2-Chloro-7-methyl-quinoline-3-carbaldehyde.

The quinoline fused-ring system of the title compound, C(11)H(8)ClNO, is planar (r.m.s. deviation = 0.007 Å); the formyl group is bent slightly out of the plane [C-C-C-O torsion angles = -9.6 (5) and 170.4 (3)°].

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 = 15.458 (3) Å

b = 3.9382 (8) Å

c = 16.923 (3) Å

β = 112.854 (3)°

V = 949.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 290 K

0.24 × 0.18 × 0.06 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.918, T max = 0.979

6484 measured reflections

1796 independent reflections

1356 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.209

S = 1.13

1796 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.49 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/S1600536809040823/xu2629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040823/xu2629Isup2.hkl

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

C11H8ClNO	F(000) = 424
Mr = 205.63	Dx = 1.439 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 973 reflections
a = 15.458 (3) Å	θ = 1.3–24.9°
b = 3.9382 (8) Å	µ = 0.36 mm−1
c = 16.923 (3) Å	T = 290 K
β = 112.854 (3)°	Block, colorless
V = 949.3 (3) Å3	0.24 × 0.18 × 0.06 mm
Z = 4

Bruker SMART area-detector diffractometer	1796 independent reflections
Radiation source: fine-focus sealed tube	1356 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 25.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.918, Tmax = 0.979	k = −4→4
6484 measured reflections	l = −20→20

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.1371P)2] where P = (Fo2 + 2Fc2)/3
1796 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.37647 (6)	0.6903 (3)	0.18658 (6)	0.0603 (4)
O1	0.36833 (17)	0.1214 (8)	0.39875 (18)	0.0705 (9)
N1	0.55664 (19)	0.6719 (7)	0.27097 (16)	0.0402 (7)
C1	0.4781 (2)	0.5835 (8)	0.27548 (19)	0.0393 (7)
C2	0.4683 (2)	0.4068 (8)	0.34482 (19)	0.0383 (7)
C3	0.5497 (2)	0.3312 (8)	0.4129 (2)	0.0387 (7)
H3	0.5468	0.2182	0.4601	0.046*
C4	0.6373 (2)	0.4210 (7)	0.41281 (18)	0.0347 (7)
C5	0.7243 (2)	0.3490 (8)	0.48060 (19)	0.0407 (8)
H5	0.7253	0.2376	0.5294	0.049*
C6	0.8064 (2)	0.4414 (8)	0.47489 (19)	0.0424 (8)
H6	0.8628	0.3923	0.5201	0.051*
C7	0.8080 (2)	0.6125 (7)	0.4009 (2)	0.0394 (8)
C8	0.7248 (2)	0.6851 (8)	0.3354 (2)	0.0391 (7)
H8	0.7252	0.7978	0.2872	0.047*
C9	0.6379 (2)	0.5927 (7)	0.33897 (18)	0.0341 (7)
C10	0.3769 (2)	0.3059 (9)	0.3458 (2)	0.0503 (9)
H10	0.3228	0.3900	0.3029	0.060*
C11	0.9001 (3)	0.7114 (9)	0.3968 (2)	0.0523 (9)
H11A	0.8906	0.9001	0.3584	0.078*
H11B	0.9248	0.5226	0.3764	0.078*
H11C	0.9436	0.7746	0.4530	0.078*

	U11	U22	U33	U12	U13	U23
Cl1	0.0499 (6)	0.0826 (8)	0.0457 (6)	0.0050 (4)	0.0157 (4)	0.0154 (4)
O1	0.0512 (17)	0.103 (2)	0.0731 (18)	−0.0030 (14)	0.0416 (15)	0.0286 (15)
N1	0.0478 (16)	0.0474 (15)	0.0341 (14)	0.0010 (12)	0.0252 (13)	0.0033 (10)
C1	0.0427 (18)	0.0452 (17)	0.0380 (16)	0.0017 (13)	0.0245 (14)	0.0012 (13)
C2	0.0407 (18)	0.0452 (17)	0.0395 (17)	0.0026 (12)	0.0272 (14)	0.0014 (12)
C3	0.0476 (19)	0.0439 (17)	0.0383 (16)	0.0018 (13)	0.0316 (15)	0.0017 (12)
C4	0.0424 (17)	0.0396 (15)	0.0323 (15)	0.0025 (12)	0.0257 (13)	−0.0005 (11)
C5	0.0439 (18)	0.0549 (19)	0.0338 (16)	0.0035 (14)	0.0267 (14)	0.0011 (13)
C6	0.0390 (17)	0.0560 (19)	0.0386 (17)	0.0053 (14)	0.0221 (14)	−0.0053 (14)
C7	0.0467 (19)	0.0403 (16)	0.0449 (18)	−0.0047 (13)	0.0328 (16)	−0.0095 (12)
C8	0.0477 (19)	0.0440 (17)	0.0400 (17)	−0.0032 (13)	0.0327 (15)	−0.0016 (12)
C9	0.0423 (17)	0.0391 (15)	0.0322 (15)	−0.0007 (12)	0.0268 (13)	−0.0019 (11)
C10	0.0388 (19)	0.065 (2)	0.055 (2)	0.0019 (15)	0.0272 (17)	0.0066 (17)
C11	0.0469 (19)	0.060 (2)	0.063 (2)	−0.0075 (15)	0.0351 (17)	−0.0042 (16)

Cl1—C1	1.753 (3)	C5—H5	0.9300
O1—C10	1.200 (4)	C6—C7	1.430 (4)
N1—C1	1.293 (4)	C6—H6	0.9300
N1—C9	1.370 (4)	C7—C8	1.363 (4)
C1—C2	1.422 (4)	C7—C11	1.502 (5)
C2—C3	1.369 (4)	C8—C9	1.416 (4)
C2—C10	1.473 (4)	C8—H8	0.9300
C3—C4	1.400 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.417 (4)	C11—H11B	0.9600
C4—C9	1.424 (4)	C11—H11C	0.9600
C5—C6	1.359 (4)
C1—N1—C9	117.7 (3)	C8—C7—C6	118.6 (3)
N1—C1—C2	125.7 (3)	C8—C7—C11	121.3 (3)
N1—C1—Cl1	115.7 (2)	C6—C7—C11	120.1 (3)
C2—C1—Cl1	118.5 (2)	C7—C8—C9	121.5 (3)
C3—C2—C1	116.3 (3)	C7—C8—H8	119.3
C3—C2—C10	120.2 (3)	C9—C8—H8	119.3
C1—C2—C10	123.5 (3)	N1—C9—C8	118.8 (3)
C2—C3—C4	121.2 (3)	N1—C9—C4	121.9 (3)
C2—C3—H3	119.4	C8—C9—C4	119.3 (3)
C4—C3—H3	119.4	O1—C10—C2	123.8 (3)
C3—C4—C5	124.3 (3)	O1—C10—H10	118.1
C3—C4—C9	117.2 (3)	C2—C10—H10	118.1
C5—C4—C9	118.5 (3)	C7—C11—H11A	109.5
C6—C5—C4	120.5 (3)	C7—C11—H11B	109.5
C6—C5—H5	119.7	H11A—C11—H11B	109.5
C4—C5—H5	119.7	C7—C11—H11C	109.5
C5—C6—C7	121.5 (3)	H11A—C11—H11C	109.5
C5—C6—H6	119.3	H11B—C11—H11C	109.5
C7—C6—H6	119.3
C9—N1—C1—C2	−0.7 (5)	C5—C6—C7—C11	179.9 (3)
C9—N1—C1—Cl1	−179.8 (2)	C6—C7—C8—C9	−0.5 (4)
N1—C1—C2—C3	1.3 (5)	C11—C7—C8—C9	−180.0 (3)
Cl1—C1—C2—C3	−179.6 (2)	C1—N1—C9—C8	179.6 (3)
N1—C1—C2—C10	−178.7 (3)	C1—N1—C9—C4	−0.4 (4)
Cl1—C1—C2—C10	0.5 (4)	C7—C8—C9—N1	−179.8 (3)
C1—C2—C3—C4	−0.8 (4)	C7—C8—C9—C4	0.2 (4)
C10—C2—C3—C4	179.2 (3)	C3—C4—C9—N1	0.8 (4)
C2—C3—C4—C5	−179.5 (3)	C5—C4—C9—N1	−179.8 (3)
C2—C3—C4—C9	−0.2 (4)	C3—C4—C9—C8	−179.2 (3)
C3—C4—C5—C6	179.1 (3)	C5—C4—C9—C8	0.1 (4)
C9—C4—C5—C6	−0.2 (4)	C3—C2—C10—O1	−9.6 (5)
C4—C5—C6—C7	−0.1 (5)	C1—C2—C10—O1	170.4 (3)
C5—C6—C7—C8	0.5 (5)