Trans-reduction of 5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole. X-ray crystallographic study of the geometry of an intermolecular N-H ⋯ phenyl hydrogen bond

The stereochemistries of the two isomeric products (5) and (6) obtained in equal amounts from trans-reduction of 3-benzyl-5-phenyl-1,2,3,4,5,6- hexahydroazepino[4,5-b]indole (3) have been determined by spectral and single-crystal X-ray analyses. Monoclinic crystals of (5) belong to space group P21/c, with a = 22.005(10), b = 10.270(5), c = 13.577(7) Å, β = 106.42(1)°, Z = 8. The crystal structure was solved by direct methods, and atomic positional and thermal parameters refined by least-squares calculations to R 0.051 over 3 293 reflections measured by diffractometer. The two molecules defining the asymmetric crystal unit have identical conformations and are associated in a like manner in the solid state by N-H ⋯ N (mean N ⋯ N 3.26 Å) and N-H ⋯ phenyl (mean calculated H ⋯ phenyl 2.32 Å) hydrogen bonds.

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Author Andrew T. McPhail Chemistry