Abstract
The equimolar reaction between a racemic mixture of (R)- and (S)-camphorquinone with thio-semicarbazide yielded the title compound, C11H17N3OS [common name: (R)- and (S)-camphor thio-semicarbazone], which maintains the chirality of the methyl-ated chiral carbon atoms and crystallizes in the centrosymmetric space group C2/c. There are two mol-ecules in general positions in the asymmetric unit, one of them being the (1R)-camphor thio-semicarbazone isomer and the second the (1S)- isomer. In the crystal, the mol-ecular units are linked by C-H⋯S, N-H⋯O and N-H⋯S inter-actions, building a tape-like structure parallel to the (01) plane, generating R 2 1(7) and R 2 2(8) graph-set motifs for the H⋯S inter-actions. The Hirshfeld surface analysis indicates that the major contributions for crystal cohesion are from H⋯H (55.00%), H⋯S (22.00%), H⋯N (8.90%) and H⋯O (8.40%) inter-actions.
Highlights
The equimolar reaction between a racemic mixture of (R)- and (S)camphorquinone with thiosemicarbazide yielded the title compound, C11H17N3OS [common name: (R)- and (S)-camphor thiosemicarbazone], which maintains the chirality of the methylated chiral carbon atoms and crystallizes in the centrosymmetric space group C2/c
The molecular units are linked by C—HÁ Á ÁS, N—HÁ Á ÁO and N—HÁ Á ÁS interactions, building a tape-like structure parallel to the (101) plane, generating R12(7) and R22(8) graph-set motifs for the HÁ Á ÁS interactions
The second approach deals with the biological activity of coordination compounds, with TSCs acting as ligands
Summary
The origin of thiosemicarbazone (TSC) chemistry can be traced back to the beginning of the 20th century, when thiosemicarbazide was used for the chemical characterization of the R1R2C O group and it was pointed out that the R1R2C N—N(H)C( S)NH2 compound was the main product of the condensation reaction (Freund & Schander, 1902). The biological research concerning TSC derivatives was focused on the molecules as free ligands, but very quickly the scope expanded to coordination compounds. One of the first reports about metal compounds of thiosemicarbazones in medicinal chemistry regards a CuII complex with Mycobacterium tuberculosis growth inhibition activity that was published few years later (Kuhn & Zilliken, 1954). Another milestone in this chemistry, after the reported tuberculostatic property, was the discovery of the antineoplastic activity of TSC derivatives in the 19600s (Sartorelli & Booth, 1967).
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