Role of weak C-H...O and strong N-H...O intermolecular interactions on the high-symmetry molecular packing of trans -cyclohexane-1,4-dicarboxamide

GARCÍA-REYES, FERNANDO; FANTONI, ADOLFO C.; BARÓN, MÁXIMO; ROMANO, ROSANA M.; PUNTE, GRACIELA M.; ECHEVERRÍA, GUSTAVO A.

Acta Crystallographica Section C Structural Chemistry

Wiley-Blackwell

Año: 2018 vol. 74

An unpredicted fourfold screw N?H O hydrogen bond C(4) motif in aprimary dicarboxamide (trans-cyclohexane-1,4-dicarboxamide, C8H14N2O2) wasinvestigated by single-crystal X-ray diffraction and IR and Raman spectroscopies.Electron-density topology and intermolecular energy analyses determinedfrom ab initio calculations were employed to examine the influence ofweak C?H O hydrogen-bond interactions on the peculiar arrangement ofmolecules in the tetragonal P43212 space group. In addition, the way in which theco-operative effects of those weak bonds might modify their relative influenceon molecular packing was estimated from cluster calculations. Based on theresults, a structural model is proposed which helps to rationalize the unusualfourfold screw molecular arrangement.