Crystal structures, packing features, Hirshfeld surface analyses and DFT calculations of hydrogen‐bond energy of two homologous 8a‐aryl‐2,3,4,7,8,8a‐hexahydropyrrolopyrimidin‐6(1H)‐ones

The crystal structures and packing features of two homologous Meyer's bicyclic lactams with fused pyrrolidone and medium‐sized perhydropyrimidine rings, namely, 8a‐phenyl‐2,3,4,7,8,8a‐hexahydropyrrolo[1,2‐a]pyrimidin‐6(1H)‐one, C13H16N2O (1), and 8a‐(4‐methylphenyl)‐2,3,4,7,8,8a‐hexahydropyrrol...

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Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2020-05, Vol.76 (5), p.483-489
Main Authors: Grinev, Vyacheslav S, Linkova, Elena I, Krainov, Mikhail N, Dmitriev, Maksim V, Alevtina Yu Yegorova
Format: Article
Language:English
Subjects:
Aromatic compounds
Bond energy
Bonding strength
Chemical bonds
Crystal structure
Crystals
Homology
Hydrogen bonds
Hydrogen-based energy
Mathematical analysis
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Summary:The crystal structures and packing features of two homologous Meyer's bicyclic lactams with fused pyrrolidone and medium‐sized perhydropyrimidine rings, namely, 8a‐phenyl‐2,3,4,7,8,8a‐hexahydropyrrolo[1,2‐a]pyrimidin‐6(1H)‐one, C13H16N2O (1), and 8a‐(4‐methylphenyl)‐2,3,4,7,8,8a‐hexahydropyrrolo[1,2‐a]pyrimidin‐6(1H)‐one, C14H18N2O (2), were elucidated, and Hirshfeld surface plots were calculated and drawn for visualization and a deeper analysis of the intermolecular noncovalent interactions. Molecules of 1 and 2 are weakly linked by intermolecular C=O…H—N hydrogen bonds into chains, which are in turn weakly linked by other C=O…H—Car interactions. The steric volume of the substituent significantly affects the crystal packing pattern.
ISSN:0108-2701
1600-5759
DOI:10.1107/S2053229620005409