3,5-Dimethyl­pyrazolium 3,5-dinitro­salicylate

Wei, S.; Jin, S.; Hu, Z.; Zhou, Y.; Zhou, Y.

doi:10.1107/S1600536812041906

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 (C-C) = 0.005 Å
R = 0.047
wR = 0.105
Data-to-parameter ratio = 11.1
Details

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate

Shuaishuai Wei,^a Shouwen Jin,^a ^* Zhaofeng Hu,^a Yong Zhou ^a and Yingping Zhou ^a

^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-HO hydrogen bond in the anion generates an S(6) ring. In the crystal, the components are linked by cation-to-anion N-HO and N-H(O,O) hydrogen bonds, generating [010] double chains. Weak C-HO interactions consolidate the packing.

Related literature

For a related structure and background to hydrogen-bonding interactions, see: Jin et al. (2010). For another related structure, see: Smith et al. (2011).

Experimental

Crystal data

C₅H₉N₂⁺·C₇H₃N₂O₇^-
M_r = 324.26
Monoclinic, P 2₁
a = 8.1183 (7) Å
b = 6.0636 (5) Å
c = 14.1453 (11) Å
= 91.904 (1)°
V = 695.93 (10) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.959, T_max = 0.986
3523 measured reflections
2301 independent reflections
1659 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.105
S = 1.02
2301 reflections
208 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O7ⁱ	0.86	2.09	2.859 (4)	148
N1-H1O1ⁱ	0.86	2.16	2.809 (4)	132
N2-H2O3	0.86	1.88	2.684 (3)	156
O2-H2AO1	0.82	1.72	2.481 (3)	154
C1-H1AO7ⁱ	0.96	2.32	3.166 (5)	147
C5-H5BO4ⁱⁱ	0.96	2.49	3.414 (5)	160
C10-H10O6ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Wermuth, U. D., Healy, P. C. & White, J. M. (2011). J. Chem. Crystallogr. 41, 1649-1662.

organic compounds