Ethyl 2-amino-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromene-3-carboxylate

Ahmed M El-Agrody,Tze Shyang Chia,Hoong-Kun Fun,Abdel-Galil E Amr,Mohamed A Al-Omar

doi:10.1107/s1600536812021939

Abstract

In the title compound, C23H20FNO4, the fluoro-substituted benzene ring is approximately perpendicular to the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.264 (1) Å], with a dihedral angle of 83.79 (6)°. The pyran ring adopts a flattened boat conformation. The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −2.1 (2)°]. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O and N—H⋯F hydrogen bonds into a layer parallel to the bc plane. The crystal packing also features C—H⋯π interactions.

Highlights

C23H20FNO4, the fluoro-substituted benzene ring is approximately perpendicular to the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.264 (1) Å], with a dihedral angle of 83.79 (6)
Cg1, Cg2 and Cg3 are the centroids of C4–C6/C11–C13, C14–C19 and C6–C11 rings, respectively
In view of the above observations and in continuation of our program on the chemistry of 4H-pyran derivatives (Bedair et al, 2001; El-Agrody et al, 2002, 2011; Abd-El-Aziz et al, 2004; Sabry et al, 2011), we report the crystal structure of the title compound

Summary

Data collection

R factor = 0.039; wR factor = 0.117; data-to-parameter ratio = 13.4. C23H20FNO4, the fluoro-substituted benzene ring is approximately perpendicular to the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.264 (1) Å], with a dihedral angle of 83.79 (6). The pyran ring adopts a flattened boat conformation. The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C =. An intramolecular N—H O hydrogen bond generates an S(6) ring motif. Molecules are linked by N—H O and N—H F hydrogen bonds into a layer parallel to the bc plane.

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Special details