6,8-Dibromo­quinoline

Çelik, Í.; Akkurt, M.; Çakmak, O.; Ökten, S.; García-Granda, S.

doi:10.1107/S1600536810043242

Volume 66
Part 11
Pages o2997-o2998
November 2010

Received 20 October 2010
Accepted 23 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.010 Å
R = 0.045
wR = 0.141
Data-to-parameter ratio = 14.7
Details

6,8-Dibromoquinoline

Ísmail Çelik,^a Mehmet Akkurt,^b ^* Osman Çakmak,^c Salih Ökten ^c and Santiago García-Granda ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey,^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^cDepartment of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60240 Tokat, Turkey, and ^dDepartamento Química Física y Analítica, Facultad de Química, Universidad Oviedo, C/ Julián Clavería, 8, 33006 Oviedo (Asturias), Spain
Correspondence e-mail: akkurt@erciyes.edu.tr

The title molecule, C₉H₅Br₂N, is almost planar, with an r.m.s. deviation of 0.027 Å. The dihedral angle between the aromatic rings is 1.5 (3)°. In the crystal, [pi] - [pi] stacking interactions are present between the pyridine and benzene rings of adjacent molecules [centroid-centroid distances = 3.634 (4) Å], and short BrBr contacts [3.4443 (13) Å] occur.

Related literature

For the biological and pharmacological activities of quinolines and their derivatives, see: Abadi et al. (2005); Blackie et al. (2007); Chen et al. (2006); Gómez et al. (2008); Gómez-Barrio et al. (2006); Kouznetsov et al. (2005, 2007); Lindley (1984); Metwally et al. (2006); Muscia et al. (2006); Musiol et al. (2007); Sissi & Palumbo (2003); Vangapandu et al. (2004); Vinsova et al. (2008); Vladímir et al. (2005); Zhao et al. (2005); Zhu et al. (2007); Sahin et al. (2008). For the synthesis, see: Ökten et al. (2010).

Experimental

Crystal data

C₉H₅Br₂N
M_r = 286.94
Monoclinic, P 2₁ /c
a = 7.3436 (12) Å
b = 9.8961 (15) Å
c = 13.0108 (18) Å
= 109.589 (17)°
V = 890.8 (3) Å³
Z = 4
Cu K radiation
= 11.04 mm^-1
T = 297 K
0.12 × 0.09 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini CCD detector
Absorption correction: part of the refinement model (F) (XABS2; Parkin et al., 1995)T_min = 0.052, T_max = 0.080
1598 measured reflections
1598 independent reflections
1075 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.141
S = 1.02
1598 reflections
109 parameters
H-atom parameters constrained
_max = 0.68 e Å^-3
_min = -0.56 e Å^-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1997) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5698 ).

Acknowledgements

The authors thank the Cumhuriyet University Research Foundation (CUBAP grant No. 2009/ F-266) for financial support.

References

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organic compounds