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Volume 69 
Part 4 
Page o572  
April 2013  

Received 27 February 2013
Accepted 18 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.102
Data-to-parameter ratio = 25.7
Details
Open access

Methyl (2Z)-2-bromomethyl-3-(2,4-dichlorophenyl)prop-2-enoate

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound C11H9BrCl2O2, which represents the Z isomer, the methylacrylate moiety is essentially planar within 0.039 (2) Å and has an extended trans configuration. The benzene ring makes a dihedral angle of 28.3 (1)° with the mean plane of the methylacrylate moiety. The crystal packing is characterized by C-H...O hydrogen bonding and halogen-halogen interactions [Cl...Cl = 3.486 (3) Å], resulting in the formation of R22(11) ring motifs and connecting the molecules into chains propagating along the b axis.

Related literature

For the uses of cinnamic acid and its derivatives, see: Xiao et al. (2008[Xiao, Z.-P., Fang, R.-Q., Li, H.-Q., Xue, J.-Y., Zheng, Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 1828-1836.]); De Fraine & Martin (1991[De Fraine, P. J. & Martin, A. (1991). US Patent No. 5 055 471.]). For the extended conformation of acrylate, see: Schweizer & Dunitz (1982[Schweizer, W. B. & Dunitz, J. D. (1982). Helv. Chim. Acta, 65, 1547-1554.]). For a related structure, see: Karthikeyan et al. (2012[Karthikeyan, S., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2012). Acta Cryst. E68, o1273.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For type I halogen interactions, see: Johnson & Lemmerer (2012[Johnson, M. & Lemmerer, A. (2012). Acta Cryst. E68, o385.]); Schmidt et al. (2011[Schmidt, N., Schwarzer, A. & Weber, E. (2011). Acta Cryst. E67, o794.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9BrCl2O2

  • Mr = 323.99

  • Triclinic, [P \overline 1]

  • a = 7.9174 (3) Å

  • b = 8.8032 (3) Å

  • c = 9.3585 (3) Å

  • [alpha] = 78.374 (2)°

  • [beta] = 86.599 (2)°

  • [gamma] = 73.528 (2)°

  • V = 612.67 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.77 mm-1

  • T = 293 K

  • 0.25 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.405, Tmax = 0.470

  • 16418 measured reflections

  • 3748 independent reflections

  • 2262 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.102

  • S = 1.00

  • 3748 reflections

  • 146 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.93 2.33 3.238 (3) 167
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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 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: LD2096 ).


Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection. KS thanks the University Grant Commission (UGC), India, for a Minor Research Project.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
De Fraine, P. J. & Martin, A. (1991). US Patent No. 5 055 471.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Johnson, M. & Lemmerer, A. (2012). Acta Cryst. E68, o385.  [CSD] [CrossRef] [details]
Karthikeyan, S., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2012). Acta Cryst. E68, o1273.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Schmidt, N., Schwarzer, A. & Weber, E. (2011). Acta Cryst. E67, o794.  [CSD] [CrossRef] [details]
Schweizer, W. B. & Dunitz, J. D. (1982). Helv. Chim. Acta, 65, 1547-1554.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Xiao, Z.-P., Fang, R.-Q., Li, H.-Q., Xue, J.-Y., Zheng, Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 1828-1836.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o572  [ doi:10.1107/S1600536813007368 ]

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