)	C8—C2—Ru1	133.44 (19)
C4—Ru1—C6	69.37 (10)	C2—C3—C4	119.3 (2)
O1—Ru1—C3	153.68 (8)	C2—C3—C9	120.3 (3)
O4—Ru1—C3	96.43 (8)	C4—C3—C9	120.4 (2)
C4—Ru1—C3	38.55 (9)	C2—C3—Ru1	71.79 (14)
C6—Ru1—C3	81.77 (9)	C4—C3—Ru1	69.88 (13)
O1—Ru1—N1	83.41 (8)	C9—C3—Ru1	132.0 (2)
O4—Ru1—N1	81.15 (7)	C5—C4—C3	119.9 (2)
C4—Ru1—N1	157.71 (9)	C5—C4—C10	120.3 (3)
C6—Ru1—N1	126.92 (9)	C3—C4—C10	119.7 (3)
C3—Ru1—N1	122.43 (9)	C5—C4—Ru1	72.07 (14)
O1—Ru1—C5	87.55 (8)	C3—C4—Ru1	71.58 (14)
O4—Ru1—C5	111.12 (8)	C10—C4—Ru1	124.4 (2)
C4—Ru1—C5	37.80 (10)	C4—C5—C6	120.4 (2)
C6—Ru1—C5	38.35 (10)	C4—C5—C11	121.0 (2)
C3—Ru1—C5	68.52 (9)	C6—C5—C11	118.4 (2)
N1—Ru1—C5	163.57 (9)	C4—C5—Ru1	70.13 (14)
O1—Ru1—C1	113.67 (8)	C6—C5—Ru1	70.03 (14)
O4—Ru1—C1	164.36 (8)	C11—C5—Ru1	128.06 (19)
C4—Ru1—C1	81.63 (10)	C1—C6—C5	119.8 (2)
C6—Ru1—C1	37.95 (9)	C1—C6—C12	120.8 (2)
C3—Ru1—C1	68.55 (9)	C5—C6—C12	119.3 (2)
N1—Ru1—C1	102.84 (9)	C1—C6—Ru1	72.25 (14)
C5—Ru1—C1	68.41 (9)	C5—C6—Ru1	71.63 (14)
O1—Ru1—C2	151.37 (8)	C12—C6—Ru1	126.62 (19)
O4—Ru1—C2	126.88 (8)	C14—C13—C18	121.7 (2)
C4—Ru1—C2	68.59 (9)	C14—C13—N1	119.1 (2)
C6—Ru1—C2	68.33 (9)	C18—C13—N1	119.2 (2)
C3—Ru1—C2	37.61 (9)	C15—C14—C13	117.8 (2)
N1—Ru1—C2	101.44 (9)	C15—C14—C19	120.8 (3)
C5—Ru1—C2	80.27 (9)	C13—C14—C19	121.3 (2)
C1—Ru1—C2	37.70 (9)	C16—C15—C14	122.3 (3)
O5—S1—O6	116.26 (13)	C17—C16—C15	118.1 (2)
O5—S1—O4	114.41 (12)	C17—C16—C20	120.9 (3)
O6—S1—O4	113.06 (11)	C15—C16—C20	121.0 (3)
O5—S1—C23	104.30 (13)	C16—C17—C18	122.2 (3)
O6—S1—C23	105.66 (13)	C17—C18—C13	117.8 (2)
O4—S1—C23	101.03 (12)	C17—C18—C21	120.8 (2)
O2—S2—O3	118.39 (14)	C13—C18—C21	121.3 (2)
O2—S2—O1	114.21 (13)	F2—C22—F3	108.0 (3)
O3—S2—O1	112.68 (12)	F2—C22—F1	107.8 (2)
O2—S2—C22	103.94 (13)	F3—C22—F1	107.5 (2)
O3—S2—C22	104.85 (13)	F2—C22—S2	112.31 (19)
O1—S2—C22	99.99 (12)	F3—C22—S2	111.1 (2)
S2—O1—Ru1	134.68 (11)	F1—C22—S2	110.0 (2)
S1—O4—Ru1	136.99 (11)	F6—C23—F4	108.7 (2)
C13—N1—Ru1	124.89 (16)	F6—C23—F5	108.5 (2)
C6—C1—C2	119.4 (2)	F4—C23—F5	108.1 (2)
C6—C1—C7	121.2 (2)	F6—C23—S1	112.03 (19)
C2—C1—C7	119.3 (2)	F5—C23—S1	108.98 (19)
C6—C1—Ru1	69.81 (14)