4-Bromo-N-phenyl­benzamide

Fun, H.-K.; Chantrapromma, S.; Sripet, W.; Ruanwas, P.; Boonnak, N.

doi:10.1107/S1600536812013487

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 (C-C) = 0.003 Å
R = 0.032
wR = 0.076
Data-to-parameter ratio = 25.8
Details

4-Bromo-N-phenylbenzamide

Hoong-Kun Fun,^a ^*⁺ Suchada Chantrapromma,^b ⁺⁺ Weerawat Sripet,^b Pumsak Ruanwas ^b and Nawong Boonnak ^b

^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-HO hydrogen bonds into chains along [100]. C-H [pi] contacts combine with the N-HO hydrogen bonds, to form a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987). For related structures, see: Johnston & Taylor (2011); Li & Cui (2011); Saeed et al. (2008); Sripet et al. (2012). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010); Brown et al. (1991); Hu et al. (2008); Mobinikhaledi et al. (2006); Olsson et al. (2002); World Health Organization (2003); Xu et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₃H₁₀BrNO
M_r = 276.12
Triclinic, $[P \overline 1]$
a = 5.3552 (2) Å
b = 7.6334 (2) Å
c = 13.9956 (5) Å
= 105.757 (3)°
= 100.585 (3)°
= 90.086 (2)°
V = 540.45 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.406, T_max = 0.791
11303 measured reflections
3844 independent reflections
3193 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(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
_max = 0.66 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N1-H1N1O1ⁱ	0.84 (3)	2.37 (3)	3.150 (2)	156 (2)
C2-H2ACg2ⁱⁱ	0.95	2.77	3.4855 (19)	132
C5-H5ACg2ⁱⁱⁱ	0.95	2.70	3.4258 (19)	134
C10-H10ACg1^iv	0.95	2.90	3.5444 (19)	126
C13-H13ACg1^v	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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

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organic compounds