4-Bromo-8-methoxy-quinoline.

The non-H atoms of the title mol-ecule, C(10)H(8)BrNO, are essentially coplanar. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯π(arene) inter-actions, forming one-dimensional chains along the a axis.

Related literature

For related literature, see: Michael (2008 ▶); Kulkarni et al. (2006 ▶); Irving & Pinnington (1957 ▶).

Experimental

Crystal data

C10H8BrNO

M = 238.08

Orthorhombic,

a = 5.1615 (1) Å

b = 12.1337 (6) Å

c = 14.2436 (7) Å

V = 892.05 (6) Å3

Z = 4

Mo Kα radiation

μ = 4.56 mm−1

T = 150 (1) K

0.30 × 0.12 × 0.11 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing 1995 ▶) T min = 0.545, T max = 0.607

6134 measured reflections

2026 independent reflections

1872 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.059

S = 1.01

2026 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 815 Friedel pairs

Flack parameter: −0.017 (11)

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014591/pv2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014591/pv2082Isup2.hkl

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

C10H8BrNO	F000 = 472
Mr = 238.08	Dx = 1.773 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6134 reflections
a = 5.1615 (1) Å	θ = 2.9–27.5º
b = 12.1337 (6) Å	µ = 4.56 mm−1
c = 14.2436 (7) Å	T = 150 (1) K
V = 892.05 (6) Å3	Needle, colourless
Z = 4	0.30 × 0.12 × 0.11 mm

Nonius KappaCCD diffractometer	2026 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 9 pixels mm-1	θmax = 27.5º
T = 150(2) K	θmin = 2.9º
φ scans and ω scans with κ offsets	h = −5→6
Absorption correction: multi-scan(SORTAV; Blessing 1995)	k = −14→15
Tmin = 0.545, Tmax = 0.607	l = −18→18
6134 measured reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0306P)2 + 0.0333P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.028	(Δ/σ)max = 0.001
wR(F2) = 0.059	Δρmax = 0.38 e Å−3
S = 1.01	Δρmin = −0.40 e Å−3
2026 reflections	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
120 parameters	Extinction coefficient: 0.0062 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 815 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.017 (11)
Hydrogen site location: inferred from neighbouring sites

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	1.02034 (5)	0.36147 (2)	0.509948 (18)	0.02940 (11)
O1	0.1007 (3)	0.62674 (16)	0.72708 (14)	0.0259 (4)
N1	0.4260 (4)	0.64140 (17)	0.58326 (14)	0.0233 (4)
C1	0.5884 (5)	0.6481 (2)	0.51287 (18)	0.0278 (6)
H1A	0.5819	0.7126	0.4752	0.033*
C2	0.7717 (5)	0.5671 (2)	0.48878 (19)	0.0268 (6)
H2A	0.8842	0.5768	0.4366	0.032*
C3	0.7833 (5)	0.4746 (2)	0.54217 (19)	0.0239 (6)
C4	0.6190 (5)	0.4611 (2)	0.62176 (17)	0.0188 (5)
C5	0.6239 (5)	0.3694 (2)	0.68244 (18)	0.0232 (6)
H5A	0.7429	0.3109	0.6718	0.028*
C6	0.4556 (5)	0.3650 (2)	0.75705 (17)	0.0243 (6)
H6A	0.4624	0.3038	0.7986	0.029*
C7	0.2739 (5)	0.4487 (2)	0.77325 (18)	0.0235 (6)
H7A	0.1558	0.4424	0.8241	0.028*
C8	0.2656 (5)	0.5400 (2)	0.71586 (17)	0.0195 (5)
C9	0.4408 (5)	0.54916 (19)	0.63810 (16)	0.0199 (5)
C10	−0.0731 (5)	0.6201 (2)	0.80535 (18)	0.0271 (7)
H10C	−0.1784	0.6872	0.8083	0.041*
H10D	0.0269	0.6126	0.8635	0.041*
H10A	−0.1865	0.5559	0.7978	0.041*

	U11	U22	U33	U12	U13	U23
Br1	0.02472 (15)	0.03108 (16)	0.03239 (16)	0.00303 (10)	0.00306 (11)	−0.00756 (11)
O1	0.0264 (10)	0.0255 (11)	0.0259 (10)	0.0030 (8)	0.0047 (7)	0.0004 (8)
N1	0.0281 (10)	0.0212 (11)	0.0206 (11)	−0.0009 (9)	−0.0021 (8)	0.0001 (10)
C1	0.0339 (13)	0.0259 (14)	0.0237 (14)	−0.0019 (10)	0.0030 (10)	0.0087 (14)
C2	0.0265 (12)	0.0299 (14)	0.0240 (14)	−0.0065 (10)	0.0049 (12)	0.0001 (13)
C3	0.0215 (13)	0.0257 (14)	0.0246 (15)	−0.0015 (10)	−0.0025 (10)	−0.0078 (12)
C4	0.0210 (13)	0.0184 (13)	0.0169 (13)	−0.0037 (9)	−0.0018 (9)	−0.0016 (11)
C5	0.0224 (12)	0.0215 (14)	0.0257 (14)	0.0016 (11)	−0.0064 (10)	−0.0019 (12)
C6	0.0328 (15)	0.0176 (13)	0.0225 (13)	−0.0037 (13)	−0.0074 (11)	0.0035 (11)
C7	0.0257 (14)	0.0258 (15)	0.0191 (14)	−0.0088 (11)	0.0018 (11)	−0.0010 (11)
C8	0.0208 (13)	0.0185 (13)	0.0193 (13)	−0.0003 (10)	−0.0021 (10)	−0.0014 (11)
C9	0.0207 (12)	0.0204 (13)	0.0186 (12)	−0.0042 (10)	−0.0046 (10)	0.0010 (10)
C10	0.0240 (14)	0.0314 (17)	0.0258 (15)	0.0015 (12)	0.0047 (11)	−0.0028 (12)

Br1—C3	1.895 (2)	C4—C9	1.429 (3)
O1—C8	1.362 (3)	C5—C6	1.374 (4)
O1—C10	1.433 (3)	C5—H5A	0.9500
N1—C1	1.309 (3)	C6—C7	1.402 (4)
N1—C9	1.367 (3)	C6—H6A	0.9500
C1—C2	1.407 (4)	C7—C8	1.378 (4)
C1—H1A	0.9500	C7—H7A	0.9500
C2—C3	1.357 (3)	C8—C9	1.434 (3)
C2—H2A	0.9500	C10—H10C	0.9800
C3—C4	1.425 (3)	C10—H10D	0.9800
C4—C5	1.409 (4)	C10—H10A	0.9800
C8—O1—C10	116.0 (2)	C5—C6—H6A	119.3
C1—N1—C9	116.9 (2)	C7—C6—H6A	119.3
N1—C1—C2	125.0 (2)	C8—C7—C6	120.4 (2)
N1—C1—H1A	117.5	C8—C7—H7A	119.8
C2—C1—H1A	117.5	C6—C7—H7A	119.8
C3—C2—C1	118.1 (2)	O1—C8—C7	124.8 (2)
C3—C2—H2A	121.0	O1—C8—C9	115.1 (2)
C1—C2—H2A	121.0	C7—C8—C9	120.0 (2)
C2—C3—C4	121.0 (2)	N1—C9—C4	123.7 (2)
C2—C3—Br1	119.4 (2)	N1—C9—C8	118.0 (2)
C4—C3—Br1	119.58 (19)	C4—C9—C8	118.3 (2)
C5—C4—C3	124.6 (2)	O1—C10—H10C	109.5
C5—C4—C9	120.1 (2)	O1—C10—H10D	109.5
C3—C4—C9	115.3 (2)	H10C—C10—H10D	109.5
C6—C5—C4	119.6 (3)	O1—C10—H10A	109.5
C6—C5—H5A	120.2	H10C—C10—H10A	109.5
C4—C5—H5A	120.2	H10D—C10—H10A	109.5
C5—C6—C7	121.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cgi	0.98	2.66	3.531 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cgi	0.98	2.66	3.531 (3)	148

Symmetry code: (i) . Cg is the centroid of the C4–C9 ring.