Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
-
Ming Li
and
Wei-Na Wu
Abstract
C23H30N4O4Ni, triclinic, P1̄ (no. 2), a = 7.5883(9) Å, b = 12.3110(15) Å, c = 12.7718(15) Å, α = 95.621(2)°, β = 99.908(2)°, γ = 101.30(2)°, V = 1141.8(2) Å3, Z = 2, Rgt(F) = 0.0433, wRref(F2) = 0.1239, T = 296 K.
The crystal structure is shown in the figure (Hydrogen atoms are omitted for clarity). Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Brown block |
| Size: | 0.19 × 0.18 × 0.16 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.89 mm−1 |
| Diffractometer, scan mode: | SMART detector, φ and ω |
| θmax, completeness: | 25.0°, 99% |
| N(hkl)measured, N(hkl)unique, Rint: | 5995, 3976, 0.053 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 3471 |
| N(param)refined: | 293 |
| Programs: | SHELX [1], Bruker [2] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Ni1 | 0.47371(4) | 0.47536(2) | 0.23179(2) | 0.03240(15) |
| O1 | 1.0777(3) | 0.84442(17) | 0.46845(17) | 0.0530(5) |
| O2 | 1.1071(4) | 0.7695(2) | 0.62107(19) | 0.0755(8) |
| O3 | 0.2304(4) | 0.85102(18) | −0.03955(18) | 0.0626(6) |
| O4 | 0.2230(5) | 0.8981(2) | 0.1320(2) | 0.0875(9) |
| N1 | 0.6577(3) | 0.56542(17) | 0.34353(17) | 0.0339(5) |
| N2 | 0.5053(3) | 0.35975(18) | 0.31607(19) | 0.0412(5) |
| N3 | 0.3404(3) | 0.37672(17) | 0.10850(18) | 0.0386(5) |
| N4 | 0.3805(3) | 0.58554(17) | 0.15816(17) | 0.0338(5) |
| C1 | 1.2515(5) | 1.0168(3) | 0.4415(4) | 0.0748(11) |
| H1A | 1.346984 | 1.080302 | 0.474448 | 0.112* |
| H1B | 1.286678 | 0.979963 | 0.381153 | 0.112* |
| H1C | 1.140436 | 1.041261 | 0.417786 | 0.112* |
| C2 | 1.2213(5) | 0.9386(3) | 0.5200(3) | 0.0698(10) |
| H2A | 1.333044 | 0.913705 | 0.544708 | 0.084* |
| H2B | 1.186261 | 0.975229 | 0.581477 | 0.084* |
| C3 | 1.0304(4) | 0.7633(2) | 0.5288(2) | 0.0436(7) |
| C4 | 0.8824(3) | 0.6730(2) | 0.4719(2) | 0.0364(6) |
| C5 | 0.7834(3) | 0.6625(2) | 0.3646(2) | 0.0351(6) |
| C7 | 0.6824(3) | 0.5112(2) | 0.4340(2) | 0.0346(6) |
| C6 | 0.8159(4) | 0.5745(2) | 0.5150(2) | 0.0362(6) |
| C8 | 0.8126(4) | 0.7365(2) | 0.2809(2) | 0.0475(7) |
| H8A | 0.928851 | 0.734779 | 0.261483 | 0.071* |
| H8B | 0.811018 | 0.811622 | 0.308357 | 0.071* |
| H8C | 0.716646 | 0.710687 | 0.218737 | 0.071* |
| C9 | 0.8813(4) | 0.5423(3) | 0.6228(2) | 0.0452(7) |
| H9A | 1.011831 | 0.550167 | 0.635001 | 0.068* |
| H9B | 0.823745 | 0.466068 | 0.625006 | 0.068* |
| H9C | 0.850105 | 0.590170 | 0.677535 | 0.068* |
| C10 | 0.5941(4) | 0.3959(2) | 0.4129(2) | 0.0391(6) |
| H10 | 0.600086 | 0.349205 | 0.465823 | 0.047* |
| C11 | 0.4328(5) | 0.2388(2) | 0.2863(3) | 0.0672(10) |
| H11A | 0.532287 | 0.204076 | 0.272526 | 0.081* |
| H11B | 0.389533 | 0.208710 | 0.346951 | 0.081* |
| C12 | 0.2832(6) | 0.2070(3) | 0.1923(3) | 0.0777(12) |
| H12A | 0.176006 | 0.229212 | 0.211640 | 0.093* |
| H12B | 0.253979 | 0.126162 | 0.176051 | 0.093* |
| C13 | 0.3153(5) | 0.2537(2) | 0.0931(3) | 0.0548(8) |
| H13A | 0.423588 | 0.233811 | 0.073035 | 0.066* |
| H13B | 0.211730 | 0.221659 | 0.035292 | 0.066* |
| C14 | 0.2855(4) | 0.4266(2) | 0.0287(2) | 0.0393(6) |
| H14 | 0.235825 | 0.387603 | −0.039456 | 0.047* |
| C15 | 0.3052(3) | 0.5443(2) | 0.0506(2) | 0.0355(6) |
| C16 | 0.2426(4) | 0.6241(2) | −0.0036(2) | 0.0377(6) |
| C17 | 0.2721(4) | 0.7187(2) | 0.0746(2) | 0.0395(6) |
| C18 | 0.3526(4) | 0.6898(2) | 0.1735(2) | 0.0364(6) |
| C19 | 0.1509(4) | 0.6069(3) | −0.1205(2) | 0.0490(7) |
| H19A | 0.230998 | 0.648133 | −0.160356 | 0.074* |
| H19B | 0.038729 | 0.632932 | −0.127572 | 0.074* |
| H19C | 0.124808 | 0.528837 | −0.147906 | 0.074* |
| C20 | 0.3918(4) | 0.7577(2) | 0.2821(2) | 0.0488(7) |
| H20A | 0.279493 | 0.771931 | 0.299411 | 0.073* |
| H20B | 0.474493 | 0.827480 | 0.281679 | 0.073* |
| H20C | 0.446539 | 0.717357 | 0.334676 | 0.073* |
| C21 | 0.2384(4) | 0.8297(3) | 0.0615(3) | 0.0493(7) |
| C22 | 0.2068(7) | 0.9618(3) | −0.0599(3) | 0.0792(12) |
| H22A | 0.080746 | 0.967060 | −0.060461 | 0.095* |
| H22B | 0.285429 | 1.017648 | −0.003522 | 0.095* |
| C23 | 0.2532(9) | 0.9817(4) | −0.1620(4) | 0.120(2) |
| H23A | 0.237913 | 1.054885 | −0.175972 | 0.180* |
| H23B | 0.378323 | 0.977021 | −0.160669 | 0.180* |
| H23C | 0.174262 | 0.926588 | −0.217436 | 0.180* |
Source of material
Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate (0.390 g, 2 mmol) and propane-1,3-diamine (0.074 g, 1 mmol) were dissolved in an ethanol/THF (1:1) solution (10 mL). The mixture was stirred for 4 h at room temperture, and then nickel acetate (0.175 g, 1 mmol) was added. The resulting solution was left in air for a few days, yielding brown block crystals.
Experimental details
The structure was solved by direct methods and refined with the SHELX software package [7]. The hydrogen atoms were placed at calculated positions and refined as riding atoms.
Comment
Schiff base ligands bearing pyrrole units have attracted much recent attention due to their excellent coordination abilities [3], [4]. The crystal structures of copper(II) and zinc(II) complexes with bis(pyrrol-2-ylmethyleneamine) ligands have been investigated [3], [4], [5], [6], [7], [8], while those of the nickel(II) complexes are rarely reported [7].
In the title complex, the Ni(II) ion is coordinated by the ligand via its four N atoms, giving a distorted square planar geometry (r.m.s. deviation 0.2330 Å). The dihedral angle, defined by the intersection of two pyrrol-2-ylmethyleneamine planes (N1/C4-C7, r.m.s. deviation 0.0115 Å; N4/C15-C18, r.m.s. deviation 0.0159 Å) at the nickel center, is 45.4°. The N—Cu—N angles range from 83.70(9) to 166.03(10)°, and the bond distances of Ni—N span from 1.890(2) to 1.903(2) Å. The molecular structure of the title complex is isostructural with that of a copper(II) complex [8]. Similarly, there exist no classical hydrogen bonds in the crystal.
References
1. Sheldrick, G. M.: Crystal refinement with SHELX. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central
2. BRUKER. SMART and SAINT. Bruker AXS Inc., Madison, WI, USA (2007).Search in Google Scholar
3. Wu, Z.; Chen, Q.; Xiong, S.; Xin, B.; Zhao, Z.; Jiang, L.; Ma, J. S.: Double-stranded helicates, triangles, and squares formed by the self-assembly of pyrrol-2-ylmethyleneamines and ZnII ions. Angew. Chem. Int. Ed. 42 (2003) 3271–3274.10.1002/anie.200350908Search in Google Scholar PubMed
4. Yang, L.; Chen, Q.; Li, Y.; Xiong, S.; Li, G.; Ma, J. S.: Self-assembly of bis(pyrrol-2-ylmethyleneamine) ligands with Cu(II) controlled by bridging [-(CH2)n-] spacers and weak intermolecular C—H⋯Cu hydrogen bonding. Eur. J. Inorg. Chem. 2004 (2004) 1478–1487.10.1002/ejic.200300639Search in Google Scholar
5. Wang, Y.; Yang, Z.-Y.; Chen, Z.-N.: Synthesis, characterization and DNA binding properties of four Zn(II) complexes with bis(pyrrol-2-yl-methyleneamine) ligands. Bioorg. Med. Chem. Lett. 18 (2008) 298–303.10.1016/j.bmcl.2007.10.085Search in Google Scholar PubMed
6. Wang, Y.; Wu, W.-N.; Wang, Q.; Yang, Z.-Y.: Synthesis, characterization, and antioxidant activities of three Cu(II) complexes with Schiff-base ligands. J. Coord. Chem. 63 (2010) 147–155.10.1080/00958970903295836Search in Google Scholar
7. Mao, P. D.; Yan, L.-L.; Wu, W.-N.; Song, Y.-H.; Yao, B.-X.: Ni(II)/Cu(II)/Zn(II) complexes baded on a bis(pyrrol-2-yl-methyleneamine) ligand: syntheses, characterization, fluorescence properties and crystal structures of Ni(II)/Cu(II) complexes. Chin. J. Inorg. Chem. 32 (2016) 879–883.Search in Google Scholar
8. Han, X.-F.; Yang, Q.-W.; Yang, Q.-W.; Wu, W.-N.: Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]copper(II), C23H30N4O4Cu. Z. Kristallogr. NCS 233 (2018) 319–320.10.1515/ncrs-2017-0315Search in Google Scholar
©2018 Ming Li et al., published by De Gruyter, Berlin/Boston
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