Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101100X/ya6028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680101100X/ya6028Isup2.hkl |
CCDC reference: 170904
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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.
Hydrogen atoms were refined isotropically; the C—H bond lengths are in the range 0.90–1.02 Å.
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.
Fig. 1. ORTEP-3 (Farrugia, 1998b) plot of the molecule of title compound. Displacement ellipsoids are drawn at the 50% probability level |
C17H16N2O2 | F(000) = 296 |
Mr = 280.32 | Dx = 1.321 Mg m−3 |
Triclinic, P1 | Melting point: 561-563_C K |
a = 7.075 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.783 (5) Å | Cell parameters from 22 reflections |
c = 12.469 (5) Å | θ = 15.7–17.7° |
α = 105.85 (4)° | µ = 0.09 mm−1 |
β = 93.44 (3)° | T = 293 K |
γ = 106.89 (3)° | Prism, colourless |
V = 705.0 (6) Å3 | 0.43 × 0.33 × 0.18 mm |
Z = 2 |
Enraf Nonius CAD4 diffractometer | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −8→8 |
2956 measured reflections | k = 0→10 |
2765 independent reflections | l = −15→14 |
1912 reflections with I > 2σ(I) | 2 standard reflections every 200 reflections |
Rint = 0.017 | intensity decay: 1% |
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) = 0.104 | Δρmax = 0.21 e Å−3 |
S = 1.10 | Δρmin = −0.20 e Å−3 |
2765 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997a) |
255 parameters | Extinction coefficient: 0.029 (5) |
All H-atom parameters refined |
C17H16N2O2 | γ = 106.89 (3)° |
Mr = 280.32 | V = 705.0 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.075 (3) Å | Mo Kα radiation |
b = 8.783 (5) Å | µ = 0.09 mm−1 |
c = 12.469 (5) Å | T = 293 K |
α = 105.85 (4)° | 0.43 × 0.33 × 0.18 mm |
β = 93.44 (3)° |
Enraf Nonius CAD4 diffractometer | Rint = 0.017 |
2956 measured reflections | 2 standard reflections every 200 reflections |
2765 independent reflections | intensity decay: 1% |
1912 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.046 | 255 parameters |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.10 | Δρmax = 0.21 e Å−3 |
2765 reflections | Δρmin = −0.20 e Å−3 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.3302 (2) | 0.5856 (2) | 0.57407 (13) | 0.0343 (4) | |
C2 | 0.3134 (2) | 0.4534 (2) | 0.61421 (15) | 0.0333 (4) | |
O21 | 0.4355 (2) | 0.3743 (2) | 0.59408 (12) | 0.0499 (4) | |
C3 | 0.1540 (3) | 0.4123 (2) | 0.67582 (15) | 0.0334 (4) | |
C4 | 0.0216 (2) | 0.4986 (2) | 0.69438 (15) | 0.0318 (4) | |
N41 | −0.1416 (2) | 0.4544 (2) | 0.7477 (2) | 0.0443 (4) | |
C5 | 0.0523 (2) | 0.6465 (2) | 0.65758 (14) | 0.0320 (4) | |
C6 | −0.0586 (3) | 0.7563 (3) | 0.6831 (2) | 0.0449 (5) | |
C7 | −0.0175 (3) | 0.8956 (3) | 0.6475 (2) | 0.0498 (5) | |
C8 | 0.1360 (3) | 0.9295 (2) | 0.5841 (2) | 0.0423 (5) | |
C9 | 0.2469 (3) | 0.8248 (2) | 0.5577 (2) | 0.0356 (4) | |
C10 | 0.2084 (2) | 0.6839 (2) | 0.59548 (14) | 0.0296 (4) | |
C11 | −0.1855 (3) | 0.3181 (2) | 0.7926 (2) | 0.0363 (4) | |
C12 | −0.3678 (3) | 0.1944 (2) | 0.7587 (2) | 0.0404 (5) | |
C13 | −0.4152 (3) | 0.0619 (2) | 0.8031 (2) | 0.0413 (5) | |
C14 | −0.2768 (3) | 0.0526 (2) | 0.8821 (2) | 0.0375 (4) | |
O141 | −0.3045 (2) | −0.0749 (2) | 0.92861 (11) | 0.0489 (4) | |
C15 | −0.0944 (3) | 0.1797 (2) | 0.9191 (2) | 0.0428 (5) | |
C16 | −0.0510 (3) | 0.3111 (2) | 0.8759 (2) | 0.0437 (5) | |
C17 | −0.4821 (3) | −0.2150 (3) | 0.8858 (2) | 0.0453 (5) | |
C18 | −0.4656 (4) | −0.3439 (3) | 0.9401 (3) | 0.0581 (6) | |
H1 | 0.425 (3) | 0.604 (3) | 0.5253 (18) | 0.056 (6)* | |
H3 | 0.143 (3) | 0.320 (2) | 0.7003 (14) | 0.036 (5)* | |
H6 | −0.158 (3) | 0.739 (3) | 0.7323 (17) | 0.057 (6)* | |
H7 | −0.087 (3) | 0.967 (3) | 0.6655 (19) | 0.069 (7)* | |
H8 | 0.163 (3) | 1.030 (3) | 0.5608 (16) | 0.049 (5)* | |
H9 | 0.355 (3) | 0.843 (2) | 0.5142 (15) | 0.040 (5)* | |
H12 | −0.458 (3) | 0.204 (2) | 0.7058 (17) | 0.050 (6)* | |
H13 | −0.546 (3) | −0.024 (3) | 0.7808 (16) | 0.049 (5)* | |
H15 | −0.004 (3) | 0.174 (3) | 0.9774 (17) | 0.050 (5)* | |
H16 | 0.072 (3) | 0.405 (3) | 0.9048 (16) | 0.052 (6)* | |
H41 | −0.243 (4) | 0.478 (3) | 0.7251 (19) | 0.066 (7)* | |
H171 | −0.598 (3) | −0.177 (2) | 0.9037 (16) | 0.044 (5)* | |
H172 | −0.486 (3) | −0.254 (3) | 0.8010 (19) | 0.056 (6)* | |
H181 | −0.459 (4) | −0.303 (3) | 1.020 (2) | 0.083 (9)* | |
H182 | −0.339 (4) | −0.375 (3) | 0.926 (2) | 0.093 (9)* | |
H183 | −0.580 (4) | −0.442 (4) | 0.915 (2) | 0.100 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0333 (8) | 0.0380 (9) | 0.0429 (9) | 0.0171 (7) | 0.0153 (7) | 0.0220 (7) |
C2 | 0.0334 (9) | 0.0364 (10) | 0.0385 (10) | 0.0164 (8) | 0.0095 (8) | 0.0184 (8) |
O21 | 0.0516 (8) | 0.0618 (9) | 0.0684 (10) | 0.0396 (7) | 0.0321 (7) | 0.0429 (8) |
C3 | 0.0370 (9) | 0.0302 (9) | 0.0398 (10) | 0.0131 (8) | 0.0103 (8) | 0.0179 (8) |
C4 | 0.0304 (9) | 0.0312 (9) | 0.0370 (10) | 0.0098 (7) | 0.0084 (7) | 0.0147 (8) |
N41 | 0.0379 (9) | 0.0477 (10) | 0.0671 (12) | 0.0228 (8) | 0.0255 (8) | 0.0356 (9) |
C5 | 0.0319 (9) | 0.0307 (9) | 0.0364 (10) | 0.0118 (7) | 0.0065 (7) | 0.0127 (8) |
C6 | 0.0474 (11) | 0.0450 (11) | 0.0562 (13) | 0.0255 (9) | 0.0221 (10) | 0.0231 (10) |
C7 | 0.0575 (13) | 0.0410 (11) | 0.0658 (14) | 0.0309 (10) | 0.0167 (11) | 0.0224 (11) |
C8 | 0.0508 (12) | 0.0332 (10) | 0.0479 (12) | 0.0157 (9) | 0.0038 (9) | 0.0187 (9) |
C9 | 0.0373 (10) | 0.0358 (10) | 0.0370 (10) | 0.0110 (8) | 0.0048 (8) | 0.0173 (8) |
C10 | 0.0304 (9) | 0.0289 (9) | 0.0309 (9) | 0.0097 (7) | 0.0033 (7) | 0.0110 (7) |
C11 | 0.0357 (10) | 0.0383 (10) | 0.0446 (11) | 0.0158 (8) | 0.0173 (8) | 0.0213 (9) |
C12 | 0.0333 (10) | 0.0484 (11) | 0.0458 (11) | 0.0133 (8) | 0.0055 (8) | 0.0240 (9) |
C13 | 0.0337 (10) | 0.0414 (11) | 0.0457 (11) | 0.0032 (8) | 0.0008 (8) | 0.0189 (9) |
C14 | 0.0395 (10) | 0.0364 (10) | 0.0371 (10) | 0.0077 (8) | 0.0062 (8) | 0.0166 (8) |
O141 | 0.0471 (8) | 0.0431 (8) | 0.0535 (9) | −0.0003 (6) | −0.0060 (6) | 0.0284 (7) |
C15 | 0.0361 (10) | 0.0462 (11) | 0.0442 (12) | 0.0040 (9) | −0.0010 (9) | 0.0224 (10) |
C16 | 0.0339 (10) | 0.0425 (11) | 0.0508 (12) | 0.0018 (9) | 0.0047 (9) | 0.0196 (9) |
C17 | 0.0384 (11) | 0.0417 (11) | 0.0541 (14) | 0.0025 (9) | 0.0061 (9) | 0.0230 (10) |
C18 | 0.058 (2) | 0.0477 (13) | 0.071 (2) | 0.0060 (12) | 0.0079 (13) | 0.0344 (13) |
N1—C2 | 1.363 (2) | C9—H9 | 0.96 (2) |
N1—C10 | 1.375 (2) | C11—C12 | 1.375 (3) |
C2—O21 | 1.254 (2) | C11—C16 | 1.392 (3) |
C2—C3 | 1.419 (2) | C12—C13 | 1.386 (3) |
C3—C4 | 1.359 (2) | C12—H12 | 0.92 (2) |
C3—H3 | 0.93 (2) | C13—C14 | 1.382 (3) |
C4—N41 | 1.378 (2) | C13—H13 | 0.97 (2) |
C4—C5 | 1.455 (2) | C14—O141 | 1.367 (2) |
N41—C11 | 1.419 (2) | C14—C15 | 1.391 (3) |
N41—H41 | 0.86 (2) | O141—C17 | 1.428 (2) |
C5—C6 | 1.396 (3) | C15—C16 | 1.368 (3) |
C5—C10 | 1.400 (2) | C15—H15 | 0.96 (2) |
C6—C7 | 1.373 (3) | C16—H16 | 0.97 (2) |
C6—H6 | 0.96 (2) | C17—C18 | 1.497 (3) |
C7—C8 | 1.391 (3) | C17—H171 | 0.99 (2) |
C7—H7 | 0.90 (2) | C17—H172 | 1.01 (2) |
C8—C9 | 1.362 (3) | C18—H181 | 0.96 (3) |
C8—H8 | 0.98 (2) | C18—H182 | 1.02 (3) |
C9—C10 | 1.402 (2) | C18—H183 | 0.95 (3) |
C2—N1—C10 | 123.42 (15) | C5—C10—C9 | 120.5 (2) |
C2—N1—H1 | 116.8 (12) | C12—C11—C16 | 118.6 (2) |
C10—N1—H1 | 119.6 (12) | C12—C11—N41 | 120.2 (2) |
O21—C2—N1 | 119.2 (2) | C16—C11—N41 | 121.1 (2) |
O21—C2—C3 | 123.8 (2) | C11—C12—C13 | 121.1 (2) |
N1—C2—C3 | 117.00 (15) | C11—C12—H12 | 117.5 (12) |
C4—C3—C2 | 122.4 (2) | C13—C12—H12 | 121.3 (12) |
C4—C3—H3 | 121.9 (11) | C14—C13—C12 | 119.7 (2) |
C2—C3—H3 | 115.7 (11) | C14—C13—H13 | 119.2 (11) |
C3—C4—N41 | 123.4 (2) | C12—C13—H13 | 121.1 (11) |
C3—C4—C5 | 119.2 (2) | O141—C14—C13 | 124.7 (2) |
N41—C4—C5 | 117.42 (15) | O141—C14—C15 | 115.8 (2) |
C4—N41—C11 | 123.7 (2) | C13—C14—C15 | 119.5 (2) |
C4—N41—H41 | 114.7 (15) | C14—O141—C17 | 117.59 (14) |
C11—N41—H41 | 115.3 (15) | C16—C15—C14 | 120.2 (2) |
C6—C5—C10 | 117.9 (2) | C16—C15—H15 | 122.0 (12) |
C6—C5—C4 | 124.6 (2) | C14—C15—H15 | 117.8 (12) |
C10—C5—C4 | 117.49 (15) | C15—C16—C11 | 120.8 (2) |
C7—C6—C5 | 121.2 (2) | C15—C16—H16 | 120.9 (11) |
C7—C6—H6 | 119.6 (12) | C11—C16—H16 | 118.2 (11) |
C5—C6—H6 | 119.0 (12) | O141—C17—C18 | 107.2 (2) |
C6—C7—C8 | 120.3 (2) | O141—C17—H171 | 108.5 (11) |
C6—C7—H7 | 120.7 (14) | C18—C17—H171 | 112.3 (11) |
C8—C7—H7 | 119.0 (14) | O141—C17—H172 | 106.1 (11) |
C9—C8—C7 | 120.0 (2) | C18—C17—H172 | 112.6 (12) |
C9—C8—H8 | 121.6 (12) | H171—C17—H172 | 109.8 (16) |
C7—C8—H8 | 118.4 (11) | C17—C18—H181 | 111.0 (16) |
C8—C9—C10 | 120.1 (2) | C17—C18—H182 | 111.3 (15) |
C8—C9—H9 | 123.3 (11) | H181—C18—H182 | 107 (2) |
C10—C9—H9 | 116.6 (10) | C17—C18—H183 | 111.8 (16) |
N1—C10—C5 | 120.22 (15) | H181—C18—H183 | 106 (2) |
N1—C10—C9 | 119.2 (2) | H182—C18—H183 | 110 (2) |
Experimental details
Crystal data | |
Chemical formula | C17H16N2O2 |
Mr | 280.32 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 705.0 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.43 × 0.33 × 0.18 |
Data collection | |
Diffractometer | Enraf Nonius CAD4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2956, 2765, 1912 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.104, 1.10 |
No. of reflections | 2765 |
No. of parameters | 255 |
No. of restraints | ? |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 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.
N1—C2 | 1.363 (2) | C8—C9 | 1.362 (3) |
N1—C10 | 1.375 (2) | C9—C10 | 1.402 (2) |
C2—O21 | 1.254 (2) | C11—C12 | 1.375 (3) |
C2—C3 | 1.419 (2) | C11—C16 | 1.392 (3) |
C3—C4 | 1.359 (2) | C12—C13 | 1.386 (3) |
C4—N41 | 1.378 (2) | C13—C14 | 1.382 (3) |
C4—C5 | 1.455 (2) | C14—O141 | 1.367 (2) |
N41—C11 | 1.419 (2) | C14—C15 | 1.391 (3) |
C5—C6 | 1.396 (3) | O141—C17 | 1.428 (2) |
C5—C10 | 1.400 (2) | C15—C16 | 1.368 (3) |
C6—C7 | 1.373 (3) | C17—C18 | 1.497 (3) |
C7—C8 | 1.391 (3) | ||
C2—N1—C10 | 123.42 (15) | N1—C10—C5 | 120.22 (15) |
O21—C2—N1 | 119.2 (2) | N1—C10—C9 | 119.2 (2) |
O21—C2—C3 | 123.8 (2) | C5—C10—C9 | 120.5 (2) |
N1—C2—C3 | 117.00 (15) | C12—C11—C16 | 118.6 (2) |
C4—C3—C2 | 122.4 (2) | C12—C11—N41 | 120.2 (2) |
C3—C4—N41 | 123.4 (2) | C16—C11—N41 | 121.1 (2) |
C3—C4—C5 | 119.2 (2) | C11—C12—C13 | 121.1 (2) |
N41—C4—C5 | 117.42 (15) | C14—C13—C12 | 119.7 (2) |
C4—N41—C11 | 123.7 (2) | O141—C14—C13 | 124.7 (2) |
C6—C5—C10 | 117.9 (2) | O141—C14—C15 | 115.8 (2) |
C6—C5—C4 | 124.6 (2) | C13—C14—C15 | 119.5 (2) |
C10—C5—C4 | 117.49 (15) | C14—O141—C17 | 117.59 (14) |
C7—C6—C5 | 121.2 (2) | C16—C15—C14 | 120.2 (2) |
C6—C7—C8 | 120.3 (2) | C15—C16—C11 | 120.8 (2) |
C9—C8—C7 | 120.0 (2) | O141—C17—C18 | 107.2 (2) |
C8—C9—C10 | 120.1 (2) |
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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.