2-Chloro-quinoline-3-carbaldehyde.

The quinolinyl fused ring system of the title compound, C(10)H(6)ClNO, is planar (r.m.s. deviation = 0.018 Å); the formyl group is slightly bent out of the plane of the fused ring system [C-C-C-O torsion angle = 8.2 (3)°].

Related literature

For the synthesis of 2-chloro­quinoline-3-carbaldehyde by Vilsmeier–Haack cyclization, see: Ali et al. (2001 ▶, 2002 ▶); Mogilaiah et al. (2002 ▶); Pawar et al. (1990 ▶); Srivastava & Singh (2005 ▶). For a review of the synthesis of quinolines by this reaction, see: Meth-Cohn (1993 ▶).

Experimental

Crystal data

C10H6ClNO

M = 191.61

Monoclinic,

a = 11.8784 (9) Å

b = 3.9235 (3) Å

c = 18.1375 (12) Å

β = 101.365 (4)°

V = 828.72 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 290 K

0.24 × 0.18 × 0.14 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.945

6886 measured reflections

1889 independent reflections

1626 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.145

S = 1.19

1889 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.29 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/S1600536809040665/tk2549sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040665/tk2549Isup2.hkl

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

C10H6ClNO	F(000) = 392
Mr = 191.61	Dx = 1.536 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 781 reflections
a = 11.8784 (9) Å	θ = 2.1–24.3°
b = 3.9235 (3) Å	µ = 0.41 mm−1
c = 18.1375 (12) Å	T = 290 K
β = 101.365 (4)°	Block, colorless
V = 828.72 (10) Å3	0.24 × 0.18 × 0.14 mm
Z = 4

Bruker SMART area-detector diffractometer	1889 independent reflections
Radiation source: fine-focus sealed tube	1626 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.908, Tmax = 0.945	k = −3→5
6886 measured reflections	l = −23→23

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0923P)2 + 0.077P] where P = (Fo2 + 2Fc2)/3
1889 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.24556 (4)	0.22180 (12)	0.67041 (2)	0.0464 (2)
O1	0.51095 (11)	0.8482 (4)	0.61287 (8)	0.0550 (4)
N1	0.15508 (12)	0.2731 (3)	0.52950 (9)	0.0353 (3)
C1	0.24476 (14)	0.3582 (4)	0.57833 (9)	0.0319 (4)
C2	0.34039 (13)	0.5468 (4)	0.56384 (9)	0.0323 (4)
C3	0.33695 (13)	0.6369 (4)	0.49061 (9)	0.0334 (4)
H3	0.3977	0.7585	0.4781	0.040*
C4	0.24263 (13)	0.5477 (4)	0.43407 (9)	0.0324 (4)
C5	0.23434 (16)	0.6341 (5)	0.35765 (10)	0.0419 (4)
H5	0.2944	0.7483	0.3424	0.050*
C6	0.13859 (17)	0.5504 (5)	0.30635 (10)	0.0481 (5)
H6	0.1334	0.6077	0.2560	0.058*
C7	0.04727 (17)	0.3774 (6)	0.32911 (11)	0.0493 (5)
H7	−0.0180	0.3243	0.2935	0.059*
C8	0.05247 (16)	0.2861 (5)	0.40222 (12)	0.0436 (4)
H8	−0.0082	0.1699	0.4162	0.052*
C9	0.15087 (13)	0.3697 (4)	0.45629 (9)	0.0325 (4)
C10	0.43810 (15)	0.6537 (5)	0.62315 (10)	0.0407 (4)
H10	0.4432	0.5645	0.6712	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0587 (3)	0.0522 (3)	0.0308 (3)	−0.00331 (19)	0.0147 (2)	0.00444 (16)
O1	0.0435 (8)	0.0681 (10)	0.0499 (8)	−0.0161 (6)	0.0004 (6)	0.0003 (7)
N1	0.0363 (7)	0.0355 (7)	0.0355 (8)	−0.0016 (5)	0.0107 (6)	−0.0029 (5)
C1	0.0381 (8)	0.0310 (8)	0.0283 (7)	0.0020 (6)	0.0107 (6)	0.0004 (6)
C2	0.0335 (8)	0.0312 (8)	0.0321 (8)	0.0024 (6)	0.0062 (6)	−0.0007 (6)
C3	0.0329 (8)	0.0332 (8)	0.0349 (8)	−0.0001 (6)	0.0089 (6)	0.0018 (7)
C4	0.0362 (8)	0.0317 (8)	0.0299 (8)	0.0056 (6)	0.0077 (6)	−0.0005 (6)
C5	0.0489 (10)	0.0444 (9)	0.0332 (9)	0.0076 (8)	0.0101 (7)	0.0039 (7)
C6	0.0591 (11)	0.0544 (11)	0.0289 (8)	0.0166 (9)	0.0039 (8)	−0.0021 (8)
C7	0.0454 (10)	0.0560 (11)	0.0407 (10)	0.0110 (8)	−0.0058 (8)	−0.0141 (9)
C8	0.0356 (9)	0.0467 (10)	0.0466 (11)	0.0012 (7)	0.0037 (8)	−0.0120 (8)
C9	0.0331 (8)	0.0320 (8)	0.0329 (8)	0.0032 (6)	0.0072 (6)	−0.0052 (6)
C10	0.0414 (9)	0.0459 (10)	0.0332 (9)	−0.0003 (7)	0.0031 (7)	0.0017 (7)

Cl1—C1	1.7519 (16)	C4—C9	1.418 (2)
O1—C10	1.196 (2)	C5—C6	1.360 (3)
N1—C1	1.288 (2)	C5—H5	0.9300
N1—C9	1.372 (2)	C6—C7	1.409 (3)
C1—C2	1.423 (2)	C6—H6	0.9300
C2—C3	1.367 (2)	C7—C8	1.363 (3)
C2—C10	1.479 (2)	C7—H7	0.9300
C3—C4	1.406 (2)	C8—C9	1.409 (2)
C3—H3	0.9300	C8—H8	0.9300
C4—C5	1.411 (2)	C10—H10	0.9300
C1—N1—C9	117.48 (14)	C5—C6—C7	120.28 (17)
N1—C1—C2	126.15 (15)	C5—C6—H6	119.9
N1—C1—Cl1	115.14 (12)	C7—C6—H6	119.9
C2—C1—Cl1	118.71 (12)	C8—C7—C6	121.46 (17)
C3—C2—C1	116.22 (14)	C8—C7—H7	119.3
C3—C2—C10	120.14 (15)	C6—C7—H7	119.3
C1—C2—C10	123.62 (15)	C7—C8—C9	119.23 (18)
C2—C3—C4	120.74 (14)	C7—C8—H8	120.4
C2—C3—H3	119.6	C9—C8—H8	120.4
C4—C3—H3	119.6	N1—C9—C8	118.45 (15)
C3—C4—C5	123.22 (15)	N1—C9—C4	121.83 (14)
C3—C4—C9	117.52 (14)	C8—C9—C4	119.71 (16)
C5—C4—C9	119.24 (15)	O1—C10—C2	123.76 (16)
C6—C5—C4	120.07 (17)	O1—C10—H10	118.1
C6—C5—H5	120.0	C2—C10—H10	118.1
C4—C5—H5	120.0
C9—N1—C1—C2	0.6 (2)	C5—C6—C7—C8	−0.8 (3)
C9—N1—C1—Cl1	−179.13 (11)	C6—C7—C8—C9	0.7 (3)
N1—C1—C2—C3	−1.8 (2)	C1—N1—C9—C8	−178.61 (14)
Cl1—C1—C2—C3	177.90 (11)	C1—N1—C9—C4	1.8 (2)
N1—C1—C2—C10	176.39 (16)	C7—C8—C9—N1	−179.43 (15)
Cl1—C1—C2—C10	−3.9 (2)	C7—C8—C9—C4	0.1 (3)
C1—C2—C3—C4	0.6 (2)	C3—C4—C9—N1	−2.9 (2)
C10—C2—C3—C4	−177.67 (14)	C5—C4—C9—N1	178.69 (15)
C2—C3—C4—C5	179.92 (15)	C3—C4—C9—C8	177.57 (15)
C2—C3—C4—C9	1.5 (2)	C5—C4—C9—C8	−0.9 (2)
C3—C4—C5—C6	−177.55 (16)	C3—C2—C10—O1	8.2 (3)
C9—C4—C5—C6	0.8 (3)	C1—C2—C10—O1	−170.0 (2)
C4—C5—C6—C7	0.0 (3)