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3-(2-Chloro-ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one.

ABSTRACT: In the title mol-ecule, 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 chloro-ethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle between the chloro-ethyl side chain and the pyrimidine ring of 88.5?(1)°. Weak inter-molecular C-H?N and C-H?Cl hydrogen bonds along with ?-? inter-actions 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.

SUBMITTER: Jasinski JP

PROVIDER: S-EPMC2977208 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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3-(2-Chloro-ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one.

Jasinski Jerry P JP Butcher Ray J RJ Hakim Al-Arique Q N M QN Yathirajan H S HS Narayana B B

Acta crystallographica. Section E, Structure reports online 20090725 Pt 8

In the title mol-ecule, 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 chloro-ethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle between the chloro-ethyl side chain and the pyrimidine ring of 88.5 (1)°. Weak inter-molecular C-H⋯N and C-H⋯Cl hydrogen bonds along with π-π inter-actions between the pyrimidine and pyri ...[more]

PMID: 21583662

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