Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of (S)-10-propargyl-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dione.

ABSTRACT: The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt half-chair 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-HBnz?ODiazp and C-HProprg?ODiazp (Bnz = benzene, Diazp = diazepine and Proprg = proparg-yl) hydrogen bonds link the mol-ecules 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?H (49.8%), H?C/C?H (25.7%) and H?O/O?H (20.1%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, C-H?O hydrogen-bond energies are 38.8 (for C-HBnz?ODiazp) and 27.1 (for C-HProprg?ODiazp) kJ?mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311?G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

SUBMITTER: Jeroundi D 

PROVIDER: S-EPMC7133028 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature