Akademik Veri Yönetim Sistemi
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.467-477, 2020 (ESCI)
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.