CRYSTAL STRUCTURE AND HIRSHFELD SURFACE ANALYSIS OF 1,3-DIETHYL-5-NITRO-1H-BENZOIMIDAZOL-2(3H)-ONE

Abstract

The dihydrobenzodiazolone skeleton of the title compound, C11H13N3O3, is quite planar with
the 1,3-diethyl substituents rotated well out of the dihydrobenzodiazolone mean plane. In the
crystal, the molecules are linked via the intermolecular C—HBnzdaz···ODhybnzdaz (Bnzdaz =
benzodiazole and Dhybnzdaz = dihydrobenzodiazolone) hydrogen bonds, forming infinite
chains along [101]. These chains are further linked by the π-stacking interactions between the
5- and 6-membered rings to stabilize the structure with centroid···centroid distances of
3.8624(10)Å and 3.6721(9)Å, respectively. The Hirshfeld surface analysis of the crystal
structure indicates that the most important contributions for the crystal packing are from H ···
H (44.3%), H ··· O/O ··· H (34.9%), C ··· C (6.2%) and H ··· C/C ··· H (5.8%) interactions.
Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal
packing.