Cargando…

(E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate

The title 1,2,4-triazole compound, C(13)H(11)N(5)OS·C(3)H(7)NO, crystallizes as a 1:1 dimethyl­formamide (DMF) solvate. The main mol­ecule exists in a trans configuration with respect to the acyclic C=N bond. An intra­molecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a pr...

Descripción completa

Detalles Bibliográficos
Autores principales: Goh, Jia Hao, Fun, Hoong-Kun, Adhikari, Adithya, Kalluraya, B.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2972175/
https://www.ncbi.nlm.nih.gov/pubmed/21578940
http://dx.doi.org/10.1107/S1600536809050090
_version_ 1782190762431086592
author Goh, Jia Hao
Fun, Hoong-Kun
Adhikari, Adithya
Kalluraya, B.
author_facet Goh, Jia Hao
Fun, Hoong-Kun
Adhikari, Adithya
Kalluraya, B.
author_sort Goh, Jia Hao
collection PubMed
description The title 1,2,4-triazole compound, C(13)H(11)N(5)OS·C(3)H(7)NO, crystallizes as a 1:1 dimethyl­formamide (DMF) solvate. The main mol­ecule exists in a trans configuration with respect to the acyclic C=N bond. An intra­molecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a proton is transferred from the O atom of a hydr­oxy group to the quinoline group N atom. The essentially planar triazole ring and quinoline ring system [maximum deviations of 0.001 (2) and 0.013 (2) Å, respectively] form a dihedral angle of 5.86 (9)°. In the crystal structure, mol­ecules of (E)-4-[(2-hydroxy-3-­quinolyl)methyl­eneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione are linked into R (2) (2)(8) centrosymmteric dimers via N—H⋯O hydrogen bonds. These dimers are further linked into an extended three-dimensional structure by the DMF solvent mol­ecules via inter­molecular N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure is consolidated by two different inter­molecular π–π inter­actions [centroid–centroid distances = 3.6593 (12) and 3.6892 (12) Å].
format Text
id pubmed-2972175
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29721752010-12-30 (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate Goh, Jia Hao Fun, Hoong-Kun Adhikari, Adithya Kalluraya, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title 1,2,4-triazole compound, C(13)H(11)N(5)OS·C(3)H(7)NO, crystallizes as a 1:1 dimethyl­formamide (DMF) solvate. The main mol­ecule exists in a trans configuration with respect to the acyclic C=N bond. An intra­molecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a proton is transferred from the O atom of a hydr­oxy group to the quinoline group N atom. The essentially planar triazole ring and quinoline ring system [maximum deviations of 0.001 (2) and 0.013 (2) Å, respectively] form a dihedral angle of 5.86 (9)°. In the crystal structure, mol­ecules of (E)-4-[(2-hydroxy-3-­quinolyl)methyl­eneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione are linked into R (2) (2)(8) centrosymmteric dimers via N—H⋯O hydrogen bonds. These dimers are further linked into an extended three-dimensional structure by the DMF solvent mol­ecules via inter­molecular N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure is consolidated by two different inter­molecular π–π inter­actions [centroid–centroid distances = 3.6593 (12) and 3.6892 (12) Å]. International Union of Crystallography 2009-11-28 /pmc/articles/PMC2972175/ /pubmed/21578940 http://dx.doi.org/10.1107/S1600536809050090 Text en © Goh et al. 2009 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
Adhikari, Adithya
Kalluraya, B.
(E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate
title (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate
title_full (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate
title_fullStr (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate
title_full_unstemmed (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate
title_short (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate
title_sort (e)-3-methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1h-1,2,4-triazole-5(4h)-thione n,n-dimethyl­formamide solvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2972175/
https://www.ncbi.nlm.nih.gov/pubmed/21578940
http://dx.doi.org/10.1107/S1600536809050090
work_keys_str_mv AT gohjiahao e3methyl42oxidoquinolin1ium3ylmethyleneamino1h124triazole54hthionenndimethylformamidesolvate
AT funhoongkun e3methyl42oxidoquinolin1ium3ylmethyleneamino1h124triazole54hthionenndimethylformamidesolvate
AT adhikariadithya e3methyl42oxidoquinolin1ium3ylmethyleneamino1h124triazole54hthionenndimethylformamidesolvate
AT kallurayab e3methyl42oxidoquinolin1ium3ylmethyleneamino1h124triazole54hthionenndimethylformamidesolvate