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The crystal structures of seven ammonium carboxyl-ate salts are reported, namely ( RS )-1-phenyl-ethan-1-aminium isonicotinate, C 8 H 12 N + ·C 6 H 4 N 1 O 2  - , (I), ( RS )-1-phenyl-ethan-1-aminium flurbiprofenate [or 2-(3-fluoro-4-phenyl-phen-yl)propano-ate], C 8 H 12 N + ·C 15 H 12 FO 2  - , (II), ( RS )-1-phenyl-ethan-1-aminium 2-chloro-4-nitro-benzoate, C 8 H 12 N + ·C 7 H 3 ClNO 4  - , (III), ( RS )-1-phenyl-ethan-1-aminium 4-iodo-benzoate, C 8 H 12 N + ·C 7 H 4 IO 2  - , (IV), ( S )-1-cyclo-hexyl-ethan-1-aminium 2-chloro-4-nitro-benzoate, C 8 H 18 N + ·C 7 H 3 ClNO 4  - , (V), 2-(cyclo-hex-1-en-1-yl)ethan-1-aminium 4-bromo-benzoate, C 8 H 16 N + ·C 7 H 4 BrO 2  - , (VI), and ( S )-1-cyclo-hexyl-ethan-1-aminium 4-bromo-benzoate, C 8 H 18 N + ·C 7 H 4 BrO 2  - , (VII). Salts (II) to (VII) feature three N + -H⋯O - hydrogen bonds, which form one-dimensional hydrogen-bonded ladders. Salts (II), (III), (IV), (V) and (VII) have a type II ladder system despite the presence of halogen bonding and other inter-molecular inter-actions, whereas (VI) has a type III ladder system. Salt (I) has a unique hydrogen-bonded system of ladders, featuring both N + -H⋯O - and N + -H⋯N hydrogen bonds owing to the presence of the pyridine functional group. The presence of an additional hydrogen-bond acceptor on the carboxyl-ate cation disrupts the formation of the ubiquitous type II and III ladder found predominately in ammonium carboxyl-ate salts. Halogen bonding, however, has no influence on their formation.

An investigation to elucidate the factors dictating the crystal structure of seven ammonium carboxylate molecular salts