6,8-Dibromo-quinoline.

The title mol-ecule, C(9)H(5)Br(2)N, 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, π-π stacking inter-actions are present between the pyridine and benzene rings of adjacent mol-ecules [centroid-centroid distances = 3.634 (4) Å], and short Br⋯Br 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 ▶); Şahin et al. (2008 ▶). For the synthesis, see: Ökten et al. (2010 ▶).

Experimental

Crystal data

C9H5Br2N

M = 286.94

Monoclinic,

a = 7.3436 (12) Å

b = 9.8961 (15) Å

c = 13.0108 (18) Å

β = 109.589 (17)°

V = 890.8 (3) Å3

Z = 4

Cu Kα radiation

μ = 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 (ΔF) (XABS2; Parkin et al., 1995 ▶)T min = 0.052, T max = 0.080

1598 measured reflections

1598 independent reflections

1075 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.141

S = 1.02

1598 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.56 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043242/hb5698sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043242/hb5698Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H5Br2N	F(000) = 544
Mr = 286.94	Dx = 2.140 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 1247 reflections
a = 7.3436 (12) Å	θ = 3.6–70.3°
b = 9.8961 (15) Å	µ = 11.04 mm−1
c = 13.0108 (18) Å	T = 297 K
β = 109.589 (17)°	Plate, colourless
V = 890.8 (3) Å3	0.12 × 0.09 × 0.02 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini CCD detector	1598 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1075 reflections with I > 2σ(I)
graphite	Rint = 0.0000
ω scans	θmax = 70.5°, θmin = 5.8°
Absorption correction: part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters]	h = −8→8
Tmin = 0.052, Tmax = 0.080	k = 0→11
1598 measured reflections	l = 0→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0642P)2] where P = (Fo2 + 2Fc2)/3
1598 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.93324 (12)	0.16374 (8)	0.01474 (6)	0.0736 (3)
Br2	0.54665 (13)	0.49672 (10)	−0.34185 (6)	0.0832 (4)
N1	0.8781 (8)	0.4050 (6)	0.1454 (4)	0.0641 (19)
C1	0.8034 (8)	0.4311 (7)	0.0368 (5)	0.055 (2)
C2	0.8120 (8)	0.3287 (6)	−0.0384 (5)	0.0528 (19)
C3	0.7418 (9)	0.3499 (7)	−0.1488 (5)	0.0595 (19)
C4	0.6545 (9)	0.4739 (7)	−0.1875 (5)	0.0550 (19)
C5	0.6420 (9)	0.5744 (7)	−0.1208 (5)	0.059 (2)
C6	0.7184 (9)	0.5558 (7)	−0.0071 (5)	0.058 (2)
C7	0.7125 (10)	0.6584 (8)	0.0673 (6)	0.067 (3)
C8	0.7919 (11)	0.6338 (9)	0.1768 (6)	0.075 (3)
C9	0.8687 (11)	0.5055 (9)	0.2115 (6)	0.075 (3)
H3	0.75210	0.28330	−0.19700	0.0710*
H5	0.58330	0.65570	−0.14950	0.0710*
H7	0.65560	0.74140	0.04220	0.0800*
H8	0.79470	0.70100	0.22730	0.0900*
H9	0.91680	0.48940	0.28620	0.0900*

	U11	U22	U33	U12	U13	U23
Br1	0.0902 (6)	0.0440 (5)	0.0739 (5)	0.0092 (4)	0.0106 (4)	0.0044 (3)
Br2	0.1024 (7)	0.0722 (7)	0.0649 (5)	0.0056 (5)	0.0146 (4)	0.0115 (4)
N1	0.065 (3)	0.056 (4)	0.068 (3)	−0.007 (3)	0.018 (2)	−0.005 (3)
C1	0.047 (3)	0.040 (4)	0.074 (4)	−0.003 (3)	0.014 (3)	−0.004 (3)
C2	0.052 (3)	0.033 (4)	0.070 (3)	0.001 (3)	0.016 (3)	0.005 (3)
C3	0.057 (3)	0.049 (4)	0.066 (3)	−0.001 (3)	0.012 (3)	−0.001 (3)
C4	0.056 (3)	0.046 (4)	0.061 (3)	−0.001 (3)	0.017 (3)	0.009 (3)
C5	0.055 (3)	0.043 (4)	0.076 (4)	0.004 (3)	0.019 (3)	0.002 (3)
C6	0.050 (3)	0.047 (4)	0.078 (4)	0.001 (3)	0.024 (3)	−0.004 (3)
C7	0.067 (4)	0.052 (5)	0.084 (4)	0.005 (3)	0.030 (3)	−0.007 (4)
C8	0.079 (5)	0.068 (6)	0.084 (5)	−0.004 (4)	0.036 (4)	−0.013 (4)
C9	0.077 (5)	0.078 (6)	0.070 (4)	−0.016 (4)	0.025 (3)	−0.015 (4)

Br1—C2	1.877 (6)	C5—C6	1.407 (9)
Br2—C4	1.909 (6)	C6—C7	1.414 (10)
N1—C1	1.358 (8)	C7—C8	1.368 (10)
N1—C9	1.332 (10)	C8—C9	1.401 (12)
C1—C2	1.425 (9)	C3—H3	0.9300
C1—C6	1.414 (10)	C5—H5	0.9300
C2—C3	1.370 (9)	C7—H7	0.9300
C3—C4	1.398 (10)	C8—H8	0.9300
C4—C5	1.343 (9)	C9—H9	0.9300
Br1···Br1i	3.4443 (13)
C1—N1—C9	116.1 (6)	C5—C6—C7	122.2 (6)
N1—C1—C2	118.9 (6)	C6—C7—C8	119.0 (7)
N1—C1—C6	123.8 (6)	C7—C8—C9	118.8 (7)
C2—C1—C6	117.3 (6)	N1—C9—C8	124.8 (7)
Br1—C2—C1	119.4 (5)	C2—C3—H3	121.00
Br1—C2—C3	119.0 (5)	C4—C3—H3	121.00
C1—C2—C3	121.6 (6)	C4—C5—H5	120.00
C2—C3—C4	118.6 (6)	C6—C5—H5	120.00
Br2—C4—C3	117.5 (5)	C6—C7—H7	120.00
Br2—C4—C5	119.9 (5)	C8—C7—H7	120.00
C3—C4—C5	122.7 (6)	C7—C8—H8	121.00
C4—C5—C6	119.5 (6)	C9—C8—H8	121.00
C1—C6—C5	120.3 (6)	N1—C9—H9	118.00
C1—C6—C7	117.5 (6)	C8—C9—H9	118.00
C9—N1—C1—C2	178.9 (6)	C1—C2—C3—C4	−2.1 (10)
C9—N1—C1—C6	−0.3 (10)	C2—C3—C4—C5	2.1 (11)
C1—N1—C9—C8	−1.3 (12)	C2—C3—C4—Br2	−176.9 (5)
N1—C1—C2—Br1	−2.1 (8)	Br2—C4—C5—C6	178.7 (5)
N1—C1—C2—C3	−179.0 (6)	C3—C4—C5—C6	−0.3 (11)
C6—C1—C2—C3	0.3 (9)	C4—C5—C6—C7	179.0 (7)
N1—C1—C6—C5	−179.2 (6)	C4—C5—C6—C1	−1.6 (10)
C6—C1—C2—Br1	177.2 (5)	C1—C6—C7—C8	1.4 (11)
C2—C1—C6—C5	1.6 (10)	C5—C6—C7—C8	−179.2 (7)
C2—C1—C6—C7	−179.0 (6)	C6—C7—C8—C9	−2.8 (12)
N1—C1—C6—C7	0.2 (10)	C7—C8—C9—N1	2.9 (13)
Br1—C2—C3—C4	−179.0 (5)