Open AccessPolymorphism in ammonium 2,4,6‐trimethylbenzenesulfonate
Author(s) -
Aucott Stephen M.,
Dale Sophie H.,
Elsegood Mark R. J.,
Holmes Kathryn E.,
Gilby Liam M.,
Kelly Paul F.
Publication year - 2005
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270104034274
Subject(s) - ammonium , chemistry , organic chemistry
During investigations into sulfide‐ and selenide‐amination reactions using the aminating agent o ‐mesitylsulfonylhydroxylamine, the monoclinic, (I), and orthorhombic, (II), polymorphs of ammonium 2,4,6‐trimethylbenzenesulfonate, NH 4 + ·C 9 H 11 O 3 S − , have been crystallized. Investigation of the hydrogen‐bonding motifs within the two polymorphs shows that both contain N + —H⋯O − hydrogen bonds between the ammonium cations and the 2,4,6‐trimethylbenzenesulfonate anions. Polymorph (I) contains (12) and (8) graph‐set ring motifs, while polymorph (II) contains the same (12) ring motif in combination with an (10) motif. The two hydrogen‐bonding patterns result in slightly different packing structures for the two polymorphs, but both are based on a thick‐sheet arrangement, in which the NH 4 + cations are enveloped between two layers of 2,4,6‐trimethylbenzenesulfonate anions. In (I), the aromatic rings of the anions are approximately coplanar, giving parallel sheets, whereas in (II) the sheets are antiparallel and the anions pack in a herring‐bone manner within the sheets, with angles of 78.76 (8)° between the planes of the aromatic rings.