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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o651.
Published online 2009 February 28. doi:  10.1107/S1600536809006461
PMCID: PMC2968527

(E)-N′-[1-(4-Hydroxy­phen­yl)ethyl­idene]-2-(quinolin-8-yl­oxy)acetohydrazide methanol solvate

Abstract

In the title compound, C19H17N3O3·CH4O, the mean planes of the benzene ring and the quinoline rings make a dihedral angle of 75.5 (2)°. The acetohydrazide mol­ecules are connected via pairs of inter­molecular O—H(...)O hydrogen bonds into inversion dimers, and the methanol solvent mol­ecule is linked to the acetohydrazide mol­ecule via inter­molecular N—H(...)O and bifurcated O—H(...)(N,O) hydrogen bonds.

Related literature

For background on the coordination chemistry of 8-hydroxy­quinoline and its derivatives, see: Chen & Shi (1998 [triangle]). For related structures, see: Wen et al. (2005 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o651-scheme1.jpg

Experimental

Crystal data

  • C19H17N3O3·CH4O
  • M r = 367.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o651-efi1.jpg
  • a = 9.552 (3) Å
  • b = 10.622 (2) Å
  • c = 10.665 (4) Å
  • α = 70.055 (5)°
  • β = 83.033 (4)°
  • γ = 65.845 (4)°
  • V = 927.9 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.20 × 0.18 × 0.15 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.982, T max = 0.986
  • 4927 measured reflections
  • 3261 independent reflections
  • 2430 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.143
  • S = 1.08
  • 3261 reflections
  • 246 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006461/hb2916sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006461/hb2916Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

8-Hydroxyquinoline and its derivatives constitute well known ligands in coordination chemistry (Chen & Shi, 1998). In our search for new extractants of metal ions and biologically active materials, the title compound, (I), has been synthesized. We report here its crystal structure. All bond lengths and angles are normal (Allen et al., 1987), and are comparable to those in the related compound N'-(2-Fluorobenzylidene) -2-(quinolin-8-yloxy)-acetohydrazide methanol solvate (Wen et al., 2005). The mean planes of the benzene ring and the quinoline rings make a dihedral angle of 75.5 (2)°. In the crystal structure, the methanol molecule is linked to the C19H17N3O3 molecule via intermolecular O—H···O, N—H···O and O—H···N hydrogen bonds (Fig. 1), intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2).

Experimental

2-(Quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 1-(4-hydroxyphenyl)ethanone (1.36 g, 10 mmol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 3 h. After cooling to room temperature, the mixture was filtered. Pale yellow blocks of (I) were obtained by slow evaporation of a acetone-methanol (1:2, v/v) solution over a period of 3 d. Analysis calculated for C20H21N3O4: C 65.38, H 5.76, N 11.43%; found: C 65.76, H 5.47, N 11.67%.

Refinement

All H atoms were initially located in a difference Fourier map. The methylene H atoms were constrained to an ideal geometry, with C—H = 0.93 Å for aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms, O—H = 0.82 Å and N—H = 0.86 Å. Uiso(H) = 1.2Ueq(C,N), or 1.5Ueq(C) for the methyl groups, and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
Fig. 2.
The structure of the dimers formed via hydrogen bonds, H atoms have been omitted for clarity. The dashed lines indicate hydrogen bonds.

Crystal data

C19H17N3O3·CH4OZ = 2
Mr = 367.40F(000) = 388
Triclinic, P1Dx = 1.315 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.552 (3) ÅCell parameters from 1866 reflections
b = 10.622 (2) Åθ = 2.5–26.5°
c = 10.665 (4) ŵ = 0.09 mm1
α = 70.055 (5)°T = 295 K
β = 83.033 (4)°Block, light yellow
γ = 65.845 (4)°0.20 × 0.18 × 0.15 mm
V = 927.9 (5) Å3

Data collection

Bruker SMART CCD diffractometer3261 independent reflections
Radiation source: fine-focus sealed tube2430 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→8
Tmin = 0.982, Tmax = 0.986k = −12→7
4927 measured reflectionsl = −12→12

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0478P)2 + 0.5262P] where P = (Fo2 + 2Fc2)/3
3261 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.19 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.
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)

xyzUiso*/Ueq
O10.32959 (17)0.65533 (18)0.12916 (16)0.0512 (4)
O20.0115 (2)0.8800 (2)−0.09376 (17)0.0620 (5)
O3−0.83771 (19)1.1439 (3)0.2526 (2)0.0726 (6)
H3−0.87621.12850.19770.109*
O40.1513 (2)0.5644 (2)0.3745 (2)0.0666 (5)
H40.24440.53470.36430.100*
N10.4677 (2)0.4420 (2)0.3533 (2)0.0523 (5)
N20.0236 (2)0.7950 (2)0.1324 (2)0.0516 (5)
H20.08070.74940.20340.062*
N3−0.1361 (2)0.8523 (2)0.1406 (2)0.0509 (5)
C10.5370 (3)0.3362 (3)0.4623 (3)0.0624 (7)
H10.47610.30850.53210.075*
C20.6963 (3)0.2631 (3)0.4795 (3)0.0694 (8)
H2A0.73930.18820.55810.083*
C30.7866 (3)0.3033 (3)0.3797 (3)0.0672 (8)
H3A0.89280.25580.38950.081*
C40.7203 (3)0.4173 (3)0.2607 (3)0.0528 (6)
C50.8077 (3)0.4653 (3)0.1532 (3)0.0638 (8)
H50.91430.42250.15890.077*
C60.7356 (3)0.5740 (3)0.0418 (3)0.0646 (8)
H60.79400.6059−0.02820.078*
C70.5749 (3)0.6397 (3)0.0292 (3)0.0540 (6)
H70.52830.7127−0.04930.065*
C80.4869 (3)0.5969 (3)0.1319 (2)0.0451 (6)
C90.5576 (3)0.4842 (3)0.2515 (2)0.0449 (6)
C100.2571 (3)0.7563 (3)0.0056 (2)0.0486 (6)
H10A0.29090.7093−0.06270.058*
H10B0.28840.8376−0.01990.058*
C110.0854 (3)0.8127 (3)0.0119 (2)0.0455 (6)
C12−0.1908 (3)0.8900 (3)0.2445 (2)0.0463 (6)
C13−0.0992 (3)0.8864 (3)0.3513 (3)0.0587 (7)
H13A−0.00810.79830.37220.088*
H13B−0.15970.88970.42980.088*
H13C−0.07120.96890.32030.088*
C14−0.3614 (3)0.9510 (3)0.2510 (2)0.0447 (6)
C15−0.4388 (3)1.0446 (3)0.3227 (3)0.0577 (7)
H15−0.38311.06540.37290.069*
C16−0.5971 (3)1.1082 (3)0.3218 (3)0.0640 (8)
H16−0.64641.17160.37050.077*
C17−0.6820 (3)1.0784 (3)0.2495 (2)0.0508 (6)
C18−0.6079 (3)0.9839 (3)0.1787 (3)0.0578 (7)
H18−0.66440.96220.13000.069*
C19−0.4494 (3)0.9211 (3)0.1796 (3)0.0554 (7)
H19−0.40060.85730.13130.067*
C200.0957 (4)0.4729 (4)0.3498 (5)0.1075 (14)
H20A0.12920.38110.42020.161*
H20B0.13380.45760.26640.161*
H20C−0.01440.51680.34560.161*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0323 (9)0.0558 (10)0.0498 (10)−0.0091 (7)−0.0026 (7)−0.0074 (8)
O20.0498 (11)0.0737 (13)0.0533 (11)−0.0199 (9)−0.0132 (9)−0.0100 (9)
O30.0358 (10)0.0972 (16)0.0839 (15)−0.0128 (10)−0.0033 (9)−0.0429 (12)
O40.0499 (11)0.0642 (12)0.0743 (13)−0.0161 (10)0.0034 (10)−0.0174 (10)
N10.0471 (12)0.0523 (12)0.0533 (12)−0.0163 (10)−0.0040 (10)−0.0142 (10)
N20.0341 (11)0.0552 (13)0.0525 (13)−0.0051 (9)−0.0079 (9)−0.0144 (10)
N30.0346 (11)0.0521 (12)0.0560 (13)−0.0064 (9)−0.0049 (9)−0.0166 (10)
C10.0664 (18)0.0619 (17)0.0547 (16)−0.0257 (15)−0.0087 (13)−0.0096 (14)
C20.0640 (19)0.0627 (18)0.0703 (19)−0.0161 (15)−0.0258 (16)−0.0099 (15)
C30.0456 (16)0.0624 (18)0.085 (2)−0.0084 (13)−0.0224 (15)−0.0211 (16)
C40.0409 (14)0.0533 (15)0.0679 (17)−0.0133 (12)−0.0092 (12)−0.0268 (13)
C50.0331 (13)0.0740 (19)0.086 (2)−0.0173 (13)0.0023 (14)−0.0330 (17)
C60.0447 (15)0.0720 (19)0.077 (2)−0.0245 (14)0.0125 (14)−0.0252 (16)
C70.0457 (14)0.0550 (15)0.0571 (16)−0.0182 (12)0.0020 (12)−0.0152 (12)
C80.0355 (12)0.0448 (13)0.0546 (14)−0.0122 (10)−0.0009 (11)−0.0194 (11)
C90.0383 (13)0.0446 (13)0.0544 (15)−0.0132 (11)−0.0038 (11)−0.0211 (11)
C100.0424 (13)0.0505 (14)0.0477 (14)−0.0162 (11)−0.0022 (11)−0.0114 (11)
C110.0408 (13)0.0409 (13)0.0514 (14)−0.0118 (10)−0.0062 (11)−0.0134 (11)
C120.0388 (13)0.0423 (13)0.0495 (14)−0.0100 (10)−0.0044 (11)−0.0104 (11)
C130.0438 (14)0.0680 (18)0.0578 (16)−0.0124 (13)−0.0077 (12)−0.0215 (14)
C140.0385 (12)0.0462 (13)0.0431 (13)−0.0127 (10)−0.0031 (10)−0.0103 (11)
C150.0410 (14)0.0717 (18)0.0655 (17)−0.0133 (13)−0.0071 (12)−0.0362 (15)
C160.0456 (15)0.0753 (19)0.0713 (18)−0.0074 (13)−0.0030 (13)−0.0427 (16)
C170.0358 (13)0.0590 (16)0.0503 (14)−0.0131 (11)−0.0026 (11)−0.0147 (12)
C180.0463 (15)0.0756 (19)0.0649 (17)−0.0263 (14)−0.0011 (12)−0.0349 (15)
C190.0450 (15)0.0657 (17)0.0630 (16)−0.0187 (13)0.0031 (12)−0.0341 (14)
C200.088 (3)0.082 (3)0.168 (4)−0.045 (2)0.025 (3)−0.052 (3)

Geometric parameters (Å, °)

O1—C81.371 (3)C7—C81.364 (3)
O1—C101.420 (3)C7—H70.9300
O2—C111.229 (3)C8—C91.423 (3)
O3—C171.361 (3)C10—C111.501 (3)
O3—H30.8200C10—H10A0.9700
O4—C201.389 (4)C10—H10B0.9700
O4—H40.8200C12—C141.490 (3)
N1—C11.319 (3)C12—C131.501 (3)
N1—C91.369 (3)C13—H13A0.9600
N2—C111.333 (3)C13—H13B0.9600
N2—N31.396 (3)C13—H13C0.9600
N2—H20.8600C14—C151.379 (3)
N3—C121.286 (3)C14—C191.387 (3)
C1—C21.399 (4)C15—C161.380 (4)
C1—H10.9300C15—H150.9300
C2—C31.352 (4)C16—C171.372 (4)
C2—H2A0.9300C16—H160.9300
C3—C41.413 (4)C17—C181.372 (4)
C3—H3A0.9300C18—C191.382 (4)
C4—C51.410 (4)C18—H180.9300
C4—C91.420 (3)C19—H190.9300
C5—C61.353 (4)C20—H20A0.9600
C5—H50.9300C20—H20B0.9600
C6—C71.404 (4)C20—H20C0.9600
C6—H60.9300
C8—O1—C10116.27 (18)C11—C10—H10B109.1
C17—O3—H3109.5H10A—C10—H10B107.9
C20—O4—H4109.5O2—C11—N2124.5 (2)
C1—N1—C9117.8 (2)O2—C11—C10117.8 (2)
C11—N2—N3118.39 (19)N2—C11—C10117.4 (2)
C11—N2—H2120.8N3—C12—C14115.1 (2)
N3—N2—H2120.8N3—C12—C13125.8 (2)
C12—N3—N2116.1 (2)C14—C12—C13118.9 (2)
N1—C1—C2124.1 (3)C12—C13—H13A109.5
N1—C1—H1117.9C12—C13—H13B109.5
C2—C1—H1117.9H13A—C13—H13B109.5
C3—C2—C1118.7 (3)C12—C13—H13C109.5
C3—C2—H2A120.6H13A—C13—H13C109.5
C1—C2—H2A120.6H13B—C13—H13C109.5
C2—C3—C4120.3 (3)C15—C14—C19117.1 (2)
C2—C3—H3A119.9C15—C14—C12121.7 (2)
C4—C3—H3A119.9C19—C14—C12121.1 (2)
C5—C4—C3123.2 (2)C14—C15—C16121.5 (2)
C5—C4—C9119.7 (2)C14—C15—H15119.2
C3—C4—C9117.1 (3)C16—C15—H15119.2
C6—C5—C4119.7 (2)C17—C16—C15120.4 (2)
C6—C5—H5120.2C17—C16—H16119.8
C4—C5—H5120.2C15—C16—H16119.8
C5—C6—C7121.7 (3)O3—C17—C18122.9 (2)
C5—C6—H6119.2O3—C17—C16117.8 (2)
C7—C6—H6119.2C18—C17—C16119.3 (2)
C8—C7—C6120.2 (3)C17—C18—C19120.0 (2)
C8—C7—H7119.9C17—C18—H18120.0
C6—C7—H7119.9C19—C18—H18120.0
C7—C8—O1124.3 (2)C18—C19—C14121.6 (2)
C7—C8—C9120.1 (2)C18—C19—H19119.2
O1—C8—C9115.5 (2)C14—C19—H19119.2
N1—C9—C4122.0 (2)O4—C20—H20A109.5
N1—C9—C8119.4 (2)O4—C20—H20B109.5
C4—C9—C8118.6 (2)H20A—C20—H20B109.5
O1—C10—C11112.4 (2)O4—C20—H20C109.5
O1—C10—H10A109.1H20A—C20—H20C109.5
C11—C10—H10A109.1H20B—C20—H20C109.5
O1—C10—H10B109.1
C11—N2—N3—C12−151.2 (2)O1—C8—C9—C4179.2 (2)
C9—N1—C1—C2−1.0 (4)C8—O1—C10—C11179.3 (2)
N1—C1—C2—C30.9 (5)N3—N2—C11—O22.2 (4)
C1—C2—C3—C40.0 (5)N3—N2—C11—C10177.3 (2)
C2—C3—C4—C5179.6 (3)O1—C10—C11—O2−167.4 (2)
C2—C3—C4—C9−0.7 (4)O1—C10—C11—N217.2 (3)
C3—C4—C5—C6179.2 (3)N2—N3—C12—C14179.9 (2)
C9—C4—C5—C6−0.5 (4)N2—N3—C12—C134.1 (4)
C4—C5—C6—C7−0.8 (4)N3—C12—C14—C15−154.8 (3)
C5—C6—C7—C81.5 (4)C13—C12—C14—C1521.3 (4)
C6—C7—C8—O1179.5 (2)N3—C12—C14—C1922.1 (3)
C6—C7—C8—C9−0.7 (4)C13—C12—C14—C19−161.8 (2)
C10—O1—C8—C76.5 (3)C19—C14—C15—C16−1.2 (4)
C10—O1—C8—C9−173.2 (2)C12—C14—C15—C16175.9 (3)
C1—N1—C9—C40.2 (4)C14—C15—C16—C170.5 (5)
C1—N1—C9—C8179.3 (2)C15—C16—C17—O3179.8 (3)
C5—C4—C9—N1−179.7 (2)C15—C16—C17—C180.4 (4)
C3—C4—C9—N10.6 (4)O3—C17—C18—C19180.0 (3)
C5—C4—C9—C81.2 (4)C16—C17—C18—C19−0.7 (4)
C3—C4—C9—C8−178.5 (2)C17—C18—C19—C140.0 (4)
C7—C8—C9—N1−179.7 (2)C15—C14—C19—C180.9 (4)
O1—C8—C9—N10.1 (3)C12—C14—C19—C18−176.1 (2)
C7—C8—C9—C4−0.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.852.647 (3)165
O4—H4···N10.821.962.773 (3)174
O4—H4···O10.822.603.036 (3)115
N2—H2···O40.862.102.856 (3)146

Symmetry codes: (i) −x−1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2916).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev.171, 161—174.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Wen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045–o2046.

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