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Volume 69 
Part 5 
Page o785  
May 2013  

Received 21 March 2013
Accepted 11 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.059
wR = 0.167
Data-to-parameter ratio = 19.7
Details
Open access

Diethyl 4-(2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: chrc@zjut.edu.cn

In the title compound, C20H25NO5, the dihydropyridine ring adopts a flattened boat conformation. The methoxyphenyl ring is almost perpendicular to the mean plane of the pyridine ring [dihedral angle = 88.42 (3)°]. The two carbonyl units adopt a synperiplanar conformation with respect to the double bonds in the dihydropyridine ring. In the crystal, molecules are connected by N-H...O hydrogen bonds into R44(24) tetrameric rings. A region of disordered electron density, located at the center of four adjacent molecules, was treated with the SQUEEZE routine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. It is probably the result of traces of the solvent of crystallization and was not taken into account during the structure refinement.

Related literature

For general background to 1,4-dihydropyridine compounds, see: Franke et al. (2008[Franke, P. T., Johansen, R. L., Bertelsen, S. & Jorgensen, K. A. (2008). Chem. Asian J. 3, 216-224.]); Takemoto et al. (2010[Takemoto, Y., Yoshida, K., Inokuma, T. & Takasu, K. (2010). Synlett, pp. 1865-1869.]). For related structures, see: Fun et al. (2012[Fun, H.-K., Hemamalini, M., Reddy, B. P., Vijayakumar, V. & Sarveswari, S. (2012). Acta Cryst. E68, o287-o288.]); Kapoor et al. (2011[Kapoor, K., Gupta, V. K., Kant, R., Pawar, M. P. & Joshi, H. S. (2011). Acta Cryst. E67, o2979.]).

[Scheme 1]

Experimental

Crystal data
  • C20H25NO5

  • Mr = 359.41

  • Tetragonal, [P \overline 42_1 c ]

  • a = 22.4689 (7) Å

  • c = 8.2443 (3) Å

  • V = 4162.1 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.47 × 0.31 × 0.22 mm

Data collection
  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.952, Tmax = 0.982

  • 60800 measured reflections

  • 4755 independent reflections

  • 3128 reflections with I > 2[sigma](I)

  • Rint = 0.078

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.167

  • S = 1.00

  • 4755 reflections

  • 241 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O5i 0.86 2.07 2.924 (3) 170
Symmetry code: (i) y, -x+1, -z.

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.]); 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2102).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2475 ).


Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (No. Y4110373). We are also grateful for the help of Professor Jian-Ming Gu of Zhejiang University.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Franke, P. T., Johansen, R. L., Bertelsen, S. & Jorgensen, K. A. (2008). Chem. Asian J. 3, 216-224.  [CrossRef] [PubMed] [ChemPort]
Fun, H.-K., Hemamalini, M., Reddy, B. P., Vijayakumar, V. & Sarveswari, S. (2012). Acta Cryst. E68, o287-o288.  [CrossRef] [ChemPort] [details]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Kapoor, K., Gupta, V. K., Kant, R., Pawar, M. P. & Joshi, H. S. (2011). Acta Cryst. E67, o2979.  [CSD] [CrossRef] [details]
Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Takemoto, Y., Yoshida, K., Inokuma, T. & Takasu, K. (2010). Synlett, pp. 1865-1869.  [ISI] [CrossRef]


Acta Cryst (2013). E69, o785  [ doi:10.1107/S1600536813009951 ]

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