Ritter reactions. X. Structure of a new multicyclic amide-benzene inclusion compound

5H-Dibenzo[a, d]cyclohepten-5-ol1 can undergo Ritter reaction with acetonitrile and sulfuric acid to afford either the acetamide derivative2 or the multicyclic amide3 depending on the conditions used. The X-ray structure of the inclusion compound of3 with benzene is reported here and analysed in structural terms. This material [(C₁₉H₁₈N₂O)–(C₆H₆),Cc,a=10.694(5),b=22.843(5),c=9.901(4) Å,=124.02(2)°,Z=4,R=0.054] has molecules of3 linked by –N–HO=C intermolecular hydrogen bonds to form parallel chains alongc. Additional inter-host stabilisation is achieved by face-face interactions involving one of the two benzo rings of3. A hydrogen atom of the other host benzo group participates in an edge-face interaction with the benzene guest molecule to produce the inclusion compound. Benzenebenzene inter-guest interactions provide a further, but minor, contribution to the net stability of the structure.Supplementary Data relating to this article are deposited with the British Library as supplementary publication No. SUP 82189 (10 pages).