Research Article: 4-Meth­oxy­benzoyl-meso-octa­methyl­calix[2]pyrrolidino[2]pyrrole: an acyl chloride derivative of a partially reduced calix[4]pyrrole

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Guillaume Journot, Reinhard Neier, Helen Stoeckli-Evans.


In the title compound, C36H50N4O2, the two pyrrolidine rings have envelope conformations. The conformation of the macrocycle is stabilized by N—H⋯N hydrogen bonds and a C—H⋯N inter­action. The benzoyl ring is inclined to an adjacent pyrrole ring by 6.76 (9)°, with a centroid-to-centroid distance of 3.6285 (10) Å. In the crystal, apart from a C—H⋯O and a C—H⋯π inter­action, mol­ecules are linked via an N—H⋯O hydrogen bond, leading to the formation of helical chains propagating along [010].

Partial Text

For the heterogeneous catalytic hydrogenation of meso-octa­methyl­calix[4]pyrrole, which gave meso-octa­methyl­calix[2]pyrrole­[2]pyrrolidine, see: Blangy et al. (2009 ▶). For the N-acyl­ation of pyrrolidines using substituted benzoyl chlorides, see: Journot et al. (2012a ▶); Zhang et al. (2009 ▶). For the synthesis and reactivity of the title compound, see: Journot & Neier (2012 ▶). For the crystal structures of similar compounds, see: Journot et al. (2012b ▶,c ▶,d ▶,e ▶)