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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2114.
Published online 2008 October 15. doi:  10.1107/S1600536808032674
PMCID: PMC2959671

(E)-N′-(Furan-2-ylmethyl­ene)-4-(quinolin-8-yl­oxy)butanohydrazide

Abstract

In the title mol­ecule, C18H17N3O3, the dihedral angle between the mean planes of the furan ring and the quinoline group is 77.4 (2)°. In the crystal structure, inter­molecular N—H(...)N hydrogen bonds link the mol­ecules into centrosymmetric dimers.

Related literature

For general background, see: Cai et al. (2003 [triangle]); Chen et al. (2005 [triangle]); Park et al. (2006 [triangle]); Karmakar et al. (2007 [triangle]). For related structures, see: Zheng (2006 [triangle]); Zheng, Wu et al. (2006 [triangle]); Zheng, Li et al. (2006 [triangle]); Zheng et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2114-scheme1.jpg

Experimental

Crystal data

  • C18H17N3O3
  • M r = 323.35
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2114-efi1.jpg
  • a = 8.2685 (17) Å
  • b = 8.6324 (17) Å
  • c = 12.765 (3) Å
  • α = 100.64 (3)°
  • β = 100.36 (4)°
  • γ = 109.50 (3)°
  • V = 814.9 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.33 × 0.26 × 0.21 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.970, T max = 0.981
  • 9399 measured reflections
  • 2865 independent reflections
  • 1632 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.193
  • S = 1.06
  • 2865 reflections
  • 218 parameters
  • 21 restraints
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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/S1600536808032674/lh2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032674/lh2705Isup2.hkl

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

Acknowledgments

This work was supported by a key grant from the Shanxi Datong University Foundation of Shanxi Province (grant No. 2008K1).

supplementary crystallographic information

Comment

Synthsis of 8-Hydroxyquinoline and its derivatives have attracted a great interest due to their interesting biological activities and applications in coordination chemistry (Cai et al., 2003; Chen et al., 2005; Park et al., 2006; Karmakar et al. 2007). Herein, we report the synthesis and crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1. The conformation along the O1—C10—C11—C12—C13—N2—N3—C14 bond sequence is (-)gauche-trans-trans-(-)gauche-trans. The mean planes of the furan ring and quinoline group make a dihedral angle of 77.4 (2) °. In the crystal structure (Fig. 2), intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. Some crystal structures which are closely related to the title compound have already been studied (Zheng, 2006; Zheng, Wu et al.,2006; Zheng, et al.,2007; Zheng, Li et al., 2006; Zheng, et al., 2008.

Experimental

Reagents and solvents used were of commercially available quality. The title complex (I) was synthesized according to the method of Zheng (2006). 4-(Quinolin-8-yloxy)butanohydrazide (0.01 mol), furan-2-carbaldehyde (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask and refluxed for 6 h. After cooling to room temperature, the solid product was separated by filtration. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a tetrahydrofuran solution over a period of 2 d.

Refinement

All H atoms were placed in idealized positions (C—H = 0.93–0.97Å and N—H = 0.86Å) and refined as riding atoms with Uiso(H) = 1.2Ueq(C,N). In the molecule, some anisotropic displacemnt parameters of the atoms are larger than normal and restraints were applied in the form of the DELU and SIMU instructions in the SHELXL (Sheldrick, 2008) program.

Figures

Fig. 1.
The molecular structure with displacement ellipsoids at the 30% probability level.
Fig. 2.
Part of the crystal structure showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

Crystal data

C18H17N3O3Z = 2
Mr = 323.35F(000) = 340
Triclinic, P1Dx = 1.318 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2685 (17) ÅCell parameters from 1197 reflections
b = 8.6324 (17) Åθ = 2.6–20.5°
c = 12.765 (3) ŵ = 0.09 mm1
α = 100.64 (3)°T = 295 K
β = 100.36 (4)°Block, colorless
γ = 109.50 (3)°0.33 × 0.26 × 0.21 mm
V = 814.9 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer2865 independent reflections
Radiation source: fine-focus sealed tube1632 reflections with I > 2σ(I)
graphiteRint = 0.043
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→8
Tmin = 0.970, Tmax = 0.981k = −10→10
9399 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.193w = 1/[σ2(Fo2) + (0.0865P)2 + 0.1859P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2865 reflectionsΔρmax = 0.24 e Å3
218 parametersΔρmin = −0.20 e Å3
21 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.015 (6)

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
N10.2058 (3)0.5842 (4)0.8792 (2)0.0700 (8)
N2−0.0972 (4)0.3300 (3)0.3273 (2)0.0681 (8)
H1−0.11740.37540.27430.082*
N3−0.2378 (4)0.2174 (3)0.3521 (2)0.0608 (7)
O10.2645 (3)0.3778 (2)0.72254 (16)0.0631 (6)
O20.1947 (3)0.4670 (3)0.3574 (2)0.0890 (8)
C16−0.7219 (5)0.0732 (5)0.2779 (3)0.0811 (10)
H16−0.76440.13490.23530.097*
C10.2775 (4)0.3409 (4)0.8220 (3)0.0682 (9)
C20.3186 (5)0.2071 (5)0.8455 (4)0.1060 (15)
H20.33940.13300.79160.127*
C30.3287 (7)0.1846 (8)0.9529 (6)0.147 (2)
H30.35250.09200.96820.176*
C40.3056 (7)0.2905 (10)1.0325 (5)0.154 (3)
H40.31760.27271.10260.184*
C50.2631 (5)0.4296 (8)1.0135 (4)0.1188 (17)
C60.2347 (8)0.5503 (12)1.0944 (5)0.164 (3)
H60.24090.53921.16590.197*
C70.1999 (8)0.6759 (9)1.0659 (4)0.154 (3)
H70.18580.75701.11850.185*
C80.1837 (5)0.6903 (6)0.9582 (3)0.1034 (15)
H80.15560.78000.94110.124*
C90.2483 (4)0.4547 (5)0.9052 (2)0.0717 (10)
C100.3224 (4)0.2872 (4)0.6405 (3)0.0767 (10)
H10A0.25430.16570.62330.092*
H10B0.44700.30770.66770.092*
C110.2946 (4)0.3499 (4)0.5394 (3)0.0737 (10)
H11A0.35150.30510.48800.088*
H11B0.35170.47310.56000.088*
C120.1001 (4)0.2989 (4)0.4818 (3)0.0660 (9)
H12A0.04460.17560.45690.079*
H12B0.04130.33750.53440.079*
C130.0731 (5)0.3712 (4)0.3847 (3)0.0657 (9)
C14−0.3915 (4)0.2060 (4)0.3007 (2)0.0617 (8)
H14−0.39840.27460.25320.074*
C15−0.5530 (4)0.0908 (4)0.3141 (2)0.0591 (8)
O3−0.5432 (3)−0.0227 (3)0.3737 (2)0.0872 (8)
C18−0.7117 (6)−0.1128 (5)0.3740 (4)0.1000 (13)
H18−0.7433−0.19980.40890.120*
C17−0.8239 (5)−0.0625 (5)0.3191 (3)0.0867 (12)
H17−0.9466−0.10550.30840.104*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0610 (17)0.0779 (18)0.0552 (16)0.0069 (14)0.0221 (13)0.0102 (14)
N20.0650 (18)0.0685 (17)0.0741 (17)0.0177 (14)0.0275 (14)0.0316 (14)
N30.0621 (17)0.0560 (15)0.0643 (15)0.0150 (13)0.0258 (13)0.0206 (12)
O10.0712 (14)0.0671 (13)0.0592 (13)0.0337 (11)0.0168 (10)0.0224 (10)
O20.0729 (17)0.0872 (17)0.1058 (19)0.0133 (13)0.0390 (14)0.0396 (14)
C160.070 (2)0.097 (3)0.073 (2)0.032 (2)0.0116 (18)0.020 (2)
C10.0464 (18)0.068 (2)0.077 (2)0.0050 (15)−0.0011 (15)0.0366 (19)
C20.062 (2)0.086 (3)0.154 (4)0.011 (2)−0.011 (2)0.065 (3)
C30.086 (3)0.140 (4)0.180 (5)−0.006 (3)−0.031 (4)0.122 (4)
C40.081 (3)0.199 (5)0.126 (4)−0.028 (3)−0.024 (3)0.119 (4)
C50.055 (2)0.178 (4)0.077 (3)−0.024 (2)−0.0051 (19)0.079 (3)
C60.079 (4)0.269 (8)0.046 (3)−0.051 (4)0.011 (2)0.031 (4)
C70.087 (4)0.208 (7)0.067 (4)−0.039 (4)0.036 (3)−0.037 (4)
C80.078 (3)0.109 (3)0.082 (3)−0.004 (2)0.040 (2)−0.015 (2)
C90.0455 (19)0.092 (3)0.0510 (19)−0.0082 (17)0.0031 (14)0.0302 (19)
C100.061 (2)0.072 (2)0.088 (2)0.0296 (18)0.0090 (18)0.0025 (19)
C110.058 (2)0.082 (2)0.069 (2)0.0210 (17)0.0216 (17)−0.0016 (18)
C120.060 (2)0.0655 (19)0.069 (2)0.0189 (16)0.0242 (16)0.0123 (16)
C130.071 (2)0.0574 (19)0.070 (2)0.0195 (17)0.0317 (18)0.0178 (16)
C140.067 (2)0.0621 (19)0.0605 (18)0.0215 (16)0.0234 (16)0.0245 (15)
C150.068 (2)0.0585 (18)0.0535 (17)0.0218 (16)0.0202 (15)0.0199 (14)
O30.0827 (18)0.0858 (17)0.1002 (18)0.0247 (14)0.0323 (14)0.0469 (14)
C180.083 (3)0.092 (3)0.113 (3)0.004 (2)0.046 (3)0.034 (2)
C170.054 (2)0.096 (3)0.081 (2)0.005 (2)0.0213 (19)−0.002 (2)

Geometric parameters (Å, °)

N1—C81.314 (4)C6—C71.306 (10)
N1—C91.357 (4)C6—H60.9300
N2—C131.358 (4)C7—C81.389 (7)
N2—N31.374 (3)C7—H70.9300
N2—H10.8600C8—H80.9300
N3—C141.283 (4)C10—C111.499 (5)
O1—C11.360 (4)C10—H10A0.9700
O1—C101.437 (4)C10—H10B0.9700
O2—C131.222 (4)C11—C121.517 (4)
C16—C151.337 (5)C11—H11A0.9700
C16—C171.445 (5)C11—H11B0.9700
C16—H160.9300C12—C131.501 (4)
C1—C21.375 (5)C12—H12A0.9700
C1—C91.419 (5)C12—H12B0.9700
C2—C31.412 (7)C14—C151.435 (4)
C2—H20.9300C14—H140.9300
C3—C41.322 (9)C15—O31.361 (4)
C3—H30.9300O3—C181.351 (4)
C4—C51.408 (9)C18—C171.300 (5)
C4—H40.9300C18—H180.9300
C5—C91.428 (5)C17—H170.9300
C5—C61.436 (9)
C8—N1—C9117.8 (3)C1—C9—C5119.4 (4)
C13—N2—N3121.3 (3)O1—C10—C11107.8 (3)
C13—N2—H1119.3O1—C10—H10A110.2
N3—N2—H1119.3C11—C10—H10A110.2
C14—N3—N2114.7 (3)O1—C10—H10B110.2
C1—O1—C10118.0 (3)C11—C10—H10B110.2
C15—C16—C17105.0 (3)H10A—C10—H10B108.5
C15—C16—H16127.5C10—C11—C12113.4 (3)
C17—C16—H16127.5C10—C11—H11A108.9
O1—C1—C2124.8 (4)C12—C11—H11A108.9
O1—C1—C9115.0 (3)C10—C11—H11B108.9
C2—C1—C9120.2 (4)C12—C11—H11B108.9
C1—C2—C3118.7 (5)H11A—C11—H11B107.7
C1—C2—H2120.7C13—C12—C11113.1 (3)
C3—C2—H2120.7C13—C12—H12A109.0
C4—C3—C2122.3 (6)C11—C12—H12A109.0
C4—C3—H3118.8C13—C12—H12B109.0
C2—C3—H3118.8C11—C12—H12B109.0
C3—C4—C5121.5 (6)H12A—C12—H12B107.8
C3—C4—H4119.2O2—C13—N2119.3 (3)
C5—C4—H4119.2O2—C13—C12123.6 (3)
C4—C5—C9117.7 (6)N2—C13—C12117.1 (3)
C4—C5—C6125.4 (5)N3—C14—C15122.2 (3)
C9—C5—C6116.8 (6)N3—C14—H14118.9
C7—C6—C5118.9 (6)C15—C14—H14118.9
C7—C6—H6120.5C16—C15—O3110.4 (3)
C5—C6—H6120.5C16—C15—C14130.9 (3)
C6—C7—C8121.1 (7)O3—C15—C14118.7 (3)
C6—C7—H7119.5C18—O3—C15106.4 (3)
C8—C7—H7119.5C17—C18—O3111.3 (4)
N1—C8—C7123.6 (5)C17—C18—H18124.4
N1—C8—H8118.2O3—C18—H18124.4
C7—C8—H8118.2C18—C17—C16106.9 (3)
N1—C9—C1118.9 (3)C18—C17—H17126.5
N1—C9—C5121.7 (4)C16—C17—H17126.5
C13—N2—N3—C14171.9 (3)C6—C5—C9—N1−1.4 (5)
C10—O1—C1—C2−9.5 (4)C4—C5—C9—C1−0.4 (5)
C10—O1—C1—C9169.3 (2)C6—C5—C9—C1179.1 (4)
O1—C1—C2—C3179.6 (3)C1—O1—C10—C11179.9 (2)
C9—C1—C2—C30.8 (5)O1—C10—C11—C12−68.5 (3)
C1—C2—C3—C4−2.2 (7)C10—C11—C12—C13176.4 (3)
C2—C3—C4—C52.2 (9)N3—N2—C13—O2177.3 (3)
C3—C4—C5—C9−0.9 (7)N3—N2—C13—C12−4.6 (4)
C3—C4—C5—C6179.6 (5)C11—C12—C13—O2−2.9 (4)
C4—C5—C6—C7178.5 (5)C11—C12—C13—N2179.1 (3)
C9—C5—C6—C7−1.0 (8)N2—N3—C14—C15178.1 (3)
C5—C6—C7—C82.4 (10)C17—C16—C15—O30.2 (4)
C9—N1—C8—C7−0.6 (5)C17—C16—C15—C14−179.2 (3)
C6—C7—C8—N1−1.7 (8)N3—C14—C15—C16172.0 (3)
C8—N1—C9—C1−178.4 (3)N3—C14—C15—O3−7.3 (4)
C8—N1—C9—C52.1 (4)C16—C15—O3—C180.0 (4)
O1—C1—C9—N12.0 (4)C14—C15—O3—C18179.5 (3)
C2—C1—C9—N1−179.2 (3)C15—O3—C18—C17−0.2 (4)
O1—C1—C9—C5−178.5 (3)O3—C18—C17—C160.3 (5)
C2—C1—C9—C50.4 (4)C15—C16—C17—C18−0.2 (4)
C4—C5—C9—N1179.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H1···N1i0.862.102.936 (4)164

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2705).

References

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