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(R,S)-5-(4-Chlorophenyl)-3-{(E)-2-[(R,S)-2,6,6-trimethylcyclohex-2-en-1-yl]vinyl}-4,5-dihydro-1H-pyrazole-1-carboximidamide Hydrochloride
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Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, No. 5 Jalan Universiti, Bandar Sunway 47500, Selangor Darul Ehsan, Malaysia
Author to whom correspondence should be addressed.
Molbank 2019, 2019(1), M1047;
Received: 18 January 2019 / Revised: 18 February 2019 / Accepted: 19 February 2019 / Published: 19 February 2019
(This article belongs to the Section Structure Determination)
The title compound, 4-(4-chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione (1), was synthesized by a hetero-cyclization reaction of 4-chlorophenyl isothiocyanate and formic hydrazide. Compound 1 was characterized by a single-crystal X-ray structure determination as well as 1H and 13C{1H} NMR, IR, and UV spectroscopy, and microelemental analysis. X-ray crystallography on 1 confirms the molecule exists as the thione tautomer and shows the five-membered ring to be planar and to form a dihedral angle of 82.70(5)° with the appended chlorophenyl ring, indicating an almost orthogonal relationship. In the molecular packing, supramolecular dimers are formed via thioamide-N–H⋯S(thione) hydrogen bonds and these are connected by C=S⋯π(triazolyl) and C-Cl⋯π(triazolyl) interactions, leading to a three-dimensional architecture. View Full-Text
Keywords: 1,2,4-triazole-5-thione; hetero-cyclization reaction; hydrogen bonding; X-ray crystallography 1,2,4-triazole-5-thione; hetero-cyclization reaction; hydrogen bonding; X-ray crystallography
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Yeo, C.I.; Azizan, A.H.S.; Tiekink, E.R. 4-(4-Chlorophenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione. Molbank 2019, 2019, M1047.

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