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Chalcones of type 4- X C 6 H 4 C(O)CH=CHC 6 H 4 (OCH 2 CCH)-4, where X = Cl, Br or MeO, have been converted to the corresponding 4,5-di-hydro-pyrazole-1-carbo-thio-amides using a cyclo-condensation reaction with thio-semicarbazide. The chalcones 1-(4-chloro-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, C 18 H 13 ClO 2 , (I), and 1-(4-bromo-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, C 18 H 13 BrO 2 , (II), are isomorphous, and their mol-ecules are linked into sheets by two independent C-H⋯π(arene) inter-actions, both involving the same aryl ring with one C-H donor approaching each face. In each of the products ( RS )-3-(4-chloro-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, C 19 H 16 ClN 3 OS, (IV), ( RS )-3-(4-bromo-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, C 19 H 16 BrN 3 OS, (V), and ( RS )-3-(4-meth-oxy-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, C 20 H 19 N 3 O 2 S, (VI), the reduced pyrazole ring adopts an envelope conformation with the C atom bearing the 4-prop-2-yn-yloxy)phenyl substituent, which occupies the axial site, displaced from the plane of the four ring atoms. Compounds (IV) and (V) are isomorphous and their mol-ecules are linked into chains of edge-fused rings by a combination of N-H⋯S and C-H⋯S hydrogen bonds. The mol-ecules of (VI) are linked into sheets by a combination of N-H⋯S, N-H⋯N and C-H⋯π(arene) hydrogen bonds. Comparisons are made with the structures of some related compounds.

Conversion of diarylchalcones into 4,5-dihydropyrazole-1-carbothioamides: molecular and supramolecular structures of two precursors and three products