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4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone
In the title sydnone compound, C(24)H(18)N(6)O(3)S {systematic name: 4-[3-(1-naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thiadiaz...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979609/ https://www.ncbi.nlm.nih.gov/pubmed/21579474 http://dx.doi.org/10.1107/S1600536810017812 |
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author | Goh, Jia Hao Fun, Hoong-Kun Nithinchandra, Kalluraya, B. |
author_facet | Goh, Jia Hao Fun, Hoong-Kun Nithinchandra, Kalluraya, B. |
author_sort | Goh, Jia Hao |
collection | PubMed |
description | In the title sydnone compound, C(24)H(18)N(6)O(3)S {systematic name: 4-[3-(1-naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thiadiazine ring adopts a twist-boat conformation. The essentially planar 1,2,3-oxadiazole and 1,2,4-triazole rings [maximum deviations of 0.006 (1) and 0.008 (1) Å, respectively] are inclined to one another at interplanar angle of 44.11 (4)°. The naphthalene unit forms an interplanar angle of 66.40 (4)° with the 1,2,4-triazole ring. In the crystal packing, pairs of intermolecular C—H⋯O hydrogen bonds link adjacent molecules into dimers incorporating R (2) (2)(12) ring motifs. Further stabilization is provided by weak C—H⋯π interactions. |
format | Text |
id | pubmed-2979609 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29796092010-12-30 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone Goh, Jia Hao Fun, Hoong-Kun Nithinchandra, Kalluraya, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title sydnone compound, C(24)H(18)N(6)O(3)S {systematic name: 4-[3-(1-naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thiadiazine ring adopts a twist-boat conformation. The essentially planar 1,2,3-oxadiazole and 1,2,4-triazole rings [maximum deviations of 0.006 (1) and 0.008 (1) Å, respectively] are inclined to one another at interplanar angle of 44.11 (4)°. The naphthalene unit forms an interplanar angle of 66.40 (4)° with the 1,2,4-triazole ring. In the crystal packing, pairs of intermolecular C—H⋯O hydrogen bonds link adjacent molecules into dimers incorporating R (2) (2)(12) ring motifs. Further stabilization is provided by weak C—H⋯π interactions. International Union of Crystallography 2010-05-22 /pmc/articles/PMC2979609/ /pubmed/21579474 http://dx.doi.org/10.1107/S1600536810017812 Text en © Goh et al. 2010 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 Goh, Jia Hao Fun, Hoong-Kun Nithinchandra, Kalluraya, B. 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
title | 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
title_full | 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
title_fullStr | 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
title_full_unstemmed | 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
title_short | 4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
title_sort | 4-[3-(1-naphthyloxymethyl)-7h-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979609/ https://www.ncbi.nlm.nih.gov/pubmed/21579474 http://dx.doi.org/10.1107/S1600536810017812 |
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