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Crystal structure 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

Edited by H. Ishida, Okayama University, Japan (Received 9 May 2015; accepted 27 July 2015; online 31 July 2015)

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 ππ 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.

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 ππ stacking inter­actions between terpyridine moieties (Hayami et al., 2011[Hayami, S., Komatsu, Y., Shimizu, T., Kamihata, H. & Lee, Y. H. (2011). Coord. Chem. Rev. 255, 1981-1990.]). 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.

[Scheme 1]

2. Structural commentary

The asymmetric unit of the title compound consists of one [Co(crown–terpy)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[link]. 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)°.

[Figure 1]
Figure 1
A view of the complex cation of the title compound, showing displacement ellipsoids at the 50% probability level.

3. Supra­molecular feature

The overall packing of structure is shown in Fig. 2[link]. 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[link]). 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[link]) and a ππ inter­action are observed. The centroid–centroid distance between the N1/C1–C5 and N3/C11–C15 pyridine rings is 3.923 (7) Å.

Table 1
Hydrogen-bond geometry (Å, °)

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 DA 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.
[Figure 2]
Figure 2
Crystal packing diagram of the title compound.

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 refinement details are summarized in Table 2[link]. 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).

Table 2
Experimental details

Crystal data
Chemical formula [Co(C25H30N4O4)2](ClO4)3·CH4O·H2O
Mr 1308.42
Crystal system, space group Triclinic, P1
Temperature (K) 100
a, b, c (Å) 8.8080 (8), 9.5032 (8), 16.9321 (14)
α, β, γ (°) 84.237 (2), 81.674 (2), 85.652 (3)
V3) 1392.6 (2)
Z 1
Radiation type Mo Kα
μ (mm−1) 0.54
Crystal size (mm) 0.50 × 0.10 × 0.05
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
Absorption correction Multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). RAPID-AUTO and ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.370, 0.973
No. of measured, independent and observed [F2 > 2σ(F2)] reflections 13693, 10375, 6395
Rint 0.098
(sin θ/λ)max−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.256, 1.04
No. of reflections 10375
No. of parameters 774
No. of restraints 6
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.96, −1.09
Absolute structure Flack x determined using 1715 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])
Absolute structure parameter 0.02 (3)
Computer programs: RAPID-AUTO (Rigaku, 1995[Rigaku (1995). RAPID-AUTO and ABSCOR. Rigaku Corporation, Tokyo, Japan.]), SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), CrystalStructure (Rigaku, 2014[Rigaku (2014). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Computing details top

Data collection: RAPID-AUTO (Rigaku, 1995); cell refinement: 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).

Bis[4'-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)-2,2':6',2''-terpyridine]cobalt(III) tris(perchlorate) methanol monosolvate monohydrate top
Crystal data top
[Co(C25H30N4O4)2](ClO4)3·CH4O·H2OZ = 1
Mr = 1308.42F(000) = 682.00
Triclinic, P1Dx = 1.560 Mg m3
a = 8.8080 (8) ÅMo Kα radiation, λ = 0.71075 Å
b = 9.5032 (8) ÅCell parameters from 9503 reflections
c = 16.9321 (14) Åθ = 3.1–27.5°
α = 84.237 (2)°µ = 0.54 mm1
β = 81.674 (2)°T = 100 K
γ = 85.652 (3)°Platelet, brown
V = 1392.6 (2) Å30.50 × 0.10 × 0.05 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6395 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.098
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1111
Tmin = 0.370, Tmax = 0.973k = 1212
13693 measured reflectionsl = 2121
10375 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.086H 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 reflectionsΔρmax = 0.96 e Å3
774 parametersΔρmin = 1.09 e Å3
6 restraintsAbsolute structure: Flack x determined using 1715 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (3)
Secondary atom site location: difference Fourier map
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.76909 (15)0.08790 (13)0.13275 (9)0.0288 (4)
Cl10.3213 (4)0.1579 (4)0.1139 (2)0.0467 (8)
Cl20.4623 (5)0.5336 (3)0.2794 (2)0.0496 (9)
Cl30.0656 (4)0.0376 (3)0.43350 (17)0.0349 (7)
O10.2434 (10)0.2957 (9)0.5627 (5)0.040 (2)
O20.2493 (11)0.5893 (9)0.6131 (5)0.039 (2)
O30.5560 (11)0.7130 (9)0.5627 (5)0.040 (2)
O40.7922 (11)0.5239 (8)0.5341 (5)0.038 (2)
O50.6674 (11)0.4750 (8)0.2506 (5)0.041 (2)
O60.5788 (10)0.7563 (9)0.2955 (5)0.0355 (19)
O70.7867 (12)0.9733 (9)0.2658 (5)0.043 (2)
O80.9854 (12)0.7656 (9)0.1865 (6)0.044 (2)
O90.2713 (15)0.2838 (16)0.0750 (8)0.089 (5)
O100.379 (2)0.1901 (16)0.1895 (8)0.119 (7)
O110.1913 (16)0.0748 (15)0.1079 (11)0.101 (5)
O120.433 (2)0.0815 (19)0.0708 (14)0.147 (8)
O130.4992 (13)0.4261 (11)0.3397 (6)0.059 (3)
O140.5172 (15)0.4906 (12)0.2014 (5)0.061 (3)
O150.2926 (16)0.5578 (13)0.2866 (9)0.090 (5)
O160.532 (2)0.6637 (12)0.2864 (7)0.092 (5)
O170.1782 (13)0.1141 (11)0.4618 (6)0.056 (3)
O180.0058 (11)0.1245 (9)0.3700 (6)0.047 (2)
O190.1408 (12)0.0920 (10)0.4047 (6)0.049 (2)
O200.0586 (11)0.0040 (10)0.4955 (6)0.050 (3)
O211.0569 (13)0.7203 (12)0.0296 (7)0.058 (3)
O220.5440 (14)0.4499 (11)0.0796 (6)0.058 (3)
N10.5582 (12)0.1554 (9)0.1505 (5)0.029 (2)
N20.7229 (11)0.0005 (10)0.2348 (6)0.027 (2)
N30.9705 (12)0.0059 (10)0.1438 (5)0.028 (2)
N40.6214 (12)0.1840 (10)0.4670 (6)0.031 (2)
N50.7192 (12)0.0609 (10)0.0721 (6)0.030 (2)
N60.8196 (12)0.1781 (10)0.0318 (5)0.030 (2)
N70.8311 (12)0.2623 (10)0.1661 (5)0.029 (2)
N80.9469 (13)0.3779 (10)0.1943 (6)0.034 (2)
C10.4792 (16)0.2376 (12)0.0982 (7)0.035 (3)
C20.3246 (16)0.2856 (12)0.1191 (7)0.038 (3)
C30.2545 (16)0.2508 (13)0.1965 (8)0.037 (3)
C40.3316 (15)0.1623 (12)0.2487 (7)0.034 (3)
C50.4812 (13)0.1165 (11)0.2256 (7)0.028 (2)
C60.5781 (14)0.0217 (11)0.2748 (7)0.029 (3)
C70.5383 (15)0.0367 (12)0.3520 (7)0.032 (3)
C80.6496 (14)0.1234 (12)0.3894 (7)0.028 (3)
C90.8020 (13)0.1426 (11)0.3471 (6)0.027 (2)
C100.8303 (14)0.0796 (12)0.2689 (7)0.029 (2)
C110.9784 (15)0.0824 (12)0.2149 (7)0.032 (3)
C121.1133 (15)0.1560 (11)0.2315 (7)0.032 (3)
C131.2438 (15)0.1510 (12)0.1753 (7)0.034 (3)
C141.2326 (15)0.0707 (13)0.1017 (7)0.034 (3)
C151.0963 (16)0.0005 (12)0.0896 (7)0.037 (3)
C160.4678 (14)0.1757 (12)0.5139 (7)0.032 (3)
C170.3766 (15)0.3032 (13)0.5053 (8)0.036 (3)
C180.1299 (15)0.3849 (13)0.5462 (8)0.040 (3)
C190.1884 (17)0.5405 (14)0.5399 (8)0.042 (3)
C200.2917 (17)0.7374 (14)0.6149 (9)0.045 (3)
C210.4214 (16)0.7781 (13)0.5537 (8)0.040 (3)
C220.6712 (17)0.7252 (13)0.4948 (7)0.040 (3)
C230.8174 (17)0.6641 (13)0.5112 (8)0.043 (3)
C240.7705 (17)0.4219 (12)0.4687 (7)0.037 (3)
C250.7350 (15)0.2780 (11)0.5036 (7)0.033 (3)
C260.6618 (14)0.1841 (12)0.1009 (7)0.034 (3)
C270.6197 (15)0.2781 (13)0.0522 (7)0.036 (3)
C280.6395 (17)0.2449 (13)0.0316 (8)0.038 (3)
C290.7026 (15)0.1173 (12)0.0633 (7)0.034 (3)
C300.7400 (13)0.0264 (11)0.0100 (6)0.027 (2)
C310.8041 (15)0.1133 (12)0.0339 (7)0.033 (3)
C320.8445 (14)0.1755 (12)0.1095 (7)0.033 (3)
C330.9060 (15)0.3130 (13)0.1208 (7)0.033 (3)
C340.9234 (14)0.3770 (12)0.0500 (6)0.031 (3)
C350.8782 (14)0.3093 (12)0.0243 (7)0.033 (3)
C360.8802 (14)0.3583 (11)0.1029 (7)0.031 (3)
C370.9269 (15)0.4901 (12)0.1171 (7)0.036 (3)
C380.9210 (17)0.5219 (13)0.1950 (8)0.043 (3)
C390.8734 (17)0.4287 (14)0.2562 (8)0.041 (3)
C400.8241 (15)0.2973 (12)0.2417 (6)0.031 (3)
C411.0265 (17)0.5099 (12)0.2036 (7)0.036 (3)
C420.9121 (16)0.6387 (11)0.1958 (8)0.040 (3)
C431.0336 (17)0.8480 (14)0.2601 (8)0.045 (3)
C440.9077 (17)0.8978 (14)0.3117 (8)0.043 (3)
C450.6521 (18)0.9962 (14)0.3080 (9)0.045 (3)
C460.5347 (16)0.8952 (12)0.2743 (7)0.036 (3)
C470.4694 (17)0.6548 (14)0.2622 (9)0.045 (3)
C480.5297 (17)0.5122 (14)0.2852 (8)0.043 (3)
C490.7317 (16)0.3359 (12)0.2671 (7)0.039 (3)
C500.9005 (17)0.3271 (13)0.2658 (7)0.040 (3)
C511.2209 (19)0.689 (2)0.0377 (11)0.069 (5)
H10.528470.263040.046910.0416*
H20.270990.339210.081910.0452*
H30.155360.287320.213060.0444*
H40.282380.133620.299510.0406*
H50.460 (11)0.409 (19)0.076 (10)0.0869*
H60.600 (16)0.427 (19)0.123 (7)0.0869*
H70.439930.019520.378970.0387*
H90.879220.195330.370990.0324*
H121.116220.2090.28060.0388*
H131.335740.198940.185790.0408*
H141.317080.065760.061860.0414*
H151.090690.053890.041190.0441*
H16A0.411930.08930.496010.0384*
H16B0.477750.171850.56990.0384*
H17A0.348850.298990.451730.0433*
H17B0.437280.391040.515360.0433*
H18A0.093710.347910.496310.0484*
H18B0.042960.381050.588430.0484*
H19A0.104830.597230.533140.0499*
H19B0.267870.548190.494150.0499*
H20A0.202820.786670.607810.0536*
H20B0.318810.76990.667530.0536*
H21A0.440770.880190.558820.0484*
H21B0.394110.750.500680.0484*
H211.030520.739520.074170.0872*
H22A0.635650.674010.44770.0482*
H22B0.691840.8240.48470.0482*
H23A0.859690.724290.553440.0513*
H23B0.892630.664730.463310.0513*
H24A0.685760.445090.442610.0445*
H24B0.862610.419410.429640.0445*
H25A0.698990.294830.560470.0397*
H25B0.829820.230030.498080.0397*
H260.649630.207820.155970.0411*
H270.578410.362710.074530.0430*
H280.611090.306950.065230.0458*
H290.719360.093480.118370.0404*
H320.832130.128960.15370.0392*
H340.965380.464770.054240.0377*
H370.961220.554910.07460.0431*
H380.950670.609430.20510.0518*
H390.872720.450660.308530.0495*
H400.786570.234420.284490.0368*
H41A1.08910.518810.25570.0437*
H41B1.094220.506890.162980.0437*
H42A0.86060.653870.243080.0475*
H42B0.834720.619670.149740.0475*
H43A1.112530.79240.291570.0539*
H43B1.080390.930840.247590.0539*
H44A0.949910.958620.357930.0514*
H44B0.868530.81670.330820.0514*
H45A0.682950.984470.364410.0541*
H45B0.608431.092360.303350.0541*
H46A0.518380.894390.216410.0435*
H46B0.438280.926430.293760.0435*
H47A0.372250.679840.282250.0538*
H47B0.452030.654260.204320.0538*
H48A0.454170.443190.265760.0519*
H48B0.551080.513450.343070.0519*
H49A0.710530.315310.319310.0465*
H49B0.684370.2660.227250.0465*
H50A0.93910.229230.269280.0481*
H50B0.948540.382190.312930.0481*
H51A1.272420.774390.056230.1031*
H51B1.24990.620050.07560.1031*
H51C1.249680.652750.013340.1031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0355 (9)0.0233 (7)0.0266 (8)0.0017 (6)0.0056 (7)0.0036 (6)
Cl10.048 (2)0.0461 (18)0.0415 (17)0.0059 (16)0.0020 (15)0.0076 (14)
Cl20.075 (3)0.0331 (17)0.0392 (17)0.0001 (16)0.0137 (18)0.0077 (14)
Cl30.0405 (17)0.0311 (14)0.0323 (14)0.0015 (13)0.0064 (13)0.0018 (12)
O10.035 (5)0.039 (5)0.041 (5)0.000 (4)0.009 (4)0.001 (4)
O20.042 (5)0.032 (4)0.039 (5)0.007 (4)0.005 (4)0.006 (4)
O30.041 (5)0.037 (5)0.043 (5)0.006 (4)0.006 (4)0.011 (4)
O40.055 (6)0.024 (4)0.034 (4)0.002 (4)0.007 (4)0.005 (3)
O50.056 (6)0.026 (4)0.041 (5)0.001 (4)0.012 (4)0.003 (4)
O60.043 (5)0.034 (4)0.030 (4)0.005 (4)0.010 (4)0.001 (4)
O70.058 (6)0.030 (4)0.041 (5)0.007 (4)0.015 (4)0.000 (4)
O80.052 (6)0.027 (4)0.053 (5)0.012 (4)0.015 (5)0.008 (4)
O90.063 (8)0.120 (11)0.095 (9)0.027 (8)0.022 (7)0.066 (9)
O100.21 (2)0.080 (9)0.048 (7)0.033 (11)0.028 (10)0.016 (7)
O110.063 (9)0.083 (10)0.162 (15)0.031 (8)0.002 (10)0.031 (10)
O120.134 (16)0.101 (12)0.22 (2)0.054 (12)0.097 (16)0.038 (14)
O130.063 (7)0.056 (6)0.054 (6)0.003 (5)0.023 (5)0.034 (5)
O140.089 (9)0.067 (7)0.031 (5)0.026 (6)0.013 (5)0.001 (5)
O150.080 (9)0.070 (8)0.104 (10)0.047 (7)0.003 (8)0.012 (7)
O160.175 (16)0.052 (7)0.051 (7)0.047 (8)0.001 (8)0.009 (5)
O170.059 (7)0.057 (6)0.059 (6)0.010 (5)0.030 (5)0.010 (5)
O180.047 (6)0.036 (5)0.049 (5)0.004 (4)0.005 (5)0.013 (4)
O190.055 (6)0.045 (5)0.048 (5)0.006 (5)0.016 (5)0.005 (4)
O200.047 (6)0.050 (6)0.042 (5)0.000 (5)0.016 (5)0.015 (4)
O210.063 (7)0.050 (6)0.059 (6)0.009 (5)0.011 (6)0.012 (5)
O220.074 (8)0.052 (6)0.044 (6)0.005 (6)0.004 (6)0.000 (5)
N10.033 (6)0.024 (5)0.027 (5)0.009 (4)0.003 (4)0.005 (4)
N20.023 (5)0.029 (5)0.027 (5)0.005 (4)0.001 (4)0.003 (4)
N30.032 (5)0.031 (5)0.021 (4)0.009 (4)0.006 (4)0.004 (4)
N40.032 (6)0.025 (5)0.032 (5)0.005 (4)0.004 (4)0.011 (4)
N50.033 (5)0.025 (5)0.032 (5)0.002 (4)0.009 (4)0.003 (4)
N60.039 (6)0.033 (5)0.021 (5)0.008 (4)0.013 (4)0.012 (4)
N70.039 (6)0.025 (5)0.020 (4)0.005 (4)0.001 (4)0.004 (4)
N80.045 (6)0.027 (5)0.026 (5)0.000 (5)0.004 (5)0.012 (4)
C10.045 (8)0.027 (6)0.031 (6)0.002 (5)0.008 (6)0.003 (5)
C20.054 (9)0.027 (6)0.031 (6)0.004 (6)0.012 (6)0.006 (5)
C30.034 (7)0.031 (6)0.043 (7)0.001 (5)0.003 (6)0.004 (6)
C40.037 (7)0.031 (6)0.032 (6)0.004 (5)0.001 (6)0.003 (5)
C50.024 (6)0.025 (5)0.031 (6)0.003 (5)0.006 (5)0.003 (5)
C60.031 (6)0.019 (5)0.035 (6)0.000 (5)0.001 (5)0.001 (5)
C70.035 (7)0.028 (6)0.032 (6)0.012 (5)0.004 (5)0.011 (5)
C80.024 (6)0.029 (6)0.029 (6)0.003 (5)0.001 (5)0.006 (5)
C90.029 (6)0.027 (5)0.025 (5)0.003 (5)0.012 (5)0.008 (4)
C100.036 (7)0.026 (5)0.027 (5)0.005 (5)0.011 (5)0.002 (5)
C110.042 (7)0.024 (5)0.034 (6)0.013 (5)0.013 (6)0.004 (5)
C120.049 (8)0.021 (5)0.026 (5)0.005 (5)0.010 (5)0.006 (4)
C130.039 (7)0.025 (6)0.038 (6)0.006 (5)0.011 (6)0.001 (5)
C140.037 (7)0.035 (6)0.029 (6)0.012 (6)0.005 (5)0.015 (5)
C150.046 (8)0.029 (6)0.033 (6)0.004 (5)0.002 (6)0.008 (5)
C160.037 (7)0.024 (5)0.031 (6)0.001 (5)0.007 (5)0.002 (5)
C170.038 (7)0.033 (6)0.038 (6)0.009 (5)0.007 (6)0.003 (5)
C180.036 (7)0.033 (6)0.049 (7)0.003 (6)0.002 (6)0.012 (6)
C190.041 (8)0.041 (7)0.044 (7)0.011 (6)0.015 (6)0.009 (6)
C200.044 (8)0.032 (7)0.056 (8)0.006 (6)0.005 (7)0.008 (6)
C210.044 (8)0.030 (6)0.048 (7)0.001 (6)0.012 (6)0.004 (6)
C220.055 (9)0.033 (6)0.032 (6)0.002 (6)0.005 (6)0.008 (5)
C230.055 (9)0.027 (6)0.040 (7)0.010 (6)0.012 (6)0.008 (5)
C240.053 (8)0.032 (6)0.024 (6)0.002 (6)0.005 (6)0.002 (5)
C250.040 (7)0.024 (5)0.033 (6)0.001 (5)0.004 (5)0.006 (5)
C260.037 (7)0.030 (6)0.032 (6)0.000 (5)0.002 (6)0.006 (5)
C270.042 (8)0.027 (6)0.036 (7)0.006 (5)0.000 (6)0.004 (5)
C280.049 (8)0.033 (6)0.034 (6)0.001 (6)0.006 (6)0.008 (5)
C290.038 (7)0.031 (6)0.032 (6)0.002 (5)0.013 (5)0.009 (5)
C300.032 (6)0.026 (5)0.023 (5)0.005 (5)0.000 (5)0.002 (4)
C310.043 (7)0.029 (6)0.026 (6)0.001 (5)0.012 (5)0.007 (5)
C320.033 (7)0.031 (6)0.033 (6)0.002 (5)0.004 (5)0.000 (5)
C330.037 (7)0.030 (6)0.028 (6)0.002 (5)0.006 (5)0.005 (5)
C340.040 (7)0.027 (5)0.027 (6)0.002 (5)0.009 (5)0.007 (5)
C350.035 (7)0.028 (6)0.036 (6)0.002 (5)0.006 (5)0.006 (5)
C360.042 (7)0.023 (5)0.026 (5)0.004 (5)0.007 (5)0.006 (4)
C370.041 (7)0.028 (6)0.034 (6)0.001 (5)0.004 (6)0.004 (5)
C380.063 (10)0.024 (6)0.044 (7)0.009 (6)0.012 (7)0.003 (5)
C390.048 (8)0.036 (7)0.040 (7)0.006 (6)0.008 (6)0.003 (6)
C400.043 (7)0.031 (6)0.014 (5)0.002 (5)0.001 (5)0.007 (4)
C410.056 (8)0.024 (5)0.027 (5)0.009 (5)0.003 (6)0.007 (5)
C420.050 (8)0.020 (5)0.049 (7)0.008 (5)0.010 (7)0.005 (5)
C430.049 (9)0.034 (7)0.048 (8)0.006 (6)0.000 (7)0.007 (6)
C440.057 (9)0.035 (7)0.035 (7)0.006 (6)0.006 (6)0.008 (6)
C450.061 (9)0.031 (6)0.047 (7)0.005 (6)0.026 (7)0.002 (6)
C460.044 (7)0.032 (6)0.028 (6)0.007 (5)0.000 (5)0.005 (5)
C470.045 (8)0.036 (7)0.048 (8)0.002 (6)0.002 (7)0.005 (6)
C480.054 (9)0.036 (7)0.044 (7)0.010 (6)0.021 (7)0.006 (6)
C490.055 (9)0.031 (6)0.031 (6)0.005 (6)0.013 (6)0.007 (5)
C500.066 (10)0.028 (6)0.028 (6)0.004 (6)0.013 (6)0.004 (5)
C510.039 (9)0.096 (13)0.069 (11)0.019 (9)0.004 (8)0.027 (10)
Geometric parameters (Å, º) top
Co1—N11.910 (10)C33—C341.430 (17)
Co1—N21.844 (9)C34—C351.374 (15)
Co1—N31.949 (10)C35—C361.457 (17)
Co1—N51.940 (10)C36—C371.401 (17)
Co1—N61.844 (9)C37—C381.375 (19)
Co1—N71.944 (10)C38—C391.334 (18)
Cl1—O91.433 (15)C39—C401.409 (19)
Cl1—O101.322 (13)C41—C421.529 (17)
Cl1—O111.425 (15)C43—C441.53 (2)
Cl1—O121.42 (2)C45—C461.478 (19)
Cl2—O131.424 (11)C47—C481.485 (18)
Cl2—O141.427 (10)C49—C501.49 (2)
Cl2—O151.484 (15)O21—H210.820
Cl2—O161.444 (15)O22—H50.86 (13)
Cl3—O171.435 (12)O22—H60.86 (12)
Cl3—O181.426 (10)C1—H10.930
Cl3—O191.448 (10)C2—H20.930
Cl3—O201.434 (9)C3—H30.930
O1—C171.413 (15)C4—H40.930
O1—C181.433 (17)C7—H70.930
O2—C191.443 (17)C9—H90.930
O2—C201.427 (15)C12—H120.930
O3—C211.412 (17)C13—H130.930
O3—C221.428 (15)C14—H140.930
O4—C231.418 (15)C15—H150.930
O4—C241.421 (14)C16—H16A0.970
O5—C481.427 (18)C16—H16B0.970
O5—C491.435 (14)C17—H17A0.970
O6—C461.413 (14)C17—H17B0.970
O6—C471.432 (16)C18—H18A0.970
O7—C441.418 (16)C18—H18B0.970
O7—C451.463 (19)C19—H19A0.970
O8—C421.442 (16)C19—H19B0.970
O8—C431.431 (15)C20—H20A0.970
O21—C511.44 (2)C20—H20B0.970
N1—C11.355 (16)C21—H21A0.970
N1—C51.382 (14)C21—H21B0.970
N2—C61.366 (14)C22—H22A0.970
N2—C101.329 (15)C22—H22B0.970
N3—C111.350 (14)C23—H23A0.970
N3—C151.333 (15)C23—H23B0.970
N4—C81.376 (14)C24—H24A0.970
N4—C161.466 (15)C24—H24B0.970
N4—C251.455 (16)C25—H25A0.970
N5—C261.329 (15)C25—H25B0.970
N5—C301.386 (14)C26—H260.930
N6—C311.352 (16)C27—H270.930
N6—C351.371 (15)C28—H280.930
N7—C361.375 (13)C29—H290.930
N7—C401.346 (14)C32—H320.930
N8—C331.345 (15)C34—H340.930
N8—C411.468 (16)C37—H370.930
N8—C501.469 (17)C38—H380.930
C1—C21.410 (19)C39—H390.930
C2—C31.383 (17)C40—H400.930
C3—C41.375 (18)C41—H41A0.970
C4—C51.370 (16)C41—H41B0.970
C5—C61.474 (16)C42—H42A0.970
C6—C71.374 (15)C42—H42B0.970
C7—C81.412 (17)C43—H43A0.970
C8—C91.436 (16)C43—H43B0.970
C9—C101.393 (14)C44—H44A0.970
C10—C111.481 (17)C44—H44B0.970
C11—C121.383 (18)C45—H45A0.970
C12—C131.383 (17)C45—H45B0.970
C13—C141.406 (16)C46—H46A0.970
C14—C151.360 (18)C46—H46B0.970
C16—C171.533 (18)C47—H47A0.970
C18—C191.538 (18)C47—H47B0.970
C20—C211.482 (19)C48—H48A0.970
C22—C231.52 (2)C48—H48B0.970
C24—C251.537 (16)C49—H49A0.970
C26—C271.378 (19)C49—H49B0.970
C27—C281.412 (17)C50—H50A0.970
C28—C291.398 (17)C50—H50B0.970
C29—C301.398 (18)C51—H51A0.960
C30—C311.478 (16)C51—H51B0.960
C31—C321.366 (16)C51—H51C0.960
C32—C331.437 (17)
N1—Co1—N282.8 (4)C4—C3—H3120.021
N1—Co1—N3164.5 (4)C3—C4—H4120.141
N1—Co1—N591.1 (4)C5—C4—H4120.134
N1—Co1—N698.1 (4)C6—C7—H7120.652
N1—Co1—N790.5 (4)C8—C7—H7120.652
N2—Co1—N381.7 (4)C8—C9—H9121.141
N2—Co1—N599.0 (4)C10—C9—H9121.144
N2—Co1—N6178.3 (5)C11—C12—H12119.971
N2—Co1—N795.9 (4)C13—C12—H12119.965
N3—Co1—N591.2 (4)C12—C13—H13121.168
N3—Co1—N697.5 (4)C14—C13—H13121.166
N3—Co1—N791.2 (4)C13—C14—H14120.481
N5—Co1—N682.5 (4)C15—C14—H14120.483
N5—Co1—N7165.2 (4)N3—C15—H15118.383
N6—Co1—N782.7 (4)C14—C15—H15118.390
O9—Cl1—O10110.7 (9)N4—C16—H16A109.257
O9—Cl1—O11107.3 (8)N4—C16—H16B109.253
O9—Cl1—O12107.7 (11)C17—C16—H16A109.253
O10—Cl1—O11111.5 (12)C17—C16—H16B109.259
O10—Cl1—O12111.0 (13)H16A—C16—H16B107.926
O11—Cl1—O12108.5 (10)O1—C17—H17A110.452
O13—Cl2—O14110.7 (6)O1—C17—H17B110.444
O13—Cl2—O15108.7 (7)C16—C17—H17A110.452
O13—Cl2—O16111.3 (8)C16—C17—H17B110.448
O14—Cl2—O15108.3 (8)H17A—C17—H17B108.644
O14—Cl2—O16107.4 (7)O1—C18—H18A108.759
O15—Cl2—O16110.4 (9)O1—C18—H18B108.762
O17—Cl3—O18108.1 (6)C19—C18—H18A108.763
O17—Cl3—O19108.1 (6)C19—C18—H18B108.766
O17—Cl3—O20111.7 (6)H18A—C18—H18B107.654
O18—Cl3—O19110.5 (6)O2—C19—H19A110.294
O18—Cl3—O20108.9 (6)O2—C19—H19B110.295
O19—Cl3—O20109.5 (6)C18—C19—H19A110.291
C17—O1—C18111.2 (10)C18—C19—H19B110.289
C19—O2—C20110.2 (10)H19A—C19—H19B108.538
C21—O3—C22111.7 (10)O2—C20—H20A108.474
C23—O4—C24112.8 (9)O2—C20—H20B108.478
C48—O5—C49112.6 (10)C21—C20—H20A108.465
C46—O6—C47113.5 (9)C21—C20—H20B108.478
C44—O7—C45110.5 (10)H20A—C20—H20B107.499
C42—O8—C43114.5 (11)O3—C21—H21A109.410
Co1—N1—C1127.0 (8)O3—C21—H21B109.415
Co1—N1—C5115.2 (7)C20—C21—H21A109.416
C1—N1—C5117.8 (10)C20—C21—H21B109.416
Co1—N2—C6118.8 (7)H21A—C21—H21B108.037
Co1—N2—C10120.1 (7)O3—C22—H22A109.885
C6—N2—C10121.0 (9)O3—C22—H22B109.885
Co1—N3—C11114.3 (8)C23—C22—H22A109.877
Co1—N3—C15126.9 (8)C23—C22—H22B109.879
C11—N3—C15118.8 (11)H22A—C22—H22B108.297
C8—N4—C16122.0 (10)O4—C23—H23A109.006
C8—N4—C25122.2 (9)O4—C23—H23B109.008
C16—N4—C25115.1 (9)C22—C23—H23A109.009
Co1—N5—C26127.4 (8)C22—C23—H23B109.015
Co1—N5—C30113.6 (7)H23A—C23—H23B107.796
C26—N5—C30118.8 (10)O4—C24—H24A110.387
Co1—N6—C31120.2 (8)O4—C24—H24B110.388
Co1—N6—C35119.1 (8)C25—C24—H24A110.389
C31—N6—C35120.7 (9)C25—C24—H24B110.393
Co1—N7—C36113.4 (7)H24A—C24—H24B108.597
Co1—N7—C40127.0 (7)N4—C25—H25A108.460
C36—N7—C40119.6 (10)N4—C25—H25B108.456
C33—N8—C41120.0 (11)C24—C25—H25A108.463
C33—N8—C50121.3 (11)C24—C25—H25B108.461
C41—N8—C50118.4 (9)H25A—C25—H25B107.486
N1—C1—C2122.0 (10)N5—C26—H26118.708
C1—C2—C3118.3 (12)C27—C26—H26118.704
C2—C3—C4120.0 (12)C26—C27—H27120.236
C3—C4—C5119.7 (11)C28—C27—H27120.239
N1—C5—C4122.0 (10)C27—C28—H28120.568
N1—C5—C6112.1 (9)C29—C28—H28120.559
C4—C5—C6125.9 (10)C28—C29—H29120.888
N2—C6—C5111.0 (9)C30—C29—H29120.881
N2—C6—C7121.6 (11)C31—C32—H32120.008
C5—C6—C7127.4 (11)C33—C32—H32120.011
C6—C7—C8118.7 (11)C33—C34—H34119.888
N4—C8—C7122.9 (10)C35—C34—H34119.902
N4—C8—C9118.0 (10)C36—C37—H37120.610
C7—C8—C9119.0 (10)C38—C37—H37120.594
C8—C9—C10117.7 (10)C37—C38—H38119.558
N2—C10—C9121.9 (10)C39—C38—H38119.575
N2—C10—C11110.9 (9)C38—C39—H39119.913
C9—C10—C11127.1 (11)C40—C39—H39119.926
N3—C11—C10113.0 (11)N7—C40—H40119.898
N3—C11—C12121.2 (11)C39—C40—H40119.886
C10—C11—C12125.8 (10)N8—C41—H41A109.396
C11—C12—C13120.1 (10)N8—C41—H41B109.392
C12—C13—C14117.7 (11)C42—C41—H41A109.398
C13—C14—C15119.0 (11)C42—C41—H41B109.394
N3—C15—C14123.2 (11)H41A—C41—H41B108.007
N4—C16—C17111.8 (9)O8—C42—H42A109.132
O1—C17—C16106.4 (10)O8—C42—H42B109.132
O1—C18—C19114.0 (11)C41—C42—H42A109.128
O2—C19—C18107.1 (11)C41—C42—H42B109.134
O2—C20—C21115.2 (11)H42A—C42—H42B107.861
O3—C21—C20111.1 (11)O8—C43—H43A108.294
O3—C22—C23109.0 (11)O8—C43—H43B108.291
O4—C23—C22112.9 (11)C44—C43—H43A108.307
O4—C24—C25106.7 (9)C44—C43—H43B108.303
N4—C25—C24115.3 (11)H43A—C43—H43B107.409
N5—C26—C27122.6 (11)O7—C44—H44A109.754
C26—C27—C28119.5 (11)O7—C44—H44B109.758
C27—C28—C29118.9 (12)C43—C44—H44A109.758
C28—C29—C30118.2 (11)C43—C44—H44B109.758
N5—C30—C29121.9 (10)H44A—C44—H44B108.224
N5—C30—C31113.3 (10)O7—C45—H45A109.466
C29—C30—C31124.8 (10)O7—C45—H45B109.463
N6—C31—C30110.3 (9)C46—C45—H45A109.470
N6—C31—C32121.7 (11)C46—C45—H45B109.471
C30—C31—C32128.0 (11)H45A—C45—H45B108.057
C31—C32—C33120.0 (12)O6—C46—H46A109.215
N8—C33—C32121.8 (11)O6—C46—H46B109.219
N8—C33—C34121.5 (11)C45—C46—H46A109.216
C32—C33—C34116.7 (10)C45—C46—H46B109.217
C33—C34—C35120.2 (11)H46A—C46—H46B107.910
N6—C35—C34120.7 (11)O6—C47—H47A109.862
N6—C35—C36110.5 (9)O6—C47—H47B109.865
C34—C35—C36128.7 (11)C48—C47—H47A109.870
N7—C36—C35114.2 (10)C48—C47—H47B109.868
N7—C36—C37120.3 (10)H47A—C47—H47B108.282
C35—C36—C37125.5 (10)O5—C48—H48A110.013
C36—C37—C38118.8 (11)O5—C48—H48B110.017
C37—C38—C39120.9 (13)C47—C48—H48A110.013
C38—C39—C40120.2 (13)C47—C48—H48B110.016
N7—C40—C39120.2 (10)H48A—C48—H48B108.374
N8—C41—C42111.2 (11)O5—C49—H49A109.631
O8—C42—C41112.4 (11)O5—C49—H49B109.634
O8—C43—C44115.9 (12)C50—C49—H49A109.629
O7—C44—C43109.6 (11)C50—C49—H49B109.629
O7—C45—C46110.9 (11)H49A—C49—H49B108.155
O6—C46—C45112.0 (10)N8—C50—H50A108.683
O6—C47—C48109.1 (11)N8—C50—H50B108.676
O5—C48—C47108.4 (12)C49—C50—H50A108.681
O5—C49—C50110.1 (11)C49—C50—H50B108.680
N8—C50—C49114.3 (10)H50A—C50—H50B107.616
C51—O21—H21109.475O21—C51—H51A109.476
H5—O22—H6107 (16)O21—C51—H51B109.467
N1—C1—H1119.021O21—C51—H51C109.476
C2—C1—H1119.019H51A—C51—H51B109.467
C1—C2—H2120.833H51A—C51—H51C109.471
C3—C2—H2120.842H51B—C51—H51C109.469
C2—C3—H3120.023
N1—Co1—N2—C61.5 (7)C25—N4—C16—C1779.3 (12)
N1—Co1—N2—C10179.7 (8)Co1—N5—C26—C27175.0 (7)
N2—Co1—N1—C1178.0 (8)Co1—N5—C30—C29176.7 (7)
N2—Co1—N1—C53.0 (6)Co1—N5—C30—C313.3 (11)
N1—Co1—N5—C2680.1 (8)C26—N5—C30—C290.1 (16)
N1—Co1—N5—C3096.2 (6)C26—N5—C30—C31179.9 (9)
N5—Co1—N1—C179.1 (8)C30—N5—C26—C271.1 (17)
N5—Co1—N1—C5101.9 (6)Co1—N6—C31—C301.9 (13)
N1—Co1—N6—C3190.3 (8)Co1—N6—C31—C32178.2 (7)
N1—Co1—N6—C3592.1 (8)Co1—N6—C35—C34177.2 (7)
N6—Co1—N1—C13.5 (9)Co1—N6—C35—C363.7 (13)
N6—Co1—N1—C5175.5 (6)C31—N6—C35—C340.5 (17)
N1—Co1—N7—C3698.9 (6)C31—N6—C35—C36178.6 (10)
N1—Co1—N7—C4078.2 (8)C35—N6—C31—C30179.6 (9)
N7—Co1—N1—C186.2 (8)C35—N6—C31—C320.5 (18)
N7—Co1—N1—C592.9 (6)Co1—N7—C36—C351.0 (12)
N2—Co1—N3—C110.3 (6)Co1—N7—C36—C37179.2 (7)
N2—Co1—N3—C15179.8 (9)Co1—N7—C40—C39179.8 (7)
N3—Co1—N2—C6178.5 (8)C36—N7—C40—C392.9 (16)
N3—Co1—N2—C100.3 (7)C40—N7—C36—C35178.2 (9)
N2—Co1—N5—C262.8 (9)C40—N7—C36—C371.9 (16)
N2—Co1—N5—C30179.1 (6)C33—N8—C41—C4286.0 (13)
N5—Co1—N2—C691.6 (7)C41—N8—C33—C32172.5 (10)
N5—Co1—N2—C1089.7 (8)C41—N8—C33—C346.7 (17)
N2—Co1—N7—C36178.3 (6)C33—N8—C50—C4963.4 (14)
N2—Co1—N7—C404.6 (8)C50—N8—C33—C3213.5 (17)
N7—Co1—N2—C688.2 (7)C50—N8—C33—C34167.3 (10)
N7—Co1—N2—C1090.6 (7)C41—N8—C50—C49110.7 (11)
N3—Co1—N5—C2684.6 (8)C50—N8—C41—C4288.1 (12)
N3—Co1—N5—C3099.2 (6)N1—C1—C2—C32.2 (18)
N5—Co1—N3—C1199.2 (7)C1—C2—C3—C45.1 (19)
N5—Co1—N3—C1581.3 (8)C2—C3—C4—C54.4 (19)
N3—Co1—N6—C3190.1 (8)C3—C4—C5—N10.6 (18)
N3—Co1—N6—C3587.6 (7)C3—C4—C5—C6180.0 (11)
N6—Co1—N3—C11178.2 (6)N1—C5—C6—N22.5 (13)
N6—Co1—N3—C151.3 (9)N1—C5—C6—C7180.0 (10)
N3—Co1—N7—C3696.6 (6)C4—C5—C6—N2178.1 (11)
N3—Co1—N7—C4086.4 (8)C4—C5—C6—C70.6 (19)
N7—Co1—N3—C1195.5 (6)N2—C6—C7—C81.5 (17)
N7—Co1—N3—C1584.1 (8)C5—C6—C7—C8178.9 (10)
N5—Co1—N6—C310.2 (7)C6—C7—C8—N4178.6 (10)
N5—Co1—N6—C35177.9 (8)C6—C7—C8—C92.6 (17)
N6—Co1—N5—C26178.1 (9)N4—C8—C9—C10179.2 (9)
N6—Co1—N5—C301.8 (6)C7—C8—C9—C103.1 (16)
N6—Co1—N7—C360.8 (6)C8—C9—C10—N22.6 (17)
N6—Co1—N7—C40176.2 (8)C8—C9—C10—C11178.5 (10)
N7—Co1—N6—C31179.7 (8)N2—C10—C11—N30.9 (14)
N7—Co1—N6—C352.6 (7)N2—C10—C11—C12179.6 (10)
C17—O1—C18—C1955.3 (12)C9—C10—C11—N3177.2 (11)
C18—O1—C17—C16164.1 (8)C9—C10—C11—C124 (2)
C19—O2—C20—C2166.0 (14)N3—C11—C12—C130.7 (18)
C20—O2—C19—C18174.2 (9)C10—C11—C12—C13179.3 (10)
C21—O3—C22—C23175.3 (8)C11—C12—C13—C140.8 (17)
C22—O3—C21—C20167.2 (8)C12—C13—C14—C151.1 (18)
C23—O4—C24—C25176.6 (9)C13—C14—C15—N31.4 (19)
C24—O4—C23—C2274.7 (12)N4—C16—C17—O1170.5 (8)
C48—O5—C49—C50153.2 (9)O1—C18—C19—O255.2 (13)
C49—O5—C48—C47177.9 (8)O2—C20—C21—O360.1 (15)
C46—O6—C47—C48177.6 (9)O3—C22—C23—O453.7 (12)
C47—O6—C46—C45178.5 (9)O4—C24—C25—N4142.6 (9)
C44—O7—C45—C46101.9 (11)N5—C26—C27—C281.0 (18)
C45—O7—C44—C43168.2 (9)C26—C27—C28—C290.4 (18)
C42—O8—C43—C4457.6 (13)C27—C28—C29—C301.5 (18)
C43—O8—C42—C4191.5 (12)C28—C29—C30—N51.4 (17)
Co1—N1—C1—C2177.5 (7)C28—C29—C30—C31178.6 (10)
Co1—N1—C5—C4176.8 (7)N5—C30—C31—N63.3 (14)
Co1—N1—C5—C63.7 (11)N5—C30—C31—C32176.8 (10)
C1—N1—C5—C42.3 (16)C29—C30—C31—N6176.7 (10)
C1—N1—C5—C6177.2 (9)C29—C30—C31—C323 (2)
C5—N1—C1—C21.5 (16)N6—C31—C32—C330.4 (18)
Co1—N2—C6—C50.1 (12)C30—C31—C32—C33179.8 (10)
Co1—N2—C6—C7177.8 (7)C31—C32—C33—N8179.9 (11)
Co1—N2—C10—C9177.3 (7)C31—C32—C33—C340.8 (17)
Co1—N2—C10—C110.7 (13)N8—C33—C34—C35178.9 (10)
C6—N2—C10—C91.5 (17)C32—C33—C34—C351.8 (17)
C6—N2—C10—C11178.0 (9)C33—C34—C35—N61.7 (18)
C10—N2—C6—C5178.7 (9)C33—C34—C35—C36177.3 (10)
C10—N2—C6—C70.9 (17)N6—C35—C36—N72.8 (14)
Co1—N3—C11—C100.7 (12)N6—C35—C36—C37177.3 (10)
Co1—N3—C11—C12179.5 (7)C34—C35—C36—N7178.1 (11)
Co1—N3—C15—C14179.2 (7)C34—C35—C36—C372 (2)
C11—N3—C15—C141.3 (18)N7—C36—C37—C380.7 (17)
C15—N3—C11—C10179.7 (10)C35—C36—C37—C38179.4 (10)
C15—N3—C11—C120.9 (17)C36—C37—C38—C391 (2)
C8—N4—C16—C1791.8 (11)C37—C38—C39—C402 (2)
C16—N4—C8—C76.8 (17)C38—C39—C40—N73 (2)
C16—N4—C8—C9177.1 (9)N8—C41—C42—O8167.0 (9)
C8—N4—C25—C2468.2 (14)O8—C43—C44—O755.0 (14)
C25—N4—C8—C7177.3 (10)O7—C45—C46—O672.7 (13)
C25—N4—C8—C96.7 (16)O6—C47—C48—O563.1 (13)
C16—N4—C25—C24102.8 (10)O5—C49—C50—N850.2 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N7/C36–C40 and N2/C6–C10 pyridine rings, respectively.
D—H···AD—HH···AD···AD—H···A
O21—H21···O80.821.992.802 (15)173
O22—H5···O90.86 (13)2.11 (14)2.960 (19)172 (15)
O22—H6···O50.86 (12)2.17 (11)2.934 (13)148 (14)
C4—H4···O180.932.563.299 (16)137
C15—H15···O11i0.932.543.35 (2)145
C16—H16B···O6ii0.972.583.491 (15)157
C20—H20B···O10ii0.972.543.50 (2)170
C22—H22A···O13iii0.972.413.365 (17)168
C25—H25A···O6ii0.972.593.517 (14)160
C25—H25B···O20i0.972.493.331 (15)145
C26—H26···O16iii0.932.543.400 (17)155
C27—H27···O14iii0.932.453.249 (16)143
C28—H28···O22iii0.932.473.290 (17)147
C29—H29···O7iii0.932.513.437 (14)175
C37—H37···O210.932.353.276 (16)177
C44—H44A···O20iv0.972.493.297 (17)141
C3—H3···Cg1v0.932.703.540 (15)151
C40—H40···Cg20.932.973.713 (12)138
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z+1; (iii) x, y1, z; (iv) x+1, y+1, z1; (v) x1, y, z.
 

Acknowledgements

This work was supported by Innovative Areas `Coordination Programming' (area 2107) from the MEXT, Japan.

References

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