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Volume 69 
Part 5 
Page o767  
May 2013  

Received 5 November 2012
Accepted 2 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 12.3
Details
Open access

1-(2,3-Dicyanophenyl)pyridin-1-ium-4-olate monohydrate

aSchool of Materials Science and Engineering of Shandong University, 250014 Jinan, People's Republic of China,bNew Materials Institute of Shandong Academy of Sciences, 250014 Jinan, People's Republic of China, and cSchool of Environmental Science and Engineering of Shandong University, 250100 Jinan, People's Republic of China
Correspondence e-mail: fengsuping@126.com

In the crystal structure of the title compound, C13H7N3O·H2O, the components are associated into chains along [010] through strong O-H...O hydrogen bonds with the free water molecules as bridging ligands. These chains are further cross-linked by C-H...O and C-H...N hydrogen bonds, forming a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Archibald et al. (1994[Archibald, S. J., Blake, A. J., Schroder, M. & Winpenny, R. E. P. (1994). Chem. Commun. pp. 1669-1670.])

[Scheme 1]

Experimental

Crystal data
  • C13H7N3O·H2O

  • Mr = 239.23

  • Monoclinic, P 21 /c

  • a = 11.977 (2) Å

  • b = 7.2497 (12) Å

  • c = 13.850 (2) Å

  • [beta] = 94.244 (3)°

  • V = 1199.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.12 × 0.10 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.989, Tmax = 0.993

  • 5795 measured reflections

  • 2112 independent reflections

  • 1349 reflections with I > 2[sigma](I)

  • Rint = 0.042

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

  • wR(F2) = 0.124

  • S = 1.03

  • 2112 reflections

  • 172 parameters

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

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1WA...O1 0.98 (3) 1.79 (3) 2.763 (2) 170 (3)
O1W-H1WB...O1i 0.87 (3) 1.88 (3) 2.721 (2) 162 (3)
C6-H6A...O1Wii 0.93 2.37 3.302 (3) 177
C13-H13A...O1Wiii 0.93 2.38 3.311 (3) 175
C9-H9A...N1iv 0.93 2.55 3.440 (2) 160
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2216 ).


References

Archibald, S. J., Blake, A. J., Schroder, M. & Winpenny, R. E. P. (1994). Chem. Commun. pp. 1669-1670.
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o767  [ doi:10.1107/S1600536813008891 ]

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