Acta Cryst. (2008). E64, m589 [ doi:10.1107/S1600536808005357 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-6,6'-Dimethoxy-2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}dimethanoltrinitratonickel(II)praseodymium(III) methanol disolvateIn the title dinuclear complex, [NiPr(C19H20N2O4)(NO3)3(CH3OH)2]·2CH3OH, the NiII ion is coordinated by two O atoms and two N atoms of a Schiff base ligand and by two methanol ligands, forming a slightly distorted octahedral geometry. The PrIII ion is coordinated by six O atoms from three chelating nitrate ligands and four O atoms from a Schiff base ligand, forming a distorted bicapped square-antiprismatic environment. In the crystal structure, intermolecular O-H
O hydrogen bonds connect complex molecules and methanol solvent molecules to form (10
) sheets.
The title complex was obtained by the treatment of Ni(II)acetate tetrahydrate (0.0622 g,0.25 mmol) with the Schiff base (0.0855 g,0.25 mmol) in methanol (25 ml) at room temperature. Then the mixture was refluxed for 3 h after the addition of praseodymium (III) nitrate hexahydrate (0.1042 g, 0.25 mmol). The reaction mixture was cooled and filtered; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis calculated for C23H34NiN5O17Pr: C, 32.38; H, 4.12; N, 8.18; found: C, 32.42; H, 4.02; N, 8.22
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 (methyl C) and with Uiso(H) = 1.5Ueq(C). H atoms bonded to O atoms were placed in calculated positions which gave the theoretically best locations to be involved in hydrogen bonding and treated as riding on their parent atoms, with O—H = 0.85 Å, and with Uiso(H) = 1.5Ueq(O).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./lh2586fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing 40% probability displacement ellipsoids. The solvent methanol molecules have been omitted for clarity. |
| [NiPr(C19H20N2O4)(NO3)3(CH4O)2]·2CH4O | F000 = 1728 |
| Mr = 854.17 | Dx = 1.752 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 24596 reflections |
| a = 13.101 (3) Å | θ = 3.0–27.5º |
| b = 11.128 (2) Å | µ = 2.15 mm−1 |
| c = 22.213 (4) Å | T = 293 (2) K |
| β = 90.73 (3)º | Block, green |
| V = 3238.1 (11) Å3 | 0.33 × 0.31 × 0.20 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 7364 independent reflections |
| Radiation source: fine-focus sealed tube | 6223 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.036 |
| T = 293(2) K | θmax = 27.5º |
| ω scans | θmin = 3.0º |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −17→16 |
| Tmin = 0.536, Tmax = 0.674 | k = −14→12 |
| 30138 measured reflections | l = −28→28 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
| wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0247P)2 + 3.534P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.004 |
| 7364 reflections | Δρmax = 0.68 e Å−3 |
| 430 parameters | Δρmin = −0.34 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [NiPr(C19H20N2O4)(NO3)3(CH4O)2]·2CH4O | V = 3238.1 (11) Å3 |
| Mr = 854.17 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 13.101 (3) Å | µ = 2.15 mm−1 |
| b = 11.128 (2) Å | T = 293 (2) K |
| c = 22.213 (4) Å | 0.33 × 0.31 × 0.20 mm |
| β = 90.73 (3)º |
| Rigaku R-AXIS RAPID diffractometer | 7364 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6223 reflections with I > 2σ(I) |
| Tmin = 0.536, Tmax = 0.674 | Rint = 0.036 |
| 30138 measured reflections |
| R[F2 > 2σ(F2)] = 0.029 | 430 parameters |
| wR(F2) = 0.067 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.68 e Å−3 |
| 7364 reflections | Δρmin = −0.34 e Å−3 |
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 | ||
| Pr1 | 0.216569 (12) | 0.702799 (13) | 0.077562 (7) | 0.03122 (5) | |
| Ni2 | 0.17232 (3) | 0.98440 (3) | 0.146000 (15) | 0.03016 (8) | |
| O1 | 0.28024 (14) | 0.90073 (17) | 0.09639 (9) | 0.0331 (4) | |
| O2 | 0.40132 (16) | 0.7479 (2) | 0.04462 (10) | 0.0443 (5) | |
| O3 | 0.10030 (14) | 0.82365 (17) | 0.13252 (9) | 0.0327 (4) | |
| O4 | 0.03400 (16) | 0.61709 (18) | 0.09151 (10) | 0.0412 (5) | |
| O5 | 0.0847 (2) | 0.7706 (3) | −0.00279 (12) | 0.0713 (8) | |
| O6 | 0.1076 (3) | 0.8251 (4) | −0.09346 (14) | 0.1064 (13) | |
| O7 | 0.2344 (2) | 0.7767 (3) | −0.03470 (14) | 0.0868 (10) | |
| O8 | 0.2129 (3) | 0.5235 (3) | 0.00588 (16) | 0.0864 (11) | |
| O9 | 0.2963 (3) | 0.3558 (3) | 0.01513 (19) | 0.0981 (12) | |
| O10 | 0.3143 (3) | 0.4978 (3) | 0.07861 (15) | 0.0910 (11) | |
| O11 | 0.1916 (2) | 0.5814 (3) | 0.17783 (13) | 0.0689 (8) | |
| O12 | 0.3064 (3) | 0.5697 (4) | 0.24869 (14) | 0.1008 (12) | |
| O13 | 0.3325 (2) | 0.6765 (2) | 0.16994 (11) | 0.0538 (6) | |
| O14 | 0.23893 (18) | 0.9184 (2) | 0.22722 (9) | 0.0477 (5) | |
| H14O | 0.2809 | 0.9580 | 0.2489 | 0.072* | |
| O15 | 0.10034 (18) | 1.0504 (2) | 0.06495 (9) | 0.0491 (6) | |
| H15O | 0.0438 | 1.0841 | 0.0727 | 0.074* | |
| N1 | 0.2617 (2) | 1.1332 (2) | 0.15446 (11) | 0.0388 (6) | |
| N2 | 0.0495 (2) | 1.0458 (2) | 0.19041 (10) | 0.0366 (5) | |
| N3 | 0.1414 (3) | 0.7903 (3) | −0.04484 (14) | 0.0579 (8) | |
| N4 | 0.2736 (2) | 0.4548 (3) | 0.03316 (16) | 0.0560 (8) | |
| N5 | 0.2774 (3) | 0.6073 (3) | 0.20013 (14) | 0.0566 (8) | |
| C1 | 0.3769 (2) | 0.9339 (3) | 0.09110 (12) | 0.0333 (6) | |
| C2 | 0.4459 (2) | 0.8550 (3) | 0.06371 (13) | 0.0374 (6) | |
| C3 | 0.5472 (3) | 0.8817 (3) | 0.05670 (16) | 0.0499 (8) | |
| H3A | 0.5904 | 0.8274 | 0.0380 | 0.060* | |
| C4 | 0.5842 (3) | 0.9906 (4) | 0.07772 (18) | 0.0567 (9) | |
| H4A | 0.6530 | 1.0094 | 0.0737 | 0.068* | |
| C5 | 0.5199 (3) | 1.0699 (3) | 0.10423 (17) | 0.0540 (9) | |
| H5A | 0.5455 | 1.1428 | 0.1181 | 0.065* | |
| C6 | 0.4161 (2) | 1.0446 (3) | 0.11116 (13) | 0.0395 (7) | |
| C7 | 0.3546 (3) | 1.1377 (3) | 0.13829 (14) | 0.0413 (7) | |
| H7A | 0.3873 | 1.2108 | 0.1448 | 0.050* | |
| C8 | 0.2245 (3) | 1.2444 (3) | 0.18456 (18) | 0.0564 (9) | |
| H8A | 0.2503 | 1.3137 | 0.1631 | 0.068* | |
| H8B | 0.2525 | 1.2471 | 0.2252 | 0.068* | |
| C9 | 0.1106 (3) | 1.2537 (3) | 0.18762 (17) | 0.0558 (9) | |
| H9A | 0.0827 | 1.2504 | 0.1470 | 0.067* | |
| H9B | 0.0932 | 1.3315 | 0.2043 | 0.067* | |
| C10 | 0.0603 (3) | 1.1579 (3) | 0.22453 (16) | 0.0527 (9) | |
| H10A | 0.1008 | 1.1432 | 0.2606 | 0.063* | |
| H10B | −0.0066 | 1.1855 | 0.2367 | 0.063* | |
| C11 | −0.0395 (2) | 1.0003 (3) | 0.18771 (13) | 0.0403 (7) | |
| H11A | −0.0911 | 1.0428 | 0.2067 | 0.048* | |
| C12 | −0.0691 (2) | 0.8885 (3) | 0.15801 (12) | 0.0355 (6) | |
| C13 | −0.1738 (2) | 0.8634 (3) | 0.15589 (15) | 0.0444 (7) | |
| H13A | −0.2194 | 0.9190 | 0.1714 | 0.053* | |
| C14 | −0.2104 (2) | 0.7590 (3) | 0.13152 (16) | 0.0501 (8) | |
| H14A | −0.2804 | 0.7448 | 0.1295 | 0.060* | |
| C15 | −0.1421 (2) | 0.6738 (3) | 0.10978 (14) | 0.0420 (7) | |
| H15A | −0.1661 | 0.6014 | 0.0941 | 0.050* | |
| C16 | −0.0397 (2) | 0.6973 (3) | 0.11158 (12) | 0.0341 (6) | |
| C17 | 0.0003 (2) | 0.8059 (3) | 0.13400 (12) | 0.0312 (6) | |
| C18 | 0.0043 (3) | 0.4945 (3) | 0.0871 (2) | 0.0624 (11) | |
| H18A | −0.0303 | 0.4712 | 0.1231 | 0.094* | |
| H18B | 0.0639 | 0.4453 | 0.0822 | 0.094* | |
| H18C | −0.0406 | 0.4842 | 0.0530 | 0.094* | |
| C19 | 0.4576 (3) | 0.6741 (3) | 0.0038 (2) | 0.0649 (11) | |
| H19A | 0.4859 | 0.7234 | −0.0273 | 0.097* | |
| H19B | 0.4128 | 0.6153 | −0.0140 | 0.097* | |
| H19C | 0.5117 | 0.6340 | 0.0253 | 0.097* | |
| C20 | 0.1849 (4) | 0.8569 (4) | 0.27271 (18) | 0.0739 (13) | |
| H20A | 0.2319 | 0.8112 | 0.2970 | 0.111* | |
| H20B | 0.1358 | 0.8038 | 0.2544 | 0.111* | |
| H20C | 0.1503 | 0.9141 | 0.2976 | 0.111* | |
| C21 | 0.1500 (3) | 1.0961 (4) | 0.01370 (16) | 0.0643 (11) | |
| H21A | 0.1109 | 1.0764 | −0.0218 | 0.096* | |
| H21B | 0.2168 | 1.0611 | 0.0110 | 0.096* | |
| H21C | 0.1561 | 1.1818 | 0.0171 | 0.096* | |
| O16 | 0.3699 (3) | 1.0418 (3) | 0.29578 (16) | 0.1010 (12) | |
| H16O | 0.4077 | 1.0979 | 0.2828 | 0.151* | |
| C22 | 0.4115 (5) | 0.9988 (7) | 0.3500 (3) | 0.127 (2) | |
| H22A | 0.4757 | 0.9605 | 0.3424 | 0.191* | |
| H22B | 0.3655 | 0.9417 | 0.3674 | 0.191* | |
| H22C | 0.4217 | 1.0646 | 0.3773 | 0.191* | |
| O17 | 0.5098 (3) | 0.7213 (4) | 0.2466 (2) | 0.1223 (15) | |
| H17O | 0.4579 | 0.7078 | 0.2242 | 0.183* | |
| C23 | 0.5316 (4) | 0.8313 (5) | 0.2238 (2) | 0.0912 (15) | |
| H23A | 0.4757 | 0.8849 | 0.2311 | 0.137* | |
| H23B | 0.5422 | 0.8248 | 0.1813 | 0.137* | |
| H23C | 0.5923 | 0.8620 | 0.2430 | 0.137* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Pr1 | 0.02647 (8) | 0.02928 (8) | 0.03787 (9) | 0.00184 (6) | −0.00064 (6) | −0.00402 (6) |
| Ni2 | 0.02980 (19) | 0.02824 (17) | 0.03245 (18) | 0.00080 (14) | 0.00038 (14) | −0.00305 (14) |
| O1 | 0.0260 (10) | 0.0323 (10) | 0.0412 (10) | −0.0017 (8) | 0.0033 (8) | −0.0039 (8) |
| O2 | 0.0329 (12) | 0.0451 (12) | 0.0550 (13) | 0.0028 (10) | 0.0102 (10) | −0.0096 (10) |
| O3 | 0.0254 (10) | 0.0331 (10) | 0.0395 (10) | −0.0007 (8) | 0.0023 (8) | −0.0058 (8) |
| O4 | 0.0332 (11) | 0.0323 (11) | 0.0581 (13) | −0.0039 (9) | 0.0015 (10) | −0.0054 (9) |
| O5 | 0.0480 (16) | 0.110 (2) | 0.0565 (16) | 0.0155 (16) | 0.0019 (13) | 0.0115 (16) |
| O6 | 0.097 (3) | 0.156 (4) | 0.066 (2) | 0.010 (3) | −0.0267 (18) | 0.047 (2) |
| O7 | 0.0560 (19) | 0.133 (3) | 0.0713 (19) | 0.0041 (19) | −0.0019 (15) | 0.0353 (19) |
| O8 | 0.074 (2) | 0.073 (2) | 0.112 (2) | 0.0265 (17) | −0.0351 (19) | −0.0507 (18) |
| O9 | 0.069 (2) | 0.0542 (18) | 0.171 (3) | 0.0109 (15) | 0.006 (2) | −0.053 (2) |
| O10 | 0.130 (3) | 0.0625 (19) | 0.080 (2) | 0.0355 (19) | −0.025 (2) | −0.0164 (16) |
| O11 | 0.0482 (16) | 0.079 (2) | 0.0792 (19) | −0.0052 (14) | −0.0038 (14) | 0.0269 (15) |
| O12 | 0.090 (3) | 0.141 (3) | 0.071 (2) | 0.005 (2) | −0.0150 (18) | 0.055 (2) |
| O13 | 0.0548 (15) | 0.0523 (14) | 0.0540 (14) | −0.0093 (12) | −0.0132 (11) | 0.0091 (11) |
| O14 | 0.0496 (14) | 0.0531 (14) | 0.0403 (12) | −0.0043 (11) | −0.0052 (10) | 0.0072 (10) |
| O15 | 0.0446 (14) | 0.0628 (15) | 0.0399 (12) | 0.0076 (11) | −0.0007 (10) | 0.0083 (10) |
| N1 | 0.0467 (16) | 0.0302 (13) | 0.0394 (13) | −0.0045 (11) | −0.0014 (11) | −0.0027 (10) |
| N2 | 0.0371 (14) | 0.0386 (13) | 0.0342 (12) | 0.0052 (11) | 0.0007 (10) | −0.0062 (10) |
| N3 | 0.054 (2) | 0.0603 (19) | 0.0587 (19) | 0.0014 (16) | −0.0162 (16) | 0.0103 (15) |
| N4 | 0.0458 (18) | 0.0390 (16) | 0.084 (2) | −0.0042 (13) | 0.0132 (16) | −0.0199 (15) |
| N5 | 0.056 (2) | 0.0598 (19) | 0.0539 (18) | 0.0065 (16) | 0.0000 (15) | 0.0146 (15) |
| C1 | 0.0291 (15) | 0.0411 (16) | 0.0297 (13) | −0.0023 (12) | −0.0037 (11) | 0.0061 (11) |
| C2 | 0.0286 (15) | 0.0449 (17) | 0.0387 (15) | −0.0006 (13) | 0.0007 (12) | 0.0042 (13) |
| C3 | 0.0310 (17) | 0.061 (2) | 0.058 (2) | 0.0007 (15) | 0.0055 (15) | 0.0071 (17) |
| C4 | 0.0290 (17) | 0.069 (2) | 0.072 (2) | −0.0102 (17) | 0.0045 (16) | 0.0066 (19) |
| C5 | 0.043 (2) | 0.055 (2) | 0.064 (2) | −0.0178 (17) | −0.0035 (17) | 0.0033 (17) |
| C6 | 0.0351 (17) | 0.0419 (17) | 0.0413 (16) | −0.0074 (13) | −0.0027 (13) | 0.0049 (13) |
| C7 | 0.0466 (19) | 0.0345 (16) | 0.0427 (16) | −0.0128 (14) | −0.0052 (14) | 0.0014 (12) |
| C8 | 0.064 (3) | 0.0385 (18) | 0.066 (2) | −0.0066 (17) | 0.0016 (19) | −0.0156 (16) |
| C9 | 0.070 (3) | 0.0344 (17) | 0.062 (2) | 0.0127 (17) | −0.0095 (19) | −0.0133 (16) |
| C10 | 0.052 (2) | 0.050 (2) | 0.056 (2) | 0.0082 (16) | 0.0050 (17) | −0.0218 (16) |
| C11 | 0.0379 (17) | 0.0450 (17) | 0.0380 (15) | 0.0119 (14) | 0.0065 (13) | −0.0019 (13) |
| C12 | 0.0302 (15) | 0.0437 (16) | 0.0326 (14) | 0.0052 (13) | 0.0039 (11) | 0.0037 (12) |
| C13 | 0.0290 (16) | 0.0530 (19) | 0.0513 (18) | 0.0068 (14) | 0.0065 (13) | 0.0035 (15) |
| C14 | 0.0255 (16) | 0.068 (2) | 0.057 (2) | −0.0038 (15) | 0.0005 (14) | 0.0039 (17) |
| C15 | 0.0322 (16) | 0.0441 (17) | 0.0496 (18) | −0.0067 (13) | −0.0009 (13) | −0.0017 (14) |
| C16 | 0.0305 (15) | 0.0382 (15) | 0.0336 (14) | 0.0008 (12) | 0.0004 (11) | 0.0042 (12) |
| C17 | 0.0263 (13) | 0.0379 (15) | 0.0295 (13) | 0.0010 (12) | 0.0008 (10) | 0.0045 (11) |
| C18 | 0.052 (2) | 0.0362 (18) | 0.100 (3) | −0.0080 (16) | 0.009 (2) | −0.0035 (18) |
| C19 | 0.059 (2) | 0.052 (2) | 0.084 (3) | 0.0058 (18) | 0.032 (2) | −0.0128 (19) |
| C20 | 0.090 (3) | 0.077 (3) | 0.055 (2) | −0.014 (3) | 0.002 (2) | 0.019 (2) |
| C21 | 0.069 (3) | 0.073 (3) | 0.051 (2) | 0.004 (2) | 0.0041 (18) | 0.0223 (19) |
| O16 | 0.107 (3) | 0.101 (3) | 0.093 (2) | −0.009 (2) | −0.046 (2) | −0.006 (2) |
| C22 | 0.128 (6) | 0.160 (7) | 0.092 (4) | 0.022 (5) | −0.049 (4) | −0.010 (4) |
| O17 | 0.085 (3) | 0.119 (3) | 0.161 (4) | −0.011 (2) | −0.052 (3) | 0.011 (3) |
| C23 | 0.085 (4) | 0.096 (4) | 0.093 (4) | 0.014 (3) | −0.011 (3) | 0.017 (3) |
| Pr1—O3 | 2.3804 (19) | C4—H4A | 0.9300 |
| Pr1—O1 | 2.3903 (19) | C5—C6 | 1.399 (4) |
| Pr1—O8 | 2.552 (3) | C5—H5A | 0.9300 |
| Pr1—O13 | 2.554 (2) | C6—C7 | 1.448 (4) |
| Pr1—O5 | 2.580 (3) | C7—H7A | 0.9300 |
| Pr1—O2 | 2.587 (2) | C8—C9 | 1.498 (5) |
| Pr1—O4 | 2.597 (2) | C8—H8A | 0.9700 |
| Pr1—O10 | 2.616 (3) | C8—H8B | 0.9700 |
| Pr1—O11 | 2.629 (3) | C9—C10 | 1.502 (5) |
| Pr1—O7 | 2.639 (3) | C9—H9A | 0.9700 |
| Pr1—Ni2 | 3.5340 (6) | C9—H9B | 0.9700 |
| Ni2—N2 | 2.018 (2) | C10—H10A | 0.9700 |
| Ni2—O1 | 2.0298 (19) | C10—H10B | 0.9700 |
| Ni2—N1 | 2.035 (2) | C11—C12 | 1.459 (4) |
| Ni2—O3 | 2.0427 (19) | C11—H11A | 0.9300 |
| Ni2—O14 | 2.125 (2) | C12—C13 | 1.400 (4) |
| Ni2—O15 | 2.151 (2) | C12—C17 | 1.403 (4) |
| O1—C1 | 1.325 (3) | C13—C14 | 1.366 (5) |
| O2—C2 | 1.391 (4) | C13—H13A | 0.9300 |
| O2—C19 | 1.434 (4) | C14—C15 | 1.394 (5) |
| O3—C17 | 1.325 (3) | C14—H14A | 0.9300 |
| O4—C16 | 1.393 (3) | C15—C16 | 1.367 (4) |
| O4—C18 | 1.422 (4) | C15—H15A | 0.9300 |
| O5—N3 | 1.221 (4) | C16—C17 | 1.406 (4) |
| O6—N3 | 1.225 (4) | C18—H18A | 0.9600 |
| O7—N3 | 1.245 (4) | C18—H18B | 0.9600 |
| O8—N4 | 1.254 (4) | C18—H18C | 0.9600 |
| O9—N4 | 1.210 (4) | C19—H19A | 0.9600 |
| O10—N4 | 1.232 (4) | C19—H19B | 0.9600 |
| O11—N5 | 1.256 (4) | C19—H19C | 0.9600 |
| O12—N5 | 1.213 (4) | C20—H20A | 0.9600 |
| O13—N5 | 1.256 (4) | C20—H20B | 0.9600 |
| O14—C20 | 1.417 (4) | C20—H20C | 0.9600 |
| O14—H14O | 0.8501 | C21—H21A | 0.9600 |
| O15—C21 | 1.413 (4) | C21—H21B | 0.9600 |
| O15—H15O | 0.8500 | C21—H21C | 0.9600 |
| N1—C7 | 1.274 (4) | O16—C22 | 1.399 (6) |
| N1—C8 | 1.492 (4) | O16—H16O | 0.8499 |
| N2—C11 | 1.271 (4) | C22—H22A | 0.9600 |
| N2—C10 | 1.466 (4) | C22—H22B | 0.9600 |
| C1—C2 | 1.405 (4) | C22—H22C | 0.9600 |
| C1—C6 | 1.406 (4) | O17—C23 | 1.356 (6) |
| C2—C3 | 1.370 (4) | O17—H17O | 0.8500 |
| C3—C4 | 1.384 (5) | C23—H23A | 0.9600 |
| C3—H3A | 0.9300 | C23—H23B | 0.9600 |
| C4—C5 | 1.360 (5) | C23—H23C | 0.9600 |
| O3—Pr1—O1 | 67.28 (6) | O5—N3—O7 | 116.3 (3) |
| O3—Pr1—O8 | 138.96 (9) | O6—N3—O7 | 122.7 (4) |
| O1—Pr1—O8 | 146.42 (10) | O9—N4—O10 | 121.2 (4) |
| O3—Pr1—O13 | 91.75 (8) | O9—N4—O8 | 123.5 (4) |
| O1—Pr1—O13 | 76.24 (7) | O10—N4—O8 | 115.1 (3) |
| O8—Pr1—O13 | 114.71 (10) | O12—N5—O11 | 122.7 (3) |
| O3—Pr1—O5 | 76.27 (8) | O12—N5—O13 | 120.7 (4) |
| O1—Pr1—O5 | 94.63 (9) | O11—N5—O13 | 116.6 (3) |
| O8—Pr1—O5 | 77.86 (11) | O1—C1—C2 | 119.1 (3) |
| O13—Pr1—O5 | 167.18 (9) | O1—C1—C6 | 124.2 (3) |
| O3—Pr1—O2 | 129.99 (7) | C2—C1—C6 | 116.8 (3) |
| O1—Pr1—O2 | 62.94 (7) | C3—C2—O2 | 123.7 (3) |
| O8—Pr1—O2 | 89.17 (10) | C3—C2—C1 | 122.9 (3) |
| O13—Pr1—O2 | 72.56 (8) | O2—C2—C1 | 113.4 (2) |
| O5—Pr1—O2 | 111.60 (8) | C2—C3—C4 | 119.2 (3) |
| O3—Pr1—O4 | 63.26 (7) | C2—C3—H3A | 120.4 |
| O1—Pr1—O4 | 129.60 (6) | C4—C3—H3A | 120.4 |
| O8—Pr1—O4 | 77.13 (10) | C5—C4—C3 | 119.8 (3) |
| O13—Pr1—O4 | 113.66 (8) | C5—C4—H4A | 120.1 |
| O5—Pr1—O4 | 65.20 (9) | C3—C4—H4A | 120.1 |
| O2—Pr1—O4 | 166.28 (7) | C4—C5—C6 | 121.8 (3) |
| O3—Pr1—O10 | 143.55 (9) | C4—C5—H5A | 119.1 |
| O1—Pr1—O10 | 129.23 (10) | C6—C5—H5A | 119.1 |
| O8—Pr1—O10 | 47.88 (10) | C5—C6—C1 | 119.5 (3) |
| O13—Pr1—O10 | 66.87 (9) | C5—C6—C7 | 116.7 (3) |
| O5—Pr1—O10 | 125.74 (10) | C1—C6—C7 | 123.8 (3) |
| O2—Pr1—O10 | 73.27 (11) | N1—C7—C6 | 128.9 (3) |
| O4—Pr1—O10 | 97.47 (10) | N1—C7—H7A | 115.6 |
| O3—Pr1—O11 | 76.63 (8) | C6—C7—H7A | 115.6 |
| O1—Pr1—O11 | 111.86 (8) | N1—C8—C9 | 114.2 (3) |
| O8—Pr1—O11 | 97.19 (11) | N1—C8—H8A | 108.7 |
| O13—Pr1—O11 | 48.68 (8) | C9—C8—H8A | 108.7 |
| O5—Pr1—O11 | 130.31 (9) | N1—C8—H8B | 108.7 |
| O2—Pr1—O11 | 117.78 (8) | C9—C8—H8B | 108.7 |
| O4—Pr1—O11 | 65.52 (8) | H8A—C8—H8B | 107.6 |
| O10—Pr1—O11 | 67.06 (11) | C8—C9—C10 | 114.8 (3) |
| O3—Pr1—O7 | 111.93 (9) | C8—C9—H9A | 108.6 |
| O1—Pr1—O7 | 80.99 (10) | C10—C9—H9A | 108.6 |
| O8—Pr1—O7 | 69.83 (13) | C8—C9—H9B | 108.6 |
| O13—Pr1—O7 | 137.39 (9) | C10—C9—H9B | 108.6 |
| O5—Pr1—O7 | 47.29 (9) | H9A—C9—H9B | 107.5 |
| O2—Pr1—O7 | 65.04 (9) | N2—C10—C9 | 111.2 (3) |
| O4—Pr1—O7 | 108.65 (9) | N2—C10—H10A | 109.4 |
| O10—Pr1—O7 | 103.36 (11) | C9—C10—H10A | 109.4 |
| O11—Pr1—O7 | 166.94 (11) | N2—C10—H10B | 109.4 |
| O3—Pr1—Ni2 | 33.79 (5) | C9—C10—H10B | 109.4 |
| O1—Pr1—Ni2 | 33.53 (5) | H10A—C10—H10B | 108.0 |
| O8—Pr1—Ni2 | 163.62 (8) | N2—C11—C12 | 126.8 (3) |
| O13—Pr1—Ni2 | 81.66 (6) | N2—C11—H11A | 116.6 |
| O5—Pr1—Ni2 | 85.78 (7) | C12—C11—H11A | 116.6 |
| O2—Pr1—Ni2 | 96.25 (5) | C13—C12—C17 | 119.7 (3) |
| O4—Pr1—Ni2 | 96.77 (5) | C13—C12—C11 | 116.1 (3) |
| O10—Pr1—Ni2 | 148.47 (7) | C17—C12—C11 | 124.1 (3) |
| O11—Pr1—Ni2 | 93.93 (7) | C14—C13—C12 | 121.5 (3) |
| O7—Pr1—Ni2 | 98.46 (9) | C14—C13—H13A | 119.3 |
| N2—Ni2—O1 | 170.50 (9) | C12—C13—H13A | 119.3 |
| N2—Ni2—N1 | 98.11 (10) | C13—C14—C15 | 119.4 (3) |
| O1—Ni2—N1 | 91.11 (9) | C13—C14—H14A | 120.3 |
| N2—Ni2—O3 | 89.90 (9) | C15—C14—H14A | 120.3 |
| O1—Ni2—O3 | 80.93 (8) | C16—C15—C14 | 119.6 (3) |
| N1—Ni2—O3 | 171.92 (9) | C16—C15—H15A | 120.2 |
| N2—Ni2—O14 | 91.34 (10) | C14—C15—H15A | 120.2 |
| O1—Ni2—O14 | 91.21 (9) | C15—C16—O4 | 123.5 (3) |
| N1—Ni2—O14 | 88.46 (10) | C15—C16—C17 | 122.5 (3) |
| O3—Ni2—O14 | 90.33 (9) | O4—C16—C17 | 114.0 (2) |
| N2—Ni2—O15 | 87.12 (10) | O3—C17—C12 | 123.9 (3) |
| O1—Ni2—O15 | 90.18 (9) | O3—C17—C16 | 119.0 (2) |
| N1—Ni2—O15 | 92.60 (10) | C12—C17—C16 | 117.2 (3) |
| O3—Ni2—O15 | 88.82 (9) | O4—C18—H18A | 109.5 |
| O14—Ni2—O15 | 178.24 (9) | O4—C18—H18B | 109.5 |
| N2—Ni2—Pr1 | 130.30 (7) | H18A—C18—H18B | 109.5 |
| O1—Ni2—Pr1 | 40.58 (5) | O4—C18—H18C | 109.5 |
| N1—Ni2—Pr1 | 131.58 (8) | H18A—C18—H18C | 109.5 |
| O3—Ni2—Pr1 | 40.40 (5) | H18B—C18—H18C | 109.5 |
| O14—Ni2—Pr1 | 89.48 (7) | O2—C19—H19A | 109.5 |
| O15—Ni2—Pr1 | 90.87 (7) | O2—C19—H19B | 109.5 |
| C1—O1—Ni2 | 126.40 (18) | H19A—C19—H19B | 109.5 |
| C1—O1—Pr1 | 124.92 (17) | O2—C19—H19C | 109.5 |
| Ni2—O1—Pr1 | 105.89 (8) | H19A—C19—H19C | 109.5 |
| C2—O2—C19 | 117.8 (3) | H19B—C19—H19C | 109.5 |
| C2—O2—Pr1 | 118.10 (16) | O14—C20—H20A | 109.5 |
| C19—O2—Pr1 | 123.9 (2) | O14—C20—H20B | 109.5 |
| C17—O3—Ni2 | 125.58 (17) | H20A—C20—H20B | 109.5 |
| C17—O3—Pr1 | 124.57 (17) | O14—C20—H20C | 109.5 |
| Ni2—O3—Pr1 | 105.82 (8) | H20A—C20—H20C | 109.5 |
| C16—O4—C18 | 116.6 (2) | H20B—C20—H20C | 109.5 |
| C16—O4—Pr1 | 116.51 (16) | O15—C21—H21A | 109.5 |
| C18—O4—Pr1 | 126.5 (2) | O15—C21—H21B | 109.5 |
| N3—O5—Pr1 | 100.0 (2) | H21A—C21—H21B | 109.5 |
| N3—O7—Pr1 | 96.4 (2) | O15—C21—H21C | 109.5 |
| N4—O8—Pr1 | 99.7 (2) | H21A—C21—H21C | 109.5 |
| N4—O10—Pr1 | 97.2 (2) | H21B—C21—H21C | 109.5 |
| N5—O11—Pr1 | 95.5 (2) | C22—O16—H16O | 108.8 |
| N5—O13—Pr1 | 99.1 (2) | O16—C22—H22A | 109.5 |
| C20—O14—Ni2 | 124.7 (2) | O16—C22—H22B | 109.5 |
| C20—O14—H14O | 99.9 | H22A—C22—H22B | 109.5 |
| Ni2—O14—H14O | 123.9 | O16—C22—H22C | 109.5 |
| C21—O15—Ni2 | 126.6 (2) | H22A—C22—H22C | 109.5 |
| C21—O15—H15O | 114.5 | H22B—C22—H22C | 109.5 |
| Ni2—O15—H15O | 110.8 | C23—O17—H17O | 96.4 |
| C7—N1—C8 | 114.4 (3) | O17—C23—H23A | 109.5 |
| C7—N1—Ni2 | 123.8 (2) | O17—C23—H23B | 109.5 |
| C8—N1—Ni2 | 121.7 (2) | H23A—C23—H23B | 109.5 |
| C11—N2—C10 | 116.5 (3) | O17—C23—H23C | 109.5 |
| C11—N2—Ni2 | 125.3 (2) | H23A—C23—H23C | 109.5 |
| C10—N2—Ni2 | 117.9 (2) | H23B—C23—H23C | 109.5 |
| O5—N3—O6 | 121.0 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O14—H14O···O16 | 0.85 | 1.81 | 2.661 (4) | 180 |
| O15—H15O···O6i | 0.85 | 2.28 | 3.128 (5) | 180 |
| O16—H16O···O17ii | 0.85 | 1.87 | 2.720 (6) | 179 |
| O17—H17O···O13 | 0.85 | 2.05 | 2.905 (5) | 180 |
| Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, y+1/2, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O14—H14O···O16 | 0.85 | 1.81 | 2.661 (4) | 180 |
| O15—H15O···O6i | 0.85 | 2.28 | 3.128 (5) | 180 |
| O16—H16O···O17ii | 0.85 | 1.87 | 2.720 (6) | 179 |
| O17—H17O···O13 | 0.85 | 2.05 | 2.905 (5) | 180 |
| Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, y+1/2, −z+1/2. |
The authors gratefully acknowledge financial support from the Education Department of Liaoning Province (2006 B 112) and Liaoning University.
Elmali, A. & Elerman, Y. (2003). Z. Naturforsch. Teil B, 58, 639–643.
Elmali, A. & Elerman, Y. (2004). Z. Naturforsch. Teil B, 59, 535–540.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
The molecular structure is shown in Fig. 1. The hexadentate Schiff base ligand links NiII and PrIII ions to form a dinuclear complex via two bridging phenolate O atoms, similar to reported copper-lanthanum complexes of the same ligand (Elmali & Elerman (2003,2004). The PrIII ion is ten-coordinated by four O atoms from the Schiff base ligand and six O atoms from three chelating nitrate ligands. The NiII ion is coordinated by two N atoms and two O atoms from the Schiff base ligand and two methanol oxygen atoms. In the crystal structure, intermolecular O—H···O hydrogen bonds connect complex molecules and methanol solvent molecules to form (1 0 - 2) sheets.