PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2710.
Published online 2009 October 10. doi:  10.1107/S1600536809040665
PMCID: PMC2971064

2-Chloro­quinoline-3-carbaldehyde

Abstract

The quinolinyl fused ring system of the title compound, C10H6ClNO, is planar (r.m.s. deviation = 0.018 Å); the formyl group is slightly bent out of the plane of the fused ring system [C—C—C—O torsion angle = 8.2 (3)°].

Related literature

For the synthesis of 2-chloro­quinoline-3-carbaldehyde by Vilsmeier–Haack cyclization, see: Ali et al. (2001 [triangle], 2002 [triangle]); Mogilaiah et al. (2002 [triangle]); Pawar et al. (1990 [triangle]); Srivastava & Singh (2005 [triangle]). For a review of the synthesis of quinolines by this reaction, see: Meth-Cohn (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2710-scheme1.jpg

Experimental

Crystal data

  • C10H6ClNO
  • M r = 191.61
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2710-efi1.jpg
  • a = 11.8784 (9) Å
  • b = 3.9235 (3) Å
  • c = 18.1375 (12) Å
  • β = 101.365 (4)°
  • V = 828.72 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 290 K
  • 0.24 × 0.18 × 0.14 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.908, T max = 0.945
  • 6886 measured reflections
  • 1889 independent reflections
  • 1626 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.145
  • S = 1.19
  • 1889 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.29 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/S1600536809040665/tk2549sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040665/tk2549Isup2.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-phenylacetamide (1.35 g, 10 mmol), 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 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C10H6ClNO at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H6ClNOF(000) = 392
Mr = 191.61Dx = 1.536 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 781 reflections
a = 11.8784 (9) Åθ = 2.1–24.3°
b = 3.9235 (3) ŵ = 0.41 mm1
c = 18.1375 (12) ÅT = 290 K
β = 101.365 (4)°Block, colorless
V = 828.72 (10) Å30.24 × 0.18 × 0.14 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer1889 independent reflections
Radiation source: fine-focus sealed tube1626 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.908, Tmax = 0.945k = −3→5
6886 measured reflectionsl = −23→23

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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.19w = 1/[σ2(Fo2) + (0.0923P)2 + 0.077P] where P = (Fo2 + 2Fc2)/3
1889 reflections(Δ/σ)max = 0.001
118 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.29 e Å3

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

xyzUiso*/Ueq
Cl10.24556 (4)0.22180 (12)0.67041 (2)0.0464 (2)
O10.51095 (11)0.8482 (4)0.61287 (8)0.0550 (4)
N10.15508 (12)0.2731 (3)0.52950 (9)0.0353 (3)
C10.24476 (14)0.3582 (4)0.57833 (9)0.0319 (4)
C20.34039 (13)0.5468 (4)0.56384 (9)0.0323 (4)
C30.33695 (13)0.6369 (4)0.49061 (9)0.0334 (4)
H30.39770.75850.47810.040*
C40.24263 (13)0.5477 (4)0.43407 (9)0.0324 (4)
C50.23434 (16)0.6341 (5)0.35765 (10)0.0419 (4)
H50.29440.74830.34240.050*
C60.13859 (17)0.5504 (5)0.30635 (10)0.0481 (5)
H60.13340.60770.25600.058*
C70.04727 (17)0.3774 (6)0.32911 (11)0.0493 (5)
H7−0.01800.32430.29350.059*
C80.05247 (16)0.2861 (5)0.40222 (12)0.0436 (4)
H8−0.00820.16990.41620.052*
C90.15087 (13)0.3697 (4)0.45629 (9)0.0325 (4)
C100.43810 (15)0.6537 (5)0.62315 (10)0.0407 (4)
H100.44320.56450.67120.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0587 (3)0.0522 (3)0.0308 (3)−0.00331 (19)0.0147 (2)0.00444 (16)
O10.0435 (8)0.0681 (10)0.0499 (8)−0.0161 (6)0.0004 (6)0.0003 (7)
N10.0363 (7)0.0355 (7)0.0355 (8)−0.0016 (5)0.0107 (6)−0.0029 (5)
C10.0381 (8)0.0310 (8)0.0283 (7)0.0020 (6)0.0107 (6)0.0004 (6)
C20.0335 (8)0.0312 (8)0.0321 (8)0.0024 (6)0.0062 (6)−0.0007 (6)
C30.0329 (8)0.0332 (8)0.0349 (8)−0.0001 (6)0.0089 (6)0.0018 (7)
C40.0362 (8)0.0317 (8)0.0299 (8)0.0056 (6)0.0077 (6)−0.0005 (6)
C50.0489 (10)0.0444 (9)0.0332 (9)0.0076 (8)0.0101 (7)0.0039 (7)
C60.0591 (11)0.0544 (11)0.0289 (8)0.0166 (9)0.0039 (8)−0.0021 (8)
C70.0454 (10)0.0560 (11)0.0407 (10)0.0110 (8)−0.0058 (8)−0.0141 (9)
C80.0356 (9)0.0467 (10)0.0466 (11)0.0012 (7)0.0037 (8)−0.0120 (8)
C90.0331 (8)0.0320 (8)0.0329 (8)0.0032 (6)0.0072 (6)−0.0052 (6)
C100.0414 (9)0.0459 (10)0.0332 (9)−0.0003 (7)0.0031 (7)0.0017 (7)

Geometric parameters (Å, °)

Cl1—C11.7519 (16)C4—C91.418 (2)
O1—C101.196 (2)C5—C61.360 (3)
N1—C11.288 (2)C5—H50.9300
N1—C91.372 (2)C6—C71.409 (3)
C1—C21.423 (2)C6—H60.9300
C2—C31.367 (2)C7—C81.363 (3)
C2—C101.479 (2)C7—H70.9300
C3—C41.406 (2)C8—C91.409 (2)
C3—H30.9300C8—H80.9300
C4—C51.411 (2)C10—H100.9300
C1—N1—C9117.48 (14)C5—C6—C7120.28 (17)
N1—C1—C2126.15 (15)C5—C6—H6119.9
N1—C1—Cl1115.14 (12)C7—C6—H6119.9
C2—C1—Cl1118.71 (12)C8—C7—C6121.46 (17)
C3—C2—C1116.22 (14)C8—C7—H7119.3
C3—C2—C10120.14 (15)C6—C7—H7119.3
C1—C2—C10123.62 (15)C7—C8—C9119.23 (18)
C2—C3—C4120.74 (14)C7—C8—H8120.4
C2—C3—H3119.6C9—C8—H8120.4
C4—C3—H3119.6N1—C9—C8118.45 (15)
C3—C4—C5123.22 (15)N1—C9—C4121.83 (14)
C3—C4—C9117.52 (14)C8—C9—C4119.71 (16)
C5—C4—C9119.24 (15)O1—C10—C2123.76 (16)
C6—C5—C4120.07 (17)O1—C10—H10118.1
C6—C5—H5120.0C2—C10—H10118.1
C4—C5—H5120.0
C9—N1—C1—C20.6 (2)C5—C6—C7—C8−0.8 (3)
C9—N1—C1—Cl1−179.13 (11)C6—C7—C8—C90.7 (3)
N1—C1—C2—C3−1.8 (2)C1—N1—C9—C8−178.61 (14)
Cl1—C1—C2—C3177.90 (11)C1—N1—C9—C41.8 (2)
N1—C1—C2—C10176.39 (16)C7—C8—C9—N1−179.43 (15)
Cl1—C1—C2—C10−3.9 (2)C7—C8—C9—C40.1 (3)
C1—C2—C3—C40.6 (2)C3—C4—C9—N1−2.9 (2)
C10—C2—C3—C4−177.67 (14)C5—C4—C9—N1178.69 (15)
C2—C3—C4—C5179.92 (15)C3—C4—C9—C8177.57 (15)
C2—C3—C4—C91.5 (2)C5—C4—C9—C8−0.9 (2)
C3—C4—C5—C6−177.55 (16)C3—C2—C10—O18.2 (3)
C9—C4—C5—C60.8 (3)C1—C2—C10—O1−170.0 (2)
C4—C5—C6—C70.0 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2549).

References

  • Ali, M. M., Sana, S., Tasneem, Rajanna, K. C. & Saiprakash, P. K. (2002). Synth. Commun.32, 1351–1356.
  • Ali, M. M., Tasneem, Rajanna, K. C. & Prakash, P. K. S. (2001). Synlett, pp. 251–253.
  • 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.
  • Mogilaiah, K., Reddy, N. V. & Rao, R. B. (2002). Indian J. Heterocycl. Chem.11, 253–254. .
  • Pawar, R. A., Bajare, P. B. & Mundade, S. B. (1990). J. Indian Chem. Soc.67, 685-686.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Srivastava, A. & Singh, R. M. (2005). Indian J. Chem. Sect. B, 44, 1868–1875.
  • 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