Crystal structures of the dioxane hemisolvates of N-(7-bromo-methyl-1,8-naphthyridin-2-yl)acetamide and bis-[N-(7-di-bromo-methyl-1,8-naphthyridin-2-yl)acetamide].

ABSTRACT: The syntheses and crystal structures of N-(7-bromo-methyl-1,8-naphthyridin-2-yl)acetamide dioxane hemisolvate, C₁₁H₁₀BrN₃O·0.5C₄H₈O₂, (I), and bis-[N-(7-di-bromo-methyl-1,8-naphthyridin-2-yl)acetamide] dioxane hemisolvate, 2C₁₁H₉Br₂N₃O·0.5C₄H₈O₂, (II), are described. The mol-ecules adopt a conformation with the N-H hydrogen pointing towards the lone electron pair of the adjacent naphthyridine N atom. The crystals of (I) are stabilized by a three-dimensional supra-molecular network comprising N-H?N, C-H?N and C-H?O hydrogen bonds, as well as C-Br?? halogen bonds. The crystals of compound (II) are stabilized by a three-dimensional supra-molecular network comprising N-H?N, C-H?N and C-H?O hydrogen bonds, as well as C-H?? contacts and C-Br?? halogen bonds. The structure of the substituent attached in the 7-position of the naphthyridine skeleton has a fundamental influence on the pattern of inter-molecular noncovalent bonding. While the Br atom of (I) participates in weak C-Br?O_guest and C-Br?? contacts, the Br atoms of compound (II) are involved in host-host inter-actions via C-Br?O=C, C-Br?N and C-Br?? bonding.

SUBMITTER: Rosin R 

PROVIDER: S-EPMC5730284 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature