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Volume 69 
Part 4 
Page o490  
April 2013  

Received 18 February 2013
Accepted 27 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.111
Data-to-parameter ratio = 13.1
Details
Open access

(E)-N'-(3,4-Dihydroxybenzylidene)-2,4-dimethylbenzohydrazide monohydrate

aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia,bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D. E., Malaysia,cDepartment of Chemical Sciences, Faculty of Science and Technology, University Malaysia Terengganu, 21030, Kuala Terengganu, Malaysia, and dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title compound, C16H16N2O3·H2O, the dihedral angle between the benzene rings is 30.27 (7)°. In the crystal, the components are linked by N-H...O, O-H...O and C-H...O interactions into a three-dimensional network.

Related literature

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012[Musharraf, S. G., Bibi, A., Shahid, N., Najam-ul-Haq, M., Khan, M., Taha, M., Mughal, U. R. & Khan, K. M. (2012). Am. J. Anal. Chem. 3, 779-789.]); Khan et al. (2012[Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705-710.]). For the crystal structures of related compounds, see: Taha et al. (2012[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012). Acta Cryst. E68, o2778.]); Baharudin et al. (2012[Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O3·H2O

  • Mr = 302.32

  • Monoclinic, P 21 /n

  • a = 8.1373 (3) Å

  • b = 13.9025 (5) Å

  • c = 13.7886 (5) Å

  • [beta] = 92.913 (1)°

  • V = 1557.87 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.30 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.991

  • 9012 measured reflections

  • 2897 independent reflections

  • 2535 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.111

  • S = 1.05

  • 2897 reflections

  • 221 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1W1...N2i 0.87 (2) 2.20 (2) 3.059 (2) 169 (2)
O1W-H2W1...O1 0.94 (2) 2.01 (2) 2.935 (2) 173 (2)
N1-H1A...O3ii 0.91 (2) 2.08 (2) 2.962 (2) 163 (2)
O2-H2A...O1i 0.88 (2) 1.94 (2) 2.791 (2) 162 (2)
O3-H3A...O1Wiii 0.85 (2) 1.79 (2) 2.629 (2) 172 (2)
C8-H8A...O3ii 0.93 2.58 3.382 (2) 145
C15-H15B...O2i 0.96 2.52 3.351 (2) 144
Symmetry codes: (i) -x, -y+1, -z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2622 ).


Acknowledgements

The authors thank the Research Management Institute of UiTM for financial support under the Dana Kecemerlangan Grant Scheme [grant No. 600-RMI/DANA 5/3 RIF (143/2012)].

References

Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255.  [CSD] [CrossRef] [details]
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705-710.  [ChemPort] [PubMed]
Musharraf, S. G., Bibi, A., Shahid, N., Najam-ul-Haq, M., Khan, M., Taha, M., Mughal, U. R. & Khan, K. M. (2012). Am. J. Anal. Chem. 3, 779-789.  [CrossRef]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012). Acta Cryst. E68, o2778.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o490  [ doi:10.1107/S1600536813005692 ]

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