2,4-Dichloro-6-methoxy-quinoline.

The title compound, C(10)H(7)Cl(2)NO, features a planar mol-ecule, excluding the methyl H atoms [maximum deviation = 0.0385 (1) Å]. The crystal packing is stabilized by π-π stacking inter-actions across inversion centres [centroid-to-centroid distance = 3.736 (3) Å].

Related literature

For general background, see: Fournet et al. (1981 ▶) and references cited therein; Towers et al. (1981 ▶); Biavatti et al. (2002 ▶); McCormick et al. (1996 ▶); Ziegler & Gelfert, (1959 ▶). For related crystal structures, see: Somvanshi et al. (2008 ▶).

Experimental

Crystal data

C10H7Cl2NO

M = 228.07

Triclinic,

a = 7.431 (2) Å

b = 8.889 (2) Å

c = 9.083 (4) Å

α = 116.660 (19)°

β = 102.301 (2)°

γ = 104.150 (14)°

V = 482.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.63 mm−1

T = 290 (2) K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.811, T max = 0.909

5720 measured reflections

1782 independent reflections

1272 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.197

S = 1.15

1782 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1999 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002402/bt2852sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002402/bt2852Isup2.hkl

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

C10H7Cl2NO	Z = 2
Mr = 228.07	F(000) = 232
Triclinic, P1	Dx = 1.570 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.431 (2) Å	Cell parameters from 856 reflections
b = 8.889 (2) Å	θ = 1.9–20.7°
c = 9.083 (4) Å	µ = 0.63 mm−1
α = 116.660 (19)°	T = 290 K
β = 102.301 (2)°	Block, colourless
γ = 104.150 (14)°	0.25 × 0.18 × 0.15 mm
V = 482.5 (3) Å3

Bruker SMART CCD area-detector diffractometer	1782 independent reflections
Radiation source: fine-focus sealed tube	1272 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→8
Tmin = 0.811, Tmax = 0.909	k = −10→10
5720 measured reflections	l = −11→11

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0844P)2 + 0.6982P] where P = (Fo2 + 2Fc2)/3
1782 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

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
Cl1	0.3126 (2)	1.55448 (15)	0.76004 (16)	0.0555 (4)
Cl2	0.2701 (2)	0.98994 (16)	0.84707 (16)	0.0592 (5)
N1	0.2689 (5)	1.2373 (5)	0.5081 (5)	0.0400 (9)
O1	0.2020 (5)	0.5198 (4)	0.1887 (4)	0.0517 (8)
C1	0.2837 (6)	1.3262 (5)	0.6714 (6)	0.0383 (10)
C2	0.2849 (6)	1.2594 (5)	0.7862 (5)	0.0382 (9)
H2	0.2972	1.3312	0.9031	0.046*
C3	0.2666 (6)	1.0805 (6)	0.7130 (5)	0.0378 (9)
C4	0.2323 (6)	0.7880 (5)	0.4545 (6)	0.0380 (9)
H4	0.2318	0.7305	0.5184	0.046*
C5	0.2168 (6)	0.6950 (5)	0.2814 (6)	0.0392 (10)
C6	0.2134 (7)	0.7815 (6)	0.1824 (6)	0.0422 (10)
H6	0.1994	0.7169	0.0641	0.051*
C7	0.2302 (7)	0.9572 (6)	0.2591 (6)	0.0421 (10)
H7	0.2294	1.0119	0.1926	0.051*
C8	0.2489 (6)	1.0586 (5)	0.4363 (5)	0.0350 (9)
C9	0.2491 (6)	0.9716 (5)	0.5361 (5)	0.0344 (9)
C10	0.2067 (8)	0.4245 (7)	0.2807 (7)	0.0573 (13)
H10A	0.3330	0.4855	0.3778	0.086*
H10B	0.1897	0.3014	0.2006	0.086*
H10C	0.1007	0.4228	0.3254	0.086*

	U11	U22	U33	U12	U13	U23
Cl1	0.0789 (9)	0.0407 (6)	0.0592 (8)	0.0310 (6)	0.0316 (6)	0.0293 (6)
Cl2	0.0927 (11)	0.0533 (7)	0.0488 (7)	0.0298 (7)	0.0288 (6)	0.0383 (6)
N1	0.049 (2)	0.0396 (19)	0.046 (2)	0.0226 (17)	0.0195 (17)	0.0300 (17)
O1	0.070 (2)	0.0391 (16)	0.0490 (18)	0.0252 (16)	0.0202 (16)	0.0246 (15)
C1	0.038 (2)	0.035 (2)	0.047 (2)	0.0168 (18)	0.0141 (19)	0.0248 (19)
C2	0.038 (2)	0.044 (2)	0.038 (2)	0.0176 (19)	0.0164 (18)	0.0234 (19)
C3	0.040 (2)	0.042 (2)	0.041 (2)	0.0169 (18)	0.0150 (18)	0.0284 (19)
C4	0.039 (2)	0.039 (2)	0.044 (2)	0.0151 (18)	0.0138 (19)	0.0295 (19)
C5	0.039 (2)	0.035 (2)	0.045 (2)	0.0148 (18)	0.0130 (19)	0.0232 (19)
C6	0.053 (3)	0.045 (2)	0.036 (2)	0.023 (2)	0.0185 (19)	0.0234 (19)
C7	0.055 (3)	0.044 (2)	0.042 (2)	0.025 (2)	0.020 (2)	0.030 (2)
C8	0.036 (2)	0.037 (2)	0.038 (2)	0.0151 (17)	0.0127 (17)	0.0239 (18)
C9	0.032 (2)	0.036 (2)	0.039 (2)	0.0127 (17)	0.0127 (17)	0.0235 (18)
C10	0.070 (3)	0.048 (3)	0.074 (3)	0.028 (2)	0.030 (3)	0.043 (3)

Cl1—C1	1.749 (4)	C4—C9	1.415 (5)
Cl2—C3	1.734 (4)	C4—H4	0.9300
N1—C1	1.293 (5)	C5—C6	1.422 (6)
N1—C8	1.372 (5)	C6—C7	1.352 (6)
O1—C5	1.359 (5)	C6—H6	0.9300
O1—C10	1.433 (5)	C7—C8	1.402 (6)
C1—C2	1.412 (5)	C7—H7	0.9300
C2—C3	1.377 (6)	C8—C9	1.432 (5)
C2—H2	0.9300	C10—H10A	0.9600
C3—C9	1.411 (6)	C10—H10B	0.9600
C4—C5	1.370 (6)	C10—H10C	0.9600
C1—N1—C8	117.4 (3)	C7—C6—H6	119.8
C5—O1—C10	117.2 (4)	C5—C6—H6	119.8
N1—C1—C2	126.7 (4)	C6—C7—C8	121.6 (4)
N1—C1—Cl1	116.3 (3)	C6—C7—H7	119.2
C2—C1—Cl1	117.0 (3)	C8—C7—H7	119.2
C3—C2—C1	115.3 (4)	N1—C8—C7	119.1 (3)
C3—C2—H2	122.3	N1—C8—C9	122.6 (4)
C1—C2—H2	122.3	C7—C8—C9	118.3 (4)
C2—C3—C9	122.4 (3)	C3—C9—C4	125.0 (4)
C2—C3—Cl2	117.9 (3)	C3—C9—C8	115.5 (3)
C9—C3—Cl2	119.6 (3)	C4—C9—C8	119.5 (4)
C5—C4—C9	120.1 (4)	O1—C10—H10A	109.5
C5—C4—H4	120.0	O1—C10—H10B	109.5
C9—C4—H4	120.0	H10A—C10—H10B	109.5
O1—C5—C4	125.8 (4)	O1—C10—H10C	109.5
O1—C5—C6	114.1 (4)	H10A—C10—H10C	109.5
C4—C5—C6	120.0 (4)	H10B—C10—H10C	109.5
C7—C6—C5	120.5 (4)
C8—N1—C1—C2	1.2 (6)	C1—N1—C8—C9	−1.6 (6)
C8—N1—C1—Cl1	179.1 (3)	C6—C7—C8—N1	178.9 (4)
N1—C1—C2—C3	−0.6 (6)	C6—C7—C8—C9	−0.2 (7)
Cl1—C1—C2—C3	−178.5 (3)	C2—C3—C9—C4	179.2 (4)
C1—C2—C3—C9	0.4 (6)	Cl2—C3—C9—C4	0.4 (6)
C1—C2—C3—Cl2	179.2 (3)	C2—C3—C9—C8	−0.8 (6)
C10—O1—C5—C4	−1.2 (6)	Cl2—C3—C9—C8	−179.6 (3)
C10—O1—C5—C6	179.3 (4)	C5—C4—C9—C3	−179.8 (4)
C9—C4—C5—O1	179.3 (4)	C5—C4—C9—C8	0.3 (6)
C9—C4—C5—C6	−1.3 (6)	N1—C8—C9—C3	1.5 (6)
O1—C5—C6—C7	−178.9 (4)	C7—C8—C9—C3	−179.5 (4)
C4—C5—C6—C7	1.6 (7)	N1—C8—C9—C4	−178.6 (4)
C5—C6—C7—C8	−0.8 (7)	C7—C8—C9—C4	0.5 (6)
C1—N1—C8—C7	179.3 (4)