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Acta Cryst. (2007). E63, m2039-m2040    [ doi:10.1107/S1600536807031121 ]

{6,6'-Diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}trinitratoeuropium(III)zinc(II)

R.-H. Hu, Y. Sui, X.-N. Fang and H.-M. Chen

Abstract top

A heteronuclear ZnII-EuIII complex (systematic name: {6,6'-diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1[kappa]4O1,O1',O6,O6':2[kappa]4O1,N,N',O1'}trinitrato-1[kappa]6O,O'-europium(III)zinc(II)), [EuZn(C20H22N2O4)(NO3)3], with the hexadentate Schiff base compartmental ligand N,N'-bis(3-ethoxysalicylidene)ethylenediamine, has been synthesized and structurally characterized. The Zn and Eu atoms are doubly bridged by two phenolate O atoms provided by the Schiff base ligand. The coordination of Zn is square planar with the donor centers of two imine N atoms and two phenolate O atoms. The Eu center has a decacoordination environment formed by the phenolate O atoms, two ethoxy O atoms and two O atoms from each of the three nitrates. No classical intermolecular hydrogen bonds are found. Some weak C-H...O and O...Zn interactions [O...Zn = 3.193 (4) Å] generate a two-dimensional zigzag sheet.

Comment top

The potential applications of trivalent lanthanide complexes as contrast agent for magnetic resonance imaging and stains for fluorescence imaging have prompted considerable interest in the preparation, magnetic and optical properties of 3 d-4f hetorometallic dinuclear complexes (Baggio et al., 2000; Caravan et al., 1999; Edder et al., 2000; Knoer et al., 2005). As part of our investigations into the structure and applications of 3 d-4f hetorometallic Schiff base complexes(Sui et al., 2006), we report here the synthesis and X-ray crystal structure analysis of the title complex, (I), a new ZnII—EuIII complex with salen-type Schiff base N,N'-bis(3-ethoxysalicylidene) ethylenediamine(H2L).

Complex (I) crystallizes in the space group P212121, with zinc and europium doubly bridged by two phenolate O atoms provided by a salen-type Schiff base ligand. The inner salen-type cavity is occupied by zinc(II), while europium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand. The dihedral angles between the mean planes of Zn1/O1/O2 and Eu1/O1/O2 is 3.59 (15)° suggesting that the bridging moiety is almost planar; the deviation of atoms from the least squares Zn1/O1/O2/Eu1 plane being 0.0301 (3)Å for Zn, 0.0210 (2)Å for Eu, -0.0259 (3)Å for O1 and -0.0252 (3)Å for O2.

The europium(III) center in (I) has a decacoordination environment of O atoms. In addition to the phenolate ligands, two ethoxy O atoms coordinate to this metal center, two O atoms from each of the three nitrates chelate to europium to complete the decacoordination. The three kinds of Eu—O bond distances are significantly different, the shortest being the Eu—O(phenolate) and longest being the Eu—O(ethoxy) separations.

The coordination of zinc(II) is approximately square planar. The donor centers are alternatively above and below the mean N2O2 plane with an average deviation from the plane of 0.0873 (2) Å, while Zn1 is 0.0401 (3)Å below this square plane.

Adjacent molecules are held together by weak interactions (O7···Zn1=3.193 (4) Å, C8—H8A···O13i=3.297 (5) and C10—H10···O13ii=3.289 (5); symmetry codes:(i)-x + 1, y, z; (ii)1 - x, 1/2 + y, 1/2 - z). these link the molecules into a two-dimensional zigzag sheet(Fig 2).

Related literature top

For related literature, see: Baggio et al. (2000); Caravan et al. (1999); Edder et al. (2000); Knoer et al. (2005); Sui et al. (2006).

Experimental top

H2L was prepared by the 2:1 condensation of 3-ethoxysalicylaldehyde and ethylenediamine in methanol. Complex (I) was obtained by the treatment of zinc(II) acetate dihydrate (0.188 g, 1 mmol) with H2L(0.356 g, 1 mmol) in methanol solution (80 ml) under reflux for 3 h and then for another 3 h after the addition of europium(III) nitrate hexahydrate (0.447 g, 1 mmol). The reaction mixture was cooled and the resulting precipitate was filtered off, washed with diethyl ether and dried in vacuo. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation at room temperature of a methanol solution. Analysis calculated for C20H22EuN5O13Zn: C 31.70, H 2.93, Eu 20.05, N 9.24,Zn 8.63%; found: C 31.80, H 2.95, Eu 20.10, N 9.29, Zn 8.59%. IR(KBr, cm-1): 1642(C=N), 1386,1490(nitrate).

Refinement top

The H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distances of 0.97 (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. All the H atoms on carbon have been omitted for clarity.
[Figure 2] Fig. 2. The packing diagram of (I), viewed along the b axis; hydrogen bonds are shown as dashed lines..
{6,6'-diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-\ 1κ4O1,O1',O6,O6':2κ4O1,\ N,N',O1'}trinitrato-1κ6O,O'-\ europium(III)zinc(II)) top
Crystal data top
[EuZn(C20H22N2O4)(NO3)3]F(000) = 1496
Mr = 757.76Dx = 1.984 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 19197 reflections
a = 8.6599 (3) Åθ = 1.8–28.3°
b = 13.8416 (5) ŵ = 3.47 mm−1
c = 21.1681 (7) ÅT = 293 K
V = 2537.35 (15) Å3Block, yellow
Z = 40.25 × 0.23 × 0.21 mm
Data collection top
Bruker APEX II area-detector
diffractometer		6234 independent reflections
Radiation source: fine-focus sealed tube5081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 1.8°
φ and ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		k = −18→18
Tmin = 0.438, Tmax = 0.484l = −28→28
19197 measured reflections
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)] = 0.025H-atom parameters constrained
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.0245P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
6234 reflectionsΔρmax = 0.54 e Å−3
363 parametersΔρmin = −0.70 e Å−3
0 restraintsAbsolute structure: Flack (1983), 2674 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.016 (10)
Crystal data top
[EuZn(C20H22N2O4)(NO3)3]V = 2537.35 (15) Å3
Mr = 757.76Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6599 (3) ŵ = 3.47 mm−1
b = 13.8416 (5) ÅT = 293 K
c = 21.1681 (7) Å0.25 × 0.23 × 0.21 mm
Data collection top
Bruker APEX II area-detector
diffractometer		6234 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		5081 reflections with I > 2σ(I)
Tmin = 0.438, Tmax = 0.484Rint = 0.028
19197 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.058Δρmax = 0.54 e Å−3
S = 1.00Δρmin = −0.70 e Å−3
6234 reflectionsAbsolute structure: Flack (1983), 2674 Friedel pairs
363 parametersFlack parameter: 0.016 (10)
0 restraints
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*/Ueq
Eu10.242201 (18)0.499235 (12)0.097727 (7)0.03628 (5)
Zn10.56391 (5)0.55577 (3)0.18350 (2)0.04392 (11)
O20.4097 (3)0.62355 (15)0.13762 (11)0.0419 (6)
N40.3637 (4)0.5069 (3)−0.02934 (15)0.0566 (8)
C20.5193 (4)0.3547 (2)0.15599 (15)0.0359 (8)
N20.6759 (4)0.6680 (2)0.20904 (14)0.0414 (8)
O40.1869 (3)0.68330 (16)0.07006 (12)0.0432 (6)
C120.4098 (4)0.7190 (2)0.12700 (16)0.0359 (8)
C160.5074 (5)0.8813 (2)0.13284 (19)0.0513 (10)
H160.58210.92460.14680.062*
C100.6457 (4)0.7550 (3)0.19084 (18)0.0435 (9)
H100.71110.80370.20500.052*
C130.2871 (4)0.7543 (2)0.09017 (15)0.0371 (8)
C10.4575 (4)0.2880 (2)0.11395 (16)0.0368 (8)
C150.3925 (5)0.9137 (2)0.0968 (2)0.0566 (11)
H150.38820.97870.08600.068*
C110.5195 (4)0.7832 (2)0.15049 (17)0.0400 (8)
O30.3415 (3)0.32452 (16)0.07600 (12)0.0417 (6)
C140.2790 (5)0.8508 (2)0.07525 (17)0.0465 (9)
H140.19780.87400.05080.056*
O80.2234 (3)0.4914 (2)−0.01720 (12)0.0567 (7)
O10.4588 (3)0.44371 (16)0.15447 (10)0.0387 (5)
N10.6990 (3)0.4858 (2)0.23870 (13)0.0420 (7)
O110.1820 (4)0.5324 (2)0.21299 (13)0.0563 (8)
O120.1404 (3)0.38857 (18)0.18092 (14)0.0544 (7)
O100.4189 (5)0.5000 (3)−0.08457 (14)0.0880 (10)
N30.1395 (4)0.4483 (3)0.22528 (17)0.0534 (9)
O90.4472 (3)0.5278 (2)0.01736 (13)0.0632 (8)
O5−0.0346 (3)0.53691 (19)0.11283 (15)0.0589 (7)
O60.0026 (4)0.4113 (2)0.05566 (15)0.0716 (9)
C90.8113 (5)0.6449 (3)0.24831 (18)0.0502 (10)
H9A0.82980.69610.27860.060*
H9B0.90240.63780.22210.060*
C170.0523 (5)0.7141 (3)0.03450 (17)0.0487 (9)
H17A0.01040.65920.01170.058*
H17B0.08330.76220.00370.058*
C190.2698 (5)0.2597 (2)0.02957 (16)0.0491 (10)
H19A0.34980.22170.00930.059*
H19B0.21990.2983−0.00280.059*
C70.7200 (4)0.3941 (3)0.23771 (17)0.0416 (8)
H70.79020.36840.26640.050*
O7−0.2336 (4)0.4603 (3)0.07427 (19)0.1008 (12)
O130.0984 (4)0.4247 (3)0.27906 (14)0.0865 (12)
C30.6437 (5)0.3281 (3)0.19573 (18)0.0424 (9)
C60.5145 (4)0.1941 (2)0.1115 (2)0.0479 (9)
H60.47290.14980.08320.057*
C18−0.0701 (6)0.7556 (3)0.0759 (2)0.0619 (11)
H18A−0.10750.70660.10410.093*
H18B−0.15360.77890.05030.093*
H18C−0.02780.80810.10000.093*
N5−0.0911 (4)0.4696 (3)0.08097 (17)0.0595 (10)
C40.6946 (5)0.2322 (3)0.1937 (2)0.0529 (11)
H40.77140.21170.22130.063*
C80.7765 (5)0.5516 (3)0.28201 (17)0.0501 (9)
H8A0.87180.52260.29700.060*
H8B0.71090.56410.31830.060*
C50.6319 (5)0.1673 (3)0.1509 (2)0.0562 (11)
H50.67030.10470.14900.067*
C200.1536 (6)0.1932 (3)0.0580 (2)0.0638 (12)
H20A0.20450.14910.08610.096*
H20B0.10300.15750.02500.096*
H20C0.07860.23010.08100.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.03650 (9)0.02909 (7)0.04323 (9)−0.00144 (11)−0.00520 (7)−0.00242 (8)
Zn10.0443 (2)0.03303 (19)0.0544 (2)−0.00166 (19)−0.0123 (2)−0.0040 (2)
O20.0413 (15)0.0242 (10)0.0603 (15)−0.0015 (11)−0.0160 (12)−0.0026 (10)
N40.073 (2)0.0412 (17)0.055 (2)−0.001 (2)−0.0013 (17)0.004 (2)
C20.039 (2)0.0262 (15)0.0424 (17)0.0016 (14)0.0071 (16)0.0025 (14)
N20.0392 (19)0.0394 (16)0.0456 (17)−0.0043 (14)−0.0003 (15)−0.0108 (14)
O40.0390 (14)0.0331 (12)0.0575 (16)0.0024 (11)−0.0120 (12)0.0036 (11)
C120.040 (2)0.0265 (15)0.0415 (18)−0.0019 (15)0.0044 (17)−0.0041 (14)
C160.060 (3)0.0266 (17)0.067 (3)−0.0089 (17)0.003 (2)−0.0052 (17)
C100.040 (2)0.0377 (18)0.053 (2)−0.0100 (16)0.0055 (19)−0.0121 (17)
C130.043 (2)0.0274 (15)0.0407 (18)0.0019 (14)0.0041 (16)−0.0032 (13)
C10.038 (2)0.0266 (15)0.0462 (19)−0.0005 (14)0.0041 (17)0.0033 (15)
C150.074 (3)0.0262 (17)0.070 (3)0.0011 (17)0.016 (2)0.0038 (18)
C110.043 (2)0.0291 (16)0.048 (2)−0.0067 (15)0.0066 (18)−0.0020 (16)
O30.0491 (16)0.0280 (11)0.0481 (14)−0.0025 (11)−0.0042 (12)−0.0058 (11)
C140.059 (3)0.0315 (17)0.049 (2)0.0056 (17)0.002 (2)0.0037 (15)
O80.0579 (18)0.0592 (17)0.0530 (14)−0.0081 (18)−0.0075 (12)0.0009 (13)
O10.0375 (14)0.0260 (10)0.0526 (13)0.0022 (11)−0.0108 (11)−0.0034 (11)
N10.0379 (15)0.0454 (18)0.0426 (15)0.0027 (13)−0.0063 (12)−0.0050 (14)
O110.059 (2)0.0578 (17)0.0515 (16)0.0024 (14)−0.0056 (14)−0.0162 (13)
O120.0609 (19)0.0451 (14)0.0571 (16)0.0023 (13)0.0048 (15)0.0038 (15)
O100.123 (3)0.081 (2)0.0597 (17)−0.016 (3)0.0224 (19)0.003 (2)
N30.043 (2)0.066 (2)0.051 (2)0.0182 (19)0.0018 (16)0.014 (2)
O90.0508 (17)0.086 (2)0.0531 (15)−0.0078 (15)−0.0056 (14)0.0006 (14)
O50.0466 (17)0.0468 (14)0.083 (2)−0.0018 (13)−0.0086 (15)−0.0024 (14)
O60.051 (2)0.087 (2)0.076 (2)−0.0141 (17)−0.0012 (16)−0.0347 (19)
C90.040 (2)0.060 (2)0.051 (2)−0.0020 (18)−0.0094 (18)−0.0168 (19)
C170.043 (2)0.046 (2)0.057 (2)0.0049 (18)−0.012 (2)0.0046 (18)
C190.064 (3)0.0359 (17)0.048 (2)−0.0046 (19)−0.008 (2)−0.0070 (15)
C70.035 (2)0.0441 (19)0.0453 (19)0.0080 (16)−0.0031 (17)0.0031 (17)
O70.045 (2)0.140 (3)0.117 (3)−0.023 (2)−0.008 (2)−0.001 (3)
O130.088 (3)0.118 (3)0.0534 (17)0.043 (2)0.0201 (17)0.0235 (19)
C30.042 (2)0.0388 (18)0.047 (2)0.0036 (16)−0.0056 (18)−0.0016 (17)
C60.043 (2)0.0292 (17)0.071 (3)0.0032 (15)0.005 (2)−0.0088 (18)
C180.057 (3)0.053 (2)0.076 (3)0.012 (2)0.005 (2)0.010 (2)
N50.044 (2)0.076 (3)0.058 (2)−0.0154 (18)−0.0044 (17)0.0121 (18)
C40.045 (2)0.042 (2)0.072 (3)0.0097 (17)−0.007 (2)0.011 (2)
C80.047 (2)0.051 (2)0.053 (2)0.0015 (19)−0.0118 (18)−0.0137 (18)
C50.061 (3)0.0314 (18)0.076 (3)0.0110 (19)−0.002 (2)−0.001 (2)
C200.071 (3)0.047 (2)0.074 (3)−0.015 (2)−0.017 (2)0.001 (2)
Geometric parameters (Å, º) top
Eu1—O12.356 (2)C15—H150.9300
Eu1—O22.404 (2)O3—C191.468 (4)
Eu1—O32.608 (2)C14—H140.9300
Eu1—O42.658 (2)N1—C71.282 (4)
Eu1—O52.474 (3)N1—C81.456 (4)
Eu1—O62.565 (3)O11—N31.249 (4)
Eu1—O82.441 (2)O12—N31.251 (4)
Eu1—O92.491 (3)N3—O131.237 (4)
Eu1—O112.537 (3)O5—N51.250 (4)
Eu1—O122.495 (3)O6—N51.263 (4)
Zn1—O11.901 (2)C9—C81.506 (6)
Zn1—O21.899 (2)C9—H9A0.9700
Zn1—N11.916 (3)C9—H9B0.9700
Zn1—N21.909 (3)C17—C181.491 (6)
O2—C121.340 (4)C17—H17A0.9700
N4—O91.259 (4)C17—H17B0.9700
N4—O101.266 (4)C19—C201.490 (6)
N4—O81.260 (4)C19—H19A0.9700
C2—O11.339 (4)C19—H19B0.9700
C2—C11.390 (5)C7—C31.436 (5)
C2—C31.415 (5)C7—H70.9300
N2—C101.291 (4)O7—N51.249 (4)
N2—C91.472 (5)C3—C41.399 (5)
O4—C131.378 (4)C6—C51.366 (6)
O4—C171.452 (4)C6—H60.9300
C12—C111.393 (5)C18—H18A0.9600
C12—C131.405 (5)C18—H18B0.9600
C16—C151.332 (5)C18—H18C0.9600
C16—C111.412 (5)C4—C51.385 (6)
C16—H160.9300C4—H40.9300
C10—C111.440 (5)C8—H8A0.9700
C10—H100.9300C8—H8B0.9700
C13—C141.374 (4)C5—H50.9300
C1—O31.382 (4)C20—H20A0.9600
C1—C61.391 (5)C20—H20B0.9600
C15—C141.390 (6)C20—H20C0.9600
O1—Eu1—O264.79 (8)C16—C15—C14120.4 (3)
O1—Eu1—O8123.15 (8)C16—C15—H15119.8
O2—Eu1—O8114.98 (9)C14—C15—H15119.8
O1—Eu1—O5140.73 (9)C12—C11—C16117.9 (4)
O2—Eu1—O5112.86 (9)C12—C11—C10123.8 (3)
O8—Eu1—O594.22 (10)C16—C11—C10118.3 (3)
O1—Eu1—O980.36 (9)C1—O3—C19118.2 (3)
O2—Eu1—O972.30 (9)C1—O3—Eu1118.47 (18)
O8—Eu1—O951.23 (9)C19—O3—Eu1123.0 (2)
O5—Eu1—O9138.20 (9)C13—C14—C15119.8 (4)
O1—Eu1—O1273.81 (9)C13—C14—H14120.1
O2—Eu1—O12113.87 (8)C15—C14—H14120.1
O8—Eu1—O12130.74 (10)N4—O8—Eu197.5 (2)
O5—Eu1—O1272.29 (9)C2—O1—Zn1123.7 (2)
O9—Eu1—O12146.26 (9)C2—O1—Eu1128.6 (2)
O1—Eu1—O1174.48 (9)Zn1—O1—Eu1106.25 (10)
O2—Eu1—O1169.91 (9)C7—N1—C8124.3 (3)
O8—Eu1—O11162.36 (10)C7—N1—Zn1125.2 (3)
O5—Eu1—O1168.80 (10)C8—N1—Zn1110.5 (2)
O9—Eu1—O11140.77 (9)N3—O11—Eu195.3 (2)
O12—Eu1—O1150.19 (9)N3—O12—Eu197.3 (2)
O1—Eu1—O6131.77 (10)O13—N3—O11121.5 (4)
O2—Eu1—O6161.76 (10)O13—N3—O12121.2 (4)
O8—Eu1—O665.09 (10)O11—N3—O12117.2 (3)
O5—Eu1—O650.29 (9)N4—O9—Eu195.2 (2)
O9—Eu1—O6114.52 (9)N5—O5—Eu198.8 (2)
O12—Eu1—O670.61 (10)N5—O6—Eu194.0 (2)
O11—Eu1—O6104.69 (10)N2—C9—C8107.1 (3)
O1—Eu1—O361.63 (8)N2—C9—H9A110.3
O2—Eu1—O3121.79 (8)C8—C9—H9A110.3
O8—Eu1—O378.75 (9)N2—C9—H9B110.3
O5—Eu1—O3122.53 (8)C8—C9—H9B110.3
O9—Eu1—O377.99 (9)H9A—C9—H9B108.5
O12—Eu1—O370.83 (8)O4—C17—C18112.3 (3)
O11—Eu1—O3113.91 (9)O4—C17—H17A109.1
O6—Eu1—O376.43 (9)C18—C17—H17A109.1
O1—Eu1—O4124.64 (8)O4—C17—H17B109.1
O2—Eu1—O459.99 (7)C18—C17—H17B109.1
O8—Eu1—O479.11 (9)H17A—C17—H17B107.9
O5—Eu1—O469.63 (8)O3—C19—C20113.1 (3)
O9—Eu1—O479.95 (9)O3—C19—H19A109.0
O12—Eu1—O4132.88 (8)C20—C19—H19A109.0
O11—Eu1—O490.07 (9)O3—C19—H19B109.0
O6—Eu1—O4103.45 (9)C20—C19—H19B109.0
O3—Eu1—O4155.45 (9)H19A—C19—H19B107.8
O2—Zn1—O184.32 (10)N1—C7—C3125.1 (3)
O2—Zn1—N295.74 (12)N1—C7—H7117.4
O1—Zn1—N2177.16 (12)C3—C7—H7117.4
O2—Zn1—N1172.23 (12)C4—C3—C2117.9 (3)
O1—Zn1—N194.44 (11)C4—C3—C7118.6 (4)
N2—Zn1—N185.88 (14)C2—C3—C7123.5 (3)
C12—O2—Zn1124.9 (2)C5—C6—C1119.7 (4)
C12—O2—Eu1130.3 (2)C5—C6—H6120.2
Zn1—O2—Eu1104.50 (9)C1—C6—H6120.2
O9—N4—O10121.7 (4)C17—C18—H18A109.5
O9—N4—O8115.7 (3)C17—C18—H18B109.5
O10—N4—O8122.6 (3)H18A—C18—H18B109.5
O1—C2—C1116.4 (3)C17—C18—H18C109.5
O1—C2—C3123.5 (3)H18A—C18—H18C109.5
C1—C2—C3120.0 (3)H18B—C18—H18C109.5
C10—N2—C9122.2 (3)O7—N5—O5121.6 (4)
C10—N2—Zn1124.9 (3)O7—N5—O6121.4 (4)
C9—N2—Zn1112.8 (2)O5—N5—O6117.0 (3)
C13—O4—C17117.2 (3)C5—C4—C3120.7 (4)
C13—O4—Eu1120.13 (19)C5—C4—H4119.6
C17—O4—Eu1122.7 (2)C3—C4—H4119.6
O2—C12—C11124.7 (3)N1—C8—C9109.3 (3)
O2—C12—C13115.8 (3)N1—C8—H8A109.8
C11—C12—C13119.5 (3)C9—C8—H8A109.8
C15—C16—C11122.1 (4)N1—C8—H8B109.8
C15—C16—H16119.0C9—C8—H8B109.8
C11—C16—H16119.0H8A—C8—H8B108.3
N2—C10—C11125.7 (3)C6—C5—C4121.0 (3)
N2—C10—H10117.2C6—C5—H5119.5
C11—C10—H10117.2C4—C5—H5119.5
C14—C13—O4126.1 (3)C19—C20—H20A109.5
C14—C13—C12120.3 (3)C19—C20—H20B109.5
O4—C13—C12113.5 (3)H20A—C20—H20B109.5
O3—C1—C2114.1 (3)C19—C20—H20C109.5
O3—C1—C6125.3 (3)H20A—C20—H20C109.5
C2—C1—C6120.5 (3)H20B—C20—H20C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O50.962.443.142 (5)130
C8—H8A···O13i0.972.423.295 (5)151
C10—H10···O13ii0.932.373.291 (5)169
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2.
Selected bond lengths (Å) top
Eu1—O12.356 (2)Eu1—O92.491 (3)
Eu1—O22.404 (2)Eu1—O112.537 (3)
Eu1—O32.608 (2)Eu1—O122.495 (3)
Eu1—O42.658 (2)Zn1—O11.901 (2)
Eu1—O52.474 (3)Zn1—O21.899 (2)
Eu1—O62.565 (3)Zn1—N11.916 (3)
Eu1—O82.441 (2)Zn1—N21.909 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O50.962.443.142 (5)129.8
C8—H8A···O13i0.972.423.295 (5)150.6
C10—H10···O13ii0.932.373.291 (5)168.5
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2.
Acknowledgements top

We gratefully acknowledge financial support from the Department of Education, JiangXi Province (No. 2007317), and the Natural Science Foundation of JiangXi Province (No. 0620029).

references
References top

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