Related Experiment Video
Updated: Jun 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
2-((E)-{2-[(E)-2,3-Dihydroxy-benzyl-ideneamino]-5-methyl-phen-yl}iminiometh-yl)-6-hydroxy-phenolate
Abstract:
The asymmetric unit of the title Schiff base compound, C(21)H(18)N(2)O(4), consists of four independent zwitterions (A, B, C and D) with similar conformations. In each independent mol-ecule, the methyl group is disordered over two positions; the occupancies of the two positions are 0.819 (5) and 0.181 (5) in mol-ecule A, 0.912 (5) and 0.088 (5) in B, 0.734 (5) and 0.266 (5) in C, and 0.940 (6) and 0.060 (6) in D. The dihydroxy-phenyl and the hydroxy-phenolate rings in mol-ecule A form dihedral angles of 17.36 (12) and 13.30 (12)°, respectively, with the central benzene ring, whereas the respective angles for mol-ecules B, C and D are 30.22 (11)/7.46 (11), 35.26 (12)/11.01 (12) and 39.89 (12)/4.29 (12)°. In all independent mol-ecules, intra-molecular N-H⋯O and O-H⋯N hydrogen bonds generate S(6) ring motifs. The four independent mol-ecules are linked into two pairs, viz. A-B and C-D, by inter-molecular O-H⋯O hydrogen bonds. These pairs are linked into a two-dimensional network parallel to the ab plane by C-H⋯O hydrogen bonds. In addition, C-H⋯π and π-π [centroid-centroid distance = 3.5153 (14)-3.7810 (15) Å] inter-actions stabilize the crystal structure.
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