1,4-Dibenzyl-1,4-diazo­niabicyclo­[2.2.2]octane bis­(trifluoro­methane­sulfonate)

Chen, C.; Zhang, Y.; Brad, K.

doi:10.1107/S1600536807052063

1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate)

In the title compound, C₂₀H₂₆N₂²⁺·2CF₃SO₃⁻, the dihedral angle between the phenyl rings of the dication is 9.4 (3)°. The –CF₃ groups of both anions are disordered over two sets of positions in ratios of 0.920 (10):0.080 (10) and 0.76 (3):0.24 (3). In the crystal structure, C—H

O interactions link the molecules into columns.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052063/hb2583sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052063/hb2583Isup2.hkl Contains datablock I

CCDC reference: 667464

checkCIF report

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

Comment top

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).

Related literature top

For ammonium cations containing a 1,4-diazabicyclo[2.2.2]octane core, see: Chantrapromma et al. (2002); Mansikkamäki et al. (2005).

Experimental top

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.

Structure description top

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).

Computing details top

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).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms). Only one orientation of each trifluoromethanesulfonate ion is shown.

1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) top

Crystal data top

C₂₀H₂₆N₂²⁺·2CF₃O₃S⁻	F(000) = 2448
M_r = 592.57	D_x = 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

Data collection top

Bruker SMART 1K CCD diffractometer	4560 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.149
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.950, T_max = 0.972	k = −12→17
24969 measured reflections	l = −31→23

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) = 0.173	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
4560 reflections	(Δ/σ)_max = 0.002
399 parameters	Δρ_max = 0.29 e Å⁻³
144 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₂₆N₂²⁺·2CF₃O₃S⁻	V = 5166 (2) Å³
M_r = 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

Data collection top

Bruker SMART 1K CCD diffractometer	4560 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1952 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.972	R_int = 0.149
24969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	144 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
4560 reflections	Δρ_min = −0.27 e Å⁻³
399 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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⁻
M_r	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)
T_min, T_max	0.950, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	24969, 4560, 1952
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

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