Abstract
The title acridone alkaloid [systematic name: 1,3,5-trihydroxy-2,4-bis(3-methylbut-2-enyl)acridin-9(10H)-one], C23H25NO4, known as atalaphylline, was isolated from Atalantia monophylla Corrêa, a mangrove plant. The molecule contains three fused planar rings with an r.m.s. deviation of 0.026 (2) Å. Both 3-methylbut-2-enyl substituents are in a (−)anticlinal conformation. An intramolecular N—H⋯O hydrogen bond generates an S(5) ring motif, while an intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, the molecules are linked into screw chains along [010] by intermolecular O—H⋯O hydrogen bonds. These chains are stacked along the a axis by π–π interactions with centroid–centroid distances of 3.6695 (13) and 3.6696 (13) Å.
Highlights
The title acridone alkaloid [systematic name: 1,3,5-trihydroxy2,4-bis(3-methylbut-2-enyl)acridin-9(10H)-one], C23H25NO4, known as atalaphylline, was isolated from Atalantia monophylla Corrêa, a mangrove plant
The molecules are linked into screw chains along
We previously reported the crystal structure of N-methylataphyllinine, an acridone alkaloid which was isolated from the same plant (Chukaew et al, 2007)
Summary
Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
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