Abstract
The molecular and crystal structures of a series of 5-Ph-2-(arylCH=NNH)-1,3,4-thiadiazoles [2: aryl = 4-XC6H4 (X = H [2a], 4-Cl [2b], 4-Br [2c], 4-F3CO [2d], 2-HO [2e], 2-HO-3-MeO [2f] as well as [5-Ph-2-(4-HOC6H4CH=NNH)-1,3,4-thiadiazole](3)(H2O)(2)] [(2g)(3) center dot 2 (H2O)] are reported. The compounds were prepared as part of a study on typanocide reagents as possible treatments for Chagas' disease. The asymmetric unit of [(2g)(3) center dot 2 (H2O)] consists of three independent molecules and two water molecules, in contrast to the single molecules comprising the asymmetric units of 2a-2f. In all cases, N-H center dot center dot center dot N intermolecular hydrogen bonding results in the formation of dimers linked by R-2(2)(8) rings. As well as the hydrogen-bonded dimers, the molecules of 2a-2f are also linked by other weak interactions including aromatic pi-pi stacking and C-H center dot center dot center dot X bonds.
Original language | English |
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Pages (from-to) | 598-606 |
Number of pages | 9 |
Journal | Zeitschrift für Kristallographie |
Volume | 224 |
Issue number | 12 |
DOIs | |
Publication status | Published - Dec 2009 |
Keywords
- Chagas' disease
- hydrazones
- thiadiazoles
- hydrogen bonding
- pi-pi stacking interactions
- single crystal structure analysis
- synchrotron X-ray radiation
- 1,3,4-thiadiazole-2-arylhydrazone derivatives
- trypanosoma-cruzi
- crystal-structure
- megazol
- analogs
- 2-amino-1,3,4-thiadiazole
- chloride
- drug