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Volume 69 
Part 7 
Page o1127  
July 2013  

Received 1 April 2013
Accepted 14 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.128
Data-to-parameter ratio = 17.5
Details
Open access

Ethyl 4-(4-chlorophenyl)-2-methyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate

aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and bZhejiang Huanke Environment Consultancy Co.,Ltd, No. 111 Tianmushan Road, Hangzhou 310007, People's Republic of China
Correspondence e-mail: chrc@zjut.edu.cn

In the title compound, C19H18ClNO3, the non-aromatic part of the fused ring system adopts an envelope conformation with the central methylene C atom as the flap. The dihedral angle between the pyridine and benzene rings is 56.98 (3)°. In the crystal, molecules are linked into double layers parallel to (100) by a network of weak C-H...O interactions.

Related literature

For the synthetic procedure, see: Fang et al. (2007[Fang, X., Liu, Y.-C. & Li, C. (2007). J. Org. Chem. 72, 8608-8610.]); Mirza-Aghayan et al. (2012[Mirza-Aghayan, M., Boukherroub, R., Nemati, M. & Rahimifard, M. (2012). Tetrahedron Lett. 53, 2473-2475.]). For a related structure, see: Sicheri et al. (1992[Sicheri, F. V., Derry, W. B., Gupta, R. S. & Yang, D. S.-C. (1992). Acta Cryst. C48, 1687-1689.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18ClNO3

  • Mr = 343.79

  • Monoclinic, P 21 /c

  • a = 12.5736 (7) Å

  • b = 8.3815 (4) Å

  • c = 17.4945 (8) Å

  • [beta] = 112.151 (2)°

  • V = 1707.59 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 296 K

  • 0.49 × 0.42 × 0.30 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.891, Tmax = 0.932

  • 15658 measured reflections

  • 3860 independent reflections

  • 2725 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.128

  • S = 1.00

  • 3860 reflections

  • 220 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6B...O3i 0.97 2.67 3.454 (3) 139
C11-H11...O1ii 0.93 2.45 3.357 (2) 164
C12-H12...O3iii 0.93 2.70 3.569 (2) 156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2095 ).


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

Fang, X., Liu, Y.-C. & Li, C. (2007). J. Org. Chem. 72, 8608-8610.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Mirza-Aghayan, M., Boukherroub, R., Nemati, M. & Rahimifard, M. (2012). Tetrahedron Lett. 53, 2473-2475.  [ChemPort]
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] [IUCr Journals]
Sicheri, F. V., Derry, W. B., Gupta, R. S. & Yang, D. S.-C. (1992). Acta Cryst. C48, 1687-1689.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1127  [ doi:10.1107/S1600536813016541 ]

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