3-(9H-Carbazol-9-yl)-2H-chromen-2-one

The title compound, C21H13NO2, was prepared as an example of a new synthesis of carbazoles from a cyclic dibenzo-iodolium salt via a twofold Pd-catalysed arylation of a primary amine. The two essentially planar π-subsystems [maximum deviations from the mean square plane of 0.038 (2) Å in the carbazole and 0.059 (2) Å in the coumarine unit] open a dihedral angle of 63.05 (4)°. Two molecules form a centrosymmetrical pair connected via π–π interactions between the pyrrole and pyrone rings [centroid–centroid distance = 3.882 (1) Å] and one benzene of the carbazole and the pyrone unit [centroid–centroid distance 3.824 (1) Å]. The lattice is stabilized by C—H⋯O bridging to both coumarin O atoms.

[1]  Benjamin Dassonneville,et al.  [2+2+2] Cycloadditions of Alkynylynamides – A Total Synthesis of Perlolyrine and the First Total Synthesis of “Isoperlolyrine” , 2011 .

[2]  Maria Cristina Burla,et al.  SIR97: a new tool for crystal structure determination and refinement , 1999 .

[3]  Nicolai A. Nemkovich,et al.  Subnanosecond spectrofluorimetry of new indolocarbazole derivatives in solutions and protein complexes and their dipole moments , 2009 .

[4]  Stefano Mariani,et al.  Thermal, Mechanical and MultiPhysics Simulation and Experiments in Microelectronics and Microsystems (EUROSIME'2006) , 2008 .

[5]  Dieter Schollmeyer,et al.  5-Benzyl-5H-pyrido[3,2-b]indole , 2011, Acta crystallographica. Section E, Structure reports online.

[6]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[7]  Dieter Schollmeyer,et al.  5-Methyl-3-(3-methylphenyl)-7-phenyl-1,2,4-triazolo[4,3-c]pyrimidine , 2011, Acta crystallographica. Section E, Structure reports online.

[8]  R. Lathe Phd by thesis , 1988, Nature.

[9]  G. Gattow,et al.  Kristallographische Computer-Programme für die CDC-3300. , 1971 .

[10]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[11]  M. Leclerc,et al.  Organic Microelectronics: Design, Synthesis, and Characterization of 6,12-Dimethylindolo[3,2-b]Carbazoles , 2004 .

[12]  Felix Nissen,et al.  Total Synthesis of Lavendamycin by a [2+2+2] Cycloaddition , 2011 .