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Volume 69 
Part 7 
Pages o1076-o1077  
July 2013  

Received 6 June 2013
Accepted 6 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.067
wR = 0.188
Data-to-parameter ratio = 18.8
Details
Open access

(2E)-1-(Pyridin-2-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

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: suchada.c@psu.ac.th

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-H...N and C-H...O interactions into (100) sheets and an aromatic [pi]-[pi] stacking interaction between the pyridine and benzene ring, with a centroid-centroid separation of 3.7036 (14) Å also occurs.

Related literature

For the fluorescence properties of heteroaryl chalcones, see: Suwunwong et al. (2011[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Chem. Pap. 65, 890-897.]). For related structures, see: Chantrapromma et al. (2009[Chantrapromma, S., Suwunwong, T., Karalai, C. & Fun, H.-K. (2009). Acta Cryst. E65, o893-o894.]); Fun et al. (2010[Fun, H.-K., Suwunwong, T., Chantrapromma, S. & Karalai, C. (2010). Acta Cryst. E66, o2559-o2560.], 2011[Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o2406-o2407.]); Suwunwong et al. (2012[Suwunwong, T., Chantrapromma, S., Karalai, C., Wisitsak, P. & Fun, H.-K. (2012). Acta Cryst. E68, o317-o318.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17NO4

  • Mr = 299.32

  • Monoclinic, P 21 /c

  • a = 8.4047 (3) Å

  • b = 8.7285 (3) Å

  • c = 19.5086 (7) Å

  • [beta] = 94.113 (2)°

  • V = 1427.47 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.32 × 0.27 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.984

  • 14970 measured reflections

  • 3792 independent reflections

  • 2435 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.188

  • S = 1.07

  • 3792 reflections

  • 202 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...O4i 0.93 2.39 3.277 (3) 160
C15-H15A...N1ii 0.96 2.47 3.349 (3) 153
Symmetry codes: (i) [x-1, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL ; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[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.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7090 ).


Acknowledgements

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.

References

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.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o2406-o2407.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Suwunwong, T., Chantrapromma, S. & Karalai, C. (2010). Acta Cryst. E66, o2559-o2560.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Chem. Pap. 65, 890-897.  [CSD] [CrossRef] [ChemPort]
Suwunwong, T., Chantrapromma, S., Karalai, C., Wisitsak, P. & Fun, H.-K. (2012). Acta Cryst. E68, o317-o318.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1076-o1077   [ doi:10.1107/S1600536813015821 ]

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