3-Benzyl-1-methyl­imidazolium picrate

Pi, M.; Liu, X.-L.; Xu, J.-J.; Jin, C.-M.

doi:10.1107/S1600536809035454

Volume 65
Part 10
Page o2386
October 2009

Received 24 August 2009
Accepted 2 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.056
wR = 0.144
Data-to-parameter ratio = 10.8
Details

3-Benzyl-1-methylimidazolium picrate

Min Pi,^a Xiu-Ling Liu,^a Ji-Jun Xu ^a and Chuan-Ming Jin ^a ^*

^aHubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi, Hubei 435002, People's Republic of China
Correspondence e-mail: cmjin@email.hbnu.edu.cn

In the title salt, C₁₁H₁₃N₂⁺·C₆H₂N₃O₇^-, the dihedral angles between the benzene ring in the cation and the imidazolium ring and the benzene ring of the picrate anion are 113.7 (2) and 116.3 (2)°, respectively. The imidazolium ring is nearly parallel to the benzene ring of the picrate anion, the dihedral angle between the planes being 2.6 (1)°. The nitro groups in the picrate anions are disordered (occupancy ratio 0.54:0.46). The crystal packing is stabilized by weak C-HO interactions between the cation-anion pairs.

Related literature

For civilian and military applications of energetic materials, see: Sikder & Sikder (2004). Heterocyclic organic salts with low melting points are a new class of energetic materials, which have attracted considerable interest because of their `green chemistry' properties, see: Singh et al. (2006). Picric acid is a polynitrogen compound with explosive character and imidazolium-based cation picrate salts are good candidates for energetic ionic salts, see: Jin et al. (2005).

Experimental

Crystal data

C₁₁H₁₃N₂⁺·C₆H₂N₃O₇^-
M_r = 401.34
Triclinic, $[P \overline 1]$
a = 9.1322 (6) Å
b = 10.2060 (7) Å
c = 10.8744 (7) Å
= 63.6190 (10)°
= 80.1660 (10)°
= 86.4820 (10)°
V = 894.52 (10) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.986, T_max = 0.988
5623 measured reflections
3447 independent reflections
2610 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.144
S = 1.04
3447 reflections
320 parameters
15 restraints
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C17-H17CO7ⁱ	0.96	2.42	3.346 (10)	162
C14-H14O5ⁱⁱ	0.93	2.39	3.283 (11)	161
C17-H17AO2ⁱⁱⁱ	0.96	2.32	3.205 (11)	153
C16-H16O2ⁱⁱⁱ	0.93	2.39	3.159 (9)	140
C16-H16O1ⁱⁱⁱ	0.93	2.19	3.021 (2)	149
C13-H13AO1ⁱⁱⁱ	0.97	2.58	3.382 (3)	140
C17-H17CO7ⁱ	0.96	2.42	3.346 (10)	162
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) x, y-1, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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: JJ2007 ).

Acknowledgements

We gratefully acknowledge the financial support of the National Science Funds for Distinguished Young Scholars of Hubei Province (grant No. 2006ABB038), the Outstanding Mid-young Scholars' Programs, Hubei Provincial Department of Education (Q20072203) and the project sponsored by SRF for ROCS, SEM (200724).

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.
Jin, C. M., Ye, C., Piekarski, C., Twamley, B. & Shreeve, J. M. (2005). Eur. J. Inorg. Chem. pp. 3760-3767.
Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sikder, A. K. & Sikder, N. J. (2004). J. Hazardous Materials A, 112, 1-15.
Singh, R. P., Verma, R. D., Meshri, D. T. & Shreeve, J. M. (2006). Angew. Chem. Int. Ed. 45, 3584-3601.

organic compounds