organic compounds
(E)-N′-(4-Nitrobenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate
aCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Shandong 266109, People's Republic of China
*Correspondence e-mail: furbear01@163.com
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); Mona & Wageih (2002). For a related structure, see: Tan (2009).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809015992/bi2363sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809015992/bi2363Isup2.hkl
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.
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).
Data collection: SMART (Siemens, 1996); cell
SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C18H14N4O4·CH4O | F(000) = 800 |
Mr = 382.37 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1871 reflections |
a = 11.345 (10) Å | θ = 2.3–22.8° |
b = 11.559 (11) Å | µ = 0.10 mm−1 |
c = 16.234 (12) Å | T = 295 K |
β = 120.06 (5)° | Block, colorless |
V = 1843 (3) Å3 | 0.20 × 0.18 × 0.16 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 3258 independent reflections |
Radiation source: fine-focus sealed tube | 1872 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ϕ and ω scans | θmax = 25.1°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→10 |
Tmin = 0.980, Tmax = 0.984 | k = −12→13 |
9196 measured reflections | l = −17→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1106P)2 + 0.0143P] where P = (Fo2 + 2Fc2)/3 |
3258 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C18H14N4O4·CH4O | V = 1843 (3) Å3 |
Mr = 382.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.345 (10) Å | µ = 0.10 mm−1 |
b = 11.559 (11) Å | T = 295 K |
c = 16.234 (12) Å | 0.20 × 0.18 × 0.16 mm |
β = 120.06 (5)° |
Bruker SMART CCD diffractometer | 3258 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1872 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.984 | Rint = 0.050 |
9196 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.21 e Å−3 |
3258 reflections | Δρmin = −0.26 e Å−3 |
255 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1624 (2) | 0.23691 (14) | 1.11105 (14) | 0.0547 (6) | |
O2 | 0.1325 (2) | −0.07065 (16) | 1.10099 (16) | 0.0694 (7) | |
O3 | 0.4318 (3) | −0.4685 (3) | 0.7787 (2) | 0.1065 (10) | |
O4 | 0.5020 (4) | −0.3368 (3) | 0.7175 (2) | 0.1177 (12) | |
O5 | 0.2556 (3) | 0.27429 (19) | 0.9641 (2) | 0.0938 (9) | |
H5 | 0.2540 | 0.3180 | 1.0033 | 0.141* | |
N1 | 0.2147 (3) | 0.45024 (19) | 1.06723 (17) | 0.0541 (7) | |
N2 | 0.2130 (3) | 0.05140 (19) | 1.02969 (17) | 0.0547 (7) | |
H2 | 0.2310 | 0.1214 | 1.0219 | 0.066* | |
N3 | 0.2403 (3) | −0.0398 (2) | 0.98661 (17) | 0.0538 (7) | |
N4 | 0.4508 (3) | −0.3671 (3) | 0.7651 (2) | 0.0834 (9) | |
C1 | 0.2366 (3) | 0.5556 (3) | 1.0457 (2) | 0.0621 (9) | |
H1 | 0.2848 | 0.5621 | 1.0135 | 0.075* | |
C2 | 0.1921 (4) | 0.6582 (2) | 1.0679 (2) | 0.0652 (9) | |
H2A | 0.2101 | 0.7298 | 1.0504 | 0.078* | |
C3 | 0.1227 (4) | 0.6509 (2) | 1.1152 (2) | 0.0602 (9) | |
H3 | 0.0909 | 0.7176 | 1.1296 | 0.072* | |
C4 | 0.0985 (3) | 0.5417 (2) | 1.14255 (19) | 0.0510 (8) | |
C5 | 0.0322 (3) | 0.5278 (3) | 1.1966 (2) | 0.0605 (9) | |
H5A | −0.0014 | 0.5924 | 1.2123 | 0.073* | |
C6 | 0.0173 (3) | 0.4215 (3) | 1.2255 (2) | 0.0618 (9) | |
H6 | −0.0221 | 0.4141 | 1.2635 | 0.074* | |
C7 | 0.0611 (3) | 0.3223 (2) | 1.1981 (2) | 0.0569 (8) | |
H7 | 0.0483 | 0.2498 | 1.2172 | 0.068* | |
C8 | 0.1224 (3) | 0.3306 (2) | 1.14367 (19) | 0.0474 (7) | |
C9 | 0.1459 (3) | 0.4422 (2) | 1.11638 (18) | 0.0456 (7) | |
C10 | 0.1252 (3) | 0.1263 (2) | 1.1307 (2) | 0.0564 (8) | |
H10A | 0.0283 | 0.1263 | 1.1084 | 0.068* | |
H10B | 0.1728 | 0.1145 | 1.1990 | 0.068* | |
C11 | 0.1570 (3) | 0.0270 (2) | 1.0849 (2) | 0.0521 (8) | |
C12 | 0.2988 (3) | −0.0149 (2) | 0.9392 (2) | 0.0543 (8) | |
H12 | 0.3186 | 0.0619 | 0.9339 | 0.065* | |
C13 | 0.3350 (3) | −0.1051 (2) | 0.89341 (19) | 0.0511 (7) | |
C14 | 0.2917 (3) | −0.2196 (2) | 0.8882 (2) | 0.0602 (8) | |
H14 | 0.2367 | −0.2386 | 0.9135 | 0.072* | |
C15 | 0.3289 (3) | −0.3049 (3) | 0.8461 (2) | 0.0630 (9) | |
H15 | 0.2996 | −0.3808 | 0.8429 | 0.076* | |
C16 | 0.4108 (3) | −0.2748 (3) | 0.8090 (2) | 0.0604 (8) | |
C17 | 0.4521 (3) | −0.1636 (3) | 0.8101 (2) | 0.0663 (9) | |
H17 | 0.5048 | −0.1452 | 0.7828 | 0.080* | |
C18 | 0.4146 (3) | −0.0785 (3) | 0.8526 (2) | 0.0610 (9) | |
H18 | 0.4427 | −0.0026 | 0.8539 | 0.073* | |
C19 | 0.3321 (4) | 0.3241 (3) | 0.9278 (3) | 0.0858 (12) | |
H19A | 0.2805 | 0.3851 | 0.8845 | 0.129* | |
H19B | 0.3535 | 0.2664 | 0.8948 | 0.129* | |
H19C | 0.4149 | 0.3552 | 0.9791 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0850 (16) | 0.0254 (10) | 0.0755 (13) | −0.0023 (9) | 0.0564 (13) | −0.0003 (9) |
O2 | 0.1058 (19) | 0.0270 (11) | 0.1018 (17) | −0.0034 (10) | 0.0717 (16) | 0.0019 (10) |
O3 | 0.121 (3) | 0.069 (2) | 0.136 (3) | 0.0176 (17) | 0.069 (2) | −0.0199 (19) |
O4 | 0.142 (3) | 0.125 (3) | 0.131 (3) | 0.015 (2) | 0.102 (3) | −0.0246 (19) |
O5 | 0.158 (3) | 0.0435 (14) | 0.135 (2) | 0.0016 (14) | 0.115 (2) | 0.0028 (14) |
N1 | 0.0780 (19) | 0.0345 (13) | 0.0612 (15) | −0.0063 (11) | 0.0433 (15) | 0.0001 (11) |
N2 | 0.0777 (19) | 0.0262 (12) | 0.0716 (16) | −0.0015 (11) | 0.0458 (15) | −0.0002 (11) |
N3 | 0.0709 (18) | 0.0345 (13) | 0.0654 (15) | 0.0027 (11) | 0.0412 (15) | −0.0025 (11) |
N4 | 0.080 (2) | 0.092 (3) | 0.082 (2) | 0.0172 (19) | 0.0434 (19) | −0.016 (2) |
C1 | 0.089 (3) | 0.0418 (18) | 0.070 (2) | −0.0116 (16) | 0.050 (2) | 0.0019 (15) |
C2 | 0.098 (3) | 0.0310 (17) | 0.0654 (19) | −0.0110 (15) | 0.040 (2) | 0.0003 (14) |
C3 | 0.087 (3) | 0.0307 (16) | 0.0627 (19) | −0.0032 (14) | 0.037 (2) | −0.0045 (14) |
C4 | 0.068 (2) | 0.0328 (16) | 0.0490 (16) | −0.0031 (13) | 0.0269 (16) | −0.0067 (12) |
C5 | 0.077 (2) | 0.0457 (19) | 0.069 (2) | 0.0000 (15) | 0.0442 (19) | −0.0144 (15) |
C6 | 0.082 (3) | 0.0512 (19) | 0.072 (2) | −0.0057 (16) | 0.053 (2) | −0.0076 (16) |
C7 | 0.083 (2) | 0.0366 (16) | 0.0660 (19) | −0.0038 (14) | 0.0488 (19) | 0.0007 (14) |
C8 | 0.065 (2) | 0.0309 (15) | 0.0525 (16) | −0.0004 (12) | 0.0337 (16) | −0.0022 (12) |
C9 | 0.062 (2) | 0.0324 (15) | 0.0469 (15) | −0.0053 (12) | 0.0306 (15) | −0.0034 (12) |
C10 | 0.088 (2) | 0.0266 (14) | 0.0736 (19) | −0.0052 (14) | 0.0549 (19) | 0.0000 (13) |
C11 | 0.069 (2) | 0.0314 (16) | 0.0642 (19) | −0.0019 (13) | 0.0396 (18) | −0.0020 (13) |
C12 | 0.069 (2) | 0.0382 (17) | 0.0608 (18) | −0.0017 (14) | 0.0365 (18) | 0.0021 (13) |
C13 | 0.060 (2) | 0.0408 (17) | 0.0543 (17) | −0.0012 (13) | 0.0301 (16) | 0.0014 (13) |
C14 | 0.077 (2) | 0.0435 (17) | 0.080 (2) | −0.0036 (15) | 0.054 (2) | −0.0005 (16) |
C15 | 0.074 (2) | 0.0431 (18) | 0.079 (2) | −0.0003 (15) | 0.044 (2) | −0.0031 (16) |
C16 | 0.062 (2) | 0.059 (2) | 0.0636 (19) | 0.0077 (16) | 0.0339 (18) | −0.0069 (16) |
C17 | 0.071 (2) | 0.074 (2) | 0.069 (2) | −0.0113 (17) | 0.046 (2) | −0.0087 (18) |
C18 | 0.069 (2) | 0.0535 (19) | 0.070 (2) | −0.0128 (15) | 0.0422 (19) | −0.0046 (16) |
C19 | 0.100 (3) | 0.083 (3) | 0.086 (3) | −0.002 (2) | 0.055 (3) | 0.005 (2) |
O1—C8 | 1.378 (3) | C6—C7 | 1.407 (4) |
O1—C10 | 1.431 (3) | C6—H6 | 0.930 |
O2—C11 | 1.222 (3) | C7—C8 | 1.375 (4) |
O3—N4 | 1.232 (4) | C7—H7 | 0.930 |
O4—N4 | 1.227 (4) | C8—C9 | 1.431 (4) |
O5—C19 | 1.394 (4) | C10—C11 | 1.506 (4) |
O5—H5 | 0.820 | C10—H10A | 0.970 |
N1—C1 | 1.324 (4) | C10—H10B | 0.970 |
N1—C9 | 1.371 (4) | C12—C13 | 1.455 (4) |
N2—C11 | 1.362 (4) | C12—H12 | 0.930 |
N2—N3 | 1.383 (3) | C13—C18 | 1.395 (4) |
N2—H2 | 0.860 | C13—C14 | 1.399 (4) |
N3—C12 | 1.275 (4) | C14—C15 | 1.380 (4) |
N4—C16 | 1.476 (4) | C14—H14 | 0.930 |
C1—C2 | 1.406 (4) | C15—C16 | 1.381 (4) |
C1—H1 | 0.930 | C15—H15 | 0.930 |
C2—C3 | 1.350 (5) | C16—C17 | 1.366 (4) |
C2—H2A | 0.930 | C17—C18 | 1.385 (4) |
C3—C4 | 1.411 (4) | C17—H17 | 0.930 |
C3—H3 | 0.930 | C18—H18 | 0.930 |
C4—C9 | 1.421 (4) | C19—H19A | 0.960 |
C4—C5 | 1.422 (4) | C19—H19B | 0.960 |
C5—C6 | 1.355 (4) | C19—H19C | 0.960 |
C5—H5A | 0.930 | ||
C8—O1—C10 | 115.2 (2) | O1—C10—C11 | 113.6 (2) |
C19—O5—H5 | 109.5 | O1—C10—H10A | 108.8 |
C1—N1—C9 | 116.9 (2) | C11—C10—H10A | 108.8 |
C11—N2—N3 | 118.1 (2) | O1—C10—H10B | 108.8 |
C11—N2—H2 | 121.0 | C11—C10—H10B | 108.8 |
N3—N2—H2 | 120.9 | H10A—C10—H10B | 107.7 |
C12—N3—N2 | 116.6 (2) | O2—C11—N2 | 124.3 (3) |
O4—N4—O3 | 124.4 (3) | O2—C11—C10 | 117.5 (3) |
O4—N4—C16 | 117.1 (4) | N2—C11—C10 | 118.2 (2) |
O3—N4—C16 | 118.5 (3) | N3—C12—C13 | 120.8 (3) |
N1—C1—C2 | 124.7 (3) | N3—C12—H12 | 119.6 |
N1—C1—H1 | 117.6 | C13—C12—H12 | 119.6 |
C2—C1—H1 | 117.6 | C18—C13—C14 | 118.1 (3) |
C3—C2—C1 | 118.7 (3) | C18—C13—C12 | 120.0 (3) |
C3—C2—H2A | 120.7 | C14—C13—C12 | 121.9 (3) |
C1—C2—H2A | 120.7 | C15—C14—C13 | 121.4 (3) |
C2—C3—C4 | 119.8 (3) | C15—C14—H14 | 119.3 |
C2—C3—H3 | 120.1 | C13—C14—H14 | 119.3 |
C4—C3—H3 | 120.1 | C14—C15—C16 | 118.3 (3) |
C3—C4—C9 | 117.9 (3) | C14—C15—H15 | 120.8 |
C3—C4—C5 | 122.8 (3) | C16—C15—H15 | 120.8 |
C9—C4—C5 | 119.3 (3) | C17—C16—C15 | 122.3 (3) |
C6—C5—C4 | 120.8 (3) | C17—C16—N4 | 120.0 (3) |
C6—C5—H5A | 119.6 | C15—C16—N4 | 117.8 (3) |
C4—C5—H5A | 119.6 | C16—C17—C18 | 119.0 (3) |
C5—C6—C7 | 120.3 (3) | C16—C17—H17 | 120.5 |
C5—C6—H6 | 119.9 | C18—C17—H17 | 120.5 |
C7—C6—H6 | 119.9 | C17—C18—C13 | 120.9 (3) |
C8—C7—C6 | 121.3 (3) | C17—C18—H18 | 119.6 |
C8—C7—H7 | 119.4 | C13—C18—H18 | 119.6 |
C6—C7—H7 | 119.4 | O5—C19—H19A | 109.5 |
C7—C8—O1 | 124.2 (2) | O5—C19—H19B | 109.5 |
C7—C8—C9 | 119.6 (2) | H19A—C19—H19B | 109.5 |
O1—C8—C9 | 116.2 (2) | O5—C19—H19C | 109.5 |
N1—C9—C4 | 122.0 (2) | H19A—C19—H19C | 109.5 |
N1—C9—C8 | 119.3 (2) | H19B—C19—H19C | 109.5 |
C4—C9—C8 | 118.7 (3) | ||
C11—N2—N3—C12 | −176.7 (3) | O1—C8—C9—C4 | 175.8 (3) |
C9—N1—C1—C2 | −1.3 (5) | C8—O1—C10—C11 | 173.7 (3) |
N1—C1—C2—C3 | 0.4 (5) | N3—N2—C11—O2 | 2.0 (5) |
C1—C2—C3—C4 | 1.1 (5) | N3—N2—C11—C10 | −179.0 (3) |
C2—C3—C4—C9 | −1.7 (5) | O1—C10—C11—O2 | 177.6 (3) |
C2—C3—C4—C5 | 176.8 (3) | O1—C10—C11—N2 | −1.4 (4) |
C3—C4—C5—C6 | −176.6 (3) | N2—N3—C12—C13 | 178.4 (3) |
C9—C4—C5—C6 | 1.9 (5) | N3—C12—C13—C18 | −171.6 (3) |
C4—C5—C6—C7 | −3.3 (5) | N3—C12—C13—C14 | 8.8 (5) |
C5—C6—C7—C8 | 1.5 (5) | C18—C13—C14—C15 | 1.6 (5) |
C6—C7—C8—O1 | −177.1 (3) | C12—C13—C14—C15 | −178.7 (3) |
C6—C7—C8—C9 | 1.8 (5) | C13—C14—C15—C16 | 0.1 (5) |
C10—O1—C8—C7 | 5.2 (4) | C14—C15—C16—C17 | −2.0 (5) |
C10—O1—C8—C9 | −173.7 (3) | C14—C15—C16—N4 | 179.4 (3) |
C1—N1—C9—C4 | 0.6 (4) | O4—N4—C16—C17 | −11.5 (5) |
C1—N1—C9—C8 | −178.4 (3) | O3—N4—C16—C17 | 168.2 (4) |
C3—C4—C9—N1 | 0.9 (4) | O4—N4—C16—C15 | 167.1 (3) |
C5—C4—C9—N1 | −177.7 (3) | O3—N4—C16—C15 | −13.2 (5) |
C3—C4—C9—C8 | 179.9 (3) | C15—C16—C17—C18 | 2.1 (5) |
C5—C4—C9—C8 | 1.4 (4) | N4—C16—C17—C18 | −179.3 (3) |
C7—C8—C9—N1 | 175.9 (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—C17 | 178.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···N1 | 0.82 | 2.02 | 2.817 (4) | 164 |
N2—H2···O5 | 0.86 | 2.08 | 2.919 (4) | 164 |
C17—H17···O3i | 0.93 | 2.53 | 3.287 (5) | 139 |
C18—H18···O4i | 0.93 | 2.48 | 3.329 (5) | 152 |
C3—H3···O2ii | 0.93 | 2.58 | 3.233 (5) | 128 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H14N4O4·CH4O |
Mr | 382.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 11.345 (10), 11.559 (11), 16.234 (12) |
β (°) | 120.06 (5) |
V (Å3) | 1843 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.980, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9196, 3258, 1872 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.195, 1.00 |
No. of reflections | 3258 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.26 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···N1 | 0.82 | 2.02 | 2.817 (4) | 164.2 |
N2—H2···O5 | 0.86 | 2.08 | 2.919 (4) | 163.8 |
C17—H17···O3i | 0.93 | 2.53 | 3.287 (5) | 138.6 |
C18—H18···O4i | 0.93 | 2.48 | 3.329 (5) | 152.0 |
C3—H3···O2ii | 0.93 | 2.58 | 3.233 (5) | 127.8 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z. |
References
Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161–174. Web of Science CrossRef CAS Google Scholar
Mona, M. M. & Wageih, G. H. (2002). J. Coord. Chem. 55, 439–457. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Tan, J. (2009). Acta Cryst. E65, o651. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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.