Ethyl 4-hydroxy-9-tosyl-9H-carbazole-3-carboxylate

Tuncer Hökelek,Barış Tercan,Sibel Gülle,Hakan Dal,Yavuz Ergün

doi:10.1107/s1600536809021035

Abstract

In the title compound, C22H19NO5S, the carbazole skeleton is nearly planar [maximum deviation = 0.043 (1) Å] with the pyrrole ring oriented at dihedral angles of 2.32 (6) and 1.77 (6)° with respect to the adjacent benzene rings. The dihedral angle between the benzene ring of the tosyl group and the carbazole skeleton is 82.25 (5)°. Intramolecular O—H⋯O hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of 3.06 (4)° with respect to the adjacent carbazole skeleton. In the crystal structure, weak intermolecular C—H⋯O interactions link the molecules into infinite chains and π–π contacts between the benzene rings and between the pyrrole and benzene rings [centroid–centroid distances = 3.374 (1) and 3.730 (1) Å, respectively] may further stabilize the structure. A weak C—H⋯π interaction is also present.

Highlights

C22H19NO5S, the carbazole skeleton is nearly planar [maximum deviation = 0.043 (1) Å] with the pyrrole ring oriented at dihedral angles of 2.32 (6) and
H O hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of
Weak intermolecular C—H O interactions link the molecules into infinite chains and – contacts between the benzene rings and between the pyrrole and benzene rings [centroid–centroid distances = 3.374 (1) and

Summary

Structure Reports

C22H19NO5S, the carbazole skeleton is nearly planar [maximum deviation = 0.043 (1) Å] with the pyrrole ring oriented at dihedral angles of 2.32 (6) and. 1.77 (6) with respect to the adjacent benzene rings. The dihedral angle between the benzene ring of the tosyl group and the carbazole skeleton is 82.25 (5). H O hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of. 3.06 (4) with respect to the adjacent carbazole skeleton. Weak intermolecular C—H O interactions link the molecules into infinite chains and – contacts between the benzene rings and between the pyrrole and benzene rings [centroid–centroid distances = 3.374 (1) and. 3.730 (1) Å, respectively] may further stabilize the structure.

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