Home Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2
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Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2

  • Peng-Peng Li , Li Zhao EMAIL logo , Guo-Hua Liu , Ji-Xing Zhao and Zhao-Bin Zhu
Published/Copyright: October 16, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 6

Abstract

C15H14N2O2, monoclinic, P21/c (no. 14), a = 13.5809(12) Å, b = 9.7794(14) Å, c = 9.8883(9) Å, β = 97.972(9)°, Z = 4, V = 1300.6(3) Å3, Rgt(F) = 0.0635, wRref(F2) = 0.1758, T = 291(2) K.

CCDC no.:: 1577291

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 orange
Size:0.21 × 0.17 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:SuperNova, ω-scans
2θmax, completeness:52°, >99%
N(hkl)measured, N(hkl)unique, Rint:4966, 2551, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1248
N(param)refined:178
Programs:CrysAlisPRO [1], SHELX [2], OLEX2 [3]
Table 2

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

AtomxyzUiso*/Ueq
O1−0.60627(16)0.0413(3)0.0040(2)0.0615(7)
H1−0.562(2)0.052(4)0.082(3)0.081(12)*
O20.00342(14)0.0658(3)0.6523(2)0.0658(7)
H20.04860.03700.61300.099*
N1−0.52562(17)0.0860(3)0.2524(2)0.0502(7)
N2−0.08717(18)0.0587(3)0.5634(2)0.0543(7)
C1−0.6937(2)0.0739(3)0.0458(3)0.0478(8)
C2−0.7794(2)0.0669(4)−0.0466(3)0.0599(10)
H2A−0.77600.0392−0.13580.072*
C3−0.8700(2)0.1003(4)−0.0082(3)0.0681(11)
H3−0.92730.0940−0.07140.082*
C4−0.8769(2)0.1432(4)0.1233(4)0.0680(10)
H4−0.93810.16630.14880.082*
C5−0.7913(2)0.1512(3)0.2163(3)0.0574(9)
H5−0.79550.18080.30480.069*
C6−0.6988(2)0.1160(3)0.1807(3)0.0466(8)
C7−0.6110(2)0.1218(3)0.2818(3)0.0505(8)
H7−0.61660.15190.36960.061*
C8−0.4381(2)0.0941(3)0.3487(3)0.0466(8)
C9−0.3655(2)−0.0028(3)0.3420(3)0.0522(9)
H9−0.3766−0.07320.27850.063*
C10−0.2764(2)0.0031(3)0.4280(3)0.0497(8)
H10−0.2290−0.06480.42370.060*
C11−0.2565(2)0.1109(3)0.5223(3)0.0451(8)
C12−0.3308(2)0.2057(4)0.5288(3)0.0592(9)
H12−0.32050.27600.59250.071*
C13−0.4200(2)0.1990(4)0.4433(3)0.0601(9)
H13−0.46830.26520.44910.072*
C14−0.1591(2)0.1206(3)0.6089(3)0.0489(8)
C15−0.1479(2)0.1989(4)0.7415(3)0.0672(10)
H15A−0.09120.16520.80090.101*
H15B−0.20660.18720.78430.101*
H15C−0.13880.29420.72350.101*

Source of material

The title compound was prepared by modification of the reported method [4], [5], [6]. The solution of salicylaldehyde (122 mg, 1 mmol) in ethanol (10 mL) was slowly added to the solution of 4-amino-acetophenone oxime (150.17 mg, 1 mmol) in ethanol (10 mL). The solution had been stirred at 328 K for 9h. The mixture was cooled down to room temperature and filtered. The residue was washed successively with ethanol and n-hexane, respectively. The product was dried under vacuum and obtained orange solid (yield 76.5%, m.p. 413–415 K). The single crystals were obtained by slow evaporation from a mixture of chloroform/ethanol (2:1) solution at room temperature. Elemental analysis − Anal. Calcd. for C15H14N2O2: C, 70.85%; H, 5.55%; N, 11.02%; Found: C, 70.87%; H, 5.57%; N, 10.98%.

Experimental details

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

Discussion

The term “oxime” is formed by the combination of the words oxy and imine, and oximes are amphoteric compounds: weak acid due to hydroxyl group (OH) and weak base due to the azomethine group (C=N) [7], [8], [9]. Oxime-type compounds can form stable complexes with transition metal ions [10], [11], [12]. Particular attention has been paid to the synthesis and application of oxime-type compounds and their complexes. For example: it has been used in the chemistry of materials [13], [14], [15], [16], and also been used to supramolecular architectures [17], [18], [19] etc.

The title compound, built up by the C15H14N2O2 molecules, has been synthesized. The single crystal structure verifies that all bond lengths are in normal ranges. In the title compound, there is a strong intramolecular O1—H1⋯N1 hydrogen bond [d(N1⋯H1) = 1.721 Å, d(O1—H1) = 0.92(3) Å, d(O1⋯N1) = 2.584 Å]; cf. the figure.

Acknowledgement

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

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Received: 2017-5-1
Accepted: 2017-9-29
Published Online: 2017-10-16
Published in Print: 2017-11-27

©2017 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.

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  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
https://doi.org/10.1515/ncrs-2017-0134
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of potassium 1-methyl-1H-1,2,3,4-tetrazole-5-thiolate, C2H3N4SK
  3. Crystal structure of bis(3-(3-ethylureido)-N,N-dimethylpropan-1-aminium) bis (μ3-2-(hydroxymethyl)-2-(oxidomethyl)propane-1,3-bis(olato))-(μ6-oxo)-hexakis(μ2-oxo)-hexaoxo-hexavanadium(V) – dichloromethane (1/1), C27H60Cl2N6O23V6
  4. Crystal structure of bis(μ3-methanolato-κ3O:O:O)-bis(μ2-methanolato-κ2O:O)-dimethanol-bis{6,6′-(1,3-dihydroxyl-2-acetylpropane-1,3-diyl)bis(2-chloro-4-bromophenolato)}tetramanganese(III) C40H40Br4Cl4Mn4O16
  5. Synthesis and crystal structure of tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dibromo-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5)tetramanganese(III), C40H40Br8Mn4O16
  6. Synthesis and crystal structure tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dichloro-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5), tetramanganese(III), C40H40Cl8Mn4O16
  7. Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O)}copper(II), C34H34CuN4O6
  8. Crystal structure of (E)-1-(2-hydroxy-3-{[2-hydroxybenzylidene]amino}phenyl)ethan-1-one, C15H13NO3
  9. Crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′′:O′′}tricobalt(II), C44H49Cl2Co3N6O12
  10. Crystal structure of bis{μ2-2,4-dichloro-6-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ5O:O,N,N′,O′}dicobalt(II) acetone solvate, C43H48Br4Co2N6O9
  11. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3
  12. Crystal structure of bis{5-(N,N′-diethylamine)-5′-methoxy -2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato}-bis(μ2-acetato-κ2O:O′)trizinc(II), C46H56Zn3N6O14
  13. Crystal structure of tris(cyano-(hydrogen tris(3,5-dimethylpyrazolyl)borate))-iron(III) 4-methoxypyridinium monohydrate, C24H32BN10O2Fe
  14. Synthesis and crystal structure of bis{1-(((4-(1-(hydroxyimino)ethyl)phenyl)imino)methyl)naphthalen-2-olato-κ2O,N}copper(II), C38H30CuN4O4
  15. Crystal structure of (E)-1-(4-{[(E)-2-Hydroxy-1-naphthalenylmethylene] amino}phenyl)ethanone oxime, C19H16N2O2
  16. The pseudosymmetric crystal structure of 2-(2-naphthalenyl)-3-nitro-2H-1-benzopyran, C38H26N2O6
  17. Crystal structure of 2-benzoyl-3-(4-methoxyphenyl)cyclopropane-1,1-dicarbonitrile, C19H14N2O2
  18. N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C17H21N3O5
  19. The crystal structure of carbonyl-[4-(2,4-dichlorophenylamino)pent-3-en-2-onato-κ2N,O]-(triphenylphosphine-κP)rhodium(I), RhC30H25Cl2NO2P
  20. Crystal structure of (E)-5-(diethylamino)-2-(((1,1,2-trihydroxyethyl)iminio)methyl)phenolate, C15H24N2O4
  21. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)(μ2-isophthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C34H30N4O4Cd
  22. Crystal structure of 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]chinolizinium 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate - methanol - water (1/1/1), C36H33NO10
  23. A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3
  24. Crystal structure of the salt 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) diperchlorate, C14H28N4(ClO4)2
  25. Crystal structure of 2,5-bis((E)-2-(trifluoromethyl)benzylidene)cyclopentan-1-one, C21H14F6O
  26. Crystal structure of catena-poly[(μ2-benzene-1,4-dicarboxylato-κ2O:O′)-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)zinc(II)] 1.25 hydrate, C25H26.5N3O8.25FZn
  27. Crystal structure of 1-methyl-1,4-diazabicyclo[2.2.2]octan-1-ium poly[aqua-bis(μ2-perchlorato-κ3O,O′:O′′)sodium], C7H17Cl2N2NaO9
  28. Crystal structure of trimethyammonium 2,6-dicarboxyisonicotinate monohydrate, C11H16N2O7
  29. Crystal structure of dodecaguanidinium bis(tetrapropylammonium) heptacarbonate, C43H128N38O21
  30. Crystal structure of poly[tetraaqua-bis(μ6-benzene-1,2,4,5-tetracarboxylato)nickel(II)diyttrium(III)]dihydrate, C20H16NiO22Y2
  31. Halogen bonds and π–π interactions in the crystal structure of 1,3,5-trifluoro-2,4,6-triiodobenzene–N,N-dimethylformamide (1/1), C9H7F3I3NO
  32. Crystal structure of guanidinium tetraethylammonium carbonate dihydrate, C10H30N4O5
  33. The crystal structure of oxonium chlorido-ethylenediaminetetraactetotin(IV) hydrate, C10H17ClN2O10Sn
  34. Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4
  35. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}copper(II), C40H38CuN4O6
  36. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri(p-tolyl)phosphine-κP)rhenium(I), C29H28O5PRe
  37. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(benzyldiphenylphosphine-κP)rhenium(I), C27H24O5PRe
  38. Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8
  39. Crystal structure of bis(N,N,N-ethyldimethylethanaminium) bis(heptaselenido-κ2Se1,Se7)palladate(II), C12H32N2PdSe14
  40. Crystal structure of bis(4-(1H-pyrazol-5-yl)pyridine-κ2N:N′)-bis(2-(2-((2,6-difluorophenyl)amino)phenyl)acetate-κO)cadmium(II), C44H34N8CdCl4O4
  41. Crystal structure of 4,4′-(1,4-phenylene)bis(pyridin-1-ium) catena-poly[diaqua-bis(μ2-3′,5′-dicarboxy-[1,1′-biphenyl]-2,5-dicarboxylato-κ2O:O′] dihydrate, C48H42O22N2Ca
  42. The crystal structure of (S)-2-benzylsuccinic acid, C11H12O4
  43. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)yttrium(III)], C26H17N2O9Y
  44. Crystal structure of ethyl 1-(3,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate, C14H17N3O2
  45. Crystal structure of tetrakis(methanol-κO)-bis{μ2-3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olate-κ4O,N;O′:O′}dizinc(II), C38H38Zn2N2O14
  46. Crystal structure of bromido(4,4′-dimethoxy-2,2′-bipyridine-κ2N,N′)(isopropyl(diphenyl)phosphane-κP)copper(I), C27H29BrCuN2O2P
  47. Crystal structure of bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene, C41H64B2O4
  48. Crystal structure of 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde - a julolidine derivative, C16H15NO3
  49. Crystal structure of 1,3-dimethyl-5,5-dibenzylbarbituric acid, C20H20N2O3
  50. Crystal structure of bis(N,N,N-trimethylethanaminium) poly[bis(μ2-heptaselenido-κ2Se1,Se7)palladate(II)], C10H28N2PdSe14
  51. Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl} ethanone O-ethyl-oxime, C17H17ClN2O2
  52. The crystal structure of methyl N-(4-bromophenyl)carbamate, C8H8BrNO2
  53. Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2
  54. Crystal structure of 1,1′-butanebis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C12H20F12N4P2
  55. (E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S
  56. Crystal structure of ethyl 5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate, C11H12N4O2
  57. Crystal structure of 5,5-difluoro-10-(4-fluorophenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine - a Z′ = 3 structure, C19H18B2F3N2
  58. The crystal structure of the Matrine derivative: 12-(1H-indol-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one hydrate, C23H29N3O
  59. The crystal structure of tris(μ2-1,3-bis(4,4,4-trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-κ2O,O′)dilutetium(III), C50H38F18Lu2O16
  60. The crystal structure of (Z)-2-(3-(2-(4-chlorobenzoyl)hydrazono)-2-oxoindolin-1-yl) acetic acid, C17H12ClN3O4
  61. Synthesis and crystal structure of trans-tetraqua-bis(2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetato-κO)cobalt(II) hexahydrate, C36H48CoN2O28S2
  62. The crystal structure of N,N-dimethyl-2,6-di-p-tolylpyrimidin-4-amine, C20H21N3
  63. The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S
  64. Crystal structure of catena-poly[(μ2-1,3-bis(benzimidazol-1-yl)propane κ2N:N′)-(μ2-5-methoxyisophthalato-κ2O:O′)zinc(II)] hydrate, C26H24ZnN4O6
  65. The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3
  66. Crystal structure of 2,8-diphenyl-3,7,9-trioxa-1-azaspiro[4.5]dec-1-ene, C18H17N1O3
  67. Crystal structure of diethyl 2-(4-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19ClO6
  68. Crystal structure of 1-(carboxymethyl)-1H-benzo[d][1,2,3]triazole 3-oxide, C8H7N3O3
  69. Crystal structure of (acetylacetonato-κ2O,O′)-(2-amino-6-chlorobenzoato-κO)-oxido(1,10-phenanthroline-κ2N,N′)vanadium(IV) – trichloromethane (1/1)
  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
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