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

The quinolinyl fused-ring of the title compound, C(11)H(8)ClNO, is almost planar (r.m.s. deviation = 0.013 Å); the formyl group is slightly bent out of the plane of the fused ring system [C-C-C-O torsion angle = 13.5 (4)°].

Related literature

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

Experimental

Crystal data

C11H8ClNO

M = 205.63

Monoclinic,

a = 5.944 (1) Å

b = 3.9210 (19) Å

c = 20.390 (2) Å

β = 101.377 (15)°

V = 465.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 290 K

0.25 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Excalibur diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.913, T max = 0.947

5980 measured reflections

2052 independent reflections

1831 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.00

2052 reflections

128 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 990 Friedel pairs

Flack parameter: 0.02 (6)

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; 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/S1600536809040653/tk2550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040653/tk2550Isup2.hkl

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

C11H8ClNO	F(000) = 212
Mr = 205.63	Dx = 1.466 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 1352 reflections
a = 5.944 (1) Å	θ = 2.0–20.7°
b = 3.9210 (19) Å	µ = 0.37 mm−1
c = 20.390 (2) Å	T = 290 K
β = 101.377 (15)°	Block, colorless
V = 465.9 (2) Å3	0.25 × 0.15 × 0.15 mm
Z = 2

Oxford Diffraction Excalibur diffractometer	2052 independent reflections
Radiation source: fine-focus sealed tube	1831 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.913, Tmax = 0.947	k = −5→5
5980 measured reflections	l = −26→25

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2052 reflections	Δρmax = 0.19 e Å−3
128 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack (1983), 990 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (6)

	x	y	z	Uiso*/Ueq
Cl1	1.00002 (8)	1.11653 (14)	0.50000 (3)	0.04862 (17)
O1	0.4626 (4)	0.5444 (6)	0.55814 (8)	0.0676 (6)
N1	0.7865 (3)	0.9885 (5)	0.37983 (9)	0.0382 (4)
C1	0.7703 (3)	0.9492 (5)	0.44201 (10)	0.0351 (5)
C2	0.5905 (3)	0.7858 (5)	0.46557 (10)	0.0340 (4)
C3	0.4137 (4)	0.6644 (5)	0.41837 (10)	0.0341 (4)
H3	0.2906	0.5561	0.4315	0.041*
C4	0.4163 (3)	0.7021 (5)	0.34984 (10)	0.0320 (4)
C5	0.2378 (4)	0.5831 (5)	0.29839 (10)	0.0366 (4)
H5	0.1096	0.4792	0.3094	0.044*
C6	0.2519 (4)	0.6196 (5)	0.23214 (10)	0.0383 (5)
C7	0.4490 (4)	0.7786 (6)	0.21674 (10)	0.0454 (5)
H7	0.4598	0.8019	0.1721	0.054*
C8	0.6212 (4)	0.8971 (6)	0.26419 (11)	0.0441 (5)
H8	0.7474	1.0015	0.2521	0.053*
C9	0.6099 (4)	0.8627 (5)	0.33289 (10)	0.0335 (4)
C10	0.5895 (4)	0.7365 (7)	0.53783 (11)	0.0470 (5)
H10	0.6930	0.8615	0.5688	0.056*
C11	0.0664 (4)	0.4932 (7)	0.17678 (10)	0.0501 (6)
H11A	−0.0398	0.3562	0.1952	0.075*
H11B	0.1332	0.3584	0.1463	0.075*
H11C	−0.0131	0.6841	0.1534	0.075*

	U11	U22	U33	U12	U13	U23
Cl1	0.0366 (3)	0.0578 (3)	0.0488 (3)	−0.0066 (3)	0.00193 (19)	−0.0056 (3)
O1	0.0607 (12)	0.1037 (15)	0.0375 (9)	−0.0252 (12)	0.0074 (8)	0.0170 (10)
N1	0.0348 (9)	0.0388 (8)	0.0428 (10)	−0.0031 (7)	0.0118 (7)	−0.0002 (7)
C1	0.0309 (11)	0.0349 (11)	0.0389 (11)	0.0019 (8)	0.0056 (8)	−0.0021 (8)
C2	0.0325 (11)	0.0377 (10)	0.0325 (9)	0.0060 (9)	0.0083 (8)	0.0028 (8)
C3	0.0310 (10)	0.0375 (10)	0.0354 (11)	0.0007 (8)	0.0106 (8)	0.0031 (8)
C4	0.0327 (10)	0.0302 (10)	0.0337 (10)	0.0022 (8)	0.0077 (8)	0.0012 (8)
C5	0.0346 (11)	0.0376 (11)	0.0375 (10)	−0.0002 (8)	0.0067 (8)	0.0003 (8)
C6	0.0412 (12)	0.0384 (11)	0.0348 (10)	0.0030 (9)	0.0062 (9)	−0.0016 (8)
C7	0.0575 (15)	0.0519 (12)	0.0294 (10)	0.0032 (11)	0.0148 (10)	0.0014 (9)
C8	0.0480 (13)	0.0471 (12)	0.0421 (11)	−0.0048 (10)	0.0207 (10)	0.0018 (10)
C9	0.0355 (10)	0.0326 (10)	0.0337 (10)	0.0021 (8)	0.0099 (8)	0.0003 (8)
C10	0.0412 (13)	0.0631 (14)	0.0350 (10)	−0.0026 (11)	0.0035 (9)	0.0021 (11)
C11	0.0573 (15)	0.0555 (13)	0.0346 (11)	−0.0024 (12)	0.0019 (10)	−0.0041 (10)

Cl1—C1	1.748 (2)	C5—H5	0.9300
O1—C10	1.196 (3)	C6—C7	1.416 (3)
N1—C1	1.300 (2)	C6—C11	1.498 (3)
N1—C9	1.365 (3)	C7—C8	1.345 (3)
C1—C2	1.409 (3)	C7—H7	0.9300
C2—C3	1.363 (3)	C8—C9	1.422 (3)
C2—C10	1.487 (3)	C8—H8	0.9300
C3—C4	1.408 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—H11A	0.9600
C4—C9	1.414 (3)	C11—H11B	0.9600
C4—C5	1.416 (3)	C11—H11C	0.9600
C5—C6	1.377 (3)
C1—N1—C9	116.50 (17)	C8—C7—C6	122.5 (2)
N1—C1—C2	126.42 (19)	C8—C7—H7	118.7
N1—C1—Cl1	114.64 (15)	C6—C7—H7	118.7
C2—C1—Cl1	118.93 (14)	C7—C8—C9	119.9 (2)
C3—C2—C1	116.68 (17)	C7—C8—H8	120.0
C3—C2—C10	120.06 (19)	C9—C8—H8	120.0
C1—C2—C10	123.25 (19)	N1—C9—C4	122.69 (17)
C2—C3—C4	120.41 (18)	N1—C9—C8	118.51 (19)
C2—C3—H3	119.8	C4—C9—C8	118.81 (19)
C4—C3—H3	119.8	O1—C10—C2	123.4 (2)
C3—C4—C9	117.27 (17)	O1—C10—H10	118.3
C3—C4—C5	123.20 (18)	C2—C10—H10	118.3
C9—C4—C5	119.53 (17)	C6—C11—H11A	109.5
C6—C5—C4	120.73 (19)	C6—C11—H11B	109.5
C6—C5—H5	119.6	H11A—C11—H11B	109.5
C4—C5—H5	119.6	C6—C11—H11C	109.5
C5—C6—C7	118.4 (2)	H11A—C11—H11C	109.5
C5—C6—C11	121.8 (2)	H11B—C11—H11C	109.5
C7—C6—C11	119.78 (19)
C9—N1—C1—C2	1.0 (3)	C5—C6—C7—C8	−0.6 (3)
C9—N1—C1—Cl1	−179.69 (15)	C11—C6—C7—C8	−180.0 (2)
N1—C1—C2—C3	−1.7 (3)	C6—C7—C8—C9	0.4 (3)
Cl1—C1—C2—C3	179.00 (15)	C1—N1—C9—C4	0.9 (3)
N1—C1—C2—C10	177.0 (2)	C1—N1—C9—C8	−179.45 (19)
Cl1—C1—C2—C10	−2.3 (3)	C3—C4—C9—N1	−2.0 (3)
C1—C2—C3—C4	0.5 (3)	C5—C4—C9—N1	178.91 (17)
C10—C2—C3—C4	−178.30 (18)	C3—C4—C9—C8	178.38 (18)
C2—C3—C4—C9	1.2 (3)	C5—C4—C9—C8	−0.7 (3)
C2—C3—C4—C5	−179.73 (19)	C7—C8—C9—N1	−179.4 (2)
C3—C4—C5—C6	−178.44 (18)	C7—C8—C9—C4	0.2 (3)
C9—C4—C5—C6	0.6 (3)	C3—C2—C10—O1	13.5 (4)
C4—C5—C6—C7	0.0 (3)	C1—C2—C10—O1	−165.1 (3)
C4—C5—C6—C11	179.4 (2)