Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione


Jeroundi D., Mazzah A., HÖKELEK T. , El Hadrami E. M. , Renard C., Haoudi A., ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.467-477, 2020 (ESCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 76
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1107/s2056989020002698
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Sayfa Sayıları: ss.467-477

Özet

The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt halfchair and boat conformations, respectively. The absolute configuration was assigned on the the basis of l-proline, which was used in the synthesis of benzodiazepine. In the crystal, weak C-H-Bnz center dot center dot center dot O-Diazp and C-H-Proprg center dot center dot center dot O-Diazp (Bnz = benzene, Diazp = diazepine and Proprg = propargyl) hydrogen bonds link the molecules into two-dimensional networks parallel to the bc plane, enclosing R-4(4)(28) ring motifs, with the networks forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (49.8%), H center dot center dot center dot C/C center dot center dot center dot H (25.7%) and H center dot center dot center dot O/O center dot center dot center dot H (20.1%) interactions. Hydrogen bonding and van derWaals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C-H center dot center dot center dot O hydrogen-bond energies are 38.8 (for C-H-Bnz center dot center dot center dot O-Diazp) and 27.1 (for C-H-Proprg center dot center dot center dot O-Diazp) kJ mol(-1). Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.