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Volume 70 
Part 1 
Page o4  
January 2014  

Received 20 November 2013
Accepted 27 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.044
wR = 0.119
Data-to-parameter ratio = 27.0
Details
Open access

2,6-Bis(bromo­meth­yl)pyridine

aInstitute of Chemistry of the Academy of Sciences of Moldova, 3 Academiei Street, Chisinau MD-2028, Republic of Moldova, and bAix Marseille Université, ISM2 UMR 7313, Campus de St. Jérôme, Av. Escadrille Normandie Niemen, 13397 Marseille Cedex 20, France
Correspondence e-mail: olesea_cuzan@yahoo.com

In the title mol­ecule, C7H7Br2N, the C-Br vectors of the bromo­methyl groups extend to opposite sides of the pyridine ring and are oriented nearly perpendicular to its plane. In the crystal, the mol­ecules related by a c-glide-plane operation are arranged into stacks along the c axis, with centroid-centroid distances between neighboring aromatic rings of 3.778 (2) Å. A short Br...Br contact of 3.6025 (11) Å is observed within a pair of inversion-related mol­ecules.

Related literature

For the isomorphous crystal structure of 2,6-bis­(chloro­meth­yl)pyridine, see: Betz et al. (2011[Betz, R., Gerber, T. & Schalekamp, H. (2011). Acta Cryst. E67, o1577.]). For the synthesis of the title compound, see: Dioury et al. (2009[Dioury, F., Ferroud, C., Guy, A. & Port, M. (2009). Tetrahedron, 65, 7573-7579.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7Br2N

  • Mr = 264.96

  • Monoclinic, P 21 /c

  • a = 9.2955 (19) Å

  • b = 12.980 (3) Å

  • c = 7.5288 (15) Å

  • [beta] = 110.75 (3)°

  • V = 849.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 9.47 mm-1

  • T = 293 K

  • 0.28 × 0.26 × 0.12 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.088, Tmax = 0.321

  • 10219 measured reflections

  • 2480 independent reflections

  • 1923 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.119

  • S = 1.04

  • 2480 reflections

  • 92 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.99 e Å-3

  • [Delta][rho]min = -1.06 e Å-3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]) 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: GK2596 ).


Acknowledgements

We thank Dr Michel Giorgi (Spectropole, Aix Marseille University) for helpful advice. This research was supported by the bilateral Moldo-French project entitled `Nickel and iron complexes as models of active centre of hydrogenases' 13.820.08.01/FrF; nr. 170783.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Betz, R., Gerber, T. & Schalekamp, H. (2011). Acta Cryst. E67, o1577.  [CSD] [CrossRef] [IUCr Journals]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [IUCr Journals]
Dioury, F., Ferroud, C., Guy, A. & Port, M. (2009). Tetrahedron, 65, 7573-7579.  [Web of Science] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o4  [ doi:10.1107/S1600536813032364 ]

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