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The reaction product of 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ic acid with p-phenetidine is 4-(4-ethoxy­phenyl­amino)-2-oxo-1,2-di­hydro­quinoline, C17H16N2O2. The mol­ecules form centrosymmetric hydrogen-bonded dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101100X/ya6028sup1.cif
Contains datablocks ibs2, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680101100X/ya6028Isup2.hkl
Contains datablock I

CCDC reference: 170904

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.104
  • Data-to-parameter ratio = 10.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.088 Value of mu given = 0.090
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

N,N'-dicyclohexylcarbodiimide (DCC) (Kurzer & Douraghi-Zaden, 1967) is widely used in organic chemistry for the synthesis of amides of carboxylic acids. We investigated the possibility of using this condensing reagent for the synthesis of 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxamide (3) (see scheme below), which was supposed to possess bioactive properties. We carried out the reaction between 4-chloro-2-oxo-1,2-dihydroquinoline (1) with p-phenetidine (2) in a boiling mixture of N,N-dimethylformamide (DMF) and (DCC) and obtained 4-(4-ethoxyphenylamino)-2-oxo-1,2-dihydroquinoline, C17H16N2O2 (4) instead of (3).

The X-ray single-crystal analysis showed, that the 10-membered heterobicycle (N1···C10) (Fig. 1) is planar to within 0.06 Å, the O21 and N41 atoms showing small displacements from its least-squares plane [0.135 (2) and -0.166 (3) Å respectively]. The C11 atom also lies essentially in the same plane, as indicated by the C5—C4—N41—C11 torsion angle of -177.1 (2) °. The C11–C16 phenyl ring, however, is rotated out of the dihydroquinoline plane and forms a dihedral angle of 63.63 (4)° with the latter.

The N1—H1···O21 hydrogen bond [N1—H1···O21i 1.86 (2), N1···O21i 2.784 (2) Å, N1—H1···O21i 168 (2)°; symmetry operation (i) 1 - x, 1 - y, 1 - z] links the molecules in the crystal into centrosymmetric dimers.

Experimental top

2.23 g, (0.01 mol) of (1) was refluxed for 2 h in 30 ml of N,N-dimethylformamide (DMF) with 1.51 g (0.011 mol) of p-phenetidine and 2.26 g (0.011 mol) of DCC. 4-(4-ethoxyphenylamino)-2-oxo-1,2-dihydroquinoline, C17H16N2O2 (4) was obtained (2.07 g, yield 74%) and was recrystallized from H2O.

Refinement top

Hydrogen atoms were refined isotropically; the C—H bond lengths are in the range 0.90–1.02 Å.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: WinGX98 (Farrugia, 1998a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 (Farrugia, 1998b); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1998b) plot of the molecule of title compound. Displacement ellipsoids are drawn at the 50% probability level
4-(4-ethoxyphenylamino)-2-oxo-1,2-dihydroquinoline top
Crystal data top
C17H16N2O2F(000) = 296
Mr = 280.32Dx = 1.321 Mg m3
Triclinic, P1Melting point: 561-563_C K
a = 7.075 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.783 (5) ÅCell parameters from 22 reflections
c = 12.469 (5) Åθ = 15.7–17.7°
α = 105.85 (4)°µ = 0.09 mm1
β = 93.44 (3)°T = 293 K
γ = 106.89 (3)°Prism, colourless
V = 705.0 (6) Å30.43 × 0.33 × 0.18 mm
Z = 2
Data collection top
Enraf Nonius CAD4
diffractometer
θmax = 26.0°, θmin = 1.7°
ω scansh = 88
2956 measured reflectionsk = 010
2765 independent reflectionsl = 1514
1912 reflections with I > 2σ(I)2 standard reflections every 200 reflections
Rint = 0.017 intensity decay: 1%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.046(Δ/σ)max = 0.049
wR(F2) = 0.104Δρmax = 0.21 e Å3
S = 1.10Δρmin = 0.20 e Å3
2765 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997a)
255 parametersExtinction coefficient: 0.029 (5)
All H-atom parameters refined
Crystal data top
C17H16N2O2γ = 106.89 (3)°
Mr = 280.32V = 705.0 (6) Å3
Triclinic, P1Z = 2
a = 7.075 (3) ÅMo Kα radiation
b = 8.783 (5) ŵ = 0.09 mm1
c = 12.469 (5) ÅT = 293 K
α = 105.85 (4)°0.43 × 0.33 × 0.18 mm
β = 93.44 (3)°
Data collection top
Enraf Nonius CAD4
diffractometer
Rint = 0.017
2956 measured reflections2 standard reflections every 200 reflections
2765 independent reflections intensity decay: 1%
1912 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.046255 parameters
wR(F2) = 0.104All H-atom parameters refined
S = 1.10Δρmax = 0.21 e Å3
2765 reflectionsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3302 (2)0.5856 (2)0.57407 (13)0.0343 (4)
C20.3134 (2)0.4534 (2)0.61421 (15)0.0333 (4)
O210.4355 (2)0.3743 (2)0.59408 (12)0.0499 (4)
C30.1540 (3)0.4123 (2)0.67582 (15)0.0334 (4)
C40.0216 (2)0.4986 (2)0.69438 (15)0.0318 (4)
N410.1416 (2)0.4544 (2)0.7477 (2)0.0443 (4)
C50.0523 (2)0.6465 (2)0.65758 (14)0.0320 (4)
C60.0586 (3)0.7563 (3)0.6831 (2)0.0449 (5)
C70.0175 (3)0.8956 (3)0.6475 (2)0.0498 (5)
C80.1360 (3)0.9295 (2)0.5841 (2)0.0423 (5)
C90.2469 (3)0.8248 (2)0.5577 (2)0.0356 (4)
C100.2084 (2)0.6839 (2)0.59548 (14)0.0296 (4)
C110.1855 (3)0.3181 (2)0.7926 (2)0.0363 (4)
C120.3678 (3)0.1944 (2)0.7587 (2)0.0404 (5)
C130.4152 (3)0.0619 (2)0.8031 (2)0.0413 (5)
C140.2768 (3)0.0526 (2)0.8821 (2)0.0375 (4)
O1410.3045 (2)0.0749 (2)0.92861 (11)0.0489 (4)
C150.0944 (3)0.1797 (2)0.9191 (2)0.0428 (5)
C160.0510 (3)0.3111 (2)0.8759 (2)0.0437 (5)
C170.4821 (3)0.2150 (3)0.8858 (2)0.0453 (5)
C180.4656 (4)0.3439 (3)0.9401 (3)0.0581 (6)
H10.425 (3)0.604 (3)0.5253 (18)0.056 (6)*
H30.143 (3)0.320 (2)0.7003 (14)0.036 (5)*
H60.158 (3)0.739 (3)0.7323 (17)0.057 (6)*
H70.087 (3)0.967 (3)0.6655 (19)0.069 (7)*
H80.163 (3)1.030 (3)0.5608 (16)0.049 (5)*
H90.355 (3)0.843 (2)0.5142 (15)0.040 (5)*
H120.458 (3)0.204 (2)0.7058 (17)0.050 (6)*
H130.546 (3)0.024 (3)0.7808 (16)0.049 (5)*
H150.004 (3)0.174 (3)0.9774 (17)0.050 (5)*
H160.072 (3)0.405 (3)0.9048 (16)0.052 (6)*
H410.243 (4)0.478 (3)0.7251 (19)0.066 (7)*
H1710.598 (3)0.177 (2)0.9037 (16)0.044 (5)*
H1720.486 (3)0.254 (3)0.8010 (19)0.056 (6)*
H1810.459 (4)0.303 (3)1.020 (2)0.083 (9)*
H1820.339 (4)0.375 (3)0.926 (2)0.093 (9)*
H1830.580 (4)0.442 (4)0.915 (2)0.100 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0333 (8)0.0380 (9)0.0429 (9)0.0171 (7)0.0153 (7)0.0220 (7)
C20.0334 (9)0.0364 (10)0.0385 (10)0.0164 (8)0.0095 (8)0.0184 (8)
O210.0516 (8)0.0618 (9)0.0684 (10)0.0396 (7)0.0321 (7)0.0429 (8)
C30.0370 (9)0.0302 (9)0.0398 (10)0.0131 (8)0.0103 (8)0.0179 (8)
C40.0304 (9)0.0312 (9)0.0370 (10)0.0098 (7)0.0084 (7)0.0147 (8)
N410.0379 (9)0.0477 (10)0.0671 (12)0.0228 (8)0.0255 (8)0.0356 (9)
C50.0319 (9)0.0307 (9)0.0364 (10)0.0118 (7)0.0065 (7)0.0127 (8)
C60.0474 (11)0.0450 (11)0.0562 (13)0.0255 (9)0.0221 (10)0.0231 (10)
C70.0575 (13)0.0410 (11)0.0658 (14)0.0309 (10)0.0167 (11)0.0224 (11)
C80.0508 (12)0.0332 (10)0.0479 (12)0.0157 (9)0.0038 (9)0.0187 (9)
C90.0373 (10)0.0358 (10)0.0370 (10)0.0110 (8)0.0048 (8)0.0173 (8)
C100.0304 (9)0.0289 (9)0.0309 (9)0.0097 (7)0.0033 (7)0.0110 (7)
C110.0357 (10)0.0383 (10)0.0446 (11)0.0158 (8)0.0173 (8)0.0213 (9)
C120.0333 (10)0.0484 (11)0.0458 (11)0.0133 (8)0.0055 (8)0.0240 (9)
C130.0337 (10)0.0414 (11)0.0457 (11)0.0032 (8)0.0008 (8)0.0189 (9)
C140.0395 (10)0.0364 (10)0.0371 (10)0.0077 (8)0.0062 (8)0.0166 (8)
O1410.0471 (8)0.0431 (8)0.0535 (9)0.0003 (6)0.0060 (6)0.0284 (7)
C150.0361 (10)0.0462 (11)0.0442 (12)0.0040 (9)0.0010 (9)0.0224 (10)
C160.0339 (10)0.0425 (11)0.0508 (12)0.0018 (9)0.0047 (9)0.0196 (9)
C170.0384 (11)0.0417 (11)0.0541 (14)0.0025 (9)0.0061 (9)0.0230 (10)
C180.058 (2)0.0477 (13)0.071 (2)0.0060 (12)0.0079 (13)0.0344 (13)
Geometric parameters (Å, º) top
N1—C21.363 (2)C9—H90.96 (2)
N1—C101.375 (2)C11—C121.375 (3)
C2—O211.254 (2)C11—C161.392 (3)
C2—C31.419 (2)C12—C131.386 (3)
C3—C41.359 (2)C12—H120.92 (2)
C3—H30.93 (2)C13—C141.382 (3)
C4—N411.378 (2)C13—H130.97 (2)
C4—C51.455 (2)C14—O1411.367 (2)
N41—C111.419 (2)C14—C151.391 (3)
N41—H410.86 (2)O141—C171.428 (2)
C5—C61.396 (3)C15—C161.368 (3)
C5—C101.400 (2)C15—H150.96 (2)
C6—C71.373 (3)C16—H160.97 (2)
C6—H60.96 (2)C17—C181.497 (3)
C7—C81.391 (3)C17—H1710.99 (2)
C7—H70.90 (2)C17—H1721.01 (2)
C8—C91.362 (3)C18—H1810.96 (3)
C8—H80.98 (2)C18—H1821.02 (3)
C9—C101.402 (2)C18—H1830.95 (3)
C2—N1—C10123.42 (15)C5—C10—C9120.5 (2)
C2—N1—H1116.8 (12)C12—C11—C16118.6 (2)
C10—N1—H1119.6 (12)C12—C11—N41120.2 (2)
O21—C2—N1119.2 (2)C16—C11—N41121.1 (2)
O21—C2—C3123.8 (2)C11—C12—C13121.1 (2)
N1—C2—C3117.00 (15)C11—C12—H12117.5 (12)
C4—C3—C2122.4 (2)C13—C12—H12121.3 (12)
C4—C3—H3121.9 (11)C14—C13—C12119.7 (2)
C2—C3—H3115.7 (11)C14—C13—H13119.2 (11)
C3—C4—N41123.4 (2)C12—C13—H13121.1 (11)
C3—C4—C5119.2 (2)O141—C14—C13124.7 (2)
N41—C4—C5117.42 (15)O141—C14—C15115.8 (2)
C4—N41—C11123.7 (2)C13—C14—C15119.5 (2)
C4—N41—H41114.7 (15)C14—O141—C17117.59 (14)
C11—N41—H41115.3 (15)C16—C15—C14120.2 (2)
C6—C5—C10117.9 (2)C16—C15—H15122.0 (12)
C6—C5—C4124.6 (2)C14—C15—H15117.8 (12)
C10—C5—C4117.49 (15)C15—C16—C11120.8 (2)
C7—C6—C5121.2 (2)C15—C16—H16120.9 (11)
C7—C6—H6119.6 (12)C11—C16—H16118.2 (11)
C5—C6—H6119.0 (12)O141—C17—C18107.2 (2)
C6—C7—C8120.3 (2)O141—C17—H171108.5 (11)
C6—C7—H7120.7 (14)C18—C17—H171112.3 (11)
C8—C7—H7119.0 (14)O141—C17—H172106.1 (11)
C9—C8—C7120.0 (2)C18—C17—H172112.6 (12)
C9—C8—H8121.6 (12)H171—C17—H172109.8 (16)
C7—C8—H8118.4 (11)C17—C18—H181111.0 (16)
C8—C9—C10120.1 (2)C17—C18—H182111.3 (15)
C8—C9—H9123.3 (11)H181—C18—H182107 (2)
C10—C9—H9116.6 (10)C17—C18—H183111.8 (16)
N1—C10—C5120.22 (15)H181—C18—H183106 (2)
N1—C10—C9119.2 (2)H182—C18—H183110 (2)

Experimental details

Crystal data
Chemical formulaC17H16N2O2
Mr280.32
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.075 (3), 8.783 (5), 12.469 (5)
α, β, γ (°)105.85 (4), 93.44 (3), 106.89 (3)
V3)705.0 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.43 × 0.33 × 0.18
Data collection
DiffractometerEnraf Nonius CAD4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2956, 2765, 1912
Rint0.017
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.104, 1.10
No. of reflections2765
No. of parameters255
No. of restraints?
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.21, 0.20

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, WinGX98 (Farrugia, 1998a), SHELXS97 (Sheldrick, 1997b), SHELXL97 (Sheldrick, 1997a), ORTEP-3 (Farrugia, 1998b), SHELXL97.

Selected geometric parameters (Å, º) top
N1—C21.363 (2)C8—C91.362 (3)
N1—C101.375 (2)C9—C101.402 (2)
C2—O211.254 (2)C11—C121.375 (3)
C2—C31.419 (2)C11—C161.392 (3)
C3—C41.359 (2)C12—C131.386 (3)
C4—N411.378 (2)C13—C141.382 (3)
C4—C51.455 (2)C14—O1411.367 (2)
N41—C111.419 (2)C14—C151.391 (3)
C5—C61.396 (3)O141—C171.428 (2)
C5—C101.400 (2)C15—C161.368 (3)
C6—C71.373 (3)C17—C181.497 (3)
C7—C81.391 (3)
C2—N1—C10123.42 (15)N1—C10—C5120.22 (15)
O21—C2—N1119.2 (2)N1—C10—C9119.2 (2)
O21—C2—C3123.8 (2)C5—C10—C9120.5 (2)
N1—C2—C3117.00 (15)C12—C11—C16118.6 (2)
C4—C3—C2122.4 (2)C12—C11—N41120.2 (2)
C3—C4—N41123.4 (2)C16—C11—N41121.1 (2)
C3—C4—C5119.2 (2)C11—C12—C13121.1 (2)
N41—C4—C5117.42 (15)C14—C13—C12119.7 (2)
C4—N41—C11123.7 (2)O141—C14—C13124.7 (2)
C6—C5—C10117.9 (2)O141—C14—C15115.8 (2)
C6—C5—C4124.6 (2)C13—C14—C15119.5 (2)
C10—C5—C4117.49 (15)C14—O141—C17117.59 (14)
C7—C6—C5121.2 (2)C16—C15—C14120.2 (2)
C6—C7—C8120.3 (2)C15—C16—C11120.8 (2)
C9—C8—C7120.0 (2)O141—C17—C18107.2 (2)
C8—C9—C10120.1 (2)
 

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