Abstract
The title pyrrolidine compound, C18H23NO7, is a tetra-substituted species in which the five-membered ring has a twisted conformation with the twist occurring in the C-C bond bearing the adjacent acet-yloxy substituents; the Cm-Ca-Ca-Cp torsion angle is -40.76 (18)° [m = methyl-ene, a = acet-yloxy and p = phen-yl]. The N atom, which is sp 2-hybridized [sum of bond angles = 359.4°], bears an ethyl-carboxyl-ate substitutent and is connected to a methyl-ene-C atom on one side and a carbon atom bearing a 4-meth-oxy-phenyl group on the other side. Minor disorder is noted in the ethyl-carboxyl-ate substituent as well as in one of the acet-yloxy groups; the major components of the disorder have site occupancies of 0.729 (9) and 0.62 (3), respectively. The most notable feature of the mol-ecular packing is the formation of helical, supra-molecular chains aligned along the b-axis direction whereby the carbonyl-O atom not involved in a disordered residue accepts C-H⋯O inter-actions from methyl-ene-H and two-C atom separated methine-H atoms to form a six-membered {⋯HCCCH⋯O} synthon.
Highlights
The title pyrrolidine compound, C18H23NO7, is a tetra-substituted species in which the five-membered ring has a twisted conformation with the twist occurring in the C—C bond bearing the adjacent acetyloxy substituents; the Cm—Ca—Ca—Cp torsion angle is À40.76 (18) [m = methylene, a = acetyloxy and p = phenyl]
The most notable feature of the molecular packing is the formation of helical, supramolecular chains aligned along the b-axis direction whereby the carbonyl-O atom not involved in a disordered residue accepts C—HÁ Á ÁO interactions from methylene-H and two-C atom separated methine-H atoms to form a six-membered {Á Á ÁHCCCHÁ Á ÁO} synthon
The conformation of the five-membered ring is best described as being twisted about the C2—C3 bond as seen in the value of the C1—C2— C3—C4 torsion angle of À40.76 (18), which is consistent with a (À)syn-clinal configuration
Summary
134 139 the N1-bound substituent is a 4-nitrophenylmethyl group while the other groups are the same (Dallasta Pedroso et al, 2020a) while in the other, only the substituent at the C4 differs, with the literature structure having a methylcarboxylate group (Dallasta Pedroso et al, 2020b). Owing to the presence of disorder in the residues bound at the N1 and C3 atoms, a detailed analysis of the molecular packing is problematic. Supramolecular chains propagating along the b-axis direction may be discerned, Fig. 2(a). These have a helical topology being generated by 21screw symmetry and arise as the carbonyl-O1 accepts two C— HÁ Á ÁO interactions, Table 1, from the C1-methylene and C3methine substituents with the result that six-membered {Á Á ÁHCCCHÁ Á ÁO} synthons are apparent.
Sign-in/Register to view highlights & summary 
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call