Acta Cryst. (2007). E63, m2335 [ doi:10.1107/S1600536807039451 ]
In the crystal structure of the title compound, [Ni(C31H22Cl2N4O2)], the Ni atoms are coordinated by four N atoms of the macrocyclic ligand in a distorted square-planar configuration. Three C atoms are disordered over two positions, with site occupancy factors of 0.85 and 0.15.
The synthesis of the reactand 2, 2'-(oxalyldiimino)bis(chlorobenzaldehyde) was described previously (Zhang et al., 2005). 2.96 mmol 2, 2'-(oxalyldiimino)bis(chlorobenzaldehyde), 5.92 mmol 1,2-diaminopropane and 2.96 mmol nickel(II)acetate were refluxed for 10 h in 50 ml of methanol and 2.80 ml of 2 M sodium hydroxide. The mixture was cooled down and the red precipitate of the title compound was filtered off. Crystals of the title compound were obtained by slow evaporation of the solvent from the deep red filtrate at room temperature.
The H atoms were positioned with idealized geometry and were refined isotropic (Uiso (H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model. The carbon atoms C16, C17 and C18 are disordered in two orientations and were refined using a split model and site occupation factors of 75:25. The carbon atoms of lower occupany were refined only isotropic.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
![[Figure 1]](./nc2051fig1thm.gif)
| Fig. 1. Crystal structure of compound I with labelling and displacement ellipsoids drawn at the 50% probability level. |
| [Ni(C31H22Cl2N4O2)] | F000 = 1256 |
| Mr = 612.14 | Dx = 1.495 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| a = 11.7341 (17) Å | Cell parameters from 4332 reflections |
| b = 14.900 (2) Å | θ = 2.5–26.0º |
| c = 16.235 (2) Å | µ = 0.95 mm−1 |
| β = 106.582 (2)º | T = 293 (2) K |
| V = 2720.4 (6) Å3 | Block, red |
| Z = 4 | 0.28 × 0.20 × 0.14 mm |
| Bruker SMART CCD area-detector diffractometer | 5556 independent reflections |
| Radiation source: fine-focus sealed tube | 3780 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.034 |
| T = 293(2) K | θmax = 26.4º |
| φ and ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→14 |
| Tmin = 0.805, Tmax = 0.891 | k = −18→18 |
| 15103 measured reflections | l = −20→10 |
| 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)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0349P)2 + 1.2682P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 5556 reflections | Δρmax = 0.53 e Å−3 |
| 373 parameters | Δρmin = −0.28 e Å−3 |
| 4 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Ni(C31H22Cl2N4O2)] | V = 2720.4 (6) Å3 |
| Mr = 612.14 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 11.7341 (17) Å | µ = 0.95 mm−1 |
| b = 14.900 (2) Å | T = 293 (2) K |
| c = 16.235 (2) Å | 0.28 × 0.20 × 0.14 mm |
| β = 106.582 (2)º |
| Bruker SMART CCD area-detector diffractometer | 5556 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3780 reflections with I > 2σ(I) |
| Tmin = 0.805, Tmax = 0.891 | Rint = 0.034 |
| 15103 measured reflections |
| R[F2 > 2σ(F2)] = 0.038 | 4 restraints |
| wR(F2) = 0.095 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.53 e Å−3 |
| 5556 reflections | Δρmin = −0.28 e Å−3 |
| 373 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 > 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 | Occ. (<1) | |
| Ni1 | 0.60785 (3) | 0.66024 (2) | 0.08881 (2) | 0.03775 (11) | |
| Cl1 | 0.07277 (7) | 0.39951 (6) | 0.04929 (6) | 0.0701 (3) | |
| Cl2 | 1.23327 (7) | 0.75094 (7) | 0.16199 (6) | 0.0721 (3) | |
| O1 | 0.58144 (19) | 0.55245 (16) | 0.29861 (12) | 0.0666 (6) | |
| O2 | 0.81015 (19) | 0.60420 (15) | 0.31840 (12) | 0.0643 (6) | |
| N1 | 0.54278 (18) | 0.58085 (14) | 0.15208 (13) | 0.0395 (5) | |
| N2 | 0.75073 (19) | 0.64553 (15) | 0.17400 (14) | 0.0427 (6) | |
| N3 | 0.66880 (19) | 0.75272 (15) | 0.03553 (14) | 0.0435 (6) | |
| N4 | 0.46670 (19) | 0.67016 (15) | −0.00050 (14) | 0.0444 (6) | |
| C1 | 0.6104 (2) | 0.57871 (19) | 0.23642 (17) | 0.0442 (7) | |
| C2 | 0.7364 (3) | 0.61159 (18) | 0.24794 (18) | 0.0449 (7) | |
| C3 | 0.8631 (2) | 0.66991 (19) | 0.16892 (17) | 0.0449 (7) | |
| C4 | 0.9652 (3) | 0.6247 (2) | 0.2172 (2) | 0.0610 (9) | |
| H4 | 0.9570 | 0.5774 | 0.2525 | 0.073* | |
| C5 | 1.0769 (3) | 0.6482 (2) | 0.2137 (2) | 0.0661 (9) | |
| H5 | 1.1432 | 0.6167 | 0.2457 | 0.079* | |
| C6 | 1.0897 (2) | 0.7189 (2) | 0.1625 (2) | 0.0542 (8) | |
| C7 | 0.9931 (2) | 0.7629 (2) | 0.11227 (18) | 0.0489 (7) | |
| H7 | 1.0036 | 0.8099 | 0.0775 | 0.059* | |
| C8 | 0.8774 (2) | 0.73791 (18) | 0.11249 (17) | 0.0416 (6) | |
| C9 | 0.7764 (2) | 0.78221 (18) | 0.05036 (17) | 0.0414 (6) | |
| C10 | 0.8029 (2) | 0.86080 (18) | 0.00121 (17) | 0.0415 (7) | |
| C11 | 0.8030 (3) | 0.9470 (2) | 0.0326 (2) | 0.0596 (8) | |
| H11 | 0.7879 | 0.9570 | 0.0850 | 0.071* | |
| C12 | 0.8260 (3) | 1.0182 (2) | −0.0149 (3) | 0.0760 (11) | |
| H12 | 0.8246 | 1.0765 | 0.0053 | 0.091* | |
| C13 | 0.8508 (3) | 1.0040 (3) | −0.0916 (2) | 0.0700 (10) | |
| H13 | 0.8667 | 1.0524 | −0.1227 | 0.084* | |
| C14 | 0.8522 (3) | 0.9188 (2) | −0.1220 (2) | 0.0576 (8) | |
| H14 | 0.8700 | 0.9093 | −0.1736 | 0.069* | |
| C15 | 0.8275 (2) | 0.8472 (2) | −0.07685 (19) | 0.0497 (7) | |
| H15 | 0.8273 | 0.7894 | −0.0984 | 0.060* | |
| C16 | 0.5678 (3) | 0.8024 (2) | −0.0258 (2) | 0.0444 (9) | 0.85 |
| H16 | 0.5976 | 0.8347 | −0.0681 | 0.053* | 0.85 |
| C17 | 0.5088 (4) | 0.8678 (3) | 0.0195 (3) | 0.0659 (11) | 0.85 |
| H17A | 0.4463 | 0.8987 | −0.0219 | 0.099* | 0.85 |
| H17B | 0.5664 | 0.9104 | 0.0507 | 0.099* | 0.85 |
| H17C | 0.4759 | 0.8359 | 0.0588 | 0.099* | 0.85 |
| C18 | 0.4826 (3) | 0.7307 (2) | −0.0705 (2) | 0.0471 (9) | 0.85 |
| H18A | 0.5148 | 0.6975 | −0.1102 | 0.057* | 0.85 |
| H18B | 0.4071 | 0.7568 | −0.1023 | 0.057* | 0.85 |
| C16' | 0.4666 (15) | 0.7683 (9) | −0.0329 (12) | 0.038 (5)* | 0.15 |
| H16' | 0.4057 | 0.7700 | −0.0886 | 0.046* | 0.15 |
| C17' | 0.436 (3) | 0.8440 (16) | 0.0189 (17) | 0.084 (9)* | 0.15 |
| H17D | 0.3598 | 0.8329 | 0.0277 | 0.126* | 0.15 |
| H17E | 0.4337 | 0.8995 | −0.0115 | 0.126* | 0.15 |
| H17F | 0.4954 | 0.8477 | 0.0736 | 0.126* | 0.15 |
| C18' | 0.5836 (17) | 0.771 (2) | −0.0533 (12) | 0.076 (11)* | 0.15 |
| H18C | 0.5979 | 0.8296 | −0.0749 | 0.091* | 0.15 |
| H18D | 0.5886 | 0.7253 | −0.0944 | 0.091* | 0.15 |
| C19 | 0.3662 (2) | 0.62871 (17) | −0.01172 (17) | 0.0379 (6) | |
| C20 | 0.2648 (2) | 0.64962 (18) | −0.08949 (17) | 0.0394 (6) | |
| C21 | 0.1782 (2) | 0.7101 (2) | −0.0846 (2) | 0.0518 (8) | |
| H21 | 0.1822 | 0.7382 | −0.0327 | 0.062* | |
| C22 | 0.0852 (3) | 0.7291 (2) | −0.1571 (2) | 0.0645 (10) | |
| H22 | 0.0275 | 0.7706 | −0.1538 | 0.077* | |
| C23 | 0.0778 (3) | 0.6872 (3) | −0.2331 (2) | 0.0664 (10) | |
| H23 | 0.0146 | 0.6996 | −0.2812 | 0.080* | |
| C24 | 0.1633 (3) | 0.6271 (3) | −0.2385 (2) | 0.0805 (11) | |
| H24 | 0.1585 | 0.5987 | −0.2904 | 0.097* | |
| C25 | 0.3475 (2) | 0.56027 (17) | 0.04796 (17) | 0.0378 (6) | |
| C26 | 0.2372 (2) | 0.51519 (18) | 0.02465 (19) | 0.0444 (7) | |
| H26 | 0.1814 | 0.5290 | −0.0272 | 0.053* | |
| C27 | 0.2112 (3) | 0.45165 (19) | 0.0770 (2) | 0.0496 (7) | |
| C28 | 0.2941 (3) | 0.4282 (2) | 0.1531 (2) | 0.0590 (8) | |
| H28 | 0.2764 | 0.3841 | 0.1881 | 0.071* | |
| C29 | 0.4022 (3) | 0.4702 (2) | 0.17671 (19) | 0.0561 (8) | |
| H29 | 0.4578 | 0.4530 | 0.2275 | 0.067* | |
| C30 | 0.4322 (2) | 0.53880 (17) | 0.12656 (17) | 0.0390 (6) | |
| C31 | 0.2567 (3) | 0.6084 (2) | −0.1668 (2) | 0.0629 (9) | |
| H31 | 0.3147 | 0.5676 | −0.1708 | 0.076* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.03631 (19) | 0.0415 (2) | 0.03085 (19) | −0.00117 (15) | 0.00221 (14) | 0.00725 (16) |
| Cl1 | 0.0572 (5) | 0.0555 (5) | 0.0975 (7) | −0.0167 (4) | 0.0221 (5) | 0.0114 (5) |
| Cl2 | 0.0373 (4) | 0.0993 (7) | 0.0743 (6) | −0.0043 (4) | 0.0072 (4) | −0.0041 (5) |
| O1 | 0.0724 (15) | 0.0953 (18) | 0.0321 (11) | −0.0104 (13) | 0.0147 (11) | 0.0105 (11) |
| O2 | 0.0642 (14) | 0.0843 (16) | 0.0322 (11) | −0.0081 (12) | −0.0058 (10) | 0.0055 (11) |
| N1 | 0.0432 (13) | 0.0445 (13) | 0.0287 (12) | 0.0010 (10) | 0.0069 (10) | 0.0063 (10) |
| N2 | 0.0376 (12) | 0.0540 (15) | 0.0323 (12) | −0.0008 (10) | 0.0033 (10) | 0.0078 (11) |
| N3 | 0.0382 (12) | 0.0481 (14) | 0.0368 (13) | −0.0053 (10) | −0.0011 (10) | 0.0114 (11) |
| N4 | 0.0390 (13) | 0.0502 (14) | 0.0390 (13) | −0.0041 (11) | 0.0030 (10) | 0.0155 (11) |
| C1 | 0.0537 (17) | 0.0465 (17) | 0.0313 (15) | 0.0021 (13) | 0.0104 (13) | 0.0025 (13) |
| C2 | 0.0519 (17) | 0.0438 (17) | 0.0343 (16) | 0.0015 (13) | 0.0048 (14) | −0.0005 (13) |
| C3 | 0.0416 (16) | 0.0509 (18) | 0.0358 (15) | 0.0009 (13) | 0.0006 (12) | 0.0012 (13) |
| C4 | 0.0479 (18) | 0.070 (2) | 0.055 (2) | 0.0021 (16) | −0.0023 (15) | 0.0191 (17) |
| C5 | 0.0402 (17) | 0.082 (3) | 0.063 (2) | 0.0065 (17) | −0.0052 (15) | 0.0115 (19) |
| C6 | 0.0375 (16) | 0.069 (2) | 0.0510 (19) | −0.0060 (15) | 0.0039 (14) | −0.0086 (17) |
| C7 | 0.0419 (16) | 0.0561 (19) | 0.0430 (17) | −0.0045 (14) | 0.0029 (13) | 0.0002 (14) |
| C8 | 0.0364 (14) | 0.0480 (17) | 0.0350 (15) | −0.0025 (12) | 0.0013 (12) | −0.0032 (13) |
| C9 | 0.0406 (15) | 0.0449 (16) | 0.0349 (15) | −0.0071 (13) | 0.0047 (12) | −0.0016 (13) |
| C10 | 0.0326 (14) | 0.0478 (17) | 0.0374 (15) | −0.0080 (12) | −0.0006 (12) | 0.0057 (13) |
| C11 | 0.068 (2) | 0.057 (2) | 0.0495 (19) | −0.0166 (17) | 0.0106 (16) | −0.0070 (16) |
| C12 | 0.092 (3) | 0.045 (2) | 0.086 (3) | −0.0238 (19) | 0.018 (2) | −0.0063 (19) |
| C13 | 0.073 (2) | 0.064 (2) | 0.069 (2) | −0.0216 (18) | 0.014 (2) | 0.0187 (19) |
| C14 | 0.0483 (17) | 0.071 (2) | 0.0527 (19) | −0.0113 (16) | 0.0130 (15) | 0.0119 (17) |
| C15 | 0.0446 (16) | 0.0505 (18) | 0.0522 (18) | −0.0064 (14) | 0.0108 (14) | 0.0014 (15) |
| C16 | 0.0367 (19) | 0.046 (2) | 0.043 (2) | −0.0021 (16) | −0.0005 (16) | 0.0172 (19) |
| C17 | 0.071 (3) | 0.061 (3) | 0.058 (3) | 0.008 (2) | 0.005 (2) | 0.004 (2) |
| C18 | 0.0385 (18) | 0.056 (2) | 0.0381 (19) | −0.0064 (16) | −0.0029 (15) | 0.0164 (18) |
| C19 | 0.0352 (14) | 0.0389 (15) | 0.0378 (15) | 0.0003 (12) | 0.0075 (12) | 0.0039 (12) |
| C20 | 0.0344 (14) | 0.0401 (15) | 0.0403 (15) | −0.0041 (12) | 0.0052 (11) | 0.0093 (13) |
| C21 | 0.0471 (17) | 0.059 (2) | 0.0516 (19) | 0.0070 (15) | 0.0179 (15) | 0.0105 (15) |
| C22 | 0.0428 (17) | 0.075 (2) | 0.077 (3) | 0.0173 (16) | 0.0190 (17) | 0.034 (2) |
| C23 | 0.0477 (19) | 0.085 (3) | 0.055 (2) | −0.0020 (18) | −0.0049 (16) | 0.0267 (19) |
| C24 | 0.082 (3) | 0.087 (3) | 0.052 (2) | 0.010 (2) | −0.0128 (19) | −0.0062 (19) |
| C25 | 0.0396 (14) | 0.0337 (14) | 0.0409 (15) | 0.0003 (12) | 0.0128 (12) | 0.0033 (12) |
| C26 | 0.0424 (15) | 0.0389 (16) | 0.0501 (17) | −0.0016 (13) | 0.0105 (13) | 0.0081 (13) |
| C27 | 0.0468 (17) | 0.0426 (17) | 0.061 (2) | −0.0059 (13) | 0.0175 (15) | 0.0017 (15) |
| C28 | 0.068 (2) | 0.054 (2) | 0.057 (2) | −0.0100 (17) | 0.0218 (17) | 0.0136 (16) |
| C29 | 0.0602 (19) | 0.060 (2) | 0.0438 (18) | −0.0056 (16) | 0.0078 (15) | 0.0145 (15) |
| C30 | 0.0432 (15) | 0.0388 (15) | 0.0365 (15) | 0.0021 (12) | 0.0139 (12) | 0.0035 (12) |
| C31 | 0.066 (2) | 0.063 (2) | 0.052 (2) | 0.0161 (17) | 0.0025 (17) | −0.0050 (17) |
| Ni1—N2 | 1.857 (2) | C15—H15 | 0.9300 |
| Ni1—N1 | 1.867 (2) | C16—C18 | 1.502 (4) |
| Ni1—N4 | 1.870 (2) | C16—C17 | 1.504 (6) |
| Ni1—N3 | 1.874 (2) | C16—H16 | 0.9800 |
| Cl1—C27 | 1.740 (3) | C17—H17A | 0.9600 |
| Cl2—C6 | 1.753 (3) | C17—H17B | 0.9600 |
| O1—C1 | 1.218 (3) | C17—H17C | 0.9600 |
| O2—C2 | 1.226 (3) | C18—H18A | 0.9700 |
| N1—C1 | 1.373 (3) | C18—H18B | 0.9700 |
| N1—C30 | 1.394 (3) | C16'—C18' | 1.501 (17) |
| N2—C2 | 1.356 (3) | C16'—C17' | 1.510 (17) |
| N2—C3 | 1.392 (3) | C16'—H16' | 0.9800 |
| N3—C9 | 1.293 (3) | C17'—H17D | 0.9600 |
| N3—C16 | 1.508 (3) | C17'—H17E | 0.9600 |
| N3—C18' | 1.527 (17) | C17'—H17F | 0.9600 |
| N4—C19 | 1.297 (3) | C18'—H18C | 0.9700 |
| N4—C18 | 1.503 (4) | C18'—H18D | 0.9700 |
| N4—C16' | 1.553 (14) | C19—C25 | 1.466 (3) |
| C1—C2 | 1.518 (4) | C19—C20 | 1.500 (3) |
| C3—C4 | 1.403 (4) | C20—C31 | 1.376 (4) |
| C3—C8 | 1.408 (4) | C20—C21 | 1.377 (4) |
| C4—C5 | 1.373 (4) | C21—C22 | 1.387 (4) |
| C4—H4 | 0.9300 | C21—H21 | 0.9300 |
| C5—C6 | 1.377 (4) | C22—C23 | 1.363 (5) |
| C5—H5 | 0.9300 | C22—H22 | 0.9300 |
| C6—C7 | 1.360 (4) | C23—C24 | 1.366 (5) |
| C7—C8 | 1.409 (4) | C23—H23 | 0.9300 |
| C7—H7 | 0.9300 | C24—C31 | 1.380 (4) |
| C8—C9 | 1.475 (4) | C24—H24 | 0.9300 |
| C9—C10 | 1.499 (4) | C25—C26 | 1.411 (4) |
| C10—C11 | 1.382 (4) | C25—C30 | 1.412 (3) |
| C10—C15 | 1.393 (4) | C26—C27 | 1.364 (4) |
| C11—C12 | 1.383 (4) | C26—H26 | 0.9300 |
| C11—H11 | 0.9300 | C27—C28 | 1.381 (4) |
| C12—C13 | 1.373 (5) | C28—C29 | 1.368 (4) |
| C12—H12 | 0.9300 | C28—H28 | 0.9300 |
| C13—C14 | 1.363 (5) | C29—C30 | 1.413 (4) |
| C13—H13 | 0.9300 | C29—H29 | 0.9300 |
| C14—C15 | 1.372 (4) | C31—H31 | 0.9300 |
| C14—H14 | 0.9300 | ||
| N2—Ni1—N1 | 86.53 (9) | C17—C16—H16 | 109.4 |
| N2—Ni1—N4 | 176.84 (10) | N3—C16—H16 | 109.4 |
| N1—Ni1—N4 | 93.78 (9) | C16—C17—H17A | 109.5 |
| N2—Ni1—N3 | 92.76 (9) | C16—C17—H17B | 109.5 |
| N1—Ni1—N3 | 171.82 (10) | H17A—C17—H17B | 109.5 |
| N4—Ni1—N3 | 87.37 (9) | C16—C17—H17C | 109.5 |
| C1—N1—C30 | 120.7 (2) | H17A—C17—H17C | 109.5 |
| C1—N1—Ni1 | 110.65 (18) | H17B—C17—H17C | 109.5 |
| C30—N1—Ni1 | 127.86 (17) | C16—C18—N4 | 105.7 (3) |
| C2—N2—C3 | 120.5 (2) | C16—C18—H18A | 110.6 |
| C2—N2—Ni1 | 112.94 (18) | N4—C18—H18A | 110.6 |
| C3—N2—Ni1 | 126.44 (18) | C16—C18—H18B | 110.6 |
| C9—N3—C16 | 119.9 (2) | N4—C18—H18B | 110.6 |
| C9—N3—C18' | 117.1 (9) | H18A—C18—H18B | 108.7 |
| C9—N3—Ni1 | 130.16 (19) | C18'—C16'—C17' | 119 (2) |
| C16—N3—Ni1 | 109.55 (18) | C18'—C16'—N4 | 101.0 (15) |
| C18'—N3—Ni1 | 109.6 (11) | C17'—C16'—N4 | 119.5 (16) |
| C19—N4—C18 | 118.9 (2) | C18'—C16'—H16' | 105.5 |
| C19—N4—C16' | 119.2 (7) | C17'—C16'—H16' | 105.5 |
| C19—N4—Ni1 | 129.77 (19) | N4—C16'—H16' | 105.5 |
| C18—N4—Ni1 | 111.12 (17) | C16'—C17'—H17D | 109.5 |
| C16'—N4—Ni1 | 104.6 (7) | C16'—C17'—H17E | 109.5 |
| O1—C1—N1 | 128.0 (3) | H17D—C17'—H17E | 109.5 |
| O1—C1—C2 | 119.6 (3) | C16'—C17'—H17F | 109.5 |
| N1—C1—C2 | 112.4 (2) | H17D—C17'—H17F | 109.5 |
| O2—C2—N2 | 128.8 (3) | H17E—C17'—H17F | 109.5 |
| O2—C2—C1 | 119.3 (3) | C16'—C18'—N3 | 100.4 (14) |
| N2—C2—C1 | 111.9 (2) | C16'—C18'—H18C | 111.7 |
| N2—C3—C4 | 120.9 (3) | N3—C18'—H18C | 111.7 |
| N2—C3—C8 | 121.1 (2) | C16'—C18'—H18D | 111.7 |
| C4—C3—C8 | 117.9 (3) | N3—C18'—H18D | 111.7 |
| C5—C4—C3 | 121.9 (3) | H18C—C18'—H18D | 109.5 |
| C5—C4—H4 | 119.1 | N4—C19—C25 | 122.7 (2) |
| C3—C4—H4 | 119.1 | N4—C19—C20 | 119.4 (2) |
| C4—C5—C6 | 119.3 (3) | C25—C19—C20 | 117.9 (2) |
| C4—C5—H5 | 120.3 | C31—C20—C21 | 119.0 (3) |
| C6—C5—H5 | 120.3 | C31—C20—C19 | 120.5 (2) |
| C7—C6—C5 | 121.0 (3) | C21—C20—C19 | 120.5 (3) |
| C7—C6—Cl2 | 120.2 (3) | C20—C21—C22 | 119.9 (3) |
| C5—C6—Cl2 | 118.8 (2) | C20—C21—H21 | 120.0 |
| C6—C7—C8 | 120.6 (3) | C22—C21—H21 | 120.0 |
| C6—C7—H7 | 119.7 | C23—C22—C21 | 120.4 (3) |
| C8—C7—H7 | 119.7 | C23—C22—H22 | 119.8 |
| C3—C8—C7 | 119.1 (2) | C21—C22—H22 | 119.8 |
| C3—C8—C9 | 123.1 (2) | C22—C23—C24 | 120.0 (3) |
| C7—C8—C9 | 117.8 (2) | C22—C23—H23 | 120.0 |
| N3—C9—C8 | 121.8 (2) | C24—C23—H23 | 120.0 |
| N3—C9—C10 | 120.4 (2) | C23—C24—C31 | 119.9 (3) |
| C8—C9—C10 | 117.8 (2) | C23—C24—H24 | 120.1 |
| C11—C10—C15 | 119.5 (3) | C31—C24—H24 | 120.1 |
| C11—C10—C9 | 120.6 (3) | C26—C25—C30 | 119.3 (2) |
| C15—C10—C9 | 119.9 (3) | C26—C25—C19 | 116.9 (2) |
| C10—C11—C12 | 119.2 (3) | C30—C25—C19 | 123.8 (2) |
| C10—C11—H11 | 120.4 | C27—C26—C25 | 120.9 (3) |
| C12—C11—H11 | 120.4 | C27—C26—H26 | 119.5 |
| C13—C12—C11 | 120.8 (3) | C25—C26—H26 | 119.5 |
| C13—C12—H12 | 119.6 | C26—C27—C28 | 120.5 (3) |
| C11—C12—H12 | 119.6 | C26—C27—Cl1 | 120.4 (2) |
| C14—C13—C12 | 120.0 (3) | C28—C27—Cl1 | 119.0 (2) |
| C14—C13—H13 | 120.0 | C29—C28—C27 | 119.6 (3) |
| C12—C13—H13 | 120.0 | C29—C28—H28 | 120.2 |
| C13—C14—C15 | 120.3 (3) | C27—C28—H28 | 120.2 |
| C13—C14—H14 | 119.9 | C28—C29—C30 | 122.2 (3) |
| C15—C14—H14 | 119.9 | C28—C29—H29 | 118.9 |
| C14—C15—C10 | 120.2 (3) | C30—C29—H29 | 118.9 |
| C14—C15—H15 | 119.9 | N1—C30—C25 | 121.5 (2) |
| C10—C15—H15 | 119.9 | N1—C30—C29 | 121.2 (2) |
| C18—C16—C17 | 111.2 (3) | C25—C30—C29 | 117.3 (2) |
| C18—C16—N3 | 105.0 (3) | C20—C31—C24 | 120.8 (3) |
| C17—C16—N3 | 112.3 (3) | C20—C31—H31 | 119.6 |
| C18—C16—H16 | 109.4 | C24—C31—H31 | 119.6 |
| Ni1—N2 | 1.857 (2) | Ni1—N4 | 1.870 (2) |
| Ni1—N1 | 1.867 (2) | Ni1—N3 | 1.874 (2) |
| N2—Ni1—N1 | 86.53 (9) | N2—Ni1—N3 | 92.76 (9) |
| N2—Ni1—N4 | 176.84 (10) | N1—Ni1—N3 | 171.82 (10) |
| N1—Ni1—N4 | 93.78 (9) | N4—Ni1—N3 | 87.37 (9) |
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2000). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Zhang, R.-H., Wang, Q.-L., Wang, Y.-F., Yang, G.-M., Liu, Z.-Q., Ding, B. & Xu, G.-F. (2005). J. Coord. Chem. 58, 857–862.
The crystal structure of the title compound was determined as a part of a project on the structural properties of new nickel complexes with macrocyclic ligands. In the crystal structure of the title compound the nickel atoms are coordinated by four nitrogen atoms of the 2,3-dioxo-5,6:13,14-dichlorobenzo-7,12-diphenyl-1,4,8,11- tetraazacyclo-pentadeca-7,11-diene ligand within a slightly distorted square planar coordination (Fig 1). The nickel atom is located in the molecular plane of the ligand and deviates −0.0405 (12)Å from the plane calculated for N1, N2, N3 and N4.