Abstract
There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C13H17N3S, one of them being disordered over the methyl group [site-occupancy ratio = 0.705 (5):0.295 (5)]. The maximum r.m.s. deviations from the mean plane of the non-H atoms for the tetra-lone fragments amount to 0.4572 (17) and 0.4558 (15) Å. The N-N-C-N fragments are not planar and torsion angles are -9.4 (2) and 8.3 (2)°. In the crystal, the mol-ecules are linked by weak N-H⋯S inter-actions into chains along [100] with graph-set motif C(4) and connected by weak N-H⋯S and C-H⋯S inter-actions, forming R21(10) rings. The Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯H (64.20%), H⋯S (12.60%) and H⋯C (12.00%) inter-actions. The crystal packing resembles a herringbone arrangement when viewed along [001].
Highlights
Adriano Bof de Oliveira,a* Johannes Beck,b Christian Landvogt,b Renan Lira de Fariasc and Barbara Regina Santos Feitozaa
The molecules are linked by weak N—HÁ Á ÁS interactions into chains along [100] with graph-set motif C(4) and connected by weak N—HÁ Á ÁS and C—HÁ Á ÁS interactions, forming R12(10) rings
The Hirshfeld surface analysis (Hirshfeld, 1977) of the crystal structure suggests that the contribution of the HÁ Á ÁH intermolecular interactions to the crystal packing amounts to 64.20%, the HÁ Á ÁS interactions amount to 12.60% and the HÁ Á ÁC interactions amount to 12.00%
Summary
The synthesis of thiosemicarbazone derivatives can be traced back to the early 19000s (Freund & Schander, 1902). In the 1940s it was reported that in in vitro assays, the thiosemicarbazone turned out to be very effective against tuberculosis. The related oxygen-containing semicarbazones did not shown biological activity in the same assays, so that the sulfur atom in the molecular structure is essential for Mycobacterium tuberculosis growth inhibition, a true milestone in the thiosemicarbazone pharmacological research (Domagk et al, 1946). The synthesis, the molecular docking calculation and the in vitro inhibition of Chikungunya virus replication by a thiosemicarbazone derivative was published in the past year (Mishra et al, 2016). The crystal structure determination of thiosemicarbazone derivatives is an intensive research field, especially for biological chemistry
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