Crystal structure and Hirshfeld surface analysis of (4 Z)-1-butyl-4-(2-oxo-propyl-idene)-2,3,4,5-tetra-hydro-1 H-1,5-benzodiazepin-2-one

Acta Crystallogr E Crystallogr Commun. 2018 Oct 26;74(Pt 11):1669-1673. doi: 10.1107/S2056989018014779. eCollection 2018 Nov 1.

Abstract

The asymmetric unit of the title compound, C16H20N2O2, consists of two independent mol-ecules differing slightly in the conformations of the seven-membered rings and the butyl substituents, where the benzene rings are oriented at a dihedral angle of 34.56 (3)°. In the crystal, pairwise inter-molecular C-H⋯O and complementary intra-molecular C-H⋯O hydrogen bonds form twisted strips extending parallel to (012). These strips are connected into layers parallel to (111) by additional inter-molecular C-H⋯O hydrogen bonds. The layers are further joined by C-H⋯π inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (65.5%), H⋯C/C⋯H (16.0%) and H⋯O/O⋯H (15.8%) inter-actions.

Keywords: Hirshfeld surface; benzodiazepine; crystal structure; hydrogen bond; π-stacking.

Grants and funding

This work was funded by Tulane University grant . Hacettepe University Scientific Research Project Unit grant 013 D04 602 004 to T. Hökelek.