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

• Main Authors: Sofia Dallasta Pedroso, Ignez Caracelli, Julio Zukerman-Schpector, Monica Soto-Monsalve, Regina H. De Almeida Santos, Carlos Roque D. Correia, Ariel L. Llanes Garcia, Huey Chong Kwong, Edward R. T. Tiekink
• Format: Article
• Language: English
• Published: International Union of Crystallography 2020-07-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; pyrrolidine; hirshfeld surface analysis; nci plots; computational chemistry
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989020007914

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 sp2-N atom [sum of angles = 357°] bears a 4-nitrobenzyloxycarbonyl substituent. In the crystal, ring-methylene-C—H...O(acetyloxy-carbonyl) and methylene-C—H...O(carbonyl) interactions lead to supramolecular layers lying parallel to (\overline{1}01); the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces indicates the combined importance of H...H (42.3%), H...O/O...H (37.3%) and H...C/C...H (14.9%) surface contacts. Further, the interaction energies, largely dominated by the dispersive term, point to the stabilizing influence of H...H and O...O contacts in the inter-layer region.