6533b824fe1ef96bd128081e

RESEARCH PRODUCT

A noncentrosymmetric crystal structure of a zwitterionic compound, pyridinium 5,7-dihydro-5,7-dioxo-6H-cyclopenta[b]pyridin-6-ylide, realized by weak hydrogen bonds

Ojars NeilandsHiroyuki YoshidaJun'ya TsutsumiTakahiro SasamoriNaoki SatoInta MuzikanteNorihiro TokitohShigeki Kato

subject

Diffractionchemistry.chemical_classificationLattice energyHydrogen bondOrganic ChemistryCrystal structureAnalytical ChemistryInorganic Chemistrychemistry.chemical_compoundCrystallographychemistryYlideIntermolecular interactionMoleculePyridiniumSpectroscopy

description

Abstract Crystal structures of pyridinium 1,3-dihydro-1,3-dioxo-2 H -inden-2-ylide (PI) of a zwitterionic molecule and its nitrogen substituted compounds, 4N-PI and 5N-PI, were solved with X-ray diffraction analyses. Whereas PI and 5N-PI showed centrosymmetric crystal structures, 4N-PI demonstrated a noncentrosymmetric crystal structure where all the molecules orient to almost the same direction. To elucidate the stability of such a polarized structure, we examined interatomic close contacts among the nearest neighbor molecules in the crystals and calculated intermolecular interaction energies with relation to those contacts. As a result, the noncentrosymmetric crystal structure of 4N-PI turns out to be realized by a weak hydrogen bond in the C–H···N manner formed only in the case of this compound.

yearjournalcountryeditionlanguage
2009-02-01Journal of Molecular Structure
https://doi.org/10.1016/j.molstruc.2008.10.021