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Acta Cryst. (2007). E63, m2192    [ doi:10.1107/S1600536807034460 ]

Acetone[[mu]-N,N'-bis(3-methoxy-2-oxidobenzylidene)-1,2-propanediamine]trinitratocopper(II)praseodymium(III)

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

Abstract top

In the title complex (systematic name: (acetone-2[kappa]O){6,6'-dimethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1[kappa]4O1,O1',O6,O6':2[kappa]4O1,N,N',O1'}trinitrato-1[kappa]6O,O'-copper(II)praseodymium(III)), [CuPr(C19H20N2O4)(NO3)3(C3H6O)], the CuII ion is five-coordinated by two O atoms and two N atoms of the deprotonated Schiff base and by the acetone, giving rise to a square-pyramidal geometry, whereas the PrIII ion is ten-coordinated by six nitrate O atoms and four O atoms of the deprotonated Schiff base. The C atoms, with attached H atoms, of the diaminopropane link are disordered over two positions with site occupancy factors of ca 0.7 and 0.3.

Comment top

As shown in Fig. 1, the octodentate Schiff base ligand links Cu and Pr atoms into a dinuclear complex through two phenolate O atoms, which is similar with the bonding reported for another copper-lanthanum complex of the same ligand (Kara et al., 2000). The PrIII 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 five-coordinate by two nitrogen atoms and two oxygen atoms from the ligand and one oxygen atom from acetone in a square-pyramidal geometry.

Related literature top

See Kara 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 methanol/acetone (4:1). The first two reactants were refluxed for 6 h, and the mixture was refluxed for another 3 h after the addition of praseodymium (III) nitrate hexahydrate. 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 C22H26CuN5O14Pr: C, 33.49; H, 3.32; Cu, 8.05; N, 8.88; Pr, 17.86; found: C, 33.10; H, 3.05; Cu, 7.85; N, 8.25; Pr, 17.23%.

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), C—H = 0.98 Å (methine C), and with Uiso(H) = 1.2Ueq(C) or C—H = 0.96 Å (methly C) and with Uiso(H) = 1.5Ueq(C). In complex (I), the diaminopropane is disordered and was refined with a split model over two positions, and with an occupancy of 0.289 (11) for C8, C9, C10, and 0.711 (11) for C8', C9', C10'.

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. The disordered C8', C9', C10' and all H atoms have been omitted.
(acetone-2κO){6,6'-dimethoxy-2,2'-[propane-1,2- diylbis(nitrilomethylidyne)]diphenolato- 1κ4O1,O1',O6,O6':2κ4O1,N,N',O1'}trinitrato- 1κ6O,O'-copper(II)neodymium(III) top
Crystal data top
[CuPr(C19H20N2O4)(NO3)3(C3H6O)]F(000) = 1555
Mr = 784.64Dx = 1.790 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 20972 reflections
a = 9.879 (3) Åθ = 3.0–27.5°
b = 18.887 (7) ŵ = 2.46 mm−1
c = 15.676 (5) ÅT = 295 K
β = 95.376 (14)°Block, colourless
V = 2912.2 (16) Å30.39 × 0.25 × 0.24 mm
Z = 4
Data collection top
Rigaku RAXIS-RAPID
diffractometer		6654 independent reflections
Radiation source: fine-focus sealed tube5376 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −12→12
Tmin = 0.447, Tmax = 0.567k = −24→24
25560 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0596P)2 + 1.9949P]
where P = (Fo2 + 2Fc2)/3
6654 reflections(Δ/σ)max = 0.004
421 parametersΔρmax = 1.00 e Å−3
56 restraintsΔρmin = −0.75 e Å−3
Crystal data top
[CuPr(C19H20N2O4)(NO3)3(C3H6O)]V = 2912.2 (16) Å3
Mr = 784.64Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.879 (3) ŵ = 2.46 mm−1
b = 18.887 (7) ÅT = 295 K
c = 15.676 (5) Å0.39 × 0.25 × 0.24 mm
β = 95.376 (14)°
Data collection top
Rigaku RAXIS-RAPID
diffractometer		6654 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		5376 reflections with I > 2σ(I)
Tmin = 0.447, Tmax = 0.567Rint = 0.033
25560 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.110Δρmax = 1.00 e Å−3
S = 1.11Δρmin = −0.75 e Å−3
6654 reflectionsAbsolute structure: ?
421 parametersFlack parameter: ?
56 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)
C10.8680 (4)0.2350 (2)0.3353 (3)0.0444 (9)
C20.9441 (5)0.1951 (2)0.3985 (3)0.0480 (10)
C31.0029 (6)0.2261 (3)0.4713 (4)0.0676 (15)
H11.05140.19890.51310.081*
C40.9895 (6)0.2994 (3)0.4825 (4)0.0748 (17)
H21.02670.32070.53280.090*
C50.9234 (5)0.3387 (3)0.4211 (4)0.0684 (16)
H30.91780.38740.42910.082*
C60.8622 (5)0.3091 (2)0.3451 (3)0.0520 (11)
C70.7993 (6)0.3557 (3)0.2800 (5)0.0760 (18)
H40.80570.40410.29070.091*
C110.5822 (7)0.2497 (4)0.0017 (4)0.0783 (19)
H110.54420.2763−0.04440.094*
C120.5947 (5)0.1744 (3)−0.0112 (3)0.0594 (13)
C130.5531 (6)0.1477 (4)−0.0920 (3)0.0750 (18)
H120.51490.1782−0.13420.090*
C140.5669 (7)0.0777 (4)−0.1105 (3)0.0761 (19)
H130.53690.0608−0.16470.091*
C150.6248 (5)0.0325 (3)−0.0499 (3)0.0606 (13)
H140.6348−0.0151−0.06300.073*
C160.6688 (5)0.0572 (3)0.0312 (3)0.0492 (11)
C170.6527 (5)0.1276 (3)0.0526 (3)0.0493 (11)
C180.7768 (6)−0.0526 (3)0.0730 (4)0.0636 (14)
H150.6997−0.08160.05460.095*
H170.8273−0.07420.12140.095*
H160.8340−0.04800.02700.095*
C191.0568 (7)0.0843 (3)0.4255 (4)0.0703 (16)
H181.14060.11020.42680.106*
H191.06670.03970.39760.106*
H201.03450.07640.48300.106*
C200.3179 (7)0.1927 (4)0.1389 (4)0.0841 (19)
H210.28960.22850.09750.126*
H220.24430.16040.14440.126*
H230.39420.16740.12040.126*
C210.3576 (6)0.2265 (3)0.2231 (4)0.0620 (13)
C220.2484 (8)0.2423 (5)0.2793 (5)0.102 (2)
H240.21310.19870.29970.154*
H250.17670.26800.24740.154*
H260.28490.27030.32720.154*
Cu10.70339 (7)0.24136 (3)0.17375 (4)0.05314 (16)
Pr10.78327 (2)0.072680 (11)0.251884 (13)0.03820 (9)
N10.7363 (6)0.3368 (2)0.2097 (4)0.0833 (17)
N20.6188 (6)0.2829 (3)0.0708 (3)0.0736 (14)
N31.0501 (4)0.0451 (2)0.1849 (3)0.0553 (10)
N40.7742 (5)−0.0693 (2)0.3381 (3)0.0607 (11)
N50.5171 (6)0.0863 (3)0.3227 (4)0.0774 (15)
O10.8088 (3)0.19986 (16)0.2688 (2)0.0501 (7)
O20.9507 (3)0.12417 (17)0.3795 (2)0.0516 (8)
O30.6936 (4)0.14686 (17)0.13258 (18)0.0510 (8)
O40.7309 (3)0.01636 (17)0.09667 (19)0.0496 (7)
O50.9915 (4)0.1033 (2)0.1734 (3)0.0686 (10)
O61.1512 (6)0.0298 (3)0.1524 (4)0.1089 (19)
O70.9956 (4)0.00182 (18)0.2334 (3)0.0631 (9)
O80.7247 (5)−0.0603 (2)0.2635 (2)0.0707 (11)
O90.7751 (6)−0.1266 (2)0.3731 (3)0.1046 (17)
O100.8210 (5)−0.0157 (2)0.3766 (2)0.0715 (10)
O110.5273 (5)0.0602 (3)0.2508 (3)0.0887 (14)
O120.4092 (6)0.0918 (4)0.3531 (5)0.133 (2)
O130.6254 (5)0.1080 (3)0.3616 (3)0.0890 (13)
O140.4757 (4)0.2408 (2)0.2439 (3)0.0718 (11)
C80.622 (2)0.3855 (8)0.1689 (15)0.067 (6)0.289 (11)
H50.55400.39320.20970.080*0.289 (11)
C90.674 (4)0.4528 (12)0.143 (2)0.139 (15)0.289 (11)
H60.70420.44850.08680.209*0.289 (11)
H70.74910.46680.18290.209*0.289 (11)
H80.60360.48790.14230.209*0.289 (11)
C100.5539 (19)0.3537 (8)0.0867 (10)0.044 (4)0.289 (11)
H90.45750.34740.09170.053*0.289 (11)
H100.56430.38530.03900.053*0.289 (11)
C8'0.7006 (12)0.3867 (5)0.1348 (6)0.083 (3)0.711 (11)
C9'0.7917 (14)0.3991 (6)0.0717 (10)0.128 (6)0.711 (11)
C10'0.6150 (14)0.3613 (5)0.0732 (7)0.088 (3)0.711 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.042 (2)0.037 (2)0.054 (2)−0.0015 (18)0.0044 (19)−0.0046 (18)
C20.048 (2)0.046 (2)0.049 (2)−0.006 (2)−0.004 (2)−0.0070 (19)
C30.069 (3)0.064 (3)0.066 (3)0.001 (3)−0.014 (3)−0.013 (3)
C40.071 (4)0.064 (4)0.086 (4)−0.003 (3)−0.013 (3)−0.036 (3)
C50.055 (3)0.043 (3)0.106 (5)−0.002 (2)−0.003 (3)−0.024 (3)
C60.040 (2)0.038 (2)0.077 (3)−0.0029 (19)0.000 (2)−0.007 (2)
C70.065 (3)0.029 (2)0.131 (6)−0.001 (2)−0.009 (4)0.003 (3)
C110.081 (4)0.098 (5)0.055 (3)0.029 (4)0.003 (3)0.038 (3)
C120.053 (3)0.086 (4)0.038 (2)0.012 (3)0.000 (2)0.017 (2)
C130.066 (3)0.115 (6)0.042 (3)0.005 (4)−0.004 (2)0.019 (3)
C140.066 (3)0.122 (6)0.038 (2)−0.010 (4)−0.009 (2)0.003 (3)
C150.055 (3)0.086 (4)0.040 (2)−0.014 (3)0.003 (2)−0.008 (2)
C160.045 (2)0.065 (3)0.038 (2)−0.006 (2)0.0057 (19)−0.001 (2)
C170.046 (2)0.069 (3)0.0327 (19)0.001 (2)0.0031 (18)0.007 (2)
C180.077 (4)0.054 (3)0.060 (3)0.006 (3)0.008 (3)−0.014 (2)
C190.076 (4)0.054 (3)0.074 (4)0.009 (3)−0.027 (3)0.001 (3)
C200.067 (4)0.092 (5)0.090 (4)−0.020 (3)−0.006 (3)−0.011 (4)
C210.055 (3)0.057 (3)0.074 (3)−0.003 (2)0.005 (3)0.004 (3)
C220.073 (4)0.131 (7)0.107 (5)0.001 (5)0.026 (4)−0.014 (5)
Cu10.0654 (4)0.0380 (3)0.0542 (3)0.0070 (3)−0.0038 (3)0.0120 (2)
Pr10.04735 (15)0.03195 (13)0.03429 (13)0.00098 (9)−0.00148 (9)0.00179 (8)
N10.096 (4)0.031 (2)0.116 (4)−0.002 (2)−0.026 (3)0.014 (3)
N20.094 (4)0.065 (3)0.062 (3)0.027 (3)0.003 (3)0.029 (2)
N30.055 (2)0.043 (2)0.069 (3)−0.0001 (19)0.014 (2)−0.0002 (19)
N40.080 (3)0.041 (2)0.057 (2)−0.011 (2)−0.014 (2)0.0130 (18)
N50.072 (3)0.081 (4)0.084 (4)0.004 (3)0.030 (3)0.008 (3)
O10.0594 (19)0.0348 (16)0.0529 (17)0.0021 (14)−0.0111 (15)0.0018 (13)
O20.0605 (19)0.0394 (16)0.0507 (17)0.0038 (14)−0.0174 (15)0.0000 (14)
O30.068 (2)0.0476 (18)0.0362 (15)0.0119 (15)−0.0032 (14)0.0074 (13)
O40.0578 (18)0.0493 (18)0.0407 (15)0.0011 (15)−0.0005 (14)−0.0058 (13)
O50.068 (2)0.052 (2)0.089 (3)0.0092 (18)0.024 (2)0.021 (2)
O60.098 (3)0.073 (3)0.169 (5)0.016 (3)0.080 (4)0.014 (3)
O70.062 (2)0.0446 (19)0.084 (2)0.0074 (16)0.0117 (19)0.0159 (17)
O80.098 (3)0.052 (2)0.056 (2)−0.020 (2)−0.023 (2)0.0102 (16)
O90.147 (4)0.064 (3)0.094 (3)−0.021 (3)−0.035 (3)0.031 (2)
O100.095 (2)0.0604 (19)0.0561 (17)−0.0169 (17)−0.0104 (17)0.0087 (15)
O110.058 (2)0.114 (4)0.094 (3)−0.008 (2)0.009 (2)−0.020 (3)
O120.081 (4)0.170 (6)0.159 (6)0.005 (4)0.070 (4)0.004 (5)
O130.0882 (15)0.0920 (16)0.0874 (15)0.0007 (10)0.0117 (10)−0.0043 (10)
O140.060 (2)0.080 (3)0.075 (2)−0.012 (2)0.004 (2)−0.017 (2)
C80.076 (12)0.023 (7)0.106 (15)0.018 (8)0.029 (11)0.014 (8)
C90.17 (4)0.10 (2)0.15 (3)0.07 (2)0.04 (3)0.00 (2)
C100.042 (5)0.043 (5)0.047 (5)−0.001 (3)0.002 (3)0.009 (3)
C8'0.090 (4)0.069 (4)0.088 (4)0.001 (3)0.006 (3)0.013 (3)
C9'0.128 (10)0.070 (7)0.197 (15)−0.013 (7)0.073 (10)0.023 (8)
C10'0.089 (3)0.088 (3)0.088 (3)0.0016 (11)0.0086 (11)0.0014 (11)
Geometric parameters (Å, °) top
C1—O11.325 (5)C21—C221.485 (9)
C1—C21.406 (7)C22—H240.9600
C1—C61.410 (6)C22—H250.9600
C2—C31.363 (7)C22—H260.9600
C2—O21.375 (5)Cu1—O31.897 (3)
C3—C41.404 (8)Cu1—O11.905 (3)
C3—H10.9300Cu1—N11.907 (5)
C4—C51.336 (9)Cu1—N21.915 (4)
C4—H20.9300Cu1—O142.594 (4)
C5—C61.401 (7)Cu1—Pr13.4774 (12)
C5—H30.9300Pr1—O12.427 (3)
C6—C71.443 (8)Pr1—O32.436 (3)
C7—N11.266 (9)Pr1—O132.518 (5)
C7—H40.9300Pr1—O72.528 (4)
C11—N21.273 (9)Pr1—O112.538 (4)
C11—C121.444 (9)Pr1—O52.559 (4)
C11—H110.9300Pr1—O102.571 (4)
C12—C131.388 (8)Pr1—O82.588 (4)
C12—C171.416 (7)Pr1—O22.658 (3)
C13—C141.363 (9)Pr1—O42.661 (3)
C13—H120.9300N1—C81.549 (19)
C14—C151.363 (8)N2—C101.514 (17)
C14—H130.9300N3—O61.199 (6)
C15—C161.384 (6)N3—O51.247 (6)
C15—H140.9300N3—O71.270 (5)
C16—O41.381 (6)N4—O91.214 (5)
C16—C171.384 (7)N4—O81.236 (5)
C17—O31.331 (5)N4—O101.244 (5)
C18—O41.440 (6)N5—O121.212 (7)
C18—H150.9600N5—O111.244 (7)
C18—H170.9600N5—O131.250 (7)
C18—H160.9600C8—C91.444 (19)
C19—O21.430 (6)C8—C101.52 (3)
C19—H180.9600C8—H50.9800
C19—H190.9600C9—H60.9600
C19—H200.9600C9—H70.9600
C20—C211.486 (8)C9—H80.9600
C20—H210.9600C10—H90.9700
C20—H220.9600C10—H100.9700
C20—H230.9600C8'—C10'1.313 (12)
C21—O141.213 (6)C8'—C9'1.417 (13)
O1—C1—C2116.9 (4)O1—Pr1—O8167.01 (13)
O1—C1—C6124.3 (4)O3—Pr1—O8123.00 (12)
C2—C1—C6118.7 (4)O13—Pr1—O893.01 (16)
C3—C2—O2125.1 (5)O7—Pr1—O871.80 (14)
C3—C2—C1121.1 (5)O11—Pr1—O871.42 (16)
O2—C2—C1113.8 (4)O5—Pr1—O8116.62 (14)
C2—C3—C4119.4 (6)O10—Pr1—O848.21 (12)
C2—C3—H1120.3O1—Pr1—O260.30 (10)
C4—C3—H1120.3O3—Pr1—O2121.56 (11)
C5—C4—C3120.2 (5)O13—Pr1—O276.72 (15)
C5—C4—H2119.9O7—Pr1—O279.38 (12)
C3—C4—H2119.9O11—Pr1—O2126.05 (14)
C4—C5—C6122.2 (5)O5—Pr1—O278.91 (13)
C4—C5—H3118.9O10—Pr1—O268.27 (11)
C6—C5—H3118.9O8—Pr1—O2115.44 (11)
C5—C6—C1118.1 (5)O1—Pr1—O4120.33 (10)
C5—C6—C7118.7 (5)O3—Pr1—O460.17 (11)
C1—C6—C7123.2 (5)O13—Pr1—O4130.59 (15)
N1—C7—C6126.0 (5)O7—Pr1—O477.04 (12)
N1—C7—H4117.0O11—Pr1—O481.28 (14)
C6—C7—H4117.0O5—Pr1—O475.36 (13)
N2—C11—C12125.7 (5)O10—Pr1—O4115.93 (11)
N2—C11—H11117.2O8—Pr1—O469.57 (11)
C12—C11—H11117.2O2—Pr1—O4152.68 (11)
C13—C12—C17118.9 (6)O1—Pr1—Cu131.75 (8)
C13—C12—C11117.7 (5)O3—Pr1—Cu131.62 (8)
C17—C12—C11123.4 (5)O13—Pr1—Cu182.12 (12)
C14—C13—C12121.3 (6)O7—Pr1—Cu1127.44 (8)
C14—C13—H12119.3O11—Pr1—Cu183.65 (13)
C12—C13—H12119.3O5—Pr1—Cu177.87 (8)
C13—C14—C15120.1 (5)O10—Pr1—Cu1151.01 (9)
C13—C14—H13119.9O8—Pr1—Cu1150.37 (9)
C15—C14—H13119.9O2—Pr1—Cu191.98 (7)
C14—C15—C16120.3 (6)O4—Pr1—Cu191.49 (7)
C14—C15—H14119.9C7—N1—C8118.2 (9)
C16—C15—H14119.9C7—N1—Cu1125.5 (4)
O4—C16—C17114.1 (4)C8—N1—Cu1110.0 (8)
O4—C16—C15125.0 (5)C11—N2—C10119.0 (7)
C17—C16—C15120.9 (5)C11—N2—Cu1125.6 (4)
O3—C17—C16117.4 (4)C10—N2—Cu1112.4 (7)
O3—C17—C12124.2 (5)O6—N3—O5123.1 (4)
C16—C17—C12118.4 (4)O6—N3—O7121.0 (5)
O14—C21—C22122.0 (6)O5—N3—O7115.9 (4)
O14—C21—C20120.1 (5)O9—N4—O8122.3 (5)
C22—C21—C20117.9 (6)O9—N4—O10121.3 (5)
O3—Cu1—O183.45 (13)O8—N4—O10116.3 (4)
O3—Cu1—N1172.5 (2)O12—N5—O11122.6 (7)
O1—Cu1—N195.29 (19)O12—N5—O13121.7 (7)
O3—Cu1—N295.40 (19)O11—N5—O13115.7 (5)
O1—Cu1—N2172.52 (19)C1—O1—Cu1125.3 (3)
N1—Cu1—N284.9 (2)C1—O1—Pr1128.0 (3)
O3—Cu1—O1496.98 (14)Cu1—O1—Pr1106.14 (14)
O1—Cu1—O1495.65 (14)C2—O2—C19116.8 (4)
N1—Cu1—O1490.5 (2)C2—O2—Pr1118.7 (3)
N2—Cu1—O1491.82 (19)C19—O2—Pr1124.2 (3)
O3—Cu1—Pr142.32 (9)C17—O3—Cu1125.4 (3)
O1—Cu1—Pr142.11 (9)C17—O3—Pr1128.5 (3)
N1—Cu1—Pr1137.31 (17)Cu1—O3—Pr1106.06 (13)
N2—Cu1—Pr1137.64 (17)C16—O4—C18116.3 (4)
O14—Cu1—Pr191.37 (10)C16—O4—Pr1119.4 (3)
O1—Pr1—O362.71 (11)C18—O4—Pr1124.0 (3)
O1—Pr1—O1374.17 (15)N3—O5—Pr196.6 (3)
O3—Pr1—O1399.66 (15)N3—O7—Pr197.5 (3)
O1—Pr1—O7117.25 (12)N4—O8—Pr197.3 (3)
O3—Pr1—O7117.54 (11)N4—O10—Pr198.0 (3)
O13—Pr1—O7142.44 (15)N5—O11—Pr197.0 (4)
O1—Pr1—O11100.69 (14)N5—O13—Pr197.9 (4)
O3—Pr1—O1175.97 (15)C21—O14—Cu1137.6 (4)
O13—Pr1—O1149.37 (16)C9—C8—C10105 (2)
O7—Pr1—O11141.92 (14)C9—C8—N1112 (2)
O1—Pr1—O575.49 (12)C10—C8—N1111.2 (12)
O3—Pr1—O575.65 (12)C9—C8—H5109.7
O13—Pr1—O5147.72 (16)C10—C8—H5109.7
O7—Pr1—O549.57 (11)N1—C8—H5109.7
O11—Pr1—O5149.61 (16)N2—C10—C8109.2 (12)
O1—Pr1—O10123.59 (12)N2—C10—H9109.8
O3—Pr1—O10166.77 (13)C8—C10—H9109.8
O13—Pr1—O1073.02 (16)N2—C10—H10109.8
O7—Pr1—O1071.38 (13)C8—C10—H10109.8
O11—Pr1—O1091.06 (16)H9—C10—H10108.3
O5—Pr1—O10116.49 (13)C10'—C8'—C9'87.5 (10)
O1—C1—C2—C3−176.6 (5)O11—Pr1—O2—C19117.3 (4)
C6—C1—C2—C35.0 (7)O5—Pr1—O2—C19−81.8 (4)
O1—C1—C2—O22.8 (6)O10—Pr1—O2—C1942.7 (4)
C6—C1—C2—O2−175.6 (4)O8—Pr1—O2—C1932.5 (5)
O2—C2—C3—C4179.4 (5)O4—Pr1—O2—C19−62.0 (5)
C1—C2—C3—C4−1.3 (8)Cu1—Pr1—O2—C19−159.1 (4)
C2—C3—C4—C5−2.1 (10)C16—C17—O3—Cu1171.8 (3)
C3—C4—C5—C61.8 (10)C12—C17—O3—Cu1−8.0 (6)
C4—C5—C6—C12.0 (8)C16—C17—O3—Pr1−3.9 (6)
C4—C5—C6—C7−176.6 (6)C12—C17—O3—Pr1176.3 (3)
O1—C1—C6—C5176.5 (4)O1—Cu1—O3—C17−165.9 (4)
C2—C1—C6—C5−5.2 (7)N2—Cu1—O3—C176.7 (4)
O1—C1—C6—C7−5.1 (8)O14—Cu1—O3—C1799.2 (4)
C2—C1—C6—C7173.3 (5)Pr1—Cu1—O3—C17−176.5 (4)
C5—C6—C7—N1−177.4 (6)O1—Cu1—O3—Pr110.57 (15)
C1—C6—C7—N14.1 (10)N2—Cu1—O3—Pr1−176.85 (19)
N2—C11—C12—C13−178.1 (6)O14—Cu1—O3—Pr1−84.35 (15)
N2—C11—C12—C17−1.1 (10)O1—Pr1—O3—C17167.1 (4)
C17—C12—C13—C140.0 (9)O13—Pr1—O3—C17−126.4 (4)
C11—C12—C13—C14177.1 (6)O7—Pr1—O3—C1758.9 (4)
C12—C13—C14—C15−1.1 (10)O11—Pr1—O3—C17−82.8 (4)
C13—C14—C15—C160.6 (9)O5—Pr1—O3—C1786.2 (4)
C14—C15—C16—O4−178.7 (5)O10—Pr1—O3—C17−71.2 (7)
C14—C15—C16—C171.2 (7)O8—Pr1—O3—C17−26.4 (4)
O4—C16—C17—O3−2.2 (6)O2—Pr1—O3—C17153.3 (3)
C15—C16—C17—O3177.9 (4)O4—Pr1—O3—C175.1 (3)
O4—C16—C17—C12177.6 (4)Cu1—Pr1—O3—C17176.3 (5)
C15—C16—C17—C12−2.3 (7)O1—Pr1—O3—Cu1−9.26 (13)
C13—C12—C17—O3−178.5 (5)O13—Pr1—O3—Cu157.21 (19)
C11—C12—C17—O34.5 (8)O7—Pr1—O3—Cu1−117.44 (15)
C13—C12—C17—C161.7 (7)O11—Pr1—O3—Cu1100.87 (18)
C11—C12—C17—C16−175.3 (5)O5—Pr1—O3—Cu1−90.11 (17)
O3—Cu1—Pr1—O1164.2 (2)O10—Pr1—O3—Cu1112.4 (5)
N1—Cu1—Pr1—O1−4.6 (3)O8—Pr1—O3—Cu1157.23 (16)
N2—Cu1—Pr1—O1168.9 (3)O2—Pr1—O3—Cu1−23.1 (2)
O14—Cu1—Pr1—O1−96.91 (18)O4—Pr1—O3—Cu1−171.2 (2)
O1—Cu1—Pr1—O3−164.2 (2)C17—C16—O4—C18−166.9 (4)
N1—Cu1—Pr1—O3−168.8 (3)C15—C16—O4—C1813.0 (6)
N2—Cu1—Pr1—O34.6 (3)C17—C16—O4—Pr16.4 (5)
O14—Cu1—Pr1—O398.87 (18)C15—C16—O4—Pr1−173.7 (4)
O3—Cu1—Pr1—O13−123.2 (2)O1—Pr1—O4—C16−24.4 (3)
O1—Cu1—Pr1—O1372.6 (2)O3—Pr1—O4—C16−5.8 (3)
N1—Cu1—Pr1—O1368.0 (3)O13—Pr1—O4—C1670.5 (3)
N2—Cu1—Pr1—O13−118.6 (3)O7—Pr1—O4—C16−138.5 (3)
O14—Cu1—Pr1—O13−24.35 (15)O11—Pr1—O4—C1673.0 (3)
O3—Cu1—Pr1—O782.4 (2)O5—Pr1—O4—C16−87.4 (3)
O1—Cu1—Pr1—O7−81.86 (19)O10—Pr1—O4—C16159.9 (3)
N1—Cu1—Pr1—O7−86.5 (3)O8—Pr1—O4—C16146.3 (3)
N2—Cu1—Pr1—O787.0 (3)O2—Pr1—O4—C16−107.6 (3)
O14—Cu1—Pr1—O7−178.77 (15)Cu1—Pr1—O4—C16−10.4 (3)
O3—Cu1—Pr1—O11−73.46 (19)O1—Pr1—O4—C18148.4 (4)
O1—Cu1—Pr1—O11122.31 (19)O3—Pr1—O4—C18167.0 (4)
N1—Cu1—Pr1—O11117.7 (3)O13—Pr1—O4—C18−116.7 (4)
N2—Cu1—Pr1—O11−68.8 (3)O7—Pr1—O4—C1834.2 (4)
O14—Cu1—Pr1—O1125.40 (14)O11—Pr1—O4—C18−114.3 (4)
O3—Cu1—Pr1—O582.27 (19)O5—Pr1—O4—C1885.3 (4)
O1—Cu1—Pr1—O5−81.96 (19)O10—Pr1—O4—C18−27.3 (4)
N1—Cu1—Pr1—O5−86.6 (3)O8—Pr1—O4—C18−40.9 (4)
N2—Cu1—Pr1—O586.9 (3)O2—Pr1—O4—C1865.2 (4)
O14—Cu1—Pr1—O5−178.87 (13)Cu1—Pr1—O4—C18162.4 (4)
O3—Cu1—Pr1—O10−154.1 (3)O6—N3—O5—Pr1173.0 (6)
O1—Cu1—Pr1—O1041.7 (3)O7—N3—O5—Pr1−6.6 (5)
N1—Cu1—Pr1—O1037.0 (3)O1—Pr1—O5—N3151.2 (3)
N2—Cu1—Pr1—O10−149.5 (3)O3—Pr1—O5—N3−143.8 (3)
O14—Cu1—Pr1—O10−55.3 (2)O13—Pr1—O5—N3130.8 (4)
O3—Cu1—Pr1—O8−41.0 (3)O7—Pr1—O5—N33.9 (3)
O1—Cu1—Pr1—O8154.7 (3)O11—Pr1—O5—N3−122.4 (4)
N1—Cu1—Pr1—O8150.1 (3)O10—Pr1—O5—N330.6 (4)
N2—Cu1—Pr1—O8−36.4 (3)O8—Pr1—O5—N3−23.7 (4)
O14—Cu1—Pr1—O857.8 (2)O2—Pr1—O5—N389.3 (3)
O3—Cu1—Pr1—O2160.48 (17)O4—Pr1—O5—N3−81.4 (3)
O1—Cu1—Pr1—O2−3.74 (17)Cu1—Pr1—O5—N3−176.2 (3)
N1—Cu1—Pr1—O2−8.4 (3)O6—N3—O7—Pr1−172.9 (5)
N2—Cu1—Pr1—O2165.1 (3)O5—N3—O7—Pr16.6 (5)
O14—Cu1—Pr1—O2−100.65 (12)O1—Pr1—O7—N3−39.8 (3)
O3—Cu1—Pr1—O47.59 (17)O3—Pr1—O7—N331.9 (3)
O1—Cu1—Pr1—O4−156.63 (17)O13—Pr1—O7—N3−139.4 (3)
N1—Cu1—Pr1—O4−161.2 (3)O11—Pr1—O7—N3134.8 (3)
N2—Cu1—Pr1—O412.2 (3)O5—Pr1—O7—N3−3.8 (3)
O14—Cu1—Pr1—O4106.45 (11)O10—Pr1—O7—N3−158.7 (3)
C6—C7—N1—C8151.3 (10)O8—Pr1—O7—N3150.3 (3)
C6—C7—N1—Cu12.2 (10)O2—Pr1—O7—N3−88.2 (3)
O1—Cu1—N1—C7−5.6 (6)O4—Pr1—O7—N377.9 (3)
N2—Cu1—N1—C7−178.1 (7)Cu1—Pr1—O7—N3−3.9 (3)
O14—Cu1—N1—C790.1 (6)O9—N4—O8—Pr1−177.8 (6)
Pr1—Cu1—N1—C7−2.5 (8)O10—N4—O8—Pr13.7 (6)
O1—Cu1—N1—C8−156.8 (9)O1—Pr1—O8—N4−57.1 (7)
N2—Cu1—N1—C830.7 (9)O3—Pr1—O8—N4−169.7 (3)
O14—Cu1—N1—C8−61.1 (9)O13—Pr1—O8—N4−66.1 (4)
Pr1—Cu1—N1—C8−153.7 (9)O7—Pr1—O8—N478.8 (4)
C12—C11—N2—C10−157.0 (9)O11—Pr1—O8—N4−111.2 (4)
C12—C11—N2—Cu11.6 (10)O5—Pr1—O8—N4100.6 (4)
O3—Cu1—N2—C11−3.6 (6)O10—Pr1—O8—N4−2.2 (3)
N1—Cu1—N2—C11168.9 (6)O2—Pr1—O8—N410.6 (4)
O14—Cu1—N2—C11−100.7 (6)O4—Pr1—O8—N4161.4 (4)
Pr1—Cu1—N2—C11−6.7 (7)Cu1—Pr1—O8—N4−145.4 (3)
O3—Cu1—N2—C10156.2 (8)O9—N4—O10—Pr1177.7 (6)
N1—Cu1—N2—C10−31.4 (8)O8—N4—O10—Pr1−3.7 (6)
O14—Cu1—N2—C1059.0 (8)O1—Pr1—O10—N4169.4 (3)
Pr1—Cu1—N2—C10153.1 (8)O3—Pr1—O10—N454.6 (7)
C2—C1—O1—Cu1−178.7 (3)O13—Pr1—O10—N4112.4 (4)
C6—C1—O1—Cu1−0.4 (6)O7—Pr1—O10—N4−79.7 (4)
C2—C1—O1—Pr110.9 (6)O11—Pr1—O10—N465.8 (4)
C6—C1—O1—Pr1−170.8 (3)O5—Pr1—O10—N4−100.9 (4)
O3—Cu1—O1—C1177.2 (4)O8—Pr1—O10—N42.2 (3)
N1—Cu1—O1—C14.7 (4)O2—Pr1—O10—N4−165.4 (4)
O14—Cu1—O1—C1−86.4 (4)O4—Pr1—O10—N4−15.0 (4)
Pr1—Cu1—O1—C1−172.2 (4)Cu1—Pr1—O10—N4144.6 (3)
O3—Cu1—O1—Pr1−10.62 (15)O12—N5—O11—Pr1−179.4 (6)
N1—Cu1—O1—Pr1176.9 (2)O13—N5—O11—Pr12.0 (6)
O14—Cu1—O1—Pr185.78 (15)O1—Pr1—O11—N5−59.3 (4)
O3—Pr1—O1—C1−178.9 (4)O3—Pr1—O11—N5−117.5 (4)
O13—Pr1—O1—C171.1 (4)O13—Pr1—O11—N5−1.2 (4)
O7—Pr1—O1—C1−70.3 (4)O7—Pr1—O11—N5125.6 (4)
O11—Pr1—O1—C1113.1 (4)O5—Pr1—O11—N5−138.8 (4)
O5—Pr1—O1—C1−97.8 (4)O10—Pr1—O11—N565.2 (4)
O10—Pr1—O1—C114.6 (4)O8—Pr1—O11—N5110.0 (4)
O8—Pr1—O1—C161.8 (7)O2—Pr1—O11—N51.6 (5)
O2—Pr1—O1—C1−12.4 (3)O4—Pr1—O11—N5−178.7 (4)
O4—Pr1—O1—C1−160.8 (3)Cu1—Pr1—O11—N5−86.2 (4)
Cu1—Pr1—O1—C1171.9 (4)O12—N5—O13—Pr1179.4 (6)
O3—Pr1—O1—Cu19.23 (13)O11—N5—O13—Pr1−2.0 (6)
O13—Pr1—O1—Cu1−100.80 (19)O1—Pr1—O13—N5121.0 (4)
O7—Pr1—O1—Cu1117.86 (15)O3—Pr1—O13—N563.1 (4)
O11—Pr1—O1—Cu1−58.74 (19)O7—Pr1—O13—N5−124.6 (4)
O5—Pr1—O1—Cu190.34 (17)O11—Pr1—O13—N51.2 (4)
O10—Pr1—O1—Cu1−157.25 (15)O5—Pr1—O13—N5141.5 (4)
O8—Pr1—O1—Cu1−110.1 (5)O10—Pr1—O13—N5−105.5 (4)
O2—Pr1—O1—Cu1175.69 (19)O8—Pr1—O13—N5−61.1 (4)
O4—Pr1—O1—Cu127.34 (19)O2—Pr1—O13—N5−176.5 (4)
C3—C2—O2—C19−19.1 (7)O4—Pr1—O13—N54.4 (5)
C1—C2—O2—C19161.5 (5)Cu1—Pr1—O13—N589.6 (4)
C3—C2—O2—Pr1166.4 (4)C22—C21—O14—Cu1−171.4 (5)
C1—C2—O2—Pr1−13.0 (5)C20—C21—O14—Cu18.2 (10)
O1—Pr1—O2—C212.7 (3)O3—Cu1—O14—C21−52.6 (6)
O3—Pr1—O2—C226.8 (3)O1—Cu1—O14—C21−136.6 (6)
O13—Pr1—O2—C2−66.4 (3)N1—Cu1—O14—C21128.0 (6)
O7—Pr1—O2—C2142.7 (3)N2—Cu1—O14—C2143.1 (6)
O11—Pr1—O2—C2−68.6 (4)Pr1—Cu1—O14—C21−94.7 (6)
O5—Pr1—O2—C292.2 (3)C7—N1—C8—C965 (2)
O10—Pr1—O2—C2−143.2 (3)Cu1—N1—C8—C9−140.9 (18)
O8—Pr1—O2—C2−153.4 (3)C7—N1—C8—C10−178.0 (11)
O4—Pr1—O2—C2112.1 (3)Cu1—N1—C8—C10−24.4 (16)
Cu1—Pr1—O2—C215.0 (3)C11—N2—C10—C8−175.3 (11)
O1—Pr1—O2—C19−161.3 (5)Cu1—N2—C10—C823.4 (15)
O3—Pr1—O2—C19−147.2 (4)C9—C8—C10—N2121.7 (18)
O13—Pr1—O2—C19119.5 (4)N1—C8—C10—N20.8 (18)
O7—Pr1—O2—C19−31.3 (4)
Table 1
Selected geometric parameters (Å) top
Cu1—O31.897 (3)Pr1—O72.528 (4)
Cu1—O11.905 (3)Pr1—O112.538 (4)
Cu1—N11.907 (5)Pr1—O52.559 (4)
Cu1—N21.915 (4)Pr1—O102.571 (4)
Cu1—O142.594 (4)Pr1—O82.588 (4)
Pr1—O12.427 (3)Pr1—O22.658 (3)
Pr1—O32.436 (3)Pr1—O42.661 (3)
Pr1—O132.518 (5)
Acknowledgements top

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

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