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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

([2.2.2]Cryptand-κ6O)potassium (η4-cyclo­octa­diene)bis­­(η2-pyrene)cobaltate(1−) pentane hemisolvate

aDepartment of Chemistry, 207 Pleasant Street SE, University of Minnesota, Minneapolis, MN 55455, USA
*Correspondence e-mail: brennessel@chem.rochester.edu

(Received 14 June 2012; accepted 26 June 2012; online 30 June 2012)

The cation, anion, and solvent in the title compound, [K(C18H36N2O6)][Co(C8H12)(C16H10)2]·0.5C5H12, are well separated. The pentane solvent mol­ecules are found in channels along [100] and were modeled as disordered over crystallographic inversion centers. Using the mid-points of the coordinated olefins, the angle between the Cpy/Cpy–Co–Cpy/Cpy and the Ccod/Ccod–Co–Ccod/Ccod planes (py is pyrene and cod is cyclo­octa­diene) is 67.6 (2)°. Thus, the overall geometry of the coordination sphere around cobalt is best described as distorted tetra­hedral.

Related literature

For the synthesis of the precursor mol­ecule, see: Brennessel et al. (2006[Brennessel, W. W., Young, V. G. Jr & Ellis, J. E. (2006). Angew. Chem. Int. Ed. 45, 7268-7271.]). For cobalt anions with non-conjugated olefin ligands, see: Jonas (1981[Jonas, K. (1981). Adv. Organomet. Chem. 19, 97-122.], 1984[Jonas, K. (1984). Pure Appl. Chem. 56, 63-80.], 1985[Jonas, K. (1985). Angew. Chem. Int. Ed. Engl. 24, 295-311.]); Jonas et al. (1976[Jonas, K., Mynott, R., Krüger, C., Sekutowski, J. C. & Tsay, Y.-H. (1976). Angew. Chem. Int. Ed. 15, 767-768.]); Jonas & Krüger (1980[Jonas, K. & Krüger, C. (1980). Angew. Chem. Int. Ed. Engl. 19, 520-537.]). For the structure of free pyrene, see: Frampton et al. (2000[Frampton, C. S., Knight, K. S., Shankland, N. & Shankland, K. (2000). J. Mol. Struct. 520, 29-32.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [K(C18H36N2O6)][Co(C8H12)(C16H10)2]·0.5C5H12

  • Mr = 1023.25

  • Triclinic, [P \overline 1]

  • a = 12.1007 (9) Å

  • b = 12.9869 (10) Å

  • c = 18.7501 (14) Å

  • α = 72.064 (1)°

  • β = 81.595 (1)°

  • γ = 68.558 (1)°

  • V = 2607.5 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.46 mm−1

  • T = 173 K

  • 0.40 × 0.24 × 0.08 mm

Data collection
  • Bruker SMART CCD Platform diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.837, Tmax = 0.964

  • 29850 measured reflections

  • 11375 independent reflections

  • 7919 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.108

  • S = 1.01

  • 11375 reflections

  • 678 parameters

  • 5 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.74 e Å−3

  • Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Klaus Jonas had shown that cobalt anions could be ligated solely by olefinic moieties, whether by ethylene itself or by isolobal analogs like 1,5-cyclooctadiene (Jonas et al., 1976; Jonas & Krüger, 1980; Jonas, 1981, 1984, 1985). This led to the possibility that η2-coordinated pyrene ligands could offer a similar stabilization of the metal center. Pyrene is an interesting molecule in that when coordinated η2 through two side carbon atoms (C4/C5 and C20/C21 in figure), it can be behave as a coordinated ethylene ligand with an exo-phenanthrene unit. Thus pyrene could offer the ethylene-type ligation, with the possible bonuses of resonance stabilization energy in the exo-phenanthrene portion and additional electron withdrawing capabilities.

The structure is unique. Of the ten reported transition metal structures to date containing a pyrene or substituted (not by additional fused rings) pyrene ligand (Allen, 2002), only the title compound is mononuclear and has a pyrene-to-transition metal ratio of greater than one. The coordinated ethylene moieties of the pyrene ligands have C–C bond distances of 1.420 (3) and 1.425 (3) Å, which are much longer than the respective distances in free pyrene (average 1.341 Å) (Frampton et al., 2000), and provide evidence of significant back-bonding.

Related literature top

For the synthesis of the precursor molecule, see: Brennessel et al. (2006). For cobalt anions with non-conjugated olefin ligands, see: Jonas (1981, 1984, 1985); Jonas et al. (1976); Jonas & Krüger (1980). For the structure of free pyrene, see: Frampton et al. (2000). For a descripotion of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Room temperature tetrahydrofuran (THF) was added to a flask containing excess cryptand[2.2.2], excess pyrene, and bright magenta and highly air-sensitive [K(THF)x][Co(η4-1,5-cyclooctadiene)(η4-C10H8)] (Brennessel et al., 2006). The reaction mixture was swirled briefly, layered with pentane, and stored at 0 °C for two days. During that time, purple-black plates formed that were suitable for single-crystal X-ray diffraction.

Refinement top

Hydrogen atoms on metal-coordinated carbon atoms were found from the difference Fourier map, and their positional and isotropic displacement parameters were refined independently from those of their respective bonded carbon atoms. All other hydrogen atoms were placed geometrically, and refined relative to their respective bonded carbon atoms: Uiso[H]= 1.5*Ueq[C] for methyl and Uiso[H] = 1.2*Ueq[C] for methylene and aromatic hydrogen atoms.

The cocrystallized pentane solvent molecule is modeled as disordered over a crystallographic inversion center (50:50). Corresponding bond lengths and angles in both directions along the pentane molecule were restrained to be similar. Anisotropic displacement parameters for spatially close symmetry-related atoms were constrained to be equivalent. Bond lengths C59–C60 and C60–C61 were restrained toward ideal distances (1.52 Å).

Structure description top

Klaus Jonas had shown that cobalt anions could be ligated solely by olefinic moieties, whether by ethylene itself or by isolobal analogs like 1,5-cyclooctadiene (Jonas et al., 1976; Jonas & Krüger, 1980; Jonas, 1981, 1984, 1985). This led to the possibility that η2-coordinated pyrene ligands could offer a similar stabilization of the metal center. Pyrene is an interesting molecule in that when coordinated η2 through two side carbon atoms (C4/C5 and C20/C21 in figure), it can be behave as a coordinated ethylene ligand with an exo-phenanthrene unit. Thus pyrene could offer the ethylene-type ligation, with the possible bonuses of resonance stabilization energy in the exo-phenanthrene portion and additional electron withdrawing capabilities.

The structure is unique. Of the ten reported transition metal structures to date containing a pyrene or substituted (not by additional fused rings) pyrene ligand (Allen, 2002), only the title compound is mononuclear and has a pyrene-to-transition metal ratio of greater than one. The coordinated ethylene moieties of the pyrene ligands have C–C bond distances of 1.420 (3) and 1.425 (3) Å, which are much longer than the respective distances in free pyrene (average 1.341 Å) (Frampton et al., 2000), and provide evidence of significant back-bonding.

For the synthesis of the precursor molecule, see: Brennessel et al. (2006). For cobalt anions with non-conjugated olefin ligands, see: Jonas (1981, 1984, 1985); Jonas et al. (1976); Jonas & Krüger (1980). For the structure of free pyrene, see: Frampton et al. (2000). For a descripotion of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the anion showing displacement ellipsoids at the 50% probability level.
([2.2.2]Cryptand-κ6O)potassium (η4-cyclooctadiene)bis(η2-pyrene)cobaltate(1-) pentane hemisolvate top
Crystal data top
[K(C18H36N2O6)][Co(C8H12)(C16H10)2]·0.5C5H12Z = 2
Mr = 1023.25F(000) = 1090
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.1007 (9) ÅCell parameters from 3044 reflections
b = 12.9869 (10) Åθ = 2.5–26.3°
c = 18.7501 (14) ŵ = 0.46 mm1
α = 72.064 (1)°T = 173 K
β = 81.595 (1)°Plate, purple-black
γ = 68.558 (1)°0.40 × 0.24 × 0.08 mm
V = 2607.5 (3) Å3
Data collection top
Bruker SMART CCD Platform
diffractometer
11375 independent reflections
Radiation source: normal-focus sealed tube7919 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
area detector, ω scans per φθmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 1515
Tmin = 0.837, Tmax = 0.964k = 1616
29850 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0421P)2 + 1.344P]
where P = (Fo2 + 2Fc2)/3
11375 reflections(Δ/σ)max = 0.001
678 parametersΔρmax = 0.74 e Å3
5 restraintsΔρmin = 0.48 e Å3
Crystal data top
[K(C18H36N2O6)][Co(C8H12)(C16H10)2]·0.5C5H12γ = 68.558 (1)°
Mr = 1023.25V = 2607.5 (3) Å3
Triclinic, P1Z = 2
a = 12.1007 (9) ÅMo Kα radiation
b = 12.9869 (10) ŵ = 0.46 mm1
c = 18.7501 (14) ÅT = 173 K
α = 72.064 (1)°0.40 × 0.24 × 0.08 mm
β = 81.595 (1)°
Data collection top
Bruker SMART CCD Platform
diffractometer
11375 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
7919 reflections with I > 2σ(I)
Tmin = 0.837, Tmax = 0.964Rint = 0.037
29850 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0425 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.74 e Å3
11375 reflectionsΔρmin = 0.48 e Å3
678 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
xyzUiso*/UeqOcc. (<1)
Co10.33875 (3)0.99538 (2)0.695903 (16)0.02569 (9)
C10.6218 (2)0.5743 (2)0.63059 (16)0.0444 (6)
H10.64400.50210.62020.053*
C20.6095 (2)0.6726 (2)0.57259 (15)0.0451 (6)
H20.62380.66790.52230.054*
C30.5761 (2)0.7792 (2)0.58711 (14)0.0386 (6)
H30.57070.84590.54640.046*
C40.51596 (19)0.90131 (18)0.67510 (13)0.0273 (5)
H40.544 (2)0.958 (2)0.6390 (13)0.032 (6)*
C50.49812 (19)0.90716 (18)0.75050 (12)0.0264 (5)
H50.5152 (18)0.9648 (19)0.7633 (12)0.026 (6)*
C60.5048 (2)0.8047 (2)0.88655 (13)0.0362 (5)
H60.48120.87650.89770.043*
C70.5272 (2)0.7032 (2)0.94513 (14)0.0411 (6)
H70.51920.70660.99560.049*
C80.5606 (2)0.5986 (2)0.93018 (14)0.0399 (6)
H80.57570.53020.97050.048*
C90.6059 (2)0.48408 (19)0.83857 (16)0.0409 (6)
H9A0.61900.41500.87820.049*
C100.6191 (2)0.4786 (2)0.76748 (16)0.0413 (6)
H10A0.64060.40570.75810.050*
C110.6017 (2)0.57987 (19)0.70492 (15)0.0354 (5)
C120.55070 (19)0.79043 (19)0.65970 (13)0.0296 (5)
C130.51646 (18)0.80227 (18)0.81235 (12)0.0268 (5)
C140.57259 (19)0.59134 (19)0.85637 (14)0.0336 (5)
C150.56647 (18)0.68839 (18)0.72026 (13)0.0289 (5)
C160.55072 (18)0.69424 (18)0.79645 (13)0.0281 (5)
C170.3968 (3)1.1287 (2)0.94023 (15)0.0476 (7)
H170.41961.12250.98820.057*
C180.2855 (3)1.1296 (2)0.93170 (15)0.0484 (7)
H180.23131.12570.97370.058*
C190.2512 (2)1.1360 (2)0.86258 (14)0.0395 (6)
H190.17371.13670.85820.047*
C200.2928 (2)1.14793 (18)0.72689 (13)0.0289 (5)
H200.209 (2)1.1841 (18)0.7192 (12)0.027 (6)*
C210.3748 (2)1.15244 (18)0.66417 (13)0.0281 (5)
H210.3493 (19)1.1879 (19)0.6153 (13)0.028 (6)*
C220.5656 (2)1.17953 (19)0.60968 (14)0.0368 (6)
H220.54521.18230.56190.044*
C230.6723 (2)1.1930 (2)0.61679 (16)0.0469 (7)
H230.72271.20650.57370.056*
C240.7055 (2)1.1870 (2)0.68517 (17)0.0467 (7)
H240.77891.19560.68920.056*
C250.6641 (2)1.1577 (2)0.82256 (17)0.0458 (7)
H250.73881.16210.82820.055*
C260.5916 (2)1.1419 (2)0.88334 (16)0.0467 (7)
H260.61711.13380.93100.056*
C270.4768 (2)1.1370 (2)0.87815 (14)0.0385 (6)
C280.3279 (2)1.14161 (18)0.79916 (13)0.0297 (5)
C290.4885 (2)1.16202 (17)0.67139 (13)0.0294 (5)
C300.6317 (2)1.16822 (19)0.74938 (15)0.0378 (6)
C310.4425 (2)1.14376 (18)0.80709 (13)0.0307 (5)
C320.5217 (2)1.15711 (17)0.74237 (13)0.0303 (5)
C330.2752 (2)0.85817 (19)0.74074 (13)0.0321 (5)
H330.3383 (19)0.7945 (19)0.7704 (12)0.025 (6)*
C340.2124 (2)0.9475 (2)0.77208 (14)0.0320 (5)
H340.232 (2)0.9431 (19)0.8179 (13)0.032 (6)*
C350.0879 (2)1.0284 (2)0.74944 (14)0.0383 (6)
H35A0.06601.09390.77130.046*
H35B0.03090.98700.77000.046*
C360.0790 (2)1.0741 (2)0.66415 (14)0.0381 (6)
H36A0.05341.02300.64560.046*
H36B0.01751.15160.65150.046*
C370.1960 (2)1.0814 (2)0.62439 (13)0.0321 (5)
H370.1962 (19)1.158 (2)0.6021 (12)0.031 (6)*
C380.2813 (2)0.9961 (2)0.59624 (13)0.0333 (5)
H380.332 (2)1.019 (2)0.5558 (14)0.037 (7)*
C390.2674 (2)0.8827 (2)0.60230 (14)0.0390 (6)
H39A0.34380.82980.58770.047*
H39B0.20730.89560.56690.047*
C400.2291 (2)0.8262 (2)0.68208 (14)0.0380 (6)
H40A0.14130.85130.68670.046*
H40B0.26000.74150.69140.046*
K10.04995 (4)0.61799 (4)0.72291 (3)0.03135 (12)
N10.0702 (2)0.6880 (2)0.86364 (12)0.0449 (5)
N20.1725 (2)0.54589 (18)0.58168 (12)0.0440 (5)
O10.11276 (14)0.84204 (14)0.70849 (10)0.0443 (4)
O20.01292 (16)0.76423 (14)0.58045 (10)0.0450 (4)
O30.10080 (14)0.50457 (14)0.81502 (9)0.0385 (4)
O40.03226 (14)0.42536 (14)0.69175 (9)0.0396 (4)
O50.18022 (16)0.56685 (16)0.84697 (10)0.0502 (5)
O60.29744 (15)0.51687 (14)0.71414 (11)0.0453 (4)
C410.1290 (3)0.8133 (3)0.84052 (19)0.0658 (10)
H41A0.06840.85050.83320.079*
H41B0.18500.83660.88140.079*
C420.1957 (3)0.8566 (2)0.7698 (2)0.0637 (9)
H42A0.24970.81310.77370.076*
H42B0.24420.93900.76180.076*
C430.1721 (2)0.8815 (2)0.63935 (19)0.0577 (8)
H43A0.22950.96050.63360.069*
H43B0.21650.83070.63950.069*
C440.0833 (3)0.8804 (2)0.57631 (16)0.0519 (7)
H44A0.12370.91760.52800.062*
H44B0.03240.92360.57950.062*
C450.0782 (3)0.7543 (2)0.52382 (15)0.0531 (7)
H45A0.14580.76860.53790.064*
H45B0.04820.81170.47590.064*
C460.1173 (3)0.6363 (3)0.51506 (15)0.0565 (8)
H46A0.04770.62230.50350.068*
H46B0.17490.63130.47190.068*
C470.1578 (2)0.6298 (2)0.89382 (15)0.0468 (7)
H47A0.23060.67200.86460.056*
H47B0.17940.63190.94650.056*
C480.1122 (2)0.5073 (2)0.89102 (14)0.0442 (6)
H48A0.03400.46670.91440.053*
H48B0.16780.46770.91930.053*
C490.0697 (2)0.3906 (2)0.80932 (16)0.0465 (7)
H49A0.12870.35570.83800.056*
H49B0.00920.34290.83060.056*
C500.0666 (2)0.3946 (2)0.72899 (16)0.0471 (7)
H50A0.05950.31830.72470.056*
H50B0.14090.45180.70560.056*
C510.0398 (2)0.4303 (2)0.61475 (15)0.0447 (6)
H51A0.02470.49830.58790.054*
H51B0.03120.36040.60890.054*
C520.1589 (2)0.4384 (2)0.58261 (16)0.0469 (7)
H52A0.22220.37310.61260.056*
H52B0.16930.43150.53070.056*
C530.0180 (3)0.6550 (3)0.91963 (16)0.0654 (9)
H53A0.02430.57770.95320.078*
H53B0.00960.70990.95060.078*
C540.1393 (3)0.6531 (3)0.88536 (16)0.0584 (8)
H54A0.13440.72900.85000.070*
H54B0.19460.63550.92500.070*
C550.3064 (2)0.5230 (2)0.83743 (17)0.0543 (8)
H55A0.34270.47850.88660.065*
H55B0.33750.58730.81540.065*
C560.3365 (2)0.4479 (2)0.78696 (18)0.0548 (8)
H56A0.42340.40750.78500.066*
H56B0.29720.38930.80600.066*
C570.3517 (2)0.4597 (3)0.6580 (2)0.0624 (9)
H57A0.34030.38420.67150.075*
H57B0.43810.44610.65400.075*
C580.2974 (3)0.5320 (3)0.58454 (19)0.0611 (9)
H58A0.30430.60910.57370.073*
H58B0.34330.49690.54460.073*
C590.183 (3)0.834 (3)1.007 (5)0.148 (9)0.50
H59A0.21370.76810.98580.222*0.50
H59B0.18490.80641.06180.222*0.50
H59C0.23250.88270.98820.222*0.50
C600.0578 (10)0.9024 (10)0.9840 (7)0.129 (3)0.50
H60A0.00810.85291.00230.155*0.50
H60B0.05570.92940.92860.155*0.50
C610.008 (3)1.004 (2)1.016 (2)0.153 (7)0.50
H61A0.06681.04281.01190.183*0.50
H61B0.02090.98301.06840.183*0.50
C620.0921 (9)1.0770 (10)0.9632 (7)0.129 (3)0.50
H62A0.14401.03300.96350.155*0.50
H62B0.06041.10080.91140.155*0.50
C630.162 (3)1.182 (3)0.991 (5)0.148 (9)0.50
H63A0.22561.23310.95670.222*0.50
H63B0.10831.22240.99250.222*0.50
H62C0.19551.15721.04130.222*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02717 (16)0.02066 (15)0.02826 (17)0.00811 (12)0.00491 (12)0.00371 (12)
C10.0376 (14)0.0356 (14)0.0643 (18)0.0045 (11)0.0036 (13)0.0286 (14)
C20.0409 (15)0.0491 (16)0.0461 (16)0.0058 (12)0.0005 (12)0.0263 (13)
C30.0384 (14)0.0371 (14)0.0368 (14)0.0086 (11)0.0005 (11)0.0115 (11)
C40.0273 (11)0.0222 (11)0.0303 (12)0.0082 (9)0.0020 (9)0.0042 (9)
C50.0268 (11)0.0190 (10)0.0338 (12)0.0076 (9)0.0040 (9)0.0066 (9)
C60.0386 (13)0.0345 (13)0.0342 (13)0.0121 (11)0.0044 (11)0.0068 (10)
C70.0415 (15)0.0479 (16)0.0292 (13)0.0159 (12)0.0030 (11)0.0022 (11)
C80.0327 (13)0.0375 (14)0.0386 (14)0.0140 (11)0.0045 (11)0.0085 (11)
C90.0308 (13)0.0206 (12)0.0623 (18)0.0095 (10)0.0080 (12)0.0049 (11)
C100.0308 (13)0.0227 (12)0.0690 (19)0.0075 (10)0.0039 (12)0.0116 (12)
C110.0269 (12)0.0265 (12)0.0542 (16)0.0062 (10)0.0062 (11)0.0144 (11)
C120.0246 (11)0.0290 (12)0.0348 (13)0.0073 (9)0.0033 (9)0.0097 (10)
C130.0229 (11)0.0252 (11)0.0314 (12)0.0080 (9)0.0050 (9)0.0051 (9)
C140.0226 (11)0.0266 (12)0.0467 (15)0.0100 (9)0.0053 (10)0.0005 (10)
C150.0216 (11)0.0247 (11)0.0396 (13)0.0067 (9)0.0039 (9)0.0078 (10)
C160.0228 (11)0.0231 (11)0.0361 (13)0.0083 (9)0.0041 (9)0.0031 (9)
C170.0661 (19)0.0477 (16)0.0332 (14)0.0197 (14)0.0066 (13)0.0145 (12)
C180.0608 (18)0.0502 (16)0.0365 (15)0.0205 (14)0.0084 (13)0.0178 (13)
C190.0411 (14)0.0371 (14)0.0423 (15)0.0147 (11)0.0022 (11)0.0138 (11)
C200.0268 (12)0.0210 (11)0.0372 (13)0.0064 (9)0.0051 (10)0.0060 (9)
C210.0332 (12)0.0199 (11)0.0281 (12)0.0075 (9)0.0054 (10)0.0023 (9)
C220.0399 (14)0.0279 (12)0.0399 (14)0.0131 (11)0.0016 (11)0.0049 (10)
C230.0414 (15)0.0397 (15)0.0590 (18)0.0194 (12)0.0114 (13)0.0121 (13)
C240.0343 (14)0.0372 (14)0.073 (2)0.0174 (12)0.0005 (13)0.0154 (14)
C250.0391 (15)0.0333 (14)0.071 (2)0.0107 (11)0.0178 (14)0.0181 (13)
C260.0534 (17)0.0378 (14)0.0536 (17)0.0114 (13)0.0190 (14)0.0166 (13)
C270.0484 (15)0.0274 (12)0.0407 (14)0.0091 (11)0.0129 (12)0.0101 (11)
C280.0344 (12)0.0189 (10)0.0348 (13)0.0072 (9)0.0027 (10)0.0076 (9)
C290.0334 (12)0.0170 (10)0.0360 (13)0.0084 (9)0.0003 (10)0.0059 (9)
C300.0339 (13)0.0231 (12)0.0575 (17)0.0095 (10)0.0056 (12)0.0114 (11)
C310.0364 (13)0.0185 (11)0.0371 (13)0.0068 (9)0.0061 (10)0.0083 (9)
C320.0308 (12)0.0173 (10)0.0412 (13)0.0053 (9)0.0045 (10)0.0079 (9)
C330.0300 (12)0.0242 (12)0.0399 (14)0.0119 (10)0.0074 (10)0.0004 (10)
C340.0320 (13)0.0334 (13)0.0290 (13)0.0143 (10)0.0042 (10)0.0011 (10)
C350.0313 (13)0.0361 (13)0.0478 (15)0.0151 (11)0.0011 (11)0.0077 (11)
C360.0317 (13)0.0285 (12)0.0520 (16)0.0072 (10)0.0138 (11)0.0062 (11)
C370.0359 (13)0.0260 (12)0.0340 (13)0.0109 (10)0.0125 (10)0.0021 (10)
C380.0372 (13)0.0340 (13)0.0293 (13)0.0135 (11)0.0089 (11)0.0045 (10)
C390.0398 (14)0.0360 (13)0.0462 (15)0.0121 (11)0.0121 (11)0.0143 (11)
C400.0374 (13)0.0269 (12)0.0527 (16)0.0125 (10)0.0123 (12)0.0083 (11)
K10.0304 (3)0.0288 (3)0.0311 (3)0.0072 (2)0.0031 (2)0.0058 (2)
N10.0541 (14)0.0572 (14)0.0372 (12)0.0345 (12)0.0118 (10)0.0195 (11)
N20.0510 (13)0.0439 (13)0.0420 (13)0.0194 (11)0.0043 (10)0.0173 (10)
O10.0291 (9)0.0360 (10)0.0614 (12)0.0055 (7)0.0031 (8)0.0134 (9)
O20.0578 (12)0.0309 (9)0.0412 (10)0.0145 (8)0.0106 (9)0.0003 (8)
O30.0415 (10)0.0334 (9)0.0395 (10)0.0143 (8)0.0011 (8)0.0067 (7)
O40.0353 (9)0.0410 (10)0.0454 (10)0.0125 (8)0.0021 (8)0.0163 (8)
O50.0497 (11)0.0594 (12)0.0503 (11)0.0278 (10)0.0146 (9)0.0104 (9)
O60.0370 (10)0.0307 (9)0.0663 (12)0.0025 (8)0.0094 (9)0.0183 (9)
C410.081 (2)0.062 (2)0.074 (2)0.0425 (18)0.0431 (19)0.0442 (18)
C420.0476 (17)0.0327 (15)0.095 (3)0.0077 (13)0.0281 (17)0.0180 (16)
C430.0347 (15)0.0352 (15)0.094 (2)0.0024 (12)0.0268 (16)0.0109 (15)
C440.0595 (18)0.0335 (14)0.0543 (18)0.0102 (13)0.0280 (15)0.0046 (12)
C450.082 (2)0.0545 (17)0.0290 (14)0.0363 (16)0.0028 (14)0.0040 (12)
C460.088 (2)0.0606 (19)0.0351 (15)0.0396 (17)0.0019 (15)0.0178 (14)
C470.0507 (16)0.0560 (17)0.0419 (15)0.0296 (14)0.0136 (12)0.0181 (13)
C480.0436 (15)0.0506 (16)0.0384 (15)0.0226 (13)0.0011 (12)0.0054 (12)
C490.0453 (16)0.0315 (13)0.0586 (18)0.0144 (12)0.0001 (13)0.0062 (12)
C500.0397 (15)0.0414 (15)0.0662 (19)0.0168 (12)0.0005 (13)0.0208 (14)
C510.0484 (16)0.0406 (15)0.0500 (16)0.0123 (12)0.0100 (13)0.0189 (12)
C520.0529 (17)0.0426 (15)0.0490 (16)0.0129 (13)0.0004 (13)0.0231 (13)
C530.084 (2)0.107 (3)0.0357 (16)0.067 (2)0.0149 (15)0.0278 (17)
C540.073 (2)0.087 (2)0.0383 (16)0.0528 (19)0.0003 (14)0.0197 (16)
C550.0478 (17)0.0512 (17)0.0626 (19)0.0215 (14)0.0312 (14)0.0047 (14)
C560.0389 (15)0.0308 (14)0.089 (2)0.0071 (12)0.0277 (15)0.0038 (15)
C570.0299 (14)0.064 (2)0.109 (3)0.0060 (13)0.0011 (16)0.059 (2)
C580.0556 (19)0.076 (2)0.073 (2)0.0348 (17)0.0239 (17)0.0469 (19)
C590.184 (12)0.192 (10)0.113 (7)0.120 (11)0.002 (13)0.038 (10)
C600.092 (5)0.113 (6)0.187 (9)0.004 (4)0.045 (5)0.066 (6)
C610.074 (10)0.096 (7)0.26 (3)0.044 (7)0.044 (12)0.011 (11)
C620.092 (5)0.113 (6)0.187 (9)0.004 (4)0.045 (5)0.066 (6)
C630.184 (12)0.192 (10)0.113 (7)0.120 (11)0.002 (13)0.038 (10)
Geometric parameters (Å, º) top
Co1—C342.067 (2)K1—O22.7810 (17)
Co1—C52.078 (2)K1—O62.7989 (18)
Co1—C382.083 (2)K1—O12.8106 (17)
Co1—C332.089 (2)K1—O32.8208 (17)
Co1—C372.091 (2)K1—O42.8237 (17)
Co1—C42.092 (2)K1—N13.048 (2)
Co1—C202.093 (2)K1—N23.074 (2)
Co1—C212.129 (2)N1—C531.463 (4)
C1—C21.374 (4)N1—C411.467 (4)
C1—C111.399 (4)N1—C471.471 (3)
C1—H10.9500N2—C521.459 (3)
C2—C31.395 (3)N2—C581.463 (4)
C2—H20.9500N2—C461.467 (4)
C3—C121.391 (3)O1—C421.422 (3)
C3—H30.9500O1—C431.433 (3)
C4—C51.420 (3)O2—C451.413 (3)
C4—C121.453 (3)O2—C441.420 (3)
C4—H40.96 (2)O3—C491.421 (3)
C5—C131.460 (3)O3—C481.422 (3)
C5—H50.95 (2)O4—C511.416 (3)
C6—C131.387 (3)O4—C501.418 (3)
C6—C71.397 (3)O5—C541.416 (3)
C6—H60.9500O5—C551.427 (3)
C7—C81.374 (4)O6—C571.420 (3)
C7—H70.9500O6—C561.420 (3)
C8—C141.399 (3)C41—C421.500 (5)
C8—H80.9500C41—H41A0.9900
C9—C101.340 (4)C41—H41B0.9900
C9—C141.432 (3)C42—H42A0.9900
C9—H9A0.9500C42—H42B0.9900
C10—C111.439 (3)C43—C441.477 (4)
C10—H10A0.9500C43—H43A0.9900
C11—C151.423 (3)C43—H43B0.9900
C12—C151.426 (3)C44—H44A0.9900
C13—C161.423 (3)C44—H44B0.9900
C14—C161.422 (3)C45—C461.483 (4)
C15—C161.435 (3)C45—H45A0.9900
C17—C181.375 (4)C45—H45B0.9900
C17—C271.405 (4)C46—H46A0.9900
C17—H170.9500C46—H46B0.9900
C18—C191.387 (4)C47—C481.496 (4)
C18—H180.9500C47—H47A0.9900
C19—C281.398 (3)C47—H47B0.9900
C19—H190.9500C48—H48A0.9900
C20—C211.425 (3)C48—H48B0.9900
C20—C281.448 (3)C49—C501.487 (4)
C20—H200.97 (2)C49—H49A0.9900
C21—C291.455 (3)C49—H49B0.9900
C21—H210.93 (2)C50—H50A0.9900
C22—C291.392 (3)C50—H50B0.9900
C22—C231.395 (3)C51—C521.506 (4)
C22—H220.9500C51—H51A0.9900
C23—C241.370 (4)C51—H51B0.9900
C23—H230.9500C52—H52A0.9900
C24—C301.404 (4)C52—H52B0.9900
C24—H240.9500C53—C541.509 (4)
C25—C261.344 (4)C53—H53A0.9900
C25—C301.435 (4)C53—H53B0.9900
C25—H250.9500C54—H54A0.9900
C26—C271.432 (4)C54—H54B0.9900
C26—H260.9500C55—C561.480 (4)
C27—C311.421 (3)C55—H55A0.9900
C28—C311.427 (3)C55—H55B0.9900
C29—C321.422 (3)C56—H56A0.9900
C30—C321.418 (3)C56—H56B0.9900
C31—C321.440 (3)C57—C581.492 (5)
C33—C341.383 (3)C57—H57A0.9900
C33—C401.524 (3)C57—H57B0.9900
C33—H330.98 (2)C58—H58A0.9900
C34—C351.519 (3)C58—H58B0.9900
C34—H340.90 (2)C59—C601.50 (3)
C35—C361.530 (3)C59—H59A0.9800
C35—H35A0.9900C59—H59B0.9800
C35—H35B0.9900C59—H59C0.9800
C36—C371.522 (3)C60—C611.504 (9)
C36—H36A0.9900C60—H60A0.9900
C36—H36B0.9900C60—H60B0.9900
C37—C381.391 (3)C61—C621.507 (9)
C37—H370.95 (2)C61—H61A0.9900
C38—C391.511 (3)C61—H61B0.9900
C38—H380.94 (2)C62—C631.51 (3)
C39—C401.536 (3)C62—H62A0.9900
C39—H39A0.9900C62—H62B0.9900
C39—H39B0.9900C63—H63A0.9800
C40—H40A0.9900C63—H63B0.9800
C40—H40B0.9900C63—H62C0.9800
K1—O52.7735 (18)
C34—Co1—C5104.80 (9)O5—K1—O389.39 (5)
C34—Co1—C38101.05 (10)O2—K1—O3121.84 (5)
C5—Co1—C38132.69 (9)O6—K1—O3123.64 (5)
C34—Co1—C3338.88 (9)O1—K1—O395.76 (5)
C5—Co1—C3393.32 (9)O5—K1—O4114.96 (5)
C38—Co1—C3382.73 (9)O2—K1—O494.50 (5)
C34—Co1—C3783.55 (10)O6—K1—O488.43 (5)
C5—Co1—C37170.29 (9)O1—K1—O4131.57 (5)
C38—Co1—C3738.94 (9)O3—K1—O460.80 (5)
C33—Co1—C3790.20 (9)O5—K1—N159.07 (6)
C34—Co1—C4130.49 (9)O2—K1—N1121.33 (6)
C5—Co1—C439.81 (8)O6—K1—N1119.57 (6)
C38—Co1—C493.94 (9)O1—K1—N160.79 (6)
C33—Co1—C498.53 (9)O3—K1—N160.29 (5)
C37—Co1—C4130.65 (9)O4—K1—N1120.75 (5)
C34—Co1—C2090.25 (9)O5—K1—N2120.56 (6)
C5—Co1—C2098.15 (9)O2—K1—N259.08 (6)
C38—Co1—C20120.80 (9)O6—K1—N260.08 (6)
C33—Co1—C20128.96 (9)O1—K1—N2119.61 (6)
C37—Co1—C2086.60 (9)O3—K1—N2119.65 (5)
C4—Co1—C20121.38 (9)O4—K1—N259.13 (5)
C34—Co1—C21129.33 (9)N1—K1—N2179.58 (7)
C5—Co1—C2191.27 (9)C53—N1—C41110.7 (2)
C38—Co1—C21102.03 (9)C53—N1—C47110.0 (2)
C33—Co1—C21168.19 (9)C41—N1—C47110.7 (2)
C37—Co1—C2187.03 (9)C53—N1—K1110.29 (17)
C4—Co1—C2191.96 (9)C41—N1—K1106.74 (16)
C20—Co1—C2139.43 (9)C47—N1—K1108.34 (14)
C2—C1—C11120.4 (2)C52—N2—C58111.4 (2)
C2—C1—H1119.8C52—N2—C46109.4 (2)
C11—C1—H1119.8C58—N2—C46111.5 (2)
C1—C2—C3120.4 (2)C52—N2—K1109.78 (15)
C1—C2—H2119.8C58—N2—K1105.63 (15)
C3—C2—H2119.8C46—N2—K1109.06 (16)
C12—C3—C2121.7 (2)C42—O1—C43111.1 (2)
C12—C3—H3119.2C42—O1—K1115.73 (15)
C2—C3—H3119.2C43—O1—K1109.12 (15)
C5—C4—C12119.7 (2)C45—O2—C44112.7 (2)
C5—C4—Co169.57 (12)C45—O2—K1116.06 (15)
C12—C4—Co1122.28 (15)C44—O2—K1116.55 (15)
C5—C4—H4117.6 (14)C49—O3—C48111.70 (19)
C12—C4—H4115.8 (14)C49—O3—K1111.61 (14)
Co1—C4—H4102.8 (14)C48—O3—K1114.58 (13)
C4—C5—C13120.27 (19)C51—O4—C50111.35 (19)
C4—C5—Co170.62 (12)C51—O4—K1115.36 (14)
C13—C5—Co1122.81 (15)C50—O4—K1113.36 (14)
C4—C5—H5119.6 (13)C54—O5—C55113.6 (2)
C13—C5—H5112.4 (13)C54—O5—K1113.55 (16)
Co1—C5—H5104.0 (13)C55—O5—K1116.69 (16)
C13—C6—C7121.0 (2)C57—O6—C56112.4 (2)
C13—C6—H6119.5C57—O6—K1119.78 (15)
C7—C6—H6119.5C56—O6—K1108.17 (16)
C8—C7—C6120.4 (2)N1—C41—C42113.8 (2)
C8—C7—H7119.8N1—C41—H41A108.8
C6—C7—H7119.8C42—C41—H41A108.8
C7—C8—C14121.0 (2)N1—C41—H41B108.8
C7—C8—H8119.5C42—C41—H41B108.8
C14—C8—H8119.5H41A—C41—H41B107.7
C10—C9—C14121.7 (2)O1—C42—C41108.8 (2)
C10—C9—H9A119.1O1—C42—H42A109.9
C14—C9—H9A119.1C41—C42—H42A109.9
C9—C10—C11121.9 (2)O1—C42—H42B109.9
C9—C10—H10A119.1C41—C42—H42B109.9
C11—C10—H10A119.1H42A—C42—H42B108.3
C1—C11—C15119.6 (2)O1—C43—C44109.2 (2)
C1—C11—C10122.2 (2)O1—C43—H43A109.8
C15—C11—C10118.1 (2)C44—C43—H43A109.8
C3—C12—C15118.1 (2)O1—C43—H43B109.8
C3—C12—C4121.9 (2)C44—C43—H43B109.8
C15—C12—C4119.9 (2)H43A—C43—H43B108.3
C6—C13—C16118.9 (2)O2—C44—C43108.4 (2)
C6—C13—C5121.6 (2)O2—C44—H44A110.0
C16—C13—C5119.5 (2)C43—C44—H44A110.0
C8—C14—C16119.0 (2)O2—C44—H44B110.0
C8—C14—C9122.6 (2)C43—C44—H44B110.0
C16—C14—C9118.5 (2)H44A—C44—H44B108.4
C11—C15—C12119.7 (2)O2—C45—C46108.4 (2)
C11—C15—C16119.9 (2)O2—C45—H45A110.0
C12—C15—C16120.36 (19)C46—C45—H45A110.0
C14—C16—C13119.8 (2)O2—C45—H45B110.0
C14—C16—C15119.9 (2)C46—C45—H45B110.0
C13—C16—C15120.34 (19)H45A—C45—H45B108.4
C18—C17—C27120.1 (2)N2—C46—C45113.7 (2)
C18—C17—H17120.0N2—C46—H46A108.8
C27—C17—H17120.0C45—C46—H46A108.8
C17—C18—C19120.9 (3)N2—C46—H46B108.8
C17—C18—H18119.5C45—C46—H46B108.8
C19—C18—H18119.5H46A—C46—H46B107.7
C18—C19—C28121.6 (2)N1—C47—C48112.5 (2)
C18—C19—H19119.2N1—C47—H47A109.1
C28—C19—H19119.2C48—C47—H47A109.1
C21—C20—C28119.6 (2)N1—C47—H47B109.1
C21—C20—Co171.65 (12)C48—C47—H47B109.1
C28—C20—Co1118.60 (15)H47A—C47—H47B107.8
C21—C20—H20119.8 (13)O3—C48—C47109.3 (2)
C28—C20—H20114.3 (13)O3—C48—H48A109.8
Co1—C20—H20104.4 (13)C47—C48—H48A109.8
C20—C21—C29119.7 (2)O3—C48—H48B109.8
C20—C21—Co168.92 (12)C47—C48—H48B109.8
C29—C21—Co1124.87 (15)H48A—C48—H48B108.3
C20—C21—H21121.6 (14)O3—C49—C50109.0 (2)
C29—C21—H21110.8 (14)O3—C49—H49A109.9
Co1—C21—H21104.6 (14)C50—C49—H49A109.9
C29—C22—C23121.1 (2)O3—C49—H49B109.9
C29—C22—H22119.4C50—C49—H49B109.9
C23—C22—H22119.4H49A—C49—H49B108.3
C24—C23—C22120.9 (2)O4—C50—C49108.9 (2)
C24—C23—H23119.6O4—C50—H50A109.9
C22—C23—H23119.6C49—C50—H50A109.9
C23—C24—C30120.3 (2)O4—C50—H50B109.9
C23—C24—H24119.8C49—C50—H50B109.9
C30—C24—H24119.8H50A—C50—H50B108.3
C26—C25—C30121.8 (2)O4—C51—C52108.4 (2)
C26—C25—H25119.1O4—C51—H51A110.0
C30—C25—H25119.1C52—C51—H51A110.0
C25—C26—C27121.7 (2)O4—C51—H51B110.0
C25—C26—H26119.2C52—C51—H51B110.0
C27—C26—H26119.2H51A—C51—H51B108.4
C17—C27—C31119.4 (2)N2—C52—C51113.0 (2)
C17—C27—C26122.2 (2)N2—C52—H52A109.0
C31—C27—C26118.3 (2)C51—C52—H52A109.0
C19—C28—C31117.8 (2)N2—C52—H52B109.0
C19—C28—C20121.9 (2)C51—C52—H52B109.0
C31—C28—C20120.3 (2)H52A—C52—H52B107.8
C22—C29—C32118.3 (2)N1—C53—C54113.1 (2)
C22—C29—C21121.6 (2)N1—C53—H53A109.0
C32—C29—C21120.0 (2)C54—C53—H53A109.0
C24—C30—C32119.2 (2)N1—C53—H53B109.0
C24—C30—C25122.4 (2)C54—C53—H53B109.0
C32—C30—C25118.4 (2)H53A—C53—H53B107.8
C27—C31—C28120.1 (2)O5—C54—C53107.3 (2)
C27—C31—C32120.0 (2)O5—C54—H54A110.2
C28—C31—C32119.9 (2)C53—C54—H54A110.2
C30—C32—C29120.2 (2)O5—C54—H54B110.2
C30—C32—C31119.7 (2)C53—C54—H54B110.2
C29—C32—C31120.2 (2)H54A—C54—H54B108.5
C34—C33—C40125.4 (2)O5—C55—C56108.2 (2)
C34—C33—Co169.70 (13)O5—C55—H55A110.1
C40—C33—Co1113.60 (16)C56—C55—H55A110.1
C34—C33—H33116.7 (13)O5—C55—H55B110.1
C40—C33—H33113.8 (13)C56—C55—H55B110.1
Co1—C33—H33107.1 (12)H55A—C55—H55B108.4
C33—C34—C35122.8 (2)O6—C56—C55108.7 (2)
C33—C34—Co171.42 (14)O6—C56—H56A109.9
C35—C34—Co1110.95 (15)C55—C56—H56A109.9
C33—C34—H34118.5 (15)O6—C56—H56B109.9
C35—C34—H34114.8 (15)C55—C56—H56B109.9
Co1—C34—H34107.1 (15)H56A—C56—H56B108.3
C34—C35—C36111.8 (2)O6—C57—C58109.4 (2)
C34—C35—H35A109.3O6—C57—H57A109.8
C36—C35—H35A109.3C58—C57—H57A109.8
C34—C35—H35B109.3O6—C57—H57B109.8
C36—C35—H35B109.3C58—C57—H57B109.8
H35A—C35—H35B107.9H57A—C57—H57B108.2
C37—C36—C35112.64 (19)N2—C58—C57114.1 (3)
C37—C36—H36A109.1N2—C58—H58A108.7
C35—C36—H36A109.1C57—C58—H58A108.7
C37—C36—H36B109.1N2—C58—H58B108.7
C35—C36—H36B109.1C57—C58—H58B108.7
H36A—C36—H36B107.8H58A—C58—H58B107.6
C38—C37—C36125.5 (2)C60—C59—H59A109.5
C38—C37—Co170.23 (13)C60—C59—H59B109.5
C36—C37—Co1112.29 (16)H59A—C59—H59B109.5
C38—C37—H37116.2 (14)C60—C59—H59C109.5
C36—C37—H37114.3 (14)H59A—C59—H59C109.5
Co1—C37—H37107.3 (14)H59B—C59—H59C109.5
C37—C38—C39122.9 (2)C59—C60—C61111 (2)
C37—C38—Co170.83 (13)C59—C60—H60A109.5
C39—C38—Co1111.38 (16)C61—C60—H60A109.5
C37—C38—H38117.9 (15)C59—C60—H60B109.5
C39—C38—H38114.2 (15)C61—C60—H60B109.5
Co1—C38—H38109.7 (15)H60A—C60—H60B108.1
C38—C39—C40112.1 (2)C60—C61—C6299.0 (10)
C38—C39—H39A109.2C60—C61—H61A112.0
C40—C39—H39A109.2C62—C61—H61A112.0
C38—C39—H39B109.2C60—C61—H61B112.0
C40—C39—H39B109.2C62—C61—H61B112.0
H39A—C39—H39B107.9H61A—C61—H61B109.6
C33—C40—C39111.38 (19)C61—C62—C63107 (3)
C33—C40—H40A109.4C61—C62—H62A110.3
C39—C40—H40A109.4C63—C62—H62A110.3
C33—C40—H40B109.4C61—C62—H62B110.3
C39—C40—H40B109.4C63—C62—H62B110.3
H40A—C40—H40B108.0H62A—C62—H62B108.6
O5—K1—O2145.58 (6)C62—C63—H63A109.5
O5—K1—O660.69 (6)C62—C63—H63B109.5
O2—K1—O6105.31 (6)H63A—C63—H63B109.5
O5—K1—O1105.64 (6)C62—C63—H62C109.5
O2—K1—O160.77 (5)H63A—C63—H62C109.5
O6—K1—O1135.93 (5)H63B—C63—H62C109.5
C11—C1—C2—C30.4 (4)C34—Co1—C38—C3764.93 (15)
C1—C2—C3—C122.1 (4)C5—Co1—C38—C37172.78 (14)
C34—Co1—C4—C560.02 (17)C33—Co1—C38—C3799.40 (15)
C38—Co1—C4—C5168.16 (13)C4—Co1—C38—C37162.49 (15)
C33—Co1—C4—C584.93 (14)C20—Co1—C38—C3732.05 (18)
C37—Co1—C4—C5177.41 (13)C21—Co1—C38—C3769.64 (15)
C20—Co1—C4—C561.81 (15)C34—Co1—C38—C3953.84 (19)
C21—Co1—C4—C589.64 (13)C5—Co1—C38—C3968.4 (2)
C34—Co1—C4—C1252.9 (2)C33—Co1—C38—C3919.38 (18)
C5—Co1—C4—C12112.9 (2)C37—Co1—C38—C39118.8 (2)
C38—Co1—C4—C1255.25 (19)C4—Co1—C38—C3978.74 (18)
C33—Co1—C4—C1228.0 (2)C20—Co1—C38—C39150.82 (16)
C37—Co1—C4—C1269.7 (2)C21—Co1—C38—C39171.59 (17)
C20—Co1—C4—C12174.72 (17)C37—C38—C39—C4048.1 (3)
C21—Co1—C4—C12157.46 (19)Co1—C38—C39—C4032.3 (2)
C12—C4—C5—C131.0 (3)C34—C33—C40—C3994.8 (3)
Co1—C4—C5—C13117.4 (2)Co1—C33—C40—C3913.7 (2)
C12—C4—C5—Co1116.3 (2)C38—C39—C40—C3329.8 (3)
C34—Co1—C5—C4137.05 (13)O5—K1—N1—C532.07 (17)
C38—Co1—C5—C416.17 (18)O2—K1—N1—C53137.48 (17)
C33—Co1—C5—C499.35 (14)O6—K1—N1—C532.98 (19)
C37—Co1—C5—C411.7 (6)O1—K1—N1—C53131.97 (19)
C20—Co1—C5—C4130.52 (13)O3—K1—N1—C53111.19 (19)
C21—Co1—C5—C491.53 (13)O4—K1—N1—C53104.54 (18)
C34—Co1—C5—C1322.9 (2)N2—K1—N1—C5330 (8)
C38—Co1—C5—C1398.0 (2)O5—K1—N1—C41122.41 (19)
C33—Co1—C5—C1314.79 (19)O2—K1—N1—C4117.15 (19)
C37—Co1—C5—C13125.9 (5)O6—K1—N1—C41117.35 (18)
C4—Co1—C5—C13114.1 (2)O1—K1—N1—C4111.63 (17)
C20—Co1—C5—C13115.34 (19)O3—K1—N1—C41128.47 (19)
C21—Co1—C5—C13154.33 (19)O4—K1—N1—C41135.13 (17)
C13—C6—C7—C80.4 (4)N2—K1—N1—C41150 (8)
C6—C7—C8—C140.2 (4)O5—K1—N1—C47118.38 (18)
C14—C9—C10—C110.6 (4)O2—K1—N1—C47102.07 (17)
C2—C1—C11—C151.1 (4)O6—K1—N1—C47123.43 (17)
C2—C1—C11—C10176.9 (2)O1—K1—N1—C47107.59 (18)
C9—C10—C11—C1176.4 (2)O3—K1—N1—C479.25 (16)
C9—C10—C11—C151.7 (3)O4—K1—N1—C4715.91 (19)
C2—C3—C12—C153.7 (3)N2—K1—N1—C4790 (8)
C2—C3—C12—C4180.0 (2)O5—K1—N2—C5297.28 (17)
C5—C4—C12—C3176.1 (2)O2—K1—N2—C52123.00 (18)
Co1—C4—C12—C3100.5 (2)O6—K1—N2—C52102.57 (17)
C5—C4—C12—C150.1 (3)O1—K1—N2—C52128.64 (16)
Co1—C4—C12—C1583.3 (2)O3—K1—N2—C5211.49 (18)
C7—C6—C13—C160.6 (3)O4—K1—N2—C525.32 (15)
C7—C6—C13—C5177.5 (2)N1—K1—N2—C5269 (8)
C4—C5—C13—C6177.1 (2)O5—K1—N2—C5822.92 (19)
Co1—C5—C13—C697.5 (2)O2—K1—N2—C58116.80 (19)
C4—C5—C13—C160.9 (3)O6—K1—N2—C5817.62 (17)
Co1—C5—C13—C1684.5 (2)O1—K1—N2—C58111.16 (18)
C7—C8—C14—C160.6 (3)O3—K1—N2—C58131.69 (17)
C7—C8—C14—C9179.3 (2)O4—K1—N2—C58125.51 (19)
C10—C9—C14—C8178.7 (2)N1—K1—N2—C5851 (8)
C10—C9—C14—C161.4 (3)O5—K1—N2—C46142.90 (16)
C1—C11—C15—C120.7 (3)O2—K1—N2—C463.18 (16)
C10—C11—C15—C12178.7 (2)O6—K1—N2—C46137.61 (18)
C1—C11—C15—C16177.3 (2)O1—K1—N2—C468.82 (18)
C10—C11—C15—C160.7 (3)O3—K1—N2—C46108.33 (17)
C3—C12—C15—C113.0 (3)O4—K1—N2—C46114.50 (18)
C4—C12—C15—C11179.3 (2)N1—K1—N2—C46171 (71)
C3—C12—C15—C16175.0 (2)O5—K1—O1—C4262.1 (2)
C4—C12—C15—C161.3 (3)O2—K1—O1—C42152.4 (2)
C8—C14—C16—C130.4 (3)O6—K1—O1—C42125.86 (19)
C9—C14—C16—C13179.5 (2)O3—K1—O1—C4228.9 (2)
C8—C14—C16—C15177.9 (2)O4—K1—O1—C4284.5 (2)
C9—C14—C16—C152.2 (3)N1—K1—O1—C4222.24 (19)
C6—C13—C16—C140.2 (3)N2—K1—O1—C42157.91 (19)
C5—C13—C16—C14177.91 (19)O5—K1—O1—C43171.77 (16)
C6—C13—C16—C15178.4 (2)O2—K1—O1—C4326.19 (16)
C5—C13—C16—C150.4 (3)O6—K1—O1—C43107.97 (17)
C11—C15—C16—C141.2 (3)O3—K1—O1—C4397.25 (16)
C12—C15—C16—C14176.79 (19)O4—K1—O1—C4341.72 (18)
C11—C15—C16—C13179.5 (2)N1—K1—O1—C43148.41 (17)
C12—C15—C16—C131.5 (3)N2—K1—O1—C4331.74 (17)
C27—C17—C18—C191.4 (4)O5—K1—O2—C4569.85 (19)
C17—C18—C19—C280.2 (4)O6—K1—O2—C459.73 (17)
C34—Co1—C20—C21172.99 (14)O1—K1—O2—C45144.18 (17)
C5—Co1—C20—C2182.02 (14)O3—K1—O2—C45138.06 (16)
C38—Co1—C20—C2169.95 (16)O4—K1—O2—C4579.87 (16)
C33—Co1—C20—C21176.96 (13)N1—K1—O2—C45149.70 (16)
C37—Co1—C20—C2189.46 (14)N2—K1—O2—C4530.19 (16)
C4—Co1—C20—C2147.26 (16)O5—K1—O2—C4466.6 (2)
C34—Co1—C20—C2872.67 (19)O6—K1—O2—C44126.68 (17)
C5—Co1—C20—C2832.32 (19)O1—K1—O2—C447.77 (16)
C38—Co1—C20—C28175.71 (17)O3—K1—O2—C4485.53 (17)
C33—Co1—C20—C2868.7 (2)O4—K1—O2—C44143.72 (17)
C37—Co1—C20—C28156.20 (19)N1—K1—O2—C4413.29 (19)
C4—Co1—C20—C2867.1 (2)N2—K1—O2—C44166.60 (19)
C21—Co1—C20—C28114.3 (2)O5—K1—O3—C4998.89 (16)
C28—C20—C21—C296.0 (3)O2—K1—O3—C4996.46 (16)
Co1—C20—C21—C29119.04 (19)O6—K1—O3—C4945.41 (17)
C28—C20—C21—Co1113.05 (19)O1—K1—O3—C49155.45 (15)
C34—Co1—C21—C209.08 (18)O4—K1—O3—C4920.42 (15)
C5—Co1—C21—C20101.32 (14)N1—K1—O3—C49153.03 (17)
C38—Co1—C21—C20124.41 (14)N2—K1—O3—C4926.49 (17)
C33—Co1—C21—C2011.6 (5)O5—K1—O3—C4829.32 (15)
C37—Co1—C21—C2088.25 (14)O2—K1—O3—C48135.34 (15)
C4—Co1—C21—C20141.14 (14)O6—K1—O3—C4882.80 (16)
C34—Co1—C21—C29121.4 (2)O1—K1—O3—C4876.35 (15)
C5—Co1—C21—C2911.0 (2)O4—K1—O3—C48148.62 (16)
C38—Co1—C21—C29123.3 (2)N1—K1—O3—C4824.83 (15)
C33—Co1—C21—C29123.9 (4)N2—K1—O3—C48154.69 (15)
C37—Co1—C21—C29159.5 (2)O5—K1—O4—C51140.78 (15)
C4—Co1—C21—C2928.8 (2)O2—K1—O4—C5120.90 (15)
C20—Co1—C21—C29112.3 (2)O6—K1—O4—C5184.34 (15)
C29—C22—C23—C241.4 (4)O1—K1—O4—C5175.10 (16)
C22—C23—C24—C300.6 (4)O3—K1—O4—C51145.11 (16)
C30—C25—C26—C271.3 (4)N1—K1—O4—C51151.73 (15)
C18—C17—C27—C311.3 (4)N2—K1—O4—C5128.74 (15)
C18—C17—C27—C26177.0 (2)O5—K1—O4—C5089.16 (16)
C25—C26—C27—C17175.4 (2)O2—K1—O4—C50109.16 (16)
C25—C26—C27—C313.0 (4)O6—K1—O4—C50145.60 (16)
C18—C19—C28—C311.7 (3)O1—K1—O4—C5054.96 (18)
C18—C19—C28—C20179.8 (2)O3—K1—O4—C5015.05 (15)
C21—C20—C28—C19179.5 (2)N1—K1—O4—C5021.67 (18)
Co1—C20—C28—C1995.4 (2)N2—K1—O4—C50158.80 (17)
C21—C20—C28—C312.1 (3)O2—K1—O5—C5465.8 (2)
Co1—C20—C28—C3186.2 (2)O6—K1—O5—C54139.32 (17)
C23—C22—C29—C320.6 (3)O1—K1—O5—C545.02 (17)
C23—C22—C29—C21177.5 (2)O3—K1—O5—C5490.79 (16)
C20—C21—C29—C22172.8 (2)O4—K1—O5—C54147.89 (16)
Co1—C21—C29—C22103.4 (2)N1—K1—O5—C5435.64 (16)
C20—C21—C29—C325.3 (3)N2—K1—O5—C54144.59 (16)
Co1—C21—C29—C3278.6 (2)O2—K1—O5—C5569.2 (2)
C23—C24—C30—C320.9 (4)O6—K1—O5—C554.30 (16)
C23—C24—C30—C25178.0 (2)O1—K1—O5—C55129.99 (17)
C26—C25—C30—C24178.7 (2)O3—K1—O5—C55134.19 (17)
C26—C25—C30—C322.4 (4)O4—K1—O5—C5577.09 (17)
C17—C27—C31—C280.3 (3)N1—K1—O5—C55170.66 (19)
C26—C27—C31—C28178.7 (2)N2—K1—O5—C559.57 (19)
C17—C27—C31—C32177.4 (2)O5—K1—O6—C57160.2 (2)
C26—C27—C31—C321.0 (3)O2—K1—O6—C5754.1 (2)
C19—C28—C31—C271.8 (3)O1—K1—O6—C57117.6 (2)
C20—C28—C31—C27179.7 (2)O3—K1—O6—C5793.0 (2)
C19—C28—C31—C32175.9 (2)O4—K1—O6—C5740.2 (2)
C20—C28—C31—C322.6 (3)N1—K1—O6—C57165.1 (2)
C24—C30—C32—C291.6 (3)N2—K1—O6—C5714.6 (2)
C25—C30—C32—C29177.3 (2)O5—K1—O6—C5629.56 (14)
C24—C30—C32—C31176.8 (2)O2—K1—O6—C56175.36 (14)
C25—C30—C32—C314.3 (3)O1—K1—O6—C56111.79 (15)
C22—C29—C32—C300.9 (3)O3—K1—O6—C5637.59 (16)
C21—C29—C32—C30179.02 (19)O4—K1—O6—C5690.40 (15)
C22—C29—C32—C31177.51 (19)N1—K1—O6—C5634.53 (16)
C21—C29—C32—C310.6 (3)N2—K1—O6—C56145.21 (16)
C27—C31—C32—C302.6 (3)C53—N1—C41—C42164.6 (2)
C28—C31—C32—C30175.10 (19)C47—N1—C41—C4273.2 (3)
C27—C31—C32—C29179.0 (2)K1—N1—C41—C4244.5 (3)
C28—C31—C32—C293.3 (3)C43—O1—C42—C41179.6 (2)
C5—Co1—C33—C34109.61 (15)K1—O1—C42—C4154.4 (3)
C38—Co1—C33—C34117.76 (15)N1—C41—C42—O169.1 (3)
C37—Co1—C33—C3479.44 (15)C42—O1—C43—C44171.9 (2)
C4—Co1—C33—C34149.32 (14)K1—O1—C43—C4459.3 (2)
C20—Co1—C33—C346.34 (19)C45—O2—C44—C43177.7 (2)
C21—Co1—C33—C343.1 (5)K1—O2—C44—C4339.9 (3)
C34—Co1—C33—C40120.8 (2)O1—C43—C44—O267.6 (3)
C5—Co1—C33—C40129.62 (17)C44—O2—C45—C46160.0 (2)
C38—Co1—C33—C403.01 (17)K1—O2—C45—C4662.0 (2)
C37—Co1—C33—C4041.32 (18)C52—N2—C46—C45154.5 (2)
C4—Co1—C33—C4089.91 (17)C58—N2—C46—C4581.8 (3)
C20—Co1—C33—C40127.11 (17)K1—N2—C46—C4534.4 (3)
C21—Co1—C33—C40117.6 (4)O2—C45—C46—N264.5 (3)
C40—C33—C34—C351.7 (4)C53—N1—C47—C4879.0 (3)
Co1—C33—C34—C35103.4 (2)C41—N1—C47—C48158.4 (2)
C40—C33—C34—Co1105.1 (2)K1—N1—C47—C4841.6 (3)
C5—Co1—C34—C3376.58 (15)C49—O3—C48—C47173.9 (2)
C38—Co1—C34—C3363.42 (15)K1—O3—C48—C4758.0 (2)
C37—Co1—C34—C3398.38 (15)N1—C47—C48—O368.9 (3)
C4—Co1—C34—C3341.57 (19)C48—O3—C49—C50176.5 (2)
C20—Co1—C34—C33175.08 (15)K1—O3—C49—C5053.7 (2)
C21—Co1—C34—C33179.17 (14)C51—O4—C50—C49179.9 (2)
C5—Co1—C34—C35164.53 (16)K1—O4—C50—C4948.0 (2)
C38—Co1—C34—C3555.47 (18)O3—C49—C50—O469.8 (3)
C33—Co1—C34—C35118.9 (2)C50—O4—C51—C52168.2 (2)
C37—Co1—C34—C3520.52 (17)K1—O4—C51—C5260.8 (2)
C4—Co1—C34—C35160.47 (15)C58—N2—C52—C51153.5 (2)
C20—Co1—C34—C3566.03 (18)C46—N2—C52—C5182.7 (3)
C21—Co1—C34—C3560.3 (2)K1—N2—C52—C5136.9 (3)
C33—C34—C35—C3648.3 (3)O4—C51—C52—N266.1 (3)
Co1—C34—C35—C3632.6 (2)C41—N1—C53—C5489.0 (3)
C34—C35—C36—C3729.0 (3)C47—N1—C53—C54148.4 (3)
C35—C36—C37—C3893.0 (3)K1—N1—C53—C5429.0 (3)
C35—C36—C37—Co112.0 (2)C55—O5—C54—C53156.5 (2)
C34—Co1—C37—C38116.53 (16)K1—O5—C54—C5367.0 (3)
C5—Co1—C37—C3833.2 (6)N1—C53—C54—O563.6 (3)
C33—Co1—C37—C3878.14 (15)C54—O5—C55—C56171.3 (2)
C4—Co1—C37—C3823.31 (19)K1—O5—C55—C5636.3 (3)
C20—Co1—C37—C38152.83 (15)C57—O6—C56—C55162.8 (2)
C21—Co1—C37—C38113.34 (15)K1—O6—C56—C5562.7 (2)
C34—Co1—C37—C364.76 (17)O5—C55—C56—O667.6 (3)
C5—Co1—C37—C36154.5 (5)C56—O6—C57—C58174.1 (2)
C38—Co1—C37—C36121.3 (2)K1—O6—C57—C5845.4 (3)
C33—Co1—C37—C3643.15 (17)C52—N2—C58—C5769.6 (3)
C4—Co1—C37—C36144.60 (15)C46—N2—C58—C57167.9 (2)
C20—Co1—C37—C3685.88 (17)K1—N2—C58—C5749.5 (3)
C21—Co1—C37—C36125.37 (17)O6—C57—C58—N266.3 (3)
C36—C37—C38—C390.2 (4)C59—C60—C61—C62160 (4)
Co1—C37—C38—C39103.6 (2)C60—C61—C62—C63175 (3)
C36—C37—C38—Co1103.8 (2)

Experimental details

Crystal data
Chemical formula[K(C18H36N2O6)][Co(C8H12)(C16H10)2]·0.5C5H12
Mr1023.25
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)12.1007 (9), 12.9869 (10), 18.7501 (14)
α, β, γ (°)72.064 (1), 81.595 (1), 68.558 (1)
V3)2607.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.46
Crystal size (mm)0.40 × 0.24 × 0.08
Data collection
DiffractometerBruker SMART CCD Platform
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008)
Tmin, Tmax0.837, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
29850, 11375, 7919
Rint0.037
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.108, 1.01
No. of reflections11375
No. of parameters678
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.74, 0.48

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This research was supported by the US National Science Foundation and the donors of the Petroleum Research Fund, administered by the American Chemical Society.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBrennessel, W. W., Young, V. G. Jr & Ellis, J. E. (2006). Angew. Chem. Int. Ed. 45, 7268–7271.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFrampton, C. S., Knight, K. S., Shankland, N. & Shankland, K. (2000). J. Mol. Struct. 520, 29–32.  Web of Science CSD CrossRef CAS Google Scholar
First citationJonas, K. (1981). Adv. Organomet. Chem. 19, 97–122.  CrossRef CAS Google Scholar
First citationJonas, K. (1984). Pure Appl. Chem. 56, 63–80.  CrossRef CAS Web of Science Google Scholar
First citationJonas, K. (1985). Angew. Chem. Int. Ed. Engl. 24, 295–311.  CrossRef Web of Science Google Scholar
First citationJonas, K. & Krüger, C. (1980). Angew. Chem. Int. Ed. Engl. 19, 520–537.  CrossRef Web of Science Google Scholar
First citationJonas, K., Mynott, R., Krüger, C., Sekutowski, J. C. & Tsay, Y.-H. (1976). Angew. Chem. Int. Ed. 15, 767–768.  CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds