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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2982.
Published online 2009 November 4. doi:  10.1107/S1600536809045334
PMCID: PMC2971778

Ethyl 2,6-dichloro-4-phenyl­quinoline-3-carboxyl­ate

Abstract

In the title compound, C18H13Cl2NO2, the quinoline ring system is almost planar (r.m.s. deviation 0.009 Å), and the phenyl and carboxyl­ate planes are twisted away from it by 59.2 (1) and 65.9 (2)°, respectively.

Related literature

The title compound is a 6-chloro analouge of ethyl 2-chloro-4-phenyl­quinoline-3-carboxyl­ate, which has been examined for endothelin binding affinity; for details, see: Anzini et al. (1991 [triangle], 1992 [triangle], 2001 [triangle]); Cappelli et al. (2008 [triangle]); Pittala et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2982-scheme1.jpg

Experimental

Crystal data

  • C18H13Cl2NO2
  • M r = 346.19
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2982-efi1.jpg
  • a = 8.3553 (3) Å
  • b = 10.1861 (5) Å
  • c = 10.6731 (6) Å
  • α = 110.537 (5)°
  • β = 101.421 (4)°
  • γ = 95.980 (4)°
  • V = 818.73 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 295 K
  • 0.34 × 0.26 × 0.25 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.875, T max = 0.906
  • 18102 measured reflections
  • 3700 independent reflections
  • 2537 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.144
  • S = 1.02
  • 3700 reflections
  • 209 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.36 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/S1600536809045334/ci2954sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045334/ci2954Isup2.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

An excess of phosphorus oxychloride (0.9 ml, 10 mmol) and 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate (0.33 g, 1 mmol) were heated for 1 h. The mixture was then added to crushed ice. The solid that formed was collected and recrystallized from methanol.

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 1.2–1.5Ueq(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 C18H13Cl2NO2 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H13Cl2NO2Z = 2
Mr = 346.19F(000) = 356
Triclinic, P1Dx = 1.404 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3553 (3) ÅCell parameters from 1235 reflections
b = 10.1861 (5) Åθ = 1.7–21.3°
c = 10.6731 (6) ŵ = 0.40 mm1
α = 110.537 (5)°T = 295 K
β = 101.421 (4)°Block, colourless
γ = 95.980 (4)°0.34 × 0.26 × 0.25 mm
V = 818.73 (7) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3700 independent reflections
Radiation source: fine-focus sealed tube2537 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.875, Tmax = 0.906k = −13→12
18102 measured reflectionsl = −13→13

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.07P)2 + 0.2927P] where P = (Fo2 + 2Fc2)/3
3700 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = −0.35 e Å3

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

xyzUiso*/Ueq
Cl10.38082 (9)0.27696 (7)0.20007 (7)0.0656 (2)
Cl20.09541 (10)0.80809 (9)0.87358 (6)0.0737 (3)
N10.2968 (2)0.38235 (19)0.42803 (19)0.0464 (4)
O10.4425 (2)0.66274 (18)0.20689 (15)0.0522 (4)
O20.2357 (2)0.48698 (19)0.05569 (16)0.0651 (5)
C10.3141 (3)0.4086 (2)0.3210 (2)0.0432 (5)
C20.2874 (3)0.5342 (2)0.2978 (2)0.0394 (5)
C30.2357 (3)0.6384 (2)0.3963 (2)0.0372 (5)
C40.2145 (3)0.6144 (2)0.5166 (2)0.0381 (5)
C50.1637 (3)0.7137 (2)0.6250 (2)0.0436 (5)
H50.13970.79890.61950.052*
C60.1503 (3)0.6832 (3)0.7373 (2)0.0479 (5)
C70.1808 (3)0.5550 (3)0.7485 (2)0.0534 (6)
H70.16950.53680.82610.064*
C80.2271 (3)0.4575 (3)0.6448 (2)0.0509 (6)
H80.24590.37140.65120.061*
C90.2472 (3)0.4845 (2)0.5278 (2)0.0421 (5)
C100.2017 (3)0.7710 (2)0.3758 (2)0.0399 (5)
C110.0839 (3)0.7647 (3)0.2608 (2)0.0479 (5)
H110.02350.67690.19630.057*
C120.0565 (3)0.8896 (3)0.2421 (3)0.0607 (7)
H12−0.02350.88550.16590.073*
C130.1478 (4)1.0192 (3)0.3363 (3)0.0650 (7)
H130.13011.10240.32270.078*
C140.2633 (4)1.0268 (3)0.4490 (3)0.0641 (7)
H140.32401.11510.51230.077*
C150.2910 (3)0.9030 (2)0.4697 (2)0.0506 (6)
H150.37010.90880.54720.061*
C160.3163 (3)0.5558 (2)0.1716 (2)0.0443 (5)
C170.4740 (4)0.7060 (3)0.0971 (3)0.0749 (9)
H17A0.37130.68520.02670.090*
H17B0.55220.65330.05470.090*
C180.5432 (6)0.8615 (3)0.1550 (4)0.1137 (15)
H18A0.55720.89160.08150.170*
H18B0.64900.88060.21950.170*
H18C0.46830.91290.20160.170*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0792 (5)0.0546 (4)0.0702 (4)0.0224 (3)0.0354 (4)0.0209 (3)
Cl20.0878 (5)0.1001 (6)0.0420 (3)0.0331 (4)0.0288 (3)0.0264 (3)
N10.0512 (11)0.0404 (10)0.0507 (11)0.0064 (8)0.0109 (9)0.0226 (8)
O10.0616 (10)0.0593 (10)0.0393 (8)0.0039 (8)0.0178 (7)0.0223 (7)
O20.0851 (13)0.0648 (11)0.0359 (9)0.0015 (10)0.0110 (9)0.0135 (8)
C10.0424 (12)0.0393 (11)0.0472 (12)0.0081 (9)0.0125 (9)0.0148 (9)
C20.0419 (12)0.0405 (11)0.0377 (10)0.0071 (9)0.0108 (9)0.0170 (8)
C30.0372 (11)0.0390 (11)0.0361 (10)0.0051 (9)0.0072 (8)0.0167 (8)
C40.0366 (11)0.0431 (11)0.0348 (10)0.0053 (9)0.0062 (8)0.0171 (8)
C50.0448 (12)0.0528 (13)0.0375 (11)0.0119 (10)0.0111 (9)0.0210 (9)
C60.0428 (12)0.0664 (15)0.0338 (11)0.0074 (11)0.0098 (9)0.0189 (10)
C70.0545 (14)0.0694 (16)0.0382 (12)−0.0051 (12)0.0054 (10)0.0309 (11)
C80.0577 (15)0.0511 (13)0.0479 (13)0.0015 (11)0.0063 (11)0.0298 (11)
C90.0406 (12)0.0441 (11)0.0423 (11)0.0017 (9)0.0065 (9)0.0212 (9)
C100.0461 (12)0.0414 (11)0.0398 (11)0.0128 (9)0.0176 (9)0.0193 (9)
C110.0505 (14)0.0519 (13)0.0484 (12)0.0093 (10)0.0132 (10)0.0272 (10)
C120.0577 (16)0.0768 (19)0.0698 (16)0.0248 (14)0.0205 (13)0.0486 (15)
C130.0747 (19)0.0517 (15)0.091 (2)0.0255 (14)0.0355 (16)0.0417 (15)
C140.0769 (19)0.0414 (13)0.0749 (18)0.0124 (13)0.0264 (15)0.0191 (12)
C150.0595 (15)0.0447 (12)0.0461 (12)0.0109 (11)0.0142 (11)0.0148 (10)
C160.0535 (14)0.0451 (12)0.0397 (12)0.0166 (11)0.0175 (10)0.0173 (9)
C170.115 (2)0.0674 (17)0.0481 (14)−0.0004 (16)0.0374 (15)0.0240 (13)
C180.189 (4)0.082 (2)0.075 (2)−0.008 (3)0.052 (3)0.0349 (18)

Geometric parameters (Å, °)

Cl1—C11.732 (2)C8—C91.407 (3)
Cl2—C61.742 (2)C8—H80.93
N1—C11.292 (3)C10—C151.385 (3)
N1—C91.369 (3)C10—C111.390 (3)
O1—C161.325 (3)C11—C121.389 (3)
O1—C171.448 (3)C11—H110.93
O2—C161.199 (3)C12—C131.375 (4)
C1—C21.417 (3)C12—H120.93
C2—C31.382 (3)C13—C141.358 (4)
C2—C161.499 (3)C13—H130.93
C3—C41.429 (3)C14—C151.389 (4)
C3—C101.488 (3)C14—H140.93
C4—C51.416 (3)C15—H150.93
C4—C91.419 (3)C17—C181.485 (2)
C5—C61.361 (3)C17—H17A0.97
C5—H50.93C17—H17B0.97
C6—C71.397 (4)C18—H18A0.96
C7—C81.356 (4)C18—H18B0.96
C7—H70.93C18—H18C0.96
C1—N1—C9117.23 (18)C11—C10—C3120.90 (19)
C16—O1—C17116.36 (18)C12—C11—C10120.0 (2)
N1—C1—C2125.8 (2)C12—C11—H11120.0
N1—C1—Cl1115.05 (16)C10—C11—H11120.0
C2—C1—Cl1119.09 (17)C13—C12—C11120.0 (2)
C3—C2—C1118.10 (19)C13—C12—H12120.0
C3—C2—C16120.40 (18)C11—C12—H12120.0
C1—C2—C16121.50 (19)C14—C13—C12120.6 (2)
C2—C3—C4118.21 (18)C14—C13—H13119.7
C2—C3—C10120.49 (18)C12—C13—H13119.7
C4—C3—C10121.30 (18)C13—C14—C15120.1 (3)
C5—C4—C9118.57 (19)C13—C14—H14120.0
C5—C4—C3123.39 (19)C15—C14—H14120.0
C9—C4—C3118.04 (19)C10—C15—C14120.5 (2)
C6—C5—C4119.4 (2)C10—C15—H15119.8
C6—C5—H5120.3C14—C15—H15119.8
C4—C5—H5120.3O2—C16—O1125.1 (2)
C5—C6—C7122.4 (2)O2—C16—C2124.8 (2)
C5—C6—Cl2119.40 (19)O1—C16—C2110.14 (18)
C7—C6—Cl2118.20 (17)O1—C17—C18109.4 (2)
C8—C7—C6119.2 (2)O1—C17—H17A109.8
C8—C7—H7120.4C18—C17—H17A109.8
C6—C7—H7120.4O1—C17—H17B109.8
C7—C8—C9121.1 (2)C18—C17—H17B109.8
C7—C8—H8119.5H17A—C17—H17B108.2
C9—C8—H8119.5C17—C18—H18A109.5
N1—C9—C8118.0 (2)C17—C18—H18B109.5
N1—C9—C4122.57 (19)H18A—C18—H18B109.5
C8—C9—C4119.4 (2)C17—C18—H18C109.5
C15—C10—C11118.9 (2)H18A—C18—H18C109.5
C15—C10—C3120.20 (19)H18B—C18—H18C109.5
C9—N1—C1—C20.5 (3)C7—C8—C9—C4−1.6 (3)
C9—N1—C1—Cl1178.84 (15)C5—C4—C9—N1179.98 (19)
N1—C1—C2—C3−1.1 (3)C3—C4—C9—N1−0.4 (3)
Cl1—C1—C2—C3−179.37 (16)C5—C4—C9—C80.5 (3)
N1—C1—C2—C16178.0 (2)C3—C4—C9—C8−179.88 (19)
Cl1—C1—C2—C16−0.3 (3)C2—C3—C10—C15−119.8 (2)
C1—C2—C3—C40.8 (3)C4—C3—C10—C1560.9 (3)
C16—C2—C3—C4−178.25 (19)C2—C3—C10—C1158.2 (3)
C1—C2—C3—C10−178.5 (2)C4—C3—C10—C11−121.1 (2)
C16—C2—C3—C102.4 (3)C15—C10—C11—C12−0.5 (3)
C2—C3—C4—C5179.40 (19)C3—C10—C11—C12−178.6 (2)
C10—C3—C4—C5−1.3 (3)C10—C11—C12—C131.0 (4)
C2—C3—C4—C9−0.2 (3)C11—C12—C13—C14−0.9 (4)
C10—C3—C4—C9179.14 (19)C12—C13—C14—C150.3 (4)
C9—C4—C5—C61.1 (3)C11—C10—C15—C14−0.1 (4)
C3—C4—C5—C6−178.5 (2)C3—C10—C15—C14178.0 (2)
C4—C5—C6—C7−1.7 (3)C13—C14—C15—C100.2 (4)
C4—C5—C6—Cl2177.61 (16)C17—O1—C16—O25.6 (3)
C5—C6—C7—C80.7 (4)C17—O1—C16—C2−173.7 (2)
Cl2—C6—C7—C8−178.63 (18)C3—C2—C16—O2−114.0 (3)
C6—C7—C8—C91.0 (4)C1—C2—C16—O266.9 (3)
C1—N1—C9—C8179.8 (2)C3—C2—C16—O165.3 (3)
C1—N1—C9—C40.3 (3)C1—C2—C16—O1−113.8 (2)
C7—C8—C9—N1179.0 (2)C16—O1—C17—C18148.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2954).

References

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  • Anzini, M., Cappelli, A., Vomero, S., Campiani, G., Cagnotto, A. & Skorupska, M. (1991). Il Farm 46, 1435–1447. [PubMed]
  • Anzini, M., Cappelli, A., Vomero, S., Seeber, M., Menziani, M. C., Langer, T., Hagen, B., Manzoni, C. & Bourguignon, J.-J. (2001). J. Med. Chem. 44, 1134–1150. [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cappelli, A., Giuliani, G., Anzini, M., Riitano, D., Giorgi, G. & Vomero, S. (2008). Bioorg. Med. Chem. 16, 6850–6859. [PubMed]
  • Pittala, V., Modica, M., Salerno, L., Siracusa, M. A., Guerrera, F., Mereghetti, I., Cagnotto, A., Mennini, T. & Romeo, G. (2008). Med. Chem. 4, 129–137. [PubMed]
  • 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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