Abstract
Purpose: To elucidate the solid-state conformation as well as the imine double bond configuration of a potential anti-Candida agent ({[(1E)-3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)(3,4,5-trimethoxyphenyl) methanone.
Methods: Acetophenone was used as a starting material to prepare the target oximino ester in a four-step reaction sequence. Nuclear magnetic resonance (H-1-NMR and C-13-NMR) and mass spectrometry were used to confirm the chemical structure of the synthesized compounds. Thereafter, x-ray crystallography was performed on single crystals of the target compound. The solid-state conformation of the target molecule and the (E)-configuration of its imine double bond were determined via the investigation of its single crystal x-ray molecular structure.
Results: The titled compound crystallized in the triclinic space group P-1 with a = 11.0719 (7) angstrom, b = 14.6602 (9) angstrom, c = 14.8530 (9) angstrom, alpha = 67.205 (4)degrees, beta = 80.388 (5)degrees, gamma = 70.100 (5)degrees, V = 2088.2 (2) angstrom(3), and Z = 4. Individual molecules were packed in the crystal by three weak non-classical intermolecular hydrogen interactions, including C9A-H9AA center dot center dot center dot O3A, C9B-H9BA center dot center dot center dot O3B, C18B-H18C center dot center dot center dot O2A and C20B-H20B center dot center dot center dot O4B.
Conclusion: The results of the single crystal x-ray molecular structure of the titled anti-Candida agent unequivocally confirmed its (E)-configuration.