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.
Highlights
Dounia Jeroundi,a* Ahmed Mazzah,b Tuncer Hokelek,c El Mestafa El Hadrami,a Catherine Renard,d Amal Haoudia and El Mokhtar Essassie
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
Summary
Over the past few decades, compounds bearing heterocyclic nuclei have received much attention of chemists and biologists because of their importance in the development of chemotherapeutic agents and a wide variety of drugs (Cargill et al, 1974; Micale et al, 2004; Hadac et al, 2006; Ourahou et al, 2011). 1,4-Benzodiazepines and their derivatives have attracted the attention of chemists since the early 1960s, mainly because of the broad spectrum of biological properties exhibited by this class of compounds, in particular their psychopharmacological properties (Thurston & Langley, 1986; Kamal et al, 2007; Antonow et al, 2007; Archer & Sternbach, 1968; Mohiuddin et al, 1986, Bose et al, 1992; Gregson et al, 2004). 1,4-Benzodiazepines and their derivatives have attracted the attention of chemists since the early 1960s, mainly because of the broad spectrum of biological properties exhibited by this class of compounds, in particular their psychopharmacological properties (Thurston & Langley, 1986; Kamal et al, 2007; Antonow et al, 2007; Archer & Sternbach, 1968; Mohiuddin et al, 1986, Bose et al, 1992; Gregson et al, 2004). Pyrrolo[2,1-c][1,4]benzodiazepines are a group of potent chemicals produced by Streptomyces species. For their anticancer activity, see: Bose et al (1992); Cargill et al (1974); Gregson et al (2004). The results of the calculations by density functional theory (DFT), carried out at the B3LYP/6-311G (d,p) level, are compared with the experimentally determined molecular structure in the solid state
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