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Volume 69 
Part 3 
Page o322  
March 2013  

Received 24 January 2013
Accepted 28 January 2013
Online 2 February 2013

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.033
wR = 0.092
Data-to-parameter ratio = 13.6
Details
Open access

3-(2-Bromoacetyl)phenyl benzoate

Sachin P Ambekar,a H. C. Devarajegowda,b* J. ShylajaKumari,c K. Mahesh Kumara and O. Kotresha

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India,bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and cDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C15H11BrO3, the dihedral angle between the benzene rings is 72.59 (6)°. In the crystal, pairs of C-H...[pi] contacts form inversion dimers. Additional C-H...O hydrogen bonds generate R21(6) ring motifs and stack these dimers along the b axis. Short intermolecular Br...O contacts of 3.254 (3) Å are also observed and link the stacks into a three-dimensional network.

Related literature

For the biological applications and synthesis of the title compound, see: Naoto et al. (2008[Naoto, O., Mariko, O., Takashi, S., Satoshi, K., Atsuko, M., Noriaki, U., Yoshisuke, N., Keishi, K., Masamori, S. & Yushi, K. (2008). PCT Int. Appl. WO 2008029825/A1 20080313.]); Shwu-Jiuan & Mei-Hua (1984[Shwu-Jiuan, L. & Mei-Hua, L. (1984). Bull. Inst. Chem. Acad. Sin. 31, 55-58.]); Jaakko & Erkki (1959[Jaakko, H. & Erkki, H. (1959). Acta Chem. Scand. 13, 329-33.]); Junichi et al. (1956[Junichi, I., Takuro, I., Chikara, K. & Mitsutaka, K. (1956). Ann. Rept. G. Tanabe Co. Ltd, 1, 17-20.]); D'Amico et al. (1956[D'Amico, A., Bertolini, L. & Monreale, C. (1956). Chim. l'Ind. (Milan, Italy), 38, 93-99.]). For hydrogen-bond motifs, 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

  • C15H11BrO3

  • Mr = 319.15

  • Monoclinic, P 21 /n

  • a = 12.5055 (4) Å

  • b = 5.4409 (2) Å

  • c = 19.5178 (6) Å

  • [beta] = 90.859 (2)°

  • V = 1327.86 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.10 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 11209 measured reflections

  • 2344 independent reflections

  • 1929 reflections with I > 2[sigma](I)

  • Rint = 0.033
Refinement

  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.092

  • S = 1.05

  • 2344 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10-C15 benzene ring.
D-H...A D-H H...A D...A D-H...A
C4-H4...O3i 0.93 2.70 3.557 (4) 153
C1-H1B...O3i 0.97 2.65 3.550 (4) 155
C6-H6...Cg2ii 0.93 2.88 3.627 (3) 138
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. 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.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5298 ).

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection and GCMS, IR, CHNS and NMR data. SPA is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
D'Amico, A., Bertolini, L. & Monreale, C. (1956). Chim. l'Ind. (Milan, Italy), 38, 93-99.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jaakko, H. & Erkki, H. (1959). Acta Chem. Scand. 13, 329-33.
Junichi, I., Takuro, I., Chikara, K. & Mitsutaka, K. (1956). Ann. Rept. G. Tanabe Co. Ltd, 1, 17-20.
Naoto, O., Mariko, O., Takashi, S., Satoshi, K., Atsuko, M., Noriaki, U., Yoshisuke, N., Keishi, K., Masamori, S. & Yushi, K. (2008). PCT Int. Appl. WO 2008029825/A1 20080313.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shwu-Jiuan, L. & Mei-Hua, L. (1984). Bull. Inst. Chem. Acad. Sin. 31, 55-58.

Acta Cryst (2013). E69, o322  [ doi:10.1107/S1600536813002900 ]

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