Title of article :
4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: 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 , Schpector, Julio Zukerman- 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, Brazil , De Almeida Santos, Regina H. Instituto de Química de São Carlos - Universidade de São Paulo, 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, 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—HO(acetyloxy-carbonyl) and methylene-C—
HO(carbonyl) interactions lead to supramolecular layers lying parallel to
(101); the layers stack without directional interactions between them. The
analysis of the calculated Hirshfeld surfaces indicates the combined importance
of HH (42.3%), HO/OH (37.3%) and HC/CH (14.9%) surface
contacts. Further, the interaction energies, largely dominated by the dispersive
term, point to the stabilizing influence of HH and OO contacts in the interlayer region.
Keywords :
crystal structure , pyrrolidine , computational chemistry , NCI plots , Hirshfeld surface analysis , pyrrolidine
