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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‐hexahydropyrrolo[1,2‐ a ]pyrimidin‐6(1 H )‐ones
Author(s) -
Grinev Vyacheslav S.,
Linkova Elena I.,
Krainov Mikhail N.,
Dmitriev Maksim V.,
Yegorova Alevtina Yu.
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620005409
Subject(s) - steric effects , intermolecular force , hydrogen bond , chemistry , crystallography , substituent , crystal structure , molecule , non covalent interactions , crystal (programming language) , aryl , homologous series , stereochemistry , alkyl , organic chemistry , computer science , programming language
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(1 H )‐one, C 13 H 16 N 2 O ( 1 ), and 8a‐(4‐methylphenyl)‐2,3,4,7,8,8a‐hexahydropyrrolo[1,2‐ a ]pyrimidin‐6(1 H )‐one, C 14 H 18 N 2 O ( 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—C ar interactions. The steric volume of the substituent significantly affects the crystal packing pattern.