metal-organic compounds
Bis(μ-4,4′′-difluoro-1,1′:3′,1′′-terphenyl-2′-carboxylato-κ2O:O′)bis[aqua(4,4′′-difluoro-1,1′:3′,1′′-terphenyl-2′-carboxylato-κO)(pyridine-κN)cobalt(II)] diethyl ether disolvate
aDepartment of Bio & Nano Chemistry, College of Natural Sciences, Kookmin University, 861-1 Jeongneung-dong, Seongbuk-gu, Seoul 136-702, Republic of Korea, and bJeonju Center, Korea Basic Science Institute (KBSI), 664-14 Dukjin dong 1-ga, Dukjin-gu, Jeonju 561-756, Republic of Korea
*Correspondence e-mail: yoona@kookmin.ac.kr
The structure of the title compound, [Co2(C19H11F2O2)4(C5H5N)2(H2O)2]·2C4H10O, comprises two CoII atoms in a distorted square pyramidal coordination environment, straddling a crystallographic inversion center with a Co⋯Co separation of 3.1923 (15) Å. Each Co2+ cation is coordinated by three O atoms of three 4,4′′-difluoro-1,1′:3′,1′′-terphenyl-2′-carboxylate ligands, one water O atom and one pyridine N atom, forming a CoO4N polyhedron. Strong intramolecular O—H⋯O hydrogen bonds are observed between terminal metal-bound carboxylate groups and water O atoms.
Related literature
For background to metal complexes with 4,4′′-difluoro-1,1′:3′,1′′-terphenyl-2′-carboxylate ligands, see: Kannan et al. (2011) and to water-bridged di-cobalt complexes, see: Lee et al. (2002). Bimetal systems, ligated by four carboxylates and two histidines derived from the side chains of amino acids, are often found in active sites, see: Holm et al. (1996); Lippard & Berg (1994).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812038391/ru2042sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038391/ru2042Isup2.hkl
The sodium 4,4''-difluoro-1,1':3',1''-terphenyl-2'-carboxylate (0.200 g, 0.602 mmol) was added into cobalt(II) trifluoromethansulfonate (0.529 g, 1.21 mmol) in 10 ml of tetrahydrofuran at room temperature. After stirring for 30 min, triethylamine (0.122 g, 1.21 mmol) and pyridine (0.134 g, 1.69 mmol) were added. Immediately, the color of solution was changed from light violet to dark purple. After 30 min, water (0.0218 g, 1.21 mmol) was further added. The volatile fractions were removed under the reduced pressure. Resulting purple powder was dissolved in dicloromethane and insoluble fractions were filtered off. Purple block-shaped crystals were collected upon vapor diffusion of diethyl ether. Yield = 2.26% (0.0230 g)
H atoms were placed at calculated positions and refined as riding with C–H(aromatic) = 0.95 Å, C–H(CH3) = 0.98 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl groups. The O-bound H atoms of waters were located in a difference Fourier map and refined isotropically.
In 1 with one half molecule in the Bond distances to the metal are given in Table 1 with the structure of the molecule shown in Fig 1. and its strong intramolecular O—H···O interactions detailed in Table 2.
active sites, bimetal systems, ligated by four carboxylates and two histidines derived from the side chains of amino acids, are often found (Lippard et al. 1994; Holm et al. 1996). Here, we report the structure of the water-containing di-nuclear Co(II) complex which crystallizes in the triclinic PFor background to metal complexes with 4,4''-difluoro-1,1':3',1''-terphenyl -2'-carboxylate ligands, see: Kannan et al., (2011) and to water-bridged di-cobalt complexes, see: Lee et al. (2002). Bimetal systems, ligated by four carboxylates and two histidines derived from the side chains of amino acids, are often found in
active sites, see: Holm et al. (1996); Lippard & Berg (1994).Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, showing the atom-numbering, the hydrogen bonds and with displacement ellipsoids drawn at the 50% probability level. |
[Co2(C19H11F2O2)4(C5H5N)2(H2O)2]·2C4H10O | Z = 1 |
Mr = 1697.44 | F(000) = 878 |
Triclinic, P1 | Dx = 1.406 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.0347 (16) Å | Cell parameters from 3108 reflections |
b = 14.0597 (18) Å | θ = 2.2–24.3° |
c = 14.3547 (18) Å | µ = 0.50 mm−1 |
α = 113.199 (3)° | T = 200 K |
β = 91.182 (3)° | Block, pink |
γ = 113.336 (3)° | 0.24 × 0.16 × 0.10 mm |
V = 2004.4 (4) Å3 |
Bruker SMART CCD area-detector diffractometer | 9861 independent reflections |
Radiation source: sealed tube | 4923 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
phi and ω scans | θmax = 28.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→15 |
Tmin = 0.403, Tmax = 1 | k = −18→17 |
15130 measured reflections | l = −14→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.239 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0806P)2 + 3.4487P] where P = (Fo2 + 2Fc2)/3 |
9861 reflections | (Δ/σ)max < 0.001 |
539 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −1.68 e Å−3 |
[Co2(C19H11F2O2)4(C5H5N)2(H2O)2]·2C4H10O | γ = 113.336 (3)° |
Mr = 1697.44 | V = 2004.4 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 12.0347 (16) Å | Mo Kα radiation |
b = 14.0597 (18) Å | µ = 0.50 mm−1 |
c = 14.3547 (18) Å | T = 200 K |
α = 113.199 (3)° | 0.24 × 0.16 × 0.10 mm |
β = 91.182 (3)° |
Bruker SMART CCD area-detector diffractometer | 9861 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4923 reflections with I > 2σ(I) |
Tmin = 0.403, Tmax = 1 | Rint = 0.042 |
15130 measured reflections |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.239 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.83 e Å−3 |
9861 reflections | Δρmin = −1.68 e Å−3 |
539 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. |
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. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.60580 (6) | 0.59297 (6) | 0.60114 (5) | 0.0361 (2) | |
O5 | 0.4457 (3) | 0.4290 (3) | 0.5772 (3) | 0.0395 (8) | |
H5 | 0.4256 | 0.4347 | 0.6342 | 0.059* | |
O2 | 0.4692 (3) | 0.6439 (3) | 0.6041 (2) | 0.0379 (8) | |
N1 | 0.7461 (4) | 0.7539 (3) | 0.6268 (3) | 0.0371 (9) | |
O3 | 0.6498 (3) | 0.6358 (3) | 0.7548 (2) | 0.0387 (8) | |
O4 | 0.6902 (3) | 0.4936 (3) | 0.5279 (2) | 0.0381 (8) | |
C1 | 0.3618 (5) | 0.6013 (4) | 0.5535 (4) | 0.0354 (11) | |
C29 | 0.8383 (5) | 0.7648 (5) | 0.5777 (4) | 0.0516 (14) | |
H29 | 0.8413 | 0.6972 | 0.5283 | 0.062* | |
O6 | 0.4785 (3) | 0.5124 (3) | 0.7781 (3) | 0.0457 (9) | |
C25 | 0.2179 (5) | 0.4920 (5) | 0.6837 (4) | 0.0466 (13) | |
H25 | 0.3031 | 0.5443 | 0.7098 | 0.056* | |
C22 | 0.2740 (6) | 0.8489 (5) | 0.6312 (4) | 0.0545 (15) | |
H22 | 0.3024 | 0.9217 | 0.6300 | 0.065* | |
C24 | 0.1389 (5) | 0.5206 (5) | 0.6390 (4) | 0.0422 (12) | |
C19 | 0.1880 (5) | 0.6339 (5) | 0.6338 (4) | 0.0462 (13) | |
C3 | 0.5839 (5) | 0.5962 (4) | 0.8106 (4) | 0.0369 (11) | |
C10 | 0.6781 (5) | 0.4879 (5) | 0.9112 (4) | 0.0410 (12) | |
C26 | 0.4369 (5) | 0.8181 (5) | 0.5376 (4) | 0.0452 (13) | |
C21 | 0.3327 (5) | 0.7785 (5) | 0.5877 (4) | 0.0440 (13) | |
C4 | 0.6390 (4) | 0.6573 (4) | 0.9245 (4) | 0.0365 (11) | |
C8 | 0.7213 (5) | 0.6549 (5) | 1.0786 (4) | 0.0528 (15) | |
H8 | 0.7450 | 0.6165 | 1.1109 | 0.063* | |
C13 | 0.7536 (5) | 0.4762 (5) | 0.8393 (4) | 0.0504 (14) | |
H13 | 0.7966 | 0.5380 | 0.8220 | 0.061* | |
C7 | 0.7322 (6) | 0.7639 (5) | 1.1381 (4) | 0.0543 (15) | |
H7 | 0.7640 | 0.8000 | 1.2107 | 0.065* | |
C14 | 0.6089 (5) | 0.8327 (4) | 0.9435 (4) | 0.0421 (12) | |
C18 | 0.4481 (6) | 0.8445 (5) | 0.8503 (4) | 0.0503 (14) | |
H18 | 0.3672 | 0.8101 | 0.8097 | 0.060* | |
C17 | 0.6448 (6) | 1.0092 (5) | 0.9324 (5) | 0.0564 (15) | |
H17 | 0.6983 | 1.0869 | 0.9478 | 0.068* | |
C5 | 0.6501 (5) | 0.7689 (5) | 0.9859 (4) | 0.0413 (12) | |
C20 | 0.2899 (5) | 0.6711 (4) | 0.5899 (4) | 0.0387 (12) | |
C9 | 0.6757 (5) | 0.6000 (4) | 0.9712 (4) | 0.0402 (12) | |
C16 | 0.6841 (5) | 0.9464 (5) | 0.9671 (4) | 0.0504 (14) | |
H16 | 0.7650 | 0.9826 | 1.0083 | 0.060* | |
C15 | 0.4889 (5) | 0.7821 (5) | 0.8853 (4) | 0.0455 (13) | |
H15 | 0.4347 | 0.7045 | 0.8696 | 0.055* | |
C12 | 0.6227 (6) | 0.2921 (5) | 0.8832 (5) | 0.0562 (15) | |
H12 | 0.5763 | 0.2278 | 0.8964 | 0.067* | |
C23 | 0.1297 (6) | 0.7061 (6) | 0.6760 (4) | 0.0572 (16) | |
H23 | 0.0593 | 0.6815 | 0.7047 | 0.069* | |
C11 | 0.6128 (5) | 0.3943 (5) | 0.9315 (5) | 0.0519 (14) | |
H11 | 0.5602 | 0.4005 | 0.9797 | 0.062* | |
C6 | 0.6975 (5) | 0.8205 (5) | 1.0934 (4) | 0.0489 (14) | |
H6 | 0.7054 | 0.8956 | 1.1354 | 0.059* | |
C28 | 0.7429 (5) | 0.8496 (4) | 0.6971 (4) | 0.0505 (14) | |
H28 | 0.6764 | 0.8423 | 0.7325 | 0.061* | |
F1 | 0.4869 (4) | 1.0186 (3) | 0.8430 (3) | 0.0703 (10) | |
F3 | 0.0045 (4) | 0.2143 (3) | 0.6617 (3) | 0.0938 (14) | |
F2 | 0.7149 (4) | 0.1870 (3) | 0.7706 (3) | 0.0806 (12) | |
C45 | 0.1733 (6) | 0.3890 (5) | 0.6903 (4) | 0.0535 (15) | |
H45 | 0.2273 | 0.3682 | 0.7185 | 0.064* | |
C39 | 0.0140 (5) | 0.4445 (6) | 0.6039 (4) | 0.0536 (15) | |
H39 | −0.0409 | 0.4638 | 0.5750 | 0.064* | |
C34 | 0.4377 (6) | 0.7469 (5) | 0.4357 (4) | 0.0508 (14) | |
H34 | 0.3704 | 0.6728 | 0.3985 | 0.061* | |
C44 | 0.5280 (6) | 0.9570 (5) | 0.8759 (4) | 0.0499 (14) | |
C41 | 0.0492 (7) | 0.3168 (5) | 0.6554 (5) | 0.0603 (17) | |
C38 | 0.5357 (6) | 0.7841 (5) | 0.3893 (4) | 0.0565 (16) | |
H38 | 0.5355 | 0.7364 | 0.3204 | 0.068* | |
C42 | 0.7665 (6) | 0.3747 (5) | 0.7925 (4) | 0.0581 (16) | |
H42 | 0.8199 | 0.3672 | 0.7451 | 0.070* | |
C40 | −0.0312 (6) | 0.3408 (6) | 0.6105 (5) | 0.0632 (17) | |
H40 | −0.1162 | 0.2875 | 0.5846 | 0.076* | |
C36 | 0.6355 (6) | 0.9644 (5) | 0.5419 (5) | 0.0586 (16) | |
H36 | 0.7029 | 1.0389 | 0.5771 | 0.070* | |
C37 | 0.6318 (7) | 0.8897 (5) | 0.4439 (5) | 0.0579 (16) | |
C43 | 0.7007 (6) | 0.2865 (5) | 0.8166 (5) | 0.0547 (15) | |
C33 | 0.1753 (6) | 0.8128 (6) | 0.6754 (5) | 0.0643 (18) | |
H33 | 0.1374 | 0.8622 | 0.7064 | 0.077* | |
C35 | 0.5366 (6) | 0.9270 (5) | 0.5876 (5) | 0.0577 (16) | |
H35 | 0.5370 | 0.9775 | 0.6553 | 0.069* | |
C32 | 0.9283 (6) | 0.9697 (6) | 0.6685 (6) | 0.0684 (19) | |
H32 | 0.9912 | 1.0440 | 0.6831 | 0.082* | |
C31 | 0.8321 (6) | 0.9566 (5) | 0.7190 (5) | 0.0620 (17) | |
H31 | 0.8275 | 1.0226 | 0.7696 | 0.074* | |
C30 | 0.9310 (6) | 0.8715 (6) | 0.5956 (5) | 0.0635 (17) | |
H30 | 0.9957 | 0.8769 | 0.5582 | 0.076* | |
F4 | 0.7304 (4) | 0.9255 (3) | 0.3996 (3) | 0.0778 (11) | |
O7 | 0.0379 (4) | 0.7330 (4) | 0.9186 (3) | 0.0700 (12) | |
C47 | −0.0130 (6) | 0.8100 (6) | 0.9638 (5) | 0.0666 (18) | |
H47A | 0.0462 | 0.8774 | 1.0263 | 0.080* | |
H47B | −0.0898 | 0.7718 | 0.9848 | 0.080* | |
C46 | −0.0415 (7) | 0.8488 (6) | 0.8852 (5) | 0.078 (2) | |
H46A | 0.0350 | 0.8869 | 0.8650 | 0.117* | |
H46B | −0.0772 | 0.9029 | 0.9159 | 0.117* | |
H46C | −0.1006 | 0.7817 | 0.8238 | 0.117* | |
C48 | 0.0575 (7) | 0.6834 (6) | 0.9825 (5) | 0.075 (2) | |
H48A | −0.0216 | 0.6417 | 0.9989 | 0.090* | |
H48B | 0.1163 | 0.7441 | 1.0483 | 0.090* | |
C49 | 0.1097 (7) | 0.6012 (7) | 0.9234 (6) | 0.083 (2) | |
H49A | 0.0526 | 0.5437 | 0.8570 | 0.125* | |
H49B | 0.1204 | 0.5622 | 0.9641 | 0.125* | |
H49C | 0.1899 | 0.6441 | 0.9109 | 0.125* | |
H2 | 0.461 (8) | 0.368 (8) | 0.558 (7) | 0.13 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0396 (4) | 0.0341 (4) | 0.0313 (3) | 0.0161 (3) | 0.0051 (3) | 0.0114 (3) |
O5 | 0.037 (2) | 0.036 (2) | 0.0378 (19) | 0.0103 (17) | 0.0062 (16) | 0.0154 (16) |
O2 | 0.041 (2) | 0.0329 (18) | 0.0312 (17) | 0.0115 (16) | −0.0016 (15) | 0.0108 (15) |
N1 | 0.038 (2) | 0.038 (2) | 0.032 (2) | 0.013 (2) | 0.0040 (18) | 0.0151 (19) |
O3 | 0.041 (2) | 0.047 (2) | 0.0231 (16) | 0.0160 (17) | 0.0015 (14) | 0.0142 (15) |
O4 | 0.042 (2) | 0.039 (2) | 0.0347 (18) | 0.0213 (17) | 0.0067 (15) | 0.0138 (16) |
C1 | 0.049 (3) | 0.030 (3) | 0.029 (2) | 0.018 (2) | 0.008 (2) | 0.015 (2) |
C29 | 0.051 (3) | 0.048 (3) | 0.050 (3) | 0.020 (3) | 0.014 (3) | 0.018 (3) |
O6 | 0.037 (2) | 0.042 (2) | 0.042 (2) | 0.0055 (17) | 0.0018 (16) | 0.0152 (17) |
C25 | 0.046 (3) | 0.052 (3) | 0.036 (3) | 0.019 (3) | 0.005 (2) | 0.016 (3) |
C22 | 0.063 (4) | 0.053 (4) | 0.055 (3) | 0.033 (3) | 0.012 (3) | 0.024 (3) |
C24 | 0.047 (3) | 0.047 (3) | 0.027 (2) | 0.020 (3) | 0.014 (2) | 0.011 (2) |
C19 | 0.046 (3) | 0.049 (3) | 0.036 (3) | 0.024 (3) | 0.002 (2) | 0.010 (2) |
C3 | 0.043 (3) | 0.042 (3) | 0.031 (2) | 0.020 (3) | 0.007 (2) | 0.020 (2) |
C10 | 0.036 (3) | 0.044 (3) | 0.039 (3) | 0.016 (2) | 0.004 (2) | 0.015 (2) |
C26 | 0.065 (4) | 0.037 (3) | 0.036 (3) | 0.030 (3) | 0.005 (3) | 0.011 (2) |
C21 | 0.059 (3) | 0.045 (3) | 0.037 (3) | 0.033 (3) | 0.011 (3) | 0.016 (2) |
C4 | 0.035 (3) | 0.036 (3) | 0.034 (2) | 0.015 (2) | 0.009 (2) | 0.011 (2) |
C8 | 0.061 (4) | 0.066 (4) | 0.033 (3) | 0.030 (3) | 0.008 (3) | 0.022 (3) |
C13 | 0.050 (3) | 0.054 (4) | 0.042 (3) | 0.020 (3) | 0.011 (3) | 0.018 (3) |
C7 | 0.062 (4) | 0.058 (4) | 0.031 (3) | 0.028 (3) | 0.006 (3) | 0.007 (3) |
C14 | 0.047 (3) | 0.031 (3) | 0.039 (3) | 0.014 (2) | 0.009 (2) | 0.010 (2) |
C18 | 0.064 (4) | 0.049 (3) | 0.040 (3) | 0.034 (3) | 0.007 (3) | 0.014 (3) |
C17 | 0.064 (4) | 0.037 (3) | 0.068 (4) | 0.022 (3) | 0.028 (3) | 0.023 (3) |
C5 | 0.040 (3) | 0.045 (3) | 0.032 (3) | 0.013 (2) | 0.011 (2) | 0.016 (2) |
C20 | 0.045 (3) | 0.047 (3) | 0.030 (2) | 0.027 (3) | 0.004 (2) | 0.016 (2) |
C9 | 0.040 (3) | 0.044 (3) | 0.037 (3) | 0.019 (2) | 0.012 (2) | 0.017 (2) |
C16 | 0.048 (3) | 0.039 (3) | 0.050 (3) | 0.014 (3) | 0.015 (3) | 0.011 (3) |
C15 | 0.050 (3) | 0.037 (3) | 0.043 (3) | 0.017 (3) | 0.005 (3) | 0.013 (2) |
C12 | 0.056 (4) | 0.048 (4) | 0.067 (4) | 0.026 (3) | 0.013 (3) | 0.025 (3) |
C23 | 0.054 (4) | 0.066 (4) | 0.054 (3) | 0.037 (3) | 0.010 (3) | 0.018 (3) |
C11 | 0.049 (3) | 0.056 (4) | 0.062 (4) | 0.025 (3) | 0.019 (3) | 0.034 (3) |
C6 | 0.055 (3) | 0.049 (3) | 0.035 (3) | 0.022 (3) | 0.007 (3) | 0.013 (3) |
C28 | 0.056 (4) | 0.029 (3) | 0.047 (3) | 0.016 (3) | 0.008 (3) | 0.002 (2) |
F1 | 0.111 (3) | 0.061 (2) | 0.065 (2) | 0.055 (2) | 0.026 (2) | 0.0334 (19) |
F3 | 0.112 (4) | 0.066 (3) | 0.101 (3) | 0.022 (3) | 0.042 (3) | 0.051 (3) |
F2 | 0.091 (3) | 0.055 (2) | 0.084 (3) | 0.044 (2) | 0.009 (2) | 0.008 (2) |
C45 | 0.060 (4) | 0.057 (4) | 0.045 (3) | 0.023 (3) | 0.018 (3) | 0.027 (3) |
C39 | 0.042 (3) | 0.074 (4) | 0.040 (3) | 0.024 (3) | 0.015 (3) | 0.020 (3) |
C34 | 0.075 (4) | 0.045 (3) | 0.038 (3) | 0.032 (3) | 0.005 (3) | 0.018 (3) |
C44 | 0.076 (4) | 0.047 (3) | 0.041 (3) | 0.040 (3) | 0.024 (3) | 0.020 (3) |
C41 | 0.073 (5) | 0.049 (4) | 0.057 (4) | 0.018 (3) | 0.029 (3) | 0.029 (3) |
C38 | 0.087 (5) | 0.049 (4) | 0.043 (3) | 0.039 (4) | 0.016 (3) | 0.020 (3) |
C42 | 0.060 (4) | 0.058 (4) | 0.045 (3) | 0.027 (3) | 0.015 (3) | 0.010 (3) |
C40 | 0.057 (4) | 0.062 (4) | 0.052 (4) | 0.011 (3) | 0.021 (3) | 0.022 (3) |
C36 | 0.071 (4) | 0.043 (3) | 0.056 (4) | 0.021 (3) | 0.015 (3) | 0.021 (3) |
C37 | 0.082 (5) | 0.053 (4) | 0.051 (3) | 0.035 (4) | 0.024 (3) | 0.029 (3) |
C43 | 0.054 (4) | 0.044 (3) | 0.056 (4) | 0.025 (3) | 0.003 (3) | 0.009 (3) |
C33 | 0.079 (5) | 0.068 (4) | 0.065 (4) | 0.055 (4) | 0.017 (4) | 0.024 (4) |
C35 | 0.081 (5) | 0.047 (4) | 0.043 (3) | 0.031 (3) | 0.009 (3) | 0.014 (3) |
C32 | 0.053 (4) | 0.047 (4) | 0.086 (5) | 0.000 (3) | −0.007 (4) | 0.034 (4) |
C31 | 0.067 (4) | 0.036 (3) | 0.065 (4) | 0.016 (3) | 0.003 (3) | 0.013 (3) |
C30 | 0.055 (4) | 0.057 (4) | 0.074 (4) | 0.014 (3) | 0.017 (3) | 0.035 (4) |
F4 | 0.101 (3) | 0.070 (3) | 0.078 (3) | 0.041 (2) | 0.045 (2) | 0.043 (2) |
O7 | 0.074 (3) | 0.083 (3) | 0.062 (3) | 0.043 (3) | 0.019 (2) | 0.033 (3) |
C47 | 0.050 (4) | 0.059 (4) | 0.067 (4) | 0.014 (3) | 0.014 (3) | 0.015 (3) |
C46 | 0.070 (5) | 0.083 (5) | 0.071 (5) | 0.042 (4) | −0.003 (4) | 0.018 (4) |
C48 | 0.061 (4) | 0.081 (5) | 0.068 (4) | 0.020 (4) | 0.001 (4) | 0.031 (4) |
C49 | 0.077 (5) | 0.100 (6) | 0.072 (5) | 0.047 (5) | 0.008 (4) | 0.029 (4) |
Co1—O4 | 2.025 (3) | C17—H17 | 0.9500 |
Co1—O2 | 2.032 (3) | C5—C6 | 1.409 (7) |
Co1—O3 | 2.040 (3) | C16—H16 | 0.9500 |
Co1—N1 | 2.097 (4) | C15—H15 | 0.9500 |
Co1—O5 | 2.230 (4) | C12—C43 | 1.356 (8) |
O5—H5 | 0.8400 | C12—C11 | 1.383 (8) |
O5—H2 | 0.89 (9) | C12—H12 | 0.9500 |
O2—C1 | 1.250 (6) | C23—C33 | 1.381 (9) |
N1—C29 | 1.317 (7) | C23—H23 | 0.9500 |
N1—C28 | 1.342 (6) | C11—H11 | 0.9500 |
O3—C3 | 1.267 (6) | C6—H6 | 0.9500 |
O4—C1i | 1.273 (5) | C28—C31 | 1.360 (8) |
C1—O4i | 1.273 (5) | C28—H28 | 0.9500 |
C1—C20 | 1.507 (7) | F1—C44 | 1.367 (6) |
C29—C30 | 1.385 (8) | F3—C41 | 1.366 (7) |
C29—H29 | 0.9500 | F2—C43 | 1.374 (6) |
O6—O6 | 0.000 (8) | C45—C41 | 1.372 (8) |
O6—C3 | 1.255 (6) | C45—H45 | 0.9500 |
C25—C45 | 1.375 (8) | C39—C40 | 1.384 (9) |
C25—C24 | 1.400 (7) | C39—H39 | 0.9500 |
C25—H25 | 0.9500 | C34—C38 | 1.387 (8) |
C22—C33 | 1.371 (9) | C34—H34 | 0.9500 |
C22—C21 | 1.398 (7) | C41—C40 | 1.366 (9) |
C22—H22 | 0.9500 | C38—C37 | 1.357 (9) |
C24—C39 | 1.388 (8) | C38—H38 | 0.9500 |
C24—C19 | 1.498 (8) | C42—C43 | 1.363 (9) |
C19—C20 | 1.399 (7) | C42—H42 | 0.9500 |
C19—C23 | 1.409 (7) | C40—H40 | 0.9500 |
C3—O6 | 1.255 (6) | C36—C37 | 1.372 (8) |
C3—C4 | 1.499 (7) | C36—C35 | 1.389 (9) |
C10—C11 | 1.389 (7) | C36—H36 | 0.9500 |
C10—C13 | 1.394 (7) | C37—F4 | 1.369 (7) |
C10—C9 | 1.481 (7) | C33—H33 | 0.9500 |
C26—C35 | 1.394 (8) | C35—H35 | 0.9500 |
C26—C34 | 1.413 (7) | C32—C31 | 1.369 (9) |
C26—C21 | 1.483 (8) | C32—C30 | 1.379 (9) |
C21—C20 | 1.403 (7) | C32—H32 | 0.9500 |
C4—C9 | 1.411 (7) | C31—H31 | 0.9500 |
C4—C5 | 1.413 (7) | C30—H30 | 0.9500 |
C8—C7 | 1.378 (8) | O7—C47 | 1.398 (7) |
C8—C9 | 1.401 (7) | O7—C48 | 1.418 (8) |
C8—H8 | 0.9500 | C47—C46 | 1.519 (9) |
C13—C42 | 1.392 (8) | C47—H47A | 0.9900 |
C13—H13 | 0.9500 | C47—H47B | 0.9900 |
C7—C6 | 1.370 (8) | C46—H46A | 0.9800 |
C7—H7 | 0.9500 | C46—H46B | 0.9800 |
C14—C16 | 1.380 (7) | C46—H46C | 0.9800 |
C14—C15 | 1.399 (7) | C48—C49 | 1.508 (9) |
C14—C5 | 1.480 (7) | C48—H48A | 0.9900 |
C18—C44 | 1.373 (8) | C48—H48B | 0.9900 |
C18—C15 | 1.393 (7) | C49—H49A | 0.9800 |
C18—H18 | 0.9500 | C49—H49B | 0.9800 |
C17—C44 | 1.356 (8) | C49—H49C | 0.9800 |
C17—C16 | 1.385 (8) | ||
O4—Co1—O2 | 151.94 (13) | C43—C12—C11 | 117.9 (6) |
O4—Co1—O3 | 106.05 (13) | C43—C12—H12 | 121.0 |
O2—Co1—O3 | 99.17 (13) | C11—C12—H12 | 121.0 |
O4—Co1—N1 | 98.68 (15) | C33—C23—C19 | 119.8 (6) |
O2—Co1—N1 | 93.70 (15) | C33—C23—H23 | 120.1 |
O3—Co1—N1 | 89.24 (14) | C19—C23—H23 | 120.1 |
O4—Co1—O5 | 86.10 (14) | C12—C11—C10 | 121.6 (6) |
O2—Co1—O5 | 81.46 (14) | C12—C11—H11 | 119.2 |
O3—Co1—O5 | 90.60 (13) | C10—C11—H11 | 119.2 |
N1—Co1—O5 | 175.07 (16) | C7—C6—C5 | 120.9 (5) |
Co1—O5—H5 | 109.5 | C7—C6—H6 | 119.6 |
Co1—O5—H2 | 116 (6) | C5—C6—H6 | 119.6 |
H5—O5—H2 | 101.1 | N1—C28—C31 | 121.9 (6) |
C1—O2—Co1 | 136.2 (3) | N1—C28—H28 | 119.1 |
C29—N1—C28 | 118.7 (5) | C31—C28—H28 | 119.1 |
C29—N1—Co1 | 122.5 (4) | C41—C45—C25 | 118.4 (6) |
C28—N1—Co1 | 118.8 (4) | C41—C45—H45 | 120.8 |
C3—O3—Co1 | 129.3 (3) | C25—C45—H45 | 120.8 |
C1i—O4—Co1 | 124.6 (3) | C40—C39—C24 | 120.7 (6) |
O2—C1—O4i | 125.7 (4) | C40—C39—H39 | 119.6 |
O2—C1—C20 | 116.9 (4) | C24—C39—H39 | 119.6 |
O4i—C1—C20 | 117.3 (4) | C38—C34—C26 | 120.8 (6) |
N1—C29—C30 | 122.1 (6) | C38—C34—H34 | 119.6 |
N1—C29—H29 | 118.9 | C26—C34—H34 | 119.6 |
C30—C29—H29 | 118.9 | C17—C44—F1 | 119.0 (5) |
O6—O6—C3 | 0 (10) | C17—C44—C18 | 122.9 (5) |
C45—C25—C24 | 120.7 (6) | F1—C44—C18 | 118.0 (6) |
C45—C25—H25 | 119.7 | F3—C41—C40 | 118.4 (6) |
C24—C25—H25 | 119.7 | F3—C41—C45 | 118.7 (6) |
C33—C22—C21 | 120.0 (6) | C40—C41—C45 | 122.9 (6) |
C33—C22—H22 | 120.0 | C37—C38—C34 | 118.9 (5) |
C21—C22—H22 | 120.0 | C37—C38—H38 | 120.5 |
C39—C24—C25 | 118.8 (5) | C34—C38—H38 | 120.5 |
C39—C24—C19 | 120.9 (5) | C43—C42—C13 | 118.3 (6) |
C25—C24—C19 | 120.2 (5) | C43—C42—H42 | 120.9 |
C20—C19—C23 | 119.0 (5) | C13—C42—H42 | 120.9 |
C20—C19—C24 | 122.6 (5) | C41—C40—C39 | 118.4 (6) |
C23—C19—C24 | 118.4 (5) | C41—C40—H40 | 120.8 |
O6—C3—O6 | 0.0 (5) | C39—C40—H40 | 120.8 |
O6—C3—O3 | 125.4 (4) | C37—C36—C35 | 117.4 (6) |
O6—C3—O3 | 125.4 (4) | C37—C36—H36 | 121.3 |
O6—C3—C4 | 118.8 (4) | C35—C36—H36 | 121.3 |
O6—C3—C4 | 118.8 (4) | C38—C37—F4 | 119.2 (5) |
O3—C3—C4 | 115.7 (4) | C38—C37—C36 | 123.4 (6) |
C11—C10—C13 | 118.2 (5) | F4—C37—C36 | 117.4 (6) |
C11—C10—C9 | 120.6 (5) | C12—C43—C42 | 123.5 (6) |
C13—C10—C9 | 121.0 (5) | C12—C43—F2 | 118.7 (6) |
C35—C26—C34 | 117.2 (6) | C42—C43—F2 | 117.8 (6) |
C35—C26—C21 | 121.9 (5) | C22—C33—C23 | 121.4 (6) |
C34—C26—C21 | 120.9 (5) | C22—C33—H33 | 119.3 |
C22—C21—C20 | 119.5 (5) | C23—C33—H33 | 119.3 |
C22—C21—C26 | 118.9 (5) | C36—C35—C26 | 122.4 (5) |
C20—C21—C26 | 121.6 (4) | C36—C35—H35 | 118.8 |
C9—C4—C5 | 119.8 (4) | C26—C35—H35 | 118.8 |
C9—C4—C3 | 119.1 (4) | C31—C32—C30 | 117.8 (6) |
C5—C4—C3 | 121.1 (4) | C31—C32—H32 | 121.1 |
C7—C8—C9 | 121.1 (5) | C30—C32—H32 | 121.1 |
C7—C8—H8 | 119.5 | C28—C31—C32 | 120.3 (6) |
C9—C8—H8 | 119.5 | C28—C31—H31 | 119.9 |
C42—C13—C10 | 120.5 (6) | C32—C31—H31 | 119.9 |
C42—C13—H13 | 119.8 | C32—C30—C29 | 119.2 (6) |
C10—C13—H13 | 119.8 | C32—C30—H30 | 120.4 |
C6—C7—C8 | 120.5 (5) | C29—C30—H30 | 120.4 |
C6—C7—H7 | 119.8 | C47—O7—C48 | 113.1 (5) |
C8—C7—H7 | 119.8 | O7—C47—C46 | 108.7 (5) |
C16—C14—C15 | 118.2 (5) | O7—C47—H47A | 110.0 |
C16—C14—C5 | 120.9 (5) | C46—C47—H47A | 110.0 |
C15—C14—C5 | 120.7 (5) | O7—C47—H47B | 110.0 |
C44—C18—C15 | 118.2 (5) | C46—C47—H47B | 110.0 |
C44—C18—H18 | 120.9 | H47A—C47—H47B | 108.3 |
C15—C18—H18 | 120.9 | C47—C46—H46A | 109.5 |
C44—C17—C16 | 118.3 (6) | C47—C46—H46B | 109.5 |
C44—C17—H17 | 120.8 | H46A—C46—H46B | 109.5 |
C16—C17—H17 | 120.8 | C47—C46—H46C | 109.5 |
C6—C5—C4 | 118.9 (5) | H46A—C46—H46C | 109.5 |
C6—C5—C14 | 118.0 (5) | H46B—C46—H46C | 109.5 |
C4—C5—C14 | 123.0 (4) | O7—C48—C49 | 107.3 (6) |
C19—C20—C21 | 120.3 (5) | O7—C48—H48A | 110.3 |
C19—C20—C1 | 120.3 (5) | C49—C48—H48A | 110.3 |
C21—C20—C1 | 119.2 (5) | O7—C48—H48B | 110.3 |
C8—C9—C4 | 118.9 (5) | C49—C48—H48B | 110.3 |
C8—C9—C10 | 117.9 (5) | H48A—C48—H48B | 108.5 |
C4—C9—C10 | 123.0 (4) | C48—C49—H49A | 109.5 |
C14—C16—C17 | 121.7 (6) | C48—C49—H49B | 109.5 |
C14—C16—H16 | 119.1 | H49A—C49—H49B | 109.5 |
C17—C16—H16 | 119.1 | C48—C49—H49C | 109.5 |
C18—C15—C14 | 120.6 (5) | H49A—C49—H49C | 109.5 |
C18—C15—H15 | 119.7 | H49B—C49—H49C | 109.5 |
C14—C15—H15 | 119.7 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Co2(C19H11F2O2)4(C5H5N)2(H2O)2]·2C4H10O |
Mr | 1697.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 200 |
a, b, c (Å) | 12.0347 (16), 14.0597 (18), 14.3547 (18) |
α, β, γ (°) | 113.199 (3), 91.182 (3), 113.336 (3) |
V (Å3) | 2004.4 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.24 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.403, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15130, 9861, 4923 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.239, 1.06 |
No. of reflections | 9861 |
No. of parameters | 539 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.83, −1.68 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Co1—O4 | 2.025 (3) | Co1—N1 | 2.097 (4) |
Co1—O2 | 2.032 (3) | Co1—O5 | 2.230 (4) |
Co1—O3 | 2.040 (3) |
Acknowledgements
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010-0012349).
References
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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.
In metalloenzyme active sites, bimetal systems, ligated by four carboxylates and two histidines derived from the side chains of amino acids, are often found (Lippard et al. 1994; Holm et al. 1996). Here, we report the structure of the water-containing di-nuclear Co(II) complex which crystallizes in the triclinic space group P1 with one half molecule in the asymmetric unit. Bond distances to the metal are given in Table 1 with the structure of the molecule shown in Fig 1. and its strong intramolecular O—H···O interactions detailed in Table 2.