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Volume 69 
Part 3 
Page o351  
March 2013  

Received 28 January 2013
Accepted 31 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.142
Data-to-parameter ratio = 15.2
Details
Open access

(E)-Ethyl 2-anilino-5-[3-(dimethylamino)acryloyl]-4-phenylthiophene-3-carboxylate

aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia,bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia, 21321 Alexandria, Egypt, and cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: yahia@ksu.edu.sa, dr.sammer.yousuf@gmail.com

In the title compound, C24H24N2O3S, the phenyl rings form dihedral angles of 55.65 (11) and 79.60 (11)° with the plane of the thiophene ring. The molecular conformation is stabilized by an intramolecular N-H...O hydrogen bond, generating an S(6) ring motif. In the crystal, centrosymmetrically related molecules are linked into dimers by two pairs of C-H...O interactions.

Related literature

For background to biological activity of thiophene derivatives see: Mishra et al. (2011[Mishra, R., Tomar, I., Singhal, S. & Jha, K. K. (2011). Pharma Chem. 3, 38-54.]). For the synthesis of different thiophene derivatives, see: Mabkhot et al. (2011[Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Al-Othman, Z. A. & Alamary, A. S. (2011). Int. J. Mol. Sci. 12, 7824-7834.]); Mabkhot, Barakat & Alshahrani (2012[Mabkhot, Y. N., Barakat, A. & Alshahrani, S. (2012). J. Mol. Struct., 1027, 15-19.]); Mabkhot, Barakat, Al-Majid, Alamary & Al-Nahary (2012[Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Alamary, A. S. & Al-Nahary, T. T. (2012). Int. J. Mol. Sci. 13, 5035-5047.]); Mabkhot, Barakat, Al-Majid & Alshahrani (2012[Mabkhot, Y. N., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.]). For related structures, see: Cao et al. (2003[Cao, K.-G., Wang, Z.-W., Zhao, X.-Q. & Fang, T. (2003). Chin. J. Org. Chem. 23, 1411-1415.]).

[Scheme 1]

Experimental

Crystal data
  • C24H24N2O3S

  • Mr = 420.51

  • Triclinic, [P \overline 1]

  • a = 6.5776 (9) Å

  • b = 10.7119 (14) Å

  • c = 16.516 (2) Å

  • [alpha] = 78.459 (3)°

  • [beta] = 79.743 (3)°

  • [gamma] = 80.765 (3)°

  • V = 1112.5 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 273 K

  • 0.28 × 0.27 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.970

  • 12618 measured reflections

  • 4123 independent reflections

  • 3373 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.142

  • S = 1.05

  • 4123 reflections

  • 272 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 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...O2 0.86 2.07 2.709 (3) 130
C19-H19A...O3i 0.93 2.42 3.294 (3) 157
C21-H21A...O3i 0.96 2.60 3.491 (4) 155
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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: RZ5041 ).


Acknowledgements

This project was supported by King Saud University, Deanship of Scientific Research, College of Science Research Center.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, K.-G., Wang, Z.-W., Zhao, X.-Q. & Fang, T. (2003). Chin. J. Org. Chem. 23, 1411-1415.  [ChemPort]
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Alamary, A. S. & Al-Nahary, T. T. (2012). Int. J. Mol. Sci. 13, 5035-5047.  [CrossRef] [ChemPort] [PubMed]
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Al-Othman, Z. A. & Alamary, A. S. (2011). Int. J. Mol. Sci. 12, 7824-7834.  [ChemPort] [PubMed]
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.  [CrossRef] [ChemPort] [PubMed]
Mabkhot, Y. N., Barakat, A. & Alshahrani, S. (2012). J. Mol. Struct., 1027, 15-19.  [ISI] [CrossRef] [ChemPort]
Mishra, R., Tomar, I., Singhal, S. & Jha, K. K. (2011). Pharma Chem. 3, 38-54.  [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o351  [ doi:10.1107/S1600536813003231 ]

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