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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2686.
Published online 2009 October 10. doi:  10.1107/S1600536809040653
PMCID: PMC2971281

2-Chloro-6-methyl­quinoline-3-carbaldehyde

Abstract

The quinolinyl fused-ring of the title compound, C11H8ClNO, 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 [triangle]).

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Object name is e-65-o2686-scheme1.jpg

Experimental

Crystal data

  • C11H8ClNO
  • M r = 205.63
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2686-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 990 Friedel pairs
  • Flack parameter: 0.02 (6)

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

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

Acknowledgments

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA-DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

A Vilsmeier-Haack adduct prepared from phosphorus oxytrichloride (6.5 ml, 70 mmol) and N,N-dimethylformamide (2.3 ml, 30 mmol) at 273 K was added to N-(4-tolyl)acetamide (1.49 g, 10 mmol), and heated at 353 K for 15 h. The mixture was then poured onto ice, and the white product was collected and dried. The compound was purified by recrystallization from a petroleum ether/ethyl acetate mixture.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C11H8ClNO at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H8ClNOF(000) = 212
Mr = 205.63Dx = 1.466 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 1352 reflections
a = 5.944 (1) Åθ = 2.0–20.7°
b = 3.9210 (19) ŵ = 0.37 mm1
c = 20.390 (2) ÅT = 290 K
β = 101.377 (15)°Block, colorless
V = 465.9 (2) Å30.25 × 0.15 × 0.15 mm
Z = 2

Data collection

Oxford Diffraction Excalibur diffractometer2052 independent reflections
Radiation source: fine-focus sealed tube1831 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −7→7
Tmin = 0.913, Tmax = 0.947k = −5→5
5980 measured reflectionsl = −26→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.089w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2052 reflectionsΔρmax = 0.19 e Å3
128 parametersΔρmin = −0.17 e Å3
2 restraintsAbsolute structure: Flack (1983), 990 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl11.00002 (8)1.11653 (14)0.50000 (3)0.04862 (17)
O10.4626 (4)0.5444 (6)0.55814 (8)0.0676 (6)
N10.7865 (3)0.9885 (5)0.37983 (9)0.0382 (4)
C10.7703 (3)0.9492 (5)0.44201 (10)0.0351 (5)
C20.5905 (3)0.7858 (5)0.46557 (10)0.0340 (4)
C30.4137 (4)0.6644 (5)0.41837 (10)0.0341 (4)
H30.29060.55610.43150.041*
C40.4163 (3)0.7021 (5)0.34984 (10)0.0320 (4)
C50.2378 (4)0.5831 (5)0.29839 (10)0.0366 (4)
H50.10960.47920.30940.044*
C60.2519 (4)0.6196 (5)0.23214 (10)0.0383 (5)
C70.4490 (4)0.7786 (6)0.21674 (10)0.0454 (5)
H70.45980.80190.17210.054*
C80.6212 (4)0.8971 (6)0.26419 (11)0.0441 (5)
H80.74741.00150.25210.053*
C90.6099 (4)0.8627 (5)0.33289 (10)0.0335 (4)
C100.5895 (4)0.7365 (7)0.53783 (11)0.0470 (5)
H100.69300.86150.56880.056*
C110.0664 (4)0.4932 (7)0.17678 (10)0.0501 (6)
H11A−0.03980.35620.19520.075*
H11B0.13320.35840.14630.075*
H11C−0.01310.68410.15340.075*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0366 (3)0.0578 (3)0.0488 (3)−0.0066 (3)0.00193 (19)−0.0056 (3)
O10.0607 (12)0.1037 (15)0.0375 (9)−0.0252 (12)0.0074 (8)0.0170 (10)
N10.0348 (9)0.0388 (8)0.0428 (10)−0.0031 (7)0.0118 (7)−0.0002 (7)
C10.0309 (11)0.0349 (11)0.0389 (11)0.0019 (8)0.0056 (8)−0.0021 (8)
C20.0325 (11)0.0377 (10)0.0325 (9)0.0060 (9)0.0083 (8)0.0028 (8)
C30.0310 (10)0.0375 (10)0.0354 (11)0.0007 (8)0.0106 (8)0.0031 (8)
C40.0327 (10)0.0302 (10)0.0337 (10)0.0022 (8)0.0077 (8)0.0012 (8)
C50.0346 (11)0.0376 (11)0.0375 (10)−0.0002 (8)0.0067 (8)0.0003 (8)
C60.0412 (12)0.0384 (11)0.0348 (10)0.0030 (9)0.0062 (9)−0.0016 (8)
C70.0575 (15)0.0519 (12)0.0294 (10)0.0032 (11)0.0148 (10)0.0014 (9)
C80.0480 (13)0.0471 (12)0.0421 (11)−0.0048 (10)0.0207 (10)0.0018 (10)
C90.0355 (10)0.0326 (10)0.0337 (10)0.0021 (8)0.0099 (8)0.0003 (8)
C100.0412 (13)0.0631 (14)0.0350 (10)−0.0026 (11)0.0035 (9)0.0021 (11)
C110.0573 (15)0.0555 (13)0.0346 (11)−0.0024 (12)0.0019 (10)−0.0041 (10)

Geometric parameters (Å, °)

Cl1—C11.748 (2)C5—H50.9300
O1—C101.196 (3)C6—C71.416 (3)
N1—C11.300 (2)C6—C111.498 (3)
N1—C91.365 (3)C7—C81.345 (3)
C1—C21.409 (3)C7—H70.9300
C2—C31.363 (3)C8—C91.422 (3)
C2—C101.487 (3)C8—H80.9300
C3—C41.408 (3)C10—H100.9300
C3—H30.9300C11—H11A0.9600
C4—C91.414 (3)C11—H11B0.9600
C4—C51.416 (3)C11—H11C0.9600
C5—C61.377 (3)
C1—N1—C9116.50 (17)C8—C7—C6122.5 (2)
N1—C1—C2126.42 (19)C8—C7—H7118.7
N1—C1—Cl1114.64 (15)C6—C7—H7118.7
C2—C1—Cl1118.93 (14)C7—C8—C9119.9 (2)
C3—C2—C1116.68 (17)C7—C8—H8120.0
C3—C2—C10120.06 (19)C9—C8—H8120.0
C1—C2—C10123.25 (19)N1—C9—C4122.69 (17)
C2—C3—C4120.41 (18)N1—C9—C8118.51 (19)
C2—C3—H3119.8C4—C9—C8118.81 (19)
C4—C3—H3119.8O1—C10—C2123.4 (2)
C3—C4—C9117.27 (17)O1—C10—H10118.3
C3—C4—C5123.20 (18)C2—C10—H10118.3
C9—C4—C5119.53 (17)C6—C11—H11A109.5
C6—C5—C4120.73 (19)C6—C11—H11B109.5
C6—C5—H5119.6H11A—C11—H11B109.5
C4—C5—H5119.6C6—C11—H11C109.5
C5—C6—C7118.4 (2)H11A—C11—H11C109.5
C5—C6—C11121.8 (2)H11B—C11—H11C109.5
C7—C6—C11119.78 (19)
C9—N1—C1—C21.0 (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—C90.4 (3)
Cl1—C1—C2—C3179.00 (15)C1—N1—C9—C40.9 (3)
N1—C1—C2—C10177.0 (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—C40.5 (3)C5—C4—C9—N1178.91 (17)
C10—C2—C3—C4−178.30 (18)C3—C4—C9—C8178.38 (18)
C2—C3—C4—C91.2 (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—C40.2 (3)
C9—C4—C5—C60.6 (3)C3—C2—C10—O113.5 (4)
C4—C5—C6—C70.0 (3)C1—C2—C10—O1−165.1 (3)
C4—C5—C6—C11179.4 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2550).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Meth-Cohn, O. (1993). Heterocycles, 35, 539–557.
  • Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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