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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1212.
Published online 2009 May 7. doi:  10.1107/S1600536809015992
PMCID: PMC2969732

(E)-N′-(4-Nitro­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Abstract

In the title compound, C18H14N4O4·CH3OH, the mean planes of the benzene ring and the quinoline ring system make a dihedral angle of 15.5 (2)°. The methanol solvent mol­ecule forms an O—H(...)N hydrogen bond to the quinoline ring system and accepts an N—H(...)O hydrogen bond from the hydrazide NH group. The mol­ecules lie in layers approximately parallel to (101) and C—H(...)O inter­actions exist between mol­ecules within the layers.

Related literature

For the coordination chemistry of 8-hydroxy­quinoline and its derivatives, see: Chen & Shi (1998 [triangle]); Mona & Wageih (2002 [triangle]). For a related structure, see: Tan (2009 [triangle]).

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Object name is e-65-o1212-scheme1.jpg

Experimental

Crystal data

  • C18H14N4O4·CH4O
  • M r = 382.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1212-efi1.jpg
  • a = 11.345 (10) Å
  • b = 11.559 (11) Å
  • c = 16.234 (12) Å
  • β = 120.06 (5)°
  • V = 1843 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 K
  • 0.20 × 0.18 × 0.16 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.980, T max = 0.984
  • 9196 measured reflections
  • 3258 independent reflections
  • 1872 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.195
  • S = 1.00
  • 3258 reflections
  • 255 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.26 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/S1600536809015992/bi2363sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015992/bi2363Isup2.hkl

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

supplementary crystallographic information

Comment

8-Hydroxyquinoline and its derivatives are well-known ligands in coordination chemistry (Chen & Shi, 1998; Mona & Wageih, 2002). In our search for new extractants of metal ions and biologically active materials, the title compound has been synthesized. In the crystal structure, all bond lengths and angles are normal and comparable to those in the related compound (E)-N'-[1-(4-hydroxyphenyl) ethylidene]-2-(quinolin-8-yloxy)acetohydrazide methanol solvate (Tan, 2009). The mean planes of the benzene ring and the quinoline rings make a dihedral angle of 15.5 (2)°. The methanol molecule is linked to the C18H14N4O4 molecule via intermolecular O—H···N and N—H···O hydrogen bonds (Fig. 1). The molecules lie in layers approximately parallel to (101) and C—H···O interactions exist between molecules.

Experimental

2-(Quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-nitrobenzaldehyde (1.51 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 were obtained by slow evaporation of an acetone-methanol (1:2, v/v) solution over a period of 3 d.

Refinement

All H atoms were visible in a difference Fourier map, but were placed in calculated positions with C—H = 0.93 Å for aryl, 0.97 Å for methylene and 0.96 Å for the methyl H atoms, O—H = 0.82 Å and N—H = 0.86 Å, and refined as riding with Uiso(H) = 1.2Ueq(C/N), or 1.5Ueq(C) for the methyl groups, and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure with displacement ellipsoids drawn at the 30% probability level for non-H atoms. The dashed lines indicate hydrogen bonds.
Fig. 2.
Intermolecular C—H···O interactions (dashed lines). H atoms have been omitted for clarity.

Crystal data

C18H14N4O4·CH4OF(000) = 800
Mr = 382.37Dx = 1.378 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1871 reflections
a = 11.345 (10) Åθ = 2.3–22.8°
b = 11.559 (11) ŵ = 0.10 mm1
c = 16.234 (12) ÅT = 295 K
β = 120.06 (5)°Block, colorless
V = 1843 (3) Å30.20 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer3258 independent reflections
Radiation source: fine-focus sealed tube1872 reflections with I > 2σ(I)
graphiteRint = 0.050
[var phi] and ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→10
Tmin = 0.980, Tmax = 0.984k = −12→13
9196 measured reflectionsl = −17→19

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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.1106P)2 + 0.0143P] where P = (Fo2 + 2Fc2)/3
3258 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.26 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
O10.1624 (2)0.23691 (14)1.11105 (14)0.0547 (6)
O20.1325 (2)−0.07065 (16)1.10099 (16)0.0694 (7)
O30.4318 (3)−0.4685 (3)0.7787 (2)0.1065 (10)
O40.5020 (4)−0.3368 (3)0.7175 (2)0.1177 (12)
O50.2556 (3)0.27429 (19)0.9641 (2)0.0938 (9)
H50.25400.31801.00330.141*
N10.2147 (3)0.45024 (19)1.06723 (17)0.0541 (7)
N20.2130 (3)0.05140 (19)1.02969 (17)0.0547 (7)
H20.23100.12141.02190.066*
N30.2403 (3)−0.0398 (2)0.98661 (17)0.0538 (7)
N40.4508 (3)−0.3671 (3)0.7651 (2)0.0834 (9)
C10.2366 (3)0.5556 (3)1.0457 (2)0.0621 (9)
H10.28480.56211.01350.075*
C20.1921 (4)0.6582 (2)1.0679 (2)0.0652 (9)
H2A0.21010.72981.05040.078*
C30.1227 (4)0.6509 (2)1.1152 (2)0.0602 (9)
H30.09090.71761.12960.072*
C40.0985 (3)0.5417 (2)1.14255 (19)0.0510 (8)
C50.0322 (3)0.5278 (3)1.1966 (2)0.0605 (9)
H5A−0.00140.59241.21230.073*
C60.0173 (3)0.4215 (3)1.2255 (2)0.0618 (9)
H6−0.02210.41411.26350.074*
C70.0611 (3)0.3223 (2)1.1981 (2)0.0569 (8)
H70.04830.24981.21720.068*
C80.1224 (3)0.3306 (2)1.14367 (19)0.0474 (7)
C90.1459 (3)0.4422 (2)1.11638 (18)0.0456 (7)
C100.1252 (3)0.1263 (2)1.1307 (2)0.0564 (8)
H10A0.02830.12631.10840.068*
H10B0.17280.11451.19900.068*
C110.1570 (3)0.0270 (2)1.0849 (2)0.0521 (8)
C120.2988 (3)−0.0149 (2)0.9392 (2)0.0543 (8)
H120.31860.06190.93390.065*
C130.3350 (3)−0.1051 (2)0.89341 (19)0.0511 (7)
C140.2917 (3)−0.2196 (2)0.8882 (2)0.0602 (8)
H140.2367−0.23860.91350.072*
C150.3289 (3)−0.3049 (3)0.8461 (2)0.0630 (9)
H150.2996−0.38080.84290.076*
C160.4108 (3)−0.2748 (3)0.8090 (2)0.0604 (8)
C170.4521 (3)−0.1636 (3)0.8101 (2)0.0663 (9)
H170.5048−0.14520.78280.080*
C180.4146 (3)−0.0785 (3)0.8526 (2)0.0610 (9)
H180.4427−0.00260.85390.073*
C190.3321 (4)0.3241 (3)0.9278 (3)0.0858 (12)
H19A0.28050.38510.88450.129*
H19B0.35350.26640.89480.129*
H19C0.41490.35520.97910.129*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0850 (16)0.0254 (10)0.0755 (13)−0.0023 (9)0.0564 (13)−0.0003 (9)
O20.1058 (19)0.0270 (11)0.1018 (17)−0.0034 (10)0.0717 (16)0.0019 (10)
O30.121 (3)0.069 (2)0.136 (3)0.0176 (17)0.069 (2)−0.0199 (19)
O40.142 (3)0.125 (3)0.131 (3)0.015 (2)0.102 (3)−0.0246 (19)
O50.158 (3)0.0435 (14)0.135 (2)0.0016 (14)0.115 (2)0.0028 (14)
N10.0780 (19)0.0345 (13)0.0612 (15)−0.0063 (11)0.0433 (15)0.0001 (11)
N20.0777 (19)0.0262 (12)0.0716 (16)−0.0015 (11)0.0458 (15)−0.0002 (11)
N30.0709 (18)0.0345 (13)0.0654 (15)0.0027 (11)0.0412 (15)−0.0025 (11)
N40.080 (2)0.092 (3)0.082 (2)0.0172 (19)0.0434 (19)−0.016 (2)
C10.089 (3)0.0418 (18)0.070 (2)−0.0116 (16)0.050 (2)0.0019 (15)
C20.098 (3)0.0310 (17)0.0654 (19)−0.0110 (15)0.040 (2)0.0003 (14)
C30.087 (3)0.0307 (16)0.0627 (19)−0.0032 (14)0.037 (2)−0.0045 (14)
C40.068 (2)0.0328 (16)0.0490 (16)−0.0031 (13)0.0269 (16)−0.0067 (12)
C50.077 (2)0.0457 (19)0.069 (2)0.0000 (15)0.0442 (19)−0.0144 (15)
C60.082 (3)0.0512 (19)0.072 (2)−0.0057 (16)0.053 (2)−0.0076 (16)
C70.083 (2)0.0366 (16)0.0660 (19)−0.0038 (14)0.0488 (19)0.0007 (14)
C80.065 (2)0.0309 (15)0.0525 (16)−0.0004 (12)0.0337 (16)−0.0022 (12)
C90.062 (2)0.0324 (15)0.0469 (15)−0.0053 (12)0.0306 (15)−0.0034 (12)
C100.088 (2)0.0266 (14)0.0736 (19)−0.0052 (14)0.0549 (19)0.0000 (13)
C110.069 (2)0.0314 (16)0.0642 (19)−0.0019 (13)0.0396 (18)−0.0020 (13)
C120.069 (2)0.0382 (17)0.0608 (18)−0.0017 (14)0.0365 (18)0.0021 (13)
C130.060 (2)0.0408 (17)0.0543 (17)−0.0012 (13)0.0301 (16)0.0014 (13)
C140.077 (2)0.0435 (17)0.080 (2)−0.0036 (15)0.054 (2)−0.0005 (16)
C150.074 (2)0.0431 (18)0.079 (2)−0.0003 (15)0.044 (2)−0.0031 (16)
C160.062 (2)0.059 (2)0.0636 (19)0.0077 (16)0.0339 (18)−0.0069 (16)
C170.071 (2)0.074 (2)0.069 (2)−0.0113 (17)0.046 (2)−0.0087 (18)
C180.069 (2)0.0535 (19)0.070 (2)−0.0128 (15)0.0422 (19)−0.0046 (16)
C190.100 (3)0.083 (3)0.086 (3)−0.002 (2)0.055 (3)0.005 (2)

Geometric parameters (Å, °)

O1—C81.378 (3)C6—C71.407 (4)
O1—C101.431 (3)C6—H60.930
O2—C111.222 (3)C7—C81.375 (4)
O3—N41.232 (4)C7—H70.930
O4—N41.227 (4)C8—C91.431 (4)
O5—C191.394 (4)C10—C111.506 (4)
O5—H50.820C10—H10A0.970
N1—C11.324 (4)C10—H10B0.970
N1—C91.371 (4)C12—C131.455 (4)
N2—C111.362 (4)C12—H120.930
N2—N31.383 (3)C13—C181.395 (4)
N2—H20.860C13—C141.399 (4)
N3—C121.275 (4)C14—C151.380 (4)
N4—C161.476 (4)C14—H140.930
C1—C21.406 (4)C15—C161.381 (4)
C1—H10.930C15—H150.930
C2—C31.350 (5)C16—C171.366 (4)
C2—H2A0.930C17—C181.385 (4)
C3—C41.411 (4)C17—H170.930
C3—H30.930C18—H180.930
C4—C91.421 (4)C19—H19A0.960
C4—C51.422 (4)C19—H19B0.960
C5—C61.355 (4)C19—H19C0.960
C5—H5A0.930
C8—O1—C10115.2 (2)O1—C10—C11113.6 (2)
C19—O5—H5109.5O1—C10—H10A108.8
C1—N1—C9116.9 (2)C11—C10—H10A108.8
C11—N2—N3118.1 (2)O1—C10—H10B108.8
C11—N2—H2121.0C11—C10—H10B108.8
N3—N2—H2120.9H10A—C10—H10B107.7
C12—N3—N2116.6 (2)O2—C11—N2124.3 (3)
O4—N4—O3124.4 (3)O2—C11—C10117.5 (3)
O4—N4—C16117.1 (4)N2—C11—C10118.2 (2)
O3—N4—C16118.5 (3)N3—C12—C13120.8 (3)
N1—C1—C2124.7 (3)N3—C12—H12119.6
N1—C1—H1117.6C13—C12—H12119.6
C2—C1—H1117.6C18—C13—C14118.1 (3)
C3—C2—C1118.7 (3)C18—C13—C12120.0 (3)
C3—C2—H2A120.7C14—C13—C12121.9 (3)
C1—C2—H2A120.7C15—C14—C13121.4 (3)
C2—C3—C4119.8 (3)C15—C14—H14119.3
C2—C3—H3120.1C13—C14—H14119.3
C4—C3—H3120.1C14—C15—C16118.3 (3)
C3—C4—C9117.9 (3)C14—C15—H15120.8
C3—C4—C5122.8 (3)C16—C15—H15120.8
C9—C4—C5119.3 (3)C17—C16—C15122.3 (3)
C6—C5—C4120.8 (3)C17—C16—N4120.0 (3)
C6—C5—H5A119.6C15—C16—N4117.8 (3)
C4—C5—H5A119.6C16—C17—C18119.0 (3)
C5—C6—C7120.3 (3)C16—C17—H17120.5
C5—C6—H6119.9C18—C17—H17120.5
C7—C6—H6119.9C17—C18—C13120.9 (3)
C8—C7—C6121.3 (3)C17—C18—H18119.6
C8—C7—H7119.4C13—C18—H18119.6
C6—C7—H7119.4O5—C19—H19A109.5
C7—C8—O1124.2 (2)O5—C19—H19B109.5
C7—C8—C9119.6 (2)H19A—C19—H19B109.5
O1—C8—C9116.2 (2)O5—C19—H19C109.5
N1—C9—C4122.0 (2)H19A—C19—H19C109.5
N1—C9—C8119.3 (2)H19B—C19—H19C109.5
C4—C9—C8118.7 (3)
C11—N2—N3—C12−176.7 (3)O1—C8—C9—C4175.8 (3)
C9—N1—C1—C2−1.3 (5)C8—O1—C10—C11173.7 (3)
N1—C1—C2—C30.4 (5)N3—N2—C11—O22.0 (5)
C1—C2—C3—C41.1 (5)N3—N2—C11—C10−179.0 (3)
C2—C3—C4—C9−1.7 (5)O1—C10—C11—O2177.6 (3)
C2—C3—C4—C5176.8 (3)O1—C10—C11—N2−1.4 (4)
C3—C4—C5—C6−176.6 (3)N2—N3—C12—C13178.4 (3)
C9—C4—C5—C61.9 (5)N3—C12—C13—C18−171.6 (3)
C4—C5—C6—C7−3.3 (5)N3—C12—C13—C148.8 (5)
C5—C6—C7—C81.5 (5)C18—C13—C14—C151.6 (5)
C6—C7—C8—O1−177.1 (3)C12—C13—C14—C15−178.7 (3)
C6—C7—C8—C91.8 (5)C13—C14—C15—C160.1 (5)
C10—O1—C8—C75.2 (4)C14—C15—C16—C17−2.0 (5)
C10—O1—C8—C9−173.7 (3)C14—C15—C16—N4179.4 (3)
C1—N1—C9—C40.6 (4)O4—N4—C16—C17−11.5 (5)
C1—N1—C9—C8−178.4 (3)O3—N4—C16—C17168.2 (4)
C3—C4—C9—N10.9 (4)O4—N4—C16—C15167.1 (3)
C5—C4—C9—N1−177.7 (3)O3—N4—C16—C15−13.2 (5)
C3—C4—C9—C8179.9 (3)C15—C16—C17—C182.1 (5)
C5—C4—C9—C81.4 (4)N4—C16—C17—C18−179.3 (3)
C7—C8—C9—N1175.9 (3)C16—C17—C18—C13−0.3 (5)
O1—C8—C9—N1−5.1 (4)C14—C13—C18—C17−1.5 (5)
C7—C8—C9—C4−3.2 (4)C12—C13—C18—C17178.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···N10.822.022.817 (4)164
N2—H2···O50.862.082.919 (4)164
C17—H17···O3i0.932.533.287 (5)139
C18—H18···O4i0.932.483.329 (5)152
C3—H3···O2ii0.932.583.233 (5)128

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2363).

References

  • Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev.171, 161–174.
  • Mona, M. M. & Wageih, G. H. (2002). J. Coord. Chem.55, 439–457.
  • 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.
  • Tan, J. (2009). Acta Cryst. E65, o651. [PMC free article] [PubMed]

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