Polymorphic inclusion structure types of solvated 2,4-dichloro-5-carboxy-benzsulfonimide. A study of solvation patterns and their influence on molecular conformation

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Abstract

The inclusion behavior of 2,4-dichloro-5-carboxy-benzsulfonimide in protic (water, acetic acid and methanol) and aprotic (N,N-dimethylacetamide) environments has been examined by crystal structure determinations of the solvated compound, providing an illustration of the relationship between solvation effects and structural polymorphism. Three different crystal structure types of the corresponding complexes in which the benzsulfonimide moiety, C14H7Cl4NO8S2, exhibits different conformations have been observed [I (with 4 mol of water) - {Mathematical expression}, a=8.227, b=8.964, c=16.945 Å, α=89.64, β=97.51, γ=114.28°;II (with acetic acid + 2 H2O) - {Mathematical expression}, a=7.857, b=11.379, c=13.831 Å, α=92.50, β=101.21, γ=101.12° and III (with methanol + 2H2O) - {Mathematical expression} or P1, a=7.840, b=11.235, c=13.697 Å, α=95.56, β=102.05, γ=102.21°;IV (with 2 N,N-dimethylacetamide + 2H2O) -P212121, a=14.838, b=14.818, c=14.500 Å]. Crystallization from water and from acetic acid leads to layered structures consisting of alternating zones of the host (with a folded conformation) and the solvent. Crystals obtained from N,N-dimethylacetamide are composed of a three-dimensional lattice of loosely packed host species (with an extended conformation) which are interspaced by solvent molecules. This polymorphism can be correlated to hydrogen bonding in that the extended conformation of the title compound is favored in a solvent which is a poor hydrogen donor, while the folded conformation is induced in solvation environments that are good donors of hydrogen bonds.

Original languageEnglish
Pages (from-to)349-364
Number of pages16
JournalJournal of Inclusion Phenomena
Volume1
Issue number4
DOIs
StatePublished - Dec 1984

Keywords

  • solvation patterns
  • solvent inclusion
  • structural polymorphism

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