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Volume 69 
Part 12 
Pages o1757-o1758  
December 2013  

Received 4 November 2013
Accepted 6 November 2013
Online 9 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.096
Data-to-parameter ratio = 14.5
Details
Open access

Ethyl 4-anilino-2-methyl-5-oxo-1-phenyl-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, C20H20N2O3, the central 2,5-di­hydro-1H-pyrrole ring [r.m.s. deviation = 0.014 (1) Å] is oriented at dihedral angles of 77.81 (6) and 25.33 (6)°, respectively, to the attached phenyl ring and the aniline phenyl ring. An intra­molecular N-H...O hydrogen bond occurs. In the crystal, mol­ecules are linked through pairs of N-H...O hydrogen bonds, forming inversion dimers with an R22(10) ring motif. Two weak C-H...[pi] inter­actions are also observed.

Related literature

For the synthesis of pyrrolone compounds, see: Shiraki et al. (1996[Shiraki, R., Sumino, A., Tadano, K.-I. & Ogawa, S. (1996). J. Org. Chem. 61, 2845-2852.]). For the biological activity of lactams, see: Alvi et al. (1998[Alvi, K. A., Casey, A. & Nair, B. G. (1998). J. Antibiot. 51, 515-517.]); Li et al. (2002[Li, W.-R., Lin, S. T., Hsu, N.-M. & Chern, M.-S. (2002). J. Org. Chem. 67, 4702-4706.]); Mase et al. (1999[Mase, N., Nishi, T., Takamori, Y., Yoda, H. & Takabe, K. (1999). Tetrahedron Asymmetry, 10, 4469-4471.]); Wiedhopf et al. (1973[Wiedhopf, R. M., Trumbull, E. R. & Cole, J. R. (1973). J. Pharm. Sci. 62, 1206-1207.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). 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
  • C20H20N2O3

  • Mr = 336.38

  • Triclinic, [P \overline 1]

  • a = 5.9071 (6) Å

  • b = 11.3474 (12) Å

  • c = 14.1716 (14) Å

  • [alpha] = 111.467 (2)°

  • [beta] = 101.113 (3)°

  • [gamma] = 95.328 (3)°

  • V = 853.45 (15) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 100 K

  • 0.34 × 0.29 × 0.21 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.783, Tmax = 0.860

  • 18887 measured reflections

  • 3367 independent reflections

  • 3156 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.04

  • 3367 reflections

  • 232 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C8-C13 and C15-C20 phenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
N2-H2N...O3 0.898 (17) 2.443 (16) 2.8247 (14) 105.9 (12)
N2-H2N...O3i 0.898 (17) 2.033 (17) 2.9135 (14) 166.3 (14)
C1-H1B...Cg2ii 0.98 2.91 3.6177 (15) 130
C12-H12...Cg3iii 0.95 2.84 3.4865 (14) 126
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z+2.

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; 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: IS5318 ).


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

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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]
Alvi, K. A., Casey, A. & Nair, B. G. (1998). J. Antibiot. 51, 515-517.  [CrossRef] [ChemPort] [PubMed]
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Li, W.-R., Lin, S. T., Hsu, N.-M. & Chern, M.-S. (2002). J. Org. Chem. 67, 4702-4706.  [CrossRef] [PubMed] [ChemPort]
Mase, N., Nishi, T., Takamori, Y., Yoda, H. & Takabe, K. (1999). Tetrahedron Asymmetry, 10, 4469-4471.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shiraki, R., Sumino, A., Tadano, K.-I. & Ogawa, S. (1996). J. Org. Chem. 61, 2845-2852.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wiedhopf, R. M., Trumbull, E. R. & Cole, J. R. (1973). J. Pharm. Sci. 62, 1206-1207.  [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1757-o1758   [ doi:10.1107/S1600536813030390 ]

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