(E)-N′-(5-Bromo-2-hy­droxy­benzyl­idene)-3,5-dihy­droxy­benzohydrazide monohydrate

Saharin, S.M.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810027856

Volume 66
Part 8
Page o2045
August 2010

Received 6 July 2010
Accepted 13 July 2010
Online 17 July 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.077
Data-to-parameter ratio = 11.9
Details

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate

Siti Munirah Saharin,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: khaledi@siswa.um.edu.my

The Schiff base molecule in the title compound, C₁₄H₁₁BrN₂O₄·H₂O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.16 Å. In the crystal structure, the Schiff base molecules and the water molecules are linked together by intermolecular N-HO and O-HO hydrogen bonds, leading to layers parallel to the bc plane. An intramolecular O-HN hydrogen bond involving the imine N atom and a hydroxy substituent is also observed.

Related literature

For the isotypic Cl analogue C₁₄H₁₁ClN₂O₄·H₂O, see: Deng et al. (2009).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₄·H₂O
M_r = 369.17
Monoclinic, P 2₁ /c
a = 13.5685 (3) Å
b = 8.0532 (2) Å
c = 13.2447 (2) Å
= 100.186 (1)°
V = 1424.44 (5) Å³
Z = 4
Mo K radiation
= 2.91 mm^-1
T = 296 K
0.58 × 0.33 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.283, T_max = 0.845
9148 measured reflections
2579 independent reflections
2183 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.077
S = 1.04
2579 reflections
217 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.45 e Å^-3
_min = -0.56 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.81 (2)	1.95 (2)	2.657 (2)	145 (3)
N2-H2NO2	0.85 (2)	2.07 (2)	2.913 (3)	170 (2)
O11-H11O8ⁱ	0.83 (2)	1.94 (2)	2.750 (2)	168 (3)
O13-H13O1ⁱⁱ	0.79 (2)	2.19 (2)	2.959 (2)	165 (3)
O2-H2AO8ⁱ	0.81 (2)	1.98 (2)	2.776 (3)	171 (4)
O2-H2BO11ⁱⁱⁱ	0.83 (2)	2.06 (2)	2.861 (3)	165 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2299 ).

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C)

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, S., Han, L., Huang, S., Zhang, H., Diao, Y. & Liu, K. (2009). Acta Cryst. E65, o721.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds