4-Nitro-benzyl 3,4-bis-(acet-yloxy)-2-(4-meth-oxy-phen-yl)pyrrolidine-1-carboxyl-ate: crystal structure, Hirshfeld surface analysis and computational chemistry

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 76; no. Pt 7; pp. 1080 - 1086
• Main Authors: Dallasta Pedroso, Sofia, Caracelli, Ignez, Zukerman-Schpector, Julio, Soto-Monsalve, Monica, De Almeida Santos, Regina H, Correia, Carlos Roque D, Llanes Garcia, Ariel L, Kwong, Huey Chong, Tiekink, Edward R T
• Format: Journal Article
• Language: English
• Published: England International Union of Crystallography 01-07-2020
• Subjects: Research Communications; crystal structure; NCI plots; Hirshfeld surface analysis; computational chemistry; pyrrolidine
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989020007914

The title compound, C
H
N
O
, is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C-C bond bearing the adjacent acet-yloxy substituents. These are flanked on one side by a C-bound 4-meth-oxy-phen-yl group and on the other by a methyl-ene group. The almost
-N atom [sum of angles = 357°] bears a 4-nitro-benzyl-oxycarbonyl substituent. In the crystal, ring-methyl-ene-C-H⋯O(acet-yloxy-carbon-yl) and methyl-ene-C-H⋯O(carbon-yl) inter-actions lead to supra-molecular layers lying parallel to (01); the layers stack without directional inter-actions 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 inter-action energies, largely dominated by the dispersive term, point to the stabilizing influence of H⋯H and O⋯O contacts in the inter-layer region.