research communications
of bis[4′-(1,4,7,10-tetraoxa-13- azacyclopentadecan-13-yl)-2,2′:6′,2′′-terpyridine]cobalt(III) tris(perchlorate) methanol monosolvate monohydrate
aDepartment of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1 Kurokami Kumamoto 860-8555, Japan
*Correspondence e-mail: hayami@sci.kumamoto-u.ac.jp
In the title compound, [Co(C25H30N4O4)2](ClO4)3·CH3OH·H2O, the metal atom is coordinated by two tridentate crown ether terpyridine ligands, forming a distorted CoN6 octahedron. The three pyridine rings in each crown–terpyridine ligand are approximately coplanar [maximum deviations = 0.088 (12) and 0.102 (15) Å] and the mean planes through the three pyridine rings are perpendicular to each other, making a dihedral angle of 89.95 (17)°. An intramolecular C—H⋯π interaction is observed between the two terpyridine ligands. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds, a π–π stacking interaction [centroid–centroid distance = 3.923 (7) Å] and a C—H⋯π interaction connect the complex cation, the perchlorate anions and the two types of solvent molecules, forming a three-dimensional network.
Keywords: crystal structure; terpyridine; crown ether; hydrogen bonding; C—H⋯π interactions; π–π stacking interactions.
CCDC reference: 1415327
1. Chemical context
Metal complexes with terpyridine derivatives, [M(R-terpy)]X2 (M = transition metal ions; R-terpy = substituted 2,2′:6′,2′′-terpyridine; X = anion), have been investigated because of their interesting properties such as magnetic and photochemical characteristics. Cobalt(II) complexes with R-terpy ligands are known as spin-crossover compounds. Previously, we observed the unique spin-transition behavior in [Co(II)(R-terpy)2](BF4)2 with long-alkylated terpyridine ligands, and showed that the magnetic behaviors are influenced not only by inter-chain interactions between long alkyl chains but also by π–π stacking interactions between terpyridine moieties (Hayami et al., 2011). We suggested that intermolecular interactions play an important role for the magnetic behaviors of metal complexes. Herein we focused on the terpyridine ligand with a crown ether ring, and synthesized the title compound.
2. Structural commentary
The 2] complex cation, three perchlorate anions, one methanol solvent molecule and one water solvent molecule. The molecular structure of the complex cation is shown in Fig. 1. The cobalt(III) atom is octahedrally coordinated by six nitrogen atoms of two crown–terpy ligands, i.e. an N6 donor set. The coordination bond lengths are typical of those for low-spin cobalt(III) compounds. The Co—N distances of the central pyridine in the terpyridine unit [1.844 (9) Å] are shorter than the Co—N distances of the side pyridine in the terpyridine unit [1.910 (10)–1.949 (10) Å], which induces a pronounced distortion of the CoN6 octahedron. The three pyridine rings in each crown–terpy ligand are approximately coplanar [maximum deviations 0.102 (15) and 0.088 (12) Å], and the two mean planes through the three pyridine rings in the complex are nearly perpendicular to each other, making a dihedral angle of 89.95 (17)°.
of the title compound consists of one [Co(crown–terpy)3. Supramolecular feature
The overall packing of structure is shown in Fig. 2. In the crystal, O—H⋯O hydrogen bonds are formed between the water molecule and the complex cation, between the water molecule and the perchlorate anion, and between the methanol molecule and the complex cation (Table 1). Together with these hydrogen bonds, C—H⋯O hydrogen bonds connect the four components, forming a three-dimensional network. In addition, between pyridine rings of neighboring molecules a C—H⋯π interaction (Table 1) and a π–π interaction are observed. The centroid–centroid distance between the N1/C1–C5 and N3/C11–C15 pyridine rings is 3.923 (7) Å.
4. Synthesis and crystallization
The crown-terpyridine ligand was prepared by the reaction of 4′-bromo-2,2′:6′,2′′-terpyridine (249.2 mg, 1 mmol) and 1,4,7,10-tetraoxa-13-azacyclopentadecane (459.2 mg, 1 mmol) in DMF. The mixed solution was evaporated to give the ligand as a white powder. Co(ClO4)3 (68.16 mg, 0.5 mmol) dissolved in methanol (20 ml) was poured dropwise into a solution of the crown–terpy ligand (100 mg, 0.21 mmol) in 1:1 methanol–chloroform. The precipitate formed immediately and was filtered. Single crystals of the title compound suitable for X-ray diffraction were obtained from a methanol solution.
5. Refinement
Crystal data, data collection and structure . H atoms in the complex cation and the methanol molecule were placed in calculated positions (C—H = 0.93–0.97 Å and O—H = 0.82 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O, Cmethyl). The positions of the H atoms of the water molecule were refined with restraints of O—H = 0.85 (2) and H⋯H = 1.38 (2) Å, and with Uiso(H) = 1.5Ueq(O).
details are summarized in Table 2
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Supporting information
CCDC reference: 1415327
https://doi.org/10.1107/S2056989015014164/is5400sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014164/is5400Isup2.hkl
Data collection: RAPID-AUTO (Rigaku, 1995); cell
RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2014); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).[Co(C25H30N4O4)2](ClO4)3·CH4O·H2O | Z = 1 |
Mr = 1308.42 | F(000) = 682.00 |
Triclinic, P1 | Dx = 1.560 Mg m−3 |
a = 8.8080 (8) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 9.5032 (8) Å | Cell parameters from 9503 reflections |
c = 16.9321 (14) Å | θ = 3.1–27.5° |
α = 84.237 (2)° | µ = 0.54 mm−1 |
β = 81.674 (2)° | T = 100 K |
γ = 85.652 (3)° | Platelet, brown |
V = 1392.6 (2) Å3 | 0.50 × 0.10 × 0.05 mm |
Rigaku R-AXIS RAPID diffractometer | 6395 reflections with F2 > 2σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.098 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | h = −11→11 |
Tmin = 0.370, Tmax = 0.973 | k = −12→12 |
13693 measured reflections | l = −21→21 |
10375 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.256 | w = 1/[σ2(Fo2) + (0.1411P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
10375 reflections | Δρmax = 0.96 e Å−3 |
774 parameters | Δρmin = −1.09 e Å−3 |
6 restraints | Absolute structure: Flack x determined using 1715 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (3) |
Secondary atom site location: difference Fourier map |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.76909 (15) | 0.08790 (13) | 0.13275 (9) | 0.0288 (4) | |
Cl1 | 0.3213 (4) | 0.1579 (4) | −0.1139 (2) | 0.0467 (8) | |
Cl2 | 0.4623 (5) | 0.5336 (3) | 0.2794 (2) | 0.0496 (9) | |
Cl3 | 0.0656 (4) | 0.0376 (3) | 0.43350 (17) | 0.0349 (7) | |
O1 | 0.2434 (10) | −0.2957 (9) | 0.5627 (5) | 0.040 (2) | |
O2 | 0.2493 (11) | −0.5893 (9) | 0.6131 (5) | 0.039 (2) | |
O3 | 0.5560 (11) | −0.7130 (9) | 0.5627 (5) | 0.040 (2) | |
O4 | 0.7922 (11) | −0.5239 (8) | 0.5341 (5) | 0.038 (2) | |
O5 | 0.6674 (11) | 0.4750 (8) | −0.2506 (5) | 0.041 (2) | |
O6 | 0.5788 (10) | 0.7563 (9) | −0.2955 (5) | 0.0355 (19) | |
O7 | 0.7867 (12) | 0.9733 (9) | −0.2658 (5) | 0.043 (2) | |
O8 | 0.9854 (12) | 0.7656 (9) | −0.1865 (6) | 0.044 (2) | |
O9 | 0.2713 (15) | 0.2838 (16) | −0.0750 (8) | 0.089 (5) | |
O10 | 0.379 (2) | 0.1901 (16) | −0.1895 (8) | 0.119 (7) | |
O11 | 0.1913 (16) | 0.0748 (15) | −0.1079 (11) | 0.101 (5) | |
O12 | 0.433 (2) | 0.0815 (19) | −0.0708 (14) | 0.147 (8) | |
O13 | 0.4992 (13) | 0.4261 (11) | 0.3397 (6) | 0.059 (3) | |
O14 | 0.5172 (15) | 0.4906 (12) | 0.2014 (5) | 0.061 (3) | |
O15 | 0.2926 (16) | 0.5578 (13) | 0.2866 (9) | 0.090 (5) | |
O16 | 0.532 (2) | 0.6637 (12) | 0.2864 (7) | 0.092 (5) | |
O17 | 0.1782 (13) | 0.1141 (11) | 0.4618 (6) | 0.056 (3) | |
O18 | 0.0058 (11) | 0.1245 (9) | 0.3700 (6) | 0.047 (2) | |
O19 | 0.1408 (12) | −0.0920 (10) | 0.4047 (6) | 0.049 (2) | |
O20 | −0.0586 (11) | 0.0040 (10) | 0.4955 (6) | 0.050 (3) | |
O21 | 1.0569 (13) | 0.7203 (12) | −0.0296 (7) | 0.058 (3) | |
O22 | 0.5440 (14) | 0.4499 (11) | −0.0796 (6) | 0.058 (3) | |
N1 | 0.5582 (12) | 0.1554 (9) | 0.1505 (5) | 0.029 (2) | |
N2 | 0.7229 (11) | 0.0005 (10) | 0.2348 (6) | 0.027 (2) | |
N3 | 0.9705 (12) | −0.0059 (10) | 0.1438 (5) | 0.028 (2) | |
N4 | 0.6214 (12) | −0.1840 (10) | 0.4670 (6) | 0.031 (2) | |
N5 | 0.7192 (12) | −0.0609 (10) | 0.0721 (6) | 0.030 (2) | |
N6 | 0.8196 (12) | 0.1781 (10) | 0.0318 (5) | 0.030 (2) | |
N7 | 0.8311 (12) | 0.2623 (10) | 0.1661 (5) | 0.029 (2) | |
N8 | 0.9469 (13) | 0.3779 (10) | −0.1943 (6) | 0.034 (2) | |
C1 | 0.4792 (16) | 0.2376 (12) | 0.0982 (7) | 0.035 (3) | |
C2 | 0.3246 (16) | 0.2856 (12) | 0.1191 (7) | 0.038 (3) | |
C3 | 0.2545 (16) | 0.2508 (13) | 0.1965 (8) | 0.037 (3) | |
C4 | 0.3316 (15) | 0.1623 (12) | 0.2487 (7) | 0.034 (3) | |
C5 | 0.4812 (13) | 0.1165 (11) | 0.2256 (7) | 0.028 (2) | |
C6 | 0.5781 (14) | 0.0217 (11) | 0.2748 (7) | 0.029 (3) | |
C7 | 0.5383 (15) | −0.0367 (12) | 0.3520 (7) | 0.032 (3) | |
C8 | 0.6496 (14) | −0.1234 (12) | 0.3894 (7) | 0.028 (3) | |
C9 | 0.8020 (13) | −0.1426 (11) | 0.3471 (6) | 0.027 (2) | |
C10 | 0.8303 (14) | −0.0796 (12) | 0.2689 (7) | 0.029 (2) | |
C11 | 0.9784 (15) | −0.0824 (12) | 0.2149 (7) | 0.032 (3) | |
C12 | 1.1133 (15) | −0.1560 (11) | 0.2315 (7) | 0.032 (3) | |
C13 | 1.2438 (15) | −0.1510 (12) | 0.1753 (7) | 0.034 (3) | |
C14 | 1.2326 (15) | −0.0707 (13) | 0.1017 (7) | 0.034 (3) | |
C15 | 1.0963 (16) | −0.0005 (12) | 0.0896 (7) | 0.037 (3) | |
C16 | 0.4678 (14) | −0.1757 (12) | 0.5139 (7) | 0.032 (3) | |
C17 | 0.3766 (15) | −0.3032 (13) | 0.5053 (8) | 0.036 (3) | |
C18 | 0.1299 (15) | −0.3849 (13) | 0.5462 (8) | 0.040 (3) | |
C19 | 0.1884 (17) | −0.5405 (14) | 0.5399 (8) | 0.042 (3) | |
C20 | 0.2917 (17) | −0.7374 (14) | 0.6149 (9) | 0.045 (3) | |
C21 | 0.4214 (16) | −0.7781 (13) | 0.5537 (8) | 0.040 (3) | |
C22 | 0.6712 (17) | −0.7252 (13) | 0.4948 (7) | 0.040 (3) | |
C23 | 0.8174 (17) | −0.6641 (13) | 0.5112 (8) | 0.043 (3) | |
C24 | 0.7705 (17) | −0.4219 (12) | 0.4687 (7) | 0.037 (3) | |
C25 | 0.7350 (15) | −0.2780 (11) | 0.5036 (7) | 0.033 (3) | |
C26 | 0.6618 (14) | −0.1841 (12) | 0.1009 (7) | 0.034 (3) | |
C27 | 0.6197 (15) | −0.2781 (13) | 0.0522 (7) | 0.036 (3) | |
C28 | 0.6395 (17) | −0.2449 (13) | −0.0316 (8) | 0.038 (3) | |
C29 | 0.7026 (15) | −0.1173 (12) | −0.0633 (7) | 0.034 (3) | |
C30 | 0.7400 (13) | −0.0264 (11) | −0.0100 (6) | 0.027 (2) | |
C31 | 0.8041 (15) | 0.1133 (12) | −0.0339 (7) | 0.033 (3) | |
C32 | 0.8445 (14) | 0.1755 (12) | −0.1095 (7) | 0.033 (3) | |
C33 | 0.9060 (15) | 0.3130 (13) | −0.1208 (7) | 0.033 (3) | |
C34 | 0.9234 (14) | 0.3770 (12) | −0.0500 (6) | 0.031 (3) | |
C35 | 0.8782 (14) | 0.3093 (12) | 0.0243 (7) | 0.033 (3) | |
C36 | 0.8802 (14) | 0.3583 (11) | 0.1029 (7) | 0.031 (3) | |
C37 | 0.9269 (15) | 0.4901 (12) | 0.1171 (7) | 0.036 (3) | |
C38 | 0.9210 (17) | 0.5219 (13) | 0.1950 (8) | 0.043 (3) | |
C39 | 0.8734 (17) | 0.4287 (14) | 0.2562 (8) | 0.041 (3) | |
C40 | 0.8241 (15) | 0.2973 (12) | 0.2417 (6) | 0.031 (3) | |
C41 | 1.0265 (17) | 0.5099 (12) | −0.2036 (7) | 0.036 (3) | |
C42 | 0.9121 (16) | 0.6387 (11) | −0.1958 (8) | 0.040 (3) | |
C43 | 1.0336 (17) | 0.8480 (14) | −0.2601 (8) | 0.045 (3) | |
C44 | 0.9077 (17) | 0.8978 (14) | −0.3117 (8) | 0.043 (3) | |
C45 | 0.6521 (18) | 0.9962 (14) | −0.3080 (9) | 0.045 (3) | |
C46 | 0.5347 (16) | 0.8952 (12) | −0.2743 (7) | 0.036 (3) | |
C47 | 0.4694 (17) | 0.6548 (14) | −0.2622 (9) | 0.045 (3) | |
C48 | 0.5297 (17) | 0.5122 (14) | −0.2852 (8) | 0.043 (3) | |
C49 | 0.7317 (16) | 0.3359 (12) | −0.2671 (7) | 0.039 (3) | |
C50 | 0.9005 (17) | 0.3271 (13) | −0.2658 (7) | 0.040 (3) | |
C51 | 1.2209 (19) | 0.689 (2) | −0.0377 (11) | 0.069 (5) | |
H1 | 0.52847 | 0.26304 | 0.04691 | 0.0416* | |
H2 | 0.27099 | 0.33921 | 0.08191 | 0.0452* | |
H3 | 0.15536 | 0.28732 | 0.21306 | 0.0444* | |
H4 | 0.28238 | 0.13362 | 0.29951 | 0.0406* | |
H5 | 0.460 (11) | 0.409 (19) | −0.076 (10) | 0.0869* | |
H6 | 0.600 (16) | 0.427 (19) | −0.123 (7) | 0.0869* | |
H7 | 0.43993 | −0.01952 | 0.37897 | 0.0387* | |
H9 | 0.87922 | −0.19533 | 0.37099 | 0.0324* | |
H12 | 1.11622 | −0.209 | 0.2806 | 0.0388* | |
H13 | 1.33574 | −0.19894 | 0.18579 | 0.0408* | |
H14 | 1.31708 | −0.06576 | 0.06186 | 0.0414* | |
H15 | 1.09069 | 0.05389 | 0.04119 | 0.0441* | |
H16A | 0.41193 | −0.0893 | 0.49601 | 0.0384* | |
H16B | 0.47775 | −0.17185 | 0.5699 | 0.0384* | |
H17A | 0.34885 | −0.29899 | 0.45173 | 0.0433* | |
H17B | 0.43728 | −0.39104 | 0.51536 | 0.0433* | |
H18A | 0.09371 | −0.34791 | 0.49631 | 0.0484* | |
H18B | 0.04296 | −0.38105 | 0.58843 | 0.0484* | |
H19A | 0.10483 | −0.59723 | 0.53314 | 0.0499* | |
H19B | 0.26787 | −0.54819 | 0.49415 | 0.0499* | |
H20A | 0.20282 | −0.78667 | 0.60781 | 0.0536* | |
H20B | 0.31881 | −0.7699 | 0.66753 | 0.0536* | |
H21A | 0.44077 | −0.88019 | 0.55882 | 0.0484* | |
H21B | 0.39411 | −0.75 | 0.50068 | 0.0484* | |
H21 | 1.03052 | 0.73952 | −0.07417 | 0.0872* | |
H22A | 0.63565 | −0.67401 | 0.4477 | 0.0482* | |
H22B | 0.69184 | −0.824 | 0.4847 | 0.0482* | |
H23A | 0.85969 | −0.72429 | 0.55344 | 0.0513* | |
H23B | 0.89263 | −0.66473 | 0.46331 | 0.0513* | |
H24A | 0.68576 | −0.44509 | 0.44261 | 0.0445* | |
H24B | 0.86261 | −0.41941 | 0.42964 | 0.0445* | |
H25A | 0.69899 | −0.29483 | 0.56047 | 0.0397* | |
H25B | 0.82982 | −0.23003 | 0.49808 | 0.0397* | |
H26 | 0.64963 | −0.20782 | 0.15597 | 0.0411* | |
H27 | 0.57841 | −0.36271 | 0.07453 | 0.0430* | |
H28 | 0.61109 | −0.30695 | −0.06523 | 0.0458* | |
H29 | 0.71936 | −0.09348 | −0.11837 | 0.0404* | |
H32 | 0.83213 | 0.12896 | −0.1537 | 0.0392* | |
H34 | 0.96538 | 0.46477 | −0.05424 | 0.0377* | |
H37 | 0.96122 | 0.55491 | 0.0746 | 0.0431* | |
H38 | 0.95067 | 0.60943 | 0.2051 | 0.0518* | |
H39 | 0.87272 | 0.45066 | 0.30853 | 0.0495* | |
H40 | 0.78657 | 0.23442 | 0.28449 | 0.0368* | |
H41A | 1.0891 | 0.51881 | −0.2557 | 0.0437* | |
H41B | 1.09422 | 0.50689 | −0.16298 | 0.0437* | |
H42A | 0.8606 | 0.65387 | −0.24308 | 0.0475* | |
H42B | 0.83472 | 0.61967 | −0.14974 | 0.0475* | |
H43A | 1.11253 | 0.7924 | −0.29157 | 0.0539* | |
H43B | 1.08039 | 0.93084 | −0.24759 | 0.0539* | |
H44A | 0.94991 | 0.95862 | −0.35793 | 0.0514* | |
H44B | 0.86853 | 0.8167 | −0.33082 | 0.0514* | |
H45A | 0.68295 | 0.98447 | −0.36441 | 0.0541* | |
H45B | 0.60843 | 1.09236 | −0.30335 | 0.0541* | |
H46A | 0.51838 | 0.89439 | −0.21641 | 0.0435* | |
H46B | 0.43828 | 0.92643 | −0.29376 | 0.0435* | |
H47A | 0.37225 | 0.67984 | −0.28225 | 0.0538* | |
H47B | 0.45203 | 0.65426 | −0.20432 | 0.0538* | |
H48A | 0.45417 | 0.44319 | −0.26576 | 0.0519* | |
H48B | 0.55108 | 0.51345 | −0.34307 | 0.0519* | |
H49A | 0.71053 | 0.31531 | −0.31931 | 0.0465* | |
H49B | 0.68437 | 0.266 | −0.22725 | 0.0465* | |
H50A | 0.9391 | 0.22923 | −0.26928 | 0.0481* | |
H50B | 0.94854 | 0.38219 | −0.31293 | 0.0481* | |
H51A | 1.27242 | 0.77439 | −0.05623 | 0.1031* | |
H51B | 1.2499 | 0.62005 | −0.0756 | 0.1031* | |
H51C | 1.24968 | 0.65275 | 0.01334 | 0.1031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0355 (9) | 0.0233 (7) | 0.0266 (8) | −0.0017 (6) | −0.0056 (7) | 0.0036 (6) |
Cl1 | 0.048 (2) | 0.0461 (18) | 0.0415 (17) | 0.0059 (16) | −0.0020 (15) | 0.0076 (14) |
Cl2 | 0.075 (3) | 0.0331 (17) | 0.0392 (17) | −0.0001 (16) | −0.0137 (18) | 0.0077 (14) |
Cl3 | 0.0405 (17) | 0.0311 (14) | 0.0323 (14) | −0.0015 (13) | −0.0064 (13) | 0.0018 (12) |
O1 | 0.035 (5) | 0.039 (5) | 0.041 (5) | −0.000 (4) | 0.009 (4) | 0.001 (4) |
O2 | 0.042 (5) | 0.032 (4) | 0.039 (5) | 0.007 (4) | −0.005 (4) | 0.006 (4) |
O3 | 0.041 (5) | 0.037 (5) | 0.043 (5) | −0.006 (4) | −0.006 (4) | −0.011 (4) |
O4 | 0.055 (6) | 0.024 (4) | 0.034 (4) | 0.002 (4) | −0.007 (4) | 0.005 (3) |
O5 | 0.056 (6) | 0.026 (4) | 0.041 (5) | 0.001 (4) | −0.012 (4) | −0.003 (4) |
O6 | 0.043 (5) | 0.034 (4) | 0.030 (4) | −0.005 (4) | −0.010 (4) | 0.001 (4) |
O7 | 0.058 (6) | 0.030 (4) | 0.041 (5) | 0.007 (4) | −0.015 (4) | −0.000 (4) |
O8 | 0.052 (6) | 0.027 (4) | 0.053 (5) | −0.012 (4) | −0.015 (5) | 0.008 (4) |
O9 | 0.063 (8) | 0.120 (11) | 0.095 (9) | 0.027 (8) | −0.022 (7) | −0.066 (9) |
O10 | 0.21 (2) | 0.080 (9) | 0.048 (7) | −0.033 (11) | 0.028 (10) | 0.016 (7) |
O11 | 0.063 (9) | 0.083 (10) | 0.162 (15) | −0.031 (8) | −0.002 (10) | −0.031 (10) |
O12 | 0.134 (16) | 0.101 (12) | 0.22 (2) | 0.054 (12) | −0.097 (16) | −0.038 (14) |
O13 | 0.063 (7) | 0.056 (6) | 0.054 (6) | −0.003 (5) | −0.023 (5) | 0.034 (5) |
O14 | 0.089 (9) | 0.067 (7) | 0.031 (5) | −0.026 (6) | −0.013 (5) | 0.001 (5) |
O15 | 0.080 (9) | 0.070 (8) | 0.104 (10) | 0.047 (7) | −0.003 (8) | 0.012 (7) |
O16 | 0.175 (16) | 0.052 (7) | 0.051 (7) | −0.047 (8) | 0.001 (8) | −0.009 (5) |
O17 | 0.059 (7) | 0.057 (6) | 0.059 (6) | −0.010 (5) | −0.030 (5) | −0.010 (5) |
O18 | 0.047 (6) | 0.036 (5) | 0.049 (5) | 0.004 (4) | 0.005 (5) | 0.013 (4) |
O19 | 0.055 (6) | 0.045 (5) | 0.048 (5) | 0.006 (5) | −0.016 (5) | −0.005 (4) |
O20 | 0.047 (6) | 0.050 (6) | 0.042 (5) | 0.000 (5) | 0.016 (5) | 0.015 (4) |
O21 | 0.063 (7) | 0.050 (6) | 0.059 (6) | −0.009 (5) | −0.011 (6) | 0.012 (5) |
O22 | 0.074 (8) | 0.052 (6) | 0.044 (6) | 0.005 (6) | −0.004 (6) | 0.000 (5) |
N1 | 0.033 (6) | 0.024 (5) | 0.027 (5) | −0.009 (4) | 0.003 (4) | 0.005 (4) |
N2 | 0.023 (5) | 0.029 (5) | 0.027 (5) | −0.005 (4) | −0.001 (4) | 0.003 (4) |
N3 | 0.032 (5) | 0.031 (5) | 0.021 (4) | −0.009 (4) | −0.006 (4) | 0.004 (4) |
N4 | 0.032 (6) | 0.025 (5) | 0.032 (5) | −0.005 (4) | −0.004 (4) | 0.011 (4) |
N5 | 0.033 (5) | 0.025 (5) | 0.032 (5) | 0.002 (4) | −0.009 (4) | 0.003 (4) |
N6 | 0.039 (6) | 0.033 (5) | 0.021 (5) | −0.008 (4) | −0.013 (4) | 0.012 (4) |
N7 | 0.039 (6) | 0.025 (5) | 0.020 (4) | 0.005 (4) | 0.001 (4) | 0.004 (4) |
N8 | 0.045 (6) | 0.027 (5) | 0.026 (5) | 0.000 (5) | −0.004 (5) | 0.012 (4) |
C1 | 0.045 (8) | 0.027 (6) | 0.031 (6) | −0.002 (5) | −0.008 (6) | 0.003 (5) |
C2 | 0.054 (9) | 0.027 (6) | 0.031 (6) | 0.004 (6) | −0.012 (6) | 0.006 (5) |
C3 | 0.034 (7) | 0.031 (6) | 0.043 (7) | −0.001 (5) | −0.003 (6) | 0.004 (6) |
C4 | 0.037 (7) | 0.031 (6) | 0.032 (6) | −0.004 (5) | 0.001 (6) | 0.003 (5) |
C5 | 0.024 (6) | 0.025 (5) | 0.031 (6) | 0.003 (5) | 0.006 (5) | 0.003 (5) |
C6 | 0.031 (6) | 0.019 (5) | 0.035 (6) | −0.000 (5) | 0.001 (5) | −0.001 (5) |
C7 | 0.035 (7) | 0.028 (6) | 0.032 (6) | −0.012 (5) | −0.004 (5) | 0.011 (5) |
C8 | 0.024 (6) | 0.029 (6) | 0.029 (6) | −0.003 (5) | −0.001 (5) | 0.006 (5) |
C9 | 0.029 (6) | 0.027 (5) | 0.025 (5) | −0.003 (5) | −0.012 (5) | 0.008 (4) |
C10 | 0.036 (7) | 0.026 (5) | 0.027 (5) | −0.005 (5) | −0.011 (5) | −0.002 (5) |
C11 | 0.042 (7) | 0.024 (5) | 0.034 (6) | −0.013 (5) | −0.013 (6) | 0.004 (5) |
C12 | 0.049 (8) | 0.021 (5) | 0.026 (5) | 0.005 (5) | −0.010 (5) | 0.006 (4) |
C13 | 0.039 (7) | 0.025 (6) | 0.038 (6) | 0.006 (5) | −0.011 (6) | −0.001 (5) |
C14 | 0.037 (7) | 0.035 (6) | 0.029 (6) | −0.012 (6) | −0.005 (5) | 0.015 (5) |
C15 | 0.046 (8) | 0.029 (6) | 0.033 (6) | −0.004 (5) | −0.002 (6) | 0.008 (5) |
C16 | 0.037 (7) | 0.024 (5) | 0.031 (6) | −0.001 (5) | 0.007 (5) | −0.002 (5) |
C17 | 0.038 (7) | 0.033 (6) | 0.038 (6) | −0.009 (5) | −0.007 (6) | 0.003 (5) |
C18 | 0.036 (7) | 0.033 (6) | 0.049 (7) | −0.003 (6) | −0.002 (6) | 0.012 (6) |
C19 | 0.041 (8) | 0.041 (7) | 0.044 (7) | −0.011 (6) | −0.015 (6) | 0.009 (6) |
C20 | 0.044 (8) | 0.032 (7) | 0.056 (8) | −0.006 (6) | −0.005 (7) | 0.008 (6) |
C21 | 0.044 (8) | 0.030 (6) | 0.048 (7) | 0.001 (6) | −0.012 (6) | −0.004 (6) |
C22 | 0.055 (9) | 0.033 (6) | 0.032 (6) | 0.002 (6) | −0.005 (6) | −0.008 (5) |
C23 | 0.055 (9) | 0.027 (6) | 0.040 (7) | 0.010 (6) | 0.012 (6) | −0.008 (5) |
C24 | 0.053 (8) | 0.032 (6) | 0.024 (6) | 0.002 (6) | −0.005 (6) | 0.002 (5) |
C25 | 0.040 (7) | 0.024 (5) | 0.033 (6) | −0.001 (5) | −0.004 (5) | 0.006 (5) |
C26 | 0.037 (7) | 0.030 (6) | 0.032 (6) | 0.000 (5) | 0.002 (6) | 0.006 (5) |
C27 | 0.042 (8) | 0.027 (6) | 0.036 (7) | −0.006 (5) | 0.000 (6) | 0.004 (5) |
C28 | 0.049 (8) | 0.033 (6) | 0.034 (6) | 0.001 (6) | −0.006 (6) | −0.008 (5) |
C29 | 0.038 (7) | 0.031 (6) | 0.032 (6) | −0.002 (5) | −0.013 (5) | 0.009 (5) |
C30 | 0.032 (6) | 0.026 (5) | 0.023 (5) | 0.005 (5) | −0.000 (5) | −0.002 (4) |
C31 | 0.043 (7) | 0.029 (6) | 0.026 (6) | −0.001 (5) | −0.012 (5) | 0.007 (5) |
C32 | 0.033 (7) | 0.031 (6) | 0.033 (6) | −0.002 (5) | −0.004 (5) | −0.000 (5) |
C33 | 0.037 (7) | 0.030 (6) | 0.028 (6) | 0.002 (5) | 0.006 (5) | 0.005 (5) |
C34 | 0.040 (7) | 0.027 (5) | 0.027 (6) | −0.002 (5) | −0.009 (5) | 0.007 (5) |
C35 | 0.035 (7) | 0.028 (6) | 0.036 (6) | −0.002 (5) | −0.006 (5) | 0.006 (5) |
C36 | 0.042 (7) | 0.023 (5) | 0.026 (5) | 0.004 (5) | −0.007 (5) | 0.006 (4) |
C37 | 0.041 (7) | 0.028 (6) | 0.034 (6) | −0.001 (5) | 0.004 (6) | 0.004 (5) |
C38 | 0.063 (10) | 0.024 (6) | 0.044 (7) | −0.009 (6) | −0.012 (7) | 0.003 (5) |
C39 | 0.048 (8) | 0.036 (7) | 0.040 (7) | −0.006 (6) | −0.008 (6) | −0.003 (6) |
C40 | 0.043 (7) | 0.031 (6) | 0.014 (5) | 0.002 (5) | 0.001 (5) | 0.007 (4) |
C41 | 0.056 (8) | 0.024 (5) | 0.027 (5) | −0.009 (5) | −0.003 (6) | 0.007 (5) |
C42 | 0.050 (8) | 0.020 (5) | 0.049 (7) | −0.008 (5) | −0.010 (7) | 0.005 (5) |
C43 | 0.049 (9) | 0.034 (7) | 0.048 (8) | −0.006 (6) | −0.000 (7) | 0.007 (6) |
C44 | 0.057 (9) | 0.035 (7) | 0.035 (7) | −0.006 (6) | −0.006 (6) | 0.008 (6) |
C45 | 0.061 (9) | 0.031 (6) | 0.047 (7) | 0.005 (6) | −0.026 (7) | −0.002 (6) |
C46 | 0.044 (7) | 0.032 (6) | 0.028 (6) | 0.007 (5) | −0.000 (5) | 0.005 (5) |
C47 | 0.045 (8) | 0.036 (7) | 0.048 (8) | −0.002 (6) | 0.002 (7) | 0.005 (6) |
C48 | 0.054 (9) | 0.036 (7) | 0.044 (7) | −0.010 (6) | −0.021 (7) | 0.006 (6) |
C49 | 0.055 (9) | 0.031 (6) | 0.031 (6) | −0.005 (6) | −0.013 (6) | 0.007 (5) |
C50 | 0.066 (10) | 0.028 (6) | 0.028 (6) | −0.004 (6) | −0.013 (6) | 0.004 (5) |
C51 | 0.039 (9) | 0.096 (13) | 0.069 (11) | 0.019 (9) | 0.004 (8) | −0.027 (10) |
Co1—N1 | 1.910 (10) | C33—C34 | 1.430 (17) |
Co1—N2 | 1.844 (9) | C34—C35 | 1.374 (15) |
Co1—N3 | 1.949 (10) | C35—C36 | 1.457 (17) |
Co1—N5 | 1.940 (10) | C36—C37 | 1.401 (17) |
Co1—N6 | 1.844 (9) | C37—C38 | 1.375 (19) |
Co1—N7 | 1.944 (10) | C38—C39 | 1.334 (18) |
Cl1—O9 | 1.433 (15) | C39—C40 | 1.409 (19) |
Cl1—O10 | 1.322 (13) | C41—C42 | 1.529 (17) |
Cl1—O11 | 1.425 (15) | C43—C44 | 1.53 (2) |
Cl1—O12 | 1.42 (2) | C45—C46 | 1.478 (19) |
Cl2—O13 | 1.424 (11) | C47—C48 | 1.485 (18) |
Cl2—O14 | 1.427 (10) | C49—C50 | 1.49 (2) |
Cl2—O15 | 1.484 (15) | O21—H21 | 0.820 |
Cl2—O16 | 1.444 (15) | O22—H5 | 0.86 (13) |
Cl3—O17 | 1.435 (12) | O22—H6 | 0.86 (12) |
Cl3—O18 | 1.426 (10) | C1—H1 | 0.930 |
Cl3—O19 | 1.448 (10) | C2—H2 | 0.930 |
Cl3—O20 | 1.434 (9) | C3—H3 | 0.930 |
O1—C17 | 1.413 (15) | C4—H4 | 0.930 |
O1—C18 | 1.433 (17) | C7—H7 | 0.930 |
O2—C19 | 1.443 (17) | C9—H9 | 0.930 |
O2—C20 | 1.427 (15) | C12—H12 | 0.930 |
O3—C21 | 1.412 (17) | C13—H13 | 0.930 |
O3—C22 | 1.428 (15) | C14—H14 | 0.930 |
O4—C23 | 1.418 (15) | C15—H15 | 0.930 |
O4—C24 | 1.421 (14) | C16—H16A | 0.970 |
O5—C48 | 1.427 (18) | C16—H16B | 0.970 |
O5—C49 | 1.435 (14) | C17—H17A | 0.970 |
O6—C46 | 1.413 (14) | C17—H17B | 0.970 |
O6—C47 | 1.432 (16) | C18—H18A | 0.970 |
O7—C44 | 1.418 (16) | C18—H18B | 0.970 |
O7—C45 | 1.463 (19) | C19—H19A | 0.970 |
O8—C42 | 1.442 (16) | C19—H19B | 0.970 |
O8—C43 | 1.431 (15) | C20—H20A | 0.970 |
O21—C51 | 1.44 (2) | C20—H20B | 0.970 |
N1—C1 | 1.355 (16) | C21—H21A | 0.970 |
N1—C5 | 1.382 (14) | C21—H21B | 0.970 |
N2—C6 | 1.366 (14) | C22—H22A | 0.970 |
N2—C10 | 1.329 (15) | C22—H22B | 0.970 |
N3—C11 | 1.350 (14) | C23—H23A | 0.970 |
N3—C15 | 1.333 (15) | C23—H23B | 0.970 |
N4—C8 | 1.376 (14) | C24—H24A | 0.970 |
N4—C16 | 1.466 (15) | C24—H24B | 0.970 |
N4—C25 | 1.455 (16) | C25—H25A | 0.970 |
N5—C26 | 1.329 (15) | C25—H25B | 0.970 |
N5—C30 | 1.386 (14) | C26—H26 | 0.930 |
N6—C31 | 1.352 (16) | C27—H27 | 0.930 |
N6—C35 | 1.371 (15) | C28—H28 | 0.930 |
N7—C36 | 1.375 (13) | C29—H29 | 0.930 |
N7—C40 | 1.346 (14) | C32—H32 | 0.930 |
N8—C33 | 1.345 (15) | C34—H34 | 0.930 |
N8—C41 | 1.468 (16) | C37—H37 | 0.930 |
N8—C50 | 1.469 (17) | C38—H38 | 0.930 |
C1—C2 | 1.410 (19) | C39—H39 | 0.930 |
C2—C3 | 1.383 (17) | C40—H40 | 0.930 |
C3—C4 | 1.375 (18) | C41—H41A | 0.970 |
C4—C5 | 1.370 (16) | C41—H41B | 0.970 |
C5—C6 | 1.474 (16) | C42—H42A | 0.970 |
C6—C7 | 1.374 (15) | C42—H42B | 0.970 |
C7—C8 | 1.412 (17) | C43—H43A | 0.970 |
C8—C9 | 1.436 (16) | C43—H43B | 0.970 |
C9—C10 | 1.393 (14) | C44—H44A | 0.970 |
C10—C11 | 1.481 (17) | C44—H44B | 0.970 |
C11—C12 | 1.383 (18) | C45—H45A | 0.970 |
C12—C13 | 1.383 (17) | C45—H45B | 0.970 |
C13—C14 | 1.406 (16) | C46—H46A | 0.970 |
C14—C15 | 1.360 (18) | C46—H46B | 0.970 |
C16—C17 | 1.533 (18) | C47—H47A | 0.970 |
C18—C19 | 1.538 (18) | C47—H47B | 0.970 |
C20—C21 | 1.482 (19) | C48—H48A | 0.970 |
C22—C23 | 1.52 (2) | C48—H48B | 0.970 |
C24—C25 | 1.537 (16) | C49—H49A | 0.970 |
C26—C27 | 1.378 (19) | C49—H49B | 0.970 |
C27—C28 | 1.412 (17) | C50—H50A | 0.970 |
C28—C29 | 1.398 (17) | C50—H50B | 0.970 |
C29—C30 | 1.398 (18) | C51—H51A | 0.960 |
C30—C31 | 1.478 (16) | C51—H51B | 0.960 |
C31—C32 | 1.366 (16) | C51—H51C | 0.960 |
C32—C33 | 1.437 (17) | ||
N1—Co1—N2 | 82.8 (4) | C4—C3—H3 | 120.021 |
N1—Co1—N3 | 164.5 (4) | C3—C4—H4 | 120.141 |
N1—Co1—N5 | 91.1 (4) | C5—C4—H4 | 120.134 |
N1—Co1—N6 | 98.1 (4) | C6—C7—H7 | 120.652 |
N1—Co1—N7 | 90.5 (4) | C8—C7—H7 | 120.652 |
N2—Co1—N3 | 81.7 (4) | C8—C9—H9 | 121.141 |
N2—Co1—N5 | 99.0 (4) | C10—C9—H9 | 121.144 |
N2—Co1—N6 | 178.3 (5) | C11—C12—H12 | 119.971 |
N2—Co1—N7 | 95.9 (4) | C13—C12—H12 | 119.965 |
N3—Co1—N5 | 91.2 (4) | C12—C13—H13 | 121.168 |
N3—Co1—N6 | 97.5 (4) | C14—C13—H13 | 121.166 |
N3—Co1—N7 | 91.2 (4) | C13—C14—H14 | 120.481 |
N5—Co1—N6 | 82.5 (4) | C15—C14—H14 | 120.483 |
N5—Co1—N7 | 165.2 (4) | N3—C15—H15 | 118.383 |
N6—Co1—N7 | 82.7 (4) | C14—C15—H15 | 118.390 |
O9—Cl1—O10 | 110.7 (9) | N4—C16—H16A | 109.257 |
O9—Cl1—O11 | 107.3 (8) | N4—C16—H16B | 109.253 |
O9—Cl1—O12 | 107.7 (11) | C17—C16—H16A | 109.253 |
O10—Cl1—O11 | 111.5 (12) | C17—C16—H16B | 109.259 |
O10—Cl1—O12 | 111.0 (13) | H16A—C16—H16B | 107.926 |
O11—Cl1—O12 | 108.5 (10) | O1—C17—H17A | 110.452 |
O13—Cl2—O14 | 110.7 (6) | O1—C17—H17B | 110.444 |
O13—Cl2—O15 | 108.7 (7) | C16—C17—H17A | 110.452 |
O13—Cl2—O16 | 111.3 (8) | C16—C17—H17B | 110.448 |
O14—Cl2—O15 | 108.3 (8) | H17A—C17—H17B | 108.644 |
O14—Cl2—O16 | 107.4 (7) | O1—C18—H18A | 108.759 |
O15—Cl2—O16 | 110.4 (9) | O1—C18—H18B | 108.762 |
O17—Cl3—O18 | 108.1 (6) | C19—C18—H18A | 108.763 |
O17—Cl3—O19 | 108.1 (6) | C19—C18—H18B | 108.766 |
O17—Cl3—O20 | 111.7 (6) | H18A—C18—H18B | 107.654 |
O18—Cl3—O19 | 110.5 (6) | O2—C19—H19A | 110.294 |
O18—Cl3—O20 | 108.9 (6) | O2—C19—H19B | 110.295 |
O19—Cl3—O20 | 109.5 (6) | C18—C19—H19A | 110.291 |
C17—O1—C18 | 111.2 (10) | C18—C19—H19B | 110.289 |
C19—O2—C20 | 110.2 (10) | H19A—C19—H19B | 108.538 |
C21—O3—C22 | 111.7 (10) | O2—C20—H20A | 108.474 |
C23—O4—C24 | 112.8 (9) | O2—C20—H20B | 108.478 |
C48—O5—C49 | 112.6 (10) | C21—C20—H20A | 108.465 |
C46—O6—C47 | 113.5 (9) | C21—C20—H20B | 108.478 |
C44—O7—C45 | 110.5 (10) | H20A—C20—H20B | 107.499 |
C42—O8—C43 | 114.5 (11) | O3—C21—H21A | 109.410 |
Co1—N1—C1 | 127.0 (8) | O3—C21—H21B | 109.415 |
Co1—N1—C5 | 115.2 (7) | C20—C21—H21A | 109.416 |
C1—N1—C5 | 117.8 (10) | C20—C21—H21B | 109.416 |
Co1—N2—C6 | 118.8 (7) | H21A—C21—H21B | 108.037 |
Co1—N2—C10 | 120.1 (7) | O3—C22—H22A | 109.885 |
C6—N2—C10 | 121.0 (9) | O3—C22—H22B | 109.885 |
Co1—N3—C11 | 114.3 (8) | C23—C22—H22A | 109.877 |
Co1—N3—C15 | 126.9 (8) | C23—C22—H22B | 109.879 |
C11—N3—C15 | 118.8 (11) | H22A—C22—H22B | 108.297 |
C8—N4—C16 | 122.0 (10) | O4—C23—H23A | 109.006 |
C8—N4—C25 | 122.2 (9) | O4—C23—H23B | 109.008 |
C16—N4—C25 | 115.1 (9) | C22—C23—H23A | 109.009 |
Co1—N5—C26 | 127.4 (8) | C22—C23—H23B | 109.015 |
Co1—N5—C30 | 113.6 (7) | H23A—C23—H23B | 107.796 |
C26—N5—C30 | 118.8 (10) | O4—C24—H24A | 110.387 |
Co1—N6—C31 | 120.2 (8) | O4—C24—H24B | 110.388 |
Co1—N6—C35 | 119.1 (8) | C25—C24—H24A | 110.389 |
C31—N6—C35 | 120.7 (9) | C25—C24—H24B | 110.393 |
Co1—N7—C36 | 113.4 (7) | H24A—C24—H24B | 108.597 |
Co1—N7—C40 | 127.0 (7) | N4—C25—H25A | 108.460 |
C36—N7—C40 | 119.6 (10) | N4—C25—H25B | 108.456 |
C33—N8—C41 | 120.0 (11) | C24—C25—H25A | 108.463 |
C33—N8—C50 | 121.3 (11) | C24—C25—H25B | 108.461 |
C41—N8—C50 | 118.4 (9) | H25A—C25—H25B | 107.486 |
N1—C1—C2 | 122.0 (10) | N5—C26—H26 | 118.708 |
C1—C2—C3 | 118.3 (12) | C27—C26—H26 | 118.704 |
C2—C3—C4 | 120.0 (12) | C26—C27—H27 | 120.236 |
C3—C4—C5 | 119.7 (11) | C28—C27—H27 | 120.239 |
N1—C5—C4 | 122.0 (10) | C27—C28—H28 | 120.568 |
N1—C5—C6 | 112.1 (9) | C29—C28—H28 | 120.559 |
C4—C5—C6 | 125.9 (10) | C28—C29—H29 | 120.888 |
N2—C6—C5 | 111.0 (9) | C30—C29—H29 | 120.881 |
N2—C6—C7 | 121.6 (11) | C31—C32—H32 | 120.008 |
C5—C6—C7 | 127.4 (11) | C33—C32—H32 | 120.011 |
C6—C7—C8 | 118.7 (11) | C33—C34—H34 | 119.888 |
N4—C8—C7 | 122.9 (10) | C35—C34—H34 | 119.902 |
N4—C8—C9 | 118.0 (10) | C36—C37—H37 | 120.610 |
C7—C8—C9 | 119.0 (10) | C38—C37—H37 | 120.594 |
C8—C9—C10 | 117.7 (10) | C37—C38—H38 | 119.558 |
N2—C10—C9 | 121.9 (10) | C39—C38—H38 | 119.575 |
N2—C10—C11 | 110.9 (9) | C38—C39—H39 | 119.913 |
C9—C10—C11 | 127.1 (11) | C40—C39—H39 | 119.926 |
N3—C11—C10 | 113.0 (11) | N7—C40—H40 | 119.898 |
N3—C11—C12 | 121.2 (11) | C39—C40—H40 | 119.886 |
C10—C11—C12 | 125.8 (10) | N8—C41—H41A | 109.396 |
C11—C12—C13 | 120.1 (10) | N8—C41—H41B | 109.392 |
C12—C13—C14 | 117.7 (11) | C42—C41—H41A | 109.398 |
C13—C14—C15 | 119.0 (11) | C42—C41—H41B | 109.394 |
N3—C15—C14 | 123.2 (11) | H41A—C41—H41B | 108.007 |
N4—C16—C17 | 111.8 (9) | O8—C42—H42A | 109.132 |
O1—C17—C16 | 106.4 (10) | O8—C42—H42B | 109.132 |
O1—C18—C19 | 114.0 (11) | C41—C42—H42A | 109.128 |
O2—C19—C18 | 107.1 (11) | C41—C42—H42B | 109.134 |
O2—C20—C21 | 115.2 (11) | H42A—C42—H42B | 107.861 |
O3—C21—C20 | 111.1 (11) | O8—C43—H43A | 108.294 |
O3—C22—C23 | 109.0 (11) | O8—C43—H43B | 108.291 |
O4—C23—C22 | 112.9 (11) | C44—C43—H43A | 108.307 |
O4—C24—C25 | 106.7 (9) | C44—C43—H43B | 108.303 |
N4—C25—C24 | 115.3 (11) | H43A—C43—H43B | 107.409 |
N5—C26—C27 | 122.6 (11) | O7—C44—H44A | 109.754 |
C26—C27—C28 | 119.5 (11) | O7—C44—H44B | 109.758 |
C27—C28—C29 | 118.9 (12) | C43—C44—H44A | 109.758 |
C28—C29—C30 | 118.2 (11) | C43—C44—H44B | 109.758 |
N5—C30—C29 | 121.9 (10) | H44A—C44—H44B | 108.224 |
N5—C30—C31 | 113.3 (10) | O7—C45—H45A | 109.466 |
C29—C30—C31 | 124.8 (10) | O7—C45—H45B | 109.463 |
N6—C31—C30 | 110.3 (9) | C46—C45—H45A | 109.470 |
N6—C31—C32 | 121.7 (11) | C46—C45—H45B | 109.471 |
C30—C31—C32 | 128.0 (11) | H45A—C45—H45B | 108.057 |
C31—C32—C33 | 120.0 (12) | O6—C46—H46A | 109.215 |
N8—C33—C32 | 121.8 (11) | O6—C46—H46B | 109.219 |
N8—C33—C34 | 121.5 (11) | C45—C46—H46A | 109.216 |
C32—C33—C34 | 116.7 (10) | C45—C46—H46B | 109.217 |
C33—C34—C35 | 120.2 (11) | H46A—C46—H46B | 107.910 |
N6—C35—C34 | 120.7 (11) | O6—C47—H47A | 109.862 |
N6—C35—C36 | 110.5 (9) | O6—C47—H47B | 109.865 |
C34—C35—C36 | 128.7 (11) | C48—C47—H47A | 109.870 |
N7—C36—C35 | 114.2 (10) | C48—C47—H47B | 109.868 |
N7—C36—C37 | 120.3 (10) | H47A—C47—H47B | 108.282 |
C35—C36—C37 | 125.5 (10) | O5—C48—H48A | 110.013 |
C36—C37—C38 | 118.8 (11) | O5—C48—H48B | 110.017 |
C37—C38—C39 | 120.9 (13) | C47—C48—H48A | 110.013 |
C38—C39—C40 | 120.2 (13) | C47—C48—H48B | 110.016 |
N7—C40—C39 | 120.2 (10) | H48A—C48—H48B | 108.374 |
N8—C41—C42 | 111.2 (11) | O5—C49—H49A | 109.631 |
O8—C42—C41 | 112.4 (11) | O5—C49—H49B | 109.634 |
O8—C43—C44 | 115.9 (12) | C50—C49—H49A | 109.629 |
O7—C44—C43 | 109.6 (11) | C50—C49—H49B | 109.629 |
O7—C45—C46 | 110.9 (11) | H49A—C49—H49B | 108.155 |
O6—C46—C45 | 112.0 (10) | N8—C50—H50A | 108.683 |
O6—C47—C48 | 109.1 (11) | N8—C50—H50B | 108.676 |
O5—C48—C47 | 108.4 (12) | C49—C50—H50A | 108.681 |
O5—C49—C50 | 110.1 (11) | C49—C50—H50B | 108.680 |
N8—C50—C49 | 114.3 (10) | H50A—C50—H50B | 107.616 |
C51—O21—H21 | 109.475 | O21—C51—H51A | 109.476 |
H5—O22—H6 | 107 (16) | O21—C51—H51B | 109.467 |
N1—C1—H1 | 119.021 | O21—C51—H51C | 109.476 |
C2—C1—H1 | 119.019 | H51A—C51—H51B | 109.467 |
C1—C2—H2 | 120.833 | H51A—C51—H51C | 109.471 |
C3—C2—H2 | 120.842 | H51B—C51—H51C | 109.469 |
C2—C3—H3 | 120.023 | ||
N1—Co1—N2—C6 | −1.5 (7) | C25—N4—C16—C17 | −79.3 (12) |
N1—Co1—N2—C10 | 179.7 (8) | Co1—N5—C26—C27 | 175.0 (7) |
N2—Co1—N1—C1 | −178.0 (8) | Co1—N5—C30—C29 | −176.7 (7) |
N2—Co1—N1—C5 | 3.0 (6) | Co1—N5—C30—C31 | 3.3 (11) |
N1—Co1—N5—C26 | −80.1 (8) | C26—N5—C30—C29 | −0.1 (16) |
N1—Co1—N5—C30 | 96.2 (6) | C26—N5—C30—C31 | 179.9 (9) |
N5—Co1—N1—C1 | −79.1 (8) | C30—N5—C26—C27 | −1.1 (17) |
N5—Co1—N1—C5 | 101.9 (6) | Co1—N6—C31—C30 | 1.9 (13) |
N1—Co1—N6—C31 | −90.3 (8) | Co1—N6—C31—C32 | −178.2 (7) |
N1—Co1—N6—C35 | 92.1 (8) | Co1—N6—C35—C34 | 177.2 (7) |
N6—Co1—N1—C1 | 3.5 (9) | Co1—N6—C35—C36 | −3.7 (13) |
N6—Co1—N1—C5 | −175.5 (6) | C31—N6—C35—C34 | −0.5 (17) |
N1—Co1—N7—C36 | −98.9 (6) | C31—N6—C35—C36 | 178.6 (10) |
N1—Co1—N7—C40 | 78.2 (8) | C35—N6—C31—C30 | 179.6 (9) |
N7—Co1—N1—C1 | 86.2 (8) | C35—N6—C31—C32 | −0.5 (18) |
N7—Co1—N1—C5 | −92.9 (6) | Co1—N7—C36—C35 | −1.0 (12) |
N2—Co1—N3—C11 | −0.3 (6) | Co1—N7—C36—C37 | 179.2 (7) |
N2—Co1—N3—C15 | −179.8 (9) | Co1—N7—C40—C39 | −179.8 (7) |
N3—Co1—N2—C6 | 178.5 (8) | C36—N7—C40—C39 | −2.9 (16) |
N3—Co1—N2—C10 | −0.3 (7) | C40—N7—C36—C35 | −178.2 (9) |
N2—Co1—N5—C26 | 2.8 (9) | C40—N7—C36—C37 | 1.9 (16) |
N2—Co1—N5—C30 | 179.1 (6) | C33—N8—C41—C42 | −86.0 (13) |
N5—Co1—N2—C6 | −91.6 (7) | C41—N8—C33—C32 | −172.5 (10) |
N5—Co1—N2—C10 | 89.7 (8) | C41—N8—C33—C34 | 6.7 (17) |
N2—Co1—N7—C36 | 178.3 (6) | C33—N8—C50—C49 | 63.4 (14) |
N2—Co1—N7—C40 | −4.6 (8) | C50—N8—C33—C32 | 13.5 (17) |
N7—Co1—N2—C6 | 88.2 (7) | C50—N8—C33—C34 | −167.3 (10) |
N7—Co1—N2—C10 | −90.6 (7) | C41—N8—C50—C49 | −110.7 (11) |
N3—Co1—N5—C26 | 84.6 (8) | C50—N8—C41—C42 | 88.1 (12) |
N3—Co1—N5—C30 | −99.2 (6) | N1—C1—C2—C3 | 2.2 (18) |
N5—Co1—N3—C11 | −99.2 (7) | C1—C2—C3—C4 | −5.1 (19) |
N5—Co1—N3—C15 | 81.3 (8) | C2—C3—C4—C5 | 4.4 (19) |
N3—Co1—N6—C31 | 90.1 (8) | C3—C4—C5—N1 | −0.6 (18) |
N3—Co1—N6—C35 | −87.6 (7) | C3—C4—C5—C6 | −180.0 (11) |
N6—Co1—N3—C11 | 178.2 (6) | N1—C5—C6—N2 | 2.5 (13) |
N6—Co1—N3—C15 | −1.3 (9) | N1—C5—C6—C7 | −180.0 (10) |
N3—Co1—N7—C36 | 96.6 (6) | C4—C5—C6—N2 | −178.1 (11) |
N3—Co1—N7—C40 | −86.4 (8) | C4—C5—C6—C7 | −0.6 (19) |
N7—Co1—N3—C11 | 95.5 (6) | N2—C6—C7—C8 | −1.5 (17) |
N7—Co1—N3—C15 | −84.1 (8) | C5—C6—C7—C8 | −178.9 (10) |
N5—Co1—N6—C31 | −0.2 (7) | C6—C7—C8—N4 | 178.6 (10) |
N5—Co1—N6—C35 | −177.9 (8) | C6—C7—C8—C9 | 2.6 (17) |
N6—Co1—N5—C26 | −178.1 (9) | N4—C8—C9—C10 | −179.2 (9) |
N6—Co1—N5—C30 | −1.8 (6) | C7—C8—C9—C10 | −3.1 (16) |
N6—Co1—N7—C36 | −0.8 (6) | C8—C9—C10—N2 | 2.6 (17) |
N6—Co1—N7—C40 | 176.2 (8) | C8—C9—C10—C11 | 178.5 (10) |
N7—Co1—N6—C31 | −179.7 (8) | N2—C10—C11—N3 | −0.9 (14) |
N7—Co1—N6—C35 | 2.6 (7) | N2—C10—C11—C12 | −179.6 (10) |
C17—O1—C18—C19 | 55.3 (12) | C9—C10—C11—N3 | −177.2 (11) |
C18—O1—C17—C16 | 164.1 (8) | C9—C10—C11—C12 | 4 (2) |
C19—O2—C20—C21 | 66.0 (14) | N3—C11—C12—C13 | 0.7 (18) |
C20—O2—C19—C18 | 174.2 (9) | C10—C11—C12—C13 | 179.3 (10) |
C21—O3—C22—C23 | −175.3 (8) | C11—C12—C13—C14 | −0.8 (17) |
C22—O3—C21—C20 | −167.2 (8) | C12—C13—C14—C15 | 1.1 (18) |
C23—O4—C24—C25 | 176.6 (9) | C13—C14—C15—N3 | −1.4 (19) |
C24—O4—C23—C22 | −74.7 (12) | N4—C16—C17—O1 | 170.5 (8) |
C48—O5—C49—C50 | 153.2 (9) | O1—C18—C19—O2 | 55.2 (13) |
C49—O5—C48—C47 | 177.9 (8) | O2—C20—C21—O3 | 60.1 (15) |
C46—O6—C47—C48 | −177.6 (9) | O3—C22—C23—O4 | −53.7 (12) |
C47—O6—C46—C45 | 178.5 (9) | O4—C24—C25—N4 | −142.6 (9) |
C44—O7—C45—C46 | 101.9 (11) | N5—C26—C27—C28 | 1.0 (18) |
C45—O7—C44—C43 | −168.2 (9) | C26—C27—C28—C29 | 0.4 (18) |
C42—O8—C43—C44 | 57.6 (13) | C27—C28—C29—C30 | −1.5 (18) |
C43—O8—C42—C41 | 91.5 (12) | C28—C29—C30—N5 | 1.4 (17) |
Co1—N1—C1—C2 | −177.5 (7) | C28—C29—C30—C31 | −178.6 (10) |
Co1—N1—C5—C4 | 176.8 (7) | N5—C30—C31—N6 | −3.3 (14) |
Co1—N1—C5—C6 | −3.7 (11) | N5—C30—C31—C32 | 176.8 (10) |
C1—N1—C5—C4 | −2.3 (16) | C29—C30—C31—N6 | 176.7 (10) |
C1—N1—C5—C6 | 177.2 (9) | C29—C30—C31—C32 | −3 (2) |
C5—N1—C1—C2 | 1.5 (16) | N6—C31—C32—C33 | 0.4 (18) |
Co1—N2—C6—C5 | −0.1 (12) | C30—C31—C32—C33 | −179.8 (10) |
Co1—N2—C6—C7 | −177.8 (7) | C31—C32—C33—N8 | −179.9 (11) |
Co1—N2—C10—C9 | 177.3 (7) | C31—C32—C33—C34 | 0.8 (17) |
Co1—N2—C10—C11 | 0.7 (13) | N8—C33—C34—C35 | 178.9 (10) |
C6—N2—C10—C9 | −1.5 (17) | C32—C33—C34—C35 | −1.8 (17) |
C6—N2—C10—C11 | −178.0 (9) | C33—C34—C35—N6 | 1.7 (18) |
C10—N2—C6—C5 | 178.7 (9) | C33—C34—C35—C36 | −177.3 (10) |
C10—N2—C6—C7 | 0.9 (17) | N6—C35—C36—N7 | 2.8 (14) |
Co1—N3—C11—C10 | 0.7 (12) | N6—C35—C36—C37 | −177.3 (10) |
Co1—N3—C11—C12 | 179.5 (7) | C34—C35—C36—N7 | −178.1 (11) |
Co1—N3—C15—C14 | −179.2 (7) | C34—C35—C36—C37 | 2 (2) |
C11—N3—C15—C14 | 1.3 (18) | N7—C36—C37—C38 | −0.7 (17) |
C15—N3—C11—C10 | −179.7 (10) | C35—C36—C37—C38 | 179.4 (10) |
C15—N3—C11—C12 | −0.9 (17) | C36—C37—C38—C39 | 1 (2) |
C8—N4—C16—C17 | 91.8 (11) | C37—C38—C39—C40 | −2 (2) |
C16—N4—C8—C7 | 6.8 (17) | C38—C39—C40—N7 | 3 (2) |
C16—N4—C8—C9 | −177.1 (9) | N8—C41—C42—O8 | 167.0 (9) |
C8—N4—C25—C24 | −68.2 (14) | O8—C43—C44—O7 | 55.0 (14) |
C25—N4—C8—C7 | 177.3 (10) | O7—C45—C46—O6 | −72.7 (13) |
C25—N4—C8—C9 | −6.7 (16) | O6—C47—C48—O5 | 63.1 (13) |
C16—N4—C25—C24 | 102.8 (10) | O5—C49—C50—N8 | 50.2 (12) |
Cg1 and Cg2 are the centroids of the N7/C36–C40 and N2/C6–C10 pyridine rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O21—H21···O8 | 0.82 | 1.99 | 2.802 (15) | 173 |
O22—H5···O9 | 0.86 (13) | 2.11 (14) | 2.960 (19) | 172 (15) |
O22—H6···O5 | 0.86 (12) | 2.17 (11) | 2.934 (13) | 148 (14) |
C4—H4···O18 | 0.93 | 2.56 | 3.299 (16) | 137 |
C15—H15···O11i | 0.93 | 2.54 | 3.35 (2) | 145 |
C16—H16B···O6ii | 0.97 | 2.58 | 3.491 (15) | 157 |
C20—H20B···O10ii | 0.97 | 2.54 | 3.50 (2) | 170 |
C22—H22A···O13iii | 0.97 | 2.41 | 3.365 (17) | 168 |
C25—H25A···O6ii | 0.97 | 2.59 | 3.517 (14) | 160 |
C25—H25B···O20i | 0.97 | 2.49 | 3.331 (15) | 145 |
C26—H26···O16iii | 0.93 | 2.54 | 3.400 (17) | 155 |
C27—H27···O14iii | 0.93 | 2.45 | 3.249 (16) | 143 |
C28—H28···O22iii | 0.93 | 2.47 | 3.290 (17) | 147 |
C29—H29···O7iii | 0.93 | 2.51 | 3.437 (14) | 175 |
C37—H37···O21 | 0.93 | 2.35 | 3.276 (16) | 177 |
C44—H44A···O20iv | 0.97 | 2.49 | 3.297 (17) | 141 |
C3—H3···Cg1v | 0.93 | 2.70 | 3.540 (15) | 151 |
C40—H40···Cg2 | 0.93 | 2.97 | 3.713 (12) | 138 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z+1; (iii) x, y−1, z; (iv) x+1, y+1, z−1; (v) x−1, y, z. |
Acknowledgements
This work was supported by Innovative Areas `Coordination Programming' (area 2107) from the MEXT, Japan.
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