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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2709.
Published online 2009 October 10. doi:  10.1107/S1600536809040860
PMCID: PMC2971046

2-Chloro-7,8-dimethyl­quinoline-3-carbaldehyde

Abstract

All the non-H atoms of the title compound, C12H10ClNO, lie on a crystallographic mirror plane orientated perpendicular to the crystallographic b axis.

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-o2709-scheme1.jpg

Experimental

Crystal data

  • C12H10ClNO
  • M r = 219.66
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2709-efi1.jpg
  • a = 20.4542 (13) Å
  • b = 6.7393 (4) Å
  • c = 7.5675 (4) Å
  • V = 1043.16 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 290 K
  • 0.28 × 0.21 × 0.17 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.912, T max = 0.945
  • 7145 measured reflections
  • 1299 independent reflections
  • 1078 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.115
  • S = 1.07
  • 1299 reflections
  • 94 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 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/S1600536809040860/bt5086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040860/bt5086Isup2.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-(2,3-dimethylphenyl)acetamide (1.63 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 C12H10ClNO at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C12H10ClNOF(000) = 456
Mr = 219.66Dx = 1.399 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 753 reflections
a = 20.4542 (13) Åθ = 2.0–24.4°
b = 6.7393 (4) ŵ = 0.34 mm1
c = 7.5675 (4) ÅT = 290 K
V = 1043.16 (11) Å3Block, colorless
Z = 40.28 × 0.21 × 0.17 mm

Data collection

Bruker SMART area-detector diffractometer1299 independent reflections
Radiation source: fine-focus sealed tube1078 reflections with I > 2σ(I)
graphiteRint = 0.022
[var phi] and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −25→26
Tmin = 0.912, Tmax = 0.945k = −8→4
7145 measured reflectionsl = −9→9

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) = 0.115w = 1/[σ2(Fo2) + (0.0706P)2 + 0.1712P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
1299 reflectionsΔρmax = 0.29 e Å3
94 parametersΔρmin = −0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (2)

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

xyzUiso*/UeqOcc. (<1)
Cl10.59400 (3)0.25000.07517 (7)0.0568 (2)
N10.48555 (8)0.25000.24995 (19)0.0363 (4)
O10.68317 (9)0.25000.5872 (3)0.0672 (5)
C10.54815 (9)0.25000.2711 (2)0.0369 (4)
C20.58228 (10)0.25000.4343 (3)0.0385 (4)
C30.54382 (10)0.25000.5832 (3)0.0382 (4)
H30.56350.25000.69390.046*
C40.47569 (10)0.25000.5712 (2)0.0347 (4)
C50.43407 (11)0.25000.7208 (3)0.0428 (5)
H50.45170.25000.83410.051*
C60.36779 (11)0.25000.6971 (3)0.0461 (5)
H60.34080.25000.79600.055*
C70.33908 (10)0.25000.5279 (3)0.0411 (5)
C80.37829 (9)0.25000.3777 (3)0.0361 (4)
C90.44701 (9)0.25000.3993 (2)0.0322 (4)
C100.65428 (11)0.25000.4503 (3)0.0531 (6)
H100.67870.25000.34670.064*
C110.26571 (11)0.25000.5126 (4)0.0583 (6)
H11A0.24680.27660.62620.087*0.50
H11B0.25120.12270.47130.087*0.50
H11C0.25240.35070.43050.087*0.50
C120.34939 (11)0.25000.1950 (3)0.0532 (6)
H12A0.37940.18820.11440.080*0.50
H12B0.34140.38420.15830.080*0.50
H12C0.30900.17760.19570.080*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0424 (3)0.0881 (5)0.0400 (3)0.0000.0087 (2)0.000
N10.0355 (8)0.0437 (8)0.0298 (7)0.000−0.0008 (6)0.000
O10.0480 (10)0.0820 (12)0.0716 (12)0.000−0.0252 (9)0.000
C10.0356 (10)0.0415 (9)0.0336 (9)0.0000.0018 (7)0.000
C20.0344 (10)0.0387 (9)0.0423 (11)0.000−0.0058 (7)0.000
C30.0417 (11)0.0389 (9)0.0341 (9)0.000−0.0097 (7)0.000
C40.0411 (10)0.0344 (9)0.0286 (9)0.000−0.0022 (7)0.000
C50.0497 (12)0.0513 (11)0.0275 (9)0.0000.0003 (8)0.000
C60.0483 (12)0.0556 (11)0.0343 (10)0.0000.0078 (9)0.000
C70.0357 (10)0.0453 (10)0.0423 (10)0.0000.0028 (8)0.000
C80.0351 (10)0.0386 (9)0.0346 (9)0.000−0.0021 (7)0.000
C90.0361 (9)0.0324 (8)0.0281 (8)0.000−0.0014 (7)0.000
C100.0375 (11)0.0623 (13)0.0595 (14)0.000−0.0064 (10)0.000
C110.0367 (11)0.0783 (16)0.0600 (15)0.0000.0085 (10)0.000
C120.0395 (11)0.0814 (15)0.0387 (11)0.000−0.0054 (9)0.000

Geometric parameters (Å, °)

Cl1—C11.7545 (19)C6—C71.409 (3)
N1—C11.290 (2)C6—H60.9300
N1—C91.378 (2)C7—C81.391 (3)
O1—C101.192 (3)C7—C111.505 (3)
C1—C21.419 (3)C8—C91.415 (3)
C2—C31.374 (3)C8—C121.504 (3)
C2—C101.478 (3)C10—H100.9300
C3—C41.396 (3)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—C51.416 (3)C11—H11C0.9600
C4—C91.427 (2)C12—H12A0.9600
C5—C61.367 (3)C12—H12B0.9600
C5—H50.9300C12—H12C0.9600
C1—N1—C9117.76 (16)C7—C8—C9118.58 (17)
N1—C1—C2126.61 (17)C7—C8—C12121.64 (18)
N1—C1—Cl1115.19 (14)C9—C8—C12119.79 (17)
C2—C1—Cl1118.20 (15)N1—C9—C8118.25 (15)
C3—C2—C1115.60 (18)N1—C9—C4120.82 (16)
C3—C2—C10120.21 (18)C8—C9—C4120.92 (16)
C1—C2—C10124.20 (19)O1—C10—C2124.4 (2)
C2—C3—C4121.19 (17)O1—C10—H10117.8
C2—C3—H3119.4C2—C10—H10117.8
C4—C3—H3119.4C7—C11—H11A109.5
C3—C4—C5123.21 (17)C7—C11—H11B109.5
C3—C4—C9118.02 (16)H11A—C11—H11B109.5
C5—C4—C9118.77 (18)C7—C11—H11C109.5
C6—C5—C4119.43 (18)H11A—C11—H11C109.5
C6—C5—H5120.3H11B—C11—H11C109.5
C4—C5—H5120.3C8—C12—H12A109.5
C5—C6—C7122.15 (18)C8—C12—H12B109.5
C5—C6—H6118.9H12A—C12—H12B109.5
C7—C6—H6118.9C8—C12—H12C109.5
C8—C7—C6120.15 (19)H12A—C12—H12C109.5
C8—C7—C11120.8 (2)H12B—C12—H12C109.5
C6—C7—C11119.0 (2)
C9—N1—C1—C20.0C11—C7—C8—C9180.0
C9—N1—C1—Cl1180.0C6—C7—C8—C12180.0
N1—C1—C2—C30.0C11—C7—C8—C120.0
Cl1—C1—C2—C3180.0C1—N1—C9—C8180.0
N1—C1—C2—C10180.0C1—N1—C9—C40.0
Cl1—C1—C2—C100.0C7—C8—C9—N1180.0
C1—C2—C3—C40.0C12—C8—C9—N10.0
C10—C2—C3—C4180.0C7—C8—C9—C40.0
C2—C3—C4—C5180.0C12—C8—C9—C4180.0
C2—C3—C4—C90.0C3—C4—C9—N10.0
C3—C4—C5—C6180.0C5—C4—C9—N1180.0
C9—C4—C5—C60.0C3—C4—C9—C8180.0
C4—C5—C6—C70.0C5—C4—C9—C80.0
C5—C6—C7—C80.0C3—C2—C10—O10.0
C5—C6—C7—C11180.0C1—C2—C10—O1180.0
C6—C7—C8—C90.0

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5086).

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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