supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m2201-m2202    [ doi:10.1107/S1600536807034903 ]

[[mu]-N,N'-Bis(2-oxidobenzylidene)-1,2-ethanediamine](methanol)trinitratocopper(II)europium(III)

T. Gao, W.-B. Sun, P.-F. Yan, G.-M. Li and G.-F. Hou

Abstract top

The title complex (systematic name: {2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1[kappa]4O1,O1',O6,O6':2[kappa]4O1,N,N',O1'}(methanol-1[kappa]O)trinitrato-1[kappa]6O,O'-copper(II)europium(III)), [CuEu(C16H14N2O2)(NO3)3(CH3OH)], is a heterodinuclear 3d-4f metal Schiff base dimer. The CuII ion is five-coordinated by two O atoms, two N atoms of the deprotonated Schiff base and one nitrate O atom from a neighboring dinuclear unit, giving rise to a square-pyramidal geometry, whereas the EuIII ion is nine-coordinated by six O atoms from nitrate groups, two O atoms from the deprotonated Schiff base and one O atom from methanol. The ethylene link is disordered over two positions with a site occupancy ratio of ca 3:1. The crystal structure involves O-H...O hydrogen bonds.

Comment top

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.

Related literature top

See Kahn et al. (2000) for a similar copper–lanthanum complex of the same Schiff base.

Experimental top

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%.

Refinement top

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'.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. Disordered atoms (C8', C9') have been omitted for clarity.
{2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ4O1,O1',O6,O6': 2κ4O1,N,N',O1'}(methanol- 1κO)trinitrato-1κ6O,O'-copper(II)europium(III) top
Crystal data top
[CuEu(C16H14N2O2)(NO3)3(CH4O)]F(000) = 1372
Mr = 699.87Dx = 2.041 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 18713 reflections
a = 12.223 (4) Åθ = 6.0–54.9°
b = 10.363 (3) ŵ = 3.74 mm−1
c = 18.414 (5) ÅT = 296 K
β = 102.451 (12)°Block, black
V = 2277.6 (12) Å30.33 × 0.20 × 0.19 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5201 independent reflections
Radiation source: fine-focus sealed tube4693 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −15→15
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −13→13
Tmin = 0.376, Tmax = 0.543l = −23→22
21558 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H-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 parametersΔρmax = 0.31 e Å−3
2 restraintsΔρmin = −0.59 e Å−3
Crystal data top
[CuEu(C16H14N2O2)(NO3)3(CH4O)]V = 2277.6 (12) Å3
Mr = 699.87Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.223 (4) ŵ = 3.74 mm−1
b = 10.363 (3) ÅT = 296 K
c = 18.414 (5) Å0.33 × 0.20 × 0.19 mm
β = 102.451 (12)°
Data collection top
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 = 0.543Rint = 0.030
21558 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.047Δρmax = 0.31 e Å−3
S = 1.06Δρmin = −0.59 e Å−3
5201 reflectionsAbsolute structure: ?
345 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1201 (2)0.7351 (3)0.60899 (13)0.0310 (5)
C20.0762 (2)0.6757 (3)0.66454 (15)0.0413 (6)
H10.07940.58630.66900.050*
C30.0284 (2)0.7464 (3)0.71266 (16)0.0464 (7)
H2−0.00040.70410.74900.056*
C40.0225 (3)0.8791 (3)0.70797 (17)0.0535 (8)
H3−0.00880.92660.74120.064*
C50.0635 (3)0.9394 (3)0.65357 (18)0.0510 (8)
H40.05891.02880.64980.061*
C60.1127 (2)0.8705 (3)0.60289 (15)0.0377 (6)
C70.1553 (3)0.9448 (3)0.54848 (17)0.0450 (7)
H50.15321.03430.55220.054*
C80.2543 (9)0.9774 (6)0.4478 (4)0.0442 (17)0.72 (2)
H60.22411.06430.44280.053*
H70.33370.98240.47010.053*
C90.2369 (9)0.9143 (5)0.3736 (4)0.0434 (19)0.72 (2)
H90.16170.93110.34520.052*
H80.29010.94730.34600.052*
C100.2881 (2)0.7069 (3)0.33908 (15)0.0438 (7)
H100.31710.74890.30280.053*
C110.2860 (2)0.5681 (3)0.33729 (14)0.0344 (5)
C120.3126 (3)0.5076 (3)0.27460 (16)0.0462 (7)
H110.33850.55800.24010.055*
C130.3018 (3)0.3784 (3)0.26293 (16)0.0521 (8)
H120.32070.34080.22140.063*
C140.2622 (3)0.3039 (3)0.31397 (17)0.0500 (7)
H130.25180.21580.30580.060*
C150.2379 (2)0.3589 (3)0.37687 (16)0.0426 (6)
H140.21250.30680.41090.051*
C160.2507 (2)0.4903 (2)0.39041 (13)0.0310 (5)
C170.4417 (3)0.7572 (3)0.61542 (19)0.0522 (8)
H150.38020.77870.63800.078*
H160.45510.82720.58430.078*
H170.50770.74240.65350.078*
Cu20.20183 (3)0.71765 (3)0.471852 (16)0.03015 (7)
Eu10.279281 (10)0.471486 (11)0.579103 (6)0.02628 (4)
N10.1952 (2)0.8978 (2)0.49601 (13)0.0397 (5)
N20.2534 (2)0.7769 (2)0.38641 (13)0.0413 (5)
N30.40354 (19)0.4886 (2)0.73120 (12)0.0404 (5)
N40.08119 (18)0.3280 (2)0.59421 (13)0.0378 (5)
N50.4077 (2)0.2526 (2)0.54166 (14)0.0434 (6)
O10.16860 (14)0.66089 (16)0.56505 (9)0.0309 (4)
O20.22848 (16)0.53808 (16)0.45385 (10)0.0343 (4)
O30.41493 (16)0.64166 (19)0.57093 (12)0.0463 (5)
H180.45800.63260.54070.056*
O40.32467 (16)0.5670 (2)0.70399 (10)0.0430 (5)
O50.4574 (2)0.5002 (3)0.79437 (11)0.0645 (7)
O60.42138 (17)0.3997 (2)0.68870 (11)0.0470 (5)
O70.15586 (16)0.3634 (2)0.64981 (10)0.0414 (4)
O80.00002 (18)0.2658 (2)0.60258 (14)0.0623 (7)
O90.09572 (17)0.3610 (2)0.53148 (11)0.0503 (5)
O100.31744 (18)0.23862 (19)0.56357 (13)0.0491 (5)
O110.4658 (2)0.1628 (2)0.53211 (17)0.0735 (8)
O120.43392 (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)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0286 (11)0.0361 (14)0.0289 (12)0.0057 (10)0.0078 (10)−0.0022 (10)
C20.0475 (15)0.0414 (15)0.0398 (14)0.0083 (13)0.0203 (12)0.0055 (12)
C30.0469 (16)0.059 (2)0.0399 (15)0.0091 (14)0.0239 (13)0.0027 (14)
C40.0624 (19)0.059 (2)0.0455 (16)0.0185 (16)0.0265 (15)−0.0091 (15)
C50.067 (2)0.0382 (16)0.0532 (18)0.0131 (15)0.0241 (16)−0.0060 (14)
C60.0430 (14)0.0349 (14)0.0372 (14)0.0042 (12)0.0130 (12)−0.0036 (11)
C70.0645 (19)0.0242 (13)0.0484 (16)−0.0005 (12)0.0167 (15)−0.0026 (12)
C80.050 (4)0.029 (2)0.060 (3)−0.008 (3)0.028 (3)0.002 (2)
C90.066 (5)0.031 (2)0.041 (3)0.002 (3)0.026 (3)0.008 (2)
C100.0550 (17)0.0459 (16)0.0376 (14)0.0043 (14)0.0254 (13)0.0102 (13)
C110.0353 (13)0.0424 (15)0.0273 (12)0.0026 (11)0.0109 (10)0.0014 (11)
C120.0509 (16)0.060 (2)0.0321 (14)0.0063 (14)0.0184 (12)0.0022 (13)
C130.0574 (18)0.067 (2)0.0340 (14)0.0060 (16)0.0144 (14)−0.0165 (15)
C140.0586 (18)0.0465 (17)0.0452 (16)−0.0046 (14)0.0116 (14)−0.0187 (14)
C150.0552 (17)0.0373 (15)0.0382 (14)−0.0068 (13)0.0162 (13)−0.0059 (12)
C160.0326 (12)0.0361 (14)0.0240 (11)0.0000 (10)0.0056 (10)−0.0041 (10)
C170.0521 (17)0.0452 (17)0.0592 (19)−0.0135 (14)0.0119 (15)−0.0148 (15)
Cu20.03982 (16)0.02575 (15)0.02774 (14)−0.00171 (13)0.01360 (12)0.00176 (12)
Eu10.03128 (7)0.02506 (7)0.02520 (6)−0.00126 (5)0.01204 (5)0.00007 (5)
N10.0573 (14)0.0278 (11)0.0368 (12)−0.0056 (11)0.0164 (11)0.0005 (10)
N20.0560 (14)0.0316 (12)0.0436 (13)0.0033 (11)0.0272 (11)0.0079 (10)
N30.0397 (12)0.0537 (15)0.0298 (11)0.0027 (11)0.0117 (10)0.0038 (11)
N40.0332 (11)0.0355 (12)0.0457 (13)−0.0022 (9)0.0106 (10)0.0097 (10)
N50.0463 (13)0.0380 (13)0.0491 (14)0.0035 (11)0.0173 (11)−0.0083 (11)
O10.0397 (9)0.0275 (9)0.0291 (8)0.0044 (7)0.0157 (7)0.0013 (7)
O20.0518 (11)0.0280 (9)0.0265 (8)−0.0031 (8)0.0162 (8)−0.0011 (7)
O30.0473 (11)0.0414 (11)0.0589 (12)−0.0149 (9)0.0310 (10)−0.0169 (10)
O40.0463 (11)0.0488 (12)0.0336 (9)0.0112 (9)0.0082 (8)−0.0057 (9)
O50.0611 (14)0.101 (2)0.0282 (10)0.0171 (13)0.0023 (10)−0.0018 (12)
O60.0515 (12)0.0453 (12)0.0432 (11)0.0133 (10)0.0081 (9)−0.0024 (10)
O70.0412 (10)0.0502 (12)0.0345 (10)−0.0073 (9)0.0115 (8)0.0065 (9)
O80.0444 (12)0.0700 (16)0.0719 (15)−0.0220 (11)0.0114 (11)0.0244 (13)
O90.0476 (11)0.0671 (15)0.0355 (10)−0.0177 (10)0.0075 (9)0.0069 (10)
O100.0553 (12)0.0333 (10)0.0674 (14)−0.0063 (9)0.0328 (11)−0.0066 (10)
O110.0754 (16)0.0431 (13)0.113 (2)0.0172 (12)0.0450 (16)−0.0089 (14)
O120.0458 (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)
Geometric parameters (Å, °) top
C1—O11.343 (3)C15—C161.387 (4)
C1—C21.396 (4)C15—H140.9300
C1—C61.408 (4)C16—O21.349 (3)
C2—C31.373 (4)C17—O31.448 (3)
C2—H10.9300C17—H150.9600
C3—C41.379 (5)C17—H160.9600
C3—H20.9300C17—H170.9600
C4—C51.364 (5)Cu2—N21.918 (2)
C4—H30.9300Cu2—N11.925 (2)
C5—C61.409 (4)Cu2—O21.9301 (18)
C5—H40.9300Cu2—O11.9382 (17)
C6—C71.447 (4)Cu2—O82.557 (19)
C7—N11.270 (4)Eu1—O22.3589 (18)
C7—H50.9300Eu1—O12.3662 (17)
C8—C91.488 (8)Eu1—O32.4474 (19)
C8—N11.505 (7)Eu1—O42.455 (2)
C8—H60.9700Eu1—O72.4643 (19)
C8—H70.9700Eu1—O62.476 (2)
C9—N21.450 (5)Eu1—O102.486 (2)
C9—H90.9700Eu1—O92.503 (2)
C9—H80.9700Eu1—O122.5050 (19)
C10—N21.275 (4)N3—O51.213 (3)
C10—C111.439 (4)N3—O61.258 (3)
C10—H100.9300N3—O41.278 (3)
C11—C161.405 (4)N4—O81.221 (3)
C11—C121.412 (4)N4—O91.253 (3)
C12—C131.357 (5)N4—O71.270 (3)
C12—H110.9300N5—O111.206 (3)
C13—C141.382 (5)N5—O101.262 (3)
C13—H120.9300N5—O121.280 (3)
C14—C151.380 (4)O3—H180.8500
C14—H130.9300C8'—C9'1.51 (3)
O1—C1—C2118.6 (2)O2—Eu1—O4139.18 (7)
O1—C1—C6123.4 (2)O1—Eu1—O477.08 (6)
C2—C1—C6118.0 (2)O3—Eu1—O475.39 (7)
C3—C2—C1121.4 (3)O2—Eu1—O7125.98 (6)
C3—C2—H1119.3O1—Eu1—O791.96 (7)
C1—C2—H1119.3O3—Eu1—O7149.33 (7)
C2—C3—C4121.0 (3)O4—Eu1—O774.26 (7)
C2—C3—H2119.5O2—Eu1—O6151.09 (7)
C4—C3—H2119.5O1—Eu1—O6128.50 (6)
C5—C4—C3118.7 (3)O3—Eu1—O684.33 (8)
C5—C4—H3120.6O4—Eu1—O651.72 (7)
C3—C4—H3120.6O7—Eu1—O680.47 (7)
C4—C5—C6122.1 (3)O2—Eu1—O10100.83 (7)
C4—C5—H4119.0O1—Eu1—O10155.46 (7)
C6—C5—H4119.0O3—Eu1—O10123.09 (7)
C1—C6—C5118.8 (3)O4—Eu1—O10119.28 (7)
C1—C6—C7124.0 (2)O7—Eu1—O1076.76 (7)
C5—C6—C7117.2 (3)O6—Eu1—O1071.70 (7)
N1—C7—C6125.2 (2)O2—Eu1—O976.36 (6)
N1—C7—H5117.4O1—Eu1—O983.86 (7)
C6—C7—H5117.4O3—Eu1—O9151.18 (7)
C9—C8—N1108.0 (5)O4—Eu1—O9121.14 (7)
C9—C8—H6110.1O7—Eu1—O951.14 (6)
N1—C8—H6110.1O6—Eu1—O9124.49 (7)
C9—C8—H7110.1O10—Eu1—O972.05 (7)
N1—C8—H7110.1O2—Eu1—O1280.12 (7)
H6—C8—H7108.4O1—Eu1—O12140.39 (6)
N2—C9—C8107.2 (5)O3—Eu1—O1273.07 (7)
N2—C9—H9110.3O4—Eu1—O12118.43 (7)
C8—C9—H9110.3O7—Eu1—O12126.55 (7)
N2—C9—H8110.3O6—Eu1—O1273.59 (7)
C8—C9—H8110.3O10—Eu1—O1251.07 (6)
H9—C9—H8108.5O9—Eu1—O12111.60 (7)
N2—C10—C11125.3 (2)C7—N1—C8123.4 (3)
N2—C10—H10117.4C7—N1—Cu2126.17 (19)
C11—C10—H10117.4C8—N1—Cu2110.2 (3)
C16—C11—C12118.3 (3)C10—N2—C9120.2 (3)
C16—C11—C10124.3 (2)C10—N2—Cu2126.5 (2)
C12—C11—C10117.2 (2)C9—N2—Cu2112.9 (2)
C13—C12—C11122.4 (3)O5—N3—O6122.6 (2)
C13—C12—H11118.8O5—N3—O4121.4 (2)
C11—C12—H11118.8O6—N3—O4116.1 (2)
C12—C13—C14118.7 (3)O8—N4—O9122.7 (2)
C12—C13—H12120.7O8—N4—O7120.9 (2)
C14—C13—H12120.7O9—N4—O7116.4 (2)
C15—C14—C13120.7 (3)O11—N5—O10122.8 (3)
C15—C14—H13119.7O11—N5—O12121.6 (3)
C13—C14—H13119.7O10—N5—O12115.6 (2)
C14—C15—C16121.4 (3)C1—O1—Cu2124.30 (15)
C14—C15—H14119.3C1—O1—Eu1136.48 (15)
C16—C15—H14119.3Cu2—O1—Eu197.16 (7)
O2—C16—C15118.7 (2)C16—O2—Cu2125.12 (16)
O2—C16—C11122.8 (2)C16—O2—Eu1132.82 (16)
C15—C16—C11118.5 (2)Cu2—O2—Eu197.62 (7)
N2—Cu2—N185.22 (10)C17—O3—Eu1129.40 (17)
N2—Cu2—O294.04 (9)C17—O3—H18111.5
N1—Cu2—O2172.68 (10)Eu1—O3—H18118.9
N2—Cu2—O1172.90 (9)N3—O4—Eu196.31 (15)
N1—Cu2—O193.58 (8)N3—O6—Eu195.84 (15)
O2—Cu2—O186.27 (7)N4—O7—Eu196.93 (14)
O2—Eu1—O168.07 (6)N4—O9—Eu195.52 (14)
O2—Eu1—O376.59 (7)N5—O10—Eu197.13 (15)
O1—Eu1—O376.97 (7)N5—O12—Eu195.71 (14)
O1—C1—C2—C3178.1 (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—C1623.5 (2)
C2—C3—C4—C51.1 (5)O1—Eu1—O2—Cu223.20 (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—C51.1 (4)O7—Eu1—O2—Cu298.92 (9)
O1—C1—C6—C70.6 (4)O6—Eu1—O2—Cu2−108.02 (13)
C2—C1—C6—C7179.5 (3)O10—Eu1—O2—Cu2−179.67 (7)
C4—C5—C6—C1−0.3 (5)O9—Eu1—O2—Cu2112.00 (9)
C4—C5—C6—C7−178.8 (3)O12—Eu1—O2—Cu2−132.73 (8)
C1—C6—C7—N16.4 (5)O2—Eu1—O3—C17125.7 (2)
C5—C6—C7—N1−175.1 (3)O1—Eu1—O3—C1755.5 (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—C12171.0 (3)O6—Eu1—O3—C17−76.2 (2)
C16—C11—C12—C132.2 (4)O10—Eu1—O3—C17−140.0 (2)
C10—C11—C12—C13−172.8 (3)O9—Eu1—O3—C17105.1 (3)
C11—C12—C13—C140.7 (5)O12—Eu1—O3—C17−150.8 (3)
C12—C13—C14—C15−2.3 (5)O5—N3—O4—Eu1177.3 (2)
C13—C14—C15—C161.0 (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—C111.9 (4)O1—Eu1—O4—N3−172.43 (16)
C12—C11—C16—O2176.8 (2)O3—Eu1—O4—N3−92.76 (16)
C10—C11—C16—O2−8.7 (4)O7—Eu1—O4—N391.77 (16)
C12—C11—C16—C15−3.4 (4)O6—Eu1—O4—N31.58 (14)
C10—C11—C16—C15171.2 (3)O10—Eu1—O4—N327.29 (18)
C6—C7—N1—C8−170.4 (5)O9—Eu1—O4—N3113.04 (16)
C6—C7—N1—Cu23.7 (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—Cu234.0 (10)O4—N3—O6—Eu12.7 (2)
N2—Cu2—N1—C7173.2 (3)O2—Eu1—O6—N3122.81 (17)
O1—Cu2—N1—C7−13.8 (3)O1—Eu1—O6—N35.87 (19)
N2—Cu2—N1—C8−12.0 (4)O3—Eu1—O6—N374.25 (16)
O1—Cu2—N1—C8161.0 (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—Cu25.7 (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—Cu235.1 (10)O12—Eu1—O6—N3148.23 (17)
N1—Cu2—N2—C10174.0 (3)O8—N4—O7—Eu1178.6 (2)
O2—Cu2—N2—C101.3 (3)O9—N4—O7—Eu1−1.6 (2)
N1—Cu2—N2—C9−13.2 (5)O2—Eu1—O7—N417.35 (18)
O2—Cu2—N2—C9174.1 (5)O1—Eu1—O7—N481.45 (15)
C2—C1—O1—Cu2164.73 (18)O3—Eu1—O7—N4148.83 (15)
C6—C1—O1—Cu2−16.4 (3)O4—Eu1—O7—N4157.44 (16)
C2—C1—O1—Eu1−35.6 (3)O6—Eu1—O7—N4−149.81 (16)
C6—C1—O1—Eu1143.3 (2)O10—Eu1—O7—N4−76.52 (16)
N1—Cu2—O1—C119.80 (19)O9—Eu1—O7—N40.94 (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—Eu126.44 (7)O7—N4—O9—Eu11.6 (2)
O2—Eu1—O1—C1173.8 (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—C145.5 (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—C1107.0 (2)O6—Eu1—O9—N434.82 (19)
O9—Eu1—O1—C196.0 (2)O10—Eu1—O9—N486.29 (17)
O12—Eu1—O1—C1−147.2 (2)O12—Eu1—O9—N4119.27 (16)
O2—Eu1—O1—Cu2−23.08 (6)O11—N5—O10—Eu1173.6 (3)
O3—Eu1—O1—Cu257.52 (7)O12—N5—O10—Eu1−6.8 (2)
O4—Eu1—O1—Cu2135.25 (8)O2—Eu1—O10—N571.73 (17)
O7—Eu1—O1—Cu2−151.39 (7)O1—Eu1—O10—N5131.96 (17)
O6—Eu1—O1—Cu2129.24 (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—Cu215.99 (13)O6—Eu1—O10—N5−79.37 (17)
C15—C16—O2—Cu2−162.6 (2)O9—Eu1—O10—N5143.41 (18)
C11—C16—O2—Cu217.2 (3)O12—Eu1—O10—N54.01 (15)
C15—C16—O2—Eu146.6 (3)O11—N5—O12—Eu1−173.7 (3)
C11—C16—O2—Eu1−133.5 (2)O10—N5—O12—Eu16.7 (2)
N2—Cu2—O2—C16−12.5 (2)O2—Eu1—O12—N5−116.63 (16)
O1—Cu2—O2—C16174.6 (2)O1—Eu1—O12—N5−153.03 (14)
N2—Cu2—O2—Eu1146.33 (9)O3—Eu1—O12—N5164.50 (17)
O1—Cu2—O2—Eu1−26.56 (7)O4—Eu1—O12—N5102.18 (16)
O1—Eu1—O2—C16179.4 (2)O7—Eu1—O12—N511.19 (18)
O3—Eu1—O2—C1698.3 (2)O6—Eu1—O12—N575.53 (16)
O4—Eu1—O2—C16146.0 (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—C1648.2 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H18···O12i0.852.042.886 (3)174
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Cu2—N21.918 (2)Eu1—O32.4474 (19)
Cu2—N11.925 (2)Eu1—O42.455 (2)
Cu2—O21.9301 (18)Eu1—O72.4643 (19)
Cu2—O11.9382 (17)Eu1—O62.476 (2)
Cu2—O82.557 (19)Eu1—O102.486 (2)
Eu1—O22.3589 (18)Eu1—O92.503 (2)
Eu1—O12.3662 (17)Eu1—O122.5050 (19)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H18···O12i0.852.042.886 (3)174
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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.

references
References top

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Kahn, M. L., Rajendiran, T. M., Jeannin, Y., Mathoniére, C. & Kahn, O. (2000). Chim. Chem. 3, 131–137.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.