Shaibah Mohammed A E, Yathirajan Hemmige S, Manju Nagaraja, Kalluraya Balakrishna, Rathore Ravindranath S, Glidewell Christopher
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.
Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574 199, India.
Acta Crystallogr E Crystallogr Commun. 2020 Feb 14;76(Pt 3):360-365. doi: 10.1107/S2056989020001735. eCollection 2020 Mar 1.
Chalcones of type 4-CHC(O)CH=CHCH(OCHCCH)-4, where = 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, CHClO, (I), and 1-(4-bromo-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, CHBrO, (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 ()-3-(4-chloro-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, CHClNOS, (IV), ()-3-(4-bromo-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, CHBrNOS, (V), and ()-3-(4-meth-oxy-phen-yl)-5-[4-(prop-2-yn-yloxy)phen-yl]-4,5-di-hydro-pyrazole-1-carbo-thio-amide, CHNOS, (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.
4-CHC(O)CH=CHCH(OCHCCH)-4型查尔酮（其中 = Cl、Br或MeO）已通过与硫代氨基脲的环缩合反应转化为相应的4,5-二氢吡唑-1-碳硫酰胺。查尔酮1-(4-氯苯基)-3-[4-(丙-2-炔氧基)苯基]丙-2-烯-1-酮，CHClO，(I)，和1-(4-溴苯基)-3-[4-(丙-2-炔氧基)苯基]丙-2-烯-1-酮，CHBrO，(II)，是同构的，并且它们的分子通过两种独立的C-H⋯π(芳烃)相互作用连接成片，这两种相互作用都涉及同一个芳环，一个C-H供体接近每个面。在每种产物()-3-(4-氯苯基)-5-[4-(丙-2-炔氧基)苯基]-4,5-二氢吡唑-1-碳硫酰胺，CHClNOS，(IV)，()-3-(4-溴苯基)-5-[4-(丙-2-炔氧基)苯基]-4,5-二氢吡唑-1-碳硫酰胺，CHBrNOS，(V)，和()-3-(4-甲氧基苯基)-5-[4-(丙-2-炔氧基)苯基]-4,5-二氢吡唑-1-碳硫酰胺，CHNOS，(VI)中，还原的吡唑环采用信封构象，带有4-(丙-2-炔氧基)苯基取代基的C原子占据轴向位置，偏离四个环原子的平面。化合物(IV)和(V)是同构的，并且它们的分子通过N-H⋯S和C-H⋯S氢键的组合连接成边稠合环的链。(VI)的分子通过N-H⋯S、N-H⋯N和C-H⋯π(芳烃)氢键的组合连接成片。与一些相关化合物的结构进行了比较。
