(E)-N′-(4-Bromo­benzyl­idene)-2-(8-quin­ol­yloxy)acetohydrazide mono­hydrate

Jun Tan

doi:10.1107/S1600536809020418

. 2009 Jun 6;65(Pt 7):o1474. doi: 10.1107/S1600536809020418

(E)-N′-(4-Bromobenzylidene)-2-(8-quinolyloxy)acetohydrazide monohydrate

Jun Tan ^a,^*

PMCID: PMC2969315 PMID: 21582776

Abstract

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

C₁₈H₁₄BrN₃O₂·H₂O
M _r = 402.25
Monoclinic,
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 ▶) T _min = 0.640, T _max = 0.710
8378 measured reflections
2988 independent reflections
1334 reflections with I > 2σ(I)
R _int = 0.141

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.178
S = 1.04
2988 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.75 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020418/hb2981sup1.cif

e-65-o1474-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020418/hb2981Isup2.hkl

e-65-o1474-Isup2.hkl^{(146.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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.