Home Physical Sciences Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4
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Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4

  • Jing Li , Hao-Ran Jia and Yin-Xia Sun EMAIL logo
Published/Copyright: September 29, 2017

Abstract

C26H22N2O4, triclinic P1̅, a = 8.035(3) Å, b = 10.387(4) Å, c = 13.126(5) Å, α = 83.831(10)°, β = 78.214(10)°, γ = 81.470(10)°, Z = 2, V = 1101.78(19) Å3, Rgt(F) = 0.0663, wRref(F2) = 0.1830, T = 296(2) K.

CCDC no.:: 1540632

The asymmetric unit of the title 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.

Source of material

4-Aminoacetophenone, O-benzylhydroxylamine, 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde were obtained from commercial suppliers and used as received. All other reagents and solvents were analytical grade reagents and were used without further purification. ({4-amino}phenyl)ethanoneO-benzyloxime was synthesized according to an analogous method reported previously in the literature [1]. The title compound was synthesized according to the analogous method [2], [3], [4], [5]. To an ethanol solution (4 mL) of ({4-amino}phenyl)ethanoneO-benzyloxime (240.0 mg, 1 mmol) was added an ethanol (3 mL) solution of 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde (204.18 mg, 1 mmol). The reaction mixture was stirred at 333 K for 18 h. After cooling to room temperature, the formed precipitate was filtered and washed successively with ethanol and ethanol/n-hexane (1:4), respectively. The product was dried in vacuo and purified by recrystallization from ethanol to yield 284.54 mg of a solid. Yield, 64.3%. m.p. 502–503 K. Elemental analysis − Anal. calcd for C26H22N2O4 (%): C, 73.23; H, 5.20; N, 6.57. Found: C, 75.05; H, 5.01; N, 6.78. Dark-orange block-shaped crystals were obtained after about two weeks by slow evaporation from an ethanol/acetonitrile (2:1) solution of the title compound.

Table 1

Data collection and handling.

Crystal:Block, dark-orange
Size:0.28 × 0.26 × 0.22 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
2θmax, completeness:27.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:7085, 3716, 0.047
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2503
N(param)refined:292
Programs:SHELX [19], Bruker programs [20]
Table 2

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

AtomxyzUiso*/Ueq
O11.0137(3)0.76485(19)−0.01835(15)0.0281(5)
O20.0775(3)0.6731(2)0.61349(17)0.0314(6)
H20.14450.68160.55770.047*
O30.2072(3)0.23086(19)0.52936(15)0.0263(5)
O40.2673(3)0.0300(2)0.4800(2)0.0503(7)
N10.8913(3)0.7097(2)0.06110(18)0.0234(6)
N20.3055(3)0.6047(2)0.45654(18)0.0225(6)
C11.2998(4)0.7611(3)−0.2260(2)0.0281(7)
H11.20490.7616−0.25650.034*
C21.4455(4)0.8097(3)−0.2847(2)0.0307(8)
H2A1.44760.8428−0.35360.037*
C31.5872(4)0.8082(3)−0.2394(3)0.0353(8)
H31.68520.8401−0.27800.042*
C41.5830(4)0.7592(3)−0.1366(3)0.0377(9)
H41.67840.7581−0.10640.045*
C51.4376(4)0.7118(3)−0.0787(2)0.0319(8)
H51.43610.6797−0.00960.038*
C61.2935(4)0.7115(3)−0.1220(2)0.0243(7)
C71.1371(4)0.6577(3)−0.0605(3)0.0343(8)
H7A1.08750.6118−0.10510.041*
H7B1.16760.5964−0.00410.041*
C80.7762(4)0.7980(3)0.1048(2)0.0208(7)
C90.7670(4)0.9420(3)0.0755(3)0.0316(8)
H9A0.81810.98190.12200.047*
H9B0.64930.97940.08040.047*
H9C0.82770.95700.00510.047*
C100.6507(3)0.7464(3)0.1945(2)0.0203(7)
C110.5702(4)0.8238(3)0.2758(2)0.0230(7)
H110.59110.91000.27250.028*
C120.4600(4)0.7742(3)0.3610(2)0.0240(7)
H120.40950.82680.41500.029*
C130.4235(3)0.6457(3)0.3669(2)0.0217(7)
C140.5006(4)0.5684(3)0.2849(2)0.0236(7)
H140.47680.48310.28730.028*
C150.6118(4)0.6177(3)0.2003(2)0.0248(7)
C160.2777(4)0.4843(3)0.4792(2)0.0217(7)
H160.33860.41980.43710.026*
C170.1514(4)0.4501(3)0.5706(2)0.0214(7)
H170.66200.56520.14630.030*
C180.0557(4)0.5475(3)0.6357(2)0.0261(7)
C19−0.0637(4)0.5121(3)0.7233(2)0.0320(8)
H19−0.12610.57570.76570.038*
C20−0.0899(4)0.3834(3)0.7474(2)0.0315(8)
H20−0.16800.36180.80730.038*
C21−0.0022(4)0.2827(3)0.6844(2)0.0256(7)
C220.1161(4)0.3203(3)0.5963(2)0.0233(7)
C230.1825(4)0.0998(3)0.5444(3)0.0328(8)
C240.0611(4)0.0616(3)0.6361(3)0.0378(8)
H240.0432−0.02560.64850.045*
C25−0.0269(4)0.1467(3)0.7041(2)0.0327(8)
C26−0.1493(4)0.1023(4)0.8005(3)0.0430(9)
H26A−0.14230.00890.80590.065*
H26B−0.26410.14030.79580.065*
H26C−0.11910.12970.86120.065*

Experimental details

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

Discussion

Schiff base as an important class of organic compounds have received long-lasting attention [6], [7], [8], [9], especially synthesis and structures of new derivatives [10], [11], [12], [13]. Because these compounds can be applied in many fields including analytical, biological, inorganic chemistry and material science [14], [15], [16], [17], [18]. In this paper, we report on the synthesis and crystal structure of a new compound containing double functional oxime and Schiff Base group.

One intramolecular O2—H2⋯N2 hydrogen bond between the hydroxyl group and the O atom of carbonyl group forms a six-membered ring in each molecule. In addition, the molecules of the title compound are linked into an infinite 2D-layer structure via C1—H1⋯O2, C12—H12⋯O4, C14—H14⋯πcentroid(C1–C6) and C26—H26B⋯πcentroid(C10–C15) hydrogen bond interactions. This linkage is further stabilized by the ππ stacking interactions (πcentroid(O3,C21–C25)πcentroid(C10–C15), πcentroid(C10–C15)πcentroid(C17–C22), πcentroid(C10–C15)πcentroid(O3,C20–C25)) of molecules with the centroid-centroid in the rage: 3.621(2)–3.919(2) Å to form a 3D networks structure.

Acknowledgement

The supports by Program for Excellent Team of Scientific Research in Lanzhou Jiaotong University (201706) are gratefully acknowledged.

References

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Received: 2017-5-23
Accepted: 2017-9-13
Published Online: 2017-9-29
Published in Print: 2017-11-27

©2017 Jing 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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  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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