Startseite Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2
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Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2

  • Peng-Peng Li , Li Zhao EMAIL logo , Ji-Xing Zhao und Zhao-Bin Zhu
Veröffentlicht/Copyright: 15. November 2017
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 233 Heft 1

Abstract

C19H23N3O2, monoclinic, P21/n (no. 14), a = 17.8421(15) Å, b = 9.4778(9) Å, c = 22.116(2) Å, β = 108.230(10)°, Z = 8, V = 3552.2(6) Å3, Rgt(F) = 0.0649, wRref(F2) = 0.1506, T = 293(2) K.

CCDC no.: 1581469

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 light yellow
Size:0.33 × 0.31 × 0.23 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.64 mm−1
Diffractometer, scan mode:SuperNova, ω-scans
θmax, completeness:70.2°, >96.9%
N(hkl)measured, N(hkl)unique, Rint:12972, 6558, 0.039
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3553
N(param)refined:446
Programs:CrysAlisPRO [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.71151(12)0.7864(2)0.09344(11)0.0542(6)
O21.20727(12)0.6934(3)0.47063(11)0.0679(7)
H2A1.20820.69370.50790.102*
O31.30637(13)1.3894(3)0.35409(16)0.0837(9)
H31.25991.37010.33630.126*
O40.74617(12)1.0546(3)0.12949(14)0.0725(8)
H4A0.73150.97630.11480.109*
N10.44416(14)0.6325(3)0.03029(13)0.0538(7)
N20.80871(14)0.6938(3)0.20193(12)0.0505(7)
N31.12874(14)0.6869(3)0.43078(12)0.0548(7)
N41.55787(16)1.1725(4)0.43286(18)0.0855(11)
N51.18722(14)1.2407(3)0.28582(13)0.0543(7)
N60.82973(14)1.0574(3)0.15334(14)0.0568(7)
C10.65467(17)0.7138(3)0.10506(14)0.0448(7)
C20.57813(16)0.7164(3)0.06382(14)0.0458(7)
H20.56620.77620.02880.055*
C30.51790(17)0.6323(3)0.07285(15)0.0473(7)
C40.5366(2)0.5447(4)0.12805(17)0.0591(9)
H40.49790.48720.13510.071*
C50.6100(2)0.5451(4)0.16996(17)0.0597(9)
H50.62030.48820.20590.072*
C60.67203(17)0.6276(3)0.16204(14)0.0468(7)
C70.74625(18)0.6233(4)0.20672(15)0.0540(8)
H70.75300.56730.24260.065*
C80.88589(17)0.6895(3)0.24576(14)0.0479(8)
C90.94488(19)0.7528(4)0.22766(15)0.0585(9)
H90.93280.79720.18830.070*
C101.02227(19)0.7511(4)0.26779(16)0.0614(10)
H101.06160.79240.25440.074*
C111.04201(17)0.6889(4)0.32751(14)0.0492(8)
C120.98163(18)0.6258(4)0.34457(15)0.0538(8)
H120.99360.58200.38410.065*
C130.90410(18)0.6253(4)0.30518(15)0.0543(8)
H130.86480.58270.31820.065*
C141.12358(18)0.6920(4)0.37199(15)0.0534(8)
C151.1930(2)0.7038(5)0.34810(18)0.0869(14)
H15A1.17790.67450.30440.130*
H15B1.23480.64440.37310.130*
H15C1.21070.79990.35150.130*
C160.42241(19)0.7318(4)−0.02271(17)0.0655(10)
H16A0.37490.6981−0.05450.079*
H16B0.46420.7341−0.04210.079*
C170.4083(2)0.8782(4)−0.0039(2)0.0946(15)
H17A0.39670.9389−0.04040.142*
H17B0.45460.91180.02830.142*
H17C0.36450.87810.01260.142*
C180.3819(2)0.5382(4)0.03603(19)0.0713(11)
H18A0.40540.44940.05410.086*
H18B0.34600.5189−0.00620.086*
C190.3360(3)0.5959(6)0.0761(2)0.120(2)
H19A0.31260.68420.05870.179*
H19B0.37060.61040.11860.179*
H19C0.29530.53050.07680.179*
C201.35082(18)1.2724(4)0.35771(17)0.0569(9)
C211.42974(18)1.2807(4)0.39314(17)0.0601(9)
H211.45011.36460.41350.072*
C221.47921(18)1.1636(4)0.39849(17)0.0614(10)
C231.44664(19)1.0394(4)0.36634(18)0.0670(10)
H231.47840.96060.36840.080*
C241.36802(19)1.0338(4)0.33186(17)0.0642(10)
H241.34760.94990.31160.077*
C251.31757(17)1.1487(4)0.32605(15)0.0485(8)
C261.23508(17)1.1368(4)0.29151(15)0.0523(8)
H261.21571.05100.27260.063*
C271.10501(17)1.2233(3)0.25418(16)0.0503(8)
C281.05433(18)1.3096(4)0.27315(18)0.0627(10)
H281.07461.37720.30450.075*
C290.97340(19)1.2964(4)0.24577(18)0.0623(10)
H290.94011.35530.25920.075*
C300.94111(17)1.1975(4)0.19888(17)0.0526(8)
C310.99234(18)1.1154(4)0.17833(17)0.0636(10)
H310.97211.05060.14580.076*
C321.07367(18)1.1279(4)0.20539(17)0.0617(9)
H321.10711.07200.19070.074*
C330.85469(18)1.1811(4)0.17210(17)0.0544(8)
C340.8015(2)1.3053(4)0.1698(2)0.0809(13)
H34A0.75741.30110.13150.121*
H34B0.83031.39110.17030.121*
H34C0.78301.30300.20610.121*
C351.5932(2)1.2996(6)0.4682(2)0.1011(16)
H35A1.64961.29760.47530.121*
H35B1.57211.38170.44230.121*
C361.5795(3)1.3152(6)0.5290(3)0.132(2)
H36A1.52391.32170.52240.199*
H36B1.60511.39930.54960.199*
H36C1.60061.23490.55520.199*
C371.6135(2)1.0547(5)0.4317(2)0.0997(14)
H37A1.59811.01200.38970.120*
H37B1.66651.09190.44050.120*
C381.6127(3)0.9501(6)0.4783(3)0.140(2)
H38A1.56080.90990.46820.209*
H38B1.62660.99310.51960.209*
H38C1.65010.87720.47830.209*
H10.748(5)0.749(3)0.125(3)0.48(7)*

Source of material

All chemicals used were of the analytical reagent grade available. 4-Amino acetophenone oxime was prepared by a similar method reported earlier [4]. To an ethanol solution (5 mL) of 4-amino acetophenone oxime (164.0 mg, 1 mmol) was added an ethanol solution (5 mL) of 4–(diethylamino)salicylaldehyde (200.0 mg, 1 mmol). After the solution had been stirred at 330 K for 12 h, the mixture was filtered, washed successively with dichloromethane and ethanol/hexane (1:4), respectively. The isolated compound was dried under reduced pressure and purified with recrystallization from ethanol to obtained yellow crystalline solid (yield 65.7%, m.p. 432–435 K). The single crystals were obtained by slow evaporation from a mixture of ethanol and dichloromethane (1:2) at room temperature. Elemental analysis – Anal. calcd. for C19H23N3O2: C, 70.13%; H, 7.12%; N, 12.91%; Found: C, 70.15%; H, 7.14%; N, 12.87%.

Experimental details

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

Discussion

Oxime-type compounds are considered a very important class of organic ligands possessing diverse applications. Recently particular attention has been paid to the synthesis [5], [6], [7]. The application of oxime-type compounds and their complexes, for instance: they have been used to identify metal ions [8, 9] , have fascinating magnetic properties [10], many other fields of materials sciences [11], [12], [13], [14], [15], [16], [17] materials.

All bond lengths are in normal ranges [18]. The asymmetric unit of the title structure contains two crystallographically independent but chemically identical molecules (cf. the figure). In the molecules, there are strong intramolecular O—H⋯N hydrogen bonds (O1—H1⋯N2: d(O1⋯N2) = 2.633 Å; O3—H3⋯N5: d(O3⋯N5) = 2.603(3) Å). In addition, the structure of the title compound formed a chain structure via strong intermolecular O2—H2A⋯O1, O4—H4A⋯O1, 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: 2017-7-12
Accepted: 2017-10-23
Published Online: 2017-11-15
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
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  49. Crystal structure of 1-(4-fluorophenyl)-N-(5-((triphenylstannyl)thio)thiophen-2-yl)methanimine, C27H20FN3S2Sn
  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
  55. Crystal structural of 2-amino-4-(4-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C19H20N2O3
  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
  57. The crystal structure of bis(2-benzoyl-5-hydroxylphenolato-κ2O,O′)copper(II), C26H18CuO6
  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
https://doi.org/10.1515/ncrs-2017-0071
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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
  20. Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8
  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
  37. Crystal structure of [N,N-bis((pyrrol-2-yl)ethylidene)butane-1,4-diamine-κ4N,N′,N′′,N′′′]-nickel(II), C16H20N4Ni
  38. Crystal structure of poly[aqua-(μ5-2,5-dicarboxybenzoato-κ5O:O:O′:O′′:O′′′)sodium(I)], C9H7NaO7
  39. Crystal structure of bis(N′-((1H-pyrrol-2-yl)methylene)-1-methylthio-methanethiohydrazido-κ2S,N)nickel(II), C14H16N6NiS4
  40. Crystal structure of 1-(4-((benzo[d][1,3]dioxol-5-yloxy)methyl)phenethyl)-4-(3-chlorophenyl) piperazin-1-ium chloride, C26H28Cl2N2O3
  41. Crystal structure of 2-(4-(2-(4-(2-fluorophenyl)piperazin-1-yl)ethyl)benzyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide, C26H26FN3O3S – a saccharin dervative
  42. Crystal structure of 3-(2-dimethylaminoethyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C12H15N3OS
  43. Crystal structure of 3-(3-dimethylaminopropyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C13H17N3OS
  44. The crystal structure of trans-tetraaqua-bis(p-tolylsulfinato-κO)calcium(II)), C14H22O8S2Ca
  45. The crystal structure of (E)-N′-(pyridin-2-ylmethylene)pyrazine-2-carbohydrazide, C11H9N5O
  46. Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO
  47. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)cobalt(II)], C4H8CoO8
  48. Crystal structure of 4-chloro-2-methyl-6-(4-(trifluoromethoxy)phenyl)pyrimidine, C12H8ClF3N2O
  49. Crystal structure of 1-(4-fluorophenyl)-N-(5-((triphenylstannyl)thio)thiophen-2-yl)methanimine, C27H20FN3S2Sn
  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
  55. Crystal structural of 2-amino-4-(4-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C19H20N2O3
  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
  57. The crystal structure of bis(2-benzoyl-5-hydroxylphenolato-κ2O,O′)copper(II), C26H18CuO6
  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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