tert-Butyl 3-(8-bromo-4H,10H-1,2-oxazolo[4,3-c][1]benzoxepin-10-yl)-2-methyl-1H-indole-1-carboxylate

Abstract

In the title compound, C25H23BrN2O4, the seven-membered ring adopts a twisted-boat conformation. The indole ring system is planar within 0.021 (2) Å and the ester group [–C(=O)—O—C–] is almost coplanar with it [dihedral angle = 3.0 (2)°]. The conformation of the ester group is influenced by intra­molecular C—H⋯O inter­actions. In the crystal structure, mol­ecules are linked into chains along the b axis by C—H⋯N hydrogen bonds.

cis-6-Bromo-4-(1-methyl-1H-indol-3-yl)-10,10a-dihydro-1H,4H-2,9-dioxa-3-azabenz[f]azulene

“…The maximum deviation of the atom Br1 from the phenyl ring (C15-C20) is 0.0635 (4)Å. The angles around atom C10 [C9-C10-C20 = 113.84 (18)°, C11-C10-C9 = 116.65 (18)° and C11-C10-C20 = 107.06 (17)°] deviates significantly from ideal tetrahedral values which may be as a result of steric interactions between isoxazole, bromophenol and indole moieties (Trigunait et al, 2010).…”

“…For intramolecular nitrile oxide cycloaddition (INOC) reactions, see: Scott et al (2006); Mukaiyama & Hoshino (1960). For a related structure, see: Trigunait et al (2010). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).…”