4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry

The title compound, C23H24N2O9, is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C- C bond bearing the adjacent acetyloxy substituents. These are flanked on one side by a C-bound 4-methoxyphenyl group and on the other by a methylene group. The almost sp(2)- N atom [sum of angles = 357 degrees] bears a 4-nitrobenzyloxycarbonyl substituent. In the crystal, ring-methylene-C-H center dot center dot center dot O(acetyloxy-carbonyl) and methylene-C-H center dot center dot center dot O(carbonyl) interactions lead to supramolecular layers lying parallel to ((1) over bar 01); the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces indicates the combined importance of H center dot center dot center dot H (42.3%), H center dot center dot center dot O/O center dot center dot center dot H (37.3%) and H center dot center dot center dot C/C center dot center dot center dot H (14.9%) surface contacts. Further, the interaction energies, largely dominated by the dispersive term, point to the stabilizing influence of H center dot center dot center dot H and O center dot center dot center dot O contacts in the interlayer region.