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Volume 69 
Part 7 
Page o1049  
July 2013  

Received 28 May 2013
Accepted 4 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.126
Data-to-parameter ratio = 19.1
Details
Open access

Ethyl 4-acetyl-5-anilino-3-methylthiophene-2-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: dr.sammer.yousuf@gmail.com

In the title compound, C16H17NO3S, a thiophene derivative with amino phenyl, acetyl, methyl and ethyl carboxyl susbtituents attached to a central thiophene ring, the phenyl and thiophene rings form a dihedral angle of 36.92 (9) Å. The molecular conformation is stabilized by an intramolecular N-H...O hydrogen bond, which forms an S(6) ring motif.

Related literature

For the biological activity of thiophene derivatives, see: Mishra et al. (2011[Mishra, R., Jha, K. K., Kumar, S. & Tomer, S. (2011). Pharma Chem. 3, 38-54.]); Mabkhot et al. (2013b[Mabkhot, Y. N., Barakat, A., Al-Majid, A. & Choudhary, M. I. (2013b). Int. J. Mol. Sci. 14, 5712-5722.]). For the synthesis of fused heterocyclic compounds, see: Sommen et al. (2003[Sommen, G., Comel, A. & Kirsch, G. (2003). Tetrahedron 59, 1557-1564.]). For crystal data for related thiophene compounds, see: Mabkhot et al. (2013a[Mabkhot, Y. N., Barakat, A., Alatibi, F., Choudhary, M. I. & Yousuf, S. (2013a). Acta Cryst. E69, o351.],b[Mabkhot, Y. N., Barakat, A., Al-Majid, A. & Choudhary, M. I. (2013b). Int. J. Mol. Sci. 14, 5712-5722.]); Buehrdel et al. (2007[Buehrdel, G., Beckert, R., Birckner, E., Grummt, U.-W., Beyer, B., Kluge, S., Weston, J. & Goerls, H. (2007). Eur. J. Org. Chem. 32, 5404-5409.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17NO3S

  • Mr = 303.37

  • Triclinic, [P \overline 1]

  • a = 7.9443 (6) Å

  • b = 9.5038 (7) Å

  • c = 11.8706 (9) Å

  • [alpha] = 66.759 (2)°

  • [beta] = 89.754 (2)°

  • [gamma] = 66.785 (2)°

  • V = 744.60 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 273 K

  • 0.45 × 0.42 × 0.23 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 = 0.905, Tmax = 0.950

  • 10410 measured reflections

  • 3699 independent reflections

  • 2848 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.126

  • S = 1.05

  • 3699 reflections

  • 194 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1 0.82 (3) 1.93 (3) 2.607 (3) 140 (2)

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; 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: RZ5071 ).


Acknowledgements

The authors are thankful to King Saud University, Deanship of Scientific Research, College of Science Research Center, for financial support of this project.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Buehrdel, G., Beckert, R., Birckner, E., Grummt, U.-W., Beyer, B., Kluge, S., Weston, J. & Goerls, H. (2007). Eur. J. Org. Chem. 32, 5404-5409.  [CSD] [CrossRef]
Mabkhot, Y. N., Barakat, A., Alatibi, F., Choudhary, M. I. & Yousuf, S. (2013a). Acta Cryst. E69, o351.  [CrossRef] [IUCr Journals]
Mabkhot, Y. N., Barakat, A., Al-Majid, A. & Choudhary, M. I. (2013b). Int. J. Mol. Sci. 14, 5712-5722.  [CrossRef] [ChemPort] [PubMed]
Mishra, R., Jha, K. K., Kumar, S. & Tomer, S. (2011). Pharma Chem. 3, 38-54.  [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sommen, G., Comel, A. & Kirsch, G. (2003). Tetrahedron 59, 1557-1564.  [Web of Science] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1049  [ doi:10.1107/S160053681301547X ]

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