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Acta Cryst. (2007). E63, m2087-m2088    [ doi:10.1107/S1600536807032552 ]

{[mu]-6,6'-Diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}trinitratoneodymium(III)copper(II)

Y. Sui, X.-N. Fang, X.-C. Zhou, Q.-Y. Luo and Y.-P. Xu

Abstract top

In the title heteronuclear CuII-NdIII 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'-neodymium(III)copper(II)), [CuNd(C20H22N2O4)(NO3)3], with the hexadentate Schiff base compartmental ligand N,N'-bis(3-ethoxysalicylidene)ethylenediamine, the Cu and Nd atoms are doubly bridged by two phenolate O atoms provided by the Schiff base ligand. The coordination of the Cu atom is square planar with the donor centers of two imine N atoms and two phenolate O atoms. The neodymium(III) center has a decacoordination environment of O atoms, involving the phenolate O atoms, two ethoxy O atoms and two O atoms each from the three nitrate ligands. Some weak C-H...O and O...Cu [O...Cu = 3.169 (3) Å] interactions 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 CuII—NdIII complex with salen-type Schiff base N,N'-bis(3-ethoxysalicylidene) ethylenediamine(H2L).

Complex (I) crystallizes in the space group P212121, with copper and neodymium doubly bridged by two phenolate O atoms provided by a salen-type Schiff base ligand. The inner salen-type cavity is occupied by copper(II), while neodymium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand. The dihedral angles between the mean planes of Cu1/O1/O2 and Nd1/O1/O2 is 3.63 (14)° suggesting that the bridging moiety is almost planar; the deviation of atoms from the least squares Cu1/O1/O2/Nd1 plane being -0.0308 (3)Å for Cu, -0.0211 (2)Å for Nd, 0.0256 (3)Å for O1 and 0.0262 (3)Å for O2.

The neodymium(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 neodymium to complete the decacoordination. The three kinds of Nd—O bond distances are significantly different, the shortest being the Nd—O(phenolate) and longest being the Nd—O(ethoxy) separations.

The coordination of copper(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 0.0887 (2) Å, while Cu1 is 0.0395 (3)Å above this square plane.

Adjacent molecules are held together by weak interactions (O13···Cu1=3.169 (3) Å, C7—H7···O7i=3.277 (4) and C9—H9A···O7ii=3.290 (5); symmetry codes:(i)-x + 1, y - 1/2, 3/2 - z; (ii)1 + x, y, 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 copper(II) acetate monohydrate (0.168 g, 1 mmol) with H2L(0.356 g, 1 mmol) in methanol solution (60 ml) under reflux for 3 h and then for another 3 h after the addition of neodymium(III) nitrate hexahydrate (0.438 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 C20H22CuN5NdO13: C 32.11, H 2.96, Cu 8.49, N 9.36,Nd 19.28%; found: C 32.00, H 2.86, Cu 8.53, N 9.47,Nd 19.30%. 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.
[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'-\ neodymium(III)copper(II)) top
Crystal data top
[CuNd(C20H22N2O4)(NO3)3]F(000) = 1480
Mr = 748.21Dx = 1.962 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 19224 reflections
a = 8.6439 (16) Åθ = 1.8–28.3°
b = 13.861 (3) ŵ = 2.95 mm−1
c = 21.135 (4) ÅT = 293 K
V = 2532.4 (8) Å3Block, red
Z = 40.22 × 0.17 × 0.08 mm
Data collection top
Bruker APEX II area-detector
diffractometer		6179 independent reflections
Radiation source: fine-focus sealed tube4830 reflections with I > 2σ(I)
graphiteRint = 0.030
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 = 0.570, Tmax = 0.794l = −28→27
19224 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) = 0.051 w = 1/[σ2(Fo2) + (0.017P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6179 reflectionsΔρmax = 0.41 e Å−3
363 parametersΔρmin = −0.85 e Å−3
0 restraintsAbsolute structure: Flack (1983), 2611 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.008 (10)
Crystal data top
[CuNd(C20H22N2O4)(NO3)3]V = 2532.4 (8) Å3
Mr = 748.21Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6439 (16) ŵ = 2.95 mm−1
b = 13.861 (3) ÅT = 293 K
c = 21.135 (4) Å0.22 × 0.17 × 0.08 mm
Data collection top
Bruker APEX II area-detector
diffractometer		6179 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		4830 reflections with I > 2σ(I)
Tmin = 0.570, Tmax = 0.794Rint = 0.030
19224 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.051Δρmax = 0.41 e Å−3
S = 1.01Δρmin = −0.85 e Å−3
6179 reflectionsAbsolute structure: Flack (1983), 2611 Friedel pairs
363 parametersFlack parameter: −0.008 (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
C110.6447 (4)1.1718 (2)0.80399 (17)0.0393 (9)
O20.4613 (2)1.05648 (15)0.84587 (10)0.0361 (5)
C140.5175 (4)1.3051 (2)0.88820 (18)0.0446 (9)
H140.47671.34960.91660.053*
Nd10.241515 (18)0.999977 (13)0.904190 (7)0.03374 (5)
Cu10.56585 (5)0.94407 (3)0.81664 (2)0.03818 (10)
O10.4129 (3)0.87540 (14)0.86294 (11)0.0393 (6)
N30.3700 (4)0.9940 (3)1.03348 (15)0.0519 (7)
N20.6995 (3)1.0138 (2)0.76099 (13)0.0409 (7)
O90.4502 (3)0.9690 (2)0.98654 (12)0.0620 (8)
N10.6781 (4)0.8324 (2)0.79083 (14)0.0399 (8)
C10.4124 (4)0.7805 (2)0.87300 (16)0.0325 (8)
O30.1882 (3)0.81437 (15)0.93014 (11)0.0396 (6)
O100.4244 (4)1.0009 (2)1.08698 (13)0.0815 (8)
C20.2910 (4)0.7440 (2)0.90989 (16)0.0357 (8)
C70.6500 (4)0.7459 (3)0.80840 (18)0.0413 (9)
H70.71610.69780.79390.050*
C50.5126 (4)0.6185 (2)0.86622 (18)0.0494 (10)
H50.58750.57560.85190.059*
O80.2296 (3)1.0111 (2)1.02179 (11)0.0565 (6)
C40.3961 (4)0.5855 (2)0.90305 (19)0.0513 (10)
H40.39250.52050.91390.062*
C100.7205 (4)1.1050 (3)0.76113 (16)0.0415 (8)
H100.78921.13050.73170.050*
C60.5231 (4)0.7166 (2)0.84912 (16)0.0367 (8)
C190.0527 (4)0.7830 (2)0.96501 (17)0.0446 (9)
H19A0.00970.83750.98780.053*
H19B0.08320.73480.99580.053*
O60.1803 (3)0.9675 (2)0.78716 (13)0.0539 (8)
O50.1368 (3)1.11173 (18)0.81937 (13)0.0523 (6)
N40.1369 (4)1.0515 (3)0.77486 (17)0.0520 (8)
C30.2823 (4)0.6474 (2)0.92465 (17)0.0448 (9)
H30.20080.62410.94890.054*
C80.8123 (4)0.8556 (3)0.75078 (18)0.0478 (9)
H8A0.83050.80420.72050.057*
H8B0.90430.86320.77660.057*
C90.7763 (4)0.9481 (3)0.71683 (16)0.0463 (9)
H9A0.87100.97720.70130.056*
H9B0.70930.93540.68100.056*
C20−0.0682 (5)0.7417 (3)0.9226 (2)0.0627 (12)
H20A−0.10440.79070.89410.094*
H20B−0.15310.71850.94760.094*
H20C−0.02500.68920.89880.094*
O11−0.0411 (3)0.96243 (18)0.88817 (13)0.0575 (7)
O40.3447 (3)1.17580 (15)0.92475 (11)0.0390 (6)
O13−0.2383 (3)1.0394 (3)0.92662 (16)0.0963 (11)
C160.5209 (4)1.1451 (2)0.84417 (15)0.0334 (7)
O12−0.0021 (3)1.0835 (2)0.94837 (15)0.0706 (9)
O70.0968 (4)1.0759 (2)0.72145 (14)0.0835 (11)
C130.6365 (5)1.3318 (3)0.84766 (19)0.0536 (10)
H130.67481.39450.84920.064*
N5−0.0977 (4)1.0284 (2)0.92122 (16)0.0559 (9)
C150.4601 (4)1.2122 (2)0.88621 (16)0.0352 (8)
C120.6984 (4)1.2675 (3)0.80550 (19)0.0492 (11)
H120.77591.28720.77780.059*
C170.2725 (4)1.2405 (2)0.97093 (16)0.0447 (9)
H17A0.35201.27930.99100.054*
H17B0.22231.20241.00350.054*
C180.1549 (5)1.3063 (3)0.9406 (2)0.0595 (12)
H18A0.20711.35390.91550.089*
H18B0.09521.33770.97290.089*
H18C0.08731.26900.91400.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.036 (2)0.0354 (18)0.047 (2)−0.0048 (15)0.0028 (17)−0.0019 (18)
O20.0360 (12)0.0246 (10)0.0477 (13)−0.0027 (10)0.0114 (11)−0.0024 (11)
C140.048 (2)0.0276 (18)0.058 (2)−0.0006 (14)−0.0061 (19)−0.0105 (17)
Nd10.03385 (8)0.02793 (7)0.03943 (8)0.00136 (11)0.00417 (8)−0.00230 (9)
Cu10.0381 (2)0.02996 (18)0.0464 (2)0.00145 (18)0.0109 (2)−0.0040 (2)
O10.0419 (14)0.0237 (10)0.0523 (15)0.0026 (10)0.0147 (12)0.0001 (10)
N30.067 (2)0.0368 (15)0.0518 (19)0.001 (2)−0.0018 (16)0.007 (2)
N20.0382 (14)0.0444 (18)0.0401 (15)−0.0006 (13)0.0055 (11)−0.0015 (15)
O90.0502 (15)0.084 (2)0.0516 (15)0.0084 (14)0.0009 (14)0.0027 (14)
N10.0384 (17)0.0395 (17)0.0417 (18)0.0031 (13)0.0055 (14)−0.0102 (15)
C10.037 (2)0.0277 (16)0.0329 (18)0.0005 (14)−0.0024 (16)−0.0024 (15)
O30.0354 (13)0.0328 (12)0.0506 (15)−0.0020 (10)0.0100 (11)0.0016 (11)
O100.114 (2)0.0766 (19)0.0540 (17)0.012 (2)−0.0269 (17)−0.002 (2)
C20.0441 (19)0.0260 (15)0.0369 (18)−0.0003 (13)−0.0045 (16)−0.0048 (15)
C70.038 (2)0.0379 (19)0.048 (2)0.0122 (15)−0.0037 (18)−0.0101 (18)
C50.056 (2)0.0292 (18)0.063 (3)0.0116 (16)−0.003 (2)−0.0040 (18)
O80.0605 (17)0.0622 (17)0.0469 (13)0.0087 (17)0.0071 (12)−0.0003 (13)
C40.066 (3)0.0263 (17)0.061 (2)0.0002 (16)−0.012 (2)−0.0049 (18)
C100.039 (2)0.047 (2)0.0385 (19)−0.0080 (17)0.0035 (16)0.0003 (17)
C60.041 (2)0.0271 (16)0.0415 (19)0.0031 (14)−0.0063 (17)−0.0028 (16)
C190.0379 (19)0.0436 (19)0.052 (2)−0.0067 (16)0.0101 (19)0.0034 (18)
O60.0582 (18)0.0578 (17)0.0457 (16)−0.0026 (13)0.0010 (13)−0.0126 (13)
O50.0603 (17)0.0462 (14)0.0503 (16)−0.0021 (12)−0.0057 (14)0.0040 (15)
N40.0408 (18)0.069 (2)0.046 (2)−0.0183 (19)−0.0010 (16)0.012 (2)
C30.053 (2)0.0341 (17)0.048 (2)−0.0029 (16)−0.0019 (18)0.0059 (16)
C80.038 (2)0.057 (2)0.049 (2)0.0061 (17)0.0084 (18)−0.0130 (19)
C90.046 (2)0.0496 (19)0.0436 (19)−0.0016 (18)0.0120 (17)−0.0123 (18)
C200.057 (3)0.052 (2)0.079 (3)−0.013 (2)−0.003 (2)0.009 (2)
O110.0442 (15)0.0472 (15)0.081 (2)0.0035 (12)0.0041 (14)−0.0056 (14)
O40.0468 (14)0.0273 (11)0.0431 (14)0.0019 (10)0.0070 (11)−0.0051 (11)
O130.0380 (16)0.139 (3)0.113 (3)0.022 (2)0.0050 (18)−0.003 (2)
C160.0365 (19)0.0275 (16)0.0362 (17)0.0000 (13)−0.0041 (15)0.0000 (15)
O120.0493 (18)0.086 (2)0.077 (2)0.0160 (15)0.0005 (16)−0.0320 (19)
O70.087 (2)0.115 (3)0.0478 (16)−0.047 (2)−0.0185 (17)0.0250 (19)
C130.055 (2)0.0370 (19)0.069 (3)−0.0125 (18)−0.001 (2)−0.001 (2)
N50.0396 (19)0.072 (3)0.057 (2)0.0079 (16)0.0062 (16)0.0123 (17)
C150.036 (2)0.0303 (17)0.0387 (19)0.0008 (14)−0.0041 (16)0.0029 (15)
C120.044 (2)0.0382 (19)0.065 (3)−0.0093 (16)0.007 (2)0.0051 (19)
C170.060 (2)0.0344 (17)0.0399 (19)0.0043 (17)0.0102 (19)−0.0106 (15)
C180.063 (3)0.044 (2)0.071 (3)0.0109 (19)0.019 (2)0.004 (2)
Geometric parameters (Å, °) top
C11—C121.407 (5)C5—C41.353 (5)
C11—C161.415 (5)C5—C61.409 (4)
C11—C101.451 (5)C5—H50.9300
O2—C161.333 (3)C4—C31.383 (5)
C14—C151.380 (4)C4—H40.9300
C14—C131.389 (5)C10—H100.9300
C14—H140.9300C19—C201.492 (5)
Nd1—O12.437 (2)C19—H19A0.9700
Nd1—O32.671 (2)C19—H19B0.9700
Nd1—O42.631 (2)O6—N41.250 (4)
Nd1—O52.536 (3)O5—N41.258 (4)
Nd1—O62.569 (3)N4—O71.229 (4)
Nd1—O82.493 (2)C3—H30.9300
Nd1—O92.543 (3)C8—C91.502 (5)
Nd1—O112.521 (3)C8—H8A0.9700
Nd1—O122.578 (3)C8—H8B0.9700
O2—Cu11.904 (2)C9—H9A0.9700
O2—Nd12.396 (2)C9—H9B0.9700
Cu1—O11.900 (2)C20—H20A0.9600
Cu1—N11.906 (3)C20—H20B0.9600
Cu1—N21.911 (3)C20—H20C0.9600
O1—C11.333 (3)O11—N51.250 (4)
N3—O101.228 (4)O4—C151.383 (4)
N3—O91.259 (4)O4—C171.465 (4)
N3—O81.261 (4)O13—N51.230 (4)
N2—C101.278 (4)C16—C151.390 (4)
N2—C91.463 (4)O12—N51.263 (4)
N1—C71.280 (4)C13—C121.369 (5)
N1—C81.472 (4)C13—H130.9300
C1—C61.398 (4)C12—H120.9300
C1—C21.402 (5)C17—C181.509 (5)
O3—C21.387 (4)C17—H17A0.9700
O3—C191.450 (4)C17—H17B0.9700
C2—C31.376 (4)C18—H18A0.9600
C7—C61.452 (5)C18—H18B0.9600
C7—H70.9300C18—H18C0.9600
C12—C11—C16118.8 (3)O3—C2—C1113.4 (3)
C12—C11—C10117.8 (3)N1—C7—C6125.3 (3)
C16—C11—C10123.3 (3)N1—C7—H7117.4
C16—O2—Cu1124.18 (19)C6—C7—H7117.4
C16—O2—Nd1128.46 (19)C4—C5—C6121.5 (3)
Cu1—O2—Nd1106.00 (9)C4—C5—H5119.3
C15—C14—C13119.8 (3)C6—C5—H5119.3
C15—C14—H14120.1N3—O8—Nd198.3 (2)
C13—C14—H14120.1C5—C4—C3120.6 (3)
O2—Nd1—O164.25 (7)C5—C4—H4119.7
O2—Nd1—O8121.70 (8)C3—C4—H4119.7
O1—Nd1—O8115.21 (8)N2—C10—C11124.6 (3)
O2—Nd1—O11140.06 (8)N2—C10—H10117.7
O1—Nd1—O11113.26 (8)C11—C10—H10117.7
O8—Nd1—O1196.12 (9)C1—C6—C5118.3 (3)
O2—Nd1—O573.72 (8)C1—C6—C7123.7 (3)
O1—Nd1—O5113.39 (8)C5—C6—C7118.0 (3)
O8—Nd1—O5130.71 (9)O3—C19—C20112.1 (3)
O11—Nd1—O571.65 (8)O3—C19—H19A109.2
O2—Nd1—O981.07 (9)C20—C19—H19A109.2
O1—Nd1—O972.18 (9)O3—C19—H19B109.2
O8—Nd1—O950.01 (8)C20—C19—H19B109.2
O11—Nd1—O9138.13 (9)H19A—C19—H19B107.9
O5—Nd1—O9147.13 (9)N4—O6—Nd195.7 (2)
O2—Nd1—O674.05 (8)N4—O5—Nd197.1 (2)
O1—Nd1—O669.91 (9)O7—N4—O6122.2 (4)
O8—Nd1—O6164.25 (9)O7—N4—O5120.3 (4)
O11—Nd1—O668.60 (9)O6—N4—O5117.6 (3)
O5—Nd1—O649.68 (8)C2—C3—C4119.4 (3)
O9—Nd1—O6140.84 (9)C2—C3—H3120.3
O2—Nd1—O12133.41 (9)C4—C3—H3120.3
O1—Nd1—O12160.81 (9)N1—C8—C9107.3 (3)
O8—Nd1—O1264.99 (9)N1—C8—H8A110.3
O11—Nd1—O1249.43 (9)C9—C8—H8A110.3
O5—Nd1—O1271.96 (10)N1—C8—H8B110.3
O9—Nd1—O12114.04 (9)C9—C8—H8B110.3
O6—Nd1—O12105.02 (10)H8A—C8—H8B108.5
O2—Nd1—O460.89 (7)N2—C9—C8108.7 (3)
O1—Nd1—O4120.62 (7)N2—C9—H9A110.0
O8—Nd1—O477.98 (8)C8—C9—H9A110.0
O11—Nd1—O4122.82 (8)N2—C9—H9B110.0
O5—Nd1—O470.86 (8)C8—C9—H9B110.0
O9—Nd1—O478.62 (8)H9A—C9—H9B108.3
O6—Nd1—O4113.02 (8)C19—C20—H20A109.5
O12—Nd1—O478.54 (9)C19—C20—H20B109.5
O2—Nd1—O3123.87 (7)H20A—C20—H20B109.5
O1—Nd1—O359.71 (7)C19—C20—H20C109.5
O8—Nd1—O381.25 (8)H20A—C20—H20C109.5
O11—Nd1—O370.21 (8)H20B—C20—H20C109.5
O5—Nd1—O3132.22 (8)N5—O11—Nd198.8 (2)
O9—Nd1—O379.59 (8)C15—O4—C17118.4 (2)
O6—Nd1—O389.63 (8)C15—O4—Nd1119.02 (18)
O12—Nd1—O3102.54 (9)C17—O4—Nd1122.19 (19)
O4—Nd1—O3156.47 (8)O2—C16—C15117.0 (3)
O1—Cu1—O284.99 (9)O2—C16—C11123.3 (3)
O1—Cu1—N195.44 (11)C15—C16—C11119.7 (3)
O2—Cu1—N1177.03 (12)N5—O12—Nd195.7 (2)
O1—Cu1—N2172.22 (12)C12—C13—C14121.1 (3)
O2—Cu1—N294.18 (11)C12—C13—H13119.4
N1—Cu1—N285.79 (13)C14—C13—H13119.4
C1—O1—Cu1125.4 (2)O13—N5—O11122.0 (4)
C1—O1—Nd1129.8 (2)O13—N5—O12121.9 (4)
Cu1—O1—Nd1104.61 (8)O11—N5—O12116.1 (3)
O10—N3—O9122.4 (3)C14—C15—O4125.6 (3)
O10—N3—O8122.3 (3)C14—C15—C16120.5 (3)
O9—N3—O8115.3 (3)O4—C15—C16113.9 (3)
C10—N2—C9123.6 (3)C13—C12—C11120.0 (4)
C10—N2—Cu1125.8 (3)C13—C12—H12120.0
C9—N2—Cu1110.6 (2)C11—C12—H12120.0
N3—O9—Nd195.9 (2)O4—C17—C18111.9 (3)
C7—N1—C8121.4 (3)O4—C17—H17A109.2
C7—N1—Cu1125.6 (3)C18—C17—H17A109.2
C8—N1—Cu1112.9 (2)O4—C17—H17B109.2
O1—C1—C6124.4 (3)C18—C17—H17B109.2
O1—C1—C2116.6 (3)H17A—C17—H17B107.9
C6—C1—C2119.0 (3)C17—C18—H18A109.5
C2—O3—C19117.6 (2)C17—C18—H18B109.5
C2—O3—Nd1120.25 (18)H18A—C18—H18B109.5
C19—O3—Nd1122.16 (18)C17—C18—H18C109.5
C3—C2—O3125.4 (3)H18A—C18—H18C109.5
C3—C2—C1121.2 (3)H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O7i0.932.363.277 (4)168
C9—H9A···O7ii0.972.423.290 (5)149
C20—H20A···O110.962.453.154 (5)130
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z.
Table 1
Selected geometric parameters (Å) top
Nd1—O12.437 (2)Nd1—O112.521 (3)
Nd1—O32.671 (2)Nd1—O122.578 (3)
Nd1—O42.631 (2)O2—Cu11.904 (2)
Nd1—O52.536 (3)O2—Nd12.396 (2)
Nd1—O62.569 (3)Cu1—O11.900 (2)
Nd1—O82.493 (2)Cu1—N11.906 (3)
Nd1—O92.543 (3)Cu1—N21.911 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O7i0.932.363.277 (4)168
C9—H9A···O7ii0.972.423.290 (5)149
C20—H20A···O110.962.453.154 (5)130
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z.
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
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