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Volume 69 
Part 8 
Pages o1342-o1343  
August 2013  

Received 30 June 2013
Accepted 20 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.114
Data-to-parameter ratio = 15.2
Details
Open access

N'-{(E)-[5-(Hydroxymethyl)furan-2-yl]methylidene}pyridine-4-carbohydrazide dihydrate

aDepartment of Chemistry and Research Centre, PRNSS College, Mattanur 670 702, Kannur, Kerala, 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

In the title compound, C12H11N3O3·2H2O, the dihedral angle formed by the planes of the pyridine and the furan rings of the organic carbohydrazide molecule is 4.66 (7)°. In the crystal, these molecules form stacks along the b-axis direction, neighbouring molecules within each stack being related by inversion and the shortest distance between the centroids of the pyridine and furan rings being 3.714 (1) Å. Molecules from neighboring stacks are linked by pairs of N-H...O hydrogen bonds. The water molecules fill the channels between the stacks being linked by O-H...O hydrogen bonds into helices along [010]. Besides this, water molecules are involved in O-H...N and O-H...O hydrogen bonds with the carbohydrazide molecules, thus forming a three-dimensional network, augmented by weak C-H...O interactions.

Related literature

For biological properties of carbohydrazide and its derivatives, see: Rollas & Kucukguzel (2007[Rollas, S. & Kucukguzel, S. G. (2007). Molecules, 12, 1910-1939.]); Bakir & Brown (2002[Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129-136.]). For the synthesis of related compounds, see: Sreeja & Kurup (2005[Sreeja, P. B. & Kurup, M. R. P. (2005). Spectrochim. Acta Part A, 61, 331-336.]). For related structures, see: Nair et al. (2012[Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.]); Reshma et al. (2012[Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2785.]); Prasanna et al. (2013[Prasanna, M. K., Sithambaresan, M., Pradeepkumar, K. & Kurup, M. R. P. (2013). Acta Cryst. E69, o881.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11N3O3·2H2O

  • Mr = 281.27

  • Monoclinic, P 21 /c

  • a = 10.7020 (14) Å

  • b = 7.0263 (8) Å

  • c = 18.024 (3) Å

  • [beta] = 106.252 (7)°

  • V = 1301.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.50 × 0.25 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.972

  • 9681 measured reflections

  • 3139 independent reflections

  • 2308 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.114

  • S = 1.03

  • 3139 reflections

  • 206 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2S-H2A...N3 0.85 (2) 2.49 (2) 3.2272 (17) 146 (2)
O2S-H2A...O1 0.85 (2) 2.22 (2) 2.9648 (15) 146 (2)
O3-H3'...O1Si 0.89 (2) 1.90 (2) 2.7937 (16) 174.9 (18)
O2S-H2B...O1Sii 0.86 (2) 2.06 (2) 2.9145 (18) 171 (2)
O1S-H1B...O2Siii 0.87 (2) 1.94 (2) 2.7924 (17) 167 (2)
N2-H2'...O3iv 0.876 (18) 2.024 (18) 2.8485 (16) 156.3 (16)
O1S-H1A...N1 0.87 (2) 2.03 (2) 2.8501 (16) 157 (2)
C4-H4...O3iv 0.93 2.50 3.3897 (18) 160
C12-H12B...O1v 0.97 2.43 3.3621 (19) 162
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+2, -z+1; (iii) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) -x+1, -y+2, -z+2; (v) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SADABS, 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: 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: YK2097 ).


Acknowledgements

MKP is thankful to the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK is thankful to the UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. 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.

References

Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129-136.  [Web of Science] [CrossRef] [ChemPort]
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.  [CrossRef] [IUCr Journals]
Prasanna, M. K., Sithambaresan, M., Pradeepkumar, K. & Kurup, M. R. P. (2013). Acta Cryst. E69, o881.  [CrossRef] [IUCr Journals]
Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2785.  [CrossRef] [IUCr Journals]
Rollas, S. & Kucukguzel, S. G. (2007). Molecules, 12, 1910-1939.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreeja, P. B. & Kurup, M. R. P. (2005). Spectrochim. Acta Part A, 61, 331-336.  [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1342-o1343   [ doi:10.1107/S1600536813020114 ]

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