1,2-Bis(N-fluoro-p-toluene­sulfon­amido)­ethane chloroform solvate

The title compound, N,N′-difluoro-N,N′-ethylenedi-p-tolu­enesulfonamide, C₁₆H₁₈F₂N₂O₄S₂·CHCl₃, is a novel stable compound of the N—F class of reagents containing two R₂N—F functionalities. The compound, as the chloro­form solvate, is the first such bis(N—F) compound to be structurally characterized. It adopts a solid-state structure in which the two aromatic rings are antiperiplanar and a combination of weak C—H...F and C—H...O hydrogen bonds [distances and angles range from 3.265 (4) to 3.439 (4) Å and 150 to 170°, respectively] and π-stacking between the rings of different mol­ecules (separations of 3.717 and 3.926 Å) results in a solid-state structure containing well defined channels in which CHCl₃ solvent mol­ecules are located. The N—F distances are 1.428 (3) and 1.433 (3) Å.

S1. Comment

Fluorine and fluorine-containing substituents can exert a profound influence on the activity and selectivity of bio-organic molecules. This realisation has lead to much work in identifying reagents which can be used as site-selective fluorinating agents, and many of the more recent advances in this area have involved compounds in which fluorine is bound to a nitrogen atom. Included in this class of compounds are reagents featuring neutral N atoms of the type R₂NF, for example N-fluoro-N-alkylsulfonamides (Barnett et al., 1984) and the electrophilic fluorine-delivery agents [R₃N⁺F] such as 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]-octane [BF₄]₂ (Banks et al., 1996, 1998). However, the amount of structural data for such N—F containing systems is quite limited. There are just twelve crystal structures in the Cambridge Structural Database (Allen & Kennard, 1993) for organic compounds containing N–F bonds, of these six are NF₂-containing materials, i.e. formally organic derivatives of NF₃. Of the remaining six structures three compounds contain neutral N—F moieties and the other three contain the ⁺N—F group. There are no structures of compounds which contain two separate, single N—F moieties (neutral or charged) within the same organic molecule. Recent work (Ardeshir et al., 1999) has shown that bis(N-halogeno) compounds such as 1,2-bis(N-bromo-2,5-dimethyl benzenesulfamido)ethane are good selective brominating agents and relatively accessible. Here we report an extension of that work to give the fluorinated analogue which has resulted in the first structural characterization of an organic bis(N—F)-containing compound. \sch

The title compound, (I), may be synthesized by passing dilute elemental fluorine through a CHCl₃ solution of 1,2-bis(benzenesulfonamido)ethane at low temperature. Crystallization of (I) from a CHCl₃ solution resulted in crystals of (I) as the CHCl₃ solvate which crystallizes in the space group P2/n. A view of molecule (I) with our numbering scheme is shown in Fig. 1 and selected geometric parameters are given in Table 1. The bond lengths obtained for compound (I) are mostly in accord with anticipated values (Orpen et al., 1994). Of particular interest are the two N—F distances in this molecule which are the same within experimental limits, 1.428 (3) and 1.433 (3) Å. These distances are comparable with those found in the related neutral N—F containing organic systems, 1.435 (3) Å (Kakuda et al., 1997), 1.420 (4) Å (Davis et al., 1998) and 1.437 (6) Å (Batail et al., 1974), average 1.431 (7) Å. However, as expected, the N—F distances are longer than the distances found in molecules which formally contain ⁺N—F bonds 1.106 (2) Å (Klapötke et al., 1993), 1.37 (2) (Banks, Pritchard & Sharif et al., 1993) and 1.406 (3) Å (Banks, Sharif & Pritchard et al., 1993) [average = 1.294 (20) Å]. However, this average figure is distorted by the very short N—F distance observed by Klapötke for the hexafluoroarsenate salt of N-fluoro-2,4,6-trichlorotriazine, which the authors describe as being unreliable due to severe disorder problems.

The molecule is symmetric about the central C—C bond; this results in an overall Z-like shape and the two N—F moieties are located on opposite sides of the molecule. The two aromatic rings are anti-periplanar with torsion angles of C3—S1—N1—C1 = 50.4 (3), N1—C1—C2—N2 = 179.4 (3) and C2—N2—S2—C10 = -52.2 (2)°. In the solid state there are weak hydrogen bonds between the electronegative fluorine atoms F1 and F2 and the protons attached to the carbon centres C2 and C1, respectively, of the central aliphatic chain, Fig. 2. The average C—H···F distance is 3.429 (6) Å and the angle is 170°. Hydrogen bonding also occurs between the O atoms of the SO₂ groups and the ortho protons of the aromatic rings with (C—H···O)_av 3.330 (7) Å, 153°. These two features result in a two-dimensional stack of molecules in an alternate head-to-tail fashion in the a axis direction. The aromatic rings of one stack interweave with those of a second stack resulting in the generation of an approximately square arrangement when viewed down the a axis. The next pair of stacks is separated in the c direction by a distance of ca 3.8 Å between the aromatic rings and is offset (Fig. 3); the offset and short distance being indicative of pi-interactions between the aromatic rings.

This combination of intermolecular interactions results in the generation of channels running parallel to the a axis in which solvent molecules may be located. In this case molecules of CHCl₃ solvent are located in the channels but are disordered over two equally populated sites.

Related literature

For related literature, see: Allen & Kennard (1993); Ardeshir & Abbas (1999); Banks (1998); Banks et al. (1996); Banks, Pritchard & Sharif (1993); Banks, Sharif & Pritchard (1993); Barnett (1984); Batail et al. (1974); Davis et al. (1998); Kakuda et al. (1997); Klapötke et al. (1993); Orpen et al. (1994).

S2. Experimental

The compound was synthesized in two stages. 1,2-Bis(benzenesulfanamido)ethane was obtained by the dropwise addition of diethylamine (6.21 g, 0.085 mol) to benzenesulfonyl chloride (30.0 g, 0.170 mol) at room temperature with vigorous stirring. The reaction mixture was heated to 353 K for 0.5 h and then cooled and washed with water (100 ml). The resulting white solid was filtered and recystallized from boiling ethanol. 1,2-bis(benzenesulfanamido)ethane (0.5 g, 1.5 mmol) was dissolved in chloroform (180 ml) and the solution cooled to 195 K. Elemental fluorine (15 mmol, 5% in N₂) was bubbled through the cold, stirred solution for 15 min. After warming to room temperature the solvent was removed under vacuum and the crude solid was washed with diethyl ether. Crystals suitable for X-ray diffraction studies were grown by slow evaporation of the solvent from a CHCl₃ solution.

S3. Refinement

Molecule (I) crystallized in the monoclininc system; space group P2/n from the systematic absences. H atoms were treated as riding atoms (C—H 0.93 and 0.97 Å). The solvent molecules located in the channels within the structure exist as disordered pairs (50:50 occupancy) around the crystallographic twofold axis. This leads to the chlorine atoms nearly coalescing with another from a symmetry-related molecule so distorting the vibrational ellipsoids for these atoms.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures

	Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are omitted for clarity.
	Fig. 2. A view of the intermolecular hydrogen bonds in the crystal structure of (I).
	Fig. 3. A view of the crystal packing illustrating the resulting channels formed in the solid state structure of (I).

1,2-bis(N-fluoro-p-toluenesulfonamido)ethane

Crystal data

C16H18F2N2O4S2·CHCl3	F(000) = 1072
Mr = 523.81	Dx = 1.532 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 25 reflections
a = 10.9948 (10) Å	θ = 12.7–17.2°
b = 9.6922 (10) Å	µ = 0.63 mm^−1
c = 21.381 (5) Å	T = 293 K
β = 94.815 (10)°	Plate, colourless
V = 2270.4 (6) Å^3	0.35 × 0.3 × 0.1 mm
Z = 4

Data collection

Enraf Nonius CAD4 diffractometer	2572 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.017
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
non–profiled ω scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.810, Tmax = 0.940	l = −25→25
4222 measured reflections	3 standard reflections every 60 min
3999 independent reflections	intensity decay: 3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0717P)^2 + 0.3412P] where P = (Fo^2 + 2Fc^2)/3
3999 reflections	(Δ/σ)max = 0.026
309 parameters	Δρmax = 0.36 e Å^−3
72 restraints	Δρmin = −0.30 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.44043 (8)	0.73110 (9)	0.09126 (4)	0.0288 (2)
S2	0.55434 (8)	0.66118 (9)	0.39870 (4)	0.0296 (2)
O1	0.3355 (2)	0.7897 (2)	0.05851 (11)	0.0371 (6)
O2	0.5580 (2)	0.7885 (3)	0.08700 (11)	0.0374 (6)
O3	0.4355 (2)	0.6062 (3)	0.40219 (11)	0.0376 (6)
O4	0.6586 (2)	0.5992 (3)	0.43060 (11)	0.0394 (7)
N1	0.4215 (2)	0.7556 (3)	0.16913 (13)	0.0318 (7)
N2	0.5732 (2)	0.6425 (3)	0.32075 (13)	0.0334 (7)
F1	0.30386 (18)	0.7000 (3)	0.17801 (10)	0.0469 (6)
F2	0.69174 (18)	0.6982 (3)	0.31291 (10)	0.0507 (6)
C1	0.5056 (3)	0.6782 (4)	0.21174 (15)	0.0335 (8)
H1A	0.5888	0.6957	0.2021	0.04*
H1B	0.4897	0.5802	0.2069	0.04*
C2	0.4895 (3)	0.7215 (4)	0.27823 (15)	0.0339 (8)
H2A	0.5063	0.8193	0.2833	0.041*
H2B	0.4061	0.7047	0.2878	0.041*
C3	0.4433 (3)	0.5535 (3)	0.07972 (14)	0.0261 (8)
C4	0.3341 (3)	0.4847 (4)	0.06630 (16)	0.0333 (9)
H4	0.2611	0.5331	0.0602	0.04*
C5	0.3358 (3)	0.3441 (4)	0.06220 (16)	0.0374 (9)
H5	0.2629	0.2968	0.0529	0.045*
C6	0.4435 (4)	0.2705 (4)	0.07166 (16)	0.0361 (9)
C7	0.5514 (3)	0.3431 (4)	0.08387 (16)	0.0367 (9)
H7	0.6246	0.2948	0.0895	0.044*
C8	0.5532 (3)	0.4838 (4)	0.08793 (16)	0.0325 (8)
H8	0.6263	0.5314	0.096	0.039*
C9	0.4425 (4)	0.1149 (4)	0.0684 (2)	0.0541 (12)
H9A	0.4153	0.0781	0.1065	0.081*
H9B	0.5234	0.082	0.0632	0.081*
H9C	0.3882	0.0855	0.0334	0.081*
C10	0.5556 (3)	0.8378 (3)	0.41312 (15)	0.0275 (8)
C11	0.4480 (3)	0.9117 (4)	0.40652 (16)	0.0320 (8)
H11	0.374	0.867	0.3967	0.038*
C12	0.4519 (3)	1.0521 (4)	0.41466 (16)	0.0367 (9)
H12	0.3797	1.1025	0.4101	0.044*
C13	0.5612 (4)	1.1203 (4)	0.42947 (16)	0.0358 (9)
C14	0.6681 (3)	1.0424 (4)	0.43703 (16)	0.0379 (9)
H14	0.7419	1.0865	0.4482	0.045*
C15	0.6667 (3)	0.9027 (4)	0.42838 (16)	0.0325 (8)
H15	0.7388	0.8521	0.4326	0.039*
C16	0.5664 (4)	1.2734 (4)	0.4374 (2)	0.0538 (12)
H16A	0.6176	1.2958	0.4746	0.081*
H16B	0.4857	1.3084	0.4412	0.081*
H16C	0.5993	1.3144	0.4016	0.081*
C1A	0.7322 (13)	0.1319 (14)	0.2707 (5)	0.111 (5)	0.5
H1A1	0.7019	0.1311	0.3125	0.133*	0.5
Cl1A	0.7819 (8)	0.3068 (5)	0.2331 (3)	0.167 (3)	0.5
Cl2A	0.6507 (5)	0.0434 (6)	0.2067 (2)	0.1073 (15)	0.5
Cl3A	0.8873 (8)	0.0958 (11)	0.2615 (4)	0.224 (4)	0.5
C1B	0.2276 (14)	0.2717 (13)	0.2700 (5)	0.104 (5)	0.5
H1B1	0.191	0.301	0.3081	0.125*	0.5
Cl1B	0.2203 (10)	0.1003 (4)	0.2645 (5)	0.157 (4)	0.5
Cl2B	0.1552 (6)	0.3600 (7)	0.2045 (2)	0.0919 (14)	0.5
Cl3B	0.3801 (9)	0.3230 (12)	0.2748 (5)	0.222 (5)	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0290 (5)	0.0237 (5)	0.0335 (5)	0.0003 (4)	0.0008 (4)	−0.0001 (4)
S2	0.0270 (5)	0.0279 (5)	0.0336 (5)	0.0003 (4)	0.0004 (4)	−0.0029 (4)
O1	0.0368 (15)	0.0325 (14)	0.0405 (14)	0.0067 (12)	−0.0048 (11)	0.0037 (11)
O2	0.0327 (15)	0.0322 (14)	0.0476 (15)	−0.0067 (12)	0.0061 (12)	−0.0015 (11)
O3	0.0302 (14)	0.0372 (15)	0.0457 (15)	−0.0092 (12)	0.0056 (11)	−0.0018 (12)
O4	0.0370 (16)	0.0342 (15)	0.0451 (15)	0.0055 (12)	−0.0078 (12)	−0.0001 (12)
N1	0.0231 (16)	0.0346 (17)	0.0377 (16)	0.0002 (14)	0.0024 (12)	−0.0060 (14)
N2	0.0203 (16)	0.0418 (18)	0.0378 (17)	0.0035 (14)	0.0014 (12)	−0.0050 (14)
F1	0.0231 (11)	0.0726 (16)	0.0455 (13)	−0.0024 (11)	0.0065 (9)	−0.0049 (11)
F2	0.0242 (12)	0.0849 (18)	0.0436 (12)	−0.0050 (12)	0.0063 (9)	−0.0087 (12)
C1	0.028 (2)	0.037 (2)	0.0356 (19)	0.0037 (17)	0.0018 (15)	−0.0067 (16)
C2	0.031 (2)	0.037 (2)	0.0344 (19)	0.0028 (17)	0.0016 (15)	−0.0037 (16)
C3	0.0265 (19)	0.0268 (18)	0.0252 (17)	0.0009 (16)	0.0036 (14)	−0.0016 (14)
C4	0.028 (2)	0.033 (2)	0.038 (2)	0.0020 (17)	−0.0016 (15)	−0.0001 (16)
C5	0.037 (2)	0.033 (2)	0.041 (2)	−0.0085 (18)	−0.0028 (17)	−0.0032 (17)
C6	0.050 (3)	0.028 (2)	0.0310 (19)	0.0003 (19)	0.0055 (17)	−0.0014 (16)
C7	0.035 (2)	0.038 (2)	0.037 (2)	0.0134 (18)	0.0002 (16)	−0.0041 (17)
C8	0.026 (2)	0.036 (2)	0.035 (2)	0.0029 (17)	−0.0002 (15)	−0.0052 (16)
C9	0.075 (3)	0.029 (2)	0.057 (3)	0.003 (2)	0.000 (2)	−0.0056 (19)
C10	0.0275 (19)	0.0269 (19)	0.0282 (18)	−0.0002 (17)	0.0041 (14)	−0.0018 (15)
C11	0.0243 (19)	0.036 (2)	0.035 (2)	0.0014 (16)	0.0027 (15)	−0.0037 (16)
C12	0.037 (2)	0.035 (2)	0.038 (2)	0.0098 (18)	0.0018 (16)	−0.0022 (17)
C13	0.050 (2)	0.027 (2)	0.0304 (19)	−0.0052 (19)	0.0046 (17)	−0.0025 (15)
C14	0.032 (2)	0.041 (2)	0.040 (2)	−0.0091 (18)	0.0012 (16)	−0.0045 (17)
C15	0.027 (2)	0.036 (2)	0.035 (2)	0.0006 (17)	0.0028 (15)	−0.0024 (16)
C16	0.073 (3)	0.034 (2)	0.054 (3)	0.001 (2)	0.002 (2)	−0.0018 (19)
C1A	0.116 (10)	0.160 (12)	0.054 (8)	0.023 (10)	−0.021 (8)	−0.007 (6)
Cl1A	0.213 (9)	0.148 (3)	0.131 (6)	−0.045 (4)	−0.043 (5)	0.023 (3)
Cl2A	0.111 (4)	0.128 (3)	0.078 (3)	−0.030 (3)	−0.018 (2)	0.005 (2)
Cl3A	0.174 (7)	0.280 (11)	0.211 (8)	0.077 (7)	−0.020 (6)	−0.102 (7)
C1B	0.124 (12)	0.127 (10)	0.058 (8)	0.017 (10)	−0.015 (8)	0.021 (6)
Cl1B	0.178 (10)	0.110 (3)	0.169 (9)	−0.030 (4)	−0.058 (6)	0.035 (4)
Cl2B	0.107 (3)	0.099 (3)	0.0668 (19)	0.029 (2)	−0.0142 (19)	0.0148 (19)
Cl3B	0.178 (8)	0.225 (10)	0.246 (11)	−0.076 (7)	−0.073 (7)	0.115 (8)

Geometric parameters (Å, º)

S1—O1	1.417 (2)	C8—H8	0.93
S1—O2	1.418 (2)	C9—H9A	0.96
S1—N1	1.712 (3)	C9—H9B	0.96
S1—C3	1.740 (3)	C9—H9C	0.96
S2—O4	1.417 (2)	C10—C11	1.380 (5)
S2—O3	1.419 (2)	C10—C15	1.389 (5)
S2—N2	1.706 (3)	C11—C12	1.373 (5)
S2—C10	1.739 (3)	C11—H11	0.93
N1—F1	1.428 (3)	C12—C13	1.385 (5)
N1—C1	1.451 (4)	C12—H12	0.93
N2—F2	1.433 (3)	C13—C14	1.395 (5)
N2—C2	1.456 (4)	C13—C16	1.494 (5)
C1—C2	1.507 (5)	C14—C15	1.366 (5)
C1—H1A	0.97	C14—H14	0.93
C1—H1B	0.97	C15—H15	0.93
C2—H2A	0.97	C16—H16A	0.96
C2—H2B	0.97	C16—H16B	0.96
C3—C4	1.382 (5)	C16—H16C	0.96
C3—C8	1.382 (5)	C1A—Cl3A	1.767 (15)
C4—C5	1.366 (5)	C1A—Cl2A	1.790 (13)
C4—H4	0.93	C1A—Cl1A	1.973 (13)
C5—C6	1.383 (5)	C1A—H1A1	0.98
C5—H5	0.93	Cl1A—Cl3A	2.403 (11)
C6—C7	1.385 (5)	C1B—Cl1B	1.666 (13)
C6—C9	1.510 (5)	C1B—Cl3B	1.744 (15)
C7—C8	1.367 (5)	C1B—Cl2B	1.773 (11)
C7—H7	0.93	C1B—H1B1	0.98
O1—S1—O2	121.33 (16)	C7—C8—H8	120.9
O1—S1—N1	105.35 (15)	C3—C8—H8	120.9
O2—S1—N1	101.20 (14)	C6—C9—H9A	109.5
O1—S1—C3	110.51 (16)	C6—C9—H9B	109.5
O2—S1—C3	110.60 (16)	H9A—C9—H9B	109.5
N1—S1—C3	106.26 (15)	C6—C9—H9C	109.5
O4—S2—O3	121.78 (16)	H9A—C9—H9C	109.5
O4—S2—N2	105.39 (15)	H9B—C9—H9C	109.5
O3—S2—N2	101.51 (14)	C11—C10—C15	121.2 (3)
O4—S2—C10	109.75 (16)	C11—C10—S2	119.9 (3)
O3—S2—C10	110.72 (16)	C15—C10—S2	118.8 (3)
N2—S2—C10	106.13 (15)	C12—C11—C10	119.0 (3)
F1—N1—C1	105.0 (3)	C12—C11—H11	120.5
F1—N1—S1	105.22 (18)	C10—C11—H11	120.5
C1—N1—S1	114.6 (2)	C11—C12—C13	121.3 (4)
F2—N2—C2	105.2 (3)	C11—C12—H12	119.4
F2—N2—S2	105.10 (19)	C13—C12—H12	119.4
C2—N2—S2	115.6 (2)	C12—C13—C14	118.4 (3)
N1—C1—C2	109.2 (3)	C12—C13—C16	121.6 (4)
N1—C1—H1A	109.8	C14—C13—C16	120.0 (4)
C2—C1—H1A	109.8	C15—C14—C13	121.4 (3)
N1—C1—H1B	109.8	C15—C14—H14	119.3
C2—C1—H1B	109.8	C13—C14—H14	119.3
H1A—C1—H1B	108.3	C14—C15—C10	118.7 (3)
N2—C2—C1	109.0 (3)	C14—C15—H15	120.6
N2—C2—H2A	109.9	C10—C15—H15	120.6
C1—C2—H2A	109.9	C13—C16—H16A	109.5
N2—C2—H2B	109.9	C13—C16—H16B	109.5
C1—C2—H2B	109.9	H16A—C16—H16B	109.5
H2A—C2—H2B	108.3	C13—C16—H16C	109.5
C8—C3—C4	121.7 (3)	H16A—C16—H16C	109.5
C8—C3—S1	119.5 (3)	H16B—C16—H16C	109.5
C4—C3—S1	118.8 (3)	Cl3A—C1A—Cl2A	104.2 (7)
C5—C4—C3	118.6 (3)	Cl3A—C1A—Cl1A	79.7 (7)
C5—C4—H4	120.7	Cl2A—C1A—Cl1A	103.8 (6)
C3—C4—H4	120.7	Cl3A—C1A—H1A1	120.4
C4—C5—C6	121.4 (4)	Cl2A—C1A—H1A1	120.4
C4—C5—H5	119.3	Cl1A—C1A—H1A1	120.4
C6—C5—H5	119.3	C1A—Cl1A—Cl3A	46.4 (4)
C5—C6—C7	118.4 (3)	C1A—Cl3A—Cl1A	53.9 (5)
C5—C6—C9	120.4 (4)	Cl1B—C1B—Cl3B	109.2 (9)
C7—C6—C9	121.3 (4)	Cl1B—C1B—Cl2B	114.2 (9)
C8—C7—C6	121.8 (3)	Cl3B—C1B—Cl2B	105.9 (7)
C8—C7—H7	119.1	Cl1B—C1B—H1B1	109.1
C6—C7—H7	119.1	Cl3B—C1B—H1B1	109.1
C7—C8—C3	118.1 (3)	Cl2B—C1B—H1B1	109.1
O1—S1—N1—F1	52.9 (2)	C4—C5—C6—C7	−1.7 (5)
O2—S1—N1—F1	−179.94 (19)	C4—C5—C6—C9	178.5 (3)
C3—S1—N1—F1	−64.4 (2)	C5—C6—C7—C8	1.3 (5)
O1—S1—N1—C1	167.6 (2)	C9—C6—C7—C8	−178.9 (3)
O2—S1—N1—C1	−65.2 (3)	C6—C7—C8—C3	0.3 (5)
C3—S1—N1—C1	50.4 (3)	C4—C3—C8—C7	−1.5 (5)
O4—S2—N2—F2	−53.0 (2)	S1—C3—C8—C7	174.5 (3)
O3—S2—N2—F2	179.1 (2)	O4—S2—C10—C11	−157.3 (3)
C10—S2—N2—F2	63.4 (2)	O3—S2—C10—C11	−20.0 (3)
O4—S2—N2—C2	−168.5 (2)	N2—S2—C10—C11	89.3 (3)
O3—S2—N2—C2	63.6 (3)	O4—S2—C10—C15	25.7 (3)
C10—S2—N2—C2	−52.2 (3)	O3—S2—C10—C15	162.9 (3)
F1—N1—C1—C2	−71.8 (3)	N2—S2—C10—C15	−87.8 (3)
S1—N1—C1—C2	173.3 (2)	C15—C10—C11—C12	0.7 (5)
F2—N2—C2—C1	72.7 (3)	S2—C10—C11—C12	−176.3 (3)
S2—N2—C2—C1	−171.8 (2)	C10—C11—C12—C13	−0.2 (5)
N1—C1—C2—N2	179.4 (3)	C11—C12—C13—C14	−1.0 (5)
O1—S1—C3—C8	157.4 (3)	C11—C12—C13—C16	179.0 (4)
O2—S1—C3—C8	20.2 (3)	C12—C13—C14—C15	1.9 (5)
N1—S1—C3—C8	−88.8 (3)	C16—C13—C14—C15	−178.2 (3)
O1—S1—C3—C4	−26.6 (3)	C13—C14—C15—C10	−1.4 (5)
O2—S1—C3—C4	−163.7 (3)	C11—C10—C15—C14	0.2 (5)
N1—S1—C3—C4	87.2 (3)	S2—C10—C15—C14	177.2 (3)
C8—C3—C4—C5	1.1 (5)	Cl2A—C1A—Cl1A—Cl3A	−102.3 (7)
S1—C3—C4—C5	−174.9 (3)	Cl2A—C1A—Cl3A—Cl1A	101.7 (6)
C3—C4—C5—C6	0.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F2^i	0.97	2.46	3.418 (4)	169
C2—H2B···F1^ii	0.97	2.48	3.439 (4)	170
C4—H4···O3^ii	0.93	2.47	3.311 (4)	150
C8—H8···O4^i	0.93	2.56	3.415 (4)	152
C15—H15···O2^i	0.93	2.39	3.265 (4)	157

Symmetry codes: (i) −x+3/2, y, −z+1/2; (ii) −x+1/2, y, −z+1/2.