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3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate
In the cation of the title salt, C(11)H(12)ClN(2)O(+)·C(6)H(2)N(3)O(7) (−), the chloroethyl side chain is in a syn conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle of 78.9 (6)° between the plane of the chloroethyl chain and the pyrimidine ring. The dihedral angle betwe...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2970075/ https://www.ncbi.nlm.nih.gov/pubmed/21577604 http://dx.doi.org/10.1107/S1600536809032693 |
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author | Jasinski, Jerry P. Butcher, Ray J. Hakim Al-Arique, Q. N. M. Yathirajan, H. S. Narayana, B. |
author_facet | Jasinski, Jerry P. Butcher, Ray J. Hakim Al-Arique, Q. N. M. Yathirajan, H. S. Narayana, B. |
author_sort | Jasinski, Jerry P. |
collection | PubMed |
description | In the cation of the title salt, C(11)H(12)ClN(2)O(+)·C(6)H(2)N(3)O(7) (−), the chloroethyl side chain is in a syn conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle of 78.9 (6)° between the plane of the chloroethyl chain and the pyrimidine ring. The dihedral angle between the fused rings is 4.3 (3)°. In the picrate anion, the benzene mean plane makes dihedral angles of 26.7 (1), 33.6 (2) and 5.3 (6)° with the two o-NO(2) groups and the p-NO(2) group, respectively. Extensive hydrogen-bond interactions occur between the cation–anion pair which help to establish the crystal packing. A three-center O⋯(H,H)—(N,C) acceptor hydrogen bond is observed between the phenolate O atom of the picrate anion and the amine and methyl groups of the cation. An N—H⋯(O,O) bifurcated hydrogen bond is observed between the amine group and two O atoms from the phenolate and o-NO(2) groups. |
format | Text |
id | pubmed-2970075 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29700752010-12-30 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate Jasinski, Jerry P. Butcher, Ray J. Hakim Al-Arique, Q. N. M. Yathirajan, H. S. Narayana, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the cation of the title salt, C(11)H(12)ClN(2)O(+)·C(6)H(2)N(3)O(7) (−), the chloroethyl side chain is in a syn conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle of 78.9 (6)° between the plane of the chloroethyl chain and the pyrimidine ring. The dihedral angle between the fused rings is 4.3 (3)°. In the picrate anion, the benzene mean plane makes dihedral angles of 26.7 (1), 33.6 (2) and 5.3 (6)° with the two o-NO(2) groups and the p-NO(2) group, respectively. Extensive hydrogen-bond interactions occur between the cation–anion pair which help to establish the crystal packing. A three-center O⋯(H,H)—(N,C) acceptor hydrogen bond is observed between the phenolate O atom of the picrate anion and the amine and methyl groups of the cation. An N—H⋯(O,O) bifurcated hydrogen bond is observed between the amine group and two O atoms from the phenolate and o-NO(2) groups. International Union of Crystallography 2009-08-22 /pmc/articles/PMC2970075/ /pubmed/21577604 http://dx.doi.org/10.1107/S1600536809032693 Text en © Jasinski 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 Jasinski, Jerry P. Butcher, Ray J. Hakim Al-Arique, Q. N. M. Yathirajan, H. S. Narayana, B. 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
title | 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
title_full | 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
title_fullStr | 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
title_full_unstemmed | 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
title_short | 3-(2-Chloroethyl)-2-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
title_sort | 3-(2-chloroethyl)-2-methyl-4-oxo-4h-pyrido[1,2-a]pyrimidinium 2,4,6-trinitrophenolate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2970075/ https://www.ncbi.nlm.nih.gov/pubmed/21577604 http://dx.doi.org/10.1107/S1600536809032693 |
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