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Volume 68 
Part 12 
Page o3489  
December 2012  

Received 15 November 2012
Accepted 26 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.003 Å
R = 0.060
wR = 0.149
Data-to-parameter ratio = 17.4
Details
Open access

Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]-1,4,5,6-tetrahydropyridine-3-carboxylate

aLatvian Institute of Organic Synthesis, Riga, LV 1006, Latvia
Correspondence e-mail: gduburs@osi.lv

In the title molecule, C20H18N2O3, an intramolecular N-H...O hydrogen bond leads to a cis conformation of the pyridinyl-vinyl fragment. The phenyl and pyridine rings are inclined to one another by 77.3 (1) °. In the crystal, molecules are linked via pairs of C-H...O hydrogen bonds, forming inversion dimers. The dimers are linked by C-H...O hydrogen bonds and C-H...[pi] interactions, forming a three-dimensional structure.

Related literature

For applications of dihydropyridones, see: Dong et al. (2005[Dong, D., Bi, X., Liu, Q. & Cong, F. (2005). Chem. Commun. pp. 3580-3582.]); Elias et al. (2008[Elias, R. S., Saeed, B. A., Saour, K. Y. & Al-Masoudi, N. A. (2008). Tetrahedron Lett. 49, 3049-3051.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O3

  • Mr = 334.36

  • Monoclinic, P 21 /c

  • a = 5.5746 (2) Å

  • b = 16.4083 (6) Å

  • c = 18.0930 (8) Å

  • [beta] = 96.5018 (14)°

  • V = 1644.32 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 193 K

  • 0.41 × 0.12 × 0.07 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • 7024 measured reflections

  • 4206 independent reflections

  • 2483 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.149

  • S = 0.96

  • 4206 reflections

  • 242 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8-C13 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C25-H25...O15i 0.93 2.42 3.257 (3) 150
C24-H24...O7ii 0.93 2.49 3.318 (3) 149
C13-H13...O16iii 0.93 2.54 3.300 (3) 139
C23-H23...Cgii 0.93 2.66 3.480 147
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) x-1, y, z.

Data collection: KappaCCD Server Software (Nonius, 1999[Nonius (1999). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: maXus (Mackay et al., 1999[Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999). maXus. Bruker-Nonius, The Netherlands, MacScience, Japan, and The University of Glasgow, Scotland.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5365 ).


Acknowledgements

This study was supported by the Latvian National Research Programme 2010-2013 Development of prevention, treatment, diagnostic means and practice and biomedicine technologies for improvement of public health.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Dong, D., Bi, X., Liu, Q. & Cong, F. (2005). Chem. Commun. pp. 3580-3582.  [CrossRef]
Elias, R. S., Saeed, B. A., Saour, K. Y. & Al-Masoudi, N. A. (2008). Tetrahedron Lett. 49, 3049-3051.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999). maXus. Bruker-Nonius, The Netherlands, MacScience, Japan, and The University of Glasgow, Scotland.
Nonius (1999). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3489  [ doi:10.1107/S1600536812048532 ]

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