X-ray Structure and Density Functional Theory Investigations of 4-((2R)-2-(3,4-dibromophenyl)-1-fluoro cyclopropyl)-N-(o-tolyl)benzamide Compound

In this work, the structure of 4-((2R)-2-(3,4-dibromophenyl)-1-fluorocyclopropyl)-N-(o-tolyl) benzamide (DBFB) has been determined at room temperature using single-crystal X-ray diffraction data. The structure of the compound was solved using 1464 observed reflections with I >= 2 sigma(I). It crystallizes in monoclinic space group P2(1) with a = 20.0820(10), b = 10.2770(10), c = 4.860(2) angstrom, beta = 95.9600(10)degrees, V = 997.6(4) angstrom(3), Z = 2, D-c = 1.675 g/m(3), F(000) = 500, M-r = 503.18, mu = 4.09 mm(-1) and the fmal R = 0.0639. The molecular packing of the title compound exhibits C-H center dot center dot center dot O and C-H center dot center dot center dot F hydrogen bonds forming a supramolecular network. Furthermore, conformational analysis has been performed in order to confirm the most stable conformer of the title compound. Geometrical parameters of the keto conformer in the ground state have been obtained using density functional theory (DFT) method with B3LYP/6-31G(d,p) level of theory. In general, a good agreement between the calculated and experimental results was observed. The normal modes of vibration, molecular boundary orbitals (HOMO and LUMO), reactivity descriptors, Mullikan atomic charges and molecular electrostatic potential for the title compound have been evaluated and discussed.