C—I...NC halogen bonding in two polymorphs of the mixed-valence 2:1 charge-transfer salt (EDT-TTF-I₂)₂(TCNQF₄), with segregated versus alternated stacks

Oxidation of diiodoethylenedithiotetrathiafulvalene (EDT-TTF-I₂), C₈H₄I₂S₆, with the strong oxidizer tetrafluorotetracyanoquinodimethane (TCNQF₄), C₁₂F₄N₄, affords, depending on the crystallization solvent, two polymorphs of the 2:1 charge-transfer salt (EDT-TTF-I₂)₂(TCNQF₄), represented as D₂A. In both salts, the TCNQF₄ is reduced to the radical anion state, and is associated through short C—I...NC halogen bonds to two EDT-TTF-I₂ molecules. The two polymorphs differ in the solid-state association of these trimeric D–A–D motifs. In polymorph (I) the trimeric motif is located on an inversion centre, and hence both EDT-TTF-I₂ molecules have +0.5 charge. Together with segregation of the TTF and TCNQ derivatives into stacks, this leads to a charge-transfer salt with high conductivity. In polymorph (II) two crystallographically independent EDT-TTF-I₂ molecules bear different charges, close to 0 and +1, as deduced from an established correlation between intramolecular bond lengths and charge. Overlap interactions between the halogen-bonded D⁰–A–D motifs give rise, in a perpendicular direction, to diamagnetic A₂²⁻ and D⁰–D₂²⁺–D⁰ entities, where the radical species are paired into the bonding combination of respectively the acceptor LUMOs and donor HOMOs. The strikingly different solid-state organization of the halogen-bonded D–A–D motifs provides an illustrative example of two modes of face-to-face interaction between π-type radicals, into either delocalized, uniform chains with partial charge transfer and conducting behaviour, or localized association of radicals into face-to-face A₂²⁻ and D₂²⁺ dyads.

Computing details

Data collection: APEX2 (Bruker, 2005) for NCCH22S2TTFI2, EDTTTFI2; COLLECT (Nonius, 1998) for (I), (II). Cell refinement: SAINT (Bruker, 2003) for NCCH22S2TTFI2, EDTTTFI2; DIRAX (Duisenberg, 1992) for (I), (II). Data reduction: SAINT for NCCH22S2TTFI2, EDTTTFI2; EVALCCD (Duisenberg et al., 2003) for (I), (II). For all compounds, program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Brendt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures

(NCCH22S2TTFI2)

Crystal data

C12H8I2N2S6	F(000) = 2368
Mr = 626.36	Dx = 2.258 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5889 reflections
a = 14.6070 (4) Å	θ = 3.3–27.4°
b = 12.0315 (3) Å	µ = 4.09 mm^−1
c = 20.9654 (7) Å	T = 100 K
V = 3684.55 (18) Å^3	Prism, orange
Z = 8	0.28 × 0.19 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	4208 independent reflections
Radiation source: fine-focus sealed tube	3600 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan SADABS (Bruker, 2003)	h = −18→18
Tmin = 0.353, Tmax = 0.520	k = −15→13
15787 measured reflections	l = −27→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0222P)^2 + 2.9001P] where P = (Fo^2 + 2Fc^2)/3
4208 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 1.17 e Å^−3
0 restraints	Δρmin = −1.17 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
I1	0.200427 (14)	0.272589 (18)	0.492671 (12)	0.01592 (7)
I2	0.378402 (15)	0.054808 (18)	0.460938 (13)	0.01896 (8)
S1	0.36195 (6)	0.44142 (7)	0.44370 (5)	0.0170 (2)
S2	0.50198 (5)	0.26785 (7)	0.41888 (5)	0.0164 (2)
S3	0.51071 (5)	0.63211 (7)	0.40735 (5)	0.0166 (2)
S4	0.64904 (6)	0.45850 (7)	0.38103 (5)	0.0175 (2)
S5	0.63225 (6)	0.81815 (7)	0.36206 (5)	0.0184 (2)
S6	0.78970 (5)	0.62023 (7)	0.33396 (5)	0.0163 (2)
C1	0.3315 (2)	0.3024 (3)	0.45773 (18)	0.0153 (8)
C2	0.3944 (2)	0.2247 (3)	0.44696 (19)	0.0154 (8)
C3	0.4749 (2)	0.4105 (3)	0.41963 (18)	0.0140 (8)
C4	0.5359 (2)	0.4889 (3)	0.40355 (18)	0.0150 (8)
C5	0.6142 (2)	0.6752 (3)	0.37192 (18)	0.0140 (7)
C6	0.6777 (2)	0.5965 (3)	0.36047 (18)	0.0140 (7)
C7A	0.5239 (2)	0.8666 (3)	0.33014 (19)	0.0187 (8)
H7A1	0.4738	0.8325	0.3552	0.022*
H7A2	0.5203	0.9480	0.3363	0.022*
C8A	0.5078 (3)	0.8411 (3)	0.2594 (2)	0.0241 (9)
H8A1	0.4498	0.8764	0.2457	0.029*
H8A2	0.5580	0.8743	0.2340	0.029*
C9A	0.5032 (2)	0.7213 (3)	0.24578 (19)	0.0187 (8)
N10A	0.5019 (2)	0.6285 (3)	0.23563 (17)	0.0246 (8)
C7B	0.7894 (2)	0.5462 (3)	0.25845 (19)	0.0187 (8)
H7B1	0.8534	0.5377	0.2437	0.022*
H7B2	0.7642	0.4708	0.2655	0.022*
C8B	0.7343 (2)	0.6027 (3)	0.2059 (2)	0.0234 (9)
H8B1	0.7408	0.5597	0.1659	0.028*
H8B2	0.6687	0.6026	0.2179	0.028*
C9B	0.7642 (3)	0.7178 (4)	0.1947 (2)	0.0267 (9)
N10B	0.7884 (3)	0.8066 (3)	0.18646 (19)	0.0380 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01048 (11)	0.01484 (12)	0.02243 (15)	−0.00136 (8)	0.00074 (9)	0.00340 (11)
I2	0.01606 (12)	0.01279 (12)	0.02804 (17)	0.00007 (8)	−0.00321 (10)	0.00138 (11)
S1	0.0111 (4)	0.0131 (4)	0.0268 (6)	−0.0001 (3)	0.0038 (4)	0.0027 (4)
S2	0.0108 (4)	0.0155 (4)	0.0230 (6)	0.0006 (3)	0.0012 (4)	0.0003 (4)
S3	0.0121 (4)	0.0147 (4)	0.0231 (6)	0.0008 (3)	0.0031 (4)	0.0036 (4)
S4	0.0118 (4)	0.0149 (4)	0.0259 (6)	0.0007 (3)	0.0039 (4)	0.0052 (4)
S5	0.0170 (4)	0.0143 (4)	0.0238 (6)	−0.0039 (3)	−0.0029 (4)	0.0023 (4)
S6	0.0104 (4)	0.0202 (4)	0.0183 (5)	−0.0037 (3)	0.0009 (4)	0.0008 (4)
C1	0.0106 (15)	0.0189 (18)	0.016 (2)	−0.0025 (13)	0.0010 (15)	0.0026 (17)
C2	0.0126 (15)	0.0132 (17)	0.021 (2)	−0.0025 (13)	−0.0024 (15)	−0.0010 (16)
C3	0.0115 (15)	0.0137 (16)	0.017 (2)	0.0010 (12)	0.0038 (15)	0.0012 (16)
C4	0.0114 (15)	0.0163 (17)	0.017 (2)	0.0040 (13)	−0.0009 (15)	−0.0018 (17)
C5	0.0131 (15)	0.0179 (17)	0.0109 (19)	−0.0044 (13)	−0.0046 (14)	0.0012 (16)
C6	0.0094 (14)	0.0172 (17)	0.015 (2)	−0.0029 (13)	−0.0015 (15)	0.0028 (16)
C7A	0.0192 (17)	0.0107 (16)	0.026 (2)	0.0029 (13)	−0.0011 (17)	0.0030 (17)
C8A	0.0255 (19)	0.0208 (19)	0.026 (2)	−0.0026 (15)	−0.0088 (18)	0.0061 (19)
C9A	0.0146 (17)	0.0229 (19)	0.019 (2)	−0.0023 (14)	−0.0046 (16)	0.0021 (19)
N10A	0.0165 (15)	0.0291 (18)	0.028 (2)	−0.0026 (13)	−0.0041 (15)	−0.0043 (17)
C7B	0.0165 (17)	0.0153 (17)	0.024 (2)	−0.0011 (13)	0.0051 (16)	−0.0005 (17)
C8B	0.0190 (18)	0.033 (2)	0.018 (2)	−0.0013 (16)	0.0006 (17)	−0.0046 (19)
C9B	0.027 (2)	0.039 (3)	0.014 (2)	0.0124 (18)	−0.0008 (18)	−0.001 (2)
N10B	0.049 (2)	0.036 (2)	0.029 (2)	0.0112 (18)	0.0011 (19)	0.008 (2)

Geometric parameters (Å, º)

I1—C1	2.082 (3)	C5—C6	1.347 (5)
I2—C2	2.078 (3)	C7A—C8A	1.533 (5)
S1—C1	1.755 (4)	C7A—H7A1	0.9900
S1—C3	1.765 (3)	C7A—H7A2	0.9900
S2—C2	1.757 (3)	C8A—C9A	1.471 (5)
S2—C3	1.762 (3)	C8A—H8A1	0.9900
S3—C5	1.762 (3)	C8A—H8A2	0.9900
S3—C4	1.763 (3)	C9A—N10A	1.137 (4)
S4—C4	1.758 (3)	C7B—C8B	1.524 (5)
S4—C6	1.766 (3)	C7B—H7B1	0.9900
S5—C5	1.752 (3)	C7B—H7B2	0.9900
S5—C7A	1.814 (3)	C8B—C9B	1.472 (6)
S6—C6	1.752 (3)	C8B—H8B1	0.9900
S6—C7B	1.816 (4)	C8B—H8B2	0.9900
C1—C2	1.330 (5)	C9B—N10B	1.139 (5)
C3—C4	1.341 (5)
C1—S1—C3	94.81 (16)	C8A—C7A—H7A1	108.5
C2—S2—C3	94.82 (15)	S5—C7A—H7A1	108.5
C5—S3—C4	95.16 (16)	C8A—C7A—H7A2	108.5
C4—S4—C6	95.31 (16)	S5—C7A—H7A2	108.5
C5—S5—C7A	103.14 (15)	H7A1—C7A—H7A2	107.5
C6—S6—C7B	101.21 (17)	C9A—C8A—C7A	113.0 (3)
C2—C1—S1	117.8 (3)	C9A—C8A—H8A1	109.0
C2—C1—I1	125.0 (3)	C7A—C8A—H8A1	109.0
S1—C1—I1	117.15 (18)	C9A—C8A—H8A2	109.0
C1—C2—S2	117.8 (3)	C7A—C8A—H8A2	109.0
C1—C2—I2	126.2 (3)	H8A1—C8A—H8A2	107.8
S2—C2—I2	116.01 (17)	N10A—C9A—C8A	178.3 (4)
C4—C3—S2	122.3 (3)	C8B—C7B—S6	114.4 (2)
C4—C3—S1	123.0 (3)	C8B—C7B—H7B1	108.7
S2—C3—S1	114.70 (18)	S6—C7B—H7B1	108.7
C3—C4—S4	123.1 (3)	C8B—C7B—H7B2	108.7
C3—C4—S3	122.5 (3)	S6—C7B—H7B2	108.7
S4—C4—S3	114.31 (18)	H7B1—C7B—H7B2	107.6
C6—C5—S5	124.4 (3)	C9B—C8B—C7B	112.2 (3)
C6—C5—S3	117.3 (3)	C9B—C8B—H8B1	109.2
S5—C5—S3	117.9 (2)	C7B—C8B—H8B1	109.2
C5—C6—S6	125.8 (3)	C9B—C8B—H8B2	109.2
C5—C6—S4	117.0 (3)	C7B—C8B—H8B2	109.2
S6—C6—S4	116.87 (19)	H8B1—C8B—H8B2	107.9
C8A—C7A—S5	115.3 (3)	N10B—C9B—C8B	179.1 (5)
C3—S1—C1—C2	−0.5 (4)	C5—S3—C4—C3	−173.8 (3)
C3—S1—C1—I1	177.8 (2)	C5—S3—C4—S4	9.4 (2)
S1—C1—C2—S2	−0.6 (5)	C7A—S5—C5—C6	141.9 (3)
I1—C1—C2—S2	−178.70 (19)	C7A—S5—C5—S3	−45.4 (3)
S1—C1—C2—I2	178.8 (2)	C4—S3—C5—C6	−6.4 (3)
I1—C1—C2—I2	0.7 (5)	C4—S3—C5—S5	−179.6 (2)
C3—S2—C2—C1	1.3 (4)	S5—C5—C6—S6	0.1 (5)
C3—S2—C2—I2	−178.1 (2)	S3—C5—C6—S6	−172.6 (2)
C2—S2—C3—C4	177.9 (3)	S5—C5—C6—S4	173.9 (2)
C2—S2—C3—S1	−1.6 (2)	S3—C5—C6—S4	1.1 (4)
C1—S1—C3—C4	−178.2 (3)	C7B—S6—C6—C5	−118.9 (4)
C1—S1—C3—S2	1.4 (2)	C7B—S6—C6—S4	67.4 (2)
S2—C3—C4—S4	−0.8 (5)	C4—S4—C6—C5	4.8 (3)
S1—C3—C4—S4	178.7 (2)	C4—S4—C6—S6	179.1 (2)
S2—C3—C4—S3	−177.3 (2)	C5—S5—C7A—C8A	−76.7 (3)
S1—C3—C4—S3	2.2 (5)	S5—C7A—C8A—C9A	63.6 (4)
C6—S4—C4—C3	174.2 (3)	C6—S6—C7B—C8B	72.3 (3)
C6—S4—C4—S3	−8.9 (2)	S6—C7B—C8B—C9B	55.3 (4)

(EDTTTFI2)

Crystal data

C8H4I2S6	F(000) = 1016
Mr = 546.27	Dx = 2.619 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 9968 reflections
a = 17.3371 (5) Å	θ = 2.4–27.5°
b = 12.6274 (4) Å	µ = 5.41 mm^−1
c = 6.3276 (2) Å	T = 150 K
V = 1385.25 (7) Å^3	Prism, red
Z = 4	0.36 × 0.27 × 0.18 mm

Data collection

Bruker APEX-II CCD diffractometer	1653 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan SADABS (Bruker, 2003)	h = −18→22
Tmin = 0.189, Tmax = 0.377	k = −16→15
21142 measured reflections	l = −8→8

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.043	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.P)^2 + 4.9473P] where P = (Fo^2 + 2Fc^2)/3
1650 reflections	(Δ/σ)max = 0.002
86 parameters	Δρmax = 0.97 e Å^−3
2 restraints	Δρmin = −1.00 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)
I1	0.735136 (12)	0.101182 (17)	1.17264 (3)	0.02797 (7)
S1	0.62485 (4)	0.13263 (6)	0.76051 (12)	0.02139 (15)
S2	0.51753 (5)	0.13273 (6)	0.34058 (12)	0.02377 (16)
S3	0.41620 (5)	0.11009 (7)	−0.02834 (14)	0.03017 (18)
C1	0.67524 (15)	0.1973 (2)	0.9627 (4)	0.0183 (5)
C2	0.5947 (2)	0.2500	0.6339 (6)	0.0169 (8)
C3	0.5503 (2)	0.2500	0.4599 (6)	0.0165 (7)
C4	0.46386 (16)	0.1971 (2)	0.1428 (4)	0.0190 (6)
C5A	0.3479 (4)	0.2051 (5)	−0.1396 (11)	0.0259 (13)	0.50
H5AA	0.3184	0.1688	−0.2523	0.031*	0.50
H5AB	0.3107	0.2246	−0.0273	0.031*	0.50
C5B	0.3806 (4)	0.3060 (5)	−0.2310 (10)	0.0293 (14)	0.50
H5BA	0.3399	0.3435	−0.3113	0.035*	0.50
H5BB	0.4229	0.2885	−0.3301	0.035*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02796 (11)	0.03419 (12)	0.02175 (11)	0.00625 (8)	−0.00845 (8)	0.00658 (8)
S1	0.0290 (4)	0.0162 (3)	0.0190 (3)	0.0020 (3)	−0.0083 (3)	0.0001 (3)
S2	0.0351 (4)	0.0147 (3)	0.0215 (3)	0.0003 (3)	−0.0124 (3)	−0.0011 (3)
S3	0.0327 (4)	0.0272 (4)	0.0306 (4)	−0.0010 (3)	−0.0140 (3)	−0.0082 (3)
C1	0.0158 (12)	0.0263 (14)	0.0128 (12)	0.0015 (11)	−0.0020 (10)	0.0005 (11)
C2	0.0205 (19)	0.0147 (17)	0.0156 (19)	0.000	−0.0009 (15)	0.000
C3	0.0230 (19)	0.0128 (17)	0.0137 (18)	0.000	−0.0033 (15)	0.000
C4	0.0181 (12)	0.0230 (14)	0.0159 (13)	0.0008 (11)	−0.0039 (10)	−0.0017 (11)
C5A	0.027 (3)	0.033 (3)	0.017 (3)	−0.007 (3)	−0.010 (3)	0.000 (3)
C5B	0.040 (4)	0.033 (4)	0.014 (3)	0.009 (3)	0.000 (3)	0.001 (3)

Geometric parameters (Å, º)

I1—C1	2.078 (3)	C2—S1^i	1.764 (2)
S1—C1	1.751 (3)	C3—S2^i	1.757 (2)
S1—C2	1.764 (2)	C4—C4^i	1.336 (6)
S2—C3	1.757 (2)	C5A—C5B	1.510 (8)
S2—C4	1.759 (3)	C5A—H5AA	0.9900
S3—C4	1.750 (3)	C5A—H5AB	0.9900
S3—C5B^i	1.774 (5)	C5B—S3^i	1.774 (5)
S3—C5A	1.827 (5)	C5B—H5BA	0.9900
C1—C1^i	1.331 (6)	C5B—H5BB	0.9900
C2—C3	1.344 (5)
C1—S1—C2	95.04 (15)	C4^i—C4—S2	117.52 (10)
C3—S2—C4	95.01 (15)	S3—C4—S2	113.58 (16)
C4—S3—C5B^i	103.7 (2)	C5B—C5A—S3	117.3 (4)
C4—S3—C5A	97.6 (2)	C5B—C5A—H5AA	108.0
C1^i—C1—S1	117.80 (10)	S3—C5A—H5AA	108.0
C1^i—C1—I1	125.74 (8)	C5B—C5A—H5AB	108.0
S1—C1—I1	116.36 (15)	S3—C5A—H5AB	108.0
C3—C2—S1^i	122.82 (11)	H5AA—C5A—H5AB	107.2
C3—C2—S1	122.82 (11)	C5A—C5B—S3^i	111.0 (4)
S1^i—C2—S1	114.3 (2)	C5A—C5B—H5BA	109.4
C2—C3—S2	122.51 (11)	S3^i—C5B—H5BA	109.4
C2—C3—S2^i	122.51 (11)	C5A—C5B—H5BB	109.4
S2—C3—S2^i	114.9 (2)	S3^i—C5B—H5BB	109.4
C4^i—C4—S3	128.89 (10)	H5BA—C5B—H5BB	108.0
C2—S1—C1—C1^i	0.64 (14)	C5B^i—S3—C4—C4^i	9.6 (3)
C2—S1—C1—I1	−176.03 (18)	C5A—S3—C4—C4^i	−16.5 (3)
C1—S1—C2—C3	−178.9 (4)	C5B^i—S3—C4—S2	−171.1 (3)
C1—S1—C2—S1^i	−1.0 (2)	C5A—S3—C4—S2	162.8 (3)
S1^i—C2—C3—S2	−177.6 (2)	C3—S2—C4—C4^i	−0.18 (15)
S1—C2—C3—S2	0.1 (5)	C3—S2—C4—S3	−179.56 (19)
S1^i—C2—C3—S2^i	−0.1 (5)	C4—S3—C5A—C5B	52.9 (5)
S1—C2—C3—S2^i	177.6 (2)	C5B^i—S3—C5A—C5B	−52.6 (7)
C4—S2—C3—C2	177.9 (4)	S3—C5A—C5B—S3^i	−70.6 (5)
C4—S2—C3—S2^i	0.3 (2)

Symmetry code: (i) x, −y+1/2, z.

(I)

Crystal data

C12F4N4·2(C8H4I2S6)	Z = 1
Mr = 1368.70	F(000) = 644
Triclinic, P1	Dx = 2.355 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8311 (2) Å	Cell parameters from 23458 reflections
b = 12.0457 (4) Å	θ = 1.0–27.5°
c = 16.6577 (6) Å	µ = 3.93 mm^−1
α = 91.128 (2)°	T = 293 K
β = 92.950 (2)°	Needle, black
γ = 94.213 (2)°	0.24 × 0.08 × 0.05 mm
V = 965.21 (6) Å^3

Data collection

Nonius KappaCCD diffractometer	4430 independent reflections
Radiation source: fine-focus sealed tube	3215 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.040
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.6°
ω and φ scans	h = −5→6
Absorption correction: multi-scan SADABS (Bruker, 2003)	k = −15→15
Tmin = 0.693, Tmax = 0.822	l = −20→21
12784 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 1.1208P] where P = (Fo^2 + 2Fc^2)/3
4430 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.75 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
I1	1.00367 (7)	−0.09562 (3)	0.318460 (19)	0.03919 (10)
I2	0.78123 (9)	0.13172 (3)	0.45511 (2)	0.05213 (12)
S1	0.6357 (3)	0.03250 (10)	0.18459 (7)	0.0382 (3)
S2	0.4524 (3)	0.20477 (11)	0.29232 (7)	0.0415 (3)
S3	0.2534 (3)	0.11929 (10)	0.03856 (7)	0.0388 (3)
S4	0.0728 (3)	0.29612 (10)	0.14334 (7)	0.0380 (3)
S5	−0.0852 (4)	0.17208 (12)	−0.10330 (8)	0.0528 (4)
S6	−0.3050 (3)	0.38475 (11)	0.01644 (8)	0.0412 (3)
C1	0.7579 (10)	0.0323 (4)	0.2858 (3)	0.0353 (10)
C2	0.6766 (10)	0.1115 (4)	0.3331 (3)	0.0344 (10)
C3	0.4328 (10)	0.1450 (4)	0.1962 (3)	0.0320 (10)
C4	0.2719 (10)	0.1822 (4)	0.1338 (3)	0.0335 (10)
C5	0.0087 (11)	0.2041 (4)	−0.0027 (3)	0.0345 (10)
C6	−0.0741 (10)	0.2859 (4)	0.0451 (3)	0.0317 (10)
C7	−0.2932 (15)	0.2835 (5)	−0.1352 (4)	0.0634 (18)
H7A	−0.2617	0.2977	−0.1913	0.076*
H7B	−0.4877	0.2585	−0.1319	0.076*
C8	−0.2396 (15)	0.3890 (5)	−0.0892 (3)	0.0552 (15)
H8A	−0.3533	0.4435	−0.1138	0.066*
H8B	−0.0468	0.4152	−0.0943	0.066*
F9	1.3673 (7)	0.3446 (3)	0.48016 (19)	0.0517 (8)
F10	1.0769 (7)	0.4063 (3)	0.35481 (18)	0.0553 (9)
C9	0.7104 (13)	0.5277 (5)	0.2822 (3)	0.0527 (15)
C10	0.6844 (11)	0.5703 (4)	0.3619 (3)	0.0399 (11)
C11	0.4878 (12)	0.6515 (5)	0.3648 (3)	0.0429 (12)
C12	0.8378 (10)	0.5349 (4)	0.4297 (3)	0.0335 (10)
C13	1.0356 (11)	0.4535 (4)	0.4263 (3)	0.0383 (11)
C14	1.1843 (10)	0.4219 (4)	0.4913 (3)	0.0357 (11)
N1	0.7192 (16)	0.4984 (6)	0.2172 (4)	0.091 (2)
N2	0.3279 (12)	0.7161 (4)	0.3626 (3)	0.0598 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0454 (2)	0.04073 (18)	0.03315 (17)	0.01852 (14)	−0.00352 (13)	0.00190 (13)
I2	0.0703 (3)	0.0540 (2)	0.03304 (19)	0.02177 (19)	−0.01066 (17)	−0.00419 (15)
S1	0.0436 (7)	0.0417 (7)	0.0309 (6)	0.0187 (6)	−0.0039 (5)	−0.0013 (5)
S2	0.0526 (8)	0.0418 (7)	0.0322 (6)	0.0233 (6)	−0.0052 (5)	−0.0015 (5)
S3	0.0478 (7)	0.0386 (6)	0.0319 (6)	0.0205 (6)	−0.0033 (5)	0.0001 (5)
S4	0.0468 (7)	0.0403 (6)	0.0285 (6)	0.0190 (6)	−0.0039 (5)	−0.0008 (5)
S5	0.0784 (11)	0.0468 (8)	0.0341 (7)	0.0252 (7)	−0.0165 (7)	−0.0074 (6)
S6	0.0456 (8)	0.0411 (7)	0.0390 (7)	0.0203 (6)	−0.0032 (5)	0.0025 (5)
C1	0.036 (3)	0.037 (3)	0.033 (2)	0.008 (2)	−0.006 (2)	0.0045 (19)
C2	0.037 (3)	0.038 (3)	0.028 (2)	0.008 (2)	−0.0068 (19)	0.0031 (19)
C3	0.035 (3)	0.031 (2)	0.031 (2)	0.013 (2)	0.0001 (19)	0.0048 (18)
C4	0.035 (3)	0.038 (3)	0.029 (2)	0.012 (2)	0.0018 (19)	0.0047 (19)
C5	0.045 (3)	0.030 (2)	0.028 (2)	0.007 (2)	−0.003 (2)	0.0022 (18)
C6	0.032 (3)	0.035 (2)	0.029 (2)	0.010 (2)	−0.0019 (19)	0.0035 (18)
C7	0.078 (5)	0.068 (4)	0.047 (3)	0.036 (4)	−0.018 (3)	−0.007 (3)
C8	0.083 (4)	0.048 (3)	0.038 (3)	0.025 (3)	−0.006 (3)	0.009 (2)
F9	0.055 (2)	0.0544 (18)	0.0499 (19)	0.0332 (15)	−0.0013 (15)	−0.0035 (14)
F10	0.064 (2)	0.068 (2)	0.0369 (17)	0.0365 (17)	−0.0047 (15)	−0.0108 (15)
C9	0.061 (4)	0.063 (4)	0.038 (3)	0.030 (3)	−0.004 (3)	0.011 (3)
C10	0.039 (3)	0.041 (3)	0.040 (3)	0.014 (2)	−0.004 (2)	0.007 (2)
C11	0.046 (3)	0.046 (3)	0.038 (3)	0.011 (2)	−0.007 (2)	0.007 (2)
C12	0.034 (3)	0.034 (2)	0.033 (2)	0.010 (2)	−0.003 (2)	0.0028 (19)
C13	0.044 (3)	0.038 (3)	0.034 (3)	0.013 (2)	0.000 (2)	−0.005 (2)
C14	0.034 (3)	0.030 (2)	0.045 (3)	0.014 (2)	0.003 (2)	0.000 (2)
N1	0.120 (6)	0.120 (5)	0.041 (3)	0.066 (5)	−0.007 (3)	0.004 (3)
N2	0.066 (3)	0.059 (3)	0.058 (3)	0.031 (3)	−0.007 (3)	0.012 (2)

Geometric parameters (Å, º)

I1—C1	2.077 (5)	C7—C8	1.470 (8)
I2—C2	2.074 (5)	C7—H7A	0.9700
S1—C3	1.743 (4)	C7—H7B	0.9700
S1—C1	1.757 (5)	C8—H8A	0.9700
S2—C3	1.738 (5)	C8—H8B	0.9700
S2—C2	1.741 (5)	F9—C14	1.346 (5)
S3—C4	1.740 (5)	F10—C13	1.340 (5)
S3—C5	1.742 (5)	C9—N1	1.135 (8)
S4—C4	1.742 (5)	C9—C10	1.430 (8)
S4—C6	1.748 (5)	C10—C12	1.408 (7)
S5—C5	1.742 (5)	C10—C11	1.415 (7)
S5—C7	1.807 (6)	C11—N2	1.136 (7)
S6—C6	1.747 (5)	C12—C14^i	1.419 (6)
S6—C8	1.805 (6)	C12—C13	1.421 (7)
C1—C2	1.320 (7)	C13—C14	1.344 (7)
C3—C4	1.368 (7)	C14—C12^i	1.419 (6)
C5—C6	1.351 (6)
C3—S1—C1	95.3 (2)	C8—C7—H7A	108.4
C3—S2—C2	95.0 (2)	S5—C7—H7A	108.4
C4—S3—C5	95.4 (2)	C8—C7—H7B	108.4
C4—S4—C6	95.4 (2)	S5—C7—H7B	108.4
C5—S5—C7	104.5 (3)	H7A—C7—H7B	107.5
C6—S6—C8	98.7 (2)	C7—C8—S6	116.4 (5)
C2—C1—S1	116.4 (4)	C7—C8—H8A	108.2
C2—C1—I1	127.2 (4)	S6—C8—H8A	108.2
S1—C1—I1	116.4 (2)	C7—C8—H8B	108.2
C1—C2—S2	118.5 (4)	S6—C8—H8B	108.2
C1—C2—I2	125.4 (4)	H8A—C8—H8B	107.3
S2—C2—I2	116.1 (2)	N1—C9—C10	175.7 (6)
C4—C3—S2	123.3 (3)	C12—C10—C11	124.2 (5)
C4—C3—S1	121.9 (4)	C12—C10—C9	123.5 (5)
S2—C3—S1	114.8 (3)	C11—C10—C9	112.3 (5)
C3—C4—S3	122.2 (4)	N2—C11—C10	176.2 (6)
C3—C4—S4	122.8 (4)	C10—C12—C14^i	123.7 (4)
S3—C4—S4	115.0 (3)	C10—C12—C13	123.9 (4)
C6—C5—S5	129.3 (4)	C14^i—C12—C13	112.4 (4)
C6—C5—S3	117.3 (4)	F10—C13—C14	118.4 (4)
S5—C5—S3	113.4 (3)	F10—C13—C12	118.3 (4)
C5—C6—S6	125.8 (4)	C14—C13—C12	123.3 (4)
C5—C6—S4	116.7 (4)	C13—C14—F9	117.6 (4)
S6—C6—S4	117.4 (3)	C13—C14—C12^i	124.3 (4)
C8—C7—S5	115.5 (4)	F9—C14—C12^i	118.1 (4)
C3—S1—C1—C2	−2.5 (5)	S5—C5—C6—S6	−0.3 (7)
C3—S1—C1—I1	175.5 (3)	S3—C5—C6—S6	177.2 (3)
S1—C1—C2—S2	1.7 (6)	S5—C5—C6—S4	−178.0 (3)
I1—C1—C2—S2	−176.1 (3)	S3—C5—C6—S4	−0.5 (6)
S1—C1—C2—I2	179.1 (3)	C8—S6—C6—C5	−27.8 (5)
I1—C1—C2—I2	1.3 (7)	C8—S6—C6—S4	149.9 (3)
C3—S2—C2—C1	0.1 (5)	C4—S4—C6—C5	−1.5 (4)
C3—S2—C2—I2	−177.6 (3)	C4—S4—C6—S6	−179.4 (3)
C2—S2—C3—C4	178.2 (4)	C5—S5—C7—C8	24.8 (6)
C2—S2—C3—S1	−1.8 (3)	S5—C7—C8—S6	−61.7 (7)
C1—S1—C3—C4	−177.5 (4)	C6—S6—C8—C7	59.5 (5)
C1—S1—C3—S2	2.5 (3)	C11—C10—C12—C14^i	−1.0 (8)
S2—C3—C4—S3	−179.1 (3)	C9—C10—C12—C14^i	179.0 (5)
S1—C3—C4—S3	0.9 (6)	C11—C10—C12—C13	−179.8 (5)
S2—C3—C4—S4	1.3 (7)	C9—C10—C12—C13	0.2 (8)
S1—C3—C4—S4	−178.7 (3)	C10—C12—C13—F10	−0.9 (8)
C5—S3—C4—C3	177.2 (4)	C14^i—C12—C13—F10	−179.8 (4)
C5—S3—C4—S4	−3.3 (3)	C10—C12—C13—C14	178.8 (5)
C6—S4—C4—C3	−177.4 (4)	C14^i—C12—C13—C14	−0.1 (8)
C6—S4—C4—S3	3.1 (3)	F10—C13—C14—F9	0.2 (7)
C7—S5—C5—C6	6.3 (6)	C12—C13—C14—F9	−179.4 (5)
C7—S5—C5—S3	−171.3 (3)	F10—C13—C14—C12^i	179.8 (5)
C4—S3—C5—C6	2.3 (4)	C12—C13—C14—C12^i	0.2 (9)
C4—S3—C5—S5	−179.8 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

(II)

Crystal data

C12F4N4·2(C8H4I2S6)	Z = 2
Mr = 1368.70	F(000) = 1288
Triclinic, P1	Dx = 2.383 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.0030 (4) Å	Cell parameters from 883 reflections
b = 12.7689 (4) Å	θ = 3.6–27.5°
c = 14.9201 (5) Å	µ = 3.98 mm^−1
α = 104.906 (2)°	T = 293 K
β = 106.449 (2)°	Plate, black
γ = 95.863 (2)°	0.32 × 0.22 × 0.03 mm
V = 1907.83 (11) Å^3

Data collection

Nonius KappaCCD diffractometer	8748 independent reflections
Radiation source: fine-focus sealed tube	5762 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.057
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.6°
ω and φ scans	h = −14→14
Absorption correction: multi-scan SADABS (Bruker, 2003)	k = −16→16
Tmin = 0.364, Tmax = 0.888	l = −19→19
33190 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 19.0915P] where P = (Fo^2 + 2Fc^2)/3
8748 reflections	(Δ/σ)max < 0.001
478 parameters	Δρmax = 1.71 e Å^−3
0 restraints	Δρmin = −2.62 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)
I1	0.77321 (6)	0.94918 (4)	0.43167 (4)	0.03971 (16)
I2	0.60745 (7)	0.85875 (6)	0.59966 (5)	0.0527 (2)
C1	0.6727 (8)	0.7923 (6)	0.4087 (6)	0.0326 (18)
C2	0.6168 (9)	0.7599 (7)	0.4686 (6)	0.0369 (19)
C3	0.5631 (9)	0.5878 (7)	0.3175 (7)	0.0368 (19)
C4	0.5130 (9)	0.4899 (7)	0.2481 (7)	0.038 (2)
C5	0.4421 (8)	0.3276 (7)	0.0876 (7)	0.037 (2)
C6	0.3859 (8)	0.2933 (7)	0.1486 (7)	0.0341 (18)
C7A	0.409 (3)	0.120 (2)	−0.024 (3)	0.084 (12)	0.50
H7A1	0.3599	0.0733	−0.0899	0.101*	0.50
H7A2	0.4945	0.1017	−0.0106	0.101*	0.50
C7B	0.346 (2)	0.122 (2)	−0.0539 (17)	0.042 (6)	0.50
H7B1	0.2553	0.1183	−0.0873	0.051*	0.50
H7B2	0.3777	0.0714	−0.0985	0.051*	0.50
C8	0.3564 (16)	0.0818 (9)	0.0352 (10)	0.074 (4)
H8A	0.4223	0.0509	0.0731	0.088*
H8B	0.2880	0.0201	−0.0072	0.088*
S1	0.6632 (2)	0.69217 (17)	0.30031 (18)	0.0404 (5)
S2	0.5402 (2)	0.62156 (18)	0.43267 (18)	0.0423 (5)
S3	0.5418 (3)	0.45688 (19)	0.13586 (19)	0.0471 (6)
S4	0.4201 (3)	0.38139 (19)	0.26758 (19)	0.0481 (6)
S5	0.4286 (3)	0.2572 (2)	−0.0320 (2)	0.0557 (7)
S6	0.2894 (3)	0.1625 (2)	0.1218 (2)	0.0515 (6)
I3	0.58507 (6)	0.12328 (5)	0.79223 (5)	0.04406 (17)
I4	0.73283 (8)	0.20781 (6)	0.62038 (5)	0.0586 (2)
C9	0.7017 (8)	0.2753 (7)	0.8226 (7)	0.0363 (19)
C10	0.7520 (8)	0.3071 (7)	0.7581 (7)	0.0368 (19)
C11	0.8222 (8)	0.4769 (7)	0.9115 (6)	0.0332 (18)
C12	0.8763 (8)	0.5807 (7)	0.9791 (7)	0.0344 (18)
C13	0.9348 (8)	0.7514 (7)	1.1281 (6)	0.0338 (18)
C14	0.9840 (8)	0.7834 (7)	1.0628 (6)	0.0346 (18)
C15	1.0245 (16)	0.9622 (10)	1.2554 (10)	0.081 (4)
H15A	1.0006	1.0192	1.3005	0.097*
H15B	1.1138	0.9596	1.2869	0.097*
C16	1.0192 (15)	0.9965 (9)	1.1719 (10)	0.076 (4)
H16A	1.0736	1.0690	1.1943	0.091*
H16B	0.9314	1.0057	1.1440	0.091*
S7	0.7368 (2)	0.37295 (18)	0.93643 (18)	0.0402 (5)
S8	0.8399 (2)	0.43943 (18)	0.79558 (17)	0.0382 (5)
S9	0.8572 (2)	0.61502 (19)	1.09266 (18)	0.0410 (5)
S10	0.9645 (2)	0.68241 (17)	0.95366 (17)	0.0369 (5)
S11	0.9267 (3)	0.8305 (2)	1.2405 (2)	0.0588 (7)
S12	1.0635 (3)	0.91458 (19)	1.0760 (2)	0.0500 (6)
F3	0.8932 (5)	0.4354 (4)	0.2278 (4)	0.0449 (13)
F2	0.7762 (5)	0.4861 (4)	0.5643 (4)	0.0434 (13)
F4	0.9793 (5)	0.6248 (4)	0.3655 (4)	0.0431 (12)
F1	0.6884 (5)	0.2972 (4)	0.4256 (4)	0.0438 (13)
C20	0.7872 (7)	0.3533 (6)	0.3191 (6)	0.0275 (16)
C22	0.8059 (8)	0.4760 (7)	0.4829 (6)	0.0305 (17)
C26	0.9293 (8)	0.6690 (6)	0.5486 (6)	0.0321 (18)
C25	0.8639 (8)	0.4472 (6)	0.3114 (6)	0.0303 (17)
C18	0.7390 (8)	0.2517 (7)	0.2447 (6)	0.0332 (18)
C19	0.7675 (10)	0.2270 (8)	0.1564 (7)	0.043 (2)
C23	0.8829 (7)	0.5658 (6)	0.4741 (6)	0.0294 (17)
C21	0.7611 (8)	0.3776 (7)	0.4104 (6)	0.0306 (17)
C24	0.9088 (8)	0.5447 (6)	0.3836 (6)	0.0304 (17)
C17	0.6605 (9)	0.1614 (7)	0.2521 (6)	0.039 (2)
C27	0.9020 (9)	0.6920 (7)	0.6399 (8)	0.043 (2)
C28	1.0108 (9)	0.7599 (7)	0.5418 (7)	0.041 (2)
N1	0.5933 (9)	0.0846 (7)	0.2484 (7)	0.058 (2)
N2	0.7835 (11)	0.2002 (8)	0.0809 (7)	0.067 (3)
N4	1.0747 (9)	0.8366 (7)	0.5432 (8)	0.062 (3)
N3	0.8864 (11)	0.7194 (8)	0.7150 (7)	0.069 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0465 (3)	0.0238 (3)	0.0457 (3)	−0.0031 (2)	0.0198 (3)	0.0034 (2)
I2	0.0608 (4)	0.0450 (4)	0.0435 (4)	−0.0072 (3)	0.0258 (3)	−0.0047 (3)
C1	0.038 (4)	0.022 (4)	0.034 (4)	0.003 (3)	0.010 (4)	0.003 (3)
C2	0.042 (5)	0.028 (4)	0.039 (5)	0.000 (4)	0.019 (4)	0.002 (4)
C3	0.041 (5)	0.025 (4)	0.050 (5)	0.005 (4)	0.024 (4)	0.012 (4)
C4	0.042 (5)	0.025 (4)	0.046 (5)	−0.001 (4)	0.019 (4)	0.008 (4)
C5	0.038 (5)	0.021 (4)	0.044 (5)	0.004 (3)	0.015 (4)	−0.005 (4)
C6	0.033 (4)	0.021 (4)	0.044 (5)	0.000 (3)	0.013 (4)	0.004 (3)
C7A	0.08 (2)	0.016 (10)	0.15 (4)	0.004 (16)	0.06 (2)	−0.010 (16)
C7B	0.033 (12)	0.042 (12)	0.032 (10)	0.000 (11)	0.003 (9)	−0.010 (8)
C8	0.126 (12)	0.032 (6)	0.066 (8)	0.019 (7)	0.042 (8)	0.005 (5)
S1	0.0539 (14)	0.0237 (10)	0.0446 (13)	−0.0018 (9)	0.0267 (11)	0.0031 (9)
S2	0.0555 (14)	0.0267 (11)	0.0455 (13)	−0.0037 (10)	0.0269 (11)	0.0046 (9)
S3	0.0626 (16)	0.0308 (11)	0.0463 (14)	−0.0065 (11)	0.0284 (12)	0.0026 (10)
S4	0.0680 (16)	0.0284 (11)	0.0454 (13)	−0.0093 (11)	0.0288 (12)	0.0019 (10)
S5	0.0744 (18)	0.0415 (14)	0.0438 (14)	0.0009 (13)	0.0243 (13)	−0.0016 (11)
S6	0.0490 (14)	0.0320 (12)	0.0640 (17)	−0.0099 (10)	0.0219 (12)	0.0007 (11)
I3	0.0469 (4)	0.0305 (3)	0.0500 (4)	−0.0028 (2)	0.0198 (3)	0.0033 (3)
I4	0.0689 (5)	0.0529 (4)	0.0471 (4)	0.0041 (4)	0.0181 (3)	0.0068 (3)
C9	0.029 (4)	0.027 (4)	0.049 (5)	0.001 (3)	0.011 (4)	0.008 (4)
C10	0.034 (4)	0.032 (4)	0.038 (5)	0.003 (4)	0.008 (4)	0.006 (4)
C11	0.037 (4)	0.024 (4)	0.041 (5)	0.005 (3)	0.019 (4)	0.008 (4)
C12	0.034 (4)	0.028 (4)	0.042 (5)	0.002 (3)	0.014 (4)	0.012 (4)
C13	0.033 (4)	0.029 (4)	0.037 (5)	0.001 (3)	0.012 (4)	0.008 (4)
C14	0.039 (5)	0.027 (4)	0.035 (5)	0.001 (3)	0.010 (4)	0.008 (3)
C15	0.118 (12)	0.041 (6)	0.061 (8)	−0.018 (7)	0.024 (8)	−0.006 (6)
C16	0.105 (10)	0.032 (6)	0.092 (10)	−0.009 (6)	0.062 (8)	−0.004 (6)
S7	0.0464 (13)	0.0289 (11)	0.0467 (13)	−0.0027 (9)	0.0245 (10)	0.0070 (9)
S8	0.0449 (12)	0.0305 (11)	0.0391 (12)	−0.0015 (9)	0.0171 (10)	0.0098 (9)
S9	0.0510 (13)	0.0315 (11)	0.0446 (13)	0.0002 (10)	0.0260 (11)	0.0093 (10)
S10	0.0444 (12)	0.0268 (10)	0.0397 (12)	−0.0006 (9)	0.0171 (10)	0.0091 (9)
S11	0.0750 (19)	0.0471 (15)	0.0459 (15)	−0.0104 (13)	0.0302 (14)	−0.0035 (12)
S12	0.0626 (16)	0.0266 (11)	0.0551 (15)	−0.0065 (11)	0.0206 (13)	0.0068 (10)
F3	0.057 (3)	0.041 (3)	0.037 (3)	−0.008 (2)	0.026 (2)	0.008 (2)
F2	0.057 (3)	0.036 (3)	0.039 (3)	−0.001 (2)	0.028 (3)	0.003 (2)
F4	0.051 (3)	0.029 (3)	0.050 (3)	−0.010 (2)	0.024 (3)	0.012 (2)
F1	0.053 (3)	0.029 (3)	0.045 (3)	−0.016 (2)	0.024 (3)	0.004 (2)
C20	0.026 (4)	0.021 (4)	0.030 (4)	−0.001 (3)	0.005 (3)	0.004 (3)
C22	0.036 (4)	0.029 (4)	0.030 (4)	0.006 (3)	0.015 (3)	0.009 (3)
C26	0.031 (4)	0.015 (3)	0.043 (5)	0.002 (3)	0.010 (4)	−0.001 (3)
C25	0.031 (4)	0.025 (4)	0.032 (4)	−0.001 (3)	0.008 (3)	0.008 (3)
C18	0.036 (4)	0.022 (4)	0.034 (4)	−0.007 (3)	0.009 (4)	0.002 (3)
C19	0.051 (6)	0.036 (5)	0.034 (5)	−0.007 (4)	0.012 (4)	0.004 (4)
C23	0.024 (4)	0.024 (4)	0.037 (4)	0.002 (3)	0.012 (3)	0.003 (3)
C21	0.031 (4)	0.030 (4)	0.031 (4)	−0.004 (3)	0.014 (3)	0.008 (3)
C24	0.030 (4)	0.020 (4)	0.042 (5)	−0.002 (3)	0.014 (4)	0.010 (3)
C17	0.042 (5)	0.028 (4)	0.035 (5)	−0.002 (4)	0.008 (4)	−0.002 (4)
C27	0.040 (5)	0.026 (4)	0.053 (6)	0.003 (4)	0.012 (4)	−0.001 (4)
C28	0.047 (5)	0.025 (4)	0.043 (5)	0.006 (4)	0.012 (4)	0.004 (4)
N1	0.075 (6)	0.031 (4)	0.053 (5)	−0.024 (4)	0.020 (5)	0.000 (4)
N2	0.086 (7)	0.048 (5)	0.059 (6)	−0.011 (5)	0.034 (5)	0.000 (5)
N4	0.066 (6)	0.030 (4)	0.082 (7)	−0.009 (4)	0.027 (5)	0.008 (4)
N3	0.087 (7)	0.055 (6)	0.050 (6)	0.003 (5)	0.031 (5)	−0.014 (5)

Geometric parameters (Å, º)

I1—C1	2.082 (8)	C12—S9	1.716 (9)
I2—C2	2.073 (8)	C12—S10	1.725 (8)
C1—C2	1.341 (12)	C13—C14	1.368 (12)
C1—S1	1.753 (8)	C13—S9	1.734 (8)
C2—S2	1.753 (9)	C13—S11	1.752 (9)
C3—C4	1.344 (12)	C14—S10	1.739 (9)
C3—S2	1.757 (9)	C14—S12	1.744 (8)
C3—S1	1.758 (8)	C15—C16	1.411 (18)
C4—S3	1.746 (9)	C15—S11	1.827 (12)
C4—S4	1.771 (8)	C15—H15A	0.9700
C5—C6	1.368 (12)	C15—H15B	0.9700
C5—S5	1.736 (9)	C16—S12	1.763 (12)
C5—S3	1.738 (8)	C16—H16A	0.9700
C6—S4	1.751 (9)	C16—H16B	0.9700
C6—S6	1.769 (8)	F3—C25	1.350 (9)
C7A—C8	1.34 (4)	F2—C22	1.324 (9)
C7A—S5	1.79 (3)	F4—C24	1.348 (8)
C7A—H7A1	0.9700	F1—C21	1.342 (8)
C7A—H7A2	0.9700	C20—C18	1.407 (11)
C7B—C8	1.53 (3)	C20—C21	1.434 (11)
C7B—S5	1.77 (3)	C20—C25	1.443 (10)
C7B—H7B1	0.9700	C22—C21	1.365 (11)
C7B—H7B2	0.9700	C22—C23	1.411 (11)
C8—S6	1.812 (12)	C26—C23	1.421 (11)
C8—H8A	0.9700	C26—C28	1.436 (12)
C8—H8B	0.9700	C26—C27	1.441 (13)
I3—C9	2.080 (8)	C25—C24	1.356 (11)
I4—C10	2.058 (9)	C18—C19	1.405 (12)
C9—C10	1.362 (13)	C18—C17	1.416 (11)
C9—S7	1.740 (9)	C19—N2	1.160 (13)
C10—S8	1.725 (9)	C23—C24	1.422 (11)
C11—C12	1.393 (12)	C17—N1	1.145 (11)
C11—S7	1.726 (8)	C27—N3	1.152 (13)
C11—S8	1.744 (9)	C28—N4	1.137 (12)
C2—C1—S1	117.1 (6)	C11—C12—S9	121.5 (6)
C2—C1—I1	126.8 (6)	C11—C12—S10	122.3 (7)
S1—C1—I1	116.0 (4)	S9—C12—S10	116.2 (5)
C1—C2—S2	117.7 (7)	C14—C13—S9	116.6 (7)
C1—C2—I2	126.4 (6)	C14—C13—S11	129.6 (7)
S2—C2—I2	115.9 (4)	S9—C13—S11	113.6 (5)
C4—C3—S2	124.1 (7)	C13—C14—S10	116.5 (6)
C4—C3—S1	121.5 (7)	C13—C14—S12	127.3 (7)
S2—C3—S1	114.3 (5)	S10—C14—S12	116.1 (5)
C3—C4—S3	123.2 (7)	C16—C15—S11	119.2 (9)
C3—C4—S4	121.8 (7)	C16—C15—H15A	107.5
S3—C4—S4	114.9 (5)	S11—C15—H15A	107.5
C6—C5—S5	128.2 (7)	C16—C15—H15B	107.5
C6—C5—S3	116.3 (6)	S11—C15—H15B	107.5
S5—C5—S3	115.5 (5)	H15A—C15—H15B	107.0
C5—C6—S4	118.1 (6)	C15—C16—S12	119.9 (11)
C5—C6—S6	125.9 (7)	C15—C16—H16A	107.3
S4—C6—S6	115.8 (5)	S12—C16—H16A	107.3
C8—C7A—S5	127 (2)	C15—C16—H16B	107.3
C8—C7A—H7A1	105.5	S12—C16—H16B	107.3
S5—C7A—H7A1	105.5	H16A—C16—H16B	106.9
C8—C7A—H7A2	105.5	C11—S7—C9	96.6 (4)
S5—C7A—H7A2	105.5	C10—S8—C11	95.9 (4)
H7A1—C7A—H7A2	106.1	C12—S9—C13	95.4 (4)
C8—C7B—S5	116.9 (14)	C12—S10—C14	95.1 (4)
C8—C7B—H7B1	108.1	C13—S11—C15	100.6 (5)
S5—C7B—H7B1	108.1	C14—S12—C16	101.3 (5)
C8—C7B—H7B2	108.1	C18—C20—C21	123.9 (7)
S5—C7B—H7B2	108.1	C18—C20—C25	124.4 (7)
H7B1—C7B—H7B2	107.3	C21—C20—C25	111.6 (7)
C7A—C8—S6	125.6 (14)	F2—C22—C21	118.1 (7)
C7B—C8—S6	113.5 (12)	F2—C22—C23	119.5 (7)
C7A—C8—H8A	105.9	C21—C22—C23	122.4 (7)
C7B—C8—H8A	132.6	C23—C26—C28	123.6 (8)
S6—C8—H8A	105.9	C23—C26—C27	123.3 (8)
C7A—C8—H8B	105.9	C28—C26—C27	113.1 (7)
C7B—C8—H8B	87.6	F3—C25—C24	119.0 (7)
S6—C8—H8B	105.9	F3—C25—C20	117.4 (7)
H8A—C8—H8B	106.2	C24—C25—C20	123.6 (8)
C1—S1—C3	95.2 (4)	C19—C18—C20	123.8 (7)
C2—S2—C3	95.0 (4)	C19—C18—C17	112.4 (7)
C5—S3—C4	96.0 (4)	C20—C18—C17	123.8 (8)
C6—S4—C4	94.2 (4)	N2—C19—C18	175.0 (10)
C5—S5—C7B	105.5 (9)	C22—C23—C26	123.0 (8)
C5—S5—C7A	98.7 (14)	C22—C23—C24	114.2 (7)
C6—S6—C8	99.0 (5)	C26—C23—C24	122.8 (7)
C10—C9—S7	115.7 (6)	F1—C21—C22	117.9 (7)
C10—C9—I3	124.7 (7)	F1—C21—C20	117.3 (7)
S7—C9—I3	119.6 (5)	C22—C21—C20	124.7 (7)
C9—C10—S8	117.5 (7)	F4—C24—C25	116.6 (7)
C9—C10—I4	124.6 (7)	F4—C24—C23	119.9 (7)
S8—C10—I4	117.9 (5)	C25—C24—C23	123.5 (7)
C12—C11—S7	123.1 (7)	N1—C17—C18	173.3 (10)
C12—C11—S8	122.6 (6)	N3—C27—C26	174.1 (10)
S7—C11—S8	114.2 (5)	N4—C28—C26	174.6 (11)
S1—C1—C2—S2	0.0 (11)	S11—C15—C16—S12	−60.0 (17)
I1—C1—C2—S2	−178.9 (5)	C12—C11—S7—C9	179.6 (8)
S1—C1—C2—I2	−178.4 (5)	S8—C11—S7—C9	−2.4 (6)
I1—C1—C2—I2	2.7 (13)	C10—C9—S7—C11	2.3 (8)
S2—C3—C4—S3	−177.7 (5)	I3—C9—S7—C11	−176.1 (5)
S1—C3—C4—S3	0.1 (13)	C9—C10—S8—C11	−0.2 (8)
S2—C3—C4—S4	−1.7 (13)	I4—C10—S8—C11	−179.3 (5)
S1—C3—C4—S4	176.1 (5)	C12—C11—S8—C10	179.8 (8)
S5—C5—C6—S4	178.5 (6)	S7—C11—S8—C10	1.8 (6)
S3—C5—C6—S4	−0.3 (10)	C11—C12—S9—C13	−175.6 (8)
S5—C5—C6—S6	3.4 (13)	S10—C12—S9—C13	3.9 (6)
S3—C5—C6—S6	−175.5 (5)	C14—C13—S9—C12	−1.7 (8)
S5—C7A—C8—C7B	74 (4)	S11—C13—S9—C12	173.7 (5)
S5—C7A—C8—S6	1 (5)	C11—C12—S10—C14	175.2 (8)
S5—C7B—C8—C7A	−60 (3)	S9—C12—S10—C14	−4.3 (6)
S5—C7B—C8—S6	62.3 (19)	C13—C14—S10—C12	3.1 (8)
C2—C1—S1—C3	5.0 (8)	S12—C14—S10—C12	−176.5 (5)
I1—C1—S1—C3	−176.0 (5)	C14—C13—S11—C15	−8.6 (11)
C4—C3—S1—C1	173.7 (8)	S9—C13—S11—C15	176.8 (7)
S2—C3—S1—C1	−8.3 (6)	C16—C15—S11—C13	35.8 (14)
C1—C2—S2—C3	−5.0 (8)	C13—C14—S12—C16	−17.0 (11)
I2—C2—S2—C3	173.6 (5)	S10—C14—S12—C16	162.6 (7)
C4—C3—S2—C2	−173.8 (9)	C15—C16—S12—C14	45.2 (13)
S1—C3—S2—C2	8.3 (6)	C18—C20—C25—F3	−1.5 (12)
C6—C5—S3—C4	−3.9 (8)	C21—C20—C25—F3	−178.9 (7)
S5—C5—S3—C4	177.1 (6)	C18—C20—C25—C24	179.5 (8)
C3—C4—S3—C5	−176.9 (9)	C21—C20—C25—C24	2.1 (12)
S4—C4—S3—C5	6.8 (6)	C21—C20—C18—C19	−178.3 (9)
C5—C6—S4—C4	4.4 (8)	C25—C20—C18—C19	4.7 (14)
S6—C6—S4—C4	180.0 (5)	C21—C20—C18—C17	−0.9 (14)
C3—C4—S4—C6	176.8 (9)	C25—C20—C18—C17	−178.0 (8)
S3—C4—S4—C6	−6.9 (6)	F2—C22—C23—C26	−1.1 (13)
C6—C5—S5—C7B	−8.5 (12)	C21—C22—C23—C26	179.5 (8)
S3—C5—S5—C7B	170.3 (9)	F2—C22—C23—C24	179.6 (7)
C6—C5—S5—C7A	−31.4 (14)	C21—C22—C23—C24	0.2 (12)
S3—C5—S5—C7A	147.5 (12)	C28—C26—C23—C22	178.1 (8)
C8—C7B—S5—C5	−25.2 (18)	C27—C26—C23—C22	−0.2 (13)
C8—C7B—S5—C7A	51 (4)	C28—C26—C23—C24	−2.7 (13)
C8—C7A—S5—C5	29 (4)	C27—C26—C23—C24	179.0 (8)
C8—C7A—S5—C7B	−80 (4)	F2—C22—C21—F1	0.7 (12)
C5—C6—S6—C8	27.3 (10)	C23—C22—C21—F1	−179.9 (7)
S4—C6—S6—C8	−147.9 (6)	F2—C22—C21—C20	−178.6 (8)
C7A—C8—S6—C6	−29 (3)	C23—C22—C21—C20	0.8 (14)
C7B—C8—S6—C6	−58.6 (14)	C18—C20—C21—F1	1.5 (13)
S7—C9—C10—S8	−1.5 (10)	C25—C20—C21—F1	178.8 (7)
I3—C9—C10—S8	176.8 (5)	C18—C20—C21—C22	−179.3 (8)
S7—C9—C10—I4	177.6 (5)	C25—C20—C21—C22	−1.9 (12)
I3—C9—C10—I4	−4.1 (11)	F3—C25—C24—F4	0.9 (12)
S7—C11—C12—S9	−2.1 (11)	C20—C25—C24—F4	179.9 (7)
S8—C11—C12—S9	−180.0 (5)	F3—C25—C24—C23	179.6 (7)
S7—C11—C12—S10	178.4 (5)	C20—C25—C24—C23	−1.4 (14)
S8—C11—C12—S10	0.6 (11)	C22—C23—C24—F4	178.8 (7)
S9—C13—C14—S10	−1.0 (10)	C26—C23—C24—F4	−0.5 (12)
S11—C13—C14—S10	−175.5 (6)	C22—C23—C24—C25	0.1 (12)
S9—C13—C14—S12	178.6 (5)	C26—C23—C24—C25	−179.2 (8)
S11—C13—C14—S12	4.0 (14)