Received 19 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,cDepartment of Pharmaceutical Chemistry, 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, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromobenzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C-C-C-O = 3.4 (5)°]; the methoxy substituent is also coplanar [C-O-C-C = 174.5 (3)°]. In addition to an intramolecular N-HO(ester carbonyl) hydrogen bond, the ester carbonyl O atom also forms an intermolecular N-HO hydrogen bond with the second amine H atom, generating a zigzag supramolecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N-HBr hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C-H interactions.
For background to the pharmaceutical activity of 4H-chromene and its derivatives, see: Abd-El-Aziz et al. (2004, 2007); Kemnitzer et al. (2007); Alvey et al. (2009). For the isostructural 4-fluoro analogue, see: El-Agrody 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: HG5295 ).
The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University. 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).
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