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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The title compound, C21H15FN2O2, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052 Å), with the fluorobenzene ring being almost perpendicular to this [dihedral angle = 85.30 (7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132 (2) Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å). In the crystal, inversion dimers are formed via pairs of amine-cyano N-HN hydrogen bonds. The dimers are connected into a three-dimensional architecture by C-HN(cyano), C-H and - [intercentroid distance = 3.6671 (10) Å] interactions.
For background and various applications of benzo- and naphthopyran- derivatives, see: Bonsignore et al. (1993); Hafez et al. (1987). For background to the chemistry and biological activity of 4H-pyran derivatives, see: El-Agrody et al. (2011); Sabry et al. (2011). For related structures, see: Wang et al. (2008); Shekhar et al. (2012); Amr et al. (2013).
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: HB7047 ).
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).
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