Date Published: June 01, 2012
Publisher: International Union of Crystallography
Author(s): Ahmed M. El-Agrody, Mohamed A. Al-Omar, Abdel-Galil E. Amr, Tze Shyang Chia, Hoong-Kun Fun.
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.
For background to and applications of 4H-chromene and its derivatives, see: Jeso & Nicolaou (2009 ▶); Alvey et al. (2008 ▶, 2009 ▶); Symeonidis et al. (2009 ▶); Brühlmann et al. (2001 ▶); Bedair et al. (2001 ▶); El-Agrody et al. (2002 ▶, 2011 ▶); Abd-El-Aziz et al. (2004 ▶); Sabry et al. (2011 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).