1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: 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 2020-06-01
• 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?S205698902000701X

The title compound, C13H19NO8, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the Cm—Ca—Ca—Cme torsion angle is 38.26 (15)° [m = methylcarboxylate, a = acetyloxy and me = methylene]. While the N-bound ethylcarboxylate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supramolecular double-layers are formed by weak methyl- and methylene-C—H...O(carbonyl) interactions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional interactions between them. The Hirshfeld surface is dominated by H...H (55.7%) and H...C/C...H (37.0%) contacts; H...H contacts are noted in the inter-double-layer region. The interaction energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal.