organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 27 October 2009; accepted 29 October 2009; online 4 November 2009)

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[Baumer, V. N., Shishkin, O. V., Ukrainets, I. V., Taran, S. G. & Amin, J. N. (2001). Acta Cryst. E57, o254-o255.]); Subashini et al. (2009[Subashini, R., Hathwar, V. R., Manivel, P., Prabakaran, K. & Khan, F. N. (2009). Acta Cryst. E65, o370.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16ClNO2

  • Mr = 325.78

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.945, Tmax = 0.970

  • 15008 measured reflections

  • 3775 independent reflections

  • 2854 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 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 top
Bruker SMART CCD area-detector
diffractometer
3775 independent reflections
Radiation source: fine-focus sealed tube2854 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.945, Tmax = 0.970k = 1213
15008 measured reflectionsl = 1310
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 Å3
1 restraintΔρmin = 0.38 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.147H-atom parameters constrained
S = 1.04Δρmax = 0.33 e Å3
3775 reflectionsΔρmin = 0.38 e Å3
210 parameters
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, º) 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—C40.8 (3)
C9—N1—C1—C10179.69 (16)C5—C4—C9—N1179.81 (15)
N1—C1—C2—C31.0 (3)C3—C4—C9—N10.2 (2)
C10—C1—C2—C3179.86 (16)C5—C4—C9—C80.2 (2)
N1—C1—C2—C11178.43 (16)C3—C4—C9—C8179.76 (15)
C10—C1—C2—C110.7 (3)C12—O1—C11—O26.4 (3)
C1—C2—C3—C41.1 (2)C12—O1—C11—C2174.03 (17)
C11—C2—C3—C4178.39 (15)C3—C2—C11—O2119.9 (2)
C1—C2—C3—C14177.78 (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—O1118.93 (17)
C14—C3—C4—C51.4 (2)C11—O1—C12—C13156.4 (2)
C2—C3—C4—C90.7 (2)C2—C3—C14—C19119.39 (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—C6178.74 (16)C4—C3—C14—C15120.12 (18)
C4—C5—C6—C72.3 (3)C19—C14—C15—C160.7 (3)
C4—C5—C6—Cl1177.19 (13)C3—C14—C15—C16178.83 (17)
C5—C6—C7—C81.3 (3)C14—C15—C16—C170.5 (3)
Cl1—C6—C7—C8178.20 (14)C15—C16—C17—C180.1 (3)
C6—C7—C8—C90.3 (3)C16—C17—C18—C190.2 (3)
C1—N1—C9—C8179.84 (16)C15—C14—C19—C180.5 (3)
C1—N1—C9—C40.1 (3)C3—C14—C19—C18178.57 (18)
C7—C8—C9—N1179.20 (17)C17—C18—C19—C140.0 (3)

Experimental details

Crystal data
Chemical formulaC19H16ClNO2
Mr325.78
Crystal system, space groupTriclinic, P1
Temperature (K)290
a, b, c (Å)8.3622 (3), 10.1971 (3), 10.7052 (3)
α, β, γ (°)110.440 (2), 101.588 (2), 94.860 (2)
V3)825.91 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.24 × 0.18 × 0.13
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.945, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
15008, 3775, 2854
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.147, 1.04
No. of reflections3775
No. of parameters210
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.38

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBaumer, V. N., Shishkin, O. V., Ukrainets, I. V., Taran, S. G. & Amin, J. N. (2001). Acta Cryst. E57, o254–o255.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSubashini, R., Hathwar, V. R., Manivel, P., Prabakaran, K. & Khan, F. N. (2009). Acta Cryst. E65, o370.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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