8-Bromo-2-methyl-quinoline.

In the crystal structure of the title compound, C(10)H(8)BrN, the dihedral angle between the two six-membered rings of the quinoline system is 0.49 (16)°. The mol-ecules are packed in a face-to-face arrangement fashion, with a centroid-centroid distance of 3.76 Å between the benzene and pyridine rings of adjacent mol-ecules. No hydrogen bonding is found in the crystal structure.

Related literature

The title compound is an important inter­mediate in the pharmaceutical industry, see: Shen & Hartwig (2006 ▶); Ranu et al. (2000 ▶); Lee & Hartwig (2005 ▶). For related structures, see: Amini et al. (2008 ▶); Faza­eli et al. (2008 ▶); Sattarzadeh et al. (2009 ▶).

Experimental

Crystal data

C10H8BrN

M = 222.08

Monoclinic,

a = 5.0440 (17) Å

b = 13.467 (4) Å

c = 13.391 (4) Å

β = 97.678 (4)°

V = 901.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.50 mm−1

T = 291 K

0.36 × 0.31 × 0.28 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.235, T max = 0.286

4668 measured reflections

1765 independent reflections

1039 reflections with I > 2σ(I)

R int = 0.156

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.195

S = 1.01

1765 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.91 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809020625/xu2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020625/xu2533Isup2.hkl

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

C10H8BrN	F(000) = 440
Mr = 222.08	Dx = 1.636 Mg m−3
Monoclinic, P21/c	Melting point: 343 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.0440 (17) Å	Cell parameters from 1765 reflections
b = 13.467 (4) Å	θ = 2.2–26.0°
c = 13.391 (4) Å	µ = 4.50 mm−1
β = 97.678 (4)°	T = 291 K
V = 901.4 (5) Å3	Block, colourless
Z = 4	0.36 × 0.31 × 0.28 mm

Bruker SMART APEX CCD diffractometer	1765 independent reflections
Radiation source: fine-focus sealed tube	1039 reflections with I > 2σ(I)
graphite	Rint = 0.156
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.235, Tmax = 0.286	k = −13→16
4668 measured reflections	l = −15→16

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0989P)2] where P = (Fo2 + 2Fc2)/3
1765 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.91 e Å−3

Experimental. 1H NMR (CDCl3, 400 MHz) δ: 2.82 (s, 3H, CH3), 7.33(m, 2H, quinoline 3,6-H), 7.73 (dd, J=8.0 Hz, J=1.2 Hz, 1H, quinoline 7-H), 8.02 (m, 2H, quinoline 4,5-H).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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	1.04425 (17)	0.41478 (5)	0.40291 (5)	0.0783 (4)
N1	0.6713 (11)	0.2556 (3)	0.2991 (3)	0.0507 (12)
C1	0.9974 (14)	0.3782 (4)	0.2655 (4)	0.0536 (16)
C8	0.8122 (12)	0.3021 (4)	0.2325 (4)	0.0429 (13)
C9	0.7845 (13)	0.2775 (4)	0.1287 (4)	0.0517 (15)
C7	0.5039 (14)	0.1846 (4)	0.2646 (5)	0.0568 (16)
C2	1.1397 (14)	0.4256 (4)	0.2022 (6)	0.0586 (16)
H2	1.2578	0.4757	0.2266	0.070*
C5	0.6014 (14)	0.2003 (5)	0.0957 (5)	0.0643 (18)
H5	0.5778	0.1807	0.0285	0.077*
C3	1.1122 (15)	0.4004 (5)	0.0989 (5)	0.0621 (18)
H3	1.2156	0.4321	0.0561	0.074*
C6	0.4624 (16)	0.1559 (5)	0.1622 (5)	0.070 (2)
H6	0.3394	0.1064	0.1408	0.084*
C4	0.9318 (15)	0.3287 (5)	0.0624 (5)	0.068 (2)
H4	0.9066	0.3138	−0.0061	0.082*
C10	0.3468 (14)	0.1364 (5)	0.3370 (6)	0.0694 (19)
H10A	0.3969	0.0677	0.3444	0.104*
H10B	0.1596	0.1412	0.3123	0.104*
H10C	0.3821	0.1690	0.4011	0.104*

	U11	U22	U33	U12	U13	U23
Br1	0.1139 (9)	0.0735 (6)	0.0436 (4)	−0.0082 (4)	−0.0042 (4)	−0.0114 (3)
N1	0.059 (3)	0.050 (3)	0.042 (3)	0.011 (3)	0.004 (2)	0.005 (2)
C1	0.074 (5)	0.044 (3)	0.040 (3)	0.005 (3)	−0.001 (3)	−0.001 (2)
C8	0.037 (3)	0.050 (3)	0.040 (3)	0.012 (3)	0.001 (2)	−0.001 (2)
C9	0.054 (4)	0.063 (3)	0.037 (3)	0.009 (3)	0.002 (3)	−0.001 (3)
C7	0.059 (4)	0.053 (3)	0.059 (4)	0.011 (3)	0.009 (3)	0.007 (3)
C2	0.051 (4)	0.055 (3)	0.070 (4)	0.002 (3)	0.010 (3)	0.004 (3)
C5	0.057 (5)	0.083 (4)	0.050 (4)	0.003 (4)	−0.006 (3)	−0.015 (3)
C3	0.054 (5)	0.073 (4)	0.063 (4)	0.004 (4)	0.021 (3)	0.013 (3)
C6	0.080 (6)	0.063 (4)	0.062 (4)	−0.002 (4)	−0.008 (4)	−0.007 (3)
C4	0.081 (6)	0.085 (5)	0.039 (3)	0.013 (4)	0.012 (3)	0.004 (3)
C10	0.054 (4)	0.068 (4)	0.088 (5)	0.002 (4)	0.015 (4)	0.007 (4)

Br1—C1	1.889 (6)	C2—H2	0.9300
N1—C7	1.318 (8)	C5—C6	1.344 (10)
N1—C8	1.365 (7)	C5—H5	0.9300
C1—C2	1.344 (9)	C3—C4	1.371 (10)
C1—C8	1.416 (8)	C3—H3	0.9300
C8—C9	1.418 (7)	C6—H6	0.9300
C9—C4	1.411 (9)	C4—H4	0.9300
C9—C5	1.422 (9)	C10—H10A	0.9600
C7—C6	1.414 (8)	C10—H10B	0.9600
C7—C10	1.481 (9)	C10—H10C	0.9600
C2—C3	1.412 (10)
C7—N1—C8	118.0 (5)	C6—C5—H5	120.2
C2—C1—C8	122.1 (6)	C9—C5—H5	120.2
C2—C1—Br1	118.9 (5)	C4—C3—C2	119.5 (6)
C8—C1—Br1	119.0 (4)	C4—C3—H3	120.2
N1—C8—C1	120.5 (5)	C2—C3—H3	120.2
N1—C8—C9	122.8 (5)	C5—C6—C7	119.9 (7)
C1—C8—C9	116.7 (5)	C5—C6—H6	120.1
C4—C9—C8	120.8 (6)	C7—C6—H6	120.1
C4—C9—C5	122.4 (6)	C3—C4—C9	119.9 (6)
C8—C9—C5	116.8 (5)	C3—C4—H4	120.1
N1—C7—C6	122.9 (6)	C9—C4—H4	120.1
N1—C7—C10	117.6 (6)	C7—C10—H10A	109.5
C6—C7—C10	119.5 (7)	C7—C10—H10B	109.5
C1—C2—C3	120.9 (6)	H10A—C10—H10B	109.5
C1—C2—H2	119.6	C7—C10—H10C	109.5
C3—C2—H2	119.6	H10A—C10—H10C	109.5
C6—C5—C9	119.6 (6)	H10B—C10—H10C	109.5