Acta Cryst. (2008). E64, m1207 [ doi:10.1107/S1600536808026986 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-6,6'-Dimethoxy-2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}dimethanoltrinitratonickel(II)lanthanum(III) methanol disolvateIn the title dinuclear complex, [NiLa(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 O atoms of two methanol ligands, forming a slightly distorted octahedral geometry. The LaIII ion is coordinated by six O atoms from three chelating nitrate ligands and four O atoms from the 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, forming a two-dimensional network.
The title complex was obtained by the treatment of nickel(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 lanthanum (III) nitrate hexahydrate (0.1082 g, 0.25 mmol). The reaction mixture was cooled and filtered; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Blue single crystals were obtained after several days. Analysis calculated for C23H36NiN5O17La: C, 32.48; H, 4.02; N, 8.27; found: C, 32.49; H, 4.03; N, 8.24
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) and with Uiso(H) = 1.2Ueq(C) or C—H = 0.96 Å (methly C) and with Uiso(H) = 1.5Ueq(C). H atoms bond to O atoms of methanol were initially located in a difference Fourier map, but were subsequently treated as riding on their parent atoms, with O—H = 0.85 Å, and with Uiso(H) = 1.2Ueq(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]](./lh2680fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids. The dashed line indicates a hydrogen bond. |
| [NiLa(C19H20N2O4)(NO3)3(CH3OH)2]·2CH3OH | F000 = 1716 |
| Mr = 852.19 | Dx = 1.739 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 24213 reflections |
| a = 13.123 (4) Å | θ = 6.0–55.0º |
| b = 11.141 (3) Å | µ = 1.96 mm−1 |
| c = 22.245 (8) Å | T = 291 (2) K |
| β = 90.911 (13)º | Block, green |
| V = 3252.0 (17) Å3 | 0.30 × 0.27 × 0.25 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 7431 independent reflections |
| Radiation source: fine-focus sealed tube | 6035 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.039 |
| T = 291(2) K | θmax = 27.5º |
| ω scans | θmin = 3.0º |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→17 |
| Tmin = 0.594, Tmax = 0.635 | k = −14→14 |
| 29897 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)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0311P)2 + 2.8126P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.005 |
| 7431 reflections | Δρmax = 0.67 e Å−3 |
| 430 parameters | Δρmin = −0.56 e Å−3 |
| 19 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [NiLa(C19H20N2O4)(NO3)3(CH3OH)2]·2CH3OH | V = 3252.0 (17) Å3 |
| Mr = 852.19 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 13.123 (4) Å | µ = 1.96 mm−1 |
| b = 11.141 (3) Å | T = 291 (2) K |
| c = 22.245 (8) Å | 0.30 × 0.27 × 0.25 mm |
| β = 90.911 (13)º |
| Rigaku R-AXIS RAPID diffractometer | 7431 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6035 reflections with I > 2σ(I) |
| Tmin = 0.594, Tmax = 0.635 | Rint = 0.039 |
| 29897 measured reflections |
| R[F2 > 2σ(F2)] = 0.032 | 19 restraints |
| wR(F2) = 0.078 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.67 e Å−3 |
| 7431 reflections | Δρmin = −0.56 e Å−3 |
| 430 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 | ||
| C1 | 0.8780 (2) | 0.0634 (3) | 0.09172 (14) | 0.0366 (7) | |
| C2 | 0.9465 (2) | 0.1419 (3) | 0.06390 (15) | 0.0401 (7) | |
| C3 | 1.0476 (3) | 0.1149 (4) | 0.05748 (18) | 0.0537 (9) | |
| H1 | 1.0910 | 0.1693 | 0.0391 | 0.064* | |
| C4 | 1.0845 (3) | 0.0066 (4) | 0.0784 (2) | 0.0643 (12) | |
| H2 | 1.1531 | −0.0123 | 0.0743 | 0.077* | |
| C5 | 1.0206 (3) | −0.0725 (4) | 0.10520 (19) | 0.0589 (10) | |
| H3 | 1.0465 | −0.1451 | 0.1193 | 0.071* | |
| C6 | 0.9159 (3) | −0.0475 (3) | 0.11218 (16) | 0.0431 (8) | |
| C7 | 0.8545 (3) | −0.1397 (3) | 0.13938 (15) | 0.0451 (8) | |
| H4 | 0.8874 | −0.2124 | 0.1465 | 0.054* | |
| C8 | 0.7240 (3) | −0.2462 (4) | 0.1852 (2) | 0.0601 (11) | |
| H5 | 0.7502 | −0.3157 | 0.1642 | 0.072* | |
| H6 | 0.7514 | −0.2484 | 0.2260 | 0.072* | |
| C9 | 0.6108 (3) | −0.2557 (3) | 0.18749 (19) | 0.0594 (11) | |
| H7 | 0.5932 | −0.3335 | 0.2039 | 0.071* | |
| H8 | 0.5835 | −0.2521 | 0.1468 | 0.071* | |
| C10 | 0.5605 (3) | −0.1597 (4) | 0.22441 (18) | 0.0576 (10) | |
| H9 | 0.4938 | −0.1873 | 0.2365 | 0.069* | |
| H10 | 0.6010 | −0.1451 | 0.2606 | 0.069* | |
| C11 | 0.4605 (3) | −0.0025 (3) | 0.18742 (15) | 0.0431 (8) | |
| H11 | 0.4089 | −0.0455 | 0.2059 | 0.052* | |
| C12 | 0.4305 (2) | 0.1090 (3) | 0.15813 (14) | 0.0368 (7) | |
| C13 | 0.3254 (3) | 0.1336 (4) | 0.15613 (16) | 0.0482 (9) | |
| H12 | 0.2801 | 0.0778 | 0.1715 | 0.058* | |
| C14 | 0.2889 (3) | 0.2375 (4) | 0.13210 (18) | 0.0530 (9) | |
| H13 | 0.2190 | 0.2515 | 0.1302 | 0.064* | |
| C15 | 0.3559 (3) | 0.3222 (3) | 0.11042 (16) | 0.0459 (8) | |
| H14 | 0.3314 | 0.3941 | 0.0946 | 0.055* | |
| C16 | 0.4587 (2) | 0.3001 (3) | 0.11238 (14) | 0.0368 (7) | |
| C17 | 0.4991 (2) | 0.1913 (3) | 0.13444 (13) | 0.0322 (6) | |
| C18 | 0.5015 (3) | 0.5034 (3) | 0.0877 (2) | 0.0700 (13) | |
| H15 | 0.4575 | 0.5132 | 0.0532 | 0.105* | |
| H16 | 0.5608 | 0.5530 | 0.0835 | 0.105* | |
| H17 | 0.4658 | 0.5265 | 0.1233 | 0.105* | |
| C19 | 0.9595 (3) | 0.3228 (4) | 0.0049 (2) | 0.0700 (13) | |
| H18 | 1.0106 | 0.3659 | 0.0275 | 0.105* | |
| H19 | 0.9145 | 0.3788 | −0.0148 | 0.105* | |
| H20 | 0.9917 | 0.2736 | −0.0247 | 0.105* | |
| C20 | 0.6496 (3) | −0.0934 (4) | 0.01313 (18) | 0.0659 (12) | |
| H22 | 0.7123 | −0.0503 | 0.0081 | 0.099* | |
| H23 | 0.6061 | −0.0807 | −0.0214 | 0.099* | |
| H24 | 0.6639 | −0.1775 | 0.0173 | 0.099* | |
| C21 | 0.6865 (4) | 0.1415 (5) | 0.2730 (2) | 0.0808 (15) | |
| H26 | 0.6287 | 0.1829 | 0.2560 | 0.121* | |
| H27 | 0.7315 | 0.1984 | 0.2920 | 0.121* | |
| H28 | 0.6638 | 0.0845 | 0.3023 | 0.121* | |
| C22 | 0.0864 (6) | 0.5031 (8) | 0.1513 (3) | 0.149 (3) | |
| H30 | 0.0580 | 0.4386 | 0.1279 | 0.223* | |
| H31 | 0.1406 | 0.5403 | 0.1296 | 0.223* | |
| H32 | 0.0344 | 0.5614 | 0.1591 | 0.223* | |
| C23 | 0.0337 (5) | 0.1674 (7) | 0.2229 (3) | 0.117 (2) | |
| H34 | 0.0975 | 0.1417 | 0.2402 | 0.175* | |
| H35 | 0.0392 | 0.1713 | 0.1800 | 0.175* | |
| H36 | −0.0187 | 0.1113 | 0.2333 | 0.175* | |
| La1 | 0.716978 (13) | 0.298199 (16) | 0.077571 (8) | 0.03422 (6) | |
| N1 | 0.7614 (2) | −0.1353 (2) | 0.15504 (12) | 0.0418 (6) | |
| N2 | 0.5498 (2) | −0.0480 (2) | 0.19058 (12) | 0.0390 (6) | |
| N3 | 0.7794 (3) | 0.3947 (3) | 0.20112 (16) | 0.0617 (9) | |
| N4 | 0.7756 (3) | 0.5503 (3) | 0.03456 (19) | 0.0611 (9) | |
| N5 | 0.6410 (3) | 0.2140 (3) | −0.04698 (17) | 0.0621 (9) | |
| Ni2 | 0.67227 (3) | 0.01383 (3) | 0.146167 (17) | 0.03239 (10) | |
| O1 | 0.78086 (15) | 0.09678 (19) | 0.09686 (10) | 0.0356 (5) | |
| O2 | 0.90251 (18) | 0.2485 (2) | 0.04465 (11) | 0.0470 (6) | |
| O3 | 0.59889 (15) | 0.17423 (19) | 0.13315 (10) | 0.0356 (5) | |
| O4 | 0.53172 (17) | 0.3812 (2) | 0.09263 (11) | 0.0443 (6) | |
| O5 | 0.6940 (2) | 0.4204 (3) | 0.17893 (15) | 0.0735 (9) | |
| O6 | 0.8089 (3) | 0.4327 (4) | 0.24951 (17) | 0.1125 (15) | |
| O7 | 0.8346 (2) | 0.3244 (3) | 0.17146 (13) | 0.0589 (7) | |
| O8 | 0.8196 (3) | 0.5040 (3) | 0.07811 (17) | 0.0959 (12) | |
| O9 | 0.7975 (3) | 0.6493 (3) | 0.0170 (2) | 0.1064 (14) | |
| O10 | 0.7118 (3) | 0.4850 (3) | 0.00799 (18) | 0.0955 (12) | |
| O11 | 0.5842 (2) | 0.2296 (3) | −0.00488 (15) | 0.0778 (9) | |
| O12 | 0.6076 (3) | 0.1809 (4) | −0.09563 (17) | 0.1162 (16) | |
| O13 | 0.7331 (3) | 0.2290 (4) | −0.03695 (16) | 0.0968 (12) | |
| O14 | 0.60041 (19) | −0.0515 (2) | 0.06531 (11) | 0.0509 (6) | |
| H21 | 0.5412 | −0.0823 | 0.0666 | 0.061* | |
| O15 | 0.73884 (19) | 0.0805 (2) | 0.22691 (11) | 0.0502 (6) | |
| H25 | 0.7842 | 0.0402 | 0.2457 | 0.060* | |
| O16 | 0.1250 (4) | 0.4577 (4) | 0.2063 (2) | 0.1259 (17) | |
| H29 | 0.1888 | 0.4494 | 0.2018 | 0.151* | |
| O17 | 0.0099 (4) | 0.2770 (5) | 0.2444 (3) | 0.147 (2) | |
| H33 | 0.0169 | 0.3201 | 0.2133 | 0.177* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0312 (15) | 0.0446 (18) | 0.0340 (16) | 0.0024 (14) | −0.0012 (12) | −0.0059 (14) |
| C2 | 0.0315 (16) | 0.0459 (19) | 0.0431 (18) | −0.0004 (15) | 0.0033 (14) | −0.0053 (15) |
| C3 | 0.0344 (17) | 0.067 (3) | 0.060 (2) | −0.0023 (18) | 0.0070 (16) | −0.012 (2) |
| C4 | 0.0324 (18) | 0.081 (3) | 0.080 (3) | 0.011 (2) | 0.0056 (19) | −0.008 (2) |
| C5 | 0.049 (2) | 0.060 (2) | 0.067 (3) | 0.020 (2) | −0.0034 (19) | −0.006 (2) |
| C6 | 0.0384 (17) | 0.0447 (19) | 0.0462 (19) | 0.0099 (15) | −0.0024 (15) | −0.0058 (15) |
| C7 | 0.053 (2) | 0.0370 (18) | 0.0453 (19) | 0.0136 (16) | −0.0050 (16) | 0.0010 (15) |
| C8 | 0.072 (3) | 0.0383 (19) | 0.070 (3) | 0.008 (2) | 0.003 (2) | 0.0148 (19) |
| C9 | 0.079 (3) | 0.0354 (18) | 0.063 (3) | −0.013 (2) | −0.009 (2) | 0.0147 (18) |
| C10 | 0.057 (2) | 0.057 (2) | 0.059 (2) | −0.007 (2) | 0.0079 (19) | 0.028 (2) |
| C11 | 0.0400 (17) | 0.050 (2) | 0.0393 (18) | −0.0118 (16) | 0.0064 (14) | 0.0010 (15) |
| C12 | 0.0349 (15) | 0.0425 (17) | 0.0330 (16) | −0.0029 (15) | 0.0039 (12) | −0.0029 (14) |
| C13 | 0.0346 (17) | 0.060 (2) | 0.050 (2) | −0.0089 (17) | 0.0062 (15) | −0.0038 (18) |
| C14 | 0.0301 (17) | 0.069 (3) | 0.060 (2) | 0.0017 (18) | 0.0024 (16) | −0.001 (2) |
| C15 | 0.0372 (17) | 0.052 (2) | 0.049 (2) | 0.0082 (16) | −0.0002 (15) | −0.0011 (16) |
| C16 | 0.0319 (15) | 0.0423 (17) | 0.0363 (16) | −0.0011 (15) | 0.0025 (12) | −0.0015 (14) |
| C17 | 0.0310 (14) | 0.0381 (16) | 0.0277 (14) | −0.0014 (13) | 0.0022 (11) | −0.0043 (12) |
| C18 | 0.055 (2) | 0.035 (2) | 0.121 (4) | 0.0074 (18) | 0.007 (3) | 0.003 (2) |
| C19 | 0.061 (3) | 0.060 (3) | 0.090 (3) | −0.007 (2) | 0.034 (2) | 0.010 (2) |
| C20 | 0.070 (3) | 0.076 (3) | 0.052 (2) | −0.001 (2) | 0.003 (2) | −0.021 (2) |
| C21 | 0.098 (4) | 0.085 (3) | 0.060 (3) | 0.016 (3) | −0.001 (3) | −0.020 (3) |
| C22 | 0.155 (7) | 0.177 (8) | 0.112 (6) | 0.019 (6) | −0.064 (5) | −0.007 (5) |
| C23 | 0.092 (5) | 0.143 (7) | 0.115 (5) | −0.007 (5) | −0.012 (4) | −0.039 (5) |
| La1 | 0.03002 (9) | 0.03160 (10) | 0.04102 (11) | −0.00190 (8) | 0.00050 (7) | 0.00396 (8) |
| N1 | 0.0503 (17) | 0.0328 (14) | 0.0423 (16) | 0.0019 (13) | −0.0010 (13) | 0.0016 (12) |
| N2 | 0.0446 (15) | 0.0386 (14) | 0.0339 (14) | −0.0070 (13) | 0.0011 (12) | 0.0049 (11) |
| N3 | 0.067 (2) | 0.062 (2) | 0.056 (2) | −0.0094 (19) | 0.0026 (17) | −0.0179 (18) |
| N4 | 0.0447 (18) | 0.0439 (18) | 0.095 (3) | 0.0017 (15) | 0.0128 (18) | 0.0207 (19) |
| N5 | 0.058 (2) | 0.068 (2) | 0.059 (2) | −0.0034 (19) | −0.0150 (18) | −0.0095 (18) |
| Ni2 | 0.0339 (2) | 0.03021 (19) | 0.0331 (2) | −0.00145 (17) | 0.00085 (15) | 0.00297 (16) |
| O1 | 0.0286 (10) | 0.0347 (11) | 0.0436 (12) | 0.0027 (9) | 0.0029 (9) | 0.0027 (10) |
| O2 | 0.0375 (12) | 0.0459 (13) | 0.0578 (15) | −0.0013 (11) | 0.0123 (11) | 0.0073 (12) |
| O3 | 0.0284 (10) | 0.0345 (11) | 0.0439 (12) | 0.0007 (9) | 0.0029 (9) | 0.0058 (9) |
| O4 | 0.0358 (12) | 0.0323 (12) | 0.0648 (16) | 0.0040 (10) | 0.0035 (11) | 0.0042 (11) |
| O5 | 0.0490 (16) | 0.088 (2) | 0.084 (2) | 0.0074 (16) | −0.0002 (15) | −0.0301 (18) |
| O6 | 0.099 (3) | 0.156 (4) | 0.081 (3) | −0.001 (3) | −0.018 (2) | −0.066 (3) |
| O7 | 0.0612 (17) | 0.0586 (17) | 0.0564 (16) | 0.0114 (14) | −0.0124 (13) | −0.0126 (13) |
| O8 | 0.132 (3) | 0.067 (2) | 0.087 (3) | −0.038 (2) | −0.028 (2) | 0.0169 (19) |
| O9 | 0.074 (2) | 0.056 (2) | 0.189 (4) | −0.0085 (18) | 0.007 (2) | 0.056 (2) |
| O10 | 0.088 (2) | 0.084 (2) | 0.113 (3) | −0.0284 (19) | −0.031 (2) | 0.050 (2) |
| O11 | 0.0567 (17) | 0.114 (3) | 0.0626 (18) | −0.0191 (18) | −0.0022 (15) | −0.0078 (18) |
| O12 | 0.107 (3) | 0.165 (4) | 0.076 (3) | −0.007 (3) | −0.033 (2) | −0.049 (3) |
| O13 | 0.064 (2) | 0.153 (4) | 0.073 (2) | −0.011 (2) | 0.0007 (17) | −0.035 (2) |
| O14 | 0.0452 (13) | 0.0647 (16) | 0.0429 (14) | −0.0058 (13) | −0.0006 (11) | −0.0085 (12) |
| O15 | 0.0513 (14) | 0.0556 (15) | 0.0436 (13) | 0.0066 (13) | −0.0059 (11) | −0.0066 (12) |
| O16 | 0.134 (4) | 0.129 (4) | 0.113 (3) | −0.016 (3) | −0.068 (3) | 0.004 (3) |
| O17 | 0.117 (4) | 0.135 (4) | 0.187 (6) | 0.001 (3) | −0.069 (4) | 0.005 (4) |
| C1—O1 | 1.334 (4) | C20—O14 | 1.417 (4) |
| C1—C6 | 1.405 (5) | C20—H22 | 0.9600 |
| C1—C2 | 1.405 (5) | C20—H23 | 0.9600 |
| C2—C3 | 1.370 (5) | C20—H24 | 0.9600 |
| C2—O2 | 1.386 (4) | C21—O15 | 1.417 (5) |
| C3—C4 | 1.378 (6) | C21—H26 | 0.9600 |
| C3—H1 | 0.9300 | C21—H27 | 0.9600 |
| C4—C5 | 1.361 (6) | C21—H28 | 0.9600 |
| C4—H2 | 0.9300 | C22—O16 | 1.410 (7) |
| C5—C6 | 1.412 (5) | C22—H30 | 0.9600 |
| C5—H3 | 0.9300 | C22—H31 | 0.9600 |
| C6—C7 | 1.445 (5) | C22—H32 | 0.9600 |
| C7—N1 | 1.276 (4) | C23—O17 | 1.349 (6) |
| C7—H4 | 0.9300 | C23—H34 | 0.9600 |
| C8—C9 | 1.491 (6) | C23—H35 | 0.9600 |
| C8—N1 | 1.493 (5) | C23—H36 | 0.9600 |
| C8—H5 | 0.9700 | La1—O3 | 2.429 (2) |
| C8—H6 | 0.9700 | La1—O1 | 2.431 (2) |
| C9—C10 | 1.507 (6) | La1—O10 | 2.594 (3) |
| C9—H7 | 0.9700 | La1—O7 | 2.594 (3) |
| C9—H8 | 0.9700 | La1—O2 | 2.613 (2) |
| C10—N2 | 1.460 (4) | La1—O11 | 2.623 (3) |
| C10—H9 | 0.9700 | La1—O4 | 2.628 (2) |
| C10—H10 | 0.9700 | La1—O5 | 2.655 (3) |
| C11—N2 | 1.278 (4) | La1—O8 | 2.659 (3) |
| C11—C12 | 1.455 (5) | La1—O13 | 2.673 (4) |
| C11—H11 | 0.9300 | La1—Ni2 | 3.5692 (10) |
| C12—C17 | 1.394 (4) | N1—Ni2 | 2.040 (3) |
| C12—C13 | 1.406 (5) | N2—Ni2 | 2.022 (3) |
| C13—C14 | 1.359 (6) | N3—O6 | 1.214 (4) |
| C13—H12 | 0.9300 | N3—O5 | 1.251 (4) |
| C14—C15 | 1.383 (5) | N3—O7 | 1.261 (4) |
| C14—H13 | 0.9300 | N4—O9 | 1.207 (4) |
| C15—C16 | 1.371 (4) | N4—O8 | 1.233 (5) |
| C15—H14 | 0.9300 | N4—O10 | 1.250 (5) |
| C16—O4 | 1.394 (4) | N5—O12 | 1.218 (4) |
| C16—C17 | 1.408 (4) | N5—O11 | 1.218 (5) |
| C17—O3 | 1.324 (3) | N5—O13 | 1.238 (5) |
| C18—O4 | 1.421 (4) | Ni2—O1 | 2.034 (2) |
| C18—H15 | 0.9600 | Ni2—O3 | 2.048 (2) |
| C18—H16 | 0.9600 | Ni2—O15 | 2.119 (2) |
| C18—H17 | 0.9600 | Ni2—O14 | 2.145 (2) |
| C19—O2 | 1.431 (4) | O14—H21 | 0.8500 |
| C19—H18 | 0.9600 | O15—H25 | 0.8501 |
| C19—H19 | 0.9600 | O16—H29 | 0.8500 |
| C19—H20 | 0.9600 | O17—H33 | 0.8501 |
| O1—C1—C6 | 123.5 (3) | O1—La1—O11 | 94.47 (10) |
| O1—C1—C2 | 118.9 (3) | O10—La1—O11 | 78.79 (12) |
| C6—C1—C2 | 117.6 (3) | O7—La1—O11 | 167.40 (10) |
| C3—C2—O2 | 123.7 (3) | O2—La1—O11 | 110.72 (10) |
| C3—C2—C1 | 122.5 (3) | O3—La1—O4 | 62.36 (7) |
| O2—C2—C1 | 113.8 (3) | O1—La1—O4 | 128.28 (7) |
| C2—C3—C4 | 119.5 (4) | O10—La1—O4 | 77.19 (10) |
| C2—C3—H1 | 120.2 | O7—La1—O4 | 113.45 (9) |
| C4—C3—H1 | 120.2 | O2—La1—O4 | 168.09 (7) |
| C5—C4—C3 | 120.0 (4) | O11—La1—O4 | 65.55 (10) |
| C5—C4—H2 | 120.0 | O3—La1—O5 | 77.13 (9) |
| C3—C4—H2 | 120.0 | O1—La1—O5 | 111.52 (9) |
| C4—C5—C6 | 121.8 (4) | O10—La1—O5 | 95.35 (13) |
| C4—C5—H3 | 119.1 | O7—La1—O5 | 48.14 (9) |
| C6—C5—H3 | 119.1 | O2—La1—O5 | 117.74 (9) |
| C1—C6—C5 | 118.6 (3) | O11—La1—O5 | 131.30 (10) |
| C1—C6—C7 | 124.3 (3) | O4—La1—O5 | 66.02 (8) |
| C5—C6—C7 | 117.1 (3) | O3—La1—O8 | 144.62 (11) |
| N1—C7—C6 | 129.0 (3) | O1—La1—O8 | 128.46 (11) |
| N1—C7—H4 | 115.5 | O10—La1—O8 | 47.10 (11) |
| C6—C7—H4 | 115.5 | O7—La1—O8 | 66.71 (10) |
| C9—C8—N1 | 114.1 (3) | O2—La1—O8 | 73.12 (11) |
| C9—C8—H5 | 108.7 | O11—La1—O8 | 125.80 (11) |
| N1—C8—H5 | 108.7 | O4—La1—O8 | 99.53 (11) |
| C9—C8—H6 | 108.7 | O5—La1—O8 | 67.57 (12) |
| N1—C8—H6 | 108.7 | O3—La1—O13 | 112.47 (10) |
| H5—C8—H6 | 107.6 | O1—La1—O13 | 82.52 (11) |
| C8—C9—C10 | 114.4 (4) | O10—La1—O13 | 70.38 (14) |
| C8—C9—H7 | 108.7 | O7—La1—O13 | 138.12 (10) |
| C10—C9—H7 | 108.7 | O2—La1—O13 | 65.38 (10) |
| C8—C9—H8 | 108.7 | O11—La1—O13 | 46.49 (10) |
| C10—C9—H8 | 108.7 | O4—La1—O13 | 108.09 (10) |
| H7—C9—H8 | 107.6 | O5—La1—O13 | 165.67 (13) |
| N2—C10—C9 | 111.3 (3) | O8—La1—O13 | 101.83 (13) |
| N2—C10—H9 | 109.4 | O3—La1—Ni2 | 33.59 (5) |
| C9—C10—H9 | 109.4 | O1—La1—Ni2 | 33.26 (5) |
| N2—C10—H10 | 109.4 | O10—La1—Ni2 | 164.67 (8) |
| C9—C10—H10 | 109.4 | O7—La1—Ni2 | 81.68 (7) |
| H9—C10—H10 | 108.0 | O2—La1—Ni2 | 95.28 (6) |
| N2—C11—C12 | 127.2 (3) | O11—La1—Ni2 | 85.90 (8) |
| N2—C11—H11 | 116.4 | O4—La1—Ni2 | 95.69 (5) |
| C12—C11—H11 | 116.4 | O5—La1—Ni2 | 94.03 (8) |
| C17—C12—C13 | 119.9 (3) | O8—La1—Ni2 | 148.23 (8) |
| C17—C12—C11 | 124.0 (3) | O13—La1—Ni2 | 99.65 (10) |
| C13—C12—C11 | 116.0 (3) | C7—N1—C8 | 114.4 (3) |
| C14—C13—C12 | 121.2 (3) | C7—N1—Ni2 | 123.7 (2) |
| C14—C13—H12 | 119.4 | C8—N1—Ni2 | 121.7 (2) |
| C12—C13—H12 | 119.4 | C11—N2—C10 | 116.6 (3) |
| C13—C14—C15 | 119.7 (3) | C11—N2—Ni2 | 125.0 (2) |
| C13—C14—H13 | 120.1 | C10—N2—Ni2 | 118.1 (2) |
| C15—C14—H13 | 120.1 | O6—N3—O5 | 122.7 (4) |
| C16—C15—C14 | 119.8 (3) | O6—N3—O7 | 120.2 (4) |
| C16—C15—H14 | 120.1 | O5—N3—O7 | 117.0 (3) |
| C14—C15—H14 | 120.1 | O9—N4—O8 | 121.7 (4) |
| C15—C16—O4 | 123.7 (3) | O9—N4—O10 | 122.7 (4) |
| C15—C16—C17 | 122.1 (3) | O8—N4—O10 | 115.5 (3) |
| O4—C16—C17 | 114.3 (3) | O12—N5—O11 | 120.7 (4) |
| O3—C17—C12 | 124.0 (3) | O12—N5—O13 | 122.5 (4) |
| O3—C17—C16 | 118.9 (3) | O11—N5—O13 | 116.7 (4) |
| C12—C17—C16 | 117.1 (3) | N2—Ni2—O1 | 171.07 (10) |
| O4—C18—H15 | 109.5 | N2—Ni2—N1 | 97.73 (12) |
| O4—C18—H16 | 109.5 | O1—Ni2—N1 | 90.95 (10) |
| H15—C18—H16 | 109.5 | N2—Ni2—O3 | 89.47 (10) |
| O4—C18—H17 | 109.5 | O1—Ni2—O3 | 81.91 (8) |
| H15—C18—H17 | 109.5 | N1—Ni2—O3 | 172.70 (10) |
| H16—C18—H17 | 109.5 | N2—Ni2—O15 | 91.47 (10) |
| O2—C19—H18 | 109.5 | O1—Ni2—O15 | 90.85 (10) |
| O2—C19—H19 | 109.5 | N1—Ni2—O15 | 88.59 (11) |
| H18—C19—H19 | 109.5 | O3—Ni2—O15 | 90.02 (10) |
| O2—C19—H20 | 109.5 | N2—Ni2—O14 | 87.22 (10) |
| H18—C19—H20 | 109.5 | O1—Ni2—O14 | 90.25 (9) |
| H19—C19—H20 | 109.5 | N1—Ni2—O14 | 92.79 (11) |
| O14—C20—H22 | 109.5 | O3—Ni2—O14 | 88.74 (10) |
| O14—C20—H23 | 109.5 | O15—Ni2—O14 | 178.21 (10) |
| H22—C20—H23 | 109.5 | N2—Ni2—La1 | 130.47 (8) |
| O14—C20—H24 | 109.5 | O1—Ni2—La1 | 40.96 (6) |
| H22—C20—H24 | 109.5 | N1—Ni2—La1 | 131.79 (8) |
| H23—C20—H24 | 109.5 | O3—Ni2—La1 | 41.00 (6) |
| O15—C21—H26 | 109.5 | O15—Ni2—La1 | 89.01 (7) |
| O15—C21—H27 | 109.5 | O14—Ni2—La1 | 90.90 (8) |
| H26—C21—H27 | 109.5 | C1—O1—Ni2 | 126.7 (2) |
| O15—C21—H28 | 109.5 | C1—O1—La1 | 124.71 (19) |
| H26—C21—H28 | 109.5 | Ni2—O1—La1 | 105.78 (8) |
| H27—C21—H28 | 109.5 | C2—O2—C19 | 117.9 (3) |
| O16—C22—H30 | 109.5 | C2—O2—La1 | 118.70 (19) |
| O16—C22—H31 | 109.5 | C19—O2—La1 | 123.3 (2) |
| H30—C22—H31 | 109.5 | C17—O3—Ni2 | 125.81 (19) |
| O16—C22—H32 | 109.5 | C17—O3—La1 | 124.66 (18) |
| H30—C22—H32 | 109.5 | Ni2—O3—La1 | 105.41 (9) |
| H31—C22—H32 | 109.5 | C16—O4—C18 | 116.9 (3) |
| O17—C23—H34 | 109.5 | C16—O4—La1 | 117.03 (18) |
| O17—C23—H35 | 109.5 | C18—O4—La1 | 125.8 (2) |
| H34—C23—H35 | 109.5 | N3—O5—La1 | 96.0 (2) |
| O17—C23—H36 | 109.5 | N3—O7—La1 | 98.7 (2) |
| H34—C23—H36 | 109.5 | N4—O8—La1 | 97.2 (2) |
| H35—C23—H36 | 109.5 | N4—O10—La1 | 100.0 (2) |
| O3—La1—O1 | 66.81 (7) | N5—O11—La1 | 99.9 (2) |
| O3—La1—O10 | 138.52 (10) | N5—O13—La1 | 96.8 (3) |
| O1—La1—O10 | 148.37 (11) | C20—O14—Ni2 | 126.8 (2) |
| O3—La1—O7 | 91.75 (9) | C20—O14—H21 | 108.8 |
| O1—La1—O7 | 76.26 (8) | Ni2—O14—H21 | 119.9 |
| O10—La1—O7 | 113.57 (11) | C21—O15—Ni2 | 125.7 (3) |
| O3—La1—O2 | 128.84 (7) | C21—O15—H25 | 104.0 |
| O1—La1—O2 | 62.21 (7) | Ni2—O15—H25 | 120.5 |
| O10—La1—O2 | 91.05 (11) | C22—O16—H29 | 106.2 |
| O7—La1—O2 | 72.79 (9) | C23—O17—H33 | 101.2 |
| O3—La1—O11 | 76.60 (9) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O17—H33···O16 | 0.85 | 2.10 | 2.665 (7) | 124 |
| O15—H25···O16i | 0.85 | 1.83 | 2.681 (5) | 174 |
| O14—H21···O12ii | 0.85 | 2.34 | 3.169 (5) | 165 |
| O16—H29···O15iii | 0.85 | 2.35 | 2.681 (5) | 104 |
| Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z; (iii) −x+1, y+1/2, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O17—H33···O16 | 0.85 | 2.10 | 2.665 (7) | 124 |
| O15—H25···O16i | 0.85 | 1.83 | 2.681 (5) | 174 |
| O14—H21···O12ii | 0.85 | 2.34 | 3.169 (5) | 165 |
| O16—H29···O15iii | 0.85 | 2.35 | 2.681 (5) | 104 |
| Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z; (iii) −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.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Liu, F. & Zhang, F. (2008). Acta Cryst. E64, m589.
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.
Wang, J.-H., Gao, P., Yan, P.-F., Li, G.-M. & Hou, G.-F. (2008). Acta Cryst. E64, m344.
As shown in Fig. 1, the hexadentate Schiff base ligand links Ni and La atoms into a dinuclear complex through two phenolate O atoms, which is the same as the bonding in the isostructural Pr(III) complex of the same ligand (Liu & Zhang, 2008) and a related Cu(II)/Sm(III) complex (Wang et al., 2008). The LaIII ion in (I) is ten-coordinated by four oxygen atoms from the ligand and six oxygen atoms from three nitrate ions. The NiII center is six-coordinate by two nitrogen atoms and two oxygen atoms from the ligand and two methanol oxygen atoms. The are two solvent methanol molecules for each complex molecule. In the crystal structure, intermolecular O—H—O hydrogen bonds connect complex molecules and methanol solvent molecules to form two-dimension structure.