Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: Dimeric structure formation via [O-H-O]- negative charge-assisted hydrogen bonds (-CAHB) with benzyltrimethylammonium counter-ions

Ravell Bengiat, Maayan Gil, Asne Klein, Benny Bogoslavsky, Shmuel Cohen, Joseph Almog*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8 -·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O⋯O = 2.4395(13)Å] [O-H-O]- bonds of the type negative charge-assisted hydrogen bonds (-CAHB). The central aromatic rings of the ligands create parallel-displaced π-π stacking at an interplanar distance of 3.381(1)Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O-H⋯O hydrogen bonds, forming chains along [101].

Original languageEnglish
Pages (from-to)399-402
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
DOIs
StatePublished - 2016

Bibliographical note

Publisher Copyright:
© 2016 Bengiat et al.s.

Keywords

  • crystal structure
  • negative charge-assisted hydrogen bond [(-)CAHB]
  • ninhydrin
  • supramolecular dimer
  • vasarene

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