Startseite Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3
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Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3

  • Peng-Peng Li , Li Zhao EMAIL logo , Ji-Xing Zhao und Zhao-Bin Zhu
Veröffentlicht/Copyright: 8. November 2017

Abstract

C20H27ClN3O3, monoclinic, P21/n (no. 14), a = 10.7351(5) Å, b = 14.1177(6) Å, c = 14.3355(9) Å, β = 101.284(6)°, Z = 4, V = 2130.6(2) Å3, Rgt(F) = 0.0569, wRref(F2) = 0.1767, T = 293(2) K.

CCDC no.:: 1580214

The crystal structure is shown in the figure. 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:Block, clear dark brown
Size:0.33 × 0.31 × 0.25 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:1.78 mm−1
Diffractometer, scan mode:SuperNova, ω-scans
2θmax, completeness:140°, >98%
N(hkl)measured, N(hkl)unique, Rint:7644, 3951, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2891
N(param)refined:252
Programs:CrysAlisPRO [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.04073(8)0.56350(6)0.35325(7)0.0748(3)
O10.62367(18)0.44948(12)0.38662(16)0.0604(5)
H10.70110.45150.40410.091*
O20.0710(2)−0.10444(13)0.39017(18)0.0699(6)
O30.1365(2)0.57609(18)0.57179(19)0.0786(7)
H3D0.09890.53120.59450.118*
H3E0.11610.57530.51140.118*
N10.6623(2)0.78435(16)0.35311(19)0.0603(6)
N20.3907(2)0.38164(16)0.37570(17)0.0573(6)
N30.1475(2)−0.02397(16)0.38696(18)0.0592(6)
C10.8191(3)0.7542(3)0.2518(3)0.0835(10)
H1A0.77230.79740.20630.125*
H1B0.79070.69070.23590.125*
H1C0.90800.75900.25080.125*
C20.7974(3)0.7783(2)0.3494(2)0.0647(8)
H2A0.83710.73040.39400.078*
H2B0.83770.83850.36900.078*
C30.5945(4)0.9403(3)0.4044(3)0.0958(12)
H3A0.55720.99960.38090.144*
H3B0.67850.95110.44050.144*
H3C0.54320.91130.44440.144*
C40.6014(3)0.8765(2)0.3228(2)0.0701(8)
H4A0.51620.86520.28720.084*
H4B0.64910.90780.28070.084*
C50.5950(3)0.70720(18)0.36773(19)0.0514(6)
C60.6496(2)0.61642(18)0.37737(18)0.0492(6)
H60.73660.60970.38060.059*
C70.5764(3)0.53758(18)0.38213(18)0.0478(6)
C80.4428(2)0.54649(19)0.37986(18)0.0508(6)
C90.3922(3)0.6381(2)0.3770(2)0.0573(7)
H90.30670.64560.37870.069*
C100.4636(3)0.7161(2)0.3717(2)0.0602(7)
H100.42700.77590.37060.072*
C110.3592(3)0.47031(19)0.37759(19)0.0550(7)
H110.27440.48420.37740.066*
C120.3066(3)0.30248(19)0.37401(19)0.0536(6)
C130.3533(3)0.2146(2)0.3554(2)0.0626(7)
H130.43500.20920.34330.075*
C140.2790(3)0.13541(19)0.3548(2)0.0586(7)
H140.31120.07700.34130.070*
C150.1570(3)0.13982(17)0.37389(18)0.0490(6)
C160.1107(3)0.22865(19)0.3903(2)0.0554(6)
H160.02850.23430.40140.066*
C170.1853(3)0.30998(19)0.3906(2)0.0577(7)
H170.15280.36900.40200.069*
C180.0822(3)0.05213(17)0.37743(18)0.0487(6)
C19−0.0578(3)0.0549(2)0.3710(2)0.0637(8)
H19A−0.07660.04720.43340.096*
H19B−0.09670.00460.33050.096*
H19C−0.09030.11470.34510.096*
C200.1505(4)−0.1849(2)0.4051(3)0.0894(12)
H20A0.1984−0.18910.35520.134*
H20B0.0995−0.24080.40470.134*
H20C0.2077−0.17950.46530.134*

Source of material

4-Aminoacetophenone methoxy oxime was prepared by a similar method reported earlier [4]. 4-Aminoacetophenone methoxy oxime (148.2 mg, 1 mmol) dissolved in ethanol solution (5 mL) was added to 4-(diethylamino)salicylaldehyde (200.0 mg, 1 mmol) dissolved in ethanol solution (5 mL). After the solution had been stirred at 330 K for 12 h, cooling to room temperature, the precipitate was filtered and washed with ethanol and hexane. The product was dried under vacuum and obtained red solid (yield 70.2%, m.p. 447−450 K). The single crystals were obtained by slow evaporation from a mixture of dichloromethane and ethanol and HCl (100:50:1) solution at room temperature. Elemental analysis: Anal. calcd. for C20H27ClN3O3: C, 61.14%; H, 6.93%; N, 10.69%; Found: C, 61.17%; H, 6.95%; N, 10.66%.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Discussion

As we know, many interesting oxime-type compounds have been reported over the past decade, the researches of application fields remains a challenge [5]. Recently particular attention has been paid to the synthesis and application fields of oxime-type compounds and their complexes [6, 7] . So far, oxime-type compounds and their complexes have been used in many fields, such as: materials [8], [9], [10], [11] and supramolecular architectures [12], [13], [14], [15] etc. The current work reports the synthesis of the title compound, which is built up by the C20H27ClN3O3 molecules (cf. the figure).

And all bond lengths are in normal ranges [4]. In the title compound, there are weak non-classical intermolecular C—H⋯Cl and C—H⋯O hydrogen bonds.

Acknowledgements

This work was supported by the Science Foundation of Gansu Education Department of China (2017A-023).

References

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Received: 2017-6-25
Accepted: 2017-10-16
Published Online: 2017-11-8
Published in Print: 2018-1-26

©2018 Peng-Peng Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial 2018
  3. Crystal structure of dimethanol-bis{3-(((2-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N:O′}dizinc(II), C42H30Zn2N2O10
  4. Crystal structure of aqua-bis{[2,6-dimethyl-N-(pyridin-2-ylmethylene)aniline-κ2N,N′]}zinc(II) triflate monohydrate [ZnC29H31N4O]CF3SO3⋅H2O
  5. Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3
  6. Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2
  7. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4,4′-sulfonyldibenzoato-κ2O:O′)zinc(II)], C40H34N4O6SZn
  8. Crystal structure of catena-poly[diaqua(μ3-pyrazine-2,3-dicarboxylato-κ4O,N:O′:O′′)zinc(II)] 1.25 hydrate, C6H8.5N2O7.25Zn
  9. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri-m-tolyl phosphane-κP)rhenium(I), C29H28O5PRe
  10. Crystal structure of bis(μ2-methanolato-κ2O:O)-bis(methanol-κ1O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,O′,N}dichromium(III), C38H36Cr2N2O14
  11. Crystal structure of poly[aqua-(μ3-pyridine-3,5-dicarboxylato-κ5O,O′:O′′,O′′′,N)zinc(II)], C7H7NO6Zn
  12. Crystal structure of bis((1-(((4-(((benzyloxy)imino)methyl)phenyl)imino)methyl)naphthalen-2-yl)oxy-κ2O,N)copper(II), C52H42CuN4O4
  13. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}cobalt(II), C40H38CoN4O6
  14. Crystal structure of diaqua-bis(N,N-dimethylformamide-κ1O)-bis{3-((5-chloro-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ4N,O,O′:O′}dinickel(II), C38H34Ni2Cl2N4O12
  15. Crystal structure of tetrakis(methanol-κO)bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}bicobalt(II), C38H38Co2N2O14
  16. Crystal structure of (S)-tert-butyl-(1-hydroxypropan-2-yl)carbamate, C8H17NO3
  17. Crystal structure of 4-(4′-(pyridin-4-yl)-[1,1′-biphenyl]-4-yl)pyridin-1-ium catena-poly[{5-carboxy-4′-methyl-[1,1′-biphenyl]-3-carboxylato-κ2O,O′}-(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-κ4O,O′:O′′,O′′′)lead(II)], C52H40N2O9Pb
  18. Crystal structure of catena-poly[diaqua-(μ2-5-methylisophthalato-κ2O:O′)(μ2-1,4-bis((1H-1,2,4-triazol-1-yl)methyl)benzene-κ2N:N′)], NiC21H22O6N6
  19. Crystal structure of the salt tris(guanidinium) tris(tetrapropylammonium) bis(pyridine-2,4,6-tricarboxylate) – water (1/10), C55H126N14O22
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  21. Crystal structure of poly{[μ2-1,1′-(sulfonylbis(4,1-phenylene))bis(2-methyl-1H-imidazole)-κ2N:N′][μ2-4,4′-oxydibenzoato-κ2O:O′]cobalt(II)} hemihydrate, C34H27N4O7.5SCo
  22. The crystal structure of 25,27-(2,2′-[(2-thioxo-1,3-dithiole-4,5-diyl)disulfanediyl]diethanolate)-26,28-dihydroxycalix[4]arene — dichloromethane (1/1), C36H32Cl2O4S5
  23. The crystal structure of 1,2-bis(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)ethane, C16H12N6O2
  24. Crystal structure of 1-benzyl-3-((4-bromophenyl)amino)-4-(4-methoxyphenyl)-1H-pyrrole-2,5-dione, C24H19BrN2O3
  25. Crystal structure of bis(2-((allylcarbamothioyl)imino)-4-methylthiazol-3-ido-κ2N,S)palladium(II), C16H20N6PdS4
  26. Crystal structure of pyrimidine-2,5-dicarboxylic acid 1.5 hydrate, C12H14N4O11
  27. Crystal structure of trans-diaqua-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II), C8H10N4O6Mn
  28. Crystal structure of catena-(μ3-5-bromoisophthatato-κO,O′: O′′,O′′′′)-(1,2-bis(imidazol-1-yl)ethane-κN:N′)cobalt(II), C16H13CoN4O4Br
  29. Investigation of the compound La5Zn2−xPb1 + x (x = 0.20–0.32)
  30. Crystal structure of (OC-6-13)-diaqua-bis(3,5-di(pyridin-3-yl)-4H-1,2,4-triazol-4-amine-κ1N)-bis(dicyanamido-κ1N)zinc(II) tetrahydrate, ZnC28H32N18O6
  31. Crystal structure of Ga0.62(3)Sb0.38(3)Pd3
  32. Crystal structure of Ga0.47(1)Sb0.53(1)Pd2
  33. A derivative of the Corey lactone – crystal structure of (3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate, C21H30O5Si
  34. A Corey lactone: crystal structure of (3aR,4R,5R,6aS)-5-benzoyloxy-4(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one, C15H16O5
  35. Hydrothermal synthesis and crystal structure of poly[aqua-(μ2-1,3-bis(4-pyridyl)propane-κ2N:N′)-(μ2-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylato-κ2O:O′)manganese(II) hydrate, C22H20Cl6N2O6Mn
  36. Crystal structure of 2-acetylpyrrole S-methylthiosemicarbazonium hydroiodide, C8H13IN4S
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  38. Crystal structure of poly[aqua-(μ5-2,5-dicarboxybenzoato-κ5O:O:O′:O′′:O′′′)sodium(I)], C9H7NaO7
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  48. Crystal structure of 4-chloro-2-methyl-6-(4-(trifluoromethoxy)phenyl)pyrimidine, C12H8ClF3N2O
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  50. Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2
  51. Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2
  52. The crystal structure of (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid, C16H15N3O2S
  53. Crystal structure of 2-chloro-1,3-di-tert-pentyl-4,4-diphenyl-1,3,2λ3,4-diazaphosphasiletidine, C22H32ClN2PSi
  54. Crystal structure of tetramethyl 5,5′-(buta-1,3-diyne-1,4-diyl)diisophthalate, C24H18O8
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  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
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  58. Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
  59. The crystal structure of (E)-N-benzyl-N′-benzylidene-4-methylbenzenesulfonohydrazide, C21H20N2O2S
  60. Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6
  61. The crystal structure of (E)-4-(3-ethoxy-2-hydroxybenzylideneamino)benzoic acid, C16H15NO4
  62. Crystal structure of (μ2-N,N′-bis((pyridin-4-yl)methyl)ethanediamide-κ2N:N′)-tetrakis(diethylcarbamodithioato-κ2S,S′)dizinc(II), C34H54N8O2S8Zn2
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