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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2987.
Published online 2009 November 4. doi:  10.1107/S1600536809045425
PMCID: PMC2972051

Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro­quinoline-3-carboxyl­ate

Abstract

In the title compound, C18H14ClNO3, the dihydro­quinolin-2-one ring system is almost planar (r.m.s. deviation = 0.033 Å). The carboxyl­ate plane and the phenyl group are twisted away from the dihydro­quinolin-2-one ring system by 50.3 (1) and 64.9 (1)°, respectively. In the crystal structure, inversion-related mol­ecules form R 2 2(8) dimers via pairs of N—H(...)O hydrogen bonds.

Related literature

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

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Object name is e-65-o2987-scheme1.jpg

Experimental

Crystal data

  • C18H14ClNO3
  • M r = 327.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2987-efi1.jpg
  • a = 10.176 (1) Å
  • b = 15.629 (2) Å
  • c = 11.282 (1) Å
  • β = 115.463 (1)°
  • V = 1619.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 290 K
  • 0.35 × 0.31 × 0.23 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.918, T max = 0.945
  • 13600 measured reflections
  • 3699 independent reflections
  • 2906 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.129
  • S = 1.00
  • 3699 reflections
  • 213 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.20 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]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045425/ci2958sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045425/ci2958Isup2.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-chlorophenyl)(phenyl)methanone (1 mmol) and diethyl malonate (1.2 mmol) along with a catalytic amount of piperidine were heated at 453 K; the reaction was monitored by TLC. After completion, the reaction mixture was poured into the water. The organic product was extracted with ethyl acetate. The crude product was then purified by silica-gel column chromatography, with petroleum ether and ethyl acetate as eluant. Single crystals were obtained by recrystallization from ethyl acetate.

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 amino H-atom was located in a difference Fourier map, and was freely refined without any restraint.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C18H14ClNO3 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H14ClNO3F(000) = 680
Mr = 327.75Dx = 1.344 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1123 reflections
a = 10.176 (1) Åθ = 2.9–20.7°
b = 15.629 (2) ŵ = 0.25 mm1
c = 11.282 (1) ÅT = 290 K
β = 115.463 (1)°Block, colourless
V = 1619.9 (3) Å30.35 × 0.31 × 0.23 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3699 independent reflections
Radiation source: fine-focus sealed tube2906 reflections with I > 2σ(I)
graphiteRint = 0.022
[var phi] and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.918, Tmax = 0.945k = −20→19
13600 measured reflectionsl = −14→14

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) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0664P)2 + 0.4015P] where P = (Fo2 + 2Fc2)/3
3699 reflections(Δ/σ)max = 0.001
213 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

xyzUiso*/Ueq
Cl10.54343 (6)0.02895 (3)0.68514 (6)0.0743 (2)
N10.46268 (16)0.38491 (9)0.50054 (15)0.0526 (4)
H10.527 (2)0.4235 (14)0.546 (2)0.066 (6)*
O10.33674 (13)0.49099 (7)0.36051 (13)0.0569 (3)
O20.13633 (14)0.40486 (9)0.08985 (13)0.0605 (4)
O30.00732 (12)0.38779 (8)0.20662 (11)0.0487 (3)
C10.35167 (17)0.41406 (10)0.38896 (17)0.0454 (4)
C20.25139 (17)0.34892 (10)0.30798 (15)0.0404 (3)
C30.26581 (16)0.26477 (10)0.34062 (15)0.0384 (3)
C40.38454 (16)0.23795 (10)0.46323 (16)0.0405 (4)
C50.40613 (18)0.15305 (11)0.50898 (16)0.0450 (4)
H50.34520.10980.45800.054*
C60.5166 (2)0.13411 (12)0.62836 (19)0.0530 (4)
C70.6110 (2)0.19671 (14)0.7067 (2)0.0648 (5)
H70.68530.18260.78800.078*
C80.5932 (2)0.27920 (13)0.6629 (2)0.0634 (5)
H80.65660.32130.71440.076*
C90.48116 (18)0.30096 (11)0.54190 (17)0.0465 (4)
C100.12728 (17)0.38317 (10)0.18746 (15)0.0411 (4)
C11−0.1227 (2)0.42135 (14)0.09932 (19)0.0620 (5)
H11A−0.09610.46810.05730.074*
H11B−0.18820.44370.13380.074*
C12−0.1985 (2)0.3536 (2)0.0004 (2)0.0894 (8)
H12A−0.29070.3749−0.06250.134*
H12B−0.21400.30440.04380.134*
H12C−0.13980.3378−0.04370.134*
C130.15864 (17)0.20196 (10)0.25160 (15)0.0400 (3)
C140.1482 (2)0.18833 (13)0.12633 (19)0.0605 (5)
H140.21260.21560.10010.073*
C150.0423 (3)0.13422 (15)0.0401 (2)0.0782 (7)
H150.03580.1254−0.04380.094*
C16−0.0525 (3)0.09389 (13)0.0781 (2)0.0717 (6)
H16−0.12310.05740.02020.086*
C17−0.0437 (2)0.10699 (12)0.2011 (2)0.0619 (5)
H17−0.10870.07960.22640.074*
C180.06135 (19)0.16075 (11)0.28790 (17)0.0499 (4)
H180.06670.16930.37140.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0758 (4)0.0599 (3)0.0810 (4)0.0093 (2)0.0277 (3)0.0260 (3)
N10.0408 (8)0.0370 (8)0.0583 (9)−0.0040 (6)0.0007 (7)−0.0097 (7)
O10.0437 (7)0.0348 (6)0.0701 (8)−0.0018 (5)0.0034 (6)−0.0062 (6)
O20.0600 (8)0.0724 (9)0.0500 (7)0.0001 (7)0.0246 (6)0.0108 (6)
O30.0396 (6)0.0591 (7)0.0424 (6)0.0039 (5)0.0127 (5)0.0059 (5)
C10.0350 (8)0.0384 (9)0.0528 (9)−0.0012 (6)0.0095 (7)−0.0072 (7)
C20.0370 (8)0.0392 (8)0.0407 (8)−0.0041 (6)0.0126 (7)−0.0051 (6)
C30.0355 (8)0.0392 (8)0.0395 (8)−0.0040 (6)0.0152 (7)−0.0057 (6)
C40.0362 (8)0.0400 (8)0.0427 (8)−0.0010 (6)0.0145 (7)−0.0050 (7)
C50.0426 (9)0.0419 (9)0.0486 (9)−0.0011 (7)0.0178 (7)−0.0018 (7)
C60.0515 (10)0.0491 (10)0.0568 (10)0.0070 (8)0.0218 (9)0.0085 (8)
C70.0559 (11)0.0654 (13)0.0508 (10)0.0066 (9)0.0018 (9)0.0056 (9)
C80.0521 (11)0.0556 (11)0.0571 (11)−0.0020 (9)−0.0007 (9)−0.0076 (9)
C90.0382 (8)0.0423 (9)0.0477 (9)0.0008 (7)0.0079 (7)−0.0049 (7)
C100.0413 (8)0.0349 (8)0.0405 (8)−0.0062 (6)0.0115 (7)−0.0048 (6)
C110.0442 (10)0.0760 (14)0.0559 (11)0.0132 (9)0.0121 (9)0.0111 (10)
C120.0518 (13)0.133 (2)0.0645 (14)−0.0043 (14)0.0072 (11)−0.0217 (15)
C130.0406 (8)0.0347 (8)0.0398 (8)−0.0046 (6)0.0127 (7)−0.0029 (6)
C140.0770 (13)0.0589 (12)0.0531 (10)−0.0188 (10)0.0352 (10)−0.0146 (9)
C150.1034 (18)0.0738 (15)0.0521 (12)−0.0204 (13)0.0283 (12)−0.0255 (10)
C160.0731 (14)0.0518 (12)0.0663 (13)−0.0210 (10)0.0073 (11)−0.0175 (10)
C170.0506 (11)0.0514 (11)0.0736 (13)−0.0162 (8)0.0171 (10)0.0005 (9)
C180.0511 (10)0.0508 (10)0.0450 (9)−0.0105 (8)0.0181 (8)−0.0008 (7)

Geometric parameters (Å, °)

Cl1—C61.7424 (19)C8—C91.393 (2)
N1—C11.359 (2)C8—H80.93
N1—C91.378 (2)C11—C121.490 (3)
N1—H10.88 (2)C11—H11A0.97
O1—C11.237 (2)C11—H11B0.97
O2—C101.193 (2)C12—H12A0.96
O3—C101.330 (2)C12—H12B0.96
O3—C111.454 (2)C12—H12C0.96
C1—C21.453 (2)C13—C181.382 (2)
C2—C31.357 (2)C13—C141.388 (2)
C2—C101.501 (2)C14—C151.386 (3)
C3—C41.453 (2)C14—H140.93
C3—C131.490 (2)C15—C161.367 (3)
C4—C91.405 (2)C15—H150.93
C4—C51.406 (2)C16—C171.367 (3)
C5—C61.365 (2)C16—H160.93
C5—H50.93C17—C181.381 (3)
C6—C71.389 (3)C17—H170.93
C7—C81.365 (3)C18—H180.93
C7—H70.93
C1—N1—C9124.83 (14)O2—C10—C2124.65 (15)
C1—N1—H1115.4 (14)O3—C10—C2110.23 (13)
C9—N1—H1119.8 (14)O3—C11—C12111.10 (18)
C10—O3—C11117.05 (13)O3—C11—H11A109.4
O1—C1—N1121.80 (15)C12—C11—H11A109.4
O1—C1—C2122.91 (15)O3—C11—H11B109.4
N1—C1—C2115.28 (15)C12—C11—H11B109.4
C3—C2—C1122.95 (15)H11A—C11—H11B108.0
C3—C2—C10122.83 (14)C11—C12—H12A109.5
C1—C2—C10114.18 (14)C11—C12—H12B109.5
C2—C3—C4119.12 (14)H12A—C12—H12B109.5
C2—C3—C13119.56 (14)C11—C12—H12C109.5
C4—C3—C13121.31 (14)H12A—C12—H12C109.5
C9—C4—C5118.23 (15)H12B—C12—H12C109.5
C9—C4—C3117.95 (14)C18—C13—C14118.65 (15)
C5—C4—C3123.80 (14)C18—C13—C3121.14 (14)
C6—C5—C4119.94 (16)C14—C13—C3120.06 (14)
C6—C5—H5120.0C15—C14—C13120.29 (18)
C4—C5—H5120.0C15—C14—H14119.9
C5—C6—C7121.72 (17)C13—C14—H14119.9
C5—C6—Cl1119.97 (15)C16—C15—C14120.11 (19)
C7—C6—Cl1118.31 (15)C16—C15—H15119.9
C8—C7—C6119.16 (18)C14—C15—H15119.9
C8—C7—H7120.4C15—C16—C17120.18 (18)
C6—C7—H7120.4C15—C16—H16119.9
C7—C8—C9120.70 (18)C17—C16—H16119.9
C7—C8—H8119.6C16—C17—C18120.24 (19)
C9—C8—H8119.6C16—C17—H17119.9
N1—C9—C8119.95 (16)C18—C17—H17119.9
N1—C9—C4119.80 (15)C17—C18—C13120.53 (17)
C8—C9—C4120.24 (16)C17—C18—H18119.7
O2—C10—O3125.10 (15)C13—C18—H18119.7
C9—N1—C1—O1176.16 (17)C7—C8—C9—C40.1 (3)
C9—N1—C1—C2−2.6 (3)C5—C4—C9—N1−179.57 (16)
O1—C1—C2—C3−178.45 (16)C3—C4—C9—N1−1.1 (2)
N1—C1—C2—C30.3 (2)C5—C4—C9—C8−1.2 (3)
O1—C1—C2—C10−0.6 (2)C3—C4—C9—C8177.35 (16)
N1—C1—C2—C10178.23 (15)C11—O3—C10—O20.5 (2)
C1—C2—C3—C41.4 (2)C11—O3—C10—C2178.93 (14)
C10—C2—C3—C4−176.30 (14)C3—C2—C10—O2−104.7 (2)
C1—C2—C3—C13−179.62 (14)C1—C2—C10—O277.4 (2)
C10—C2—C3—C132.7 (2)C3—C2—C10—O376.87 (19)
C2—C3—C4—C9−1.0 (2)C1—C2—C10—O3−101.02 (16)
C13—C3—C4—C9−179.99 (14)C10—O3—C11—C1282.5 (2)
C2—C3—C4—C5177.38 (15)C2—C3—C13—C18−111.20 (19)
C13—C3—C4—C5−1.6 (2)C4—C3—C13—C1867.7 (2)
C9—C4—C5—C61.5 (2)C2—C3—C13—C1464.3 (2)
C3—C4—C5—C6−176.91 (15)C4—C3—C13—C14−116.78 (19)
C4—C5—C6—C7−0.8 (3)C18—C13—C14—C15−0.2 (3)
C4—C5—C6—Cl1179.98 (13)C3—C13—C14—C15−175.75 (19)
C5—C6—C7—C8−0.4 (3)C13—C14—C15—C16−0.1 (4)
Cl1—C6—C7—C8178.89 (17)C14—C15—C16—C170.3 (4)
C6—C7—C8—C90.7 (3)C15—C16—C17—C18−0.3 (4)
C1—N1—C9—C8−175.35 (18)C16—C17—C18—C130.1 (3)
C1—N1—C9—C43.1 (3)C14—C13—C18—C170.2 (3)
C7—C8—C9—N1178.5 (2)C3—C13—C18—C17175.69 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (2)1.89 (2)2.763 (2)178 (2)
C11—H11A···O2ii0.972.513.420 (3)157
C17—H17···O1iii0.932.513.299 (3)143
C18—H18···O2iv0.932.533.317 (2)142

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x, y−1/2, −z+1/2; (iv) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2958).

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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