Three ruthenocene derivatives: (η⁵-4,7-dimethylindenyl)(η⁵-pentamethylcyclopentadienyl)ruthenium(II), [η⁵-[2](4,7)indeno[2]paracyclophanyl](η⁵-pentamethylcyclopentadienyl)ruthenium(II) and bis[η⁵-[2](4,7)indeno[2]paracyclophanyl]­ruthenium(II)

In the title compounds, [Ru(C₁₀H₁₅)(C₁₁H₁₁)], (III), [Ru(C₁₀H₁₅)(C₁₉H₁₇)], (IV), and [Ru(C₁₉H₁₇)₂], (V), respectively, the coordinating ring systems are planar and parallel, with the Ru atoms lying at perpendicular distances of Ru–Cp* 1.790 (1) Å and Ru–indenyl 1.836 (1) Å in (III), Ru–Cp* 1.791 (1) Å and Ru–indenyl 1.837 (1) Å in (IV), and Ru–indenyl 1.812 (1) Å and 1.809 (1) Å in (V) (Cp* is penta­methyl­cyclo­penta­dienyl). The ring conformations are eclipsed for (III), staggered for (IV) and intermediate for (V). All three compounds show short intermolecular contacts from C—H groups to some ring centroids; these could be regarded as C—H...π hydrogen bonds. The mol­ecules of each compound are thus connected via the 2₁ screw axis to form layers parallel to the xy plane.

S1. Comment

We have previously shown that indenophanes, such as (I) and (II), can be used for the preparation of novel multi-metal ferrocenophanes (Hopf & Dannheim, 1988). In an extension of these studies, we needed the title Ru complexes (III)-(V) for comparison. Whereas complex (III) can be considered as a `half' metallocenophane, the derivatives (IV) and (V) both contain cyclophane units. Here, we present the structures of compounds (III)-(V). \sch

The molecules are shown in Figs. 1–3. Compound (III) is isostructural with its Fe analogue (Jones et al., 2002). The coordinating ring systems are planar (details of the planes are given in the deposited material), except for the cyclophane bridgehead atoms, which are, as usual, displaced from the plane of the remaining four atoms of the respective rings [atoms C3 and C7 in (IV) by 0.150 (3) and 0.147 (3) Å, respectively, and atoms C12, C15, C12' and C15' in (V) by 0.150 (4), 0.144 (5), 0.149 (4) and 0.139 (4) Å, respectively]. These atoms were omitted from calculations of the best planes.

The distances of the Ru atoms from the best planes of the ligands (in Å) are, in (III), Ru—Cp* 1.790 (1) and Ru-indenyl (nine-atom plane) 1.836 (1), in (IV), Ru—Cp* 1.791 (1) and Ru-indenyl (seven-atom plane) 1.837 (1), and in (V), Ru-indenyl (seven-atom plane) 1.812 (1) and 1.809 (1). The absence of a Cp* ligand thus leads to shorter Ru-indenyl distances in (V). It is tempting to attribute this to the reduction of steric pressure from the methyl groups, but this supposition is difficult to prove. The planes are essentially parallel, with interplanar angles of 1.7 (1), 0.2 (1) and 4.5 (2)°, respectively. The individual Ru—C distances (Tables 1–3) indicate a slight distortion towards an η³ coordination of the indenyl ligands in (III) [Ru—C3a 2.220 (2) and Ru—C7a 2.226 (2) Å are somewhat longer than the other Ru—C] and in (IV) [Ru—C3a 2.224 (2) and Ru—C6a 2.221 (2) Å], but not in (V). The values may be compared with the range of 2.181–2.188 (2) Å in ruthenocene itself (Seiler & Dunitz, 1980).

The mutual ring conformation differs in the three structures. In (III), the rings are eclipsed, with a typical torsion angle of 1.3° for C1—Cg1—Cg2—C17 (Cg indicates a ring centroid); in (IV), they are staggered (C4—Cg1—Cg2—C27 - 29.8°), and in (V), the conformation is intermediate (C5—Cg1—Cg2—C5' 12.6°). Ruthenocene itself is almost ideally eclipsed (Hardgrove & Templeton, 1959; Seiler & Dunitz, 1980).

The molecular packing (Figs. 4–6) shows considerable qualitative similarity in all three compounds. All crystallize in the same space group (P2₁/n), all form layers of molecules parallel to the xy plane (two layers per z-axis repeat) and all involve short H···Cg contacts that could be classified as C—H···π hydrogen bonds. In (III), this contact is C6—H6···Cg(C15–19) [symmetry code: 1/2 - x, 1/2 + y, 1/2 - z], with a contact distance of 2.80 Å and an angle at H6 of 154°. For (IV), the contact is C2—H2A···Cg(C23–27) [symmetry code: 1/2 - x, 1/2 + y, 1/2 - z], with H···Cg 2.63 Å and an angle of 150°. For (V), the contact is C6'-H6'···Cg(C13/C14/C16/C17) [symmetry code: 3/2 - x, y - 1/2, 1/2 - z], with H···Cg 2.75 Å and an angle of 169°.

S2. Experimental

All three compounds were prepared by conventional methods, namely the metallation of the respective indene with methyl lithium in anhydrous tetrahydrofuran, followed by treatment of the anions thus formed with pentamethylcyclopentadienyl ruthenium chloride tetramer (Fagan et al., 1989) for (III) (83% yield) and (IV) (86%), and with commercial cyclooctadiene ruthenium dichloride for (V) (38%); for the original preparation see Bennett & Wilkinson (1959). All compounds were fully characterized by their spectroscopic and analytical data (Hartig, 1991). Single crystals were obtained by slow cooling of warm saturated solutions in hexane.

S3. Refinement

Methyl H atoms were identified in difference syntheses, idealized and then refined using rigid methyl groups allowed to rotate but not tip. Other H atoms were included using a riding model with fixed C—H bond lengths (aromatic 0.93, methyl 0.96 and methylene 0.97 Å); U_iso(H) values were fixed at 1.2 times the U_eq of the parent atom.

Computing details

For all compounds, data collection: P3 Software (Nicolet, 1987); cell refinement: P3 Software; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecule of (III) in the crystal. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecule of (IV) in the crystal. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. The molecule of (V) in the crystal. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. The packing diagram for (III) viewed along the z axis. Weak hydrogen bonds are indicated by dashed lines.
	Fig. 5. The packing diagram for (IV) viewed along the z axis. Weak hydrogen bonds are indicated by dashed lines.
	Fig. 6. The packing diagram for (V) viewed along the z axis. Weak hydrogen bonds are indicated by dashed lines.

(III) (η⁵-4,7-dimethylindenyl)(η⁵-pentamethylcyclopentadienyl)ruthenium(II)

Crystal data

[Ru(C10H15)(C11H11)]	F(000) = 784
Mr = 379.49	Dx = 1.407 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.609 (2) Å	Cell parameters from 46 reflections
b = 14.232 (3) Å	θ = 10.0–11.5°
c = 14.752 (3) Å	µ = 0.87 mm^−1
β = 97.50 (2)°	T = 293 K
V = 1792.1 (7) Å^3	Prism, orange-yellow
Z = 4	0.70 × 0.50 × 0.35 mm

Data collection

Nicolet R3 diffractometer	2605 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.011
Graphite monochromator	θmax = 25.1°, θmin = 3.1°
ω/θ scan	h = −10→2
Absorption correction: ψ scan (XEMP; Nicolet, 1987)	k = 0→16
Tmin = 0.608, Tmax = 0.737	l = −17→17
4248 measured reflections	3 standard reflections every 147 reflections
3172 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0275P)^2 + 0.4415P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
3172 reflections	Δρmax = 0.33 e Å^−3
207 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: Patterson	Extinction coefficient: 0.0025 (4)

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.8824 (0.0072) x + 8.1674 (0.0156) y - 4.1403 (0.0190) z = 6.1911 (0.0063)

* -0.0102 (0.0016) C1 * 0.0119 (0.0017) C2 * -0.0087 (0.0017) C3 * 0.0024 (0.0015) C3a * 0.0047 (0.0015) C7a -1.8378 (0.0013) Ru

Rms deviation of fitted atoms = 0.0084

6.9182 (0.0068) x + 8.1553 (0.0147) y - 3.9027 (0.0176) z = 2.6375 (0.0055)

Angle to previous plane (with approximate e.s.d.) = 0.99 (0.18)

* -0.0005 (0.0015) C15 * 0.0019 (0.0015) C16 * -0.0026 (0.0015) C17 * 0.0023 (0.0015) C18 * -0.0011 (0.0015) C19 1.7898 (0.0013) Ru

Rms deviation of fitted atoms = 0.0018

6.8521 (0.0038) x + 8.1827 (0.0078) y - 4.3081 (0.0122) z = 6.1360 (0.0044)

Angle to previous plane (with approximate e.s.d.) = 1.71 (0.14)

* -0.0236 (0.0021) C1 * 0.0061 (0.0021) C2 * 0.0031 (0.0021) C3 * 0.0177 (0.0022) C3a * -0.0114 (0.0020) C4 * -0.0110 (0.0022) C5 * 0.0066 (0.0022) C6 * 0.0080 (0.0021) C7 * 0.0043 (0.0022) C7a -1.8363 (0.0013) Ru

Rms deviation of fitted atoms = 0.0120

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
Ru	0.53074 (2)	0.208586 (13)	0.242271 (13)	0.03617 (8)
C1	0.7361 (3)	0.2891 (2)	0.3012 (2)	0.0548 (7)
H1	0.7674	0.2920	0.3639	0.066*
C2	0.7837 (3)	0.2213 (2)	0.2410 (2)	0.0625 (8)
H2	0.8544	0.1728	0.2573	0.075*
C3	0.7065 (3)	0.2387 (2)	0.1520 (2)	0.0555 (7)
H3	0.7153	0.2028	0.1002	0.067*
C3a	0.6125 (3)	0.32108 (17)	0.15565 (18)	0.0429 (6)
C4	0.5081 (3)	0.36936 (19)	0.08810 (18)	0.0500 (6)
C5	0.4340 (3)	0.4458 (2)	0.1154 (2)	0.0581 (8)
H5	0.3662	0.4785	0.0722	0.070*
C6	0.4548 (4)	0.47847 (19)	0.2063 (2)	0.0577 (8)
H6	0.4012	0.5321	0.2205	0.069*
C7	0.5503 (3)	0.43449 (19)	0.2743 (2)	0.0504 (7)
C7a	0.6312 (3)	0.35299 (17)	0.24904 (17)	0.0420 (6)
C8	0.5734 (5)	0.4675 (3)	0.3716 (2)	0.0812 (10)
H8A	0.5030	0.5186	0.3785	0.097*
H8B	0.6795	0.4884	0.3874	0.097*
H8C	0.5524	0.4168	0.4111	0.097*
C9	0.4842 (5)	0.3333 (2)	−0.0084 (2)	0.0750 (10)
H9A	0.4047	0.3699	−0.0440	0.090*
H9B	0.4521	0.2687	−0.0085	0.090*
H9C	0.5806	0.3383	−0.0343	0.090*
C10	0.3973 (5)	0.0328 (2)	0.1115 (2)	0.0738 (9)
H10A	0.3118	−0.0109	0.1023	0.089*
H10B	0.4946	−0.0009	0.1198	0.089*
H10C	0.3941	0.0730	0.0590	0.089*
C11	0.5590 (4)	−0.01095 (19)	0.3149 (2)	0.0671 (9)
H11A	0.6388	0.0077	0.3632	0.080*
H11B	0.6071	−0.0339	0.2641	0.080*
H11C	0.4961	−0.0597	0.3365	0.080*
C12	0.4496 (4)	0.1447 (2)	0.44619 (18)	0.0633 (8)
H12A	0.3780	0.1060	0.4743	0.076*
H12B	0.4432	0.2082	0.4673	0.076*
H12C	0.5544	0.1217	0.4623	0.076*
C13	0.2228 (3)	0.2890 (2)	0.3235 (2)	0.0608 (8)
H13A	0.1135	0.2753	0.3228	0.073*
H13B	0.2347	0.3414	0.2840	0.073*
H13C	0.2682	0.3041	0.3847	0.073*
C14	0.1838 (4)	0.2167 (2)	0.1202 (2)	0.0665 (9)
H14A	0.2110	0.1935	0.0633	0.080*
H14B	0.1963	0.2837	0.1225	0.080*
H14C	0.0769	0.2009	0.1253	0.080*
C15	0.3836 (3)	0.09090 (17)	0.19428 (17)	0.0452 (6)
C16	0.4577 (3)	0.07186 (17)	0.28518 (18)	0.0432 (6)
C17	0.4079 (3)	0.14192 (17)	0.34443 (16)	0.0412 (6)
C18	0.3044 (3)	0.20450 (17)	0.29048 (18)	0.0426 (6)
C19	0.2890 (3)	0.17282 (18)	0.19787 (18)	0.0442 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru	0.02903 (11)	0.03217 (11)	0.04723 (12)	−0.00019 (9)	0.00462 (7)	0.00597 (9)
C1	0.0354 (14)	0.0569 (16)	0.0690 (18)	−0.0093 (13)	−0.0054 (12)	0.0113 (15)
C2	0.0302 (14)	0.0529 (17)	0.104 (3)	0.0033 (12)	0.0089 (15)	0.0148 (17)
C3	0.0456 (16)	0.0501 (16)	0.076 (2)	−0.0037 (13)	0.0291 (15)	0.0024 (14)
C3a	0.0362 (14)	0.0383 (13)	0.0565 (16)	−0.0084 (10)	0.0143 (12)	0.0065 (11)
C4	0.0509 (16)	0.0472 (15)	0.0526 (15)	−0.0142 (13)	0.0090 (12)	0.0125 (12)
C5	0.0522 (17)	0.0488 (16)	0.071 (2)	−0.0039 (14)	−0.0013 (14)	0.0240 (15)
C6	0.0503 (17)	0.0347 (14)	0.090 (2)	0.0030 (12)	0.0169 (16)	0.0053 (14)
C7	0.0475 (16)	0.0395 (14)	0.0652 (17)	−0.0092 (12)	0.0115 (13)	−0.0034 (12)
C7a	0.0338 (13)	0.0386 (13)	0.0535 (15)	−0.0090 (10)	0.0053 (11)	0.0057 (11)
C8	0.090 (3)	0.073 (2)	0.081 (2)	−0.006 (2)	0.014 (2)	−0.0219 (19)
C9	0.092 (3)	0.077 (2)	0.0551 (19)	−0.020 (2)	0.0060 (17)	0.0109 (16)
C10	0.091 (3)	0.065 (2)	0.066 (2)	−0.0169 (19)	0.0151 (18)	−0.0122 (16)
C11	0.068 (2)	0.0430 (16)	0.090 (2)	0.0106 (14)	0.0078 (18)	0.0152 (15)
C12	0.0618 (19)	0.076 (2)	0.0507 (17)	−0.0089 (16)	0.0011 (14)	0.0086 (15)
C13	0.0451 (16)	0.0548 (17)	0.086 (2)	0.0082 (14)	0.0212 (15)	0.0065 (16)
C14	0.0471 (17)	0.081 (2)	0.0662 (18)	−0.0093 (16)	−0.0107 (14)	0.0276 (17)
C15	0.0481 (15)	0.0393 (13)	0.0488 (14)	−0.0118 (11)	0.0090 (12)	−0.0002 (11)
C16	0.0425 (14)	0.0327 (12)	0.0543 (15)	−0.0027 (11)	0.0056 (12)	0.0086 (11)
C17	0.0366 (13)	0.0413 (13)	0.0454 (13)	−0.0050 (11)	0.0043 (10)	0.0070 (11)
C18	0.0334 (13)	0.0390 (13)	0.0560 (15)	−0.0031 (11)	0.0079 (11)	0.0065 (12)
C19	0.0333 (14)	0.0464 (14)	0.0513 (15)	−0.0089 (11)	−0.0001 (11)	0.0141 (11)

Geometric parameters (Å, º)

Ru—C19	2.160 (2)	C8—H8C	0.9600
Ru—C18	2.161 (3)	C9—H9A	0.9600
Ru—C15	2.163 (2)	C9—H9B	0.9600
Ru—C16	2.165 (2)	C9—H9C	0.9600
Ru—C17	2.169 (2)	C10—C15	1.492 (4)
Ru—C3	2.185 (3)	C10—H10A	0.9600
Ru—C2	2.188 (3)	C10—H10B	0.9600
Ru—C1	2.190 (3)	C10—H10C	0.9600
Ru—C3a	2.220 (2)	C11—C16	1.498 (3)
Ru—C7a	2.227 (2)	C11—H11A	0.9600
C1—C2	1.408 (4)	C11—H11B	0.9600
C1—C7a	1.433 (4)	C11—H11C	0.9600
C1—H1	0.9300	C12—C17	1.498 (3)
C2—C3	1.415 (4)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C3a	1.430 (4)	C12—H12C	0.9600
C3—H3	0.9300	C13—C18	1.505 (4)
C3a—C4	1.428 (4)	C13—H13A	0.9600
C3a—C7a	1.440 (4)	C13—H13B	0.9600
C4—C5	1.349 (4)	C13—H13C	0.9600
C4—C9	1.502 (4)	C14—C19	1.500 (3)
C5—C6	1.408 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.363 (4)	C14—H14C	0.9600
C6—H6	0.9300	C15—C19	1.427 (4)
C7—C7a	1.427 (4)	C15—C16	1.434 (3)
C7—C8	1.498 (4)	C16—C17	1.428 (4)
C8—H8A	0.9600	C17—C18	1.427 (3)
C8—H8B	0.9600	C18—C19	1.428 (4)
C19—Ru—C18	38.61 (10)	C7a—C7—C8	119.8 (3)
C19—Ru—C15	38.57 (10)	C7—C7a—C1	132.1 (3)
C18—Ru—C15	64.66 (10)	C7—C7a—C3a	120.6 (2)
C19—Ru—C16	64.63 (9)	C1—C7a—C3a	107.3 (2)
C18—Ru—C16	64.57 (9)	C7—C7a—Ru	124.19 (18)
C15—Ru—C16	38.69 (9)	C1—C7a—Ru	69.68 (14)
C19—Ru—C17	64.51 (9)	C3a—C7a—Ru	70.84 (13)
C18—Ru—C17	38.47 (9)	C7—C8—H8A	109.5
C15—Ru—C17	64.59 (9)	C7—C8—H8B	109.5
C16—Ru—C17	38.48 (9)	H8A—C8—H8B	109.5
C19—Ru—C3	125.31 (11)	C7—C8—H8C	109.5
C18—Ru—C3	158.77 (11)	H8A—C8—H8C	109.5
C15—Ru—C3	112.01 (11)	H8B—C8—H8C	109.5
C16—Ru—C3	127.24 (10)	C4—C9—H9A	109.5
C17—Ru—C3	161.54 (10)	C4—C9—H9B	109.5
C19—Ru—C2	159.71 (12)	H9A—C9—H9B	109.5
C18—Ru—C2	161.18 (12)	C4—C9—H9C	109.5
C15—Ru—C2	127.03 (11)	H9A—C9—H9C	109.5
C16—Ru—C2	113.83 (10)	H9B—C9—H9C	109.5
C17—Ru—C2	128.17 (11)	C15—C10—H10A	109.5
C3—Ru—C2	37.76 (12)	C15—C10—H10B	109.5
C19—Ru—C1	160.06 (11)	H10A—C10—H10B	109.5
C18—Ru—C1	126.85 (11)	C15—C10—H10C	109.5
C15—Ru—C1	160.65 (11)	H10A—C10—H10C	109.5
C16—Ru—C1	127.22 (10)	H10B—C10—H10C	109.5
C17—Ru—C1	113.26 (10)	C16—C11—H11A	109.5
C3—Ru—C1	63.37 (12)	C16—C11—H11B	109.5
C2—Ru—C1	37.53 (11)	H11A—C11—H11B	109.5
C19—Ru—C3a	111.16 (9)	C16—C11—H11C	109.5
C18—Ru—C3a	125.19 (9)	H11A—C11—H11C	109.5
C15—Ru—C3a	125.90 (10)	H11B—C11—H11C	109.5
C16—Ru—C3a	160.52 (10)	C17—C12—H12A	109.5
C17—Ru—C3a	159.30 (10)	C17—C12—H12B	109.5
C3—Ru—C3a	37.88 (10)	H12A—C12—H12B	109.5
C2—Ru—C3a	62.93 (11)	C17—C12—H12C	109.5
C1—Ru—C3a	63.29 (10)	H12A—C12—H12C	109.5
C19—Ru—C7a	125.75 (9)	H12B—C12—H12C	109.5
C18—Ru—C7a	111.82 (9)	C18—C13—H13A	109.5
C15—Ru—C7a	159.53 (9)	C18—C13—H13B	109.5
C16—Ru—C7a	160.45 (9)	H13A—C13—H13B	109.5
C17—Ru—C7a	126.45 (10)	C18—C13—H13C	109.5
C3—Ru—C7a	63.30 (10)	H13A—C13—H13C	109.5
C2—Ru—C7a	62.82 (10)	H13B—C13—H13C	109.5
C1—Ru—C7a	37.85 (9)	C19—C14—H14A	109.5
C3a—Ru—C7a	37.78 (9)	C19—C14—H14B	109.5
C2—C1—C7a	108.2 (3)	H14A—C14—H14B	109.5
C2—C1—Ru	71.15 (16)	C19—C14—H14C	109.5
C7a—C1—Ru	72.47 (14)	H14A—C14—H14C	109.5
C2—C1—H1	125.9	H14B—C14—H14C	109.5
C7a—C1—H1	125.9	C19—C15—C16	107.8 (2)
Ru—C1—H1	122.1	C19—C15—C10	126.1 (3)
C1—C2—C3	109.0 (3)	C16—C15—C10	126.0 (3)
C1—C2—Ru	71.32 (16)	C19—C15—Ru	70.60 (14)
C3—C2—Ru	71.00 (16)	C16—C15—Ru	70.74 (13)
C1—C2—H2	125.5	C10—C15—Ru	126.3 (2)
C3—C2—H2	125.5	C17—C16—C15	107.9 (2)
Ru—C2—H2	123.8	C17—C16—C11	125.5 (2)
C2—C3—C3a	107.9 (3)	C15—C16—C11	126.4 (3)
C2—C3—Ru	71.24 (16)	C17—C16—Ru	70.93 (13)
C3a—C3—Ru	72.39 (15)	C15—C16—Ru	70.57 (13)
C2—C3—H3	126.0	C11—C16—Ru	127.8 (2)
C3a—C3—H3	126.0	C18—C17—C16	108.1 (2)
Ru—C3—H3	122.0	C18—C17—C12	126.4 (2)
C4—C3a—C3	132.5 (3)	C16—C17—C12	125.4 (2)
C4—C3a—C7a	119.8 (2)	C18—C17—Ru	70.44 (14)
C3—C3a—C7a	107.6 (2)	C16—C17—Ru	70.59 (14)
C4—C3a—Ru	122.07 (17)	C12—C17—Ru	127.56 (18)
C3—C3a—Ru	69.73 (14)	C17—C18—C19	108.0 (2)
C7a—C3a—Ru	71.38 (13)	C17—C18—C13	127.0 (2)
C5—C4—C3a	117.3 (3)	C19—C18—C13	124.9 (2)
C5—C4—C9	123.2 (3)	C17—C18—Ru	71.09 (14)
C3a—C4—C9	119.5 (3)	C19—C18—Ru	70.65 (15)
C4—C5—C6	123.0 (3)	C13—C18—Ru	124.33 (18)
C4—C5—H5	118.5	C15—C19—C18	108.1 (2)
C6—C5—H5	118.5	C15—C19—C14	127.0 (3)
C7—C6—C5	122.6 (3)	C18—C19—C14	124.8 (3)
C7—C6—H6	118.7	C15—C19—Ru	70.83 (14)
C5—C6—H6	118.7	C18—C19—Ru	70.74 (14)
C6—C7—C7a	116.7 (3)	C14—C19—Ru	126.52 (18)
C6—C7—C8	123.6 (3)

(IV) (η⁵-[2](4,7)indeno[2]paracyclophanyl)(η⁵-pentamethylcyclopentadienyl) ruthenium(II)

Crystal data

[Ru(C10H15)(C19H17)]	F(000) = 1000
Mr = 481.62	Dx = 1.385 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.648 (2) Å	Cell parameters from 46 reflections
b = 14.757 (3) Å	θ = 10.0–11.5°
c = 13.798 (3) Å	µ = 0.69 mm^−1
β = 103.134 (15)°	T = 293 K
V = 2309.7 (7) Å^3	Prism, orange-yellow
Z = 4	0.7 × 0.4 × 0.3 mm

Data collection

Nicolet R3 diffractometer	3547 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 25.1°, θmin = 3.0°
ω/θ scan	h = −13→13
Absorption correction: ψ scan (XEMP; Nicolet, 1987)	k = 0→17
Tmin = 0.643, Tmax = 0.819	l = −16→16
8161 measured reflections	3 standard reflections every 147 reflections
4086 independent reflections	intensity decay: none

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0326P)^2 + 0.5968P] where P = (Fo^2 + 2Fc^2)/3
4086 reflections	(Δ/σ)max = 0.003
276 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.19 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

8.9450 (0.0082) x + 8.6253 (0.0128) y - 5.9291 (0.0132) z = 5.6794 (0.0067)

* 0.0032 (0.0012) C23 * -0.0044 (0.0013) C24 * 0.0039 (0.0013) C25 * -0.0019 (0.0013) C26 * -0.0008 (0.0013) C27 1.7904 (0.0010) Ru

Rms deviation of fitted atoms = 0.0031

8.9599 (0.0073) x + 8.6266 (0.0098) y - 5.8795 (0.0070) z = 9.3226 (0.0045)

Angle to previous plane (with approximate e.s.d.) = 0.24 (0.14)

* 0.0165 (0.0016) C3a * -0.0080 (0.0014) C4 * -0.0070 (0.0016) C5 * -0.0043 (0.0014) C6 * 0.0163 (0.0016) C6a * -0.0098 (0.0015) C8 * -0.0037 (0.0015) C9 0.1501 (0.0027) C3 0.1471 (0.0027) C7 - 1.8373 (0.0010) Ru

Rms deviation of fitted atoms = 0.0106

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
Ru	0.397052 (12)	0.575810 (10)	0.176806 (11)	0.03145 (6)
C1	0.4906 (3)	0.92382 (17)	0.1263 (2)	0.0680 (8)
H1A	0.4647	0.9156	0.0549	0.082*
H1B	0.4912	0.9883	0.1399	0.082*
C2	0.4006 (2)	0.87628 (17)	0.1786 (2)	0.0620 (7)
H2A	0.3774	0.9188	0.2242	0.074*
H2B	0.3305	0.8604	0.1286	0.074*
C3	0.44888 (18)	0.79210 (14)	0.23512 (17)	0.0422 (5)
C3a	0.47379 (16)	0.71415 (13)	0.18143 (15)	0.0347 (4)
C4	0.43159 (18)	0.68667 (14)	0.08096 (15)	0.0405 (4)
H4	0.3722	0.7150	0.0343	0.049*
C5	0.49519 (19)	0.60907 (14)	0.06387 (15)	0.0425 (5)
H5	0.4854	0.5782	0.0038	0.051*
C6	0.57674 (18)	0.58600 (13)	0.15385 (17)	0.0408 (5)
H6	0.6286	0.5372	0.1629	0.049*
C6a	0.56512 (16)	0.65096 (13)	0.22793 (15)	0.0356 (4)
C7	0.63001 (19)	0.66686 (15)	0.32790 (16)	0.0445 (5)
C8	0.5860 (2)	0.73028 (17)	0.38062 (16)	0.0526 (6)
H8	0.6153	0.7332	0.4491	0.063*
C9	0.4968 (2)	0.79255 (16)	0.33491 (18)	0.0523 (6)
H9	0.4701	0.8350	0.3745	0.063*
C10	0.7546 (2)	0.63185 (18)	0.3592 (2)	0.0631 (7)
H10A	0.7551	0.5678	0.3433	0.076*
H10B	0.7811	0.6379	0.4308	0.076*
C11	0.8434 (2)	0.6820 (2)	0.3086 (3)	0.0757 (8)
H11A	0.9122	0.6992	0.3592	0.091*
H11B	0.8690	0.6407	0.2630	0.091*
C12	0.7914 (2)	0.76602 (19)	0.2519 (2)	0.0602 (6)
C13	0.7452 (2)	0.76266 (19)	0.1503 (2)	0.0611 (7)
H13	0.7730	0.7197	0.1119	0.073*
C14	0.6577 (2)	0.82285 (18)	0.10524 (18)	0.0583 (6)
H14	0.6278	0.8197	0.0368	0.070*
C15	0.6139 (2)	0.88750 (16)	0.16019 (18)	0.0542 (6)
C16	0.6785 (2)	0.90198 (17)	0.25672 (19)	0.0553 (6)
H16	0.6627	0.9526	0.2916	0.066*
C17	0.7655 (2)	0.84280 (17)	0.30148 (19)	0.0585 (6)
H17	0.8078	0.8542	0.3660	0.070*
C18	0.1763 (2)	0.4822 (2)	0.01872 (18)	0.0638 (7)
H18A	0.1129	0.4400	0.0158	0.077*
H18B	0.2302	0.4588	−0.0184	0.077*
H18C	0.1451	0.5391	−0.0093	0.077*
C19	0.3743 (3)	0.35263 (16)	0.1445 (2)	0.0639 (7)
H19A	0.4557	0.3439	0.1768	0.077*
H19B	0.3665	0.3559	0.0738	0.077*
H19C	0.3286	0.3027	0.1598	0.077*
C20	0.4544 (3)	0.4327 (2)	0.3640 (2)	0.0699 (8)
H20A	0.4153	0.3974	0.4052	0.084*
H20B	0.4988	0.4802	0.4029	0.084*
H20C	0.5067	0.3945	0.3377	0.084*
C21	0.2956 (3)	0.6053 (2)	0.37816 (19)	0.0668 (7)
H21A	0.2835	0.6682	0.3608	0.080*
H21B	0.3707	0.5979	0.4237	0.080*
H21C	0.2342	0.5848	0.4089	0.080*
C22	0.1228 (2)	0.6368 (2)	0.1654 (2)	0.0718 (8)
H22A	0.1023	0.6459	0.0947	0.086*
H22B	0.1520	0.6924	0.1978	0.086*
H22C	0.0542	0.6178	0.1877	0.086*
C23	0.24018 (18)	0.49602 (15)	0.12551 (15)	0.0419 (5)
C24	0.33080 (19)	0.43906 (13)	0.18064 (16)	0.0417 (5)
C25	0.36433 (19)	0.47335 (15)	0.27971 (15)	0.0434 (5)
C26	0.2932 (2)	0.55080 (15)	0.28601 (16)	0.0447 (5)
C27	0.21610 (19)	0.56524 (15)	0.19054 (17)	0.0442 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru	0.03165 (9)	0.02852 (9)	0.03413 (9)	−0.00338 (6)	0.00739 (6)	−0.00144 (6)
C1	0.0758 (18)	0.0433 (14)	0.0765 (18)	−0.0057 (12)	−0.0001 (15)	0.0124 (13)
C2	0.0585 (15)	0.0388 (13)	0.0865 (19)	0.0123 (11)	0.0120 (13)	−0.0050 (12)
C3	0.0391 (10)	0.0342 (10)	0.0561 (12)	−0.0010 (8)	0.0163 (9)	−0.0073 (9)
C3a	0.0328 (9)	0.0298 (9)	0.0424 (10)	−0.0048 (8)	0.0102 (8)	−0.0016 (8)
C4	0.0434 (11)	0.0367 (10)	0.0396 (10)	−0.0068 (9)	0.0057 (8)	0.0029 (9)
C5	0.0528 (12)	0.0390 (10)	0.0395 (10)	−0.0118 (9)	0.0185 (9)	−0.0078 (9)
C6	0.0363 (10)	0.0313 (10)	0.0581 (13)	−0.0021 (8)	0.0176 (9)	−0.0054 (9)
C6a	0.0318 (9)	0.0311 (10)	0.0438 (10)	−0.0047 (8)	0.0087 (8)	−0.0007 (8)
C7	0.0448 (11)	0.0385 (11)	0.0462 (12)	−0.0087 (9)	0.0018 (9)	0.0012 (9)
C8	0.0642 (14)	0.0543 (13)	0.0374 (11)	−0.0157 (12)	0.0074 (10)	−0.0072 (10)
C9	0.0599 (14)	0.0460 (13)	0.0573 (14)	−0.0066 (11)	0.0266 (11)	−0.0177 (10)
C10	0.0529 (14)	0.0531 (14)	0.0699 (16)	0.0004 (11)	−0.0142 (12)	0.0011 (13)
C11	0.0406 (13)	0.0729 (18)	0.107 (2)	0.0021 (13)	0.0021 (14)	0.0023 (17)
C12	0.0371 (12)	0.0622 (15)	0.0801 (17)	−0.0139 (11)	0.0107 (11)	−0.0042 (14)
C13	0.0531 (14)	0.0633 (16)	0.0739 (17)	−0.0184 (12)	0.0291 (13)	−0.0128 (13)
C14	0.0658 (16)	0.0632 (15)	0.0475 (13)	−0.0272 (13)	0.0163 (11)	−0.0024 (12)
C15	0.0604 (14)	0.0413 (12)	0.0588 (14)	−0.0187 (11)	0.0087 (11)	0.0063 (11)
C16	0.0629 (15)	0.0413 (12)	0.0595 (14)	−0.0170 (11)	0.0095 (12)	−0.0060 (11)
C17	0.0502 (13)	0.0585 (15)	0.0599 (15)	−0.0234 (12)	−0.0021 (11)	−0.0043 (12)
C18	0.0541 (14)	0.0853 (19)	0.0491 (13)	−0.0233 (14)	0.0056 (11)	−0.0052 (13)
C19	0.0814 (18)	0.0381 (13)	0.0811 (18)	−0.0069 (12)	0.0373 (15)	−0.0056 (12)
C20	0.0766 (19)	0.0716 (18)	0.0567 (15)	0.0036 (14)	0.0052 (14)	0.0210 (13)
C21	0.086 (2)	0.0673 (16)	0.0535 (15)	−0.0103 (15)	0.0304 (14)	−0.0124 (13)
C22	0.0525 (15)	0.0784 (19)	0.088 (2)	0.0180 (14)	0.0229 (14)	0.0069 (16)
C23	0.0387 (11)	0.0466 (12)	0.0408 (11)	−0.0134 (9)	0.0094 (9)	−0.0008 (9)
C24	0.0462 (11)	0.0335 (10)	0.0486 (12)	−0.0103 (9)	0.0173 (9)	−0.0005 (9)
C25	0.0453 (11)	0.0438 (12)	0.0410 (11)	−0.0074 (9)	0.0097 (9)	0.0070 (9)
C26	0.0482 (12)	0.0470 (12)	0.0427 (11)	−0.0086 (10)	0.0185 (10)	−0.0022 (9)
C27	0.0363 (10)	0.0478 (12)	0.0508 (12)	−0.0043 (9)	0.0151 (9)	0.0020 (10)

Geometric parameters (Å, º)

Ru—C3a	2.2238 (19)	C23—C24	1.426 (3)
Ru—C4	2.197 (2)	C23—C27	1.429 (3)
Ru—C5	2.188 (2)	C24—C25	1.426 (3)
Ru—C6	2.192 (2)	C25—C26	1.426 (3)
Ru—C6a	2.2209 (19)	C26—C27	1.431 (3)
Ru—C23	2.154 (2)	C1—H1A	0.9700
Ru—C24	2.165 (2)	C1—H1B	0.9700
Ru—C25	2.166 (2)	C2—H2A	0.9700
Ru—C26	2.168 (2)	C2—H2B	0.9700
Ru—C27	2.164 (2)	C4—H4	0.9300
C1—C15	1.504 (4)	C5—H5	0.9300
C1—C2	1.567 (4)	C6—H6	0.9300
C2—C3	1.506 (3)	C8—H8	0.9300
C3—C9	1.363 (3)	C9—H9	0.9300
C3—C3a	1.433 (3)	C10—H10A	0.9700
C3a—C4	1.421 (3)	C10—H10B	0.9700
C3a—C6a	1.450 (3)	C11—H11A	0.9700
C4—C5	1.413 (3)	C11—H11B	0.9700
C5—C6	1.423 (3)	C13—H13	0.9300
C6—C6a	1.430 (3)	C14—H14	0.9300
C6a—C7	1.434 (3)	C16—H16	0.9300
C7—C8	1.355 (3)	C17—H17	0.9300
C7—C10	1.509 (3)	C18—H18A	0.9600
C8—C9	1.423 (4)	C18—H18B	0.9600
C10—C11	1.559 (4)	C18—H18C	0.9600
C11—C12	1.517 (4)	C19—H19A	0.9600
C12—C13	1.385 (4)	C19—H19B	0.9600
C12—C17	1.391 (4)	C19—H19C	0.9600
C13—C14	1.388 (4)	C20—H20A	0.9600
C14—C15	1.386 (4)	C20—H20B	0.9600
C15—C16	1.390 (3)	C20—H20C	0.9600
C16—C17	1.373 (4)	C21—H21A	0.9600
C18—C23	1.506 (3)	C21—H21B	0.9600
C19—C24	1.499 (3)	C21—H21C	0.9600
C20—C25	1.503 (3)	C22—H22A	0.9600
C21—C26	1.499 (3)	C22—H22B	0.9600
C22—C27	1.499 (3)	C22—H22C	0.9600
C23—Ru—C27	38.64 (8)	C25—C24—C19	125.5 (2)
C23—Ru—C24	38.56 (8)	C23—C24—C19	126.1 (2)
C27—Ru—C24	64.60 (8)	C25—C24—Ru	70.81 (11)
C23—Ru—C25	64.62 (8)	C23—C24—Ru	70.28 (11)
C27—Ru—C25	64.69 (8)	C19—C24—Ru	129.45 (16)
C24—Ru—C25	38.45 (8)	C26—C25—C24	107.84 (19)
C23—Ru—C26	64.50 (8)	C26—C25—C20	125.9 (2)
C27—Ru—C26	38.59 (8)	C24—C25—C20	126.2 (2)
C24—Ru—C26	64.28 (8)	C26—C25—Ru	70.84 (12)
C25—Ru—C26	38.42 (9)	C24—C25—Ru	70.74 (11)
C23—Ru—C5	115.48 (8)	C20—C25—Ru	126.15 (17)
C27—Ru—C5	139.07 (9)	C25—C26—C27	108.35 (19)
C24—Ru—C5	118.25 (8)	C25—C26—C21	125.6 (2)
C25—Ru—C5	145.25 (9)	C27—C26—C21	126.0 (2)
C26—Ru—C5	176.28 (8)	C25—C26—Ru	70.74 (12)
C23—Ru—C6	139.17 (8)	C27—C26—Ru	70.57 (12)
C27—Ru—C6	176.80 (8)	C21—C26—Ru	126.30 (17)
C24—Ru—C6	115.14 (8)	C23—C27—C26	107.46 (19)
C25—Ru—C6	117.30 (8)	C23—C27—C22	126.4 (2)
C26—Ru—C6	144.51 (9)	C26—C27—C22	126.0 (2)
C5—Ru—C6	37.91 (8)	C23—C27—Ru	70.28 (11)
C23—Ru—C4	117.83 (8)	C26—C27—Ru	70.84 (12)
C27—Ru—C4	114.93 (8)	C22—C27—Ru	126.79 (17)
C24—Ru—C4	145.43 (8)	C15—C1—H1A	109.0
C25—Ru—C4	175.98 (8)	C2—C1—H1A	109.0
C26—Ru—C4	138.80 (8)	C15—C1—H1B	109.0
C5—Ru—C4	37.58 (8)	C2—C1—H1B	109.0
C6—Ru—C4	63.29 (8)	H1A—C1—H1B	107.8
C23—Ru—C6a	176.55 (8)	C3—C2—H2A	108.9
C27—Ru—C6a	144.48 (8)	C1—C2—H2A	108.9
C24—Ru—C6a	138.67 (8)	C3—C2—H2B	108.9
C25—Ru—C6a	114.46 (8)	C1—C2—H2B	108.9
C26—Ru—C6a	117.08 (8)	H2A—C2—H2B	107.7
C5—Ru—C6a	63.17 (8)	C5—C4—H4	125.8
C6—Ru—C6a	37.81 (7)	C3a—C4—H4	125.8
C4—Ru—C6a	63.30 (7)	Ru—C4—H4	122.8
C23—Ru—C3a	144.77 (8)	C4—C5—H5	125.7
C27—Ru—C3a	117.18 (8)	C6—C5—H5	125.7
C24—Ru—C3a	176.38 (8)	Ru—C5—H5	123.2
C25—Ru—C3a	138.71 (8)	C5—C6—H6	126.0
C26—Ru—C3a	114.87 (8)	C6a—C6—H6	126.0
C5—Ru—C3a	62.79 (7)	Ru—C6—H6	122.7
C6—Ru—C3a	63.28 (7)	C7—C8—H8	118.8
C4—Ru—C3a	37.48 (7)	C9—C8—H8	118.8
C6a—Ru—C3a	38.08 (7)	C3—C9—H9	118.8
C15—C1—C2	112.9 (2)	C8—C9—H9	118.8
C3—C2—C1	113.4 (2)	C7—C10—H10A	108.8
C9—C3—C3a	116.2 (2)	C11—C10—H10A	108.8
C9—C3—C2	122.5 (2)	C7—C10—H10B	108.8
C3a—C3—C2	119.3 (2)	C11—C10—H10B	108.8
C4—C3a—C3	131.90 (19)	H10A—C10—H10B	107.7
C4—C3a—C6a	107.73 (17)	C12—C11—H11A	109.0
C3—C3a—C6a	120.12 (18)	C10—C11—H11A	109.0
C4—C3a—Ru	70.26 (11)	C12—C11—H11B	109.0
C3—C3a—Ru	128.64 (14)	C10—C11—H11B	109.0
C6a—C3a—Ru	70.85 (10)	H11A—C11—H11B	107.8
C5—C4—C3a	108.42 (18)	C12—C13—H13	119.8
C5—C4—Ru	70.83 (12)	C14—C13—H13	119.8
C3a—C4—Ru	72.27 (11)	C15—C14—H14	119.3
C4—C5—C6	108.65 (18)	C13—C14—H14	119.3
C4—C5—Ru	71.59 (12)	C17—C16—H16	119.4
C6—C5—Ru	71.22 (12)	C15—C16—H16	119.4
C5—C6—C6a	108.09 (18)	C16—C17—H17	119.4
C5—C6—Ru	70.87 (12)	C12—C17—H17	119.4
C6a—C6—Ru	72.19 (11)	C23—C18—H18A	109.5
C6—C6a—C7	133.04 (19)	C23—C18—H18B	109.5
C6—C6a—C3a	107.10 (17)	H18A—C18—H18B	109.5
C7—C6a—C3a	119.59 (18)	C23—C18—H18C	109.5
C6—C6a—Ru	70.01 (11)	H18A—C18—H18C	109.5
C7—C6a—Ru	128.41 (14)	H18B—C18—H18C	109.5
C3a—C6a—Ru	71.07 (10)	C24—C19—H19A	109.5
C8—C7—C6a	116.7 (2)	C24—C19—H19B	109.5
C8—C7—C10	122.6 (2)	H19A—C19—H19B	109.5
C6a—C7—C10	118.8 (2)	C24—C19—H19C	109.5
C7—C8—C9	122.4 (2)	H19A—C19—H19C	109.5
C3—C9—C8	122.3 (2)	H19B—C19—H19C	109.5
C7—C10—C11	113.7 (2)	C25—C20—H20A	109.5
C12—C11—C10	113.0 (2)	C25—C20—H20B	109.5
C13—C12—C17	116.7 (3)	H20A—C20—H20B	109.5
C13—C12—C11	120.7 (3)	C25—C20—H20C	109.5
C17—C12—C11	121.2 (3)	H20A—C20—H20C	109.5
C12—C13—C14	120.5 (3)	H20B—C20—H20C	109.5
C15—C14—C13	121.3 (2)	C26—C21—H21A	109.5
C14—C15—C16	116.3 (2)	C26—C21—H21B	109.5
C14—C15—C1	121.3 (2)	H21A—C21—H21B	109.5
C16—C15—C1	120.9 (3)	C26—C21—H21C	109.5
C17—C16—C15	121.1 (2)	H21A—C21—H21C	109.5
C16—C17—C12	121.1 (2)	H21B—C21—H21C	109.5
C24—C23—C27	108.26 (18)	C27—C22—H22A	109.5
C24—C23—C18	125.7 (2)	C27—C22—H22B	109.5
C27—C23—C18	126.0 (2)	H22A—C22—H22B	109.5
C24—C23—Ru	71.16 (11)	C27—C22—H22C	109.5
C27—C23—Ru	71.08 (12)	H22A—C22—H22C	109.5
C18—C23—Ru	126.09 (15)	H22B—C22—H22C	109.5
C25—C24—C23	108.08 (19)

(V) bis(η⁵-[2](4,7)indeno[2]paracyclophanyl)ruthenium(II)

Crystal data

[Ru(C19H17)2]	F(000) = 1224
Mr = 591.72	Dx = 1.414 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.620 (3) Å	Cell parameters from 50 reflections
b = 17.026 (4) Å	θ = 10.0–11.5°
c = 13.005 (3) Å	µ = 0.59 mm^−1
β = 95.92 (2)°	T = 293 K
V = 2779.5 (11) Å^3	Parallelepiped, orange-yellow
Z = 4	0.5 × 0.5 × 0.4 mm

Data collection

Nicolet R3 diffractometer	4008 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 3.2°
ω scan	h = −15→5
Absorption correction: ψ scan (XEMP; Nicolet, 1987)	k = 0→20
Tmin = 0.716, Tmax = 0.775	l = −15→15
7056 measured reflections	3 standard reflections every 147 reflections
4889 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.9725P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4889 reflections	Δρmax = 0.56 e Å^−3
353 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

9.4185 (0.0178) x + 11.2633 (0.0277) y - 0.0519 (0.0171) z = 14.1634 (0.0065)

* 0.0027 (0.0015) C13 * -0.0027 (0.0015) C14 * 0.0027 (0.0015) C16 * -0.0027 (0.0015) C17 - 0.1504 (0.0043) C12 - 0.1444 (0.0049) C15

Rms deviation of fitted atoms = 0.0027

9.4985 (0.0100) x + 11.0883 (0.0159) y + 0.2431 (0.0089) z = 11.1639 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 1.51 (0.24)

* -0.0127 (0.0019) C4 * -0.0224 (0.0022) C5 * -0.0022 (0.0018) C6 * 0.0325 (0.0022) C3a * 0.0340 (0.0020) C6a * -0.0241 (0.0018) C8 * -0.0051 (0.0019) C9 0.1652 (0.0037) C3 0.1448 (0.0033) C7 - 1.8123 (0.0013) Ru

Rms deviation of fitted atoms = 0.0223

9.7910 (0.0091) x + 10.7338 (0.0147) y - 0.7154 (0.0100) z = 7.4369 (0.0032)

Angle to previous plane (with approximate e.s.d.) = 4.48 (0.16)

* 0.0083 (0.0018) C4' * 0.0412 (0.0021) C5' * 0.0066 (0.0018) C6' * -0.0516 (0.0021) C3a' * -0.0511 (0.0021) C6a' * 0.0234 (0.0019) C8' * 0.0232 (0.0019) C9' -0.1738 (0.0035) C3' -0.1720 (0.0033) C7' 1.8089 (0.0013) Ru

Rms deviation of fitted atoms = 0.0342

9.7944 (0.0155) x + 10.7299 (0.0258) y - 0.7503 (0.0188) z = 4.3534 (0.0048)

Angle to previous plane (with approximate e.s.d.) = 0.15 (0.22)

* 0.0011 (0.0014) C13' * -0.0011 (0.0014) C14' * 0.0011 (0.0014) C16' * -0.0011 (0.0014) C17' 0.1491 (0.0044) C12' 0.1393 (0.0043) C15'

Rms deviation of fitted atoms = 0.0011

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
Ru	0.550639 (16)	0.368568 (11)	0.142080 (14)	0.03400 (9)
C1	0.9114 (3)	0.4297 (3)	0.3812 (4)	0.1039 (15)
H1A	0.9560	0.4310	0.4466	0.125*
H1B	0.9543	0.4098	0.3292	0.125*
C2	0.8168 (3)	0.3722 (2)	0.3909 (4)	0.0882 (14)
H2A	0.8285	0.3247	0.3523	0.106*
H2B	0.8160	0.3576	0.4629	0.106*
C3	0.7102 (2)	0.40560 (17)	0.3522 (2)	0.0498 (7)
C3a	0.6846 (2)	0.41799 (14)	0.24308 (19)	0.0377 (6)
C4	0.7224 (2)	0.38345 (18)	0.1539 (2)	0.0519 (7)
H4	0.7695	0.3414	0.1541	0.062*
C5	0.6770 (3)	0.42343 (19)	0.0657 (2)	0.0581 (8)
H5	0.6895	0.4127	−0.0021	0.070*
C6	0.6087 (2)	0.48303 (17)	0.0976 (2)	0.0512 (8)
H6	0.5685	0.5177	0.0542	0.061*
C6a	0.61248 (19)	0.48066 (14)	0.20791 (19)	0.0353 (5)
C7	0.5660 (2)	0.52881 (15)	0.2820 (2)	0.0465 (7)
C8	0.5763 (2)	0.50261 (18)	0.3802 (3)	0.0577 (8)
H8	0.5344	0.5253	0.4269	0.069*
C9	0.6476 (3)	0.44246 (18)	0.4156 (2)	0.0569 (8)
H9	0.6518	0.4276	0.4847	0.068*
C10	0.5318 (3)	0.61097 (18)	0.2516 (4)	0.0792 (12)
H10A	0.4827	0.6297	0.2988	0.095*
H10B	0.4940	0.6098	0.1828	0.095*
C11	0.6264 (3)	0.66976 (19)	0.2526 (3)	0.0772 (11)
H11A	0.6286	0.6908	0.1835	0.093*
H11B	0.6141	0.7132	0.2980	0.093*
C12	0.7320 (3)	0.63333 (17)	0.2875 (3)	0.0584 (8)
C13	0.7638 (3)	0.6208 (2)	0.3924 (3)	0.0628 (9)
H13	0.7371	0.6528	0.4416	0.075*
C14	0.8340 (3)	0.5618 (3)	0.4237 (3)	0.0713 (10)
H14	0.8535	0.5540	0.4939	0.086*
C15	0.8760 (2)	0.5138 (2)	0.3522 (3)	0.0704 (10)
C16	0.8627 (3)	0.5375 (2)	0.2505 (3)	0.0701 (10)
H16	0.9022	0.5135	0.2028	0.084*
C17	0.7921 (3)	0.5959 (2)	0.2185 (2)	0.0624 (9)
H17	0.7843	0.6107	0.1493	0.075*
C1'	0.1274 (3)	0.3687 (2)	0.1505 (3)	0.0773 (11)
H1'1	0.0626	0.3892	0.1745	0.093*
H1'2	0.1133	0.3590	0.0768	0.093*
C2'	0.2165 (3)	0.4319 (2)	0.1685 (3)	0.0776 (11)
H2'1	0.2311	0.4530	0.1022	0.093*
H2'2	0.1908	0.4746	0.2086	0.093*
C3'	0.3187 (2)	0.40086 (15)	0.2238 (3)	0.0512 (7)
C3a'	0.3841 (2)	0.34898 (14)	0.1701 (2)	0.0376 (6)
C4'	0.3960 (2)	0.33658 (16)	0.0632 (2)	0.0460 (7)
H4'	0.3624	0.3650	0.0081	0.055*
C5'	0.4679 (2)	0.27358 (16)	0.0557 (2)	0.0491 (7)
H5'	0.4892	0.2537	−0.0055	0.059*
C6'	0.5023 (2)	0.24569 (15)	0.1559 (2)	0.0429 (6)
H6'	0.5497	0.2046	0.1720	0.051*
C6a'	0.45100 (19)	0.29191 (13)	0.22826 (19)	0.0347 (5)
C7'	0.4516 (2)	0.28740 (17)	0.3382 (2)	0.0440 (6)
C8'	0.4079 (2)	0.34859 (19)	0.3841 (2)	0.0539 (8)
H8'	0.4213	0.3542	0.4554	0.065*
C9'	0.3425 (2)	0.40451 (18)	0.3283 (3)	0.0583 (8)
H9'	0.3144	0.4455	0.3643	0.070*
C10'	0.4764 (3)	0.2113 (2)	0.3934 (2)	0.0614 (8)
H10C	0.4849	0.2210	0.4673	0.074*
H10D	0.5436	0.1913	0.3741	0.074*
C11'	0.3878 (3)	0.1472 (2)	0.3684 (3)	0.0736 (10)
H11C	0.4145	0.1072	0.3247	0.088*
H11D	0.3726	0.1223	0.4324	0.088*
C12'	0.2857 (3)	0.18083 (16)	0.3148 (3)	0.0543 (7)
C13'	0.2664 (3)	0.17718 (17)	0.2080 (3)	0.0584 (8)
H13'	0.2972	0.1373	0.1723	0.070*
C14'	0.2023 (2)	0.23175 (19)	0.1542 (3)	0.0595 (8)
H14'	0.1906	0.2283	0.0826	0.071*
C15'	0.1549 (2)	0.29166 (18)	0.2046 (3)	0.0571 (8)
C16'	0.1568 (3)	0.28449 (19)	0.3119 (3)	0.0593 (8)
H16'	0.1142	0.3173	0.3475	0.071*
C17'	0.2205 (3)	0.22993 (19)	0.3656 (3)	0.0590 (8)
H17'	0.2199	0.2258	0.4368	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru	0.03511 (13)	0.03297 (13)	0.03338 (13)	−0.00512 (9)	0.00102 (8)	−0.00155 (8)
C1	0.052 (2)	0.134 (4)	0.119 (4)	0.010 (3)	−0.021 (2)	0.002 (3)
C2	0.089 (3)	0.077 (3)	0.088 (3)	0.020 (2)	−0.045 (2)	−0.002 (2)
C3	0.0519 (17)	0.0417 (15)	0.0521 (16)	−0.0049 (13)	−0.0122 (14)	0.0075 (13)
C3a	0.0310 (13)	0.0364 (13)	0.0445 (14)	−0.0026 (11)	−0.0015 (11)	−0.0035 (11)
C4	0.0361 (15)	0.0574 (18)	0.0630 (19)	−0.0034 (13)	0.0090 (14)	−0.0154 (14)
C5	0.0592 (19)	0.069 (2)	0.0489 (17)	−0.0275 (17)	0.0189 (15)	−0.0112 (15)
C6	0.0535 (18)	0.0488 (16)	0.0473 (15)	−0.0245 (14)	−0.0139 (14)	0.0156 (13)
C6a	0.0295 (13)	0.0308 (12)	0.0442 (14)	−0.0091 (10)	−0.0031 (11)	0.0029 (10)
C7	0.0281 (13)	0.0338 (13)	0.078 (2)	−0.0069 (11)	0.0052 (13)	−0.0118 (13)
C8	0.0537 (19)	0.0585 (19)	0.066 (2)	−0.0253 (16)	0.0284 (16)	−0.0273 (16)
C9	0.073 (2)	0.0586 (18)	0.0385 (15)	−0.0249 (17)	0.0040 (15)	−0.0032 (14)
C10	0.057 (2)	0.0402 (17)	0.137 (4)	0.0051 (16)	−0.005 (2)	−0.016 (2)
C11	0.084 (3)	0.0375 (17)	0.107 (3)	−0.0076 (18)	−0.001 (2)	−0.0011 (18)
C12	0.059 (2)	0.0469 (17)	0.070 (2)	−0.0320 (15)	0.0114 (17)	−0.0094 (14)
C13	0.056 (2)	0.072 (2)	0.061 (2)	−0.0326 (18)	0.0148 (17)	−0.0263 (17)
C14	0.048 (2)	0.106 (3)	0.058 (2)	−0.033 (2)	−0.0045 (16)	−0.010 (2)
C15	0.0302 (16)	0.096 (3)	0.083 (3)	−0.0122 (17)	−0.0055 (16)	−0.012 (2)
C16	0.0407 (18)	0.100 (3)	0.071 (2)	−0.0270 (19)	0.0170 (17)	−0.026 (2)
C17	0.058 (2)	0.077 (2)	0.0529 (18)	−0.0365 (19)	0.0094 (16)	−0.0054 (17)
C1'	0.0432 (19)	0.084 (3)	0.102 (3)	−0.0001 (18)	−0.0066 (19)	0.009 (2)
C2'	0.052 (2)	0.0517 (19)	0.129 (3)	0.0115 (16)	0.010 (2)	0.009 (2)
C3'	0.0389 (16)	0.0286 (13)	0.086 (2)	−0.0013 (12)	0.0068 (15)	−0.0014 (14)
C3a'	0.0312 (13)	0.0324 (13)	0.0479 (15)	−0.0079 (10)	−0.0028 (11)	−0.0001 (11)
C4'	0.0463 (16)	0.0465 (15)	0.0423 (14)	−0.0165 (13)	−0.0097 (12)	0.0060 (12)
C5'	0.0580 (18)	0.0455 (16)	0.0444 (15)	−0.0186 (14)	0.0083 (14)	−0.0133 (12)
C6'	0.0427 (15)	0.0311 (13)	0.0555 (16)	−0.0033 (12)	0.0081 (13)	−0.0049 (11)
C6a'	0.0311 (13)	0.0307 (12)	0.0419 (13)	−0.0059 (10)	0.0021 (11)	0.0000 (10)
C7'	0.0370 (15)	0.0526 (16)	0.0423 (14)	−0.0119 (13)	0.0032 (12)	0.0001 (12)
C8'	0.0488 (17)	0.068 (2)	0.0468 (16)	−0.0216 (16)	0.0122 (14)	−0.0144 (15)
C9'	0.0514 (18)	0.0475 (17)	0.080 (2)	−0.0134 (15)	0.0251 (17)	−0.0280 (16)
C10'	0.0548 (19)	0.077 (2)	0.0519 (17)	−0.0037 (17)	0.0009 (15)	0.0219 (16)
C11'	0.067 (2)	0.061 (2)	0.093 (3)	−0.0050 (18)	0.012 (2)	0.0217 (18)
C12'	0.0527 (18)	0.0406 (15)	0.071 (2)	−0.0140 (14)	0.0119 (16)	0.0049 (14)
C13'	0.0561 (19)	0.0404 (16)	0.080 (2)	−0.0170 (14)	0.0151 (17)	−0.0119 (15)
C14'	0.0481 (18)	0.066 (2)	0.0637 (19)	−0.0242 (16)	0.0015 (15)	−0.0124 (16)
C15'	0.0310 (15)	0.0560 (18)	0.083 (2)	−0.0116 (14)	−0.0004 (15)	−0.0043 (16)
C16'	0.0461 (18)	0.0594 (19)	0.075 (2)	−0.0125 (15)	0.0195 (16)	−0.0144 (17)
C17'	0.060 (2)	0.0575 (19)	0.0609 (19)	−0.0207 (16)	0.0146 (16)	−0.0002 (15)

Geometric parameters (Å, º)

Ru—C4	2.172 (3)	C14—H14	0.9300
Ru—C5'	2.174 (3)	C15—C16	1.377 (5)
Ru—C5	2.175 (3)	C16—C17	1.371 (5)
Ru—C4'	2.178 (3)	C16—H16	0.9300
Ru—C6	2.181 (3)	C17—H17	0.9300
Ru—C6'	2.192 (3)	C1'—C15'	1.512 (5)
Ru—C3a'	2.195 (3)	C1'—C2'	1.557 (5)
Ru—C6a'	2.198 (2)	C1'—H1'1	0.9700
Ru—C3a	2.198 (2)	C1'—H1'2	0.9700
Ru—C6a	2.201 (2)	C2'—C3'	1.506 (4)
C1—C15	1.534 (6)	C2'—H2'1	0.9700
C1—C2	1.560 (6)	C2'—H2'2	0.9700
C1—H1A	0.9700	C3'—C9'	1.362 (4)
C1—H1B	0.9700	C3'—C3a'	1.438 (4)
C2—C3	1.499 (5)	C3a'—C4'	1.430 (4)
C2—H2A	0.9700	C3a'—C6a'	1.448 (3)
C2—H2B	0.9700	C4'—C5'	1.415 (4)
C3—C9	1.353 (4)	C4'—H4'	0.9300
C3—C3a	1.439 (4)	C5'—C6'	1.412 (4)
C3a—C4	1.426 (4)	C5'—H5'	0.9300
C3a—C6a	1.446 (3)	C6'—C6a'	1.431 (4)
C4—C5	1.404 (5)	C6'—H6'	0.9300
C4—H4	0.9300	C6a'—C7'	1.431 (3)
C5—C6	1.421 (5)	C7'—C8'	1.347 (4)
C5—H5	0.9300	C7'—C10'	1.498 (4)
C6—C6a	1.431 (4)	C8'—C9'	1.411 (5)
C6—H6	0.9300	C8'—H8'	0.9300
C6a—C7	1.435 (4)	C9'—H9'	0.9300
C7—C8	1.346 (4)	C10'—C11'	1.573 (5)
C7—C10	1.505 (4)	C10'—H10C	0.9700
C8—C9	1.409 (5)	C10'—H10D	0.9700
C8—H8	0.9300	C11'—C12'	1.513 (5)
C9—H9	0.9300	C11'—H11C	0.9700
C10—C11	1.557 (5)	C11'—H11D	0.9700
C10—H10A	0.9700	C12'—C13'	1.386 (4)
C10—H10B	0.9700	C12'—C17'	1.387 (4)
C11—C12	1.497 (5)	C13'—C14'	1.375 (5)
C11—H11A	0.9700	C13'—H13'	0.9300
C11—H11B	0.9700	C14'—C15'	1.382 (4)
C12—C17	1.388 (5)	C14'—H14'	0.9300
C12—C13	1.399 (5)	C15'—C16'	1.399 (5)
C13—C14	1.372 (5)	C16'—C17'	1.371 (5)
C13—H13	0.9300	C16'—H16'	0.9300
C14—C15	1.385 (5)	C17'—H17'	0.9300
C4—Ru—C5'	123.08 (11)	C10—C11—H11A	108.9
C4—Ru—C5	37.69 (12)	C12—C11—H11B	108.9
C5'—Ru—C5	114.79 (11)	C10—C11—H11B	108.9
C4—Ru—C4'	154.36 (11)	H11A—C11—H11B	107.8
C5'—Ru—C4'	37.94 (11)	C17—C12—C13	116.1 (3)
C5—Ru—C4'	123.77 (11)	C17—C12—C11	121.5 (3)
C4—Ru—C6	63.53 (12)	C13—C12—C11	121.1 (3)
C5'—Ru—C6	133.19 (10)	C14—C13—C12	120.8 (3)
C5—Ru—C6	38.07 (12)	C14—C13—H13	119.6
C4'—Ru—C6	114.06 (10)	C12—C13—H13	119.6
C4—Ru—C6'	112.94 (11)	C13—C14—C15	120.9 (3)
C5'—Ru—C6'	37.75 (10)	C13—C14—H14	119.6
C5—Ru—C6'	132.14 (12)	C15—C14—H14	119.6
C4'—Ru—C6'	63.67 (11)	C16—C15—C14	117.1 (4)
C6—Ru—C6'	168.13 (11)	C16—C15—C1	120.9 (4)
C4—Ru—C3a'	166.28 (11)	C14—C15—C1	120.5 (4)
C5'—Ru—C3a'	63.63 (10)	C17—C16—C15	121.1 (3)
C5—Ru—C3a'	154.28 (12)	C17—C16—H16	119.5
C4'—Ru—C3a'	38.17 (10)	C15—C16—H16	119.5
C6—Ru—C3a'	122.24 (11)	C16—C17—C12	121.2 (3)
C6'—Ru—C3a'	64.02 (10)	C16—C17—H17	119.4
C4—Ru—C6a'	130.72 (11)	C12—C17—H17	119.4
C5'—Ru—C6a'	63.39 (10)	C15'—C1'—C2'	113.7 (3)
C5—Ru—C6a'	166.65 (12)	C15'—C1'—H1'1	108.8
C4'—Ru—C6a'	63.89 (10)	C2'—C1'—H1'1	108.8
C6—Ru—C6a'	153.04 (11)	C15'—C1'—H1'2	108.8
C6'—Ru—C6a'	38.06 (9)	C2'—C1'—H1'2	108.8
C3a'—Ru—C6a'	38.48 (9)	H1'1—C1'—H1'2	107.7
C4—Ru—C3a	38.08 (10)	C3'—C2'—C1'	113.5 (3)
C5'—Ru—C3a	153.15 (11)	C3'—C2'—H2'1	108.9
C5—Ru—C3a	63.49 (11)	C1'—C2'—H2'1	108.9
C4'—Ru—C3a	166.78 (10)	C3'—C2'—H2'2	108.9
C6—Ru—C3a	63.75 (10)	C1'—C2'—H2'2	108.9
C6'—Ru—C3a	121.31 (10)	H2'1—C2'—H2'2	107.7
C3a'—Ru—C3a	130.48 (10)	C9'—C3'—C3a'	115.7 (3)
C6a'—Ru—C3a	111.57 (9)	C9'—C3'—C2'	123.4 (3)
C4—Ru—C6a	63.91 (10)	C3a'—C3'—C2'	119.3 (3)
C5'—Ru—C6a	167.97 (10)	C4'—C3a'—C3'	133.3 (3)
C5—Ru—C6a	63.77 (10)	C4'—C3a'—C6a'	107.1 (2)
C4'—Ru—C6a	131.64 (10)	C3'—C3a'—C6a'	119.4 (2)
C6—Ru—C6a	38.12 (9)	C4'—C3a'—Ru	70.27 (15)
C6'—Ru—C6a	152.38 (10)	C3'—C3a'—Ru	126.50 (18)
C3a'—Ru—C6a	111.97 (9)	C6a'—C3a'—Ru	70.88 (14)
C6a'—Ru—C6a	120.99 (9)	C5'—C4'—C3a'	108.1 (2)
C3a—Ru—C6a	38.36 (9)	C5'—C4'—Ru	70.87 (15)
C15—C1—C2	113.5 (3)	C3a'—C4'—Ru	71.56 (14)
C15—C1—H1A	108.9	C5'—C4'—H4'	125.9
C2—C1—H1A	108.9	C3a'—C4'—H4'	125.9
C15—C1—H1B	108.9	Ru—C4'—H4'	123.3
C2—C1—H1B	108.9	C6'—C5'—C4'	109.2 (2)
H1A—C1—H1B	107.7	C6'—C5'—Ru	71.83 (15)
C3—C2—C1	113.7 (3)	C4'—C5'—Ru	71.19 (15)
C3—C2—H2A	108.8	C6'—C5'—H5'	125.4
C1—C2—H2A	108.8	C4'—C5'—H5'	125.4
C3—C2—H2B	108.8	Ru—C5'—H5'	123.2
C1—C2—H2B	108.8	C5'—C6'—C6a'	107.8 (2)
H2A—C2—H2B	107.7	C5'—C6'—Ru	70.42 (15)
C9—C3—C3a	116.6 (3)	C6a'—C6'—Ru	71.20 (14)
C9—C3—C2	122.1 (3)	C5'—C6'—H6'	126.1
C3a—C3—C2	119.3 (3)	C6a'—C6'—H6'	126.1
C4—C3a—C3	133.0 (3)	Ru—C6'—H6'	123.9
C4—C3a—C6a	107.4 (2)	C6'—C6a'—C7'	132.1 (2)
C3—C3a—C6a	119.4 (2)	C6'—C6a'—C3a'	107.7 (2)
C4—C3a—Ru	69.98 (15)	C7'—C6a'—C3a'	120.0 (2)
C3—C3a—Ru	127.90 (19)	C6'—C6a'—Ru	70.74 (14)
C6a—C3a—Ru	70.93 (13)	C7'—C6a'—Ru	126.64 (17)
C5—C4—C3a	108.8 (3)	C3a'—C6a'—Ru	70.64 (14)
C5—C4—Ru	71.24 (18)	C8'—C7'—C6a'	116.2 (3)
C3a—C4—Ru	71.94 (15)	C8'—C7'—C10'	122.1 (3)
C5—C4—H4	125.6	C6a'—C7'—C10'	120.3 (3)
C3a—C4—H4	125.6	C7'—C8'—C9'	122.6 (3)
Ru—C4—H4	122.8	C7'—C8'—H8'	118.7
C4—C5—C6	108.5 (3)	C9'—C8'—H8'	118.7
C4—C5—Ru	71.07 (17)	C3'—C9'—C8'	122.6 (3)
C6—C5—Ru	71.22 (16)	C3'—C9'—H9'	118.7
C4—C5—H5	125.8	C8'—C9'—H9'	118.7
C6—C5—H5	125.8	C7'—C10'—C11'	113.1 (3)
Ru—C5—H5	123.6	C7'—C10'—H10C	109.0
C5—C6—C6a	108.3 (3)	C11'—C10'—H10C	109.0
C5—C6—Ru	70.71 (16)	C7'—C10'—H10D	109.0
C6a—C6—Ru	71.71 (14)	C11'—C10'—H10D	109.0
C5—C6—H6	125.8	H10C—C10'—H10D	107.8
C6a—C6—H6	125.8	C12'—C11'—C10'	112.7 (3)
Ru—C6—H6	123.4	C12'—C11'—H11C	109.0
C6—C6a—C7	133.1 (3)	C10'—C11'—H11C	109.0
C6—C6a—C3a	107.0 (2)	C12'—C11'—H11D	109.0
C7—C6a—C3a	119.8 (2)	C10'—C11'—H11D	109.0
C6—C6a—Ru	70.18 (14)	H11C—C11'—H11D	107.8
C7—C6a—Ru	127.10 (17)	C13'—C12'—C17'	116.9 (3)
C3a—C6a—Ru	70.70 (13)	C13'—C12'—C11'	119.9 (3)
C8—C7—C6a	116.2 (3)	C17'—C12'—C11'	121.8 (3)
C8—C7—C10	123.6 (3)	C14'—C13'—C12'	120.9 (3)
C6a—C7—C10	118.8 (3)	C14'—C13'—H13'	119.6
C7—C8—C9	123.1 (3)	C12'—C13'—H13'	119.6
C7—C8—H8	118.4	C13'—C14'—C15'	121.2 (3)
C9—C8—H8	118.4	C13'—C14'—H14'	119.4
C3—C9—C8	122.1 (3)	C15'—C14'—H14'	119.4
C3—C9—H9	119.0	C14'—C15'—C16'	116.4 (3)
C8—C9—H9	119.0	C14'—C15'—C1'	120.6 (3)
C7—C10—C11	113.3 (3)	C16'—C15'—C1'	121.3 (3)
C7—C10—H10A	108.9	C17'—C16'—C15'	121.1 (3)
C11—C10—H10A	108.9	C17'—C16'—H16'	119.5
C7—C10—H10B	108.9	C15'—C16'—H16'	119.5
C11—C10—H10B	108.9	C16'—C17'—C12'	120.8 (3)
H10A—C10—H10B	107.7	C16'—C17'—H17'	119.6
C12—C11—C10	113.2 (3)	C12'—C17'—H17'	119.6
C12—C11—H11A	108.9