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

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.

Fig. 1.

The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.

Fig. 2.

A view of the supramolecular zigzag tape along the b axis in (I). The N—H···N and N—H···O hydrogen bonds are shown as blue and orange dashed lines, respectively.

Fig. 3.

A view in projection down the a axis of the crystal packing in (I). The N—H···N, N—H···O, C—H···π and π—π interactions are shown as blue, orange, brown and purple dashed lines, respectively.