Abstract
C40H34N4NiO4, monoclinic, P21/c (no. 14), a = 21.443(7) Å, b = 13.862(5) Å, c = 11.733(4) Å, β = 103.690(5)°, Z = 4, V = 3388(2) Å3, Rgt(F) = 0.0484, wRref(F2) = 0.1411, T = 296(2) K.
Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Crystal: | Yellow block |
Size: | 0.26 × 0.25 × 0.22 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.62 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II CCD, φ and ω |
θmax, completeness: | 25.0°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 17636, 5967, 0.055 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 4549 |
N(param)refined: | 446 |
Programs: | Bruker [13], SHELX [14] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
Ni1 | 0.75995(2) | 0.36359(2) | 0.54960(3) | 0.04258(15) |
O1 | 0.73871(11) | 0.49026(15) | 0.5525(2) | 0.0596(6) |
O2 | 0.78242(9) | 0.23682(14) | 0.5506(2) | 0.0531(5) |
O3 | 1.02081(13) | −0.02023(18) | 0.2678(3) | 0.0860(9) |
O4 | 0.47754(11) | 0.76237(16) | 0.7232(2) | 0.0700(7) |
N1 | 0.82561(11) | 0.38926(16) | 0.4706(2) | 0.0413(5) |
N2 | 0.97484(13) | 0.04831(19) | 0.2852(3) | 0.0611(7) |
N3 | 0.69320(10) | 0.33773(16) | 0.6266(2) | 0.0408(5) |
N4 | 0.51226(13) | 0.68776(18) | 0.6838(3) | 0.0577(7) |
C30 | 0.70183(13) | 0.1618(2) | 0.6308(2) | 0.0418(6) |
C6 | 0.82199(14) | 0.6484(2) | 0.3841(3) | 0.0456(7) |
C7 | 0.80547(13) | 0.5620(2) | 0.4396(2) | 0.0424(6) |
C21 | 0.67527(13) | 0.0723(2) | 0.6617(3) | 0.0459(7) |
C31 | 0.67484(13) | 0.2525(2) | 0.6505(3) | 0.0440(7) |
H31 | 0.6399 | 0.2502 | 0.6847 | 0.053* |
C12 | 0.86761(12) | 0.31311(19) | 0.4507(2) | 0.0388(6) |
C11 | 0.83745(13) | 0.4732(2) | 0.4309(2) | 0.0428(6) |
H11 | 0.8706 | 0.4755 | 0.3923 | 0.051* |
C15 | 0.95068(13) | 0.1709(2) | 0.4053(2) | 0.0429(6) |
C32 | 0.65801(12) | 0.4158(2) | 0.6623(2) | 0.0416(6) |
C29 | 0.75625(13) | 0.1608(2) | 0.5844(3) | 0.0427(6) |
C5 | 0.78723(14) | 0.7348(2) | 0.3925(3) | 0.0488(7) |
C26 | 0.70649(14) | −0.0156(2) | 0.6489(3) | 0.0468(7) |
C35 | 0.58830(13) | 0.5655(2) | 0.7332(3) | 0.0443(7) |
C38 | 0.55037(14) | 0.6450(2) | 0.7690(3) | 0.0478(7) |
C27 | 0.76324(14) | −0.0124(2) | 0.6053(3) | 0.0525(8) |
H27 | 0.7845 | −0.0697 | 0.5980 | 0.063* |
C8 | 0.75690(14) | 0.5642(2) | 0.5009(3) | 0.0472(7) |
C36 | 0.64179(14) | 0.5271(2) | 0.8083(3) | 0.0488(7) |
H36 | 0.6547 | 0.5509 | 0.8843 | 0.059* |
C18 | 0.99593(14) | 0.0974(2) | 0.3789(3) | 0.0505(7) |
C37 | 0.67683(14) | 0.4537(2) | 0.7728(3) | 0.0480(7) |
H37 | 0.7134 | 0.4300 | 0.8244 | 0.058* |
C13 | 0.92608(14) | 0.2989(2) | 0.5267(3) | 0.0511(7) |
H13 | 0.9385 | 0.3367 | 0.5938 | 0.061* |
C1 | 0.86896(16) | 0.6530(2) | 0.3190(3) | 0.0566(8) |
H1 | 0.8932 | 0.5984 | 0.3131 | 0.068* |
C28 | 0.78696(15) | 0.0705(2) | 0.5745(3) | 0.0523(8) |
H28 | 0.8240 | 0.0694 | 0.5462 | 0.063* |
C17 | 0.84954(15) | 0.2543(2) | 0.3538(3) | 0.0582(8) |
H17 | 0.8093 | 0.2622 | 0.3033 | 0.070* |
C10 | 0.73983(15) | 0.7337(2) | 0.4572(3) | 0.0574(8) |
H10 | 0.7180 | 0.7905 | 0.4643 | 0.069* |
C14 | 0.96667(14) | 0.2276(2) | 0.5030(3) | 0.0543(8) |
H14 | 1.0061 | 0.2182 | 0.5554 | 0.065* |
C9 | 0.72500(16) | 0.6532(2) | 0.5094(3) | 0.0572(8) |
H9 | 0.6934 | 0.6557 | 0.5517 | 0.069* |
C16 | 0.89014(15) | 0.1843(3) | 0.3306(3) | 0.0594(9) |
H16 | 0.8772 | 0.1454 | 0.2646 | 0.071* |
C25 | 0.68148(16) | −0.1032(2) | 0.6773(3) | 0.0577(8) |
H25 | 0.7023 | −0.1605 | 0.6680 | 0.069* |
C4 | 0.79995(17) | 0.8188(2) | 0.3345(3) | 0.0627(9) |
H4 | 0.7767 | 0.8747 | 0.3397 | 0.075* |
C2 | 0.87998(17) | 0.7364(2) | 0.2636(3) | 0.0657(9) |
H2 | 0.9111 | 0.7369 | 0.2203 | 0.079* |
C34 | 0.57124(16) | 0.5282(3) | 0.6206(3) | 0.0736(11) |
H34 | 0.5359 | 0.5536 | 0.5673 | 0.088* |
C3 | 0.84538(18) | 0.8203(2) | 0.2710(3) | 0.0676(9) |
H3 | 0.8532 | 0.8764 | 0.2331 | 0.081* |
C24 | 0.62695(19) | −0.1062(3) | 0.7183(3) | 0.0719(10) |
H24 | 0.6107 | −0.1649 | 0.7365 | 0.086* |
C22 | 0.61934(16) | 0.0666(2) | 0.7051(3) | 0.0663(9) |
H22 | 0.5977 | 0.1229 | 0.7154 | 0.080* |
C33 | 0.60539(16) | 0.4542(3) | 0.5860(3) | 0.0735(11) |
H33 | 0.5927 | 0.4300 | 0.5100 | 0.088* |
C23 | 0.59627(18) | −0.0209(3) | 0.7325(4) | 0.0785(11) |
H23 | 0.5594 | −0.0226 | 0.7611 | 0.094* |
C39 | 0.55765(19) | 0.6702(3) | 0.8949(3) | 0.0805(12) |
H39A | 0.5211 | 0.7069 | 0.9036 | 0.121* |
H39B | 0.5959 | 0.7078 | 0.9217 | 0.121* |
H39C | 0.5606 | 0.6122 | 0.9405 | 0.121* |
C19 | 1.06072(17) | 0.0852(3) | 0.4577(4) | 0.0764(11) |
H19A | 1.0832 | 0.0347 | 0.4281 | 0.115* |
H19B | 1.0566 | 0.0686 | 0.5350 | 0.115* |
H19C | 1.0843 | 0.1444 | 0.4609 | 0.115* |
C20 | 0.9945(2) | −0.0744(3) | 0.1680(5) | 0.1120(19) |
H20A | 0.9511 | −0.0914 | 0.1678 | 0.168* |
H20B | 1.0193 | −0.1321 | 0.1681 | 0.168* |
H20C | 0.9950 | −0.0371 | 0.0992 | 0.168* |
C40 | 0.4389(2) | 0.8086(3) | 0.6232(4) | 0.1030(16) |
H40A | 0.4653 | 0.8291 | 0.5722 | 0.154* |
H40B | 0.4182 | 0.8636 | 0.6476 | 0.154* |
H40C | 0.4070 | 0.7642 | 0.5822 | 0.154* |
Source of material
Synthesis of the ligand: All solvents and other reagents were of analytical grade. 4-Amino acetophenone methoxy oxime was prepared by a similar method reported earlier [1]. The ligand was prepared by refluxing a mixture of a solution containing 2-hydroxy-naphthalene-1-carbaldehyde (516.6 mg, 3 mmol) in EtOH (5 mL) and a solution containing 1-(4-aminophenyl)ethanone O-methyl-oxime (492.6 mg, 3 mmol) in EtOH (5 mL) at 328 K. 7 h later, the mixture was cooled to the room temperature and filtered. The product was dried under vacuum and a yellow solid was obtained (yield 67.4%, m.p. 485–491 K). Elemental analysis: Anal. Calcd. for C20H18N2O2: C, 75.45%; H, 5.70%; N, 8.80%; Found: C, 75.52%; H, 5.67%; N, 8.75%.
Synthesis of the nickel(II) complex: A solution of nickel(II) acetate tetrahydrate (2.5 mg, 10 mmol) in EtOH (2 mL) was added dropwise to the solution of ligand (6.4 mg, 20 mmol) in CHCl3 (4 mL) at room temperature. The color of the solution turned yellow, immediately. The mixture was filtered after being stirred for 2 h at room temperature and the filtrate was allowed to stand for 17 days at room temperature. The solvent was partially evaporated and several light yellow crystals were obtained. Anal. Calcd. for C40H34N4NiO4: C, 69.28%; H, 4.94%; N, 8.08%. Found: C, 69.34%; H, 4.86%; N, 8.02%.
Experimental details
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.
Comment
Oxime-type compounds are often synthesized by aldehydes or ketones with hydroxylamine or its derivatives through condensation reaction, with a general formula of R1R2C = N—OR3 [2], [3], [4]. Oxime-type compound and their metal complexes have been widely studied and some studies on this subject are already available [5], [6]. For example: it has been used to nonlinear optical materials field and supramolecular architectures [7], [8], [9], [10], [11], [12].
In the title complex, Ni1 is four-coordinated by two O atoms and two N atoms from two different ligands. The Ni1—N1 bond length is 1.894(2) Å and the Ni1—N3 bond lengths is 1.899(2) Å; and the Ni1—O1 bond length is 1.816(2) Å and the Ni1—O2 bond lengths is 1.821(2) Å, respectively. All geometric parameters are in the typical ranges.
Acknowledgements
This work was supported by the Science Foundation of Gansu Education Department of China (2017 A–023).
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