metal-organic compounds
Bis(μ2-benzoato-κ2O:O′)bis[(benzoato-κ2O,O′)bis(4,4′-bipyridine-κN)cobalt(II)]–benzoic acid (1/6)
aFacultad de Ciencias Químicas, Universidad Veracruzana, Prolongación Oriente 6, No. 1009, Colonia Rafael Alvarado, Apartado Postal 215, CP 94340, Orizaba, Veracruz, Mexico, and bDepartamento de Química, Centro de Investigación y de Estudios Avanzados del, Instituto Politécnico Nacional, CP 07360, México, DF, Mexico
*Correspondence e-mail: chemax7@yahoo.com.mx
In the title compound, [Co2(C7H5O2)4(C10H8N2)4]·6C6H5COOH, the centrosymmetric cobalt dimer co-crystallizes with six molecules of benzoic acid. Each CoII atom is coordinated by four O atoms in a distorted square-planar arrangement while the N atoms are located in apical positions. The dihedral angles between the rings comprising each of the 4,4′-bipyridyl ligands are 25.2 (2) and 22.8 (2)°. In the crystal, the three-dimensional network is assembled by O—H⋯O and C—H⋯O hydrogen bonds.
CCDC reference: 942607
Related literature
For polymer structures with benzoate and 4,4′-bipyridyl ligands coordinated to cobalt(II), see: Song et al. (2009), Zhang et al. (2007); to copper(II), see: Wu et al. (2007); to cadmium(II) and zinc(II), see: Murugesapandian & Roesky (2011a,b).
Experimental
Crystal data
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Data collection: COLLECT (Bruker, 2004); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012), enCIFer (Allen, 2004) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 942607
https://doi.org/10.1107/S1600536813033357/mw2119sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033357/mw2119Isup2.hkl
A solution of cobalt(II) nitrate hexahydrate (93.1 mg 0.32 mmol) in 5 mL of deionized water was added dropwise to 5 mL of a methanol solution of benzoic anhydride (72.4 mg 0.32 mmol). The reaction mixture was refluxed at 80 °C without stirring after which a solution of 4,4'-bipyridine (50 mg 0.32 mmol) in 10 mL of methanol was slowly added at room temperature. The solid was crystallized from solution giving red crystals of the title compound which were suitablefor X-ray
analysis and fully characterized by standard analytical methods. M.p. > 350°C.H atoms were positioned geometrically and refined using a riding model approximation with distance O—H = 0.82 Å and C—H = 0.93 Å, with Uiso(H) = 1.2Ueq(C,O).
The design of metal-organic coordination compounds is of current interest in the fields of supramolecular chemistry and crystal engineering. This interest stems from their potential applications as functional materials, such as in gas storage, ion-exchange, catalysis, magnetism and molecular sensing (Song et al., 2009; Zhang et al., 2007). 4,4'-Bipyridine is an excellent, rigid bridging ligand for the construction of novel metal-organic coordination compounds due to its various coordinative modes with metal ions (Wu et al., 2007; Murugesapandian & Roesky, 2011a, 2011b). Currently all the metal-organic coordination compounds obtained with benzoic acid and 4,4'-bipyridine are polymeric. The title compound is the first example of a dimeric species with these two ligands.
The title compound is a cobalt(II) dimer having crystallographically-imposed centrosymmetry (Fig. 1) together with six molecules of benzoic acid in the lattice. Each cobalt(II) ion displays a distorted octahedral coordination geometry being surrounded by four oxygen atoms of one chelating and two bridging benzoate anions and two trans-disposed, monodentate 4,4'-bipyridine ligands. In the central portion of the dimer, the two metal ions and the two bidentate bridging benzoate ions form an eight-membered ring. The dihedral angles between the rings of the 4,4'-bipyridine ligands are 25.2 (2)° (ligand containing N1 and N2) and 22.8 (2)° (ligand containing N3 and N5). In the
weak O—H···O and C—H···O hydrogen bonds link the molecules into an infinite one-dimensional chain extending along the b axis [O7—H7a···O1,1.859 Å, 164.10°; C6—H6···O2, 2.366 Å, 167.54°]. (Fig. 2).For polymer structures with benzoate and 4,4'-bipyridyl ligands coordinated to cobalt(II), see: Song et al. (2009), Zhang et al. (2007); to copper(II), see: Wu et al. (2007); to cadmium(II) and zinc(II), see: Murugesapandian & Roesky (2011a,b).
Data collection: COLLECT (Bruker, 2004); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012), enCIFer (Allen, 2004) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level, three benzoic acid molecules are represented by sticks and H atoms are omitted for clarity. | |
Fig. 2. Crystal packing of the title compound viewed along b axis. Intermolecular hydrogen bonds are shown as blue dashed lines. |
[Co2(C7H5O2)4(C10H8N2)4]·6C7H6O2 | Z = 1 |
Mr = 1959.74 | F(000) = 1018 |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
Hall symbol: -P 1 | Melting point: 350 K |
a = 10.4977 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.8329 (7) Å | Cell parameters from 28061 reflections |
c = 16.3994 (8) Å | θ = 1.0–27.5° |
α = 64.222 (3)° | µ = 0.41 mm−1 |
β = 87.792 (3)° | T = 293 K |
γ = 86.469 (3)° | Prism, red |
V = 2449.6 (2) Å3 | 0.2 × 0.1 × 0.05 mm |
Nonius KappaCCD diffractometer | 11064 independent reflections |
Radiation source: Enraf–Nonius FR590 | 5118 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
Detector resolution: 9 pixels mm-1 | θmax = 27.4°, θmin = 2.4° |
CCD rotation images, thick slices scans | h = −13→12 |
Absorption correction: multi-scan (SORTAV; Blessing, 1987, 1989, 1995) | k = −20→20 |
Tmin = 0.925, Tmax = 0.980 | l = −20→21 |
28546 measured reflections |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0388P)2 + 1.8382P] where P = (Fo2 + 2Fc2)/3 |
11064 reflections | (Δ/σ)max = 0.001 |
631 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Co2(C7H5O2)4(C10H8N2)4]·6C7H6O2 | γ = 86.469 (3)° |
Mr = 1959.74 | V = 2449.6 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.4977 (6) Å | Mo Kα radiation |
b = 15.8329 (7) Å | µ = 0.41 mm−1 |
c = 16.3994 (8) Å | T = 293 K |
α = 64.222 (3)° | 0.2 × 0.1 × 0.05 mm |
β = 87.792 (3)° |
Nonius KappaCCD diffractometer | 11064 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1987, 1989, 1995) | 5118 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 0.980 | Rint = 0.082 |
28546 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.32 e Å−3 |
11064 reflections | Δρmin = −0.31 e Å−3 |
631 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 | 0.13907 (4) | 0.09130 (3) | 0.51110 (3) | 0.04482 (16) | |
O1 | 0.1879 (2) | 0.16963 (17) | 0.58558 (17) | 0.0566 (7) | |
O2 | 0.3130 (2) | 0.17380 (17) | 0.47431 (17) | 0.0573 (7) | |
O3 | −0.0072 (2) | 0.02611 (18) | 0.59081 (16) | 0.0605 (7) | |
O4 | 0.1804 (2) | 0.04234 (18) | 0.41807 (16) | 0.0563 (7) | |
N1 | 0.0204 (3) | 0.2073 (2) | 0.4218 (2) | 0.0511 (8) | |
N2 | −0.3787 (5) | 0.6089 (3) | 0.1719 (3) | 0.0927 (13) | |
N3 | 0.2633 (3) | −0.0192 (2) | 0.60462 (19) | 0.0477 (7) | |
N5 | 0.6503 (5) | −0.3951 (3) | 0.9135 (3) | 0.0887 (12) | |
C1 | 0.4254 (3) | −0.1614 (2) | 0.7278 (2) | 0.0517 (9) | |
C2 | 0.5065 (4) | −0.2405 (3) | 0.7921 (3) | 0.0583 (10) | |
C3 | 0.3224 (4) | −0.1222 (3) | 0.7567 (3) | 0.0636 (11) | |
H3 | 0.3052 | −0.1427 | 0.8182 | 0.076* | |
C4 | 0.2452 (4) | −0.0522 (3) | 0.6933 (3) | 0.0602 (10) | |
H4 | 0.1765 | −0.0268 | 0.7143 | 0.072* | |
C5 | 0.3647 (3) | −0.0556 (2) | 0.5767 (2) | 0.0490 (9) | |
H5 | 0.3806 | −0.0327 | 0.5148 | 0.059* | |
C6 | 0.4468 (3) | −0.1251 (2) | 0.6347 (2) | 0.0516 (9) | |
H6 | 0.5162 | −0.1478 | 0.6118 | 0.062* | |
C7 | 0.4598 (5) | −0.2980 (3) | 0.8773 (3) | 0.0776 (13) | |
H7 | 0.3786 | −0.2856 | 0.8956 | 0.093* | |
C8 | 0.5339 (6) | −0.3730 (3) | 0.9344 (3) | 0.0919 (16) | |
H8 | 0.5007 | −0.4106 | 0.9913 | 0.11* | |
C9 | 0.6958 (5) | −0.3408 (4) | 0.8324 (4) | 0.0938 (16) | |
H9 | 0.777 | −0.3556 | 0.8161 | 0.113* | |
C10 | 0.6279 (4) | −0.2627 (3) | 0.7704 (3) | 0.0837 (14) | |
H10 | 0.6642 | −0.2254 | 0.7145 | 0.1* | |
C11 | −0.1404 (4) | 0.3636 (3) | 0.3194 (2) | 0.0538 (10) | |
C12 | −0.2251 (4) | 0.4474 (3) | 0.2685 (3) | 0.0605 (10) | |
C13 | −0.1842 (4) | 0.2761 (3) | 0.3651 (3) | 0.0786 (14) | |
H13 | −0.2705 | 0.2668 | 0.3634 | 0.094* | |
C14 | −0.1030 (4) | 0.2013 (3) | 0.4138 (3) | 0.0778 (14) | |
H14 | −0.1368 | 0.1424 | 0.4431 | 0.093* | |
C15 | 0.0627 (4) | 0.2928 (3) | 0.3749 (3) | 0.0853 (15) | |
H15 | 0.1494 | 0.3005 | 0.377 | 0.102* | |
C16 | −0.0126 (4) | 0.3702 (3) | 0.3238 (3) | 0.0846 (15) | |
H16 | 0.0239 | 0.4278 | 0.2918 | 0.101* | |
C17 | −0.1911 (5) | 0.5364 (3) | 0.2540 (3) | 0.0911 (16) | |
H17 | −0.1145 | 0.5437 | 0.2763 | 0.109* | |
C18 | −0.2705 (6) | 0.6136 (4) | 0.2066 (4) | 0.1049 (18) | |
H18 | −0.2462 | 0.6722 | 0.1988 | 0.126* | |
C19 | −0.4141 (5) | 0.5272 (5) | 0.1853 (3) | 0.0924 (16) | |
H19 | −0.4916 | 0.5231 | 0.1619 | 0.111* | |
C20 | −0.3392 (5) | 0.4428 (4) | 0.2345 (3) | 0.0889 (15) | |
H20 | −0.3682 | 0.3851 | 0.2433 | 0.107* | |
C21 | 0.2930 (3) | 0.1908 (2) | 0.5415 (3) | 0.0523 (9) | |
C22 | 0.3932 (4) | 0.2327 (3) | 0.5724 (3) | 0.0592 (10) | |
C23 | 0.3760 (4) | 0.2431 (3) | 0.6515 (3) | 0.0746 (12) | |
H23 | 0.3006 | 0.2258 | 0.6849 | 0.089* | |
C24 | 0.4712 (5) | 0.2794 (4) | 0.6811 (4) | 0.1020 (17) | |
H24 | 0.4595 | 0.2866 | 0.7342 | 0.122* | |
C25 | 0.5817 (6) | 0.3044 (4) | 0.6327 (5) | 0.116 (2) | |
H25 | 0.6454 | 0.3289 | 0.6527 | 0.14* | |
C26 | 0.5993 (5) | 0.2940 (5) | 0.5558 (5) | 0.124 (2) | |
H26 | 0.6753 | 0.3112 | 0.5231 | 0.149* | |
C27 | 0.5054 (4) | 0.2580 (4) | 0.5248 (4) | 0.0937 (16) | |
H27 | 0.5186 | 0.2509 | 0.4716 | 0.112* | |
C28 | −0.1194 (3) | 0.0033 (2) | 0.6124 (2) | 0.0420 (8) | |
C29 | −0.1875 (3) | 0.0308 (2) | 0.6794 (2) | 0.0431 (8) | |
C30 | −0.3148 (4) | 0.0119 (3) | 0.7003 (3) | 0.0595 (10) | |
H30 | −0.3578 | −0.0171 | 0.6716 | 0.071* | |
C31 | −0.3783 (4) | 0.0354 (4) | 0.7630 (3) | 0.0842 (14) | |
H31 | −0.464 | 0.023 | 0.7763 | 0.101* | |
C32 | −0.3144 (6) | 0.0772 (4) | 0.8054 (3) | 0.0948 (16) | |
H32 | −0.3569 | 0.0923 | 0.8484 | 0.114* | |
C33 | −0.1893 (5) | 0.0970 (3) | 0.7856 (3) | 0.0824 (14) | |
H33 | −0.1472 | 0.1257 | 0.815 | 0.099* | |
C34 | −0.1249 (4) | 0.0747 (3) | 0.7221 (3) | 0.0609 (10) | |
H34 | −0.0399 | 0.0891 | 0.7079 | 0.073* | |
O5 | 0.3391 (4) | 0.6953 (3) | 0.0736 (3) | 0.1194 (14) | |
O6 | 0.5022 (4) | 0.7786 (2) | 0.0694 (2) | 0.1021 (11) | |
H6A | 0.5358 | 0.7265 | 0.0994 | 0.153* | |
C42 | 0.3856 (6) | 0.7699 (4) | 0.0509 (3) | 0.0842 (14) | |
C43 | 0.3183 (4) | 0.8629 (3) | −0.0038 (3) | 0.0627 (11) | |
C44 | 0.1891 (5) | 0.8649 (4) | −0.0154 (3) | 0.0866 (14) | |
H44 | 0.146 | 0.8094 | 0.0106 | 0.104* | |
C45 | 0.1230 (5) | 0.9484 (5) | −0.0651 (4) | 0.1014 (17) | |
H45 | 0.0355 | 0.9495 | −0.0725 | 0.122* | |
C46 | 0.1856 (6) | 1.0296 (4) | −0.1035 (4) | 0.1030 (18) | |
H46 | 0.1408 | 1.0863 | −0.1365 | 0.124* | |
C47 | 0.3141 (6) | 1.0277 (3) | −0.0935 (3) | 0.0933 (16) | |
H47 | 0.3571 | 1.0831 | −0.1208 | 0.112* | |
C48 | 0.3802 (5) | 0.9451 (3) | −0.0436 (3) | 0.0749 (12) | |
H48 | 0.4678 | 0.9446 | −0.0366 | 0.09* | |
O7 | −0.0189 (3) | 0.6991 (2) | 0.4128 (2) | 0.0877 (9) | |
H7A | −0.0735 | 0.7415 | 0.4032 | 0.132* | |
O8 | −0.0534 (3) | 0.7343 (2) | 0.2686 (3) | 0.0932 (10) | |
C49 | 0.0020 (4) | 0.6876 (3) | 0.3376 (4) | 0.0683 (12) | |
C50 | 0.1003 (4) | 0.6121 (3) | 0.3495 (3) | 0.0649 (11) | |
C51 | 0.1503 (4) | 0.6056 (3) | 0.2726 (4) | 0.0782 (13) | |
H51 | 0.1215 | 0.6478 | 0.2156 | 0.094* | |
C52 | 0.2422 (5) | 0.5369 (4) | 0.2805 (5) | 0.0965 (16) | |
H52 | 0.2754 | 0.5326 | 0.229 | 0.116* | |
C53 | 0.2843 (6) | 0.4755 (4) | 0.3636 (6) | 0.1079 (19) | |
H53 | 0.3467 | 0.4292 | 0.3685 | 0.129* | |
C54 | 0.2367 (5) | 0.4804 (4) | 0.4403 (5) | 0.1045 (18) | |
H54 | 0.2661 | 0.4377 | 0.4969 | 0.125* | |
C55 | 0.1436 (5) | 0.5500 (3) | 0.4328 (4) | 0.0834 (14) | |
H55 | 0.1109 | 0.5541 | 0.4846 | 0.1* | |
O9 | −0.2055 (3) | 0.4497 (2) | 0.0229 (2) | 0.0972 (10) | |
H9A | −0.2473 | 0.4977 | −0.0088 | 0.146* | |
O10 | −0.0947 (3) | 0.4821 (2) | −0.1046 (2) | 0.1078 (12) | |
C35 | −0.1129 (5) | 0.4338 (3) | −0.0259 (4) | 0.0774 (13) | |
C36 | −0.0322 (4) | 0.3462 (3) | 0.0283 (3) | 0.0711 (12) | |
C37 | 0.0617 (5) | 0.3194 (4) | −0.0164 (4) | 0.1078 (19) | |
H37 | 0.0745 | 0.3556 | −0.0781 | 0.129* | |
C38 | 0.1384 (6) | 0.2389 (4) | 0.0287 (4) | 0.118 (2) | |
H38 | 0.2014 | 0.2205 | −0.0026 | 0.141* | |
C39 | 0.1209 (6) | 0.1874 (4) | 0.1187 (4) | 0.1061 (18) | |
H39 | 0.173 | 0.1339 | 0.1498 | 0.127* | |
C40 | 0.0265 (6) | 0.2138 (4) | 0.1645 (4) | 0.1014 (17) | |
H40 | 0.0138 | 0.178 | 0.2262 | 0.122* | |
C41 | −0.0491 (5) | 0.2937 (3) | 0.1181 (3) | 0.0863 (14) | |
H41 | −0.1128 | 0.3119 | 0.1491 | 0.104* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0362 (3) | 0.0504 (3) | 0.0510 (3) | −0.0013 (2) | 0.0021 (2) | −0.0252 (2) |
O1 | 0.0409 (15) | 0.0625 (16) | 0.0784 (18) | −0.0047 (12) | 0.0067 (13) | −0.0421 (14) |
O2 | 0.0486 (16) | 0.0696 (17) | 0.0632 (17) | −0.0057 (13) | 0.0042 (13) | −0.0378 (15) |
O3 | 0.0380 (15) | 0.0825 (18) | 0.0580 (16) | −0.0074 (13) | 0.0108 (12) | −0.0280 (14) |
O4 | 0.0479 (16) | 0.0741 (17) | 0.0585 (16) | −0.0023 (13) | 0.0033 (12) | −0.0400 (14) |
N1 | 0.0431 (19) | 0.0514 (19) | 0.0581 (19) | −0.0026 (15) | 0.0005 (15) | −0.0230 (16) |
N2 | 0.089 (3) | 0.100 (3) | 0.078 (3) | 0.026 (3) | −0.013 (2) | −0.031 (3) |
N3 | 0.0403 (18) | 0.0574 (18) | 0.0470 (19) | −0.0008 (14) | 0.0029 (14) | −0.0246 (15) |
N5 | 0.101 (3) | 0.070 (3) | 0.077 (3) | 0.016 (2) | −0.021 (3) | −0.017 (2) |
C1 | 0.043 (2) | 0.055 (2) | 0.055 (2) | −0.0056 (18) | 0.0011 (18) | −0.0213 (19) |
C2 | 0.055 (3) | 0.051 (2) | 0.063 (3) | 0.0023 (19) | −0.008 (2) | −0.019 (2) |
C3 | 0.061 (3) | 0.077 (3) | 0.048 (2) | 0.011 (2) | 0.002 (2) | −0.025 (2) |
C4 | 0.049 (2) | 0.075 (3) | 0.060 (3) | 0.008 (2) | 0.005 (2) | −0.034 (2) |
C5 | 0.037 (2) | 0.058 (2) | 0.048 (2) | −0.0008 (17) | 0.0086 (17) | −0.0211 (19) |
C6 | 0.033 (2) | 0.057 (2) | 0.062 (2) | 0.0048 (17) | 0.0045 (18) | −0.024 (2) |
C7 | 0.084 (3) | 0.073 (3) | 0.063 (3) | 0.014 (3) | 0.000 (2) | −0.019 (2) |
C8 | 0.108 (5) | 0.081 (3) | 0.068 (3) | 0.018 (3) | 0.001 (3) | −0.018 (3) |
C9 | 0.059 (3) | 0.088 (3) | 0.109 (4) | 0.018 (3) | −0.005 (3) | −0.022 (3) |
C10 | 0.061 (3) | 0.079 (3) | 0.085 (3) | 0.014 (2) | −0.005 (3) | −0.014 (3) |
C11 | 0.046 (2) | 0.059 (2) | 0.053 (2) | 0.0037 (19) | −0.0004 (18) | −0.021 (2) |
C12 | 0.051 (3) | 0.067 (3) | 0.061 (3) | 0.009 (2) | −0.002 (2) | −0.026 (2) |
C13 | 0.046 (3) | 0.076 (3) | 0.088 (3) | −0.010 (2) | −0.021 (2) | −0.009 (3) |
C14 | 0.060 (3) | 0.060 (3) | 0.091 (3) | −0.016 (2) | −0.020 (2) | −0.008 (2) |
C15 | 0.047 (3) | 0.062 (3) | 0.115 (4) | −0.002 (2) | −0.004 (3) | −0.009 (3) |
C16 | 0.054 (3) | 0.055 (3) | 0.115 (4) | −0.003 (2) | −0.012 (3) | −0.009 (3) |
C17 | 0.067 (3) | 0.067 (3) | 0.114 (4) | 0.012 (3) | −0.010 (3) | −0.016 (3) |
C18 | 0.099 (5) | 0.079 (4) | 0.115 (5) | 0.019 (3) | −0.006 (4) | −0.025 (3) |
C19 | 0.072 (4) | 0.125 (5) | 0.089 (4) | 0.013 (3) | −0.025 (3) | −0.056 (4) |
C20 | 0.079 (4) | 0.087 (3) | 0.105 (4) | 0.020 (3) | −0.036 (3) | −0.046 (3) |
C21 | 0.041 (2) | 0.045 (2) | 0.069 (3) | 0.0019 (17) | −0.003 (2) | −0.024 (2) |
C22 | 0.047 (2) | 0.064 (2) | 0.076 (3) | −0.0024 (19) | −0.007 (2) | −0.038 (2) |
C23 | 0.055 (3) | 0.094 (3) | 0.087 (3) | −0.008 (2) | −0.008 (2) | −0.050 (3) |
C24 | 0.075 (4) | 0.151 (5) | 0.121 (4) | −0.015 (4) | −0.005 (3) | −0.096 (4) |
C25 | 0.078 (4) | 0.158 (6) | 0.155 (6) | −0.038 (4) | −0.005 (4) | −0.103 (5) |
C26 | 0.077 (4) | 0.186 (6) | 0.151 (6) | −0.068 (4) | 0.023 (4) | −0.105 (5) |
C27 | 0.063 (3) | 0.129 (4) | 0.116 (4) | −0.042 (3) | 0.024 (3) | −0.076 (4) |
C28 | 0.034 (2) | 0.0437 (19) | 0.0396 (19) | 0.0041 (16) | −0.0016 (16) | −0.0107 (16) |
C29 | 0.041 (2) | 0.0428 (19) | 0.043 (2) | 0.0038 (16) | −0.0002 (16) | −0.0167 (16) |
C30 | 0.047 (2) | 0.075 (3) | 0.064 (3) | −0.005 (2) | 0.012 (2) | −0.038 (2) |
C31 | 0.058 (3) | 0.124 (4) | 0.091 (3) | −0.010 (3) | 0.025 (3) | −0.067 (3) |
C32 | 0.096 (4) | 0.122 (4) | 0.091 (4) | 0.001 (3) | 0.024 (3) | −0.072 (3) |
C33 | 0.093 (4) | 0.096 (4) | 0.082 (3) | −0.007 (3) | −0.001 (3) | −0.061 (3) |
C34 | 0.055 (3) | 0.070 (3) | 0.065 (3) | −0.004 (2) | −0.001 (2) | −0.036 (2) |
O5 | 0.145 (4) | 0.067 (2) | 0.124 (3) | −0.001 (2) | 0.011 (3) | −0.022 (2) |
O6 | 0.107 (3) | 0.089 (2) | 0.102 (3) | 0.032 (2) | −0.035 (2) | −0.035 (2) |
C42 | 0.100 (4) | 0.090 (4) | 0.067 (3) | 0.016 (3) | −0.004 (3) | −0.040 (3) |
C43 | 0.070 (3) | 0.067 (3) | 0.050 (2) | 0.017 (2) | −0.004 (2) | −0.027 (2) |
C44 | 0.087 (4) | 0.085 (3) | 0.092 (4) | −0.003 (3) | 0.001 (3) | −0.041 (3) |
C45 | 0.065 (4) | 0.125 (5) | 0.124 (5) | 0.015 (4) | −0.012 (3) | −0.065 (4) |
C46 | 0.107 (5) | 0.097 (4) | 0.094 (4) | 0.036 (4) | −0.027 (4) | −0.033 (3) |
C47 | 0.101 (4) | 0.073 (3) | 0.092 (4) | 0.001 (3) | −0.008 (3) | −0.023 (3) |
C48 | 0.071 (3) | 0.077 (3) | 0.066 (3) | 0.010 (3) | −0.008 (2) | −0.022 (2) |
O7 | 0.084 (2) | 0.082 (2) | 0.095 (2) | 0.0141 (17) | 0.0120 (18) | −0.0397 (19) |
O8 | 0.075 (2) | 0.102 (2) | 0.107 (3) | 0.0221 (19) | −0.018 (2) | −0.050 (2) |
C49 | 0.053 (3) | 0.064 (3) | 0.092 (4) | −0.006 (2) | 0.009 (3) | −0.038 (3) |
C50 | 0.047 (3) | 0.056 (3) | 0.091 (3) | −0.009 (2) | 0.008 (2) | −0.031 (3) |
C51 | 0.058 (3) | 0.083 (3) | 0.102 (4) | −0.003 (3) | 0.005 (3) | −0.048 (3) |
C52 | 0.071 (4) | 0.101 (4) | 0.143 (5) | −0.001 (3) | 0.013 (3) | −0.079 (4) |
C53 | 0.087 (4) | 0.075 (4) | 0.163 (6) | 0.008 (3) | 0.014 (4) | −0.056 (4) |
C54 | 0.093 (4) | 0.067 (3) | 0.124 (5) | 0.006 (3) | 0.003 (4) | −0.015 (3) |
C55 | 0.075 (3) | 0.062 (3) | 0.100 (4) | −0.001 (3) | 0.017 (3) | −0.025 (3) |
O9 | 0.095 (3) | 0.089 (2) | 0.091 (2) | 0.0281 (19) | −0.011 (2) | −0.0262 (19) |
O10 | 0.103 (3) | 0.089 (2) | 0.085 (3) | 0.017 (2) | 0.000 (2) | 0.002 (2) |
C35 | 0.072 (3) | 0.073 (3) | 0.076 (3) | 0.005 (3) | −0.011 (3) | −0.022 (3) |
C36 | 0.066 (3) | 0.061 (3) | 0.072 (3) | 0.001 (2) | −0.009 (2) | −0.015 (2) |
C37 | 0.095 (4) | 0.099 (4) | 0.087 (4) | 0.018 (3) | 0.011 (3) | −0.004 (3) |
C38 | 0.099 (4) | 0.104 (4) | 0.113 (5) | 0.033 (4) | 0.011 (4) | −0.018 (4) |
C39 | 0.093 (4) | 0.080 (4) | 0.109 (5) | 0.016 (3) | −0.019 (4) | −0.008 (3) |
C40 | 0.108 (5) | 0.091 (4) | 0.076 (3) | 0.006 (3) | −0.016 (3) | −0.009 (3) |
C41 | 0.092 (4) | 0.082 (3) | 0.077 (3) | 0.008 (3) | −0.013 (3) | −0.028 (3) |
Co1—O3 | 1.999 (2) | C26—C27 | 1.384 (6) |
Co1—O4 | 2.013 (2) | C26—H26 | 0.93 |
Co1—N1 | 2.142 (3) | C27—H27 | 0.93 |
Co1—N3 | 2.157 (3) | C28—O4i | 1.257 (4) |
Co1—O1 | 2.176 (2) | C28—C29 | 1.491 (5) |
Co1—O2 | 2.220 (2) | C29—C30 | 1.385 (5) |
O1—C21 | 1.275 (4) | C29—C34 | 1.385 (5) |
O2—C21 | 1.250 (4) | C30—C31 | 1.374 (5) |
O3—C28 | 1.247 (4) | C30—H30 | 0.93 |
O4—C28i | 1.257 (4) | C31—C32 | 1.364 (6) |
N1—C14 | 1.321 (5) | C31—H31 | 0.93 |
N1—C15 | 1.327 (5) | C32—C33 | 1.363 (6) |
N2—C19 | 1.290 (6) | C32—H32 | 0.93 |
N2—C18 | 1.311 (6) | C33—C34 | 1.380 (6) |
N3—C4 | 1.324 (4) | C33—H33 | 0.93 |
N3—C5 | 1.338 (4) | C34—H34 | 0.93 |
N5—C9 | 1.320 (6) | O5—C42 | 1.204 (6) |
N5—C8 | 1.324 (6) | O6—C42 | 1.302 (6) |
C1—C3 | 1.383 (5) | O6—H6A | 0.82 |
C1—C6 | 1.392 (5) | C42—C43 | 1.497 (6) |
C1—C2 | 1.482 (5) | C43—C48 | 1.370 (6) |
C2—C10 | 1.375 (6) | C43—C44 | 1.374 (6) |
C2—C7 | 1.385 (5) | C44—C45 | 1.374 (7) |
C3—C4 | 1.385 (5) | C44—H44 | 0.93 |
C3—H3 | 0.93 | C45—C46 | 1.359 (7) |
C4—H4 | 0.93 | C45—H45 | 0.93 |
C5—C6 | 1.376 (5) | C46—C47 | 1.362 (7) |
C5—H5 | 0.93 | C46—H46 | 0.93 |
C6—H6 | 0.93 | C47—C48 | 1.365 (6) |
C7—C8 | 1.367 (6) | C47—H47 | 0.93 |
C7—H7 | 0.93 | C48—H48 | 0.93 |
C8—H8 | 0.93 | O7—C49 | 1.330 (5) |
C9—C10 | 1.388 (6) | O7—H7A | 0.82 |
C9—H9 | 0.93 | O8—C49 | 1.198 (5) |
C10—H10 | 0.93 | C49—C50 | 1.482 (6) |
C11—C13 | 1.358 (5) | C50—C55 | 1.366 (6) |
C11—C16 | 1.359 (5) | C50—C51 | 1.390 (6) |
C11—C12 | 1.482 (5) | C51—C52 | 1.373 (6) |
C12—C20 | 1.359 (6) | C51—H51 | 0.93 |
C12—C17 | 1.391 (6) | C52—C53 | 1.356 (8) |
C13—C14 | 1.368 (6) | C52—H52 | 0.93 |
C13—H13 | 0.93 | C53—C54 | 1.368 (8) |
C14—H14 | 0.93 | C53—H53 | 0.93 |
C15—C16 | 1.367 (6) | C54—C55 | 1.394 (7) |
C15—H15 | 0.93 | C54—H54 | 0.93 |
C16—H16 | 0.93 | C55—H55 | 0.93 |
C17—C18 | 1.375 (6) | O9—C35 | 1.316 (5) |
C17—H17 | 0.93 | O9—H9A | 0.82 |
C18—H18 | 0.93 | O10—C35 | 1.196 (5) |
C19—C20 | 1.427 (7) | C35—C36 | 1.507 (6) |
C19—H19 | 0.93 | C36—C41 | 1.350 (6) |
C20—H20 | 0.93 | C36—C37 | 1.362 (6) |
C21—C22 | 1.491 (5) | C37—C38 | 1.385 (7) |
C22—C27 | 1.368 (5) | C37—H37 | 0.93 |
C22—C23 | 1.382 (5) | C38—C39 | 1.352 (7) |
C23—C24 | 1.383 (6) | C38—H38 | 0.93 |
C23—H23 | 0.93 | C39—C40 | 1.372 (7) |
C24—C25 | 1.358 (7) | C39—H39 | 0.93 |
C24—H24 | 0.93 | C40—C41 | 1.377 (7) |
C25—C26 | 1.346 (7) | C40—H40 | 0.93 |
C25—H25 | 0.93 | C41—H41 | 0.93 |
O3—Co1—O4 | 111.24 (10) | C23—C24—H24 | 119.9 |
O3—Co1—N1 | 93.58 (11) | C26—C25—C24 | 120.2 (5) |
O4—Co1—N1 | 93.96 (11) | C26—C25—H25 | 119.9 |
O3—Co1—N3 | 87.57 (11) | C24—C25—H25 | 119.9 |
O4—Co1—N3 | 89.12 (11) | C25—C26—C27 | 120.7 (5) |
N1—Co1—N3 | 176.07 (11) | C25—C26—H26 | 119.7 |
O3—Co1—O1 | 96.72 (10) | C27—C26—H26 | 119.7 |
O4—Co1—O1 | 151.17 (10) | C22—C27—C26 | 120.0 (5) |
N1—Co1—O1 | 91.07 (10) | C22—C27—H27 | 120 |
N3—Co1—O1 | 85.06 (10) | C26—C27—H27 | 120 |
O3—Co1—O2 | 155.49 (10) | O3—C28—O4i | 124.4 (3) |
O4—Co1—O2 | 91.70 (10) | O3—C28—C29 | 118.8 (3) |
N1—Co1—O2 | 93.29 (10) | O4i—C28—C29 | 116.8 (3) |
N3—Co1—O2 | 84.17 (10) | C30—C29—C34 | 119.0 (3) |
O1—Co1—O2 | 59.65 (9) | C30—C29—C28 | 120.1 (3) |
C21—O1—Co1 | 90.4 (2) | C34—C29—C28 | 120.9 (3) |
C21—O2—Co1 | 89.0 (2) | C31—C30—C29 | 120.8 (4) |
C28—O3—Co1 | 157.9 (2) | C31—C30—H30 | 119.6 |
C28i—O4—Co1 | 133.3 (2) | C29—C30—H30 | 119.6 |
C14—N1—C15 | 114.3 (3) | C32—C31—C30 | 119.3 (4) |
C14—N1—Co1 | 122.7 (3) | C32—C31—H31 | 120.3 |
C15—N1—Co1 | 122.8 (3) | C30—C31—H31 | 120.3 |
C19—N2—C18 | 118.2 (5) | C33—C32—C31 | 121.1 (4) |
C4—N3—C5 | 116.6 (3) | C33—C32—H32 | 119.5 |
C4—N3—Co1 | 121.2 (2) | C31—C32—H32 | 119.5 |
C5—N3—Co1 | 122.2 (2) | C32—C33—C34 | 120.1 (4) |
C9—N5—C8 | 117.2 (4) | C32—C33—H33 | 119.9 |
C3—C1—C6 | 116.7 (3) | C34—C33—H33 | 119.9 |
C3—C1—C2 | 121.9 (3) | C33—C34—C29 | 119.7 (4) |
C6—C1—C2 | 121.3 (3) | C33—C34—H34 | 120.2 |
C10—C2—C7 | 116.9 (4) | C29—C34—H34 | 120.2 |
C10—C2—C1 | 122.8 (4) | C42—O6—H6A | 109.6 |
C7—C2—C1 | 120.3 (4) | O5—C42—O6 | 123.4 (5) |
C1—C3—C4 | 119.5 (4) | O5—C42—C43 | 124.3 (6) |
C1—C3—H3 | 120.2 | O6—C42—C43 | 112.3 (5) |
C4—C3—H3 | 120.2 | C48—C43—C44 | 119.0 (4) |
N3—C4—C3 | 123.9 (4) | C48—C43—C42 | 122.9 (5) |
N3—C4—H4 | 118 | C44—C43—C42 | 118.1 (5) |
C3—C4—H4 | 118 | C43—C44—C45 | 120.3 (5) |
N3—C5—C6 | 123.6 (3) | C43—C44—H44 | 119.9 |
N3—C5—H5 | 118.2 | C45—C44—H44 | 119.9 |
C6—C5—H5 | 118.2 | C46—C45—C44 | 120.1 (5) |
C5—C6—C1 | 119.7 (3) | C46—C45—H45 | 120 |
C5—C6—H6 | 120.2 | C44—C45—H45 | 120 |
C1—C6—H6 | 120.2 | C45—C46—C47 | 119.8 (5) |
C8—C7—C2 | 119.5 (5) | C45—C46—H46 | 120.1 |
C8—C7—H7 | 120.3 | C47—C46—H46 | 120.1 |
C2—C7—H7 | 120.3 | C46—C47—C48 | 120.5 (5) |
N5—C8—C7 | 123.8 (5) | C46—C47—H47 | 119.8 |
N5—C8—H8 | 118.1 | C48—C47—H47 | 119.8 |
C7—C8—H8 | 118.1 | C47—C48—C43 | 120.3 (5) |
N5—C9—C10 | 122.9 (5) | C47—C48—H48 | 119.8 |
N5—C9—H9 | 118.5 | C43—C48—H48 | 119.8 |
C10—C9—H9 | 118.5 | C49—O7—H7A | 109.3 |
C2—C10—C9 | 119.7 (4) | O8—C49—O7 | 122.7 (4) |
C2—C10—H10 | 120.2 | O8—C49—C50 | 124.7 (5) |
C9—C10—H10 | 120.2 | O7—C49—C50 | 112.5 (5) |
C13—C11—C16 | 115.6 (4) | C55—C50—C51 | 119.5 (4) |
C13—C11—C12 | 122.9 (4) | C55—C50—C49 | 122.2 (5) |
C16—C11—C12 | 121.5 (4) | C51—C50—C49 | 118.3 (4) |
C20—C12—C17 | 116.1 (4) | C52—C51—C50 | 120.2 (5) |
C20—C12—C11 | 123.2 (4) | C52—C51—H51 | 119.9 |
C17—C12—C11 | 120.7 (4) | C50—C51—H51 | 119.9 |
C11—C13—C14 | 120.8 (4) | C53—C52—C51 | 119.9 (5) |
C11—C13—H13 | 119.6 | C53—C52—H52 | 120.1 |
C14—C13—H13 | 119.6 | C51—C52—H52 | 120.1 |
N1—C14—C13 | 124.3 (4) | C52—C53—C54 | 121.1 (5) |
N1—C14—H14 | 117.9 | C52—C53—H53 | 119.5 |
C13—C14—H14 | 117.9 | C54—C53—H53 | 119.5 |
N1—C15—C16 | 124.5 (4) | C53—C54—C55 | 119.4 (6) |
N1—C15—H15 | 117.8 | C53—C54—H54 | 120.3 |
C16—C15—H15 | 117.8 | C55—C54—H54 | 120.3 |
C11—C16—C15 | 120.4 (4) | C50—C55—C54 | 119.9 (5) |
C11—C16—H16 | 119.8 | C50—C55—H55 | 120 |
C15—C16—H16 | 119.8 | C54—C55—H55 | 120 |
C18—C17—C12 | 120.1 (5) | C35—O9—H9A | 109.7 |
C18—C17—H17 | 119.9 | O10—C35—O9 | 124.4 (5) |
C12—C17—H17 | 119.9 | O10—C35—C36 | 123.1 (5) |
N2—C18—C17 | 123.3 (5) | O9—C35—C36 | 112.5 (4) |
N2—C18—H18 | 118.3 | C41—C36—C37 | 119.1 (4) |
C17—C18—H18 | 118.3 | C41—C36—C35 | 123.2 (5) |
N2—C19—C20 | 122.6 (5) | C37—C36—C35 | 117.7 (4) |
N2—C19—H19 | 118.7 | C36—C37—C38 | 120.9 (5) |
C20—C19—H19 | 118.7 | C36—C37—H37 | 119.5 |
C12—C20—C19 | 119.6 (5) | C38—C37—H37 | 119.5 |
C12—C20—H20 | 120.2 | C39—C38—C37 | 119.3 (6) |
C19—C20—H20 | 120.2 | C39—C38—H38 | 120.3 |
O2—C21—O1 | 120.0 (3) | C37—C38—H38 | 120.3 |
O2—C21—C22 | 120.3 (3) | C38—C39—C40 | 120.2 (5) |
O1—C21—C22 | 119.7 (4) | C38—C39—H39 | 119.9 |
C27—C22—C23 | 119.0 (4) | C40—C39—H39 | 119.9 |
C27—C22—C21 | 120.6 (4) | C39—C40—C41 | 119.4 (5) |
C23—C22—C21 | 120.3 (4) | C39—C40—H40 | 120.3 |
C22—C23—C24 | 119.9 (4) | C41—C40—H40 | 120.3 |
C22—C23—H23 | 120 | C36—C41—C40 | 121.0 (5) |
C24—C23—H23 | 120 | C36—C41—H41 | 119.5 |
C25—C24—C23 | 120.2 (5) | C40—C41—H41 | 119.5 |
C25—C24—H24 | 119.9 | ||
O3—Co1—O1—C21 | 167.4 (2) | C11—C12—C17—C18 | 179.9 (4) |
O4—Co1—O1—C21 | 1.4 (3) | C19—N2—C18—C17 | 2.2 (9) |
N1—Co1—O1—C21 | −98.8 (2) | C12—C17—C18—N2 | −1.2 (9) |
N3—Co1—O1—C21 | 80.5 (2) | C18—N2—C19—C20 | −1.3 (8) |
O2—Co1—O1—C21 | −5.7 (2) | C17—C12—C20—C19 | 1.6 (7) |
O3—Co1—O2—C21 | −11.0 (4) | C11—C12—C20—C19 | −179.1 (4) |
O4—Co1—O2—C21 | −170.8 (2) | N2—C19—C20—C12 | −0.6 (8) |
N1—Co1—O2—C21 | 95.1 (2) | Co1—O2—C21—O1 | −9.8 (3) |
N3—Co1—O2—C21 | −81.9 (2) | Co1—O2—C21—C22 | 168.1 (3) |
O1—Co1—O2—C21 | 5.8 (2) | Co1—O1—C21—O2 | 10.0 (3) |
O4—Co1—O3—C28 | −69.3 (7) | Co1—O1—C21—C22 | −167.9 (3) |
N1—Co1—O3—C28 | 26.4 (7) | O2—C21—C22—C27 | 3.6 (6) |
N3—Co1—O3—C28 | −157.4 (7) | O1—C21—C22—C27 | −178.4 (4) |
O1—Co1—O3—C28 | 117.9 (7) | O2—C21—C22—C23 | −173.8 (4) |
O2—Co1—O3—C28 | 132.4 (6) | O1—C21—C22—C23 | 4.2 (6) |
O3—Co1—O4—C28i | 18.2 (3) | C27—C22—C23—C24 | 0.5 (7) |
N1—Co1—O4—C28i | −77.2 (3) | C21—C22—C23—C24 | 177.9 (4) |
N3—Co1—O4—C28i | 105.2 (3) | C22—C23—C24—C25 | −0.2 (8) |
O1—Co1—O4—C28i | −176.7 (3) | C23—C24—C25—C26 | −0.1 (10) |
O2—Co1—O4—C28i | −170.6 (3) | C24—C25—C26—C27 | 0.2 (11) |
O3—Co1—N1—C14 | −23.0 (3) | C23—C22—C27—C26 | −0.5 (8) |
O4—Co1—N1—C14 | 88.6 (3) | C21—C22—C27—C26 | −177.9 (5) |
O1—Co1—N1—C14 | −119.8 (3) | C25—C26—C27—C22 | 0.2 (10) |
O2—Co1—N1—C14 | −179.4 (3) | Co1—O3—C28—O4i | 65.7 (8) |
O3—Co1—N1—C15 | 152.1 (3) | Co1—O3—C28—C29 | −114.8 (6) |
O4—Co1—N1—C15 | −96.3 (3) | O3—C28—C29—C30 | 175.8 (3) |
O1—Co1—N1—C15 | 55.3 (3) | O4i—C28—C29—C30 | −4.7 (5) |
O2—Co1—N1—C15 | −4.3 (3) | O3—C28—C29—C34 | −4.7 (5) |
O3—Co1—N3—C4 | −41.7 (3) | O4i—C28—C29—C34 | 174.9 (3) |
O4—Co1—N3—C4 | −153.0 (3) | C34—C29—C30—C31 | −0.6 (6) |
O1—Co1—N3—C4 | 55.3 (3) | C28—C29—C30—C31 | 179.0 (4) |
O2—Co1—N3—C4 | 115.2 (3) | C29—C30—C31—C32 | −0.6 (7) |
O3—Co1—N3—C5 | 140.8 (3) | C30—C31—C32—C33 | 0.9 (8) |
O4—Co1—N3—C5 | 29.5 (3) | C31—C32—C33—C34 | −0.2 (8) |
O1—Co1—N3—C5 | −122.3 (3) | C32—C33—C34—C29 | −1.0 (7) |
O2—Co1—N3—C5 | −62.3 (3) | C30—C29—C34—C33 | 1.3 (6) |
C3—C1—C2—C10 | −160.3 (4) | C28—C29—C34—C33 | −178.2 (4) |
C6—C1—C2—C10 | 22.2 (6) | O5—C42—C43—C48 | −166.7 (5) |
C3—C1—C2—C7 | 21.8 (6) | O6—C42—C43—C48 | 11.4 (6) |
C6—C1—C2—C7 | −155.8 (4) | O5—C42—C43—C44 | 12.2 (7) |
C6—C1—C3—C4 | 1.6 (6) | O6—C42—C43—C44 | −169.6 (4) |
C2—C1—C3—C4 | −176.0 (4) | C48—C43—C44—C45 | −0.9 (7) |
C5—N3—C4—C3 | −1.5 (6) | C42—C43—C44—C45 | −179.9 (4) |
Co1—N3—C4—C3 | −179.2 (3) | C43—C44—C45—C46 | 0.3 (8) |
C1—C3—C4—N3 | 0.0 (6) | C44—C45—C46—C47 | 0.8 (9) |
C4—N3—C5—C6 | 1.4 (5) | C45—C46—C47—C48 | −1.3 (9) |
Co1—N3—C5—C6 | 179.0 (3) | C46—C47—C48—C43 | 0.7 (8) |
N3—C5—C6—C1 | 0.3 (5) | C44—C43—C48—C47 | 0.4 (7) |
C3—C1—C6—C5 | −1.8 (5) | C42—C43—C48—C47 | 179.3 (4) |
C2—C1—C6—C5 | 175.9 (3) | O8—C49—C50—C55 | −167.8 (4) |
C10—C2—C7—C8 | −0.8 (7) | O7—C49—C50—C55 | 12.5 (6) |
C1—C2—C7—C8 | 177.3 (4) | O8—C49—C50—C51 | 12.8 (6) |
C9—N5—C8—C7 | 0.0 (8) | O7—C49—C50—C51 | −166.9 (4) |
C2—C7—C8—N5 | 0.1 (8) | C55—C50—C51—C52 | 0.2 (6) |
C8—N5—C9—C10 | 0.7 (8) | C49—C50—C51—C52 | 179.7 (4) |
C7—C2—C10—C9 | 1.4 (7) | C50—C51—C52—C53 | −0.1 (7) |
C1—C2—C10—C9 | −176.6 (4) | C51—C52—C53—C54 | 0.2 (9) |
N5—C9—C10—C2 | −1.5 (8) | C52—C53—C54—C55 | −0.3 (9) |
C13—C11—C12—C20 | −25.2 (6) | C51—C50—C55—C54 | −0.4 (7) |
C16—C11—C12—C20 | 155.5 (5) | C49—C50—C55—C54 | −179.8 (4) |
C13—C11—C12—C17 | 154.0 (5) | C53—C54—C55—C50 | 0.4 (8) |
C16—C11—C12—C17 | −25.2 (6) | O10—C35—C36—C41 | 177.0 (5) |
C16—C11—C13—C14 | 1.6 (7) | O9—C35—C36—C41 | −3.8 (7) |
C12—C11—C13—C14 | −177.7 (4) | O10—C35—C36—C37 | −3.2 (7) |
C15—N1—C14—C13 | −2.8 (7) | O9—C35—C36—C37 | 176.0 (5) |
Co1—N1—C14—C13 | 172.6 (4) | C41—C36—C37—C38 | 0.8 (9) |
C11—C13—C14—N1 | 1.3 (8) | C35—C36—C37—C38 | −179.1 (5) |
C14—N1—C15—C16 | 1.7 (7) | C36—C37—C38—C39 | −1.1 (10) |
Co1—N1—C15—C16 | −173.8 (4) | C37—C38—C39—C40 | 1.1 (10) |
C13—C11—C16—C15 | −2.7 (7) | C38—C39—C40—C41 | −0.8 (9) |
C12—C11—C16—C15 | 176.6 (4) | C37—C36—C41—C40 | −0.4 (8) |
N1—C15—C16—C11 | 1.1 (8) | C35—C36—C41—C40 | 179.5 (5) |
C20—C12—C17—C18 | −0.8 (7) | C39—C40—C41—C36 | 0.4 (8) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···N2ii | 0.82 | 1.91 | 2.726 (5) | 177 |
O7—H7A···O1iii | 0.82 | 1.86 | 2.656 (4) | 164 |
O9—H9A···N5iv | 0.82 | 1.91 | 2.732 (5) | 176 |
Symmetry codes: (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x−1, y+1, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···N2i | 0.82 | 1.91 | 2.726 (5) | 177 |
O7—H7A···O1ii | 0.82 | 1.86 | 2.656 (4) | 164 |
O9—H9A···N5iii | 0.82 | 1.91 | 2.732 (5) | 176 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z+1; (iii) x−1, y+1, z−1. |
Acknowledgements
The authors acknowledge financial support from the Consejo Nacional de Ciencia y Tecnología (CONACyT), Fondo Mixto Veracruz (127835).
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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.
The design of metal-organic coordination compounds is of current interest in the fields of supramolecular chemistry and crystal engineering. This interest stems from their potential applications as functional materials, such as in gas storage, ion-exchange, catalysis, magnetism and molecular sensing (Song et al., 2009; Zhang et al., 2007). 4,4'-Bipyridine is an excellent, rigid bridging ligand for the construction of novel metal-organic coordination compounds due to its various coordinative modes with metal ions (Wu et al., 2007; Murugesapandian & Roesky, 2011a, 2011b). Currently all the metal-organic coordination compounds obtained with benzoic acid and 4,4'-bipyridine are polymeric. The title compound is the first example of a dimeric species with these two ligands.
The title compound is a cobalt(II) dimer having crystallographically-imposed centrosymmetry (Fig. 1) together with six molecules of benzoic acid in the lattice. Each cobalt(II) ion displays a distorted octahedral coordination geometry being surrounded by four oxygen atoms of one chelating and two bridging benzoate anions and two trans-disposed, monodentate 4,4'-bipyridine ligands. In the central portion of the dimer, the two metal ions and the two bidentate bridging benzoate ions form an eight-membered ring. The dihedral angles between the rings of the 4,4'-bipyridine ligands are 25.2 (2)° (ligand containing N1 and N2) and 22.8 (2)° (ligand containing N3 and N5). In the crystal structure weak O—H···O and C—H···O hydrogen bonds link the molecules into an infinite one-dimensional chain extending along the b axis [O7—H7a···O1,1.859 Å, 164.10°; C6—H6···O2, 2.366 Å, 167.54°]. (Fig. 2).