Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616000274/wm5256sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314616000274/wm5256Isup2.hkl |
CCDC reference: 1445626
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.022
- wR factor = 0.060
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 4 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 2 Note
Alert level G PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct. 8 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 1 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.
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.
Crystal data, data collection and structure refinement details are summarized in Table 1.
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.
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).
[Co(C8H12)(C9H7)] | F(000) = 1184 |
Mr = 282.25 | Dx = 1.465 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0307 (2) Å | Cell parameters from 3014 reflections |
b = 14.4939 (3) Å | θ = 1.6–27.1° |
c = 22.2528 (6) Å | µ = 1.32 mm−1 |
β = 98.814 (2)° | T = 150 K |
V = 2559.55 (11) Å3 | Prism, red-brown |
Z = 8 | 0.35 × 0.34 × 0.27 mm |
Stoe IPDS II diffractometer | 4307 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω–scans | h = −9→9 |
35986 measured reflections | k = −17→17 |
5024 independent reflections | l = −27→27 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.022 | H 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 reflections | Δρmax = 0.36 e Å−3 |
357 parameters | Δρmin = −0.39 e Å−3 |
[Co(C8H12)(C9H7)] | V = 2559.55 (11) Å3 |
Mr = 282.25 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.0307 (2) Å | µ = 1.32 mm−1 |
b = 14.4939 (3) Å | T = 150 K |
c = 22.2528 (6) Å | 0.35 × 0.34 × 0.27 mm |
β = 98.814 (2)° |
Stoe IPDS II diffractometer | 4307 reflections with I > 2σ(I) |
35986 measured reflections | Rint = 0.032 |
5024 independent reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.36 e Å−3 |
5024 reflections | Δρmin = −0.39 e Å−3 |
357 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.59531 (2) | −0.00072 (2) | 0.23597 (2) | 0.02402 (7) | |
C1 | 0.84516 (16) | 0.06045 (10) | 0.24041 (7) | 0.0262 (3) | |
C2 | 0.78946 (18) | 0.01032 (10) | 0.18505 (7) | 0.0294 (3) | |
H2 | 0.7702 | 0.0359 | 0.1453 | 0.035* | |
C3 | 0.76847 (18) | −0.08314 (10) | 0.19994 (7) | 0.0318 (3) | |
H3 | 0.7427 | −0.1324 | 0.1719 | 0.038* | |
C4 | 0.79252 (18) | −0.09065 (10) | 0.26417 (7) | 0.0300 (3) | |
H4 | 0.7762 | −0.1448 | 0.2866 | 0.036* | |
C5 | 0.84612 (18) | −0.00198 (9) | 0.28988 (7) | 0.0270 (3) | |
C6 | 0.88758 (18) | 0.03005 (11) | 0.35024 (7) | 0.0320 (3) | |
H6 | 0.8853 | −0.0106 | 0.3836 | 0.038* | |
C7 | 0.93101 (19) | 0.12060 (11) | 0.35988 (7) | 0.0351 (3) | |
H7 | 0.9605 | 0.1425 | 0.4004 | 0.042* | |
C8 | 0.93288 (19) | 0.18232 (11) | 0.31084 (8) | 0.0344 (3) | |
H8 | 0.9652 | 0.2447 | 0.3190 | 0.041* | |
C9 | 0.88928 (18) | 0.15423 (10) | 0.25217 (7) | 0.0310 (3) | |
H9 | 0.8884 | 0.1967 | 0.2196 | 0.037* | |
C10 | 0.47123 (19) | 0.11738 (10) | 0.21129 (7) | 0.0316 (3) | |
H10 | 0.547 (2) | 0.1588 (12) | 0.1943 (8) | 0.039 (5)* | |
C11 | 0.40445 (19) | 0.04573 (10) | 0.17247 (7) | 0.0311 (3) | |
H11 | 0.444 (2) | 0.0405 (11) | 0.1338 (8) | 0.030 (4)* | |
C12 | 0.2365 (2) | 0.00024 (11) | 0.17674 (8) | 0.0363 (4) | |
H12A | 0.1815 | −0.0179 | 0.1356 | 0.044* | |
H12B | 0.1620 | 0.0450 | 0.1932 | 0.044* | |
C13 | 0.25913 (19) | −0.08530 (11) | 0.21783 (8) | 0.0362 (4) | |
H13A | 0.1589 | −0.0924 | 0.2384 | 0.043* | |
H13B | 0.2671 | −0.1408 | 0.1924 | 0.043* | |
C14 | 0.41473 (18) | −0.07912 (11) | 0.26525 (7) | 0.0316 (3) | |
H14 | 0.463 (2) | −0.1390 (12) | 0.2795 (8) | 0.035 (4)* | |
C15 | 0.45397 (19) | −0.00372 (10) | 0.30418 (7) | 0.0305 (3) | |
H15 | 0.526 (2) | −0.0130 (10) | 0.3411 (8) | 0.031 (4)* | |
C16 | 0.3418 (2) | 0.08051 (11) | 0.30450 (8) | 0.0377 (4) | |
H16A | 0.3503 | 0.1045 | 0.3465 | 0.045* | |
H16B | 0.2231 | 0.0626 | 0.2907 | 0.045* | |
C17 | 0.3921 (2) | 0.15631 (11) | 0.26299 (8) | 0.0387 (4) | |
H17A | 0.2909 | 0.1924 | 0.2463 | 0.046* | |
H17B | 0.4729 | 0.1987 | 0.2872 | 0.046* | |
Co2 | 0.03476 (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 | −0.2044 | 0.9113 | 0.9633 | 0.037* | |
C20 | −0.14008 (19) | 0.85315 (11) | 1.05075 (7) | 0.0325 (3) | |
H20 | −0.1194 | 0.9047 | 1.0772 | 0.039* | |
C21 | −0.12338 (19) | 0.75916 (11) | 1.06809 (7) | 0.0313 (3) | |
H21 | −0.0803 | 0.7369 | 1.1076 | 0.038* | |
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 | −0.1673 | 0.5649 | 1.0392 | 0.041* | |
C24 | −0.2546 (2) | 0.57421 (11) | 0.94931 (8) | 0.0384 (4) | |
H24 | −0.2671 | 0.5096 | 0.9430 | 0.046* | |
C25 | −0.29577 (19) | 0.63447 (11) | 0.89959 (8) | 0.0373 (4) | |
H25 | −0.3344 | 0.6096 | 0.8604 | 0.045* | |
C26 | −0.28128 (19) | 0.72780 (11) | 0.90658 (7) | 0.0329 (3) | |
H26 | −0.3078 | 0.7678 | 0.8726 | 0.040* | |
C27 | 0.1724 (2) | 0.87766 (11) | 0.96298 (8) | 0.0365 (4) | |
H27 | 0.108 (2) | 0.9323 (13) | 0.9565 (9) | 0.048 (5)* | |
C28 | 0.1180 (2) | 0.80406 (12) | 0.92464 (8) | 0.0365 (4) | |
H28 | 0.026 (3) | 0.8137 (13) | 0.8947 (9) | 0.050 (5)* | |
C29 | 0.2226 (2) | 0.72263 (13) | 0.91177 (8) | 0.0458 (4) | |
H29A | 0.3078 | 0.7431 | 0.8868 | 0.055* | |
H29B | 0.1491 | 0.6767 | 0.8878 | 0.055* | |
C30 | 0.3114 (2) | 0.67713 (12) | 0.96903 (8) | 0.0415 (4) | |
H30A | 0.4269 | 0.7024 | 0.9789 | 0.050* | |
H30B | 0.3206 | 0.6100 | 0.9619 | 0.050* | |
C31 | 0.21792 (19) | 0.69281 (11) | 1.02245 (7) | 0.0310 (3) | |
H31 | 0.166 (2) | 0.6412 (12) | 1.0364 (8) | 0.037 (5)* | |
C32 | 0.25222 (19) | 0.76667 (11) | 1.06207 (7) | 0.0329 (3) | |
H32 | 0.226 (2) | 0.7578 (11) | 1.1021 (8) | 0.037 (5)* | |
C33 | 0.3829 (2) | 0.83998 (13) | 1.05601 (9) | 0.0458 (4) | |
H33A | 0.4962 | 0.8113 | 1.0622 | 0.055* | |
H33B | 0.3806 | 0.8870 | 1.0882 | 0.055* | |
C34 | 0.3530 (2) | 0.88699 (12) | 0.99418 (10) | 0.0466 (4) | |
H34A | 0.3814 | 0.9533 | 0.9994 | 0.056* | |
H34B | 0.4290 | 0.8596 | 0.9679 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.02222 (10) | 0.02618 (11) | 0.02454 (11) | 0.00065 (7) | 0.00640 (8) | 0.00204 (7) |
C1 | 0.0193 (6) | 0.0305 (7) | 0.0301 (8) | 0.0012 (5) | 0.0078 (6) | 0.0028 (6) |
C2 | 0.0257 (7) | 0.0364 (8) | 0.0280 (8) | −0.0009 (6) | 0.0099 (6) | 0.0023 (6) |
C3 | 0.0288 (7) | 0.0330 (8) | 0.0363 (9) | 0.0009 (6) | 0.0134 (6) | −0.0057 (6) |
C4 | 0.0267 (7) | 0.0265 (7) | 0.0382 (9) | 0.0039 (6) | 0.0095 (6) | 0.0043 (6) |
C5 | 0.0197 (7) | 0.0306 (7) | 0.0312 (8) | 0.0039 (5) | 0.0058 (6) | 0.0030 (6) |
C6 | 0.0250 (7) | 0.0430 (8) | 0.0281 (8) | 0.0037 (6) | 0.0047 (6) | 0.0061 (7) |
C7 | 0.0253 (7) | 0.0472 (9) | 0.0320 (8) | 0.0022 (6) | 0.0016 (6) | −0.0080 (7) |
C8 | 0.0261 (7) | 0.0315 (8) | 0.0454 (10) | 0.0004 (6) | 0.0052 (7) | −0.0062 (7) |
C9 | 0.0248 (7) | 0.0296 (7) | 0.0389 (9) | 0.0001 (5) | 0.0056 (6) | 0.0043 (6) |
C10 | 0.0282 (7) | 0.0299 (7) | 0.0363 (9) | 0.0044 (6) | 0.0033 (6) | 0.0074 (6) |
C11 | 0.0281 (7) | 0.0370 (8) | 0.0277 (8) | 0.0035 (6) | 0.0027 (6) | 0.0057 (6) |
C12 | 0.0268 (8) | 0.0455 (9) | 0.0357 (9) | −0.0011 (6) | 0.0020 (7) | −0.0023 (7) |
C13 | 0.0290 (8) | 0.0397 (9) | 0.0413 (9) | −0.0066 (6) | 0.0097 (7) | −0.0036 (7) |
C14 | 0.0278 (7) | 0.0331 (8) | 0.0363 (9) | −0.0015 (6) | 0.0124 (6) | 0.0057 (7) |
C15 | 0.0261 (7) | 0.0395 (9) | 0.0277 (8) | 0.0010 (6) | 0.0101 (6) | 0.0034 (6) |
C16 | 0.0345 (8) | 0.0444 (9) | 0.0364 (9) | 0.0045 (7) | 0.0117 (7) | −0.0083 (7) |
C17 | 0.0378 (9) | 0.0326 (8) | 0.0453 (10) | 0.0075 (6) | 0.0056 (7) | −0.0045 (7) |
Co2 | 0.02156 (10) | 0.02390 (10) | 0.02391 (11) | 0.00029 (7) | 0.00638 (7) | 0.00126 (7) |
C18 | 0.0190 (7) | 0.0306 (7) | 0.0334 (8) | 0.0017 (5) | 0.0061 (6) | 0.0031 (6) |
C19 | 0.0257 (7) | 0.0280 (7) | 0.0412 (9) | 0.0051 (6) | 0.0088 (6) | 0.0018 (6) |
C20 | 0.0285 (7) | 0.0333 (8) | 0.0384 (9) | 0.0004 (6) | 0.0139 (6) | −0.0072 (7) |
C21 | 0.0279 (7) | 0.0411 (8) | 0.0265 (8) | −0.0033 (6) | 0.0098 (6) | 0.0012 (6) |
C22 | 0.0218 (7) | 0.0325 (7) | 0.0310 (8) | −0.0015 (5) | 0.0088 (6) | 0.0026 (6) |
C23 | 0.0314 (8) | 0.0318 (8) | 0.0412 (9) | −0.0033 (6) | 0.0077 (7) | 0.0082 (7) |
C24 | 0.0339 (8) | 0.0289 (8) | 0.0529 (10) | −0.0047 (6) | 0.0082 (7) | −0.0059 (7) |
C25 | 0.0296 (8) | 0.0454 (9) | 0.0369 (9) | −0.0038 (7) | 0.0050 (7) | −0.0092 (7) |
C26 | 0.0258 (7) | 0.0401 (8) | 0.0323 (8) | 0.0005 (6) | 0.0024 (6) | 0.0033 (7) |
C27 | 0.0313 (8) | 0.0332 (8) | 0.0473 (10) | −0.0007 (6) | 0.0135 (7) | 0.0131 (7) |
C28 | 0.0328 (8) | 0.0501 (10) | 0.0283 (8) | 0.0003 (7) | 0.0107 (7) | 0.0117 (7) |
C29 | 0.0470 (10) | 0.0585 (11) | 0.0359 (9) | −0.0013 (8) | 0.0193 (8) | −0.0079 (8) |
C30 | 0.0398 (9) | 0.0423 (9) | 0.0444 (10) | 0.0100 (7) | 0.0132 (8) | −0.0062 (8) |
C31 | 0.0278 (7) | 0.0300 (8) | 0.0356 (9) | 0.0054 (6) | 0.0066 (6) | 0.0040 (6) |
C32 | 0.0252 (7) | 0.0458 (9) | 0.0269 (8) | 0.0016 (6) | 0.0020 (6) | 0.0006 (7) |
C33 | 0.0305 (8) | 0.0565 (11) | 0.0496 (11) | −0.0103 (7) | 0.0041 (7) | −0.0130 (9) |
C34 | 0.0336 (9) | 0.0368 (9) | 0.0710 (13) | −0.0109 (7) | 0.0135 (8) | 0.0023 (8) |
Co1—C10 | 2.0142 (14) | Co2—C28 | 2.0169 (16) |
Co1—C14 | 2.0269 (14) | Co2—C31 | 2.0173 (15) |
Co1—C15 | 2.0304 (15) | Co2—C32 | 2.0199 (16) |
Co1—C11 | 2.0336 (15) | Co2—C27 | 2.0200 (15) |
Co1—C2 | 2.0693 (14) | Co2—C19 | 2.0615 (14) |
Co1—C4 | 2.0727 (14) | Co2—C21 | 2.0751 (15) |
Co1—C3 | 2.0844 (14) | Co2—C20 | 2.0770 (14) |
Co1—C5 | 2.1808 (15) | Co2—C18 | 2.1757 (14) |
Co1—C1 | 2.1820 (13) | Co2—C22 | 2.1859 (14) |
C1—C9 | 1.419 (2) | C18—C26 | 1.412 (2) |
C1—C5 | 1.424 (2) | C18—C22 | 1.426 (2) |
C1—C2 | 1.441 (2) | C18—C19 | 1.448 (2) |
C2—C3 | 1.411 (2) | C19—C20 | 1.410 (2) |
C2—H2 | 0.9500 | C19—H19 | 0.9500 |
C3—C4 | 1.417 (2) | C20—C21 | 1.417 (2) |
C3—H3 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.445 (2) | C21—C22 | 1.445 (2) |
C4—H4 | 0.9500 | C21—H21 | 0.9500 |
C5—C6 | 1.412 (2) | C22—C23 | 1.416 (2) |
C6—C7 | 1.366 (2) | C23—C24 | 1.365 (2) |
C6—H6 | 0.9500 | C23—H23 | 0.9500 |
C7—C8 | 1.413 (2) | C24—C25 | 1.408 (2) |
C7—H7 | 0.9500 | C24—H24 | 0.9500 |
C8—C9 | 1.361 (2) | C25—C26 | 1.365 (2) |
C8—H8 | 0.9500 | C25—H25 | 0.9500 |
C9—H9 | 0.9500 | C26—H26 | 0.9500 |
C10—C11 | 1.404 (2) | C27—C28 | 1.394 (2) |
C10—C17 | 1.506 (2) | C27—C34 | 1.515 (2) |
C10—H10 | 0.974 (18) | C27—H27 | 0.945 (19) |
C11—C12 | 1.518 (2) | C28—C29 | 1.502 (2) |
C11—H11 | 0.964 (17) | C28—H28 | 0.93 (2) |
C12—C13 | 1.535 (2) | C29—C30 | 1.513 (3) |
C12—H12A | 0.9900 | C29—H29A | 0.9900 |
C12—H12B | 0.9900 | C29—H29B | 0.9900 |
C13—C14 | 1.510 (2) | C30—C31 | 1.517 (2) |
C13—H13A | 0.9900 | C30—H30A | 0.9900 |
C13—H13B | 0.9900 | C30—H30B | 0.9900 |
C14—C15 | 1.400 (2) | C31—C32 | 1.387 (2) |
C14—H14 | 0.984 (17) | C31—H31 | 0.934 (18) |
C15—C16 | 1.518 (2) | C32—C33 | 1.514 (2) |
C15—H15 | 0.939 (18) | C32—H32 | 0.957 (18) |
C16—C17 | 1.529 (2) | C33—C34 | 1.521 (3) |
C16—H16A | 0.9900 | C33—H33A | 0.9900 |
C16—H16B | 0.9900 | C33—H33B | 0.9900 |
C17—H17A | 0.9900 | C34—H34A | 0.9900 |
C17—H17B | 0.9900 | C34—H34B | 0.9900 |
C10—Co1—C14 | 102.45 (6) | C28—Co2—C31 | 85.13 (7) |
C10—Co1—C15 | 84.96 (6) | C28—Co2—C32 | 101.68 (7) |
C14—Co1—C15 | 40.37 (6) | C31—Co2—C32 | 40.20 (7) |
C10—Co1—C11 | 40.58 (6) | C28—Co2—C27 | 40.40 (7) |
C14—Co1—C11 | 84.77 (6) | C31—Co2—C27 | 95.39 (7) |
C15—Co1—C11 | 94.50 (6) | C32—Co2—C27 | 84.84 (7) |
C10—Co1—C2 | 99.66 (6) | C28—Co2—C19 | 100.47 (7) |
C14—Co1—C2 | 148.83 (6) | C31—Co2—C19 | 164.95 (6) |
C15—Co1—C2 | 164.90 (6) | C32—Co2—C19 | 148.37 (7) |
C11—Co1—C2 | 98.33 (6) | C27—Co2—C19 | 97.88 (6) |
C10—Co1—C4 | 160.07 (6) | C28—Co2—C21 | 160.50 (7) |
C14—Co1—C4 | 95.81 (6) | C31—Co2—C21 | 103.44 (6) |
C15—Co1—C4 | 104.41 (6) | C32—Co2—C21 | 95.93 (6) |
C11—Co1—C4 | 151.42 (6) | C27—Co2—C21 | 151.64 (7) |
C2—Co1—C4 | 67.02 (6) | C19—Co2—C21 | 67.16 (6) |
C10—Co1—C3 | 135.52 (6) | C28—Co2—C20 | 136.49 (7) |
C14—Co1—C3 | 110.78 (6) | C31—Co2—C20 | 138.07 (7) |
C15—Co1—C3 | 139.25 (6) | C32—Co2—C20 | 110.38 (7) |
C11—Co1—C3 | 113.50 (6) | C27—Co2—C20 | 113.49 (7) |
C2—Co1—C3 | 39.71 (6) | C19—Co2—C20 | 39.83 (6) |
C4—Co1—C3 | 39.85 (6) | C21—Co2—C20 | 39.90 (6) |
C10—Co1—C5 | 122.26 (6) | C28—Co2—C18 | 94.90 (6) |
C14—Co1—C5 | 117.67 (6) | C31—Co2—C18 | 126.28 (6) |
C15—Co1—C5 | 99.41 (6) | C32—Co2—C18 | 156.24 (6) |
C11—Co1—C5 | 156.82 (6) | C27—Co2—C18 | 118.53 (6) |
C2—Co1—C5 | 65.92 (6) | C19—Co2—C18 | 39.84 (6) |
C4—Co1—C5 | 39.62 (5) | C21—Co2—C18 | 65.84 (6) |
C3—Co1—C5 | 65.95 (6) | C20—Co2—C18 | 66.02 (6) |
C10—Co1—C1 | 94.59 (6) | C28—Co2—C22 | 122.44 (7) |
C14—Co1—C1 | 155.71 (6) | C31—Co2—C22 | 99.18 (6) |
C15—Co1—C1 | 126.18 (6) | C32—Co2—C22 | 118.15 (6) |
C11—Co1—C1 | 119.14 (6) | C27—Co2—C22 | 156.30 (7) |
C2—Co1—C1 | 39.52 (6) | C19—Co2—C22 | 65.99 (6) |
C4—Co1—C1 | 65.62 (5) | C21—Co2—C22 | 39.53 (6) |
C3—Co1—C1 | 65.62 (6) | C20—Co2—C22 | 65.93 (6) |
C5—Co1—C1 | 38.10 (5) | C18—Co2—C22 | 38.16 (5) |
C9—C1—C5 | 119.64 (14) | C26—C18—C22 | 120.14 (14) |
C9—C1—C2 | 132.58 (14) | C26—C18—C19 | 132.39 (14) |
C5—C1—C2 | 107.74 (13) | C22—C18—C19 | 107.39 (13) |
C9—C1—Co1 | 126.84 (10) | C26—C18—Co2 | 125.78 (10) |
C5—C1—Co1 | 70.90 (8) | C22—C18—Co2 | 71.31 (8) |
C2—C1—Co1 | 66.02 (8) | C19—C18—Co2 | 65.83 (8) |
C3—C2—C1 | 108.41 (13) | C20—C19—C18 | 108.45 (13) |
C3—C2—Co1 | 70.72 (8) | C20—C19—Co2 | 70.68 (8) |
C1—C2—Co1 | 74.46 (8) | C18—C19—Co2 | 74.34 (8) |
C3—C2—H2 | 125.8 | C20—C19—H19 | 125.8 |
C1—C2—H2 | 125.8 | C18—C19—H19 | 125.8 |
Co1—C2—H2 | 120.7 | Co2—C19—H19 | 120.9 |
C2—C3—C4 | 107.94 (13) | C19—C20—C21 | 108.09 (13) |
C2—C3—Co1 | 69.57 (8) | C19—C20—Co2 | 69.49 (8) |
C4—C3—Co1 | 69.63 (8) | C21—C20—Co2 | 69.98 (8) |
C2—C3—H3 | 126.0 | C19—C20—H20 | 126.0 |
C4—C3—H3 | 126.0 | C21—C20—H20 | 126.0 |
Co1—C3—H3 | 126.3 | Co2—C20—H20 | 126.1 |
C3—C4—C5 | 108.50 (13) | C20—C21—C22 | 108.44 (14) |
C3—C4—Co1 | 70.52 (8) | C20—C21—Co2 | 70.12 (8) |
C5—C4—Co1 | 74.22 (8) | C22—C21—Co2 | 74.37 (8) |
C3—C4—H4 | 125.8 | C20—C21—H21 | 125.8 |
C5—C4—H4 | 125.8 | C22—C21—H21 | 125.8 |
Co1—C4—H4 | 121.2 | Co2—C21—H21 | 121.4 |
C6—C5—C1 | 119.93 (13) | C23—C22—C18 | 119.49 (14) |
C6—C5—C4 | 132.96 (14) | C23—C22—C21 | 133.15 (14) |
C1—C5—C4 | 107.04 (13) | C18—C22—C21 | 107.30 (13) |
C6—C5—Co1 | 125.72 (10) | C23—C22—Co2 | 126.47 (10) |
C1—C5—Co1 | 71.00 (8) | C18—C22—Co2 | 70.54 (8) |
C4—C5—Co1 | 66.15 (8) | C21—C22—Co2 | 66.10 (8) |
C7—C6—C5 | 118.85 (15) | C24—C23—C22 | 118.78 (15) |
C7—C6—H6 | 120.6 | C24—C23—H23 | 120.6 |
C5—C6—H6 | 120.6 | C22—C23—H23 | 120.6 |
C6—C7—C8 | 121.30 (15) | C23—C24—C25 | 121.56 (15) |
C6—C7—H7 | 119.3 | C23—C24—H24 | 119.2 |
C8—C7—H7 | 119.3 | C25—C24—H24 | 119.2 |
C9—C8—C7 | 121.32 (14) | C26—C25—C24 | 121.30 (15) |
C9—C8—H8 | 119.3 | C26—C25—H25 | 119.3 |
C7—C8—H8 | 119.3 | C24—C25—H25 | 119.3 |
C8—C9—C1 | 118.93 (14) | C25—C26—C18 | 118.71 (15) |
C8—C9—H9 | 120.5 | C25—C26—H26 | 120.6 |
C1—C9—H9 | 120.5 | C18—C26—H26 | 120.6 |
C11—C10—C17 | 125.52 (14) | C28—C27—C34 | 122.49 (15) |
C11—C10—Co1 | 70.45 (8) | C28—C27—Co2 | 69.68 (9) |
C17—C10—Co1 | 111.05 (11) | C34—C27—Co2 | 113.45 (11) |
C11—C10—H10 | 114.9 (10) | C28—C27—H27 | 115.8 (12) |
C17—C10—H10 | 115.4 (10) | C34—C27—H27 | 117.2 (12) |
Co1—C10—H10 | 108.4 (10) | Co2—C27—H27 | 106.4 (11) |
C10—C11—C12 | 122.84 (14) | C27—C28—C29 | 125.88 (16) |
C10—C11—Co1 | 68.97 (8) | C27—C28—Co2 | 69.92 (9) |
C12—C11—Co1 | 113.28 (11) | C29—C28—Co2 | 110.72 (11) |
C10—C11—H11 | 117.5 (10) | C27—C28—H28 | 117.8 (12) |
C12—C11—H11 | 116.0 (10) | C29—C28—H28 | 112.9 (12) |
Co1—C11—H11 | 106.2 (10) | Co2—C28—H28 | 108.5 (12) |
C11—C12—C13 | 111.27 (13) | C28—C29—C30 | 112.79 (14) |
C11—C12—H12A | 109.4 | C28—C29—H29A | 109.0 |
C13—C12—H12A | 109.4 | C30—C29—H29A | 109.0 |
C11—C12—H12B | 109.4 | C28—C29—H29B | 109.0 |
C13—C12—H12B | 109.4 | C30—C29—H29B | 109.0 |
H12A—C12—H12B | 108.0 | H29A—C29—H29B | 107.8 |
C14—C13—C12 | 112.24 (13) | C29—C30—C31 | 111.63 (13) |
C14—C13—H13A | 109.2 | C29—C30—H30A | 109.3 |
C12—C13—H13A | 109.2 | C31—C30—H30A | 109.3 |
C14—C13—H13B | 109.2 | C29—C30—H30B | 109.3 |
C12—C13—H13B | 109.2 | C31—C30—H30B | 109.3 |
H13A—C13—H13B | 107.9 | H30A—C30—H30B | 108.0 |
C15—C14—C13 | 124.23 (14) | C32—C31—C30 | 122.65 (15) |
C15—C14—Co1 | 69.95 (8) | C32—C31—Co2 | 70.00 (9) |
C13—C14—Co1 | 111.40 (10) | C30—C31—Co2 | 112.77 (11) |
C15—C14—H14 | 116.6 (10) | C32—C31—H31 | 117.5 (11) |
C13—C14—H14 | 114.7 (10) | C30—C31—H31 | 116.2 (11) |
Co1—C14—H14 | 109.3 (10) | Co2—C31—H31 | 105.4 (11) |
C14—C15—C16 | 123.58 (15) | C31—C32—C33 | 123.91 (15) |
C14—C15—Co1 | 69.68 (8) | C31—C32—Co2 | 69.80 (9) |
C16—C15—Co1 | 112.73 (10) | C33—C32—Co2 | 112.20 (12) |
C14—C15—H15 | 118.6 (10) | C31—C32—H32 | 115.9 (10) |
C16—C15—H15 | 113.5 (10) | C33—C32—H32 | 115.7 (11) |
Co1—C15—H15 | 108.4 (11) | Co2—C32—H32 | 108.1 (11) |
C15—C16—C17 | 111.29 (13) | C32—C33—C34 | 112.29 (14) |
C15—C16—H16A | 109.4 | C32—C33—H33A | 109.1 |
C17—C16—H16A | 109.4 | C34—C33—H33A | 109.1 |
C15—C16—H16B | 109.4 | C32—C33—H33B | 109.1 |
C17—C16—H16B | 109.4 | C34—C33—H33B | 109.1 |
H16A—C16—H16B | 108.0 | H33A—C33—H33B | 107.9 |
C10—C17—C16 | 111.94 (13) | C27—C34—C33 | 112.45 (13) |
C10—C17—H17A | 109.2 | C27—C34—H34A | 109.1 |
C16—C17—H17A | 109.2 | C33—C34—H34A | 109.1 |
C10—C17—H17B | 109.2 | C27—C34—H34B | 109.1 |
C16—C17—H17B | 109.2 | C33—C34—H34B | 109.1 |
H17A—C17—H17B | 107.9 | H34A—C34—H34B | 107.8 |
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 |
Absorption correction | – |
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), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).