Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-di-hydro-1H-benzimidazol-2-one


Elmachkouri Y. A. , Saber A., Irrou E., Amer B., Mague J. T. , HÖKELEK T. , ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.77, pp.559-569, 2021 (Journal Indexed in ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77
  • Publication Date: 2021
  • Doi Number: 10.1107/s2056989021004291
  • Title of Journal : ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Page Numbers: pp.559-569

Abstract

The title molecule, C17H26N2O, adopts an L-shaped conformation, with the straight n-decyl chain positioned nearly perpendicular to the dihydro-benzimidazole moiety. The dihydrobenzimidazole portion is not quite planar as there is a dihedral angle of 1.20 (6)degrees between the constituent planes. In the crystal, N-H center dot center dot center dot O hydrogen bonds form inversion dimers, which are connected into the three-dimensional structure by C-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (75.9%), H center dot center dot center dot C/C center dot center dot center dot H (12.5%) and H center dot center dot center dot O/O center dot center dot center dot H (7.0%) interactions. Based on computational chemistry using the CE-B3LYP/6-31 G(d,p) energy model, C-H center dot center dot center dot O hydrogen bond energies are -74.9 (for N-H center dot center dot center dot O) and -42.7 (for C-H center dot center dot center dot O) kJ mol(-1).