Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Jasinski, Jerry P., Butcher, Ray J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S., Narayana, B.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
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
_version_ 1782191053146685440
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
work_keys_str_mv AT jasinskijerryp 32chloroethyl2methyl4hpyrido12apyrimidin4one
AT butcherrayj 32chloroethyl2methyl4hpyrido12apyrimidin4one
AT hakimalariqueqnm 32chloroethyl2methyl4hpyrido12apyrimidin4one
AT yathirajanhs 32chloroethyl2methyl4hpyrido12apyrimidin4one
AT narayanab 32chloroethyl2methyl4hpyrido12apyrimidin4one