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Volume 69 
Part 12 
Pages o1775-o1776  
December 2013  

Received 28 October 2013
Accepted 7 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.044
wR = 0.114
Data-to-parameter ratio = 13.6
Details
Open access

N'-[(E)-5-Bromo-2-hy­droxy-3-meth­oxy­benzyl­idene]benzohydrazide monohydrate

aDepartment of Chemistry, St. Joseph's College, Irinjalakuda, India,bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
Correspondence e-mail: eesans@yahoo.com

The title compound, C15H13BrN2O3·H2O, exists in an E conformation with respect to the azo­methane C=N double bond. The benzene and phenyl rings form dihedral angles of 0.46 (2) and 4.90 (3)°, respectively with the central C(=O)N2C unit. An intra­molecular O-H...N hydrogen bond occurs. In the crystal, some hydrazide mol­ecules are replaced by mol­ecules of the 6-bromo isomer. The Br atom from this admixture was refined to give a partial occupancy of 0.0443 (19). A supra­molecular network is built in the lattice by means of inter­molecular N-H...O and two O-H...O inter­actions together with non-classical C-H...O inter­actions involving the lattice water mol­ecule stacking the mol­ecules along the b-axis direction.

Related literature

For biological applications of benzohydrazones and derivatives, see: Sreeja et al. (2004[Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.]); Rada & Leto (2008[Rada, B. & Leto, T. (2008). Contrib. Microbiol. 15, 164-187.]); Rakha et al. (1996[Rakha, T. H., Ibrahim, K. M., Abdallah, A. M. & Hassanian, M. M. (1996). Synth. React. Inorg. Met. Org. Chem. 26, 1113-1123.]); Takahama (1996[Takahama, U. (1996). Physiol. Plant. 98, 731-736.]). For the synthesis of related compounds, see: Emmanuel et al. (2011[Emmanuel, J., Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o3267.]). For a related structure, see Reshma et al. (2012[Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2821-o2822.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13BrN2O3·H2O

  • Mr = 367.20

  • Orthorhombic, P 21 21 21

  • a = 4.7223 (5) Å

  • b = 13.9357 (17) Å

  • c = 23.028 (3) Å

  • V = 1515.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.73 mm-1

  • T = 293 K

  • 0.32 × 0.25 × 0.22 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.446, Tmax = 0.549

  • 12759 measured reflections

  • 2966 independent reflections

  • 2189 reflections with I > 2[sigma](I)

  • Rint = 0.090

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.114

  • S = 0.89

  • 2966 reflections

  • 218 parameters

  • 7 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1203 Friedel pairs

  • Absolute structure parameter: 0.016 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1Wi 0.86 2.11 2.946 (5) 163
O1-H1...N1 0.83 1.93 2.637 (5) 142
O1W-H1B...O2ii 0.86 (2) 2.50 (5) 3.178 (5) 136 (6)
O1W-H1B...O1ii 0.86 (2) 2.27 (4) 3.051 (5) 151 (6)
O1W-H1A...O3 0.86 (2) 1.91 (3) 2.736 (5) 163 (6)
C7-H7...O1Wi 0.93 2.50 3.305 (6) 145
C10-H10...O1Wi 0.93 2.42 3.329 (6) 166
C11-H11...O2i 0.93 2.55 3.435 (5) 160
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: HG5359 ).


Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the single-crystal X-ray diffraction measurements. The authors are grateful to Dr Matthias Zeller, Department of Chemistry, Youngstown State University, for support with the data refinement.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Emmanuel, J., Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o3267.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Rada, B. & Leto, T. (2008). Contrib. Microbiol. 15, 164-187.  [CrossRef] [PubMed] [ChemPort]
Rakha, T. H., Ibrahim, K. M., Abdallah, A. M. & Hassanian, M. M. (1996). Synth. React. Inorg. Met. Org. Chem. 26, 1113-1123.  [ChemPort]
Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2821-o2822.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Takahama, U. (1996). Physiol. Plant. 98, 731-736.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1775-o1776   [ doi:10.1107/S1600536813030572 ]

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