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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1601.
Published online 2009 June 17. doi:  10.1107/S1600536809021576
PMCID: PMC2969234

4-{(E)-N′-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate

Abstract

In the title compound, C19H15N3O4·CH4O, the mean planes of the benzene ring and the quinoline system make a dihedral angle of 6.7 (2)°. The acetohydrazide host mol­ecules are connected via inter­molecular O—H(...)O hydrogen bonds into two-dimensional zigzag sheets extending in the ab plane. The methanol solvent mol­ecule is linked to the host mol­ecule via inter­molecular N—H(...)O and O—H(...)N hydrogen bonds.

Related literature

For the coordination chemistry of 8-hydroxy­quinoline and its derivatives, see: Chen & Shi (1998 [triangle]). For a related structure, see: Wen et al. (2005 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1601-scheme1.jpg

Experimental

Crystal data

  • C19H15N3O4·CH4O
  • M r = 381.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1601-efi1.jpg
  • a = 10.1166 (18) Å
  • b = 11.095 (2) Å
  • c = 18.510 (3) Å
  • β = 115.896 (7)°
  • V = 1869.0 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 K
  • 0.22 × 0.19 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.982
  • 9663 measured reflections
  • 3302 independent reflections
  • 1666 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.161
  • S = 1.02
  • 3302 reflections
  • 255 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 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/S1600536809021576/cs2119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021576/cs2119Isup2.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). As part of our on going search for good extractants of metal ions or a biologically active material, the title compound was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 4-formylbenzoic acid. In the crystal structure of 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 ring make a dihedral angle of 6.7 (2)°. In the crystal structure, the methanol molecule is linked to the C19H15N3O4 host molecule via intermolecular N—H···O and O—H···N hydrogen bonds (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) fuse the molecules into two-dimensional zig-zag sheets along the a*-b* plane (Fig. 2).

Experimental

2-(quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-formylbenzoic acid (1.50 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 (1:2, v/v) solution over a period of 2 d.

Refinement

All H atoms were initially located in a difference Fourier map. C-atoms bound H atoms were constrained to 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, while O—H = 0.82 Å and N—H = 0.86 Å were applied. H-atoms displacement values were constarined as Uiso(H) = 1.2Ueq(C,N), or 1.5Ueq(C) for the methyl groups, and 1.5Ueq(O).

Figures

Fig. 1.
The asymmetric unit structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The dashed lines indicate hydrogen bonds.
Fig. 2.
The H-bonding sheet from the crystal structure supported via hydrogen bridges (dashed lines), with only relevant H atoms shown for clarity.

Crystal data

C19H15N3O4·CH4OF(000) = 800
Mr = 381.38Dx = 1.355 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1033 reflections
a = 10.1166 (18) Åθ = 2.9–20.4°
b = 11.095 (2) ŵ = 0.10 mm1
c = 18.510 (3) ÅT = 295 K
β = 115.896 (7)°Block, colorless
V = 1869.0 (6) Å30.22 × 0.19 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3302 independent reflections
Radiation source: fine-focus sealed tube1666 reflections with I > 2σ(I)
graphiteRint = 0.046
[var phi] and ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→12
Tmin = 0.979, Tmax = 0.982k = −13→11
9663 measured reflectionsl = −22→15

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0693P)2 + 0.0146P] where P = (Fo2 + 2Fc2)/3
3302 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.20 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.63801 (19)0.10228 (18)0.61156 (11)0.0599 (6)
O20.9689 (2)−0.0368 (2)0.74781 (14)0.0785 (7)
O31.7457 (2)0.4174 (2)0.71168 (15)0.0813 (7)
H31.83460.42740.72840.122*
O41.8166 (2)0.2717 (2)0.80207 (16)0.1010 (9)
O50.7722 (3)0.3037 (3)0.55054 (17)0.1139 (11)
H50.68570.28430.53430.171*
N10.4754 (3)0.2645 (3)0.50135 (15)0.0710 (8)
N20.9278 (2)0.1277 (2)0.66847 (14)0.0584 (7)
H20.86460.17620.63470.070*
N31.0764 (2)0.1439 (2)0.69304 (14)0.0571 (7)
C10.3936 (4)0.3439 (4)0.4474 (2)0.0946 (12)
H10.44140.40640.43510.113*
C20.2410 (4)0.3411 (4)0.4076 (2)0.1093 (14)
H2A0.18920.39980.37000.131*
C30.1702 (4)0.2509 (4)0.4249 (2)0.0895 (12)
H3A0.06820.24650.39880.107*
C40.2502 (3)0.1634 (3)0.48242 (18)0.0657 (9)
C50.1831 (4)0.0687 (4)0.5031 (2)0.0820 (11)
H5A0.08130.06120.47820.098*
C60.2653 (4)−0.0124 (3)0.5593 (2)0.0830 (11)
H60.2192−0.07470.57320.100*
C70.4194 (3)−0.0038 (3)0.5971 (2)0.0694 (9)
H70.4742−0.06040.63560.083*
C80.4887 (3)0.0864 (3)0.57778 (16)0.0542 (8)
C90.4050 (3)0.1729 (3)0.51962 (17)0.0563 (8)
C100.7231 (3)0.0167 (3)0.67118 (18)0.0582 (8)
H10A0.6963−0.06400.64950.070*
H10B0.70070.02380.71690.070*
C110.8852 (3)0.0348 (3)0.69869 (19)0.0569 (8)
C121.1136 (3)0.2365 (3)0.66626 (17)0.0616 (8)
H121.04180.28930.63240.074*
C131.2683 (3)0.2610 (3)0.68819 (17)0.0553 (8)
C141.3077 (3)0.3561 (3)0.65354 (18)0.0634 (9)
H141.23510.40540.61680.076*
C151.4531 (3)0.3789 (3)0.67266 (17)0.0611 (8)
H151.47740.44260.64810.073*
C161.5624 (3)0.3087 (3)0.72761 (17)0.0529 (8)
C171.5237 (3)0.2143 (3)0.76234 (19)0.0661 (9)
H171.59690.16600.79960.079*
C181.3783 (3)0.1893 (3)0.74314 (18)0.0634 (9)
H181.35440.12460.76710.076*
C191.7212 (3)0.3295 (3)0.7518 (2)0.0640 (9)
C200.7908 (5)0.3609 (5)0.4924 (3)0.158 (2)
H20A0.84340.43470.51300.236*
H20B0.69670.37860.44910.236*
H20C0.84590.31070.47310.236*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0316 (11)0.0766 (15)0.0663 (12)−0.0052 (9)0.0166 (9)0.0076 (11)
O20.0439 (13)0.0783 (16)0.1085 (17)0.0127 (11)0.0290 (12)0.0269 (14)
O30.0437 (13)0.0831 (18)0.1124 (18)−0.0145 (12)0.0296 (13)0.0009 (14)
O40.0376 (13)0.126 (2)0.120 (2)0.0027 (14)0.0169 (13)0.0300 (18)
O50.0558 (16)0.152 (3)0.114 (2)−0.0054 (17)0.0187 (15)0.065 (2)
N10.0464 (16)0.096 (2)0.0650 (16)0.0006 (15)0.0193 (13)0.0115 (15)
N20.0301 (13)0.0731 (18)0.0675 (16)0.0000 (11)0.0173 (12)0.0058 (13)
N30.0347 (14)0.0673 (19)0.0693 (16)−0.0030 (12)0.0226 (12)−0.0025 (13)
C10.063 (3)0.113 (3)0.090 (3)−0.002 (2)0.017 (2)0.034 (2)
C20.061 (3)0.146 (4)0.099 (3)0.015 (3)0.014 (2)0.035 (3)
C30.042 (2)0.130 (4)0.079 (2)0.001 (2)0.0101 (19)0.003 (2)
C40.0347 (17)0.097 (3)0.0587 (19)−0.0039 (17)0.0137 (15)−0.0129 (18)
C50.0358 (19)0.116 (3)0.086 (2)−0.015 (2)0.0189 (18)−0.018 (2)
C60.051 (2)0.097 (3)0.102 (3)−0.026 (2)0.034 (2)−0.012 (2)
C70.0426 (18)0.082 (2)0.082 (2)−0.0115 (17)0.0262 (17)0.0001 (18)
C80.0351 (16)0.072 (2)0.0551 (18)−0.0051 (15)0.0197 (14)−0.0090 (15)
C90.0375 (17)0.078 (2)0.0539 (17)−0.0065 (15)0.0199 (14)−0.0074 (16)
C100.0399 (17)0.066 (2)0.0674 (19)−0.0008 (15)0.0222 (15)0.0061 (16)
C110.0386 (17)0.063 (2)0.071 (2)−0.0008 (15)0.0256 (16)0.0017 (17)
C120.0340 (17)0.074 (2)0.069 (2)0.0005 (15)0.0151 (15)0.0062 (17)
C130.0381 (17)0.062 (2)0.0602 (18)−0.0018 (14)0.0167 (14)−0.0031 (15)
C140.0411 (18)0.070 (2)0.069 (2)0.0000 (15)0.0145 (15)0.0123 (16)
C150.0451 (19)0.063 (2)0.070 (2)−0.0090 (15)0.0208 (16)0.0031 (16)
C160.0358 (16)0.057 (2)0.0625 (18)−0.0063 (14)0.0180 (14)−0.0115 (15)
C170.0411 (18)0.073 (2)0.078 (2)0.0042 (16)0.0203 (16)0.0082 (18)
C180.0443 (18)0.067 (2)0.079 (2)0.0015 (15)0.0269 (16)0.0113 (17)
C190.044 (2)0.069 (2)0.076 (2)−0.0083 (17)0.0242 (18)−0.0094 (19)
C200.088 (4)0.201 (6)0.163 (5)0.004 (3)0.036 (3)0.073 (4)

Geometric parameters (Å, °)

O1—C81.371 (3)C6—C71.406 (4)
O1—C101.425 (3)C6—H60.9300
O2—C111.225 (3)C7—C81.357 (4)
O3—C191.313 (4)C7—H70.9300
O3—H30.8200C8—C91.415 (4)
O4—C191.193 (4)C10—C111.503 (4)
O5—C201.332 (5)C10—H10A0.9700
O5—H50.8200C10—H10B0.9700
N1—C11.318 (4)C12—C131.461 (4)
N1—C91.365 (4)C12—H120.9300
N2—C111.332 (3)C13—C141.382 (4)
N2—N31.379 (3)C13—C181.384 (4)
N2—H20.8600C14—C151.378 (4)
N3—C121.267 (3)C14—H140.9300
C1—C21.390 (5)C15—C161.372 (4)
C1—H10.9300C15—H150.9300
C2—C31.348 (5)C16—C171.372 (4)
C2—H2A0.9300C16—C191.486 (4)
C3—C41.407 (5)C17—C181.381 (4)
C3—H3A0.9300C17—H170.9300
C4—C51.393 (5)C18—H180.9300
C4—C91.413 (4)C20—H20A0.9600
C5—C61.351 (5)C20—H20B0.9600
C5—H5A0.9300C20—H20C0.9600
C8—O1—C10116.1 (2)C11—C10—H10A109.2
C19—O3—H3109.5O1—C10—H10B109.2
C20—O5—H5109.5C11—C10—H10B109.2
C1—N1—C9117.5 (3)H10A—C10—H10B107.9
C11—N2—N3118.0 (2)O2—C11—N2124.6 (3)
C11—N2—H2121.0O2—C11—C10117.6 (3)
N3—N2—H2121.0N2—C11—C10117.8 (3)
C12—N3—N2116.3 (2)N3—C12—C13120.5 (3)
N1—C1—C2124.9 (4)N3—C12—H12119.8
N1—C1—H1117.6C13—C12—H12119.8
C2—C1—H1117.6C14—C13—C18118.5 (3)
C3—C2—C1118.2 (4)C14—C13—C12120.3 (3)
C3—C2—H2A120.9C18—C13—C12121.2 (3)
C1—C2—H2A120.9C15—C14—C13120.9 (3)
C2—C3—C4120.2 (3)C15—C14—H14119.6
C2—C3—H3A119.9C13—C14—H14119.6
C4—C3—H3A119.9C16—C15—C14120.7 (3)
C5—C4—C3122.7 (3)C16—C15—H15119.7
C5—C4—C9119.5 (3)C14—C15—H15119.7
C3—C4—C9117.8 (3)C15—C16—C17118.6 (3)
C6—C5—C4120.3 (3)C15—C16—C19123.4 (3)
C6—C5—H5A119.9C17—C16—C19118.0 (3)
C4—C5—H5A119.9C16—C17—C18121.4 (3)
C5—C6—C7120.9 (3)C16—C17—H17119.3
C5—C6—H6119.5C18—C17—H17119.3
C7—C6—H6119.5C17—C18—C13119.9 (3)
C8—C7—C6120.5 (3)C17—C18—H18120.1
C8—C7—H7119.8C13—C18—H18120.1
C6—C7—H7119.8O4—C19—O3123.5 (3)
C7—C8—O1124.6 (3)O4—C19—C16123.4 (3)
C7—C8—C9119.7 (3)O3—C19—C16113.1 (3)
O1—C8—C9115.7 (3)O5—C20—H20A109.5
N1—C9—C4121.5 (3)O5—C20—H20B109.5
N1—C9—C8119.3 (3)H20A—C20—H20B109.5
C4—C9—C8119.2 (3)O5—C20—H20C109.5
O1—C10—C11112.0 (2)H20A—C20—H20C109.5
O1—C10—H10A109.2H20B—C20—H20C109.5
C11—N2—N3—C12−176.6 (3)O1—C8—C9—C4−179.5 (2)
C9—N1—C1—C2−0.2 (6)C8—O1—C10—C11174.5 (2)
N1—C1—C2—C30.0 (7)N3—N2—C11—O21.1 (5)
C1—C2—C3—C40.5 (6)N3—N2—C11—C10−179.4 (2)
C2—C3—C4—C5179.6 (4)O1—C10—C11—O2−177.3 (3)
C2—C3—C4—C9−0.9 (6)O1—C10—C11—N23.1 (4)
C3—C4—C5—C6−179.5 (3)N2—N3—C12—C13−179.4 (2)
C9—C4—C5—C61.1 (5)N3—C12—C13—C14174.4 (3)
C4—C5—C6—C7−0.8 (5)N3—C12—C13—C18−4.9 (5)
C5—C6—C7—C80.0 (5)C18—C13—C14—C150.5 (5)
C6—C7—C8—O1179.7 (3)C12—C13—C14—C15−178.9 (3)
C6—C7—C8—C90.5 (5)C13—C14—C15—C16−1.0 (5)
C10—O1—C8—C7−0.3 (4)C14—C15—C16—C170.8 (4)
C10—O1—C8—C9179.0 (2)C14—C15—C16—C19−179.0 (3)
C1—N1—C9—C4−0.1 (5)C15—C16—C17—C18−0.1 (5)
C1—N1—C9—C8−179.4 (3)C19—C16—C17—C18179.8 (3)
C5—C4—C9—N1−179.8 (3)C16—C17—C18—C13−0.5 (5)
C3—C4—C9—N10.7 (5)C14—C13—C18—C170.3 (5)
C5—C4—C9—C8−0.5 (4)C12—C13—C18—C17179.6 (3)
C3—C4—C9—C8180.0 (3)C15—C16—C19—O4176.7 (3)
C7—C8—C9—N1179.1 (3)C17—C16—C19—O4−3.2 (5)
O1—C8—C9—N1−0.3 (4)C15—C16—C19—O3−3.9 (4)
C7—C8—C9—C4−0.2 (4)C17—C16—C19—O3176.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.882.695 (3)171
O5—H5···N10.821.952.765 (3)171
N2—H2···O50.862.012.838 (4)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2119).

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.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography