Received 25 February 2013
aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia,bChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt,cPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,dDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud 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
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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-HN and amine-methoxy N-HO hydrogen bonds. 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 4H-chromene or 4H-benzochromene residue, see: Sabry et al. (2011); Amin et al. (2010); Kidwai et al. (2010); Singh et al. (2010), For the structure of the fluoro derivative, see: Al-Dies et al. (2012).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7048 ).
The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the research group project No. RGP-VPP-099. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Dies, A.-A. M., Amr, A.-G. E., El-Agrody, A. M., Chia, T. S. & Fun, H.-K. (2012). Acta Cryst. E68, o1934-o1935.
Amin, K. M., Kamel, M. M., Anwar, M. M., Khedr, M. & Syam, Y. M. (2010). Eur. J. Med. Chem. 45, 2117-2131.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kidwai, M., Poddar, R., Bhardwaj, S., Singh, S. & Mehta Luthra, P. (2010). Eur. J. Med. Chem. 45, 5031-5038.
Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765-772.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, O. M., Devi, N. S., Thokchom, D. S. & Sharma, G. J. (2010). Eur. J. Med. Chem. 45, 2250-2257.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.