An investigation to elucidate the factors dictating the crystal structure of seven ammonium carboxyl-ate mol-ecular salts

Acta Crystallographica. Section E, Crystallographic Communications
Jacques Blignaut, Andreas Lemmerer

Abstract

The crystal structures of seven ammonium carboxyl-ate salts are reported, namely (RS)-1-phenyl-ethan-1-aminium isonicotinate, C8H12N+·C6H4N1O2-, (I), (RS)-1-phenyl-ethan-1-aminium flurbiprofenate [or 2-(3-fluoro-4-phenyl-phen-yl)propano-ate], C8H12N+·C15H12FO2-, (II), (RS)-1-phenyl-ethan-1-aminium 2-chloro-4-nitro-benzoate, C8H12N+·C7H3ClNO4-, (III), (RS)-1-phenyl-ethan-1-aminium 4-iodo-benzoate, C8H12N+·C7H4IO2-, (IV), (S)-1-cyclo-hexyl-ethan-1-aminium 2-chloro-4-nitro-benzoate, C8H18N+·C7H3ClNO4-, (V), 2-(cyclo-hex-1-en-1-yl)ethan-1-aminium 4-bromo-benzoate, C8H16N+·C7H4BrO2-, (VI), and (S)-1-cyclo-hexyl-ethan-1-aminium 4-bromo-benzoate, C8H18N+·C7H4BrO2-, (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...Continue Reading

References

Jun 25, 1999·Pharmacy World & Science : PWS·A A van SorgeN J van Haeringen
Aug 31, 2002·Chemistry : a European Journal·Géraldine BouchardHubert H Girault
Nov 7, 2003·Organic Letters·Susan A OdomJohn E Anthony
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
May 31, 2013·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Simon ParsonsTrixie Wagner
Jun 12, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nick NagelsWouter A Herrebout
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick

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Citations

Feb 6, 2019·Acta Crystallographica. Section C, Structural Chemistry·Eynav KatsAndreas Lemmerer
Jun 1, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Andrei S Batsanov

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