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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1154.
Published online 2009 April 30. doi:  10.1107/S1600536809015165
PMCID: PMC2977820

(E)-N′-(2,5-Dimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Abstract

The two mol­ecules in the asymmetric unit of the title compound, C20H19N3O4·CH4O, are paired via O—H(...)(O,N), N—H(...)O, and C—H(...)O hydrogen bonds. The mol­ecular skeleton of the acetohydrazide mol­ecule is close to planar; the benzene and quinoline mean planes form a dihedral angle of 3.9 (3)°. The crystal packing exhibits weak inter­molecular C—H(...)O hydrogen bonds and π–π inter­actions, indicated by short distances of 3.668 (3) Å, between the centroids of N-containing six-membered rings from neighbouring acetohydrazide mol­ecules.

Related literature

For applications of 8-hydroxy­quinoline and its derivatives, see: Park et al. (2006 [triangle]); Karmakar et al. (2007 [triangle]). For a related structure, see Wen et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1154-scheme1.jpg

Experimental

Crystal data

  • C20H19N3O4·CH4O
  • M r = 397.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1154-efi1.jpg
  • a = 9.4199 (12) Å
  • b = 10.8652 (14) Å
  • c = 11.1721 (14) Å
  • α = 93.268 (1)°
  • β = 112.816 (2)°
  • γ = 107.859 (3)°
  • V = 982.8 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.985
  • 5196 measured reflections
  • 3456 independent reflections
  • 2363 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.149
  • S = 1.03
  • 3456 reflections
  • 263 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.33 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/S1600536809015165/cv2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015165/cv2552Isup2.hkl

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

supplementary crystallographic information

Comment

Synthesis of 8-hydroxyquinoline and its derivatives have attracted a great interest due to their interesting biological activities and applications in coordination chemistry (Park et al., 2006; Karmakar et al., 2007). As a part of our ongoing search for good extractants of metal ions and biologically active materials, the title compound, (I), was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 2,5-dimethoxybenzaldehyde.

In (I) (Fig. 1), all bond lengths and angles are normal and 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 3.9 (3)°. In the crystal structure, the methanol molecule is linked to the C20H19N3O4 molecule via intermolecular O—H···O, N—H···O, O—H···N and C—H···O hydrogen bonds(Fig. 1 and Table 1). The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds and π–π interactions proved by short distance of 3.668 (3) Å between the centroids of N-containing six-membered rings from the neighbouring molecules L.

Experimental

2-(Quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 2,5-dimethoxybenzaldehyde (1.66 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. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a acetone-methanol (1:1, v/v) solution over a period of 2 d.

Refinement

All H atoms were initially located in a difference Fourier map. C-bound 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.

Crystal data

C20H19N3O4·CH4OZ = 2
Mr = 397.42F(000) = 420
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4199 (12) ÅCell parameters from 1903 reflections
b = 10.8652 (14) Åθ = 2.5–26.9°
c = 11.1721 (14) ŵ = 0.10 mm1
α = 93.268 (1)°T = 295 K
β = 112.816 (2)°Block, colorless
γ = 107.859 (3)°0.22 × 0.18 × 0.16 mm
V = 982.8 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3456 independent reflections
Radiation source: fine-focus sealed tube2363 reflections with I > 2σ(I)
graphiteRint = 0.019
[var phi] and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.979, Tmax = 0.985k = −12→12
5196 measured reflectionsl = −13→10

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) = 0.149H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0685P)2 + 0.304P] where P = (Fo2 + 2Fc2)/3
3456 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.33 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
O1−0.24162 (17)0.13371 (15)0.32912 (13)0.0535 (4)
O20.0642 (2)0.1461 (2)0.64429 (16)0.0858 (6)
O30.4628 (2)0.39500 (19)0.28395 (18)0.0788 (5)
O40.8736 (2)0.3699 (2)0.7849 (2)0.0949 (7)
O5−0.0293 (3)0.2135 (3)0.1843 (2)0.1266 (11)
H5A−0.10810.23240.18180.190*
N1−0.3582 (2)0.19146 (18)0.08689 (17)0.0528 (5)
N20.0876 (2)0.19807 (18)0.45814 (17)0.0560 (5)
H20.03710.20200.37660.067*
N30.2580 (2)0.23818 (18)0.51768 (18)0.0558 (5)
C1−0.4175 (3)0.2184 (2)−0.0328 (2)0.0601 (6)
H1−0.34280.2594−0.06640.072*
C2−0.5851 (3)0.1892 (2)−0.1121 (2)0.0643 (7)
H2A−0.62030.2104−0.19560.077*
C3−0.6951 (3)0.1293 (2)−0.0644 (2)0.0627 (6)
H3−0.80730.1086−0.11540.075*
C4−0.6394 (3)0.0981 (2)0.0630 (2)0.0536 (6)
C5−0.7479 (3)0.0345 (3)0.1181 (3)0.0662 (7)
H5−0.86080.01410.07090.079*
C6−0.6890 (3)0.0033 (3)0.2383 (3)0.0693 (7)
H6−0.7616−0.03930.27310.083*
C7−0.5183 (3)0.0346 (2)0.3117 (2)0.0575 (6)
H7−0.47960.01160.39410.069*
C8−0.4090 (2)0.0981 (2)0.2636 (2)0.0474 (5)
C9−0.4680 (3)0.1308 (2)0.1355 (2)0.0473 (5)
C10−0.1828 (3)0.1048 (2)0.4579 (2)0.0543 (6)
H10A−0.22620.01010.45090.065*
H10B−0.22400.14500.51060.065*
C110.0023 (3)0.1532 (2)0.5280 (2)0.0549 (6)
C120.3277 (3)0.2839 (2)0.4443 (2)0.0603 (6)
H120.26220.28590.35760.072*
C130.5061 (3)0.3334 (2)0.4906 (2)0.0568 (6)
C140.5723 (3)0.3921 (2)0.4061 (3)0.0625 (6)
C150.7399 (4)0.4419 (3)0.4488 (3)0.0800 (8)
H150.78430.47980.39260.096*
C160.8436 (4)0.4366 (3)0.5739 (3)0.0842 (9)
H160.95720.47220.60200.101*
C170.7807 (3)0.3791 (3)0.6577 (3)0.0701 (7)
C180.6115 (3)0.3272 (2)0.6158 (3)0.0637 (6)
H180.56820.28790.67200.076*
C190.5240 (4)0.4653 (3)0.2014 (3)0.0892 (9)
H19A0.58710.55570.24600.134*
H19B0.43350.46160.12060.134*
H19C0.59310.42650.18140.134*
C201.0484 (4)0.4126 (4)0.8254 (4)0.1123 (12)
H20A1.07160.35720.77100.168*
H20B1.10200.40680.91640.168*
H20C1.08850.50230.81590.168*
C210.0330 (4)0.2797 (4)0.1045 (3)0.0957 (10)
H21A0.04940.37150.12450.144*
H21B−0.04320.24340.01330.144*
H21C0.13650.27050.11970.144*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0409 (8)0.0744 (10)0.0410 (8)0.0212 (7)0.0117 (7)0.0201 (7)
O20.0538 (10)0.1467 (18)0.0475 (10)0.0343 (11)0.0108 (8)0.0388 (11)
O30.0767 (12)0.0900 (13)0.0686 (12)0.0228 (10)0.0340 (10)0.0253 (10)
O40.0494 (11)0.1275 (18)0.0953 (15)0.0243 (11)0.0215 (10)0.0391 (13)
O50.0554 (12)0.231 (3)0.0757 (14)0.0286 (15)0.0217 (11)0.0755 (17)
N10.0500 (11)0.0604 (11)0.0436 (10)0.0208 (9)0.0143 (9)0.0138 (9)
N20.0412 (10)0.0703 (12)0.0432 (10)0.0135 (9)0.0089 (8)0.0160 (9)
N30.0412 (10)0.0607 (12)0.0548 (11)0.0126 (9)0.0139 (9)0.0118 (9)
C10.0621 (15)0.0668 (15)0.0468 (13)0.0245 (12)0.0164 (12)0.0188 (11)
C20.0704 (17)0.0686 (16)0.0465 (13)0.0317 (13)0.0112 (12)0.0177 (11)
C30.0519 (14)0.0673 (15)0.0549 (14)0.0260 (12)0.0052 (12)0.0122 (12)
C40.0458 (12)0.0561 (13)0.0493 (12)0.0219 (10)0.0083 (10)0.0069 (10)
C50.0405 (13)0.0817 (17)0.0658 (16)0.0215 (12)0.0121 (12)0.0161 (13)
C60.0475 (14)0.0895 (19)0.0670 (16)0.0188 (13)0.0245 (12)0.0199 (14)
C70.0506 (13)0.0723 (16)0.0487 (13)0.0231 (12)0.0186 (11)0.0167 (11)
C80.0396 (12)0.0538 (12)0.0434 (11)0.0181 (10)0.0115 (10)0.0068 (9)
C90.0452 (12)0.0485 (12)0.0431 (11)0.0191 (10)0.0124 (10)0.0071 (9)
C100.0471 (13)0.0720 (15)0.0431 (12)0.0235 (11)0.0154 (10)0.0214 (11)
C110.0467 (13)0.0679 (15)0.0437 (12)0.0211 (11)0.0117 (10)0.0174 (11)
C120.0515 (14)0.0667 (15)0.0543 (14)0.0162 (11)0.0181 (12)0.0106 (11)
C130.0510 (14)0.0536 (13)0.0624 (15)0.0152 (11)0.0240 (12)0.0073 (11)
C140.0608 (15)0.0559 (14)0.0722 (16)0.0179 (12)0.0324 (13)0.0094 (12)
C150.0690 (18)0.088 (2)0.094 (2)0.0265 (15)0.0457 (17)0.0337 (17)
C160.0548 (16)0.093 (2)0.108 (2)0.0191 (15)0.0427 (17)0.0303 (18)
C170.0496 (15)0.0756 (17)0.0789 (18)0.0232 (13)0.0203 (14)0.0169 (14)
C180.0540 (15)0.0660 (15)0.0709 (16)0.0177 (12)0.0292 (13)0.0139 (12)
C190.102 (2)0.088 (2)0.0793 (19)0.0258 (18)0.0458 (18)0.0277 (16)
C200.0522 (18)0.155 (3)0.114 (3)0.033 (2)0.0210 (18)0.041 (2)
C210.076 (2)0.121 (3)0.082 (2)0.0229 (18)0.0332 (17)0.0275 (19)

Geometric parameters (Å, °)

O1—C81.367 (2)C7—C81.364 (3)
O1—C101.420 (2)C7—H70.9300
O2—C111.219 (3)C8—C91.430 (3)
O3—C141.364 (3)C10—C111.504 (3)
O3—C191.410 (3)C10—H10A0.9700
O4—C171.378 (3)C10—H10B0.9700
O4—C201.435 (3)C12—C131.456 (3)
O5—C211.371 (3)C12—H120.9300
O5—H5A0.8200C13—C181.386 (3)
N1—C11.324 (3)C13—C141.403 (3)
N1—C91.363 (3)C14—C151.369 (4)
N2—C111.335 (3)C15—C161.378 (4)
N2—N31.385 (2)C15—H150.9300
N2—H20.8600C16—C171.374 (4)
N3—C121.271 (3)C16—H160.9300
C1—C21.398 (3)C17—C181.385 (3)
C1—H10.9300C18—H180.9300
C2—C31.355 (4)C19—H19A0.9600
C2—H2A0.9300C19—H19B0.9600
C3—C41.414 (3)C19—H19C0.9600
C3—H30.9300C20—H20A0.9600
C4—C91.411 (3)C20—H20B0.9600
C4—C51.415 (3)C20—H20C0.9600
C5—C61.348 (3)C21—H21A0.9600
C5—H50.9300C21—H21B0.9600
C6—C71.408 (3)C21—H21C0.9600
C6—H60.9300
C8—O1—C10115.50 (17)O2—C11—N2124.4 (2)
C14—O3—C19118.6 (2)O2—C11—C10117.6 (2)
C17—O4—C20116.1 (2)N2—C11—C10117.96 (18)
C21—O5—H5A109.5N3—C12—C13122.5 (2)
C1—N1—C9117.75 (19)N3—C12—H12118.7
C11—N2—N3119.67 (17)C13—C12—H12118.7
C11—N2—H2120.2C18—C13—C14119.4 (2)
N3—N2—H2120.2C18—C13—C12122.2 (2)
C12—N3—N2114.67 (19)C14—C13—C12118.4 (2)
N1—C1—C2124.2 (2)O3—C14—C15123.8 (2)
N1—C1—H1117.9O3—C14—C13116.8 (2)
C2—C1—H1117.9C15—C14—C13119.3 (3)
C3—C2—C1118.4 (2)C14—C15—C16120.8 (3)
C3—C2—H2A120.8C14—C15—H15119.6
C1—C2—H2A120.8C16—C15—H15119.6
C2—C3—C4120.1 (2)C17—C16—C15120.6 (3)
C2—C3—H3120.0C17—C16—H16119.7
C4—C3—H3120.0C15—C16—H16119.7
C9—C4—C3117.5 (2)C16—C17—O4125.0 (2)
C9—C4—C5119.7 (2)C16—C17—C18119.4 (3)
C3—C4—C5122.8 (2)O4—C17—C18115.5 (2)
C6—C5—C4120.5 (2)C17—C18—C13120.4 (2)
C6—C5—H5119.7C17—C18—H18119.8
C4—C5—H5119.7C13—C18—H18119.8
C5—C6—C7120.5 (2)O3—C19—H19A109.5
C5—C6—H6119.8O3—C19—H19B109.5
C7—C6—H6119.8H19A—C19—H19B109.5
C8—C7—C6121.0 (2)O3—C19—H19C109.5
C8—C7—H7119.5H19A—C19—H19C109.5
C6—C7—H7119.5H19B—C19—H19C109.5
C7—C8—O1124.68 (19)O4—C20—H20A109.5
C7—C8—C9119.8 (2)O4—C20—H20B109.5
O1—C8—C9115.50 (18)H20A—C20—H20B109.5
N1—C9—C4122.07 (19)O4—C20—H20C109.5
N1—C9—C8119.45 (18)H20A—C20—H20C109.5
C4—C9—C8118.5 (2)H20B—C20—H20C109.5
O1—C10—C11113.06 (18)O5—C21—H21A109.5
O1—C10—H10A109.0O5—C21—H21B109.5
C11—C10—H10A109.0H21A—C21—H21B109.5
O1—C10—H10B109.0O5—C21—H21C109.5
C11—C10—H10B109.0H21A—C21—H21C109.5
H10A—C10—H10B107.8H21B—C21—H21C109.5
C11—N2—N3—C12−177.4 (2)N3—N2—C11—O21.0 (4)
C9—N1—C1—C20.3 (3)N3—N2—C11—C10−177.22 (19)
N1—C1—C2—C3−0.1 (4)O1—C10—C11—O2172.0 (2)
C1—C2—C3—C40.2 (4)O1—C10—C11—N2−9.6 (3)
C2—C3—C4—C9−0.6 (3)N2—N3—C12—C13178.7 (2)
C2—C3—C4—C5−179.4 (2)N3—C12—C13—C183.6 (4)
C9—C4—C5—C6−0.9 (4)N3—C12—C13—C14−174.8 (2)
C3—C4—C5—C6177.9 (2)C19—O3—C14—C15−7.1 (4)
C4—C5—C6—C70.6 (4)C19—O3—C14—C13173.3 (2)
C5—C6—C7—C80.7 (4)C18—C13—C14—O3179.8 (2)
C6—C7—C8—O1179.0 (2)C12—C13—C14—O3−1.8 (3)
C6—C7—C8—C9−1.6 (3)C18—C13—C14—C150.2 (4)
C10—O1—C8—C7−2.3 (3)C12—C13—C14—C15178.6 (2)
C10—O1—C8—C9178.19 (18)O3—C14—C15—C16179.5 (3)
C1—N1—C9—C4−0.7 (3)C13—C14—C15—C16−0.9 (4)
C1—N1—C9—C8179.0 (2)C14—C15—C16—C171.1 (5)
C3—C4—C9—N10.8 (3)C15—C16—C17—O4−179.3 (3)
C5—C4—C9—N1179.7 (2)C15—C16—C17—C18−0.5 (4)
C3—C4—C9—C8−178.88 (19)C20—O4—C17—C16−6.5 (4)
C5—C4—C9—C80.0 (3)C20—O4—C17—C18174.7 (3)
C7—C8—C9—N1−178.5 (2)C16—C17—C18—C13−0.2 (4)
O1—C8—C9—N11.0 (3)O4—C17—C18—C13178.7 (2)
C7—C8—C9—C41.2 (3)C14—C13—C18—C170.4 (4)
O1—C8—C9—C4−179.29 (18)C12—C13—C18—C17−178.0 (2)
C8—O1—C10—C11−176.68 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5A···O10.822.532.996 (3)117
O5—H5A···N10.822.062.782 (3)147
N2—H2···O50.862.012.856 (3)166
C12—H12···O50.932.513.305 (3)144
C3—H3···O2i0.932.603.220 (3)125
C20—H20A···O2ii0.962.593.511 (5)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2552).

References

  • Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). CrystEngComm, 9, 379–389.
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