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Volume 68 
Part 11 
Page o3218  
November 2012  

Received 18 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.147
Data-to-parameter ratio = 18.4
Details
Open access

Ethyl (Z)-3-(4-methylanilino)-2-[(4-methylphenyl)carbamoyl]prop-2-enoate

aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The title compound, C20H22N2O3, is a secondary amine featuring an amide and an ester functionality in connection with a Michael system. The conformation about the C=C bond is E. Intramolecular N-H...O hydrogen bonds occur. In the crystal, C-H...O contacts connect the molecules into chains along the b-axis direction.

Related literature

For general information about the synthetic and industrial importance of aniline and its derivatives, see: Berry & Royd (1984[Berry, D. F. & Royd, S. A. (1984). Soil Sci. Soc. Am. J. 48, 565-569.]); Garudachari et al. (2012[Garudachari, B., Satyanarayana, M. N., Thippeswamy, B., Shivakumar, C. K., Shivananda, K. N., Hegde, G. & Isloor, A. M. (2012). Eur. J. Med. Chem. 54, 900-906.]); Sridharan et al. (2006[Sridharan, V., Perumal, S., Avendano, C. & Menendez, J. C. (2006). Synlett, pp. 91-95.]); Kasthuri et al. (2008[Kasthuri, J., Santhanalakshmi, J. & Rajendiran, N. (2008). J. Iran. Chem. Soc. 3, 436-444.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); 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
  • C20H22N2O3

  • Mr = 338.40

  • Monoclinic, C 2/c

  • a = 18.8170 (4) Å

  • b = 11.9752 (3) Å

  • c = 15.6043 (4) Å

  • [beta] = 91.470 (1)°

  • V = 3515.07 (15) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.42 × 0.26 × 0.19 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.984

  • 16569 measured reflections

  • 4353 independent reflections

  • 3411 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.147

  • S = 1.05

  • 4353 reflections

  • 237 parameters

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

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C23-H23...O1i 0.95 2.68 3.620 (2) 170
C25-H25...O2ii 0.95 2.70 3.4685 (19) 139
N1-H1...O1 0.97 (2) 1.85 (2) 2.6383 (17) 135.9 (18)
N2-H2...O2 0.88 (2) 1.92 (2) 2.6713 (18) 143.0 (19)
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 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: ZQ2185 ).


Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear sciences, Government of India, for the Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Berry, D. F. & Royd, S. A. (1984). Soil Sci. Soc. Am. J. 48, 565-569.  [CrossRef] [ChemPort]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Garudachari, B., Satyanarayana, M. N., Thippeswamy, B., Shivakumar, C. K., Shivananda, K. N., Hegde, G. & Isloor, A. M. (2012). Eur. J. Med. Chem. 54, 900-906.  [ISI] [CrossRef] [ChemPort] [PubMed]
Kasthuri, J., Santhanalakshmi, J. & Rajendiran, N. (2008). J. Iran. Chem. Soc. 3, 436-444.  [CrossRef]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sridharan, V., Perumal, S., Avendano, C. & Menendez, J. C. (2006). Synlett, pp. 91-95.


Acta Cryst (2012). E68, o3218  [ doi:10.1107/S1600536812043723 ]

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