N,N′-Bis(5-bromo­pyridin-2-yl)methane­diamine

Nichol, G.S.; Sharma, A.; Li, H.-Y.

doi:10.1107/S160053681100821X

Volume 67
Part 4
Page o833
April 2011

Received 22 February 2011
Accepted 3 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.019
wR = 0.051
Data-to-parameter ratio = 19.4
Details

N,N'-Bis(5-bromopyridin-2-yl)methanediamine

Gary S. Nichol,^a ^* Anuj Sharma ^b and Hong-Yu Li ^b

^aDepartment of Chemistry and Biochemistry, 1306 E University Boulevard, The University of Arizona, Tucson, AZ 85721, USA, and ^bSouthwest Center for Drug Discovery, College of Pharmacy, The University of Arizona, Tucson, AZ 85737, USA
Correspondence e-mail: gsnichol@email.arizona.edu

The V-shaped title compound, C₁₁H₁₀Br₂N₄, lies on a crystallographic twofold rotation axis which passes through the central C atom. In the crystal, an infinite tape motif, which propagates in the a-axis direction, is formed by inversion-related N-HN hydrogen-bonding interactions. The structure confirmed the identity of the compound as a reaction side product.

Related literature

For background information on the Groebke-Blackburn synthesis, see: Bienaymé & Bouzid (1998); Blackburn et al. (1998); Groebke et al. (1998); Mandair et al. (2002); Parchinsky et al. (2006). For the crystal structure of a similar compound, see: Wu et al. (2004). For information on graph-set notation to describe hydrogen-bonding motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₀Br₂N₄
M_r = 358.05
Monoclinic, I 2/a
a = 11.9075 (6) Å
b = 4.0523 (2) Å
c = 25.8065 (15) Å
= 98.326 (3)°
V = 1232.11 (11) Å³
Z = 4
Mo K radiation
= 6.56 mm^-1
T = 100 K
0.24 × 0.08 × 0.07 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: numerical (SADABS; Sheldrick, 1996) T_min = 0.297, T_max = 0.675
11800 measured reflections
1903 independent reflections
1674 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.019
wR(F²) = 0.051
S = 1.03
1903 reflections
98 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.70 e Å^-3
_min = -0.47 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NN1ⁱ	0.87 (1)	2.11 (1)	2.9645 (18)	168 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2010) and local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5123 ).

Acknowledgements

The diffractometer was purchased with funding from NSF grant CHE-0741837.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bienaymé, H. & Bouzid, K. (1998). Angew. Chem. Int. Ed. 37, 2234-2237.
Blackburn, C., Guan, B., Fleming, P., Shiosaki, K. & Tsai, S. (1998). Tetrahedron Lett. 39, 3635-3638.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Groebke, K., Weber, L. & Mehlin, F. (1998). Synlett, pp. 661-663.
Mandair, G. S., Light, M., Russell, A., Hursthouse, M. & Bradley, M. (2002). Tetrahedron Lett. 43, 4267-4269.
Parchinsky, V. Z., Schuvalova, O., Ushalova, O., Krachenko, D. V. & Krasavin, M. (2006). Tetrahedron Lett. 47, 947-951.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Wu, H., Zhou, J., Yu, H.-Z., Lu, L.-L., Xu, Z., Yu, K.-B. & Shi, D.-Q. (2004). Acta Cryst. E60, o2085-o2086.

organic compounds