Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613032629/bi5028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613032629/bi5028NCCH22S2TTFI2sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613032629/bi5028EDTTTFI2sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613032629/bi5028Isup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613032629/bi5028IIsup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613032629/bi5028sup6.pdf |
CCDC references: 974605; 974606; 974607; 974608
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).
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) Å3 | Prism, orange |
Z = 8 | 0.28 × 0.19 × 0.16 mm |
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 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0222P)2 + 2.9001P] where P = (Fo2 + 2Fc2)/3 |
4208 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 1.17 e Å−3 |
0 restraints | Δρmin = −1.17 e Å−3 |
C12H8I2N2S6 | V = 3684.55 (18) Å3 |
Mr = 626.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 14.6070 (4) Å | µ = 4.09 mm−1 |
b = 12.0315 (3) Å | T = 100 K |
c = 20.9654 (7) Å | 0.28 × 0.19 × 0.16 mm |
Bruker APEX-II CCD diffractometer | 4208 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2003) | 3600 reflections with I > 2σ(I) |
Tmin = 0.353, Tmax = 0.520 | Rint = 0.037 |
15787 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.17 e Å−3 |
4208 reflections | Δρmin = −1.17 e Å−3 |
199 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | Prism, red |
Z = 4 | 0.36 × 0.27 × 0.18 mm |
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 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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.043 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.P)2 + 4.9473P] where P = (Fo2 + 2Fc2)/3 |
1650 reflections | (Δ/σ)max = 0.002 |
86 parameters | Δρmax = 0.97 e Å−3 |
2 restraints | Δρmin = −1.00 e Å−3 |
C8H4I2S6 | V = 1385.25 (7) Å3 |
Mr = 546.27 | Z = 4 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 17.3371 (5) Å | µ = 5.41 mm−1 |
b = 12.6274 (4) Å | T = 150 K |
c = 6.3276 (2) Å | 0.36 × 0.27 × 0.18 mm |
Bruker APEX-II CCD diffractometer | 1653 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2003) | 1581 reflections with I > 2σ(I) |
Tmin = 0.189, Tmax = 0.377 | Rint = 0.029 |
21142 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 2 restraints |
wR(F2) = 0.043 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.97 e Å−3 |
1650 reflections | Δρmin = −1.00 e Å−3 |
86 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
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 |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
I1—C1 | 2.078 (3) | C2—S1i | 1.764 (2) |
S1—C1 | 1.751 (3) | C3—S2i | 1.757 (2) |
S1—C2 | 1.764 (2) | C4—C4i | 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—C5Bi | 1.774 (5) | C5B—S3i | 1.774 (5) |
S3—C5A | 1.827 (5) | C5B—H5BA | 0.9900 |
C1—C1i | 1.331 (6) | C5B—H5BB | 0.9900 |
C2—C3 | 1.344 (5) | ||
C1—S1—C2 | 95.04 (15) | C4i—C4—S2 | 117.52 (10) |
C3—S2—C4 | 95.01 (15) | S3—C4—S2 | 113.58 (16) |
C4—S3—C5Bi | 103.7 (2) | C5B—C5A—S3 | 117.3 (4) |
C4—S3—C5A | 97.6 (2) | C5B—C5A—H5AA | 108.0 |
C1i—C1—S1 | 117.80 (10) | S3—C5A—H5AA | 108.0 |
C1i—C1—I1 | 125.74 (8) | C5B—C5A—H5AB | 108.0 |
S1—C1—I1 | 116.36 (15) | S3—C5A—H5AB | 108.0 |
C3—C2—S1i | 122.82 (11) | H5AA—C5A—H5AB | 107.2 |
C3—C2—S1 | 122.82 (11) | C5A—C5B—S3i | 111.0 (4) |
S1i—C2—S1 | 114.3 (2) | C5A—C5B—H5BA | 109.4 |
C2—C3—S2 | 122.51 (11) | S3i—C5B—H5BA | 109.4 |
C2—C3—S2i | 122.51 (11) | C5A—C5B—H5BB | 109.4 |
S2—C3—S2i | 114.9 (2) | S3i—C5B—H5BB | 109.4 |
C4i—C4—S3 | 128.89 (10) | H5BA—C5B—H5BB | 108.0 |
C2—S1—C1—C1i | 0.64 (14) | C5Bi—S3—C4—C4i | 9.6 (3) |
C2—S1—C1—I1 | −176.03 (18) | C5A—S3—C4—C4i | −16.5 (3) |
C1—S1—C2—C3 | −178.9 (4) | C5Bi—S3—C4—S2 | −171.1 (3) |
C1—S1—C2—S1i | −1.0 (2) | C5A—S3—C4—S2 | 162.8 (3) |
S1i—C2—C3—S2 | −177.6 (2) | C3—S2—C4—C4i | −0.18 (15) |
S1—C2—C3—S2 | 0.1 (5) | C3—S2—C4—S3 | −179.56 (19) |
S1i—C2—C3—S2i | −0.1 (5) | C4—S3—C5A—C5B | 52.9 (5) |
S1—C2—C3—S2i | 177.6 (2) | C5Bi—S3—C5A—C5B | −52.6 (7) |
C4—S2—C3—C2 | 177.9 (4) | S3—C5A—C5B—S3i | −70.6 (5) |
C4—S2—C3—S2i | 0.3 (2) |
Symmetry code: (i) x, −y+1/2, z. |
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) Å3 |
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 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.029P)2 + 1.1208P] where P = (Fo2 + 2Fc2)/3 |
4430 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
C12F4N4·2(C8H4I2S6) | γ = 94.213 (2)° |
Mr = 1368.70 | V = 965.21 (6) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.8311 (2) Å | Mo Kα radiation |
b = 12.0457 (4) Å | µ = 3.93 mm−1 |
c = 16.6577 (6) Å | T = 293 K |
α = 91.128 (2)° | 0.24 × 0.08 × 0.05 mm |
β = 92.950 (2)° |
Nonius KappaCCD diffractometer | 4430 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2003) | 3215 reflections with I > 2σ(I) |
Tmin = 0.693, Tmax = 0.822 | Rint = 0.040 |
12784 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.65 e Å−3 |
4430 reflections | Δρmin = −0.75 e Å−3 |
235 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C14i | 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—C12i | 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—C14i | 123.7 (4) |
S3—C4—S4 | 115.0 (3) | C10—C12—C13 | 123.9 (4) |
C6—C5—S5 | 129.3 (4) | C14i—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—C12i | 124.3 (4) |
C8—C7—S5 | 115.5 (4) | F9—C14—C12i | 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—C14i | −1.0 (8) |
S2—C3—C4—S3 | −179.1 (3) | C9—C10—C12—C14i | 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) | C14i—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) | C14i—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—C12i | 179.8 (5) |
C4—S3—C5—C6 | 2.3 (4) | C12—C13—C14—C12i | 0.2 (9) |
C4—S3—C5—S5 | −179.8 (3) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
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) Å3 |
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 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0537P)2 + 19.0915P] where P = (Fo2 + 2Fc2)/3 |
8748 reflections | (Δ/σ)max < 0.001 |
478 parameters | Δρmax = 1.71 e Å−3 |
0 restraints | Δρmin = −2.62 e Å−3 |
C12F4N4·2(C8H4I2S6) | γ = 95.863 (2)° |
Mr = 1368.70 | V = 1907.83 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.0030 (4) Å | Mo Kα radiation |
b = 12.7689 (4) Å | µ = 3.98 mm−1 |
c = 14.9201 (5) Å | T = 293 K |
α = 104.906 (2)° | 0.32 × 0.22 × 0.03 mm |
β = 106.449 (2)° |
Nonius KappaCCD diffractometer | 8748 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2003) | 5762 reflections with I > 2σ(I) |
Tmin = 0.364, Tmax = 0.888 | Rint = 0.057 |
33190 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0537P)2 + 19.0915P] where P = (Fo2 + 2Fc2)/3 |
8748 reflections | Δρmax = 1.71 e Å−3 |
478 parameters | Δρmin = −2.62 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
Experimental details
(NCCH22S2TTFI2) | (EDTTTFI2) | (I) | (II) | |
Crystal data | ||||
Chemical formula | C12H8I2N2S6 | C8H4I2S6 | C12F4N4·2(C8H4I2S6) | C12F4N4·2(C8H4I2S6) |
Mr | 626.36 | 546.27 | 1368.70 | 1368.70 |
Crystal system, space group | Orthorhombic, Pbca | Orthorhombic, Pnma | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 100 | 150 | 293 | 293 |
a, b, c (Å) | 14.6070 (4), 12.0315 (3), 20.9654 (7) | 17.3371 (5), 12.6274 (4), 6.3276 (2) | 4.8311 (2), 12.0457 (4), 16.6577 (6) | 11.0030 (4), 12.7689 (4), 14.9201 (5) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 91.128 (2), 92.950 (2), 94.213 (2) | 104.906 (2), 106.449 (2), 95.863 (2) |
V (Å3) | 3684.55 (18) | 1385.25 (7) | 965.21 (6) | 1907.83 (11) |
Z | 8 | 4 | 1 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 4.09 | 5.41 | 3.93 | 3.98 |
Crystal size (mm) | 0.28 × 0.19 × 0.16 | 0.36 × 0.27 × 0.18 | 0.24 × 0.08 × 0.05 | 0.32 × 0.22 × 0.03 |
Data collection | ||||
Diffractometer | Bruker APEX-II CCD | Bruker APEX-II CCD | Nonius KappaCCD | Nonius KappaCCD |
Absorption correction | Multi-scan SADABS (Bruker, 2003) | Multi-scan SADABS (Bruker, 2003) | Multi-scan SADABS (Bruker, 2003) | Multi-scan SADABS (Bruker, 2003) |
Tmin, Tmax | 0.353, 0.520 | 0.189, 0.377 | 0.693, 0.822 | 0.364, 0.888 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15787, 4208, 3600 | 21142, 1653, 1581 | 12784, 4430, 3215 | 33190, 8748, 5762 |
Rint | 0.037 | 0.029 | 0.040 | 0.057 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 | 0.650 | 0.650 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.063, 1.07 | 0.022, 0.043, 1.12 | 0.035, 0.082, 1.09 | 0.057, 0.162, 1.08 |
No. of reflections | 4208 | 1650 | 4430 | 8748 |
No. of parameters | 199 | 86 | 235 | 478 |
No. of restraints | 0 | 2 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0222P)2 + 2.9001P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.P)2 + 4.9473P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.029P)2 + 1.1208P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0537P)2 + 19.0915P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.17, −1.17 | 0.97, −1.00 | 0.65, −0.75 | 1.71, −2.62 |
Computer programs: APEX2 (Bruker, 2005), COLLECT (Nonius, 1998), SAINT (Bruker, 2003), DIRAX (Duisenberg, 1992), SAINT, EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Brendt, 2001), WinGX (Farrugia, 2012).