1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry

• Main Authors: Dallasta Pedroso, Sofia, Caracelli, Ignez, Zukerman-Schpector, Julio, Soto-Monsalve, Monica, De Almeida Santos, Regina H., Correia, Carlos Roque D., Llanes Garcia, A. L., Kwong, Huey Chong *, Tiekink, Edward R. T. *
• Format: Article
• Language: English
• Published: International Union of Crystallography 2020
• Subjects: QD Chemistry
• Online Access: http://eprints.sunway.edu.my/1297/1/Tiekink%20Acta%20Cryst%202020%20E76%20967.pdf; http://eprints.sunway.edu.my/1297/; http://doi.org/10.1107/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.