(±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide

The new title thiadiazole compound, C(14)H(21)N(3)O(2)S, was semi-synthesized starting from 1-(4-methyl­cyclo­hex-3-en­yl)ethanone, a natural product isolated from Cedrus atlantica essential oil. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The thia­diazo­line ring is...

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Autores principales: Mohammed, Tebbaa, Mazoir, Noureddine, Daran, Jean-Claude, Berraho, Moha, Benharref, Ahmed
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960842/
https://www.ncbi.nlm.nih.gov/pubmed/21201946
http://dx.doi.org/10.1107/S1600536808004728
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author Mohammed, Tebbaa
Mazoir, Noureddine
Daran, Jean-Claude
Berraho, Moha
Benharref, Ahmed
author_facet Mohammed, Tebbaa
Mazoir, Noureddine
Daran, Jean-Claude
Berraho, Moha
Benharref, Ahmed
author_sort Mohammed, Tebbaa
collection PubMed
description The new title thiadiazole compound, C(14)H(21)N(3)O(2)S, was semi-synthesized starting from 1-(4-methyl­cyclo­hex-3-en­yl)ethanone, a natural product isolated from Cedrus atlantica essential oil. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The thia­diazo­line ring is roughly planar, although it may be regarded as having a half-chair conformation. The cyclo­hexenyl ring has a half-chair conformation. The most inter­esting feature is the formation of a pseudo-ring formed by four mol­ecules associated through N—H⋯O hydrogen bonds around a fourfold inversion axis, forming an R (4) (4)(28) motif.
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spelling pubmed-29608422010-12-30 (±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide Mohammed, Tebbaa Mazoir, Noureddine Daran, Jean-Claude Berraho, Moha Benharref, Ahmed Acta Crystallogr Sect E Struct Rep Online Organic Papers The new title thiadiazole compound, C(14)H(21)N(3)O(2)S, was semi-synthesized starting from 1-(4-methyl­cyclo­hex-3-en­yl)ethanone, a natural product isolated from Cedrus atlantica essential oil. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The thia­diazo­line ring is roughly planar, although it may be regarded as having a half-chair conformation. The cyclo­hexenyl ring has a half-chair conformation. The most inter­esting feature is the formation of a pseudo-ring formed by four mol­ecules associated through N—H⋯O hydrogen bonds around a fourfold inversion axis, forming an R (4) (4)(28) motif. International Union of Crystallography 2008-02-20 /pmc/articles/PMC2960842/ /pubmed/21201946 http://dx.doi.org/10.1107/S1600536808004728 Text en © Mohammed et al. 2008 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Mohammed, Tebbaa
Mazoir, Noureddine
Daran, Jean-Claude
Berraho, Moha
Benharref, Ahmed
(±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
title (±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
title_full (±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
title_fullStr (±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
title_full_unstemmed (±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
title_short (±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
title_sort (±)-n-[4-acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960842/
https://www.ncbi.nlm.nih.gov/pubmed/21201946
http://dx.doi.org/10.1107/S1600536808004728
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