Structure Morphology and Optical Properties of Chiral N-(4-X-phenyl)-N-1(S)-1-phenylethylthiourea X= Cl Br and NO2

摘要

Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2 (compounds >1->3, respectively). Large single crystals of up to 0.5 cm³ were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray diffraction studies and the crystal morphology was compared to calculations employing the Bravais-Friedel, Donnay-Harker model. Molecular packing was further studied with Hirshfeld surface calculations. Semi-empirical classical model calculations of refractive indices, optical rotation and the electro-optic effect were performed with OPTACT on the basis of experimentally determined refractive indices. Compound >3 (space group P 1 (No. 1)) was estimated to possess a large electro-optic coefficient r333 of approximately 30 pm/V, whereas >1 and >2 (space Group P 21 (No. 4) exhibit much smaller effects.