1,1′-Methyl­enebis(2,3-dimethyl­imidazolium) dipicrate acetonitrile solvate

Li, J.

doi:10.1107/S160053680705338X

1,1'-Methylenebis(2,3-dimethylimidazolium) dipicrate acetonitrile solvate

In the title salt, C₁₁H₁₈N₄²⁺·2C₆H₂N₃O₇^-·C₂H₃N, the dihedral angle between the imidazolium rings in the dication is 74.4 (2)°, and the benzene rings of the two independent picrate anions are almost parallel, with a dihedral angle of 12.0 (1)° between them.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705338X/bh2132sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680705338X/bh2132Isup2.hkl Contains datablock I

CCDC reference: 667467

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.007 Å
R factor = 0.059
wR factor = 0.148
Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N8
PLAT432_ALERT_2_B Short Inter X...Y Contact  O6     ..  C4      ..       2.91 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.85
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C9      ..       5.03 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N10
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C25
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.02
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O13    ..  C9      ..       2.98 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3115
           Count of symmetry unique reflns         3115
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Polynitrogen heterocyclic organic salts with low melting points are a new class of energetic materials that has attracted considerable interest because of their "green chemistry" properties (Singh et al., 2006). Imidazolium-based or triazolium-based dication picrate salts are good candidates for energetic ionic salts (Jin et al., 2006). Based on this, the title organic salt (I, Fig. 1) was therefore prepared and its structure is reported here.

The asymmetric unit of the title compound contains one 1,1'-methylene-bis(2,3-dimethylimidazolium) dication, two picrate anions and one acetonitrile molecule. The dihedral angle between imidazolium rings in the dication moiety is 74.4°, and methyl groups at 2-positions in the imidazolium rings are arranged in the same direction. Benzene rings of two independent picrate anions are almost parallel, with a dihedral angle of 12.0°. In the crystal structure, π–π stacking occurs between benzene rings of two different picrate anions, with the shortest separation between ring centroids being 3.767 Å. Weak C—H···O hydrogen bonding occurs between dications and picrate anions.

Related literature top

For the synthesis of the title salt, see: Jin et al. (2005). For related heterocyclic organic salts used as energetic materials, see: Jin et al. (2006); Singh et al. (2006).

Experimental top

The salt (C₁₁H₁₈N₄)²⁺ 2 (C₆H₂N₃O₇)^- was synthesized using a slightly modified literature method (Jin et al., 2005). The title solvate was crystallized by slow evaporation of an acetonitrile solution of the salt.

Structure description top

For the synthesis of the title salt, see: Jin et al. (2005). For related heterocyclic organic salts used as energetic materials, see: Jin et al. (2006); Singh et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. The structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted.

1,1'-Methylenebis(2,3-dimethylimidazolium) dipicrate acetonitrile solvate top

Crystal data top

C₁₁H₁₈N₄²⁺·2C₆H₂N₃O₇⁻·C₂H₃N	D_x = 1.513 Mg m⁻³
M_r = 703.56	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3413 reflections
a = 6.8715 (9) Å	θ = 2.2–19.1°
b = 19.892 (3) Å	µ = 0.13 mm⁻¹
c = 22.594 (3) Å	T = 292 K
V = 3088.2 (7) Å³	Block, yellow
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 1456

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3115 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
T_min = 0.963, T_max = 0.988	k = −23→23
24762 measured reflections	l = −26→26

Refinement top

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0737P)² + 1.7443P] where P = (F_o² + 2F_c²)/3
3115 reflections	(Δ/σ)_max < 0.001
455 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₁H₁₈N₄²⁺·2C₆H₂N₃O₇⁻·C₂H₃N	V = 3088.2 (7) Å³
M_r = 703.56	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.8715 (9) Å	µ = 0.13 mm⁻¹
b = 19.892 (3) Å	T = 292 K
c = 22.594 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3115 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2528 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.988	R_int = 0.061
24762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
3115 reflections	Δρ_min = −0.17 e Å⁻³
455 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7131 (11)	0.6482 (3)	0.8910 (2)	0.0741 (19)
H1A	0.8431	0.6651	0.8955	0.111*
H1B	0.7147	0.6000	0.8931	0.111*
H1C	0.6323	0.6657	0.9221	0.111*
C2	0.4502 (9)	0.6533 (2)	0.8124 (2)	0.0524 (13)
H2A	0.3555	0.6293	0.8328	0.063*
C3	0.4341 (7)	0.6785 (2)	0.7583 (2)	0.0469 (12)
H3A	0.3264	0.6751	0.7335	0.056*
C4	0.7291 (7)	0.7041 (2)	0.7922 (2)	0.0442 (11)
C5	0.9315 (8)	0.7267 (3)	0.7962 (2)	0.0616 (15)
H5A	0.9834	0.7151	0.8343	0.092*
H5B	0.9367	0.7746	0.7911	0.092*
H5C	1.0071	0.7053	0.7658	0.092*
C6	0.6454 (8)	0.7456 (2)	0.68964 (18)	0.0450 (12)
H6A	0.7822	0.7572	0.6872	0.054*
H6B	0.6151	0.7158	0.6569	0.054*
C7	0.3515 (9)	0.8090 (3)	0.6568 (2)	0.0645 (16)
H7A	0.2891	0.7739	0.6374	0.077*
C8	0.2870 (10)	0.8710 (3)	0.6629 (3)	0.0751 (18)
H8A	0.1702	0.8877	0.6482	0.090*
C9	0.5714 (9)	0.8665 (2)	0.70769 (18)	0.0489 (13)
C10	0.4020 (16)	0.9780 (3)	0.7107 (3)	0.110 (3)
H10A	0.4724	0.9864	0.7467	0.164*
H10B	0.2671	0.9886	0.7165	0.164*
H10C	0.4540	1.0054	0.6796	0.164*
C11	0.7443 (12)	0.8842 (3)	0.7422 (2)	0.084 (2)
H11A	0.8574	0.8646	0.7242	0.126*
H11B	0.7306	0.8675	0.7818	0.126*
H11C	0.7584	0.9322	0.7431	0.126*
C12	0.4963 (7)	0.3526 (2)	0.1203 (2)	0.0406 (11)
C13	0.5179 (7)	0.3387 (2)	0.0577 (2)	0.0460 (12)
C14	0.5718 (7)	0.3846 (2)	0.0162 (2)	0.0460 (12)
H14A	0.5832	0.3718	−0.0233	0.055*
C15	0.6099 (7)	0.4507 (2)	0.03285 (19)	0.0397 (11)
C16	0.5968 (7)	0.4687 (2)	0.0917 (2)	0.0398 (11)
H16C	0.6232	0.5126	0.1032	0.048*
C17	0.5452 (7)	0.4220 (2)	0.13298 (19)	0.0386 (10)
C18	0.2943 (7)	0.4320 (2)	0.47497 (19)	0.0443 (12)
C19	0.2942 (8)	0.4199 (2)	0.53872 (19)	0.0441 (11)
C20	0.3446 (7)	0.4662 (2)	0.58034 (18)	0.0438 (12)
H20A	0.3457	0.4545	0.6202	0.053*
C21	0.3941 (7)	0.5308 (2)	0.56332 (19)	0.0399 (11)
C22	0.3897 (7)	0.5490 (2)	0.50438 (18)	0.0404 (11)
H22A	0.4177	0.5930	0.4934	0.048*
C23	0.3444 (7)	0.5024 (3)	0.46242 (19)	0.0452 (12)
N1	0.6344 (7)	0.66949 (19)	0.83277 (16)	0.0471 (10)
N2	0.6081 (6)	0.71095 (18)	0.74543 (15)	0.0404 (9)
N3	0.5287 (6)	0.80642 (18)	0.68472 (15)	0.0428 (10)
N4	0.4213 (8)	0.9066 (2)	0.69458 (18)	0.0594 (13)
N5	0.4805 (8)	0.2704 (2)	0.0365 (3)	0.0695 (14)
N6	0.6621 (6)	0.5002 (2)	−0.01062 (18)	0.0478 (10)
N7	0.5364 (7)	0.4458 (2)	0.19413 (17)	0.0557 (11)
N8	0.2372 (9)	0.3548 (2)	0.5608 (2)	0.0697 (14)
N9	0.4476 (6)	0.5793 (2)	0.60762 (19)	0.0507 (11)
N10	0.3432 (8)	0.5242 (3)	0.40170 (19)	0.0655 (13)
O1	0.5078 (10)	0.2236 (2)	0.0698 (2)	0.113 (2)
O2	0.4290 (11)	0.2639 (3)	−0.0144 (3)	0.131 (3)
O3	0.6682 (7)	0.4835 (2)	−0.06244 (15)	0.0756 (13)
O4	0.7010 (6)	0.55727 (18)	0.00612 (15)	0.0638 (11)
O5	0.4936 (9)	0.5039 (2)	0.20295 (17)	0.0990 (18)
O6	0.5771 (9)	0.4075 (2)	0.23366 (16)	0.0894 (16)
O7	0.4331 (5)	0.31289 (16)	0.15760 (15)	0.0548 (9)
O8	0.2527 (13)	0.3065 (2)	0.5306 (2)	0.134 (3)
O9	0.1711 (11)	0.3505 (3)	0.6100 (2)	0.135 (3)
O10	0.4597 (7)	0.5618 (2)	0.65896 (16)	0.0778 (13)
O11	0.4817 (7)	0.6368 (2)	0.59179 (19)	0.0726 (12)
O12	0.3750 (12)	0.4856 (3)	0.36221 (18)	0.133 (3)
O13	0.3162 (10)	0.5829 (2)	0.39161 (17)	0.0992 (19)
O14	0.2484 (7)	0.39015 (19)	0.43756 (15)	0.0724 (12)
N11	0.6450 (16)	0.3457 (5)	0.6714 (3)	0.164 (4)
C24	0.7279 (13)	0.2882 (4)	0.5744 (3)	0.087 (2)
H24A	0.8665	0.2833	0.5714	0.130*
H24B	0.6812	0.3147	0.5419	0.130*
H24C	0.6678	0.2446	0.5733	0.130*
C25	0.6803 (11)	0.3209 (4)	0.6291 (3)	0.085 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.099 (5)	0.070 (4)	0.053 (3)	0.017 (4)	−0.012 (3)	0.011 (3)
C2	0.057 (4)	0.044 (3)	0.056 (3)	−0.001 (3)	0.005 (3)	0.000 (2)
C3	0.039 (3)	0.042 (3)	0.060 (3)	0.000 (2)	0.000 (2)	−0.005 (2)
C4	0.046 (3)	0.042 (3)	0.044 (3)	0.009 (2)	0.000 (2)	−0.011 (2)
C5	0.053 (3)	0.071 (4)	0.060 (3)	−0.002 (3)	−0.006 (3)	−0.017 (3)
C6	0.049 (3)	0.049 (3)	0.036 (2)	−0.002 (2)	0.007 (2)	−0.009 (2)
C7	0.067 (4)	0.055 (3)	0.071 (3)	−0.024 (3)	−0.027 (3)	0.014 (3)
C8	0.055 (4)	0.079 (5)	0.091 (4)	−0.004 (4)	−0.004 (4)	0.039 (4)
C9	0.074 (4)	0.045 (3)	0.028 (2)	−0.019 (3)	0.007 (2)	−0.001 (2)
C10	0.199 (10)	0.048 (3)	0.082 (4)	0.023 (5)	0.029 (6)	−0.002 (3)
C11	0.130 (6)	0.072 (4)	0.050 (3)	−0.048 (4)	−0.023 (4)	0.008 (3)
C12	0.032 (3)	0.037 (2)	0.052 (3)	0.006 (2)	0.002 (2)	0.008 (2)
C13	0.041 (3)	0.035 (2)	0.062 (3)	−0.001 (2)	0.002 (2)	0.002 (2)
C14	0.039 (3)	0.051 (3)	0.048 (3)	0.000 (2)	0.006 (2)	−0.005 (2)
C15	0.037 (3)	0.041 (2)	0.041 (2)	0.003 (2)	0.002 (2)	0.004 (2)
C16	0.033 (3)	0.032 (2)	0.054 (3)	0.005 (2)	−0.002 (2)	−0.002 (2)
C17	0.029 (2)	0.041 (2)	0.046 (2)	0.005 (2)	0.000 (2)	0.004 (2)
C18	0.039 (3)	0.055 (3)	0.039 (2)	−0.003 (2)	−0.004 (2)	−0.007 (2)
C19	0.047 (3)	0.041 (3)	0.044 (2)	−0.007 (2)	−0.003 (2)	0.000 (2)
C20	0.038 (3)	0.062 (3)	0.032 (2)	0.003 (2)	0.001 (2)	0.006 (2)
C21	0.032 (3)	0.046 (3)	0.042 (2)	−0.002 (2)	−0.001 (2)	−0.009 (2)
C22	0.031 (3)	0.050 (3)	0.041 (2)	−0.003 (2)	0.006 (2)	−0.001 (2)
C23	0.041 (3)	0.058 (3)	0.036 (2)	−0.003 (2)	0.000 (2)	0.004 (2)
N1	0.065 (3)	0.035 (2)	0.041 (2)	0.012 (2)	0.000 (2)	0.0040 (17)
N2	0.038 (2)	0.041 (2)	0.042 (2)	0.0032 (18)	0.0031 (18)	−0.0053 (16)
N3	0.050 (3)	0.042 (2)	0.0368 (19)	−0.010 (2)	−0.0022 (18)	0.0012 (17)
N4	0.085 (4)	0.045 (2)	0.049 (2)	0.012 (3)	0.017 (3)	0.0088 (19)
N5	0.070 (4)	0.045 (3)	0.093 (4)	−0.006 (3)	0.015 (3)	−0.013 (3)
N6	0.042 (2)	0.054 (3)	0.047 (2)	0.004 (2)	0.004 (2)	0.008 (2)
N7	0.065 (3)	0.055 (3)	0.047 (2)	0.009 (2)	0.002 (2)	0.006 (2)
N8	0.090 (4)	0.062 (3)	0.057 (3)	−0.016 (3)	−0.013 (3)	0.004 (2)
N9	0.038 (2)	0.063 (3)	0.051 (2)	−0.003 (2)	0.001 (2)	−0.020 (2)
N10	0.084 (4)	0.075 (3)	0.038 (2)	−0.008 (3)	−0.005 (2)	0.005 (2)
O1	0.173 (6)	0.043 (2)	0.124 (4)	−0.007 (3)	0.060 (4)	0.000 (3)
O2	0.188 (7)	0.077 (3)	0.127 (5)	−0.027 (4)	−0.055 (5)	−0.032 (3)
O3	0.108 (4)	0.076 (3)	0.043 (2)	−0.006 (3)	0.010 (2)	0.0103 (19)
O4	0.085 (3)	0.042 (2)	0.064 (2)	−0.010 (2)	0.002 (2)	0.0109 (17)
O5	0.161 (5)	0.070 (3)	0.066 (2)	0.049 (3)	0.004 (3)	−0.013 (2)
O6	0.156 (5)	0.065 (2)	0.047 (2)	0.006 (3)	−0.013 (3)	0.0113 (19)
O7	0.051 (2)	0.050 (2)	0.063 (2)	−0.0072 (18)	0.0027 (18)	0.0188 (17)
O8	0.240 (8)	0.055 (3)	0.106 (4)	−0.033 (4)	0.013 (5)	−0.006 (3)
O9	0.224 (8)	0.120 (4)	0.060 (3)	−0.100 (5)	0.000 (4)	0.027 (3)
O10	0.090 (3)	0.100 (3)	0.044 (2)	−0.009 (3)	−0.008 (2)	−0.019 (2)
O11	0.079 (3)	0.054 (2)	0.085 (3)	−0.013 (2)	0.003 (2)	−0.022 (2)
O12	0.234 (8)	0.122 (4)	0.043 (2)	0.001 (5)	0.016 (4)	−0.010 (3)
O13	0.157 (6)	0.078 (3)	0.063 (2)	−0.018 (3)	−0.031 (3)	0.024 (2)
O14	0.100 (3)	0.064 (2)	0.053 (2)	−0.013 (3)	−0.013 (2)	−0.0145 (18)
N11	0.223 (11)	0.178 (8)	0.091 (5)	0.074 (8)	0.045 (6)	−0.015 (5)
C24	0.086 (5)	0.095 (5)	0.079 (4)	0.002 (4)	0.009 (4)	−0.002 (4)
C25	0.090 (5)	0.090 (5)	0.076 (4)	0.028 (4)	0.013 (4)	0.012 (4)

Geometric parameters (Å, º) top

C1—N1	1.485 (6)	C13—N5	1.462 (6)
C1—H1A	0.9600	C14—C15	1.394 (6)
C1—H1B	0.9600	C14—H14A	0.9300
C1—H1C	0.9600	C15—C16	1.380 (6)
C2—C3	1.326 (7)	C15—N6	1.436 (6)
C2—N1	1.385 (7)	C16—C17	1.363 (6)
C2—H2A	0.9300	C16—H16C	0.9300
C3—N2	1.389 (6)	C17—N7	1.462 (6)
C3—H3A	0.9300	C18—O14	1.227 (5)
C4—N1	1.318 (6)	C18—C19	1.460 (6)
C4—N2	1.352 (6)	C18—C23	1.471 (7)
C4—C5	1.465 (8)	C19—C20	1.361 (6)
C5—H5A	0.9600	C19—N8	1.443 (6)
C5—H5B	0.9600	C20—C21	1.382 (6)
C5—H5C	0.9600	C20—H20A	0.9300
C6—N3	1.456 (6)	C21—C22	1.381 (6)
C6—N2	1.459 (5)	C21—N9	1.438 (6)
C6—H6A	0.9700	C22—C23	1.361 (6)
C6—H6B	0.9700	C22—H22A	0.9300
C7—C8	1.317 (8)	C23—N10	1.439 (6)
C7—N3	1.372 (7)	N5—O2	1.211 (7)
C7—H7A	0.9300	N5—O1	1.213 (7)
C8—N4	1.365 (8)	N6—O3	1.218 (5)
C8—H8A	0.9300	N6—O4	1.226 (5)
C9—N3	1.335 (6)	N7—O6	1.207 (5)
C9—N4	1.337 (7)	N7—O5	1.209 (5)
C9—C11	1.464 (8)	N8—O8	1.182 (6)
C10—N4	1.471 (7)	N8—O9	1.205 (6)
C10—H10A	0.9600	N9—O10	1.214 (5)
C10—H10B	0.9600	N9—O11	1.222 (6)
C10—H10C	0.9600	N10—O12	1.197 (6)
C11—H11A	0.9600	N10—O13	1.204 (6)
C11—H11B	0.9600	N11—C25	1.103 (8)
C11—H11C	0.9600	C24—C25	1.435 (9)
C12—O7	1.234 (5)	C24—H24A	0.9600
C12—C17	1.448 (6)	C24—H24B	0.9600
C12—C13	1.451 (7)	C24—H24C	0.9600
C13—C14	1.360 (6)

N1—C1—H1A	109.5	C17—C16—H16C	120.0
N1—C1—H1B	109.5	C15—C16—H16C	120.0
H1A—C1—H1B	109.5	C16—C17—C12	125.1 (4)
N1—C1—H1C	109.5	C16—C17—N7	115.9 (4)
H1A—C1—H1C	109.5	C12—C17—N7	119.0 (4)
H1B—C1—H1C	109.5	O14—C18—C19	124.6 (5)
C3—C2—N1	107.2 (5)	O14—C18—C23	125.0 (4)
C3—C2—H2A	126.4	C19—C18—C23	110.3 (4)
N1—C2—H2A	126.4	C20—C19—N8	116.0 (4)
C2—C3—N2	107.2 (5)	C20—C19—C18	124.8 (4)
C2—C3—H3A	126.4	N8—C19—C18	119.3 (4)
N2—C3—H3A	126.4	C19—C20—C21	119.9 (4)
N1—C4—N2	107.0 (4)	C19—C20—H20A	120.0
N1—C4—C5	126.0 (5)	C21—C20—H20A	120.0
N2—C4—C5	126.9 (5)	C22—C21—C20	120.4 (4)
C4—C5—H5A	109.5	C22—C21—N9	120.0 (4)
C4—C5—H5B	109.5	C20—C21—N9	119.5 (4)
H5A—C5—H5B	109.5	C23—C22—C21	119.9 (4)
C4—C5—H5C	109.5	C23—C22—H22A	120.1
H5A—C5—H5C	109.5	C21—C22—H22A	120.1
H5B—C5—H5C	109.5	C22—C23—N10	117.5 (4)
N3—C6—N2	111.2 (4)	C22—C23—C18	124.6 (4)
N3—C6—H6A	109.4	N10—C23—C18	118.0 (4)
N2—C6—H6A	109.4	C4—N1—C2	109.9 (4)
N3—C6—H6B	109.4	C4—N1—C1	125.8 (5)
N2—C6—H6B	109.4	C2—N1—C1	124.2 (5)
H6A—C6—H6B	108.0	C4—N2—C3	108.6 (4)
C8—C7—N3	106.6 (5)	C4—N2—C6	128.0 (4)
C8—C7—H7A	126.7	C3—N2—C6	123.4 (4)
N3—C7—H7A	126.7	C9—N3—C7	109.9 (5)
C7—C8—N4	108.2 (6)	C9—N3—C6	126.4 (4)
C7—C8—H8A	125.9	C7—N3—C6	123.7 (4)
N4—C8—H8A	125.9	C9—N4—C8	109.1 (4)
N3—C9—N4	106.2 (5)	C9—N4—C10	126.2 (6)
N3—C9—C11	126.9 (6)	C8—N4—C10	124.7 (7)
N4—C9—C11	126.9 (5)	O2—N5—O1	123.5 (5)
N4—C10—H10A	109.5	O2—N5—C13	117.5 (5)
N4—C10—H10B	109.5	O1—N5—C13	118.9 (5)
H10A—C10—H10B	109.5	O3—N6—O4	122.8 (4)
N4—C10—H10C	109.5	O3—N6—C15	118.6 (4)
H10A—C10—H10C	109.5	O4—N6—C15	118.6 (4)
H10B—C10—H10C	109.5	O6—N7—O5	122.6 (4)
C9—C11—H11A	109.5	O6—N7—C17	119.0 (4)
C9—C11—H11B	109.5	O5—N7—C17	118.4 (4)
H11A—C11—H11B	109.5	O8—N8—O9	120.6 (5)
C9—C11—H11C	109.5	O8—N8—C19	120.4 (5)
H11A—C11—H11C	109.5	O9—N8—C19	119.0 (5)
H11B—C11—H11C	109.5	O10—N9—O11	122.3 (4)
O7—C12—C17	123.9 (4)	O10—N9—C21	119.4 (5)
O7—C12—C13	125.4 (4)	O11—N9—C21	118.3 (4)
C17—C12—C13	110.6 (4)	O12—N10—O13	120.6 (5)
C14—C13—C12	124.9 (4)	O12—N10—C23	121.1 (5)
C14—C13—N5	116.5 (5)	O13—N10—C23	118.2 (5)
C12—C13—N5	118.6 (4)	C25—C24—H24A	109.5
C13—C14—C15	119.9 (4)	C25—C24—H24B	109.5
C13—C14—H14A	120.0	H24A—C24—H24B	109.5
C15—C14—H14A	120.0	C25—C24—H24C	109.5
C16—C15—C14	119.5 (4)	H24A—C24—H24C	109.5
C16—C15—N6	119.9 (4)	H24B—C24—H24C	109.5
C14—C15—N6	120.6 (4)	N11—C25—C24	179.3 (9)
C17—C16—C15	120.0 (4)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₈N₄²⁺·2C₆H₂N₃O₇⁻·C₂H₃N
M_r	703.56
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	292
a, b, c (Å)	6.8715 (9), 19.892 (3), 22.594 (3)
V (Å³)	3088.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	24762, 3115, 2528
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.148, 1.02
No. of reflections	3115
No. of parameters	455
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

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1,1'-Methyl­enebis(2,3-dimethyl­imidazolium) dipicrate acetonitrile solvate

Supporting information

Key indicators

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1,1'-Methylenebis(2,3-dimethylimidazolium) dipicrate acetonitrile solvate