(E)-Methyl 2-[(2-fluorophenyl)aminomethylene]-3-oxobutanoate: X-ray and density functional theory (DFT) study.
The title compound, C(12)H(12)FNO(3), a potential precursor for fluoroquinoline synthesis, is essentially planar, with the most outlying atoms displaced from the best-plane fit through all non-H atoms by 0.163 (2) and 0.118 (2) A. Molecules are arranged in layers oriented parallel to the (011) plane. The arrangement of the molecules in the structure is controlled mainly by electrostatic interactions, as the dipole moment of the molecule is 5.2 D. In addition, the molecules are linked by a weak C-H...O hydrogen bond which gives rise to chains with the base vector [1,1,1]. Electron transfer within the molecule is analysed using natural bond orbital (NBO) analysis. Deviations from the ideal molecular geometry are explained by the concept of non-equivalent hybrid orbitals.
Langer
Vratislav
V
Environmental Inorganic Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-412 96 Göteborg, Sweden. langer@chalmers.se
Mach
Pavel
P
Smrcok
Lubomír
L
Milata
Viktor
V
D000090:Acetoacetates / Q000737:chemistry*; D024841:Fluoroquinolones / Q000138:chemical synthesis / Q000737:chemistry; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure
D000090:Acetoacetates; D024841:Fluoroquinolones