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Volume 68 
Part 4 
Pages o1269-o1270  
April 2012  

Received 20 March 2012
Accepted 28 March 2012
Online 31 March 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.076
Data-to-parameter ratio = 25.8
Details
Open access

4-Bromo-N-phenylbenzamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

The molecule of the title benzamide derivative, C13H10BrNO, is twisted with the dihedral angle between the phenyl and 4-bromophenyl rings being 58.63 (9)°. The central N-C=O plane makes dihedral angles of 30.2 (2) and 29.2 (2)° with the phenyl and 4-bromophenyl rings, respectively. In the crystal, molecules are linked by N-H...O hydrogen bonds into chains along [100]. C-H...[pi] contacts combine with the N-H...O hydrogen bonds, to form a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structures, see: Johnston & Taylor (2011[Johnston, D. H. & Taylor, C. R. (2011). Acta Cryst. E67, o2735.]); Li & Cui (2011[Li, H.-L. & Cui, J.-T. (2011). Acta Cryst. E67, o1596.]); Saeed et al. (2008[Saeed, A., Hussain, S. & Flörke, U. (2008). Acta Cryst. E64, o705.]); Sripet et al. (2012[Sripet, W., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1234.]). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010[Boonleang, J. & Tanthana, C. (2010). Songklanakarin J. Sci. Technol. 32, 605-611.]); Brown et al. (1991[Brown, J. M., Lemmon, M. J., Horsman, M. R. & Lee, W. W. (1991). Int. J. Radiat. Biol. 59, 739-748.]); Hu et al. (2008[Hu, W.-P., Yu, H.-S., Chen, Y.-R., Tsai, Y.-M., Chen, Y.-K., Liao, C.-C., Chang, L.-S. & Wang, J.-J. (2008). Bioorg. Med. Chem. 16, 5295-5302.]); Mobinikhaledi et al. (2006[Mobinikhaledi, A., Forughifar, N., Shariatzadeh, S. M. & Fallah, M. (2006). Heterocycl. Commun. 12, 427-430.]); Olsson et al. (2002[Olsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971-978.]); World Health Organization (2003[World Health Organization (2003). Pharmaceuticals: Restriction in Use and Availability, Essential Drugs and Medicines Policy-Quality Assurance and Safely: Medicines Health Technology and Pharmaceuticals. Geneva, Switzerland.]); Xu et al. (2009[Xu, J., Lecanu, L., Tan, M., Greeson, J. & Papadopoulos, V. (2009). Molecules, 14, 3392-3410.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10BrNO

  • Mr = 276.12

  • Triclinic, [P \overline 1]

  • a = 5.3552 (2) Å

  • b = 7.6334 (2) Å

  • c = 13.9956 (5) Å

  • [alpha] = 105.757 (3)°

  • [beta] = 100.585 (3)°

  • [gamma] = 90.086 (2)°

  • V = 540.45 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.78 mm-1

  • T = 100 K

  • 0.29 × 0.09 × 0.07 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.406, Tmax = 0.791

  • 11303 measured reflections

  • 3844 independent reflections

  • 3193 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.076

  • S = 1.08

  • 3844 reflections

  • 149 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.66 e Å-3

  • [Delta][rho]min = -0.68 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1i 0.84 (3) 2.37 (3) 3.150 (2) 156 (2)
C2-H2A...Cg2ii 0.95 2.77 3.4855 (19) 132
C5-H5A...Cg2iii 0.95 2.70 3.4258 (19) 134
C10-H10A...Cg1iv 0.95 2.90 3.5444 (19) 126
C13-H13A...Cg1v 0.95 2.84 3.4950 (19) 127
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y, -z; (v) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: SJ5220 ).


Acknowledgements

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. NB also thanks Prince of Songkla University for a postdoctoral fellowship. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Boonleang, J. & Tanthana, C. (2010). Songklanakarin J. Sci. Technol. 32, 605-611.
Brown, J. M., Lemmon, M. J., Horsman, M. R. & Lee, W. W. (1991). Int. J. Radiat. Biol. 59, 739-748.  [CrossRef] [PubMed] [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [details]
Hu, W.-P., Yu, H.-S., Chen, Y.-R., Tsai, Y.-M., Chen, Y.-K., Liao, C.-C., Chang, L.-S. & Wang, J.-J. (2008). Bioorg. Med. Chem. 16, 5295-5302.  [CrossRef] [PubMed] [ChemPort]
Johnston, D. H. & Taylor, C. R. (2011). Acta Cryst. E67, o2735.  [CrossRef] [details]
Li, H.-L. & Cui, J.-T. (2011). Acta Cryst. E67, o1596.  [CrossRef] [details]
Mobinikhaledi, A., Forughifar, N., Shariatzadeh, S. M. & Fallah, M. (2006). Heterocycl. Commun. 12, 427-430.  [ChemPort]
Olsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971-978.  [ISI] [CrossRef] [PubMed] [ChemPort]
Saeed, A., Hussain, S. & Flörke, U. (2008). Acta Cryst. E64, o705.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sripet, W., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1234.  [CrossRef] [details]
World Health Organization (2003). Pharmaceuticals: Restriction in Use and Availability, Essential Drugs and Medicines Policy-Quality Assurance and Safely: Medicines Health Technology and Pharmaceuticals. Geneva, Switzerland.
Xu, J., Lecanu, L., Tan, M., Greeson, J. & Papadopoulos, V. (2009). Molecules, 14, 3392-3410.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o1269-o1270   [ doi:10.1107/S1600536812013487 ]

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