3-Amino-1-(4-fluoro-phen-yl)-7-meth-oxy-1H-benzo[f]chromene-2-carbonitrile

Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 2;69(Pt 4):o478-9. doi: 10.1107/S1600536813005473. Print 2013 Apr 1.

Abstract

In the title compound, C21H15FN2O2, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C5 plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluoro-benzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supra-molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {⋯HNC3N}2 and eight-membered {⋯HNCO}2 synthons. These are connected into a three-dimensional architecture by π-π [inter-centroid distance for centrosymmetrically related fluoro-benzene rings = 3.5181 (10) Å] and C-H⋯π inter-actions.