title: The interplay of solvation, molecular conformation and supramolecular assembly in 1,1'-({[(ethane-1,2-diyl)dioxy](1,2-phenylene)}bis(methanylylidene))bis(thiosemicarbazide) and its N,N-dimethylformamide disolvate.
abstract: The wide diversity of applications of thiosemicarbazones and bis(thiosemicarbazones) has seen them used as anticancer and antitubercular agents, and as ligands in metal complexes designed to act as site-specific radiopharmaceuticals. Molecules of 1,1'-({[(ethane-1,2-diyl)dioxy](1,2-phenylene)}bis(methanylylidene))bis(thiosemicarbazide) {alternative name: 2,2'-[ethane-1,2-diylbis(oxy)]dibenzaldehyde bis(thiosemicarbazide)}, C18H20N6O2S2, (I), lie across twofold rotation axes in the space group C2/c, with an O-C-C-O torsion angle of -59.62 (13)° and a trans-planar arrangement of the thiosemicarbazide fragments relative to the adjacent aryl rings. The molecules of (I) are linked by N-H...S hydrogen bonds to form sheets containing R(2)4(38) rings and two types of R(2)2(8) ring. In the N,N-dimethylformamide disolvate, C18H20N6O2S2·2C3H7NO, (II), the independent molecular components all lie in general positions, but one of the solvent molecules is disordered over two sets of atomic sites having occupancies of 0.839 (3) and 0.161 (3). The O-C-C-O torsion angle in the ArOCH2CH2OAr component is -75.91 (14)° and the independent thiosemicarbazide fragments both adopt a cis-planar arrangement relative to the adjacent aryl rings. The ArOCH2CH2OAr components in (II) are linked by N-H...S hydrogen bonds to form deeply puckered sheets containing R(2)2(8), R(2)4(8) and two types of R(2)2(38) rings, and which contain cavities which accommodate all of the solvent molecules in the interior of the sheets. Comparisons are made with some related compounds.
authors.affiliation: Chemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England.
authors.forename: Shaaban K
authors.initials: SK
authors.lastname: Mohamed
authors.affiliation: Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt.
authors.forename: Sabry H H
authors.initials: SH
authors.lastname: Younes
authors.affiliation: Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt.
authors.forename: Eman M M
authors.initials: EM
authors.lastname: Abdel-Raheem
authors.affiliation: Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
authors.forename: Joel T
authors.initials: JT
authors.lastname: Mague
authors.affiliation: Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
authors.forename: Mehmet
authors.initials: M
authors.lastname: Akkurt
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D018360:Crystallography, X-Ray; D005559:Formamides / Q000737:chemistry* / Q000494:pharmacology*; D008024:Ligands; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: C000605356:1,1'-((((ethane-1,2-diyl)dioxy)(1,2-phenylene))bis(methanylylidene))bis(thiosemicarbazide); D005559:Formamides; D008024:Ligands; C000605357:N,N-dimethylformamide disolvate; D012997:Solvents; D013882:Thiosemicarbazones
keywords: crystal structure; disorder; hydrogen bonding; molecular conformation; solvation; thiosemicarbazides