N-(3-Cyanoprop-2-ynyl)carbazole: synthesis, crystal structure, and solid-state reactivity

N-(3-Cyanoprop-2-ynyl)carbazole (1) was synthesized in 30% yield by reactio n of N-(3-bromoprop-2-ynyl)carbazole (2) with cuprous cyanide in tetrahydro furan, or by reaction of lithiated N-(prop-2-ynyl)carbazole (3) with 1-cyan obenzotriazole in 70% yield. Grown from hexane-dichloromethane solution, co mpound 1 crystallizes in the orthorhombic space group P2(1)2(1)2(1), with a = 6.5553(6), b = 11.3879(25), c = 16.2752(24) Angstrom, V = 1215.0(3) Angs trom (3), and Z = 4. The title compound undergoes a thermally induced solid -state oligomerization, largely following a 1,2-addition pathway, consisten t with the arrangement of molecules observed in the crystal structure.