organic compounds
(E)-N′-(4-Bromobenzylidene)-2-(8-quinolyloxy)acetohydrazide monohydrate
aCollege of Biological and Chemical Engineering, Jiaxing University, Jiaxing 314001, People's Republic of China
*Correspondence e-mail: catalyst007@126.com
In the title compound, C18H14BrN3O2·H2O, the dihedral angle between the mean planes of the benzene ring and the quinoline ring system is 34.2 (3)°. In the crystal, the constituents are linked into chains by O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds.
Related literature
For a related structure, see: Tan (2009). For background to the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998); Mona & Wageih (2002). For reference structural data, see: Allen et al. (1987).
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/S1600536809020418/hb2981sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020418/hb2981Isup2.hkl
2-(quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-bromobenzaldehyde (1.85 g, 10 mmol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 5 h. After cooling to room temperature, the mixture was filtered. Colourless blocks of (I) were obtained by slow evaporation of a acetone-methanol (1:2, v/v) solution over a period of 3 d.
The H atoms were initially located in a difference Fourier map, then relocated in idealised positions (C—H = 0.93–0.97Å O—H = 0.85 Å and N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 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).C18H14BrN3O2·H2O | F(000) = 1632 |
Mr = 402.25 | Dx = 1.578 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1037 reflections |
a = 21.95 (2) Å | θ = 2.5–19.7° |
b = 11.841 (8) Å | µ = 2.45 mm−1 |
c = 13.057 (9) Å | T = 295 K |
β = 93.70 (2)° | Block, colourless |
V = 3387 (4) Å3 | 0.20 × 0.18 × 0.15 mm |
Z = 8 |
Siemens SMART CCD area-detector diffractometer | 2988 independent reflections |
Radiation source: fine-focus sealed tube | 1334 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.141 |
ω scans | θmax = 25.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | h = −15→26 |
Tmin = 0.640, Tmax = 0.710 | k = −14→13 |
8378 measured reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.0524P)2 + 0.013P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2988 reflections | Δρmax = 0.52 e Å−3 |
227 parameters | Δρmin = −0.75 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0009 (2) |
C18H14BrN3O2·H2O | V = 3387 (4) Å3 |
Mr = 402.25 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.95 (2) Å | µ = 2.45 mm−1 |
b = 11.841 (8) Å | T = 295 K |
c = 13.057 (9) Å | 0.20 × 0.18 × 0.15 mm |
β = 93.70 (2)° |
Siemens SMART CCD area-detector diffractometer | 2988 independent reflections |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | 1334 reflections with I > 2σ(I) |
Tmin = 0.640, Tmax = 0.710 | Rint = 0.141 |
8378 measured reflections |
R[F2 > 2σ(F2)] = 0.070 | 0 restraints |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.52 e Å−3 |
2988 reflections | Δρmin = −0.75 e Å−3 |
227 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 | ||
Br1 | 0.90959 (4) | −0.09454 (8) | −0.24581 (7) | 0.0744 (4) | |
O1 | 0.6370 (2) | 0.0076 (4) | 0.4059 (4) | 0.0572 (15) | |
O2 | 0.7206 (2) | −0.2340 (5) | 0.3387 (4) | 0.0720 (18) | |
O3 | 0.6745 (2) | 0.1677 (4) | 0.2304 (4) | 0.0709 (17) | |
H19 | 0.6501 | 0.1798 | 0.2773 | 0.106* | |
H20 | 0.7041 | 0.2133 | 0.2416 | 0.106* | |
N1 | 0.5826 (3) | 0.2041 (6) | 0.3665 (5) | 0.0569 (18) | |
N2 | 0.7139 (2) | −0.0597 (5) | 0.2679 (5) | 0.0512 (17) | |
H2 | 0.7015 | 0.0089 | 0.2724 | 0.061* | |
N3 | 0.7481 (2) | −0.0944 (5) | 0.1878 (4) | 0.0498 (16) | |
C1 | 0.5556 (4) | 0.3013 (8) | 0.3491 (7) | 0.071 (2) | |
H1 | 0.5638 | 0.3395 | 0.2893 | 0.085* | |
C2 | 0.5152 (4) | 0.3521 (7) | 0.4142 (7) | 0.071 (3) | |
H2A | 0.4977 | 0.4219 | 0.3980 | 0.085* | |
C3 | 0.5024 (3) | 0.2977 (8) | 0.5002 (7) | 0.069 (3) | |
H3 | 0.4749 | 0.3292 | 0.5432 | 0.083* | |
C4 | 0.5300 (3) | 0.1940 (6) | 0.5264 (6) | 0.0469 (19) | |
C5 | 0.5217 (4) | 0.1349 (7) | 0.6158 (6) | 0.060 (2) | |
H5 | 0.4951 | 0.1631 | 0.6621 | 0.072* | |
C6 | 0.5512 (4) | 0.0379 (8) | 0.6369 (7) | 0.067 (2) | |
H6 | 0.5448 | 0.0005 | 0.6979 | 0.081* | |
C7 | 0.5913 (3) | −0.0086 (7) | 0.5699 (6) | 0.060 (2) | |
H7 | 0.6115 | −0.0760 | 0.5860 | 0.072* | |
C8 | 0.6007 (3) | 0.0465 (6) | 0.4799 (6) | 0.0462 (19) | |
C9 | 0.5708 (3) | 0.1502 (6) | 0.4560 (6) | 0.0459 (19) | |
C10 | 0.6614 (3) | −0.1020 (6) | 0.4229 (6) | 0.054 (2) | |
H10A | 0.6283 | −0.1556 | 0.4271 | 0.065* | |
H10B | 0.6855 | −0.1032 | 0.4879 | 0.065* | |
C11 | 0.7011 (3) | −0.1375 (7) | 0.3383 (6) | 0.053 (2) | |
C12 | 0.7666 (3) | −0.0121 (7) | 0.1327 (6) | 0.050 (2) | |
H12 | 0.7585 | 0.0621 | 0.1509 | 0.060* | |
C13 | 0.8002 (3) | −0.0349 (7) | 0.0416 (5) | 0.0441 (19) | |
C14 | 0.8235 (3) | 0.0555 (6) | −0.0099 (6) | 0.051 (2) | |
H14 | 0.8178 | 0.1285 | 0.0139 | 0.061* | |
C15 | 0.8551 (3) | 0.0384 (7) | −0.0965 (6) | 0.058 (2) | |
H15 | 0.8714 | 0.0993 | −0.1304 | 0.069* | |
C16 | 0.8623 (3) | −0.0703 (7) | −0.1320 (6) | 0.050 (2) | |
C17 | 0.8391 (3) | −0.1611 (7) | −0.0827 (6) | 0.050 (2) | |
H17 | 0.8437 | −0.2340 | −0.1073 | 0.060* | |
C18 | 0.8085 (3) | −0.1412 (6) | 0.0047 (5) | 0.0459 (19) | |
H18 | 0.7932 | −0.2023 | 0.0397 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0833 (7) | 0.0776 (7) | 0.0666 (6) | 0.0062 (5) | 0.0376 (5) | 0.0007 (6) |
O1 | 0.075 (4) | 0.046 (3) | 0.055 (3) | 0.009 (3) | 0.036 (3) | 0.003 (3) |
O2 | 0.096 (4) | 0.037 (3) | 0.089 (5) | 0.008 (3) | 0.056 (4) | 0.004 (3) |
O3 | 0.078 (4) | 0.055 (4) | 0.086 (4) | −0.008 (3) | 0.050 (3) | −0.008 (3) |
N1 | 0.060 (4) | 0.048 (4) | 0.066 (5) | 0.004 (3) | 0.025 (4) | −0.004 (4) |
N2 | 0.053 (4) | 0.041 (4) | 0.063 (4) | 0.001 (3) | 0.033 (3) | −0.002 (3) |
N3 | 0.053 (4) | 0.045 (4) | 0.055 (4) | −0.001 (3) | 0.031 (3) | −0.007 (4) |
C1 | 0.081 (6) | 0.069 (7) | 0.066 (6) | 0.005 (5) | 0.027 (5) | 0.015 (5) |
C2 | 0.076 (6) | 0.059 (6) | 0.080 (7) | 0.027 (5) | 0.023 (5) | 0.004 (5) |
C3 | 0.056 (6) | 0.077 (7) | 0.077 (7) | 0.004 (5) | 0.027 (5) | −0.014 (6) |
C4 | 0.047 (5) | 0.046 (5) | 0.050 (5) | −0.001 (4) | 0.024 (4) | −0.002 (4) |
C5 | 0.069 (6) | 0.064 (6) | 0.051 (5) | −0.005 (5) | 0.028 (4) | −0.011 (5) |
C6 | 0.069 (6) | 0.071 (7) | 0.066 (6) | −0.004 (5) | 0.037 (5) | 0.007 (5) |
C7 | 0.063 (5) | 0.053 (5) | 0.068 (6) | 0.003 (4) | 0.036 (5) | 0.005 (5) |
C8 | 0.053 (5) | 0.044 (5) | 0.045 (5) | −0.003 (4) | 0.024 (4) | −0.004 (4) |
C9 | 0.045 (5) | 0.046 (5) | 0.049 (5) | −0.003 (4) | 0.016 (4) | −0.004 (4) |
C10 | 0.064 (5) | 0.044 (5) | 0.058 (5) | −0.001 (4) | 0.033 (4) | 0.003 (4) |
C11 | 0.053 (5) | 0.046 (5) | 0.062 (5) | −0.012 (4) | 0.021 (4) | −0.008 (5) |
C12 | 0.049 (5) | 0.044 (5) | 0.061 (5) | 0.001 (4) | 0.025 (4) | −0.004 (4) |
C13 | 0.038 (4) | 0.050 (5) | 0.047 (5) | 0.000 (4) | 0.019 (4) | 0.003 (4) |
C14 | 0.052 (5) | 0.040 (5) | 0.063 (5) | 0.002 (4) | 0.023 (4) | −0.006 (4) |
C15 | 0.055 (5) | 0.049 (5) | 0.072 (6) | 0.000 (4) | 0.027 (4) | 0.015 (5) |
C16 | 0.044 (4) | 0.052 (6) | 0.058 (5) | 0.008 (4) | 0.016 (4) | 0.007 (4) |
C17 | 0.054 (5) | 0.049 (5) | 0.047 (5) | 0.003 (4) | 0.013 (4) | −0.009 (4) |
C18 | 0.053 (5) | 0.041 (5) | 0.045 (5) | −0.005 (4) | 0.019 (4) | 0.001 (4) |
Br1—C16 | 1.889 (7) | C5—H5 | 0.9300 |
O1—C8 | 1.371 (7) | C6—C7 | 1.394 (9) |
O1—C10 | 1.417 (8) | C6—H6 | 0.9300 |
O2—C11 | 1.220 (8) | C7—C8 | 1.371 (10) |
O3—H19 | 0.8500 | C7—H7 | 0.9300 |
O3—H20 | 0.8500 | C8—C9 | 1.417 (10) |
N1—C1 | 1.309 (9) | C10—C11 | 1.509 (9) |
N1—C9 | 1.370 (9) | C10—H10A | 0.9700 |
N2—C11 | 1.344 (9) | C10—H10B | 0.9700 |
N2—N3 | 1.389 (7) | C12—C13 | 1.464 (9) |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
N3—C12 | 1.292 (8) | C13—C18 | 1.364 (9) |
C1—C2 | 1.402 (11) | C13—C14 | 1.381 (9) |
C1—H1 | 0.9300 | C14—C15 | 1.379 (9) |
C2—C3 | 1.341 (11) | C14—H14 | 0.9300 |
C2—H2A | 0.9300 | C15—C16 | 1.380 (10) |
C3—C4 | 1.402 (10) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.368 (10) |
C4—C5 | 1.383 (10) | C17—C18 | 1.380 (9) |
C4—C9 | 1.422 (9) | C17—H17 | 0.9300 |
C5—C6 | 1.338 (10) | C18—H18 | 0.9300 |
C8—O1—C10 | 115.4 (5) | N1—C9—C4 | 122.9 (7) |
H19—O3—H20 | 106.1 | C8—C9—C4 | 118.3 (7) |
C1—N1—C9 | 116.7 (7) | O1—C10—C11 | 111.8 (6) |
C11—N2—N3 | 117.4 (6) | O1—C10—H10A | 109.3 |
C11—N2—H2 | 121.3 | C11—C10—H10A | 109.3 |
N3—N2—H2 | 121.3 | O1—C10—H10B | 109.3 |
C12—N3—N2 | 113.6 (6) | C11—C10—H10B | 109.3 |
N1—C1—C2 | 124.7 (8) | H10A—C10—H10B | 107.9 |
N1—C1—H1 | 117.7 | O2—C11—N2 | 123.8 (7) |
C2—C1—H1 | 117.7 | O2—C11—C10 | 118.4 (7) |
C3—C2—C1 | 118.5 (8) | N2—C11—C10 | 117.8 (7) |
C3—C2—H2A | 120.8 | N3—C12—C13 | 120.4 (7) |
C1—C2—H2A | 120.8 | N3—C12—H12 | 119.8 |
C2—C3—C4 | 121.0 (8) | C13—C12—H12 | 119.8 |
C2—C3—H3 | 119.5 | C18—C13—C14 | 118.7 (6) |
C4—C3—H3 | 119.5 | C18—C13—C12 | 122.9 (7) |
C5—C4—C3 | 124.8 (7) | C14—C13—C12 | 118.3 (7) |
C5—C4—C9 | 119.0 (7) | C15—C14—C13 | 120.5 (7) |
C3—C4—C9 | 116.2 (7) | C15—C14—H14 | 119.7 |
C6—C5—C4 | 121.3 (7) | C13—C14—H14 | 119.7 |
C6—C5—H5 | 119.3 | C14—C15—C16 | 119.1 (7) |
C4—C5—H5 | 119.3 | C14—C15—H15 | 120.4 |
C5—C6—C7 | 121.7 (8) | C16—C15—H15 | 120.4 |
C5—C6—H6 | 119.1 | C17—C16—C15 | 121.4 (7) |
C7—C6—H6 | 119.1 | C17—C16—Br1 | 119.4 (6) |
C8—C7—C6 | 119.1 (7) | C15—C16—Br1 | 119.1 (6) |
C8—C7—H7 | 120.5 | C16—C17—C18 | 118.1 (7) |
C6—C7—H7 | 120.5 | C16—C17—H17 | 121.0 |
C7—C8—O1 | 124.8 (7) | C18—C17—H17 | 121.0 |
C7—C8—C9 | 120.6 (7) | C13—C18—C17 | 122.2 (7) |
O1—C8—C9 | 114.7 (6) | C13—C18—H18 | 118.9 |
N1—C9—C8 | 118.7 (6) | C17—C18—H18 | 118.9 |
C11—N2—N3—C12 | −169.8 (7) | C3—C4—C9—N1 | −0.8 (11) |
C9—N1—C1—C2 | −1.2 (13) | C5—C4—C9—C8 | 0.8 (11) |
N1—C1—C2—C3 | −0.6 (14) | C3—C4—C9—C8 | 178.9 (7) |
C1—C2—C3—C4 | 1.8 (14) | C8—O1—C10—C11 | −179.5 (6) |
C2—C3—C4—C5 | 176.9 (8) | N3—N2—C11—O2 | 4.4 (12) |
C2—C3—C4—C9 | −1.1 (12) | N3—N2—C11—C10 | −177.2 (6) |
C3—C4—C5—C6 | −177.9 (8) | O1—C10—C11—O2 | −173.5 (7) |
C9—C4—C5—C6 | 0.1 (12) | O1—C10—C11—N2 | 7.9 (10) |
C4—C5—C6—C7 | −0.4 (13) | N2—N3—C12—C13 | −176.4 (6) |
C5—C6—C7—C8 | −0.1 (13) | N3—C12—C13—C18 | 6.5 (11) |
C6—C7—C8—O1 | −177.3 (7) | N3—C12—C13—C14 | −174.6 (7) |
C6—C7—C8—C9 | 1.0 (12) | C18—C13—C14—C15 | −0.6 (11) |
C10—O1—C8—C7 | 5.5 (11) | C12—C13—C14—C15 | −179.6 (7) |
C10—O1—C8—C9 | −172.9 (6) | C13—C14—C15—C16 | 1.1 (12) |
C1—N1—C9—C8 | −177.8 (7) | C14—C15—C16—C17 | −0.5 (11) |
C1—N1—C9—C4 | 1.9 (11) | C14—C15—C16—Br1 | −176.4 (6) |
C7—C8—C9—N1 | 178.3 (7) | C15—C16—C17—C18 | −0.6 (11) |
O1—C8—C9—N1 | −3.2 (10) | Br1—C16—C17—C18 | 175.3 (5) |
C7—C8—C9—C4 | −1.4 (11) | C14—C13—C18—C17 | −0.6 (11) |
O1—C8—C9—C4 | 177.1 (7) | C12—C13—C18—C17 | 178.4 (7) |
C5—C4—C9—N1 | −178.9 (7) | C16—C17—C18—C13 | 1.1 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3 | 0.86 | 2.04 | 2.860 (8) | 160 |
O3—H19···N1 | 0.85 | 1.97 | 2.806 (8) | 170 |
O3—H20···O2i | 0.85 | 2.11 | 2.783 (7) | 136 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H14BrN3O2·H2O |
Mr | 402.25 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 21.95 (2), 11.841 (8), 13.057 (9) |
β (°) | 93.70 (2) |
V (Å3) | 3387 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.45 |
Crystal size (mm) | 0.20 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Siemens, 1996) |
Tmin, Tmax | 0.640, 0.710 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8378, 2988, 1334 |
Rint | 0.141 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.178, 1.04 |
No. of reflections | 2988 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.75 |
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 |
N2—H2···O3 | 0.86 | 2.04 | 2.860 (8) | 160 |
O3—H19···N1 | 0.85 | 1.97 | 2.806 (8) | 170 |
O3—H20···O2i | 0.85 | 2.11 | 2.783 (7) | 136 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
This project was supported by the Natural Science Foundation of Zhejiang Province for Distinguished Young Students (No. 2008R40G2190024) and the Scientific Research Fund of the Zhejiang Provincial Education Department (No. Y200803569).
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. CrossRef Web of Science Google Scholar
Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161—174. Google Scholar
Mona, M. M. & Wageih, G. H. (2002). J. Coord. Chem. 55, 439–457. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. 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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
8-Hydroxyquinoline and its derivatives constitute 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, (I), has been synthesized. We report here its crystal structure.
All bond lengths and angles are normal (Allen et al., 1987), and are 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 34.2 (3)°. In the crystal structure, the C18H14BrN3O2 molecules and the water molecules are linked into chains by O—H···O, N—H···O and O—H···N hydrogen bonds.