Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034903/ng2297sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034903/ng2297Isup2.hkl |
CCDC reference: 627235
The title complex was obtained by the treatment of copper(II) acetate monohydrate with the Schiff base in water/methanol (1:3). The first two reactants were stirred for 2 h, and the mixture was stirred for another 3 h after the addition of europium (III) nitrate hexahydrate. The reaction mixture was filtered; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis calculated for for C17H17Cu1Eu1N5O12: C 29.22, H 2.45, N 10.02%; found: C 29.38, H 2.38, N 10.00%.
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). The H atoms of hydroxy were initially located in a difference Fourier map but they were treated as riding on their parent atoms with O—H=0.85 Å, Uiso(H) = 1.5Ueq(O) In complex (I), the diaminopropane is disordered and was refined with a split model over two positions, and with an occupancy of 0.72 (2) for C8, C9, and 0.28 (2) for C8', C9'.
As shown in Fig. 1, the tetradentate Schiff base ligand links Cu and Eu atoms into a dinuclear complex through two phenolate O atoms. The EuIII centre in (I) is nine-coordinated by two O atoms from the ligand, six O atoms from three nitrate and one O atoms from the methanol, which is similar with the bonding reported for another copper-lanthanum complex of the same ligand (Kahn et al., 2000). The CuII center is five-coordinate by two N atoms, two O atoms from the ligand and one nitrato oxygen of neighboring dinuclear unit in a square-pyramidal geometry.
See Kahn et al. (2000) for a similar copper–lanthanum complex of the same Schiff base.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. Disordered atoms (C8', C9') have been omitted for clarity. |
[CuEu(C16H14N2O2)(NO3)3(CH4O)] | F(000) = 1372 |
Mr = 699.87 | Dx = 2.041 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18713 reflections |
a = 12.223 (4) Å | θ = 6.0–54.9° |
b = 10.363 (3) Å | µ = 3.74 mm−1 |
c = 18.414 (5) Å | T = 296 K |
β = 102.451 (12)° | Block, black |
V = 2277.6 (12) Å3 | 0.33 × 0.20 × 0.19 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5201 independent reflections |
Radiation source: fine-focus sealed tube | 4693 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→13 |
Tmin = 0.376, Tmax = 0.543 | l = −23→22 |
21558 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.021 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0142P)2 + 1.9917P] where P = (Fo2 + 2Fc2)/3 |
5201 reflections | (Δ/σ)max = 0.003 |
345 parameters | Δρmax = 0.31 e Å−3 |
2 restraints | Δρmin = −0.59 e Å−3 |
[CuEu(C16H14N2O2)(NO3)3(CH4O)] | V = 2277.6 (12) Å3 |
Mr = 699.87 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.223 (4) Å | µ = 3.74 mm−1 |
b = 10.363 (3) Å | T = 296 K |
c = 18.414 (5) Å | 0.33 × 0.20 × 0.19 mm |
β = 102.451 (12)° |
Rigaku R-AXIS RAPID diffractometer | 5201 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4693 reflections with I > 2σ(I) |
Tmin = 0.376, Tmax = 0.543 | Rint = 0.030 |
21558 measured reflections |
R[F2 > 2σ(F2)] = 0.021 | 2 restraints |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.31 e Å−3 |
5201 reflections | Δρmin = −0.59 e Å−3 |
345 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 | Occ. (<1) | |
C1 | 0.1201 (2) | 0.7351 (3) | 0.60899 (13) | 0.0310 (5) | |
C2 | 0.0762 (2) | 0.6757 (3) | 0.66454 (15) | 0.0413 (6) | |
H1 | 0.0794 | 0.5863 | 0.6690 | 0.050* | |
C3 | 0.0284 (2) | 0.7464 (3) | 0.71266 (16) | 0.0464 (7) | |
H2 | −0.0004 | 0.7041 | 0.7490 | 0.056* | |
C4 | 0.0225 (3) | 0.8791 (3) | 0.70797 (17) | 0.0535 (8) | |
H3 | −0.0088 | 0.9266 | 0.7412 | 0.064* | |
C5 | 0.0635 (3) | 0.9394 (3) | 0.65357 (18) | 0.0510 (8) | |
H4 | 0.0589 | 1.0288 | 0.6498 | 0.061* | |
C6 | 0.1127 (2) | 0.8705 (3) | 0.60289 (15) | 0.0377 (6) | |
C7 | 0.1553 (3) | 0.9448 (3) | 0.54848 (17) | 0.0450 (7) | |
H5 | 0.1532 | 1.0343 | 0.5522 | 0.054* | |
C8 | 0.2543 (9) | 0.9774 (6) | 0.4478 (4) | 0.0442 (17) | 0.72 (2) |
H6 | 0.2241 | 1.0643 | 0.4428 | 0.053* | |
H7 | 0.3337 | 0.9824 | 0.4701 | 0.053* | |
C9 | 0.2369 (9) | 0.9143 (5) | 0.3736 (4) | 0.0434 (19) | 0.72 (2) |
H9 | 0.1617 | 0.9311 | 0.3452 | 0.052* | |
H8 | 0.2901 | 0.9473 | 0.3460 | 0.052* | |
C10 | 0.2881 (2) | 0.7069 (3) | 0.33908 (15) | 0.0438 (7) | |
H10 | 0.3171 | 0.7489 | 0.3028 | 0.053* | |
C11 | 0.2860 (2) | 0.5681 (3) | 0.33729 (14) | 0.0344 (5) | |
C12 | 0.3126 (3) | 0.5076 (3) | 0.27460 (16) | 0.0462 (7) | |
H11 | 0.3385 | 0.5580 | 0.2401 | 0.055* | |
C13 | 0.3018 (3) | 0.3784 (3) | 0.26293 (16) | 0.0521 (8) | |
H12 | 0.3207 | 0.3408 | 0.2214 | 0.063* | |
C14 | 0.2622 (3) | 0.3039 (3) | 0.31397 (17) | 0.0500 (7) | |
H13 | 0.2518 | 0.2158 | 0.3058 | 0.060* | |
C15 | 0.2379 (2) | 0.3589 (3) | 0.37687 (16) | 0.0426 (6) | |
H14 | 0.2125 | 0.3068 | 0.4109 | 0.051* | |
C16 | 0.2507 (2) | 0.4903 (2) | 0.39041 (13) | 0.0310 (5) | |
C17 | 0.4417 (3) | 0.7572 (3) | 0.61542 (19) | 0.0522 (8) | |
H15 | 0.3802 | 0.7787 | 0.6380 | 0.078* | |
H16 | 0.4551 | 0.8272 | 0.5843 | 0.078* | |
H17 | 0.5077 | 0.7424 | 0.6535 | 0.078* | |
Cu2 | 0.20183 (3) | 0.71765 (3) | 0.471852 (16) | 0.03015 (7) | |
Eu1 | 0.279281 (10) | 0.471486 (11) | 0.579103 (6) | 0.02628 (4) | |
N1 | 0.1952 (2) | 0.8978 (2) | 0.49601 (13) | 0.0397 (5) | |
N2 | 0.2534 (2) | 0.7769 (2) | 0.38641 (13) | 0.0413 (5) | |
N3 | 0.40354 (19) | 0.4886 (2) | 0.73120 (12) | 0.0404 (5) | |
N4 | 0.08119 (18) | 0.3280 (2) | 0.59421 (13) | 0.0378 (5) | |
N5 | 0.4077 (2) | 0.2526 (2) | 0.54166 (14) | 0.0434 (6) | |
O1 | 0.16860 (14) | 0.66089 (16) | 0.56505 (9) | 0.0309 (4) | |
O2 | 0.22848 (16) | 0.53808 (16) | 0.45385 (10) | 0.0343 (4) | |
O3 | 0.41493 (16) | 0.64166 (19) | 0.57093 (12) | 0.0463 (5) | |
H18 | 0.4580 | 0.6326 | 0.5407 | 0.056* | |
O4 | 0.32467 (16) | 0.5670 (2) | 0.70399 (10) | 0.0430 (5) | |
O5 | 0.4574 (2) | 0.5002 (3) | 0.79437 (11) | 0.0645 (7) | |
O6 | 0.42138 (17) | 0.3997 (2) | 0.68870 (11) | 0.0470 (5) | |
O7 | 0.15586 (16) | 0.3634 (2) | 0.64981 (10) | 0.0414 (4) | |
O8 | 0.00002 (18) | 0.2658 (2) | 0.60258 (14) | 0.0623 (7) | |
O9 | 0.09572 (17) | 0.3610 (2) | 0.53148 (11) | 0.0503 (5) | |
O10 | 0.31744 (18) | 0.23862 (19) | 0.56357 (13) | 0.0491 (5) | |
O11 | 0.4658 (2) | 0.1628 (2) | 0.53211 (17) | 0.0735 (8) | |
O12 | 0.43392 (16) | 0.36900 (18) | 0.52960 (11) | 0.0417 (4) | |
C8' | 0.202 (2) | 0.9864 (16) | 0.4356 (11) | 0.045 (4) | 0.28 (2) |
C9' | 0.293 (2) | 0.9273 (15) | 0.4025 (15) | 0.054 (6) | 0.28 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0286 (11) | 0.0361 (14) | 0.0289 (12) | 0.0057 (10) | 0.0078 (10) | −0.0022 (10) |
C2 | 0.0475 (15) | 0.0414 (15) | 0.0398 (14) | 0.0083 (13) | 0.0203 (12) | 0.0055 (12) |
C3 | 0.0469 (16) | 0.059 (2) | 0.0399 (15) | 0.0091 (14) | 0.0239 (13) | 0.0027 (14) |
C4 | 0.0624 (19) | 0.059 (2) | 0.0455 (16) | 0.0185 (16) | 0.0265 (15) | −0.0091 (15) |
C5 | 0.067 (2) | 0.0382 (16) | 0.0532 (18) | 0.0131 (15) | 0.0241 (16) | −0.0060 (14) |
C6 | 0.0430 (14) | 0.0349 (14) | 0.0372 (14) | 0.0042 (12) | 0.0130 (12) | −0.0036 (11) |
C7 | 0.0645 (19) | 0.0242 (13) | 0.0484 (16) | −0.0005 (12) | 0.0167 (15) | −0.0026 (12) |
C8 | 0.050 (4) | 0.029 (2) | 0.060 (3) | −0.008 (3) | 0.028 (3) | 0.002 (2) |
C9 | 0.066 (5) | 0.031 (2) | 0.041 (3) | 0.002 (3) | 0.026 (3) | 0.008 (2) |
C10 | 0.0550 (17) | 0.0459 (16) | 0.0376 (14) | 0.0043 (14) | 0.0254 (13) | 0.0102 (13) |
C11 | 0.0353 (13) | 0.0424 (15) | 0.0273 (12) | 0.0026 (11) | 0.0109 (10) | 0.0014 (11) |
C12 | 0.0509 (16) | 0.060 (2) | 0.0321 (14) | 0.0063 (14) | 0.0184 (12) | 0.0022 (13) |
C13 | 0.0574 (18) | 0.067 (2) | 0.0340 (14) | 0.0060 (16) | 0.0144 (14) | −0.0165 (15) |
C14 | 0.0586 (18) | 0.0465 (17) | 0.0452 (16) | −0.0046 (14) | 0.0116 (14) | −0.0187 (14) |
C15 | 0.0552 (17) | 0.0373 (15) | 0.0382 (14) | −0.0068 (13) | 0.0162 (13) | −0.0059 (12) |
C16 | 0.0326 (12) | 0.0361 (14) | 0.0240 (11) | 0.0000 (10) | 0.0056 (10) | −0.0041 (10) |
C17 | 0.0521 (17) | 0.0452 (17) | 0.0592 (19) | −0.0135 (14) | 0.0119 (15) | −0.0148 (15) |
Cu2 | 0.03982 (16) | 0.02575 (15) | 0.02774 (14) | −0.00171 (13) | 0.01360 (12) | 0.00176 (12) |
Eu1 | 0.03128 (7) | 0.02506 (7) | 0.02520 (6) | −0.00126 (5) | 0.01204 (5) | 0.00007 (5) |
N1 | 0.0573 (14) | 0.0278 (11) | 0.0368 (12) | −0.0056 (11) | 0.0164 (11) | 0.0005 (10) |
N2 | 0.0560 (14) | 0.0316 (12) | 0.0436 (13) | 0.0033 (11) | 0.0272 (11) | 0.0079 (10) |
N3 | 0.0397 (12) | 0.0537 (15) | 0.0298 (11) | 0.0027 (11) | 0.0117 (10) | 0.0038 (11) |
N4 | 0.0332 (11) | 0.0355 (12) | 0.0457 (13) | −0.0022 (9) | 0.0106 (10) | 0.0097 (10) |
N5 | 0.0463 (13) | 0.0380 (13) | 0.0491 (14) | 0.0035 (11) | 0.0173 (11) | −0.0083 (11) |
O1 | 0.0397 (9) | 0.0275 (9) | 0.0291 (8) | 0.0044 (7) | 0.0157 (7) | 0.0013 (7) |
O2 | 0.0518 (11) | 0.0280 (9) | 0.0265 (8) | −0.0031 (8) | 0.0162 (8) | −0.0011 (7) |
O3 | 0.0473 (11) | 0.0414 (11) | 0.0589 (12) | −0.0149 (9) | 0.0310 (10) | −0.0169 (10) |
O4 | 0.0463 (11) | 0.0488 (12) | 0.0336 (9) | 0.0112 (9) | 0.0082 (8) | −0.0057 (9) |
O5 | 0.0611 (14) | 0.101 (2) | 0.0282 (10) | 0.0171 (13) | 0.0023 (10) | −0.0018 (12) |
O6 | 0.0515 (12) | 0.0453 (12) | 0.0432 (11) | 0.0133 (10) | 0.0081 (9) | −0.0024 (10) |
O7 | 0.0412 (10) | 0.0502 (12) | 0.0345 (10) | −0.0073 (9) | 0.0115 (8) | 0.0065 (9) |
O8 | 0.0444 (12) | 0.0700 (16) | 0.0719 (15) | −0.0220 (11) | 0.0114 (11) | 0.0244 (13) |
O9 | 0.0476 (11) | 0.0671 (15) | 0.0355 (10) | −0.0177 (10) | 0.0075 (9) | 0.0069 (10) |
O10 | 0.0553 (12) | 0.0333 (10) | 0.0674 (14) | −0.0063 (9) | 0.0328 (11) | −0.0066 (10) |
O11 | 0.0754 (16) | 0.0431 (13) | 0.113 (2) | 0.0172 (12) | 0.0450 (16) | −0.0089 (14) |
O12 | 0.0458 (10) | 0.0358 (10) | 0.0498 (11) | −0.0023 (9) | 0.0244 (9) | −0.0041 (9) |
C8' | 0.043 (10) | 0.040 (7) | 0.059 (9) | −0.004 (7) | 0.026 (8) | 0.009 (6) |
C9' | 0.068 (12) | 0.034 (6) | 0.068 (13) | −0.001 (7) | 0.030 (11) | 0.010 (7) |
C1—O1 | 1.343 (3) | C15—C16 | 1.387 (4) |
C1—C2 | 1.396 (4) | C15—H14 | 0.9300 |
C1—C6 | 1.408 (4) | C16—O2 | 1.349 (3) |
C2—C3 | 1.373 (4) | C17—O3 | 1.448 (3) |
C2—H1 | 0.9300 | C17—H15 | 0.9600 |
C3—C4 | 1.379 (5) | C17—H16 | 0.9600 |
C3—H2 | 0.9300 | C17—H17 | 0.9600 |
C4—C5 | 1.364 (5) | Cu2—N2 | 1.918 (2) |
C4—H3 | 0.9300 | Cu2—N1 | 1.925 (2) |
C5—C6 | 1.409 (4) | Cu2—O2 | 1.9301 (18) |
C5—H4 | 0.9300 | Cu2—O1 | 1.9382 (17) |
C6—C7 | 1.447 (4) | Cu2—O8 | 2.557 (19) |
C7—N1 | 1.270 (4) | Eu1—O2 | 2.3589 (18) |
C7—H5 | 0.9300 | Eu1—O1 | 2.3662 (17) |
C8—C9 | 1.488 (8) | Eu1—O3 | 2.4474 (19) |
C8—N1 | 1.505 (7) | Eu1—O4 | 2.455 (2) |
C8—H6 | 0.9700 | Eu1—O7 | 2.4643 (19) |
C8—H7 | 0.9700 | Eu1—O6 | 2.476 (2) |
C9—N2 | 1.450 (5) | Eu1—O10 | 2.486 (2) |
C9—H9 | 0.9700 | Eu1—O9 | 2.503 (2) |
C9—H8 | 0.9700 | Eu1—O12 | 2.5050 (19) |
C10—N2 | 1.275 (4) | N3—O5 | 1.213 (3) |
C10—C11 | 1.439 (4) | N3—O6 | 1.258 (3) |
C10—H10 | 0.9300 | N3—O4 | 1.278 (3) |
C11—C16 | 1.405 (4) | N4—O8 | 1.221 (3) |
C11—C12 | 1.412 (4) | N4—O9 | 1.253 (3) |
C12—C13 | 1.357 (5) | N4—O7 | 1.270 (3) |
C12—H11 | 0.9300 | N5—O11 | 1.206 (3) |
C13—C14 | 1.382 (5) | N5—O10 | 1.262 (3) |
C13—H12 | 0.9300 | N5—O12 | 1.280 (3) |
C14—C15 | 1.380 (4) | O3—H18 | 0.8500 |
C14—H13 | 0.9300 | C8'—C9' | 1.51 (3) |
O1—C1—C2 | 118.6 (2) | O2—Eu1—O4 | 139.18 (7) |
O1—C1—C6 | 123.4 (2) | O1—Eu1—O4 | 77.08 (6) |
C2—C1—C6 | 118.0 (2) | O3—Eu1—O4 | 75.39 (7) |
C3—C2—C1 | 121.4 (3) | O2—Eu1—O7 | 125.98 (6) |
C3—C2—H1 | 119.3 | O1—Eu1—O7 | 91.96 (7) |
C1—C2—H1 | 119.3 | O3—Eu1—O7 | 149.33 (7) |
C2—C3—C4 | 121.0 (3) | O4—Eu1—O7 | 74.26 (7) |
C2—C3—H2 | 119.5 | O2—Eu1—O6 | 151.09 (7) |
C4—C3—H2 | 119.5 | O1—Eu1—O6 | 128.50 (6) |
C5—C4—C3 | 118.7 (3) | O3—Eu1—O6 | 84.33 (8) |
C5—C4—H3 | 120.6 | O4—Eu1—O6 | 51.72 (7) |
C3—C4—H3 | 120.6 | O7—Eu1—O6 | 80.47 (7) |
C4—C5—C6 | 122.1 (3) | O2—Eu1—O10 | 100.83 (7) |
C4—C5—H4 | 119.0 | O1—Eu1—O10 | 155.46 (7) |
C6—C5—H4 | 119.0 | O3—Eu1—O10 | 123.09 (7) |
C1—C6—C5 | 118.8 (3) | O4—Eu1—O10 | 119.28 (7) |
C1—C6—C7 | 124.0 (2) | O7—Eu1—O10 | 76.76 (7) |
C5—C6—C7 | 117.2 (3) | O6—Eu1—O10 | 71.70 (7) |
N1—C7—C6 | 125.2 (2) | O2—Eu1—O9 | 76.36 (6) |
N1—C7—H5 | 117.4 | O1—Eu1—O9 | 83.86 (7) |
C6—C7—H5 | 117.4 | O3—Eu1—O9 | 151.18 (7) |
C9—C8—N1 | 108.0 (5) | O4—Eu1—O9 | 121.14 (7) |
C9—C8—H6 | 110.1 | O7—Eu1—O9 | 51.14 (6) |
N1—C8—H6 | 110.1 | O6—Eu1—O9 | 124.49 (7) |
C9—C8—H7 | 110.1 | O10—Eu1—O9 | 72.05 (7) |
N1—C8—H7 | 110.1 | O2—Eu1—O12 | 80.12 (7) |
H6—C8—H7 | 108.4 | O1—Eu1—O12 | 140.39 (6) |
N2—C9—C8 | 107.2 (5) | O3—Eu1—O12 | 73.07 (7) |
N2—C9—H9 | 110.3 | O4—Eu1—O12 | 118.43 (7) |
C8—C9—H9 | 110.3 | O7—Eu1—O12 | 126.55 (7) |
N2—C9—H8 | 110.3 | O6—Eu1—O12 | 73.59 (7) |
C8—C9—H8 | 110.3 | O10—Eu1—O12 | 51.07 (6) |
H9—C9—H8 | 108.5 | O9—Eu1—O12 | 111.60 (7) |
N2—C10—C11 | 125.3 (2) | C7—N1—C8 | 123.4 (3) |
N2—C10—H10 | 117.4 | C7—N1—Cu2 | 126.17 (19) |
C11—C10—H10 | 117.4 | C8—N1—Cu2 | 110.2 (3) |
C16—C11—C12 | 118.3 (3) | C10—N2—C9 | 120.2 (3) |
C16—C11—C10 | 124.3 (2) | C10—N2—Cu2 | 126.5 (2) |
C12—C11—C10 | 117.2 (2) | C9—N2—Cu2 | 112.9 (2) |
C13—C12—C11 | 122.4 (3) | O5—N3—O6 | 122.6 (2) |
C13—C12—H11 | 118.8 | O5—N3—O4 | 121.4 (2) |
C11—C12—H11 | 118.8 | O6—N3—O4 | 116.1 (2) |
C12—C13—C14 | 118.7 (3) | O8—N4—O9 | 122.7 (2) |
C12—C13—H12 | 120.7 | O8—N4—O7 | 120.9 (2) |
C14—C13—H12 | 120.7 | O9—N4—O7 | 116.4 (2) |
C15—C14—C13 | 120.7 (3) | O11—N5—O10 | 122.8 (3) |
C15—C14—H13 | 119.7 | O11—N5—O12 | 121.6 (3) |
C13—C14—H13 | 119.7 | O10—N5—O12 | 115.6 (2) |
C14—C15—C16 | 121.4 (3) | C1—O1—Cu2 | 124.30 (15) |
C14—C15—H14 | 119.3 | C1—O1—Eu1 | 136.48 (15) |
C16—C15—H14 | 119.3 | Cu2—O1—Eu1 | 97.16 (7) |
O2—C16—C15 | 118.7 (2) | C16—O2—Cu2 | 125.12 (16) |
O2—C16—C11 | 122.8 (2) | C16—O2—Eu1 | 132.82 (16) |
C15—C16—C11 | 118.5 (2) | Cu2—O2—Eu1 | 97.62 (7) |
N2—Cu2—N1 | 85.22 (10) | C17—O3—Eu1 | 129.40 (17) |
N2—Cu2—O2 | 94.04 (9) | C17—O3—H18 | 111.5 |
N1—Cu2—O2 | 172.68 (10) | Eu1—O3—H18 | 118.9 |
N2—Cu2—O1 | 172.90 (9) | N3—O4—Eu1 | 96.31 (15) |
N1—Cu2—O1 | 93.58 (8) | N3—O6—Eu1 | 95.84 (15) |
O2—Cu2—O1 | 86.27 (7) | N4—O7—Eu1 | 96.93 (14) |
O2—Eu1—O1 | 68.07 (6) | N4—O9—Eu1 | 95.52 (14) |
O2—Eu1—O3 | 76.59 (7) | N5—O10—Eu1 | 97.13 (15) |
O1—Eu1—O3 | 76.97 (7) | N5—O12—Eu1 | 95.71 (14) |
O1—C1—C2—C3 | 178.1 (3) | O10—Eu1—O2—C16 | −23.4 (2) |
C6—C1—C2—C3 | −0.9 (4) | O9—Eu1—O2—C16 | −91.8 (2) |
C1—C2—C3—C4 | −0.3 (5) | O12—Eu1—O2—C16 | 23.5 (2) |
C2—C3—C4—C5 | 1.1 (5) | O1—Eu1—O2—Cu2 | 23.20 (7) |
C3—C4—C5—C6 | −0.8 (5) | O3—Eu1—O2—Cu2 | −57.94 (8) |
O1—C1—C6—C5 | −177.8 (3) | O4—Eu1—O2—Cu2 | −10.21 (13) |
C2—C1—C6—C5 | 1.1 (4) | O7—Eu1—O2—Cu2 | 98.92 (9) |
O1—C1—C6—C7 | 0.6 (4) | O6—Eu1—O2—Cu2 | −108.02 (13) |
C2—C1—C6—C7 | 179.5 (3) | O10—Eu1—O2—Cu2 | −179.67 (7) |
C4—C5—C6—C1 | −0.3 (5) | O9—Eu1—O2—Cu2 | 112.00 (9) |
C4—C5—C6—C7 | −178.8 (3) | O12—Eu1—O2—Cu2 | −132.73 (8) |
C1—C6—C7—N1 | 6.4 (5) | O2—Eu1—O3—C17 | 125.7 (2) |
C5—C6—C7—N1 | −175.1 (3) | O1—Eu1—O3—C17 | 55.5 (2) |
N1—C8—C9—N2 | −43.7 (12) | O4—Eu1—O3—C17 | −24.3 (2) |
N2—C10—C11—C16 | −3.7 (5) | O7—Eu1—O3—C17 | −15.8 (3) |
N2—C10—C11—C12 | 171.0 (3) | O6—Eu1—O3—C17 | −76.2 (2) |
C16—C11—C12—C13 | 2.2 (4) | O10—Eu1—O3—C17 | −140.0 (2) |
C10—C11—C12—C13 | −172.8 (3) | O9—Eu1—O3—C17 | 105.1 (3) |
C11—C12—C13—C14 | 0.7 (5) | O12—Eu1—O3—C17 | −150.8 (3) |
C12—C13—C14—C15 | −2.3 (5) | O5—N3—O4—Eu1 | 177.3 (2) |
C13—C14—C15—C16 | 1.0 (5) | O6—N3—O4—Eu1 | −2.7 (2) |
C14—C15—C16—O2 | −178.3 (3) | O2—Eu1—O4—N3 | −140.82 (15) |
C14—C15—C16—C11 | 1.9 (4) | O1—Eu1—O4—N3 | −172.43 (16) |
C12—C11—C16—O2 | 176.8 (2) | O3—Eu1—O4—N3 | −92.76 (16) |
C10—C11—C16—O2 | −8.7 (4) | O7—Eu1—O4—N3 | 91.77 (16) |
C12—C11—C16—C15 | −3.4 (4) | O6—Eu1—O4—N3 | 1.58 (14) |
C10—C11—C16—C15 | 171.2 (3) | O10—Eu1—O4—N3 | 27.29 (18) |
C6—C7—N1—C8 | −170.4 (5) | O9—Eu1—O4—N3 | 113.04 (16) |
C6—C7—N1—Cu2 | 3.7 (5) | O12—Eu1—O4—N3 | −31.66 (17) |
C9—C8—N1—C7 | −151.1 (7) | O5—N3—O6—Eu1 | −177.3 (2) |
C9—C8—N1—Cu2 | 34.0 (10) | O4—N3—O6—Eu1 | 2.7 (2) |
N2—Cu2—N1—C7 | 173.2 (3) | O2—Eu1—O6—N3 | 122.81 (17) |
O1—Cu2—N1—C7 | −13.8 (3) | O1—Eu1—O6—N3 | 5.87 (19) |
N2—Cu2—N1—C8 | −12.0 (4) | O3—Eu1—O6—N3 | 74.25 (16) |
O1—Cu2—N1—C8 | 161.0 (4) | O4—Eu1—O6—N3 | −1.60 (14) |
C11—C10—N2—C9 | −166.5 (5) | O7—Eu1—O6—N3 | −79.02 (16) |
C11—C10—N2—Cu2 | 5.7 (5) | O10—Eu1—O6—N3 | −158.11 (17) |
C8—C9—N2—C10 | −151.6 (7) | O9—Eu1—O6—N3 | −106.50 (16) |
C8—C9—N2—Cu2 | 35.1 (10) | O12—Eu1—O6—N3 | 148.23 (17) |
N1—Cu2—N2—C10 | 174.0 (3) | O8—N4—O7—Eu1 | 178.6 (2) |
O2—Cu2—N2—C10 | 1.3 (3) | O9—N4—O7—Eu1 | −1.6 (2) |
N1—Cu2—N2—C9 | −13.2 (5) | O2—Eu1—O7—N4 | 17.35 (18) |
O2—Cu2—N2—C9 | 174.1 (5) | O1—Eu1—O7—N4 | 81.45 (15) |
C2—C1—O1—Cu2 | 164.73 (18) | O3—Eu1—O7—N4 | 148.83 (15) |
C6—C1—O1—Cu2 | −16.4 (3) | O4—Eu1—O7—N4 | 157.44 (16) |
C2—C1—O1—Eu1 | −35.6 (3) | O6—Eu1—O7—N4 | −149.81 (16) |
C6—C1—O1—Eu1 | 143.3 (2) | O10—Eu1—O7—N4 | −76.52 (16) |
N1—Cu2—O1—C1 | 19.80 (19) | O9—Eu1—O7—N4 | 0.94 (14) |
O2—Cu2—O1—C1 | −167.54 (19) | O12—Eu1—O7—N4 | −88.56 (16) |
N1—Cu2—O1—Eu1 | −146.22 (9) | O8—N4—O9—Eu1 | −178.7 (2) |
O2—Cu2—O1—Eu1 | 26.44 (7) | O7—N4—O9—Eu1 | 1.6 (2) |
O2—Eu1—O1—C1 | 173.8 (2) | O2—Eu1—O9—N4 | −167.35 (17) |
O3—Eu1—O1—C1 | −105.6 (2) | O1—Eu1—O9—N4 | −98.47 (16) |
O4—Eu1—O1—C1 | −27.9 (2) | O3—Eu1—O9—N4 | −146.72 (15) |
O7—Eu1—O1—C1 | 45.5 (2) | O4—Eu1—O9—N4 | −27.60 (19) |
O6—Eu1—O1—C1 | −33.9 (2) | O7—Eu1—O9—N4 | −0.95 (15) |
O10—Eu1—O1—C1 | 107.0 (2) | O6—Eu1—O9—N4 | 34.82 (19) |
O9—Eu1—O1—C1 | 96.0 (2) | O10—Eu1—O9—N4 | 86.29 (17) |
O12—Eu1—O1—C1 | −147.2 (2) | O12—Eu1—O9—N4 | 119.27 (16) |
O2—Eu1—O1—Cu2 | −23.08 (6) | O11—N5—O10—Eu1 | 173.6 (3) |
O3—Eu1—O1—Cu2 | 57.52 (7) | O12—N5—O10—Eu1 | −6.8 (2) |
O4—Eu1—O1—Cu2 | 135.25 (8) | O2—Eu1—O10—N5 | 71.73 (17) |
O7—Eu1—O1—Cu2 | −151.39 (7) | O1—Eu1—O10—N5 | 131.96 (17) |
O6—Eu1—O1—Cu2 | 129.24 (8) | O3—Eu1—O10—N5 | −9.2 (2) |
O10—Eu1—O1—Cu2 | −89.87 (16) | O4—Eu1—O10—N5 | −100.39 (17) |
O9—Eu1—O1—Cu2 | −100.81 (8) | O7—Eu1—O10—N5 | −163.56 (18) |
O12—Eu1—O1—Cu2 | 15.99 (13) | O6—Eu1—O10—N5 | −79.37 (17) |
C15—C16—O2—Cu2 | −162.6 (2) | O9—Eu1—O10—N5 | 143.41 (18) |
C11—C16—O2—Cu2 | 17.2 (3) | O12—Eu1—O10—N5 | 4.01 (15) |
C15—C16—O2—Eu1 | 46.6 (3) | O11—N5—O12—Eu1 | −173.7 (3) |
C11—C16—O2—Eu1 | −133.5 (2) | O10—N5—O12—Eu1 | 6.7 (2) |
N2—Cu2—O2—C16 | −12.5 (2) | O2—Eu1—O12—N5 | −116.63 (16) |
O1—Cu2—O2—C16 | 174.6 (2) | O1—Eu1—O12—N5 | −153.03 (14) |
N2—Cu2—O2—Eu1 | 146.33 (9) | O3—Eu1—O12—N5 | 164.50 (17) |
O1—Cu2—O2—Eu1 | −26.56 (7) | O4—Eu1—O12—N5 | 102.18 (16) |
O1—Eu1—O2—C16 | 179.4 (2) | O7—Eu1—O12—N5 | 11.19 (18) |
O3—Eu1—O2—C16 | 98.3 (2) | O6—Eu1—O12—N5 | 75.53 (16) |
O4—Eu1—O2—C16 | 146.0 (2) | O10—Eu1—O12—N5 | −3.94 (15) |
O7—Eu1—O2—C16 | −104.8 (2) | O9—Eu1—O12—N5 | −45.68 (17) |
O6—Eu1—O2—C16 | 48.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H18···O12i | 0.85 | 2.04 | 2.886 (3) | 174 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [CuEu(C16H14N2O2)(NO3)3(CH4O)] |
Mr | 699.87 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 12.223 (4), 10.363 (3), 18.414 (5) |
β (°) | 102.451 (12) |
V (Å3) | 2277.6 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.74 |
Crystal size (mm) | 0.33 × 0.20 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.376, 0.543 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21558, 5201, 4693 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.021, 0.047, 1.06 |
No. of reflections | 5201 |
No. of parameters | 345 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.59 |
Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXL97.
Cu2—N2 | 1.918 (2) | Eu1—O3 | 2.4474 (19) |
Cu2—N1 | 1.925 (2) | Eu1—O4 | 2.455 (2) |
Cu2—O2 | 1.9301 (18) | Eu1—O7 | 2.4643 (19) |
Cu2—O1 | 1.9382 (17) | Eu1—O6 | 2.476 (2) |
Cu2—O8 | 2.557 (19) | Eu1—O10 | 2.486 (2) |
Eu1—O2 | 2.3589 (18) | Eu1—O9 | 2.503 (2) |
Eu1—O1 | 2.3662 (17) | Eu1—O12 | 2.5050 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H18···O12i | 0.85 | 2.04 | 2.886 (3) | 173.8 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
As shown in Fig. 1, the tetradentate Schiff base ligand links Cu and Eu atoms into a dinuclear complex through two phenolate O atoms. The EuIII centre in (I) is nine-coordinated by two O atoms from the ligand, six O atoms from three nitrate and one O atoms from the methanol, which is similar with the bonding reported for another copper-lanthanum complex of the same ligand (Kahn et al., 2000). The CuII center is five-coordinate by two N atoms, two O atoms from the ligand and one nitrato oxygen of neighboring dinuclear unit in a square-pyramidal geometry.