Acta Cryst. (2009). E65, m1691 [ doi:10.1107/S160053680905017X ]
![[mu]](/logos/entities/mu_rmgif.gif)
3-cis-N-(2-carboxylatophenyl)-N'-[3-(dimethylamino)propyl]oxamidato(3-)}bis(perchlorato)tetranickel(II) methanol disolvateIn the title methanol disolvate complex, [Ni4(C14H16N3O4)2(ClO4)2(C10H8N2)2]·2CH3OH, the neutral tetranickel(II) system lies on a centre of inversion. The polyhedron around each Ni(II) atom is a square pyramid. The separations of the Ni atoms bridged by the oxamide and carboxyl groups are 5.227 (9) and 5.268 (6) Å, respectively. In the crystal structure, a two-dimensional supramolecular network structure involving O-H
O and C-HO hydrogen bonding is observed.
A methanol solution (5 ml) of Ni(ClO4)2.6H2O (0.732 g, 2 mmol) was added slowly into a methanol solution (5 ml) containing N-benzyl-N'-(3-amino-3-dimethylpropyl)oxamide (1 mmol, 0.293 g) and sodium ethoxide (0.204 g, 3 mmol). The mixture was stirred quickly for 1 h, then an aqueous solution (5 ml) of 2,2'-bipyridine (0.156 g, 1 mmol) was added dropwise into the mixture. The reaction solution was heated at 343 K with stirring for 8h. The resulting solution was filtered and the filtrate was kept at room temperature. Green crystals suitable for X-ray analysis were obtained from the filtrate by slow evaporation for about one week.
H atoms were positioned geometrically [0.93 (CH), 0.97 (CH2), 0.96 (CH3) and 0.82 (OH)Å] and constrained to ride on their parent atoms with Uiso(H) =1.2(1.5 for methyl)Ueq(C/N).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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) and PLATON (Spek, 2009).
![[Figure 1]](./pv2236fig1thm.gif)
| Fig. 1. The molecular structure of (I) with 30% displacement ellipsoids (H atoms omitted for clarity). |
| [Ni4(C14H16N3O4)2(ClO4)2(C10H8N2)2] | Z = 1 |
| Mr = 1390.79 | F(000) = 716 |
| Triclinic, P1 | Dx = 1.689 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.854 (4) Å | Cell parameters from 3928 reflections |
| b = 11.309 (4) Å | θ = 2.2–28.1° |
| c = 12.728 (5) Å | µ = 1.54 mm−1 |
| α = 67.724 (4)° | T = 298 K |
| β = 73.357 (4)° | Block, green |
| γ = 75.411 (4)° | 0.21 × 0.16 × 0.14 mm |
| V = 1367.0 (9) Å3 |
| Bruker SMART CCD diffractometer | 4850 independent reflections |
| Radiation source: fine-focus sealed tube | 3963 reflections with I > 2σ(I) |
| graphite | Rint = 0.015 |
| φ and ω scans | θmax = 25.2°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→13 |
| Tmin = 0.738, Tmax = 0.814 | k = −13→9 |
| 7296 measured reflections | l = −15→12 |
| 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.087 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0445P)2 + 0.6427P] where P = (Fo2 + 2Fc2)/3 |
| 4850 reflections | (Δ/σ)max = 0.001 |
| 383 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.56 e Å−3 |
| [Ni4(C14H16N3O4)2(ClO4)2(C10H8N2)2] | γ = 75.411 (4)° |
| Mr = 1390.79 | V = 1367.0 (9) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 10.854 (4) Å | Mo Kα radiation |
| b = 11.309 (4) Å | µ = 1.54 mm−1 |
| c = 12.728 (5) Å | T = 298 K |
| α = 67.724 (4)° | 0.21 × 0.16 × 0.14 mm |
| β = 73.357 (4)° |
| Bruker SMART CCD diffractometer | 4850 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3963 reflections with I > 2σ(I) |
| Tmin = 0.738, Tmax = 0.814 | Rint = 0.015 |
| 7296 measured reflections | θmax = 25.2° |
| R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.087 | Δρmax = 0.33 e Å−3 |
| S = 1.04 | Δρmin = −0.56 e Å−3 |
| 4850 reflections | Absolute structure: ? |
| 383 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. Yield, 61%, analysis, calculated for C50H56Cl2N10O18Ni4: C 43.18, H, 4.06; N 10.07%; found: C 43.22, H 4.15, N, 10.09%. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
| Ni1 | 0.84712 (3) | −0.11565 (3) | 0.73827 (3) | 0.03336 (11) | |
| Ni2 | 0.72954 (3) | 0.35869 (3) | 0.46787 (3) | 0.03195 (11) | |
| O1 | 0.9263 (2) | −0.2738 (2) | 0.70987 (18) | 0.0586 (6) | |
| O2 | 1.06150 (19) | −0.39494 (18) | 0.61253 (18) | 0.0456 (5) | |
| O3 | 0.7747 (2) | 0.18517 (17) | 0.45514 (16) | 0.0400 (5) | |
| O4 | 0.73515 (19) | 0.26666 (17) | 0.63062 (16) | 0.0380 (4) | |
| N1 | 0.8309 (2) | −0.0280 (2) | 0.57245 (18) | 0.0318 (5) | |
| N2 | 0.7889 (2) | 0.0574 (2) | 0.74936 (19) | 0.0388 (5) | |
| N3 | 0.8932 (2) | −0.2005 (2) | 0.9003 (2) | 0.0437 (6) | |
| N4 | 0.6571 (2) | 0.4495 (2) | 0.32480 (19) | 0.0367 (5) | |
| N5 | 0.6681 (2) | 0.5300 (2) | 0.4873 (2) | 0.0363 (5) | |
| C1 | 0.9762 (3) | −0.2980 (3) | 0.6150 (3) | 0.0384 (6) | |
| C2 | 0.9259 (3) | −0.2161 (3) | 0.5073 (2) | 0.0338 (6) | |
| C3 | 0.9484 (3) | −0.2750 (3) | 0.4233 (3) | 0.0420 (7) | |
| H3 | 0.9979 | −0.3573 | 0.4349 | 0.050* | |
| C4 | 0.8995 (3) | −0.2150 (3) | 0.3240 (3) | 0.0480 (7) | |
| H4 | 0.9160 | −0.2555 | 0.2689 | 0.058* | |
| C5 | 0.8253 (3) | −0.0928 (3) | 0.3077 (3) | 0.0458 (7) | |
| H5 | 0.7905 | −0.0514 | 0.2416 | 0.055* | |
| C6 | 0.8026 (3) | −0.0321 (3) | 0.3886 (2) | 0.0407 (7) | |
| H6 | 0.7522 | 0.0498 | 0.3761 | 0.049* | |
| C7 | 0.8531 (3) | −0.0904 (2) | 0.4887 (2) | 0.0324 (6) | |
| C8 | 0.7944 (2) | 0.0971 (2) | 0.5502 (2) | 0.0309 (6) | |
| C9 | 0.7718 (3) | 0.1443 (2) | 0.6517 (2) | 0.0330 (6) | |
| C10 | 0.7595 (4) | 0.0988 (3) | 0.8514 (3) | 0.0522 (8) | |
| H10A | 0.6682 | 0.0971 | 0.8886 | 0.063* | |
| H10B | 0.7746 | 0.1873 | 0.8263 | 0.063* | |
| C11 | 0.8409 (4) | 0.0144 (3) | 0.9376 (3) | 0.0613 (10) | |
| H11A | 0.8175 | 0.0462 | 1.0028 | 0.074* | |
| H11B | 0.9316 | 0.0221 | 0.9016 | 0.074* | |
| C12 | 0.8276 (4) | −0.1261 (3) | 0.9829 (3) | 0.0593 (9) | |
| H12A | 0.7355 | −0.1321 | 1.0053 | 0.071* | |
| H12B | 0.8628 | −0.1677 | 1.0525 | 0.071* | |
| C13 | 0.8543 (4) | −0.3307 (3) | 0.9596 (3) | 0.0563 (9) | |
| H13A | 0.9003 | −0.3859 | 0.9142 | 0.084* | |
| H13B | 0.7622 | −0.3233 | 0.9678 | 0.084* | |
| H13C | 0.8754 | −0.3673 | 1.0350 | 0.084* | |
| C14 | 1.0355 (3) | −0.2162 (4) | 0.8801 (3) | 0.0675 (10) | |
| H14A | 1.0617 | −0.2516 | 0.9533 | 0.101* | |
| H14B | 1.0630 | −0.1335 | 0.8377 | 0.101* | |
| H14C | 1.0750 | −0.2738 | 0.8359 | 0.101* | |
| C15 | 0.6502 (3) | 0.3972 (3) | 0.2487 (2) | 0.0437 (7) | |
| H15 | 0.6840 | 0.3101 | 0.2603 | 0.052* | |
| C16 | 0.5948 (3) | 0.4677 (3) | 0.1537 (3) | 0.0520 (8) | |
| H16 | 0.5908 | 0.4289 | 0.1023 | 0.062* | |
| C17 | 0.5453 (3) | 0.5971 (3) | 0.1365 (3) | 0.0534 (8) | |
| H17 | 0.5081 | 0.6469 | 0.0728 | 0.064* | |
| C18 | 0.5513 (3) | 0.6523 (3) | 0.2147 (3) | 0.0462 (7) | |
| H18 | 0.5187 | 0.7393 | 0.2042 | 0.055* | |
| C19 | 0.6065 (3) | 0.5760 (3) | 0.3084 (2) | 0.0356 (6) | |
| C20 | 0.6125 (3) | 0.6218 (3) | 0.4019 (2) | 0.0351 (6) | |
| C21 | 0.5636 (3) | 0.7460 (3) | 0.4056 (3) | 0.0445 (7) | |
| H21 | 0.5251 | 0.8083 | 0.3467 | 0.053* | |
| C22 | 0.5732 (3) | 0.7761 (3) | 0.4990 (3) | 0.0488 (8) | |
| H22 | 0.5405 | 0.8588 | 0.5033 | 0.059* | |
| C23 | 0.6312 (3) | 0.6828 (3) | 0.5847 (3) | 0.0455 (7) | |
| H23 | 0.6387 | 0.7015 | 0.6476 | 0.055* | |
| C24 | 0.6781 (3) | 0.5609 (3) | 0.5758 (3) | 0.0426 (7) | |
| H24 | 0.7182 | 0.4980 | 0.6334 | 0.051* | |
| Cl1 | 0.49509 (8) | −0.11510 (8) | 0.81502 (7) | 0.0508 (2) | |
| O5 | 0.6183 (3) | −0.1925 (3) | 0.8306 (3) | 0.0928 (10) | |
| O6 | 0.4947 (4) | −0.0733 (3) | 0.6956 (3) | 0.1125 (13) | |
| O7 | 0.4736 (3) | −0.0026 (3) | 0.8472 (3) | 0.0911 (9) | |
| O8 | 0.3950 (3) | −0.1885 (3) | 0.8805 (4) | 0.1155 (13) | |
| O9 | 0.9657 (4) | 0.4193 (3) | 0.8309 (3) | 0.1074 (12) | |
| H9 | 0.9999 | 0.4646 | 0.7666 | 0.129* | |
| C25 | 0.8308 (6) | 0.4297 (5) | 0.8360 (5) | 0.123 (2) | |
| H25A | 0.7916 | 0.3737 | 0.9099 | 0.185* | |
| H25B | 0.8209 | 0.4049 | 0.7750 | 0.185* | |
| H25C | 0.7889 | 0.5176 | 0.8267 | 0.185* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0426 (2) | 0.02493 (19) | 0.02760 (19) | 0.00177 (15) | −0.00980 (15) | −0.00623 (14) |
| Ni2 | 0.0383 (2) | 0.02207 (18) | 0.03246 (19) | 0.00241 (14) | −0.01060 (15) | −0.00812 (14) |
| O1 | 0.0859 (17) | 0.0354 (11) | 0.0383 (12) | 0.0159 (11) | −0.0141 (11) | −0.0103 (10) |
| O2 | 0.0396 (11) | 0.0332 (11) | 0.0550 (13) | 0.0053 (9) | −0.0080 (9) | −0.0134 (9) |
| O3 | 0.0553 (13) | 0.0289 (10) | 0.0339 (10) | −0.0008 (9) | −0.0151 (9) | −0.0080 (8) |
| O4 | 0.0462 (12) | 0.0275 (10) | 0.0374 (10) | 0.0018 (8) | −0.0103 (9) | −0.0114 (8) |
| N1 | 0.0363 (12) | 0.0278 (11) | 0.0302 (11) | −0.0024 (10) | −0.0077 (9) | −0.0098 (9) |
| N2 | 0.0522 (15) | 0.0323 (12) | 0.0298 (12) | −0.0015 (11) | −0.0115 (11) | −0.0094 (10) |
| N3 | 0.0489 (15) | 0.0396 (14) | 0.0371 (13) | −0.0032 (11) | −0.0124 (11) | −0.0068 (11) |
| N4 | 0.0383 (13) | 0.0326 (12) | 0.0367 (12) | −0.0034 (10) | −0.0083 (10) | −0.0101 (10) |
| N5 | 0.0352 (13) | 0.0308 (12) | 0.0393 (13) | −0.0027 (10) | −0.0064 (10) | −0.0105 (10) |
| C1 | 0.0363 (16) | 0.0316 (15) | 0.0440 (17) | −0.0056 (13) | −0.0044 (13) | −0.0120 (13) |
| C2 | 0.0291 (14) | 0.0335 (14) | 0.0389 (15) | −0.0065 (11) | −0.0028 (11) | −0.0144 (12) |
| C3 | 0.0401 (16) | 0.0387 (16) | 0.0489 (18) | −0.0033 (13) | −0.0038 (13) | −0.0225 (14) |
| C4 | 0.0510 (19) | 0.0539 (19) | 0.0478 (18) | −0.0093 (15) | −0.0067 (15) | −0.0286 (15) |
| C5 | 0.0536 (19) | 0.0483 (18) | 0.0398 (16) | −0.0132 (15) | −0.0133 (14) | −0.0136 (14) |
| C6 | 0.0465 (17) | 0.0340 (15) | 0.0421 (16) | −0.0040 (13) | −0.0137 (13) | −0.0116 (13) |
| C7 | 0.0313 (14) | 0.0316 (14) | 0.0332 (14) | −0.0073 (11) | −0.0028 (11) | −0.0111 (11) |
| C8 | 0.0307 (14) | 0.0284 (13) | 0.0306 (14) | −0.0015 (11) | −0.0075 (11) | −0.0079 (11) |
| C9 | 0.0320 (14) | 0.0290 (14) | 0.0363 (15) | −0.0030 (11) | −0.0072 (11) | −0.0103 (12) |
| C10 | 0.078 (2) | 0.0426 (17) | 0.0389 (17) | 0.0012 (16) | −0.0177 (16) | −0.0195 (14) |
| C11 | 0.087 (3) | 0.058 (2) | 0.0435 (19) | 0.0010 (19) | −0.0245 (18) | −0.0219 (16) |
| C12 | 0.081 (3) | 0.055 (2) | 0.0368 (17) | −0.0009 (18) | −0.0176 (17) | −0.0119 (15) |
| C13 | 0.068 (2) | 0.0456 (19) | 0.0420 (18) | −0.0086 (17) | −0.0132 (16) | 0.0011 (14) |
| C14 | 0.049 (2) | 0.077 (3) | 0.066 (2) | −0.0087 (19) | −0.0188 (18) | −0.008 (2) |
| C15 | 0.0498 (18) | 0.0396 (16) | 0.0407 (16) | −0.0056 (14) | −0.0082 (14) | −0.0143 (13) |
| C16 | 0.062 (2) | 0.055 (2) | 0.0385 (17) | −0.0106 (17) | −0.0110 (15) | −0.0139 (15) |
| C17 | 0.054 (2) | 0.059 (2) | 0.0398 (17) | −0.0039 (16) | −0.0160 (15) | −0.0065 (15) |
| C18 | 0.0439 (18) | 0.0388 (16) | 0.0423 (17) | 0.0022 (13) | −0.0104 (14) | −0.0034 (13) |
| C19 | 0.0296 (14) | 0.0309 (14) | 0.0390 (15) | −0.0020 (11) | −0.0046 (12) | −0.0073 (12) |
| C20 | 0.0302 (14) | 0.0286 (14) | 0.0414 (15) | −0.0033 (11) | −0.0060 (12) | −0.0079 (12) |
| C21 | 0.0414 (17) | 0.0295 (15) | 0.0558 (19) | −0.0017 (13) | −0.0088 (14) | −0.0105 (14) |
| C22 | 0.0462 (18) | 0.0321 (16) | 0.065 (2) | −0.0060 (14) | −0.0026 (15) | −0.0196 (15) |
| C23 | 0.0443 (17) | 0.0427 (17) | 0.0530 (19) | −0.0094 (14) | −0.0046 (14) | −0.0223 (15) |
| C24 | 0.0446 (17) | 0.0414 (16) | 0.0444 (17) | −0.0040 (13) | −0.0116 (14) | −0.0175 (14) |
| Cl1 | 0.0531 (5) | 0.0441 (4) | 0.0561 (5) | −0.0004 (4) | −0.0177 (4) | −0.0178 (4) |
| O5 | 0.0651 (18) | 0.0728 (19) | 0.117 (2) | 0.0084 (15) | −0.0425 (17) | −0.0015 (17) |
| O6 | 0.156 (3) | 0.104 (2) | 0.074 (2) | 0.046 (2) | −0.059 (2) | −0.0422 (19) |
| O7 | 0.122 (3) | 0.0686 (18) | 0.098 (2) | −0.0174 (17) | −0.0168 (19) | −0.0475 (17) |
| O8 | 0.081 (2) | 0.076 (2) | 0.181 (4) | −0.0366 (18) | 0.016 (2) | −0.050 (2) |
| O9 | 0.180 (4) | 0.0602 (19) | 0.067 (2) | 0.002 (2) | −0.036 (2) | −0.0106 (15) |
| C25 | 0.185 (6) | 0.079 (3) | 0.143 (5) | −0.048 (4) | −0.117 (5) | 0.000 (3) |
| Ni1—O1 | 1.899 (2) | C10—H10B | 0.9700 |
| Ni1—N2 | 1.945 (2) | C11—C12 | 1.500 (5) |
| Ni1—N1 | 2.002 (2) | C11—H11A | 0.9700 |
| Ni1—N3 | 2.067 (2) | C11—H11B | 0.9700 |
| Ni2—O4 | 1.9452 (19) | C12—H12A | 0.9700 |
| Ni2—O3 | 1.957 (2) | C12—H12B | 0.9700 |
| Ni2—N5 | 1.969 (2) | C13—H13A | 0.9600 |
| Ni2—N4 | 1.996 (2) | C13—H13B | 0.9600 |
| Ni2—O2i | 2.276 (2) | C13—H13C | 0.9600 |
| O1—C1 | 1.276 (3) | C14—H14A | 0.9600 |
| O2—C1 | 1.248 (3) | C14—H14B | 0.9600 |
| O2—Ni2i | 2.276 (2) | C14—H14C | 0.9600 |
| O3—C8 | 1.276 (3) | C15—C16 | 1.380 (4) |
| O4—C9 | 1.284 (3) | C15—H15 | 0.9300 |
| N1—C8 | 1.310 (3) | C16—C17 | 1.381 (5) |
| N1—C7 | 1.426 (3) | C16—H16 | 0.9300 |
| N2—C9 | 1.288 (3) | C17—C18 | 1.384 (4) |
| N2—C10 | 1.469 (4) | C17—H17 | 0.9300 |
| N3—C14 | 1.468 (4) | C18—C19 | 1.376 (4) |
| N3—C13 | 1.484 (4) | C18—H18 | 0.9300 |
| N3—C12 | 1.504 (4) | C19—C20 | 1.488 (4) |
| N4—C15 | 1.338 (4) | C20—C21 | 1.385 (4) |
| N4—C19 | 1.355 (3) | C21—C22 | 1.390 (4) |
| N5—C24 | 1.339 (4) | C21—H21 | 0.9300 |
| N5—C20 | 1.351 (3) | C22—C23 | 1.373 (4) |
| C1—C2 | 1.498 (4) | C22—H22 | 0.9300 |
| C2—C3 | 1.400 (4) | C23—C24 | 1.380 (4) |
| C2—C7 | 1.409 (4) | C23—H23 | 0.9300 |
| C3—C4 | 1.375 (4) | C24—H24 | 0.9300 |
| C3—H3 | 0.9300 | Cl1—O8 | 1.405 (3) |
| C4—C5 | 1.386 (4) | Cl1—O6 | 1.411 (3) |
| C4—H4 | 0.9300 | Cl1—O5 | 1.422 (3) |
| C5—C6 | 1.376 (4) | Cl1—O7 | 1.426 (3) |
| C5—H5 | 0.9300 | O9—C25 | 1.424 (6) |
| C6—C7 | 1.393 (4) | O9—H9 | 0.8200 |
| C6—H6 | 0.9300 | C25—H25A | 0.9600 |
| C8—C9 | 1.513 (4) | C25—H25B | 0.9600 |
| C10—C11 | 1.494 (4) | C25—H25C | 0.9600 |
| C10—H10A | 0.9700 | ||
| O1—Ni1—N2 | 171.10 (10) | C11—C10—H10B | 109.2 |
| O1—Ni1—N1 | 91.11 (9) | H10A—C10—H10B | 107.9 |
| N2—Ni1—N1 | 84.53 (9) | C10—C11—C12 | 114.6 (3) |
| O1—Ni1—N3 | 87.70 (10) | C10—C11—H11A | 108.6 |
| N2—Ni1—N3 | 95.41 (10) | C12—C11—H11A | 108.6 |
| N1—Ni1—N3 | 171.13 (10) | C10—C11—H11B | 108.6 |
| O4—Ni2—O3 | 84.13 (8) | C12—C11—H11B | 108.6 |
| O4—Ni2—N5 | 94.63 (9) | H11A—C11—H11B | 107.6 |
| O3—Ni2—N5 | 174.87 (9) | C11—C12—N3 | 115.9 (3) |
| O4—Ni2—N4 | 159.66 (9) | C11—C12—H12A | 108.3 |
| O3—Ni2—N4 | 97.63 (9) | N3—C12—H12A | 108.3 |
| N5—Ni2—N4 | 81.80 (9) | C11—C12—H12B | 108.3 |
| O4—Ni2—O2i | 102.30 (8) | N3—C12—H12B | 108.3 |
| O3—Ni2—O2i | 91.41 (8) | H12A—C12—H12B | 107.4 |
| N5—Ni2—O2i | 93.72 (8) | N3—C13—H13A | 109.5 |
| N4—Ni2—O2i | 97.92 (9) | N3—C13—H13B | 109.5 |
| C1—O1—Ni1 | 131.07 (19) | H13A—C13—H13B | 109.5 |
| C1—O2—Ni2i | 116.82 (18) | N3—C13—H13C | 109.5 |
| C8—O3—Ni2 | 112.51 (16) | H13A—C13—H13C | 109.5 |
| C9—O4—Ni2 | 112.20 (17) | H13B—C13—H13C | 109.5 |
| C8—N1—C7 | 123.5 (2) | N3—C14—H14A | 109.5 |
| C8—N1—Ni1 | 110.62 (17) | N3—C14—H14B | 109.5 |
| C7—N1—Ni1 | 125.87 (17) | H14A—C14—H14B | 109.5 |
| C9—N2—C10 | 118.0 (2) | N3—C14—H14C | 109.5 |
| C9—N2—Ni1 | 112.66 (18) | H14A—C14—H14C | 109.5 |
| C10—N2—Ni1 | 129.33 (18) | H14B—C14—H14C | 109.5 |
| C14—N3—C13 | 108.2 (3) | N4—C15—C16 | 122.5 (3) |
| C14—N3—C12 | 111.1 (3) | N4—C15—H15 | 118.8 |
| C13—N3—C12 | 105.6 (3) | C16—C15—H15 | 118.8 |
| C14—N3—Ni1 | 106.2 (2) | C17—C16—C15 | 118.5 (3) |
| C13—N3—Ni1 | 111.19 (19) | C17—C16—H16 | 120.7 |
| C12—N3—Ni1 | 114.47 (19) | C15—C16—H16 | 120.7 |
| C15—N4—C19 | 118.7 (2) | C16—C17—C18 | 119.6 (3) |
| C15—N4—Ni2 | 126.8 (2) | C16—C17—H17 | 120.2 |
| C19—N4—Ni2 | 114.46 (19) | C18—C17—H17 | 120.2 |
| C24—N5—C20 | 119.1 (2) | C19—C18—C17 | 118.9 (3) |
| C24—N5—Ni2 | 125.47 (19) | C19—C18—H18 | 120.6 |
| C20—N5—Ni2 | 115.39 (19) | C17—C18—H18 | 120.6 |
| O2—C1—O1 | 120.4 (3) | N4—C19—C18 | 121.8 (3) |
| O2—C1—C2 | 119.2 (3) | N4—C19—C20 | 114.1 (2) |
| O1—C1—C2 | 120.3 (2) | C18—C19—C20 | 124.1 (3) |
| C3—C2—C7 | 119.0 (3) | N5—C20—C21 | 121.3 (3) |
| C3—C2—C1 | 115.6 (2) | N5—C20—C19 | 114.3 (2) |
| C7—C2—C1 | 125.3 (2) | C21—C20—C19 | 124.4 (3) |
| C4—C3—C2 | 121.9 (3) | C20—C21—C22 | 118.9 (3) |
| C4—C3—H3 | 119.0 | C20—C21—H21 | 120.6 |
| C2—C3—H3 | 119.0 | C22—C21—H21 | 120.6 |
| C3—C4—C5 | 118.7 (3) | C23—C22—C21 | 119.6 (3) |
| C3—C4—H4 | 120.7 | C23—C22—H22 | 120.2 |
| C5—C4—H4 | 120.7 | C21—C22—H22 | 120.2 |
| C6—C5—C4 | 120.6 (3) | C22—C23—C24 | 118.7 (3) |
| C6—C5—H5 | 119.7 | C22—C23—H23 | 120.7 |
| C4—C5—H5 | 119.7 | C24—C23—H23 | 120.7 |
| C5—C6—C7 | 121.6 (3) | N5—C24—C23 | 122.4 (3) |
| C5—C6—H6 | 119.2 | N5—C24—H24 | 118.8 |
| C7—C6—H6 | 119.2 | C23—C24—H24 | 118.8 |
| C6—C7—C2 | 118.2 (2) | O8—Cl1—O6 | 110.1 (3) |
| C6—C7—N1 | 122.0 (2) | O8—Cl1—O5 | 110.0 (2) |
| C2—C7—N1 | 119.8 (2) | O6—Cl1—O5 | 107.5 (2) |
| O3—C8—N1 | 129.3 (2) | O8—Cl1—O7 | 109.6 (2) |
| O3—C8—C9 | 115.1 (2) | O6—Cl1—O7 | 107.6 (2) |
| N1—C8—C9 | 115.5 (2) | O5—Cl1—O7 | 112.0 (2) |
| O4—C9—N2 | 127.6 (2) | C25—O9—H9 | 109.5 |
| O4—C9—C8 | 115.8 (2) | O9—C25—H25A | 109.5 |
| N2—C9—C8 | 116.6 (2) | O9—C25—H25B | 109.5 |
| N2—C10—C11 | 112.3 (3) | H25A—C25—H25B | 109.5 |
| N2—C10—H10A | 109.2 | O9—C25—H25C | 109.5 |
| C11—C10—H10A | 109.2 | H25A—C25—H25C | 109.5 |
| N2—C10—H10B | 109.2 | H25B—C25—H25C | 109.5 |
| Symmetry codes: (i) −x+2, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O9—H9···O1ii | 0.82 | 2.73 | 3.190 (4) | 118 |
| O9—H9···O2ii | 0.82 | 2.06 | 2.870 (4) | 170 |
| C4—H4···O9i | 0.93 | 2.52 | 3.387 (5) | 155 |
| C13—H13C···O9iii | 0.96 | 2.58 | 3.451 (5) | 151 |
| C3—H3···O2 | 0.93 | 2.41 | 2.744 (4) | 101 |
| C6—H6···O3 | 0.93 | 2.22 | 2.812 (3) | 121 |
| C10—H10B···O4 | 0.97 | 2.43 | 2.775 (4) | 100 |
| C13—H13A···O1 | 0.96 | 2.39 | 2.899 (4) | 113 |
| C13—H13B···O5 | 0.96 | 2.47 | 3.186 (4) | 131 |
| C14—H14C···O1 | 0.96 | 2.58 | 3.074 (5) | 112 |
| C24—H24···O4 | 0.93 | 2.59 | 3.065 (4) | 112 |
| Symmetry codes: (ii) x, y+1, z; (i) −x+2, −y, −z+1; (iii) −x+2, −y, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O9—H9···O1i | 0.82 | 2.73 | 3.190 (4) | 118 |
| O9—H9···O2i | 0.82 | 2.06 | 2.870 (4) | 170 |
| C4—H4···O9ii | 0.93 | 2.52 | 3.387 (5) | 155 |
| C13—H13C···O9iii | 0.96 | 2.58 | 3.451 (5) | 151 |
| C3—H3···O2 | 0.93 | 2.41 | 2.744 (4) | 101 |
| C6—H6···O3 | 0.93 | 2.22 | 2.812 (3) | 121 |
| C10—H10B···O4 | 0.97 | 2.43 | 2.775 (4) | 100 |
| C13—H13A···O1 | 0.96 | 2.39 | 2.899 (4) | 113 |
| C13—H13B···O5 | 0.96 | 2.47 | 3.186 (4) | 131 |
| C14—H14C···O1 | 0.96 | 2.58 | 3.074 (5) | 112 |
| C24—H24···O4 | 0.93 | 2.59 | 3.065 (4) | 112 |
| Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y, −z+1; (iii) −x+2, −y, −z+2. |
The financial support of the Science Foundation of Shandong is greatfully acknowledged.
Bruker, (1998). SMART and SAINT. Bruker AXS, Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Tao, R. J., Zang, S. Q., Cheng, Y. X., Wang, Q. L., Hu, N. H., Niu, J. Y. & Liao, D. Z. (2003). Polyhedron 22, 2911–2916.
The title compound (Fig. 1), is a tetranuclear nickel(II) complex. Its asymmetric unit is composed of a cis-oxamido bridged dinuclear nickel complex and a molecule of methanol solvate. Through carboxyl bridges, two dinuclear units are assembled to form a circular tetranuclear system lying about an inversion center. The cis-oxamido group coordinates to Ni1 and Ni2 in a usual mode with the bite angles of 83.53 (6) and 85.14 (11) °, respectively. Both Ni1 and Ni2 atoms are in square-pyramidal coordination geometries. The maximum displacement from the least-square plane defined by N1, N2, N3 and O1, is 0.0400 (11) Å for N1 and the Ni1 atom lies 0.1168 (12) Å out of this plane. The apical position of Ni1 is occupied by O5 with the Ni1—O5 bond length of 2.636 (8) Å. Ni2 atom coordinates to the exo-cis oxygen atoms of oxamido ligand (O3 and O4). The two oxygen atoms and the nitrogen atoms (N4 and N5) of bipyridine ligand complete the basal plane, from which the maximum deviations is 0.1311 (6) Å. The apical site is occupied by a carboxyl oxygen atom (O2i) with Ni2—O2i length of 2.276 (2) Å. The Ni—N bond lenghts in (I) (Table 1), lie in the range 1.945 (2)-2.067 (2)Å and are close to the corresponding bond lenghts reported in a nickel complex (Tao et al., 2003).
In the crystal, neutral tetranuclear complexes and methanol molecules are connected by classcial O—H···O and non-classical C—H···O hydrogen bonds into a two-dimensional network (Table 1).