Abstract
Two crystallographically independent mol-ecules are present in the asymmetric unit of the title compound, C14H11NO2, with virtually identical geometries. The carbazole units are planar. The hy-droxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the exception of two H atoms) are coplanar with the attached benzene rings. The dihedral angle between the two benzene rings is 2.20 (9)° in mol-ecule A and 2.01 (9)° in mol-ecule B. The pyrrole ring makes dihedral angles of 0.82 (10) and 1.40 (10)° [0.84 (10) and 1.18 (10)° in mol-ecule B] with the (-CH3)-substituted and (-OH and -CHO) substituted benzene rings, respectively. The mol-ecular structure is stabilized by the intra-molecular O-H⋯O hydrogen bonds, while the crystal structure features N-H⋯O and C-H⋯O hydrogen bonds. A range of π-π contacts further stabilizes the crystal structure.
Highlights
Two crystallographically independent molecules are present in the asymmetric unit of the title compound, C14H11NO2, with virtually identical geometries
The molecular structure is stabilized by the intramolecular O—HÁ Á ÁO hydrogen bonds, while the crystal structure features N—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds
We report the synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2carbaldehyde (Fig. 1), which is a potential precursor for the synthesis of many hetero-annulated carbazoles (Gunaseelan et al, 2007)
Summary
Nitrogen-containing heterocyclic compounds are key building blocks used to develop chemicals of biological and medicinal interest. Carbazole alkaloids represent an important class of natural products. The Indian medicinal plant Murraya koenigii spreng (Rutaceae) is a rich source of carbazole alkaloids (Knolker & Reddy, 2002), and a number of these natural products with novel structures and useful biological activities have been isolated from this plant over the past decades. The increase of isolable natural products as well as the pharmacological action of these carbazole derivatives has generated synthetic interest; the synthesis of carbazoles has been an active area of study. Biological and pharmacological importance of carbazole derivatives, the present investigation was to devise a viable synthetic route to these compounds using different methodologies. 2,3,4,9-tetrahydro-1H-carbazol-1-ones prepared in our laboratory were used as precursors, opening new avenues for the synthesis of highly functionalized carbazole derivatives such as 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles, 1-hydroxycarbazoles, and 1-hydroxy-2-formylcarbazoles.
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