Crystal structure and Hirshfeld surface analysis of 6-amino-8-(2,6-dichlorophenyl)-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbonitrile

In the molecular structure of the title compound, C16H13Cl2N5, the 1,4-dihydropyridine ring of the 1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine ring system adopts a screw-boat conformation, while the 1,3-diazinane ring is puckered. In the crystal, intermolecular N-H center dot center dot center dot N and C-H center dot center dot center dot N hydrogen bonds form molecular sheets parallel to the (110) and ((1) over bar 10) planes, crossing each other. Adjacent molecules are further linked by C-H center dot center dot center dot pi interactions, which form zigzag chains propagating parallel to [100]. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from N center dot center dot center dot H/H center dot center dot center dot N (28.4%), H center dot center dot center dot H (24.5%), C center dot center dot center dot H/H center dot center dot center dot C (21.4%) and Cl center dot center dot center dot H/H center dot center dot center dot Cl (16.1%) contacts.

Automated summary

The molecular structure of the title compound contains a 1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine ring, with the 1,4-dihydropyridine ring adopting a screw-boat conformation. In the crystal, intermolecular N-H and C-H hydrogen bonds form molecular sheets parallel to specific planes, while C-H...pi interactions link adjacent molecules into zigzag chains. Major contributions to the crystal packing come from N center dot center dot center dot H/H center dot center dot center dot N, H center dot center dot center dot H, C center dot center dot center dot H/H center dot center dot center dot C, and Cl center dot center dot center dot H/H center dot center dot center dot Cl contacts.