Startseite Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato-κ3O,O′,N)zinc(II), C36H26N2O4Zn
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Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato-κ3O,O′,N)zinc(II), C36H26N2O4Zn

  • Guo qiang Li , Rui ping Zhou , Xiao fang Luo , Hong Zhou und Qiang Xu EMAIL logo
Veröffentlicht/Copyright: 5. August 2017

Abstract

C36H26N2O4Zn, monoclinic, C2/c (no. 15), a = 43.237(10) Å, b = 17.201(4) Å, c = 11.271(2) Å, β = 103.009(5)°, V = 8168(3) Å3, Z = 12, Rgt(F) = 0.0442, wRref(F2) = 0.1530, T = 100(2) K.

CCDC no.:: 1494369

The crystal structure is shown in the figure. The radii of the ellipsoids are drawn with an arbitrary probability. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Yellow block
Size:0.20 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:9.5 cm−1
Diffractometer, scan mode:Bruker APEXII, φ and ω-scans
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:28278, 7220, 0.055
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4975
N(param)refined:582
Programs:Bruker [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
Zn10.326086(10)0.75276(3)0.19582(4)0.03364(16)
Zn20.50000.64801(4)0.25000.0460(2)
O40.32703(6)0.83457(17)0.0738(2)0.0429(7)
O20.30372(6)0.84088(15)0.3154(2)0.0357(6)
O50.48755(6)0.53334(16)0.3529(2)0.0389(7)
O10.33563(6)0.65285(17)0.1268(3)0.0493(8)
O30.33409(6)0.70345(16)0.4095(2)0.0368(7)
N20.37246(7)0.77719(19)0.2829(3)0.0310(7)
N10.27853(7)0.72479(18)0.1610(3)0.0276(7)
O60.50315(7)0.7127(2)0.1094(4)0.0850(13)
N30.45247(7)0.63266(18)0.1848(3)0.0344(8)
C40.27939(9)0.4828(2)−0.0741(3)0.0335(9)
C200.36676(9)0.6999(2)0.4562(3)0.0357(10)
C120.25723(9)0.7751(2)0.2050(3)0.0271(8)
C170.27090(9)0.8333(2)0.2864(3)0.0313(9)
C90.26383(9)0.5450(2)−0.0280(3)0.0285(8)
C130.22406(9)0.7716(2)0.1717(3)0.0314(9)
H130.21410.73270.11620.038*
C380.45439(8)0.5301(2)0.3330(3)0.0319(9)
C100.28304(9)0.6043(2)0.0478(3)0.0276(8)
C430.43624(9)0.5817(2)0.2497(3)0.0314(9)
C110.26688(9)0.6635(2)0.0977(3)0.0284(8)
H110.24450.65770.08320.034*
C360.35037(9)0.8790(2)0.0614(3)0.0366(9)
C450.44768(9)0.7265(2)0.0161(4)0.0392(10)
C540.42445(10)0.7656(2)−0.0809(4)0.0395(10)
C250.38669(9)0.7354(2)0.3903(3)0.0331(9)
C260.38994(9)0.8253(2)0.2372(3)0.0344(9)
H260.41150.82840.28010.041*
C10.31657(9)0.6011(2)0.0677(3)0.0361(9)
C210.37842(10)0.6581(2)0.5608(4)0.0446(11)
H210.36430.63480.60370.054*
C440.43629(9)0.6744(2)0.0948(4)0.0362(9)
H440.41390.66930.08000.043*
C50.26136(11)0.4244(2)−0.1450(4)0.0434(11)
H50.27200.3822−0.17270.052*
C160.25213(10)0.8856(2)0.3334(3)0.0392(10)
H160.26180.92480.38890.047*
C270.38154(9)0.8738(2)0.1325(3)0.0332(9)
C390.44050(10)0.4788(3)0.3987(4)0.0460(11)
H390.45350.44470.45520.055*
C30.31287(10)0.4815(2)−0.0488(4)0.0408(10)
H30.32320.4400−0.07990.049*
C460.48059(12)0.7414(3)0.0266(5)0.0616(14)
C150.21953(10)0.8806(2)0.2993(3)0.0414(10)
H150.20670.91600.33160.050*
C80.23043(9)0.5459(2)−0.0628(3)0.0337(9)
H80.21930.5874−0.03590.040*
C530.39141(11)0.7580(2)−0.0980(4)0.0455(11)
H530.38300.7242−0.04660.055*
C180.31827(10)0.8338(3)0.4434(3)0.0434(11)
H18A0.30670.86640.49140.052*
H18B0.34050.85230.45890.052*
C420.40346(9)0.5799(2)0.2382(3)0.0378(10)
H420.39040.61530.18450.045*
C490.43530(12)0.8156(3)−0.1625(4)0.0542(13)
C330.39838(11)0.9750(3)0.0023(4)0.0474(11)
C140.20548(9)0.8239(2)0.2182(3)0.0378(10)
H140.18300.82070.19420.045*
C70.21350(10)0.4890(2)−0.1343(4)0.0416(10)
H70.19100.4919−0.15620.050*
C410.38972(9)0.5277(3)0.3036(4)0.0441(11)
H410.36730.52700.29350.053*
C280.40658(9)0.9205(2)0.0985(4)0.0391(10)
C240.41929(10)0.7243(3)0.4342(4)0.0455(11)
H240.43370.74620.39090.055*
C190.31757(10)0.7504(3)0.4819(4)0.0439(11)
H19A0.32800.74520.56930.053*
H19B0.29530.73250.47020.053*
C400.40816(10)0.4763(3)0.3837(4)0.0488(12)
H400.39860.43980.42760.059*
C370.50182(9)0.4647(2)0.3175(4)0.0473(11)
H37A0.49150.41800.34250.057*
H37B0.52460.46320.35830.057*
C230.43095(11)0.6829(3)0.5378(4)0.0514(12)
H230.45320.67640.56530.062*
C20.33060(10)0.5369(2)0.0178(4)0.0419(10)
H20.35310.53360.03220.050*
C60.22914(11)0.4265(3)−0.1751(4)0.0482(12)
H60.21740.3864−0.22310.058*
C220.41076(11)0.6502(3)0.6031(4)0.0536(12)
H220.41910.62260.67630.064*
C470.48962(12)0.7918(3)−0.0609(6)0.0788(19)
H470.51160.8006−0.05620.095*
C520.37124(12)0.7985(3)−0.1874(4)0.0582(13)
H520.34900.7930−0.19560.070*
C510.38228(14)0.8474(3)−0.2669(4)0.0631(14)
H510.36780.8741−0.32960.076*
C500.41344(14)0.8563(3)−0.2537(4)0.0629(14)
H500.42120.8906−0.30650.075*
C340.36654(12)0.9824(3)−0.0581(4)0.0543(12)
H340.36091.0204−0.12030.065*
C350.34375(11)0.9380(3)−0.0316(4)0.0487(12)
H350.32250.9455−0.07550.058*
C480.46833(13)0.8271(3)−0.1492(5)0.0766(18)
H480.47560.8607−0.20420.092*
C310.45295(14)1.0100(4)0.0203(5)0.0792(18)
H310.46861.0406−0.00520.095*
C300.46182(12)0.9569(4)0.1145(5)0.0783(18)
H300.48360.95060.15330.094*
C290.43869(11)0.9128(3)0.1517(4)0.0580(13)
H290.44510.87620.21570.070*
C320.42222(13)1.0180(3)−0.0344(5)0.0657(15)
H320.41641.0538−0.09980.079*

Source of material

The educt 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-ol) (H2L) used in the present work was synthesized via a standard Schiff base condensation reaction of 2-hydroxy-1-naphthaldehyde (0.6887 g, 4 mmol) and bis(4-aminophenoxy)ethane (0.4886 g, 2 mmol) following a modified literature procedure [3]. All other reagents were commercially available and used without further purification. The title compound was prepared by a vapor diffusion method. To a yellow MeOH solution (15 mL) of H2L (0.552 g, 1 mmol) was added slowly a MeOH solution (10 mL) of Zn(CH3COO)2⋅2H2O (0.220 mg, 1 mmol), and the resulting solution was stirred for 30 min to afford a clear pale-gold colored solution. The solvent was evaporated in air to give a yellow powder, which was isolated by filtration, washed with cold MeOH, and dried under vacuum over P4O10. The yellow block-shaped crystals suitable for X-ray analysis were obtained from a acetone solution of the powdered solid after about 3 days.

Experimental details

All of the hydrogen atoms were placed in the calculated positions and all the non-hydrogen atoms were refined anisotropically.

Discussion

Schiff base is one of the oldest compound bearing the —N=CH— functional group, which can be readily synthesized by the condensation reaction of carbonyl-containing compounds with primary amines. For a long time, numerous chemists from different disciplines have redirected their efforts to Schiff-base complexes due to their potential application in photocatalysis [4], bioscience [5] and magnetic properties [6]. As part of our work, a novel zinc(II) complex with a Salen-type bisoxime ligand was synthesized and characterized by X-ray diffraction.

The title complex is a mononuclear structure. The central zinc(II) is hexa-coordinated by two nitrogen atoms (N(1), N(2)) and four oxygen atoms (O(1), O(2), O(3), O(4)), resulting a slightly distored-octahedral geometry. The equatorial plane is defined by two ether O atoms (O2 and O3) and two aromatic-oxide O atoms (O1 and O4; cf. the figure) with the Zn—O bond distance in the range of 1.968(3) Å to 2.410(3) Å, and the O—Zn—O bond angles around the Zn(II) atom vary from 70.11(13)° to 158.49(11)°. The axial positions are occupied by two imine nitrogen atoms with the N(1)-Zn(1)-N(2) bond angle is 163.15(12)°, and the bond length of Zn(1)-N(1), Zn(1)-N(2) are 2.063(3) Å and 2.067(3) Å, respectively.

All bond lengths and angles in the organic ligand system are in the expected ranges.

Acknowledgement

I acknowledge support for the publication fee by the Scientific Research Fund of Chongqing Municipal Education Commissionthe (KJ1601115), Chongqing University of Arts and Sciences (Z2015CH02), Chongqing University of Arts and Sciences (XSKY2016058) and Chongqing University of Arts and Sciences (XSKY2016067).

References

Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, Wisconsin, USA, 2009.Suche in Google Scholar

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

Zhang, Q. L.; Zhang, Y. Q.; Zhu, B. X.: Crystal structure of Ag(I) schiff base complex. Chinese. J. Inorg. Chem. 27 (2011) 2191–2194.Suche in Google Scholar

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Received: 2017-1-20
Accepted: 2017-7-18
Published Online: 2017-8-5
Published in Print: 2017-9-26

©2017 Guo qiang Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 2-(2-ethoxyphenyl)-7-propyl-5-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one, C17H20N4O2
  3. Crystal structure of catena-poly[aqua-(μ3-1,3,5-benzenetricarboxylato-κ3O:O′:O′′)-[μ3hydroxy-(1,3-di-(μ2-1,2,4-triazole-4-yl)benzoato-κ2N:N′)copper(II)], C19H16Cu2N6O9
  4. Crystal structure of poly[aqua-(μ3-3,5-di(4H-1,2,4-triazolyl-4-κ3N,N′:N′′)benzenecarboxylato)silver(I)], C11H9AgN6O3
  5. Crystal structure of tetrapropylammonium hydrogen carbonate, C13H29NO3
  6. Crystal structure of poly[μ2-acetato-κ3-O,O′:O′)diaqua(μ3-isophthalato-κ4O,O′:O′′:O′′′)yttrium(III)] monohydrate, C20H24O17Y2
  7. Crystal structure of catena-poly[dichlorido-(μ2-4-(1H-pyrazol-3-yl)-pyridine-κ2N,N′)]cadmium(II), C48H42Cd3Cl16N18
  8. Crystal structure of bis(tetraethylammonium) [1,1′-biphenyl]-2,2′-dicarboxylate trihydrate, C30H54N2O7
  9. Crystal structure of poly[(thiophene-3,4-dicarboxylato-κ1O)bis[1,2-bis(4-pyridyl)ethane-κ2N:N′]silver(I)] octahydrate, C30H42Ag2N4O12S
  10. The crystal structure of amine-(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)silver(I) dihydrate, C9H13AgN4O4
  11. Crystal structure of poly[tetrakis(μ2-cyanido-κ2N:O)-cyanido-tris(pyridine)dicobalt(II/III)], C20H15Co2N8
  12. Crystal structure of bis(pyridine)-bis(2-formyl-4,6-dichlorophenolato)cobalt(II), C24H16Cl4CoN2O4
  13. Crystal structure of (E)-1-(4-(((E)-5-bromo-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  14. Crystal structure of catena-poly[(μ2-3-(1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,2,4-triazole-κ N:N′)-bis(benzoato-κO)zinc(II)], C24H18N6O4Zn
  15. Hydrothermal synthesis and crystal structure of a poly[aqua-(μ4-4-(carboxylatomethyl)benzoato-κ4O:O′:O′′:O′′′)-(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′) dimanganese(II)], [Mn2(C9H6O4)2(C12H11N5)(H2O)]
  16. Crystal structure of diaqua-catena-poly[diaqua-bis(μ2-5-(4-(1H-1,2,4-triazol-1-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)] dihydrate, C20H24CoN14O4
  17. Crystal structure of bis(μ3-2,2′-azanediylbis(ethan-1-olato)-κ5O:O,N,O′:O′)-tetrachlorido-bis(μ2-2-((2-hydroxyethyl)amino)ethan-1-olato-κ3N,O:O)dicobalt(II)dicobalt(III), C16H38Cl4Co4N4O8
  18. Crystal structure of poly[μ4-(4-(carboxylatomethyl)benzoato-κ4O:O′:O′′:O′′′)-(2-(4-(1H-imidazol-1-yl)phenyl)-1H-benzo[d]imidazole-κN)manganese(II)] [Mn(C9H6O4)(C16H12N4)]
  19. Crystal structure of 4-chloro-6-phenylpyrimidine, C10H7ClN2
  20. The crystal structure of [6-methoxy-2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1(2H)-one]difluoroborane, C13H10BF5O3
  21. Crystal structure of 3,3′-(butane-1,4-diylbis(azanylylidene))bis(1-phenylbut-1-en-1-olato)-κ4N,N′,O,O′]copper(II), C24H26N2O2Cu
  22. Crystal structure of tetraaqua-bis((E)-N′-(2-bromobenzylidene)isonicotinohydrazide-κN)zinc(II) dinitrate, C26H28N8O12Br2Zn
  23. Crystal structure of 2-amino-4-(4-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13BrN2O2
  24. A single crystal study on tert-butyl-4-((4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-yloxy)methyl)piperidine-1-carboxylate, C26H30BrFN4O4
  25. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato-κ3O,O′,N)zinc(II), C36H26N2O4Zn
  26. Crystal structure of diaqua-bis(5′-(pyridin-1-ium-4-yl)-1H-[3,3′-bi(1,2,4-triazol)]-2′-ide-κ2N,N′)cobalt(II) — bis(5-(pyridin-4-yl-κN)-1H,1′H-3,3′-bi(1,2,4-triazole))octamolybdate – water (2/1/8), C27H33CoMo4N21O19
  27. Crystal structure of 3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-6,8-diiodo-4H-1,3-benzoxazin-4-one, C20H24I2N2O2
  28. Crystal structure of dinitrato-κO-bis(tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′)-(μ2-cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′,O′′′)dimanganese(II) – methanol – water (1/6/2), C62H80Mn2N16O18
  29. Crystal structure of bis(2-hydroxyethyl(phenyl)carbamodithioate)nickel(II), C18H20N2NiO2S4
  30. Crystal structure of methyl 1-(4-fluorobenzyl)-4-methoxy-5-oxopyrrolidine-3-carboxylate, C14H16FNO4
  31. Crystal structure of di-μ-iodido-bis(6-(p-tolyl)-2,2′-bipyridine-κ2N,N′)dicopper(I) — 2-(diphenylphosphoryl)benzoic acid (1/2), C36H29CuIN2O3P
  32. Crystal structure of 2-amino-4-(3-bromo-4-fluoro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H16BrFN2O2
  33. Crystal structure of bis(μ2-2-chlorobenzoato-κ3O,O′:O′)-(2-chlorobenzoato-κO)-(2-chlorobenzoato-κO,O′)-bis(1,10-phenanthroline-κ2N,N′)-dicadmium(II) monohydrate, C52H36Cd2Cl4N4O10
  34. Crystal structure of 2-(8a-methyl-5-oxo-hexahydroimidazo [1,2-a]pyridin-1(5H)-yl)-2-oxoethyl acetate, C12H18N2O4
  35. Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C15H17N3O2S
  36. Crystal structure of diazido-dimethanolato-bis(μ2-2-(((3-oxidopropyl)imino)methyl)phenolato-κ4O:O,O′,N)dimanganese(III), C22H28Mn2N8O6
  37. The crystal structure of bis(2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1-olato-κ2O,O′)copper(II), C24H16CuF6O4
  38. Crystal structure of hexaaquanickel(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40N6NiO12S2
  39. Crystal structure of catena-poly[aqua-(μ2-hexamethylenetetramine-κ2N:N′)-bis(2,6-difluorobenzoato-κ2O:O′)cadmium(II)]monohydrate, C20H22CdF4N4O6
  40. Crystal structure of 3-benzyl-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C15H12N2OS
  41. Crystal structure of bis(μ2-ferrocenecarboxylato-κ2O:O′)-bis(1,10-phenanthroline-κ2N,N′)-(μ2-methanolato2O,O)dicopper(II) tetrafluoroborate – acetonitrile (1/1), C49H40BCu2F4Fe2N5O5
  42. The crystal structure of tetrakis(1,3,5-triaza-7-phosphatricyclo[3.3.1.13,7]decane-κP)silver(I) chloride dihydrate, C24H60AgClN12O6P4
  43. Crystal structure of 5-ethyl-2-(p-tolyl)-1,3-dioxane-5-carboxylic acid, C14H18O4
  44. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16ClIN2
  45. Crystal structure of catena-poly[(μ2-hexamethylenetetramine-κ2N:N′)-tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)dicopper(II)], C34H24Cu2F8N4O8
  46. Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C25H24N3O3
  47. The crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-κ2O,O′)-(diphenylcyclohexylphosphine-κP)rhodium(I), C24H25NO3PRh
  48. Crystal structure of bis((pyrazin-2-ylmethyl)(pyrazine-2-carbonyl)amido-κ3N,N′,N′′)copper(II), C20H16CuN10O2
  49. Crystal structure of catena-poly[tetraaqua-(μ2-succinonitrile-κ2N:N′)cobalt(II)] dinitrate, C4H12CoN4O10
  50. The crystal structure of 1,1′-bisisoquinoline, C18H12N2
  51. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′,O)cobalt(III) perchlorate dihydrate, C22H22ClCoN4O10
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