Received 19 February 2013
aDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,bApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt,cChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia,dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
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The asymmetric unit of the title compound, C19H12ClN3O, contains two molecules with similar conformations. The 14 non-H atoms comprising the 4H-chromeno[8,7-b]pyridine residue are essentially coplanar (r.m.s. deviations = 0.037 and 0.042 Å for the two molecules) and the main difference between them is seen in the twist about the bond linking the main residue to the attached chlorobenzene rings [dihedral angles = 79.01 (12) and 76.22 (11)° for the two molecules]. Zigzag supramolecular chains along the a-axis direction mediated by amino-pyridine N-HN hydrogen bonds feature in the crystal packing; these are connected into a three-dimensional architecture by C-H interactions and ClCl contacts [ClCl = 3.3896 (14) Å].
For background to the chemistry and biological activity of 4H-pyran derivatives, see: Al-Ghamdi et al. (2012); El-Agrody et al. (2012). For the structure of the 2-chloro analogue, see: Wang et al. (2003).
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: HB7046 ).
We thank the Research Center of the College of Pharmacy and Deanship of Scientific Research of King Saud University for supporting this study. 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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