Dataset Information

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

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 ubiquitous type II and III ladder found predominately in ammonium carboxyl-ate salts. Halogen bonding, however, has no influence on their formation.

SUBMITTER: Blignaut J

PROVIDER: S-EPMC5947467 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

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

Blignaut Jacques J Lemmerer Andreas A

Acta crystallographica. Section E, Crystallographic communications 20180417 Pt 5

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-nitr ...[more]

PMID: 29850072

Similar Datasets

Project description:The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C11H19N2S+) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C11H19N2S+·C8H7O2 -, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C11H19N2S+·C7H4BrO2 -, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C11H19N2S+·C7H3N2O6 -, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C11H19N2S+·C4H2O4 2-,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C11H19N2S+·0.5C4H4O4 2-·0.5C4H5O4 -. 0.5C11H18N2S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH+=C-NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N+H2 resonance form to the structure. The packing for (I)-(V) features a robust local R 2 2(8) loop motif in which the cation forms two near-linear N-H?O hydrogen bonds from the N+-H group and syn H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H?O and N?H-O contributors but the same R 2 2(8) loop results for both disorder components]. The anti H atom of the -NH2 group also forms an N-H?O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.

Dataset Information

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

Publications

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

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets