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Volume 69 
Part 12 
Pages o1761-o1762  
December 2013  

Received 5 November 2013
Accepted 7 November 2013
Online 3 December 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.107
Data-to-parameter ratio = 21.3
Details
Open access

Ethyl 4-(4-chloro­anilino)-1-(4-chloro­phen­yl)-2-methyl-5-oxo-2,5-di­hydro-1H-pyrrole-2-carboxyl­ate

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,dChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt,eDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C20H18Cl2N2O3, the dihedral angles between the central 2,5-di­hydro-1H-pyrrole ring and the phenyl rings are 74.87 (9) and 29.09 (9)°. Intra­molecular N-H...O and C-H...O hydrogen bonds occur. In the crystal, pairs of N-H...O hydrogen bonds link adjacent mol­ecules into inversion dimers and form an R12(6)R22(10)R12(6) ring motif through C-H...O hydrogen bonds.

Related literature

For the lower toxicity of the lactam ring in comparison to lactones, see: Dembélé et al. (1992[Dembélé, Y. A., Belaud, C. & Villiéras, J. (1992). Tetrahedron Asymmetry, 3, 511-514.]). For the importance of lactams in the synthesis of significant bio-active mol­ecules see: Nay et al. (2009[Nay, B., Riache, N. & Evanno, L. (2009). Nat. Prod. Rep. 26, 1044-1062.]); Galeazzi et al. (1996[Galeazzi, R., Mobbili, G. & Orena, M. (1996). Tetrahedron, 52, 1069-1084.]); Ghelfi et al. (1999[Ghelfi, F., Bellesia, F., Forti, L., Ghirardini, G., Grandi, R., Libertini, E., Montemaggi, M. C., Pagnoni, U. M., Pinetti, A., De Buyck, L. & Parson, A. F. (1999). Tetrahedron, 55, 5839-5852.]); Hanessian et al. (1996[Hanessian, S., Reinhold, U. & Ninkovic, S. (1996). Tetrahedron Lett. 37, 8967-8970.]). For the pharmacological properties of di­hydro­pyrrolo­nes, see: Bergmann & Gericke (1990[Bergmann, R. & Gericke, R. (1990). J. Med. Chem. 33, 492-504.]); Moody & Young (1994[Moody, C. M. & Young, D. W. (1994). Tetrahedron Lett. 35, 7277-7280.]); Nilsson et al. (1990[Nilsson, B. M., Ringdhal, B. & Hacksell, U. A. (1990). J. Med. Chem. 33, 580-584.]). For a similar structure, see: Akkurt et al. (2013[Akkurt, M., Mohamed, S. K., Elremaily, M. A. A., Santoyo-Gonzalez, F. & Albayati, M. R. (2013). Acta Cryst. E69, o1757-o1758.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18Cl2N2O3

  • Mr = 405.26

  • Triclinic, [P \overline 1]

  • a = 5.8319 (3) Å

  • b = 12.3759 (6) Å

  • c = 13.5707 (6) Å

  • [alpha] = 86.484 (2)°

  • [beta] = 80.098 (2)°

  • [gamma] = 78.671 (2)°

  • V = 945.69 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 100 K

  • 0.48 × 0.08 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.990

  • 15209 measured reflections

  • 5316 independent reflections

  • 4054 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.107

  • S = 1.02

  • 5316 reflections

  • 250 parameters

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

  • [Delta][rho]max = 0.42 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
N2-H2N...O3 0.82 (2) 2.471 (19) 2.8187 (19) 107.0 (15)
N2-H2N...O3i 0.82 (2) 2.12 (2) 2.9158 (19) 164.9 (18)
C12-H12...O2ii 0.95 2.34 3.285 (2) 176
C13-H13...O2 0.95 2.41 3.142 (2) 134
C14-H14A...O2iii 0.98 2.58 3.431 (2) 146
C16-H16...O3i 0.95 2.53 3.308 (2) 139
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999)[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]; 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5367 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

Akkurt, M., Mohamed, S. K., Elremaily, M. A. A., Santoyo-Gonzalez, F. & Albayati, M. R. (2013). Acta Cryst. E69, o1757-o1758.  [CSD] [CrossRef] [IUCr Journals]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bergmann, R. & Gericke, R. (1990). J. Med. Chem. 33, 492-504.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dembélé, Y. A., Belaud, C. & Villiéras, J. (1992). Tetrahedron Asymmetry, 3, 511-514.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Galeazzi, R., Mobbili, G. & Orena, M. (1996). Tetrahedron, 52, 1069-1084.  [CrossRef] [ChemPort] [Web of Science]
Ghelfi, F., Bellesia, F., Forti, L., Ghirardini, G., Grandi, R., Libertini, E., Montemaggi, M. C., Pagnoni, U. M., Pinetti, A., De Buyck, L. & Parson, A. F. (1999). Tetrahedron, 55, 5839-5852.  [Web of Science] [CrossRef] [ChemPort]
Hanessian, S., Reinhold, U. & Ninkovic, S. (1996). Tetrahedron Lett. 37, 8967-8970.  [CrossRef] [ChemPort] [Web of Science]
Moody, C. M. & Young, D. W. (1994). Tetrahedron Lett. 35, 7277-7280.  [CrossRef] [ChemPort] [Web of Science]
Nay, B., Riache, N. & Evanno, L. (2009). Nat. Prod. Rep. 26, 1044-1062.  [CrossRef] [PubMed] [ChemPort]
Nilsson, B. M., Ringdhal, B. & Hacksell, U. A. (1990). J. Med. Chem. 33, 580-584.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
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]


Acta Cryst (2013). E69, o1761-o1762   [ doi:10.1107/S1600536813030560 ]

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