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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1379.
Published online 2010 October 9. doi:  10.1107/S1600536810039103
PMCID: PMC3008985

{μ-6,6′-Dimeth­oxy-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}methanol-μ-nitrato-dinitratocopper(II)europium(III)

Abstract

In the title dinuclear salen-type complex, [CuEu(C22H24N2O4)(NO3)3(CH3OH)], the CuII ion is five-coordinated to two imine N atoms and two phenolate O atoms and one O from the bridging nitrate group. The EuIII ion is ligated to three nitrate groups, four O atoms from the salen-type ligand and one methanol mol­ecule, leading to a distorted tenfold coordination for the rare earth cation. One of the three nitrate anions is disordered over two positions in a 0.66 (5):0.34 (5) ratio.

Related literature

For the synthesis of the ligand, see: Aslantaş et al. (2007 [triangle]); Mohamed et al. (2003 [triangle]). For similar copper lanthanide complexes with a similar salen-like ligand, see: Costes et al. (2000 [triangle], 2008 [triangle]); Koner et al. (2005 [triangle]); Sun et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1379-scheme1.jpg

Experimental

Crystal data

  • [CuEu(C22H24N2O4)(NO3)3(CH4O)]
  • M r = 814.02
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1379-efi1.jpg
  • a = 29.305 (6) Å
  • b = 14.233 (3) Å
  • c = 14.141 (3) Å
  • β = 103.36 (3)°
  • V = 5739 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.99 mm−1
  • T = 295 K
  • 0.14 × 0.12 × 0.11 mm

Data collection

  • Bruker SMART1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.677, T max = 0.727
  • 27154 measured reflections
  • 6537 independent reflections
  • 4621 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.091
  • S = 1.07
  • 6537 reflections
  • 420 parameters
  • 13 restraints
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −1.11 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2003 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039103/rk2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039103/rk2221Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported financially by the National Natural Science Foundation of China (grant Nos. 20872030 and 20972043), Heilongjiang Province (grant Nos. 2009RFXXG201, GC09A402 and 2010td03) and Heilongjiang University.

supplementary crystallographic information

Comment

In continuation of our studies of salen-type lanthanide complexes (Aslantaş et al., 2007, Mohamed et al., 2003, Sun et al., 2009), we present here the crystal structure of the title compound. The EuIII center is ligated to two bidentate nitrate groups and four oxygen atoms from the ligand, one oxygen, from the bridging nitrate group and one methanol molecule (Fig. 1). It is similar to the previously reported structures (Costes et al., 2000, 2008; Koner et al., 2005). The decacoordinated EuIII ion presents a narrow spread in Eu–O bond distances 2.338 (18)-2.786 (4)Å. The Cu(II) ion is five-coordinated by two imine nitrogen atoms, two phenol oxygen atoms from the imine-phenolate ligand and one oxygen atom from the bridgin nitrate group.

Experimental

To a 2:3 MeOH/MeCN solution (35 ml) of [(H2L)Eu(NO3)3] (0.2253 g, 0.3 mmol) was added an aqueous solution (10 ml) of Cu(OAc)2˙H2O (0.0597 g, 0.3 mmol) at ambient temperature. After stirring for 5 hrs, the solution was filtered to remove the suspended particles. Red single crystals suitable for X-ray determination were obtained by slow diffusion of diethylether into the filtrate in one week. For CuEu(C22H24N2O4)(NO3)3CH3OH elemental anal. - Calc.: for C23H28N5O14EuCu: C, 33.93; H, 3.47; N, 8.60 wt%, Found: C, 33.85; H, 3.55; N, 8.58 wt%.

Refinement

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C–H = 0.93Å (aromatic C), C–H = 0.97Å (methylene C), and with Uiso(H) = 1.2Ueq(C) or C–H = 0.96Å (methly C) and with Uiso(H) = 1.5Ueq(C). H atom bound to O atom was found from the Fourier difference map, the O–H distance was fixed, Uiso value is refined isotropically.

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Only minor fragment is presented.

Crystal data

[CuEu(C22H24N2O4)(NO3)3(CH4O)]F(000) = 3240
Mr = 814.02Dx = 1.884 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5035 reflections
a = 29.305 (6) Åθ = 3.2–27.5°
b = 14.233 (3) ŵ = 2.99 mm1
c = 14.141 (3) ÅT = 295 K
β = 103.36 (3)°Block, red
V = 5739 (2) Å30.14 × 0.12 × 0.11 mm
Z = 8

Data collection

Bruker SMART1000 CCD diffractometer6537 independent reflections
Radiation source: fine-focus sealed tube4621 reflections with I > 2σ(I)
graphiteRint = 0.061
[var phi] and ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −37→37
Tmin = 0.677, Tmax = 0.727k = −18→18
27154 measured reflectionsl = −15→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0119P)2 + 37.7609P] where P = (Fo2 + 2Fc2)/3
6537 reflections(Δ/σ)max = 0.001
420 parametersΔρmax = 0.80 e Å3
13 restraintsΔρmin = −1.11 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C10.3809 (2)0.1512 (4)1.0213 (4)0.0473 (14)
C20.3876 (2)0.1293 (4)1.1185 (4)0.0547 (16)
H20.41760.12851.15840.066*
C30.3492 (2)0.1086 (4)1.1562 (4)0.0584 (16)
H30.35370.09391.22180.070*
C40.3048 (2)0.1093 (4)1.0985 (4)0.0532 (15)
H40.27950.09541.12530.064*
C50.2970 (2)0.1309 (4)0.9987 (4)0.0441 (13)
C60.33567 (19)0.1511 (4)0.9591 (4)0.0436 (13)
C70.2496 (2)0.1251 (4)0.9423 (4)0.0537 (15)
H70.22650.11180.97590.064*
C80.1873 (2)0.1153 (7)0.7934 (5)0.083 (2)
H80.18800.05020.77130.099*
C90.1494 (2)0.1200 (6)0.8445 (5)0.082 (2)
H9B0.14880.18190.87280.099*
H9A0.15490.07420.89670.099*
C100.1024 (3)0.1002 (7)0.7742 (6)0.107 (3)
H10B0.10150.03480.75450.128*
H10A0.07740.10980.80790.128*
C110.0934 (3)0.1604 (7)0.6856 (6)0.101 (3)
H11B0.06430.14110.64190.121*
H11A0.08980.22520.70400.121*
C120.1320 (2)0.1540 (6)0.6347 (5)0.080 (2)
H12B0.12630.19800.58080.096*
H12A0.13270.09120.60840.096*
C130.1794 (2)0.1757 (6)0.7026 (5)0.0666 (19)
H130.17870.24140.72300.080*
C140.21981 (19)0.1500 (4)0.5736 (4)0.0474 (14)
H140.19050.14880.53080.057*
C150.26093 (18)0.1363 (3)0.5334 (4)0.0385 (12)
C160.25278 (19)0.1125 (4)0.4346 (4)0.0460 (13)
H160.22220.10860.39760.055*
C170.2893 (2)0.0952 (4)0.3927 (4)0.0509 (15)
H170.28320.07950.32710.061*
C180.3357 (2)0.1004 (4)0.4462 (4)0.0490 (14)
H180.36040.08660.41750.059*
C190.34390 (18)0.1265 (4)0.5425 (4)0.0403 (12)
C200.30715 (18)0.1460 (4)0.5875 (4)0.0386 (12)
C210.4269 (2)0.1079 (5)0.5650 (4)0.0580 (16)
H21C0.42240.04460.54110.087*
H21B0.45520.11130.61510.087*
H21A0.42920.14930.51280.087*
C220.4637 (2)0.1721 (6)1.0336 (5)0.078 (2)
H22C0.46700.21541.08680.117*
H22B0.48490.18910.99400.117*
H22A0.47070.10971.05840.117*
Cu10.27684 (2)0.16473 (5)0.76583 (5)0.04484 (17)
Eu10.391175 (10)0.21945 (2)0.78342 (2)0.04713 (10)
N10.23598 (16)0.1366 (4)0.8502 (3)0.0517 (12)
N20.22134 (15)0.1633 (3)0.6631 (3)0.0479 (11)
N30.4412 (2)0.0431 (4)0.8185 (4)0.0630 (14)
N40.4195 (2)0.3467 (4)0.6366 (4)0.0655 (15)
N50.3249 (2)0.3768 (4)0.8509 (4)0.0585 (14)
O10.41630 (13)0.1752 (3)0.9760 (3)0.0545 (10)
O20.33298 (13)0.1674 (3)0.8659 (3)0.0512 (10)
O30.31885 (12)0.1711 (3)0.6814 (2)0.0460 (9)
O40.38772 (12)0.1352 (3)0.6041 (3)0.0486 (9)
O50.39729 (16)0.0448 (3)0.8079 (3)0.0659 (12)
O60.4629 (2)−0.0297 (4)0.8364 (4)0.1043 (19)
O70.46107 (14)0.1212 (3)0.8105 (3)0.0603 (11)
O80.44971 (15)0.2885 (3)0.6778 (3)0.0654 (11)
O90.4283 (2)0.4068 (4)0.5823 (4)0.109 (2)
O100.37998 (17)0.3414 (3)0.6562 (3)0.0713 (13)
O11'0.3692 (5)0.3500 (9)0.882 (2)0.087 (5)0.66 (5)
O110.3575 (9)0.3580 (12)0.823 (3)0.052 (8)0.34 (5)
O120.31496 (19)0.4366 (4)0.9023 (4)0.0886 (17)
O13'0.3033 (13)0.3411 (8)0.7776 (11)0.102 (9)0.66 (5)
O130.2839 (6)0.3421 (16)0.806 (2)0.056 (6)0.34 (5)
O140.45773 (15)0.3208 (3)0.8693 (3)0.0666 (12)
H14O0.48210.30550.84860.08 (2)*
C230.4620 (4)0.4001 (7)0.9424 (8)0.145 (4)
H23C0.46390.45900.91040.218*
H23B0.48980.39130.99300.218*
H23A0.43500.40030.97000.218*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.048 (3)0.053 (3)0.038 (3)0.008 (3)0.004 (3)−0.005 (3)
C20.060 (4)0.060 (4)0.036 (3)0.017 (3)−0.006 (3)−0.004 (3)
C30.075 (5)0.065 (4)0.034 (3)0.017 (3)0.011 (3)0.004 (3)
C40.063 (4)0.058 (4)0.040 (3)0.005 (3)0.015 (3)0.002 (3)
C50.048 (3)0.049 (3)0.034 (3)0.005 (3)0.008 (2)0.001 (2)
C60.047 (3)0.048 (3)0.033 (3)0.007 (3)0.003 (2)−0.001 (2)
C70.051 (4)0.068 (4)0.047 (4)0.008 (3)0.020 (3)0.013 (3)
C80.035 (4)0.154 (8)0.055 (4)0.007 (4)0.005 (3)0.027 (5)
C90.064 (5)0.111 (6)0.071 (5)−0.007 (4)0.013 (4)0.019 (4)
C100.055 (5)0.157 (9)0.104 (7)−0.025 (5)0.011 (5)0.050 (6)
C110.056 (5)0.154 (9)0.090 (6)−0.005 (5)0.011 (4)0.014 (6)
C120.033 (3)0.139 (7)0.066 (5)0.015 (4)0.004 (3)0.013 (4)
C130.035 (3)0.109 (6)0.056 (4)0.005 (3)0.010 (3)0.017 (4)
C140.035 (3)0.058 (4)0.044 (3)−0.002 (3)−0.004 (2)0.003 (3)
C150.037 (3)0.040 (3)0.035 (3)0.001 (2)0.003 (2)0.005 (2)
C160.041 (3)0.053 (3)0.037 (3)−0.004 (3)−0.006 (2)0.002 (2)
C170.060 (4)0.060 (4)0.031 (3)−0.002 (3)0.007 (3)0.000 (3)
C180.050 (3)0.059 (4)0.040 (3)0.001 (3)0.014 (3)−0.002 (3)
C190.039 (3)0.049 (3)0.033 (3)−0.003 (2)0.010 (2)0.002 (2)
C200.040 (3)0.043 (3)0.031 (3)−0.001 (2)0.005 (2)0.006 (2)
C210.042 (3)0.079 (5)0.055 (4)0.008 (3)0.016 (3)−0.002 (3)
C220.045 (4)0.108 (6)0.067 (5)0.008 (4)−0.014 (3)0.003 (4)
Cu10.0323 (3)0.0680 (5)0.0333 (4)0.0023 (3)0.0059 (3)0.0017 (3)
Eu10.03248 (14)0.06129 (19)0.04366 (16)−0.00211 (15)0.00070 (11)−0.00113 (15)
N10.037 (3)0.077 (4)0.041 (3)0.005 (2)0.009 (2)0.014 (2)
N20.030 (2)0.069 (3)0.042 (3)0.001 (2)0.003 (2)0.003 (2)
N30.066 (4)0.070 (4)0.047 (3)0.017 (3)0.000 (3)0.001 (3)
N40.074 (4)0.074 (4)0.045 (3)−0.010 (3)0.005 (3)0.004 (3)
N50.077 (4)0.053 (3)0.053 (4)−0.003 (3)0.028 (3)0.004 (3)
O10.037 (2)0.081 (3)0.040 (2)0.007 (2)−0.0019 (18)0.0002 (19)
O20.039 (2)0.078 (3)0.034 (2)0.003 (2)0.0021 (17)0.0062 (19)
O30.034 (2)0.070 (3)0.033 (2)−0.0068 (18)0.0078 (16)−0.0075 (18)
O40.032 (2)0.073 (3)0.040 (2)0.0018 (18)0.0079 (17)−0.0034 (19)
O50.052 (3)0.072 (3)0.068 (3)−0.008 (2)0.004 (2)−0.003 (2)
O60.098 (4)0.082 (4)0.121 (5)0.035 (3)0.000 (4)0.017 (3)
O70.040 (2)0.077 (3)0.060 (3)0.002 (2)0.005 (2)0.004 (2)
O80.052 (3)0.078 (3)0.062 (3)0.000 (2)0.003 (2)0.004 (2)
O90.117 (5)0.120 (5)0.090 (4)−0.014 (4)0.025 (4)0.041 (4)
O100.057 (3)0.077 (3)0.078 (3)0.001 (2)0.011 (3)0.011 (3)
O11'0.059 (6)0.086 (7)0.114 (16)0.011 (5)0.019 (8)−0.003 (7)
O110.038 (11)0.047 (8)0.082 (18)−0.001 (6)0.034 (11)−0.008 (9)
O120.111 (4)0.077 (3)0.098 (4)−0.006 (3)0.065 (4)−0.024 (3)
O13'0.19 (2)0.064 (6)0.036 (6)0.013 (8)−0.014 (9)0.001 (4)
O130.045 (10)0.091 (11)0.034 (11)0.017 (7)0.011 (6)0.005 (8)
O140.049 (3)0.083 (3)0.067 (3)−0.015 (2)0.013 (2)−0.022 (2)
C230.121 (9)0.118 (8)0.174 (11)−0.018 (7)−0.012 (8)−0.056 (8)

Geometric parameters (Å, °)

C1—C21.378 (8)C20—O31.340 (6)
C1—O11.383 (7)C21—O41.437 (6)
C1—C61.411 (7)C21—H21C0.9600
C2—C31.383 (8)C21—H21B0.9600
C2—H20.9300C21—H21A0.9600
C3—C41.366 (8)C22—O11.439 (7)
C3—H30.9300C22—H22C0.9600
C4—C51.411 (7)C22—H22B0.9600
C4—H40.9300C22—H22A0.9600
C5—C61.404 (7)Cu1—O31.905 (3)
C5—C71.436 (8)Cu1—O21.906 (4)
C6—O21.323 (6)Cu1—N21.914 (4)
C7—N11.282 (7)Cu1—N11.917 (5)
C7—H70.9300Cu1—Eu13.3927 (10)
C8—C91.458 (9)Eu1—O112.330 (17)
C8—N11.497 (8)Eu1—O32.374 (3)
C8—C131.518 (9)Eu1—O22.395 (4)
C8—H80.9800Eu1—O72.436 (4)
C9—C101.528 (10)Eu1—O102.467 (5)
C9—H9B0.9700Eu1—O11'2.494 (18)
C9—H9A0.9700Eu1—O142.503 (4)
C10—C111.490 (10)Eu1—O52.511 (5)
C10—H10B0.9700Eu1—O82.706 (4)
C10—H10A0.9700Eu1—O12.725 (4)
C11—C121.478 (10)Eu1—O42.785 (4)
C11—H11B0.9700Eu1—N32.891 (6)
C11—H11A0.9700N3—O61.212 (7)
C12—C131.525 (8)N3—O51.261 (6)
C12—H12B0.9700N3—O71.271 (7)
C12—H12A0.9700N4—O91.215 (7)
C13—N21.475 (7)N4—O81.254 (7)
C13—H130.9800N4—O101.254 (7)
C14—N21.270 (7)N5—O111.146 (16)
C14—C151.459 (7)N5—O13'1.196 (12)
C14—H140.9300N5—O121.199 (7)
C15—C201.400 (7)N5—O131.32 (2)
C15—C161.403 (7)N5—O11'1.324 (16)
C16—C171.360 (8)O11'—O110.829 (18)
C16—H160.9300O11—O13'1.59 (2)
C17—C181.396 (8)O13'—O130.77 (2)
C17—H170.9300O14—C231.516 (10)
C18—C191.379 (7)O14—H14O0.8608
C18—H180.9300C23—H23C0.9600
C19—O41.381 (6)C23—H23B0.9600
C19—C201.399 (7)C23—H23A0.9600
C2—C1—O1124.7 (5)O7—Eu1—O1473.87 (16)
C2—C1—C6121.2 (6)O10—Eu1—O1484.60 (16)
O1—C1—C6114.1 (5)O11'—Eu1—O1464.7 (3)
C1—C2—C3119.4 (6)O11—Eu1—O5145.6 (6)
C1—C2—H2120.3O3—Eu1—O579.76 (14)
C3—C2—H2120.3O2—Eu1—O570.27 (14)
C4—C3—C2121.0 (6)O7—Eu1—O551.62 (14)
C4—C3—H3119.5O10—Eu1—O5142.23 (15)
C2—C3—H3119.5O11'—Eu1—O5132.8 (6)
C3—C4—C5120.8 (6)O14—Eu1—O5118.75 (15)
C3—C4—H4119.6O11—Eu1—O8100.6 (5)
C5—C4—H4119.6O3—Eu1—O8111.12 (12)
C6—C5—C4118.9 (5)O2—Eu1—O8174.02 (13)
C6—C5—C7123.9 (5)O7—Eu1—O871.23 (15)
C4—C5—C7117.1 (5)O10—Eu1—O848.42 (14)
O2—C6—C5124.4 (5)O11'—Eu1—O8108.4 (4)
O2—C6—C1116.9 (5)O14—Eu1—O862.38 (14)
C5—C6—C1118.7 (5)O5—Eu1—O8113.67 (15)
N1—C7—C5126.2 (5)O11—Eu1—O189.2 (10)
N1—C7—H7116.9O3—Eu1—O1122.53 (12)
C5—C7—H7116.9O2—Eu1—O160.03 (12)
C9—C8—N1117.7 (6)O7—Eu1—O171.76 (13)
C9—C8—C13114.0 (6)O10—Eu1—O1148.33 (15)
N1—C8—C13106.2 (5)O11'—Eu1—O170.1 (7)
C9—C8—H8106.0O14—Eu1—O169.39 (14)
N1—C8—H8106.0O5—Eu1—O168.86 (13)
C13—C8—H8106.0O8—Eu1—O1125.17 (12)
C8—C9—C10110.2 (7)O11—Eu1—O4130.9 (11)
C8—C9—H9B109.6O3—Eu1—O458.82 (11)
C10—C9—H9B109.6O2—Eu1—O4115.45 (12)
C8—C9—H9A109.6O7—Eu1—O475.43 (13)
C10—C9—H9A109.6O10—Eu1—O470.60 (14)
H9B—C9—H9A108.1O11'—Eu1—O4150.3 (7)
C11—C10—C9113.5 (7)O14—Eu1—O4123.37 (13)
C11—C10—H10B108.9O5—Eu1—O471.69 (13)
C9—C10—H10B108.9O8—Eu1—O463.13 (12)
C11—C10—H10A108.9O1—Eu1—O4139.01 (12)
C9—C10—H10A108.9O11—Eu1—N3156.8 (10)
H10B—C10—H10A107.7O3—Eu1—N3101.48 (15)
C12—C11—C10111.5 (7)O2—Eu1—N392.16 (16)
C12—C11—H11B109.3O7—Eu1—N325.85 (14)
C10—C11—H11B109.3O10—Eu1—N3135.45 (16)
C12—C11—H11A109.3O11'—Eu1—N3137.5 (7)
C10—C11—H11A109.3O14—Eu1—N396.30 (17)
H11B—C11—H11A108.0O5—Eu1—N325.78 (14)
C11—C12—C13111.6 (6)O8—Eu1—N392.80 (16)
C11—C12—H12B109.3O1—Eu1—N367.59 (13)
C13—C12—H12B109.3O4—Eu1—N372.12 (13)
C11—C12—H12A109.3C7—N1—C8123.6 (5)
C13—C12—H12A109.3C7—N1—Cu1124.5 (4)
H12B—C12—H12A108.0C8—N1—Cu1111.3 (4)
N2—C13—C8105.9 (5)C14—N2—C13123.7 (5)
N2—C13—C12117.0 (6)C14—N2—Cu1125.9 (4)
C8—C13—C12110.9 (6)C13—N2—Cu1110.4 (4)
N2—C13—H13107.5O6—N3—O5120.8 (7)
C8—C13—H13107.5O6—N3—O7122.5 (6)
C12—C13—H13107.5O5—N3—O7116.7 (5)
N2—C14—C15124.5 (5)O6—N3—Eu1177.7 (5)
N2—C14—H14117.8O5—N3—Eu160.0 (3)
C15—C14—H14117.8O7—N3—Eu156.7 (3)
C20—C15—C16119.2 (5)O9—N4—O8122.0 (7)
C20—C15—C14123.8 (5)O9—N4—O10121.5 (7)
C16—C15—C14117.0 (5)O8—N4—O10116.5 (6)
C17—C16—C15120.5 (5)O9—N4—Eu1172.0 (6)
C17—C16—H16119.7O8—N4—Eu163.9 (3)
C15—C16—H16119.7O10—N4—Eu152.8 (3)
C16—C17—C18121.3 (5)O11—N5—O13'85.5 (11)
C16—C17—H17119.4O11—N5—O12135.6 (13)
C18—C17—H17119.4O13'—N5—O12132.2 (17)
C19—C18—C17118.4 (5)O11—N5—O13119.4 (13)
C19—C18—H18120.8O13'—N5—O1335.4 (10)
C17—C18—H18120.8O12—N5—O13103.4 (12)
C18—C19—O4124.9 (5)O11—N5—O11'38.4 (11)
C18—C19—C20121.7 (5)O13'—N5—O11'116.5 (11)
O4—C19—C20113.4 (4)O12—N5—O11'111.2 (12)
O3—C20—C19117.1 (5)O13—N5—O11'139.9 (11)
O3—C20—C15124.1 (5)C1—O1—C22117.3 (5)
C19—C20—C15118.8 (5)C1—O1—Eu1117.5 (3)
O4—C21—H21C109.5C22—O1—Eu1125.1 (4)
O4—C21—H21B109.5C6—O2—Cu1125.4 (3)
H21C—C21—H21B109.5C6—O2—Eu1130.9 (3)
O4—C21—H21A109.5Cu1—O2—Eu1103.56 (16)
H21C—C21—H21A109.5C20—O3—Cu1123.6 (3)
H21B—C21—H21A109.5C20—O3—Eu1131.9 (3)
O1—C22—H22C109.5Cu1—O3—Eu1104.37 (15)
O1—C22—H22B109.5C19—O4—C21116.2 (4)
H22C—C22—H22B109.5C19—O4—Eu1116.5 (3)
O1—C22—H22A109.5C21—O4—Eu1127.0 (3)
H22C—C22—H22A109.5N3—O5—Eu194.2 (4)
H22B—C22—H22A109.5N3—O7—Eu197.5 (3)
O3—Cu1—O283.82 (15)N4—O8—Eu191.6 (4)
O3—Cu1—N294.78 (18)N4—O10—Eu1103.3 (4)
O2—Cu1—N2178.52 (19)O11—O11'—N559.1 (16)
O3—Cu1—N1170.7 (2)O11—O11'—Eu169 (2)
O2—Cu1—N195.66 (18)N5—O11'—Eu1113.0 (14)
N2—Cu1—N185.8 (2)O11'—O11—N583 (2)
O3—Cu1—Eu142.67 (10)O11'—O11—O13'122 (2)
O2—Cu1—Eu143.33 (11)N5—O11—O13'48.6 (8)
N2—Cu1—Eu1135.19 (14)O11'—O11—Eu192 (2)
N1—Cu1—Eu1138.63 (15)N5—O11—Eu1135.5 (12)
O11—Eu1—O391.4 (8)O13'—O11—Eu1102.4 (15)
O11—Eu1—O275.9 (5)O13—O13'—N581 (2)
O3—Eu1—O264.54 (12)O13—O13'—O11125 (2)
O11—Eu1—O7146.6 (9)N5—O13'—O1145.9 (8)
O3—Eu1—O7121.96 (14)O13—O13'—Eu1135 (2)
O2—Eu1—O7114.39 (14)N5—O13'—Eu186.7 (16)
O11—Eu1—O1065.7 (9)O11—O13'—Eu147.4 (11)
O3—Eu1—O1079.09 (14)O13'—O13—N564 (2)
O2—Eu1—O10125.68 (14)C23—O14—Eu1133.8 (5)
O7—Eu1—O10118.94 (16)C23—O14—H14O118.5
O11—Eu1—O11'19.4 (5)Eu1—O14—H14O107.7
O3—Eu1—O11'104.2 (4)O14—C23—H23C109.5
O2—Eu1—O11'69.7 (4)O14—C23—H23B109.5
O7—Eu1—O11'131.0 (6)H23C—C23—H23B109.5
O10—Eu1—O11'82.8 (7)O14—C23—H23A109.5
O11—Eu1—O1473.8 (7)H23C—C23—H23A109.5
O3—Eu1—O14161.47 (15)H23B—C23—H23A109.5
O2—Eu1—O14120.33 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2221).

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