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In order to examine packing preferences and hydrogen bond patterns in secondary ammonium salts, low-temperature X-ray analyses were conducted for six compounds of general formula R 2 NH 2  + MeSO 2 ) 2  N - , where R 2 NH 2  +  = Me 2 NH 2  +  (1, triclinic, space group P1̄̄), MeEtNH 2  + ,(2, monoclinic, P2 1 /c), Et 2 NH 2  +  (3. triclinic, P1), pyrrolidinium (4, triclinic, P1), piperidinium (5, monoclinic, C2/c) or morpholinium (6, monoclinic, P2 1/ c). Throughout the series, the constant anion retains a rigid conformation approximating to C 2  symmetry and thus provides a geometrically reliable set of five potential hydrogen bond acceptors. Nevertheless, the six compounds exhibit a variety of unpredictable packing patterns, showing that, in unfavourable cases, the steric demands of molecular fragments not involved in hydrogen bonding can substantially alter the structure of a family of ionic crystals. In the present structures, the NH 2  +  donor groups form hydrogen bonds N + -H···N - /O to two (3-6) or three (1,2) adjacent anions. The occurrence of various two-, three- and four-centre hydrogen bonds leads to six different patterns, resulting in cation-anion layers (1, 2), discrete formula unit dimers (3, 4) or cation-anion chains (5, 6); in the morpholinium salt 6, these chains are associated into layers by a weak N +  - H ··· O(cation) interaction. In each of the crystal packings, short C-H···O contacts with H···O ≤ 270 pm and C-H ···O ≥ 130° are observed.

zeitschrift für naturforschung b

Polysulfonylamine, CXVII  Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Sechs systematisch variierte sek.-Ammonium-dimesylamide mit sechs verschiedenen null-, ein-oder zweidimensionalen Wasserstoffbrückenmustern/ Polysulfonylamines, CXVII  Hydrogen Bonding in Crystalline Onium Dimesylamides: Six Systematically Varied sec. - Ammonium Dimesylamides Exhibiting Six Different Zero-, One-, or Two-Dimensional Hydrogen Bonding Patterns