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The title dimeric complex, bis{[mu]-2,2'-[hexane-1,6-diyl­bis(nitrilo­methyl­idyne)]­diphenolato-1:2[kappa]4O,N:N',O'}dicopper(II),[Cu2(C20H22N2O2)2], has been investigated by single-crystal X-ray diffraction, by thermogravimetric analysis and differential scanning calorimetry, and also by FT-IR spectroscopy. Different synthetic and crystallization procedures gave crystals which were quite different in appearance, and it was initially thought that these were different polymorphic forms. Subsequent structure determination showed, in fact, serendipitous preparation of crystals in the P41 space group by one method and in space group P43 by the other. In these enantiomorphic structures, the Cu atoms have a distorted flattened tetrahedral coordination, with Cu-N and Cu-O distances in the ranges 1.954 (4)-1.983 (4) and 1.887 (4)-1.903 (4) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102006297/sk1547sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102006297/sk1547Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102006297/sk1547IIsup3.hkl
Contains datablock II

CCDC references: 187918; 187919

Comment top

Although copper(II) and nickel(II) complexes with Schiff base ligands containing bridging aliphatic chains containing two, three or four methylene groups have been the subject of several crystallographic investigations (Freiburg et al., 1980; Akhtar, 1981; Akhtar & Drew, 1982; Drew et al., 1985; Yao et al., 1997), less work has been done on homologous compounds containing longer bridging chains (Martin et al., 1978; Kitajima et al., 1986). The aliphatic chain length can have a pronounced influence on the coordination polyhedron of the metal ion, and also on intermolecular oligomerization and polymerization in the solid state and in solution.

Previous work (Duggal & Agarwala, 1988) carried out on the complex of copper(II) with N,N'-hexamethylenebis(salicylaldimine) concluded, on the basis of IR and diffuse-reflectance spectroscopy measurements, that the complex should be monomeric, with the CuII ion in a cis-square-planar environment. We concluded that it would be interesting to examine the folding of the rather long polymethylene chain in such a compound, so the title complex was prepared and crystallized, either by a diffusion reaction technique, to give (I), or by evaporation of a dioxane solution of the complex, to give (II). The results obtained by the present structure determinations are not in agreement with the structure proposed previously by Duggal & Agarwala (1988). The title complex was found to be dimeric in the solid state, with anions of N,N'-hexamethylenebis(salicylaldimine) functioning as bridging bis-bidentate ligands. \sch

One set of crystals of the title copper complex was grown by evaporation from a dioxane solution, and the compound obtained, (II), was found to crystallize in the space group P43. However, crystals obtained by a slow interdiffusion of methanolic basic N,N'-hexamethylenebis(salicylaldimine) solution and a copper(II) nitrate solution, (I), exhibited the space group P41. Structure determination from room-temperature data indicated that the molecular geometries were the same in both crystals, the only difference being in the direction of the polar axis.

Space-group determinations and data collection were performed on several crystals from each set at room temperature, and the Flack data (Flack, 1983) were always consistent with space group P41 for diffusion-grown and P43 for dioxane-grown crystals. However, the data collected at room temperature indicated the existence of disorder in one of the bridging aliphatic chains of the dimeric complex molecule; the final structure determinations reported here were undertaken using low-temperature data, which enabled the resolution of the disorder (see Experimental).

The molecular geometry in both (I) (Fig. 1) and (II) (Fig. 2) is identical. The CuII ions in the dimers are coordinated in the form of very flattened tetrahedra, with the N and O donor atoms in a trans arrangement around each CuII centre. There is similar significant disorder in one of the two hexamethylene chains in each compound; a view of the pair of disordered chains in (I) is shown in Fig. 3.

The distance between the two CuII centres in the dimer is 7.7019 (8) Å in (I) and 7.7186 (8) Å in (II). The degree of the distortion of the metal coordination tetrahedron can be expressed by the dihedral angle between the corresponding O—Cu—N planes; in (I), this is 35.0 (2)° for atom Cu1 and 23.3 (2)° for Cu2, and in (II) the angle is 34.5 (2)° for Cu1 and 23.6 (2) for Cu2. These values fall in the range of the previously reported angles in similar complexes (Bear et al., 1970; Elder & Hill, 1979). Details of the bond lengths at the Cu atoms are given in Tables 1 and 2. The molecular dimensions in both complexes are all in accordance with values previously reported for copper(II) salicylaldiminates (Bhadbhade & Srinivas, 1993; Kani et al., 1998).

The reasons for the observed dependence of the orientation of the polar axis on crystallization conditions are, as yet, unclear.

Experimental top

The Schiff base ligand N,N'-hexamethylenebis(salicylaldimine) was prepared by the condensation of salicylaldehyde with 1,6-diaminohexane in the molar ratio 2:1 in methanol. The yellow product so obtained was identified by FT—IR, and 1H and 13 C NMR spectroscopy. The copper(II) complex was obtained as a brown powder by slow simultaneous dropwise addition of ethanol solutions of the Schiff base (containing an equimolar amount of triethylamine) and copper(II) nitrate trihydrate into a small volume of ethanol. The concentrations of the reactants varied from 0.05 to 0.10 mol dm-3. It was observed that the rate of addition, as well as the concentration of the reacting solutions, strongly influenced the nature of the product. Higher addition rates and reagent concentrations favoured the formation of green precipitates of unknown composition. The title compound was separated from the insoluble products by extraction with chloroform and subsequent precipitation with n-hexane or diethyl ether. The compound was crystallized by evaporation from dioxane solution, giving red crystals of (II) in the shape of bicapped tetragonal prisms. As the compound dissolved in dioxane tends to decompose, yielding an insoluble green precipitate (of currently unknown compostion), another method of preparation of the compound by slow diffusion of solutions of the Schiff base and copper(II) nitrate was used. As a result, long red needle-like crystals of (I) were obtained. As mentioned above, we initially considered that the crystals of (I) and (II) might be polymorphs, but the present X-ray structure determinations establish that the different preparation and crystallization conditions have instead yielded crystals of the same compound in enantiomorphic space groups, (I) in P41 and (II) in P43. The DSC measurements performed in an inert gas flow atmosphere (Ar, 200 cm3 min-1) in the temperature range 298–873 K using aluminium crucibles revealed a weak exothermic change at 499 K, followed by melting combined with decomposition at 587 K, for both crystal forms. The thermogravimetric analyses made in an oxygen gas flow atmosphere (200 cm3 min-1) in the temperature range 298–873 K gave the expected copper content of 15.73% (calculated copper content 16.38%) in both crystal forms and confirmed the chemical composition.

Refinement top

The crystal structure determination of both crystal forms using room-temperature data indicated a hardly resolvable disorder in one of the bridging hexamethylene chains. Therefore, low-temperature diffraction experiments were performed. Crystals of (I) and (II) were significantly different in appearance and both crystallized in the tetragonal system, space groups either P41 or P43 from the systematic absences. P41 was shown to be correct for (I) and P43 for (II) from the Flack parameters (Flack, 1983). H atoms were treated as riding atoms, with aromatic C—H = 0.95 Å and aliphatic C—H = 0.99 Å. Both structures were solved independently and it soon became apparent that, in each case, there was essentially identical disorder of one of the (CH2)6 chains. The occupancies of the major and minor chains were 0.714 (6) and 0.286 (6), respectively, for (I), and 0.747 (6) and 0.253 (6), respectively, for (II). Minor occupancy atoms were assigned an overall Uiso value of 0.06 Å2 and their geometry was restrained to reasonable values via SHELXL97 (Sheldrick, 1997) DFIX restraints.

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1997-2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 10% probability level and H atoms have been omitted.
[Figure 2] Fig. 2. A view of (II) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 10% probability level and H atoms have been omitted.
[Figure 3] Fig. 3. A view of the two disordered hexamethylene chains in (I). Displacement ellipsoids are drawn at the 30% probability level. The corresponding view for (II) is very similar.
(I) bis{µ-2,2'-[hexane-1,6-diylbis(nitrilomethylidyne)]diphenolato- 1:2κ4O,N:N',O'}dicopper(II) top
Crystal data top
[Cu2(C20H22N2O2)2]Dx = 1.405 Mg m3
Mr = 771.81Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 4153 reflections
Hall symbol: P 4wθ = 2.9–27.5°
a = 13.2963 (2) ŵ = 1.21 mm1
c = 20.6366 (5) ÅT = 150 K
V = 3648.38 (12) Å3Needle, red
Z = 40.22 × 0.21 × 0.20 mm
F(000) = 1608
Data collection top
Nonius KappaCCD area-detector
diffractometer
7755 independent reflections
Radiation source: fine-focus sealed X-ray tube5429 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1717
Tmin = 0.776, Tmax = 0.794k = 1212
20156 measured reflectionsl = 2326
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0485P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.003
7755 reflectionsΔρmax = 0.32 e Å3
470 parametersΔρmin = 0.36 e Å3
59 restraintsAbsolute structure: Flack (1983), 3489 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.007 (14)
Crystal data top
[Cu2(C20H22N2O2)2]Z = 4
Mr = 771.81Mo Kα radiation
Tetragonal, P41µ = 1.21 mm1
a = 13.2963 (2) ÅT = 150 K
c = 20.6366 (5) Å0.22 × 0.21 × 0.20 mm
V = 3648.38 (12) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
7755 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
5429 reflections with I > 2σ(I)
Tmin = 0.776, Tmax = 0.794Rint = 0.072
20156 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.108Δρmax = 0.32 e Å3
S = 1.00Δρmin = 0.36 e Å3
7755 reflectionsAbsolute structure: Flack (1983), 3489 Friedel pairs
470 parametersAbsolute structure parameter: 0.007 (14)
59 restraints
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891.] which effectively corrects for absorption effects. High-redundancy data were used in the scaling program, hence the `multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the `size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.16386 (4)0.30277 (4)0.50000 (3)0.04489 (14)
Cu20.67705 (4)0.15144 (4)0.35702 (3)0.04434 (14)
O10.2104 (2)0.3276 (2)0.58530 (16)0.0562 (8)
O20.0627 (2)0.2975 (2)0.43576 (18)0.0588 (9)
O30.6758 (2)0.2798 (2)0.31628 (16)0.0541 (8)
O40.7161 (2)0.0190 (2)0.37971 (15)0.0526 (8)
N10.1553 (3)0.1561 (3)0.5128 (2)0.0502 (9)
N20.2202 (3)0.4295 (3)0.46793 (19)0.0465 (8)
N30.5825 (2)0.0945 (3)0.29262 (19)0.0484 (9)
N40.7407 (3)0.2084 (3)0.4347 (2)0.0560 (10)
C110.1983 (3)0.1618 (3)0.6278 (2)0.0524 (12)
C120.2139 (3)0.2642 (3)0.6342 (2)0.0472 (11)
C130.2344 (3)0.3028 (4)0.6971 (3)0.0570 (12)
C140.2404 (4)0.2401 (4)0.7499 (3)0.0664 (13)
C150.2262 (4)0.1396 (4)0.7435 (3)0.0754 (16)
C160.2058 (4)0.1001 (4)0.6832 (3)0.0721 (15)
C170.1727 (3)0.1129 (3)0.5675 (3)0.0522 (12)
C210.0935 (3)0.4579 (3)0.3848 (2)0.0460 (10)
C220.0398 (3)0.3653 (3)0.3925 (2)0.0475 (10)
C230.0409 (3)0.3479 (3)0.3500 (3)0.0577 (12)
C240.0695 (4)0.4160 (4)0.3053 (3)0.0634 (13)
C250.0188 (4)0.5074 (4)0.2991 (3)0.0705 (14)
C260.0612 (4)0.5274 (4)0.3380 (2)0.0600 (13)
C270.1806 (3)0.4822 (3)0.4219 (2)0.0513 (11)
C310.5938 (3)0.2348 (3)0.2171 (2)0.0502 (11)
C320.6464 (3)0.3013 (3)0.2572 (2)0.0479 (11)
C330.6673 (3)0.3979 (3)0.2321 (2)0.0543 (11)
C340.6403 (4)0.4252 (4)0.1702 (3)0.0639 (13)
C350.5906 (4)0.3588 (4)0.1303 (3)0.0681 (15)
C360.5677 (4)0.2646 (4)0.1541 (2)0.0596 (13)
C370.5614 (3)0.1370 (3)0.2380 (2)0.0510 (11)
C410.8196 (3)0.0527 (3)0.4713 (2)0.0489 (11)
C420.7748 (3)0.0122 (3)0.4263 (2)0.0454 (10)
C430.7928 (3)0.1166 (3)0.4337 (3)0.0531 (11)
C440.8550 (4)0.1517 (4)0.4811 (3)0.0563 (13)
C450.9020 (4)0.0878 (4)0.5239 (3)0.0642 (14)
C460.8840 (4)0.0133 (4)0.5189 (3)0.0618 (13)
C470.8000 (4)0.1587 (4)0.4729 (2)0.0583 (12)
C10.1276 (3)0.0906 (3)0.4576 (2)0.0495 (11)
C20.2046 (3)0.0959 (4)0.4038 (2)0.0617 (13)
C30.3093 (3)0.0583 (3)0.4183 (2)0.0563 (12)
C40.3767 (3)0.0605 (3)0.3592 (2)0.0625 (13)
C50.4721 (3)0.0002 (3)0.3678 (2)0.0605 (13)
C60.5357 (3)0.0044 (3)0.3071 (2)0.0540 (11)
C610.3109 (4)0.4735 (8)0.4995 (7)0.0546 (17)0.714 (6)
C620.4067 (5)0.4349 (5)0.4689 (4)0.072 (2)0.714 (6)
C630.4265 (5)0.3248 (4)0.4815 (5)0.083 (3)0.714 (6)
C640.5256 (4)0.2896 (6)0.4531 (4)0.081 (3)0.714 (6)
C650.6183 (4)0.3293 (6)0.4872 (4)0.091 (3)0.714 (6)
C660.7162 (4)0.3150 (4)0.4509 (3)0.0499 (18)0.714 (6)
N720.2202 (3)0.4295 (3)0.46793 (19)0.0465 (8)0.00
C710.3190 (12)0.456 (2)0.496 (2)0.060*0.286 (6)
C720.3939 (7)0.3745 (14)0.4812 (10)0.060*0.286 (6)
C730.4943 (7)0.3867 (11)0.5132 (7)0.060*0.286 (6)
C740.5758 (8)0.3251 (14)0.4809 (9)0.060*0.286 (6)
C750.6795 (8)0.3482 (10)0.4989 (7)0.060*0.286 (6)
C760.7587 (10)0.3165 (9)0.4497 (10)0.060*0.286 (6)
N740.7407 (3)0.2084 (3)0.4347 (2)0.0560 (10)0.00
H130.24400.37310.70270.068*
H140.25470.26740.79140.080*
H150.23030.09680.78020.090*
H160.19670.02960.67880.086*
H170.16830.04160.56820.063*
H230.07650.28620.35290.069*
H240.12480.40150.27760.076*
H250.04010.55540.26780.085*
H260.09580.58950.33350.072*
H270.21300.54380.41170.062*
H330.70100.44540.25870.065*
H340.65610.49060.15480.077*
H350.57250.37740.08740.082*
H360.53310.21840.12700.072*
H370.52040.09990.20880.061*
H430.76110.16280.40520.064*
H440.86620.22210.48460.068*
H450.94590.11330.55620.077*
H460.91600.05790.54840.074*
H470.83400.19640.50520.070*
H51A0.06120.11150.44060.059*
H51B0.12180.02030.47290.059*
H52A0.17830.05710.36650.074*
H52B0.20990.16690.38980.074*
H53A0.30520.01150.43480.068*
H53B0.33940.10050.45270.068*
H54A0.33900.03360.32160.075*
H54B0.39460.13110.34940.075*
H55A0.45420.06910.38100.073*
H55B0.51230.03050.40310.073*
H56A0.58920.05550.31280.065*
H56B0.49330.02520.27000.065*
H61A0.31060.45630.54620.066*0.714 (6)
H61B0.30860.54770.49560.066*0.714 (6)
H62A0.40320.44600.42150.086*0.714 (6)
H62B0.46410.47460.48580.086*0.714 (6)
H63A0.37120.28460.46250.099*0.714 (6)
H63B0.42690.31280.52880.099*0.714 (6)
H64A0.52730.21520.45430.098*0.714 (6)
H64B0.52850.31040.40700.098*0.714 (6)
H65A0.60890.40200.49540.109*0.714 (6)
H65B0.62400.29550.52980.109*0.714 (6)
H66A0.71320.35420.41020.060*0.714 (6)
H66B0.77160.34300.47750.060*0.714 (6)
H71A0.31260.46410.54330.072*0.286 (6)
H71B0.34250.52040.47740.072*0.286 (6)
H72A0.36490.30920.49460.072*0.286 (6)
H72B0.40420.37190.43370.072*0.286 (6)
H73A0.48870.36630.55910.072*0.286 (6)
H73B0.51370.45860.51210.072*0.286 (6)
H74A0.56320.25330.49070.072*0.286 (6)
H74B0.56930.33350.43340.072*0.286 (6)
H75A0.69450.31480.54070.072*0.286 (6)
H75B0.68520.42170.50590.072*0.286 (6)
H76A0.75280.35750.40980.072*0.286 (6)
H76B0.82700.32580.46780.072*0.286 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0510 (3)0.0394 (3)0.0443 (3)0.0007 (2)0.0004 (3)0.0010 (2)
Cu20.0548 (3)0.0423 (3)0.0359 (3)0.0028 (2)0.0008 (2)0.0034 (2)
O10.069 (2)0.0516 (18)0.048 (2)0.0041 (15)0.0071 (16)0.0006 (15)
O20.066 (2)0.0464 (17)0.065 (2)0.0055 (14)0.0157 (17)0.0010 (17)
O30.073 (2)0.0482 (17)0.041 (2)0.0017 (14)0.0077 (16)0.0008 (14)
O40.0646 (19)0.0478 (17)0.045 (2)0.0018 (13)0.0066 (15)0.0011 (14)
N10.050 (2)0.046 (2)0.054 (3)0.0012 (15)0.0092 (19)0.0016 (19)
N20.050 (2)0.045 (2)0.044 (2)0.0010 (15)0.0005 (17)0.0051 (17)
N30.0429 (19)0.058 (2)0.044 (3)0.0050 (16)0.0035 (17)0.0020 (18)
N40.076 (3)0.045 (2)0.047 (3)0.0016 (18)0.002 (2)0.0057 (18)
C110.045 (2)0.060 (3)0.052 (3)0.005 (2)0.007 (2)0.009 (2)
C120.038 (2)0.055 (3)0.048 (3)0.0043 (19)0.004 (2)0.007 (2)
C130.053 (3)0.066 (3)0.052 (3)0.001 (2)0.005 (2)0.002 (2)
C140.064 (3)0.088 (4)0.047 (3)0.010 (2)0.003 (3)0.012 (3)
C150.079 (4)0.090 (4)0.057 (4)0.012 (3)0.010 (3)0.026 (3)
C160.087 (4)0.068 (3)0.060 (4)0.001 (3)0.003 (3)0.016 (3)
C170.051 (3)0.042 (2)0.064 (4)0.0043 (19)0.011 (2)0.008 (2)
C210.054 (3)0.050 (2)0.035 (3)0.0006 (19)0.0001 (19)0.006 (2)
C220.053 (3)0.048 (2)0.041 (3)0.002 (2)0.002 (2)0.008 (2)
C230.059 (3)0.052 (3)0.062 (4)0.006 (2)0.014 (3)0.011 (2)
C240.065 (3)0.076 (4)0.049 (3)0.009 (3)0.012 (3)0.015 (3)
C250.078 (3)0.086 (4)0.048 (3)0.019 (3)0.000 (3)0.014 (3)
C260.072 (3)0.059 (3)0.048 (3)0.005 (2)0.001 (3)0.007 (2)
C270.060 (3)0.046 (2)0.048 (3)0.002 (2)0.010 (2)0.002 (2)
C310.047 (2)0.057 (3)0.047 (3)0.002 (2)0.003 (2)0.002 (2)
C320.046 (2)0.055 (3)0.043 (3)0.0053 (18)0.007 (2)0.005 (2)
C330.065 (3)0.052 (3)0.046 (3)0.003 (2)0.012 (2)0.000 (2)
C340.065 (3)0.063 (3)0.064 (4)0.008 (2)0.001 (3)0.012 (3)
C350.080 (4)0.082 (4)0.042 (3)0.015 (3)0.011 (3)0.015 (3)
C360.062 (3)0.072 (3)0.045 (3)0.013 (2)0.009 (2)0.001 (2)
C370.047 (2)0.065 (3)0.041 (3)0.003 (2)0.000 (2)0.002 (2)
C410.057 (3)0.047 (2)0.043 (3)0.004 (2)0.009 (2)0.002 (2)
C420.046 (2)0.046 (2)0.044 (3)0.0010 (18)0.008 (2)0.003 (2)
C430.062 (3)0.044 (2)0.053 (3)0.004 (2)0.007 (2)0.001 (2)
C440.058 (3)0.051 (3)0.060 (4)0.004 (2)0.012 (3)0.010 (2)
C450.058 (3)0.079 (4)0.056 (3)0.011 (3)0.003 (2)0.015 (3)
C460.062 (3)0.066 (3)0.058 (4)0.007 (2)0.008 (2)0.002 (2)
C470.080 (3)0.057 (3)0.038 (3)0.008 (2)0.009 (3)0.009 (2)
C10.053 (3)0.042 (2)0.054 (3)0.0054 (18)0.003 (2)0.001 (2)
C20.066 (3)0.066 (3)0.053 (3)0.009 (2)0.001 (3)0.010 (3)
C30.071 (3)0.053 (3)0.046 (3)0.007 (2)0.001 (2)0.002 (2)
C40.065 (3)0.071 (3)0.051 (3)0.013 (2)0.009 (3)0.013 (3)
C50.069 (3)0.059 (3)0.054 (3)0.019 (2)0.002 (3)0.001 (2)
C60.062 (3)0.048 (2)0.052 (3)0.011 (2)0.008 (2)0.006 (2)
C610.056 (4)0.051 (5)0.057 (5)0.009 (3)0.006 (4)0.002 (5)
C620.052 (4)0.074 (5)0.089 (6)0.008 (3)0.005 (4)0.008 (4)
C630.063 (5)0.059 (5)0.126 (8)0.007 (3)0.012 (5)0.009 (5)
C640.063 (5)0.072 (5)0.109 (8)0.006 (4)0.002 (5)0.030 (5)
C650.035 (4)0.065 (4)0.172 (10)0.010 (3)0.031 (5)0.060 (5)
C660.056 (4)0.039 (3)0.055 (5)0.000 (3)0.015 (4)0.015 (3)
N720.050 (2)0.045 (2)0.044 (2)0.0010 (15)0.0005 (17)0.0051 (17)
N740.076 (3)0.045 (2)0.047 (3)0.0016 (18)0.002 (2)0.0057 (18)
Geometric parameters (Å, º) top
Cu1—O21.890 (3)C43—C441.363 (7)
Cu1—O11.895 (3)C43—H430.9500
Cu1—N21.959 (4)C44—C451.375 (7)
Cu1—N11.972 (3)C44—H440.9500
Cu2—O41.895 (3)C45—C461.370 (7)
Cu2—O31.903 (3)C45—H450.9500
Cu2—N41.965 (4)C46—H460.9500
Cu2—N31.980 (4)C47—H470.9500
O1—C121.316 (5)C1—C21.512 (3)
O2—C221.305 (5)C1—H51A0.9900
O3—C321.311 (6)C1—H51B0.9900
O4—C421.306 (5)C2—C31.509 (3)
N1—C171.286 (6)C2—H52A0.9900
N1—C11.480 (6)C2—H52B0.9900
N2—C271.293 (6)C3—C41.515 (3)
N2—C611.491 (8)C3—H53A0.9900
N3—C371.291 (6)C3—H53B0.9900
N3—C61.485 (5)C4—C51.511 (3)
N4—C471.295 (6)C4—H54A0.9900
N4—C661.492 (7)C4—H54B0.9900
C11—C121.383 (6)C5—C61.513 (3)
C11—C161.411 (7)C5—H55A0.9900
C11—C171.445 (7)C5—H55B0.9900
C12—C131.422 (7)C6—H56A0.9900
C13—C141.374 (7)C6—H56B0.9900
C13—H130.9500C61—C621.512 (3)
C14—C151.356 (8)C61—H61A0.9900
C14—H140.9500C61—H61B0.9900
C15—C161.376 (8)C62—C631.510 (3)
C15—H150.9500C62—H62A0.9900
C16—H160.9500C62—H62B0.9900
C17—H170.9500C63—C641.516 (3)
C21—C261.404 (6)C63—H63A0.9900
C21—C271.426 (6)C63—H63B0.9900
C21—C221.432 (6)C64—C651.515 (3)
C22—C231.406 (6)C64—H64A0.9900
C23—C241.347 (7)C64—H64B0.9900
C23—H230.9500C65—C661.513 (3)
C24—C251.396 (7)C65—H65A0.9900
C24—H240.9500C65—H65B0.9900
C25—C261.359 (7)C66—H66A0.9900
C25—H250.9500C66—H66B0.9900
C26—H260.9500C71—C721.501 (10)
C27—H270.9500C71—H71A0.9900
C31—C321.399 (6)C71—H71B0.9900
C31—C361.402 (7)C72—C731.498 (9)
C31—C371.437 (6)C72—H72A0.9900
C32—C331.412 (6)C72—H72B0.9900
C33—C341.375 (7)C73—C741.514 (9)
C33—H330.9500C73—H73A0.9900
C34—C351.376 (7)C73—H73B0.9900
C34—H340.9500C74—C751.461 (9)
C35—C361.380 (7)C74—H74A0.9900
C35—H350.9500C74—H74B0.9900
C36—H360.9500C75—C761.523 (9)
C37—H370.9500C75—H75A0.9900
C41—C421.402 (6)C75—H75B0.9900
C41—C461.404 (7)C76—H76A0.9900
C41—C471.433 (6)C76—H76B0.9900
C42—C431.416 (6)
O2—Cu1—O1152.95 (15)C45—C46—H46119.2
O2—Cu1—N293.86 (14)C41—C46—H46119.2
O1—Cu1—N292.23 (15)N4—C47—C41126.8 (4)
O2—Cu1—N190.93 (15)N4—C47—H47116.6
O1—Cu1—N193.82 (16)C41—C47—H47116.6
N2—Cu1—N1156.66 (15)N1—C1—C2111.7 (3)
O4—Cu2—O3160.99 (14)N1—C1—H51A109.3
O4—Cu2—N492.23 (15)C2—C1—H51A109.3
O3—Cu2—N491.06 (15)N1—C1—H51B109.3
O4—Cu2—N389.09 (14)C2—C1—H51B109.3
O3—Cu2—N392.34 (14)H51A—C1—H51B107.9
N4—Cu2—N3165.62 (16)C3—C2—C1117.6 (4)
C12—O1—Cu1127.7 (3)C3—C2—H52A107.9
C22—O2—Cu1128.3 (3)C1—C2—H52A107.9
C32—O3—Cu2127.5 (3)C3—C2—H52B107.9
C42—O4—Cu2129.9 (3)C1—C2—H52B107.9
C17—N1—C1117.2 (4)H52A—C2—H52B107.2
C17—N1—Cu1123.3 (4)C2—C3—C4112.3 (4)
C1—N1—Cu1119.5 (3)C2—C3—H53A109.1
C27—N2—C61115.9 (7)C4—C3—H53A109.1
C27—N2—Cu1124.0 (3)C2—C3—H53B109.1
C61—N2—Cu1120.0 (6)C4—C3—H53B109.1
C37—N3—C6118.1 (4)H53A—C3—H53B107.9
C37—N3—Cu2123.8 (3)C5—C4—C3113.1 (4)
C6—N3—Cu2118.0 (3)C5—C4—H54A109.0
C47—N4—C66118.8 (5)C3—C4—H54A109.0
C47—N4—Cu2124.1 (3)C5—C4—H54B109.0
C66—N4—Cu2117.1 (4)C3—C4—H54B109.0
C12—C11—C16118.9 (5)H54A—C4—H54B107.8
C12—C11—C17124.1 (4)C4—C5—C6113.2 (4)
C16—C11—C17117.0 (5)C4—C5—H55A108.9
O1—C12—C11123.5 (5)C6—C5—H55A108.9
O1—C12—C13118.4 (4)C4—C5—H55B108.9
C11—C12—C13118.1 (4)C6—C5—H55B108.9
C14—C13—C12121.0 (5)H55A—C5—H55B107.8
C14—C13—H13119.5N3—C6—C5111.4 (3)
C12—C13—H13119.5N3—C6—H56A109.4
C15—C14—C13120.9 (6)C5—C6—H56A109.4
C15—C14—H14119.6N3—C6—H56B109.4
C13—C14—H14119.6C5—C6—H56B109.4
C14—C15—C16119.4 (5)H56A—C6—H56B108.0
C14—C15—H15120.3N2—C61—C62111.5 (6)
C16—C15—H15120.3N2—C61—H61A109.3
C15—C16—C11121.6 (5)C62—C61—H61A109.3
C15—C16—H16119.2N2—C61—H61B109.3
C11—C16—H16119.2C62—C61—H61B109.3
N1—C17—C11126.7 (4)H61A—C61—H61B108.0
N1—C17—H17116.7C63—C62—C61113.8 (7)
C11—C17—H17116.7C63—C62—H62A108.8
C26—C21—C27117.9 (4)C61—C62—H62A108.8
C26—C21—C22119.3 (4)C63—C62—H62B108.8
C27—C21—C22122.7 (4)C61—C62—H62B108.8
O2—C22—C23119.4 (4)H62A—C62—H62B107.7
O2—C22—C21123.6 (4)C62—C63—C64112.6 (6)
C23—C22—C21116.9 (4)C62—C63—H63A109.1
C24—C23—C22122.2 (4)C64—C63—H63A109.1
C24—C23—H23118.9C62—C63—H63B109.1
C22—C23—H23118.9C64—C63—H63B109.1
C23—C24—C25120.7 (5)H63A—C63—H63B107.8
C23—C24—H24119.6C65—C64—C63114.9 (6)
C25—C24—H24119.6C65—C64—H64A108.5
C26—C25—C24119.6 (5)C63—C64—H64A108.6
C26—C25—H25120.2C65—C64—H64B108.6
C24—C25—H25120.2C63—C64—H64B108.6
C25—C26—C21121.1 (5)H64A—C64—H64B107.5
C25—C26—H26119.4C66—C65—C64115.2 (6)
C21—C26—H26119.4C66—C65—H65A108.5
N2—C27—C21127.1 (4)C64—C65—H65A108.5
N2—C27—H27116.5C66—C65—H65B108.5
C21—C27—H27116.5C64—C65—H65B108.5
C32—C31—C36119.6 (4)H65A—C65—H65B107.5
C32—C31—C37123.0 (5)N4—C66—C65114.8 (5)
C36—C31—C37117.4 (4)N4—C66—H66A108.6
O3—C32—C31124.1 (4)C65—C66—H66A108.6
O3—C32—C33118.7 (4)N4—C66—H66B108.6
C31—C32—C33117.1 (5)C65—C66—H66B108.6
C34—C33—C32122.0 (5)H66A—C66—H66B107.6
C34—C33—H33119.0C72—C71—H71A109.7
C32—C33—H33119.0C72—C71—H71B109.7
C35—C34—C33120.8 (5)H71A—C71—H71B108.2
C35—C34—H34119.6C73—C72—C71115.1 (9)
C33—C34—H34119.6C73—C72—H72A108.5
C34—C35—C36118.4 (5)C71—C72—H72A108.5
C34—C35—H35120.8C73—C72—H72B108.5
C36—C35—H35120.8C71—C72—H72B108.5
C35—C36—C31122.1 (5)H72A—C72—H72B107.5
C35—C36—H36118.9C72—C73—C74112.7 (9)
C31—C36—H36118.9C72—C73—H73A109.0
N3—C37—C31126.4 (4)C74—C73—H73A109.1
N3—C37—H37116.8C72—C73—H73B109.1
C31—C37—H37116.8C74—C73—H73B109.0
C42—C41—C46119.5 (4)H73A—C73—H73B107.8
C42—C41—C47122.9 (4)C75—C74—C73116.7 (10)
C46—C41—C47117.5 (4)C75—C74—H74A108.1
O4—C42—C41123.1 (4)C73—C74—H74A108.1
O4—C42—C43119.5 (4)C75—C74—H74B108.2
C41—C42—C43117.4 (4)C73—C74—H74B108.2
C44—C43—C42121.1 (5)H74A—C74—H74B107.3
C44—C43—H43119.4C74—C75—C76115.1 (9)
C42—C43—H43119.4C74—C75—H75A108.6
C43—C44—C45121.6 (5)C76—C75—H75A108.5
C43—C44—H44119.2C74—C75—H75B108.5
C45—C44—H44119.2C76—C75—H75B108.5
C46—C45—C44118.7 (5)H75A—C75—H75B107.5
C46—C45—H45120.7C75—C76—H76A110.3
C44—C45—H45120.7C75—C76—H76B110.3
C45—C46—C41121.7 (5)H76A—C76—H76B108.5
O2—Cu1—O1—C1289.0 (4)C24—C25—C26—C210.4 (8)
N2—Cu1—O1—C12168.0 (3)C27—C21—C26—C25177.3 (5)
N1—Cu1—O1—C1210.6 (4)C22—C21—C26—C251.4 (7)
O1—Cu1—O2—C2296.3 (5)C61—N2—C27—C21179.1 (5)
N2—Cu1—O2—C226.3 (4)Cu1—N2—C27—C212.6 (6)
N1—Cu1—O2—C22163.5 (4)C26—C21—C27—N2178.2 (4)
O4—Cu2—O3—C3276.1 (5)C22—C21—C27—N23.2 (7)
N4—Cu2—O3—C32176.1 (4)Cu2—O3—C32—C3111.9 (6)
N3—Cu2—O3—C3217.9 (4)Cu2—O3—C32—C33169.2 (3)
O3—Cu2—O4—C4292.3 (5)C36—C31—C32—O3178.7 (4)
N4—Cu2—O4—C427.5 (4)C37—C31—C32—O33.5 (7)
N3—Cu2—O4—C42173.2 (4)C36—C31—C32—C332.3 (6)
O2—Cu1—N1—C17149.1 (4)C37—C31—C32—C33175.5 (4)
O1—Cu1—N1—C174.3 (4)O3—C32—C33—C34178.9 (4)
N2—Cu1—N1—C17108.9 (5)C31—C32—C33—C342.1 (7)
O2—Cu1—N1—C130.8 (3)C32—C33—C34—C350.6 (8)
O1—Cu1—N1—C1175.8 (3)C33—C34—C35—C360.6 (8)
N2—Cu1—N1—C171.1 (5)C34—C35—C36—C310.3 (8)
O2—Cu1—N2—C276.1 (4)C32—C31—C36—C351.2 (7)
O1—Cu1—N2—C27147.6 (4)C37—C31—C36—C35176.7 (5)
N1—Cu1—N2—C27107.5 (5)C6—N3—C37—C31175.8 (4)
O2—Cu1—N2—C61177.5 (4)Cu2—N3—C37—C316.2 (6)
O1—Cu1—N2—C6128.8 (4)C32—C31—C37—N36.0 (7)
N1—Cu1—N2—C6176.2 (6)C36—C31—C37—N3176.1 (4)
O4—Cu2—N3—C37146.2 (4)Cu2—O4—C42—C411.7 (6)
O3—Cu2—N3—C3714.8 (4)Cu2—O4—C42—C43180.0 (3)
N4—Cu2—N3—C37118.3 (6)C46—C41—C42—O4178.2 (4)
O4—Cu2—N3—C631.7 (3)C47—C41—C42—O44.2 (7)
O3—Cu2—N3—C6167.2 (3)C46—C41—C42—C433.5 (6)
N4—Cu2—N3—C663.7 (7)C47—C41—C42—C43174.1 (4)
O4—Cu2—N4—C4710.6 (4)O4—C42—C43—C44178.8 (4)
O3—Cu2—N4—C47150.7 (4)C41—C42—C43—C442.8 (6)
N3—Cu2—N4—C47105.6 (7)C42—C43—C44—C450.6 (7)
O4—Cu2—N4—C66167.7 (4)C43—C44—C45—C461.0 (7)
O3—Cu2—N4—C6631.0 (4)C44—C45—C46—C410.2 (7)
N3—Cu2—N4—C6672.7 (8)C42—C41—C46—C452.1 (7)
Cu1—O1—C12—C1111.0 (6)C47—C41—C46—C45175.7 (5)
Cu1—O1—C12—C13168.7 (3)C66—N4—C47—C41169.4 (5)
C16—C11—C12—O1178.6 (4)Cu2—N4—C47—C418.9 (8)
C17—C11—C12—O12.4 (7)C42—C41—C47—N40.1 (8)
C16—C11—C12—C131.7 (6)C46—C41—C47—N4177.7 (5)
C17—C11—C12—C13177.3 (4)C17—N1—C1—C2116.9 (4)
O1—C12—C13—C14179.0 (4)Cu1—N1—C1—C263.1 (4)
C11—C12—C13—C141.3 (7)N1—C1—C2—C364.2 (5)
C12—C13—C14—C150.6 (7)C1—C2—C3—C4175.7 (4)
C13—C14—C15—C160.2 (8)C2—C3—C4—C5165.7 (4)
C14—C15—C16—C110.7 (9)C3—C4—C5—C6175.5 (4)
C12—C11—C16—C151.4 (8)C37—N3—C6—C5120.0 (4)
C17—C11—C16—C15177.6 (5)Cu2—N3—C6—C561.9 (4)
C1—N1—C17—C11178.3 (4)C4—C5—C6—N370.5 (5)
Cu1—N1—C17—C111.6 (6)C27—N2—C61—C6294.2 (9)
C12—C11—C17—N14.2 (7)Cu1—N2—C61—C6289.2 (10)
C16—C11—C17—N1174.8 (4)N2—C61—C62—C6368.4 (11)
Cu1—O2—C22—C23178.0 (3)C61—C62—C63—C64177.1 (7)
Cu1—O2—C22—C212.8 (6)C62—C63—C64—C6570.6 (10)
C26—C21—C22—O2178.1 (4)C63—C64—C65—C66166.5 (7)
C27—C21—C22—O23.2 (7)C47—N4—C66—C6596.2 (7)
C26—C21—C22—C232.6 (6)Cu2—N4—C66—C6582.3 (6)
C27—C21—C22—C23176.0 (4)C64—C65—C66—N458.0 (9)
O2—C22—C23—C24178.5 (5)C71—C72—C73—C74161 (3)
C21—C22—C23—C242.2 (7)C72—C73—C74—C75166.9 (18)
C22—C23—C24—C250.4 (8)C73—C74—C75—C76157.7 (16)
C23—C24—C25—C260.9 (8)
(II) bis{µ-2,2'-[hexane-1,6-diylbis(nitrilomethylidyne)]diphenolato- 1:2κ4O,N:N',O'}dicopper(II) top
Crystal data top
[Cu2(C20H22N2O2)2]Dx = 1.402 Mg m3
Mr = 771.81Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 4153 reflections
Hall symbol: P 4cwθ = 2.9–27.5°
a = 13.3288 (2) ŵ = 1.21 mm1
c = 20.5834 (7) ÅT = 150 K
V = 3656.78 (15) Å3Prism, red
Z = 40.20 × 0.18 × 0.10 mm
F(000) = 1608
Data collection top
Nonius KappaCCD area-detector
diffractometer
7763 independent reflections
Radiation source: fine-focus sealed X-ray tube4824 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.103
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1717
Tmin = 0.794, Tmax = 0.889k = 1212
20308 measured reflectionsl = 2623
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0212P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
7763 reflectionsΔρmax = 0.35 e Å3
470 parametersΔρmin = 0.47 e Å3
59 restraintsAbsolute structure: Flack (1983), 3505 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.000 (14)
Crystal data top
[Cu2(C20H22N2O2)2]Z = 4
Mr = 771.81Mo Kα radiation
Tetragonal, P43µ = 1.21 mm1
a = 13.3288 (2) ÅT = 150 K
c = 20.5834 (7) Å0.20 × 0.18 × 0.10 mm
V = 3656.78 (15) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
7763 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4824 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.889Rint = 0.103
20308 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.098Δρmax = 0.35 e Å3
S = 0.96Δρmin = 0.47 e Å3
7763 reflectionsAbsolute structure: Flack (1983), 3505 Friedel pairs
470 parametersAbsolute structure parameter: 0.000 (14)
59 restraints
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891.] which effectively corrects for absorption effects. High-redundancy data were used in the scaling program, hence the `multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the `size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.19609 (4)0.33581 (4)0.49998 (3)0.03574 (16)
Cu20.34869 (4)0.17673 (4)0.35611 (3)0.03360 (16)
O10.1703 (2)0.2884 (2)0.58532 (18)0.0410 (9)
O20.2022 (2)0.4367 (2)0.43572 (19)0.0471 (10)
O30.2201 (2)0.1761 (2)0.31595 (17)0.0388 (9)
O40.4817 (2)0.2143 (2)0.37788 (17)0.0383 (9)
N10.3429 (3)0.3433 (3)0.5133 (2)0.0354 (10)
N20.0692 (3)0.2809 (3)0.4675 (2)0.0334 (9)
N30.4046 (3)0.0810 (3)0.2919 (2)0.0348 (10)
N40.2922 (3)0.2400 (3)0.4335 (2)0.0408 (11)
C210.0427 (3)0.4077 (3)0.3839 (2)0.0326 (11)
C220.1346 (3)0.4608 (3)0.3919 (3)0.0361 (12)
C230.1531 (3)0.5418 (3)0.3505 (3)0.0432 (13)
C240.0854 (4)0.5711 (4)0.3044 (3)0.0502 (14)
C250.0068 (4)0.5208 (4)0.2977 (3)0.0503 (14)
C260.0261 (4)0.4408 (4)0.3367 (3)0.0425 (14)
C270.0176 (3)0.3207 (4)0.4217 (3)0.0385 (13)
C110.3371 (4)0.3014 (3)0.6283 (3)0.0376 (13)
C120.2329 (3)0.2854 (3)0.6353 (3)0.0338 (12)
C130.1940 (4)0.2659 (4)0.6974 (3)0.0437 (13)
C140.2567 (4)0.2613 (4)0.7507 (3)0.0500 (14)
C150.3579 (4)0.2741 (4)0.7449 (3)0.0560 (15)
C160.3974 (4)0.2934 (4)0.6845 (3)0.0526 (15)
C170.3846 (4)0.3274 (3)0.5682 (3)0.0401 (14)
C410.4493 (3)0.3197 (3)0.4700 (3)0.0357 (12)
C420.5127 (3)0.2735 (3)0.4247 (2)0.0310 (11)
C430.6173 (3)0.2920 (3)0.4319 (3)0.0377 (12)
C440.6533 (3)0.3532 (3)0.4796 (3)0.0389 (13)
C450.5891 (4)0.4011 (4)0.5228 (3)0.0443 (14)
C460.4881 (4)0.3835 (4)0.5177 (3)0.0435 (14)
C470.3434 (4)0.2991 (4)0.4721 (3)0.0439 (14)
C310.2630 (3)0.0914 (3)0.2165 (3)0.0350 (12)
C320.1973 (3)0.1459 (3)0.2572 (3)0.0349 (13)
C330.1007 (3)0.1666 (3)0.2323 (3)0.0365 (12)
C340.0727 (4)0.1390 (4)0.1703 (3)0.0435 (13)
C350.1394 (4)0.0881 (4)0.1299 (3)0.0444 (14)
C360.2326 (4)0.0643 (3)0.1532 (3)0.0418 (13)
C370.3620 (3)0.0590 (3)0.2375 (3)0.0368 (13)
C10.4079 (3)0.3716 (3)0.4581 (2)0.0376 (12)
C20.4011 (4)0.2955 (3)0.4034 (2)0.0414 (13)
C30.4413 (3)0.1916 (3)0.4187 (2)0.0383 (13)
C40.4391 (3)0.1239 (3)0.3593 (2)0.0396 (12)
C50.4994 (3)0.0280 (3)0.3666 (2)0.0418 (13)
C60.5032 (3)0.0352 (3)0.3053 (2)0.0378 (12)
C610.0247 (7)0.1899 (4)0.4985 (6)0.0362 (18)0.747 (6)
C620.0642 (4)0.0930 (4)0.4691 (4)0.047 (2)0.747 (6)
C630.1749 (4)0.0737 (4)0.4809 (4)0.054 (2)0.747 (6)
C640.2097 (5)0.0253 (4)0.4518 (4)0.052 (2)0.747 (6)
C650.1737 (5)0.1179 (4)0.4881 (4)0.053 (2)0.747 (6)
C660.1864 (4)0.2165 (4)0.4519 (3)0.0348 (18)0.747 (6)
N720.0692 (3)0.2809 (3)0.4675 (2)0.0334 (9)0.00
C710.040 (2)0.1806 (12)0.491 (3)0.060*0.253 (6)
C720.1225 (17)0.1066 (8)0.4754 (13)0.060*0.253 (6)
C730.1144 (15)0.0076 (8)0.5086 (9)0.060*0.253 (6)
C740.1749 (19)0.0746 (9)0.4762 (13)0.060*0.253 (6)
C750.1505 (13)0.1784 (9)0.4970 (10)0.060*0.253 (6)
C760.1853 (10)0.2594 (12)0.4509 (14)0.060*0.253 (6)
N740.2922 (3)0.2400 (3)0.4335 (2)0.0408 (11)0.00
H230.21440.57750.35440.052*
H240.10070.62580.27660.060*
H250.05470.54240.26660.060*
H260.08790.40610.33200.051*
H270.04440.28900.41160.046*
H130.12400.25590.70280.052*
H140.22870.24880.79240.060*
H150.40020.26980.78200.067*
H160.46790.30160.68040.063*
H170.45560.33360.56940.048*
H430.66310.26100.40280.045*
H440.72360.36330.48340.047*
H450.61460.44500.55510.053*
H460.44350.41540.54710.052*
H470.30640.33210.50530.053*
H330.05360.20060.25910.044*
H340.00730.15470.15510.052*
H350.12050.07030.08700.053*
H360.27800.02870.12600.050*
H370.39880.01780.20830.044*
H1A0.47830.37630.47320.045*
H1B0.38750.43840.44170.045*
H2A0.32980.28900.39050.050*
H2B0.43820.32210.36550.050*
H3A0.40040.16110.45370.046*
H3B0.51110.19730.43460.046*
H4A0.36850.10600.34970.048*
H4B0.46530.16180.32150.048*
H5A0.46980.01260.40210.050*
H5B0.56880.04560.37950.050*
H6A0.52330.00740.26810.045*
H6B0.55420.08870.31040.045*
H61A0.04920.19200.49360.043*0.747 (6)
H61B0.04010.19080.54560.043*0.747 (6)
H62A0.02530.03620.48720.056*0.747 (6)
H62B0.05210.09450.42170.056*0.747 (6)
H63A0.18780.07310.52830.065*0.747 (6)
H63B0.21440.12920.46170.065*0.747 (6)
H64A0.18560.02920.40630.062*0.747 (6)
H64B0.28390.02580.45070.062*0.747 (6)
H65A0.21080.12240.52970.064*0.747 (6)
H65B0.10180.10910.49860.064*0.747 (6)
H66A0.16040.27160.47950.042*0.747 (6)
H66B0.14510.21440.41200.042*0.747 (6)
H71A0.02310.15930.47030.072*0.253 (6)
H71B0.02950.18280.53880.072*0.253 (6)
H72A0.12270.09520.42790.072*0.253 (6)
H72B0.18770.13720.48710.072*0.253 (6)
H73A0.04300.01290.50970.072*0.253 (6)
H73B0.13730.01500.55410.072*0.253 (6)
H74A0.16480.06980.42870.072*0.253 (6)
H74B0.24690.06220.48490.072*0.253 (6)
H75A0.07690.18400.50230.072*0.253 (6)
H75B0.18140.19050.54010.072*0.253 (6)
H76A0.17890.32600.47180.072*0.253 (6)
H76B0.14330.25900.41120.072*0.253 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0316 (3)0.0402 (3)0.0354 (4)0.0011 (3)0.0025 (3)0.0014 (3)
Cu20.0306 (3)0.0403 (3)0.0299 (4)0.0006 (3)0.0009 (3)0.0012 (3)
O10.0400 (18)0.050 (2)0.033 (2)0.0018 (16)0.0033 (16)0.0049 (17)
O20.0348 (18)0.048 (2)0.058 (3)0.0052 (16)0.0046 (19)0.0154 (19)
O30.0333 (17)0.055 (2)0.028 (3)0.0017 (15)0.0022 (16)0.0041 (17)
O40.0345 (17)0.0455 (19)0.035 (2)0.0024 (14)0.0028 (16)0.0082 (17)
N10.036 (2)0.036 (2)0.035 (3)0.0049 (17)0.000 (2)0.004 (2)
N20.038 (2)0.035 (2)0.027 (3)0.0037 (18)0.0013 (19)0.0017 (19)
N30.037 (2)0.032 (2)0.035 (3)0.0064 (17)0.003 (2)0.005 (2)
N40.028 (2)0.061 (3)0.034 (3)0.0002 (19)0.0052 (19)0.001 (2)
C210.035 (3)0.040 (3)0.022 (3)0.003 (2)0.002 (2)0.002 (2)
C220.036 (3)0.038 (3)0.034 (4)0.005 (2)0.004 (2)0.003 (2)
C230.043 (3)0.042 (3)0.045 (4)0.004 (2)0.008 (3)0.013 (3)
C240.063 (4)0.047 (3)0.041 (4)0.012 (3)0.011 (3)0.009 (3)
C250.063 (4)0.056 (3)0.032 (4)0.013 (3)0.012 (3)0.000 (3)
C260.045 (3)0.047 (3)0.036 (4)0.001 (2)0.005 (3)0.000 (3)
C270.030 (3)0.042 (3)0.044 (4)0.002 (2)0.001 (2)0.006 (3)
C110.042 (3)0.034 (3)0.036 (4)0.006 (2)0.007 (3)0.003 (2)
C120.038 (3)0.029 (2)0.035 (4)0.001 (2)0.008 (2)0.001 (2)
C130.042 (3)0.044 (3)0.044 (4)0.001 (2)0.000 (3)0.006 (3)
C140.068 (4)0.050 (3)0.032 (4)0.011 (3)0.001 (3)0.001 (3)
C150.068 (4)0.069 (4)0.031 (4)0.015 (3)0.020 (3)0.011 (3)
C160.043 (3)0.068 (4)0.048 (4)0.004 (3)0.012 (3)0.008 (3)
C170.034 (3)0.039 (3)0.047 (4)0.004 (2)0.000 (3)0.006 (3)
C410.034 (3)0.041 (3)0.032 (3)0.000 (2)0.002 (2)0.001 (2)
C420.032 (2)0.034 (3)0.028 (3)0.003 (2)0.001 (2)0.003 (2)
C430.031 (3)0.044 (3)0.038 (4)0.006 (2)0.001 (2)0.001 (3)
C440.031 (2)0.042 (3)0.043 (4)0.004 (2)0.011 (2)0.009 (3)
C450.046 (3)0.039 (3)0.048 (4)0.006 (2)0.010 (3)0.002 (3)
C460.044 (3)0.047 (3)0.039 (4)0.002 (2)0.003 (3)0.007 (3)
C470.041 (3)0.052 (3)0.039 (4)0.008 (2)0.005 (3)0.005 (3)
C310.038 (3)0.032 (2)0.035 (3)0.002 (2)0.001 (2)0.001 (2)
C320.035 (3)0.031 (2)0.039 (4)0.006 (2)0.003 (3)0.002 (2)
C330.037 (3)0.037 (3)0.036 (4)0.003 (2)0.001 (2)0.002 (2)
C340.049 (3)0.045 (3)0.036 (4)0.002 (2)0.007 (3)0.001 (3)
C350.057 (3)0.051 (3)0.025 (3)0.008 (3)0.010 (3)0.005 (3)
C360.054 (3)0.036 (3)0.036 (4)0.005 (2)0.005 (3)0.001 (3)
C370.036 (3)0.032 (2)0.043 (4)0.000 (2)0.004 (2)0.004 (2)
C10.032 (3)0.038 (3)0.043 (4)0.008 (2)0.000 (2)0.003 (2)
C20.042 (3)0.042 (3)0.040 (4)0.002 (2)0.006 (3)0.001 (3)
C30.038 (3)0.042 (3)0.035 (4)0.004 (2)0.003 (2)0.005 (3)
C40.044 (3)0.044 (3)0.031 (3)0.007 (2)0.000 (3)0.003 (3)
C50.038 (3)0.041 (3)0.046 (4)0.006 (2)0.007 (3)0.000 (3)
C60.036 (3)0.037 (3)0.041 (4)0.006 (2)0.004 (2)0.000 (3)
C610.038 (4)0.033 (3)0.038 (5)0.001 (3)0.004 (4)0.004 (4)
C620.050 (4)0.035 (4)0.055 (6)0.001 (3)0.010 (4)0.002 (4)
C630.037 (4)0.043 (4)0.083 (7)0.011 (3)0.001 (4)0.000 (4)
C640.042 (4)0.043 (4)0.069 (7)0.000 (3)0.019 (4)0.007 (4)
C650.043 (4)0.036 (4)0.081 (7)0.009 (4)0.034 (4)0.005 (5)
C660.022 (3)0.049 (4)0.034 (5)0.007 (3)0.012 (3)0.013 (4)
N720.038 (2)0.035 (2)0.027 (3)0.0037 (18)0.0013 (19)0.0017 (19)
N740.028 (2)0.061 (3)0.034 (3)0.0002 (19)0.0052 (19)0.001 (2)
Geometric parameters (Å, º) top
Cu1—O21.887 (4)C33—C341.379 (7)
Cu1—O11.898 (4)C33—H330.9500
Cu1—N21.961 (4)C34—C351.394 (7)
Cu1—N11.979 (4)C34—H340.9500
Cu2—O41.896 (3)C35—C361.368 (7)
Cu2—O31.903 (3)C35—H350.9500
Cu2—N41.954 (4)C36—H360.9500
Cu2—N31.983 (4)C37—H370.9500
O1—C121.325 (6)C1—C21.519 (3)
O2—C221.314 (6)C1—H1A0.9900
O3—C321.311 (6)C1—H1B0.9900
O4—C421.312 (5)C2—C31.518 (3)
N1—C171.278 (6)C2—H2A0.9900
N1—C11.476 (6)C2—H2B0.9900
N2—C271.281 (6)C3—C41.521 (3)
N2—C611.493 (7)C3—H3A0.9900
N3—C371.288 (6)C3—H3B0.9900
N3—C61.475 (5)C4—C51.518 (3)
N4—C471.310 (6)C4—H4A0.9900
N4—C661.493 (6)C4—H4B0.9900
C21—C261.406 (6)C5—C61.519 (3)
C21—C221.424 (6)C5—H5A0.9900
C21—C271.437 (7)C5—H5B0.9900
C22—C231.397 (6)C6—H6A0.9900
C23—C241.366 (7)C6—H6B0.9900
C23—H230.9500C61—C621.520 (3)
C24—C251.406 (7)C61—H61A0.9900
C24—H240.9500C61—H61B0.9900
C25—C261.360 (7)C62—C631.517 (3)
C25—H250.9500C62—H62A0.9900
C26—H260.9500C62—H62B0.9900
C27—H270.9500C63—C641.522 (3)
C11—C121.412 (6)C63—H63A0.9900
C11—C161.414 (7)C63—H63B0.9900
C11—C171.431 (7)C64—C651.521 (3)
C12—C131.404 (7)C64—H64A0.9900
C13—C141.380 (7)C64—H64B0.9900
C13—H130.9500C65—C661.520 (3)
C14—C151.365 (7)C65—H65A0.9900
C14—H140.9500C65—H65B0.9900
C15—C161.375 (8)C66—H66A0.9900
C15—H150.9500C66—H66B0.9900
C16—H160.9500C71—C721.509 (10)
C17—H170.9500C71—H71A0.9900
C41—C461.398 (6)C71—H71B0.9900
C41—C421.400 (6)C72—C731.491 (10)
C41—C471.439 (6)C72—H72A0.9900
C42—C431.424 (6)C72—H72B0.9900
C43—C441.363 (7)C73—C741.515 (10)
C43—H430.9500C73—H73A0.9900
C44—C451.389 (7)C73—H73B0.9900
C44—H440.9500C74—C751.484 (9)
C45—C461.370 (6)C74—H74A0.9900
C45—H450.9500C74—H74B0.9900
C46—H460.9500C75—C761.511 (9)
C47—H470.9500C75—H75A0.9900
C31—C321.412 (7)C75—H75B0.9900
C31—C361.413 (7)C76—H76A0.9900
C31—C371.453 (6)C76—H76B0.9900
C32—C331.413 (6)
O2—Cu1—O1153.28 (15)C35—C36—H36119.2
O2—Cu1—N293.64 (15)C31—C36—H36119.2
O1—Cu1—N292.05 (16)N3—C37—C31126.2 (5)
O2—Cu1—N191.07 (15)N3—C37—H37116.9
O1—Cu1—N193.88 (17)C31—C37—H37116.9
N2—Cu1—N1156.81 (16)N1—C1—C2111.4 (4)
O4—Cu2—O3161.09 (14)N1—C1—H1A109.4
O4—Cu2—N493.08 (15)C2—C1—H1A109.4
O3—Cu2—N490.52 (15)N1—C1—H1B109.4
O4—Cu2—N388.64 (14)C2—C1—H1B109.4
O3—Cu2—N392.63 (15)H1A—C1—H1B108.0
N4—Cu2—N3165.10 (17)C3—C2—C1115.7 (4)
C12—O1—Cu1127.9 (3)C3—C2—H2A108.3
C22—O2—Cu1128.7 (3)C1—C2—H2A108.3
C32—O3—Cu2127.7 (3)C3—C2—H2B108.3
C42—O4—Cu2128.8 (3)C1—C2—H2B108.3
C17—N1—C1117.9 (4)H2A—C2—H2B107.4
C17—N1—Cu1122.9 (4)C2—C3—C4111.6 (4)
C1—N1—Cu1119.1 (3)C2—C3—H3A109.3
C27—N2—C61116.0 (6)C4—C3—H3A109.3
C27—N2—Cu1124.0 (3)C2—C3—H3B109.3
C61—N2—Cu1120.0 (6)C4—C3—H3B109.3
C37—N3—C6117.5 (4)H3A—C3—H3B108.0
C37—N3—Cu2124.0 (3)C5—C4—C3114.1 (4)
C6—N3—Cu2118.4 (3)C5—C4—H4A108.7
C47—N4—C66117.7 (5)C3—C4—H4A108.7
C47—N4—Cu2123.6 (3)C5—C4—H4B108.7
C66—N4—Cu2118.7 (4)C3—C4—H4B108.7
C26—C21—C22119.1 (4)H4A—C4—H4B107.6
C26—C21—C27118.3 (4)C4—C5—C6113.7 (4)
C22—C21—C27122.6 (4)C4—C5—H5A108.8
O2—C22—C23119.2 (4)C6—C5—H5A108.8
O2—C22—C21123.2 (4)C4—C5—H5B108.8
C23—C22—C21117.6 (5)C6—C5—H5B108.8
C24—C23—C22121.9 (5)H5A—C5—H5B107.7
C24—C23—H23119.1N3—C6—C5110.8 (4)
C22—C23—H23119.1N3—C6—H6A109.5
C23—C24—C25120.6 (5)C5—C6—H6A109.5
C23—C24—H24119.7N3—C6—H6B109.5
C25—C24—H24119.7C5—C6—H6B109.5
C26—C25—C24118.8 (5)H6A—C6—H6B108.1
C26—C25—H25120.6N2—C61—C62112.5 (5)
C24—C25—H25120.6N2—C61—H61A109.1
C25—C26—C21122.0 (5)C62—C61—H61A109.1
C25—C26—H26119.0N2—C61—H61B109.1
C21—C26—H26119.0C62—C61—H61B109.1
N2—C27—C21127.4 (4)H61A—C61—H61B107.8
N2—C27—H27116.3C63—C62—C61114.6 (6)
C21—C27—H27116.3C63—C62—H62A108.6
C12—C11—C16117.7 (5)C61—C62—H62A108.6
C12—C11—C17124.1 (5)C63—C62—H62B108.6
C16—C11—C17118.3 (5)C61—C62—H62B108.6
O1—C12—C13118.7 (4)H62A—C62—H62B107.6
O1—C12—C11122.3 (5)C62—C63—C64112.3 (5)
C13—C12—C11119.0 (5)C62—C63—H63A109.1
C14—C13—C12120.6 (5)C64—C63—H63A109.1
C14—C13—H13119.7C62—C63—H63B109.1
C12—C13—H13119.7C64—C63—H63B109.1
C15—C14—C13121.5 (6)H63A—C63—H63B107.9
C15—C14—H14119.2C65—C64—C63114.4 (5)
C13—C14—H14119.2C65—C64—H64A108.7
C14—C15—C16118.8 (6)C63—C64—H64A108.7
C14—C15—H15120.6C65—C64—H64B108.7
C16—C15—H15120.6C63—C64—H64B108.7
C15—C16—C11122.4 (5)H64A—C64—H64B107.6
C15—C16—H16118.8C66—C65—C64115.2 (5)
C11—C16—H16118.8C66—C65—H65A108.5
N1—C17—C11127.8 (5)C64—C65—H65A108.5
N1—C17—H17116.1C66—C65—H65B108.5
C11—C17—H17116.1C64—C65—H65B108.5
C46—C41—C42120.8 (4)H65A—C65—H65B107.5
C46—C41—C47117.2 (5)N4—C66—C65114.2 (5)
C42—C41—C47121.9 (5)N4—C66—H66A108.7
O4—C42—C41124.3 (4)C65—C66—H66A108.7
O4—C42—C43119.2 (4)N4—C66—H66B108.7
C41—C42—C43116.4 (5)C65—C66—H66B108.7
C44—C43—C42121.6 (5)H66A—C66—H66B107.6
C44—C43—H43119.2C72—C71—H71A109.8
C42—C43—H43119.2C72—C71—H71B109.8
C43—C44—C45121.2 (4)H71A—C71—H71B108.3
C43—C44—H44119.4C73—C72—C71115.3 (10)
C45—C44—H44119.4C73—C72—H72A108.5
C46—C45—C44118.5 (5)C71—C72—H72A108.5
C46—C45—H45120.7C73—C72—H72B108.5
C44—C45—H45120.7C71—C72—H72B108.5
C45—C46—C41121.4 (5)H72A—C72—H72B107.5
C45—C46—H46119.3C72—C73—C74113.6 (10)
C41—C46—H46119.3C72—C73—H73A108.9
N4—C47—C41127.4 (5)C74—C73—H73A108.8
N4—C47—H47116.3C72—C73—H73B108.8
C41—C47—H47116.3C74—C73—H73B108.8
C32—C31—C36120.0 (4)H73A—C73—H73B107.7
C32—C31—C37122.7 (5)C75—C74—C73115.5 (10)
C36—C31—C37117.3 (5)C75—C74—H74A108.4
O3—C32—C31124.1 (4)C73—C74—H74A108.4
O3—C32—C33119.0 (5)C75—C74—H74B108.4
C31—C32—C33116.8 (5)C73—C74—H74B108.4
C34—C33—C32122.0 (5)H74A—C74—H74B107.5
C34—C33—H33119.0C74—C75—C76114.7 (10)
C32—C33—H33119.0C74—C75—H75A108.6
C33—C34—C35120.6 (5)C76—C75—H75A108.6
C33—C34—H34119.7C74—C75—H75B108.6
C35—C34—H34119.7C76—C75—H75B108.6
C36—C35—C34118.9 (5)H75A—C75—H75B107.6
C36—C35—H35120.5C75—C76—H76A110.0
C34—C35—H35120.5C75—C76—H76B110.0
C35—C36—C31121.6 (5)H76A—C76—H76B108.4
O2—Cu1—O1—C1288.3 (5)C14—C15—C16—C110.6 (9)
N2—Cu1—O1—C12169.4 (4)C12—C11—C16—C152.1 (8)
N1—Cu1—O1—C1211.9 (4)C17—C11—C16—C15176.5 (5)
O1—Cu1—O2—C2295.5 (5)C1—N1—C17—C11178.6 (4)
N2—Cu1—O2—C226.4 (4)Cu1—N1—C17—C110.6 (7)
N1—Cu1—O2—C22163.7 (4)C12—C11—C17—N12.4 (8)
O4—Cu2—O3—C3276.0 (6)C16—C11—C17—N1176.1 (5)
N4—Cu2—O3—C32177.0 (4)Cu2—O4—C42—C411.5 (7)
N3—Cu2—O3—C3217.5 (4)Cu2—O4—C42—C43179.5 (3)
O3—Cu2—O4—C4292.8 (6)C46—C41—C42—O4178.6 (4)
N4—Cu2—O4—C427.8 (4)C47—C41—C42—O45.4 (8)
N3—Cu2—O4—C42173.0 (4)C46—C41—C42—C432.4 (7)
O2—Cu1—N1—C17147.7 (4)C47—C41—C42—C43173.6 (5)
O1—Cu1—N1—C176.0 (4)O4—C42—C43—C44179.7 (4)
N2—Cu1—N1—C17110.4 (5)C41—C42—C43—C441.3 (7)
O2—Cu1—N1—C130.2 (3)C42—C43—C44—C450.8 (8)
O1—Cu1—N1—C1176.1 (3)C43—C44—C45—C461.7 (8)
N2—Cu1—N1—C171.6 (5)C44—C45—C46—C410.5 (8)
O2—Cu1—N2—C276.1 (4)C42—C41—C46—C451.6 (8)
O1—Cu1—N2—C27147.8 (4)C47—C41—C46—C45174.6 (5)
N1—Cu1—N2—C27107.4 (5)C66—N4—C47—C41169.8 (5)
O2—Cu1—N2—C61176.9 (4)Cu2—N4—C47—C417.4 (8)
O1—Cu1—N2—C6129.2 (4)C46—C41—C47—N4178.2 (5)
N1—Cu1—N2—C6175.6 (6)C42—C41—C47—N42.0 (9)
O4—Cu2—N3—C37146.4 (4)Cu2—O3—C32—C3111.7 (7)
O3—Cu2—N3—C3714.7 (4)Cu2—O3—C32—C33169.6 (3)
N4—Cu2—N3—C37116.7 (7)C36—C31—C32—O3178.4 (4)
O4—Cu2—N3—C630.6 (3)C37—C31—C32—O32.9 (7)
O3—Cu2—N3—C6168.3 (3)C36—C31—C32—C333.0 (7)
N4—Cu2—N3—C666.3 (7)C37—C31—C32—C33175.7 (4)
O4—Cu2—N4—C4710.2 (4)O3—C32—C33—C34178.5 (4)
O3—Cu2—N4—C47151.2 (4)C31—C32—C33—C342.7 (7)
N3—Cu2—N4—C47106.5 (7)C32—C33—C34—C350.6 (7)
O4—Cu2—N4—C66166.8 (4)C33—C34—C35—C361.3 (8)
O3—Cu2—N4—C6631.7 (4)C34—C35—C36—C311.0 (8)
N3—Cu2—N4—C6670.6 (8)C32—C31—C36—C351.2 (7)
Cu1—O2—C22—C23177.2 (4)C37—C31—C36—C35177.6 (4)
Cu1—O2—C22—C213.4 (7)C6—N3—C37—C31176.3 (4)
C26—C21—C22—O2178.4 (5)Cu2—N3—C37—C316.6 (7)
C27—C21—C22—O22.2 (7)C32—C31—C37—N35.2 (7)
C26—C21—C22—C232.2 (7)C36—C31—C37—N3176.0 (5)
C27—C21—C22—C23177.2 (5)C17—N1—C1—C2119.2 (4)
O2—C22—C23—C24179.4 (5)Cu1—N1—C1—C262.7 (5)
C21—C22—C23—C241.2 (8)N1—C1—C2—C365.8 (5)
C22—C23—C24—C250.9 (9)C1—C2—C3—C4175.2 (4)
C23—C24—C25—C261.9 (9)C2—C3—C4—C5166.7 (4)
C24—C25—C26—C210.8 (8)C3—C4—C5—C6175.6 (4)
C22—C21—C26—C251.2 (7)C37—N3—C6—C5120.2 (4)
C27—C21—C26—C25178.2 (5)Cu2—N3—C6—C562.5 (4)
C61—N2—C27—C21179.9 (5)C4—C5—C6—N370.5 (5)
Cu1—N2—C27—C213.0 (7)C27—N2—C61—C6295.4 (8)
C26—C21—C27—N2178.4 (5)Cu1—N2—C61—C6287.4 (9)
C22—C21—C27—N22.3 (8)N2—C61—C62—C6366.2 (11)
Cu1—O1—C12—C13167.7 (3)C61—C62—C63—C64178.7 (6)
Cu1—O1—C12—C1112.1 (6)C62—C63—C64—C6572.9 (9)
C16—C11—C12—O1178.0 (4)C63—C64—C65—C66166.4 (6)
C17—C11—C12—O13.5 (7)C47—N4—C66—C6596.4 (6)
C16—C11—C12—C132.1 (7)Cu2—N4—C66—C6580.8 (6)
C17—C11—C12—C13176.4 (4)C64—C65—C66—N458.9 (8)
O1—C12—C13—C14179.4 (4)C71—C72—C73—C74161 (3)
C11—C12—C13—C140.7 (7)C72—C73—C74—C75166 (2)
C12—C13—C14—C150.8 (8)C73—C74—C75—C76161 (2)
C13—C14—C15—C160.9 (8)

Experimental details

(I)(II)
Crystal data
Chemical formula[Cu2(C20H22N2O2)2][Cu2(C20H22N2O2)2]
Mr771.81771.81
Crystal system, space groupTetragonal, P41Tetragonal, P43
Temperature (K)150150
a, c (Å)13.2963 (2), 20.6366 (5)13.3288 (2), 20.5834 (7)
V3)3648.38 (12)3656.78 (15)
Z44
Radiation typeMo KαMo Kα
µ (mm1)1.211.21
Crystal size (mm)0.22 × 0.21 × 0.200.20 × 0.18 × 0.10
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.776, 0.7940.794, 0.889
No. of measured, independent and
observed [I > 2σ(I)] reflections
20156, 7755, 5429 20308, 7763, 4824
Rint0.0720.103
(sin θ/λ)max1)0.6490.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.108, 1.00 0.049, 0.098, 0.96
No. of reflections77557763
No. of parameters470470
No. of restraints5959
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.360.35, 0.47
Absolute structureFlack (1983), 3489 Friedel pairsFlack (1983), 3505 Friedel pairs
Absolute structure parameter0.007 (14)0.000 (14)

Computer programs: COLLECT (Nonius, 1997-2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2002), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond lengths (Å) for (I) top
Cu1—O21.890 (3)Cu2—O41.895 (3)
Cu1—O11.895 (3)Cu2—O31.903 (3)
Cu1—N21.959 (4)Cu2—N41.965 (4)
Cu1—N11.972 (3)Cu2—N31.980 (4)
Selected bond lengths (Å) for (II) top
Cu1—O21.887 (4)Cu2—O41.896 (3)
Cu1—O11.898 (4)Cu2—O31.903 (3)
Cu1—N21.961 (4)Cu2—N41.954 (4)
Cu1—N11.979 (4)Cu2—N31.983 (4)
 

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