3-Benzyl-1-methyl-imidazolium picrate.

In the title salt, C(11)H(13)N(2) (+)·C(6)H(2)N(3)O(7) (-), 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-H⋯O inter-actions 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 = 401.34

Triclinic,

a = 9.1322 (6) Å

b = 10.2060 (7) Å

c = 10.8744 (7) Å

α = 63.6190 (10)°

β = 80.1660 (10)°

γ = 86.4820 (10)°

V = 894.52 (10) Å3

Z = 2

Mo Kα radiation

μ = 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 (; Sheldrick, 1996 ▶) T min = 0.986, T max = 0.988

5623 measured reflections

3447 independent reflections

2610 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.144

S = 1.04

3447 reflections

320 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.24 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035454/jj2007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035454/jj2007Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H13N2+·C6H2N3O7−	Z = 2
Mr = 401.34	F(000) = 416
Triclinic, P1	Dx = 1.490 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1322 (6) Å	Cell parameters from 1924 reflections
b = 10.2060 (7) Å	θ = 2.2–26.5°
c = 10.8744 (7) Å	µ = 0.12 mm−1
α = 63.619 (1)°	T = 298 K
β = 80.166 (1)°	Block, yellow
γ = 86.482 (1)°	0.20 × 0.10 × 0.10 mm
V = 894.52 (10) Å3

Bruker SMART APEX CCD area-detector diffractometer	3447 independent reflections
Radiation source: fine-focus sealed tube	2610 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.986, Tmax = 0.988	k = −12→12
5623 measured reflections	l = −11→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3
3447 reflections	(Δ/σ)max < 0.001
320 parameters	Δρmax = 0.35 e Å−3
15 restraints	Δρmin = −0.24 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6669 (2)	0.9523 (2)	0.3757 (2)	0.0412 (5)
C2	0.5960 (2)	0.8381 (2)	0.50638 (19)	0.0391 (5)
C3	0.4985 (2)	0.7359 (2)	0.5166 (2)	0.0417 (5)
H3	0.4582	0.6639	0.6035	0.050*
C4	0.4602 (2)	0.7397 (2)	0.3977 (2)	0.0421 (5)
C5	0.5191 (2)	0.8461 (2)	0.2678 (2)	0.0435 (5)
H5	0.4912	0.8496	0.1881	0.052*
C6	0.6182 (2)	0.9453 (2)	0.25820 (19)	0.0409 (5)
C7	0.9029 (2)	0.4665 (2)	0.16740 (19)	0.0448 (5)
C8	0.7605 (3)	0.4513 (3)	0.1476 (2)	0.0602 (6)
H8	0.7217	0.3584	0.1754	0.072*
C9	0.6758 (3)	0.5720 (4)	0.0873 (3)	0.0767 (8)
H9	0.5803	0.5606	0.0741	0.092*
C10	0.7316 (3)	0.7092 (3)	0.0466 (2)	0.0736 (8)
H10	0.6740	0.7908	0.0058	0.088*
C11	0.8721 (3)	0.7263 (3)	0.0659 (2)	0.0670 (7)
H11	0.9097	0.8194	0.0390	0.080*
C12	0.9572 (3)	0.6063 (2)	0.1247 (2)	0.0525 (6)
H12	1.0532	0.6188	0.1362	0.063*
C13	0.9942 (3)	0.3344 (2)	0.2325 (2)	0.0516 (6)
H13A	0.9526	0.2525	0.2267	0.062*
H13B	1.0944	0.3526	0.1807	0.062*
C14	1.0841 (2)	0.3658 (2)	0.4261 (2)	0.0495 (5)
H14	1.1477	0.4457	0.3713	0.059*
C15	1.0570 (2)	0.2983 (2)	0.5651 (2)	0.0492 (5)
H15	1.0988	0.3221	0.6249	0.059*
C16	0.9239 (2)	0.1884 (2)	0.4886 (2)	0.0428 (5)
H16	0.8581	0.1243	0.4855	0.051*
C17	0.9006 (3)	0.0830 (3)	0.7460 (2)	0.0630 (7)
H17A	0.8231	0.0235	0.7460	0.094*
H17B	0.8617	0.1349	0.7993	0.094*
H17C	0.9802	0.0218	0.7866	0.094*
N1	0.6315 (2)	0.8244 (2)	0.63649 (18)	0.0492 (5)
N2	0.3603 (2)	0.6289 (2)	0.4097 (2)	0.0525 (5)
N3	0.6791 (2)	1.0516 (2)	0.11900 (19)	0.0537 (5)
N4	1.00040 (18)	0.29513 (17)	0.37987 (16)	0.0416 (4)
N5	0.95646 (18)	0.18786 (18)	0.60292 (16)	0.0436 (4)
O1	0.75553 (19)	1.04635 (18)	0.36201 (16)	0.0646 (5)
O2	0.6926 (10)	0.9248 (11)	0.6410 (15)	0.064 (2)	0.54
O3	0.6079 (6)	0.7030 (6)	0.7381 (6)	0.0693 (15)	0.54
O4	0.3127 (14)	0.5302 (14)	0.5267 (10)	0.091 (4)	0.54
O5	0.3362 (16)	0.6282 (15)	0.3029 (9)	0.093 (4)	0.54
O6	0.5945 (15)	1.1147 (16)	0.0366 (15)	0.104 (4)	0.58
O7	0.8115 (7)	1.0704 (12)	0.0890 (11)	0.075 (2)	0.58
O2'	0.5492 (7)	0.7504 (8)	0.7465 (7)	0.0700 (18)	0.46
O3'	0.7363 (11)	0.8962 (12)	0.6320 (17)	0.060 (2)	0.46
O5'	0.3250 (14)	0.6386 (14)	0.3006 (8)	0.061 (3)	0.46
O4'	0.3061 (11)	0.5414 (13)	0.5233 (7)	0.047 (2)	0.46
O6'	0.616 (2)	1.073 (2)	0.027 (2)	0.094 (5)	0.42
O7'	0.7953 (14)	1.1148 (18)	0.0970 (19)	0.114 (6)	0.42

	U11	U22	U33	U12	U13	U23
C1	0.0384 (10)	0.0434 (11)	0.0450 (11)	−0.0048 (9)	−0.0101 (9)	−0.0205 (9)
C2	0.0363 (10)	0.0451 (11)	0.0391 (11)	0.0023 (9)	−0.0108 (8)	−0.0197 (9)
C3	0.0372 (11)	0.0410 (11)	0.0427 (11)	−0.0032 (9)	−0.0058 (9)	−0.0143 (9)
C4	0.0377 (10)	0.0424 (11)	0.0492 (12)	−0.0051 (9)	−0.0082 (9)	−0.0218 (10)
C5	0.0415 (11)	0.0514 (12)	0.0448 (11)	−0.0017 (9)	−0.0117 (9)	−0.0257 (10)
C6	0.0392 (11)	0.0431 (11)	0.0383 (10)	−0.0037 (9)	−0.0064 (8)	−0.0155 (9)
C7	0.0523 (12)	0.0520 (12)	0.0282 (10)	−0.0094 (10)	0.0025 (9)	−0.0177 (9)
C8	0.0590 (15)	0.0666 (16)	0.0465 (13)	−0.0155 (13)	−0.0010 (11)	−0.0180 (12)
C9	0.0572 (16)	0.106 (2)	0.0563 (16)	0.0023 (16)	−0.0112 (13)	−0.0260 (16)
C10	0.085 (2)	0.0757 (19)	0.0474 (14)	0.0179 (16)	−0.0074 (14)	−0.0192 (13)
C11	0.097 (2)	0.0537 (15)	0.0442 (13)	−0.0012 (14)	−0.0074 (13)	−0.0168 (11)
C12	0.0646 (14)	0.0521 (14)	0.0380 (11)	−0.0117 (11)	−0.0067 (10)	−0.0164 (10)
C13	0.0612 (14)	0.0543 (13)	0.0407 (11)	−0.0084 (11)	0.0008 (10)	−0.0242 (10)
C14	0.0472 (12)	0.0419 (12)	0.0629 (14)	−0.0066 (10)	−0.0119 (10)	−0.0242 (11)
C15	0.0530 (13)	0.0469 (12)	0.0599 (14)	0.0027 (10)	−0.0239 (11)	−0.0293 (11)
C16	0.0446 (11)	0.0424 (11)	0.0447 (11)	−0.0041 (9)	−0.0116 (9)	−0.0199 (9)
C17	0.0752 (16)	0.0644 (15)	0.0433 (13)	−0.0063 (13)	−0.0174 (11)	−0.0147 (11)
N1	0.0475 (11)	0.0565 (12)	0.0424 (10)	−0.0041 (9)	−0.0111 (8)	−0.0188 (9)
N2	0.0482 (11)	0.0498 (12)	0.0635 (13)	−0.0084 (9)	−0.0101 (11)	−0.0272 (11)
N3	0.0581 (13)	0.0584 (12)	0.0426 (11)	−0.0144 (10)	−0.0124 (10)	−0.0170 (9)
N4	0.0448 (9)	0.0405 (9)	0.0417 (9)	−0.0045 (8)	−0.0063 (7)	−0.0196 (8)
N5	0.0471 (10)	0.0443 (10)	0.0427 (10)	0.0013 (8)	−0.0156 (8)	−0.0191 (8)
O1	0.0735 (11)	0.0697 (11)	0.0521 (9)	−0.0361 (9)	−0.0076 (8)	−0.0242 (8)
O2	0.083 (5)	0.064 (4)	0.055 (3)	−0.012 (4)	−0.016 (4)	−0.032 (3)
O3	0.081 (4)	0.077 (4)	0.039 (2)	−0.019 (3)	−0.011 (3)	−0.013 (2)
O4	0.099 (7)	0.054 (5)	0.108 (7)	−0.019 (5)	−0.016 (5)	−0.023 (5)
O5	0.119 (8)	0.103 (7)	0.089 (8)	−0.022 (5)	−0.024 (5)	−0.066 (6)
O6	0.086 (4)	0.118 (8)	0.062 (5)	0.003 (5)	−0.028 (3)	0.005 (4)
O7	0.044 (2)	0.096 (5)	0.056 (3)	−0.021 (2)	0.0098 (19)	−0.011 (3)
O2'	0.068 (4)	0.094 (5)	0.040 (2)	−0.026 (3)	0.000 (3)	−0.022 (3)
O3'	0.064 (5)	0.067 (5)	0.058 (4)	−0.014 (4)	−0.021 (4)	−0.031 (3)
O5'	0.063 (5)	0.059 (5)	0.058 (6)	−0.037 (4)	−0.017 (4)	−0.014 (4)
O4'	0.048 (4)	0.053 (5)	0.039 (4)	−0.031 (4)	0.005 (3)	−0.018 (4)
O6'	0.127 (11)	0.104 (9)	0.047 (4)	−0.047 (7)	−0.034 (6)	−0.017 (5)
O7'	0.126 (9)	0.122 (11)	0.080 (5)	−0.060 (8)	−0.017 (6)	−0.026 (6)

C1—O1	1.235 (2)	C13—H13B	0.9700
C1—C2	1.451 (3)	C14—C15	1.336 (3)
C1—C6	1.454 (3)	C14—N4	1.371 (3)
C2—C3	1.368 (3)	C14—H14	0.9300
C2—N1	1.450 (2)	C15—N5	1.367 (3)
C3—C4	1.379 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—N4	1.319 (2)
C4—C5	1.383 (3)	C16—N5	1.325 (2)
C4—N2	1.443 (3)	C16—H16	0.9300
C5—C6	1.357 (3)	C17—N5	1.464 (3)
C5—H5	0.9300	C17—H17A	0.9600
C6—N3	1.451 (3)	C17—H17B	0.9600
C7—C8	1.383 (3)	C17—H17C	0.9600
C7—C12	1.385 (3)	N1—O2	1.220 (9)
C7—C13	1.493 (3)	N1—O3'	1.222 (10)
C8—C9	1.373 (4)	N1—O2'	1.235 (7)
C8—H8	0.9300	N1—O3	1.240 (6)
C9—C10	1.369 (4)	N2—O4'	1.197 (7)
C9—H9	0.9300	N2—O5	1.222 (9)
C10—C11	1.368 (4)	N2—O5'	1.243 (9)
C10—H10	0.9300	N2—O4	1.245 (9)
C11—C12	1.367 (3)	N3—O6'	1.168 (11)
C11—H11	0.9300	N3—O7	1.201 (7)
C12—H12	0.9300	N3—O7'	1.208 (11)
C13—N4	1.480 (3)	N3—O6	1.215 (10)
C13—H13A	0.9700
O1—C1—C2	126.06 (18)	N4—C14—H14	126.5
O1—C1—C6	122.83 (18)	C14—C15—N5	107.38 (18)
C2—C1—C6	111.10 (16)	C14—C15—H15	126.3
C3—C2—N1	116.05 (17)	N5—C15—H15	126.3
C3—C2—C1	124.07 (18)	N4—C16—N5	108.52 (17)
N1—C2—C1	119.85 (17)	N4—C16—H16	125.7
C2—C3—C4	119.81 (18)	N5—C16—H16	125.7
C2—C3—H3	120.1	N5—C17—H17A	109.5
C4—C3—H3	120.1	N5—C17—H17B	109.5
C3—C4—C5	120.79 (18)	H17A—C17—H17B	109.5
C3—C4—N2	119.28 (18)	N5—C17—H17C	109.5
C5—C4—N2	119.92 (19)	H17A—C17—H17C	109.5
C6—C5—C4	119.12 (19)	H17B—C17—H17C	109.5
C6—C5—H5	120.4	O2—N1—O2'	112.3 (8)
C4—C5—H5	120.4	O3'—N1—O2'	122.1 (8)
C5—C6—N3	116.53 (18)	O2—N1—O3	122.5 (7)
C5—C6—C1	125.09 (18)	O3'—N1—O3	116.7 (8)
N3—C6—C1	118.38 (17)	O2—N1—C2	120.6 (7)
C8—C7—C12	118.2 (2)	O3'—N1—C2	118.2 (8)
C8—C7—C13	120.1 (2)	O2'—N1—C2	119.5 (4)
C12—C7—C13	121.7 (2)	O3—N1—C2	116.6 (3)
C9—C8—C7	120.6 (2)	O4'—N2—O5	123.1 (7)
C9—C8—H8	119.7	O4'—N2—O5'	123.6 (5)
C7—C8—H8	119.7	O5—N2—O4	122.0 (7)
C10—C9—C8	120.2 (3)	O5'—N2—O4	123.2 (7)
C10—C9—H9	119.9	O4'—N2—C4	118.7 (4)
C8—C9—H9	119.9	O5—N2—C4	118.2 (5)
C11—C10—C9	120.1 (3)	O5'—N2—C4	117.4 (4)
C11—C10—H10	120.0	O4—N2—C4	119.5 (6)
C9—C10—H10	120.0	O6'—N3—O7	115.7 (13)
C12—C11—C10	119.9 (2)	O6'—N3—O7'	120.1 (12)
C12—C11—H11	120.0	O7—N3—O6	122.8 (9)
C10—C11—H11	120.0	O7'—N3—O6	115.6 (13)
C11—C12—C7	121.1 (2)	O6'—N3—C6	119.1 (10)
C11—C12—H12	119.5	O7—N3—C6	118.5 (5)
C7—C12—H12	119.5	O7'—N3—C6	120.8 (9)
N4—C13—C7	112.48 (16)	O6—N3—C6	118.6 (8)
N4—C13—H13A	109.1	C16—N4—C14	108.63 (17)
C7—C13—H13A	109.1	C16—N4—C13	125.71 (16)
N4—C13—H13B	109.1	C14—N4—C13	125.65 (17)
C7—C13—H13B	109.1	C16—N5—C15	108.46 (17)
H13A—C13—H13B	107.8	C16—N5—C17	126.17 (18)
C15—C14—N4	107.00 (18)	C15—N5—C17	125.31 (18)
C15—C14—H14	126.5
O1—C1—C2—C3	−179.9 (2)	C3—C2—N1—O2'	−18.1 (4)
C6—C1—C2—C3	1.3 (3)	C1—C2—N1—O2'	164.1 (4)
O1—C1—C2—N1	−2.2 (3)	C3—C2—N1—O3	20.3 (4)
C6—C1—C2—N1	178.93 (17)	C1—C2—N1—O3	−157.5 (3)
N1—C2—C3—C4	−179.13 (17)	C3—C4—N2—O4'	4.4 (8)
C1—C2—C3—C4	−1.4 (3)	C5—C4—N2—O4'	−177.1 (7)
C2—C3—C4—C5	0.0 (3)	C3—C4—N2—O5	−174.9 (10)
C2—C3—C4—N2	178.38 (18)	C5—C4—N2—O5	3.6 (10)
C3—C4—C5—C6	1.5 (3)	C3—C4—N2—O5'	177.9 (9)
N2—C4—C5—C6	−176.96 (18)	C5—C4—N2—O5'	−3.6 (9)
C4—C5—C6—N3	178.34 (19)	C3—C4—N2—O4	−1.4 (8)
C4—C5—C6—C1	−1.5 (3)	C5—C4—N2—O4	177.0 (8)
O1—C1—C6—C5	−178.7 (2)	C5—C6—N3—O6'	19.6 (10)
C2—C1—C6—C5	0.2 (3)	C1—C6—N3—O6'	−160.5 (10)
O1—C1—C6—N3	1.4 (3)	C5—C6—N3—O7	−130.6 (6)
C2—C1—C6—N3	−179.67 (17)	C1—C6—N3—O7	49.3 (7)
C12—C7—C8—C9	−0.1 (3)	C5—C6—N3—O7'	−158.5 (9)
C13—C7—C8—C9	−179.7 (2)	C1—C6—N3—O7'	21.4 (9)
C7—C8—C9—C10	−0.3 (4)	C5—C6—N3—O6	47.4 (7)
C8—C9—C10—C11	0.0 (4)	C1—C6—N3—O6	−132.7 (7)
C9—C10—C11—C12	0.6 (4)	N5—C16—N4—C14	−0.4 (2)
C10—C11—C12—C7	−1.0 (3)	N5—C16—N4—C13	−178.99 (17)
C8—C7—C12—C11	0.7 (3)	C15—C14—N4—C16	0.5 (2)
C13—C7—C12—C11	−179.68 (19)	C15—C14—N4—C13	179.14 (19)
C8—C7—C13—N4	−102.8 (2)	C7—C13—N4—C16	102.4 (2)
C12—C7—C13—N4	77.6 (2)	C7—C13—N4—C14	−76.0 (2)
N4—C14—C15—N5	−0.4 (2)	N4—C16—N5—C15	0.1 (2)
C3—C2—N1—O2	−165.4 (5)	N4—C16—N5—C17	−177.20 (19)
C1—C2—N1—O2	16.8 (5)	C14—C15—N5—C16	0.2 (2)
C3—C2—N1—O3'	167.5 (6)	C14—C15—N5—C17	177.5 (2)
C1—C2—N1—O3'	−10.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···O7i	0.96	2.42	3.346 (10)	162
C14—H14···O5ii	0.93	2.39	3.283 (11)	161
C17—H17A···O2iii	0.96	2.32	3.205 (11)	153
C16—H16···O2iii	0.93	2.39	3.159 (9)	140
C16—H16···O1iii	0.93	2.19	3.021 (2)	149
C13—H13A···O1iii	0.97	2.58	3.382 (3)	140
C17—H17C···O7i	0.96	2.42	3.346 (10)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17C⋯O7i	0.96	2.42	3.346 (10)	162
C14—H14⋯O5ii	0.93	2.39	3.283 (11)	161
C17—H17A⋯O2iii	0.96	2.32	3.205 (11)	153
C16—H16⋯O2iii	0.93	2.39	3.159 (9)	140
C16—H16⋯O1iii	0.93	2.19	3.021 (2)	149
C13—H13A⋯O1iii	0.97	2.58	3.382 (3)	140
C17—H17C⋯O7i	0.96	2.42	3.346 (10)	162

Symmetry codes: (i) ; (ii) ; (iii) .