research communications
κ2N,N′)cobalt(II)] tetranitrate N,N′-(1,4-phenylenedicarbonyl)diglycine solvate octahydrate
of bis[tris(1,10-phenanthroline-aInstitute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Strasse 4, D-38678 Clausthal-Zellerfeld, Germany
*Correspondence e-mail: niels-patrick.pook@tu-clausthal.de
The complex cation of the title compound, [Co(C12H8N2)3]2(NO3)4·C12H12N2O6·8H2O, contains a CoII atom with a distorted octahedral coordination environment defined by six N atoms from three bidentate 1,10-phenanthroline ligands. The of the title compound is completed by one-half of the N,N′-(1,4-phenylenedicarbonyl)diglycine solvent molecule, which is located on a centre of inversion, by two nitrate counter-anions and four solvent water molecules. Two [Co(C12H8N2)3]2+ cations are connected through C—H⋯O contacts and through lone-pair⋯π interactions involving the non-coordinating N,N′-(1,4-phenylenedicarbonyl)diglycine and phenanthroline molecules. The different aromatic ring systems are involved in π–π stacking and C—H⋯π interactions, with centroid-to-centroid distances in the range 3.7094 (8)–3.9973 (9) Å. The is stabilized by further anion⋯π interactions and C—H⋯O contacts, as well as O—H⋯O and N—H⋯O hydrogen bonds between water molecules, the non-coordinating nitrate anions, N,N′-(1,4-phenylenedicarbonyl)diglycine and phenanthroline molecules. These non-covalent interactions give rise to a three-dimensional supramolecular network.
Keywords: crystal structure; cobalt(II) complex; N,N′-(1,4-phenylenedicarbonyl)diglycine; phenanthroline ligand; supramolecular interactions.
CCDC reference: 1410901
1. Chemical context
In the past decades, the focus on metal-organic complexes which form coordination polymers of different dimensions has drawn much attention due to their interesting structures and physical and chemical properties. Application fields for these materials are in catalysis, in gas storage (Kitagawa et al., 2004), luminescence (Allendorf et al., 2015) and very recently as scintillation materials (Allendorf et al., 2009; Doty et al., 2009; Perry et al., 2012). The structures of coordination polymers (Leong & Vittal, 2011; Yamada et al., 2013) often show various non-covalent intermolecular interactions and forces, and therefore are intimately connected with the field of supramolecular chemistry (Schneider, 2009) and self-assembly (Cook et al., 2013). Such non-covalent interactions are also of utmost importance in biological macromolecules like DNA, RNA and proteins (Salonen et al., 2011). They are typically observed in biochemical reactions as protein–ligand recognitions and are partly utilized in drug design (Meyer et al., 2003). Apart from classical and non-classical hydrogen bonding of the types O–H⋯O, N—H⋯O and C—H⋯O, respectively, different π-interactions of aromatic rings such as π–π stacking, C—H⋯π, ion⋯π and lone-pair⋯π play a crucial role in the assembly of metal-organic polymers. Nitrogen-containing heterocycles like bipyridine and phenanthroline are metal-coordinating, electron-deficient aromatic systems and predestined for π–π stacking as π-acceptors (Janiak, 2000). In addition, π-donor⋯acceptor functions in different parts of an aromatic molecule can lead to remarkable properties (Albrecht et al., 2010).
In previously synthesized transition metal complexes with N,N′-(1,4-phenylenedicarbonyl)diglycine as metal-linking ligand, zigzag chains are formed, constructing interpenetrating networks (see Database survey). In our synthetic approach, we offer such systems another electron-deficient bidentate aromatic ring system like phenanthroline or bipyridine in order to block parts of the coordination sphere of the metal atoms so that these zigzag chains are truncated or not formed at all. Thus, an alternative route for the resultant system lies in the use of the offered π-interaction possibilities as well as in stacking interactions as a new linking mode. Recently, we have described the interactions of a cobalt(III) bipyridine complex with supramolecular synthons (Pook et al., 2014) as well as a precursor material (Pook et al., 2013) that both contain N,N′-(1,4-phenylenedicarbonyl)diglycine. The chosen ligand N,N′-(1,4-phenylenedicarbonyl)diglycine is a relatively rigid molecule with one sp3-hybridized methylene carbon atom that allows the acid moiety to rotate. Moreover, this ligand simultaneously possesses several coordination sites through the carboxylic group and the oxygen atom of the amide group. These functional groups can also be involved in hydrogen bonding and D—H⋯π interactions.
In the present contribution we have determined the structure of a novel cobalt(II) coordination polymer with a non-coordinating N,N′-(1,4-phenylenedicarbonyl)diglycine solvent molecule linking two tris(phenanthroline)cobalt(II) cationic building blocks via the mentioned non-classical interactions.
2. Structural commentary
The molecular entities (Fig. 1) of the title compound include one CoII complex cation in which three bidentate phenanthroline ligands define a distorted octahedral coordination sphere. Distances and angles of this rather common cationic species, [Co(C12H8N2)3]2+, are well within expected ranges and are comparable to those found in the literature (Li et al., 2011; Geraghty et al., 1999). A crystallographic center of inversion is located at the centroid of the protonated and non-coordinating N,N′-(1,4-phenylenedicarbonyl)diglycine molecule. The is completed by two non-coordinating nitrate counter-anions and four solvent water molecules. The N,N′-(1,4-phenylenedicarbonyl)diglycine molecule links two complex tris(phenanthroline-κ2N,N′)cobalt(II) cations via lone-pair⋯π interactions involving the carboxylic acid function and the phenanthroline aromatic system as well as C—H⋯O contacts between the oxygen atom of the amide group and one phenanthroline ligand. Moreover, π–π stacking interactions between different aromatic ring systems and C—H⋯π as well as O—H⋯O and N—H⋯O hydrogen bonding are observed and consolidate an extensive three-dimensional supramolecular network.
3. Supramolecular features
In the via O—H⋯O, C—H⋯O and partly via N—H⋯O hydrogen bonds with water, phenanthroline and N,N′-(1,4-phenylenedicarbonyl)diglycine molecules (Fig. 1 and Table 1). π–π interactions of parallel-displaced phenanthroline ligands and between phenanthroline and N,N′-(1,4-phenylenedicarbonyl)diglycine solvent molecules stack these components along the c axis (Fig. 2). The centroid-to-centroid distance of Cg1⋯Cg5 is 3.7094 (8) Å and between Cg7⋯Cg7 is 3.9973 (9) Å (Fig. 3), where Cg1, Cg5 and Cg7 are the centroids defined by the ring atoms C37–C39/C37′–C39′, N3/C13-C16/C24 and N4/C19-C23, respectively. These distances are in expected ranges (Barceló-Oliver et al., 2010; Kumar Seth et al., 2010). In addition, a T-shaped motif between aromatic rings give rise to C—H⋯π interactions and leads to an expected distance (Brandl et al., 2001; Gathergood et al., 2003; Horiguchi et al., 2007; Meyer et al., 2003; Salonen et al., 2011) between H20(Cg7)⋯Cg8 of 3.037 (1) Å, where Cg8 is the centroid defined by the ring atoms N5/C25–C28/C36. Moreover, a relatively short N—H⋯π distance of 4.08 (6) Å is observed (Fig. 3) that is comparable to reference values (Steiner & Koellner, 2001). Besides the previously mentioned forces, lone-pair⋯π and anion⋯π interactions (Fig. 4) contribute to the consolidation of the supramolecular network. The lone-pair⋯π interactions between the O3 atom of the carboxylic acid function of the N,N′-(1,4-phenylenedicarbonyl)diglycine solvent and the Cg2 centroid of a phenanthroline ligand are associated with a distance of 3.400 (5) Å. Similar distances of 3.461 (5) Å prevail between the O10 atom of a water molecule and the Cg3 centroid of a phenanthroline ligand, where Cg2 and Cg3 are the centroids defined by the ring atoms N1/C1–C4/C12 and C4–C7/C11/C12, respectively. The values are similar to those found in the literature (Egli & Sarkhel, 2007; Gao et al., 2009; Jain et al., 2009; Mooibroek et al., 2008; Wan et al., 2008). Finally, the anion⋯π interactions of the nitrate (N9/O4-O6) and Cg7 of a phenanthroline ligand are reflected by a distance of 3.628 (4) Å that is comparable to previously reported structures (Ballester, 2008; Gamez et al., 2007; Schottel et al., 2008).
numerous non-covalant interactions are observed. The two nitrate anions are linked4. Database survey
A search in the Cambridge Structural Database (Version 5.35, November 2013 with three updates; Groom & Allen, 2014) for crystal structures containing the ligand N,N′-(1,4-phenylenedicarbonyl)diglycine resulted in six metal-organic compounds (Duan et al., 2010; Kostakis et al., 2005, 2011; Zhang et al., 2005, 2006). Some of these structures are composed of interpenetrating networks. Among them is a structure which includes bipyridine besides N,N′-(1,4-phenylenedicarbonyl)diglycine and shows a number of non-classical interactions (Pook et al., 2014).
5. Synthesis and crystallization
The starting material, N,N′-(1,4-phenylenedicarbonyl)diglycine, was prepared by the method of Cleaver & Pratt (1955). Cesium carbonate (2 mmol), 1,10-phenanthroline (1 mmol) and 2,2′-(benzene-1,4-dicarboxamido)diacetatic acid (1 mmol) were dissolved in a 1:1 (v/v) mixture of water and methanol (50 ml) and refluxed for 30 minutes. The mixture was allowed to cool to room temperature, and a previously prepared aqueous solution of cobalt nitrate (1 mmol) was slowly added under continuous stirring. Deep dark-orange block-shaped crystals of the title compound were obtained by slow evaporation at room temperature.
6. details
Crystal data, data collection and structure . All C-bound H atoms were positioned with idealized geometry and refined with Uiso(H) = 1.2 Ueq(C) and C—H(aromatic) = 0.94 Å and C—H(methylene) = 0.98 Å using a riding model. The water H atoms were located in a different Fourier map and were refined with O—H distances restrained to 0.82–0.87 Å and with Uiso(H) = 1.5Ueq(O).
details are summarized in Table 2
|
Supporting information
CCDC reference: 1410901
https://doi.org/10.1107/S2056989015013006/wm5178sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013006/wm5178Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013006/wm5178Isup4.cdx
Data collection: X-AREA (Stoe & Cie, 2008); cell
X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).[Co(C12H8N2)3]2(NO3)4·C12H12N2O6·8H2O | Z = 1 |
Mr = 1871.48 | F(000) = 968.0 |
Triclinic, P1 | Dx = 1.473 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6663 (18) Å | Cell parameters from 7956 reflections |
b = 14.314 (2) Å | θ = 1.0–25.7° |
c = 14.573 (3) Å | µ = 0.49 mm−1 |
α = 85.403 (13)° | T = 223 K |
β = 73.421 (14)° | Block, orange |
γ = 82.020 (12)° | 0.25 × 0.23 × 0.15 mm |
V = 2109.8 (6) Å3 |
Stoe IPDS 2 diffractometer | 7956 independent reflections |
Radiation source: fine-focus sealed tube | 4701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.138 |
ω–scans | θmax = 25.7°, θmin = 2.0° |
Absorption correction: numerical (X-AREA; Stoe, 2008) | h = −13→13 |
Tmin = 0.819, Tmax = 0.961 | k = −17→17 |
21841 measured reflections | l = −17→17 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0452P)2 + 0.3752P] where P = (Fo2 + 2Fc2)/3 |
7956 reflections | (Δ/σ)max = 0.001 |
621 parameters | Δρmax = 0.43 e Å−3 |
8 restraints | Δρmin = −0.49 e Å−3 |
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 | ||
Co | 0.04386 (7) | 0.23362 (5) | 0.27813 (5) | 0.03230 (18) | |
O1 | −0.0043 (5) | 0.7504 (2) | 0.0769 (4) | 0.0732 (15) | |
O2 | 0.3407 (4) | 0.6495 (3) | 0.0417 (3) | 0.0512 (9) | |
O3 | 0.2889 (4) | 0.5625 (2) | 0.1806 (3) | 0.0471 (9) | |
H31 | 0.342 (5) | 0.519 (3) | 0.154 (4) | 0.071* | |
O4 | 0.3317 (4) | 0.9176 (3) | 0.1619 (4) | 0.0686 (13) | |
O5 | 0.4745 (6) | 0.9491 (4) | 0.2281 (4) | 0.1008 (19) | |
O6 | 0.4044 (5) | 0.8125 (4) | 0.2524 (4) | 0.0841 (15) | |
O7 | 0.5194 (5) | 0.5579 (4) | 0.2754 (4) | 0.0834 (15) | |
O8 | 0.6586 (5) | 0.5272 (4) | 0.3545 (4) | 0.101 (2) | |
O9 | 0.6425 (4) | 0.4256 (3) | 0.2564 (3) | 0.0613 (11) | |
O10 | 0.4710 (4) | 0.4210 (3) | 0.1299 (3) | 0.0468 (9) | |
H10A | 0.521 (5) | 0.428 (4) | 0.165 (3) | 0.049 (16)* | |
H10B | 0.528 (5) | 0.407 (5) | 0.081 (3) | 0.07 (2)* | |
O11 | 0.6055 (6) | 0.7456 (4) | 0.3503 (4) | 0.0780 (15) | |
H11A | 0.604 (7) | 0.689 (6) | 0.339 (6) | 0.09 (3)* | |
H11B | 0.557 (8) | 0.767 (6) | 0.307 (6) | 0.10 (3)* | |
O12 | 0.5530 (7) | 0.1406 (5) | 0.4875 (6) | 0.114 (2) | |
H12A | 0.494 (9) | 0.151 (9) | 0.543 (5) | 0.171* | |
H12B | 0.509 (10) | 0.121 (8) | 0.451 (7) | 0.171* | |
O13 | 0.4193 (7) | 0.0330 (5) | 0.4067 (6) | 0.115 (2) | |
H13A | 0.453 (11) | 0.014 (9) | 0.347 (4) | 0.172* | |
H13B | 0.392 (12) | −0.009 (7) | 0.454 (6) | 0.172* | |
N1 | 0.0324 (4) | 0.3664 (3) | 0.2003 (3) | 0.0368 (10) | |
N2 | 0.2048 (4) | 0.2094 (3) | 0.1525 (3) | 0.0349 (9) | |
N3 | −0.1049 (4) | 0.1827 (3) | 0.2298 (3) | 0.0387 (10) | |
N4 | 0.0544 (4) | 0.0889 (3) | 0.3308 (3) | 0.0384 (10) | |
N5 | −0.0900 (4) | 0.2861 (3) | 0.4089 (3) | 0.0354 (9) | |
N6 | 0.1757 (4) | 0.2817 (3) | 0.3482 (3) | 0.0360 (9) | |
N7 | 0.1534 (5) | 0.8007 (3) | 0.1288 (3) | 0.0419 (10) | |
H7 | 0.201 (6) | 0.840 (4) | 0.130 (5) | 0.08 (2)* | |
N8 | 0.6071 (4) | 0.5025 (4) | 0.2970 (3) | 0.0479 (11) | |
N9 | 0.4026 (5) | 0.8936 (4) | 0.2152 (4) | 0.0558 (13) | |
C1 | −0.0530 (5) | 0.4428 (3) | 0.2256 (4) | 0.0406 (12) | |
H1 | −0.1207 | 0.4403 | 0.2832 | 0.049* | |
C2 | −0.0458 (6) | 0.5276 (4) | 0.1695 (4) | 0.0484 (14) | |
H2 | −0.1077 | 0.5807 | 0.1891 | 0.058* | |
C3 | 0.0531 (6) | 0.5313 (4) | 0.0858 (4) | 0.0485 (14) | |
H3 | 0.0591 | 0.5875 | 0.0477 | 0.058* | |
C4 | 0.1455 (5) | 0.4523 (3) | 0.0564 (4) | 0.0395 (12) | |
C5 | 0.2511 (6) | 0.4493 (4) | −0.0297 (4) | 0.0515 (15) | |
H5 | 0.2589 | 0.5029 | −0.0717 | 0.062* | |
C6 | 0.3392 (6) | 0.3729 (4) | −0.0528 (4) | 0.0527 (15) | |
H6 | 0.4086 | 0.3742 | −0.1094 | 0.063* | |
C7 | 0.3288 (5) | 0.2884 (4) | 0.0086 (4) | 0.0426 (12) | |
C8 | 0.4200 (5) | 0.2073 (4) | −0.0091 (4) | 0.0521 (14) | |
H8 | 0.4932 | 0.2057 | −0.0635 | 0.062* | |
C9 | 0.4024 (6) | 0.1303 (4) | 0.0529 (4) | 0.0542 (15) | |
H9 | 0.4634 | 0.0754 | 0.0420 | 0.065* | |
C10 | 0.2927 (5) | 0.1345 (4) | 0.1325 (4) | 0.0430 (12) | |
H10 | 0.2807 | 0.0809 | 0.1743 | 0.052* | |
C11 | 0.2233 (5) | 0.2870 (3) | 0.0916 (3) | 0.0326 (10) | |
C12 | 0.1301 (5) | 0.3703 (3) | 0.1167 (3) | 0.0342 (11) | |
C13 | −0.1832 (5) | 0.2285 (4) | 0.1819 (4) | 0.0464 (13) | |
H13 | −0.1734 | 0.2921 | 0.1637 | 0.056* | |
C14 | −0.2807 (6) | 0.1887 (4) | 0.1562 (5) | 0.0564 (15) | |
H14 | −0.3334 | 0.2244 | 0.1210 | 0.068* | |
C15 | −0.2969 (6) | 0.0969 (5) | 0.1837 (5) | 0.0617 (17) | |
H15 | −0.3618 | 0.0684 | 0.1679 | 0.074* | |
C16 | −0.2172 (6) | 0.0455 (4) | 0.2353 (4) | 0.0536 (15) | |
C17 | −0.2252 (7) | −0.0525 (5) | 0.2653 (5) | 0.0682 (19) | |
H17 | −0.2886 | −0.0843 | 0.2514 | 0.082* | |
C18 | −0.1424 (7) | −0.0990 (4) | 0.3130 (5) | 0.0673 (19) | |
H18 | −0.1496 | −0.1629 | 0.3313 | 0.081* | |
C19 | −0.0449 (6) | −0.0555 (4) | 0.3367 (4) | 0.0500 (14) | |
C20 | 0.0441 (6) | −0.1004 (4) | 0.3847 (4) | 0.0574 (15) | |
H20 | 0.0426 | −0.1648 | 0.4028 | 0.069* | |
C21 | 0.1334 (6) | −0.0522 (4) | 0.4060 (4) | 0.0538 (15) | |
H21 | 0.1931 | −0.0827 | 0.4386 | 0.065* | |
C22 | 0.1340 (5) | 0.0449 (4) | 0.3776 (4) | 0.0483 (13) | |
H22 | 0.1940 | 0.0788 | 0.3932 | 0.058* | |
C23 | −0.0350 (5) | 0.0412 (3) | 0.3087 (4) | 0.0413 (12) | |
C24 | −0.1207 (5) | 0.0913 (3) | 0.2575 (4) | 0.0403 (12) | |
C25 | −0.2189 (5) | 0.2880 (4) | 0.4380 (4) | 0.0496 (14) | |
H25 | −0.2604 | 0.2593 | 0.4007 | 0.060* | |
C26 | −0.2979 (6) | 0.3309 (4) | 0.5225 (4) | 0.0554 (15) | |
H26 | −0.3896 | 0.3299 | 0.5414 | 0.066* | |
C27 | −0.2384 (6) | 0.3743 (4) | 0.5767 (4) | 0.0504 (14) | |
H27 | −0.2895 | 0.4050 | 0.6322 | 0.060* | |
C28 | −0.1017 (5) | 0.3724 (3) | 0.5489 (3) | 0.0387 (11) | |
C29 | −0.0309 (6) | 0.4149 (4) | 0.6016 (4) | 0.0456 (13) | |
H29 | −0.0781 | 0.4458 | 0.6580 | 0.055* | |
C30 | 0.1008 (6) | 0.4115 (4) | 0.5725 (4) | 0.0466 (13) | |
H30 | 0.1441 | 0.4385 | 0.6098 | 0.056* | |
C31 | 0.1770 (5) | 0.3674 (3) | 0.4854 (4) | 0.0414 (12) | |
C32 | 0.3140 (6) | 0.3644 (4) | 0.4507 (4) | 0.0504 (14) | |
H32 | 0.3614 | 0.3919 | 0.4847 | 0.061* | |
C33 | 0.3780 (5) | 0.3213 (4) | 0.3674 (4) | 0.0522 (14) | |
H33 | 0.4700 | 0.3191 | 0.3429 | 0.063* | |
C34 | 0.3053 (5) | 0.2801 (4) | 0.3186 (4) | 0.0439 (12) | |
H34 | 0.3511 | 0.2497 | 0.2616 | 0.053* | |
C35 | 0.1110 (5) | 0.3250 (3) | 0.4311 (3) | 0.0348 (11) | |
C36 | −0.0303 (5) | 0.3275 (3) | 0.4638 (3) | 0.0347 (11) | |
C37 | −0.0689 (6) | 0.9267 (4) | −0.0025 (4) | 0.0510 (15) | |
H37 | −0.1166 | 0.8767 | −0.0044 | 0.061* | |
C38 | 0.1019 (6) | 0.9861 (4) | 0.0429 (5) | 0.0528 (15) | |
H38 | 0.1712 | 0.9774 | 0.0719 | 0.063* | |
C39 | 0.0323 (5) | 0.9110 (3) | 0.0405 (4) | 0.0429 (13) | |
C40 | 0.0587 (6) | 0.8137 (3) | 0.0836 (4) | 0.0450 (13) | |
C41 | 0.1763 (5) | 0.7131 (3) | 0.1820 (4) | 0.0424 (12) | |
H41A | 0.0929 | 0.6861 | 0.2063 | 0.051* | |
H41B | 0.2040 | 0.7272 | 0.2374 | 0.051* | |
C42 | 0.2788 (5) | 0.6397 (3) | 0.1250 (4) | 0.0371 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co | 0.0358 (4) | 0.0300 (3) | 0.0299 (3) | −0.0081 (3) | −0.0054 (3) | −0.0008 (3) |
O1 | 0.101 (4) | 0.026 (2) | 0.121 (4) | −0.015 (2) | −0.076 (3) | 0.010 (2) |
O2 | 0.061 (3) | 0.050 (2) | 0.038 (2) | −0.0048 (18) | −0.0070 (19) | −0.0001 (17) |
O3 | 0.058 (2) | 0.033 (2) | 0.049 (2) | 0.0051 (17) | −0.0179 (19) | 0.0010 (17) |
O4 | 0.074 (3) | 0.043 (2) | 0.105 (4) | −0.004 (2) | −0.053 (3) | −0.002 (2) |
O5 | 0.107 (4) | 0.111 (4) | 0.114 (5) | −0.058 (4) | −0.057 (4) | 0.000 (4) |
O6 | 0.098 (4) | 0.073 (3) | 0.084 (4) | −0.015 (3) | −0.037 (3) | 0.028 (3) |
O7 | 0.074 (3) | 0.102 (4) | 0.063 (3) | 0.021 (3) | −0.017 (3) | −0.002 (3) |
O8 | 0.078 (3) | 0.143 (5) | 0.100 (4) | 0.009 (3) | −0.047 (3) | −0.069 (4) |
O9 | 0.057 (3) | 0.056 (3) | 0.068 (3) | −0.011 (2) | −0.006 (2) | −0.017 (2) |
O10 | 0.048 (2) | 0.050 (2) | 0.042 (2) | −0.0005 (18) | −0.012 (2) | −0.0065 (18) |
O11 | 0.089 (4) | 0.070 (3) | 0.086 (4) | −0.027 (3) | −0.036 (3) | 0.006 (3) |
O12 | 0.122 (6) | 0.113 (5) | 0.123 (6) | −0.050 (4) | −0.040 (4) | −0.019 (4) |
O13 | 0.109 (5) | 0.108 (5) | 0.149 (7) | 0.004 (4) | −0.068 (5) | −0.040 (5) |
N1 | 0.045 (2) | 0.029 (2) | 0.039 (2) | −0.0075 (18) | −0.013 (2) | −0.0074 (18) |
N2 | 0.041 (2) | 0.029 (2) | 0.034 (2) | −0.0050 (18) | −0.0084 (18) | −0.0033 (17) |
N3 | 0.042 (2) | 0.034 (2) | 0.041 (2) | −0.0054 (19) | −0.013 (2) | −0.0021 (19) |
N4 | 0.041 (2) | 0.036 (2) | 0.038 (2) | −0.0077 (19) | −0.0090 (19) | −0.0002 (18) |
N5 | 0.033 (2) | 0.033 (2) | 0.039 (2) | −0.0078 (17) | −0.0062 (18) | −0.0014 (17) |
N6 | 0.039 (2) | 0.034 (2) | 0.033 (2) | −0.0110 (18) | −0.0045 (18) | 0.0001 (17) |
N7 | 0.051 (3) | 0.029 (2) | 0.051 (3) | −0.002 (2) | −0.025 (2) | −0.0001 (19) |
N8 | 0.031 (2) | 0.061 (3) | 0.049 (3) | −0.011 (2) | −0.004 (2) | −0.006 (2) |
N9 | 0.049 (3) | 0.061 (3) | 0.058 (3) | −0.006 (2) | −0.014 (3) | −0.011 (3) |
C1 | 0.045 (3) | 0.031 (3) | 0.047 (3) | −0.001 (2) | −0.015 (2) | −0.007 (2) |
C2 | 0.058 (4) | 0.027 (3) | 0.069 (4) | 0.001 (2) | −0.033 (3) | −0.009 (3) |
C3 | 0.064 (4) | 0.035 (3) | 0.060 (4) | −0.015 (3) | −0.037 (3) | 0.008 (3) |
C4 | 0.054 (3) | 0.031 (3) | 0.042 (3) | −0.017 (2) | −0.026 (3) | 0.012 (2) |
C5 | 0.060 (4) | 0.055 (4) | 0.047 (3) | −0.028 (3) | −0.024 (3) | 0.018 (3) |
C6 | 0.059 (4) | 0.065 (4) | 0.036 (3) | −0.026 (3) | −0.011 (3) | 0.012 (3) |
C7 | 0.043 (3) | 0.049 (3) | 0.036 (3) | −0.016 (2) | −0.005 (2) | −0.009 (2) |
C8 | 0.045 (3) | 0.058 (4) | 0.048 (3) | −0.011 (3) | 0.004 (3) | −0.020 (3) |
C9 | 0.048 (3) | 0.046 (3) | 0.059 (4) | 0.005 (3) | 0.001 (3) | −0.024 (3) |
C10 | 0.044 (3) | 0.035 (3) | 0.044 (3) | −0.005 (2) | −0.001 (2) | −0.007 (2) |
C11 | 0.036 (3) | 0.036 (3) | 0.027 (2) | −0.006 (2) | −0.009 (2) | −0.0019 (19) |
C12 | 0.037 (3) | 0.034 (3) | 0.037 (3) | −0.009 (2) | −0.018 (2) | −0.001 (2) |
C13 | 0.054 (3) | 0.040 (3) | 0.052 (3) | −0.007 (2) | −0.025 (3) | −0.004 (2) |
C14 | 0.053 (3) | 0.058 (4) | 0.066 (4) | −0.010 (3) | −0.029 (3) | −0.002 (3) |
C15 | 0.053 (4) | 0.067 (4) | 0.079 (5) | −0.022 (3) | −0.033 (3) | −0.005 (3) |
C16 | 0.063 (4) | 0.046 (3) | 0.061 (4) | −0.023 (3) | −0.023 (3) | −0.002 (3) |
C17 | 0.069 (4) | 0.055 (4) | 0.093 (5) | −0.030 (3) | −0.030 (4) | −0.001 (4) |
C18 | 0.084 (5) | 0.040 (3) | 0.079 (5) | −0.031 (3) | −0.017 (4) | 0.004 (3) |
C19 | 0.057 (3) | 0.036 (3) | 0.053 (3) | −0.007 (3) | −0.009 (3) | 0.001 (3) |
C20 | 0.075 (4) | 0.035 (3) | 0.052 (4) | −0.007 (3) | −0.005 (3) | 0.011 (3) |
C21 | 0.060 (4) | 0.045 (3) | 0.047 (3) | 0.003 (3) | −0.007 (3) | 0.007 (3) |
C22 | 0.047 (3) | 0.051 (3) | 0.045 (3) | −0.003 (3) | −0.014 (3) | 0.007 (3) |
C23 | 0.047 (3) | 0.027 (3) | 0.046 (3) | −0.012 (2) | −0.005 (2) | 0.003 (2) |
C24 | 0.046 (3) | 0.034 (3) | 0.042 (3) | −0.011 (2) | −0.010 (2) | −0.002 (2) |
C25 | 0.046 (3) | 0.053 (3) | 0.053 (3) | −0.014 (3) | −0.013 (3) | −0.006 (3) |
C26 | 0.038 (3) | 0.065 (4) | 0.053 (4) | −0.008 (3) | 0.005 (3) | −0.004 (3) |
C27 | 0.060 (4) | 0.049 (3) | 0.036 (3) | −0.004 (3) | −0.003 (3) | −0.004 (2) |
C28 | 0.044 (3) | 0.037 (3) | 0.029 (3) | −0.004 (2) | 0.000 (2) | 0.002 (2) |
C29 | 0.070 (4) | 0.038 (3) | 0.028 (3) | −0.003 (3) | −0.014 (3) | −0.005 (2) |
C30 | 0.057 (4) | 0.046 (3) | 0.038 (3) | −0.004 (3) | −0.016 (3) | −0.005 (2) |
C31 | 0.054 (3) | 0.039 (3) | 0.037 (3) | −0.013 (2) | −0.020 (3) | 0.004 (2) |
C32 | 0.054 (3) | 0.054 (3) | 0.050 (3) | −0.015 (3) | −0.022 (3) | 0.003 (3) |
C33 | 0.038 (3) | 0.071 (4) | 0.050 (4) | −0.016 (3) | −0.011 (3) | −0.002 (3) |
C34 | 0.041 (3) | 0.059 (3) | 0.032 (3) | −0.010 (2) | −0.007 (2) | −0.002 (2) |
C35 | 0.046 (3) | 0.029 (2) | 0.031 (3) | −0.008 (2) | −0.013 (2) | 0.0037 (19) |
C36 | 0.046 (3) | 0.027 (2) | 0.032 (3) | −0.006 (2) | −0.012 (2) | 0.0026 (19) |
C37 | 0.068 (4) | 0.028 (3) | 0.069 (4) | −0.009 (3) | −0.037 (3) | −0.002 (3) |
C38 | 0.070 (4) | 0.029 (3) | 0.076 (4) | −0.002 (3) | −0.049 (3) | 0.001 (3) |
C39 | 0.060 (3) | 0.027 (3) | 0.049 (3) | −0.002 (2) | −0.029 (3) | −0.001 (2) |
C40 | 0.056 (3) | 0.028 (3) | 0.056 (3) | −0.004 (2) | −0.025 (3) | 0.002 (2) |
C41 | 0.051 (3) | 0.037 (3) | 0.039 (3) | 0.000 (2) | −0.014 (2) | 0.001 (2) |
C42 | 0.043 (3) | 0.030 (3) | 0.044 (3) | −0.003 (2) | −0.022 (2) | −0.003 (2) |
Co—N2 | 2.137 (4) | C8—C9 | 1.368 (8) |
Co—N1 | 2.141 (4) | C8—H8 | 0.9400 |
Co—N3 | 2.141 (4) | C9—C10 | 1.391 (8) |
Co—N5 | 2.148 (4) | C9—H9 | 0.9400 |
Co—N4 | 2.150 (4) | C10—H10 | 0.9400 |
Co—N6 | 2.166 (4) | C11—C12 | 1.442 (7) |
O1—C40 | 1.226 (6) | C13—C14 | 1.402 (7) |
O2—C42 | 1.212 (6) | C13—H13 | 0.9400 |
O3—C42 | 1.327 (6) | C14—C15 | 1.362 (8) |
O3—H31 | 0.822 (10) | C14—H14 | 0.9400 |
O4—N9 | 1.231 (6) | C15—C16 | 1.389 (8) |
O5—N9 | 1.237 (6) | C15—H15 | 0.9400 |
O6—N9 | 1.241 (6) | C16—C24 | 1.416 (7) |
O7—N8 | 1.235 (6) | C16—C17 | 1.442 (8) |
O8—N8 | 1.221 (6) | C17—C18 | 1.349 (9) |
O9—N8 | 1.251 (6) | C17—H17 | 0.9400 |
O10—H10A | 0.87 (2) | C18—C19 | 1.416 (8) |
O10—H10B | 0.816 (10) | C18—H18 | 0.9400 |
O11—H11A | 0.85 (8) | C19—C20 | 1.393 (8) |
O11—H11B | 0.93 (8) | C19—C23 | 1.421 (7) |
O12—H12A | 0.88 (2) | C20—C21 | 1.365 (8) |
O12—H12B | 0.88 (2) | C20—H20 | 0.9400 |
O13—H13A | 0.89 (2) | C21—C22 | 1.419 (8) |
O13—H13B | 0.88 (2) | C21—H21 | 0.9400 |
N1—C1 | 1.326 (6) | C22—H22 | 0.9400 |
N1—C12 | 1.361 (6) | C23—C24 | 1.424 (7) |
N2—C10 | 1.314 (6) | C25—C26 | 1.411 (8) |
N2—C11 | 1.365 (6) | C25—H25 | 0.9400 |
N3—C13 | 1.312 (6) | C26—C27 | 1.373 (8) |
N3—C24 | 1.358 (6) | C26—H26 | 0.9400 |
N4—C22 | 1.301 (6) | C27—C28 | 1.395 (7) |
N4—C23 | 1.368 (6) | C27—H27 | 0.9400 |
N5—C25 | 1.315 (6) | C28—C36 | 1.408 (7) |
N5—C36 | 1.368 (6) | C28—C29 | 1.437 (7) |
N6—C34 | 1.323 (6) | C29—C30 | 1.342 (8) |
N6—C35 | 1.358 (6) | C29—H29 | 0.9400 |
N7—C40 | 1.341 (6) | C30—C31 | 1.438 (7) |
N7—C41 | 1.449 (6) | C30—H30 | 0.9400 |
N7—H7 | 0.82 (2) | C31—C32 | 1.400 (8) |
N8—O8 | 1.221 (6) | C31—C35 | 1.416 (6) |
N8—O7 | 1.235 (6) | C32—C33 | 1.361 (8) |
N8—O9 | 1.251 (6) | C32—H32 | 0.9400 |
N9—O4 | 1.231 (6) | C33—C34 | 1.402 (7) |
N9—O6 | 1.241 (6) | C33—H33 | 0.9400 |
C1—C2 | 1.406 (7) | C34—H34 | 0.9400 |
C1—H1 | 0.9400 | C35—C36 | 1.440 (7) |
C2—C3 | 1.369 (8) | C37—C39 | 1.380 (7) |
C2—H2 | 0.9400 | C37—C38i | 1.381 (7) |
C3—C4 | 1.400 (8) | C37—H37 | 0.9400 |
C3—H3 | 0.9400 | C38—C37i | 1.381 (7) |
C4—C12 | 1.408 (6) | C38—C39 | 1.397 (7) |
C4—C5 | 1.426 (8) | C38—H38 | 0.9400 |
C5—C6 | 1.337 (8) | C39—C40 | 1.505 (7) |
C5—H5 | 0.9400 | C40—O1 | 1.226 (6) |
C6—C7 | 1.443 (8) | C41—C42 | 1.513 (7) |
C6—H6 | 0.9400 | C41—H41A | 0.9800 |
C7—C8 | 1.396 (8) | C41—H41B | 0.9800 |
C7—C11 | 1.398 (7) | ||
N2—Co—N1 | 78.29 (16) | C4—C12—C11 | 119.4 (5) |
N2—Co—N3 | 98.40 (15) | N3—C13—C14 | 124.3 (5) |
N1—Co—N3 | 93.74 (16) | N3—C13—H13 | 117.8 |
N2—Co—N5 | 165.26 (13) | C14—C13—H13 | 117.8 |
N1—Co—N5 | 94.13 (16) | C15—C14—C13 | 118.2 (5) |
N3—Co—N5 | 94.67 (15) | C15—C14—H14 | 120.9 |
N2—Co—N4 | 94.91 (16) | C13—C14—H14 | 120.9 |
N1—Co—N4 | 168.75 (15) | C14—C15—C16 | 119.8 (5) |
N3—Co—N4 | 78.27 (15) | C14—C15—H15 | 120.1 |
N5—Co—N4 | 94.40 (16) | C16—C15—H15 | 120.1 |
N2—Co—N6 | 89.53 (15) | C15—C16—C24 | 118.1 (5) |
N1—Co—N6 | 90.78 (14) | C15—C16—C17 | 123.6 (5) |
N3—Co—N6 | 171.53 (17) | C24—C16—C17 | 118.2 (5) |
N5—Co—N6 | 77.84 (15) | C18—C17—C16 | 120.6 (5) |
N4—Co—N6 | 98.18 (15) | C18—C17—H17 | 119.7 |
C42—O3—H31 | 114 (5) | C16—C17—H17 | 119.7 |
H10A—O10—H10B | 98 (6) | C17—C18—C19 | 122.8 (5) |
H11A—O11—H11B | 91 (7) | C17—C18—H18 | 118.6 |
H12A—O12—H12B | 105 (10) | C19—C18—H18 | 118.6 |
H13A—O13—H13B | 119 (10) | C20—C19—C18 | 125.1 (5) |
C1—N1—C12 | 118.6 (4) | C20—C19—C23 | 116.8 (5) |
C1—N1—Co | 128.1 (4) | C18—C19—C23 | 118.1 (5) |
C12—N1—Co | 113.2 (3) | C21—C20—C19 | 121.1 (5) |
C10—N2—C11 | 117.8 (4) | C21—C20—H20 | 119.5 |
C10—N2—Co | 128.4 (3) | C19—C20—H20 | 119.5 |
C11—N2—Co | 113.4 (3) | C20—C21—C22 | 118.4 (5) |
C13—N3—C24 | 117.7 (4) | C20—C21—H21 | 120.8 |
C13—N3—Co | 129.0 (3) | C22—C21—H21 | 120.8 |
C24—N3—Co | 113.2 (3) | N4—C22—C21 | 122.4 (5) |
C22—N4—C23 | 119.7 (4) | N4—C22—H22 | 118.8 |
C22—N4—Co | 128.0 (4) | C21—C22—H22 | 118.8 |
C23—N4—Co | 112.3 (3) | N4—C23—C19 | 121.7 (5) |
C25—N5—C36 | 118.1 (4) | N4—C23—C24 | 118.3 (4) |
C25—N5—Co | 128.3 (3) | C19—C23—C24 | 120.0 (5) |
C36—N5—Co | 113.4 (3) | N3—C24—C16 | 121.8 (5) |
C34—N6—C35 | 117.5 (4) | N3—C24—C23 | 117.8 (4) |
C34—N6—Co | 129.4 (3) | C16—C24—C23 | 120.3 (5) |
C35—N6—Co | 112.9 (3) | N5—C25—C26 | 123.2 (5) |
C40—N7—C41 | 121.0 (4) | N5—C25—H25 | 118.4 |
C40—N7—H7 | 125 (5) | C26—C25—H25 | 118.4 |
C41—N7—H7 | 114 (5) | C27—C26—C25 | 118.9 (5) |
O8—N8—O7 | 118.1 (5) | C27—C26—H26 | 120.6 |
O8—N8—O7 | 118.1 (5) | C25—C26—H26 | 120.6 |
O8—N8—O7 | 118.1 (5) | C26—C27—C28 | 119.6 (5) |
O8—N8—O7 | 118.1 (5) | C26—C27—H27 | 120.2 |
O8—N8—O9 | 123.1 (5) | C28—C27—H27 | 120.2 |
O8—N8—O9 | 123.1 (5) | C27—C28—C36 | 117.9 (5) |
O7—N8—O9 | 118.7 (5) | C27—C28—C29 | 123.4 (5) |
O7—N8—O9 | 118.7 (5) | C36—C28—C29 | 118.7 (5) |
O8—N8—O9 | 123.1 (5) | C30—C29—C28 | 121.7 (5) |
O8—N8—O9 | 123.1 (5) | C30—C29—H29 | 119.2 |
O7—N8—O9 | 118.7 (5) | C28—C29—H29 | 119.2 |
O7—N8—O9 | 118.7 (5) | C29—C30—C31 | 121.2 (5) |
O4—N9—O5 | 119.7 (6) | C29—C30—H30 | 119.4 |
O4—N9—O5 | 119.7 (6) | C31—C30—H30 | 119.4 |
O4—N9—O6 | 119.2 (5) | C32—C31—C35 | 117.8 (5) |
O4—N9—O6 | 119.2 (5) | C32—C31—C30 | 123.4 (5) |
O5—N9—O6 | 121.0 (6) | C35—C31—C30 | 118.9 (5) |
O4—N9—O6 | 119.2 (5) | C33—C32—C31 | 119.3 (5) |
O4—N9—O6 | 119.2 (5) | C33—C32—H32 | 120.3 |
O5—N9—O6 | 121.0 (6) | C31—C32—H32 | 120.3 |
N1—C1—C2 | 122.4 (5) | C32—C33—C34 | 119.2 (5) |
N1—C1—H1 | 118.8 | C32—C33—H33 | 120.4 |
C2—C1—H1 | 118.8 | C34—C33—H33 | 120.4 |
C3—C2—C1 | 118.7 (5) | N6—C34—C33 | 123.6 (5) |
C3—C2—H2 | 120.6 | N6—C34—H34 | 118.2 |
C1—C2—H2 | 120.6 | C33—C34—H34 | 118.2 |
C2—C3—C4 | 120.8 (5) | N6—C35—C31 | 122.5 (5) |
C2—C3—H3 | 119.6 | N6—C35—C36 | 118.0 (4) |
C4—C3—H3 | 119.6 | C31—C35—C36 | 119.5 (5) |
C3—C4—C12 | 116.5 (5) | N5—C36—C28 | 122.4 (4) |
C3—C4—C5 | 124.7 (5) | N5—C36—C35 | 117.5 (4) |
C12—C4—C5 | 118.7 (5) | C28—C36—C35 | 120.1 (4) |
C6—C5—C4 | 122.2 (5) | C39—C37—C38i | 121.7 (5) |
C6—C5—H5 | 118.9 | C39—C37—H37 | 119.1 |
C4—C5—H5 | 118.9 | C38i—C37—H37 | 119.1 |
C5—C6—C7 | 120.6 (5) | C37i—C38—C39 | 119.9 (5) |
C5—C6—H6 | 119.7 | C37i—C38—H38 | 120.0 |
C7—C6—H6 | 119.7 | C39—C38—H38 | 120.0 |
C8—C7—C11 | 117.4 (5) | C37—C39—C38 | 118.4 (5) |
C8—C7—C6 | 123.7 (5) | C37—C39—C40 | 117.4 (4) |
C11—C7—C6 | 118.9 (5) | C38—C39—C40 | 124.2 (4) |
C9—C8—C7 | 119.8 (5) | O1—C40—N7 | 122.6 (5) |
C9—C8—H8 | 120.1 | O1—C40—N7 | 122.6 (5) |
C7—C8—H8 | 120.1 | O1—C40—C39 | 120.8 (5) |
C8—C9—C10 | 118.8 (5) | O1—C40—C39 | 120.8 (5) |
C8—C9—H9 | 120.6 | N7—C40—C39 | 116.7 (4) |
C10—C9—H9 | 120.6 | N7—C41—C42 | 114.7 (4) |
N2—C10—C9 | 123.6 (5) | N7—C41—H41A | 108.6 |
N2—C10—H10 | 118.2 | C42—C41—H41A | 108.6 |
C9—C10—H10 | 118.2 | N7—C41—H41B | 108.6 |
N2—C11—C7 | 122.6 (5) | C42—C41—H41B | 108.6 |
N2—C11—C12 | 117.3 (4) | H41A—C41—H41B | 107.6 |
C7—C11—C12 | 120.0 (4) | O2—C42—O3 | 125.5 (5) |
N1—C12—C4 | 122.9 (5) | O2—C42—C41 | 125.5 (4) |
N1—C12—C11 | 117.6 (4) | O3—C42—C41 | 109.0 (4) |
N2—Co—N1—C1 | −179.5 (4) | Co—N1—C12—C11 | 1.2 (5) |
N3—Co—N1—C1 | 82.7 (4) | C3—C4—C12—N1 | −0.8 (6) |
N5—Co—N1—C1 | −12.3 (4) | C5—C4—C12—N1 | 180.0 (4) |
N4—Co—N1—C1 | 127.0 (8) | C3—C4—C12—C11 | −178.8 (4) |
N6—Co—N1—C1 | −90.1 (4) | C5—C4—C12—C11 | 2.0 (6) |
N2—Co—N1—C12 | −2.3 (3) | N2—C11—C12—N1 | 1.6 (6) |
N3—Co—N1—C12 | −100.1 (3) | C7—C11—C12—N1 | −177.4 (4) |
N5—Co—N1—C12 | 164.9 (3) | N2—C11—C12—C4 | 179.7 (4) |
N4—Co—N1—C12 | −55.8 (10) | C7—C11—C12—C4 | 0.7 (6) |
N6—Co—N1—C12 | 87.0 (3) | C24—N3—C13—C14 | −1.1 (9) |
N1—Co—N2—C10 | 175.7 (4) | Co—N3—C13—C14 | −177.9 (5) |
N3—Co—N2—C10 | −92.2 (4) | N3—C13—C14—C15 | 1.0 (10) |
N5—Co—N2—C10 | 115.6 (7) | C13—C14—C15—C16 | −0.4 (10) |
N4—Co—N2—C10 | −13.3 (4) | C14—C15—C16—C24 | 0.0 (10) |
N6—Co—N2—C10 | 84.8 (4) | C14—C15—C16—C17 | −178.4 (7) |
N1—Co—N2—C11 | 3.1 (3) | C15—C16—C17—C18 | 178.2 (7) |
N3—Co—N2—C11 | 95.2 (3) | C24—C16—C17—C18 | −0.2 (10) |
N5—Co—N2—C11 | −57.0 (8) | C16—C17—C18—C19 | 0.4 (12) |
N4—Co—N2—C11 | 174.1 (3) | C17—C18—C19—C20 | −179.1 (7) |
N6—Co—N2—C11 | −87.8 (3) | C17—C18—C19—C23 | 0.0 (10) |
N2—Co—N3—C13 | −87.7 (5) | C18—C19—C20—C21 | −178.9 (6) |
N1—Co—N3—C13 | −9.0 (5) | C23—C19—C20—C21 | 1.9 (9) |
N5—Co—N3—C13 | 85.5 (5) | C19—C20—C21—C22 | −0.2 (9) |
N4—Co—N3—C13 | 179.0 (5) | C23—N4—C22—C21 | 0.9 (8) |
N2—Co—N3—C24 | 95.3 (4) | Co—N4—C22—C21 | −178.0 (4) |
N1—Co—N3—C24 | 174.0 (4) | C20—C21—C22—N4 | −1.3 (9) |
N5—Co—N3—C24 | −91.5 (4) | C22—N4—C23—C19 | 0.9 (8) |
N4—Co—N3—C24 | 2.0 (4) | Co—N4—C23—C19 | −180.0 (4) |
N2—Co—N4—C22 | 80.9 (5) | C22—N4—C23—C24 | 180.0 (5) |
N1—Co—N4—C22 | 133.1 (8) | Co—N4—C23—C24 | −0.9 (6) |
N3—Co—N4—C22 | 178.4 (5) | C20—C19—C23—N4 | −2.3 (8) |
N5—Co—N4—C22 | −87.7 (5) | C18—C19—C23—N4 | 178.4 (6) |
N6—Co—N4—C22 | −9.4 (5) | C20—C19—C23—C24 | 178.7 (5) |
N2—Co—N4—C23 | −98.2 (4) | C18—C19—C23—C24 | −0.6 (8) |
N1—Co—N4—C23 | −45.9 (10) | C13—N3—C24—C16 | 0.6 (8) |
N3—Co—N4—C23 | −0.6 (3) | Co—N3—C24—C16 | 178.0 (4) |
N5—Co—N4—C23 | 93.3 (4) | C13—N3—C24—C23 | 179.4 (5) |
N6—Co—N4—C23 | 171.6 (4) | Co—N3—C24—C23 | −3.2 (6) |
N2—Co—N5—C25 | 148.5 (6) | C15—C16—C24—N3 | −0.1 (9) |
N1—Co—N5—C25 | 90.2 (5) | C17—C16—C24—N3 | 178.4 (6) |
N3—Co—N5—C25 | −3.9 (5) | C15—C16—C24—C23 | −178.9 (6) |
N4—Co—N5—C25 | −82.5 (5) | C17—C16—C24—C23 | −0.4 (9) |
N6—Co—N5—C25 | −179.9 (5) | N4—C23—C24—N3 | 2.9 (7) |
N2—Co—N5—C36 | −27.1 (8) | C19—C23—C24—N3 | −178.1 (5) |
N1—Co—N5—C36 | −85.4 (3) | N4—C23—C24—C16 | −178.3 (5) |
N3—Co—N5—C36 | −179.5 (3) | C19—C23—C24—C16 | 0.8 (8) |
N4—Co—N5—C36 | 101.9 (3) | C36—N5—C25—C26 | 0.3 (8) |
N6—Co—N5—C36 | 4.5 (3) | Co—N5—C25—C26 | −175.1 (4) |
N2—Co—N6—C34 | −7.2 (4) | N5—C25—C26—C27 | 1.0 (9) |
N1—Co—N6—C34 | −85.5 (4) | C25—C26—C27—C28 | −2.0 (9) |
N5—Co—N6—C34 | −179.6 (5) | C26—C27—C28—C36 | 1.6 (8) |
N4—Co—N6—C34 | 87.7 (4) | C26—C27—C28—C29 | −179.3 (5) |
N2—Co—N6—C35 | 167.8 (3) | C27—C28—C29—C30 | 180.0 (5) |
N1—Co—N6—C35 | 89.5 (3) | C36—C28—C29—C30 | −0.9 (8) |
N5—Co—N6—C35 | −4.5 (3) | C28—C29—C30—C31 | 1.8 (8) |
N4—Co—N6—C35 | −97.3 (3) | C29—C30—C31—C32 | 178.2 (5) |
O8—O8—N8—O7 | 0.0 (3) | C29—C30—C31—C35 | −1.5 (8) |
O8—O8—N8—O7 | 0.0 (3) | C35—C31—C32—C33 | −0.1 (8) |
O8—O8—N8—O9 | 0.0 (5) | C30—C31—C32—C33 | −179.8 (5) |
O8—O8—N8—O9 | 0.0 (5) | C31—C32—C33—C34 | −0.5 (9) |
O7—O7—N8—O8 | 0.0 (3) | C35—N6—C34—C33 | −0.7 (8) |
O7—O7—N8—O8 | 0.0 (3) | Co—N6—C34—C33 | 174.2 (4) |
O7—O7—N8—O9 | 0.0 (2) | C32—C33—C34—N6 | 1.0 (9) |
O7—O7—N8—O9 | 0.0 (2) | C34—N6—C35—C31 | −0.1 (7) |
O9—O9—N8—O8 | 0.0 (4) | Co—N6—C35—C31 | −175.7 (4) |
O9—O9—N8—O8 | 0.0 (4) | C34—N6—C35—C36 | 179.7 (4) |
O9—O9—N8—O7 | 0.0 (3) | Co—N6—C35—C36 | 4.0 (5) |
O9—O9—N8—O7 | 0.0 (3) | C32—C31—C35—N6 | 0.5 (7) |
O4—O4—N9—O5 | 0.0 (4) | C30—C31—C35—N6 | −179.8 (5) |
O4—O4—N9—O6 | 0.00 (14) | C32—C31—C35—C36 | −179.3 (4) |
O4—O4—N9—O6 | 0.00 (14) | C30—C31—C35—C36 | 0.4 (7) |
O6—O6—N9—O4 | 0.0 (6) | C25—N5—C36—C28 | −0.7 (7) |
O6—O6—N9—O4 | 0.0 (6) | Co—N5—C36—C28 | 175.3 (4) |
O6—O6—N9—O5 | 0.0 (8) | C25—N5—C36—C35 | 180.0 (4) |
C12—N1—C1—C2 | −0.2 (7) | Co—N5—C36—C35 | −3.9 (5) |
Co—N1—C1—C2 | 176.9 (3) | C27—C28—C36—N5 | −0.3 (7) |
N1—C1—C2—C3 | −0.1 (7) | C29—C28—C36—N5 | −179.4 (4) |
C1—C2—C3—C4 | 0.0 (7) | C27—C28—C36—C35 | 179.0 (4) |
C2—C3—C4—C12 | 0.4 (7) | C29—C28—C36—C35 | −0.1 (7) |
C2—C3—C4—C5 | 179.6 (5) | N6—C35—C36—N5 | −0.1 (6) |
C3—C4—C5—C6 | 177.7 (5) | C31—C35—C36—N5 | 179.7 (4) |
C12—C4—C5—C6 | −3.2 (7) | N6—C35—C36—C28 | −179.4 (4) |
C4—C5—C6—C7 | 1.5 (8) | C31—C35—C36—C28 | 0.4 (7) |
C5—C6—C7—C8 | −177.5 (5) | C38i—C37—C39—C38 | 0.2 (11) |
C5—C6—C7—C11 | 1.3 (7) | C38i—C37—C39—C40 | 179.0 (6) |
C11—C7—C8—C9 | 1.2 (7) | C37i—C38—C39—C37 | −0.2 (10) |
C6—C7—C8—C9 | 180.0 (5) | C37i—C38—C39—C40 | −178.9 (6) |
C7—C8—C9—C10 | 0.4 (8) | O1—O1—C40—N7 | 0.0 (3) |
C11—N2—C10—C9 | −0.2 (7) | O1—O1—C40—C39 | 0.00 (10) |
Co—N2—C10—C9 | −172.6 (4) | C41—N7—C40—O1 | −7.1 (9) |
C8—C9—C10—N2 | −0.9 (9) | C41—N7—C40—O1 | −7.1 (9) |
C10—N2—C11—C7 | 1.9 (6) | C41—N7—C40—C39 | 172.9 (5) |
Co—N2—C11—C7 | 175.4 (3) | C37—C39—C40—O1 | 2.9 (9) |
C10—N2—C11—C12 | −177.0 (4) | C38—C39—C40—O1 | −178.3 (6) |
Co—N2—C11—C12 | −3.5 (5) | C37—C39—C40—O1 | 2.9 (9) |
C8—C7—C11—N2 | −2.4 (7) | C38—C39—C40—O1 | −178.3 (6) |
C6—C7—C11—N2 | 178.7 (4) | C37—C39—C40—N7 | −177.2 (6) |
C8—C7—C11—C12 | 176.5 (4) | C38—C39—C40—N7 | 1.6 (9) |
C6—C7—C11—C12 | −2.4 (7) | C40—N7—C41—C42 | 92.4 (6) |
C1—N1—C12—C4 | 0.7 (6) | N7—C41—C42—O2 | 0.5 (7) |
Co—N1—C12—C4 | −176.8 (3) | N7—C41—C42—O3 | −178.7 (4) |
C1—N1—C12—C11 | 178.7 (4) |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···O10 | 0.82 (1) | 1.80 (2) | 2.598 (5) | 162 (7) |
O10—H10A···O9 | 0.87 (2) | 2.09 (2) | 2.954 (6) | 172 (5) |
O10—H10A···O7 | 0.87 (2) | 2.54 (4) | 3.190 (7) | 132 (5) |
O10—H10B···O2ii | 0.82 (1) | 2.07 (2) | 2.878 (6) | 171 (6) |
O11—H11A···O8 | 0.85 (8) | 2.32 (8) | 3.098 (9) | 154 (7) |
O11—H11A···O7 | 0.85 (8) | 2.53 (8) | 3.313 (8) | 154 (7) |
O11—H11B···O6 | 0.93 (8) | 2.02 (8) | 2.917 (7) | 162 (7) |
O12—H12A···O11iii | 0.88 (2) | 2.18 (7) | 2.945 (10) | 146 (11) |
O12—H12B···O13 | 0.88 (2) | 1.93 (5) | 2.766 (8) | 156 (11) |
O13—H13A···O5iv | 0.89 (2) | 1.98 (5) | 2.827 (9) | 160 (12) |
O13—H13B···O12v | 0.88 (2) | 2.09 (9) | 2.843 (11) | 143 (12) |
N7—H7···O4 | 0.82 (2) | 2.06 (3) | 2.861 (6) | 165 (7) |
C3—H3···O1 | 0.94 | 2.37 | 3.111 (6) | 135 |
C33—H33···O9 | 0.94 | 2.54 | 3.314 (7) | 140 |
C38—H38···O4 | 0.94 | 2.47 | 3.386 (7) | 166 |
C41—H41B···O6 | 0.98 | 2.67 | 3.409 (7) | 132 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x+1, −y, −z+1. |
Acknowledgements
We acknowledge support by Deutsche Forschungsgemeinschaft and the Open Access Publishing Fund of Clausthal University of Technology. Furthermore, the authors are indebted to Professor Dr A. Adam for his support and helpful suggestions.
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