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Volume 69 
Part 12 
Page o1729  
December 2013  

Received 14 October 2013
Accepted 25 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.025
wR = 0.066
Data-to-parameter ratio = 15.3
Details
Open access

2-Bromo-3-hy­droxy-6-methyl­pyridine

aDepartment of Chemistry, Sri Sathya Sai Institute of Higher Learning, Prasanthinilayam, Ananthapur, Andhra Pradesh, 515 134, India,bSchool of Chemistry, University of Hyderabad, Gachibowli, Hyderabad, 500 046, India, and cDepartment of Chemistry, Sri Sathya Sai Institute of Higher Learning, Brindavan Campus, Whitefield, Bangalore, India
Correspondence e-mail: gnageswararao@sssihl.edu.in

In the title compound, C6H6BrNO, the Br atom is displaced from the pyridine ring mean plane by 0.0948 (3) Å, while the hydroxyl O atom and the methyl C atom are displaced by 0.0173 (19) and 0.015 (3) Å, respectively. In the crystal, mol­ecules are linked via O-H...N hydrogen bonds, forming chains propagating along the a-axis direction. These chains are linked by C-H...Br hydrogen bonds, forming corrugated two-dimensional networks lying parallel to the ac plane.

Related literature

3-Hy­droxy­pyridine, the core skeleton of the title compound is an integral part of Nikkomycin Z (a potent fungicide), see: Tetsu et al. (1990[Tetsu, A., Berhane, T., Robert, F. T. & John, E. C. (1990). J. Agric. Food Chem. 38, 1712-1715.]). For the synthesis, see: Kjell et al. (1969[Kjell, U., Vegard, N. & Knut, T. (1969). Acta Chem. Scand. 23, 1704-1714.]).

[Scheme 1]

Experimental

Crystal data
  • C6H6BrNO

  • Mr = 188.03

  • Orthorhombic, P b c a

  • a = 11.4484 (19) Å

  • b = 9.0914 (15) Å

  • c = 13.230 (2) Å

  • V = 1377.1 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 5.88 mm-1

  • T = 298 K

  • 0.32 × 0.22 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.255, Tmax = 0.539

  • 12822 measured reflections

  • 1335 independent reflections

  • 1115 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.066

  • S = 1.06

  • 1335 reflections

  • 87 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.80 (3) 1.92 (3) 2.717 (3) 174 (3)
C6-H6B...Br1ii 0.96 3.04 3.993 (3) 174
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2659 ).


Acknowledgements

The authors thank Bhagavan Sri Sathya Sai Baba for constant guidance and motivation. We would like to thank Professor Ashwini Nangia, University of Hyderabad, for his help with the single-crystal X-ray diffraction facility. GNR acknowledges financial support from the Council of Scientific and Industrial Research (CSIR), 01 (2286)/08/EMR-II, India. NRG thanks the CSIR for a fellowship.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2001). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.
Kjell, U., Vegard, N. & Knut, T. (1969). Acta Chem. Scand. 23, 1704-1714.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tetsu, A., Berhane, T., Robert, F. T. & John, E. C. (1990). J. Agric. Food Chem. 38, 1712-1715.


Acta Cryst (2013). E69, o1729  [ doi:10.1107/S1600536813029498 ]

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