Received 4 March 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, C10H5FN2, is a monoclinic (P21/c) polymorph of the previously reported triclinic (P-1) form [Antipin et al. (2003). J. Mol. Struct. 650, 1-20]. The 13 non-H atoms in the title polymorph are almost coplanar (r.m.s. deviation = 0.020 Å); a small twist between the fluorobenzene and dinitrile groups [C-C-C-C torsion angle = 175.49 (16)°] is evident in the triclinic polymorph. In the crystal, C-HN interactions lead to supramolecular layers parallel to (-101); these are connected by C-F interactions.
For background to the chemistry and biological activity of 4H-pyran derivatives, see: El-Agrody et al. (2011); Sabry et al. (2011). For the structure of the triclinic polymorph, see: Antipin et al. (2003); Ng & Tiekink (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), QMol (Gans & Shalloway, 2001) 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: HB7051 ).
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.
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Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Agrody, A. M., Sabry, N. M. & Motlaq, S. S. (2011). J. Chem. Res. 35, 77-83.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Ng, S. W. & Tiekink, E. R. T. (2013). Private communication (deposition number 926904). CCDC, Cambridge, England.
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.
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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.