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Volume 69 
Part 11 
Page o1610  
November 2013  

Received 27 September 2013
Accepted 30 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.067
wR = 0.201
Data-to-parameter ratio = 12.4
Details
Open access

Ethyl (2E)-2-cyano-3-(4-meth­oxy­phen­yl)acrylate

aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,cDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C13H13NO3, the conformation across the C=C bond is synperiplanar, the torsion angle of the segment C(ring)-C=C-C(N) being 3.2 (5)°. In the crystal, mol­ecules are linked into inversion dimers, arranged in a zigzag pattern, through two C-H...O inter­actions generating R22(10) and R22(14) motifs. These dimers are arranged in a zigzag pattern in the crystal structure. The mol­ecules are further linked along the c axis through weak C-H...[pi] inter­actions, and weak [pi]...[pi] inter­actions [centroid-centroid separation = 3.9986 (17) Å] are also observed.

Related literature

For use of the title compound in the synthesis of prop-2-enoyl­amides, see: Santos et al.. (2004[Santos, S. A., Pereira, N., Da Silva, I. M., Sarquis, M. I. M. & Antunes, O. A. C. (2004). Process Biochem. 39, 2269-2275.]). For use of the title compound in the synthesis of prop-2-enoates, see: Sousa et al. (2006[Sousa, J. B., Calheiros, R., Rio, V., Borges, F. & Marques, M. P. M. (2006). J. Mol. Struct. 783, 122-128.]). 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
  • C13H13NO3

  • Mr = 231.24

  • Monoclinic, P 21 /n

  • a = 8.4889 (12) Å

  • b = 8.3552 (16) Å

  • c = 17.143 (3) Å

  • [beta] = 91.294 (11)°

  • V = 1215.6 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.74 mm-1

  • T = 296 K

  • 0.40 × 0.33 × 0.27 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 4798 measured reflections

  • 1937 independent reflections

  • 1354 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.201

  • S = 1.02

  • 1937 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.93 2.54 3.414 (3) 157
C8-H8...O2i 0.93 2.59 3.475 (3) 159
C12-H12A...Cgii 0.97 2.90 3.803 (3) 156
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP; 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: 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5355 ).


Acknowledgements

The authors acknowledge the IOE X-ray diffractometer Facility, University of Mysore, Mysore, for the data collection.

References

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 (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Santos, S. A., Pereira, N., Da Silva, I. M., Sarquis, M. I. M. & Antunes, O. A. C. (2004). Process Biochem. 39, 2269-2275.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sousa, J. B., Calheiros, R., Rio, V., Borges, F. & Marques, M. P. M. (2006). J. Mol. Struct. 783, 122-128.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1610  [ doi:10.1107/S1600536813026871 ]

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