3,6,8-Tribromo-quinoline.

The title mol-ecule, C(9)H(4)Br(3)N, is almost planar, the maximum deviation being 0.110 (1) Å. The crystal structure is stabilized by weak aromatic π-π inter-actions [centroid-centroid distance = 3.802 (4) Å] between the pyridine and benzene rings of the quinoline ring systems of adjacent mol-ecules.

Related literature

For background to the synthesis of natural biologically active quinoline derivatives and for the synthesis of the title compound, see: Şahin et al. (2008 ▶). For the structure of 6,8-dibromo­quinoline, see: Çelik et al. (2010 ▶).

Experimental

Crystal data

C9H4Br3N

M = 365.83

Monoclinic,

a = 3.9810 (2) Å

b = 12.4176 (4) Å

c = 19.7419 (6) Å

β = 92.827 (3)°

V = 974.74 (7) Å3

Z = 4

Cu Kα radiation

μ = 14.93 mm−1

T = 296 K

0.51 × 0.06 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini CCD detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.049, T max = 0.663

3688 measured reflections

1816 independent reflections

1484 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.150

S = 1.05

1816 reflections

118 parameters

H-atom parameters constrained

Δρmax = 1.45 e Å−3

Δρmin = −0.80 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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/S1600536810045484/pv2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045484/pv2350Isup2.hkl

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

C9H4Br3N	F(000) = 680
Mr = 365.83	Dx = 2.493 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 2025 reflections
a = 3.9810 (2) Å	θ = 3.6–70.4°
b = 12.4176 (4) Å	µ = 14.93 mm−1
c = 19.7419 (6) Å	T = 296 K
β = 92.827 (3)°	Needle, colourless
V = 974.74 (7) Å3	0.51 × 0.06 × 0.03 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini CCD detector	1816 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1484 reflections with I > 2σ(I)
graphite	Rint = 0.060
Detector resolution: 10.2673 pixels mm-1	θmax = 70.6°, θmin = 5.7°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→15
Tmin = 0.049, Tmax = 0.663	l = −22→24
3688 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1066P)2] where P = (Fo2 + 2Fc2)/3
1816 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 1.45 e Å−3
0 restraints	Δρmin = −0.79 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	0.6380 (2)	0.29099 (6)	0.90189 (4)	0.0568 (3)
Br2	0.11453 (19)	−0.12590 (6)	0.92944 (4)	0.0525 (3)
Br3	0.7497 (2)	0.08258 (7)	0.56672 (4)	0.0608 (3)
N1	0.7203 (14)	0.2168 (5)	0.7553 (3)	0.0440 (17)
C1	0.5666 (16)	0.1396 (5)	0.7921 (3)	0.0396 (17)
C2	0.5134 (15)	0.1576 (5)	0.8619 (3)	0.0404 (17)
C3	0.3758 (16)	0.0808 (5)	0.9010 (3)	0.0428 (17)
C4	0.2822 (16)	−0.0184 (5)	0.8725 (3)	0.0425 (17)
C5	0.3078 (15)	−0.0384 (5)	0.8042 (3)	0.0405 (17)
C6	0.4583 (15)	0.0399 (5)	0.7636 (3)	0.0387 (17)
C7	0.5126 (16)	0.0209 (5)	0.6946 (3)	0.0426 (17)
C8	0.6665 (16)	0.0996 (5)	0.6597 (3)	0.0429 (17)
C9	0.7713 (17)	0.1961 (6)	0.6919 (3)	0.0462 (17)
H3	0.34400	0.09420	0.94660	0.0520*
H5	0.22720	−0.10250	0.78520	0.0480*
H7	0.44560	−0.04330	0.67380	0.0510*
H9	0.88170	0.24730	0.66670	0.0550*

	U11	U22	U33	U12	U13	U23
Br1	0.0752 (6)	0.0456 (4)	0.0506 (5)	−0.0125 (3)	0.0119 (4)	−0.0120 (3)
Br2	0.0622 (5)	0.0498 (5)	0.0464 (4)	−0.0097 (3)	0.0107 (3)	0.0057 (3)
Br3	0.0798 (6)	0.0652 (5)	0.0385 (4)	0.0047 (4)	0.0132 (3)	−0.0003 (3)
N1	0.053 (3)	0.040 (3)	0.039 (3)	−0.003 (2)	0.003 (2)	0.002 (2)
C1	0.043 (3)	0.032 (3)	0.044 (3)	0.002 (2)	0.003 (2)	0.002 (2)
C2	0.044 (3)	0.037 (3)	0.040 (3)	0.002 (2)	0.000 (2)	−0.004 (2)
C3	0.042 (3)	0.050 (3)	0.037 (3)	−0.003 (3)	0.007 (2)	−0.006 (3)
C4	0.046 (3)	0.039 (3)	0.043 (3)	0.000 (3)	0.006 (2)	0.003 (2)
C5	0.045 (3)	0.038 (3)	0.038 (3)	0.000 (2)	−0.004 (2)	0.000 (2)
C6	0.039 (3)	0.038 (3)	0.039 (3)	0.006 (2)	0.000 (2)	0.003 (2)
C7	0.048 (3)	0.041 (3)	0.039 (3)	0.007 (3)	0.005 (2)	−0.003 (2)
C8	0.045 (3)	0.047 (3)	0.037 (3)	0.010 (3)	0.004 (2)	0.003 (2)
C9	0.053 (3)	0.047 (3)	0.039 (3)	−0.002 (3)	0.006 (3)	0.004 (2)

Br1—C2	1.891 (6)	C4—C5	1.380 (8)
Br2—C4	1.888 (6)	C5—C6	1.412 (9)
Br3—C8	1.893 (6)	C6—C7	1.410 (8)
N1—C1	1.366 (9)	C7—C8	1.359 (9)
N1—C9	1.303 (8)	C8—C9	1.410 (9)
C1—C2	1.422 (8)	C3—H3	0.9300
C1—C6	1.418 (9)	C5—H5	0.9300
C2—C3	1.359 (9)	C7—H7	0.9300
C3—C4	1.397 (9)	C9—H9	0.9300
Br1···N1	3.070 (6)	C7···C8ii	3.542 (9)
Br1···Br3i	3.6969 (12)	C7···Br1iv	3.738 (6)
Br1···C7i	3.738 (6)	C8···C7viii	3.542 (9)
Br2···C4ii	3.696 (6)	C9···Br2ix	3.553 (7)
Br2···C9iii	3.553 (7)	C9···C6viii	3.587 (9)
Br3···Br1iv	3.6969 (12)	C5···H9iv	2.9800
Br3···Br3v	3.8186 (12)	H3···Br2vii	3.1500
Br1···H7i	3.0800	H3···Br2vi	3.2000
Br2···H9iii	3.1000	H5···H7	2.5100
Br2···H3vi	3.2000	H5···H9iv	2.5800
Br2···H9iv	3.2400	H7···H5	2.5100
Br2···H3vii	3.1500	H7···Br1iv	3.0800
N1···Br1	3.070 (6)	H9···Br2ix	3.1000
C4···Br2viii	3.696 (6)	H9···Br2i	3.2400
C5···C6ii	3.572 (8)	H9···C5i	2.9800
C6···C5viii	3.572 (8)	H9···H5i	2.5800
C6···C9ii	3.587 (9)
C1—N1—C9	117.9 (6)	C5—C6—C7	121.5 (6)
N1—C1—C2	119.8 (6)	C6—C7—C8	117.7 (6)
N1—C1—C6	122.5 (6)	Br3—C8—C7	121.1 (5)
C2—C1—C6	117.7 (5)	Br3—C8—C9	118.0 (5)
Br1—C2—C1	119.6 (5)	C7—C8—C9	120.9 (6)
Br1—C2—C3	118.8 (5)	N1—C9—C8	123.0 (6)
C1—C2—C3	121.6 (6)	C2—C3—H3	120.00
C2—C3—C4	119.8 (6)	C4—C3—H3	120.00
Br2—C4—C3	118.6 (4)	C4—C5—H5	120.00
Br2—C4—C5	120.0 (5)	C6—C5—H5	121.00
C3—C4—C5	121.4 (6)	C6—C7—H7	121.00
C4—C5—C6	119.0 (6)	C8—C7—H7	121.00
C1—C6—C5	120.3 (5)	N1—C9—H9	119.00
C1—C6—C7	118.1 (5)	C8—C9—H9	118.00
C9—N1—C1—C2	178.4 (6)	C2—C3—C4—Br2	176.6 (5)
C9—N1—C1—C6	−0.9 (9)	C2—C3—C4—C5	−3.9 (10)
C1—N1—C9—C8	1.9 (10)	Br2—C4—C5—C6	−175.1 (5)
N1—C1—C2—Br1	2.9 (8)	C3—C4—C5—C6	5.4 (9)
N1—C1—C2—C3	−176.9 (6)	C4—C5—C6—C1	−3.0 (9)
C6—C1—C2—Br1	−177.8 (4)	C4—C5—C6—C7	175.5 (6)
C6—C1—C2—C3	2.5 (9)	C1—C6—C7—C8	0.1 (9)
N1—C1—C6—C5	178.5 (6)	C5—C6—C7—C8	−178.4 (6)
N1—C1—C6—C7	−0.1 (9)	C6—C7—C8—Br3	−179.7 (5)
C2—C1—C6—C5	−0.9 (9)	C6—C7—C8—C9	0.8 (9)
C2—C1—C6—C7	−179.5 (6)	Br3—C8—C9—N1	178.6 (5)
Br1—C2—C3—C4	−179.9 (5)	C7—C8—C9—N1	−1.9 (10)
C1—C2—C3—C4	−0.2 (9)

Ring 1	Ring 2(sym)	(Ring 1)···(Ring 2) (Å)
Cg1	Cg2i	3.802 (4)