Received 4 February 2009
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cSyngene International Ltd, Biocon Park, Plot Nos. 2 and 3, Bommasandra 4th Phase, Jigani Link Road, Bangalore 560 100, India,dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and eDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
Correspondence e-mail: email@example.com
In the molecule of the title compound, C21H15N3O, the 10H-9-oxa-1,3-diazaanthracene ring system is slightly bent, with dihedral angles of 3.99 (6) and 4.80 (6)° between the pyran ring and the pyrimidine and benzene rings, respectively. This ring system makes a dihedral angle of 85.23 (3)° with the naphthalene plane. In the crystal packing, molecules are linked by N-HN hydrogen bonds into chains along the a axis and these chains are stacked along the b axis. The crystal is further stabilized by weak C-HN and C-H interactions.
For values of bond lengths, see Allen et al. (1987). For background to the bioactivity and applications of naphthyrimidines, see, for example: Bedard et al. (2000); Bohme & Haake (1976); Erian (1993); Falardeau et al. (2000); Martinez & Marco (1997); Tandon et al. (1991); Taylor & McKillop (1970). For the stability of the temperature controller, see Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2571 ).
AMI is grateful to the Director, NITK, Surathkal, India, for providing research facilities. SR thanks Dr Gautam Das, Syngene International Ltd, Bangalore, India, for allocation of research resources. The authors also thank the Universiti Sains Malaysia for Research University Golden Goose Grant No. 1001/PFIZIK/811012.
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