2-Chloro-8-methyl-quinoline-3-carbaldehyde.

The quinoline fused-ring system of the title compound, C(11)H(8)ClNO, is planar (r.m.s. deviation = 0.005 Å); the formyl group is slightly bent out of the plane [C-C-C-O1 torsion angles = 8.8 (7) and -172.8 (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

Orthorhombic,

a = 6.8576 (5) Å

b = 7.4936 (6) Å

c = 18.5003 (14) Å

V = 950.70 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 290 K

0.26 × 0.22 × 0.17 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.912, T max = 0.941

8224 measured reflections

2174 independent reflections

1734 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.00

2174 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 838 Friedel pairs

Flack parameter: 0.2 (2)

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/S1600536809040859/bt5085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040859/bt5085Isup2.hkl

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

C11H8ClNO	F(000) = 424
Mr = 205.63	Dx = 1.437 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 867 reflections
a = 6.8576 (5) Å	θ = 2.0–24.4°
b = 7.4936 (6) Å	µ = 0.36 mm−1
c = 18.5003 (14) Å	T = 290 K
V = 950.70 (13) Å3	Block, colorless
Z = 4	0.26 × 0.22 × 0.17 mm

Bruker SMART area-detector diffractometer	2174 independent reflections
Radiation source: fine-focus sealed tube	1734 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.912, Tmax = 0.941	k = −9→9
8224 measured reflections	l = −22→24

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0861P)2 + 0.0263P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2174 reflections	Δρmax = 0.25 e Å−3
129 parameters	Δρmin = −0.32 e Å−3
0 restraints	Absolute structure: Flack (1983), 838 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (2)

	x	y	z	Uiso*/Ueq
Cl1	0.87010 (13)	1.14505 (9)	0.37890 (4)	0.0579 (3)
O1	0.8672 (5)	0.6106 (3)	0.29577 (10)	0.0763 (6)
N1	0.8717 (4)	0.9871 (2)	0.50346 (10)	0.0366 (4)
C1	0.8734 (5)	0.9563 (3)	0.43459 (13)	0.0368 (5)
C2	0.8754 (5)	0.7858 (3)	0.40176 (11)	0.0398 (5)
C3	0.8734 (5)	0.6423 (4)	0.44734 (12)	0.0389 (5)
H3	0.8741	0.5276	0.4281	0.047*
C4	0.8705 (4)	0.6651 (3)	0.52293 (10)	0.0344 (5)
C5	0.8691 (5)	0.5212 (3)	0.57186 (14)	0.0443 (6)
H5	0.8707	0.4045	0.5547	0.053*
C6	0.8654 (6)	0.5531 (3)	0.64410 (13)	0.0468 (6)
H6	0.8633	0.4585	0.6766	0.056*
C7	0.8648 (5)	0.7301 (4)	0.66955 (13)	0.0443 (6)
H7	0.8614	0.7491	0.7192	0.053*
C8	0.8690 (4)	0.8754 (3)	0.62492 (11)	0.0372 (5)
C9	0.8702 (4)	0.8426 (3)	0.54918 (11)	0.0327 (4)
C10	0.8840 (6)	0.7545 (5)	0.32246 (14)	0.0551 (7)
H10	0.9034	0.8521	0.2922	0.066*
C11	0.8698 (7)	1.0624 (3)	0.65349 (14)	0.0547 (7)
H11A	0.8779	1.0598	0.7053	0.082*
H11B	0.7519	1.1218	0.6392	0.082*
H11C	0.9801	1.1255	0.6343	0.082*

	U11	U22	U33	U12	U13	U23
Cl1	0.0687 (4)	0.0591 (4)	0.0459 (4)	0.0008 (5)	0.0006 (4)	0.0218 (3)
O1	0.0887 (16)	0.1007 (17)	0.0394 (10)	−0.008 (2)	−0.0031 (13)	−0.0254 (11)
N1	0.0371 (10)	0.0403 (10)	0.0324 (10)	−0.0007 (12)	0.0005 (12)	0.0028 (7)
C1	0.0327 (11)	0.0459 (13)	0.0318 (12)	0.0001 (17)	−0.0007 (16)	0.0062 (10)
C2	0.0347 (11)	0.0576 (14)	0.0272 (10)	−0.0003 (15)	−0.0008 (12)	−0.0019 (10)
C3	0.0393 (11)	0.0427 (11)	0.0348 (12)	−0.002 (2)	−0.0005 (14)	−0.0084 (10)
C4	0.0323 (10)	0.0410 (11)	0.0300 (10)	−0.0007 (15)	0.0005 (11)	−0.0004 (8)
C5	0.0509 (14)	0.0398 (12)	0.0422 (14)	0.0026 (19)	0.0008 (19)	0.0040 (10)
C6	0.0509 (14)	0.0519 (14)	0.0375 (12)	0.0021 (17)	0.0007 (16)	0.0120 (10)
C7	0.0457 (14)	0.0596 (15)	0.0276 (11)	0.0043 (19)	−0.0022 (15)	0.0020 (11)
C8	0.0344 (10)	0.0461 (12)	0.0310 (11)	0.0029 (12)	−0.0009 (13)	−0.0014 (9)
C9	0.0292 (10)	0.0407 (11)	0.0280 (10)	−0.0001 (16)	0.0004 (12)	0.0002 (9)
C10	0.0538 (17)	0.084 (2)	0.0278 (12)	0.000 (2)	−0.0010 (17)	−0.0032 (13)
C11	0.0716 (17)	0.0543 (15)	0.0384 (13)	0.003 (2)	−0.0005 (19)	−0.0128 (11)

Cl1—C1	1.750 (2)	C5—H5	0.9300
O1—C10	1.191 (4)	C6—C7	1.407 (4)
N1—C1	1.295 (3)	C6—H6	0.9300
N1—C9	1.374 (3)	C7—C8	1.367 (3)
C1—C2	1.415 (3)	C7—H7	0.9300
C2—C3	1.367 (3)	C8—C9	1.423 (3)
C2—C10	1.487 (3)	C8—C11	1.498 (3)
C3—C4	1.409 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.408 (3)	C11—H11B	0.9600
C4—C9	1.416 (3)	C11—H11C	0.9600
C5—C6	1.358 (4)
C1—N1—C9	117.73 (18)	C8—C7—C6	123.3 (2)
N1—C1—C2	125.68 (19)	C8—C7—H7	118.4
N1—C1—Cl1	115.80 (18)	C6—C7—H7	118.4
C2—C1—Cl1	118.52 (18)	C7—C8—C9	117.2 (2)
C3—C2—C1	116.47 (19)	C7—C8—C11	122.2 (2)
C3—C2—C10	119.0 (2)	C9—C8—C11	120.6 (2)
C1—C2—C10	124.5 (2)	N1—C9—C4	121.95 (19)
C2—C3—C4	121.1 (2)	N1—C9—C8	118.06 (19)
C2—C3—H3	119.4	C4—C9—C8	119.99 (19)
C4—C3—H3	119.4	O1—C10—C2	123.2 (3)
C5—C4—C3	123.0 (2)	O1—C10—H10	118.4
C5—C4—C9	119.9 (2)	C2—C10—H10	118.4
C3—C4—C9	117.0 (2)	C8—C11—H11A	109.5
C6—C5—C4	119.9 (2)	C8—C11—H11B	109.5
C6—C5—H5	120.1	H11A—C11—H11B	109.5
C4—C5—H5	120.1	C8—C11—H11C	109.5
C5—C6—C7	119.7 (2)	H11A—C11—H11C	109.5
C5—C6—H6	120.2	H11B—C11—H11C	109.5
C7—C6—H6	120.2
C9—N1—C1—C2	−0.5 (5)	C6—C7—C8—C9	1.3 (5)
C9—N1—C1—Cl1	178.7 (2)	C6—C7—C8—C11	−179.5 (4)
N1—C1—C2—C3	0.6 (5)	C1—N1—C9—C4	0.0 (4)
Cl1—C1—C2—C3	−178.6 (3)	C1—N1—C9—C8	179.8 (3)
N1—C1—C2—C10	−177.9 (3)	C5—C4—C9—N1	179.9 (3)
Cl1—C1—C2—C10	2.9 (5)	C3—C4—C9—N1	0.3 (5)
C1—C2—C3—C4	−0.3 (5)	C5—C4—C9—C8	0.2 (4)
C10—C2—C3—C4	178.3 (3)	C3—C4—C9—C8	−179.4 (2)
C2—C3—C4—C5	−179.8 (3)	C7—C8—C9—N1	179.1 (3)
C2—C3—C4—C9	−0.1 (5)	C11—C8—C9—N1	−0.1 (5)
C3—C4—C5—C6	−179.7 (4)	C7—C8—C9—C4	−1.1 (4)
C9—C4—C5—C6	0.7 (5)	C11—C8—C9—C4	179.6 (3)
C4—C5—C6—C7	−0.6 (6)	C3—C2—C10—O1	8.8 (7)
C5—C6—C7—C8	−0.4 (6)	C1—C2—C10—O1	−172.8 (4)