2-Amino-4-(4-bromo-phen-yl)-6-meth-oxy-4H-benzo[h]chromene-3-carbonitrile.

Al-Anood M Al-Dies,Mohamed A Al-Omar,Abd El-Galil E Amr,Edward R T Tiekink,Seik Weng Ng,Ahmed M El-Agrody

doi:10.1107/s1600536813005461

Abstract

In the title compound, C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446 Å). The bromobenzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34 (13)°]. In the crystal, supramolecular layers parallel to (101) are sustained by amine–cyano N—H⋯N and amine–methoxy N—H⋯O hydrogen bonds. The layers stack with interactions of the type (bromobenzene)C—H⋯π(outer-C6 ring of the fused-ring system) connecting them.

Highlights

In the title compound, C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å)
As part of our on-going program investigating the chemistry of 4H-pyran derivatives (Sabry et al, 2011), we report the synthesis of the title compound, (I), and its crystal structure
The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry

Summary

Structure Reports

Experimental a Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO. University, Nasr City, Cairo, 11884, Egypt, cPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, dDrug. University, Riyadh 11451, Saudi Arabia, eApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, fDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and gChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia. C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms The layers stack with interactions of the type (bromobenzene)C—H (outer-C6 ring of the fused-ring system) connecting them

For background to biologically active molecules having the

Agilent SuperNova Dual diffractometer with an Atlas detector

Special details