Paper
Structure of 1-(4-Methylphenylamino)-2-phenyl-1,2-ethandione-1-oxime
Published 2003 · U. Sarı, H. Batı, K. Guven
Analytical Sciences: X-ray Structure Analysis Online
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Abstract
compounds in the chemical industry and medicine due to their biological activity. Oximes have various insecticidal, miticidal and nematocidal activities and are employed as antidotes against organophosphorus poisons.1 Carbonyl-oximes are employed in the separation and spectrophotometric determination of Ni, Pd, Co, Fe and Cu metals.2,3 Oxime groups posses stronger hydrogen-bonding capabilities than alcohols, phenols and carboxylic acids.4 In this paper we report on the crystal structure of the title compound, shown in Fig. 1. The spectrum of H-NMR was recorded with a spectrometer 60-MHz VARIAN (EM-360). Wchloroisonitrosoacetophenone (2.75 g, 0.015 mol) was solved in 40 ml of dichloromethane; then a solution of (4.86 g, 0.03 mol) 4-methylaniline in 20 ml dichloromethane was added dropwise into this mixture. The precipitated product was filtered off. The filtered mixture was kept under room-temperature conditions for 3 days. Finally, the formed single crystals was filtered off and washed with ethanol. Reflection data were collected on a Rigaku AFC7S diffractometer using Mo Kα monochromated with graphite at 20.0 ̊C, as summarized in Table 1, and corrected for Lorentz and polarization effects. The structure was solved by a direct method (SIR 92),5 and refined by full-matrix least-squares with anisotropic thermal parameters for the non-hydrogen atoms. In a later stage of the refinement, reflection data were corrected for absorption and extinction. The oxime H atoms were located from a difference map and refined isotropically; the positions of the remaining H atoms were calculated geometrically. All of the calculations were performed using the program system teXsan crystallographic software package of Molecular Structure Corporation. The final results of the refinement and the atomic coordinates are shown in Tables 1 and 2, respectively. The bond distances and angles are listed in Table 3. The structure of the molecule is shown in Fig. 2. There are two molecules (A and B) in the crystal structure of the title compound. These two molecules are linked by H bonds, the geometric details of which are given in Table 4. As can be seen x61 ANALYTICAL SCIENCES 2003, VOL. 19
The crystal structure of 1-(4-Methylphenylamino)-2-phenyl-1,2-ethandione-1-oxime reveals two linked molecules with strong hydrogen-bonding capabilities, useful in various industries and medicine.
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