Crystal structure of dimethyl 3,3′-[(3-fluorophenyl)methylene]bis(1H-indole-2-carboxylate)

Abstract

In the title compound, C27H21FN2O4, the mean planes of the two indole ring systems (r.m.s. deviations = 0.0166 and 0.0086 angstrom) are approximately perpendicular to one another, making a dihedral angle of 87.8 (5)degrees; the fluorobenzene ring is twisted with respect to the mean planes of the two indole ring systems at 82.7 (5) and 85.5 (3)degrees. In the crystal, pairs of N-H center dot center dot center dot O hydrogen bonds link the molecules into the inversion dimers, which are further linked by N-H center dot center dot center dot O hydrogen bonds into supramolecular chains propagating along the b-axis direction. Weak C-H center dot center dot center dot pi interactions are observed between neighbouring chains.