Home Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
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Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn

  • Xiao-Li Gao ORCID logo EMAIL logo , Rong-Li Geng and Pai Chen
Published/Copyright: December 27, 2019

Abstract

C18H16N10O2Zn, triclinic, P1̄ (no. 2), a = 10.218(7) Å, b = 10.490(7) Å, c = 11.101(8) Å, α = 79.590(11)°, β = 65.913(12)°, γ = 66.785(10)°, V = 998.0(12) Å3, Z = 2, Rgt(F) = 0.0516, wRref(F2) = 0.1323, T = 293(2) K.

CCDC no.: 1971033

The crystal structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.12 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.27 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:5099, 3480, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2663
N(param)refined:282
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
Zn10.26960(5)0.28380(5)0.21019(5)0.0361(2)
O10.3652(3)0.3891(3)0.0410(3)0.0405(7)
O20.3943(3)0.3020(3)0.3153(3)0.0420(7)
N10.0678(4)0.2763(4)0.3943(4)0.0393(9)
N2−0.2002(5)0.3050(5)0.6139(4)0.0637(13)
N30.0973(4)0.4744(3)0.2202(3)0.0358(8)
N40.1297(4)0.5698(3)0.1181(4)0.0396(9)
N50.3674(7)0.5082(6)−0.3012(6)0.0881(17)
N60.2242(4)0.1516(3)0.1037(4)0.0369(9)
N70.1988(5)−0.0471(4)−0.0124(4)0.0541(11)
N80.4061(3)0.0815(3)0.2359(3)0.0318(8)
N90.4924(4)0.0608(3)0.3114(4)0.0377(9)
N100.8599(6)0.0908(6)0.2995(6)0.0905(18)
C10.0539(5)0.1734(5)0.4812(5)0.0525(13)
H10.13550.08910.46880.063*
C2−0.0808(6)0.1894(6)0.5906(5)0.0619(15)
H2−0.08650.11500.64990.074*
C3−0.1861(5)0.4083(5)0.5267(5)0.0500(13)
H3−0.26850.49200.53990.060*
C4−0.0527(4)0.3959(4)0.4162(4)0.0357(10)
C5−0.0319(5)0.5097(4)0.3162(4)0.0368(10)
C6−0.1548(5)0.6503(5)0.3329(5)0.0555(14)
H6A−0.11080.71720.28040.083*
H6B−0.20090.67460.42410.083*
H6C−0.23160.64920.30470.083*
C70.2723(5)0.5102(4)0.0337(4)0.0372(10)
C80.3250(5)0.6015(4)−0.0838(4)0.0424(11)
H8A0.24870.6947−0.07090.051*
H8B0.42020.6066−0.08980.051*
C90.3484(6)0.5491(5)−0.2065(6)0.0515(13)
C100.1357(5)0.1865(5)0.0346(5)0.0459(12)
H100.08040.27970.02440.055*
C110.1238(6)0.0869(6)−0.0229(5)0.0532(13)
H110.06030.1156−0.07080.064*
C120.2876(5)−0.0814(5)0.0588(5)0.0447(11)
H120.3408−0.17480.07060.054*
C130.3031(4)0.0153(4)0.1149(4)0.0327(9)
C140.4030(4)−0.0227(4)0.1921(4)0.0325(9)
C150.4917(5)−0.1708(4)0.2130(5)0.0430(11)
H15A0.5692−0.17570.24340.065*
H15B0.5395−0.21860.13140.065*
H15C0.4237−0.21340.27780.065*
C160.4757(4)0.1837(4)0.3441(4)0.0350(10)
C170.5659(5)0.1759(5)0.4275(4)0.0424(11)
H17A0.53300.26730.46090.051*
H17B0.54260.11390.50270.051*
C180.7300(6)0.1276(6)0.3547(5)0.0534(13)

Source of material

Cyanoacetic acid hydrazide (0.099 g, 1 mmol) and 2-aceto-pyrazine (0.122 g, 1 mmol) were dissolved in methanol (20 mL). The reaction mixture was refluxed for 1 h and cooled to room temperature. Then zinc(II) acetate dihydrate (0.110 g, 0.5 mmol) was added. After stirring for 1 h, the mixture was filtered and set aside to crystallize for several days, giving yellow block crystals.

Experimental details

The structure was solved by direct methods and refined with the SHELX crystallographic software package [3]. The hydrogen atoms were placed at calculated positions and refined as riding atoms with isotropic displacement parameters.

Discussion

Hydrazones derived from 2-aceto-pyrazine and their metal complexes have been widely investigated mainly due to their excellent biological activities [4], [5], [6]. However, most research has focused on aryl-hydrazones and investigations on alkyl-hydrazones are relatively few [4], [5], [6], [7]. Herein, the title complex was synthesized and characterized by X-ray diffraction in this work.

In the title crystal structure, the central Zn(II) ion is six-coordinated to two anionic hydrazone ligands by a pair of ON2 donor sets, thus giving a distorted octahedral coordination geometry. The C–O bond of the hydrazone ligand is in the enolate form, which is supported by the distance of C—O bond being 1.264(5)/1.263(5) Å for C16–O2 and C7–O1, respectively, similar to what was found in other hydrazone ligands [6], [7]. The structure is similar to that of the Zn(II) complex with the 2-aceto-pyrazine benzoylhydrazone ligand [6]. As expected, there exist no classical hydrogen bonds in the crystal.

Award Identifier / Grant number: 21671124

Funding statement: This work is supported by National Natural Science Foundation of China (grant no. 21671124).

References

1. Bruker. SMART and SAINT. Bruker AXS Inc., Madison, WI, USA (2007).Search in Google Scholar

2. Sheldrick, G. M.: SHELXT-Integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: Crystal structure refinement with SHELX. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

4. Xu, J.; Zhou, T.; Xu, Z.-Q.; Gu, X.-N.; Wu, W.-N.; Chen, H.; Wang, Y.; Jia, L.; Zhu, T.-F.; Chen, R.-H.: Synthesis, crystal structures and antitumor activities of copper(II) complexes with a 2-acetylpyrazine isonicotinoyl hydrazone ligand. J Mol. Struct. 1128 (2017) 448–454.10.1016/j.molstruc.2016.09.016Search in Google Scholar

5. Wang, W.-W.; Wang, Y.; Zhang, L.; Song, Y.-F.; Wu, W.-N.; Chen, Z.: Syntheses, crystal structures and DNA-binding properties of Cu(II)/Ni(II) complexes with acylhydrazone ligand bearing pyrazine unit. Chin. J. Inorg. Chem. 35 (2019) 563–568.Search in Google Scholar

6. Hou, X.-F.; Zhao, X.-L.; Zhang, L.; Wu, W.-N.; Wang, Y.: Co(II)/Zn(II)/Cu(II) complexes containing hydrazone ligand bearing pyrazine unit: syntheses, crystal structures and fluorescence properties. Chin. J. Inorg. Chem. 34 (2018) 201–205.Search in Google Scholar

7. Huang, W.; Li, Y.; Yong, J.; Liu, Y.; Wu, D.: Hydrazone-based cobalt complexes toward multielectron redox and spin crossover. RSC Adv. 8 (2018) 17159–17167.10.1039/C8RA02963FSearch in Google Scholar

Received: 2019-11-04
Accepted: 2019-12-10
Published Online: 2019-12-27
Published in Print: 2020-02-25

©2019 Xiao-Li Gao et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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