N-(4-Bromo-2-methyl­phen­yl)pivalamide

Qing, W.-X.; Zhang, W.

doi:10.1107/S1600536809034345

Volume 65
Part 10
Page o2313
October 2009

Received 13 August 2009
Accepted 27 August 2009
Online 5 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.014 Å
R = 0.064
wR = 0.211
Data-to-parameter ratio = 17.1
Details

N-(4-Bromo-2-methylphenyl)pivalamide

Wei-Xia Qing ^a ^* and Wei Zhang ^b

^aMedical College of Henan University, Henan University, Kaifeng 475004, People's Republic of China, and ^bDepartment of Pharmacy, Zhengzhou Railway Vocational and Technological College, Zhengzhou 450052, People's Republic of China
Correspondence e-mail: qingweixia2005@163.com

The conformation of the N-H bond in the title compound, C₁₂H₁₆BrNO, is syn to the ortho-methyl substituent. There are two unique molecules in the asymmetric unit. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules, forming infinite chains down [010].

Related literature

For a study of the effect of ring and side-chain substitution on the crystal structures of aromatic amides, see: Gowda et al. (2007). For related structures, see: Gowda et al. (2007a,b,c).

Experimental

Crystal data

C₁₂H₁₆BrNO
M_r = 270.17
Monoclinic, P 2₁ /c
a = 11.764 (3) Å
b = 19.584 (5) Å
c = 12.956 (3) Å
= 117.877 (19)°
V = 2638.5 (11) Å³
Z = 8
Mo K radiation
= 3.09 mm^-1
T = 293 K
0.42 × 0.37 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.357, T_max = 0.438
24481 measured reflections
4634 independent reflections
1875 reflections with I > 2(I)
R_int = 0.113

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.211
S = 1.01
4634 reflections
271 parameters
65 restraints
H-atom parameters constrained
_max = 0.90 e Å^-3
_min = -0.70 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2ⁱ	0.86	2.14	2.989 (8)	170
N2-H2BO1ⁱⁱ	0.86	2.14	2.943 (8)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2861 ).

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2631-o2632.
Gowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o3788.
Gowda, B. T., Foro, S. & Fuess, H. (2007c). Acta Cryst. E63, o2331-o2332.
Gowda, B. T., Kozisek, J., Tokarcík, M. & Fuess, H. (2007). Acta Cryst. E63, o1983-o1984.
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds