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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 1| January 2016| x160027
doi:10.1107/S2414314616000274

Crystal structure of (η2,η2-cyclo­octa-1,5-diene)(η5-inden­yl)cobalt(I)

Phillip Jungk,a Anke Spannenberga and Marko Hapkea*

aLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: marko.hapke@catalysis.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 14 December 2015; accepted 6 January 2016; online 23 January 2016)

The title compound, [Co(C8H12)(C9H7)], was synthesized by the reaction of metallated 2-H-indene with CoCl(PPh3)3 and 1,5-cyclo­octa­diene in tetra­hydro­furan/toluene. In the mol­ecule, the CoI atom is coordinated by the two double bonds of the 1,5-cyclo­octa­diene ligand and η5-bonded to the indenyl ligand. The asymmetric unit contains two mol­ecules of the CoI complex with very similar conformations. In the crystal, mol­ecules are arranged into rows parallel to [100]. Apart from dispersion forces, there are no notable inter­molecular inter­actions in the crystal.

CCDC reference: 1445626

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound (Fig. 1[link]) is used for the formation of poly(enones) by terpolymerization of carbon monoxide with diynes and norbornadiene (Tsuda & Tsugawa, 1996[Tsuda, T. & Tsugawa, F. (1996). Chem. Commun. pp. 907-908.]) and also as catalyst in [2 + 2 + 2] cyclo­addition reactions of acetyl­ene and nitriles to form pyridine derivatives under irradiation (Heller & Oehme, 1995[Heller, B. & Oehme, G. (1995). J. Chem. Soc. Chem. Commun. pp. 179-180.]). It was synthesized by the reaction of metallated 2-H-indene with CoCl(PPh3)3 and 1,5-cyclooctadiene in tetrahydrofuran/toluene. In the molecule, the CoI atom is coordinated by the two double bonds of the 1,5-cyclooctadiene ligand and η5-bonded to the indenyl ligand. The asymmetric unit contains two molecules of the CoI complex with very similar conformations. In the crystal, molecules are arranged into rows parallel to [100], Fig. 2[link]. Apart from dispersion forces, there are no notable intermolecular interactions in the crystal.

[Figure 1]
Figure 1
Mol­ecular structure of one of the two mol­ecules in the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms were omitted for clarity.
[Figure 2]
Figure 2
Crystal packing of the title compound in a view approximately along the a axis. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms were omitted for clarity.

For reported synthetic procedures of the title product by reducing the bis­(η5-inden­yl) cobalt(II) complex in the presence of 1,5-cyclo­octa­diene and lithium, see: Salzer & Täschler (1985[Salzer, A. & Täschler, C. (1985). J. Organomet. Chem. 294, 261-266.]), and in the presence of magnesium-anthracene, see: Bönnemann et al. (1993[Bönnemann, H., Bogdanović, B., Brinkmann, R., Spliethoff, B. & He, D.-W. (1993). J. Organomet. Chem. 451, 23-31.]). Chiral derivatives of the title compound, varying the substituent on the 1-indenyl position, were reported by Gutnov et al. (2004[Gutnov, A., Drexler, H.-J., Spannenberg, A., Oehme, G. & Heller, B. (2004). Organometallics, 23, 1002-1009.]) and Heller & Oehme (1995[Heller, B. & Oehme, G. (1995). J. Chem. Soc. Chem. Commun. pp. 179-180.]). The structure of the Cp-analog of the title compound is reported by Ondráček et al. (1990[Ondráček, J., Schehlmann, V., Maixner, J. & Kratochvíl, B. (1990). Collect. Czech. Chem. Commun. 55, 2447-2452.]). Hung-Low & Bradley (2011[Hung-Low, F. & Bradley, C. A. (2011). Organometallics, 30, 2636-2639.], 2013[Hung-Low, F. & Bradley, C. A. (2013). Inorg. Chem. 52, 2446-2457.]) report substituted indenyl derivatives.

Synthesis and crystallization

All manipulations were carried out under an argon atmosphere using standard Schlenk techniques. THF, toluene and n-hexane were dried over two columns with activated aluminium oxide with an Inert PureSolv MD5 solvent purification system (Innovative Technology) under argon. 2H-Indene (0.06 ml, 0.50 mmol) was added to a suspension of potassium hydride (20 mg, 0.50 mmol) in 5 ml THF in a Schlenk flask and stirred for 15 min at room temperature. Using a Schlenk glass adapter, solid CoCl(PPh3)3 (0.44 g, 0.50 mmol) was added, rinsed with 5 ml THF and the resulting mixture was stirred for additional 3 h. The solvent was evaporated in vacuo and the resulting residue was dissolved in 10 ml toluene. Finally, 1,5-cyclo­octa­diene (0.09 ml, 0.75 mmol) was added and the reaction mixture stirred for 6 h at 383 K and an additional 15 h at room temperature. The resulting mixture was filtered through a short column with degassed silica (2 x 3 cm) and the filtrate diluted with THF. The solvent was removed in vacuo and the product isolated as red crystals (0.12 g, 81%) after column chromatography under inert conditions over degassed silica with n-hexane as eluent. Crystals suitable for X-ray analysis were obtained by evaporation of the eluting solvent. The identity of the compound was proven by 1H and 13C NMR.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula [Co(C8H12)(C9H7)]
Mr 282.25
Crystal system, space group Monoclinic, P21/n
Temperature (K) 150
a, b, c (Å) 8.0307 (2), 14.4939 (3), 22.2528 (6)
β (°) 98.814 (2)
V (Å3) 2559.55 (11)
Z 8
Radiation type Mo Kα
μ (mm−1) 1.32
Crystal size (mm) 0.35 × 0.34 × 0.27
 
Data collection
Diffractometer Stoe IPDS II
No. of measured, independent and observed [I > 2σ(I)] reflections 35986, 5024, 4307
Rint 0.032
(sin θ/λ)max (Å−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.060, 1.03
No. of reflections 5024
No. of parameters 357
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.36, −0.39
Computer programs: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2006[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.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 1445626

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2414314616000274/wm5256sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616000274/wm5256Isup2.hkl

checkCIF report


Synthesis and crystallization top

All manipulations were carried out under argon atmosphere using standard Schlenk techniques. THF, toluene and n-hexane were dried over two columns with activated aluminium oxide with an Inert PureSolv MD5 solvent purification system (Innovative Technology) under argon. 2H-Indene (0.06 ml, 0.50 mmol) was added to a suspension of potassium hydride (20 mg, 0.50 mmol) in 5 ml THF in a Schlenk flask and stirred for 15 min at room temperature. Using a Schlenk glass adapter, solid CoCl(PPh3)3 (0.44 g, 0.50 mmol) was added, rinsed with 5 ml THF and the resulting mixture was stirred for additional 3 h. The solvent was evaporated in vacuo and the resulting residue was dissolved in 10 ml toluene. Finally, 1,5-cyclo­octa­diene (0.09 ml, 0.75 mmol) was added and the reaction mixture stirred for 6 h at 383 K and additional 15 h at room temperature. The resulting mixture was filtered over a short column with degassed silica (2x3 cm) and the filtrate diluted with THF. The solvent was removed in vacuo and the product isolated as red crystals (0.12 g, 81%) after column chromatography under inert conditions over degassed silica with n-hexane as eluent. Crystals suitable for X-ray analysis were obtained by evaporation of the eluting solvent. The identity of the compound was proven by 1H and 13C NMR.

Refinement top

H10, H11, H14, H15, H27, H28, H31 and H32 were found from a difference Fourier map and refined freely. All other H atoms were placed in idealized positions with d(C—H) = 0.95 Å (CH), 0.99 Å (CH2) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C).

Related literature top

For reported synthetic procedures of the title product by reducing the bis(η5-indenyl) cobalt(II) complex in the presence of 1,5-cyclooctadiene and lithium, see: Salzer & Täschler (1985), and in the presence of magnesium-anthracene, see: Bönnemann et al. (1993). Chiral derivatives of the title compound, varying the substituent on the 1-indenyl position, were reported by Gutnov et al. (2004) and Heller & Oehme (1995). For the structure of the Cp-analog of the title compound, see: Ondráček et al. (1990). For substituted indenyl derivatives, see: Hung-Low & Bradley (2011, 2013). The title compound is used for the formation of poly(enones) by terpolymerization of carbon monoxide with diynes and norbornadiene (Tsuda & Tsugawa, 1996) and also as catalyst in [2 + 2+2] cycloaddition reactions of acetylene and nitriles to form pyridine derivatives under irradiation (Heller & Oehme, 1995).

Experimental top

All manipulations were carried out under an argon atmosphere using standard Schlenk techniques. THF, toluene and n-hexane were dried over two columns with activated aluminium oxide with an Inert PureSolv MD5 solvent purification system (Innovative Technology) under argon. 2H-Indene (0.06 ml, 0.50 mmol) was added to a suspension of potassium hydride (20 mg, 0.50 mmol) in 5 ml THF in a Schlenk flask and stirred for 15 min at room temperature. Using a Schlenk glass adapter, solid CoCl(PPh3)3 (0.44 g, 0.50 mmol) was added, rinsed with 5 ml THF and the resulting mixture was stirred for additional 3 h. The solvent was evaporated in vacuo and the resulting residue was dissolved in 10 ml toluene. Finally, 1,5-cyclooctadiene (0.09 ml, 0.75 mmol) was added and the reaction mixture stirred for 6 h at 383 K and an additional 15 h at room temperature. The resulting mixture was filtered over a short column with degassed silica (2 x 3 cm) and the filtrate diluted with THF. The solvent was removed in vacuo and the product isolated as red crystals (0.12 g, 81%) after column chromatography under inert conditions over degassed silica with n-hexane as eluent. Crystals suitable for X-ray analysis were obtained by evaporation of the eluting solvent. The identity of the compound was proven by 1H and 13C NMR.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Structure description top

The title compound (Fig. 1) is used for the formation of poly(enones) by terpolymerization of carbon monoxide with diynes and norbornadiene (Tsuda & Tsugawa, 1996) and also as catalyst in [2 + 2 + 2] cycloaddition reactions of acetylene and nitriles to form pyridine derivatives under irradiation (Heller & Oehme, 1995). It was synthesized by the reaction of metallated 2-H-indene with CoCl(PPh3)3 and 1,5-cyclooctadiene in tetrahydrofuran/toluene. In the molecule, the CoI atom is coordinated by the two double bonds of the 1,5-cyclooctadiene ligand and η5-bonded to the indenyl ligand. The asymmetric unit contains two molecules of the CoI complex with very similar conformations. In the crystal, molecules are arranged into rows parallel to [100], Fig. 2. Apart from dispersion forces, there are no notable intermolecular interactions in the crystal.

For reported synthetic procedures of the title product by reducing the bis(η5-indenyl) cobalt(II) complex in the presence of 1,5-cyclooctadiene and lithium, see: Salzer & Täschler (1985), and in the presence of magnesium-anthracene, see: Bönnemann et al. (1993). Chiral derivatives of the title compound, varying the substituent on the 1-indenyl position, were reported by Gutnov et al. (2004) and Heller & Oehme (1995). The structure of the Cp-analog of the title compound is reported by Ondráček et al. (1990). Hung-Low & Bradley (2011, 2013) report substituted indenyl derivatives.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of one of the two molecules in the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms were omitted for clarity.
[Figure 2] Fig. 2. Crystal packing of the title compound in a view approximately along the a axis. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms were omitted for clarity.
(η2,η2-Cycloocta-1,5-diene)(η5-indenyl)cobalt(I) top
Crystal data top
[Co(C8H12)(C9H7)]F(000) = 1184
Mr = 282.25Dx = 1.465 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.0307 (2) ÅCell parameters from 3014 reflections
b = 14.4939 (3) Åθ = 1.6–27.1°
c = 22.2528 (6) ŵ = 1.32 mm−1
β = 98.814 (2)°T = 150 K
V = 2559.55 (11) Å3Prism, red-brown
Z = 80.35 × 0.34 × 0.27 mm
Data collection top
Stoe IPDS II
diffractometer		4307 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ω–scansh = −9→9
35986 measured reflectionsk = −17→17
5024 independent reflectionsl = −27→27
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0431P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5024 reflectionsΔρmax = 0.36 e Å−3
357 parametersΔρmin = −0.39 e Å−3
Crystal data top
[Co(C8H12)(C9H7)]V = 2559.55 (11) Å3
Mr = 282.25Z = 8
Monoclinic, P21/nMo Kα radiation
a = 8.0307 (2) ŵ = 1.32 mm−1
b = 14.4939 (3) ÅT = 150 K
c = 22.2528 (6) Å0.35 × 0.34 × 0.27 mm
β = 98.814 (2)°
Data collection top
Stoe IPDS II
diffractometer		4307 reflections with I > 2σ(I)
35986 measured reflectionsRint = 0.032
5024 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.36 e Å−3
5024 reflectionsΔρmin = −0.39 e Å−3
357 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.59531 (2)−0.00072 (2)0.23597 (2)0.02402 (7)
C10.84516 (16)0.06045 (10)0.24041 (7)0.0262 (3)
C20.78946 (18)0.01032 (10)0.18505 (7)0.0294 (3)
H20.77020.03590.14530.035*
C30.76847 (18)−0.08314 (10)0.19994 (7)0.0318 (3)
H30.7427−0.13240.17190.038*
C40.79252 (18)−0.09065 (10)0.26417 (7)0.0300 (3)
H40.7762−0.14480.28660.036*
C50.84612 (18)−0.00198 (9)0.28988 (7)0.0270 (3)
C60.88758 (18)0.03005 (11)0.35024 (7)0.0320 (3)
H60.8853−0.01060.38360.038*
C70.93101 (19)0.12060 (11)0.35988 (7)0.0351 (3)
H70.96050.14250.40040.042*
C80.93288 (19)0.18232 (11)0.31084 (8)0.0344 (3)
H80.96520.24470.31900.041*
C90.88928 (18)0.15423 (10)0.25217 (7)0.0310 (3)
H90.88840.19670.21960.037*
C100.47123 (19)0.11738 (10)0.21129 (7)0.0316 (3)
H100.547 (2)0.1588 (12)0.1943 (8)0.039 (5)*
C110.40445 (19)0.04573 (10)0.17247 (7)0.0311 (3)
H110.444 (2)0.0405 (11)0.1338 (8)0.030 (4)*
C120.2365 (2)0.00024 (11)0.17674 (8)0.0363 (4)
H12A0.1815−0.01790.13560.044*
H12B0.16200.04500.19320.044*
C130.25913 (19)−0.08530 (11)0.21783 (8)0.0362 (4)
H13A0.1589−0.09240.23840.043*
H13B0.2671−0.14080.19240.043*
C140.41473 (18)−0.07912 (11)0.26525 (7)0.0316 (3)
H140.463 (2)−0.1390 (12)0.2795 (8)0.035 (4)*
C150.45397 (19)−0.00372 (10)0.30418 (7)0.0305 (3)
H150.526 (2)−0.0130 (10)0.3411 (8)0.031 (4)*
C160.3418 (2)0.08051 (11)0.30450 (8)0.0377 (4)
H16A0.35030.10450.34650.045*
H16B0.22310.06260.29070.045*
C170.3921 (2)0.15631 (11)0.26299 (8)0.0387 (4)
H17A0.29090.19240.24630.046*
H17B0.47290.19870.28720.046*
Co20.03476 (2)0.78868 (2)1.00510 (2)0.02282 (6)
C18−0.22601 (17)0.76375 (10)0.96523 (7)0.0275 (3)
C19−0.19275 (18)0.85687 (10)0.98738 (7)0.0312 (3)
H19−0.20440.91130.96330.037*
C20−0.14008 (19)0.85315 (11)1.05075 (7)0.0325 (3)
H20−0.11940.90471.07720.039*
C21−0.12338 (19)0.75916 (11)1.06809 (7)0.0313 (3)
H21−0.08030.73691.10760.038*
C22−0.18288 (17)0.70295 (10)1.01557 (7)0.0279 (3)
C23−0.19716 (19)0.60644 (10)1.00634 (8)0.0346 (3)
H23−0.16730.56491.03920.041*
C24−0.2546 (2)0.57421 (11)0.94931 (8)0.0384 (4)
H24−0.26710.50960.94300.046*
C25−0.29577 (19)0.63447 (11)0.89959 (8)0.0373 (4)
H25−0.33440.60960.86040.045*
C26−0.28128 (19)0.72780 (11)0.90658 (7)0.0329 (3)
H26−0.30780.76780.87260.040*
C270.1724 (2)0.87766 (11)0.96298 (8)0.0365 (4)
H270.108 (2)0.9323 (13)0.9565 (9)0.048 (5)*
C280.1180 (2)0.80406 (12)0.92464 (8)0.0365 (4)
H280.026 (3)0.8137 (13)0.8947 (9)0.050 (5)*
C290.2226 (2)0.72263 (13)0.91177 (8)0.0458 (4)
H29A0.30780.74310.88680.055*
H29B0.14910.67670.88780.055*
C300.3114 (2)0.67713 (12)0.96903 (8)0.0415 (4)
H30A0.42690.70240.97890.050*
H30B0.32060.61000.96190.050*
C310.21792 (19)0.69281 (11)1.02245 (7)0.0310 (3)
H310.166 (2)0.6412 (12)1.0364 (8)0.037 (5)*
C320.25222 (19)0.76667 (11)1.06207 (7)0.0329 (3)
H320.226 (2)0.7578 (11)1.1021 (8)0.037 (5)*
C330.3829 (2)0.83998 (13)1.05601 (9)0.0458 (4)
H33A0.49620.81131.06220.055*
H33B0.38060.88701.08820.055*
C340.3530 (2)0.88699 (12)0.99418 (10)0.0466 (4)
H34A0.38140.95330.99940.056*
H34B0.42900.85960.96790.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02222 (10)0.02618 (11)0.02454 (11)0.00065 (7)0.00640 (8)0.00204 (7)
C10.0193 (6)0.0305 (7)0.0301 (8)0.0012 (5)0.0078 (6)0.0028 (6)
C20.0257 (7)0.0364 (8)0.0280 (8)−0.0009 (6)0.0099 (6)0.0023 (6)
C30.0288 (7)0.0330 (8)0.0363 (9)0.0009 (6)0.0134 (6)−0.0057 (6)
C40.0267 (7)0.0265 (7)0.0382 (9)0.0039 (6)0.0095 (6)0.0043 (6)
C50.0197 (7)0.0306 (7)0.0312 (8)0.0039 (5)0.0058 (6)0.0030 (6)
C60.0250 (7)0.0430 (8)0.0281 (8)0.0037 (6)0.0047 (6)0.0061 (7)
C70.0253 (7)0.0472 (9)0.0320 (8)0.0022 (6)0.0016 (6)−0.0080 (7)
C80.0261 (7)0.0315 (8)0.0454 (10)0.0004 (6)0.0052 (7)−0.0062 (7)
C90.0248 (7)0.0296 (7)0.0389 (9)0.0001 (5)0.0056 (6)0.0043 (6)
C100.0282 (7)0.0299 (7)0.0363 (9)0.0044 (6)0.0033 (6)0.0074 (6)
C110.0281 (7)0.0370 (8)0.0277 (8)0.0035 (6)0.0027 (6)0.0057 (6)
C120.0268 (8)0.0455 (9)0.0357 (9)−0.0011 (6)0.0020 (7)−0.0023 (7)
C130.0290 (8)0.0397 (9)0.0413 (9)−0.0066 (6)0.0097 (7)−0.0036 (7)
C140.0278 (7)0.0331 (8)0.0363 (9)−0.0015 (6)0.0124 (6)0.0057 (7)
C150.0261 (7)0.0395 (9)0.0277 (8)0.0010 (6)0.0101 (6)0.0034 (6)
C160.0345 (8)0.0444 (9)0.0364 (9)0.0045 (7)0.0117 (7)−0.0083 (7)
C170.0378 (9)0.0326 (8)0.0453 (10)0.0075 (6)0.0056 (7)−0.0045 (7)
Co20.02156 (10)0.02390 (10)0.02391 (11)0.00029 (7)0.00638 (7)0.00126 (7)
C180.0190 (7)0.0306 (7)0.0334 (8)0.0017 (5)0.0061 (6)0.0031 (6)
C190.0257 (7)0.0280 (7)0.0412 (9)0.0051 (6)0.0088 (6)0.0018 (6)
C200.0285 (7)0.0333 (8)0.0384 (9)0.0004 (6)0.0139 (6)−0.0072 (7)
C210.0279 (7)0.0411 (8)0.0265 (8)−0.0033 (6)0.0098 (6)0.0012 (6)
C220.0218 (7)0.0325 (7)0.0310 (8)−0.0015 (5)0.0088 (6)0.0026 (6)
C230.0314 (8)0.0318 (8)0.0412 (9)−0.0033 (6)0.0077 (7)0.0082 (7)
C240.0339 (8)0.0289 (8)0.0529 (10)−0.0047 (6)0.0082 (7)−0.0059 (7)
C250.0296 (8)0.0454 (9)0.0369 (9)−0.0038 (7)0.0050 (7)−0.0092 (7)
C260.0258 (7)0.0401 (8)0.0323 (8)0.0005 (6)0.0024 (6)0.0033 (7)
C270.0313 (8)0.0332 (8)0.0473 (10)−0.0007 (6)0.0135 (7)0.0131 (7)
C280.0328 (8)0.0501 (10)0.0283 (8)0.0003 (7)0.0107 (7)0.0117 (7)
C290.0470 (10)0.0585 (11)0.0359 (9)−0.0013 (8)0.0193 (8)−0.0079 (8)
C300.0398 (9)0.0423 (9)0.0444 (10)0.0100 (7)0.0132 (8)−0.0062 (8)
C310.0278 (7)0.0300 (8)0.0356 (9)0.0054 (6)0.0066 (6)0.0040 (6)
C320.0252 (7)0.0458 (9)0.0269 (8)0.0016 (6)0.0020 (6)0.0006 (7)
C330.0305 (8)0.0565 (11)0.0496 (11)−0.0103 (7)0.0041 (7)−0.0130 (9)
C340.0336 (9)0.0368 (9)0.0710 (13)−0.0109 (7)0.0135 (8)0.0023 (8)
Geometric parameters (Å, º) top
Co1—C102.0142 (14)Co2—C282.0169 (16)
Co1—C142.0269 (14)Co2—C312.0173 (15)
Co1—C152.0304 (15)Co2—C322.0199 (16)
Co1—C112.0336 (15)Co2—C272.0200 (15)
Co1—C22.0693 (14)Co2—C192.0615 (14)
Co1—C42.0727 (14)Co2—C212.0751 (15)
Co1—C32.0844 (14)Co2—C202.0770 (14)
Co1—C52.1808 (15)Co2—C182.1757 (14)
Co1—C12.1820 (13)Co2—C222.1859 (14)
C1—C91.419 (2)C18—C261.412 (2)
C1—C51.424 (2)C18—C221.426 (2)
C1—C21.441 (2)C18—C191.448 (2)
C2—C31.411 (2)C19—C201.410 (2)
C2—H20.9500C19—H190.9500
C3—C41.417 (2)C20—C211.417 (2)
C3—H30.9500C20—H200.9500
C4—C51.445 (2)C21—C221.445 (2)
C4—H40.9500C21—H210.9500
C5—C61.412 (2)C22—C231.416 (2)
C6—C71.366 (2)C23—C241.365 (2)
C6—H60.9500C23—H230.9500
C7—C81.413 (2)C24—C251.408 (2)
C7—H70.9500C24—H240.9500
C8—C91.361 (2)C25—C261.365 (2)
C8—H80.9500C25—H250.9500
C9—H90.9500C26—H260.9500
C10—C111.404 (2)C27—C281.394 (2)
C10—C171.506 (2)C27—C341.515 (2)
C10—H100.974 (18)C27—H270.945 (19)
C11—C121.518 (2)C28—C291.502 (2)
C11—H110.964 (17)C28—H280.93 (2)
C12—C131.535 (2)C29—C301.513 (3)
C12—H12A0.9900C29—H29A0.9900
C12—H12B0.9900C29—H29B0.9900
C13—C141.510 (2)C30—C311.517 (2)
C13—H13A0.9900C30—H30A0.9900
C13—H13B0.9900C30—H30B0.9900
C14—C151.400 (2)C31—C321.387 (2)
C14—H140.984 (17)C31—H310.934 (18)
C15—C161.518 (2)C32—C331.514 (2)
C15—H150.939 (18)C32—H320.957 (18)
C16—C171.529 (2)C33—C341.521 (3)
C16—H16A0.9900C33—H33A0.9900
C16—H16B0.9900C33—H33B0.9900
C17—H17A0.9900C34—H34A0.9900
C17—H17B0.9900C34—H34B0.9900
C10—Co1—C14102.45 (6)C28—Co2—C3185.13 (7)
C10—Co1—C1584.96 (6)C28—Co2—C32101.68 (7)
C14—Co1—C1540.37 (6)C31—Co2—C3240.20 (7)
C10—Co1—C1140.58 (6)C28—Co2—C2740.40 (7)
C14—Co1—C1184.77 (6)C31—Co2—C2795.39 (7)
C15—Co1—C1194.50 (6)C32—Co2—C2784.84 (7)
C10—Co1—C299.66 (6)C28—Co2—C19100.47 (7)
C14—Co1—C2148.83 (6)C31—Co2—C19164.95 (6)
C15—Co1—C2164.90 (6)C32—Co2—C19148.37 (7)
C11—Co1—C298.33 (6)C27—Co2—C1997.88 (6)
C10—Co1—C4160.07 (6)C28—Co2—C21160.50 (7)
C14—Co1—C495.81 (6)C31—Co2—C21103.44 (6)
C15—Co1—C4104.41 (6)C32—Co2—C2195.93 (6)
C11—Co1—C4151.42 (6)C27—Co2—C21151.64 (7)
C2—Co1—C467.02 (6)C19—Co2—C2167.16 (6)
C10—Co1—C3135.52 (6)C28—Co2—C20136.49 (7)
C14—Co1—C3110.78 (6)C31—Co2—C20138.07 (7)
C15—Co1—C3139.25 (6)C32—Co2—C20110.38 (7)
C11—Co1—C3113.50 (6)C27—Co2—C20113.49 (7)
C2—Co1—C339.71 (6)C19—Co2—C2039.83 (6)
C4—Co1—C339.85 (6)C21—Co2—C2039.90 (6)
C10—Co1—C5122.26 (6)C28—Co2—C1894.90 (6)
C14—Co1—C5117.67 (6)C31—Co2—C18126.28 (6)
C15—Co1—C599.41 (6)C32—Co2—C18156.24 (6)
C11—Co1—C5156.82 (6)C27—Co2—C18118.53 (6)
C2—Co1—C565.92 (6)C19—Co2—C1839.84 (6)
C4—Co1—C539.62 (5)C21—Co2—C1865.84 (6)
C3—Co1—C565.95 (6)C20—Co2—C1866.02 (6)
C10—Co1—C194.59 (6)C28—Co2—C22122.44 (7)
C14—Co1—C1155.71 (6)C31—Co2—C2299.18 (6)
C15—Co1—C1126.18 (6)C32—Co2—C22118.15 (6)
C11—Co1—C1119.14 (6)C27—Co2—C22156.30 (7)
C2—Co1—C139.52 (6)C19—Co2—C2265.99 (6)
C4—Co1—C165.62 (5)C21—Co2—C2239.53 (6)
C3—Co1—C165.62 (6)C20—Co2—C2265.93 (6)
C5—Co1—C138.10 (5)C18—Co2—C2238.16 (5)
C9—C1—C5119.64 (14)C26—C18—C22120.14 (14)
C9—C1—C2132.58 (14)C26—C18—C19132.39 (14)
C5—C1—C2107.74 (13)C22—C18—C19107.39 (13)
C9—C1—Co1126.84 (10)C26—C18—Co2125.78 (10)
C5—C1—Co170.90 (8)C22—C18—Co271.31 (8)
C2—C1—Co166.02 (8)C19—C18—Co265.83 (8)
C3—C2—C1108.41 (13)C20—C19—C18108.45 (13)
C3—C2—Co170.72 (8)C20—C19—Co270.68 (8)
C1—C2—Co174.46 (8)C18—C19—Co274.34 (8)
C3—C2—H2125.8C20—C19—H19125.8
C1—C2—H2125.8C18—C19—H19125.8
Co1—C2—H2120.7Co2—C19—H19120.9
C2—C3—C4107.94 (13)C19—C20—C21108.09 (13)
C2—C3—Co169.57 (8)C19—C20—Co269.49 (8)
C4—C3—Co169.63 (8)C21—C20—Co269.98 (8)
C2—C3—H3126.0C19—C20—H20126.0
C4—C3—H3126.0C21—C20—H20126.0
Co1—C3—H3126.3Co2—C20—H20126.1
C3—C4—C5108.50 (13)C20—C21—C22108.44 (14)
C3—C4—Co170.52 (8)C20—C21—Co270.12 (8)
C5—C4—Co174.22 (8)C22—C21—Co274.37 (8)
C3—C4—H4125.8C20—C21—H21125.8
C5—C4—H4125.8C22—C21—H21125.8
Co1—C4—H4121.2Co2—C21—H21121.4
C6—C5—C1119.93 (13)C23—C22—C18119.49 (14)
C6—C5—C4132.96 (14)C23—C22—C21133.15 (14)
C1—C5—C4107.04 (13)C18—C22—C21107.30 (13)
C6—C5—Co1125.72 (10)C23—C22—Co2126.47 (10)
C1—C5—Co171.00 (8)C18—C22—Co270.54 (8)
C4—C5—Co166.15 (8)C21—C22—Co266.10 (8)
C7—C6—C5118.85 (15)C24—C23—C22118.78 (15)
C7—C6—H6120.6C24—C23—H23120.6
C5—C6—H6120.6C22—C23—H23120.6
C6—C7—C8121.30 (15)C23—C24—C25121.56 (15)
C6—C7—H7119.3C23—C24—H24119.2
C8—C7—H7119.3C25—C24—H24119.2
C9—C8—C7121.32 (14)C26—C25—C24121.30 (15)
C9—C8—H8119.3C26—C25—H25119.3
C7—C8—H8119.3C24—C25—H25119.3
C8—C9—C1118.93 (14)C25—C26—C18118.71 (15)
C8—C9—H9120.5C25—C26—H26120.6
C1—C9—H9120.5C18—C26—H26120.6
C11—C10—C17125.52 (14)C28—C27—C34122.49 (15)
C11—C10—Co170.45 (8)C28—C27—Co269.68 (9)
C17—C10—Co1111.05 (11)C34—C27—Co2113.45 (11)
C11—C10—H10114.9 (10)C28—C27—H27115.8 (12)
C17—C10—H10115.4 (10)C34—C27—H27117.2 (12)
Co1—C10—H10108.4 (10)Co2—C27—H27106.4 (11)
C10—C11—C12122.84 (14)C27—C28—C29125.88 (16)
C10—C11—Co168.97 (8)C27—C28—Co269.92 (9)
C12—C11—Co1113.28 (11)C29—C28—Co2110.72 (11)
C10—C11—H11117.5 (10)C27—C28—H28117.8 (12)
C12—C11—H11116.0 (10)C29—C28—H28112.9 (12)
Co1—C11—H11106.2 (10)Co2—C28—H28108.5 (12)
C11—C12—C13111.27 (13)C28—C29—C30112.79 (14)
C11—C12—H12A109.4C28—C29—H29A109.0
C13—C12—H12A109.4C30—C29—H29A109.0
C11—C12—H12B109.4C28—C29—H29B109.0
C13—C12—H12B109.4C30—C29—H29B109.0
H12A—C12—H12B108.0H29A—C29—H29B107.8
C14—C13—C12112.24 (13)C29—C30—C31111.63 (13)
C14—C13—H13A109.2C29—C30—H30A109.3
C12—C13—H13A109.2C31—C30—H30A109.3
C14—C13—H13B109.2C29—C30—H30B109.3
C12—C13—H13B109.2C31—C30—H30B109.3
H13A—C13—H13B107.9H30A—C30—H30B108.0
C15—C14—C13124.23 (14)C32—C31—C30122.65 (15)
C15—C14—Co169.95 (8)C32—C31—Co270.00 (9)
C13—C14—Co1111.40 (10)C30—C31—Co2112.77 (11)
C15—C14—H14116.6 (10)C32—C31—H31117.5 (11)
C13—C14—H14114.7 (10)C30—C31—H31116.2 (11)
Co1—C14—H14109.3 (10)Co2—C31—H31105.4 (11)
C14—C15—C16123.58 (15)C31—C32—C33123.91 (15)
C14—C15—Co169.68 (8)C31—C32—Co269.80 (9)
C16—C15—Co1112.73 (10)C33—C32—Co2112.20 (12)
C14—C15—H15118.6 (10)C31—C32—H32115.9 (10)
C16—C15—H15113.5 (10)C33—C32—H32115.7 (11)
Co1—C15—H15108.4 (11)Co2—C32—H32108.1 (11)
C15—C16—C17111.29 (13)C32—C33—C34112.29 (14)
C15—C16—H16A109.4C32—C33—H33A109.1
C17—C16—H16A109.4C34—C33—H33A109.1
C15—C16—H16B109.4C32—C33—H33B109.1
C17—C16—H16B109.4C34—C33—H33B109.1
H16A—C16—H16B108.0H33A—C33—H33B107.9
C10—C17—C16111.94 (13)C27—C34—C33112.45 (13)
C10—C17—H17A109.2C27—C34—H34A109.1
C16—C17—H17A109.2C33—C34—H34A109.1
C10—C17—H17B109.2C27—C34—H34B109.1
C16—C17—H17B109.2C33—C34—H34B109.1
H17A—C17—H17B107.9H34A—C34—H34B107.8

Experimental details

Crystal data
Chemical formula[Co(C8H12)(C9H7)]
Mr282.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)8.0307 (2), 14.4939 (3), 22.2528 (6)
β (°) 98.814 (2)
V (Å3)2559.55 (11)
Z8
Radiation typeMo Kα
µ (mm−1)1.32
Crystal size (mm)0.35 × 0.34 × 0.27
Data collection
DiffractometerStoe IPDS II
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		35986, 5024, 4307
Rint0.032
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.060, 1.03
No. of reflections5024
No. of parameters357
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.36, −0.39

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

 

Acknowledgements

We thank Professor Dr Uwe Rosenthal for his continuing support and helpful discussions. We thank the DFG (HA3511/3–1) and the Leibniz–Gemeinschaft for financial support.

References

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ISSN: 2414-3146
Volume 1| Part 1| January 2016| x160027
doi:10.1107/S2414314616000274
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