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The molecule of the title compound, C19H18N2O3, shows a nearly planar conformation, with a dihedral angle of 8.46 (6)° between the benzene ring and the quinoline moiety. The mol­ecules are linked into dimers by C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041498/is6167sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041498/is6167Isup2.hkl
Contains datablock I

CCDC reference: 296591

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.115
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

As part of our studies on amide compounds, the title compound, (I), was synthesized and the structure was determined. The bond lengths (Table 1) are comparable with those in the related compound, N-(4-methoxyphenyl)-2-(quinolin-8-yloxy)acetamide monohydrate, (II) (Wen et al., 2005). The non-H atoms in (I) show a nearly planar conformation, with a dihedral angle of 8.46 (6)° between the benzene ring and the quinoline moiety, while the corresponding value in (II) is 67.06 (7)°. There are three intramolecular hydrogen bonds, viz. N2—H2A···O1, N2—H2A···O3 and C13—H13A···O2, forming two five-membered and one six-membered rings (Fig. 1), which contribute to the planarity of the whole molecule. In the crystal structure, the molecules are linked into a dimer by a C14—H14A···O2i hydrogen bond (symmetry code as in Table 2; Fig. 2).

Experimental top

The title compound was prepared according to the literature method of Wen et al. (2005). Colorless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether-ethylacetate (1:3, v/v) solution over 5 d.

Refinement top

All H atoms were located in a difference Fourier map and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C or N) [Uiso(H) = 1.5Ueq(C) for methyl H atoms].

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A view down the b axis, showing the hydrogen-bonded dimers. Hydrogen bonds are indicated by dashed lines.
N-(4-Ethoxyphenyl)-2-(quinolin-8-yloxy)acetamide top
Crystal data top
C19H18N2O3F(000) = 680
Mr = 322.35Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.0480 (13) ÅCell parameters from 4032 reflections
b = 8.5248 (14) Åθ = 2.5–25.7°
c = 23.821 (4) ŵ = 0.09 mm1
β = 91.676 (2)°T = 293 K
V = 1633.6 (5) Å3Plate, colourless
Z = 40.53 × 0.27 × 0.17 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3220 independent reflections
Radiation source: fine-focus sealed tube2658 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 2.5°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 710
Tmin = 0.954, Tmax = 0.985l = 2928
8662 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1712P]
where P = (Fo2 + 2Fc2)/3
3220 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C19H18N2O3V = 1633.6 (5) Å3
Mr = 322.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.0480 (13) ŵ = 0.09 mm1
b = 8.5248 (14) ÅT = 293 K
c = 23.821 (4) Å0.53 × 0.27 × 0.17 mm
β = 91.676 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3220 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2658 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.985Rint = 0.016
8662 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.04Δρmax = 0.17 e Å3
3220 reflectionsΔρmin = 0.25 e Å3
217 parameters
Special details top

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.00672 (11)0.97193 (11)0.17553 (4)0.0618 (3)
O20.34476 (13)1.04045 (18)0.08714 (5)0.0981 (4)
O30.12585 (11)0.72344 (11)0.03623 (4)0.0635 (3)
N10.31135 (14)0.86038 (14)0.19635 (5)0.0629 (3)
N20.10480 (12)0.90637 (13)0.07366 (4)0.0545 (3)
H2A0.01220.88190.09040.065*
C10.46017 (19)0.80453 (19)0.20778 (7)0.0753 (4)
H1B0.51640.75780.17860.090*
C20.5411 (2)0.8098 (2)0.26068 (8)0.0816 (5)
H2B0.64670.76710.26610.098*
C30.4622 (2)0.87854 (18)0.30357 (7)0.0759 (4)
H3A0.51310.88270.33910.091*
C40.30231 (18)0.94401 (15)0.29442 (6)0.0602 (3)
C50.2135 (2)1.02087 (18)0.33659 (6)0.0723 (4)
H5A0.26051.03150.37250.087*
C60.0597 (2)1.07919 (18)0.32484 (6)0.0731 (4)
H6A0.00231.12950.35300.088*
C70.01450 (19)1.06512 (17)0.27099 (6)0.0646 (4)
H7A0.12041.10530.26390.078*
C80.06862 (17)0.99234 (14)0.22890 (5)0.0540 (3)
C90.23151 (16)0.93046 (14)0.23956 (5)0.0534 (3)
C100.15166 (16)1.03701 (18)0.16219 (6)0.0643 (4)
H10A0.14611.15030.16570.077*
H10B0.23160.99870.18860.077*
C110.20894 (16)0.99435 (17)0.10340 (6)0.0617 (3)
C120.12822 (14)0.84898 (15)0.01848 (5)0.0511 (3)
C130.26282 (16)0.88459 (18)0.01681 (6)0.0633 (4)
H13A0.34700.94910.00420.076*
C140.27254 (18)0.8247 (2)0.07067 (6)0.0712 (4)
H14A0.36290.84980.09420.085*
C150.15032 (18)0.72893 (19)0.08964 (6)0.0708 (4)
H15A0.15780.68900.12600.085*
C160.01518 (17)0.69105 (18)0.05485 (6)0.0649 (4)
H16A0.06740.62490.06770.078*
C170.00300 (15)0.75117 (15)0.00128 (5)0.0533 (3)
C180.27288 (17)0.65097 (19)0.01583 (6)0.0661 (4)
H18A0.31190.70710.01670.079*
H18B0.25030.54320.00500.079*
C190.40048 (19)0.6567 (2)0.06267 (7)0.0825 (5)
H19A0.50160.60910.05070.124*
H19B0.36030.60070.09450.124*
H19C0.42150.76390.07290.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0589 (5)0.0722 (6)0.0541 (5)0.0186 (4)0.0015 (4)0.0073 (4)
O20.0584 (6)0.1513 (12)0.0840 (8)0.0424 (7)0.0077 (5)0.0205 (7)
O30.0577 (5)0.0760 (6)0.0565 (5)0.0223 (4)0.0063 (4)0.0064 (4)
N10.0594 (7)0.0646 (7)0.0643 (7)0.0087 (5)0.0043 (5)0.0083 (5)
N20.0467 (5)0.0628 (6)0.0540 (6)0.0109 (5)0.0009 (4)0.0020 (5)
C10.0642 (9)0.0760 (10)0.0849 (10)0.0137 (8)0.0095 (7)0.0146 (8)
C20.0710 (10)0.0728 (10)0.0993 (12)0.0101 (8)0.0260 (9)0.0068 (9)
C30.0844 (11)0.0675 (9)0.0742 (10)0.0081 (8)0.0264 (8)0.0033 (8)
C40.0725 (8)0.0501 (7)0.0575 (8)0.0146 (6)0.0067 (6)0.0028 (6)
C50.0911 (11)0.0734 (9)0.0521 (8)0.0225 (8)0.0016 (7)0.0033 (7)
C60.0935 (11)0.0684 (9)0.0581 (8)0.0137 (8)0.0162 (7)0.0130 (7)
C70.0722 (9)0.0593 (8)0.0628 (8)0.0020 (6)0.0099 (7)0.0072 (6)
C80.0632 (8)0.0481 (6)0.0508 (7)0.0014 (6)0.0023 (5)0.0020 (5)
C90.0603 (7)0.0435 (6)0.0563 (7)0.0049 (5)0.0010 (6)0.0004 (5)
C100.0557 (8)0.0748 (9)0.0627 (8)0.0160 (6)0.0072 (6)0.0029 (7)
C110.0479 (7)0.0744 (9)0.0629 (8)0.0124 (6)0.0047 (6)0.0018 (6)
C120.0464 (6)0.0539 (7)0.0530 (7)0.0011 (5)0.0007 (5)0.0041 (5)
C130.0476 (7)0.0750 (9)0.0669 (8)0.0068 (6)0.0046 (6)0.0002 (7)
C140.0562 (8)0.0887 (10)0.0676 (9)0.0016 (7)0.0159 (6)0.0008 (8)
C150.0673 (9)0.0845 (10)0.0600 (8)0.0016 (8)0.0096 (7)0.0086 (7)
C160.0622 (8)0.0712 (9)0.0610 (8)0.0078 (7)0.0028 (6)0.0084 (7)
C170.0497 (6)0.0551 (7)0.0547 (7)0.0030 (5)0.0037 (5)0.0022 (5)
C180.0585 (8)0.0760 (9)0.0637 (8)0.0202 (7)0.0001 (6)0.0035 (7)
C190.0635 (9)0.1054 (13)0.0781 (10)0.0254 (8)0.0087 (7)0.0015 (9)
Geometric parameters (Å, º) top
O1—C81.3631 (15)C7—C81.3701 (18)
O1—C101.4176 (15)C7—H7A0.9300
O2—C111.2142 (16)C8—C91.4289 (18)
O3—C171.3695 (15)C10—C111.506 (2)
O3—C181.4324 (15)C10—H10A0.9700
N1—C11.3100 (18)C10—H10B0.9700
N1—C91.3667 (17)C12—C131.3853 (17)
N2—C111.3422 (16)C12—C171.4001 (18)
N2—C121.4101 (15)C13—C141.381 (2)
N2—H2A0.8600C13—H13A0.9300
C1—C21.402 (2)C14—C151.365 (2)
C1—H1B0.9300C14—H14A0.9300
C2—C31.352 (2)C15—C161.3861 (19)
C2—H2B0.9300C15—H15A0.9300
C3—C41.413 (2)C16—C171.3760 (19)
C3—H3A0.9300C16—H16A0.9300
C4—C51.411 (2)C18—C191.495 (2)
C4—C91.4149 (18)C18—H18A0.9700
C5—C61.355 (2)C18—H18B0.9700
C5—H5A0.9300C19—H19A0.9600
C6—C71.404 (2)C19—H19B0.9600
C6—H6A0.9300C19—H19C0.9600
C8—O1—C10117.44 (10)O1—C10—H10B109.4
C17—O3—C18118.06 (10)C11—C10—H10B109.4
C1—N1—C9116.71 (13)H10A—C10—H10B108.0
C11—N2—C12128.12 (11)O2—C11—N2125.64 (14)
C11—N2—H2A115.9O2—C11—C10117.82 (12)
C12—N2—H2A115.9N2—C11—C10116.54 (11)
N1—C1—C2124.95 (15)C13—C12—C17118.96 (12)
N1—C1—H1B117.5C13—C12—N2124.79 (12)
C2—C1—H1B117.5C17—C12—N2116.24 (10)
C3—C2—C1118.46 (15)C14—C13—C12120.32 (13)
C3—C2—H2B120.8C14—C13—H13A119.8
C1—C2—H2B120.8C12—C13—H13A119.8
C2—C3—C4120.02 (14)C15—C14—C13120.45 (13)
C2—C3—H3A120.0C15—C14—H14A119.8
C4—C3—H3A120.0C13—C14—H14A119.8
C5—C4—C3123.45 (14)C14—C15—C16120.11 (14)
C5—C4—C9119.78 (14)C14—C15—H15A119.9
C3—C4—C9116.77 (14)C16—C15—H15A119.9
C6—C5—C4120.11 (14)C17—C16—C15120.07 (14)
C6—C5—H5A119.9C17—C16—H16A120.0
C4—C5—H5A119.9C15—C16—H16A120.0
C5—C6—C7121.26 (14)O3—C17—C16124.95 (12)
C5—C6—H6A119.4O3—C17—C12114.97 (11)
C7—C6—H6A119.4C16—C17—C12120.08 (12)
C8—C7—C6120.23 (14)O3—C18—C19106.79 (11)
C8—C7—H7A119.9O3—C18—H18A110.4
C6—C7—H7A119.9C19—C18—H18A110.4
O1—C8—C7124.58 (13)O3—C18—H18B110.4
O1—C8—C9115.28 (11)C19—C18—H18B110.4
C7—C8—C9120.15 (12)H18A—C18—H18B108.6
N1—C9—C4123.07 (12)C18—C19—H19A109.5
N1—C9—C8118.47 (11)C18—C19—H19B109.5
C4—C9—C8118.46 (12)H19A—C19—H19B109.5
O1—C10—C11111.27 (11)C18—C19—H19C109.5
O1—C10—H10A109.4H19A—C19—H19C109.5
C11—C10—H10A109.4H19B—C19—H19C109.5
C9—N1—C1—C20.9 (2)C7—C8—C9—C41.07 (18)
N1—C1—C2—C30.6 (3)C8—O1—C10—C11175.60 (11)
C1—C2—C3—C40.5 (2)C12—N2—C11—O20.0 (2)
C2—C3—C4—C5178.47 (15)C12—N2—C11—C10179.20 (12)
C2—C3—C4—C91.2 (2)O1—C10—C11—O2178.58 (14)
C3—C4—C5—C6179.23 (14)O1—C10—C11—N20.69 (19)
C9—C4—C5—C61.1 (2)C11—N2—C12—C134.9 (2)
C4—C5—C6—C70.1 (2)C11—N2—C12—C17176.13 (13)
C5—C6—C7—C80.4 (2)C17—C12—C13—C140.2 (2)
C10—O1—C8—C73.00 (19)N2—C12—C13—C14178.68 (13)
C10—O1—C8—C9177.43 (11)C12—C13—C14—C150.4 (2)
C6—C7—C8—O1179.48 (12)C13—C14—C15—C160.0 (2)
C6—C7—C8—C90.1 (2)C14—C15—C16—C170.7 (2)
C1—N1—C9—C40.03 (19)C18—O3—C17—C1612.0 (2)
C1—N1—C9—C8179.74 (13)C18—O3—C17—C12167.92 (12)
C5—C4—C9—N1178.71 (12)C15—C16—C17—O3178.99 (13)
C3—C4—C9—N10.98 (19)C15—C16—C17—C120.9 (2)
C5—C4—C9—C81.57 (18)C13—C12—C17—O3179.44 (11)
C3—C4—C9—C8178.74 (12)N2—C12—C17—O30.45 (17)
O1—C8—C9—N11.20 (17)C13—C12—C17—C160.4 (2)
C7—C8—C9—N1179.20 (12)N2—C12—C17—C16179.44 (12)
O1—C8—C9—C4178.53 (10)C17—O3—C18—C19171.70 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.862.172.623 (1)112
N2—H2A···O30.862.192.602 (1)109
C13—H13A···O20.932.312.903 (2)121
C14—H14A···O2i0.932.543.300 (2)139
Symmetry code: (i) x1, y+2, z.

Experimental details

Crystal data
Chemical formulaC19H18N2O3
Mr322.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.0480 (13), 8.5248 (14), 23.821 (4)
β (°) 91.676 (2)
V3)1633.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.53 × 0.27 × 0.17
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.954, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
8662, 3220, 2658
Rint0.016
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.115, 1.04
No. of reflections3220
No. of parameters217
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.25

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected bond lengths (Å) top
O1—C81.3631 (15)N2—C111.3422 (16)
O1—C101.4176 (15)N2—C121.4101 (15)
O2—C111.2142 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.862.172.623 (1)112
N2—H2A···O30.862.192.602 (1)109
C13—H13A···O20.932.312.903 (2)121
C14—H14A···O2i0.932.543.300 (2)139
Symmetry code: (i) x1, y+2, z.
 

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