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

Bakthadoss, M.; Devaraj, A.; Lakshmanan, D.; Murugavel, S.

doi:10.1107/S1600536812043164

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 (C-C) = 0.002 Å
R = 0.046
wR = 0.129
Data-to-parameter ratio = 19.6
Details

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

M. Bakthadoss,^a,^b ⁺ A. Devaraj,^a D. Lakshmanan ^c and S. Murugavel ^d ^*

^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-HO 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); Loghmani-Khouzani et al. (2009).

Experimental

Crystal data

C₁₂H₈N₂O₆
M_r = 276.20
Monoclinic, P 2₁ /n
a = 10.8191 (9) Å
b = 7.3220 (6) Å
c = 15.4133 (13) Å
= 91.691 (2)°
V = 1220.47 (18) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.972, T_max = 0.979
14190 measured reflections
3567 independent reflections
2286 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.129
S = 1.03
3567 reflections
182 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3BO4ⁱ	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); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Karthikeyan, S., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2011). Acta Cryst. E67, o3469.
Loghmani-Khouzani, H., Abdul Rahman, N., Robinson, W. T., Yaeghoobi, M. & Kia, R. (2009). Acta Cryst. E65, o2545.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References