In the title compound, [RuCl2(C21H26N2)], the Ru atom has a pseudo-octahedral geometry, with the arene occupying three adjacent sites of the octahedron. Two Cl atoms and one carbene group complete the octahedron.
Supporting information
CCDC reference: 642895
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.007 Å
- R factor = 0.041
- wR factor = 0.086
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C21 H26 Cl2 N2 Ru
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Dichloro[1-(2-methylbenzyl)-3-(2,4,6-trimethylbenzyl)imidazolidin-2-
ylidene]ruthenium
top
Crystal data top
[RuCl2(C21H26N2)] | Z = 2 |
Mr = 478.41 | F(000) = 488 |
Triclinic, P1 | Dx = 1.572 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6761 (15) Å | Cell parameters from 4728 reflections |
b = 11.228 (2) Å | θ = 3.0–26.0° |
c = 12.236 (2) Å | µ = 1.05 mm−1 |
α = 103.39 (3)° | T = 183 K |
β = 96.55 (3)° | Prism, red |
γ = 95.57 (3)° | 0.36 × 0.19 × 0.10 mm |
V = 1010.9 (4) Å3 | |
Data collection top
Rigaku Mercury CCD area-detector diffractometer | 3567 independent reflections |
Radiation source: Sealed tube | 3172 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 14.6199 pixels mm-1 | θmax = 25.1°, θmin = 3.0° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (REQAB; Rigaku/MSC, 1999) | k = −13→13 |
Tmin = 0.704, Tmax = 0.903 | l = −14→14 |
8643 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0199P)2 + 3.385P] where P = (Fo2 + 2Fc2)/3 |
3567 reflections | (Δ/σ)max = 0.001 |
239 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | −0.7144 (6) | 0.4823 (4) | 0.3280 (5) | 0.0325 (11) | |
H1A | −0.7718 | 0.5173 | 0.3914 | 0.039* | |
H1B | −0.7761 | 0.4958 | 0.2600 | 0.039* | |
C2 | −0.5207 (6) | 0.5348 (4) | 0.3458 (5) | 0.0337 (11) | |
H2A | −0.5002 | 0.5926 | 0.3004 | 0.040* | |
H2B | −0.4804 | 0.5748 | 0.4241 | 0.040* | |
C3 | −0.5406 (5) | 0.3191 (4) | 0.3003 (4) | 0.0207 (9) | |
C4 | −0.8569 (5) | 0.2590 (4) | 0.3036 (4) | 0.0258 (10) | |
H4A | −0.9442 | 0.2674 | 0.2441 | 0.031* | |
H4B | −0.9087 | 0.2690 | 0.3724 | 0.031* | |
C5 | −0.7931 (5) | 0.1334 (4) | 0.2732 (4) | 0.0226 (9) | |
C6 | −0.7385 (6) | 0.0743 (4) | 0.3605 (4) | 0.0251 (10) | |
C7 | −0.6409 (6) | −0.0286 (4) | 0.3319 (4) | 0.0233 (9) | |
H7 | −0.6040 | −0.0692 | 0.3899 | 0.028* | |
C8 | −0.5971 (6) | −0.0721 (4) | 0.2235 (4) | 0.0232 (9) | |
C9 | −0.6590 (6) | −0.0114 (4) | 0.1387 (4) | 0.0235 (9) | |
H9 | −0.6273 | −0.0386 | 0.0642 | 0.028* | |
C10 | −0.7633 (5) | 0.0853 (4) | 0.1576 (4) | 0.0224 (9) | |
C11 | −0.7777 (7) | 0.1168 (5) | 0.4799 (4) | 0.0324 (11) | |
H11A | −0.7105 | 0.1957 | 0.5151 | 0.049* | |
H11B | −0.7461 | 0.0580 | 0.5221 | 0.049* | |
H11C | −0.9015 | 0.1237 | 0.4787 | 0.049* | |
C12 | −0.4843 (7) | −0.1731 (4) | 0.1978 (4) | 0.0339 (11) | |
H12A | −0.4095 | −0.1748 | 0.2657 | 0.051* | |
H12B | −0.4127 | −0.1588 | 0.1416 | 0.051* | |
H12C | −0.5582 | −0.2507 | 0.1694 | 0.051* | |
C13 | −0.8261 (6) | 0.1422 (5) | 0.0638 (4) | 0.0301 (10) | |
H13A | −0.7773 | 0.1062 | −0.0032 | 0.045* | |
H13B | −0.7885 | 0.2295 | 0.0859 | 0.045* | |
H13C | −0.9528 | 0.1275 | 0.0484 | 0.045* | |
C14 | −0.2426 (5) | 0.4341 (4) | 0.3156 (4) | 0.0230 (9) | |
H14A | −0.2095 | 0.3558 | 0.2794 | 0.028* | |
H14B | −0.1910 | 0.4542 | 0.3939 | 0.028* | |
C15 | −0.1701 (5) | 0.5319 (4) | 0.2597 (4) | 0.0225 (9) | |
C16 | −0.0688 (6) | 0.6392 (4) | 0.3286 (4) | 0.0245 (9) | |
H16 | −0.0495 | 0.6492 | 0.4092 | 0.029* | |
C17 | 0.0040 (6) | 0.7310 (4) | 0.2831 (4) | 0.0309 (11) | |
H17 | 0.0720 | 0.8041 | 0.3319 | 0.037* | |
C18 | −0.0215 (7) | 0.7172 (5) | 0.1677 (5) | 0.0407 (13) | |
H18 | 0.0297 | 0.7800 | 0.1351 | 0.049* | |
C19 | −0.1224 (7) | 0.6114 (5) | 0.0985 (4) | 0.0419 (13) | |
H19 | −0.1409 | 0.6025 | 0.0179 | 0.050* | |
C20 | −0.1974 (7) | 0.5179 (5) | 0.1429 (4) | 0.0348 (11) | |
C21 | −0.3081 (9) | 0.4048 (5) | 0.0634 (5) | 0.0546 (17) | |
H21A | −0.2704 | 0.3316 | 0.0811 | 0.082* | |
H21B | −0.2934 | 0.4041 | −0.0136 | 0.082* | |
H21C | −0.4304 | 0.4073 | 0.0724 | 0.082* | |
Cl1 | −0.31489 (15) | 0.20395 (10) | 0.45520 (9) | 0.0295 (3) | |
Cl2 | −0.26725 (15) | 0.12511 (10) | 0.17609 (10) | 0.0318 (3) | |
N1 | −0.7034 (5) | 0.3510 (3) | 0.3183 (3) | 0.0266 (8) | |
N2 | −0.4334 (5) | 0.4241 (3) | 0.3086 (3) | 0.0221 (8) | |
Ru1 | −0.51818 (4) | 0.13564 (3) | 0.28039 (3) | 0.01787 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.025 (2) | 0.023 (2) | 0.049 (3) | 0.009 (2) | 0.006 (2) | 0.007 (2) |
C2 | 0.031 (3) | 0.018 (2) | 0.053 (3) | 0.0055 (19) | 0.011 (2) | 0.007 (2) |
C3 | 0.016 (2) | 0.025 (2) | 0.021 (2) | 0.0007 (17) | 0.0003 (17) | 0.0079 (18) |
C4 | 0.014 (2) | 0.028 (2) | 0.034 (3) | −0.0003 (18) | 0.0032 (18) | 0.006 (2) |
C5 | 0.016 (2) | 0.026 (2) | 0.024 (2) | −0.0034 (18) | 0.0055 (17) | 0.0037 (19) |
C6 | 0.020 (2) | 0.026 (2) | 0.028 (2) | −0.0084 (18) | 0.0036 (18) | 0.0060 (19) |
C7 | 0.023 (2) | 0.021 (2) | 0.024 (2) | −0.0041 (18) | −0.0020 (18) | 0.0074 (18) |
C8 | 0.024 (2) | 0.017 (2) | 0.025 (2) | −0.0049 (17) | 0.0036 (18) | 0.0001 (17) |
C9 | 0.021 (2) | 0.023 (2) | 0.023 (2) | −0.0045 (18) | 0.0019 (18) | 0.0019 (18) |
C10 | 0.013 (2) | 0.025 (2) | 0.027 (2) | −0.0067 (17) | −0.0029 (17) | 0.0068 (19) |
C11 | 0.035 (3) | 0.034 (3) | 0.026 (2) | −0.002 (2) | 0.006 (2) | 0.005 (2) |
C12 | 0.044 (3) | 0.023 (2) | 0.032 (3) | 0.003 (2) | 0.001 (2) | 0.004 (2) |
C13 | 0.023 (2) | 0.038 (3) | 0.029 (3) | 0.002 (2) | −0.0021 (19) | 0.011 (2) |
C14 | 0.019 (2) | 0.020 (2) | 0.032 (2) | 0.0018 (17) | 0.0040 (18) | 0.0094 (19) |
C15 | 0.019 (2) | 0.019 (2) | 0.028 (2) | −0.0023 (17) | −0.0022 (18) | 0.0070 (18) |
C16 | 0.019 (2) | 0.023 (2) | 0.030 (2) | 0.0016 (18) | 0.0022 (18) | 0.0033 (19) |
C17 | 0.025 (2) | 0.023 (2) | 0.043 (3) | −0.0068 (19) | −0.003 (2) | 0.010 (2) |
C18 | 0.037 (3) | 0.035 (3) | 0.052 (3) | −0.007 (2) | 0.005 (3) | 0.021 (3) |
C19 | 0.050 (3) | 0.047 (3) | 0.028 (3) | −0.007 (3) | 0.001 (2) | 0.016 (2) |
C20 | 0.036 (3) | 0.031 (3) | 0.033 (3) | −0.005 (2) | −0.002 (2) | 0.006 (2) |
C21 | 0.075 (4) | 0.044 (3) | 0.031 (3) | −0.024 (3) | −0.014 (3) | 0.005 (3) |
Cl1 | 0.0311 (6) | 0.0266 (6) | 0.0274 (6) | −0.0049 (5) | −0.0091 (5) | 0.0098 (5) |
Cl2 | 0.0226 (6) | 0.0283 (6) | 0.0402 (7) | −0.0027 (5) | 0.0142 (5) | −0.0024 (5) |
N1 | 0.0178 (18) | 0.0183 (19) | 0.043 (2) | 0.0033 (15) | 0.0034 (17) | 0.0070 (17) |
N2 | 0.0185 (18) | 0.0139 (17) | 0.035 (2) | 0.0036 (14) | 0.0038 (16) | 0.0069 (15) |
Ru1 | 0.01593 (18) | 0.01705 (18) | 0.02010 (18) | −0.00041 (12) | 0.00196 (13) | 0.00481 (13) |
Geometric parameters (Å, º) top
C5—C6 | 1.428 (6) | C7—H7 | 0.9600 |
C6—C7 | 1.435 (6) | C8—C12 | 1.490 (6) |
C7—C8 | 1.394 (6) | C9—H9 | 0.9600 |
C8—C9 | 1.430 (6) | C10—C13 | 1.494 (6) |
C9—C10 | 1.403 (6) | C11—H11A | 0.9599 |
C5—C10 | 1.445 (6) | C11—H11B | 0.9599 |
Ru1—C3 | 2.044 (4) | C11—H11C | 0.9599 |
Ru1—C5 | 2.100 (4) | C12—H12A | 0.9599 |
Ru1—C6 | 2.182 (4) | C12—H12B | 0.9599 |
Ru1—C7 | 2.240 (4) | C12—H12C | 0.9599 |
Ru1—C8 | 2.273 (4) | C13—H13A | 0.9599 |
Ru1—C9 | 2.191 (4) | C13—H13B | 0.9599 |
Ru1—C10 | 2.208 (4) | C13—H13C | 0.9599 |
Ru1—Cl1 | 2.4177 (14) | C14—C15 | 1.516 (6) |
Ru1—Cl2 | 2.4266 (13) | C14—H14A | 0.9600 |
N1—C3 | 1.361 (5) | C14—H14B | 0.9600 |
N1—C4 | 1.455 (5) | C15—C20 | 1.391 (6) |
N1—C1 | 1.462 (5) | C15—C16 | 1.402 (6) |
N2—C3 | 1.346 (5) | C16—C17 | 1.381 (6) |
N2—C14 | 1.449 (5) | C16—H16 | 0.9600 |
N2—C2 | 1.474 (5) | C17—C18 | 1.374 (7) |
C1—C2 | 1.517 (7) | C17—H17 | 0.9600 |
C1—H1A | 0.9600 | C18—C19 | 1.390 (7) |
C1—H1B | 0.9600 | C18—H18 | 0.9600 |
C2—H2A | 0.9600 | C19—C20 | 1.396 (7) |
C2—H2B | 0.9600 | C19—H19 | 0.9600 |
C4—C5 | 1.517 (6) | C20—C21 | 1.520 (7) |
C4—H4A | 0.9600 | C21—H21A | 0.9599 |
C4—H4B | 0.9600 | C21—H21B | 0.9599 |
C6—C11 | 1.502 (6) | C21—H21C | 0.9599 |
| | | |
C3—Ru1—C5 | 79.12 (17) | C11—C6—Ru1 | 130.1 (3) |
C3—Ru1—C6 | 101.99 (17) | C8—C7—C6 | 122.9 (4) |
C3—Ru1—C7 | 139.53 (16) | C8—C7—Ru1 | 73.3 (2) |
C3—Ru1—C8 | 158.41 (16) | C6—C7—Ru1 | 68.9 (2) |
C3—Ru1—C9 | 124.44 (16) | C8—C7—H7 | 118.5 |
C3—Ru1—C10 | 90.87 (16) | C6—C7—H7 | 118.5 |
C3—Ru1—Cl1 | 84.56 (12) | Ru1—C7—H7 | 132.6 |
C3—Ru1—Cl2 | 98.51 (12) | C7—C8—C9 | 116.8 (4) |
N1—C3—Ru1 | 115.0 (3) | C7—C8—C12 | 122.0 (4) |
N2—C3—Ru1 | 137.5 (3) | C9—C8—C12 | 121.2 (4) |
C5—Ru1—C6 | 38.89 (16) | C7—C8—Ru1 | 70.7 (2) |
C5—Ru1—C9 | 68.79 (17) | C9—C8—Ru1 | 68.2 (2) |
C6—Ru1—C9 | 80.26 (16) | C12—C8—Ru1 | 129.7 (3) |
C5—Ru1—C10 | 39.11 (16) | C10—C9—C8 | 124.2 (4) |
C6—Ru1—C10 | 69.47 (16) | C10—C9—Ru1 | 72.1 (2) |
C9—Ru1—C10 | 37.19 (16) | C8—C9—Ru1 | 74.5 (2) |
C5—Ru1—C7 | 68.72 (16) | C10—C9—H9 | 117.9 |
C6—Ru1—C7 | 37.84 (16) | C8—C9—H9 | 117.9 |
C9—Ru1—C7 | 65.71 (16) | Ru1—C9—H9 | 127.9 |
C10—Ru1—C7 | 79.59 (16) | C9—C10—C5 | 116.7 (4) |
C5—Ru1—C8 | 81.63 (17) | C9—C10—C13 | 121.0 (4) |
C6—Ru1—C8 | 67.76 (16) | C5—C10—C13 | 122.1 (4) |
C9—Ru1—C8 | 37.30 (16) | C9—C10—Ru1 | 70.8 (2) |
C10—Ru1—C8 | 67.90 (16) | C5—C10—Ru1 | 66.4 (2) |
C7—Ru1—C8 | 35.96 (15) | C13—C10—Ru1 | 129.6 (3) |
C5—Ru1—Cl1 | 123.23 (12) | C6—C11—H11A | 109.5 |
C6—Ru1—Cl1 | 94.73 (12) | C6—C11—H11B | 109.5 |
C9—Ru1—Cl1 | 151.00 (12) | H11A—C11—H11B | 109.5 |
C10—Ru1—Cl1 | 162.32 (12) | C6—C11—H11C | 109.5 |
C7—Ru1—Cl1 | 92.84 (12) | H11A—C11—H11C | 109.5 |
C8—Ru1—Cl1 | 114.43 (12) | H11B—C11—H11C | 109.5 |
C5—Ru1—Cl2 | 146.87 (12) | C8—C12—H12A | 109.5 |
C6—Ru1—Cl2 | 159.41 (12) | C8—C12—H12B | 109.5 |
C9—Ru1—Cl2 | 86.67 (12) | H12A—C12—H12B | 109.5 |
C10—Ru1—Cl2 | 108.59 (12) | C8—C12—H12C | 109.5 |
C7—Ru1—Cl2 | 121.86 (12) | H12A—C12—H12C | 109.5 |
C8—Ru1—Cl2 | 92.26 (12) | H12B—C12—H12C | 109.5 |
Cl1—Ru1—Cl2 | 89.00 (5) | C10—C13—H13A | 109.5 |
C3—N1—C4 | 122.0 (3) | C10—C13—H13B | 109.5 |
C3—N1—C1 | 112.9 (4) | H13A—C13—H13B | 109.5 |
C4—N1—C1 | 123.7 (3) | C10—C13—H13C | 109.5 |
C3—N2—C14 | 125.0 (3) | H13A—C13—H13C | 109.5 |
C3—N2—C2 | 112.2 (4) | H13B—C13—H13C | 109.5 |
C14—N2—C2 | 120.3 (3) | N2—C14—C15 | 112.0 (3) |
N1—C1—C2 | 101.8 (3) | N2—C14—H14A | 109.2 |
N1—C1—H1A | 111.4 | C15—C14—H14A | 109.2 |
C2—C1—H1A | 111.4 | N2—C14—H14B | 109.2 |
N1—C1—H1B | 111.4 | C15—C14—H14B | 109.2 |
C2—C1—H1B | 111.4 | H14A—C14—H14B | 107.9 |
H1A—C1—H1B | 109.3 | C20—C15—C16 | 118.9 (4) |
N2—C2—C1 | 102.7 (4) | C20—C15—C14 | 122.5 (4) |
N2—C2—H2A | 111.2 | C16—C15—C14 | 118.6 (4) |
C1—C2—H2A | 111.2 | C17—C16—C15 | 121.6 (4) |
N2—C2—H2B | 111.2 | C17—C16—H16 | 119.2 |
C1—C2—H2B | 111.2 | C15—C16—H16 | 119.2 |
H2A—C2—H2B | 109.1 | C18—C17—C16 | 119.7 (4) |
N2—C3—N1 | 107.3 (4) | C18—C17—H17 | 120.2 |
N1—C4—C5 | 107.1 (3) | C16—C17—H17 | 120.2 |
N1—C4—H4A | 110.3 | C17—C18—C19 | 119.3 (5) |
C5—C4—H4A | 110.3 | C17—C18—H18 | 120.3 |
N1—C4—H4B | 110.3 | C19—C18—H18 | 120.3 |
C5—C4—H4B | 110.3 | C18—C19—C20 | 121.8 (5) |
H4A—C4—H4B | 108.6 | C18—C19—H19 | 119.1 |
C6—C5—C10 | 121.1 (4) | C20—C19—H19 | 119.1 |
C6—C5—C4 | 120.0 (4) | C15—C20—C19 | 118.6 (4) |
C10—C5—C4 | 118.2 (4) | C15—C20—C21 | 121.8 (4) |
C6—C5—Ru1 | 73.7 (2) | C19—C20—C21 | 119.6 (5) |
C10—C5—Ru1 | 74.5 (2) | C20—C21—H21A | 109.5 |
C4—C5—Ru1 | 115.4 (3) | C20—C21—H21B | 109.5 |
C5—C6—C7 | 117.9 (4) | H21A—C21—H21B | 109.5 |
C5—C6—C11 | 122.5 (4) | C20—C21—H21C | 109.5 |
C7—C6—C11 | 119.6 (4) | H21A—C21—H21C | 109.5 |
C5—C6—Ru1 | 67.4 (2) | H21B—C21—H21C | 109.5 |
C7—C6—Ru1 | 73.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Cl2i | 0.96 | 2.75 | 3.390 (4) | 125 |
C7—H7···Cl1ii | 0.96 | 2.77 | 3.637 (5) | 150 |
C14—H14A···Cl2 | 0.96 | 2.58 | 3.470 (5) | 155 |
C21—H21A···Cl2 | 0.96 | 2.82 | 3.736 (6) | 159 |
Symmetry codes: (i) x−1, y, z; (ii) −x−1, −y, −z+1. |