2-Amino-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile

Al-Anood M Al-Dies,Abdel-Galil E Amr,Tze Shyang Chia,Hoong-Kun Fun,Ahmed M El-Agrody

doi:10.1107/s1600536812023021

Abstract

In the title molecule, C21H15FN2O2, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109 (2) Å] is 83.35 (7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −4.3 (3)°]. In the crystal, molecules are linked by intermolecular N—H⋯N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.7713 (9) Å].

Highlights

Chemistry Department, Faculty of Science, King Khalid University, 9004 Abha, Saudi Arabia, bDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, cApplied Organic
The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety
We have reported the synthesis of 4H-chromene derivatives using α-cyanocinnamonitriles and ethyl α-cyanocinnamates (Sayed et al, 2000; Bedair et al, 2001; El-Agrody et al, 2000, 2002), study of their characterization and evaluation of their antimicrobial and antitumor activities

Summary

Structure Reports

Chemistry Department, Faculty of Science, King Khalid University, 9004 Abha, Saudi Arabia, bDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, cApplied Organic. C21H15FN2O2, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109 (2) Å] is 83.35 (7). The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = 4.3 (3) ]. Molecules are linked by intermolecular N—H N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by – interactions [centroid–centroid distance = 3.7713 (9) Å]

Cu K radiation

Graphite monochromator φ and ω scans

Special details