Received 6 June 2013
aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
Correspondence e-mail: email@example.com
The title heteroaryl chalcone derivative, C17H17NO4, is close to planar: the dihedral angle between the pyridine and benzene rings is 3.71 (11)° and the methoxy C atoms deviate from their attached ring by 0.046 (3), -0.044 (2) and 0.127 (3) Å. The disposition of the pyridine N atom and the carbonyl group is anti [N-C-C-O = -177.7 (2)°]. In the crystal, molecules are linked by weak C-HN and C-HO interactions into (100) sheets and an aromatic - stacking interaction between the pyridine and benzene ring, with a centroid-centroid separation of 3.7036 (14) Å also occurs.
For the fluorescence properties of heteroaryl chalcones, see: Suwunwong et al. (2011). For related structures, see: Chantrapromma et al. (2009); Fun et al. (2010, 2011); Suwunwong et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7090 ).
Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0257/2553) is gratefully acknowledged. The authors extend their appreciation to Prince of Songkla University, the Deanship of Scientific Research at the King Saud University and Universiti Sains Malaysia for the APEX DE2012 grant No.1002/PFIZIK/910323.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Suwunwong, T., Karalai, C. & Fun, H.-K. (2009). Acta Cryst. E65, o893-o894.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o2406-o2407.
Fun, H.-K., Suwunwong, T., Chantrapromma, S. & Karalai, C. (2010). Acta Cryst. E66, o2559-o2560.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Chem. Pap. 65, 890-897.
Suwunwong, T., Chantrapromma, S., Karalai, C., Wisitsak, P. & Fun, H.-K. (2012). Acta Cryst. E68, o317-o318.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.