Title of article :
1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry
Author/Authors :
Pedroso, Sofia Dallasta Laboratório de Cristalografia - Esterodinâmica e Modelagem Molecular - Departamento de Química - Universidade Federal de São Carlos, Brazil , Caracelli, Ignez Departmento de Física - Universidade Federal de São Carlos, Brazil , Zukerman-Schpector, Julio Laboratório de Cristalografia - Esterodinâmica e Modelagem Molecular - Departamento de Química - Universidade Federal de São Carlos, Brazil , Soto-Monsalve, Monica Instituto de Química de São Carlos - Universidade de São Paulo - São Carlos, SP, Brazil , De Almeida Santos, Regina H. nstituto de Química de São Carlos - Universidade de São Paulo - São Carlos, SP, Brazil , Correia, Carlos Roque D. Instituto de Química - Universidade Estadual de Campinas, UNICAMP, Brazil , Llanes Garcia, Ariel L. Instituto de Química - Universidade Estadual de Campinas, UNICAMP, Brazil , Kwong, Huey Chong Research Centre for Crystalline Materials - School of Science and Technology - Sunway University, Malaysia , Tiekink, Edward R. T. Research Centre for Crystalline Materials - School of Science and Technology - Sunway University, Malaysia
Abstract :
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.
Keywords :
crystal structure , pyrrolidine , Hirshfeld surface analysis , NCI plots , computational chemistry
