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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 [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 25.5
Details
Open access

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

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-H...O and C-H...O 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[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.]); Moore et al. (1940[Moore, M. L., Miller, C. S. & Miller, E. (1940). J. Am. Chem. Soc. 62, 2097-2099.]); Suyama & Gerwick (2006[Suyama, T. L. & Gerwick, W. H. (2006). Org. Lett. 8, 4541-4543.]). For a related structure, see: Loureiro et al. (2008[Loureiro, R. M. S., Johnstone, R. A. W. & Labat, G. (2008). Acta Cryst. C64, o306-o308.]). For further synthetic information, see: Augustine et al. (2011[Augustine, J. K., Kumar, R., Bombrun, A. & Mandal, A. B. (2011). Tetrahedron Lett. 52, 1074-1077.]); Sollogoub et al. (2002[Sollogoub, M., Fox, K. R., Powers, V. E. C. & Brown, T. (2002). Tetrahedron Lett. 43, 3121-3123.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7BrN2O

  • Mr = 215.06

  • Triclinic, [P \overline 1]

  • a = 4.0014 (3) Å

  • b = 8.7232 (6) Å

  • c = 23.0626 (18) Å

  • [alpha] = 82.127 (1)°

  • [beta] = 86.897 (1)°

  • [gamma] = 85.932 (1)°

  • V = 794.60 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.111, Tmax = 0.665

  • 13194 measured reflections

  • 5134 independent reflections

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

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.00

  • 5134 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2A-H1NA...O1Bi 0.85 2.16 3.001 (2) 169
N2B-H1NB...O1Aii 0.83 2.20 2.985 (2) 159
C7A-H7AA...O1Bi 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: 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.  [CrossRef] [ChemPort]
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.  [CSD] [CrossRef] [details]
Moore, M. L., Miller, C. S. & Miller, E. (1940). J. Am. Chem. Soc. 62, 2097-2099.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sollogoub, M., Fox, K. R., Powers, V. E. C. & Brown, T. (2002). Tetrahedron Lett. 43, 3121-3123.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suyama, T. L. & Gerwick, W. H. (2006). Org. Lett. 8, 4541-4543.  [CrossRef] [ChemPort]


Acta Cryst (2011). E67, o2043  [ doi:10.1107/S1600536811027553 ]

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