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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2986.
Published online 2009 November 4. doi:  10.1107/S160053680904536X
PMCID: PMC2971842

Ethyl 6-chloro-2-methyl-4-phenyl­quinoline-3-carboxyl­ate

Abstract

In the title compound, C19H16ClNO2, the quinoline ring system is planar (r.m.s. deviation = 0.008 Å). The phenyl group and the –CO2 fragment of the ester unit form dihedral angles of 60.0 (1) and 60.5 (1)°, respectively, with the quinoline ring system.

Related literature

For related structures, see: Baumer et al. (2001 [triangle]); Subashini et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2986-scheme1.jpg

Experimental

Crystal data

  • C19H16ClNO2
  • M r = 325.78
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2986-efi1.jpg
  • a = 8.3622 (3) Å
  • b = 10.1971 (3) Å
  • c = 10.7052 (3) Å
  • α = 110.440 (2)°
  • β = 101.588 (2)°
  • γ = 94.860 (2)°
  • V = 825.91 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 290 K
  • 0.24 × 0.18 × 0.13 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.945, T max = 0.970
  • 15008 measured reflections
  • 3775 independent reflections
  • 2854 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.147
  • S = 1.04
  • 3775 reflections
  • 210 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.38 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/S160053680904536X/ci2957sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904536X/ci2957Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Department of Science and Technology, India, for use of the diffraction facility set up under the IRHPA–DST programme at IISc. FNK thanks the DST for Fast Track Proposal funding. The authors also thank VIT University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-Amino-5-chlorobenzophenone (0.5 mmol), ethyl acetoacete (0.6 mmol, 1.2 equiv.) and iodine (1 mol %) in ethanol (1 ml) were stirred until the reaction was completed, as indicated by TLC. The reaction was quenched with water (15 ml). The organic product was extracted with ethyl acetate. Evaporation of the solvent gave a solid that was recrystallized from DMSO.

Refinement

C-bound H-atoms were placed in calculated positions (C-H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The C—C distance of the ethyl chain was tightly restrained to 1.500 (2) Å.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C19H16ClNO2 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C19H16ClNO2Z = 2
Mr = 325.78F(000) = 340
Triclinic, P1Dx = 1.310 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3622 (3) ÅCell parameters from 1153 reflections
b = 10.1971 (3) Åθ = 1.7–24.3°
c = 10.7052 (3) ŵ = 0.24 mm1
α = 110.440 (2)°T = 290 K
β = 101.588 (2)°Block, colourless
γ = 94.860 (2)°0.24 × 0.18 × 0.13 mm
V = 825.91 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3775 independent reflections
Radiation source: fine-focus sealed tube2854 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.945, Tmax = 0.970k = −12→13
15008 measured reflectionsl = −13→10

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0795P)2 + 0.1903P] where P = (Fo2 + 2Fc2)/3
3775 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.33 e Å3
1 restraintΔρmin = −0.38 e Å3

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

xyzUiso*/Ueq
Cl10.59565 (8)0.80991 (7)0.87661 (5)0.0711 (2)
N10.79494 (19)0.38099 (15)0.42954 (15)0.0465 (4)
O10.93549 (17)0.66715 (14)0.21071 (12)0.0523 (3)
O20.7449 (2)0.48238 (16)0.06011 (14)0.0690 (4)
C10.8150 (2)0.40465 (18)0.31986 (18)0.0433 (4)
C20.7883 (2)0.53430 (18)0.30236 (17)0.0407 (4)
C30.7375 (2)0.63972 (17)0.40021 (16)0.0387 (4)
C40.71546 (19)0.61552 (17)0.52007 (16)0.0387 (4)
C50.6644 (2)0.7151 (2)0.62823 (17)0.0451 (4)
H50.64120.80090.62300.054*
C60.6496 (2)0.6845 (2)0.74006 (17)0.0481 (4)
C70.6778 (2)0.5543 (2)0.74986 (18)0.0523 (5)
H70.66470.53520.82640.063*
C80.7245 (2)0.4561 (2)0.64596 (19)0.0508 (4)
H80.74280.36960.65200.061*
C90.7459 (2)0.48359 (18)0.52871 (17)0.0422 (4)
C100.8700 (3)0.2882 (2)0.2144 (2)0.0569 (5)
H10A0.89260.21450.24840.085*
H10B0.96850.32590.19680.085*
H10C0.78390.25000.13070.085*
C110.8176 (2)0.55604 (19)0.17664 (18)0.0465 (4)
C120.9625 (4)0.7067 (2)0.0980 (2)0.0733 (7)
H12A0.85790.69180.03210.088*
H12B1.03480.64870.05140.088*
C131.0409 (5)0.8617 (3)0.1562 (3)0.1064 (11)
H13A1.05690.89040.08260.160*
H13B1.14590.87490.21910.160*
H13C0.96960.91810.20380.160*
C140.7035 (2)0.77328 (18)0.38081 (17)0.0408 (4)
C150.5843 (2)0.7689 (2)0.26713 (19)0.0492 (4)
H150.52390.68230.20360.059*
C160.5557 (3)0.8940 (2)0.2488 (2)0.0609 (5)
H160.47550.89080.17330.073*
C170.6458 (3)1.0230 (2)0.3421 (3)0.0625 (6)
H170.62631.10640.32930.075*
C180.7641 (3)1.0279 (2)0.4538 (2)0.0629 (5)
H180.82511.11470.51650.075*
C190.7927 (2)0.9034 (2)0.4729 (2)0.0521 (4)
H190.87310.90750.54870.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0823 (4)0.0947 (5)0.0429 (3)0.0315 (3)0.0267 (2)0.0238 (3)
N10.0520 (9)0.0403 (8)0.0503 (8)0.0080 (6)0.0129 (7)0.0206 (7)
O10.0608 (8)0.0592 (8)0.0419 (6)0.0060 (6)0.0191 (6)0.0223 (6)
O20.0949 (12)0.0642 (9)0.0385 (7)0.0010 (8)0.0144 (7)0.0118 (6)
C10.0431 (9)0.0404 (9)0.0472 (9)0.0068 (7)0.0130 (7)0.0163 (7)
C20.0416 (9)0.0427 (9)0.0395 (8)0.0072 (7)0.0117 (7)0.0164 (7)
C30.0387 (8)0.0410 (9)0.0380 (8)0.0071 (7)0.0089 (6)0.0170 (7)
C40.0372 (8)0.0431 (9)0.0374 (8)0.0062 (7)0.0080 (6)0.0179 (7)
C50.0446 (9)0.0547 (10)0.0413 (8)0.0146 (8)0.0125 (7)0.0221 (8)
C60.0439 (9)0.0630 (11)0.0366 (8)0.0080 (8)0.0109 (7)0.0176 (8)
C70.0528 (10)0.0662 (12)0.0395 (9)−0.0035 (9)0.0069 (7)0.0274 (9)
C80.0581 (11)0.0494 (10)0.0470 (9)0.0005 (8)0.0069 (8)0.0260 (8)
C90.0418 (9)0.0440 (9)0.0422 (8)0.0033 (7)0.0077 (7)0.0201 (7)
C100.0645 (12)0.0455 (10)0.0657 (12)0.0169 (9)0.0276 (10)0.0186 (9)
C110.0557 (10)0.0464 (10)0.0422 (9)0.0155 (8)0.0176 (8)0.0177 (8)
C120.113 (2)0.0663 (14)0.0491 (11)0.0044 (13)0.0366 (12)0.0246 (10)
C130.165 (3)0.086 (2)0.0744 (17)−0.011 (2)0.0446 (19)0.0358 (15)
C140.0453 (9)0.0429 (9)0.0410 (8)0.0124 (7)0.0171 (7)0.0192 (7)
C150.0503 (10)0.0527 (10)0.0515 (10)0.0093 (8)0.0119 (8)0.0280 (8)
C160.0559 (11)0.0731 (14)0.0729 (13)0.0208 (10)0.0185 (10)0.0469 (12)
C170.0709 (13)0.0522 (12)0.0866 (15)0.0251 (10)0.0355 (12)0.0407 (11)
C180.0757 (14)0.0423 (10)0.0725 (13)0.0136 (10)0.0271 (11)0.0180 (10)
C190.0583 (11)0.0474 (10)0.0488 (10)0.0107 (8)0.0128 (8)0.0158 (8)

Geometric parameters (Å, °)

Cl1—C61.7414 (19)C10—H10A0.96
N1—C11.317 (2)C10—H10B0.96
N1—C91.364 (2)C10—H10C0.96
O1—C111.329 (2)C12—C131.513 (2)
O1—C121.450 (2)C12—H12A0.97
O2—C111.206 (2)C12—H12B0.97
C1—C21.428 (2)C13—H13A0.96
C1—C101.503 (3)C13—H13B0.96
C2—C31.380 (2)C13—H13C0.96
C2—C111.501 (2)C14—C191.383 (3)
C3—C41.432 (2)C14—C151.394 (2)
C3—C141.489 (2)C15—C161.389 (3)
C4—C51.416 (2)C15—H150.93
C4—C91.421 (2)C16—C171.381 (3)
C5—C61.364 (2)C16—H160.93
C5—H50.93C17—C181.373 (3)
C6—C71.404 (3)C17—H170.93
C7—C81.362 (3)C18—C191.387 (3)
C7—H70.93C18—H180.93
C8—C91.419 (2)C19—H190.93
C8—H80.93
C1—N1—C9118.67 (14)H10B—C10—H10C109.5
C11—O1—C12115.60 (15)O2—C11—O1124.32 (17)
N1—C1—C2122.09 (16)O2—C11—C2124.75 (18)
N1—C1—C10116.33 (15)O1—C11—C2110.93 (14)
C2—C1—C10121.57 (15)O1—C12—C13108.36 (17)
C3—C2—C1120.68 (15)O1—C12—H12A110.0
C3—C2—C11119.90 (15)C13—C12—H12A110.0
C1—C2—C11119.42 (15)O1—C12—H12B110.0
C2—C3—C4117.83 (14)C13—C12—H12B110.0
C2—C3—C14121.20 (14)H12A—C12—H12B108.4
C4—C3—C14120.96 (14)C12—C13—H13A109.5
C5—C4—C9119.10 (15)C12—C13—H13B109.5
C5—C4—C3123.49 (15)H13A—C13—H13B109.5
C9—C4—C3117.41 (15)C12—C13—H13C109.5
C6—C5—C4119.64 (16)H13A—C13—H13C109.5
C6—C5—H5120.2H13B—C13—H13C109.5
C4—C5—H5120.2C19—C14—C15118.78 (16)
C5—C6—C7122.02 (17)C19—C14—C3120.68 (15)
C5—C6—Cl1119.74 (15)C15—C14—C3120.52 (16)
C7—C6—Cl1118.23 (13)C16—C15—C14120.00 (18)
C8—C7—C6119.22 (16)C16—C15—H15120.0
C8—C7—H7120.4C14—C15—H15120.0
C6—C7—H7120.4C17—C16—C15120.37 (19)
C7—C8—C9121.19 (17)C17—C16—H16119.8
C7—C8—H8119.4C15—C16—H16119.8
C9—C8—H8119.4C18—C17—C16119.94 (18)
N1—C9—C8117.90 (15)C18—C17—H17120.0
N1—C9—C4123.31 (15)C16—C17—H17120.0
C8—C9—C4118.79 (16)C17—C18—C19119.9 (2)
C1—C10—H10A109.5C17—C18—H18120.0
C1—C10—H10B109.5C19—C18—H18120.0
H10A—C10—H10B109.5C14—C19—C18120.97 (19)
C1—C10—H10C109.5C14—C19—H19119.5
H10A—C10—H10C109.5C18—C19—H19119.5
C9—N1—C1—C20.5 (3)C7—C8—C9—C4−0.8 (3)
C9—N1—C1—C10179.69 (16)C5—C4—C9—N1179.81 (15)
N1—C1—C2—C3−1.0 (3)C3—C4—C9—N10.2 (2)
C10—C1—C2—C3179.86 (16)C5—C4—C9—C8−0.2 (2)
N1—C1—C2—C11178.43 (16)C3—C4—C9—C8−179.76 (15)
C10—C1—C2—C11−0.7 (3)C12—O1—C11—O26.4 (3)
C1—C2—C3—C41.1 (2)C12—O1—C11—C2−174.03 (17)
C11—C2—C3—C4−178.39 (15)C3—C2—C11—O2−119.9 (2)
C1—C2—C3—C14−177.78 (15)C1—C2—C11—O260.7 (3)
C11—C2—C3—C142.8 (2)C3—C2—C11—O160.5 (2)
C2—C3—C4—C5179.76 (15)C1—C2—C11—O1−118.93 (17)
C14—C3—C4—C5−1.4 (2)C11—O1—C12—C13156.4 (2)
C2—C3—C4—C9−0.7 (2)C2—C3—C14—C19−119.39 (19)
C14—C3—C4—C9178.17 (15)C4—C3—C14—C1961.8 (2)
C9—C4—C5—C61.7 (3)C2—C3—C14—C1558.7 (2)
C3—C4—C5—C6−178.74 (16)C4—C3—C14—C15−120.12 (18)
C4—C5—C6—C7−2.3 (3)C19—C14—C15—C16−0.7 (3)
C4—C5—C6—Cl1177.19 (13)C3—C14—C15—C16−178.83 (17)
C5—C6—C7—C81.3 (3)C14—C15—C16—C170.5 (3)
Cl1—C6—C7—C8−178.20 (14)C15—C16—C17—C18−0.1 (3)
C6—C7—C8—C90.3 (3)C16—C17—C18—C19−0.2 (3)
C1—N1—C9—C8179.84 (16)C15—C14—C19—C180.5 (3)
C1—N1—C9—C4−0.1 (3)C3—C14—C19—C18178.57 (18)
C7—C8—C9—N1179.20 (17)C17—C18—C19—C140.0 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2957).

References

  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Baumer, V. N., Shishkin, O. V., Ukrainets, I. V., Taran, S. G. & Amin, J. N. (2001). Acta Cryst. E57, o254–o255.
  • Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Subashini, R., Hathwar, V. R., Manivel, P., Prabakaran, K. & Khan, F. N. (2009). Acta Cryst. E65, o370. [PMC free article] [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

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