[Journal logo]

Volume 69 
Part 4 
Page o583  
April 2013  

Received 1 March 2013
Accepted 16 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.058
Data-to-parameter ratio = 14.4
Details
Open access

5-Bromo-2-chloropyrimidin-4-amine

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Chemistry, Yuvarajas College, University of Mysore, Mysore 570 005, India, and cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: mas@physics.uni-mysore.ac.in

In the title compound, C4H3BrClN3, the pyrimidine ring is essentially planar (r.m.s. deviation from the plane = 0.087 Å). In the crystal, pairs of N-H...N hydrogen bonds connect the molecules into inversion dimers; these are connected by further N-H...N hydrogen bonds into a two-dimensional framework parallel to the bc plane.

Related literature

For background to pyrimidine derivatives, see: Yu et al. (2007[Yu, Z. H., Niu, C. W., Ban, S. R., Wen, X. & Xi, Z. (2007). Chin. Sci. Bull. 52, 1929-1941.]). For related structures, see: van Albada et al. (2012[Albada, G. van, Ghazzali, M., Al-Farhan, K. & Reedijk, J. (2012). Acta Cryst. E68, o302.]); Yang et al. (2012[Yang, Q., Xu, N., Zhu, K., Lv, X. & Han, P. (2012). Acta Cryst. E68, o111.]).

[Scheme 1]

Experimental

Crystal data
  • C4H3BrClN3

  • Mr = 208.45

  • Monoclinic, P 21 /c

  • a = 6.0297 (1) Å

  • b = 8.1542 (2) Å

  • c = 13.4163 (3) Å

  • [beta] = 90.491 (2)°

  • V = 659.62 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.54 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.306, Tmax = 1.000

  • 43395 measured reflections

  • 1297 independent reflections

  • 1164 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.058

  • S = 1.10

  • 1297 reflections

  • 90 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N7-H71...N1i 0.78 (3) 2.38 (3) 3.087 (3) 153 (3)
N7-H72...N3ii 0.91 (4) 2.19 (4) 3.088 (3) 171 (3)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: 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: GK2560 ).


Acknowledgements

MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola for his research work. RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Albada, G. van, Ghazzali, M., Al-Farhan, K. & Reedijk, J. (2012). Acta Cryst. E68, o302.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yang, Q., Xu, N., Zhu, K., Lv, X. & Han, P. (2012). Acta Cryst. E68, o111.  [CSD] [CrossRef] [details]
Yu, Z. H., Niu, C. W., Ban, S. R., Wen, X. & Xi, Z. (2007). Chin. Sci. Bull. 52, 1929-1941.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o583  [ doi:10.1107/S1600536813007228 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.