Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705338X/bh2132sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705338X/bh2132Isup2.hkl |
CCDC reference: 667467
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
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).
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.
H atoms were positioned geometrically with C—H bond lengths fixed to 0.93 (aromatic CH), 0.97 (methylene CH2) or 0.96 Å (methyl CH3). A riding model was used during the refinement process. The Uiso parameters for H atoms were constrained to be 1.2Ueq of the carrier C atom for aromatic and methylene groups, and 1.5Ueq of the carrier C atom for methyl groups. Measured Friedel pairs were merged before refinement.
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.
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).
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).
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. |
C11H18N42+·2C6H2N3O7−·C2H3N | Dx = 1.513 Mg m−3 |
Mr = 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 |
Bruker SMART 1000 CCD area-detector diffractometer | 3115 independent reflections |
Radiation source: fine-focus sealed tube | 2528 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→8 |
Tmin = 0.963, Tmax = 0.988 | k = −23→23 |
24762 measured reflections | l = −26→26 |
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(Fo2) + (0.0737P)2 + 1.7443P] where P = (Fo2 + 2Fc2)/3 |
3115 reflections | (Δ/σ)max < 0.001 |
455 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C11H18N42+·2C6H2N3O7−·C2H3N | V = 3088.2 (7) Å3 |
Mr = 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 |
Bruker SMART 1000 CCD area-detector diffractometer | 3115 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2528 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.988 | Rint = 0.061 |
24762 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.23 e Å−3 |
3115 reflections | Δρmin = −0.17 e Å−3 |
455 parameters |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.963, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24762, 3115, 2528 |
Rint | 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 |
Δρmax, Δρmin (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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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.