Rubidium bis­(tri­fluoro­methane­sulfonyl)­imidate dioxane disolvate

The bis­(tri­fluoro­methane­sulfonyl)­imidate anion crystallizes with Rb as the title dioxane 1:2 solvate, Rb⁺·CF₃SO₂NSO₂CF₃^-·2C₄H₈O₂, with the anion in a transoid conformation, as opposed to the cisoid form typically seen when there are significant cation-anion interactions. The Rb^I cation is eight-coordinate, interacting with one anion in a chelating fashion and with two other anions through the remaining sulfonyl O atoms. The latter interactions link ion pairs through the formation of Rb₂O₂ dimers about inversion centers at (0, , 0) and (, , 0), forming extended columns which run parallel to the a axis of the unit cell. Rb-dioxane bridges crosslink these salt columns in the (010), (001) and (011) directions, resulting in a three-dimensional network solid. One dioxane solvent mol­ecule is disordered over two half-occupancy sites.

S1. Comment

Salts of bis(perfluoroalkanesulfonyl)imides, particularly the trifluoromethyl derivatives, have been found to serve as solutes for polymer electrolytes, leading to dramatically improved performance (Armand et al., 1990; Nowinski et al., 1994). This behavior is due in part to the remarkable acidity of these compounds (Koppel et al., 1994; DesMarteau, 1995). The resonance stabilization of the conjugate base anions of the acids results from extensive delocalization of charge over the SO₂—N—SO₂ framework. With cations offering no strong interactions, these anions have been found to give salts with good potential as ionic liquids (Golding et al., 1998). On the other hand, with metal cations they serve as multidentate ligands that bond to multiple metal centers to maximize electrostatic interaction (DesMarteau et al., 1989, 1992; Xue et al., 1997, 2002). These interactions result in the formation of ionic hydrophilic and perfluoroalkyl hydrophobic regions, which typically associate into layers consisting of an ionic core with perfluoroalkyl surfaces. This fluorine segregation effect (Dautel et al., 2002; Wolff et al., 1999) may provide a feasible driving force for the directed design of new solid state materials.

As we (Xue et al., 1997, 2002) and others (Zak & Ruzicka, 1998) have observed, bis(perfluoroalkanesulfonyl)imides can exist in two different conformations as the anion, either a transoid form with the perfluoroalkyl groups lying on opposite sides of the S—N—S plane (C—S···S—C dihedral angle of ~180°) or a cisoid form with the perfluoroalkyl groups lying on the same side of the S—N—S plane (C—S···S—C dihedral angle of ~0°). It has been our general experience that the transoid form is favored when there are only weak cation···anion interactions, but that the cisoid form is often found when the anion is chelated to a metal center. In a recent contribution (Xue et al., 2002), the anion was found in the cisoid form in anhydrous and hydrated salts of all the alkali metal cations except rubidium, which was determined as the monohydrate salt. Here, we report the structure of the title dioxane solvate, (I), of the rubidium salt and, like the monohydrate form, the anion has a transoid conformation [C—S···S—C dihedral angle of −147.2 (4)°]. \sch

The distances and angles within the anion of (I) agree well with those of other salts (DesMarteau et al., 1989, 1992; Xue et al., 1997, 2002; Haas et al., 1996; Mikami et al., 1998; Polyakov et al., 1999). The cation is eight-coordinate, with Rb···O contacts ranging from 2.897 (4) to 3.063 (4) Å. These contacts are also within previously reported ranges for rubidium salts of this (Xue et al., 2002; Zak et al., 1998) and similar anions (Juschke et al., 1997) and for rubidium dioxane solvates (Bryan et al., 1998, 1999; Neander et al., 2000; Edelmann et al., 1992).

The cation and anion of (I) sit upon general positions within the cell. The anion interacts with the cation through atoms O1 and O3 to form a chelate. Additional contacts through atom O2 about an inversion center at (0, 1/2, 0) and atom O4 about (1/2, 1/2, 0) link ion pairs into columns running up the a axis. Each of the dioxane molecules is situated about an inversion center and bridges salt columns in the (010), (001) and (011) directions, to form a three-dimensional network solid.

Reasons for the observed preference of the transoid conformation of the anion with Rb are not yet clear, but investigation into this interesting behavior will continue.

S2. Experimental

The title compound was synthesized by neutralization of a methanol solution of bis(trifluoromethandsulfonyl)imide in acid form with rubidium carbonate, followed by recrystallization from dioxane.

S3. Refinement

Dioxane 4 (atoms O8, C9 and C10) was disordered, with equally occupied alternative sites, C9' and C10', for the C atoms. Restraints were applied to the O—C, C—C, and cross-ring C—C, O—C and O—O contacts, and all the half-occupancy non-H atoms were refined with anisotropic displacement parameters. All H atoms were included in the structure-factor calculation as a riding model at optimized positions, with a C—H distance of 0.97 Å and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: P3 Software (Siemens, 1989); cell refinement: P3 Software; data reduction: SHELXTL (Sheldrick, 2000); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of Rb[CF3SO2NSO2CF3] and four bridging dioxane molecules. Only one component of the disordered dioxane molecule (atoms O8, C9, C10) is shown, and H atoms have been omitted. Displacement ellipsoids are shown at the 30% probability level. [Symmetry codes: (A) −x, 1 − y, −z; (B) 1 − x, 1 − y, −z; (C) 1 − x, 2 − y, −z; (D) 1 − x, 1 − y, 1 − z; (E) 1 − x, 2 − y, 1 − z; (F) 2 − x, 2 − y, 1 − z.]

Fig. 2. A packing diagram for (I), viewed down the a axis. S atoms are shown as 50% probability displacement ellipsoids, Rb^I ions as large open circles, N atoms as solid circles, O atoms as partially shaded circles and C atoms as small open circles. H atoms are not shown.

Rubidium bis(trifluoromethanesulfonyl)imidate dioxane disolvate

Crystal data

[Rb(C2F6NO4S2)]·2C4H8O2	Z = 2
Mr = 541.83	F(000) = 540
Triclinic, P1	Dx = 1.768 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.732 (4) Å	Cell parameters from 50 reflections
b = 11.310 (4) Å	θ = 11.7–17.8°
c = 11.638 (4) Å	µ = 2.73 mm^−1
α = 94.61 (3)°	T = 295 K
β = 113.08 (3)°	Parallelepiped, colorless
γ = 115.24 (3)°	0.41 × 0.37 × 0.26 mm
V = 1017.7 (8) Å^3

Data collection

Nicolet R3mV diffractometer	2092 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.027
Graphite monochromator	θmax = 25.1°, θmin = 2.0°
ω/2θ scans	h = −11→0
Absorption correction: empirical (using intensity measurements) via ψ scan (P3 Software; Siemens, 1989)	k = −12→13
Tmin = 0.342, Tmax = 0.492	l = −12→13
3805 measured reflections	3 standard reflections every 97 reflections
3576 independent reflections	intensity decay: 0.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0032P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.004
3576 reflections	Δρmax = 0.36 e Å^−3
272 parameters	Δρmin = −0.29 e Å^−3
17 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0148 (4)

Special details

Experimental. Empirical absorption correction was made based on ψ scans of six reflections (P3 Software; Siemens, 1989).

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Rb1	0.46063 (7)	0.72582 (5)	0.20998 (5)	0.05530 (19)
S1	0.23225 (17)	0.33945 (12)	−0.05608 (12)	0.0566 (4)
S2	0.05932 (18)	0.47957 (13)	−0.16469 (12)	0.0610 (4)
F1	−0.0149 (5)	0.0948 (3)	−0.1048 (4)	0.1271 (15)
F2	0.1988 (5)	0.1770 (3)	0.0861 (4)	0.1161 (13)
F3	0.0231 (6)	0.2509 (4)	0.0410 (4)	0.1433 (18)
F4	0.2720 (7)	0.5780 (5)	−0.2583 (5)	0.175 (2)
F5	0.0780 (7)	0.6332 (4)	−0.3143 (3)	0.151 (2)
F6	0.0110 (7)	0.4317 (4)	−0.4015 (3)	0.153 (2)
O1	0.3509 (4)	0.4519 (3)	0.0590 (3)	0.0664 (10)
O2	0.2961 (5)	0.2712 (3)	−0.1121 (4)	0.0850 (12)
O3	0.1759 (5)	0.5980 (3)	−0.0537 (3)	0.0762 (11)
O4	−0.1204 (5)	0.4287 (4)	−0.2181 (4)	0.0985 (14)
O5	0.5583 (5)	0.9821 (4)	0.1248 (3)	0.0790 (11)
O6	0.8263 (5)	0.9252 (5)	0.4049 (4)	0.0918 (13)
O7	0.4447 (6)	0.9312 (5)	0.3744 (4)	0.140 (2)
O8	0.5239 (8)	0.5916 (6)	0.4292 (5)	0.1274 (19)
N1	0.0916 (6)	0.3555 (4)	−0.1651 (4)	0.0816 (15)
C1	0.0991 (9)	0.2084 (6)	−0.0066 (7)	0.0821 (18)
C2	0.1120 (12)	0.5313 (7)	−0.2913 (7)	0.107 (3)
C3	0.6649 (7)	1.0213 (6)	0.0632 (5)	0.0778 (17)
H3A	0.7440	0.9862	0.0918	0.093*
H3B	0.7324	1.1203	0.0890	0.093*
C4	0.5595 (8)	0.9676 (6)	−0.0811 (5)	0.0834 (18)
H4A	0.6342	0.9959	−0.1212	0.100*
H4B	0.4959	0.8683	−0.1075	0.100*
C5	0.9167 (8)	0.8604 (6)	0.4636 (7)	0.105 (2)
H5A	0.9661	0.8412	0.4116	0.126*
H5B	0.8389	0.7743	0.4686	0.126*
C6	1.0576 (9)	0.9515 (8)	0.5987 (6)	0.103 (2)
H6A	1.0072	0.9693	0.6505	0.124*
H6B	1.1182	0.9050	0.6405	0.124*
C7	0.3300 (8)	0.9096 (8)	0.4247 (7)	0.147 (4)
H7A	0.2324	0.8173	0.3819	0.176*
H7B	0.2876	0.9735	0.4100	0.176*
C8	0.4236 (12)	0.9305 (8)	0.5657 (8)	0.138 (3)
H8A	0.3453	0.9085	0.6027	0.166*
H8B	0.4731	0.8712	0.5804	0.166*
C9	0.604 (3)	0.6334 (10)	0.5686 (15)	0.162 (12)	0.50
H9A	0.6465	0.7296	0.6057	0.194*	0.50
H9B	0.7183	0.6500	0.5893	0.194*	0.50
C10	0.483 (4)	0.5331 (18)	0.6064 (18)	0.204 (16)	0.50
H10A	0.3643	0.5120	0.5722	0.245*	0.50
H10B	0.5366	0.5630	0.7011	0.245*	0.50
C9'	0.483 (3)	0.6076 (16)	0.5339 (17)	0.154 (12)	0.50
H9C	0.3673	0.5758	0.5223	0.185*	0.50
H9D	0.5265	0.7039	0.5717	0.185*	0.50
C10'	0.581 (3)	0.5546 (14)	0.6315 (8)	0.181 (15)	0.50
H10C	0.5927	0.5810	0.7176	0.217*	0.50
H10D	0.6947	0.5860	0.6388	0.217*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rb1	0.0521 (3)	0.0521 (3)	0.0447 (3)	0.0179 (3)	0.0182 (2)	0.0068 (2)
S1	0.0588 (9)	0.0422 (7)	0.0628 (9)	0.0185 (7)	0.0313 (8)	0.0126 (7)
S2	0.0633 (10)	0.0568 (9)	0.0462 (7)	0.0245 (8)	0.0181 (7)	0.0100 (7)
F1	0.102 (3)	0.056 (2)	0.162 (4)	0.000 (2)	0.054 (3)	0.023 (2)
F2	0.154 (4)	0.089 (3)	0.129 (3)	0.064 (3)	0.077 (3)	0.066 (2)
F3	0.164 (4)	0.133 (4)	0.226 (5)	0.081 (3)	0.163 (4)	0.077 (3)
F4	0.169 (5)	0.168 (5)	0.218 (6)	0.053 (4)	0.154 (5)	0.061 (4)
F5	0.255 (6)	0.102 (3)	0.096 (3)	0.093 (4)	0.074 (3)	0.054 (2)
F6	0.271 (6)	0.105 (3)	0.064 (2)	0.082 (4)	0.075 (3)	0.024 (2)
O1	0.063 (2)	0.051 (2)	0.057 (2)	0.0219 (19)	0.0134 (18)	0.0033 (17)
O2	0.092 (3)	0.072 (3)	0.107 (3)	0.040 (2)	0.066 (3)	0.012 (2)
O3	0.090 (3)	0.061 (2)	0.052 (2)	0.041 (2)	0.011 (2)	−0.0025 (18)
O4	0.051 (3)	0.114 (3)	0.095 (3)	0.031 (2)	0.019 (2)	0.010 (3)
O5	0.080 (3)	0.109 (3)	0.076 (3)	0.062 (3)	0.041 (2)	0.051 (2)
O6	0.046 (3)	0.096 (3)	0.082 (3)	0.026 (3)	0.000 (2)	−0.003 (2)
O7	0.093 (4)	0.135 (4)	0.109 (4)	0.005 (3)	0.050 (3)	−0.053 (3)
O8	0.180 (6)	0.111 (5)	0.094 (4)	0.067 (5)	0.068 (4)	0.063 (3)
N1	0.098 (4)	0.046 (3)	0.060 (3)	0.036 (3)	0.003 (3)	0.004 (2)
C1	0.082 (5)	0.065 (4)	0.110 (5)	0.039 (4)	0.051 (4)	0.037 (4)
C2	0.172 (8)	0.071 (5)	0.076 (5)	0.056 (6)	0.062 (6)	0.029 (4)
C3	0.069 (4)	0.087 (4)	0.087 (4)	0.046 (4)	0.036 (4)	0.034 (4)
C4	0.088 (5)	0.110 (5)	0.077 (4)	0.062 (4)	0.046 (4)	0.032 (4)
C5	0.067 (5)	0.089 (5)	0.113 (6)	0.028 (4)	0.018 (4)	0.006 (4)
C6	0.085 (5)	0.139 (7)	0.079 (5)	0.060 (5)	0.028 (4)	0.032 (5)
C7	0.061 (5)	0.177 (8)	0.102 (6)	−0.010 (5)	0.042 (5)	−0.043 (5)
C8	0.171 (9)	0.114 (7)	0.140 (7)	0.055 (7)	0.102 (7)	0.032 (6)
C9	0.19 (3)	0.103 (15)	0.101 (15)	0.004 (14)	0.066 (15)	0.011 (12)
C10	0.36 (5)	0.18 (3)	0.20 (3)	0.16 (3)	0.22 (3)	0.09 (2)
C9'	0.32 (4)	0.118 (16)	0.20 (2)	0.17 (2)	0.21 (3)	0.115 (16)
C10'	0.30 (3)	0.062 (13)	0.055 (10)	0.014 (15)	0.059 (14)	0.024 (9)

Geometric parameters (Å, º)

Rb1—O3	2.897 (4)	O8—C9	1.426 (14)
Rb1—O1	2.942 (3)	O8—C10'^vi	1.443 (14)
Rb1—O6	2.983 (4)	O8—C9'	1.444 (14)
Rb1—O7	2.984 (5)	C3—C4	1.482 (6)
Rb1—O2^i	2.993 (4)	C3—H3A	0.9700
Rb1—O5	3.023 (4)	C3—H3B	0.9700
Rb1—O4^ii	3.060 (4)	C4—H4A	0.9700
Rb1—O8	3.063 (4)	C4—H4B	0.9700
S1—O1	1.416 (3)	C5—C6	1.502 (7)
S1—O2	1.433 (3)	C5—H5A	0.9700
S1—N1	1.550 (4)	C5—H5B	0.9700
S1—C1	1.814 (6)	C6—H6A	0.9700
S2—O4	1.417 (4)	C6—H6B	0.9700
S2—O3	1.424 (3)	C7—C8	1.469 (8)
S2—N1	1.563 (4)	C7—H7A	0.9700
S2—C2	1.803 (7)	C7—H7B	0.9700
F1—C1	1.319 (6)	C8—H8A	0.9700
F2—C1	1.329 (6)	C8—H8B	0.9700
F3—C1	1.291 (7)	C9—C10	1.486 (17)
F4—C2	1.283 (9)	C9—H9A	0.9700
F5—C2	1.348 (8)	C9—H9B	0.9699
F6—C2	1.310 (7)	C10—H10A	0.9700
O5—C3	1.424 (6)	C10—H10B	0.9700
O5—C4^iii	1.429 (6)	C9'—C10'	1.521 (17)
O6—C6^iv	1.388 (7)	C9'—H9C	0.9700
O6—C5	1.391 (7)	C9'—H9D	0.9700
O7—C7	1.398 (7)	C10'—H10C	0.9700
O7—C8^v	1.411 (8)	C10'—H10D	0.9700
O8—C10^vi	1.402 (16)
O3—Rb1—O1	59.33 (10)	F4—C2—F6	112.0 (8)
O3—Rb1—O6	152.44 (12)	F4—C2—F5	107.2 (7)
O1—Rb1—O6	122.85 (12)	F6—C2—F5	105.8 (6)
O3—Rb1—O7	113.61 (13)	F4—C2—S2	113.0 (6)
O1—Rb1—O7	156.31 (13)	F6—C2—S2	110.7 (5)
O6—Rb1—O7	74.68 (13)	F5—C2—S2	107.8 (6)
O3—Rb1—O2^i	90.85 (11)	O5—C3—C4	110.9 (5)
O1—Rb1—O2^i	67.40 (10)	O5—C3—H3A	109.5
O6—Rb1—O2^i	68.50 (11)	C4—C3—H3A	109.5
O7—Rb1—O2^i	136.21 (13)	O5—C3—H3B	109.5
O3—Rb1—O5	84.12 (11)	C4—C3—H3B	109.5
O1—Rb1—O5	126.37 (10)	H3A—C3—H3B	108.0
O6—Rb1—O5	73.60 (13)	O5^iii—C4—C3	110.1 (5)
O7—Rb1—O5	71.22 (14)	O5^iii—C4—H4A	109.6
O2^i—Rb1—O5	76.24 (11)	C3—C4—H4A	109.6
O3—Rb1—O4^ii	70.18 (11)	O5^iii—C4—H4B	109.6
O1—Rb1—O4^ii	82.65 (11)	C3—C4—H4B	109.6
O6—Rb1—O4^ii	135.93 (12)	H4A—C4—H4B	108.2
O7—Rb1—O4^ii	73.86 (13)	O6—C5—C6	109.4 (5)
O2^i—Rb1—O4^ii	149.87 (10)	O6—C5—Rb1	47.6 (3)
O5—Rb1—O4^ii	122.64 (11)	C6—C5—Rb1	146.8 (4)
O3—Rb1—O8	126.86 (13)	O6—C5—H5A	109.8
O1—Rb1—O8	79.78 (14)	C6—C5—H5A	109.8
O6—Rb1—O8	77.52 (15)	O6—C5—H5B	109.8
O7—Rb1—O8	90.00 (18)	C6—C5—H5B	109.8
O2^i—Rb1—O8	103.99 (16)	H5A—C5—H5B	108.2
O5—Rb1—O8	148.77 (14)	O6^iv—C6—C5	111.4 (5)
O4^ii—Rb1—O8	72.43 (15)	O6^iv—C6—H6A	109.3
O1—S1—O2	118.8 (2)	C5—C6—H6A	109.3
O1—S1—N1	116.9 (2)	O6^iv—C6—H6B	109.3
O2—S1—N1	110.3 (2)	C5—C6—H6B	109.3
O1—S1—C1	104.8 (3)	H6A—C6—H6B	108.0
O2—S1—C1	102.9 (3)	O7—C7—C8	107.7 (6)
N1—S1—C1	100.0 (3)	O7—C7—H7A	110.2
O4—S2—O3	119.4 (2)	C8—C7—H7A	110.2
O4—S2—N1	108.6 (3)	O7—C7—H7B	110.2
O3—S2—N1	117.9 (2)	C8—C7—H7B	110.2
O4—S2—C2	105.4 (4)	H7A—C7—H7B	108.5
O3—S2—C2	104.0 (3)	O7^v—C8—C7	108.3 (7)
N1—S2—C2	98.3 (3)	O7^v—C8—H8A	110.0
S1—O1—Rb1	148.5 (2)	C7—C8—H8A	110.0
S1—O2—Rb1^i	151.6 (2)	O7^v—C8—H8B	110.0
S2—O3—Rb1	148.4 (2)	C7—C8—H8B	110.0
S2—O4—Rb1^ii	151.1 (2)	H8A—C8—H8B	108.4
C3—O5—C4^iii	109.3 (4)	O8—C9—C10	107.0 (12)
C3—O5—Rb1	123.7 (3)	O8—C9—H9A	113.0
C4^iii—O5—Rb1	119.9 (3)	C10—C9—H9A	117.2
C6^iv—O6—C5	107.9 (5)	O8—C9—H9B	100.1
C6^iv—O6—Rb1	130.2 (4)	C10—C9—H9B	126.0
C5—O6—Rb1	112.2 (4)	H9A—C9—H9B	92.1
C7—O7—C8^v	106.9 (5)	O8^vi—C10—C9	106.5 (13)
C7—O7—Rb1	128.9 (5)	O8^vi—C10—H10A	105.9
C8^v—O7—Rb1	123.4 (5)	C9—C10—H10A	121.9
C10^vi—O8—C9	105.7 (12)	O8^vi—C10—H10B	106.9
C9—O8—C10'^vi	114.7 (6)	C9—C10—H10B	106.9
C10^vi—O8—C9'	115.0 (7)	H10A—C10—H10B	107.8
C10'^vi—O8—C9'	101.2 (11)	O8—C9'—C10'	102.6 (11)
C10^vi—O8—Rb1	114.4 (8)	O8—C9'—H9C	124.7
C9—O8—Rb1	137.3 (7)	C10'—C9'—H9C	113.0
C10'^vi—O8—Rb1	107.0 (5)	O8—C9'—H9D	109.5
C9'—O8—Rb1	124.4 (6)	C10'—C9'—H9D	110.5
S1—N1—S2	128.6 (3)	H9C—C9'—H9D	96.2
F3—C1—F1	110.5 (6)	O8^vi—C10'—C9'	102.1 (12)
F3—C1—F2	107.8 (6)	O8^vi—C10'—H10C	112.0
F1—C1—F2	106.8 (5)	C9'—C10'—H10C	112.7
F3—C1—S1	111.4 (4)	O8^vi—C10'—H10D	109.7
F1—C1—S1	111.2 (5)	C9'—C10'—H10D	110.9
F2—C1—S1	108.9 (5)	H10C—C10'—H10D	109.3
O2—S1—O1—Rb1	140.8 (4)	O3—Rb1—O8—C10^vi	50.9 (14)
N1—S1—O1—Rb1	4.6 (5)	O1—Rb1—O8—C10^vi	12.4 (13)
C1—S1—O1—Rb1	−105.0 (4)	O6—Rb1—O8—C10^vi	−114.8 (13)
O3—Rb1—O1—S1	−5.3 (4)	O7—Rb1—O8—C10^vi	170.9 (13)
O6—Rb1—O1—S1	−152.9 (4)	O2^i—Rb1—O8—C10^vi	−51.0 (13)
O7—Rb1—O1—S1	73.6 (5)	O5—Rb1—O8—C10^vi	−137.5 (13)
O2^i—Rb1—O1—S1	−110.7 (4)	O4^ii—Rb1—O8—C10^vi	97.9 (13)
O5—Rb1—O1—S1	−59.5 (4)	O3—Rb1—O8—C9	−150.6 (15)
O4^ii—Rb1—O1—S1	65.9 (4)	O1—Rb1—O8—C9	170.9 (15)
O8—Rb1—O1—S1	139.3 (4)	O6—Rb1—O8—C9	43.7 (15)
O1—S1—O2—Rb1^i	−50.4 (5)	O7—Rb1—O8—C9	−30.6 (15)
N1—S1—O2—Rb1^i	88.5 (5)	O2^i—Rb1—O8—C9	107.5 (15)
C1—S1—O2—Rb1^i	−165.5 (5)	O5—Rb1—O8—C9	21.0 (16)
O4—S2—O3—Rb1	126.6 (4)	O4^ii—Rb1—O8—C9	−103.6 (15)
N1—S2—O3—Rb1	−8.8 (6)	O3—Rb1—O8—C10'^vi	17.1 (13)
C2—S2—O3—Rb1	−116.3 (5)	O1—Rb1—O8—C10'^vi	−21.3 (12)
O1—Rb1—O3—S2	7.8 (4)	O6—Rb1—O8—C10'^vi	−148.5 (12)
O6—Rb1—O3—S2	110.9 (4)	O7—Rb1—O8—C10'^vi	137.2 (12)
O7—Rb1—O3—S2	−146.7 (4)	O2^i—Rb1—O8—C10'^vi	−84.7 (12)
O2^i—Rb1—O3—S2	70.7 (4)	O5—Rb1—O8—C10'^vi	−171.2 (12)
O5—Rb1—O3—S2	146.8 (4)	O4^ii—Rb1—O8—C10'^vi	64.1 (12)
O4^ii—Rb1—O3—S2	−85.4 (4)	C5—Rb1—O8—C10'^vi	−134.4 (13)
O8—Rb1—O3—S2	−37.5 (5)	O3—Rb1—O8—C9'	−100.0 (12)
O3—S2—O4—Rb1^ii	−76.1 (5)	O1—Rb1—O8—C9'	−138.5 (12)
N1—S2—O4—Rb1^ii	63.1 (5)	O6—Rb1—O8—C9'	94.3 (12)
C2—S2—O4—Rb1^ii	167.6 (5)	O7—Rb1—O8—C9'	20.0 (12)
O3—Rb1—O5—C3	−88.2 (4)	O2^i—Rb1—O8—C9'	158.1 (12)
O1—Rb1—O5—C3	−43.7 (4)	O5—Rb1—O8—C9'	71.6 (12)
O6—Rb1—O5—C3	75.4 (4)	O4^ii—Rb1—O8—C9'	−53.0 (12)
O7—Rb1—O5—C3	154.4 (4)	O1—S1—N1—S2	−1.4 (5)
O2^i—Rb1—O5—C3	4.1 (4)	O2—S1—N1—S2	−141.2 (4)
O4^ii—Rb1—O5—C3	−150.1 (4)	C1—S1—N1—S2	110.9 (4)
O8—Rb1—O5—C3	98.5 (5)	O4—S2—N1—S1	−136.9 (4)
O3—Rb1—O5—C4^iii	59.4 (4)	O3—S2—N1—S1	3.0 (5)
O1—Rb1—O5—C4^iii	103.9 (4)	C2—S2—N1—S1	113.7 (5)
O6—Rb1—O5—C4^iii	−137.0 (4)	O1—S1—C1—F3	58.3 (6)
O7—Rb1—O5—C4^iii	−58.0 (4)	O2—S1—C1—F3	−176.8 (5)
O2^i—Rb1—O5—C4^iii	151.7 (4)	N1—S1—C1—F3	−63.1 (6)
O4^ii—Rb1—O5—C4^iii	−2.5 (4)	O1—S1—C1—F1	−177.9 (4)
O8—Rb1—O5—C4^iii	−113.9 (4)	O2—S1—C1—F1	−53.1 (5)
O3—Rb1—O6—C6^iv	25.5 (6)	N1—S1—C1—F1	60.6 (5)
O1—Rb1—O6—C6^iv	111.2 (5)	O1—S1—C1—F2	−60.5 (5)
O7—Rb1—O6—C6^iv	−86.4 (5)	O2—S1—C1—F2	64.4 (5)
O2^i—Rb1—O6—C6^iv	69.5 (5)	N1—S1—C1—F2	178.1 (4)
O5—Rb1—O6—C6^iv	−11.9 (5)	O4—S2—C2—F4	−178.8 (6)
O4^ii—Rb1—O6—C6^iv	−132.2 (5)	O3—S2—C2—F4	54.8 (7)
O8—Rb1—O6—C6^iv	−179.8 (5)	N1—S2—C2—F4	−66.8 (6)
O3—Rb1—O6—C5	−115.7 (4)	O4—S2—C2—F6	−52.3 (7)
O1—Rb1—O6—C5	−30.1 (4)	O3—S2—C2—F6	−178.7 (6)
O7—Rb1—O6—C5	132.4 (4)	N1—S2—C2—F6	59.7 (7)
O2^i—Rb1—O6—C5	−71.8 (4)	O4—S2—C2—F5	63.0 (6)
O5—Rb1—O6—C5	−153.1 (4)	O3—S2—C2—F5	−63.5 (6)
O4^ii—Rb1—O6—C5	86.6 (4)	N1—S2—C2—F5	174.9 (5)
O8—Rb1—O6—C5	38.9 (4)	C4^iii—O5—C3—C4	−58.4 (6)
O3—Rb1—O7—C7	69.9 (6)	Rb1—O5—C3—C4	92.1 (4)
O1—Rb1—O7—C7	2.8 (8)	O5—C3—C4—O5^iii	58.9 (6)
O6—Rb1—O7—C7	−138.0 (6)	C6^iv—O6—C5—C6	58.6 (7)
O2^i—Rb1—O7—C7	−171.4 (6)	Rb1—O6—C5—C6	−151.5 (4)
O5—Rb1—O7—C7	144.4 (6)	C6^iv—O6—C5—Rb1	−149.9 (6)
O4^ii—Rb1—O7—C7	10.7 (6)	O6—C5—C6—O6^iv	−60.8 (8)
O8—Rb1—O7—C7	−61.0 (6)	C8^v—O7—C7—C8	−63.8 (9)
O3—Rb1—O7—C8^v	−121.8 (6)	Rb1—O7—C7—C8	106.0 (6)
O1—Rb1—O7—C8^v	171.1 (5)	O7—C7—C8—O7^v	64.7 (9)
O6—Rb1—O7—C8^v	30.2 (6)	C10^vi—O8—C9—C10	−67 (2)
O2^i—Rb1—O7—C8^v	−3.2 (7)	Rb1—O8—C9—C10	133.6 (12)
O5—Rb1—O7—C8^v	−47.3 (6)	O8—C9—C10—O8^vi	67 (2)
O4^ii—Rb1—O7—C8^v	179.0 (6)	Rb1—O8—C9'—C10'	−165.4 (9)
O8—Rb1—O7—C8^v	107.3 (6)	O8—C9'—C10'—O8^vi	−75.4 (17)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+2, −z+1; (v) −x+1, −y+2, −z+1; (vi) −x+1, −y+1, −z+1.