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Acta Cryst. (2009). E65, o2986    [ doi:10.1107/S160053680904536X ]

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

R. Subashini, F. N. Khan, S. Mittal, V. R. Hathwar and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C19H16ClNO2 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
Ethyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate top
Crystal data top
C19H16ClNO2Z = 2
Mr = 325.78F(000) = 340
Triclinic, P1Dx = 1.310 Mg m−3
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 mm−1
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 top
Bruker SMART CCD area-detector
diffractometer		3775 independent reflections
Radiation source: fine-focus sealed tube2854 reflections with I > 2σ(I)
graphiteRint = 0.025
φ 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 top
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 = 1.04 w = 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 Å−3
1 restraintΔρmin = −0.38 e Å−3
Crystal data top
C19H16ClNO2γ = 94.860 (2)°
Mr = 325.78V = 825.91 (4) Å3
Triclinic, P1Z = 2
a = 8.3622 (3) ÅMo Kα radiation
b = 10.1971 (3) ŵ = 0.24 mm−1
c = 10.7052 (3) ÅT = 290 K
α = 110.440 (2)°0.24 × 0.18 × 0.13 mm
β = 101.588 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3775 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2854 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.970Rint = 0.025
15008 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.147Δρmax = 0.33 e Å−3
S = 1.04Δρmin = −0.38 e Å−3
3775 reflectionsAbsolute structure: ?
210 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
Acknowledgements top

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.

references
References top

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.

Subashini, R., Hathwar, V. R., Manivel, P., Prabakaran, K. & Khan, F. N. (2009). Acta Cryst. E65, o370.

Westrip, S. P. (2009). publCIF. In preparation.