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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2722.
Published online 2009 October 13. doi:  10.1107/S1600536809040859
PMCID: PMC2971088

2-Chloro-8-methyl­quinoline-3-carbaldehyde

Abstract

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

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Object name is e-65-o2722-scheme1.jpg

Experimental

Crystal data

  • C11H8ClNO
  • M r = 205.63
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2722-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 838 Friedel pairs
  • Flack parameter: 0.2 (2)

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/S1600536809040859/bt5085sup1.cif

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

The Vilsmeier-Haack reagent prepared from phosphorus oxytrichloride (6.5 ml, 70 mmol) and N,N-dimethylformamide (2.3 ml, 30 mmol) at 273 K was added N-(2-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).

The crystal had two domains related by a translation of (1/2, 0, 0) so that all reflections with h = 2n are affected. A scale factor was added for all reflections with h = 2n. The hkl file had a scale factor of 1 for h = 2n + 1 and a scale factor of 2 for the h = 2n reflections.

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 = 1.437 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 867 reflections
a = 6.8576 (5) Åθ = 2.0–24.4°
b = 7.4936 (6) ŵ = 0.36 mm1
c = 18.5003 (14) ÅT = 290 K
V = 950.70 (13) Å3Block, colorless
Z = 40.26 × 0.22 × 0.17 mm

Data collection

Bruker SMART area-detector diffractometer2174 independent reflections
Radiation source: fine-focus sealed tube1734 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.912, Tmax = 0.941k = −9→9
8224 measured reflectionsl = −22→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.136w = 1/[σ2(Fo2) + (0.0861P)2 + 0.0263P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2174 reflectionsΔρmax = 0.25 e Å3
129 parametersΔρmin = −0.32 e Å3
0 restraintsAbsolute structure: Flack (1983), 838 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.2 (2)

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

xyzUiso*/Ueq
Cl10.87010 (13)1.14505 (9)0.37890 (4)0.0579 (3)
O10.8672 (5)0.6106 (3)0.29577 (10)0.0763 (6)
N10.8717 (4)0.9871 (2)0.50346 (10)0.0366 (4)
C10.8734 (5)0.9563 (3)0.43459 (13)0.0368 (5)
C20.8754 (5)0.7858 (3)0.40176 (11)0.0398 (5)
C30.8734 (5)0.6423 (4)0.44734 (12)0.0389 (5)
H30.87410.52760.42810.047*
C40.8705 (4)0.6651 (3)0.52293 (10)0.0344 (5)
C50.8691 (5)0.5212 (3)0.57186 (14)0.0443 (6)
H50.87070.40450.55470.053*
C60.8654 (6)0.5531 (3)0.64410 (13)0.0468 (6)
H60.86330.45850.67660.056*
C70.8648 (5)0.7301 (4)0.66955 (13)0.0443 (6)
H70.86140.74910.71920.053*
C80.8690 (4)0.8754 (3)0.62492 (11)0.0372 (5)
C90.8702 (4)0.8426 (3)0.54918 (11)0.0327 (4)
C100.8840 (6)0.7545 (5)0.32246 (14)0.0551 (7)
H100.90340.85210.29220.066*
C110.8698 (7)1.0624 (3)0.65349 (14)0.0547 (7)
H11A0.87791.05980.70530.082*
H11B0.75191.12180.63920.082*
H11C0.98011.12550.63430.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0687 (4)0.0591 (4)0.0459 (4)0.0008 (5)0.0006 (4)0.0218 (3)
O10.0887 (16)0.1007 (17)0.0394 (10)−0.008 (2)−0.0031 (13)−0.0254 (11)
N10.0371 (10)0.0403 (10)0.0324 (10)−0.0007 (12)0.0005 (12)0.0028 (7)
C10.0327 (11)0.0459 (13)0.0318 (12)0.0001 (17)−0.0007 (16)0.0062 (10)
C20.0347 (11)0.0576 (14)0.0272 (10)−0.0003 (15)−0.0008 (12)−0.0019 (10)
C30.0393 (11)0.0427 (11)0.0348 (12)−0.002 (2)−0.0005 (14)−0.0084 (10)
C40.0323 (10)0.0410 (11)0.0300 (10)−0.0007 (15)0.0005 (11)−0.0004 (8)
C50.0509 (14)0.0398 (12)0.0422 (14)0.0026 (19)0.0008 (19)0.0040 (10)
C60.0509 (14)0.0519 (14)0.0375 (12)0.0021 (17)0.0007 (16)0.0120 (10)
C70.0457 (14)0.0596 (15)0.0276 (11)0.0043 (19)−0.0022 (15)0.0020 (11)
C80.0344 (10)0.0461 (12)0.0310 (11)0.0029 (12)−0.0009 (13)−0.0014 (9)
C90.0292 (10)0.0407 (11)0.0280 (10)−0.0001 (16)0.0004 (12)0.0002 (9)
C100.0538 (17)0.084 (2)0.0278 (12)0.000 (2)−0.0010 (17)−0.0032 (13)
C110.0716 (17)0.0543 (15)0.0384 (13)0.003 (2)−0.0005 (19)−0.0128 (11)

Geometric parameters (Å, °)

Cl1—C11.750 (2)C5—H50.9300
O1—C101.191 (4)C6—C71.407 (4)
N1—C11.295 (3)C6—H60.9300
N1—C91.374 (3)C7—C81.367 (3)
C1—C21.415 (3)C7—H70.9300
C2—C31.367 (3)C8—C91.423 (3)
C2—C101.487 (3)C8—C111.498 (3)
C3—C41.409 (3)C10—H100.9300
C3—H30.9300C11—H11A0.9600
C4—C51.408 (3)C11—H11B0.9600
C4—C91.416 (3)C11—H11C0.9600
C5—C61.358 (4)
C1—N1—C9117.73 (18)C8—C7—C6123.3 (2)
N1—C1—C2125.68 (19)C8—C7—H7118.4
N1—C1—Cl1115.80 (18)C6—C7—H7118.4
C2—C1—Cl1118.52 (18)C7—C8—C9117.2 (2)
C3—C2—C1116.47 (19)C7—C8—C11122.2 (2)
C3—C2—C10119.0 (2)C9—C8—C11120.6 (2)
C1—C2—C10124.5 (2)N1—C9—C4121.95 (19)
C2—C3—C4121.1 (2)N1—C9—C8118.06 (19)
C2—C3—H3119.4C4—C9—C8119.99 (19)
C4—C3—H3119.4O1—C10—C2123.2 (3)
C5—C4—C3123.0 (2)O1—C10—H10118.4
C5—C4—C9119.9 (2)C2—C10—H10118.4
C3—C4—C9117.0 (2)C8—C11—H11A109.5
C6—C5—C4119.9 (2)C8—C11—H11B109.5
C6—C5—H5120.1H11A—C11—H11B109.5
C4—C5—H5120.1C8—C11—H11C109.5
C5—C6—C7119.7 (2)H11A—C11—H11C109.5
C5—C6—H6120.2H11B—C11—H11C109.5
C7—C6—H6120.2
C9—N1—C1—C2−0.5 (5)C6—C7—C8—C91.3 (5)
C9—N1—C1—Cl1178.7 (2)C6—C7—C8—C11−179.5 (4)
N1—C1—C2—C30.6 (5)C1—N1—C9—C40.0 (4)
Cl1—C1—C2—C3−178.6 (3)C1—N1—C9—C8179.8 (3)
N1—C1—C2—C10−177.9 (3)C5—C4—C9—N1179.9 (3)
Cl1—C1—C2—C102.9 (5)C3—C4—C9—N10.3 (5)
C1—C2—C3—C4−0.3 (5)C5—C4—C9—C80.2 (4)
C10—C2—C3—C4178.3 (3)C3—C4—C9—C8−179.4 (2)
C2—C3—C4—C5−179.8 (3)C7—C8—C9—N1179.1 (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—C60.7 (5)C11—C8—C9—C4179.6 (3)
C4—C5—C6—C7−0.6 (6)C3—C2—C10—O18.8 (7)
C5—C6—C7—C8−0.4 (6)C1—C2—C10—O1−172.8 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5085).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2004). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • 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.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography