Home Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
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Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2

  • Tao Fu , Jin-Xia Ma , Qing-Lin Li , Ping Wei , Ji-Xing Zhao and Li Zhao ORCID logo EMAIL logo
Published/Copyright: December 20, 2019

Abstract

C16H15FN2O2, monoclinic, P21/c (no. 14), a = 6.0573(3) Å, b = 13.8341(6) Å, c = 33.0876(15) Å, β = 92.837(2)°, Z = 8, V = 2769.3(2) Å3, Rgt(F) = 0.0581, wRref(F2) = 0.1605, T = 173(2) K.

CCDC no.: 1967409

The asymmetric unit of the title structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.19 × 0.17 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:Bruker D8 Venture, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:19662, 4869, 0.063
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3089
N(param)refined:385
Programs:Bruker [1], SHELX [2], Olex2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
F1−0.0087(3)0.12484(14)0.50935(5)0.0667(6)
F2−0.4769(3)−0.13346(13)0.43786(5)0.0600(5)
O1−0.2008(3)0.17686(15)0.37224(5)0.0473(5)
H1−0.1469620.1726050.3493880.071*
O20.1567(3)0.15842(13)0.08796(5)0.0407(5)
O3−0.6599(3)−0.15860(16)0.29901(5)0.0502(6)
H3−0.600291−0.1550960.2766620.075*
O4−0.2765(3)−0.12463(18)0.01773(5)0.0592(6)
N10.0895(3)0.13760(14)0.32026(6)0.0323(5)
N20.1054(4)0.16241(15)0.12901(6)0.0352(5)
N3−0.3579(3)−0.12255(14)0.24933(6)0.0323(5)
N4−0.3284(4)−0.13147(19)0.05872(6)0.0473(6)
C1−0.0477(5)0.15035(18)0.40104(8)0.0366(6)
C2−0.1042(5)0.15280(19)0.44138(8)0.0417(7)
H2−0.2459970.1741420.4485830.050*
C30.0502(5)0.1237(2)0.47011(8)0.0455(7)
C40.2601(5)0.0938(2)0.46232(8)0.0477(8)
H40.3626850.0743590.4834200.057*
C50.3146(5)0.0933(2)0.42240(8)0.0415(7)
H50.4592150.0740890.4159480.050*
C60.1640(4)0.12031(18)0.39108(7)0.0332(6)
C70.2281(4)0.11814(18)0.34963(7)0.0342(6)
H70.3759360.1019740.3440290.041*
C80.1481(4)0.13528(17)0.27930(7)0.0310(6)
C90.3459(5)0.1001(2)0.26563(8)0.0404(7)
H90.4545640.0747360.2844170.048*
C100.3856(4)0.10185(19)0.22475(8)0.0387(7)
H100.5224220.0780870.2160150.046*
C110.2305(4)0.13740(17)0.19622(7)0.0296(6)
C120.0329(4)0.17298(19)0.21016(7)0.0349(6)
H12−0.0760510.1984580.1914480.042*
C13−0.0060(4)0.17155(18)0.25087(7)0.0330(6)
H13−0.1420790.1960610.2596660.040*
C140.2703(4)0.13629(17)0.15238(7)0.0312(6)
C150.4872(5)0.1034(2)0.13741(8)0.0423(7)
H15A0.5150890.0365250.1459350.063*
H15B0.6056420.1451170.1486940.063*
H15C0.4826810.1071720.1078030.063*
C16−0.0404(5)0.1772(2)0.06377(8)0.0526(8)
H16A−0.0075350.1750410.0350780.079*
H16B−0.0971060.2413950.0703420.079*
H16C−0.1517130.1282140.0692830.079*
C17−0.5103(4)−0.13684(19)0.32899(8)0.0353(6)
C18−0.5697(5)−0.1462(2)0.36885(8)0.0418(7)
H18−0.713108−0.1679750.3748820.050*
C19−0.4177(5)−0.1235(2)0.39901(8)0.0411(7)
C20−0.2077(5)−0.09074(19)0.39253(8)0.0432(7)
H20−0.107172−0.0743250.4144020.052*
C21−0.1499(5)−0.08285(19)0.35293(8)0.0381(7)
H21−0.005342−0.0612420.3475880.046*
C22−0.2958(4)−0.10540(17)0.32041(7)0.0310(6)
C23−0.2254(4)−0.10107(17)0.27955(7)0.0332(6)
H23−0.078258−0.0819720.2748150.040*
C24−0.2936(4)−0.12098(17)0.20884(7)0.0302(6)
C25−0.0934(4)−0.08463(19)0.19611(8)0.0373(6)
H250.013033−0.0595660.2153980.045*
C26−0.0498(4)−0.08507(18)0.15538(7)0.0359(6)
H260.087835−0.0608000.1472150.043*
C27−0.2021(4)−0.12009(17)0.12618(7)0.0319(6)
C28−0.4003(4)−0.15880(18)0.13945(7)0.0332(6)
H28−0.505579−0.1854200.1203270.040*
C29−0.4433(4)−0.15852(18)0.17973(7)0.0330(6)
H29−0.578928−0.1846600.1879730.040*
C30−0.1600(4)−0.11467(18)0.08251(7)0.0334(6)
C310.0639(5)−0.0896(2)0.06844(8)0.0448(7)
H31A0.061275−0.0919490.0388210.067*
H31B0.172709−0.1359810.0796460.067*
H31C0.104235−0.0242920.0776480.067*
C32−0.4733(6)−0.1422(3)−0.00665(9)0.0754(12)
H32A−0.582915−0.092238−0.0013800.113*
H32B−0.532949−0.205816−0.0000270.113*
H32C−0.439331−0.140666−0.0352940.113*

Source of material

All chemicals were used without further purification. 1-(4-Aminophenyl)ethan-1-one O-methyl oxime was prepared by a method reported earlier [4], [5]. 4-Fluoro-2-hydroxy-benzaldehyde (140.2 mg, 1 mmol) dissolved in EtOH (5 mL) was added to 1-(4-aminophenyl)ethanone O-methyl oxime (164.5 mg, 1 mmol) dissolved in EtOH (5 mL). After being stirred for 2 h at room temperature, the filtrate was allowed to stand for 21 days in a quiet environment. Several block clear yellow crystals were obtained (yield 71.4%, m.p. 374–382 K). Anal. calcd. for C16H15FN2O2: C, 67.12%; H, 5.28%; N, 9.78%; Found: C, 67.84%; H, 5.62%; N, 9.31%.

Experimental details

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

Comment

More and more attention is paid to the synthesis of mononuclear or multinuclear transition metal complexes with Schiff base ligands. Since the Schiff base ligand has excellent coordination ability with transition metal, it forms a stable transition metal complex [5], [6], [7], [8], [9]. So, we predict that the title compound is an excellent Schiff base ligand [10].

The current work reports the synthesis of title compound, which is built up by two C16H15FN2O2 molecules in the asymmetric unit. Compared with the structure already reported, all bond lengths of the title compound are in normal ranges [10], [11], [12], [13]. There is one strong intramolecular hydrogen bond in each of the two crystallographically independent molecules (see the figure): O1—H1⋯N1 (d(N1⋯H1) = 1.831 Å, d(O1—H1) = 0.84 Å and d(O1⋯N1) = 2.578 Å) and O3—H3⋯N3 (d(N3⋯H3) = 1.819 Å, d(O3—H3) = 0.84 Å and d(O3⋯N3) = 2.568 Å).

References

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Received: 2019-08-25
Accepted: 2019-11-22
Published Online: 2019-12-20
Published in Print: 2020-02-25

©2019 Tao Fu et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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