6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine

The title compound, C(12)H(9)ClN(4), was prepared from dichloro­pyridazine and tolyl­tetra­zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol­ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036 Å) and an intra­molecular C—H⋯N hydrogen bond o...

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Detalles Bibliográficos
Autores principales: Preis, Jasmin, Schollmeyer, Dieter, Detert, Heiner
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201469/
https://www.ncbi.nlm.nih.gov/pubmed/22058729
http://dx.doi.org/10.1107/S1600536811035288
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author Preis, Jasmin
Schollmeyer, Dieter
Detert, Heiner
author_facet Preis, Jasmin
Schollmeyer, Dieter
Detert, Heiner
author_sort Preis, Jasmin
collection PubMed
description The title compound, C(12)H(9)ClN(4), was prepared from dichloro­pyridazine and tolyl­tetra­zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol­ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036 Å) and an intra­molecular C—H⋯N hydrogen bond occurs. In the crystal, the mol­ecules form dimers connected via π–π inter­actions [centroid–centroid distance = 3.699 (2) Å], which are further connected to neighbouring mol­ecules via C—H—N bonds. The bond lengths in the pyridazine ring system indicate a strong localization of the double bonds and there is a weak C—Cl bond [1.732 (3) Å].
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spelling pubmed-32014692011-11-06 6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine Preis, Jasmin Schollmeyer, Dieter Detert, Heiner Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(12)H(9)ClN(4), was prepared from dichloro­pyridazine and tolyl­tetra­zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol­ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036 Å) and an intra­molecular C—H⋯N hydrogen bond occurs. In the crystal, the mol­ecules form dimers connected via π–π inter­actions [centroid–centroid distance = 3.699 (2) Å], which are further connected to neighbouring mol­ecules via C—H—N bonds. The bond lengths in the pyridazine ring system indicate a strong localization of the double bonds and there is a weak C—Cl bond [1.732 (3) Å]. International Union of Crystallography 2011-09-03 /pmc/articles/PMC3201469/ /pubmed/22058729 http://dx.doi.org/10.1107/S1600536811035288 Text en © Preis et al. 2011 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
Preis, Jasmin
Schollmeyer, Dieter
Detert, Heiner
6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
title 6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
title_full 6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
title_fullStr 6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
title_full_unstemmed 6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
title_short 6-Chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
title_sort 6-chloro-3-(3-methyl­phen­yl)-1,2,4-triazolo[4,3-b]pyridazine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201469/
https://www.ncbi.nlm.nih.gov/pubmed/22058729
http://dx.doi.org/10.1107/S1600536811035288
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AT schollmeyerdieter 6chloro33methylphenyl124triazolo43bpyridazine
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