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

Tan, J.

doi:10.1107/S1600536809020418

Volume 65
Part 7
Page o1474
July 2009

Received 22 May 2009
Accepted 28 May 2009
Online 6 June 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.011 Å
R = 0.070
wR = 0.178
Data-to-parameter ratio = 13.2
Details

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

Jun Tan ^a ^*

^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-HO, N-HO and O-HN 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, C 2/c
a = 21.95 (2) Å
b = 11.841 (8) Å
c = 13.057 (9) Å
= 93.70 (2)°
V = 3387 (4) Å³
Z = 8
Mo K radiation
= 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 > 2(I)
R_int = 0.141

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.178
S = 1.04
2988 reflections
227 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_min = -0.75 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O3	0.86	2.04	2.860 (8)	160
O3-H19N1	0.85	1.97	2.806 (8)	170
O3-H20O2ⁱ	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); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: HB2981 ).

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.
Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161-174.
Mona, M. M. & Wageih, G. H. (2002). J. Coord. Chem. 55, 439-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Tan, J. (2009). Acta Cryst. E65, o651.

organic compounds