Abstract
The title naturally occurring carbazole compound, C18H17NO3, known as heptazoline, was isolated from Micromelum minutum. The carbazole ring system is essentially planar. The hydroxy and aldehyde substituent groups lie in the plane of the benzene ring, while the 3-methyl-2-butenyl group is anticlinal, with a dihedral angle of 70.26 (7)° between it and the mean plane of the carbazole. In the crystal structure, an intramolecular O—H⋯O interaction generates an S(6) ring motif, while an intermolecular O—H⋯O interaction forms dimers that link into chains along the [401] direction. The structure is further stabilized by weak intramolecular C—H⋯O interactions and π–π interactions [centroid-to-centroid distances 3.5901 (8) and 3.5899 (8) A].
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