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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2721.
Published online 2009 October 13. doi:  10.1107/S1600536809040823
PMCID: PMC2971315

2-Chloro-7-methyl­quinoline-3-carbaldehyde

Abstract

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

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Object name is e-65-o2721-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-o2721-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; 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/S1600536809040823/xu2629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040823/xu2629Isup2.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 also 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 N-(3-tolyl)acetamide (1.49 g, 10 mmol). The mixture was heated at 353 K for 15 h. The mixture was poured onto ice; 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 U(H) set to 1.2–1.5U(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) = 424
Mr = 205.63Dx = 1.439 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 973 reflections
a = 15.458 (3) Åθ = 1.3–24.9°
b = 3.9382 (8) ŵ = 0.36 mm1
c = 16.923 (3) ÅT = 290 K
β = 112.854 (3)°Block, colorless
V = 949.3 (3) Å30.24 × 0.18 × 0.06 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer1796 independent reflections
Radiation source: fine-focus sealed tube1356 reflections with I > 2σ(I)
graphiteRint = 0.042
[var phi] and ω scansθmax = 25.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.918, Tmax = 0.979k = −4→4
6484 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.1371P)2] where P = (Fo2 + 2Fc2)/3
1796 reflections(Δ/σ)max = 0.001
128 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = −0.49 e Å3

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

xyzUiso*/Ueq
Cl10.37647 (6)0.6903 (3)0.18658 (6)0.0603 (4)
O10.36833 (17)0.1214 (8)0.39875 (18)0.0705 (9)
N10.55664 (19)0.6719 (7)0.27097 (16)0.0402 (7)
C10.4781 (2)0.5835 (8)0.27548 (19)0.0393 (7)
C20.4683 (2)0.4068 (8)0.34482 (19)0.0383 (7)
C30.5497 (2)0.3312 (8)0.4129 (2)0.0387 (7)
H30.54680.21820.46010.046*
C40.6373 (2)0.4210 (7)0.41281 (18)0.0347 (7)
C50.7243 (2)0.3490 (8)0.48060 (19)0.0407 (8)
H50.72530.23760.52940.049*
C60.8064 (2)0.4414 (8)0.47489 (19)0.0424 (8)
H60.86280.39230.52010.051*
C70.8080 (2)0.6125 (7)0.4009 (2)0.0394 (8)
C80.7248 (2)0.6851 (8)0.3354 (2)0.0391 (7)
H80.72520.79780.28720.047*
C90.6379 (2)0.5927 (7)0.33897 (18)0.0341 (7)
C100.3769 (2)0.3059 (9)0.3458 (2)0.0503 (9)
H100.32280.39000.30290.060*
C110.9001 (3)0.7114 (9)0.3968 (2)0.0523 (9)
H11A0.89060.90010.35840.078*
H11B0.92480.52260.37640.078*
H11C0.94360.77460.45300.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0499 (6)0.0826 (8)0.0457 (6)0.0050 (4)0.0157 (4)0.0154 (4)
O10.0512 (17)0.103 (2)0.0731 (18)−0.0030 (14)0.0416 (15)0.0286 (15)
N10.0478 (16)0.0474 (15)0.0341 (14)0.0010 (12)0.0252 (13)0.0033 (10)
C10.0427 (18)0.0452 (17)0.0380 (16)0.0017 (13)0.0245 (14)0.0012 (13)
C20.0407 (18)0.0452 (17)0.0395 (17)0.0026 (12)0.0272 (14)0.0014 (12)
C30.0476 (19)0.0439 (17)0.0383 (16)0.0018 (13)0.0316 (15)0.0017 (12)
C40.0424 (17)0.0396 (15)0.0323 (15)0.0025 (12)0.0257 (13)−0.0005 (11)
C50.0439 (18)0.0549 (19)0.0338 (16)0.0035 (14)0.0267 (14)0.0011 (13)
C60.0390 (17)0.0560 (19)0.0386 (17)0.0053 (14)0.0221 (14)−0.0053 (14)
C70.0467 (19)0.0403 (16)0.0449 (18)−0.0047 (13)0.0328 (16)−0.0095 (12)
C80.0477 (19)0.0440 (17)0.0400 (17)−0.0032 (13)0.0327 (15)−0.0016 (12)
C90.0423 (17)0.0391 (15)0.0322 (15)−0.0007 (12)0.0268 (13)−0.0019 (11)
C100.0388 (19)0.065 (2)0.055 (2)0.0019 (15)0.0272 (17)0.0066 (17)
C110.0469 (19)0.060 (2)0.063 (2)−0.0075 (15)0.0351 (17)−0.0042 (16)

Geometric parameters (Å, °)

Cl1—C11.753 (3)C5—H50.9300
O1—C101.200 (4)C6—C71.430 (4)
N1—C11.293 (4)C6—H60.9300
N1—C91.370 (4)C7—C81.363 (4)
C1—C21.422 (4)C7—C111.502 (5)
C2—C31.369 (4)C8—C91.416 (4)
C2—C101.473 (4)C8—H80.9300
C3—C41.400 (4)C10—H100.9300
C3—H30.9300C11—H11A0.9600
C4—C51.417 (4)C11—H11B0.9600
C4—C91.424 (4)C11—H11C0.9600
C5—C61.359 (4)
C1—N1—C9117.7 (3)C8—C7—C6118.6 (3)
N1—C1—C2125.7 (3)C8—C7—C11121.3 (3)
N1—C1—Cl1115.7 (2)C6—C7—C11120.1 (3)
C2—C1—Cl1118.5 (2)C7—C8—C9121.5 (3)
C3—C2—C1116.3 (3)C7—C8—H8119.3
C3—C2—C10120.2 (3)C9—C8—H8119.3
C1—C2—C10123.5 (3)N1—C9—C8118.8 (3)
C2—C3—C4121.2 (3)N1—C9—C4121.9 (3)
C2—C3—H3119.4C8—C9—C4119.3 (3)
C4—C3—H3119.4O1—C10—C2123.8 (3)
C3—C4—C5124.3 (3)O1—C10—H10118.1
C3—C4—C9117.2 (3)C2—C10—H10118.1
C5—C4—C9118.5 (3)C7—C11—H11A109.5
C6—C5—C4120.5 (3)C7—C11—H11B109.5
C6—C5—H5119.7H11A—C11—H11B109.5
C4—C5—H5119.7C7—C11—H11C109.5
C5—C6—C7121.5 (3)H11A—C11—H11C109.5
C5—C6—H6119.3H11B—C11—H11C109.5
C7—C6—H6119.3
C9—N1—C1—C2−0.7 (5)C5—C6—C7—C11179.9 (3)
C9—N1—C1—Cl1−179.8 (2)C6—C7—C8—C9−0.5 (4)
N1—C1—C2—C31.3 (5)C11—C7—C8—C9−180.0 (3)
Cl1—C1—C2—C3−179.6 (2)C1—N1—C9—C8179.6 (3)
N1—C1—C2—C10−178.7 (3)C1—N1—C9—C4−0.4 (4)
Cl1—C1—C2—C100.5 (4)C7—C8—C9—N1−179.8 (3)
C1—C2—C3—C4−0.8 (4)C7—C8—C9—C40.2 (4)
C10—C2—C3—C4179.2 (3)C3—C4—C9—N10.8 (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—C6179.1 (3)C5—C4—C9—C80.1 (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—O1170.4 (3)
C5—C6—C7—C80.5 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2629).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2004). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Meth-Cohn, O. (1993). Heterocycles, 35, 539–557.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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