Crystal structure of anagyrine perchlorate

Abstract

The title molecular salt, C15H21N2O+·ClO4−, crystallizes with four cations (A, B, C and D) and four anions in the chiral unit cell (space group P21). The alkaloid was isolated from the aerial parts of Genista Hispanica collected in the Samarkand region of Uzbekistan. Each cation is protonated at the N atom that bridges the alkaloid rings C and D. In each cation, ring A is almost planar and ring B adops a sofa conformation with the methylene group bridging to the C ring as the flap. Rings C and D adopt chair conformations with a cis ring junction in all four cations. In the crystal, A+B and C+D dimeric pairs linked by pairs of N—H...O hydrogen bonds are observed, which generate R22(16) loops in each case. The dimers are consolidated by weak aromatic π–π stacking interactions between the A rings [centroid–centroid distances = 3.913 (3) and 3.915 (3) Å].

Keywords

• crystal structure
• alkaloid
• Genista Hispanica
• anagyrine
• perchlorate
• N—H...O hydrogen bonds
• π–π stacking interactions