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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o693.
Published online 2008 March 12. doi:  10.1107/S1600536808006272
PMCID: PMC2961014

3,3′-Dibenzyl-2,2′-dimethyl-1,1′-methyl­enediimidazolium dipicrate

Abstract

In the title salt, C23H26N4 2+·2C6H2N3O7 , 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)°].

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0o693-scheme1.jpg

Experimental

Crystal data

  • C23H26N4 2+·2C6H2N3O7
  • M r = 814.69
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o693-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

Acknowledgments

We gratefully acknowledge the financial support of the National Science Funds for Distinguished Young Scholars of Hubei Province, People’s Republic of China (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).

supplementary crystallographic information

Comment

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). Picric acid is a polynitrogen compound with explosive character. Imidazolium-based or triazolium-based dication picrate salts are good candidates for energetic ionic salts (Wang et al., 2007). Based on this, the title organic salt (scheme 1) was therefore prepared and its structure is reported here.

The asymmetric unit of the title compound contains one 1, 1'-Methylenebis (2-methyl-3-benzyl- imidazolium) dication and two picrate anions (Figure 1). The dihedral angle between the imidazolium rings in the dication is 69.9 (1)°. The benzene ring of benzenyl group is almost perpendicular with the imidazole ring which is directly connected with them, making the dihedral angle of 96.8 (2)° and 102.7 (3)°, respectively. And the dihedral angle between the benzene ring of the two independent picrate anions is 42.8 (2)°. The molecules were packed by the weak C—H···O interaction between cations and anions (Table 1).

Experimental

The title salt (C23H26N4)2+.2(C6H2N3O7)- was synthesized using a slightly modified literature method (Jin et al., 2005). It was crystallized by slow evaporation of an acetonitrile solution of the salt.

Refinement

H atoms were positioned geometrically with C—H bond lengths fixed to 0.93 (aromatic CH),0.97 (methylene CH2) or 0.96Å (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.

Figures

Fig. 1.
The structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted.

Crystal data

C23H26N42+·2C6H2N3O7Z = 2
Mr = 814.69F000 = 844
Triclinic, P1Dx = 1.518 Mg m3
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 mm1
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

Data collection

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
[var phi] and ω scansh = −15→13
Absorption correction: nonek = −15→15
11547 measured reflectionsl = −15→13
6921 independent reflections

Refinement

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 Å3
534 parametersΔρmin = −0.21 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

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)

Atomic displacement parameters (Å2)

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)

Geometric parameters (Å, °)

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)

Hydrogen-bond geometry (Å, °)

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

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2431).

References

  • Bruker (2001). SAINT-Plus and SMART Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Jin, C. M., Twamley, B. & Shreeve, J. M. (2005). Organometallics, 24, 3020–3023.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, R. P., Verma, R. D., Meshri, D. T. & Shreeve, J. M. (2006). Angew. Chem. Int. Ed.45, 3584–3601. [PubMed]
  • Wang, R., Gao, H., Ye, C. & Shreeve, J. M. (2007). Chem. Mater.19, 144–152.

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