Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052063/hb2583sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052063/hb2583Isup2.hkl |
CCDC reference: 667464
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.009 Å
- Disorder in solvent or counterion
- R factor = 0.059
- wR factor = 0.173
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT221_ALERT_4_B Large Solvent/Anion F Ueq(max)/Ueq(min) ... 4.25 Ratio PLAT432_ALERT_2_B Short Inter X...Y Contact C2 .. F2' .. 2.72 Ang.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.148 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C21 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S2 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 27.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C12 .. 3.00 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C9 .. 2.94 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C1 .. F3' .. 2.93 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.00 Deg. F3 -C21 -F1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.40 Deg. F2 -C21 -F3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.10 Deg. F5 -C22 -F6' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.10 Deg. F4 -C22 -F5' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.40 Deg. F6 -C22 -F4' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 144
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 5 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For ammonium cations containing a 1,4-diazabicyclo[2.2.2]octane core, see: Chantrapromma et al. (2002); Mansikkamäki et al. (2005).
The title compound was obtained, in a 75% yield, from counterion exchange of 1,4-dibenzyl-1,4-diazonia-bicyclo[2.2.2]octane dibromide (4.52 mg, 10 mmol) with silver trifluoromethanesulfonate (2.83 mg, 11 mmol) in methanol/acetonitrile (10 ml, v/v 1:4). Colourless blocks of (I) were grown by natural evaporation of a CH3CN/CH2Cl2 (v/v 1:1) solution.
All H atoms were positioned geometrically (C—H = 0.93 and 0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The –CF3 groups of the two trifluoromethanesulfonate anions were found to be disordered. The site occupancies of one trilate ion was refined to 0.920 (10):0.080 (10) and that of the other to 0.76 (3):0.24 (3).
In the dication of the title compound, (I), (Fig. 1), the dihedral angle between the terminal phenyl rings is 9.4 (3)°, indicating a trans conformation.
A network of C—H···O interactions (Table 1) between cation and anions link the molecules into columns. The adjacent columns are stabilized by weak aromatic interactions.
For related structures, see: Chantrapromma et al. (2002); Mansikkamäki et al. (2005).
For ammonium cations containing a 1,4-diazabicyclo[2.2.2]octane core, see: Chantrapromma et al. (2002); Mansikkamäki et al. (2005).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
C20H26N22+·2CF3O3S− | F(000) = 2448 |
Mr = 592.57 | Dx = 1.524 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1753 reflections |
a = 13.759 (3) Å | θ = 2.6–19.6° |
b = 14.334 (3) Å | µ = 0.29 mm−1 |
c = 26.195 (6) Å | T = 294 K |
V = 5166 (2) Å3 | Block, colourless |
Z = 8 | 0.18 × 0.16 × 0.10 mm |
Bruker SMART 1K CCD diffractometer | 4560 independent reflections |
Radiation source: fine-focus sealed tube | 1952 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.149 |
ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.950, Tmax = 0.972 | k = −12→17 |
24969 measured reflections | l = −31→23 |
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) = 0.173 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3 |
4560 reflections | (Δ/σ)max = 0.002 |
399 parameters | Δρmax = 0.29 e Å−3 |
144 restraints | Δρmin = −0.27 e Å−3 |
C20H26N22+·2CF3O3S− | V = 5166 (2) Å3 |
Mr = 592.57 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.759 (3) Å | µ = 0.29 mm−1 |
b = 14.334 (3) Å | T = 294 K |
c = 26.195 (6) Å | 0.18 × 0.16 × 0.10 mm |
Bruker SMART 1K CCD diffractometer | 4560 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1952 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.972 | Rint = 0.149 |
24969 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 144 restraints |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.29 e Å−3 |
4560 reflections | Δρmin = −0.27 e Å−3 |
399 parameters |
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) | |
N1 | 0.5039 (3) | 0.1698 (2) | 0.28420 (15) | 0.0310 (10) | |
N2 | 0.5071 (3) | 0.0692 (2) | 0.20271 (15) | 0.0305 (10) | |
C1 | 0.3890 (4) | 0.1821 (3) | 0.3991 (2) | 0.0489 (15) | |
H1 | 0.3366 | 0.2006 | 0.3790 | 0.059* | |
C2 | 0.3725 (5) | 0.1458 (4) | 0.4476 (3) | 0.0670 (19) | |
H2 | 0.3094 | 0.1403 | 0.4599 | 0.080* | |
C3 | 0.4484 (6) | 0.1187 (4) | 0.4768 (2) | 0.070 (2) | |
H3 | 0.4370 | 0.0941 | 0.5091 | 0.084* | |
C4 | 0.5424 (6) | 0.1269 (4) | 0.4593 (3) | 0.070 (2) | |
H4 | 0.5941 | 0.1082 | 0.4797 | 0.084* | |
C5 | 0.5592 (4) | 0.1626 (4) | 0.4119 (2) | 0.0530 (16) | |
H5 | 0.6229 | 0.1682 | 0.4003 | 0.064* | |
C6 | 0.4831 (4) | 0.1908 (3) | 0.3804 (2) | 0.0359 (13) | |
C7 | 0.5038 (4) | 0.2349 (3) | 0.33045 (19) | 0.0399 (14) | |
H7A | 0.5668 | 0.2650 | 0.3325 | 0.048* | |
H7B | 0.4558 | 0.2834 | 0.3247 | 0.048* | |
C8 | 0.5599 (4) | 0.0811 (3) | 0.29332 (19) | 0.0405 (14) | |
H8A | 0.5336 | 0.0489 | 0.3228 | 0.049* | |
H8B | 0.6274 | 0.0958 | 0.3003 | 0.049* | |
C9 | 0.5532 (4) | 0.0187 (3) | 0.24675 (19) | 0.0410 (14) | |
H9A | 0.6178 | −0.0018 | 0.2371 | 0.049* | |
H9B | 0.5150 | −0.0362 | 0.2550 | 0.049* | |
C10 | 0.4022 (3) | 0.1436 (3) | 0.2681 (2) | 0.0383 (14) | |
H10A | 0.3628 | 0.1995 | 0.2650 | 0.046* | |
H10B | 0.3730 | 0.1040 | 0.2939 | 0.046* | |
C11 | 0.4043 (3) | 0.0927 (3) | 0.2176 (2) | 0.0425 (14) | |
H11A | 0.3665 | 0.0357 | 0.2202 | 0.051* | |
H11B | 0.3751 | 0.1315 | 0.1914 | 0.051* | |
C12 | 0.5512 (3) | 0.2205 (3) | 0.24066 (18) | 0.0385 (14) | |
H12A | 0.6148 | 0.2425 | 0.2512 | 0.046* | |
H12B | 0.5123 | 0.2745 | 0.2316 | 0.046* | |
C13 | 0.5621 (4) | 0.1581 (3) | 0.1945 (2) | 0.0455 (15) | |
H13A | 0.5374 | 0.1897 | 0.1644 | 0.055* | |
H13B | 0.6303 | 0.1443 | 0.1889 | 0.055* | |
C14 | 0.5103 (4) | 0.0051 (3) | 0.15592 (19) | 0.0394 (14) | |
H14A | 0.5752 | −0.0209 | 0.1532 | 0.047* | |
H14B | 0.4658 | −0.0464 | 0.1616 | 0.047* | |
C15 | 0.4850 (4) | 0.0501 (3) | 0.1062 (2) | 0.0407 (14) | |
C16 | 0.5581 (4) | 0.0838 (4) | 0.0752 (2) | 0.0556 (16) | |
H16 | 0.6223 | 0.0811 | 0.0862 | 0.067* | |
C17 | 0.5370 (6) | 0.1213 (4) | 0.0284 (3) | 0.076 (2) | |
H17 | 0.5870 | 0.1441 | 0.0080 | 0.091* | |
C18 | 0.4437 (7) | 0.1253 (4) | 0.0115 (3) | 0.081 (2) | |
H18 | 0.4297 | 0.1507 | −0.0203 | 0.097* | |
C19 | 0.3693 (6) | 0.0912 (5) | 0.0421 (3) | 0.080 (2) | |
H19 | 0.3053 | 0.0940 | 0.0308 | 0.096* | |
C20 | 0.3901 (5) | 0.0532 (4) | 0.0893 (2) | 0.0575 (17) | |
H20 | 0.3403 | 0.0298 | 0.1095 | 0.069* | |
S1 | 0.20596 (10) | 0.40619 (9) | 0.33002 (5) | 0.0408 (4) | |
F1 | 0.1019 (5) | 0.4374 (3) | 0.4105 (2) | 0.107 (2) | 0.920 (10) |
F2 | 0.2488 (4) | 0.3995 (5) | 0.42608 (18) | 0.130 (3) | 0.920 (10) |
F3 | 0.1492 (5) | 0.2968 (3) | 0.4033 (2) | 0.0942 (19) | 0.920 (10) |
F1' | 0.101 (3) | 0.323 (3) | 0.397 (3) | 0.078 (19) | 0.080 (10) |
F2' | 0.170 (4) | 0.4667 (15) | 0.4217 (13) | 0.040 (13) | 0.080 (10) |
F3' | 0.256 (2) | 0.339 (3) | 0.4140 (7) | 0.17 (2) | 0.080 (10) |
O1 | 0.2473 (3) | 0.4983 (2) | 0.33005 (16) | 0.0668 (12) | |
O2 | 0.1144 (3) | 0.4028 (3) | 0.30509 (16) | 0.0753 (13) | |
O3 | 0.2700 (4) | 0.3325 (3) | 0.31787 (18) | 0.1060 (18) | |
C21 | 0.1763 (4) | 0.3850 (4) | 0.3955 (3) | 0.0635 (19) | |
S2 | 0.28188 (10) | 0.33629 (9) | 0.17470 (5) | 0.0390 (4) | |
F4 | 0.3532 (11) | 0.4358 (5) | 0.1020 (4) | 0.085 (3) | 0.76 (3) |
F5 | 0.2433 (8) | 0.3406 (12) | 0.0780 (3) | 0.100 (3) | 0.76 (3) |
F6 | 0.3860 (9) | 0.2898 (7) | 0.0955 (5) | 0.104 (4) | 0.76 (3) |
F4' | 0.4084 (12) | 0.3128 (19) | 0.1073 (7) | 0.064 (8) | 0.24 (3) |
F5' | 0.322 (2) | 0.4388 (9) | 0.0912 (14) | 0.076 (10) | 0.24 (3) |
F6' | 0.268 (2) | 0.299 (2) | 0.0755 (8) | 0.071 (8) | 0.24 (3) |
O4 | 0.2075 (3) | 0.4040 (3) | 0.18113 (17) | 0.0884 (16) | |
O5 | 0.3699 (3) | 0.3521 (3) | 0.20207 (16) | 0.0749 (13) | |
O6 | 0.2488 (2) | 0.2410 (2) | 0.17770 (15) | 0.0563 (11) | |
C22 | 0.3177 (4) | 0.3502 (4) | 0.1094 (2) | 0.0621 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.029 (2) | 0.023 (2) | 0.041 (3) | −0.0019 (18) | −0.004 (2) | 0.007 (2) |
N2 | 0.032 (3) | 0.024 (2) | 0.036 (3) | −0.0010 (18) | 0.002 (2) | 0.0068 (19) |
C1 | 0.051 (4) | 0.043 (3) | 0.053 (4) | 0.005 (3) | 0.000 (3) | −0.008 (3) |
C2 | 0.084 (5) | 0.058 (4) | 0.059 (5) | −0.003 (4) | 0.030 (4) | −0.002 (4) |
C3 | 0.126 (7) | 0.056 (4) | 0.028 (4) | 0.012 (4) | 0.014 (5) | 0.000 (3) |
C4 | 0.093 (6) | 0.075 (5) | 0.042 (5) | 0.015 (4) | −0.010 (4) | 0.007 (3) |
C5 | 0.049 (4) | 0.068 (4) | 0.042 (4) | 0.005 (3) | −0.007 (3) | 0.000 (3) |
C6 | 0.043 (4) | 0.027 (3) | 0.038 (3) | 0.000 (2) | 0.003 (3) | 0.005 (2) |
C7 | 0.043 (3) | 0.030 (3) | 0.047 (4) | −0.006 (2) | −0.007 (3) | −0.006 (3) |
C8 | 0.041 (3) | 0.035 (3) | 0.045 (4) | 0.007 (3) | −0.003 (3) | 0.016 (3) |
C9 | 0.045 (4) | 0.037 (3) | 0.042 (3) | 0.014 (2) | −0.001 (3) | 0.010 (3) |
C10 | 0.024 (3) | 0.037 (3) | 0.054 (4) | −0.002 (2) | 0.003 (3) | 0.000 (3) |
C11 | 0.025 (3) | 0.042 (3) | 0.061 (4) | 0.007 (2) | −0.004 (3) | −0.007 (3) |
C12 | 0.043 (3) | 0.028 (3) | 0.044 (4) | −0.014 (2) | −0.001 (3) | 0.007 (3) |
C13 | 0.055 (4) | 0.040 (3) | 0.041 (4) | −0.020 (3) | 0.001 (3) | 0.013 (3) |
C14 | 0.045 (4) | 0.031 (3) | 0.042 (4) | 0.004 (2) | −0.002 (3) | −0.005 (3) |
C15 | 0.050 (4) | 0.037 (3) | 0.035 (3) | −0.004 (3) | −0.003 (3) | −0.005 (3) |
C16 | 0.058 (4) | 0.064 (4) | 0.045 (4) | −0.008 (3) | 0.003 (3) | −0.003 (3) |
C17 | 0.118 (7) | 0.062 (5) | 0.047 (5) | −0.021 (4) | 0.013 (5) | 0.003 (4) |
C18 | 0.150 (8) | 0.051 (4) | 0.040 (5) | 0.014 (5) | −0.021 (5) | −0.001 (3) |
C19 | 0.099 (6) | 0.080 (5) | 0.060 (5) | 0.018 (5) | −0.034 (5) | −0.003 (4) |
C20 | 0.057 (5) | 0.059 (4) | 0.057 (4) | −0.002 (3) | −0.014 (4) | −0.008 (3) |
S1 | 0.0411 (9) | 0.0445 (9) | 0.0369 (9) | 0.0073 (7) | −0.0002 (7) | 0.0014 (7) |
F1 | 0.139 (5) | 0.086 (3) | 0.097 (4) | 0.002 (3) | 0.069 (4) | −0.015 (3) |
F2 | 0.181 (5) | 0.146 (5) | 0.064 (3) | −0.049 (4) | −0.062 (3) | 0.012 (3) |
F3 | 0.132 (5) | 0.060 (3) | 0.090 (4) | −0.013 (3) | 0.032 (3) | 0.023 (3) |
F1' | 0.08 (2) | 0.07 (2) | 0.08 (2) | −0.004 (10) | 0.007 (10) | 0.005 (10) |
F2' | 0.045 (16) | 0.041 (15) | 0.035 (15) | 0.002 (10) | −0.003 (10) | −0.005 (9) |
F3' | 0.17 (2) | 0.17 (2) | 0.17 (2) | 0.0001 (11) | −0.0001 (11) | 0.0000 (11) |
O1 | 0.054 (3) | 0.063 (3) | 0.084 (3) | −0.021 (2) | −0.002 (2) | 0.014 (2) |
O2 | 0.070 (3) | 0.074 (3) | 0.081 (3) | −0.010 (2) | −0.043 (3) | −0.001 (2) |
O3 | 0.138 (4) | 0.103 (3) | 0.078 (3) | 0.087 (3) | 0.044 (3) | 0.023 (3) |
C21 | 0.070 (5) | 0.047 (4) | 0.073 (5) | −0.004 (3) | 0.014 (4) | −0.011 (4) |
S2 | 0.0394 (9) | 0.0416 (8) | 0.0360 (8) | 0.0076 (7) | 0.0030 (7) | −0.0011 (7) |
F4 | 0.110 (6) | 0.062 (4) | 0.083 (5) | −0.016 (3) | 0.032 (5) | 0.021 (3) |
F5 | 0.149 (6) | 0.096 (7) | 0.056 (4) | −0.002 (5) | −0.032 (4) | 0.001 (4) |
F6 | 0.134 (6) | 0.081 (5) | 0.099 (5) | 0.005 (5) | 0.066 (5) | −0.033 (4) |
F4' | 0.043 (10) | 0.074 (12) | 0.074 (11) | −0.001 (7) | 0.012 (7) | −0.018 (8) |
F5' | 0.073 (12) | 0.072 (12) | 0.082 (12) | 0.006 (7) | 0.009 (8) | 0.029 (8) |
F6' | 0.091 (12) | 0.074 (11) | 0.047 (9) | −0.004 (8) | −0.002 (7) | −0.010 (8) |
O4 | 0.101 (4) | 0.083 (3) | 0.081 (3) | 0.061 (3) | 0.042 (3) | 0.023 (3) |
O5 | 0.065 (3) | 0.081 (3) | 0.079 (3) | −0.019 (2) | −0.038 (3) | −0.003 (2) |
O6 | 0.051 (2) | 0.045 (2) | 0.073 (3) | −0.0096 (18) | −0.002 (2) | 0.012 (2) |
C22 | 0.069 (5) | 0.052 (5) | 0.065 (5) | −0.002 (4) | 0.017 (4) | −0.007 (4) |
N1—C12 | 1.501 (6) | C13—H13B | 0.9700 |
N1—C8 | 1.506 (6) | C14—C15 | 1.494 (7) |
N1—C10 | 1.509 (5) | C14—H14A | 0.9700 |
N1—C7 | 1.529 (6) | C14—H14B | 0.9700 |
N2—C13 | 1.497 (5) | C15—C16 | 1.380 (7) |
N2—C9 | 1.503 (6) | C15—C20 | 1.380 (7) |
N2—C11 | 1.506 (5) | C16—C17 | 1.371 (8) |
N2—C14 | 1.533 (6) | C16—H16 | 0.9300 |
C1—C6 | 1.389 (7) | C17—C18 | 1.360 (9) |
C1—C2 | 1.391 (8) | C17—H17 | 0.9300 |
C1—H1 | 0.9300 | C18—C19 | 1.389 (9) |
C2—C3 | 1.352 (8) | C18—H18 | 0.9300 |
C2—H2 | 0.9300 | C19—C20 | 1.379 (8) |
C3—C4 | 1.377 (9) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.363 (8) | S1—O3 | 1.411 (4) |
C4—H4 | 0.9300 | S1—O2 | 1.420 (4) |
C5—C6 | 1.393 (7) | S1—O1 | 1.438 (4) |
C5—H5 | 0.9300 | S1—C21 | 1.788 (7) |
C6—C7 | 1.482 (7) | F1—C21 | 1.330 (6) |
C7—H7A | 0.9700 | F2—C21 | 1.296 (6) |
C7—H7B | 0.9700 | F3—C21 | 1.334 (6) |
C8—C9 | 1.516 (7) | F1'—C21 | 1.367 (11) |
C8—H8A | 0.9700 | F2'—C21 | 1.359 (10) |
C8—H8B | 0.9700 | F3'—C21 | 1.370 (10) |
C9—H9A | 0.9700 | S2—O4 | 1.421 (4) |
C9—H9B | 0.9700 | S2—O5 | 1.425 (4) |
C10—C11 | 1.513 (7) | S2—O6 | 1.442 (3) |
C10—H10A | 0.9700 | S2—C22 | 1.791 (6) |
C10—H10B | 0.9700 | F4—C22 | 1.334 (7) |
C11—H11A | 0.9700 | F5—C22 | 1.321 (7) |
C11—H11B | 0.9700 | F6—C22 | 1.329 (7) |
C12—C13 | 1.512 (6) | F4'—C22 | 1.359 (9) |
C12—H12A | 0.9700 | F5'—C22 | 1.358 (10) |
C12—H12B | 0.9700 | F6'—C22 | 1.347 (10) |
C13—H13A | 0.9700 | ||
C12—N1—C8 | 107.9 (4) | C15—C14—H14B | 108.4 |
C12—N1—C10 | 108.1 (4) | N2—C14—H14B | 108.4 |
C8—N1—C10 | 108.0 (4) | H14A—C14—H14B | 107.5 |
C12—N1—C7 | 107.9 (3) | C16—C15—C20 | 119.3 (5) |
C8—N1—C7 | 112.9 (4) | C16—C15—C14 | 119.6 (5) |
C10—N1—C7 | 111.9 (3) | C20—C15—C14 | 121.0 (5) |
C13—N2—C9 | 107.9 (4) | C17—C16—C15 | 120.7 (6) |
C13—N2—C11 | 108.8 (4) | C17—C16—H16 | 119.7 |
C9—N2—C11 | 107.8 (4) | C15—C16—H16 | 119.7 |
C13—N2—C14 | 112.4 (4) | C18—C17—C16 | 120.5 (7) |
C9—N2—C14 | 108.2 (3) | C18—C17—H17 | 119.8 |
C11—N2—C14 | 111.5 (4) | C16—C17—H17 | 119.8 |
C6—C1—C2 | 120.4 (6) | C17—C18—C19 | 119.6 (7) |
C6—C1—H1 | 119.8 | C17—C18—H18 | 120.2 |
C2—C1—H1 | 119.8 | C19—C18—H18 | 120.2 |
C3—C2—C1 | 120.0 (6) | C20—C19—C18 | 120.2 (7) |
C3—C2—H2 | 120.0 | C20—C19—H19 | 119.9 |
C1—C2—H2 | 120.0 | C18—C19—H19 | 119.9 |
C2—C3—C4 | 120.7 (6) | C19—C20—C15 | 119.8 (6) |
C2—C3—H3 | 119.6 | C19—C20—H20 | 120.1 |
C4—C3—H3 | 119.6 | C15—C20—H20 | 120.1 |
C5—C4—C3 | 119.7 (6) | O3—S1—O2 | 115.1 (3) |
C5—C4—H4 | 120.1 | O3—S1—O1 | 116.1 (3) |
C3—C4—H4 | 120.1 | O2—S1—O1 | 112.5 (2) |
C4—C5—C6 | 121.3 (6) | O3—S1—C21 | 103.4 (3) |
C4—C5—H5 | 119.4 | O2—S1—C21 | 103.5 (3) |
C6—C5—H5 | 119.4 | O1—S1—C21 | 104.2 (3) |
C1—C6—C5 | 117.8 (5) | F2—C21—F1 | 108.5 (6) |
C1—C6—C7 | 121.9 (5) | F2—C21—F3 | 105.7 (6) |
C5—C6—C7 | 120.1 (5) | F1—C21—F3 | 105.9 (5) |
C6—C7—N1 | 116.1 (4) | F2—C21—F2' | 66.1 (17) |
C6—C7—H7A | 108.3 | F1—C21—F2' | 47.0 (19) |
N1—C7—H7A | 108.3 | F3—C21—F2' | 136.2 (19) |
C6—C7—H7B | 108.3 | F2—C21—F1' | 132 (2) |
N1—C7—H7B | 108.3 | F1—C21—F1' | 77 (2) |
H7A—C7—H7B | 107.4 | F3—C21—F1' | 34 (2) |
N1—C8—C9 | 109.9 (4) | F2'—C21—F1' | 120 (3) |
N1—C8—H8A | 109.7 | F2—C21—F3' | 40.4 (18) |
C9—C8—H8A | 109.7 | F1—C21—F3' | 141.6 (11) |
N1—C8—H8B | 109.7 | F3—C21—F3' | 73.6 (19) |
C9—C8—H8B | 109.7 | F2'—C21—F3' | 106.3 (10) |
H8A—C8—H8B | 108.2 | F1'—C21—F3' | 106.9 (10) |
N2—C9—C8 | 111.0 (4) | F2—C21—S1 | 113.0 (5) |
N2—C9—H9A | 109.4 | F1—C21—S1 | 111.4 (5) |
C8—C9—H9A | 109.4 | F3—C21—S1 | 111.9 (4) |
N2—C9—H9B | 109.4 | F2'—C21—S1 | 110.6 (17) |
C8—C9—H9B | 109.4 | F1'—C21—S1 | 108 (3) |
H9A—C9—H9B | 108.0 | F3'—C21—S1 | 103.7 (8) |
N1—C10—C11 | 110.3 (4) | O4—S2—O5 | 116.3 (3) |
N1—C10—H10A | 109.6 | O4—S2—O6 | 114.4 (3) |
C11—C10—H10A | 109.6 | O5—S2—O6 | 113.0 (2) |
N1—C10—H10B | 109.6 | O4—S2—C22 | 103.6 (3) |
C11—C10—H10B | 109.6 | O5—S2—C22 | 103.2 (3) |
H10A—C10—H10B | 108.1 | O6—S2—C22 | 104.2 (2) |
N2—C11—C10 | 110.6 (4) | F5—C22—F6 | 108.1 (7) |
N2—C11—H11A | 109.5 | F5—C22—F4 | 106.8 (8) |
C10—C11—H11A | 109.5 | F6—C22—F4 | 107.5 (7) |
N2—C11—H11B | 109.5 | F5—C22—F6' | 30.1 (11) |
C10—C11—H11B | 109.5 | F6—C22—F6' | 79.8 (12) |
H11A—C11—H11B | 108.1 | F4—C22—F6' | 126.7 (13) |
N1—C12—C13 | 111.4 (4) | F5—C22—F5' | 84.9 (12) |
N1—C12—H12A | 109.4 | F6—C22—F5' | 118.8 (14) |
C13—C12—H12A | 109.4 | F4—C22—F5' | 22.1 (13) |
N1—C12—H12B | 109.4 | F6'—C22—F5' | 107.7 (10) |
C13—C12—H12B | 109.4 | F5—C22—F4' | 130.2 (11) |
H12A—C12—H12B | 108.0 | F6—C22—F4' | 23.4 (11) |
N2—C13—C12 | 109.8 (4) | F4—C22—F4' | 91.2 (12) |
N2—C13—H13A | 109.7 | F6'—C22—F4' | 103.1 (14) |
C12—C13—H13A | 109.7 | F5'—C22—F4' | 108.4 (9) |
N2—C13—H13B | 109.7 | F5—C22—S2 | 111.7 (6) |
C12—C13—H13B | 109.7 | F6—C22—S2 | 112.6 (6) |
H13A—C13—H13B | 108.2 | F4—C22—S2 | 110.0 (6) |
C15—C14—N2 | 115.6 (4) | F6'—C22—S2 | 115.3 (11) |
C15—C14—H14A | 108.4 | F5'—C22—S2 | 116.9 (15) |
N2—C14—H14A | 108.4 | F4'—C22—S2 | 104.3 (7) |
C6—C1—C2—C3 | −0.2 (8) | C16—C17—C18—C19 | 0.1 (10) |
C1—C2—C3—C4 | 0.4 (9) | C17—C18—C19—C20 | −0.2 (10) |
C2—C3—C4—C5 | −0.2 (9) | C18—C19—C20—C15 | 0.7 (9) |
C3—C4—C5—C6 | −0.2 (9) | C16—C15—C20—C19 | −1.0 (8) |
C2—C1—C6—C5 | −0.3 (7) | C14—C15—C20—C19 | −176.9 (5) |
C2—C1—C6—C7 | −175.8 (5) | O3—S1—C21—F2 | 69.7 (6) |
C4—C5—C6—C1 | 0.5 (8) | O2—S1—C21—F2 | −170.0 (5) |
C4—C5—C6—C7 | 176.1 (5) | O1—S1—C21—F2 | −52.2 (5) |
C1—C6—C7—N1 | −89.4 (6) | O3—S1—C21—F1 | −167.8 (5) |
C5—C6—C7—N1 | 95.2 (5) | O2—S1—C21—F1 | −47.5 (5) |
C12—N1—C7—C6 | −165.2 (4) | O1—S1—C21—F1 | 70.3 (5) |
C8—N1—C7—C6 | −46.1 (6) | O3—S1—C21—F3 | −49.5 (6) |
C10—N1—C7—C6 | 76.0 (5) | O2—S1—C21—F3 | 70.9 (5) |
C12—N1—C8—C9 | −63.2 (5) | O1—S1—C21—F3 | −171.4 (5) |
C10—N1—C8—C9 | 53.4 (5) | O3—S1—C21—F2' | 142 (2) |
C7—N1—C8—C9 | 177.7 (4) | O2—S1—C21—F2' | −98 (2) |
C13—N2—C9—C8 | 53.6 (5) | O1—S1—C21—F2' | 20 (2) |
C11—N2—C9—C8 | −63.8 (5) | O3—S1—C21—F1' | −85 (2) |
C14—N2—C9—C8 | 175.4 (4) | O2—S1—C21—F1' | 35 (2) |
N1—C8—C9—N2 | 9.1 (6) | O1—S1—C21—F1' | 153 (2) |
C12—N1—C10—C11 | 52.1 (5) | O3—S1—C21—F3' | 28 (2) |
C8—N1—C10—C11 | −64.4 (5) | O2—S1—C21—F3' | 148 (2) |
C7—N1—C10—C11 | 170.7 (4) | O1—S1—C21—F3' | −94 (2) |
C13—N2—C11—C10 | −64.0 (5) | O4—S2—C22—F5 | −56.3 (9) |
C9—N2—C11—C10 | 52.8 (5) | O5—S2—C22—F5 | −178.0 (9) |
C14—N2—C11—C10 | 171.5 (4) | O6—S2—C22—F5 | 63.7 (9) |
N1—C10—C11—N2 | 9.4 (5) | O4—S2—C22—F6 | −178.1 (9) |
C8—N1—C12—C13 | 52.9 (5) | O5—S2—C22—F6 | 60.2 (9) |
C10—N1—C12—C13 | −63.7 (5) | O6—S2—C22—F6 | −58.1 (9) |
C7—N1—C12—C13 | 175.2 (4) | O4—S2—C22—F4 | 62.1 (9) |
C9—N2—C13—C12 | −64.1 (5) | O5—S2—C22—F4 | −59.6 (9) |
C11—N2—C13—C12 | 52.6 (5) | O6—S2—C22—F4 | −177.9 (9) |
C14—N2—C13—C12 | 176.6 (4) | O4—S2—C22—F6' | −89.0 (19) |
N1—C12—C13—N2 | 9.7 (6) | O5—S2—C22—F6' | 149.3 (19) |
C13—N2—C14—C15 | −49.7 (6) | O6—S2—C22—F6' | 31.0 (19) |
C9—N2—C14—C15 | −168.8 (4) | O4—S2—C22—F5' | 39.1 (16) |
C11—N2—C14—C15 | 72.8 (5) | O5—S2—C22—F5' | −82.6 (16) |
N2—C14—C15—C16 | 95.0 (6) | O6—S2—C22—F5' | 159.1 (16) |
N2—C14—C15—C20 | −89.1 (6) | O4—S2—C22—F4' | 158.8 (14) |
C20—C15—C16—C17 | 0.9 (8) | O5—S2—C22—F4' | 37.0 (14) |
C14—C15—C16—C17 | 176.8 (5) | O6—S2—C22—F4' | −81.2 (14) |
C15—C16—C17—C18 | −0.4 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O6i | 0.97 | 2.54 | 3.380 (6) | 145 |
C9—H9A···O1ii | 0.97 | 2.56 | 3.416 (6) | 148 |
C9—H9B···O2iii | 0.97 | 2.38 | 3.227 (6) | 146 |
C10—H10B···O1iii | 0.97 | 2.43 | 3.347 (6) | 156 |
C11—H11A···O4iii | 0.97 | 2.38 | 3.255 (6) | 150 |
C11—H11B···O6 | 0.97 | 2.37 | 3.191 (5) | 142 |
C12—H12B···O5 | 0.97 | 2.38 | 3.287 (6) | 155 |
C14—H14A···O1ii | 0.97 | 2.50 | 3.357 (7) | 148 |
C14—H14B···O4iii | 0.97 | 2.54 | 3.394 (7) | 147 |
Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C20H26N22+·2CF3O3S− |
Mr | 592.57 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 294 |
a, b, c (Å) | 13.759 (3), 14.334 (3), 26.195 (6) |
V (Å3) | 5166 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.18 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.950, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24969, 4560, 1952 |
Rint | 0.149 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.173, 1.01 |
No. of reflections | 4560 |
No. of parameters | 399 |
No. of restraints | 144 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.27 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O6i | 0.97 | 2.54 | 3.380 (6) | 145 |
C9—H9A···O1ii | 0.97 | 2.56 | 3.416 (6) | 148 |
C9—H9B···O2iii | 0.97 | 2.38 | 3.227 (6) | 146 |
C10—H10B···O1iii | 0.97 | 2.43 | 3.347 (6) | 156 |
C11—H11A···O4iii | 0.97 | 2.38 | 3.255 (6) | 150 |
C11—H11B···O6 | 0.97 | 2.37 | 3.191 (5) | 142 |
C12—H12B···O5 | 0.97 | 2.38 | 3.287 (6) | 155 |
C14—H14A···O1ii | 0.97 | 2.50 | 3.357 (7) | 148 |
C14—H14B···O4iii | 0.97 | 2.54 | 3.394 (7) | 147 |
Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, z. |
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In the dication of the title compound, (I), (Fig. 1), the dihedral angle between the terminal phenyl rings is 9.4 (3)°, indicating a trans conformation.
A network of C—H···O interactions (Table 1) between cation and anions link the molecules into columns. The adjacent columns are stabilized by weak aromatic interactions.
For related structures, see: Chantrapromma et al. (2002); Mansikkamäki et al. (2005).