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

Abstract

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.

The Solid-State Structures of Cyclic NH Carboximides

“…Eighteen structures have been published for 3-monosubstituted glutarimides. Fifteen of these structures, compounds 182 [158], 183 [159], 184 [160][161][162], 185 [163], 186 [159], 187 [159], 188 [164], 189 [165], 190 [166], 191 [167], 192 [168], 193 [169] and 194 [170] (Figure 57) exist as simple R 2 2 (8) dimers of pattern A. Compounds 185-187 have an additional S(6) interaction.…”

A Novel Green Synthesis of Thalidomide and Analogs

“…(Detailed 1 H and 13 C NMR spectra and mass spectrometry data are presented in the Supplementary Material available online at https://doi.org/10.1155/2017/6436185.) Further structural confirmation was provided by single crystal X-ray structural identifications [49]. Compounds 3 and 4 ORTEP are presented in Figure 3.…”