2-Chloro-6-methoxy-quinoline-3-carbaldehyde.

The quinoline fused-ring system of the title compound, C(11)H(8)ClNO(2), is planar (r.m.s. deviation = 0.0095 Å); the formyl group is slightly bent out of this plane [C-C-C-O torsion angles = -2.4 (3) and 175.9 (2)°].

Related literature

For a review of the synthesis of quinolines by the Vilsmeier–Haack reaction, see: Meth-Cohn (1993 ▶).

Experimental

Crystal data

C11H8ClNO2

M = 221.63

Monoclinic,

a = 7.7072 (9) Å

b = 14.3474 (13) Å

c = 9.3487 (10) Å

β = 109.415 (2)°

V = 974.98 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 290 K

0.24 × 0.21 × 0.18 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.917, T max = 0.937

6533 measured reflections

2221 independent reflections

1702 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.115

S = 1.03

2221 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040847/bt5087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040847/bt5087Isup2.hkl

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

C11H8ClNO2	F(000) = 456
Mr = 221.63	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 842 reflections
a = 7.7072 (9) Å	θ = 2.0–24.7°
b = 14.3474 (13) Å	µ = 0.37 mm−1
c = 9.3487 (10) Å	T = 290 K
β = 109.415 (2)°	Block, colorless
V = 974.98 (18) Å3	0.24 × 0.21 × 0.18 mm
Z = 4

Bruker SMART area-detector diffractometer	2221 independent reflections
Radiation source: fine-focus sealed tube	1702 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.917, Tmax = 0.937	k = −18→10
6533 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.068P)2 + 0.0419P] where P = (Fo2 + 2Fc2)/3
2221 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.12213 (7)	0.04921 (3)	0.68956 (6)	0.05816 (19)
O1	0.02629 (18)	0.34429 (9)	0.71932 (16)	0.0563 (4)
O2	0.77125 (17)	0.34949 (8)	0.35759 (14)	0.0480 (3)
N1	0.35512 (19)	0.10458 (9)	0.56310 (15)	0.0399 (3)
C1	0.2333 (2)	0.13533 (11)	0.62026 (18)	0.0386 (4)
C2	0.1913 (2)	0.23022 (11)	0.63341 (17)	0.0365 (4)
C3	0.2892 (2)	0.29435 (11)	0.58240 (18)	0.0366 (3)
H3	0.2659	0.3576	0.5885	0.044*
C4	0.4244 (2)	0.26584 (10)	0.52104 (16)	0.0340 (3)
C5	0.5323 (2)	0.32923 (11)	0.47029 (18)	0.0372 (4)
H5	0.5165	0.3931	0.4772	0.045*
C6	0.6601 (2)	0.29554 (11)	0.41088 (18)	0.0375 (4)
C7	0.6864 (2)	0.19874 (12)	0.40126 (18)	0.0406 (4)
H7	0.7733	0.1771	0.3600	0.049*
C8	0.5865 (2)	0.13662 (11)	0.45142 (18)	0.0403 (4)
H8	0.6067	0.0730	0.4456	0.048*
C9	0.4520 (2)	0.16836 (10)	0.51239 (17)	0.0342 (3)
C10	0.0534 (2)	0.26334 (14)	0.70166 (19)	0.0446 (4)
H10	−0.0153	0.2191	0.7322	0.054*
C11	0.7544 (3)	0.44805 (12)	0.3677 (2)	0.0542 (5)
H11A	0.8378	0.4783	0.3259	0.081*
H11B	0.7835	0.4657	0.4721	0.081*
H11C	0.6306	0.4665	0.3120	0.081*

	U11	U22	U33	U12	U13	U23
Cl1	0.0724 (4)	0.0424 (3)	0.0754 (4)	−0.0099 (2)	0.0455 (3)	0.0028 (2)
O1	0.0572 (8)	0.0491 (9)	0.0728 (9)	0.0069 (6)	0.0355 (7)	−0.0077 (6)
O2	0.0529 (7)	0.0395 (7)	0.0631 (8)	−0.0047 (5)	0.0347 (6)	−0.0021 (5)
N1	0.0497 (8)	0.0302 (8)	0.0442 (7)	0.0003 (6)	0.0216 (6)	−0.0002 (5)
C1	0.0455 (9)	0.0337 (8)	0.0394 (8)	−0.0033 (7)	0.0176 (7)	0.0014 (6)
C2	0.0376 (8)	0.0358 (8)	0.0369 (8)	0.0018 (6)	0.0136 (7)	−0.0017 (6)
C3	0.0423 (8)	0.0285 (8)	0.0411 (8)	0.0043 (6)	0.0168 (7)	−0.0013 (6)
C4	0.0379 (8)	0.0307 (8)	0.0346 (8)	0.0030 (6)	0.0135 (6)	0.0001 (6)
C5	0.0425 (8)	0.0278 (8)	0.0435 (8)	0.0003 (6)	0.0174 (7)	−0.0018 (6)
C6	0.0393 (8)	0.0353 (9)	0.0397 (8)	−0.0029 (6)	0.0157 (7)	−0.0001 (6)
C7	0.0437 (9)	0.0385 (9)	0.0442 (9)	0.0056 (7)	0.0209 (7)	−0.0032 (7)
C8	0.0493 (9)	0.0303 (9)	0.0448 (9)	0.0069 (7)	0.0205 (7)	−0.0013 (6)
C9	0.0406 (8)	0.0278 (8)	0.0350 (8)	0.0019 (6)	0.0138 (6)	−0.0001 (6)
C10	0.0431 (9)	0.0510 (11)	0.0445 (9)	0.0002 (8)	0.0208 (7)	−0.0024 (8)
C11	0.0605 (12)	0.0381 (10)	0.0751 (13)	−0.0109 (8)	0.0373 (10)	−0.0039 (8)

Cl1—C1	1.7461 (16)	C4—C9	1.421 (2)
O1—C10	1.201 (2)	C5—C6	1.370 (2)
O2—C6	1.3654 (18)	C5—H5	0.9300
O2—C11	1.426 (2)	C6—C7	1.411 (2)
N1—C1	1.302 (2)	C7—C8	1.359 (2)
N1—C9	1.362 (2)	C7—H7	0.9300
C1—C2	1.414 (2)	C8—C9	1.414 (2)
C2—C3	1.372 (2)	C8—H8	0.9300
C2—C10	1.487 (2)	C10—H10	0.9300
C3—C4	1.407 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.416 (2)	C11—H11C	0.9600
C6—O2—C11	117.12 (13)	C5—C6—C7	120.73 (14)
C1—N1—C9	117.96 (13)	C8—C7—C6	120.92 (14)
N1—C1—C2	125.38 (14)	C8—C7—H7	119.5
N1—C1—Cl1	114.97 (12)	C6—C7—H7	119.5
C2—C1—Cl1	119.62 (12)	C7—C8—C9	120.21 (14)
C3—C2—C1	116.56 (14)	C7—C8—H8	119.9
C3—C2—C10	119.25 (15)	C9—C8—H8	119.9
C1—C2—C10	124.17 (15)	N1—C9—C8	118.96 (14)
C2—C3—C4	120.94 (14)	N1—C9—C4	122.11 (13)
C2—C3—H3	119.5	C8—C9—C4	118.93 (14)
C4—C3—H3	119.5	O1—C10—C2	123.35 (17)
C3—C4—C5	123.14 (14)	O1—C10—H10	118.3
C3—C4—C9	117.05 (14)	C2—C10—H10	118.3
C5—C4—C9	119.81 (13)	O2—C11—H11A	109.5
C6—C5—C4	119.40 (15)	O2—C11—H11B	109.5
C6—C5—H5	120.3	H11A—C11—H11B	109.5
C4—C5—H5	120.3	O2—C11—H11C	109.5
O2—C6—C5	124.81 (15)	H11A—C11—H11C	109.5
O2—C6—C7	114.46 (13)	H11B—C11—H11C	109.5
C9—N1—C1—C2	0.5 (2)	C4—C5—C6—C7	−0.6 (2)
C9—N1—C1—Cl1	−177.49 (11)	O2—C6—C7—C8	179.38 (15)
N1—C1—C2—C3	−0.6 (2)	C5—C6—C7—C8	−0.4 (2)
Cl1—C1—C2—C3	177.35 (12)	C6—C7—C8—C9	0.9 (2)
N1—C1—C2—C10	−178.93 (16)	C1—N1—C9—C8	179.30 (15)
Cl1—C1—C2—C10	−1.0 (2)	C1—N1—C9—C4	0.3 (2)
C1—C2—C3—C4	−0.2 (2)	C7—C8—C9—N1	−179.39 (15)
C10—C2—C3—C4	178.22 (15)	C7—C8—C9—C4	−0.4 (2)
C2—C3—C4—C5	−178.40 (15)	C3—C4—C9—N1	−1.1 (2)
C2—C3—C4—C9	1.0 (2)	C5—C4—C9—N1	178.34 (14)
C3—C4—C5—C6	−179.51 (15)	C3—C4—C9—C8	179.98 (14)
C9—C4—C5—C6	1.1 (2)	C5—C4—C9—C8	−0.6 (2)
C11—O2—C6—C5	1.3 (2)	C3—C2—C10—O1	−2.4 (3)
C11—O2—C6—C7	−178.48 (16)	C1—C2—C10—O1	175.9 (2)
C4—C5—C6—O2	179.62 (15)