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Acta Cryst. (2007). E63, m2122    [ doi:10.1107/S1600536807033247 ]

[[mu]-N,N'-Bis(3-ethoxy-2-oxidobenzylidene)propane-1,2-diamine](methanol)trinitratocopper(II)neodymium(III)

Y. Sui, R.-H. Hu, J.-L. Peng and S. W. Ng

Abstract top

The Cu atom in the title compound (systematic name: {6,6'-diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1[kappa]4O1,O1',O6,O6':2[kappa]4O1,N,N',O1'}(methanol-2[kappa]O)trinitrato-1[kappa]6O,O'-copper(II)neodymium(III)), [CuNd(C21H22N2O4)(NO3)3(CH4O)], is N,N',O,O'-chelated by the deprotonated Schiff base, the four chelating atoms forming a square plane above which lies the methanol molecule. The (C21H24N2O4)(CH4O)Cu unit uses the two ethoxy and two hydroxy O atoms to chelate the (NO3)3Nd unit. The CuII atom exists in a square-pyramidal geometry and the NdIII atom in a bicapped square-antiprismatic geometry. Molecules are linked by O-H...O hydrogen bonds into a linear chain along the b axis. Some C and H atoms of the Schiff base are disordered equally over two positions.

Comment top

The isostructural lutetium compound is described in the preceding report (Sui et al., 2007).

Related literature top

For the isostructural lutetium compound structure, see Sui et al. (2007).

Experimental top

The Schiff base used to make the title compound was synthesized by the condensation of 3-ethoxysalicylaldehyde and 1,2- diaminopropane in a 2:1 molar ratio. Copper diacetate monohydrate (0.17 g, 1 mmol) and the ligand (0.37 g, 1 mmol) were heated in methanol (50 ml) for 3 h. Neodymium nitrate hexahydrate (0.44 g, 1 mmol) was added and then mixture was heated for another 3 h. Cooling the solution gave a precipitate, which was collected and washed with diethyl ether. Crystals were obtained upon recrystallization from methanol.

Refinement top

The part of the Schiff base that is made up of the C10 and C11 atoms (that belong to the cyclic system) is disordered over two positions; the occupancies of each set of atoms was arbitrarily fixed as 0.5. The displacement parameters of primed atoms were set to those of the unprimed ones. The C10—C11 and C11—C12 bond lengths were restrained to 1.50 (1) Å and the C10···C12 distance to 2.45 (1) Å. The displacement parameters of C10, C11 and C12 were restrained to approximate isotropic behaviour. The carbon- and oxygen-bound H atoms were positioned geometrically (C–H = 0.93–0.97 Å and O—H = 0.82 Å), and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C,O). The final difference Fourier map had a large peak at 1.2 Å from O6.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot of [CuNd(C21H22N2O4)(CH4O)(NO3)3]; ellipsoids are drawn at the 30% probabilty level, and H atoms are shown as spheres of arbitrary radius. Only one disorder component is shown.
({6,6'-diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ4O1,O1',O6,O6':2κ4O1, N,N',O1'}(methanol-2κO)trinitrato- 1κ6O,O'-copper(II)neodymium(III)) top
Crystal data top
[CuNd(C21H22N2O4)(NO3)3(CH4O)]F(000) = 1584
Mr = 794.27Dx = 1.785 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8519 reflections
a = 9.2004 (4) Åθ = 2.2–27.4°
b = 20.5069 (8) ŵ = 2.53 mm−1
c = 15.6901 (6) ÅT = 295 K
β = 93.111 (1)°Block, red
V = 2955.9 (2) Å30.34 × 0.13 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		6644 independent reflections
Radiation source: fine-focus sealed tube5212 reflections with I > 2σ(I)
graphiteRint = 0.027
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.426, Tmax = 0.768k = −26→26
21321 measured reflectionsl = −20→20
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0498P)2 + 17.0691P]
where P = (Fo2 + 2Fc2)/3
6644 reflections(Δ/σ)max = 0.001
395 parametersΔρmax = 1.04 e Å−3
10 restraintsΔρmin = −0.68 e Å−3
Crystal data top
[CuNd(C21H22N2O4)(NO3)3(CH4O)]V = 2955.9 (2) Å3
Mr = 794.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2004 (4) ŵ = 2.53 mm−1
b = 20.5069 (8) ÅT = 295 K
c = 15.6901 (6) Å0.34 × 0.13 × 0.11 mm
β = 93.111 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		6644 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5212 reflections with I > 2σ(I)
Tmin = 0.426, Tmax = 0.768Rint = 0.027
21321 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0498P)2 + 17.0691P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.154Δρmax = 1.04 e Å−3
S = 1.14Δρmin = −0.68 e Å−3
6644 reflectionsAbsolute structure: ?
395 parametersFlack parameter: ?
10 restraintsRogers parameter: ?
H-atom parameters constrained
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Nd10.36649 (4)0.341072 (17)0.25006 (3)0.04394 (13)
Cu10.33005 (10)0.50577 (4)0.29959 (6)0.0486 (2)
O10.1453 (6)0.3478 (2)0.1359 (4)0.0575 (14)
O20.2273 (6)0.4403 (2)0.2355 (4)0.0578 (14)
O30.4766 (6)0.4393 (2)0.3103 (4)0.0562 (14)
O40.6487 (5)0.3420 (2)0.2987 (4)0.0523 (12)
O50.4301 (11)0.5592 (4)0.1838 (5)0.118 (3)
H5O0.49260.58680.19520.141*
O60.1577 (8)0.3228 (5)0.3439 (5)0.096 (2)
O70.3543 (9)0.3409 (5)0.4117 (5)0.105 (3)
O80.1590 (10)0.3344 (3)0.4808 (5)0.095 (2)
O90.4799 (8)0.3825 (3)0.1171 (4)0.0774 (18)
O100.4850 (8)0.2788 (3)0.1368 (4)0.0755 (18)
O110.6037 (12)0.3199 (5)0.0342 (6)0.127 (3)
O120.2348 (7)0.2302 (3)0.2231 (5)0.0765 (19)
O130.4328 (7)0.2252 (3)0.3004 (4)0.0702 (17)
O140.3190 (8)0.1367 (3)0.2636 (5)0.090 (2)
N10.1700 (8)0.5660 (3)0.3028 (5)0.066 (2)
N20.4296 (8)0.5647 (3)0.3777 (5)0.0597 (17)
N30.2211 (10)0.3338 (3)0.4139 (5)0.0647 (19)
N40.5249 (10)0.3268 (4)0.0932 (5)0.076 (2)
N50.3294 (8)0.1962 (3)0.2621 (5)0.0582 (17)
C10.1630 (14)0.3442 (6)−0.0207 (7)0.101 (4)
H1A0.14430.3168−0.06970.152*
H1B0.26320.3575−0.01790.152*
H1C0.10170.3820−0.02540.152*
C20.1310 (11)0.3065 (4)0.0602 (6)0.068 (2)
H2A0.03300.28910.05450.082*
H2B0.19790.27010.06690.082*
C30.0446 (9)0.3977 (4)0.1433 (5)0.0556 (19)
C4−0.0931 (11)0.3986 (5)0.1044 (7)0.079 (3)
H4−0.12540.36470.06880.095*
C5−0.1829 (11)0.4514 (6)0.1196 (7)0.084 (3)
H5−0.27650.45270.09410.101*
C6−0.1359 (10)0.5010 (5)0.1708 (7)0.071 (3)
H6−0.19920.53520.18040.086*
C70.0062 (8)0.5027 (4)0.2104 (6)0.0553 (19)
C80.0942 (8)0.4479 (3)0.1983 (5)0.0496 (17)
C90.0431 (11)0.5567 (4)0.2632 (6)0.072 (3)
H9−0.02840.58800.27030.086*
C100.2181 (17)0.6309 (6)0.3334 (14)0.074 (5)0.50
H100.26500.65450.28800.089*0.50
C10'0.195 (2)0.6127 (7)0.3723 (10)0.074 (5)0.50
H10'0.16310.58890.42220.089*0.50
C110.1042 (13)0.6729 (5)0.3711 (9)0.108 (4)
H11A0.14910.71140.39540.162*0.50
H11B0.05810.64910.41490.162*0.50
H11C0.03250.68520.32730.162*0.50
H11D0.00310.66210.36140.162*0.50
H11E0.11810.69560.42450.162*0.50
H11F0.13420.70040.32570.162*0.50
C120.328 (3)0.6143 (14)0.405 (2)0.096 (7)0.50
H12A0.38100.65330.42190.116*0.50
H12B0.27750.59850.45320.116*0.50
C12'0.353 (2)0.6253 (11)0.395 (3)0.096 (7)0.50
H12C0.38850.66050.35990.116*0.50
H12D0.36740.63740.45420.116*0.50
C130.5624 (10)0.5605 (4)0.4056 (5)0.062 (2)
H130.60080.59440.43910.074*
C140.6573 (10)0.5057 (4)0.3882 (5)0.058 (2)
C150.8015 (10)0.5096 (4)0.4202 (6)0.066 (2)
H150.83300.54680.44970.079*
C160.8963 (10)0.4605 (4)0.4093 (6)0.066 (2)
H160.99300.46520.42890.079*
C170.8515 (8)0.4033 (4)0.3693 (5)0.0566 (19)
H170.91680.36930.36270.068*
C180.7074 (9)0.3974 (4)0.3391 (5)0.0501 (18)
C190.6091 (8)0.4481 (3)0.3459 (5)0.0471 (16)
C200.7444 (9)0.2873 (4)0.2865 (6)0.063 (2)
H20A0.83600.30340.26710.075*
H20B0.70120.25930.24230.075*
C210.7736 (12)0.2480 (5)0.3661 (7)0.087 (3)
H21A0.77470.20250.35180.130*
H21B0.69860.25610.40490.130*
H21C0.86620.26020.39240.130*
C220.3945 (19)0.5487 (7)0.1005 (8)0.131 (6)
H22A0.47790.55650.06780.196*
H22B0.31730.57770.08190.196*
H22C0.36290.50440.09260.196*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Nd10.0452 (2)0.03140 (19)0.0547 (2)0.00066 (16)−0.00207 (16)−0.00479 (16)
Cu10.0533 (5)0.0312 (4)0.0611 (6)0.0019 (4)0.0023 (4)−0.0057 (4)
O10.059 (3)0.046 (3)0.066 (3)0.000 (2)−0.013 (3)−0.008 (2)
O20.053 (3)0.038 (3)0.081 (4)0.009 (2)−0.013 (3)−0.009 (3)
O30.050 (3)0.039 (3)0.078 (4)0.007 (2)−0.018 (3)−0.015 (2)
O40.045 (3)0.041 (3)0.070 (3)−0.002 (2)−0.003 (2)−0.011 (2)
O50.164 (9)0.118 (7)0.074 (5)−0.075 (6)0.033 (5)−0.004 (5)
O60.067 (4)0.156 (8)0.066 (4)0.019 (5)0.007 (4)0.006 (5)
O70.085 (6)0.162 (9)0.066 (4)−0.037 (5)−0.002 (4)−0.010 (5)
O80.136 (7)0.077 (5)0.078 (5)−0.009 (4)0.045 (5)0.002 (4)
O90.088 (5)0.064 (4)0.081 (4)−0.002 (3)0.017 (4)0.012 (3)
O100.098 (5)0.058 (4)0.072 (4)0.000 (3)0.020 (4)−0.008 (3)
O110.156 (9)0.129 (7)0.102 (6)−0.027 (6)0.074 (6)−0.020 (5)
O120.064 (4)0.049 (3)0.114 (5)−0.006 (3)−0.019 (4)0.006 (3)
O130.059 (4)0.051 (3)0.098 (5)−0.008 (3)−0.018 (3)0.010 (3)
O140.103 (5)0.031 (3)0.137 (7)−0.012 (3)0.013 (5)−0.002 (3)
N10.059 (5)0.042 (4)0.098 (6)0.013 (3)−0.001 (4)−0.010 (4)
N20.071 (5)0.042 (3)0.067 (4)0.001 (3)0.002 (4)−0.013 (3)
N30.090 (6)0.042 (4)0.063 (5)0.000 (4)0.017 (4)−0.003 (3)
N40.083 (6)0.082 (6)0.063 (5)−0.011 (5)0.012 (4)−0.008 (4)
N50.068 (5)0.034 (3)0.074 (5)−0.007 (3)0.017 (4)−0.002 (3)
C10.111 (10)0.126 (11)0.066 (7)−0.008 (8)0.001 (6)−0.001 (7)
C20.076 (6)0.055 (5)0.070 (6)−0.001 (4)−0.018 (5)−0.014 (4)
C30.051 (5)0.049 (4)0.066 (5)0.007 (3)−0.002 (4)0.005 (4)
C40.078 (7)0.073 (6)0.084 (7)0.009 (5)−0.021 (5)0.000 (5)
C50.056 (6)0.099 (8)0.096 (8)0.021 (6)−0.012 (5)0.010 (6)
C60.048 (5)0.062 (5)0.102 (7)0.007 (4)−0.006 (5)0.008 (5)
C70.036 (4)0.055 (5)0.074 (5)0.018 (3)−0.006 (4)0.009 (4)
C80.040 (4)0.040 (4)0.069 (5)0.002 (3)0.000 (3)0.009 (3)
C90.078 (7)0.051 (5)0.089 (7)0.027 (5)0.023 (5)0.004 (4)
C100.102 (11)0.030 (7)0.091 (14)0.014 (7)0.016 (10)−0.004 (7)
C10'0.102 (11)0.030 (7)0.091 (14)0.014 (7)0.016 (10)−0.004 (7)
C110.100 (9)0.075 (7)0.151 (12)0.020 (7)0.013 (8)−0.012 (7)
C120.072 (10)0.065 (9)0.149 (13)0.015 (8)−0.016 (9)−0.058 (9)
C12'0.072 (10)0.065 (9)0.149 (13)0.015 (8)−0.016 (9)−0.058 (9)
C130.078 (6)0.045 (4)0.061 (5)−0.007 (4)−0.011 (4)−0.016 (4)
C140.075 (6)0.043 (4)0.055 (4)−0.005 (4)−0.004 (4)−0.002 (3)
C150.075 (6)0.060 (5)0.061 (5)−0.024 (5)−0.015 (4)−0.006 (4)
C160.051 (5)0.067 (6)0.078 (6)−0.008 (4)−0.015 (4)−0.006 (4)
C170.038 (4)0.063 (5)0.068 (5)0.003 (3)−0.005 (4)−0.001 (4)
C180.058 (5)0.045 (4)0.047 (4)−0.011 (3)−0.002 (3)−0.005 (3)
C190.046 (4)0.042 (4)0.053 (4)−0.003 (3)−0.004 (3)−0.003 (3)
C200.050 (5)0.055 (5)0.082 (6)0.011 (4)−0.006 (4)−0.012 (4)
C210.079 (7)0.070 (6)0.108 (8)0.000 (5)−0.013 (6)0.012 (6)
C220.195 (17)0.123 (11)0.078 (8)−0.026 (11)0.042 (9)0.018 (8)
Geometric parameters (Å, °) top
Nd1—O12.641 (5)C4—C51.390 (14)
Nd1—O22.408 (5)C4—H40.93
Nd1—O32.424 (5)C5—C61.351 (14)
Nd1—O42.666 (5)C5—H50.93
Nd1—O62.511 (7)C6—C71.417 (11)
Nd1—O72.545 (7)C6—H60.93
Nd1—O92.530 (7)C7—C81.404 (10)
Nd1—O102.487 (6)C7—C91.414 (13)
Nd1—O122.600 (6)C9—H90.93
Nd1—O132.567 (6)C10—C111.504 (10)
Cu1—O21.899 (5)C10—C121.502 (10)
Cu1—O31.918 (5)C10—H100.98
Cu1—O52.351 (7)C10'—C111.492 (9)
Cu1—N11.925 (7)C10'—C12'1.499 (10)
Cu1—N21.918 (7)C10'—H10'0.98
O1—C31.389 (9)C11—H11A0.96
O1—C21.459 (9)C11—H11B0.96
O2—C81.336 (9)C11—H11C0.96
O3—C191.326 (9)C11—H11D0.96
O4—C181.397 (8)C11—H11E0.96
O4—C201.444 (9)C11—H11F0.96
O5—C221.347 (14)C12—H12A0.97
O5—H5O0.8200C12—H12B0.97
O6—N31.236 (10)C12'—H12C0.97
O7—N31.236 (10)C12'—H12D0.97
O8—N31.221 (9)C13—C141.458 (12)
O9—N41.279 (10)C13—H130.93
O10—N41.264 (10)C14—C151.396 (12)
O11—N41.215 (11)C14—C191.414 (10)
O12—N51.249 (9)C15—C161.349 (13)
O13—N51.248 (9)C15—H150.93
O14—N51.225 (8)C16—C171.382 (12)
N1—C91.306 (12)C16—H160.93
N1—C10'1.460 (9)C17—C181.389 (11)
N1—C101.474 (9)C17—H170.93
N2—C131.278 (11)C18—C191.385 (11)
N2—C12'1.461 (10)C20—C211.498 (13)
N2—C121.461 (10)C20—H20A0.97
C1—C21.528 (14)C20—H20B0.97
C1—H1A0.96C21—H21A0.96
C1—H1B0.96C21—H21B0.96
C1—H1C0.96C21—H21C0.96
C2—H2A0.97C22—H22A0.96
C2—H2B0.97C22—H22B0.96
C3—C41.377 (12)C22—H22C0.96
C3—C81.404 (11)
O2—Nd1—O362.85 (17)O1—C2—H2A109.3
O2—Nd1—O10128.1 (2)C1—C2—H2A109.3
O3—Nd1—O10121.0 (2)O1—C2—H2B109.3
O2—Nd1—O676.2 (2)C1—C2—H2B109.3
O3—Nd1—O6102.2 (3)H2A—C2—H2B107.9
O10—Nd1—O6136.2 (3)C4—C3—O1125.1 (8)
O2—Nd1—O983.0 (2)C4—C3—C8121.5 (8)
O3—Nd1—O981.9 (2)O1—C3—C8113.3 (7)
O10—Nd1—O950.7 (2)C3—C4—C5118.4 (10)
O6—Nd1—O9153.7 (2)C3—C4—H4120.8
O2—Nd1—O792.5 (3)C5—C4—H4120.8
O3—Nd1—O769.7 (2)C6—C5—C4120.9 (9)
O10—Nd1—O7139.1 (3)C6—C5—H5119.6
O6—Nd1—O748.6 (2)C4—C5—H5119.6
O9—Nd1—O7149.8 (2)C5—C6—C7122.5 (9)
O2—Nd1—O13158.0 (2)C5—C6—H6118.7
O3—Nd1—O13124.21 (18)C7—C6—H6118.7
O10—Nd1—O1368.8 (2)C8—C7—C6116.5 (8)
O6—Nd1—O1381.8 (3)C8—C7—C9125.8 (7)
O9—Nd1—O13117.6 (2)C6—C7—C9117.6 (8)
O7—Nd1—O1373.4 (3)O2—C8—C3116.2 (7)
O2—Nd1—O12118.85 (19)O2—C8—C7123.8 (7)
O3—Nd1—O12166.3 (2)C3—C8—C7120.0 (7)
O10—Nd1—O1269.7 (2)N1—C9—C7124.9 (7)
O6—Nd1—O1266.4 (3)N1—C9—H9117.5
O9—Nd1—O12111.7 (2)C7—C9—H9117.5
O7—Nd1—O1296.6 (3)N1—C10—C11116.3 (11)
O13—Nd1—O1248.82 (19)N1—C10—C12102.5 (16)
O2—Nd1—O160.35 (17)C11—C10—C12106.9 (12)
O3—Nd1—O1120.77 (16)N1—C10—H10110.3
O10—Nd1—O183.9 (2)C11—C10—H10110.3
O6—Nd1—O179.6 (2)C12—C10—H10110.3
O9—Nd1—O176.1 (2)N1—C10'—C11117.9 (11)
O7—Nd1—O1127.0 (2)N1—C10'—C12'113.6 (16)
O13—Nd1—O1114.73 (17)C11—C10'—C12'113.2 (12)
O12—Nd1—O166.42 (18)N1—C10'—H10'103.2
O2—Nd1—O4121.74 (16)C11—C10'—H10'103.2
O3—Nd1—O460.19 (16)C12'—C10'—H10'103.2
O10—Nd1—O475.5 (2)C10—C11—H11A109.5
O6—Nd1—O4126.6 (2)C10—C11—H11B109.5
O9—Nd1—O478.2 (2)H11A—C11—H11B109.5
O7—Nd1—O479.0 (2)C10—C11—H11C109.5
O13—Nd1—O472.95 (17)H11A—C11—H11C109.5
O12—Nd1—O4119.37 (17)H11B—C11—H11C109.5
O1—Nd1—O4153.69 (19)C10'—C11—H11D110.3
O2—Cu1—O382.6 (2)C10'—C11—H11E110.0
O2—Cu1—N2172.2 (3)H11D—C11—H11E109.5
O3—Cu1—N294.7 (3)C10'—C11—H11F108.1
O2—Cu1—N196.2 (3)H11D—C11—H11F109.5
O3—Cu1—N1171.4 (3)H11E—C11—H11F109.5
N2—Cu1—N185.3 (3)N2—C12—C10111.0 (15)
O2—Cu1—O597.2 (3)N2—C12—H12A109.4
O3—Cu1—O595.5 (3)C10—C12—H12A109.4
N2—Cu1—O590.4 (3)N2—C12—H12B109.4
N1—Cu1—O593.1 (4)C10—C12—H12B109.4
C3—O1—C2117.7 (6)H12A—C12—H12B108.0
C3—O1—Nd1118.3 (4)N2—C12'—C10'106.3 (14)
C2—O1—Nd1123.7 (5)N2—C12'—H12C110.5
C8—O2—Cu1124.5 (5)C10'—C12'—H12C110.5
C8—O2—Nd1127.6 (4)N2—C12'—H12D110.5
Cu1—O2—Nd1107.5 (2)C10'—C12'—H12D110.5
C19—O3—Cu1124.5 (4)H12C—C12'—H12D108.7
C19—O3—Nd1129.2 (4)N2—C13—C14124.0 (7)
Cu1—O3—Nd1106.2 (2)N2—C13—H13118.0
C18—O4—C20117.9 (6)C14—C13—H13118.0
C18—O4—Nd1118.8 (4)C15—C14—C19119.0 (8)
C20—O4—Nd1123.2 (4)C15—C14—C13117.1 (7)
C22—O5—Cu1126.2 (8)C19—C14—C13123.8 (8)
C22—O5—H5O116.9C16—C15—C14121.3 (8)
Cu1—O5—H5O116.9C16—C15—H15119.3
N3—O6—Nd198.9 (6)C14—C15—H15119.3
N3—O7—Nd197.2 (5)C15—C16—C17120.8 (8)
N4—O9—Nd195.5 (5)C15—C16—H16119.6
N4—O10—Nd198.0 (5)C17—C16—H16119.6
N5—O12—Nd195.8 (4)C16—C17—C18119.0 (8)
N5—O13—Nd197.5 (4)C16—C17—H17120.5
C9—N1—C10'123.5 (10)C18—C17—H17120.5
C9—N1—C10122.1 (10)C19—C18—C17121.6 (7)
C9—N1—Cu1124.0 (6)C19—C18—O4114.1 (6)
C10'—N1—Cu1110.5 (7)C17—C18—O4124.3 (7)
C10—N1—Cu1111.8 (7)O3—C19—C18117.1 (6)
C13—N2—C12'117.2 (11)O3—C19—C14124.7 (7)
C13—N2—C12124.4 (12)C18—C19—C14118.3 (7)
C13—N2—Cu1126.2 (5)O4—C20—C21113.0 (8)
C12'—N2—Cu1115.7 (11)O4—C20—H20A109.0
C12—N2—Cu1109.3 (11)C21—C20—H20A109.0
O8—N3—O7122.2 (9)O4—C20—H20B109.0
O8—N3—O6123.0 (9)C21—C20—H20B109.0
O7—N3—O6114.7 (8)H20A—C20—H20B107.8
O11—N4—O10121.7 (9)C20—C21—H21A109.5
O11—N4—O9123.0 (9)C20—C21—H21B109.5
O10—N4—O9115.3 (8)H21A—C21—H21B109.5
O14—N5—O13121.6 (8)C20—C21—H21C109.5
O14—N5—O12120.8 (8)H21A—C21—H21C109.5
O13—N5—O12117.6 (6)H21B—C21—H21C109.5
C2—C1—H1A109.5O5—C22—H22A109.5
C2—C1—H1B109.5O5—C22—H22B109.5
H1A—C1—H1B109.5H22A—C22—H22B109.5
C2—C1—H1C109.5O5—C22—H22C109.5
H1A—C1—H1C109.5H22A—C22—H22C109.5
H1B—C1—H1C109.5H22B—C22—H22C109.5
O1—C2—C1111.7 (8)
O2—Nd1—O1—C3−16.6 (5)O6—Nd1—O12—N5−103.0 (5)
O3—Nd1—O1—C3−34.8 (6)O9—Nd1—O12—N5105.4 (5)
O10—Nd1—O1—C3−157.5 (6)O7—Nd1—O12—N5−64.0 (5)
O6—Nd1—O1—C363.3 (6)O13—Nd1—O12—N5−2.9 (5)
O9—Nd1—O1—C3−106.5 (6)O1—Nd1—O12—N5168.4 (6)
O7—Nd1—O1—C351.9 (6)O4—Nd1—O12—N517.1 (6)
O13—Nd1—O1—C3139.3 (5)O2—Nd1—O13—N565.8 (8)
O12—Nd1—O1—C3132.0 (6)O3—Nd1—O13—N5168.0 (4)
O4—Nd1—O1—C3−119.0 (6)O10—Nd1—O13—N5−78.2 (5)
O2—Nd1—O1—C2156.5 (7)O6—Nd1—O13—N568.7 (5)
O3—Nd1—O1—C2138.3 (6)O9—Nd1—O13—N5−92.6 (5)
O10—Nd1—O1—C215.6 (6)O7—Nd1—O13—N5117.8 (5)
O6—Nd1—O1—C2−123.6 (6)O12—Nd1—O13—N52.9 (5)
O9—Nd1—O1—C266.6 (6)O1—Nd1—O13—N5−5.9 (6)
O7—Nd1—O1—C2−135.0 (6)O4—Nd1—O13—N5−158.9 (5)
O13—Nd1—O1—C2−47.7 (6)O2—Cu1—N1—C9−4.2 (8)
O12—Nd1—O1—C2−54.9 (6)N2—Cu1—N1—C9−176.5 (8)
O4—Nd1—O1—C254.1 (7)O5—Cu1—N1—C993.3 (8)
O3—Cu1—O2—C8−179.4 (7)O2—Cu1—N1—C10'160.1 (11)
N1—Cu1—O2—C89.1 (7)N2—Cu1—N1—C10'−12.2 (11)
O5—Cu1—O2—C8−84.8 (7)O5—Cu1—N1—C10'−102.4 (11)
O3—Cu1—O2—Nd17.6 (3)O2—Cu1—N1—C10−167.9 (10)
N1—Cu1—O2—Nd1−163.9 (3)N2—Cu1—N1—C1019.8 (11)
O5—Cu1—O2—Nd1102.3 (3)O5—Cu1—N1—C10−70.3 (11)
O3—Nd1—O2—C8−179.4 (7)O3—Cu1—N2—C1313.7 (8)
O10—Nd1—O2—C871.1 (7)N1—Cu1—N2—C13−174.8 (8)
O6—Nd1—O2—C8−67.6 (6)O5—Cu1—N2—C13−81.8 (8)
O9—Nd1—O2—C896.1 (6)O3—Cu1—N2—C12−163.5 (17)
O7—Nd1—O2—C8−113.8 (6)N1—Cu1—N2—C127.9 (17)
O13—Nd1—O2—C8−64.7 (9)O5—Cu1—N2—C12101.0 (17)
O12—Nd1—O2—C8−14.8 (7)Nd1—O7—N3—O8−175.8 (7)
O1—Nd1—O2—C818.1 (6)Nd1—O7—N3—O67.7 (9)
O4—Nd1—O2—C8167.5 (6)Nd1—O6—N3—O8175.7 (7)
O3—Nd1—O2—Cu1−6.7 (2)Nd1—O6—N3—O7−7.8 (9)
O10—Nd1—O2—Cu1−116.2 (3)Nd1—O10—N4—O11171.8 (9)
O6—Nd1—O2—Cu1105.1 (3)Nd1—O10—N4—O9−6.4 (9)
O9—Nd1—O2—Cu1−91.2 (3)Nd1—O9—N4—O11−171.9 (10)
O7—Nd1—O2—Cu158.9 (3)Nd1—O9—N4—O106.2 (9)
O13—Nd1—O2—Cu1108.0 (5)Nd1—O13—N5—O14176.1 (7)
O12—Nd1—O2—Cu1157.9 (3)Nd1—O13—N5—O12−5.2 (8)
O1—Nd1—O2—Cu1−169.2 (4)Nd1—O12—N5—O14−176.2 (7)
O4—Nd1—O2—Cu1−19.8 (4)Nd1—O12—N5—O135.1 (8)
O2—Cu1—O3—C19173.7 (7)C3—O1—C2—C167.5 (11)
N2—Cu1—O3—C19−13.7 (7)Nd1—O1—C2—C1−105.7 (8)
O5—Cu1—O3—C1977.2 (6)C2—O1—C3—C424.3 (13)
O2—Cu1—O3—Nd1−7.5 (3)Nd1—O1—C3—C4−162.2 (8)
N2—Cu1—O3—Nd1165.1 (3)C2—O1—C3—C8−158.0 (7)
O5—Cu1—O3—Nd1−104.1 (3)Nd1—O1—C3—C815.5 (9)
O2—Nd1—O3—C19−174.7 (7)O1—C3—C4—C5178.5 (9)
O10—Nd1—O3—C19−54.6 (7)C8—C3—C4—C51.0 (15)
O6—Nd1—O3—C19117.9 (7)C3—C4—C5—C60.5 (17)
O9—Nd1—O3—C19−88.4 (7)C4—C5—C6—C71.1 (17)
O7—Nd1—O3—C1981.3 (7)C5—C6—C7—C8−4.0 (15)
O13—Nd1—O3—C1929.6 (7)C5—C6—C7—C9−179.5 (10)
O12—Nd1—O3—C1984.6 (10)Cu1—O2—C8—C3170.9 (6)
O1—Nd1—O3—C19−156.9 (6)Nd1—O2—C8—C3−17.5 (10)
O4—Nd1—O3—C19−7.5 (6)Cu1—O2—C8—C7−8.0 (11)
O2—Nd1—O3—Cu16.6 (2)Nd1—O2—C8—C7163.6 (6)
O10—Nd1—O3—Cu1126.7 (3)C4—C3—C8—O2177.0 (8)
O6—Nd1—O3—Cu1−60.8 (3)O1—C3—C8—O2−0.8 (10)
O9—Nd1—O3—Cu192.9 (3)C4—C3—C8—C7−4.1 (13)
O7—Nd1—O3—Cu1−97.4 (3)O1—C3—C8—C7178.2 (7)
O13—Nd1—O3—Cu1−149.1 (2)C6—C7—C8—O2−175.8 (8)
O12—Nd1—O3—Cu1−94.1 (8)C9—C7—C8—O2−0.7 (14)
O1—Nd1—O3—Cu124.4 (4)C6—C7—C8—C35.3 (12)
O4—Nd1—O3—Cu1173.8 (3)C9—C7—C8—C3−179.5 (9)
O2—Nd1—O4—C1818.1 (6)C10'—N1—C9—C7−164.5 (12)
O3—Nd1—O4—C184.7 (5)C10—N1—C9—C7159.9 (12)
O10—Nd1—O4—C18144.3 (5)Cu1—N1—C9—C7−2.2 (14)
O6—Nd1—O4—C18−78.3 (6)C8—C7—C9—N16.2 (16)
O9—Nd1—O4—C1892.2 (5)C6—C7—C9—N1−178.7 (9)
O7—Nd1—O4—C18−68.0 (5)C9—N1—C10—C1139 (2)
O13—Nd1—O4—C18−143.9 (5)C10'—N1—C10—C11−63.2 (14)
O12—Nd1—O4—C18−159.5 (5)Cu1—N1—C10—C11−156.7 (13)
O1—Nd1—O4—C18104.6 (6)C9—N1—C10—C12155.4 (16)
O2—Nd1—O4—C20−162.8 (6)C10'—N1—C10—C1253 (2)
O3—Nd1—O4—C20−176.2 (6)Cu1—N1—C10—C12−40.5 (16)
O10—Nd1—O4—C20−36.6 (6)C9—N1—C10'—C11−31 (2)
O6—Nd1—O4—C20100.8 (6)C10—N1—C10'—C1165.9 (14)
O9—Nd1—O4—C20−88.7 (6)Cu1—N1—C10'—C11164.2 (14)
O7—Nd1—O4—C20111.1 (6)C9—N1—C10'—C12'−167.3 (19)
O13—Nd1—O4—C2035.2 (6)C10—N1—C10'—C12'−70 (3)
O12—Nd1—O4—C2019.6 (7)Cu1—N1—C10'—C12'28 (2)
O1—Nd1—O4—C20−76.3 (7)N1—C10'—C11—C10−65.8 (15)
O2—Cu1—O5—C2210.2 (12)C12'—C10'—C11—C1070 (3)
O3—Cu1—O5—C2293.4 (12)N1—C10—C11—C10'62.9 (14)
N2—Cu1—O5—C22−171.8 (12)C12—C10—C11—C10'−51 (3)
N1—Cu1—O5—C22−86.4 (12)C13—N2—C12—C10148.7 (17)
O2—Nd1—O6—N3−101.4 (6)C12'—N2—C12—C1085 (9)
O3—Nd1—O6—N3−43.7 (6)Cu1—N2—C12—C10−34 (3)
O10—Nd1—O6—N3127.1 (6)N1—C10—C12—N248 (3)
O9—Nd1—O6—N3−140.3 (5)C11—C10—C12—N2170 (2)
O7—Nd1—O6—N34.6 (5)C13—N2—C12'—C10'−168.5 (18)
O13—Nd1—O6—N379.7 (6)C12—N2—C12'—C10'−45 (7)
O12—Nd1—O6—N3128.1 (6)Cu1—N2—C12'—C10'22 (3)
O1—Nd1—O6—N3−163.2 (6)N1—C10'—C12'—N2−32 (3)
O4—Nd1—O6—N318.1 (7)C11—C10'—C12'—N2−169.8 (19)
O2—Nd1—O7—N364.6 (6)C12'—N2—C13—C14−175 (2)
O3—Nd1—O7—N3124.3 (7)C12—N2—C13—C14171 (2)
O10—Nd1—O7—N3−121.4 (6)Cu1—N2—C13—C14−6.1 (13)
O6—Nd1—O7—N3−4.6 (5)N2—C13—C14—C15177.3 (9)
O9—Nd1—O7—N3145.0 (5)N2—C13—C14—C19−6.6 (14)
O13—Nd1—O7—N3−98.3 (6)C19—C14—C15—C162.0 (13)
O12—Nd1—O7—N3−54.9 (6)C13—C14—C15—C16178.2 (9)
O1—Nd1—O7—N310.5 (7)C14—C15—C16—C17−3.0 (15)
O4—Nd1—O7—N3−173.6 (6)C15—C16—C17—C181.0 (14)
O2—Nd1—O9—N4−158.2 (6)C16—C17—C18—C192.0 (13)
O3—Nd1—O9—N4138.3 (6)C16—C17—C18—O4−179.1 (8)
O10—Nd1—O9—N4−3.7 (5)C20—O4—C18—C19178.2 (7)
O6—Nd1—O9—N4−120.3 (7)Nd1—O4—C18—C19−2.7 (8)
O7—Nd1—O9—N4118.8 (7)C20—O4—C18—C17−0.8 (11)
O13—Nd1—O9—N413.8 (6)Nd1—O4—C18—C17178.3 (6)
O12—Nd1—O9—N4−39.9 (6)Cu1—O3—C19—C18−172.3 (5)
O1—Nd1—O9—N4−97.1 (6)Nd1—O3—C19—C189.2 (10)
O4—Nd1—O9—N477.2 (5)Cu1—O3—C19—C146.4 (11)
O2—Nd1—O10—N436.6 (7)Nd1—O3—C19—C14−172.1 (6)
O3—Nd1—O10—N4−41.6 (6)C17—C18—C19—O3175.8 (7)
O6—Nd1—O10—N4148.9 (5)O4—C18—C19—O3−3.3 (10)
O9—Nd1—O10—N43.7 (5)C17—C18—C19—C14−2.9 (12)
O7—Nd1—O10—N4−135.9 (6)O4—C18—C19—C14178.0 (7)
O13—Nd1—O10—N4−159.7 (6)C15—C14—C19—O3−177.6 (8)
O12—Nd1—O10—N4147.9 (6)C13—C14—C19—O36.4 (13)
O1—Nd1—O10—N480.8 (6)C15—C14—C19—C181.0 (12)
O4—Nd1—O10—N4−82.7 (6)C13—C14—C19—C18−175.0 (8)
O2—Nd1—O12—N5−160.6 (5)C18—O4—C20—C2178.0 (9)
O3—Nd1—O12—N5−67.2 (10)Nd1—O4—C20—C21−101.1 (7)
O10—Nd1—O12—N576.2 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O14i0.822.082.89 (1)165
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Nd1—O12.641 (5)Nd1—O122.600 (6)
Nd1—O22.408 (5)Nd1—O132.567 (6)
Nd1—O32.424 (5)Cu1—O21.899 (5)
Nd1—O42.666 (5)Cu1—O31.918 (5)
Nd1—O62.511 (7)Cu1—O52.351 (7)
Nd1—O72.545 (7)Cu1—N11.925 (7)
Nd1—O92.530 (7)Cu1—N21.918 (7)
Nd1—O102.487 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O14i0.822.082.89 (1)165
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
Acknowledgements top

We thank the Department of Education of Jiangxi Province (grant Nos. 2007317 and 05YB195) and the University of Malaya for supporting this study.

references
References top

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