3-(2,6-Dioxopiperidin-3-yl)-3-azabicyclo[3.2.0]heptane-2,4-dione

The title molecule, C11H12N2O4, consists of a 3-azabicyclo[3.2.0]heptane group containing a nearly planar cyclobutane ring (r.m.s. deviation of fitted atoms is 0.0609 Å), fused to a pyrrolidine ring, bonded to a 2,6-dioxopiperidine ring at the 3-position. The angle between the mea...

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Bibliographic Details
Main Authors: Jerry P. Jasinski, Ray J. Butcher, Earl Benjamin, Ellis Benjamin, Yousef M. Hijji
Format: Article
Language:English
Published: International Union of Crystallography 2009-02-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536809002839
Description
Summary:The title molecule, C11H12N2O4, consists of a 3-azabicyclo[3.2.0]heptane group containing a nearly planar cyclobutane ring (r.m.s. deviation of fitted atoms is 0.0609 Å), fused to a pyrrolidine ring, bonded to a 2,6-dioxopiperidine ring at the 3-position. The angle between the mean planes of the cyclobutane and fused pyrrolidine ring is 67.6 (6)°. The dihedral angles between the mean planes of the pyrrolidine and cyclobutane rings and the dioxopiperidine ring are 73.9 (2) and 62.4 (4)°, respectively. The pyrrolidine and dioxopiperidine rings are twisted about the 3-yl group [torsion angles = −55.0 (1) and 115.0 (1)°] in a nearly perpendicular manner. Crystal packing is influenced by extensive intermolecular C—H...O and N—H...O interactions between all four carbonyl O atoms and H atoms from the cyclobutane and dioxopiperidine rings, as well as between the N atom and an H atom from the cyclobutane ring. In addition, weak π-ring interactions also occur between H atoms from the cyclobutane ring and the five-membered pyrrolidine ring. As a result, molecules are linked into infinite chains diagonally along the [101] plane of the unit cell in an alternate inverted pattern.
ISSN:1600-5368