4-Chloro-6,7-dimeth-oxy-quinoline.

The title mol-ecule, C(11)H(10)ClNO(2), is almost planar with the C atoms of the meth-oxy groups deviating by -0.082 (2) and 0.020 (2) Å from the least-squares plane defined by the atoms of the quinoline ring system (r.m.s. deviation = 0.002 Å). An intra-molecular C-H⋯Cl inter-action generates an S(5) ring motif.

Related literature

For related structures, see: Davies & Bond (2001 ▶); Yathirajan et al. (2007 ▶). For biological properties of quinoline derivatives, see: Franck et al. (2004 ▶); Moret et al. (2006 ▶); Furuta et al. (2006 ▶); Ilovich et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10ClNO2

M = 223.65

Monoclinic,

a = 12.5530 (17) Å

b = 4.6499 (7) Å

c = 18.274 (3) Å

β = 105.786 (2)°

V = 1026.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.3 × 0.2 × 0.2 mm

Data collection

Rigaku SCXmini diffractometer

6840 measured reflections

1808 independent reflections

1542 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections every 150 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.115

S = 1.08

1808 reflections

139 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042589/lr2029sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042589/lr2029Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811042589/lr2029Isup3.cml

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

C11H10ClNO2	F(000) = 464
Mr = 223.65	Dx = 1.447 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.5530 (17) Å	Cell parameters from 30 reflections
b = 4.6499 (7) Å	θ = 3–25°
c = 18.274 (3) Å	µ = 0.35 mm−1
β = 105.786 (2)°	T = 296 K
V = 1026.4 (3) Å3	Block, pink
Z = 4	0.3 × 0.2 × 0.2 mm

Rigaku SCXmini diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.7°
graphite	h = −14→14
ω scans	k = −5→5
6840 measured reflections	l = −21→21
1808 independent reflections	3 standard reflections every 150 reflections
1542 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.1562P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1808 reflections	Δρmax = 0.29 e Å−3
139 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (4)

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
C1	0.18445 (16)	0.9064 (4)	0.34245 (10)	0.0508 (5)
C2	0.23248 (18)	0.7745 (5)	0.40978 (11)	0.0608 (5)
H2	0.2071	0.8077	0.4523	0.073*
C3	0.32020 (19)	0.5895 (5)	0.41333 (12)	0.0668 (6)
H3	0.3522	0.4999	0.4596	0.080*
C4	0.31375 (16)	0.6656 (4)	0.28823 (10)	0.0486 (5)
C5	0.35750 (15)	0.6077 (4)	0.22615 (11)	0.0503 (5)
H5	0.4173	0.4832	0.2326	0.060*
C6	0.31298 (14)	0.7325 (4)	0.15691 (10)	0.0469 (4)
C7	0.22217 (14)	0.9277 (4)	0.14727 (9)	0.0443 (4)
C8	0.17947 (14)	0.9890 (4)	0.20641 (9)	0.0441 (4)
H8	0.1208	1.1173	0.1997	0.053*
C9	0.22416 (14)	0.8581 (3)	0.27829 (9)	0.0437 (4)
C10	0.43422 (17)	0.4878 (5)	0.09810 (13)	0.0659 (6)
H10A	0.4997	0.5563	0.1344	0.099*
H10B	0.4482	0.4703	0.0492	0.099*
H10C	0.4142	0.3033	0.1139	0.099*
C11	0.09705 (17)	1.2379 (5)	0.06201 (12)	0.0580 (5)
H11A	0.0339	1.1499	0.0729	0.087*
H11B	0.0780	1.2972	0.0097	0.087*
H11C	0.1195	1.4025	0.0942	0.087*
Cl1	0.07193 (4)	1.13418 (12)	0.33477 (3)	0.0656 (3)
N1	0.36194 (14)	0.5307 (4)	0.35576 (9)	0.0623 (5)
O1	0.34547 (11)	0.6869 (3)	0.09331 (7)	0.0585 (4)
O2	0.18526 (11)	1.0371 (3)	0.07552 (7)	0.0561 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0588 (11)	0.0528 (10)	0.0423 (10)	−0.0142 (9)	0.0164 (8)	−0.0043 (8)
C2	0.0742 (13)	0.0699 (12)	0.0404 (11)	−0.0112 (10)	0.0193 (10)	0.0013 (9)
C3	0.0824 (14)	0.0736 (13)	0.0398 (11)	−0.0076 (11)	0.0088 (10)	0.0115 (10)
C4	0.0543 (10)	0.0463 (10)	0.0428 (10)	−0.0079 (8)	0.0094 (8)	0.0014 (8)
C5	0.0505 (10)	0.0487 (10)	0.0506 (11)	0.0030 (8)	0.0120 (8)	0.0001 (8)
C6	0.0498 (10)	0.0491 (9)	0.0438 (10)	−0.0047 (8)	0.0162 (8)	−0.0054 (8)
C7	0.0504 (10)	0.0460 (9)	0.0363 (9)	−0.0045 (7)	0.0114 (7)	−0.0014 (7)
C8	0.0467 (9)	0.0452 (9)	0.0405 (9)	−0.0029 (7)	0.0121 (7)	−0.0012 (7)
C9	0.0487 (9)	0.0445 (9)	0.0381 (9)	−0.0113 (7)	0.0123 (7)	−0.0036 (7)
C10	0.0635 (12)	0.0696 (13)	0.0717 (14)	0.0061 (11)	0.0303 (10)	−0.0091 (11)
C11	0.0643 (12)	0.0611 (11)	0.0474 (11)	0.0071 (10)	0.0134 (9)	0.0054 (9)
Cl1	0.0735 (4)	0.0778 (4)	0.0532 (4)	0.0040 (3)	0.0302 (3)	−0.0051 (2)
N1	0.0685 (11)	0.0630 (10)	0.0506 (10)	−0.0002 (8)	0.0083 (8)	0.0112 (8)
O1	0.0633 (8)	0.0695 (9)	0.0478 (8)	0.0123 (7)	0.0239 (6)	−0.0024 (6)
O2	0.0675 (8)	0.0654 (8)	0.0380 (7)	0.0129 (7)	0.0188 (6)	0.0068 (6)

C1—C2	1.360 (3)	C6—C7	1.430 (3)
C1—C9	1.411 (3)	C7—C8	1.361 (2)
C1—Cl1	1.740 (2)	C7—O2	1.365 (2)
C2—C3	1.385 (3)	C8—C9	1.418 (2)
C2—H2	0.9300	C8—H8	0.9300
C3—N1	1.325 (3)	C10—O1	1.433 (2)
C3—H3	0.9300	C10—H10A	0.9600
C4—N1	1.370 (2)	C10—H10B	0.9600
C4—C9	1.410 (3)	C10—H10C	0.9600
C4—C5	1.414 (3)	C11—O2	1.418 (2)
C5—C6	1.366 (3)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—O1	1.349 (2)	C11—H11C	0.9600
C2—C1—C9	120.67 (19)	C7—C8—C9	120.25 (17)
C2—C1—Cl1	119.85 (16)	C7—C8—H8	119.9
C9—C1—Cl1	119.48 (14)	C9—C8—H8	119.9
C1—C2—C3	118.27 (19)	C4—C9—C1	116.33 (16)
C1—C2—H2	120.9	C4—C9—C8	119.53 (16)
C3—C2—H2	120.9	C1—C9—C8	124.14 (17)
N1—C3—C2	124.90 (18)	O1—C10—H10A	109.5
N1—C3—H3	117.6	O1—C10—H10B	109.5
C2—C3—H3	117.6	H10A—C10—H10B	109.5
N1—C4—C9	123.24 (18)	O1—C10—H10C	109.5
N1—C4—C5	117.57 (17)	H10A—C10—H10C	109.5
C9—C4—C5	119.19 (16)	H10B—C10—H10C	109.5
C6—C5—C4	120.80 (17)	O2—C11—H11A	109.5
C6—C5—H5	119.6	O2—C11—H11B	109.5
C4—C5—H5	119.6	H11A—C11—H11B	109.5
O1—C6—C5	126.01 (17)	O2—C11—H11C	109.5
O1—C6—C7	114.29 (15)	H11A—C11—H11C	109.5
C5—C6—C7	119.69 (17)	H11B—C11—H11C	109.5
C8—C7—O2	125.52 (16)	C3—N1—C4	116.59 (18)
C8—C7—C6	120.54 (15)	C6—O1—C10	117.47 (15)
O2—C7—C6	113.94 (15)	C7—O2—C11	117.24 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl1	0.93	2.70	3.0827 (17)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl1	0.93	2.70	3.0827 (17)	105