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

Smits, R.; Belyakov, S.; Vigante, B.; Duburs, G.

doi:10.1107/S1600536812048532

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 (C-C) = 0.003 Å
R = 0.060
wR = 0.149
Data-to-parameter ratio = 17.4
Details

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

Rufus Smits,^a Sergey Belyakov,^a Brigita Vigante ^a and Gunars Duburs ^a ^*

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

In the title molecule, C₂₀H₁₈N₂O₃, an intramolecular N-HO 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-HO hydrogen bonds, forming inversion dimers. The dimers are linked by C-HO hydrogen bonds and C-H [pi] interactions, forming a three-dimensional structure.

Related literature

For applications of dihydropyridones, see: Dong et al. (2005); Elias et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₂₀H₁₈N₂O₃
M_r = 334.36
Monoclinic, P 2₁ /c
a = 5.5746 (2) Å
b = 16.4083 (6) Å
c = 18.0930 (8) Å
= 96.5018 (14)°
V = 1644.32 (11) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.053

Refinement

R[F² > 2(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
_max = 0.23 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C25-H25O15ⁱ	0.93	2.42	3.257 (3)	150
C24-H24O7ⁱⁱ	0.93	2.49	3.318 (3)	149
C13-H13O16ⁱⁱⁱ	0.93	2.54	3.300 (3)	139
C23-H23Cgⁱⁱ	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); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: maXus (Mackay et al., 1999).

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.
Dong, D., Bi, X., Liu, Q. & Cong, F. (2005). Chem. Commun. pp. 3580-3582.
Elias, R. S., Saeed, B. A., Saour, K. Y. & Al-Masoudi, N. A. (2008). Tetrahedron Lett. 49, 3049-3051.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.

organic compounds