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Acta Cryst. (2009). E65, o2982    [ doi:10.1107/S1600536809045334 ]

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

S. M. Roopan, F. N. Khan, M. Vijetha, V. R. Hathwar and S. W. Ng

Abstract top

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 top

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, 1992, 2001); Cappelli et al. (2008); Pittala et al. (2008).

Experimental top

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 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 1.2–1.5Ueq(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 C18H13Cl2NO2 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate top
Crystal data top
C18H13Cl2NO2Z = 2
Mr = 346.19F(000) = 356
Triclinic, P1Dx = 1.404 Mg m−3
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 mm−1
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 top
Bruker SMART CCD area-detector
diffractometer		3700 independent reflections
Radiation source: fine-focus sealed tube2537 reflections with I > 2σ(I)
graphiteRint = 0.031
φ 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 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.02 w = 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 Å−3
1 restraintΔρmin = −0.35 e Å−3
Crystal data top
C18H13Cl2NO2γ = 95.980 (4)°
Mr = 346.19V = 818.73 (7) Å3
Triclinic, P1Z = 2
a = 8.3553 (3) ÅMo Kα radiation
b = 10.1861 (5) ŵ = 0.40 mm−1
c = 10.6731 (6) ÅT = 295 K
α = 110.537 (5)°0.34 × 0.26 × 0.25 mm
β = 101.421 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3700 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2537 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.906Rint = 0.031
18102 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.144Δρmax = 0.41 e Å−3
S = 1.02Δρmin = −0.35 e Å−3
3700 reflectionsAbsolute structure: ?
209 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
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

Anzini, M., Cappelli, A., Vomero, S., Cagnotto, A. & Skorupska, M. (1992). Il Farm. 47, 191–202.

Anzini, M., Cappelli, A., Vomero, S., Campiani, G., Cagnotto, A. & Skorupska, M. (1991). Il Farm. 46, 1435–1447.

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.

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.

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.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

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