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Volume 69 
Part 7 
Pages o1177-o1178  
July 2013  

Received 17 June 2013
Accepted 24 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.155
Data-to-parameter ratio = 16.7
Details
Open access

(E)-N'-(4-Methoxybenzylidene)pyridine-3-carbohydrazide dihydrate

aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India,bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India, and cPG & Research Department of Chemistry, Jamal Mohamed College, Tiruchirappalli-20, India
Correspondence e-mail: vasuki.arasi@yahoo.com

In the title compound, C14H13N3O2·2H2O, the hydrazone molecule adopts an E conformation with respect to the C=N bond. The dihedral angle between the benzene and pyridine rings is 8.55 (10)°. The methylidene-hydrazide [-C(=O)-N-N=C-] fragment is essentially planar, with a maximum deviation of 0.0375 (13) Å. The mean planes of the benzene and pyridine rings make dihedral angles of 2.71 (14) and 11.25 (13)°, respectively, with mean plane of the methylidene-hydrazide fragment. In the crystal, the benzohydrazide and water molecules are linked by N-H...O, O-H...O and O-H...N hydrogen bonds into a three-dimensional network.

Related literature

For the biological activity of benzohydrazides, see: Hai-Yun (2011[Hai-Yun, Z. (2011). Chin. J. Struct. Chem. 30, 724-730.]); Havanur et al. (2010[Havanur, V. C., Badiger, D. S., Ligade, S. G. & Gudasi, K. B. (2010). Pharma Chem. 2, 390-404.]); Parashar et al. (2009[Parashar, B., Punjabi, P. B., Gupta, G. D. & Sharma, V. K. (2009). Int. J. Chem. Tech. Res. 1, 1022-1025.]). For details of the ability of benzohydrazone compounds to inhibit cell growth and DNA synthesis, see: Ambwani et al. (2011[Ambwani, J., Dikshit, S. N., Tiwari, V. K., Dubey, A. K. & Rahul, A. (2011). Asian J. Chem. Environ. Res. 4, 33-35.]); Despaigne et al. (2010[Despaigne, A. A. R., Vieira, L. F., Mendes, I. C., da Costa, F. B., Speziali, N. L. & Beraldo, H. (2010). J. Braz. Chem. Soc. 21, 1247-1257.]); Havanur et al. (2010[Havanur, V. C., Badiger, D. S., Ligade, S. G. & Gudasi, K. B. (2010). Pharma Chem. 2, 390-404.]). For background to the use of benzohydrazides as catalysts, see: Seleem et al. (2011[Seleem, H. S., El-Inany, G. A., El-Shetary, B. A., Mousa, M. A. & Hanafy, F. I. (2011). Chem. Cent. J. 5, 1-9.]); Singh & Raghav (2011[Singh, M. & Raghav, N. (2011). Int. J. Pharm. Pharm. Sci. 3, 26-32.]). For related structures, see: Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.]); Hu & Liu (2012[Hu, H.-N. & Liu, S.-Y. (2012). Acta Cryst. E68, o1613.]); Shi & Li (2012[Shi, Z.-F. & Li, J.-M. (2012). Acta Cryst. E68, o1726.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N3O2·2H2O

  • Mr = 291.31

  • Monoclinic, P 21 /n

  • a = 7.6534 (6) Å

  • b = 16.3503 (11) Å

  • c = 11.4887 (6) Å

  • [beta] = 96.889 (2)°

  • V = 1427.26 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.980

  • 11391 measured reflections

  • 3449 independent reflections

  • 2050 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.155

  • S = 0.93

  • 3449 reflections

  • 206 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N2...O1W 0.86 2.08 2.9013 (17) 161
O1W-H1O1...N3i 0.81 (1) 2.08 (1) 2.8697 (18) 166 (2)
O1W-H2O1...O2Wii 0.83 (1) 1.93 (1) 2.749 (2) 171 (2)
O2W-H1O2...N1iii 0.83 (2) 2.40 (2) 3.209 (2) 166 (3)
O2W-H2O2...O2 0.83 (2) 2.01 (2) 2.8182 (17) 164 (2)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); 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 Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: 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: SJ5336 ).


Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, STIC, Cochin University of Science & Technology, Cochin, for the data collection.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.  [CrossRef] [IUCr Journals]
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Ambwani, J., Dikshit, S. N., Tiwari, V. K., Dubey, A. K. & Rahul, A. (2011). Asian J. Chem. Environ. Res. 4, 33-35.  [ChemPort]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Despaigne, A. A. R., Vieira, L. F., Mendes, I. C., da Costa, F. B., Speziali, N. L. & Beraldo, H. (2010). J. Braz. Chem. Soc. 21, 1247-1257.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hai-Yun, Z. (2011). Chin. J. Struct. Chem. 30, 724-730.
Havanur, V. C., Badiger, D. S., Ligade, S. G. & Gudasi, K. B. (2010). Pharma Chem. 2, 390-404.  [ChemPort]
Hu, H.-N. & Liu, S.-Y. (2012). Acta Cryst. E68, o1613.  [CSD] [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Parashar, B., Punjabi, P. B., Gupta, G. D. & Sharma, V. K. (2009). Int. J. Chem. Tech. Res. 1, 1022-1025.  [ChemPort]
Seleem, H. S., El-Inany, G. A., El-Shetary, B. A., Mousa, M. A. & Hanafy, F. I. (2011). Chem. Cent. J. 5, 1-9.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shi, Z.-F. & Li, J.-M. (2012). Acta Cryst. E68, o1726.  [CrossRef] [IUCr Journals]
Singh, M. & Raghav, N. (2011). Int. J. Pharm. Pharm. Sci. 3, 26-32.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1177-o1178   [ doi:10.1107/S1600536813017406 ]

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