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Volume 69 
Part 6 
Page o852  
June 2013  

Received 6 April 2013
Accepted 3 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.092
Data-to-parameter ratio = 24.2
Details
Open access

Methyl (2Z)-2-bromomethyl-3-(3-chlorophenyl)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

There are two independent molecules (A and B) in the asymmetric unit of the title compound C11H10BrClO2, which represents the Z isomer. The methylacrylate moieties are essentially planar, within 0.084 (2) and 0.027 (5) Å in molecules A and B, respectively. The benzene ring makes dihedral angles of 13.17 (7) and 27.89 (9)° with the methylacrylate moiety in molecules A and B, respectively. The methylbromide moiety is almost orthogonal to the benzene ring, making dihedral angles of 81.46 (16)° in molecule A and 79.61 (16)° in molecule B. The methylacrylate moiety exhibits an extended trans conformation in both molecules. In the crystal, pairs of C-H...O hydrogen bonds result in the formation of quasi-centrosymmetric R22(14) AB dimers.

Related literature

For the uses of cinnamic acid and its derivatives, see: De et al. (2011[De, P., Baltas, M. & Bedos-Belval, F. (2011). Curr. Med. Chem. 18, 1672-1703.]); Sharma (2011[Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.]). For an extended acrylate conformation, see: Schweizer & Dunitz (1982[Schweizer, W. B. & Dunitz, J. D. (1982). Helv. Chim. Acta, 65, 1547-1554.]). For a related structure, see: Swaminathan et al. (2013[Swaminathan, K., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2013). Acta Cryst. E69, o572.]). 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.])

[Scheme 1]

Experimental

Crystal data
  • C11H10BrClO2

  • Mr = 289.54

  • Triclinic, [P \overline 1]

  • a = 7.4523 (3) Å

  • b = 11.7003 (4) Å

  • c = 14.3121 (5) Å

  • [alpha] = 72.078 (2)°

  • [beta] = 76.539 (2)°

  • [gamma] = 76.773 (2)°

  • V = 1137.98 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.82 mm-1

  • T = 296 K

  • 0.30 × 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, U. S. A.]) Tmin = 0.330, Tmax = 0.466

  • 27124 measured reflections

  • 6597 independent reflections

  • 4205 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.092

  • S = 1.00

  • 6597 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.85 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1A-H1A...O1Bi 0.93 2.53 3.429 (3) 161
C1B-H1B...O1Ai 0.93 2.51 3.380 (3) 156
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); 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, 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: LD2100 ).


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 Minor Research Project support.

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, U. S. A.
De, P., Baltas, M. & Bedos-Belval, F. (2011). Curr. Med. Chem. 18, 1672-1703.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Schweizer, W. B. & Dunitz, J. D. (1982). Helv. Chim. Acta, 65, 1547-1554.  [CrossRef] [ChemPort]
Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Swaminathan, K., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2013). Acta Cryst. E69, o572.  [CrossRef] [details]


Acta Cryst (2013). E69, o852  [ doi:10.1107/S1600536813012117 ]

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