Benzoyl­dicarbon­yl(η5-inden­yl)ruthenium(II)

Oudenhoven, T.A.; Walder, B.J.; Golen, J.A.; Rheingold, A.L.; D'Acchioli, J.S.

doi:10.1107/S1600536810033180

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1160

https://doi.org/10.1107/S1600536810033180

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Benzoyldicarbonyl(η⁵-indenyl)ruthenium(II)

Tracey A. Oudenhoven,^a Brennan J. Walder,^b James A. Golen,^c Arnold L. Rheingold ^d and Jason S. D'Acchioli ^a ^*

^aDepartment of Chemistry, The University of Wisconsin-Stevens Point, 2001 Fourth Avenue, Stevens Point, WI 54481, USA, ^bDepartment of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA, ^cDepartment of Chemistry, UMass Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA, and ^dDepartment of Chemistry and Biochemistry, 9500 Gilman Drive, MC 0332, La Jolla, CA 92093, USA
^*Correspondence e-mail: jdacchio@uwsp.edu

(Received 4 August 2010; accepted 17 August 2010; online 25 August 2010)

In the title molecule, [Ru(C₉H₇)(C₇H₅O)(CO)₂], the dihedral angle between the mean plane of the indene ring system and the phenyl ring is 86.28 (8)°. The crystal structure is stabilized by weak intermolecular C—H⋯O and C—H⋯π(arene) interactions. The Ru—η⁵-cyclopentadienyl centroid bond length is 1.946 (11) Å

Related literature

For background information, see: Chung et al. (1982 ). For the synthetic procedure, see: Badger et al. (2009 ).

Experimental

Crystal data

[Ru(C₉H₇)(C₇H₅O)(CO)₂]
M_r = 377.35
Monoclinic, P 2₁ /n
a = 11.531 (3) Å
b = 8.731 (2) Å
c = 15.158 (4) Å
β = 108.150 (3)°
V = 1450.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.736, T_max = 0.899
11223 measured reflections
3332 independent reflections
2730 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.05
3332 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 1.07 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O3ⁱ	0.95	2.55	3.204 (4)	126
C9—H9A⋯Cgⁱⁱ	0.95	2.72	3.657 (3)	169
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810033180/lh5113sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033180/lh5113Isup2.hkl

checkCIF report

Comment top

The title compound was synthesized via attack of the Grignard reagent phenyl-magnesium bromide on [tricarbonyl(η⁵-indenyl)ruthenium(II)]⁺. It is well established that coordination of ML_n fragments (M = for example Fe, Ru, Rh; L_n = for example CO, phosphines) to an arene ring can result in nucleophilic or electrophilic attack at the arene ring or the carbonyl ligand (Chung et al., 1982). The latter case is the subject of this structural study.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the mean plane of the indene ring system and the phenyl ring is 86.28 (8)°. The crystal structure is stabilized by weak intermolecular C-H···O and C-H···π(arene) interactions.

Related literature top

For background information, see: Chung et al. (1982). For the synthetic procedure, see: Badger et al. (2009).

Experimental top

All reactions were performed under nitrogen using standard Schlenk techniques. THF was dried using a MBraun solvent purification system and used fresh. The compound benzoyldicarbonyl(η⁵-indenyl)ruthenium(II) was prepared by reaction of tricarbonyl(η⁵-indenyl)ruthenium(II) tetrafluoroborate with the Grignard reagent phenyl-magnesium bromide; tricarbonyl(η⁵-indenyl)ruthenium(II) tetrafluoroborate was prepared according to a previously established procedure (Badger et al., 2009).

To a 100 ml three-neck round-bottom flask containing 15 ml of anhydrous THF at 273 K was added 142 mg tricarbonyl(η⁶-indenyl)ruthenium(II) tetrafluoroborate. Approximately 1.3 ml of 0.5 M phenyl-magnesium bromide (1.7 mol excess relative to tricarbonyl(η⁵-indenyl)ruthenium(II) tetrafluoroborate) was added to the flask. The solution changed from pale yellow to orange, and was allowed to stir for 10 minutes at 273 K. Excess Grignard reagent was killed with several drops of dilute HCl.

Solid magnesium salts precipitated out of the reaction mixture. The material was filtered via gravity filtration, and the solid was discarded. The mother liquor was extracted into diethyl ether and washed with two 10 ml aliquots of distilled water in a seperatory funnel. The organic layer was dried over MgSO₄. The ether layer was removed via roto-evaporation, yielding a dark-yellow oil. X-ray diffraction-quality crystals precipitated from the oil on standing overnight.

Structure description top

For background information, see: Chung et al. (1982). For the synthetic procedure, see: Badger et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Benzoyldicarbonyl(η⁵-indenyl)ruthenium(II) top

Crystal data top

[Ru(C₉H₇)(C₇H₅O)(CO)₂]	F(000) = 752
M_r = 377.35	D_x = 1.728 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5236 reflections
a = 11.531 (3) Å	θ = 2.7–28.1°
b = 8.731 (2) Å	µ = 1.09 mm⁻¹
c = 15.158 (4) Å	T = 100 K
β = 108.150 (3)°	Block, yellow
V = 1450.2 (7) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3332 independent reflections
Radiation source: fine-focus sealed tube	2730 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 28.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.736, T_max = 0.899	k = −11→11
11223 measured reflections	l = −19→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0372P)² + 1.048P] where P = (F_o² + 2F_c²)/3
3332 reflections	(Δ/σ)_max = 0.013
199 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Ru(C₉H₇)(C₇H₅O)(CO)₂]	V = 1450.2 (7) Å³
M_r = 377.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.531 (3) Å	µ = 1.09 mm⁻¹
b = 8.731 (2) Å	T = 100 K
c = 15.158 (4) Å	0.30 × 0.10 × 0.10 mm
β = 108.150 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3332 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2730 reflections with I > 2σ(I)
T_min = 0.736, T_max = 0.899	R_int = 0.037
11223 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.05	Δρ_max = 1.07 e Å⁻³
3332 reflections	Δρ_min = −0.63 e Å⁻³
199 parameters

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	U_iso*/U_eq
Ru1	0.44803 (2)	0.32604 (3)	0.139849 (16)	0.01609 (9)
O1	0.2399 (2)	0.5526 (3)	0.07196 (17)	0.0285 (5)
O2	0.4145 (2)	0.2330 (3)	0.32314 (17)	0.0328 (6)
O3	0.67033 (18)	0.4987 (3)	0.20243 (16)	0.0239 (5)
C1	0.4696 (3)	0.2829 (4)	0.0000 (2)	0.0214 (7)
H1A	0.4618	0.3618	−0.0494	0.026*
C2	0.5797 (3)	0.2380 (4)	0.0669 (2)	0.0229 (7)
H2A	0.6621	0.2819	0.0736	0.027*
C3	0.5550 (3)	0.1181 (4)	0.1223 (2)	0.0208 (6)
H3A	0.6170	0.0622	0.1732	0.025*
C4	0.4273 (3)	0.0737 (4)	0.0800 (2)	0.0193 (6)
C5	0.3748 (3)	0.1751 (3)	0.0039 (2)	0.0203 (7)
C6	0.2508 (3)	0.1615 (4)	−0.0498 (2)	0.0238 (7)
H6A	0.2153	0.2294	−0.0999	0.029*
C7	0.1830 (3)	0.0471 (4)	−0.0273 (2)	0.0270 (7)
H7A	0.0996	0.0354	−0.0628	0.032*
C8	0.2350 (3)	−0.0538 (4)	0.0478 (2)	0.0248 (7)
H8A	0.1859	−0.1325	0.0609	0.030*
C9	0.3538 (3)	−0.0408 (3)	0.1020 (2)	0.0216 (7)
H9A	0.3866	−0.1073	0.1534	0.026*
C10	0.3210 (3)	0.4708 (4)	0.1019 (2)	0.0216 (7)
C11	0.4272 (3)	0.2735 (4)	0.2550 (2)	0.0205 (7)
C12	0.5661 (3)	0.4974 (3)	0.2068 (2)	0.0179 (6)
C13	0.5309 (3)	0.6283 (3)	0.2604 (2)	0.0170 (6)
C14	0.4295 (3)	0.6266 (4)	0.2918 (2)	0.0184 (6)
H14A	0.3732	0.5441	0.2752	0.022*
C15	0.4098 (3)	0.7448 (4)	0.3472 (2)	0.0206 (7)
H15A	0.3418	0.7409	0.3699	0.025*
C16	0.4894 (3)	0.8680 (4)	0.3694 (2)	0.0234 (7)
H16A	0.4760	0.9487	0.4071	0.028*
C17	0.5889 (3)	0.8731 (4)	0.3362 (2)	0.0215 (7)
H17A	0.6425	0.9587	0.3503	0.026*
C18	0.6106 (3)	0.7542 (4)	0.2827 (2)	0.0190 (6)
H18A	0.6795	0.7580	0.2611	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01864 (15)	0.01520 (14)	0.01457 (14)	0.00019 (10)	0.00536 (10)	−0.00036 (9)
O1	0.0257 (13)	0.0278 (13)	0.0293 (13)	0.0065 (11)	0.0045 (10)	0.0040 (11)
O2	0.0520 (16)	0.0240 (12)	0.0297 (14)	0.0046 (12)	0.0233 (13)	0.0050 (11)
O3	0.0189 (11)	0.0248 (12)	0.0284 (13)	−0.0022 (10)	0.0081 (10)	−0.0058 (10)
C1	0.0278 (17)	0.0195 (15)	0.0186 (16)	−0.0024 (14)	0.0096 (14)	−0.0029 (13)
C2	0.0268 (17)	0.0247 (17)	0.0201 (16)	−0.0011 (14)	0.0117 (14)	−0.0052 (14)
C3	0.0228 (16)	0.0174 (15)	0.0215 (16)	0.0029 (13)	0.0062 (13)	−0.0047 (13)
C4	0.0229 (16)	0.0197 (15)	0.0150 (15)	0.0035 (13)	0.0056 (12)	−0.0024 (12)
C5	0.0279 (17)	0.0197 (15)	0.0145 (15)	0.0020 (13)	0.0085 (13)	−0.0037 (12)
C6	0.0291 (18)	0.0242 (17)	0.0160 (16)	0.0021 (14)	0.0039 (14)	−0.0026 (13)
C7	0.0248 (17)	0.0313 (19)	0.0230 (17)	−0.0035 (15)	0.0048 (14)	−0.0115 (15)
C8	0.0328 (19)	0.0208 (16)	0.0238 (17)	−0.0047 (14)	0.0130 (15)	−0.0054 (14)
C9	0.0270 (17)	0.0160 (15)	0.0229 (16)	−0.0005 (13)	0.0092 (14)	−0.0028 (13)
C10	0.0242 (17)	0.0208 (15)	0.0198 (15)	−0.0061 (14)	0.0070 (13)	−0.0035 (13)
C11	0.0245 (17)	0.0141 (14)	0.0229 (17)	0.0037 (13)	0.0072 (14)	−0.0016 (13)
C12	0.0191 (15)	0.0181 (15)	0.0155 (14)	0.0005 (12)	0.0040 (12)	0.0030 (12)
C13	0.0195 (15)	0.0159 (14)	0.0134 (14)	0.0024 (12)	0.0019 (12)	0.0007 (12)
C14	0.0199 (15)	0.0160 (14)	0.0183 (15)	0.0015 (12)	0.0046 (12)	0.0021 (12)
C15	0.0229 (16)	0.0204 (16)	0.0204 (16)	0.0048 (13)	0.0092 (13)	0.0026 (13)
C16	0.0264 (17)	0.0217 (16)	0.0215 (16)	0.0035 (14)	0.0065 (14)	−0.0008 (13)
C17	0.0232 (16)	0.0194 (15)	0.0202 (16)	−0.0035 (13)	0.0042 (13)	−0.0014 (13)
C18	0.0184 (15)	0.0222 (16)	0.0161 (15)	0.0006 (13)	0.0049 (12)	0.0002 (13)

Geometric parameters (Å, º) top

Ru1—C10	1.884 (3)	C5—C6	1.413 (5)
Ru1—C11	1.891 (3)	C6—C7	1.376 (5)
Ru1—C12	2.064 (3)	C6—H6A	0.9500
Ru1—C1	2.243 (3)	C7—C8	1.416 (5)
Ru1—C3	2.257 (3)	C7—H7A	0.9500
Ru1—C2	2.272 (3)	C8—C9	1.365 (5)
Ru1—C4	2.367 (3)	C8—H8A	0.9500
Ru1—C5	2.369 (3)	C9—H9A	0.9500
O1—C10	1.152 (4)	C12—C13	1.528 (4)
O2—C11	1.144 (4)	C13—C14	1.393 (4)
O3—C12	1.225 (3)	C13—C18	1.405 (4)
C1—C2	1.412 (5)	C14—C15	1.394 (4)
C1—C5	1.458 (4)	C14—H14A	0.9500
C1—H1A	1.0000	C15—C16	1.386 (5)
C2—C3	1.425 (5)	C15—H15A	0.9500
C2—H2A	1.0000	C16—C17	1.389 (4)
C3—C4	1.464 (4)	C16—H16A	0.9500
C3—H3A	1.0000	C17—C18	1.387 (4)
C4—C9	1.416 (4)	C17—H17A	0.9500
C4—C5	1.431 (4)	C18—H18A	0.9500

C10—Ru1—C11	97.72 (13)	C9—C4—C3	132.7 (3)
C10—Ru1—C12	89.69 (13)	C5—C4—C3	107.7 (3)
C11—Ru1—C12	88.61 (13)	C9—C4—Ru1	124.3 (2)
C10—Ru1—C1	97.41 (13)	C5—C4—Ru1	72.53 (17)
C11—Ru1—C1	156.27 (13)	C3—C4—Ru1	67.50 (16)
C12—Ru1—C1	109.65 (11)	C6—C5—C4	120.7 (3)
C10—Ru1—C3	154.88 (13)	C6—C5—C1	131.9 (3)
C11—Ru1—C3	98.33 (12)	C4—C5—C1	107.4 (3)
C12—Ru1—C3	109.88 (12)	C6—C5—Ru1	124.7 (2)
C1—Ru1—C3	61.82 (12)	C4—C5—Ru1	72.31 (18)
C10—Ru1—C2	130.72 (13)	C1—C5—Ru1	66.91 (16)
C11—Ru1—C2	131.54 (13)	C7—C6—C5	118.0 (3)
C12—Ru1—C2	92.65 (12)	C7—C6—H6A	121.0
C1—Ru1—C2	36.43 (12)	C5—C6—H6A	121.0
C3—Ru1—C2	36.67 (12)	C6—C7—C8	121.3 (3)
C10—Ru1—C4	122.10 (12)	C6—C7—H7A	119.4
C11—Ru1—C4	95.82 (12)	C8—C7—H7A	119.4
C12—Ru1—C4	146.71 (11)	C9—C8—C7	121.8 (3)
C1—Ru1—C4	60.58 (11)	C9—C8—H8A	119.1
C3—Ru1—C4	36.83 (11)	C7—C8—H8A	119.1
C2—Ru1—C4	60.11 (11)	C8—C9—C4	118.6 (3)
C10—Ru1—C5	94.31 (12)	C8—C9—H9A	120.7
C11—Ru1—C5	123.70 (12)	C4—C9—H9A	120.7
C12—Ru1—C5	146.36 (11)	O1—C10—Ru1	174.3 (3)
C1—Ru1—C5	36.72 (11)	O2—C11—Ru1	176.0 (3)
C3—Ru1—C5	60.65 (11)	O3—C12—C13	116.7 (3)
C2—Ru1—C5	59.98 (11)	O3—C12—Ru1	119.2 (2)
C4—Ru1—C5	35.16 (10)	C13—C12—Ru1	124.1 (2)
C2—C1—C5	108.0 (3)	C14—C13—C18	118.8 (3)
C2—C1—Ru1	72.91 (18)	C14—C13—C12	124.3 (3)
C5—C1—Ru1	76.37 (17)	C18—C13—C12	116.8 (3)
C2—C1—H1A	125.5	C13—C14—C15	120.7 (3)
C5—C1—H1A	125.5	C13—C14—H14A	119.7
Ru1—C1—H1A	125.5	C15—C14—H14A	119.7
C1—C2—C3	109.1 (3)	C16—C15—C14	120.1 (3)
C1—C2—Ru1	70.65 (17)	C16—C15—H15A	120.0
C3—C2—Ru1	71.08 (17)	C14—C15—H15A	120.0
C1—C2—H2A	125.4	C15—C16—C17	119.8 (3)
C3—C2—H2A	125.4	C15—C16—H16A	120.1
Ru1—C2—H2A	125.4	C17—C16—H16A	120.1
C2—C3—C4	107.1 (3)	C18—C17—C16	120.5 (3)
C2—C3—Ru1	72.25 (18)	C18—C17—H17A	119.8
C4—C3—Ru1	75.67 (17)	C16—C17—H17A	119.8
C2—C3—H3A	126.0	C17—C18—C13	120.2 (3)
C4—C3—H3A	126.0	C17—C18—H18A	119.9
Ru1—C3—H3A	126.0	C13—C18—H18A	119.9
C9—C4—C5	119.6 (3)

C10—Ru1—C1—C2	158.7 (2)	C2—C1—C5—C6	−176.7 (3)
C11—Ru1—C1—C2	−72.1 (4)	Ru1—C1—C5—C6	116.7 (3)
C12—Ru1—C1—C2	66.4 (2)	C2—C1—C5—C4	5.3 (3)
C3—Ru1—C1—C2	−36.26 (19)	Ru1—C1—C5—C4	−61.4 (2)
C4—Ru1—C1—C2	−78.5 (2)	C2—C1—C5—Ru1	66.6 (2)
C5—Ru1—C1—C2	−114.0 (3)	C10—Ru1—C5—C6	−29.4 (3)
C10—Ru1—C1—C5	−87.27 (19)	C11—Ru1—C5—C6	72.8 (3)
C11—Ru1—C1—C5	41.9 (4)	C12—Ru1—C5—C6	−125.4 (3)
C12—Ru1—C1—C5	−179.61 (18)	C1—Ru1—C5—C6	−126.0 (4)
C3—Ru1—C1—C5	77.78 (19)	C3—Ru1—C5—C6	152.7 (3)
C2—Ru1—C1—C5	114.0 (3)	C2—Ru1—C5—C6	−164.8 (3)
C4—Ru1—C1—C5	35.54 (17)	C4—Ru1—C5—C6	115.5 (3)
C5—C1—C2—C3	−8.0 (3)	C10—Ru1—C5—C4	−144.92 (18)
Ru1—C1—C2—C3	60.9 (2)	C11—Ru1—C5—C4	−42.7 (2)
C5—C1—C2—Ru1	−69.0 (2)	C12—Ru1—C5—C4	119.1 (2)
C10—Ru1—C2—C1	−28.4 (3)	C1—Ru1—C5—C4	118.5 (3)
C11—Ru1—C2—C1	149.2 (2)	C3—Ru1—C5—C4	37.23 (17)
C12—Ru1—C2—C1	−120.3 (2)	C2—Ru1—C5—C4	79.68 (19)
C3—Ru1—C2—C1	119.2 (3)	C10—Ru1—C5—C1	96.6 (2)
C4—Ru1—C2—C1	79.9 (2)	C11—Ru1—C5—C1	−161.14 (19)
C5—Ru1—C2—C1	39.09 (18)	C12—Ru1—C5—C1	0.7 (3)
C10—Ru1—C2—C3	−147.6 (2)	C3—Ru1—C5—C1	−81.2 (2)
C11—Ru1—C2—C3	30.0 (3)	C2—Ru1—C5—C1	−38.78 (19)
C12—Ru1—C2—C3	120.5 (2)	C4—Ru1—C5—C1	−118.5 (3)
C1—Ru1—C2—C3	−119.2 (3)	C4—C5—C6—C7	−0.8 (4)
C4—Ru1—C2—C3	−39.30 (18)	C1—C5—C6—C7	−178.7 (3)
C5—Ru1—C2—C3	−80.1 (2)	Ru1—C5—C6—C7	−89.7 (3)
C1—C2—C3—C4	7.6 (3)	C5—C6—C7—C8	0.5 (5)
Ru1—C2—C3—C4	68.2 (2)	C6—C7—C8—C9	1.0 (5)
C1—C2—C3—Ru1	−60.7 (2)	C7—C8—C9—C4	−2.1 (4)
C10—Ru1—C3—C2	73.1 (3)	C5—C4—C9—C8	1.8 (4)
C11—Ru1—C3—C2	−157.7 (2)	C3—C4—C9—C8	180.0 (3)
C12—Ru1—C3—C2	−66.2 (2)	Ru1—C4—C9—C8	90.1 (3)
C1—Ru1—C3—C2	36.03 (19)	C11—Ru1—C10—O1	−128 (3)
C4—Ru1—C3—C2	113.7 (3)	C12—Ru1—C10—O1	143 (3)
C5—Ru1—C3—C2	78.1 (2)	C1—Ru1—C10—O1	34 (3)
C10—Ru1—C3—C4	−40.6 (4)	C3—Ru1—C10—O1	1 (3)
C11—Ru1—C3—C4	88.60 (19)	C2—Ru1—C10—O1	50 (3)
C12—Ru1—C3—C4	−179.86 (17)	C4—Ru1—C10—O1	−26 (3)
C1—Ru1—C3—C4	−77.63 (19)	C5—Ru1—C10—O1	−3 (3)
C2—Ru1—C3—C4	−113.7 (3)	C10—Ru1—C11—O2	128 (4)
C5—Ru1—C3—C4	−35.53 (16)	C12—Ru1—C11—O2	−142 (4)
C2—C3—C4—C9	177.5 (3)	C1—Ru1—C11—O2	−1 (4)
Ru1—C3—C4—C9	−116.6 (3)	C3—Ru1—C11—O2	−32 (4)
C2—C3—C4—C5	−4.2 (3)	C2—Ru1—C11—O2	−50 (4)
Ru1—C3—C4—C5	61.7 (2)	C4—Ru1—C11—O2	5 (4)
C2—C3—C4—Ru1	−65.9 (2)	C5—Ru1—C11—O2	28 (4)
C10—Ru1—C4—C9	−71.8 (3)	C10—Ru1—C12—O3	−139.5 (3)
C11—Ru1—C4—C9	31.1 (3)	C11—Ru1—C12—O3	122.8 (3)
C12—Ru1—C4—C9	127.5 (3)	C1—Ru1—C12—O3	−41.7 (3)
C1—Ru1—C4—C9	−151.4 (3)	C3—Ru1—C12—O3	24.5 (3)
C3—Ru1—C4—C9	127.3 (3)	C2—Ru1—C12—O3	−8.7 (3)
C2—Ru1—C4—C9	166.4 (3)	C4—Ru1—C12—O3	24.3 (4)
C5—Ru1—C4—C9	−114.3 (3)	C5—Ru1—C12—O3	−42.1 (4)
C10—Ru1—C4—C5	42.6 (2)	C10—Ru1—C12—C13	38.8 (2)
C11—Ru1—C4—C5	145.47 (19)	C11—Ru1—C12—C13	−59.0 (2)
C12—Ru1—C4—C5	−118.2 (2)	C1—Ru1—C12—C13	136.5 (2)
C1—Ru1—C4—C5	−37.12 (18)	C3—Ru1—C12—C13	−157.3 (2)
C3—Ru1—C4—C5	−118.4 (2)	C2—Ru1—C12—C13	169.5 (2)
C2—Ru1—C4—C5	−79.28 (19)	C4—Ru1—C12—C13	−157.5 (2)
C10—Ru1—C4—C3	160.97 (18)	C5—Ru1—C12—C13	136.1 (2)
C11—Ru1—C4—C3	−96.13 (19)	O3—C12—C13—C14	−163.6 (3)
C12—Ru1—C4—C3	0.2 (3)	Ru1—C12—C13—C14	18.1 (4)
C1—Ru1—C4—C3	81.28 (19)	O3—C12—C13—C18	13.1 (4)
C2—Ru1—C4—C3	39.12 (18)	Ru1—C12—C13—C18	−165.1 (2)
C5—Ru1—C4—C3	118.4 (2)	C18—C13—C14—C15	−2.4 (5)
C9—C4—C5—C6	−0.4 (4)	C12—C13—C14—C15	174.3 (3)
C3—C4—C5—C6	−179.0 (3)	C13—C14—C15—C16	2.0 (5)
Ru1—C4—C5—C6	−120.4 (3)	C14—C15—C16—C17	−0.1 (5)
C9—C4—C5—C1	178.0 (3)	C15—C16—C17—C18	−1.4 (5)
C3—C4—C5—C1	−0.6 (3)	C16—C17—C18—C13	0.9 (5)
Ru1—C4—C5—C1	57.92 (19)	C14—C13—C18—C17	0.9 (5)
C9—C4—C5—Ru1	120.0 (3)	C12—C13—C18—C17	−176.0 (3)
C3—C4—C5—Ru1	−58.55 (19)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.95	2.55	3.204 (4)	126
C9—H9A···Cgⁱⁱ	0.95	2.72	3.657 (3)	169

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Ru(C₉H₇)(C₇H₅O)(CO)₂]
M_r	377.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.531 (3), 8.731 (2), 15.158 (4)
β (°)	108.150 (3)
V (Å³)	1450.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.736, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	11223, 3332, 2730
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.05
No. of reflections	3332
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −0.63

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.95	2.55	3.204 (4)	126
C9—H9A···Cgⁱⁱ	0.95	2.72	3.657 (3)	169

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x, y−1, z.

Acknowledgements

JSD, TAO, and BJW would like to thank Professor Nathan Bowling and Professor Robert Badger for fruitful discussions on Grignard chemistry. JSD would like to thank Professor Dwight Sweigart for stimulating discussions on ligand substitution chemistry. TAO and BJW thank the UWSP CoLS for Undergraduate Education Initiative grants. JSD gratefully acknowledges a University Professional Development grant, as well as assistance from the Department of Chemistry.

References

Badger, R. C., D'Acchioli, J. S., Gamoke, B. C., Kim, S. B., Oudenhoven, T. A., Sweigart, D. A. & Tanke, R. S. (2009). Organometallics, 28, 418–424. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chung, Y., Williard, P. & Sweigart, D. (1982). Organometallics, 1, 1053–1056. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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