(Z)-Methyl 2-[(4-bromo-2-formyl­phen­oxy)meth­yl]-3-o-tolyl­acrylate

Vijayakumar, S.; Madhanraj, R.; Murugavel, S.; Selvakumar, R.; Bakthadoss, M.

doi:10.1107/S1600536811037731

Volume 67
Part 10
Page o2690
October 2011

Received 11 September 2011
Accepted 15 September 2011
Online 20 September 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.125
Data-to-parameter ratio = 24.8
Details

(Z)-Methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-o-tolylacrylate

S. Vijayakumar,^a R. Madhanraj,^b S. Murugavel,^c ^* R. Selvakumar ^d and M. Bakthadoss ^d

^aDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India,^bDepartment of Physics, Ranipettai Engineering College, Thenkadapathangal, Walaja 632 513, India,^cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^dDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C₁₉H₁₇BrO₄, the dihedral angle between the two benzene rings is 82.1 (1)°. The molecular structure is stabilized by an intramolecular C-HO hydrogen bond which generates an S(7) ring motif. The crystal packing is stabilized by intermolecular C-HO hydrogen bonds and C-H [pi] interactions. Intermolecular C-HO interactions are involved in the formation of centrosymmetric R₂²(16) dimers, which are connected into supramolecular tapes running along the [100] direction.

Related literature

For background to the applications of acrylates, see: de Fraine et al. (1991); Zhang & Ji (1992). For related structures, see: Wang et al. (2011); Hou (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₉H₁₇BrO₄
M_r = 389.24
Triclinic, $[P \overline 1]$
a = 8.0114 (2) Å
b = 8.6138 (2) Å
c = 13.4827 (4) Å
= 96.466 (1)°
= 97.185 (1)°
= 106.546 (2)°
V = 874.08 (4) Å³
Z = 2
Mo K radiation
= 2.37 mm^-1
T = 293 K
0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.547, T_max = 0.653
21788 measured reflections
5440 independent reflections
2870 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.125
S = 1.02
5440 reflections
219 parameters
H-atom parameters constrained
_max = 0.61 e Å^-3
_min = -0.61 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13-C18 benzene ring.

D-HA	D-H	HA	DA	D-HA
C14-H14O3	0.93	2.59	3.377 (3)	143
C19-H19BO1ⁱ	0.96	2.53	3.436 (3)	157
C5-H5O4ⁱⁱ	0.93	2.44	3.273 (3)	149
C19-H19CCgⁱⁱⁱ	0.96	2.74	3.580 (3)	147
Symmetry codes: (i) -x+1, -y, -z; (ii) x+1, y, z; (iii) -x+2, -y+1, -z.

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: BT5640 ).

Acknowledgements

SM thanks Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fraine, P. J. de & Martin, A. (1991). US Patent 5 055 471.
Hou, J. (2008). Acta Cryst. E64, o2293.
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.
Wang, L., Meng, F.-Y., Lin, C.-W., Chen, H.-Y. & Luo, X. (2011). Acta Cryst. E67, o354.
Zhang, L. P. & Ji, Z. Z. (1992). Acta Pharmacol. Sin. 27, 817-823.

organic compounds