organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(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

(Received 22 May 2009; accepted 28 May 2009; online 6 June 2009)

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[Tan, J. (2009). Acta Cryst. E65, o651.]). For background to the coordination chemistry of 8-hydroxy­quinoline and its derivatives, see: Chen & Shi (1998[Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161—174.]); Mona & Wageih (2002[Mona, M. M. & Wageih, G. H. (2002). J. Coord. Chem. 55, 439-457.]). For reference structural data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H14BrN3O2·H2O

  • Mr = 402.25

  • Monoclinic, C 2/c

  • a = 21.95 (2) Å

  • b = 11.841 (8) Å

  • c = 13.057 (9) Å

  • β = 93.70 (2)°

  • V = 3387 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.45 mm−1

  • T = 295 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.640, Tmax = 0.710

  • 8378 measured reflections

  • 2988 independent reflections

  • 1334 reflections with I > 2σ(I)

  • Rint = 0.141

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.178

  • S = 1.04

  • 2988 reflections

  • 227 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.75 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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 top

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.

Refinement top

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).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The structure of the chains formed via hydrogen bonds, H atoms have been omitted for clarity. The dashed lines indicate hydrogen bonds.
(E)-N'-(4-Bromobenzylidene)-2-(8-quinolyloxy)acetohydrazide monohydrate top
Crystal data top
C18H14BrN3O2·H2OF(000) = 1632
Mr = 402.25Dx = 1.578 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1037 reflections
a = 21.95 (2) Åθ = 2.5–19.7°
b = 11.841 (8) ŵ = 2.45 mm1
c = 13.057 (9) ÅT = 295 K
β = 93.70 (2)°Block, colourless
V = 3387 (4) Å30.20 × 0.18 × 0.15 mm
Z = 8
Data collection top
Siemens SMART CCD area-detector
diffractometer
2988 independent reflections
Radiation source: fine-focus sealed tube1334 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.141
ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)
h = 1526
Tmin = 0.640, Tmax = 0.710k = 1413
8378 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070H-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 reflectionsΔρmax = 0.52 e Å3
227 parametersΔρmin = 0.75 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0009 (2)
Crystal data top
C18H14BrN3O2·H2OV = 3387 (4) Å3
Mr = 402.25Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.95 (2) ŵ = 2.45 mm1
b = 11.841 (8) ÅT = 295 K
c = 13.057 (9) Å0.20 × 0.18 × 0.15 mm
β = 93.70 (2)°
Data collection top
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 = 0.710Rint = 0.141
8378 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.04Δρmax = 0.52 e Å3
2988 reflectionsΔρmin = 0.75 e Å3
227 parameters
Special details top

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) top
xyzUiso*/Ueq
Br10.90959 (4)0.09454 (8)0.24581 (7)0.0744 (4)
O10.6370 (2)0.0076 (4)0.4059 (4)0.0572 (15)
O20.7206 (2)0.2340 (5)0.3387 (4)0.0720 (18)
O30.6745 (2)0.1677 (4)0.2304 (4)0.0709 (17)
H190.65010.17980.27730.106*
H200.70410.21330.24160.106*
N10.5826 (3)0.2041 (6)0.3665 (5)0.0569 (18)
N20.7139 (2)0.0597 (5)0.2679 (5)0.0512 (17)
H20.70150.00890.27240.061*
N30.7481 (2)0.0944 (5)0.1878 (4)0.0498 (16)
C10.5556 (4)0.3013 (8)0.3491 (7)0.071 (2)
H10.56380.33950.28930.085*
C20.5152 (4)0.3521 (7)0.4142 (7)0.071 (3)
H2A0.49770.42190.39800.085*
C30.5024 (3)0.2977 (8)0.5002 (7)0.069 (3)
H30.47490.32920.54320.083*
C40.5300 (3)0.1940 (6)0.5264 (6)0.0469 (19)
C50.5217 (4)0.1349 (7)0.6158 (6)0.060 (2)
H50.49510.16310.66210.072*
C60.5512 (4)0.0379 (8)0.6369 (7)0.067 (2)
H60.54480.00050.69790.081*
C70.5913 (3)0.0086 (7)0.5699 (6)0.060 (2)
H70.61150.07600.58600.072*
C80.6007 (3)0.0465 (6)0.4799 (6)0.0462 (19)
C90.5708 (3)0.1502 (6)0.4560 (6)0.0459 (19)
C100.6614 (3)0.1020 (6)0.4229 (6)0.054 (2)
H10A0.62830.15560.42710.065*
H10B0.68550.10320.48790.065*
C110.7011 (3)0.1375 (7)0.3383 (6)0.053 (2)
C120.7666 (3)0.0121 (7)0.1327 (6)0.050 (2)
H120.75850.06210.15090.060*
C130.8002 (3)0.0349 (7)0.0416 (5)0.0441 (19)
C140.8235 (3)0.0555 (6)0.0099 (6)0.051 (2)
H140.81780.12850.01390.061*
C150.8551 (3)0.0384 (7)0.0965 (6)0.058 (2)
H150.87140.09930.13040.069*
C160.8623 (3)0.0703 (7)0.1320 (6)0.050 (2)
C170.8391 (3)0.1611 (7)0.0827 (6)0.050 (2)
H170.84370.23400.10730.060*
C180.8085 (3)0.1412 (6)0.0047 (5)0.0459 (19)
H180.79320.20230.03970.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0833 (7)0.0776 (7)0.0666 (6)0.0062 (5)0.0376 (5)0.0007 (6)
O10.075 (4)0.046 (3)0.055 (3)0.009 (3)0.036 (3)0.003 (3)
O20.096 (4)0.037 (3)0.089 (5)0.008 (3)0.056 (4)0.004 (3)
O30.078 (4)0.055 (4)0.086 (4)0.008 (3)0.050 (3)0.008 (3)
N10.060 (4)0.048 (4)0.066 (5)0.004 (3)0.025 (4)0.004 (4)
N20.053 (4)0.041 (4)0.063 (4)0.001 (3)0.033 (3)0.002 (3)
N30.053 (4)0.045 (4)0.055 (4)0.001 (3)0.031 (3)0.007 (4)
C10.081 (6)0.069 (7)0.066 (6)0.005 (5)0.027 (5)0.015 (5)
C20.076 (6)0.059 (6)0.080 (7)0.027 (5)0.023 (5)0.004 (5)
C30.056 (6)0.077 (7)0.077 (7)0.004 (5)0.027 (5)0.014 (6)
C40.047 (5)0.046 (5)0.050 (5)0.001 (4)0.024 (4)0.002 (4)
C50.069 (6)0.064 (6)0.051 (5)0.005 (5)0.028 (4)0.011 (5)
C60.069 (6)0.071 (7)0.066 (6)0.004 (5)0.037 (5)0.007 (5)
C70.063 (5)0.053 (5)0.068 (6)0.003 (4)0.036 (5)0.005 (5)
C80.053 (5)0.044 (5)0.045 (5)0.003 (4)0.024 (4)0.004 (4)
C90.045 (5)0.046 (5)0.049 (5)0.003 (4)0.016 (4)0.004 (4)
C100.064 (5)0.044 (5)0.058 (5)0.001 (4)0.033 (4)0.003 (4)
C110.053 (5)0.046 (5)0.062 (5)0.012 (4)0.021 (4)0.008 (5)
C120.049 (5)0.044 (5)0.061 (5)0.001 (4)0.025 (4)0.004 (4)
C130.038 (4)0.050 (5)0.047 (5)0.000 (4)0.019 (4)0.003 (4)
C140.052 (5)0.040 (5)0.063 (5)0.002 (4)0.023 (4)0.006 (4)
C150.055 (5)0.049 (5)0.072 (6)0.000 (4)0.027 (4)0.015 (5)
C160.044 (4)0.052 (6)0.058 (5)0.008 (4)0.016 (4)0.007 (4)
C170.054 (5)0.049 (5)0.047 (5)0.003 (4)0.013 (4)0.009 (4)
C180.053 (5)0.041 (5)0.045 (5)0.005 (4)0.019 (4)0.001 (4)
Geometric parameters (Å, º) top
Br1—C161.889 (7)C5—H50.9300
O1—C81.371 (7)C6—C71.394 (9)
O1—C101.417 (8)C6—H60.9300
O2—C111.220 (8)C7—C81.371 (10)
O3—H190.8500C7—H70.9300
O3—H200.8500C8—C91.417 (10)
N1—C11.309 (9)C10—C111.509 (9)
N1—C91.370 (9)C10—H10A0.9700
N2—C111.344 (9)C10—H10B0.9700
N2—N31.389 (7)C12—C131.464 (9)
N2—H20.8600C12—H120.9300
N3—C121.292 (8)C13—C181.364 (9)
C1—C21.402 (11)C13—C141.381 (9)
C1—H10.9300C14—C151.379 (9)
C2—C31.341 (11)C14—H140.9300
C2—H2A0.9300C15—C161.380 (10)
C3—C41.402 (10)C15—H150.9300
C3—H30.9300C16—C171.368 (10)
C4—C51.383 (10)C17—C181.380 (9)
C4—C91.422 (9)C17—H170.9300
C5—C61.338 (10)C18—H180.9300
C8—O1—C10115.4 (5)N1—C9—C4122.9 (7)
H19—O3—H20106.1C8—C9—C4118.3 (7)
C1—N1—C9116.7 (7)O1—C10—C11111.8 (6)
C11—N2—N3117.4 (6)O1—C10—H10A109.3
C11—N2—H2121.3C11—C10—H10A109.3
N3—N2—H2121.3O1—C10—H10B109.3
C12—N3—N2113.6 (6)C11—C10—H10B109.3
N1—C1—C2124.7 (8)H10A—C10—H10B107.9
N1—C1—H1117.7O2—C11—N2123.8 (7)
C2—C1—H1117.7O2—C11—C10118.4 (7)
C3—C2—C1118.5 (8)N2—C11—C10117.8 (7)
C3—C2—H2A120.8N3—C12—C13120.4 (7)
C1—C2—H2A120.8N3—C12—H12119.8
C2—C3—C4121.0 (8)C13—C12—H12119.8
C2—C3—H3119.5C18—C13—C14118.7 (6)
C4—C3—H3119.5C18—C13—C12122.9 (7)
C5—C4—C3124.8 (7)C14—C13—C12118.3 (7)
C5—C4—C9119.0 (7)C15—C14—C13120.5 (7)
C3—C4—C9116.2 (7)C15—C14—H14119.7
C6—C5—C4121.3 (7)C13—C14—H14119.7
C6—C5—H5119.3C14—C15—C16119.1 (7)
C4—C5—H5119.3C14—C15—H15120.4
C5—C6—C7121.7 (8)C16—C15—H15120.4
C5—C6—H6119.1C17—C16—C15121.4 (7)
C7—C6—H6119.1C17—C16—Br1119.4 (6)
C8—C7—C6119.1 (7)C15—C16—Br1119.1 (6)
C8—C7—H7120.5C16—C17—C18118.1 (7)
C6—C7—H7120.5C16—C17—H17121.0
C7—C8—O1124.8 (7)C18—C17—H17121.0
C7—C8—C9120.6 (7)C13—C18—C17122.2 (7)
O1—C8—C9114.7 (6)C13—C18—H18118.9
N1—C9—C8118.7 (6)C17—C18—H18118.9
C11—N2—N3—C12169.8 (7)C3—C4—C9—N10.8 (11)
C9—N1—C1—C21.2 (13)C5—C4—C9—C80.8 (11)
N1—C1—C2—C30.6 (14)C3—C4—C9—C8178.9 (7)
C1—C2—C3—C41.8 (14)C8—O1—C10—C11179.5 (6)
C2—C3—C4—C5176.9 (8)N3—N2—C11—O24.4 (12)
C2—C3—C4—C91.1 (12)N3—N2—C11—C10177.2 (6)
C3—C4—C5—C6177.9 (8)O1—C10—C11—O2173.5 (7)
C9—C4—C5—C60.1 (12)O1—C10—C11—N27.9 (10)
C4—C5—C6—C70.4 (13)N2—N3—C12—C13176.4 (6)
C5—C6—C7—C80.1 (13)N3—C12—C13—C186.5 (11)
C6—C7—C8—O1177.3 (7)N3—C12—C13—C14174.6 (7)
C6—C7—C8—C91.0 (12)C18—C13—C14—C150.6 (11)
C10—O1—C8—C75.5 (11)C12—C13—C14—C15179.6 (7)
C10—O1—C8—C9172.9 (6)C13—C14—C15—C161.1 (12)
C1—N1—C9—C8177.8 (7)C14—C15—C16—C170.5 (11)
C1—N1—C9—C41.9 (11)C14—C15—C16—Br1176.4 (6)
C7—C8—C9—N1178.3 (7)C15—C16—C17—C180.6 (11)
O1—C8—C9—N13.2 (10)Br1—C16—C17—C18175.3 (5)
C7—C8—C9—C41.4 (11)C14—C13—C18—C170.6 (11)
O1—C8—C9—C4177.1 (7)C12—C13—C18—C17178.4 (7)
C5—C4—C9—N1178.9 (7)C16—C17—C18—C131.1 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.862.042.860 (8)160
O3—H19···N10.851.972.806 (8)170
O3—H20···O2i0.852.112.783 (7)136
Symmetry code: (i) x+3/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H14BrN3O2·H2O
Mr402.25
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)21.95 (2), 11.841 (8), 13.057 (9)
β (°) 93.70 (2)
V3)3387 (4)
Z8
Radiation typeMo Kα
µ (mm1)2.45
Crystal size (mm)0.20 × 0.18 × 0.15
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Siemens, 1996)
Tmin, Tmax0.640, 0.710
No. of measured, independent and
observed [I > 2σ(I)] reflections
8378, 2988, 1334
Rint0.141
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.178, 1.04
No. of reflections2988
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.75

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.862.042.860 (8)160
O3—H19···N10.851.972.806 (8)170
O3—H20···O2i0.852.112.783 (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

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First citationMona, M. M. & Wageih, G. H. (2002). J. Coord. Chem. 55, 439–457.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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First citationTan, J. (2009). Acta Cryst. E65, o651.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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