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Volume 68 
Part 11 
Page o3184  
November 2012  

Received 4 October 2012
Accepted 16 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.129
Data-to-parameter ratio = 19.6
Details
Open access

Methyl (E)-2-cyano-3-(6-nitro-1,3-benzodioxol-5-yl)acrylate

aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India,bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India,cDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, and dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C12H8N2O6, the 1,3-benzodioxole ring system is essentially planar [maximum deviation = 0.036 (2) Å] and the nitro group is oriented at a dihedral angle of 15.4 (1)° with respect to its mean plane. In the crystal, moleucles are linked into C(8) [101] chains by C-H...O hydrogen bonds, and weak aromatic [pi]-[pi] stacking [centroid-centroid distance = 3.887 (1) Å] also occurs.

Related literature

For a related structure and background references, see: Karthikeyan et al. (2011[Karthikeyan, S., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2011). Acta Cryst. E67, o3469.]); Loghmani-Khouzani et al. (2009[Loghmani-Khouzani, H., Abdul Rahman, N., Robinson, W. T., Yaeghoobi, M. & Kia, R. (2009). Acta Cryst. E65, o2545.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8N2O6

  • Mr = 276.20

  • Monoclinic, P 21 /n

  • a = 10.8191 (9) Å

  • b = 7.3220 (6) Å

  • c = 15.4133 (13) Å

  • [beta] = 91.691 (2)°

  • V = 1220.47 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 K

  • 0.23 × 0.22 × 0.17 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.972, Tmax = 0.979

  • 14190 measured reflections

  • 3567 independent reflections

  • 2286 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.129

  • S = 1.03

  • 3567 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3B...O4i 0.97 2.51 3.247 (2) 132
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]); 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: HB6968 ).


Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Karthikeyan, S., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2011). Acta Cryst. E67, o3469.  [CSD] [CrossRef] [details]
Loghmani-Khouzani, H., Abdul Rahman, N., Robinson, W. T., Yaeghoobi, M. & Kia, R. (2009). Acta Cryst. E65, o2545.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
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 (2012). E68, o3184  [ doi:10.1107/S1600536812043164 ]

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