Dichlorido­[1-(2-methyl­benz­yl)-3-(2,4,6-trimethyl­benz­yl)imidazolidin-2-yl­idene]ruthenium(II)

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.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](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

---

Computing details

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

Crystal data

[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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0199P)^2 + 3.385P] where P = (Fo^2 + 2Fc^2)/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

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cl2^i	0.96	2.75	3.390 (4)	125
C7—H7···Cl1^ii	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.