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Volume 68 
Part 11 
Page o3117  
November 2012  

Received 10 September 2012
Accepted 6 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.047
wR = 0.105
Data-to-parameter ratio = 11.1
Details
Open access

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate

aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China
Correspondence e-mail: shouwenjin@yahoo.cn

In the title molecular salt, C5H9N2+·C7H3N2O7-, the roughly planar anion (r.m.s. deviation = 0.120 Å) has been deprotonated at the phenol group. An intramolecular O-H...O hydrogen bond in the anion generates an S(6) ring. In the crystal, the components are linked by cation-to-anion N-H...O and N-H...(O,O) hydrogen bonds, generating [010] double chains. Weak C-H...O interactions consolidate the packing.

Related literature

For a related structure and background to hydrogen-bonding interactions, see: Jin et al. (2010[Jin, S. W., Zhang, W. B., Liu, L., Gao, H. F., Wang, D. Q., Chen, R. P. & Xu, X. L. (2010). J. Mol. Struct. 975, 128-136.]). For another related structure, see: Smith et al. (2011[Smith, G., Wermuth, U. D., Healy, P. C. & White, J. M. (2011). J. Chem. Crystallogr. 41, 1649-1662.]).

[Scheme 1]

Experimental

Crystal data
  • C5H9N2+·C7H3N2O7-

  • Mr = 324.26

  • Monoclinic, P 21

  • a = 8.1183 (7) Å

  • b = 6.0636 (5) Å

  • c = 14.1453 (11) Å

  • [beta] = 91.904 (1)°

  • V = 695.93 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.40 × 0.27 × 0.11 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.986

  • 3523 measured reflections

  • 2301 independent reflections

  • 1659 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.105

  • S = 1.02

  • 2301 reflections

  • 208 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O7i 0.86 2.09 2.859 (4) 148
N1-H1...O1i 0.86 2.16 2.809 (4) 132
N2-H2...O3 0.86 1.88 2.684 (3) 156
O2-H2A...O1 0.82 1.72 2.481 (3) 154
C1-H1A...O7i 0.96 2.32 3.166 (5) 147
C5-H5B...O4ii 0.96 2.49 3.414 (5) 160
C10-H10...O6iii 0.93 2.48 3.379 (4) 164
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x, y-{\script{3\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6958 ).


Acknowledgements

We gratefully acknowledge the financial support of the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the innovation project of Zhejiang A & F University.

References

Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jin, S. W., Zhang, W. B., Liu, L., Gao, H. F., Wang, D. Q., Chen, R. P. & Xu, X. L. (2010). J. Mol. Struct. 975, 128-136.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Wermuth, U. D., Healy, P. C. & White, J. M. (2011). J. Chem. Crystallogr. 41, 1649-1662.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3117  [ doi:10.1107/S1600536812041906 ]

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