Literature DB >> 21202085

3,3'-Dibenzyl-2,2'-dimethyl-1,1'-methyl-enediimidazolium dipicrate.

Chuan-Ming Jin1, Ling-Yan Wu, Xiao-Xia Lu, Jing-Jing Hu.   

Abstract

In the title salt, C(23)H(26)N(4) (2+)·2C(6)H(2)N(3)O(7) (-), the dihedral angle between the imidazolium rings in the dication is 69.9 (1)°. The aromatic ring of the benzyl group is almost perpendicular to the N-heterocyclic ring that is directly connected to it [dihedral angles = 83.2 (2) and 77.3 (3)°].

Entities:  

Year:  2008        PMID： 21202085      PMCID： PMC2961014          DOI： 10.1107/S1600536808006272

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis, see: Jin et al. (2005 ▶). For background literature on ‘green chemistry’, see: Singh et al. (2006 ▶). For background literature on energetic ionic salts, see: Wang et al. (2007 ▶).

Experimental

Crystal data

C23H26N4 2+·2C6H2N3O7 − M = 814.69 Triclinic, a = 12.2842 (8) Å b = 12.6802 (8) Å c = 12.9175 (8) Å α = 65.691 (1)° β = 77.601 (1)° γ = 80.003 (1)° V = 1782.7 (2) Å3 Z = 2 Mo Kα radiation μ = 0.12 mm−1 T = 294 (2) K 0.30 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: none 11547 measured reflections 6921 independent reflections 4320 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.130 S = 0.93 6921 reflections 534 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.21 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/S1600536808006272/ng2431sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006272/ng2431Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H26N42+·2C6H2N3O7–Z = 2
Mr = 814.69F000 = 844
Triclinic, P1Dx = 1.518 Mg m−3
a = 12.2842 (8) ÅMo Kα radiation λ = 0.71073 Å
b = 12.6802 (8) ÅCell parameters from 2808 reflections
c = 12.9175 (8) Åθ = 2.2–23.4º
α = 65.691 (1)ºµ = 0.12 mm−1
β = 77.601 (1)ºT = 294 (2) K
γ = 80.003 (1)ºBlock, yellow
V = 1782.7 (2) Å30.30 × 0.20 × 0.13 mm
Bruker SMART APEX CCD area-detector diffractometer4320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Monochromator: graphiteθmax = 26.0º
T = 294(2) Kθmin = 1.7º
φ and ω scansh = −15→13
Absorption correction: nonek = −15→15
11547 measured reflectionsl = −15→13
6921 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.130  w = 1/[σ2(Fo2) + (0.0604P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.002
6921 reflectionsΔρmax = 0.35 e Å−3
534 parametersΔρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
C1−0.32013 (19)0.2269 (2)0.94028 (19)0.0481 (6)
H1−0.24390.20780.92220.058*
C2−0.3562 (2)0.2944 (2)1.0040 (2)0.0589 (7)
H2−0.30430.32061.02860.071*
C3−0.4689 (3)0.3231 (2)1.0312 (2)0.0670 (8)
H3−0.49340.36791.07490.080*
C4−0.5445 (2)0.2857 (2)0.9939 (2)0.0655 (8)
H4−0.62060.30591.01160.079*
C5−0.50921 (19)0.2180 (2)0.9300 (2)0.0525 (6)
H5−0.56150.19280.90500.063*
C6−0.39585 (18)0.18755 (19)0.90311 (18)0.0415 (5)
C7−0.36084 (17)0.1092 (2)0.8373 (2)0.0462 (6)
H7A−0.37660.03050.88870.055*
H7B−0.40530.13430.77610.055*
C8−0.15951 (19)0.0230 (2)0.8316 (2)0.0509 (6)
H8−0.1699−0.04680.89470.061*
C9−0.0615 (2)0.0584 (2)0.7674 (2)0.0500 (6)
H90.00880.01790.77710.060*
C10−0.19573 (17)0.19641 (18)0.69713 (18)0.0361 (5)
C11−0.25476 (18)0.30444 (19)0.6275 (2)0.0496 (6)
H11A−0.25220.30550.55230.074*
H11B−0.21960.36940.62090.074*
H11C−0.33130.30950.66360.074*
C120.00031 (18)0.2391 (2)0.59965 (18)0.0460 (6)
H12A−0.01630.31770.59710.055*
H12B0.07280.20920.62400.055*
C130.04891 (17)0.1502 (2)0.4523 (2)0.0459 (6)
H130.07570.07650.49950.055*
C140.04486 (18)0.1872 (2)0.3408 (2)0.0504 (6)
H140.06830.14380.29560.060*
C15−0.02355 (16)0.33463 (19)0.39257 (19)0.0394 (5)
C16−0.06630 (19)0.45312 (19)0.3845 (2)0.0519 (6)
H16A−0.01380.50660.33190.078*
H16B−0.07600.45600.45900.078*
H16C−0.13690.47400.35720.078*
C17−0.0239 (2)0.3813 (2)0.1872 (2)0.0665 (8)
H17A0.01270.45140.16290.080*
H17B−0.10390.40330.19110.080*
C180.01479 (19)0.3287 (2)0.09860 (19)0.0451 (6)
C190.1118 (2)0.3592 (2)0.0223 (2)0.0547 (6)
H190.15560.40780.02970.066*
C200.1456 (2)0.3191 (2)−0.0650 (2)0.0618 (7)
H200.21180.3404−0.11590.074*
C210.0816 (3)0.2483 (2)−0.0764 (2)0.0656 (8)
H210.10310.2223−0.13620.079*
C22−0.0139 (3)0.2153 (2)−0.0005 (3)0.0728 (8)
H22−0.05640.1652−0.00740.087*
C23−0.0480 (2)0.2556 (2)0.0863 (2)0.0648 (7)
H23−0.11390.23330.13710.078*
C240.27922 (18)0.40292 (18)0.42696 (19)0.0405 (5)
C250.36650 (19)0.37045 (18)0.49657 (18)0.0434 (5)
C260.4775 (2)0.38252 (19)0.4525 (2)0.0496 (6)
H260.52940.36260.50210.059*
C270.51307 (18)0.42396 (19)0.3353 (2)0.0459 (6)
C280.43647 (18)0.45553 (18)0.26156 (19)0.0427 (5)
H280.46010.48240.18250.051*
C290.32617 (18)0.44706 (19)0.30531 (19)0.0415 (5)
C300.27633 (18)−0.03995 (19)0.67370 (19)0.0421 (5)
C310.33425 (18)−0.02705 (18)0.75420 (19)0.0414 (5)
C320.44610 (18)−0.05648 (18)0.75761 (19)0.0435 (5)
H320.4786−0.04500.81040.052*
C330.51087 (18)−0.10330 (18)0.6825 (2)0.0445 (6)
C340.46294 (18)−0.12262 (18)0.6051 (2)0.0459 (6)
H340.5069−0.15430.55480.055*
C350.35072 (18)−0.09491 (19)0.60286 (19)0.0431 (5)
N1−0.24203 (14)0.10880 (15)0.78718 (15)0.0399 (4)
N2−0.08471 (14)0.16696 (15)0.68376 (14)0.0389 (4)
N30.00576 (13)0.24197 (15)0.48479 (15)0.0390 (4)
N4−0.00050 (14)0.30187 (16)0.30376 (15)0.0448 (5)
N50.3367 (2)0.3203 (2)0.6210 (2)0.0684 (6)
N60.63001 (18)0.4290 (2)0.2899 (2)0.0686 (6)
N70.24869 (19)0.4833 (2)0.22345 (19)0.0621 (6)
N80.27178 (18)0.01525 (17)0.84116 (17)0.0500 (5)
N90.62976 (17)−0.13317 (18)0.6852 (2)0.0575 (6)
N100.30666 (18)−0.11954 (18)0.5197 (2)0.0577 (6)
O10.17779 (13)0.39644 (14)0.46220 (14)0.0561 (4)
O20.24912 (19)0.2763 (2)0.66457 (17)0.1098 (9)
O30.4034 (2)0.3208 (2)0.67838 (18)0.1245 (10)
O40.69643 (16)0.4028 (2)0.3567 (2)0.1142 (9)
O50.65990 (15)0.4578 (2)0.18593 (19)0.0872 (7)
O60.27181 (19)0.4481 (2)0.14539 (19)0.0982 (7)
O70.16644 (16)0.5492 (2)0.23414 (17)0.0850 (7)
O80.17702 (13)−0.00456 (15)0.66426 (14)0.0600 (5)
O90.32355 (15)0.05338 (15)0.88774 (16)0.0654 (5)
O100.17139 (15)0.00864 (17)0.86778 (16)0.0724 (5)
O110.67036 (14)−0.11617 (17)0.75553 (18)0.0748 (6)
O120.68460 (14)−0.17238 (18)0.61513 (19)0.0798 (6)
O130.37262 (15)−0.13424 (16)0.43990 (15)0.0676 (5)
O140.20723 (16)−0.1274 (2)0.5327 (2)0.1081 (9)
U11U22U33U12U13U23
C10.0441 (13)0.0571 (15)0.0434 (14)−0.0051 (11)−0.0059 (11)−0.0202 (12)
C20.0766 (19)0.0591 (17)0.0463 (15)−0.0073 (14)−0.0163 (14)−0.0222 (13)
C30.088 (2)0.0614 (18)0.0456 (16)0.0101 (16)−0.0061 (15)−0.0241 (14)
C40.0575 (17)0.0731 (19)0.0527 (17)0.0128 (14)−0.0009 (14)−0.0226 (15)
C50.0418 (13)0.0667 (17)0.0431 (14)−0.0019 (12)−0.0034 (11)−0.0185 (13)
C60.0403 (13)0.0490 (14)0.0311 (12)−0.0053 (10)−0.0017 (10)−0.0132 (11)
C70.0407 (13)0.0592 (15)0.0404 (13)−0.0115 (11)0.0005 (10)−0.0220 (12)
C80.0550 (15)0.0477 (15)0.0393 (14)0.0017 (12)−0.0031 (12)−0.0112 (11)
C90.0480 (14)0.0529 (15)0.0416 (14)0.0096 (11)−0.0077 (12)−0.0164 (12)
C100.0388 (12)0.0409 (13)0.0325 (12)−0.0010 (10)−0.0034 (10)−0.0203 (10)
C110.0484 (14)0.0507 (15)0.0458 (14)−0.0009 (11)−0.0047 (11)−0.0177 (12)
C120.0432 (13)0.0617 (15)0.0381 (13)−0.0116 (11)−0.0030 (11)−0.0235 (12)
C130.0404 (13)0.0507 (14)0.0446 (14)0.0066 (11)−0.0074 (11)−0.0204 (12)
C140.0492 (14)0.0603 (16)0.0438 (15)0.0133 (12)−0.0101 (11)−0.0284 (13)
C150.0314 (11)0.0468 (14)0.0379 (13)−0.0058 (10)0.0016 (10)−0.0171 (11)
C160.0515 (14)0.0507 (15)0.0504 (15)−0.0057 (11)0.0008 (12)−0.0207 (12)
C170.0777 (19)0.0726 (18)0.0427 (15)0.0220 (14)−0.0173 (14)−0.0236 (14)
C180.0444 (14)0.0523 (14)0.0332 (13)0.0045 (11)−0.0125 (11)−0.0118 (11)
C190.0511 (15)0.0636 (17)0.0554 (16)−0.0110 (12)−0.0115 (13)−0.0253 (14)
C200.0557 (16)0.0744 (19)0.0478 (16)−0.0050 (14)0.0026 (13)−0.0221 (14)
C210.091 (2)0.0614 (18)0.0455 (16)0.0103 (16)−0.0204 (16)−0.0236 (14)
C220.089 (2)0.069 (2)0.072 (2)−0.0222 (17)−0.0330 (19)−0.0247 (17)
C230.0486 (15)0.081 (2)0.0530 (17)−0.0187 (14)−0.0067 (13)−0.0101 (15)
C240.0424 (13)0.0368 (12)0.0429 (14)−0.0052 (10)0.0003 (11)−0.0191 (11)
C250.0537 (15)0.0397 (13)0.0314 (12)−0.0039 (11)−0.0046 (11)−0.0098 (10)
C260.0508 (15)0.0493 (15)0.0490 (15)−0.0037 (11)−0.0170 (12)−0.0156 (12)
C270.0378 (13)0.0464 (14)0.0479 (15)−0.0074 (10)−0.0067 (11)−0.0116 (12)
C280.0451 (13)0.0460 (13)0.0367 (13)−0.0089 (10)−0.0024 (11)−0.0159 (11)
C290.0407 (13)0.0477 (13)0.0409 (13)−0.0071 (10)−0.0094 (11)−0.0196 (11)
C300.0370 (13)0.0434 (13)0.0413 (13)−0.0025 (10)−0.0048 (10)−0.0132 (11)
C310.0405 (13)0.0413 (13)0.0390 (13)−0.0033 (10)−0.0017 (10)−0.0148 (11)
C320.0466 (14)0.0401 (13)0.0437 (13)−0.0088 (10)−0.0085 (11)−0.0138 (11)
C330.0352 (12)0.0419 (13)0.0521 (15)−0.0059 (10)−0.0057 (11)−0.0138 (12)
C340.0423 (13)0.0418 (13)0.0515 (15)−0.0075 (10)0.0039 (11)−0.0201 (12)
C350.0407 (13)0.0460 (14)0.0462 (14)−0.0083 (10)−0.0062 (11)−0.0202 (11)
N10.0393 (10)0.0459 (11)0.0335 (10)−0.0048 (9)0.0006 (8)−0.0173 (9)
N20.0367 (10)0.0467 (11)0.0313 (10)−0.0036 (8)−0.0005 (8)−0.0158 (9)
N30.0349 (10)0.0497 (11)0.0341 (10)−0.0057 (8)−0.0040 (8)−0.0181 (9)
N40.0437 (11)0.0553 (12)0.0326 (10)0.0057 (9)−0.0050 (9)−0.0189 (9)
N50.0785 (17)0.0743 (16)0.0429 (14)−0.0068 (13)−0.0128 (13)−0.0121 (12)
N60.0458 (14)0.0775 (16)0.0673 (17)−0.0099 (12)−0.0095 (13)−0.0115 (13)
N70.0525 (14)0.0846 (17)0.0495 (14)−0.0234 (13)−0.0088 (11)−0.0195 (13)
N80.0543 (13)0.0482 (12)0.0478 (13)−0.0033 (10)−0.0080 (11)−0.0196 (10)
N90.0422 (12)0.0566 (13)0.0734 (16)−0.0063 (10)−0.0057 (12)−0.0262 (12)
N100.0500 (13)0.0636 (14)0.0708 (15)−0.0052 (11)−0.0086 (12)−0.0380 (12)
O10.0449 (10)0.0662 (11)0.0544 (11)−0.0104 (8)0.0050 (8)−0.0249 (9)
O20.0825 (15)0.161 (2)0.0478 (13)−0.0346 (16)0.0045 (12)−0.0007 (14)
O30.149 (2)0.174 (3)0.0492 (14)−0.059 (2)−0.0279 (15)−0.0196 (15)
O40.0495 (12)0.171 (2)0.0856 (16)−0.0216 (14)−0.0277 (12)−0.0015 (16)
O50.0522 (12)0.1214 (18)0.0681 (14)−0.0155 (11)0.0084 (11)−0.0232 (13)
O60.1076 (17)0.146 (2)0.0743 (15)−0.0297 (15)−0.0295 (13)−0.0616 (15)
O70.0453 (11)0.1186 (18)0.0711 (14)−0.0012 (11)−0.0164 (10)−0.0164 (13)
O80.0402 (10)0.0855 (13)0.0561 (11)0.0074 (9)−0.0116 (8)−0.0328 (10)
O90.0721 (12)0.0719 (12)0.0671 (12)−0.0046 (9)−0.0167 (10)−0.0399 (10)
O100.0501 (11)0.1032 (15)0.0756 (13)−0.0103 (10)0.0066 (10)−0.0534 (12)
O110.0498 (11)0.0979 (15)0.0884 (15)−0.0044 (10)−0.0233 (10)−0.0429 (12)
O120.0420 (10)0.1008 (15)0.1119 (17)0.0027 (10)−0.0036 (11)−0.0643 (14)
O130.0761 (13)0.0797 (13)0.0572 (12)−0.0133 (10)−0.0044 (10)−0.0375 (10)
O140.0500 (12)0.180 (2)0.157 (2)−0.0119 (13)−0.0157 (13)−0.127 (2)
C1—C61.377 (3)C18—C231.380 (3)
C1—C21.378 (3)C19—C201.379 (3)
C1—H10.9300C19—H190.9300
C2—C31.377 (4)C20—C211.361 (4)
C2—H20.9300C20—H200.9300
C3—C41.360 (4)C21—C221.360 (4)
C3—H30.9300C21—H210.9300
C4—C51.381 (3)C22—C231.374 (4)
C4—H40.9300C22—H220.9300
C5—C61.387 (3)C23—H230.9300
C5—H50.9300C24—O11.236 (2)
C6—C71.512 (3)C24—C251.443 (3)
C7—N11.464 (3)C24—C291.454 (3)
C7—H7A0.9700C25—C261.369 (3)
C7—H7B0.9700C25—N51.451 (3)
C8—C91.339 (3)C26—C271.378 (3)
C8—N11.376 (3)C26—H260.9300
C8—H80.9300C27—C281.376 (3)
C9—N21.384 (3)C27—N61.432 (3)
C9—H90.9300C28—C291.356 (3)
C10—N11.335 (3)C28—H280.9300
C10—N21.343 (2)C29—N71.455 (3)
C10—C111.460 (3)C30—O81.238 (2)
C11—H11A0.9600C30—C351.450 (3)
C11—H11B0.9600C30—C311.453 (3)
C11—H11C0.9600C31—C321.365 (3)
C12—N31.457 (3)C31—N81.457 (3)
C12—N21.461 (3)C32—C331.380 (3)
C12—H12A0.9700C32—H320.9300
C12—H12B0.9700C33—C341.383 (3)
C13—C141.328 (3)C33—N91.448 (3)
C13—N31.380 (3)C34—C351.366 (3)
C13—H130.9300C34—H340.9300
C14—N41.383 (3)C35—N101.459 (3)
C14—H140.9300N5—O21.215 (3)
C15—N41.334 (3)N5—O31.219 (3)
C15—N31.347 (3)N6—O41.222 (3)
C15—C161.471 (3)N6—O51.226 (3)
C16—H16A0.9600N7—O71.217 (3)
C16—H16B0.9600N7—O61.225 (3)
C16—H16C0.9600N8—O101.215 (2)
C17—N41.483 (3)N8—O91.229 (2)
C17—C181.505 (3)N9—O111.230 (3)
C17—H17A0.9700N9—O121.230 (3)
C17—H17B0.9700N10—O141.213 (2)
C18—C191.372 (3)N10—O131.225 (2)
C6—C1—C2120.7 (2)C20—C21—H21120.0
C6—C1—H1119.7C21—C22—C23120.4 (3)
C2—C1—H1119.7C21—C22—H22119.8
C3—C2—C1120.0 (2)C23—C22—H22119.8
C3—C2—H2120.0C22—C23—C18120.6 (2)
C1—C2—H2120.0C22—C23—H23119.7
C4—C3—C2119.9 (2)C18—C23—H23119.7
C4—C3—H3120.1O1—C24—C25126.5 (2)
C2—C3—H3120.1O1—C24—C29122.8 (2)
C3—C4—C5120.6 (2)C25—C24—C29110.62 (19)
C3—C4—H4119.7C26—C25—C24124.0 (2)
C5—C4—H4119.7C26—C25—N5117.1 (2)
C4—C5—C6120.1 (2)C24—C25—N5118.9 (2)
C4—C5—H5120.0C25—C26—C27120.5 (2)
C6—C5—H5120.0C25—C26—H26119.7
C1—C6—C5118.8 (2)C27—C26—H26119.7
C1—C6—C7122.70 (19)C28—C27—C26120.0 (2)
C5—C6—C7118.5 (2)C28—C27—N6119.6 (2)
N1—C7—C6113.15 (17)C26—C27—N6120.3 (2)
N1—C7—H7A108.9C29—C28—C27119.4 (2)
C6—C7—H7A108.9C29—C28—H28120.3
N1—C7—H7B108.9C27—C28—H28120.3
C6—C7—H7B108.9C28—C29—C24125.5 (2)
H7A—C7—H7B107.8C28—C29—N7117.1 (2)
C9—C8—N1107.5 (2)C24—C29—N7117.39 (19)
C9—C8—H8126.3O8—C30—C35124.4 (2)
N1—C8—H8126.3O8—C30—C31124.0 (2)
C8—C9—N2106.9 (2)C35—C30—C31111.46 (18)
C8—C9—H9126.6C32—C31—C30124.1 (2)
N2—C9—H9126.6C32—C31—N8115.8 (2)
N1—C10—N2107.06 (18)C30—C31—N8120.05 (19)
N1—C10—C11126.33 (19)C31—C32—C33119.9 (2)
N2—C10—C11126.6 (2)C31—C32—H32120.1
C10—C11—H11A109.5C33—C32—H32120.1
C10—C11—H11B109.5C32—C33—C34120.5 (2)
H11A—C11—H11B109.5C32—C33—N9119.9 (2)
C10—C11—H11C109.5C34—C33—N9119.7 (2)
H11A—C11—H11C109.5C35—C34—C33119.7 (2)
H11B—C11—H11C109.5C35—C34—H34120.2
N3—C12—N2112.33 (17)C33—C34—H34120.2
N3—C12—H12A109.1C34—C35—C30124.2 (2)
N2—C12—H12A109.1C34—C35—N10116.2 (2)
N3—C12—H12B109.1C30—C35—N10119.54 (19)
N2—C12—H12B109.1C10—N1—C8109.43 (18)
H12A—C12—H12B107.9C10—N1—C7125.02 (18)
C14—C13—N3107.0 (2)C8—N1—C7125.31 (19)
C14—C13—H13126.5C10—N2—C9109.16 (18)
N3—C13—H13126.5C10—N2—C12126.38 (18)
C13—C14—N4107.88 (19)C9—N2—C12124.37 (18)
C13—C14—H14126.1C15—N3—C13109.25 (18)
N4—C14—H14126.1C15—N3—C12126.22 (19)
N4—C15—N3107.00 (18)C13—N3—C12124.42 (19)
N4—C15—C16124.4 (2)C15—N4—C14108.90 (18)
N3—C15—C16128.5 (2)C15—N4—C17122.33 (19)
C15—C16—H16A109.5C14—N4—C17128.77 (19)
C15—C16—H16B109.5O2—N5—O3122.2 (2)
H16A—C16—H16B109.5O2—N5—C25119.8 (2)
C15—C16—H16C109.5O3—N5—C25118.0 (2)
H16A—C16—H16C109.5O4—N6—O5122.5 (2)
H16B—C16—H16C109.5O4—N6—C27118.6 (2)
N4—C17—C18113.42 (19)O5—N6—C27118.9 (2)
N4—C17—H17A108.9O7—N7—O6123.6 (2)
C18—C17—H17A108.9O7—N7—C29118.5 (2)
N4—C17—H17B108.9O6—N7—C29117.9 (2)
C18—C17—H17B108.9O10—N8—O9122.2 (2)
H17A—C17—H17B107.7O10—N8—C31119.3 (2)
C19—C18—C23118.1 (2)O9—N8—C31118.4 (2)
C19—C18—C17119.8 (2)O11—N9—O12123.9 (2)
C23—C18—C17122.0 (2)O11—N9—C33118.5 (2)
C18—C19—C20121.3 (2)O12—N9—C33117.6 (2)
C18—C19—H19119.3O14—N10—O13122.1 (2)
C20—C19—H19119.3O14—N10—C35119.5 (2)
C21—C20—C19119.5 (2)O13—N10—C35118.3 (2)
C21—C20—H20120.2C24—O1—H12A160.3
C19—C20—H20120.2N5—O2—O8126.5 (2)
C22—C21—C20120.1 (3)C30—O8—O285.51 (14)
C22—C21—H21120.0
C6—C1—C2—C30.0 (4)C9—C8—N1—C7−174.9 (2)
C1—C2—C3—C4−0.7 (4)C6—C7—N1—C10−72.2 (3)
C2—C3—C4—C50.7 (4)C6—C7—N1—C8101.6 (2)
C3—C4—C5—C6−0.1 (4)N1—C10—N2—C90.1 (2)
C2—C1—C6—C50.6 (3)C11—C10—N2—C9179.3 (2)
C2—C1—C6—C7−177.4 (2)N1—C10—N2—C12−176.49 (18)
C4—C5—C6—C1−0.6 (3)C11—C10—N2—C122.7 (3)
C4—C5—C6—C7177.5 (2)C8—C9—N2—C10−0.3 (2)
C1—C6—C7—N1−17.7 (3)C8—C9—N2—C12176.4 (2)
C5—C6—C7—N1164.3 (2)N3—C12—N2—C10−77.6 (3)
N1—C8—C9—N20.4 (3)N3—C12—N2—C9106.4 (2)
N3—C13—C14—N40.1 (3)N4—C15—N3—C130.6 (2)
N4—C17—C18—C19−102.2 (3)C16—C15—N3—C13−175.8 (2)
N4—C17—C18—C2381.9 (3)N4—C15—N3—C12176.95 (17)
C23—C18—C19—C200.6 (4)C16—C15—N3—C120.6 (3)
C17—C18—C19—C20−175.4 (2)C14—C13—N3—C15−0.5 (2)
C18—C19—C20—C210.2 (4)C14—C13—N3—C12−176.88 (19)
C19—C20—C21—C22−1.4 (4)N2—C12—N3—C15112.0 (2)
C20—C21—C22—C231.7 (4)N2—C12—N3—C13−72.2 (3)
C21—C22—C23—C18−0.8 (4)N3—C15—N4—C14−0.5 (2)
C19—C18—C23—C22−0.3 (4)C16—C15—N4—C14176.1 (2)
C17—C18—C23—C22175.6 (2)N3—C15—N4—C17178.81 (19)
O1—C24—C25—C26−178.2 (2)C16—C15—N4—C17−4.6 (3)
C29—C24—C25—C261.3 (3)C13—C14—N4—C150.3 (3)
O1—C24—C25—N52.8 (3)C13—C14—N4—C17−179.0 (2)
C29—C24—C25—N5−177.8 (2)C18—C17—N4—C15176.6 (2)
C24—C25—C26—C27−2.4 (4)C18—C17—N4—C14−4.2 (4)
N5—C25—C26—C27176.7 (2)C26—C25—N5—O2−158.4 (3)
C25—C26—C27—C281.2 (4)C24—C25—N5—O220.7 (4)
C25—C26—C27—N6−175.8 (2)C26—C25—N5—O319.3 (4)
C26—C27—C28—C291.0 (3)C24—C25—N5—O3−161.6 (2)
N6—C27—C28—C29177.9 (2)C28—C27—N6—O4178.6 (2)
C27—C28—C29—C24−2.1 (3)C26—C27—N6—O4−4.5 (4)
C27—C28—C29—N7179.1 (2)C28—C27—N6—O5−2.5 (4)
O1—C24—C29—C28−179.5 (2)C26—C27—N6—O5174.5 (2)
C25—C24—C29—C281.0 (3)C28—C29—N7—O7−131.0 (2)
O1—C24—C29—N7−0.7 (3)C24—C29—N7—O750.1 (3)
C25—C24—C29—N7179.78 (19)C28—C29—N7—O647.0 (3)
O8—C30—C31—C32−173.8 (2)C24—C29—N7—O6−131.9 (2)
C35—C30—C31—C323.8 (3)C32—C31—N8—O10−157.1 (2)
O8—C30—C31—N88.7 (3)C30—C31—N8—O1020.6 (3)
C35—C30—C31—N8−173.68 (18)C32—C31—N8—O920.7 (3)
C30—C31—C32—C33−1.0 (3)C30—C31—N8—O9−161.6 (2)
N8—C31—C32—C33176.51 (19)C32—C33—N9—O110.2 (3)
C31—C32—C33—C34−1.2 (3)C34—C33—N9—O11−179.4 (2)
C31—C32—C33—N9179.24 (19)C32—C33—N9—O12−178.5 (2)
C32—C33—C34—C350.1 (3)C34—C33—N9—O121.9 (3)
N9—C33—C34—C35179.7 (2)C34—C35—N10—O14160.1 (2)
C33—C34—C35—C303.2 (3)C30—C35—N10—O14−22.1 (3)
C33—C34—C35—N10−179.2 (2)C34—C35—N10—O13−18.2 (3)
O8—C30—C35—C34172.7 (2)C30—C35—N10—O13159.6 (2)
C31—C30—C35—C34−4.8 (3)C25—C24—O1—H12A−34.2
O8—C30—C35—N10−4.8 (3)C29—C24—O1—H12A146.4
C31—C30—C35—N10177.59 (19)O3—N5—O2—O8−108.7 (3)
N2—C10—N1—C80.2 (2)C25—N5—O2—O869.0 (3)
C11—C10—N1—C8−179.0 (2)C35—C30—O8—O2−130.9 (2)
N2—C10—N1—C7174.79 (18)C31—C30—O8—O246.4 (2)
C11—C10—N1—C7−4.4 (3)N5—O2—O8—C3036.4 (2)
C9—C8—N1—C10−0.3 (3)
D—H···AD—HH···AD···AD—H···A
C19—H19···O60.932.523.354 (3)150
C16—H16A···O70.962.333.210 (3)152
C13—H13···O80.932.453.190 (3)136
C9—H9···O100.932.493.249 (3)139
C9—H9···O80.932.313.063 (3)138
C16—H16C···O4i0.962.383.211 (3)145
C11—H11A···O4i0.962.483.347 (3)150
C5—H5···O9i0.932.553.433 (3)159
C16—H16B···O1ii0.962.513.237 (3)132
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Energetic nitrogen-rich salts and ionic liquids.

Authors:  Rajendra P Singh; Rajendar D Verma; Dayal T Meshri; Jean'ne M Shreeve
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-26       Impact factor: 15.336
  2 in total
  1 in total

1.  Benzotriazolium picrate.

Authors:  Bo Zeng; Ji Li; Guo-Dong Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-20
  1 in total

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