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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1206.
Published online 2008 August 30. doi:  10.1107/S1600536808026329
PMCID: PMC2960587

{μ-6,6′-Dimeth­oxy-2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}trinitratocopper(II)europium(III)

Abstract

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.

Related literature

For copper–lanthanide complexes of the same Schiff base, see: Elmali & Elerman (2003 [triangle]); Elmali & Elerman (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1206-scheme1.jpg

Experimental

Crystal data

  • [CuEu(C19H20N2O4)(NO3)3]
  • M r = 741.90
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1206-efi1.jpg
  • a = 11.638 (2) Å
  • b = 14.680 (3) Å
  • c = 14.853 (3) Å
  • β = 101.52 (3)°
  • V = 2486.5 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.43 mm−1
  • T = 291 (2) K
  • 0.21 × 0.20 × 0.19 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.527, T max = 0.568 (expected range = 0.484–0.521)
  • 23524 measured reflections
  • 5660 independent reflections
  • 5072 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.058
  • S = 1.06
  • 5660 reflections
  • 354 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.72 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); 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 I, global. DOI: 10.1107/S1600536808026329/fj2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026329/fj2142Isup2.hkl

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

Acknowledgments

This work is supported financially by the National Natural Science Foundation of China (Nos. 20672032 and 20572018), the Key Laboratory of Heilongjiang Province and the Education Department of Heilongjiang Province (Nos. ZJG0504, JC200605, 1152GZD02 and 2006FRFLXG031).

supplementary crystallographic information

Comment

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.

Experimental

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%.

Refinement

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).

Figures

Fig. 1.
The molecular structure of (I), showing 40% probability displacement ellipsoids.

Crystal data

[CuEu(C19H20N2O4)(NO3)3]F000 = 1460
Mr = 741.90Dx = 1.982 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 17062 reflections
a = 11.638 (2) Åθ = 3.0–27.5º
b = 14.680 (3) ŵ = 3.43 mm1
c = 14.853 (3) ÅT = 291 (2) K
β = 101.52 (3)ºBlock, red
V = 2486.5 (9) Å30.21 × 0.20 × 0.19 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer5660 independent reflections
Radiation source: fine-focus sealed tube5072 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
Detector resolution: 10.000 pixels mm-1θmax = 27.5º
T = 291(2) Kθmin = 3.1º
ω scansh = −15→13
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)k = −19→19
Tmin = 0.527, Tmax = 0.568l = −19→19
23524 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-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 reflectionsΔρmax = 0.72 e Å3
354 parametersΔρmin = −0.44 e Å3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C10.9061 (2)0.36789 (18)−0.06244 (19)0.0317 (6)
C20.7932 (3)0.3919 (2)−0.10789 (19)0.0345 (6)
C30.7755 (3)0.4599 (2)−0.1732 (2)0.0449 (7)
H10.69990.4743−0.20380.054*
C40.8712 (3)0.5068 (2)−0.1931 (2)0.0523 (9)
H20.85940.5536−0.23610.063*
C50.9823 (3)0.4844 (2)−0.1499 (2)0.0463 (8)
H31.04560.5162−0.16390.056*
C61.0024 (3)0.4136 (2)−0.0841 (2)0.0365 (6)
C71.1218 (3)0.3936 (2)−0.0403 (2)0.0397 (7)
H41.17830.4344−0.05180.048*
C81.2885 (3)0.3275 (2)0.0496 (3)0.0536 (9)
H51.30800.38130.08760.064*
H61.32900.3320−0.00130.064*
C91.3326 (3)0.2449 (2)0.1056 (3)0.0511 (9)
H71.30380.24620.16250.061*
H81.41760.24690.12110.061*
C101.2950 (3)0.1573 (2)0.0561 (3)0.0488 (8)
H91.29750.1638−0.00850.059*
H101.34830.10880.08150.059*
C111.1568 (2)0.05275 (19)0.09083 (19)0.0336 (6)
H111.21940.01260.09540.040*
C121.0502 (2)0.01617 (18)0.11234 (18)0.0304 (6)
C131.0533 (3)−0.0754 (2)0.1430 (2)0.0380 (7)
H121.1202−0.11050.14420.046*
C140.9582 (3)−0.1123 (2)0.1709 (2)0.0458 (8)
H130.9602−0.17270.18990.055*
C150.8589 (3)−0.0602 (2)0.1710 (2)0.0413 (7)
H140.7953−0.08530.19140.050*
C160.8541 (2)0.02870 (19)0.14095 (19)0.0321 (6)
C170.9492 (2)0.06820 (17)0.10940 (17)0.0282 (5)
C180.6700 (3)0.0552 (3)0.1857 (3)0.0560 (9)
H150.63390.00160.15530.084*
H160.61190.10190.18390.084*
H170.70390.04080.24840.084*
C190.5899 (3)0.3491 (3)−0.1377 (3)0.0647 (11)
H180.56500.4115−0.13940.097*
H190.53630.3122−0.11210.097*
H200.59130.3287−0.19880.097*
Cu11.05535 (3)0.22819 (2)0.03974 (2)0.03036 (8)
Eu10.762074 (11)0.247433 (8)0.068399 (9)0.02785 (5)
N11.1594 (2)0.32671 (17)0.01249 (18)0.0382 (6)
N21.1746 (2)0.13432 (16)0.06616 (17)0.0341 (5)
N30.6075 (3)0.12249 (19)−0.0485 (2)0.0504 (7)
N40.8226 (5)0.2655 (3)0.2660 (2)0.0872 (15)
N50.6480 (2)0.42062 (17)0.09471 (18)0.0433 (6)
O10.91672 (16)0.30177 (13)0.00059 (14)0.0353 (4)
O20.70508 (18)0.34136 (15)−0.08175 (14)0.0399 (5)
O30.93757 (16)0.15332 (12)0.07838 (13)0.0324 (4)
O40.76063 (18)0.08689 (14)0.13955 (15)0.0390 (5)
O50.7096 (2)0.13933 (16)−0.06160 (16)0.0478 (5)
O60.5492 (3)0.0630 (2)−0.0900 (3)0.1037 (13)
O70.57208 (18)0.17165 (15)0.01090 (16)0.0445 (5)
O80.7188 (3)0.25602 (16)0.2249 (2)0.0633 (8)
O90.8490 (5)0.2703 (3)0.3497 (2)0.1377 (17)
O100.8992 (3)0.2700 (2)0.2174 (2)0.0809 (10)
O110.58719 (19)0.35057 (16)0.07275 (17)0.0478 (5)
O120.6061 (3)0.49507 (18)0.1043 (2)0.0779 (9)
O130.75861 (19)0.41086 (15)0.10619 (17)0.0457 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0326 (14)0.0304 (13)0.0328 (14)0.0001 (11)0.0084 (11)0.0008 (11)
C20.0338 (15)0.0357 (14)0.0341 (14)−0.0031 (12)0.0074 (12)0.0002 (12)
C30.0492 (19)0.0455 (18)0.0374 (16)0.0018 (15)0.0022 (14)0.0098 (13)
C40.062 (2)0.052 (2)0.0429 (18)−0.0013 (17)0.0104 (16)0.0185 (15)
C50.052 (2)0.0428 (17)0.0477 (18)−0.0078 (15)0.0186 (16)0.0115 (14)
C60.0382 (16)0.0335 (14)0.0408 (16)−0.0030 (12)0.0149 (13)0.0017 (12)
C70.0350 (16)0.0353 (15)0.0528 (18)−0.0075 (13)0.0186 (14)0.0013 (13)
C80.0262 (16)0.0448 (19)0.089 (3)−0.0044 (14)0.0089 (17)−0.0001 (18)
C90.0259 (16)0.059 (2)0.067 (2)−0.0044 (14)0.0062 (15)0.0024 (17)
C100.0306 (16)0.0420 (17)0.079 (2)0.0051 (14)0.0225 (16)0.0063 (16)
C110.0298 (14)0.0363 (14)0.0340 (14)0.0067 (12)0.0052 (11)0.0010 (12)
C120.0329 (14)0.0304 (13)0.0280 (13)0.0012 (11)0.0065 (11)−0.0008 (10)
C130.0431 (17)0.0323 (14)0.0382 (16)0.0068 (13)0.0070 (13)0.0022 (12)
C140.057 (2)0.0283 (14)0.0526 (19)−0.0006 (14)0.0135 (16)0.0089 (13)
C150.0448 (18)0.0352 (15)0.0463 (17)−0.0081 (13)0.0145 (14)0.0057 (13)
C160.0310 (14)0.0312 (14)0.0343 (14)−0.0015 (11)0.0072 (11)0.0011 (11)
C170.0323 (14)0.0268 (12)0.0254 (12)−0.0026 (11)0.0054 (10)−0.0005 (10)
C180.0374 (18)0.061 (2)0.077 (3)−0.0020 (16)0.0289 (18)0.0201 (19)
C190.0328 (18)0.084 (3)0.069 (2)−0.0063 (18)−0.0103 (17)0.024 (2)
Cu10.02206 (16)0.03009 (16)0.03997 (18)−0.00026 (13)0.00866 (14)0.00474 (14)
Eu10.02169 (8)0.02888 (8)0.03354 (8)−0.00131 (5)0.00688 (5)−0.00045 (5)
N10.0247 (12)0.0372 (13)0.0539 (15)−0.0038 (10)0.0110 (11)−0.0005 (11)
N20.0254 (12)0.0361 (13)0.0422 (13)0.0030 (10)0.0103 (10)0.0021 (10)
N30.0429 (16)0.0409 (15)0.0632 (18)−0.0032 (12)0.0008 (14)−0.0151 (13)
N40.119 (4)0.100 (3)0.0346 (16)0.079 (3)−0.003 (2)−0.0102 (17)
N50.0479 (17)0.0361 (14)0.0454 (15)0.0078 (12)0.0084 (12)0.0007 (11)
O10.0274 (10)0.0341 (10)0.0457 (11)0.0018 (8)0.0107 (9)0.0132 (9)
O20.0270 (10)0.0460 (12)0.0437 (12)−0.0020 (9)0.0002 (9)0.0098 (9)
O30.0269 (10)0.0276 (9)0.0447 (11)0.0020 (8)0.0122 (8)0.0073 (8)
O40.0310 (11)0.0382 (11)0.0521 (12)−0.0011 (9)0.0181 (10)0.0089 (9)
O50.0432 (13)0.0474 (13)0.0544 (13)−0.0019 (11)0.0136 (11)−0.0141 (11)
O60.068 (2)0.087 (2)0.151 (3)−0.0302 (18)0.010 (2)−0.070 (2)
O70.0293 (11)0.0483 (13)0.0551 (13)−0.0027 (9)0.0066 (10)−0.0091 (11)
O80.088 (2)0.0581 (16)0.0499 (15)0.0195 (14)0.0294 (16)0.0010 (12)
O90.166 (4)0.192 (4)0.0457 (17)0.115 (3)−0.003 (2)−0.020 (2)
O100.0621 (19)0.114 (3)0.0561 (17)0.0386 (18)−0.0146 (15)−0.0300 (17)
O110.0298 (11)0.0466 (13)0.0674 (15)0.0017 (10)0.0107 (10)−0.0029 (11)
O120.089 (2)0.0437 (14)0.099 (2)0.0295 (15)0.0140 (18)−0.0063 (15)
O130.0378 (12)0.0380 (12)0.0607 (14)−0.0067 (9)0.0087 (10)−0.0057 (10)

Geometric parameters (Å, °)

C1—O11.337 (3)C16—O41.380 (3)
C1—C61.398 (4)C16—C171.409 (4)
C1—C21.398 (4)C17—O31.329 (3)
C2—C31.378 (4)C18—O41.445 (3)
C2—O21.383 (3)C18—H150.9600
C3—C41.392 (5)C18—H160.9600
C3—H10.9300C18—H170.9600
C4—C51.363 (5)C19—O21.433 (4)
C4—H20.9300C19—H180.9600
C5—C61.414 (4)C19—H190.9600
C5—H30.9300C19—H200.9600
C6—C71.441 (4)Cu1—O31.9315 (18)
C7—N11.278 (4)Cu1—O11.9320 (19)
C7—H40.9300Cu1—N21.940 (2)
C8—N11.494 (4)Cu1—N11.980 (2)
C8—C91.501 (5)Eu1—O12.3694 (19)
C8—H50.9700Eu1—O32.4457 (18)
C8—H60.9700Eu1—O132.466 (2)
C9—C101.502 (5)Eu1—O72.470 (2)
C9—H70.9700Eu1—O82.478 (3)
C9—H80.9700Eu1—O102.478 (3)
C10—N21.478 (4)Eu1—O52.480 (2)
C10—H90.9700Eu1—O112.548 (2)
C10—H100.9700Eu1—O42.584 (2)
C11—N21.281 (4)Eu1—O22.593 (2)
C11—C121.445 (4)N3—O61.198 (4)
C11—H110.9300N3—O51.266 (4)
C12—C171.395 (4)N3—O71.271 (3)
C12—C131.418 (4)N4—O91.222 (5)
C13—C141.368 (4)N4—O81.249 (5)
C13—H120.9300N4—O101.256 (6)
C14—C151.387 (5)N5—O121.216 (3)
C14—H130.9300N5—O111.254 (3)
C15—C161.376 (4)N5—O131.273 (3)
C15—H140.9300
O1—C1—C6122.9 (3)O1—Eu1—O361.31 (6)
O1—C1—C2117.9 (2)O1—Eu1—O1379.49 (7)
C6—C1—C2119.2 (3)O3—Eu1—O13125.96 (7)
C3—C2—O2124.8 (3)O1—Eu1—O7135.09 (7)
C3—C2—C1121.1 (3)O3—Eu1—O7116.46 (7)
O2—C2—C1114.0 (2)O13—Eu1—O7117.56 (7)
C2—C3—C4119.6 (3)O1—Eu1—O8134.09 (10)
C2—C3—H1120.2O3—Eu1—O8107.21 (9)
C4—C3—H1120.2O13—Eu1—O873.82 (8)
C5—C4—C3120.3 (3)O7—Eu1—O890.65 (10)
C5—C4—H2119.8O1—Eu1—O1085.77 (10)
C3—C4—H2119.8O3—Eu1—O1068.91 (8)
C4—C5—C6120.9 (3)O13—Eu1—O1072.77 (9)
C4—C5—H3119.6O7—Eu1—O10137.83 (11)
C6—C5—H3119.6O8—Eu1—O1051.04 (12)
C1—C6—C5118.8 (3)O1—Eu1—O588.53 (8)
C1—C6—C7122.9 (3)O3—Eu1—O576.02 (8)
C5—C6—C7118.2 (3)O13—Eu1—O5141.92 (8)
N1—C7—C6127.9 (3)O7—Eu1—O551.56 (8)
N1—C7—H4116.1O8—Eu1—O5134.29 (9)
C6—C7—H4116.1O10—Eu1—O5142.67 (9)
N1—C8—C9113.9 (3)O1—Eu1—O11119.29 (7)
N1—C8—H5108.8O3—Eu1—O11174.77 (7)
C9—C8—H5108.8O13—Eu1—O1150.70 (7)
N1—C8—H6108.8O7—Eu1—O1167.17 (8)
C9—C8—H6108.8O8—Eu1—O1168.45 (9)
H5—C8—H6107.7O10—Eu1—O11105.86 (9)
C8—C9—C10112.7 (3)O5—Eu1—O11109.04 (8)
C8—C9—H7109.0O1—Eu1—O4123.26 (6)
C10—C9—H7109.0O3—Eu1—O462.20 (6)
C8—C9—H8109.0O13—Eu1—O4142.41 (8)
C10—C9—H8109.0O7—Eu1—O469.64 (7)
H7—C9—H8107.8O8—Eu1—O469.12 (7)
N2—C10—C9109.6 (3)O10—Eu1—O479.18 (10)
N2—C10—H9109.7O5—Eu1—O473.38 (8)
C9—C10—H9109.7O11—Eu1—O4117.46 (7)
N2—C10—H10109.7O1—Eu1—O262.67 (7)
C9—C10—H10109.7O3—Eu1—O2114.81 (7)
H9—C10—H10108.2O13—Eu1—O270.45 (8)
N2—C11—C12127.3 (3)O7—Eu1—O283.38 (8)
N2—C11—H11116.3O8—Eu1—O2135.61 (8)
C12—C11—H11116.3O10—Eu1—O2134.86 (10)
C17—C12—C13119.8 (3)O5—Eu1—O271.93 (8)
C17—C12—C11123.0 (2)O11—Eu1—O268.74 (8)
C13—C12—C11117.1 (3)O4—Eu1—O2144.61 (7)
C14—C13—C12120.1 (3)C7—N1—C8114.6 (3)
C14—C13—H12120.0C7—N1—Cu1122.6 (2)
C12—C13—H12120.0C8—N1—Cu1122.8 (2)
C13—C14—C15120.5 (3)C11—N2—C10117.0 (2)
C13—C14—H13119.7C11—N2—Cu1124.85 (19)
C15—C14—H13119.7C10—N2—Cu1118.15 (19)
C16—C15—C14120.1 (3)O6—N3—O5121.1 (3)
C16—C15—H14119.9O6—N3—O7122.8 (3)
C14—C15—H14119.9O5—N3—O7116.1 (2)
C15—C16—O4124.9 (3)O9—N4—O8121.7 (5)
C15—C16—C17121.0 (3)O9—N4—O10121.3 (5)
O4—C16—C17114.1 (2)O8—N4—O10117.0 (3)
O3—C17—C12123.5 (2)O12—N5—O11123.3 (3)
O3—C17—C16118.0 (2)O12—N5—O13120.2 (3)
C12—C17—C16118.5 (2)O11—N5—O13116.5 (2)
O4—C18—H15109.5C1—O1—Cu1124.84 (17)
O4—C18—H16109.5C1—O1—Eu1124.78 (16)
H15—C18—H16109.5Cu1—O1—Eu1110.09 (8)
O4—C18—H17109.5C2—O2—C19117.1 (2)
H15—C18—H17109.5C2—O2—Eu1116.77 (17)
H16—C18—H17109.5C19—O2—Eu1126.1 (2)
O2—C19—H18109.5C17—O3—Cu1127.52 (17)
O2—C19—H19109.5C17—O3—Eu1125.29 (16)
H18—C19—H19109.5Cu1—O3—Eu1107.10 (8)
O2—C19—H20109.5C16—O4—C18116.2 (2)
H18—C19—H20109.5C16—O4—Eu1120.07 (15)
H19—C19—H20109.5C18—O4—Eu1123.57 (19)
O3—Cu1—O178.94 (8)N3—O5—Eu195.64 (17)
O3—Cu1—N293.28 (9)N3—O7—Eu195.94 (17)
O1—Cu1—N2168.21 (10)N4—O8—Eu196.1 (2)
O3—Cu1—N1167.44 (9)N4—O10—Eu195.9 (3)
O1—Cu1—N192.19 (9)N5—O11—Eu194.71 (17)
N2—Cu1—N196.78 (10)N5—O13—Eu198.11 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2142).

References

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  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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