Acta Cryst. (2008). E64, m1206 [ doi:10.1107/S1600536808026329 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-6,6'-Dimethoxy-2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}trinitratocopper(II)europium(III)In the title complex, [CuEu(C19H20N2O4)(NO3)3], the CuII ion is four-coordinated in a square-planar geometry by two O atoms and two N atoms of the deprotonated Schiff base. The EuIII atom is ten-coordinate, chelated by three nitrate groups and linked to the four O atoms of the deprotonated Schiff base.
The title complex was obtained by the treatment of copper(II) acetate monohydrate (0.0499 g, 0.25 mmol) with the Schiff base (0.0855 g, 0.25 mmol) in methanol (25 ml)at room temperature. Then the mixture was refluxed for 3 h after the addition of europium (III) nitrate hexahydrate (0.1117 g, 0.25 mmol). The reaction mixture was cooled and filtered; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis calculated for C19H20CuN5O13Eu: C, 30.78; H, 2.76; Cu, 8.50; N, 9.38; Eu, 20.58; found: C, 30.73; H, 2.70; Cu, 8.56; N, 9.44; Eu, 20.61%.
H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97 Å (methylene C), and with Uiso(H) = 1.2Ueq(C) or C—H = 0.96 Å (methly C) and with Uiso(H) = 1.5Ueq(C).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./fj2142fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids. |
| [CuEu(C19H20N2O4)(NO3)3] | F000 = 1460 |
| Mr = 741.90 | Dx = 1.982 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 17062 reflections |
| a = 11.638 (2) Å | θ = 3.0–27.5º |
| b = 14.680 (3) Å | µ = 3.43 mm−1 |
| c = 14.853 (3) Å | T = 291 (2) K |
| β = 101.52 (3)º | Block, red |
| V = 2486.5 (9) Å3 | 0.21 × 0.20 × 0.19 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 5660 independent reflections |
| Radiation source: fine-focus sealed tube | 5072 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.031 |
| Detector resolution: 10.000 pixels mm-1 | θmax = 27.5º |
| T = 291(2) K | θmin = 3.1º |
| ω scans | h = −15→13 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −19→19 |
| Tmin = 0.527, Tmax = 0.568 | l = −19→19 |
| 23524 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
| wR(F2) = 0.058 | w = 1/[σ2(Fo2) + (0.0213P)2 + 2.281P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max = 0.002 |
| 5660 reflections | Δρmax = 0.72 e Å−3 |
| 354 parameters | Δρmin = −0.44 e Å−3 |
| 6 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [CuEu(C19H20N2O4)(NO3)3] | V = 2486.5 (9) Å3 |
| Mr = 741.90 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 11.638 (2) Å | µ = 3.43 mm−1 |
| b = 14.680 (3) Å | T = 291 (2) K |
| c = 14.853 (3) Å | 0.21 × 0.20 × 0.19 mm |
| β = 101.52 (3)º |
| Rigaku R-AXIS RAPID diffractometer | 5660 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5072 reflections with I > 2σ(I) |
| Tmin = 0.527, Tmax = 0.568 | Rint = 0.031 |
| 23524 measured reflections |
| R[F2 > 2σ(F2)] = 0.024 | 6 restraints |
| wR(F2) = 0.058 | H-atom parameters constrained |
| S = 1.06 | Δρmax = 0.72 e Å−3 |
| 5660 reflections | Δρmin = −0.44 e Å−3 |
| 354 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.9061 (2) | 0.36789 (18) | −0.06244 (19) | 0.0317 (6) | |
| C2 | 0.7932 (3) | 0.3919 (2) | −0.10789 (19) | 0.0345 (6) | |
| C3 | 0.7755 (3) | 0.4599 (2) | −0.1732 (2) | 0.0449 (7) | |
| H1 | 0.6999 | 0.4743 | −0.2038 | 0.054* | |
| C4 | 0.8712 (3) | 0.5068 (2) | −0.1931 (2) | 0.0523 (9) | |
| H2 | 0.8594 | 0.5536 | −0.2361 | 0.063* | |
| C5 | 0.9823 (3) | 0.4844 (2) | −0.1499 (2) | 0.0463 (8) | |
| H3 | 1.0456 | 0.5162 | −0.1639 | 0.056* | |
| C6 | 1.0024 (3) | 0.4136 (2) | −0.0841 (2) | 0.0365 (6) | |
| C7 | 1.1218 (3) | 0.3936 (2) | −0.0403 (2) | 0.0397 (7) | |
| H4 | 1.1783 | 0.4344 | −0.0518 | 0.048* | |
| C8 | 1.2885 (3) | 0.3275 (2) | 0.0496 (3) | 0.0536 (9) | |
| H5 | 1.3080 | 0.3813 | 0.0876 | 0.064* | |
| H6 | 1.3290 | 0.3320 | −0.0013 | 0.064* | |
| C9 | 1.3326 (3) | 0.2449 (2) | 0.1056 (3) | 0.0511 (9) | |
| H7 | 1.3038 | 0.2462 | 0.1625 | 0.061* | |
| H8 | 1.4176 | 0.2469 | 0.1211 | 0.061* | |
| C10 | 1.2950 (3) | 0.1573 (2) | 0.0561 (3) | 0.0488 (8) | |
| H9 | 1.2975 | 0.1638 | −0.0085 | 0.059* | |
| H10 | 1.3483 | 0.1088 | 0.0815 | 0.059* | |
| C11 | 1.1568 (2) | 0.05275 (19) | 0.09083 (19) | 0.0336 (6) | |
| H11 | 1.2194 | 0.0126 | 0.0954 | 0.040* | |
| C12 | 1.0502 (2) | 0.01617 (18) | 0.11234 (18) | 0.0304 (6) | |
| C13 | 1.0533 (3) | −0.0754 (2) | 0.1430 (2) | 0.0380 (7) | |
| H12 | 1.1202 | −0.1105 | 0.1442 | 0.046* | |
| C14 | 0.9582 (3) | −0.1123 (2) | 0.1709 (2) | 0.0458 (8) | |
| H13 | 0.9602 | −0.1727 | 0.1899 | 0.055* | |
| C15 | 0.8589 (3) | −0.0602 (2) | 0.1710 (2) | 0.0413 (7) | |
| H14 | 0.7953 | −0.0853 | 0.1914 | 0.050* | |
| C16 | 0.8541 (2) | 0.02870 (19) | 0.14095 (19) | 0.0321 (6) | |
| C17 | 0.9492 (2) | 0.06820 (17) | 0.10940 (17) | 0.0282 (5) | |
| C18 | 0.6700 (3) | 0.0552 (3) | 0.1857 (3) | 0.0560 (9) | |
| H15 | 0.6339 | 0.0016 | 0.1553 | 0.084* | |
| H16 | 0.6119 | 0.1019 | 0.1839 | 0.084* | |
| H17 | 0.7039 | 0.0408 | 0.2484 | 0.084* | |
| C19 | 0.5899 (3) | 0.3491 (3) | −0.1377 (3) | 0.0647 (11) | |
| H18 | 0.5650 | 0.4115 | −0.1394 | 0.097* | |
| H19 | 0.5363 | 0.3122 | −0.1121 | 0.097* | |
| H20 | 0.5913 | 0.3287 | −0.1988 | 0.097* | |
| Cu1 | 1.05535 (3) | 0.22819 (2) | 0.03974 (2) | 0.03036 (8) | |
| Eu1 | 0.762074 (11) | 0.247433 (8) | 0.068399 (9) | 0.02785 (5) | |
| N1 | 1.1594 (2) | 0.32671 (17) | 0.01249 (18) | 0.0382 (6) | |
| N2 | 1.1746 (2) | 0.13432 (16) | 0.06616 (17) | 0.0341 (5) | |
| N3 | 0.6075 (3) | 0.12249 (19) | −0.0485 (2) | 0.0504 (7) | |
| N4 | 0.8226 (5) | 0.2655 (3) | 0.2660 (2) | 0.0872 (15) | |
| N5 | 0.6480 (2) | 0.42062 (17) | 0.09471 (18) | 0.0433 (6) | |
| O1 | 0.91672 (16) | 0.30177 (13) | 0.00059 (14) | 0.0353 (4) | |
| O2 | 0.70508 (18) | 0.34136 (15) | −0.08175 (14) | 0.0399 (5) | |
| O3 | 0.93757 (16) | 0.15332 (12) | 0.07838 (13) | 0.0324 (4) | |
| O4 | 0.76063 (18) | 0.08689 (14) | 0.13955 (15) | 0.0390 (5) | |
| O5 | 0.7096 (2) | 0.13933 (16) | −0.06160 (16) | 0.0478 (5) | |
| O6 | 0.5492 (3) | 0.0630 (2) | −0.0900 (3) | 0.1037 (13) | |
| O7 | 0.57208 (18) | 0.17165 (15) | 0.01090 (16) | 0.0445 (5) | |
| O8 | 0.7188 (3) | 0.25602 (16) | 0.2249 (2) | 0.0633 (8) | |
| O9 | 0.8490 (5) | 0.2703 (3) | 0.3497 (2) | 0.1377 (17) | |
| O10 | 0.8992 (3) | 0.2700 (2) | 0.2174 (2) | 0.0809 (10) | |
| O11 | 0.58719 (19) | 0.35057 (16) | 0.07275 (17) | 0.0478 (5) | |
| O12 | 0.6061 (3) | 0.49507 (18) | 0.1043 (2) | 0.0779 (9) | |
| O13 | 0.75861 (19) | 0.41086 (15) | 0.10619 (17) | 0.0457 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0326 (14) | 0.0304 (13) | 0.0328 (14) | 0.0001 (11) | 0.0084 (11) | 0.0008 (11) |
| C2 | 0.0338 (15) | 0.0357 (14) | 0.0341 (14) | −0.0031 (12) | 0.0074 (12) | 0.0002 (12) |
| C3 | 0.0492 (19) | 0.0455 (18) | 0.0374 (16) | 0.0018 (15) | 0.0022 (14) | 0.0098 (13) |
| C4 | 0.062 (2) | 0.052 (2) | 0.0429 (18) | −0.0013 (17) | 0.0104 (16) | 0.0185 (15) |
| C5 | 0.052 (2) | 0.0428 (17) | 0.0477 (18) | −0.0078 (15) | 0.0186 (16) | 0.0115 (14) |
| C6 | 0.0382 (16) | 0.0335 (14) | 0.0408 (16) | −0.0030 (12) | 0.0149 (13) | 0.0017 (12) |
| C7 | 0.0350 (16) | 0.0353 (15) | 0.0528 (18) | −0.0075 (13) | 0.0186 (14) | 0.0013 (13) |
| C8 | 0.0262 (16) | 0.0448 (19) | 0.089 (3) | −0.0044 (14) | 0.0089 (17) | −0.0001 (18) |
| C9 | 0.0259 (16) | 0.059 (2) | 0.067 (2) | −0.0044 (14) | 0.0062 (15) | 0.0024 (17) |
| C10 | 0.0306 (16) | 0.0420 (17) | 0.079 (2) | 0.0051 (14) | 0.0225 (16) | 0.0063 (16) |
| C11 | 0.0298 (14) | 0.0363 (14) | 0.0340 (14) | 0.0067 (12) | 0.0052 (11) | 0.0010 (12) |
| C12 | 0.0329 (14) | 0.0304 (13) | 0.0280 (13) | 0.0012 (11) | 0.0065 (11) | −0.0008 (10) |
| C13 | 0.0431 (17) | 0.0323 (14) | 0.0382 (16) | 0.0068 (13) | 0.0070 (13) | 0.0022 (12) |
| C14 | 0.057 (2) | 0.0283 (14) | 0.0526 (19) | −0.0006 (14) | 0.0135 (16) | 0.0089 (13) |
| C15 | 0.0448 (18) | 0.0352 (15) | 0.0463 (17) | −0.0081 (13) | 0.0145 (14) | 0.0057 (13) |
| C16 | 0.0310 (14) | 0.0312 (14) | 0.0343 (14) | −0.0015 (11) | 0.0072 (11) | 0.0011 (11) |
| C17 | 0.0323 (14) | 0.0268 (12) | 0.0254 (12) | −0.0026 (11) | 0.0054 (10) | −0.0005 (10) |
| C18 | 0.0374 (18) | 0.061 (2) | 0.077 (3) | −0.0020 (16) | 0.0289 (18) | 0.0201 (19) |
| C19 | 0.0328 (18) | 0.084 (3) | 0.069 (2) | −0.0063 (18) | −0.0103 (17) | 0.024 (2) |
| Cu1 | 0.02206 (16) | 0.03009 (16) | 0.03997 (18) | −0.00026 (13) | 0.00866 (14) | 0.00474 (14) |
| Eu1 | 0.02169 (8) | 0.02888 (8) | 0.03354 (8) | −0.00131 (5) | 0.00688 (5) | −0.00045 (5) |
| N1 | 0.0247 (12) | 0.0372 (13) | 0.0539 (15) | −0.0038 (10) | 0.0110 (11) | −0.0005 (11) |
| N2 | 0.0254 (12) | 0.0361 (13) | 0.0422 (13) | 0.0030 (10) | 0.0103 (10) | 0.0021 (10) |
| N3 | 0.0429 (16) | 0.0409 (15) | 0.0632 (18) | −0.0032 (12) | 0.0008 (14) | −0.0151 (13) |
| N4 | 0.119 (4) | 0.100 (3) | 0.0346 (16) | 0.079 (3) | −0.003 (2) | −0.0102 (17) |
| N5 | 0.0479 (17) | 0.0361 (14) | 0.0454 (15) | 0.0078 (12) | 0.0084 (12) | 0.0007 (11) |
| O1 | 0.0274 (10) | 0.0341 (10) | 0.0457 (11) | 0.0018 (8) | 0.0107 (9) | 0.0132 (9) |
| O2 | 0.0270 (10) | 0.0460 (12) | 0.0437 (12) | −0.0020 (9) | 0.0002 (9) | 0.0098 (9) |
| O3 | 0.0269 (10) | 0.0276 (9) | 0.0447 (11) | 0.0020 (8) | 0.0122 (8) | 0.0073 (8) |
| O4 | 0.0310 (11) | 0.0382 (11) | 0.0521 (12) | −0.0011 (9) | 0.0181 (10) | 0.0089 (9) |
| O5 | 0.0432 (13) | 0.0474 (13) | 0.0544 (13) | −0.0019 (11) | 0.0136 (11) | −0.0141 (11) |
| O6 | 0.068 (2) | 0.087 (2) | 0.151 (3) | −0.0302 (18) | 0.010 (2) | −0.070 (2) |
| O7 | 0.0293 (11) | 0.0483 (13) | 0.0551 (13) | −0.0027 (9) | 0.0066 (10) | −0.0091 (11) |
| O8 | 0.088 (2) | 0.0581 (16) | 0.0499 (15) | 0.0195 (14) | 0.0294 (16) | 0.0010 (12) |
| O9 | 0.166 (4) | 0.192 (4) | 0.0457 (17) | 0.115 (3) | −0.003 (2) | −0.020 (2) |
| O10 | 0.0621 (19) | 0.114 (3) | 0.0561 (17) | 0.0386 (18) | −0.0146 (15) | −0.0300 (17) |
| O11 | 0.0298 (11) | 0.0466 (13) | 0.0674 (15) | 0.0017 (10) | 0.0107 (10) | −0.0029 (11) |
| O12 | 0.089 (2) | 0.0437 (14) | 0.099 (2) | 0.0295 (15) | 0.0140 (18) | −0.0063 (15) |
| O13 | 0.0378 (12) | 0.0380 (12) | 0.0607 (14) | −0.0067 (9) | 0.0087 (10) | −0.0057 (10) |
| C1—O1 | 1.337 (3) | C16—O4 | 1.380 (3) |
| C1—C6 | 1.398 (4) | C16—C17 | 1.409 (4) |
| C1—C2 | 1.398 (4) | C17—O3 | 1.329 (3) |
| C2—C3 | 1.378 (4) | C18—O4 | 1.445 (3) |
| C2—O2 | 1.383 (3) | C18—H15 | 0.9600 |
| C3—C4 | 1.392 (5) | C18—H16 | 0.9600 |
| C3—H1 | 0.9300 | C18—H17 | 0.9600 |
| C4—C5 | 1.363 (5) | C19—O2 | 1.433 (4) |
| C4—H2 | 0.9300 | C19—H18 | 0.9600 |
| C5—C6 | 1.414 (4) | C19—H19 | 0.9600 |
| C5—H3 | 0.9300 | C19—H20 | 0.9600 |
| C6—C7 | 1.441 (4) | Cu1—O3 | 1.9315 (18) |
| C7—N1 | 1.278 (4) | Cu1—O1 | 1.9320 (19) |
| C7—H4 | 0.9300 | Cu1—N2 | 1.940 (2) |
| C8—N1 | 1.494 (4) | Cu1—N1 | 1.980 (2) |
| C8—C9 | 1.501 (5) | Eu1—O1 | 2.3694 (19) |
| C8—H5 | 0.9700 | Eu1—O3 | 2.4457 (18) |
| C8—H6 | 0.9700 | Eu1—O13 | 2.466 (2) |
| C9—C10 | 1.502 (5) | Eu1—O7 | 2.470 (2) |
| C9—H7 | 0.9700 | Eu1—O8 | 2.478 (3) |
| C9—H8 | 0.9700 | Eu1—O10 | 2.478 (3) |
| C10—N2 | 1.478 (4) | Eu1—O5 | 2.480 (2) |
| C10—H9 | 0.9700 | Eu1—O11 | 2.548 (2) |
| C10—H10 | 0.9700 | Eu1—O4 | 2.584 (2) |
| C11—N2 | 1.281 (4) | Eu1—O2 | 2.593 (2) |
| C11—C12 | 1.445 (4) | N3—O6 | 1.198 (4) |
| C11—H11 | 0.9300 | N3—O5 | 1.266 (4) |
| C12—C17 | 1.395 (4) | N3—O7 | 1.271 (3) |
| C12—C13 | 1.418 (4) | N4—O9 | 1.222 (5) |
| C13—C14 | 1.368 (4) | N4—O8 | 1.249 (5) |
| C13—H12 | 0.9300 | N4—O10 | 1.256 (6) |
| C14—C15 | 1.387 (5) | N5—O12 | 1.216 (3) |
| C14—H13 | 0.9300 | N5—O11 | 1.254 (3) |
| C15—C16 | 1.376 (4) | N5—O13 | 1.273 (3) |
| C15—H14 | 0.9300 | ||
| O1—C1—C6 | 122.9 (3) | O1—Eu1—O3 | 61.31 (6) |
| O1—C1—C2 | 117.9 (2) | O1—Eu1—O13 | 79.49 (7) |
| C6—C1—C2 | 119.2 (3) | O3—Eu1—O13 | 125.96 (7) |
| C3—C2—O2 | 124.8 (3) | O1—Eu1—O7 | 135.09 (7) |
| C3—C2—C1 | 121.1 (3) | O3—Eu1—O7 | 116.46 (7) |
| O2—C2—C1 | 114.0 (2) | O13—Eu1—O7 | 117.56 (7) |
| C2—C3—C4 | 119.6 (3) | O1—Eu1—O8 | 134.09 (10) |
| C2—C3—H1 | 120.2 | O3—Eu1—O8 | 107.21 (9) |
| C4—C3—H1 | 120.2 | O13—Eu1—O8 | 73.82 (8) |
| C5—C4—C3 | 120.3 (3) | O7—Eu1—O8 | 90.65 (10) |
| C5—C4—H2 | 119.8 | O1—Eu1—O10 | 85.77 (10) |
| C3—C4—H2 | 119.8 | O3—Eu1—O10 | 68.91 (8) |
| C4—C5—C6 | 120.9 (3) | O13—Eu1—O10 | 72.77 (9) |
| C4—C5—H3 | 119.6 | O7—Eu1—O10 | 137.83 (11) |
| C6—C5—H3 | 119.6 | O8—Eu1—O10 | 51.04 (12) |
| C1—C6—C5 | 118.8 (3) | O1—Eu1—O5 | 88.53 (8) |
| C1—C6—C7 | 122.9 (3) | O3—Eu1—O5 | 76.02 (8) |
| C5—C6—C7 | 118.2 (3) | O13—Eu1—O5 | 141.92 (8) |
| N1—C7—C6 | 127.9 (3) | O7—Eu1—O5 | 51.56 (8) |
| N1—C7—H4 | 116.1 | O8—Eu1—O5 | 134.29 (9) |
| C6—C7—H4 | 116.1 | O10—Eu1—O5 | 142.67 (9) |
| N1—C8—C9 | 113.9 (3) | O1—Eu1—O11 | 119.29 (7) |
| N1—C8—H5 | 108.8 | O3—Eu1—O11 | 174.77 (7) |
| C9—C8—H5 | 108.8 | O13—Eu1—O11 | 50.70 (7) |
| N1—C8—H6 | 108.8 | O7—Eu1—O11 | 67.17 (8) |
| C9—C8—H6 | 108.8 | O8—Eu1—O11 | 68.45 (9) |
| H5—C8—H6 | 107.7 | O10—Eu1—O11 | 105.86 (9) |
| C8—C9—C10 | 112.7 (3) | O5—Eu1—O11 | 109.04 (8) |
| C8—C9—H7 | 109.0 | O1—Eu1—O4 | 123.26 (6) |
| C10—C9—H7 | 109.0 | O3—Eu1—O4 | 62.20 (6) |
| C8—C9—H8 | 109.0 | O13—Eu1—O4 | 142.41 (8) |
| C10—C9—H8 | 109.0 | O7—Eu1—O4 | 69.64 (7) |
| H7—C9—H8 | 107.8 | O8—Eu1—O4 | 69.12 (7) |
| N2—C10—C9 | 109.6 (3) | O10—Eu1—O4 | 79.18 (10) |
| N2—C10—H9 | 109.7 | O5—Eu1—O4 | 73.38 (8) |
| C9—C10—H9 | 109.7 | O11—Eu1—O4 | 117.46 (7) |
| N2—C10—H10 | 109.7 | O1—Eu1—O2 | 62.67 (7) |
| C9—C10—H10 | 109.7 | O3—Eu1—O2 | 114.81 (7) |
| H9—C10—H10 | 108.2 | O13—Eu1—O2 | 70.45 (8) |
| N2—C11—C12 | 127.3 (3) | O7—Eu1—O2 | 83.38 (8) |
| N2—C11—H11 | 116.3 | O8—Eu1—O2 | 135.61 (8) |
| C12—C11—H11 | 116.3 | O10—Eu1—O2 | 134.86 (10) |
| C17—C12—C13 | 119.8 (3) | O5—Eu1—O2 | 71.93 (8) |
| C17—C12—C11 | 123.0 (2) | O11—Eu1—O2 | 68.74 (8) |
| C13—C12—C11 | 117.1 (3) | O4—Eu1—O2 | 144.61 (7) |
| C14—C13—C12 | 120.1 (3) | C7—N1—C8 | 114.6 (3) |
| C14—C13—H12 | 120.0 | C7—N1—Cu1 | 122.6 (2) |
| C12—C13—H12 | 120.0 | C8—N1—Cu1 | 122.8 (2) |
| C13—C14—C15 | 120.5 (3) | C11—N2—C10 | 117.0 (2) |
| C13—C14—H13 | 119.7 | C11—N2—Cu1 | 124.85 (19) |
| C15—C14—H13 | 119.7 | C10—N2—Cu1 | 118.15 (19) |
| C16—C15—C14 | 120.1 (3) | O6—N3—O5 | 121.1 (3) |
| C16—C15—H14 | 119.9 | O6—N3—O7 | 122.8 (3) |
| C14—C15—H14 | 119.9 | O5—N3—O7 | 116.1 (2) |
| C15—C16—O4 | 124.9 (3) | O9—N4—O8 | 121.7 (5) |
| C15—C16—C17 | 121.0 (3) | O9—N4—O10 | 121.3 (5) |
| O4—C16—C17 | 114.1 (2) | O8—N4—O10 | 117.0 (3) |
| O3—C17—C12 | 123.5 (2) | O12—N5—O11 | 123.3 (3) |
| O3—C17—C16 | 118.0 (2) | O12—N5—O13 | 120.2 (3) |
| C12—C17—C16 | 118.5 (2) | O11—N5—O13 | 116.5 (2) |
| O4—C18—H15 | 109.5 | C1—O1—Cu1 | 124.84 (17) |
| O4—C18—H16 | 109.5 | C1—O1—Eu1 | 124.78 (16) |
| H15—C18—H16 | 109.5 | Cu1—O1—Eu1 | 110.09 (8) |
| O4—C18—H17 | 109.5 | C2—O2—C19 | 117.1 (2) |
| H15—C18—H17 | 109.5 | C2—O2—Eu1 | 116.77 (17) |
| H16—C18—H17 | 109.5 | C19—O2—Eu1 | 126.1 (2) |
| O2—C19—H18 | 109.5 | C17—O3—Cu1 | 127.52 (17) |
| O2—C19—H19 | 109.5 | C17—O3—Eu1 | 125.29 (16) |
| H18—C19—H19 | 109.5 | Cu1—O3—Eu1 | 107.10 (8) |
| O2—C19—H20 | 109.5 | C16—O4—C18 | 116.2 (2) |
| H18—C19—H20 | 109.5 | C16—O4—Eu1 | 120.07 (15) |
| H19—C19—H20 | 109.5 | C18—O4—Eu1 | 123.57 (19) |
| O3—Cu1—O1 | 78.94 (8) | N3—O5—Eu1 | 95.64 (17) |
| O3—Cu1—N2 | 93.28 (9) | N3—O7—Eu1 | 95.94 (17) |
| O1—Cu1—N2 | 168.21 (10) | N4—O8—Eu1 | 96.1 (2) |
| O3—Cu1—N1 | 167.44 (9) | N4—O10—Eu1 | 95.9 (3) |
| O1—Cu1—N1 | 92.19 (9) | N5—O11—Eu1 | 94.71 (17) |
| N2—Cu1—N1 | 96.78 (10) | N5—O13—Eu1 | 98.11 (17) |
The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (Nos. 20572018 and 20672032), Heilongjiang Province (Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.
Elmali, A. & Elerman, Y. (2003). Z. Naturforsch. Teil B, 58, 639–643.
Elmali, A. & Elerman, Y. (2004). Z. Naturforsch. Teil B, 59, 535–540.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
As shown in Fig. 1, the hexadentate Schiff base ligand links Cu and Eu atoms into a dinuclear complex through two phenolate O atoms, which is similar with the bonding reported for another copper-lanthanide complex of the same ligand (Elmali & Elerman, 2003, 2004). The EuIII centre in (I) is ten-coordinated by four oxygen atoms from the ligand and six oxygen atoms from three nitrate ions. The CuII center is four-coordinate by two nitrogen atoms and two oxygen atoms from the ligand.