Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034460/ng2296sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034460/ng2296Isup2.hkl |
CCDC reference: 625765
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.008 Å
- Disorder in main residue
- R factor = 0.036
- wR factor = 0.110
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O11 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O13 PLAT432_ALERT_2_B Short Inter X...Y Contact O12 .. C9 .. 2.75 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.14 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.94 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O7 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O8 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Pr1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 56
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 17 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
See Kara et al. (2000) for a similar copper–lanthanum complex of the same Schiff base.
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%.
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'.
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.
See Kara et al. (2000) for a similar copper–lanthanum complex of the same Schiff base.
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.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. The disordered C8', C9', C10' and all H atoms have been omitted. |
[CuPr(C19H20N2O4)(NO3)3(C3H6O)] | F(000) = 1555 |
Mr = 784.64 | Dx = 1.790 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20972 reflections |
a = 9.879 (3) Å | θ = 3.0–27.5° |
b = 18.887 (7) Å | µ = 2.46 mm−1 |
c = 15.676 (5) Å | T = 295 K |
β = 95.376 (14)° | Block, colourless |
V = 2912.2 (16) Å3 | 0.39 × 0.25 × 0.24 mm |
Z = 4 |
Rigaku RAXIS-RAPID diffractometer | 6654 independent reflections |
Radiation source: fine-focus sealed tube | 5376 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.447, Tmax = 0.567 | k = −24→24 |
25560 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-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 parameters | Δρmax = 1.01 e Å−3 |
56 restraints | Δρmin = −0.75 e Å−3 |
[CuPr(C19H20N2O4)(NO3)3(C3H6O)] | V = 2912.2 (16) Å3 |
Mr = 784.64 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.879 (3) Å | µ = 2.46 mm−1 |
b = 18.887 (7) Å | T = 295 K |
c = 15.676 (5) Å | 0.39 × 0.25 × 0.24 mm |
β = 95.376 (14)° |
Rigaku RAXIS-RAPID diffractometer | 6654 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5376 reflections with I > 2σ(I) |
Tmin = 0.447, Tmax = 0.567 | Rint = 0.033 |
25560 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 56 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.11 | Δρmax = 1.01 e Å−3 |
6654 reflections | Δρmin = −0.75 e Å−3 |
421 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.8680 (4) | 0.2350 (2) | 0.3353 (3) | 0.0444 (9) | |
C2 | 0.9441 (5) | 0.1951 (2) | 0.3985 (3) | 0.0480 (10) | |
C3 | 1.0029 (6) | 0.2261 (3) | 0.4713 (4) | 0.0676 (15) | |
H1 | 1.0514 | 0.1989 | 0.5131 | 0.081* | |
C4 | 0.9895 (6) | 0.2994 (3) | 0.4825 (4) | 0.0748 (17) | |
H2 | 1.0267 | 0.3207 | 0.5328 | 0.090* | |
C5 | 0.9234 (5) | 0.3387 (3) | 0.4211 (4) | 0.0684 (16) | |
H3 | 0.9178 | 0.3874 | 0.4291 | 0.082* | |
C6 | 0.8622 (5) | 0.3091 (2) | 0.3451 (3) | 0.0520 (11) | |
C7 | 0.7993 (6) | 0.3557 (3) | 0.2800 (5) | 0.0760 (18) | |
H4 | 0.8057 | 0.4041 | 0.2907 | 0.091* | |
C11 | 0.5822 (7) | 0.2497 (4) | 0.0017 (4) | 0.0783 (19) | |
H11 | 0.5442 | 0.2763 | −0.0444 | 0.094* | |
C12 | 0.5947 (5) | 0.1744 (3) | −0.0112 (3) | 0.0594 (13) | |
C13 | 0.5531 (6) | 0.1477 (4) | −0.0920 (3) | 0.0750 (18) | |
H12 | 0.5149 | 0.1782 | −0.1342 | 0.090* | |
C14 | 0.5669 (7) | 0.0777 (4) | −0.1105 (3) | 0.0761 (19) | |
H13 | 0.5369 | 0.0608 | −0.1647 | 0.091* | |
C15 | 0.6248 (5) | 0.0325 (3) | −0.0499 (3) | 0.0606 (13) | |
H14 | 0.6348 | −0.0151 | −0.0630 | 0.073* | |
C16 | 0.6688 (5) | 0.0572 (3) | 0.0312 (3) | 0.0492 (11) | |
C17 | 0.6527 (5) | 0.1276 (3) | 0.0526 (3) | 0.0493 (11) | |
C18 | 0.7768 (6) | −0.0526 (3) | 0.0730 (4) | 0.0636 (14) | |
H15 | 0.6997 | −0.0816 | 0.0546 | 0.095* | |
H17 | 0.8273 | −0.0742 | 0.1214 | 0.095* | |
H16 | 0.8340 | −0.0480 | 0.0270 | 0.095* | |
C19 | 1.0568 (7) | 0.0843 (3) | 0.4255 (4) | 0.0703 (16) | |
H18 | 1.1406 | 0.1102 | 0.4268 | 0.106* | |
H19 | 1.0667 | 0.0397 | 0.3976 | 0.106* | |
H20 | 1.0345 | 0.0764 | 0.4830 | 0.106* | |
C20 | 0.3179 (7) | 0.1927 (4) | 0.1389 (4) | 0.0841 (19) | |
H21 | 0.2896 | 0.2285 | 0.0975 | 0.126* | |
H22 | 0.2443 | 0.1604 | 0.1444 | 0.126* | |
H23 | 0.3942 | 0.1674 | 0.1204 | 0.126* | |
C21 | 0.3576 (6) | 0.2265 (3) | 0.2231 (4) | 0.0620 (13) | |
C22 | 0.2484 (8) | 0.2423 (5) | 0.2793 (5) | 0.102 (2) | |
H24 | 0.2131 | 0.1987 | 0.2997 | 0.154* | |
H25 | 0.1767 | 0.2680 | 0.2474 | 0.154* | |
H26 | 0.2849 | 0.2703 | 0.3272 | 0.154* | |
Cu1 | 0.70339 (7) | 0.24136 (3) | 0.17375 (4) | 0.05314 (16) | |
Pr1 | 0.78327 (2) | 0.072680 (11) | 0.251884 (13) | 0.03820 (9) | |
N1 | 0.7363 (6) | 0.3368 (2) | 0.2097 (4) | 0.0833 (17) | |
N2 | 0.6188 (6) | 0.2829 (3) | 0.0708 (3) | 0.0736 (14) | |
N3 | 1.0501 (4) | 0.0451 (2) | 0.1849 (3) | 0.0553 (10) | |
N4 | 0.7742 (5) | −0.0693 (2) | 0.3381 (3) | 0.0607 (11) | |
N5 | 0.5171 (6) | 0.0863 (3) | 0.3227 (4) | 0.0774 (15) | |
O1 | 0.8088 (3) | 0.19986 (16) | 0.2688 (2) | 0.0501 (7) | |
O2 | 0.9507 (3) | 0.12417 (17) | 0.3795 (2) | 0.0516 (8) | |
O3 | 0.6936 (4) | 0.14686 (17) | 0.13258 (18) | 0.0510 (8) | |
O4 | 0.7309 (3) | 0.01636 (17) | 0.09667 (19) | 0.0496 (7) | |
O5 | 0.9915 (4) | 0.1033 (2) | 0.1734 (3) | 0.0686 (10) | |
O6 | 1.1512 (6) | 0.0298 (3) | 0.1524 (4) | 0.1089 (19) | |
O7 | 0.9956 (4) | 0.00182 (18) | 0.2334 (3) | 0.0631 (9) | |
O8 | 0.7247 (5) | −0.0603 (2) | 0.2635 (2) | 0.0707 (11) | |
O9 | 0.7751 (6) | −0.1266 (2) | 0.3731 (3) | 0.1046 (17) | |
O10 | 0.8210 (5) | −0.0157 (2) | 0.3766 (2) | 0.0715 (10) | |
O11 | 0.5273 (5) | 0.0602 (3) | 0.2508 (3) | 0.0887 (14) | |
O12 | 0.4092 (6) | 0.0918 (4) | 0.3531 (5) | 0.133 (2) | |
O13 | 0.6254 (5) | 0.1080 (3) | 0.3616 (3) | 0.0890 (13) | |
O14 | 0.4757 (4) | 0.2408 (2) | 0.2439 (3) | 0.0718 (11) | |
C8 | 0.622 (2) | 0.3855 (8) | 0.1689 (15) | 0.067 (6) | 0.289 (11) |
H5 | 0.5540 | 0.3932 | 0.2097 | 0.080* | 0.289 (11) |
C9 | 0.674 (4) | 0.4528 (12) | 0.143 (2) | 0.139 (15) | 0.289 (11) |
H6 | 0.7042 | 0.4485 | 0.0868 | 0.209* | 0.289 (11) |
H7 | 0.7491 | 0.4668 | 0.1829 | 0.209* | 0.289 (11) |
H8 | 0.6036 | 0.4879 | 0.1423 | 0.209* | 0.289 (11) |
C10 | 0.5539 (19) | 0.3537 (8) | 0.0867 (10) | 0.044 (4) | 0.289 (11) |
H9 | 0.4575 | 0.3474 | 0.0917 | 0.053* | 0.289 (11) |
H10 | 0.5643 | 0.3853 | 0.0390 | 0.053* | 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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.042 (2) | 0.037 (2) | 0.054 (2) | −0.0015 (18) | 0.0044 (19) | −0.0046 (18) |
C2 | 0.048 (2) | 0.046 (2) | 0.049 (2) | −0.006 (2) | −0.004 (2) | −0.0070 (19) |
C3 | 0.069 (3) | 0.064 (3) | 0.066 (3) | 0.001 (3) | −0.014 (3) | −0.013 (3) |
C4 | 0.071 (4) | 0.064 (4) | 0.086 (4) | −0.003 (3) | −0.013 (3) | −0.036 (3) |
C5 | 0.055 (3) | 0.043 (3) | 0.106 (5) | −0.002 (2) | −0.003 (3) | −0.024 (3) |
C6 | 0.040 (2) | 0.038 (2) | 0.077 (3) | −0.0029 (19) | 0.000 (2) | −0.007 (2) |
C7 | 0.065 (3) | 0.029 (2) | 0.131 (6) | −0.001 (2) | −0.009 (4) | 0.003 (3) |
C11 | 0.081 (4) | 0.098 (5) | 0.055 (3) | 0.029 (4) | 0.003 (3) | 0.038 (3) |
C12 | 0.053 (3) | 0.086 (4) | 0.038 (2) | 0.012 (3) | 0.000 (2) | 0.017 (2) |
C13 | 0.066 (3) | 0.115 (6) | 0.042 (3) | 0.005 (4) | −0.004 (2) | 0.019 (3) |
C14 | 0.066 (3) | 0.122 (6) | 0.038 (2) | −0.010 (4) | −0.009 (2) | 0.003 (3) |
C15 | 0.055 (3) | 0.086 (4) | 0.040 (2) | −0.014 (3) | 0.003 (2) | −0.008 (2) |
C16 | 0.045 (2) | 0.065 (3) | 0.038 (2) | −0.006 (2) | 0.0057 (19) | −0.001 (2) |
C17 | 0.046 (2) | 0.069 (3) | 0.0327 (19) | 0.001 (2) | 0.0031 (18) | 0.007 (2) |
C18 | 0.077 (4) | 0.054 (3) | 0.060 (3) | 0.006 (3) | 0.008 (3) | −0.014 (2) |
C19 | 0.076 (4) | 0.054 (3) | 0.074 (4) | 0.009 (3) | −0.027 (3) | 0.001 (3) |
C20 | 0.067 (4) | 0.092 (5) | 0.090 (4) | −0.020 (3) | −0.006 (3) | −0.011 (4) |
C21 | 0.055 (3) | 0.057 (3) | 0.074 (3) | −0.003 (2) | 0.005 (3) | 0.004 (3) |
C22 | 0.073 (4) | 0.131 (7) | 0.107 (5) | 0.001 (5) | 0.026 (4) | −0.014 (5) |
Cu1 | 0.0654 (4) | 0.0380 (3) | 0.0542 (3) | 0.0070 (3) | −0.0038 (3) | 0.0120 (2) |
Pr1 | 0.04735 (15) | 0.03195 (13) | 0.03429 (13) | 0.00098 (9) | −0.00148 (9) | 0.00179 (8) |
N1 | 0.096 (4) | 0.031 (2) | 0.116 (4) | −0.002 (2) | −0.026 (3) | 0.014 (3) |
N2 | 0.094 (4) | 0.065 (3) | 0.062 (3) | 0.027 (3) | 0.003 (3) | 0.029 (2) |
N3 | 0.055 (2) | 0.043 (2) | 0.069 (3) | −0.0001 (19) | 0.014 (2) | −0.0002 (19) |
N4 | 0.080 (3) | 0.041 (2) | 0.057 (2) | −0.011 (2) | −0.014 (2) | 0.0130 (18) |
N5 | 0.072 (3) | 0.081 (4) | 0.084 (4) | 0.004 (3) | 0.030 (3) | 0.008 (3) |
O1 | 0.0594 (19) | 0.0348 (16) | 0.0529 (17) | 0.0021 (14) | −0.0111 (15) | 0.0018 (13) |
O2 | 0.0605 (19) | 0.0394 (16) | 0.0507 (17) | 0.0038 (14) | −0.0174 (15) | 0.0000 (14) |
O3 | 0.068 (2) | 0.0476 (18) | 0.0362 (15) | 0.0119 (15) | −0.0032 (14) | 0.0074 (13) |
O4 | 0.0578 (18) | 0.0493 (18) | 0.0407 (15) | 0.0011 (15) | −0.0005 (14) | −0.0058 (13) |
O5 | 0.068 (2) | 0.052 (2) | 0.089 (3) | 0.0092 (18) | 0.024 (2) | 0.021 (2) |
O6 | 0.098 (3) | 0.073 (3) | 0.169 (5) | 0.016 (3) | 0.080 (4) | 0.014 (3) |
O7 | 0.062 (2) | 0.0446 (19) | 0.084 (2) | 0.0074 (16) | 0.0117 (19) | 0.0159 (17) |
O8 | 0.098 (3) | 0.052 (2) | 0.056 (2) | −0.020 (2) | −0.023 (2) | 0.0102 (16) |
O9 | 0.147 (4) | 0.064 (3) | 0.094 (3) | −0.021 (3) | −0.035 (3) | 0.031 (2) |
O10 | 0.095 (2) | 0.0604 (19) | 0.0561 (17) | −0.0169 (17) | −0.0104 (17) | 0.0087 (15) |
O11 | 0.058 (2) | 0.114 (4) | 0.094 (3) | −0.008 (2) | 0.009 (2) | −0.020 (3) |
O12 | 0.081 (4) | 0.170 (6) | 0.159 (6) | 0.005 (4) | 0.070 (4) | 0.004 (5) |
O13 | 0.0882 (15) | 0.0920 (16) | 0.0874 (15) | 0.0007 (10) | 0.0117 (10) | −0.0043 (10) |
O14 | 0.060 (2) | 0.080 (3) | 0.075 (2) | −0.012 (2) | 0.004 (2) | −0.017 (2) |
C8 | 0.076 (12) | 0.023 (7) | 0.106 (15) | 0.018 (8) | 0.029 (11) | 0.014 (8) |
C9 | 0.17 (4) | 0.10 (2) | 0.15 (3) | 0.07 (2) | 0.04 (3) | 0.00 (2) |
C10 | 0.042 (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) |
C1—O1 | 1.325 (5) | C21—C22 | 1.485 (9) |
C1—C2 | 1.406 (7) | C22—H24 | 0.9600 |
C1—C6 | 1.410 (6) | C22—H25 | 0.9600 |
C2—C3 | 1.363 (7) | C22—H26 | 0.9600 |
C2—O2 | 1.375 (5) | Cu1—O3 | 1.897 (3) |
C3—C4 | 1.404 (8) | Cu1—O1 | 1.905 (3) |
C3—H1 | 0.9300 | Cu1—N1 | 1.907 (5) |
C4—C5 | 1.336 (9) | Cu1—N2 | 1.915 (4) |
C4—H2 | 0.9300 | Cu1—O14 | 2.594 (4) |
C5—C6 | 1.401 (7) | Cu1—Pr1 | 3.4774 (12) |
C5—H3 | 0.9300 | Pr1—O1 | 2.427 (3) |
C6—C7 | 1.443 (8) | Pr1—O3 | 2.436 (3) |
C7—N1 | 1.266 (9) | Pr1—O13 | 2.518 (5) |
C7—H4 | 0.9300 | Pr1—O7 | 2.528 (4) |
C11—N2 | 1.273 (9) | Pr1—O11 | 2.538 (4) |
C11—C12 | 1.444 (9) | Pr1—O5 | 2.559 (4) |
C11—H11 | 0.9300 | Pr1—O10 | 2.571 (4) |
C12—C13 | 1.388 (8) | Pr1—O8 | 2.588 (4) |
C12—C17 | 1.416 (7) | Pr1—O2 | 2.658 (3) |
C13—C14 | 1.363 (9) | Pr1—O4 | 2.661 (3) |
C13—H12 | 0.9300 | N1—C8 | 1.549 (19) |
C14—C15 | 1.363 (8) | N2—C10 | 1.514 (17) |
C14—H13 | 0.9300 | N3—O6 | 1.199 (6) |
C15—C16 | 1.384 (6) | N3—O5 | 1.247 (6) |
C15—H14 | 0.9300 | N3—O7 | 1.270 (5) |
C16—O4 | 1.381 (6) | N4—O9 | 1.214 (5) |
C16—C17 | 1.384 (7) | N4—O8 | 1.236 (5) |
C17—O3 | 1.331 (5) | N4—O10 | 1.244 (5) |
C18—O4 | 1.440 (6) | N5—O12 | 1.212 (7) |
C18—H15 | 0.9600 | N5—O11 | 1.244 (7) |
C18—H17 | 0.9600 | N5—O13 | 1.250 (7) |
C18—H16 | 0.9600 | C8—C9 | 1.444 (19) |
C19—O2 | 1.430 (6) | C8—C10 | 1.52 (3) |
C19—H18 | 0.9600 | C8—H5 | 0.9800 |
C19—H19 | 0.9600 | C9—H6 | 0.9600 |
C19—H20 | 0.9600 | C9—H7 | 0.9600 |
C20—C21 | 1.486 (8) | C9—H8 | 0.9600 |
C20—H21 | 0.9600 | C10—H9 | 0.9700 |
C20—H22 | 0.9600 | C10—H10 | 0.9700 |
C20—H23 | 0.9600 | C8'—C10' | 1.313 (12) |
C21—O14 | 1.213 (6) | C8'—C9' | 1.417 (13) |
O1—C1—C2 | 116.9 (4) | O1—Pr1—O8 | 167.01 (13) |
O1—C1—C6 | 124.3 (4) | O3—Pr1—O8 | 123.00 (12) |
C2—C1—C6 | 118.7 (4) | O13—Pr1—O8 | 93.01 (16) |
C3—C2—O2 | 125.1 (5) | O7—Pr1—O8 | 71.80 (14) |
C3—C2—C1 | 121.1 (5) | O11—Pr1—O8 | 71.42 (16) |
O2—C2—C1 | 113.8 (4) | O5—Pr1—O8 | 116.62 (14) |
C2—C3—C4 | 119.4 (6) | O10—Pr1—O8 | 48.21 (12) |
C2—C3—H1 | 120.3 | O1—Pr1—O2 | 60.30 (10) |
C4—C3—H1 | 120.3 | O3—Pr1—O2 | 121.56 (11) |
C5—C4—C3 | 120.2 (5) | O13—Pr1—O2 | 76.72 (15) |
C5—C4—H2 | 119.9 | O7—Pr1—O2 | 79.38 (12) |
C3—C4—H2 | 119.9 | O11—Pr1—O2 | 126.05 (14) |
C4—C5—C6 | 122.2 (5) | O5—Pr1—O2 | 78.91 (13) |
C4—C5—H3 | 118.9 | O10—Pr1—O2 | 68.27 (11) |
C6—C5—H3 | 118.9 | O8—Pr1—O2 | 115.44 (11) |
C5—C6—C1 | 118.1 (5) | O1—Pr1—O4 | 120.33 (10) |
C5—C6—C7 | 118.7 (5) | O3—Pr1—O4 | 60.17 (11) |
C1—C6—C7 | 123.2 (5) | O13—Pr1—O4 | 130.59 (15) |
N1—C7—C6 | 126.0 (5) | O7—Pr1—O4 | 77.04 (12) |
N1—C7—H4 | 117.0 | O11—Pr1—O4 | 81.28 (14) |
C6—C7—H4 | 117.0 | O5—Pr1—O4 | 75.36 (13) |
N2—C11—C12 | 125.7 (5) | O10—Pr1—O4 | 115.93 (11) |
N2—C11—H11 | 117.2 | O8—Pr1—O4 | 69.57 (11) |
C12—C11—H11 | 117.2 | O2—Pr1—O4 | 152.68 (11) |
C13—C12—C17 | 118.9 (6) | O1—Pr1—Cu1 | 31.75 (8) |
C13—C12—C11 | 117.7 (5) | O3—Pr1—Cu1 | 31.62 (8) |
C17—C12—C11 | 123.4 (5) | O13—Pr1—Cu1 | 82.12 (12) |
C14—C13—C12 | 121.3 (6) | O7—Pr1—Cu1 | 127.44 (8) |
C14—C13—H12 | 119.3 | O11—Pr1—Cu1 | 83.65 (13) |
C12—C13—H12 | 119.3 | O5—Pr1—Cu1 | 77.87 (8) |
C13—C14—C15 | 120.1 (5) | O10—Pr1—Cu1 | 151.01 (9) |
C13—C14—H13 | 119.9 | O8—Pr1—Cu1 | 150.37 (9) |
C15—C14—H13 | 119.9 | O2—Pr1—Cu1 | 91.98 (7) |
C14—C15—C16 | 120.3 (6) | O4—Pr1—Cu1 | 91.49 (7) |
C14—C15—H14 | 119.9 | C7—N1—C8 | 118.2 (9) |
C16—C15—H14 | 119.9 | C7—N1—Cu1 | 125.5 (4) |
O4—C16—C17 | 114.1 (4) | C8—N1—Cu1 | 110.0 (8) |
O4—C16—C15 | 125.0 (5) | C11—N2—C10 | 119.0 (7) |
C17—C16—C15 | 120.9 (5) | C11—N2—Cu1 | 125.6 (4) |
O3—C17—C16 | 117.4 (4) | C10—N2—Cu1 | 112.4 (7) |
O3—C17—C12 | 124.2 (5) | O6—N3—O5 | 123.1 (4) |
C16—C17—C12 | 118.4 (4) | O6—N3—O7 | 121.0 (5) |
O14—C21—C22 | 122.0 (6) | O5—N3—O7 | 115.9 (4) |
O14—C21—C20 | 120.1 (5) | O9—N4—O8 | 122.3 (5) |
C22—C21—C20 | 117.9 (6) | O9—N4—O10 | 121.3 (5) |
O3—Cu1—O1 | 83.45 (13) | O8—N4—O10 | 116.3 (4) |
O3—Cu1—N1 | 172.5 (2) | O12—N5—O11 | 122.6 (7) |
O1—Cu1—N1 | 95.29 (19) | O12—N5—O13 | 121.7 (7) |
O3—Cu1—N2 | 95.40 (19) | O11—N5—O13 | 115.7 (5) |
O1—Cu1—N2 | 172.52 (19) | C1—O1—Cu1 | 125.3 (3) |
N1—Cu1—N2 | 84.9 (2) | C1—O1—Pr1 | 128.0 (3) |
O3—Cu1—O14 | 96.98 (14) | Cu1—O1—Pr1 | 106.14 (14) |
O1—Cu1—O14 | 95.65 (14) | C2—O2—C19 | 116.8 (4) |
N1—Cu1—O14 | 90.5 (2) | C2—O2—Pr1 | 118.7 (3) |
N2—Cu1—O14 | 91.82 (19) | C19—O2—Pr1 | 124.2 (3) |
O3—Cu1—Pr1 | 42.32 (9) | C17—O3—Cu1 | 125.4 (3) |
O1—Cu1—Pr1 | 42.11 (9) | C17—O3—Pr1 | 128.5 (3) |
N1—Cu1—Pr1 | 137.31 (17) | Cu1—O3—Pr1 | 106.06 (13) |
N2—Cu1—Pr1 | 137.64 (17) | C16—O4—C18 | 116.3 (4) |
O14—Cu1—Pr1 | 91.37 (10) | C16—O4—Pr1 | 119.4 (3) |
O1—Pr1—O3 | 62.71 (11) | C18—O4—Pr1 | 124.0 (3) |
O1—Pr1—O13 | 74.17 (15) | N3—O5—Pr1 | 96.6 (3) |
O3—Pr1—O13 | 99.66 (15) | N3—O7—Pr1 | 97.5 (3) |
O1—Pr1—O7 | 117.25 (12) | N4—O8—Pr1 | 97.3 (3) |
O3—Pr1—O7 | 117.54 (11) | N4—O10—Pr1 | 98.0 (3) |
O13—Pr1—O7 | 142.44 (15) | N5—O11—Pr1 | 97.0 (4) |
O1—Pr1—O11 | 100.69 (14) | N5—O13—Pr1 | 97.9 (4) |
O3—Pr1—O11 | 75.97 (15) | C21—O14—Cu1 | 137.6 (4) |
O13—Pr1—O11 | 49.37 (16) | C9—C8—C10 | 105 (2) |
O7—Pr1—O11 | 141.92 (14) | C9—C8—N1 | 112 (2) |
O1—Pr1—O5 | 75.49 (12) | C10—C8—N1 | 111.2 (12) |
O3—Pr1—O5 | 75.65 (12) | C9—C8—H5 | 109.7 |
O13—Pr1—O5 | 147.72 (16) | C10—C8—H5 | 109.7 |
O7—Pr1—O5 | 49.57 (11) | N1—C8—H5 | 109.7 |
O11—Pr1—O5 | 149.61 (16) | N2—C10—C8 | 109.2 (12) |
O1—Pr1—O10 | 123.59 (12) | N2—C10—H9 | 109.8 |
O3—Pr1—O10 | 166.77 (13) | C8—C10—H9 | 109.8 |
O13—Pr1—O10 | 73.02 (16) | N2—C10—H10 | 109.8 |
O7—Pr1—O10 | 71.38 (13) | C8—C10—H10 | 109.8 |
O11—Pr1—O10 | 91.06 (16) | H9—C10—H10 | 108.3 |
O5—Pr1—O10 | 116.49 (13) | C10'—C8'—C9' | 87.5 (10) |
O1—C1—C2—C3 | −176.6 (5) | O11—Pr1—O2—C19 | 117.3 (4) |
C6—C1—C2—C3 | 5.0 (7) | O5—Pr1—O2—C19 | −81.8 (4) |
O1—C1—C2—O2 | 2.8 (6) | O10—Pr1—O2—C19 | 42.7 (4) |
C6—C1—C2—O2 | −175.6 (4) | O8—Pr1—O2—C19 | 32.5 (5) |
O2—C2—C3—C4 | 179.4 (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—Cu1 | 171.8 (3) |
C3—C4—C5—C6 | 1.8 (10) | C12—C17—O3—Cu1 | −8.0 (6) |
C4—C5—C6—C1 | 2.0 (8) | C16—C17—O3—Pr1 | −3.9 (6) |
C4—C5—C6—C7 | −176.6 (6) | C12—C17—O3—Pr1 | 176.3 (3) |
O1—C1—C6—C5 | 176.5 (4) | O1—Cu1—O3—C17 | −165.9 (4) |
C2—C1—C6—C5 | −5.2 (7) | N2—Cu1—O3—C17 | 6.7 (4) |
O1—C1—C6—C7 | −5.1 (8) | O14—Cu1—O3—C17 | 99.2 (4) |
C2—C1—C6—C7 | 173.3 (5) | Pr1—Cu1—O3—C17 | −176.5 (4) |
C5—C6—C7—N1 | −177.4 (6) | O1—Cu1—O3—Pr1 | 10.57 (15) |
C1—C6—C7—N1 | 4.1 (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—C17 | 167.1 (4) |
C17—C12—C13—C14 | 0.0 (9) | O13—Pr1—O3—C17 | −126.4 (4) |
C11—C12—C13—C14 | 177.1 (6) | O7—Pr1—O3—C17 | 58.9 (4) |
C12—C13—C14—C15 | −1.1 (10) | O11—Pr1—O3—C17 | −82.8 (4) |
C13—C14—C15—C16 | 0.6 (9) | O5—Pr1—O3—C17 | 86.2 (4) |
C14—C15—C16—O4 | −178.7 (5) | O10—Pr1—O3—C17 | −71.2 (7) |
C14—C15—C16—C17 | 1.2 (7) | O8—Pr1—O3—C17 | −26.4 (4) |
O4—C16—C17—O3 | −2.2 (6) | O2—Pr1—O3—C17 | 153.3 (3) |
C15—C16—C17—O3 | 177.9 (4) | O4—Pr1—O3—C17 | 5.1 (3) |
O4—C16—C17—C12 | 177.6 (4) | Cu1—Pr1—O3—C17 | 176.3 (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—Cu1 | 57.21 (19) |
C11—C12—C17—O3 | 4.5 (8) | O7—Pr1—O3—Cu1 | −117.44 (15) |
C13—C12—C17—C16 | 1.7 (7) | O11—Pr1—O3—Cu1 | 100.87 (18) |
C11—C12—C17—C16 | −175.3 (5) | O5—Pr1—O3—Cu1 | −90.11 (17) |
O3—Cu1—Pr1—O1 | 164.2 (2) | O10—Pr1—O3—Cu1 | 112.4 (5) |
N1—Cu1—Pr1—O1 | −4.6 (3) | O8—Pr1—O3—Cu1 | 157.23 (16) |
N2—Cu1—Pr1—O1 | 168.9 (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—C18 | 13.0 (6) |
N2—Cu1—Pr1—O3 | 4.6 (3) | C17—C16—O4—Pr1 | 6.4 (5) |
O14—Cu1—Pr1—O3 | 98.87 (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—O13 | 72.6 (2) | O3—Pr1—O4—C16 | −5.8 (3) |
N1—Cu1—Pr1—O13 | 68.0 (3) | O13—Pr1—O4—C16 | 70.5 (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—C16 | 73.0 (3) |
O3—Cu1—Pr1—O7 | 82.4 (2) | O5—Pr1—O4—C16 | −87.4 (3) |
O1—Cu1—Pr1—O7 | −81.86 (19) | O10—Pr1—O4—C16 | 159.9 (3) |
N1—Cu1—Pr1—O7 | −86.5 (3) | O8—Pr1—O4—C16 | 146.3 (3) |
N2—Cu1—Pr1—O7 | 87.0 (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—C18 | 148.4 (4) |
O1—Cu1—Pr1—O11 | 122.31 (19) | O3—Pr1—O4—C18 | 167.0 (4) |
N1—Cu1—Pr1—O11 | 117.7 (3) | O13—Pr1—O4—C18 | −116.7 (4) |
N2—Cu1—Pr1—O11 | −68.8 (3) | O7—Pr1—O4—C18 | 34.2 (4) |
O14—Cu1—Pr1—O11 | 25.40 (14) | O11—Pr1—O4—C18 | −114.3 (4) |
O3—Cu1—Pr1—O5 | 82.27 (19) | O5—Pr1—O4—C18 | 85.3 (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—O5 | 86.9 (3) | O2—Pr1—O4—C18 | 65.2 (4) |
O14—Cu1—Pr1—O5 | −178.87 (13) | Cu1—Pr1—O4—C18 | 162.4 (4) |
O3—Cu1—Pr1—O10 | −154.1 (3) | O6—N3—O5—Pr1 | 173.0 (6) |
O1—Cu1—Pr1—O10 | 41.7 (3) | O7—N3—O5—Pr1 | −6.6 (5) |
N1—Cu1—Pr1—O10 | 37.0 (3) | O1—Pr1—O5—N3 | 151.2 (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—N3 | 130.8 (4) |
O3—Cu1—Pr1—O8 | −41.0 (3) | O7—Pr1—O5—N3 | 3.9 (3) |
O1—Cu1—Pr1—O8 | 154.7 (3) | O11—Pr1—O5—N3 | −122.4 (4) |
N1—Cu1—Pr1—O8 | 150.1 (3) | O10—Pr1—O5—N3 | 30.6 (4) |
N2—Cu1—Pr1—O8 | −36.4 (3) | O8—Pr1—O5—N3 | −23.7 (4) |
O14—Cu1—Pr1—O8 | 57.8 (2) | O2—Pr1—O5—N3 | 89.3 (3) |
O3—Cu1—Pr1—O2 | 160.48 (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—O2 | 165.1 (3) | O5—N3—O7—Pr1 | 6.6 (5) |
O14—Cu1—Pr1—O2 | −100.65 (12) | O1—Pr1—O7—N3 | −39.8 (3) |
O3—Cu1—Pr1—O4 | 7.59 (17) | O3—Pr1—O7—N3 | 31.9 (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—N3 | 134.8 (3) |
N2—Cu1—Pr1—O4 | 12.2 (3) | O5—Pr1—O7—N3 | −3.8 (3) |
O14—Cu1—Pr1—O4 | 106.45 (11) | O10—Pr1—O7—N3 | −158.7 (3) |
C6—C7—N1—C8 | 151.3 (10) | O8—Pr1—O7—N3 | 150.3 (3) |
C6—C7—N1—Cu1 | 2.2 (10) | O2—Pr1—O7—N3 | −88.2 (3) |
O1—Cu1—N1—C7 | −5.6 (6) | O4—Pr1—O7—N3 | 77.9 (3) |
N2—Cu1—N1—C7 | −178.1 (7) | Cu1—Pr1—O7—N3 | −3.9 (3) |
O14—Cu1—N1—C7 | 90.1 (6) | O9—N4—O8—Pr1 | −177.8 (6) |
Pr1—Cu1—N1—C7 | −2.5 (8) | O10—N4—O8—Pr1 | 3.7 (6) |
O1—Cu1—N1—C8 | −156.8 (9) | O1—Pr1—O8—N4 | −57.1 (7) |
N2—Cu1—N1—C8 | 30.7 (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—N4 | 78.8 (4) |
C12—C11—N2—C10 | −157.0 (9) | O11—Pr1—O8—N4 | −111.2 (4) |
C12—C11—N2—Cu1 | 1.6 (10) | O5—Pr1—O8—N4 | 100.6 (4) |
O3—Cu1—N2—C11 | −3.6 (6) | O10—Pr1—O8—N4 | −2.2 (3) |
N1—Cu1—N2—C11 | 168.9 (6) | O2—Pr1—O8—N4 | 10.6 (4) |
O14—Cu1—N2—C11 | −100.7 (6) | O4—Pr1—O8—N4 | 161.4 (4) |
Pr1—Cu1—N2—C11 | −6.7 (7) | Cu1—Pr1—O8—N4 | −145.4 (3) |
O3—Cu1—N2—C10 | 156.2 (8) | O9—N4—O10—Pr1 | 177.7 (6) |
N1—Cu1—N2—C10 | −31.4 (8) | O8—N4—O10—Pr1 | −3.7 (6) |
O14—Cu1—N2—C10 | 59.0 (8) | O1—Pr1—O10—N4 | 169.4 (3) |
Pr1—Cu1—N2—C10 | 153.1 (8) | O3—Pr1—O10—N4 | 54.6 (7) |
C2—C1—O1—Cu1 | −178.7 (3) | O13—Pr1—O10—N4 | 112.4 (4) |
C6—C1—O1—Cu1 | −0.4 (6) | O7—Pr1—O10—N4 | −79.7 (4) |
C2—C1—O1—Pr1 | 10.9 (6) | O11—Pr1—O10—N4 | 65.8 (4) |
C6—C1—O1—Pr1 | −170.8 (3) | O5—Pr1—O10—N4 | −100.9 (4) |
O3—Cu1—O1—C1 | 177.2 (4) | O8—Pr1—O10—N4 | 2.2 (3) |
N1—Cu1—O1—C1 | 4.7 (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—N4 | 144.6 (3) |
O3—Cu1—O1—Pr1 | −10.62 (15) | O12—N5—O11—Pr1 | −179.4 (6) |
N1—Cu1—O1—Pr1 | 176.9 (2) | O13—N5—O11—Pr1 | 2.0 (6) |
O14—Cu1—O1—Pr1 | 85.78 (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—C1 | 71.1 (4) | O13—Pr1—O11—N5 | −1.2 (4) |
O7—Pr1—O1—C1 | −70.3 (4) | O7—Pr1—O11—N5 | 125.6 (4) |
O11—Pr1—O1—C1 | 113.1 (4) | O5—Pr1—O11—N5 | −138.8 (4) |
O5—Pr1—O1—C1 | −97.8 (4) | O10—Pr1—O11—N5 | 65.2 (4) |
O10—Pr1—O1—C1 | 14.6 (4) | O8—Pr1—O11—N5 | 110.0 (4) |
O8—Pr1—O1—C1 | 61.8 (7) | O2—Pr1—O11—N5 | 1.6 (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—C1 | 171.9 (4) | O12—N5—O13—Pr1 | 179.4 (6) |
O3—Pr1—O1—Cu1 | 9.23 (13) | O11—N5—O13—Pr1 | −2.0 (6) |
O13—Pr1—O1—Cu1 | −100.80 (19) | O1—Pr1—O13—N5 | 121.0 (4) |
O7—Pr1—O1—Cu1 | 117.86 (15) | O3—Pr1—O13—N5 | 63.1 (4) |
O11—Pr1—O1—Cu1 | −58.74 (19) | O7—Pr1—O13—N5 | −124.6 (4) |
O5—Pr1—O1—Cu1 | 90.34 (17) | O11—Pr1—O13—N5 | 1.2 (4) |
O10—Pr1—O1—Cu1 | −157.25 (15) | O5—Pr1—O13—N5 | 141.5 (4) |
O8—Pr1—O1—Cu1 | −110.1 (5) | O10—Pr1—O13—N5 | −105.5 (4) |
O2—Pr1—O1—Cu1 | 175.69 (19) | O8—Pr1—O13—N5 | −61.1 (4) |
O4—Pr1—O1—Cu1 | 27.34 (19) | O2—Pr1—O13—N5 | −176.5 (4) |
C3—C2—O2—C19 | −19.1 (7) | O4—Pr1—O13—N5 | 4.4 (5) |
C1—C2—O2—C19 | 161.5 (5) | Cu1—Pr1—O13—N5 | 89.6 (4) |
C3—C2—O2—Pr1 | 166.4 (4) | C22—C21—O14—Cu1 | −171.4 (5) |
C1—C2—O2—Pr1 | −13.0 (5) | C20—C21—O14—Cu1 | 8.2 (10) |
O1—Pr1—O2—C2 | 12.7 (3) | O3—Cu1—O14—C21 | −52.6 (6) |
O3—Pr1—O2—C2 | 26.8 (3) | O1—Cu1—O14—C21 | −136.6 (6) |
O13—Pr1—O2—C2 | −66.4 (3) | N1—Cu1—O14—C21 | 128.0 (6) |
O7—Pr1—O2—C2 | 142.7 (3) | N2—Cu1—O14—C21 | 43.1 (6) |
O11—Pr1—O2—C2 | −68.6 (4) | Pr1—Cu1—O14—C21 | −94.7 (6) |
O5—Pr1—O2—C2 | 92.2 (3) | C7—N1—C8—C9 | 65 (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—C2 | 112.1 (3) | Cu1—N1—C8—C10 | −24.4 (16) |
Cu1—Pr1—O2—C2 | 15.0 (3) | C11—N2—C10—C8 | −175.3 (11) |
O1—Pr1—O2—C19 | −161.3 (5) | Cu1—N2—C10—C8 | 23.4 (15) |
O3—Pr1—O2—C19 | −147.2 (4) | C9—C8—C10—N2 | 121.7 (18) |
O13—Pr1—O2—C19 | 119.5 (4) | N1—C8—C10—N2 | 0.8 (18) |
O7—Pr1—O2—C19 | −31.3 (4) |
Experimental details
Crystal data | |
Chemical formula | [CuPr(C19H20N2O4)(NO3)3(C3H6O)] |
Mr | 784.64 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 9.879 (3), 18.887 (7), 15.676 (5) |
β (°) | 95.376 (14) |
V (Å3) | 2912.2 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.46 |
Crystal size (mm) | 0.39 × 0.25 × 0.24 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.447, 0.567 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25560, 6654, 5376 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.110, 1.11 |
No. of reflections | 6654 |
No. of parameters | 421 |
No. of restraints | 56 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.01, −0.75 |
Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXL97.
Cu1—O3 | 1.897 (3) | Pr1—O7 | 2.528 (4) |
Cu1—O1 | 1.905 (3) | Pr1—O11 | 2.538 (4) |
Cu1—N1 | 1.907 (5) | Pr1—O5 | 2.559 (4) |
Cu1—N2 | 1.915 (4) | Pr1—O10 | 2.571 (4) |
Cu1—O14 | 2.594 (4) | Pr1—O8 | 2.588 (4) |
Pr1—O1 | 2.427 (3) | Pr1—O2 | 2.658 (3) |
Pr1—O3 | 2.436 (3) | Pr1—O4 | 2.661 (3) |
Pr1—O13 | 2.518 (5) |
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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.