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3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
In the title molecule, C(11)H(11)ClN(2)O, the pyrido[1,2-a]pyrimidine ring system is planar (maximum deviation = 0.0148 Å) and the methyl C and carbonyl O atoms are nearly coplanar to it. The chloroethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a di...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977208/ https://www.ncbi.nlm.nih.gov/pubmed/21583662 http://dx.doi.org/10.1107/S1600536809027548 |
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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 title molecule, C(11)H(11)ClN(2)O, the pyrido[1,2-a]pyrimidine ring system is planar (maximum deviation = 0.0148 Å) and the methyl C and carbonyl O atoms are nearly coplanar to it. The chloroethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle between the chloroethyl side chain and the pyrimidine ring of 88.5 (1)°. Weak intermolecular C—H⋯N and C—H⋯Cl hydrogen bonds along with π–π interactions between the pyrimidine and pyridine rings [centroid–centroid distance is 3.538 (2) Å] form a three-dimensional network. The crystal is a racemic twin with a 0.68 (12):0.32 (12) domain ratio. MOPAC AM1 and density functional theory (DFT) theoretical calculations at the B3-LYP/6–311+G(d,p) level support these observations. |
format | Text |
id | pubmed-2977208 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29772082010-12-30 3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 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 title molecule, C(11)H(11)ClN(2)O, the pyrido[1,2-a]pyrimidine ring system is planar (maximum deviation = 0.0148 Å) and the methyl C and carbonyl O atoms are nearly coplanar to it. The chloroethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle between the chloroethyl side chain and the pyrimidine ring of 88.5 (1)°. Weak intermolecular C—H⋯N and C—H⋯Cl hydrogen bonds along with π–π interactions between the pyrimidine and pyridine rings [centroid–centroid distance is 3.538 (2) Å] form a three-dimensional network. The crystal is a racemic twin with a 0.68 (12):0.32 (12) domain ratio. MOPAC AM1 and density functional theory (DFT) theoretical calculations at the B3-LYP/6–311+G(d,p) level support these observations. International Union of Crystallography 2009-07-25 /pmc/articles/PMC2977208/ /pubmed/21583662 http://dx.doi.org/10.1107/S1600536809027548 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-4H-pyrido[1,2-a]pyrimidin-4-one |
title | 3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one |
title_full | 3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one |
title_fullStr | 3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one |
title_full_unstemmed | 3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one |
title_short | 3-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one |
title_sort | 3-(2-chloroethyl)-2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977208/ https://www.ncbi.nlm.nih.gov/pubmed/21583662 http://dx.doi.org/10.1107/S1600536809027548 |
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