N-(5-Bromo­pyridin-2-yl)acetamide

Fun, H.-K.; Shahani, T.; Kumar, R.; Isloor, A.M.; Shivananda, K.N.

doi:10.1107/S1600536811027553

Volume 67
Part 8
Page o2043
August 2011

Received 25 June 2011
Accepted 9 July 2011
Online 16 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 25.5
Details

N-(5-Bromopyridin-2-yl)acetamide

Hoong-Kun Fun,^a ^*⁺ Tara Shahani,^a Rajesha Kumar,^b Arun M. Isloor ^b and Kammasandra N. Shivananda ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, C₇H₇BrN₂O, contains two molecules, in one of which the methyl H atoms are disorderd over two orientations in a 0.57 (3):0.43 (3) ratio. The dihedral angles between the pyridine rings and the acetamide groups are 7.27 (11) and 8.46 (11)°. In the crystal, molecules are linked by N-HO and C-HO hydrogen bonds generating bifurcated R₂¹(5) ring motifs, which in turn lead to [110] chains.

Related literature

For background to the acetylation of amines, see: Greene & Wuts (1999); Moore et al. (1940); Suyama & Gerwick (2006). For a related structure, see: Loureiro et al. (2008). For further synthetic information, see: Augustine et al. (2011); Sollogoub et al. (2002).

Experimental

Crystal data

C₇H₇BrN₂O
M_r = 215.06
Triclinic, $[P \overline 1]$
a = 4.0014 (3) Å
b = 8.7232 (6) Å
c = 23.0626 (18) Å
= 82.127 (1)°
= 86.897 (1)°
= 85.932 (1)°
V = 794.60 (10) Å³
Z = 4
Mo K radiation
= 5.11 mm^-1
T = 296 K
0.77 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.111, T_max = 0.665
13194 measured reflections
5134 independent reflections
3193 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.081
S = 1.00
5134 reflections
201 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2A-H1NAO1Bⁱ	0.85	2.16	3.001 (2)	169
N2B-H1NBO1Aⁱⁱ	0.83	2.20	2.985 (2)	159
C7A-H7AAO1Bⁱ	1.10	2.54	3.476 (3)	142
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: HB5933 ).

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship. AMI thanks Professor Sandeep Sanchethi, Director, National Institute of Technology-Karnataka, India, for his encouragement, and also the Defence Research and Development Organization, Government of India, for financial support.

References

Augustine, J. K., Kumar, R., Bombrun, A. & Mandal, A. B. (2011). Tetrahedron Lett. 52, 1074-1077.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Greene, T. W. & Wuts, P. G. M. (1999). Protective Groups in Organic Chemistry, 3rd ed., ch. 7, pp. 552-555. New York: Wiley and Sons.
Loureiro, R. M. S., Johnstone, R. A. W. & Labat, G. (2008). Acta Cryst. C64, o306-o308.
Moore, M. L., Miller, C. S. & Miller, E. (1940). J. Am. Chem. Soc. 62, 2097-2099.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sollogoub, M., Fox, K. R., Powers, V. E. C. & Brown, T. (2002). Tetrahedron Lett. 43, 3121-3123.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suyama, T. L. & Gerwick, W. H. (2006). Org. Lett. 8, 4541-4543.

organic compounds