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- 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.
- Authors
Mohamed, Shaaban K.; Younes, Sabry H. H.; Abdel-Raheem, Eman M. M.; Mague, Joel T.; Akkurt, Mehmet; Glidewell, Christopher
- 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 R24(38) rings and two types of R22(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 R22(8), R24(8) and two types of R22(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.
- Subjects
MOLECULAR conformation; SUPRAMOLECULAR chemistry; DIMETHYLFORMAMIDE
- Publication
Acta Crystallographica Section C: Structural Chemistry, 2015, Vol 71, Issue 11, p959
- ISSN
2053-2296
- Publication type
Article
- DOI
10.1107/S2053229615018744