title: Structure, morphology and optical properties of chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2.
abstract: 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 cm(3) 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 r(333) of approximately 30 pm/V, whereas 1 and 2 (space Group P 2(1) (No. 4) exhibit much smaller effects.
authors.affiliation: Department of Chemistry, University of Washington, Seattle, Washington 98195, USA. kaminsky@chem.washington.edu
authors.forename: Werner
authors.initials: W
authors.lastname: Kaminsky
authors.forename: Donald
authors.initials: D
authors.lastname: Responte
authors.forename: Dan
authors.initials: D
authors.lastname: Daranciang
authors.forename: Jose B
authors.initials: JB
authors.lastname: Gallegos
authors.forename: Bao-Chau
authors.initials: BC
authors.lastname: Ngoc Tran
authors.forename: Tram-Anh
authors.initials: TA
authors.lastname: Pham
mesh_terms: D001966:Bromine / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004583:Electrons; D006860:Hydrogen Bonding; D008958:Models, Molecular; D009585:Nitrogen Dioxide / Q000737:chemistry*; D055620:Optical Phenomena; D012031:Refractometry; D012399:Rotation; D013854:Thioamides / Q000737:chemistry; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D013854:Thioamides; D002713:Chlorine; D013890:Thiourea; D009585:Nitrogen Dioxide; D001966:Bromine