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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 [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.077
Data-to-parameter ratio = 11.9
Details
Open access

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

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-H...O and O-H...O hydrogen bonds, leading to layers parallel to the bc plane. An intramolecular O-H...N 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[Deng, S., Han, L., Huang, S., Zhang, H., Diao, Y. & Liu, K. (2009). Acta Cryst. E65, o721.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11BrN2O4·H2O

  • Mr = 369.17

  • Monoclinic, P 21 /c

  • a = 13.5685 (3) Å

  • b = 8.0532 (2) Å

  • c = 13.2447 (2) Å

  • [beta] = 100.186 (1)°

  • V = 1424.44 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.283, Tmax = 0.845

  • 9148 measured reflections

  • 2579 independent reflections

  • 2183 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.81 (2) 1.95 (2) 2.657 (2) 145 (3)
N2-H2N...O2 0.85 (2) 2.07 (2) 2.913 (3) 170 (2)
O11-H11...O8i 0.83 (2) 1.94 (2) 2.750 (2) 168 (3)
O13-H13...O1ii 0.79 (2) 2.19 (2) 2.959 (2) 165 (3)
O2-H2A...O8i 0.81 (2) 1.98 (2) 2.776 (3) 171 (4)
O2-H2B...O11iii 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort]
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.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2010). E66, o2045  [ doi:10.1107/S1600536810027856 ]

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