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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2723.
Published online 2009 October 13. doi:  10.1107/S1600536809040847
PMCID: PMC2971164

2-Chloro-6-methoxy­quinoline-3-carbaldehyde

Abstract

The quinoline fused-ring system of the title compound, C11H8ClNO2, is planar (r.m.s. deviation = 0.0095 Å); the formyl group is slightly bent out of this plane [C—C—C—O torsion angles = −2.4 (3) and 175.9 (2)°].

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-o2723-scheme1.jpg

Experimental

Crystal data

  • C11H8ClNO2
  • M r = 221.63
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2723-efi1.jpg
  • a = 7.7072 (9) Å
  • b = 14.3474 (13) Å
  • c = 9.3487 (10) Å
  • β = 109.415 (2)°
  • V = 974.98 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.37 mm−1
  • T = 290 K
  • 0.24 × 0.21 × 0.18 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.917, T max = 0.937
  • 6533 measured reflections
  • 2221 independent reflections
  • 1702 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.115
  • S = 1.03
  • 2221 reflections
  • 137 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.24 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/S1600536809040847/bt5087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040847/bt5087Isup2.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 to N-(4-anisyl)acetamide (1.65 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

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.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H8ClNO2F(000) = 456
Mr = 221.63Dx = 1.510 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 842 reflections
a = 7.7072 (9) Åθ = 2.0–24.7°
b = 14.3474 (13) ŵ = 0.37 mm1
c = 9.3487 (10) ÅT = 290 K
β = 109.415 (2)°Block, colorless
V = 974.98 (18) Å30.24 × 0.21 × 0.18 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer2221 independent reflections
Radiation source: fine-focus sealed tube1702 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→9
Tmin = 0.917, Tmax = 0.937k = −18→10
6533 measured reflectionsl = −12→12

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.068P)2 + 0.0419P] where P = (Fo2 + 2Fc2)/3
2221 reflections(Δ/σ)max = 0.001
137 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.24 e Å3

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

xyzUiso*/Ueq
Cl10.12213 (7)0.04921 (3)0.68956 (6)0.05816 (19)
O10.02629 (18)0.34429 (9)0.71932 (16)0.0563 (4)
O20.77125 (17)0.34949 (8)0.35759 (14)0.0480 (3)
N10.35512 (19)0.10458 (9)0.56310 (15)0.0399 (3)
C10.2333 (2)0.13533 (11)0.62026 (18)0.0386 (4)
C20.1913 (2)0.23022 (11)0.63341 (17)0.0365 (4)
C30.2892 (2)0.29435 (11)0.58240 (18)0.0366 (3)
H30.26590.35760.58850.044*
C40.4244 (2)0.26584 (10)0.52104 (16)0.0340 (3)
C50.5323 (2)0.32923 (11)0.47029 (18)0.0372 (4)
H50.51650.39310.47720.045*
C60.6601 (2)0.29554 (11)0.41088 (18)0.0375 (4)
C70.6864 (2)0.19874 (12)0.40126 (18)0.0406 (4)
H70.77330.17710.36000.049*
C80.5865 (2)0.13662 (11)0.45142 (18)0.0403 (4)
H80.60670.07300.44560.048*
C90.4520 (2)0.16836 (10)0.51239 (17)0.0342 (3)
C100.0534 (2)0.26334 (14)0.70166 (19)0.0446 (4)
H10−0.01530.21910.73220.054*
C110.7544 (3)0.44805 (12)0.3677 (2)0.0542 (5)
H11A0.83780.47830.32590.081*
H11B0.78350.46570.47210.081*
H11C0.63060.46650.31200.081*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0724 (4)0.0424 (3)0.0754 (4)−0.0099 (2)0.0455 (3)0.0028 (2)
O10.0572 (8)0.0491 (9)0.0728 (9)0.0069 (6)0.0355 (7)−0.0077 (6)
O20.0529 (7)0.0395 (7)0.0631 (8)−0.0047 (5)0.0347 (6)−0.0021 (5)
N10.0497 (8)0.0302 (8)0.0442 (7)0.0003 (6)0.0216 (6)−0.0002 (5)
C10.0455 (9)0.0337 (8)0.0394 (8)−0.0033 (7)0.0176 (7)0.0014 (6)
C20.0376 (8)0.0358 (8)0.0369 (8)0.0018 (6)0.0136 (7)−0.0017 (6)
C30.0423 (8)0.0285 (8)0.0411 (8)0.0043 (6)0.0168 (7)−0.0013 (6)
C40.0379 (8)0.0307 (8)0.0346 (8)0.0030 (6)0.0135 (6)0.0001 (6)
C50.0425 (8)0.0278 (8)0.0435 (8)0.0003 (6)0.0174 (7)−0.0018 (6)
C60.0393 (8)0.0353 (9)0.0397 (8)−0.0029 (6)0.0157 (7)−0.0001 (6)
C70.0437 (9)0.0385 (9)0.0442 (9)0.0056 (7)0.0209 (7)−0.0032 (7)
C80.0493 (9)0.0303 (9)0.0448 (9)0.0069 (7)0.0205 (7)−0.0013 (6)
C90.0406 (8)0.0278 (8)0.0350 (8)0.0019 (6)0.0138 (6)−0.0001 (6)
C100.0431 (9)0.0510 (11)0.0445 (9)0.0002 (8)0.0208 (7)−0.0024 (8)
C110.0605 (12)0.0381 (10)0.0751 (13)−0.0109 (8)0.0373 (10)−0.0039 (8)

Geometric parameters (Å, °)

Cl1—C11.7461 (16)C4—C91.421 (2)
O1—C101.201 (2)C5—C61.370 (2)
O2—C61.3654 (18)C5—H50.9300
O2—C111.426 (2)C6—C71.411 (2)
N1—C11.302 (2)C7—C81.359 (2)
N1—C91.362 (2)C7—H70.9300
C1—C21.414 (2)C8—C91.414 (2)
C2—C31.372 (2)C8—H80.9300
C2—C101.487 (2)C10—H100.9300
C3—C41.407 (2)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—C51.416 (2)C11—H11C0.9600
C6—O2—C11117.12 (13)C5—C6—C7120.73 (14)
C1—N1—C9117.96 (13)C8—C7—C6120.92 (14)
N1—C1—C2125.38 (14)C8—C7—H7119.5
N1—C1—Cl1114.97 (12)C6—C7—H7119.5
C2—C1—Cl1119.62 (12)C7—C8—C9120.21 (14)
C3—C2—C1116.56 (14)C7—C8—H8119.9
C3—C2—C10119.25 (15)C9—C8—H8119.9
C1—C2—C10124.17 (15)N1—C9—C8118.96 (14)
C2—C3—C4120.94 (14)N1—C9—C4122.11 (13)
C2—C3—H3119.5C8—C9—C4118.93 (14)
C4—C3—H3119.5O1—C10—C2123.35 (17)
C3—C4—C5123.14 (14)O1—C10—H10118.3
C3—C4—C9117.05 (14)C2—C10—H10118.3
C5—C4—C9119.81 (13)O2—C11—H11A109.5
C6—C5—C4119.40 (15)O2—C11—H11B109.5
C6—C5—H5120.3H11A—C11—H11B109.5
C4—C5—H5120.3O2—C11—H11C109.5
O2—C6—C5124.81 (15)H11A—C11—H11C109.5
O2—C6—C7114.46 (13)H11B—C11—H11C109.5
C9—N1—C1—C20.5 (2)C4—C5—C6—C7−0.6 (2)
C9—N1—C1—Cl1−177.49 (11)O2—C6—C7—C8179.38 (15)
N1—C1—C2—C3−0.6 (2)C5—C6—C7—C8−0.4 (2)
Cl1—C1—C2—C3177.35 (12)C6—C7—C8—C90.9 (2)
N1—C1—C2—C10−178.93 (16)C1—N1—C9—C8179.30 (15)
Cl1—C1—C2—C10−1.0 (2)C1—N1—C9—C40.3 (2)
C1—C2—C3—C4−0.2 (2)C7—C8—C9—N1−179.39 (15)
C10—C2—C3—C4178.22 (15)C7—C8—C9—C4−0.4 (2)
C2—C3—C4—C5−178.40 (15)C3—C4—C9—N1−1.1 (2)
C2—C3—C4—C91.0 (2)C5—C4—C9—N1178.34 (14)
C3—C4—C5—C6−179.51 (15)C3—C4—C9—C8179.98 (14)
C9—C4—C5—C61.1 (2)C5—C4—C9—C8−0.6 (2)
C11—O2—C6—C51.3 (2)C3—C2—C10—O1−2.4 (3)
C11—O2—C6—C7−178.48 (16)C1—C2—C10—O1175.9 (2)
C4—C5—C6—O2179.62 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5087).

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.

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