Supporting information
Crystallographic Information File (CIF) | |
Structure factor file (CIF format) |
CCDC reference: 134772
Cell refinement: DENZO (Otwinoski & Minor, 1993); data reduction: DENZO (Otwinoski & Minor, 1993) & CCP4 (SCALA (Evans, 1997)); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1976).
C10H8S8·1.5I | Z = 2 |
Mr = 574.99 | F(000) = 551 |
Triclinic, P1 | Dx = 2.276 Mg m−3 |
a = 6.585 Å | Synchrotron radiation, λ = 0.68870 Å |
b = 9.038 Å | Cell parameters from 896 reflections |
c = 15.205 Å | θ = 2.8–24.9° |
α = 94.90° | µ = 3.81 mm−1 |
β = 95.74° | T = 200 K |
γ = 110.00° | Plate, brown |
V = 839.1 Å3 | 0.01 × 0.01 × 0.002 mm |
Princeton CCD (1024x1024 pixels) diffractometer | 2746 reflections with I > 2σ(I) |
Radiation source: European Synchrotron Radiation Facility | Rint = 0.032 |
Si(111) monochromator | θmax = 27.3°, θmin = 3.2° |
ϕ scans | h = −8→7 |
13912 measured reflections | k = −11→11 |
3230 independent reflections | l = 0→20 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0097P)2 + 5.7148P] where P = (Fo2 + 2Fc2)/3 |
3230 reflections | (Δ/σ)max = 0.002 |
198 parameters | Δρmax = 2.28 e Å−3 |
20 restraints | Δρmin = −1.72 e Å−3 |
C10H8S8·1.5I | γ = 110.00° |
Mr = 574.99 | V = 839.1 Å3 |
Triclinic, P1 | Z = 2 |
a = 6.585 Å | Synchrotron radiation, λ = 0.68870 Å |
b = 9.038 Å | µ = 3.81 mm−1 |
c = 15.205 Å | T = 200 K |
α = 94.90° | 0.01 × 0.01 × 0.002 mm |
β = 95.74° |
Princeton CCD (1024x1024 pixels) diffractometer | 2746 reflections with I > 2σ(I) |
13912 measured reflections | Rint = 0.032 |
3230 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 20 restraints |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 2.28 e Å−3 |
3230 reflections | Δρmin = −1.72 e Å−3 |
198 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 | 0.0000 | 0.0000 | 0.0000 | 0.03994 (17) | 0.986 (3) |
I2 | 0.40573 (8) | 0.25157 (6) | −0.01721 (3) | 0.05150 (16) | 0.986 (3) |
S1 | 0.0963 (2) | −0.14611 (17) | 0.43081 (8) | 0.0288 (3) | |
S2 | 0.4627 (2) | −0.26148 (17) | 0.44813 (8) | 0.0263 (3) | |
S3 | 0.2085 (3) | 0.0071 (2) | 0.27059 (10) | 0.0392 (4) | |
S4 | 0.6385 (3) | −0.1389 (2) | 0.28793 (10) | 0.0394 (4) | |
S5 | 0.2814 (2) | −0.43049 (16) | 0.61967 (7) | 0.0249 (3) | |
S6 | −0.0835 (2) | −0.31358 (17) | 0.59826 (7) | 0.0256 (3) | |
S7 | 0.1971 (2) | −0.54159 (18) | 0.79329 (8) | 0.0322 (3) | |
S8 | −0.2374 (2) | −0.39674 (18) | 0.76841 (8) | 0.0322 (3) | |
C1 | 0.2268 (8) | −0.2543 (6) | 0.4878 (3) | 0.0217 (10) | |
C2 | 0.2721 (8) | −0.1055 (6) | 0.3496 (3) | 0.0237 (11) | |
C3 | 0.4092 (8) | 0.0204 (8) | 0.1965 (3) | 0.0376 (14) | |
H3A | 0.3478 | −0.0834 | 0.1472 | 0.045* | |
H3B | 0.4265 | 0.1226 | 0.1619 | 0.045* | |
C4 | 0.6299 (9) | 0.0335 (6) | 0.2389 (4) | 0.0350 (13) | |
H4A | 0.6896 | 0.1347 | 0.2900 | 0.042* | |
H4B | 0.7393 | 0.0559 | 0.1892 | 0.042* | |
C5 | 0.4378 (9) | −0.1576 (6) | 0.3580 (3) | 0.0251 (11) | |
C6 | 0.1496 (8) | −0.3259 (6) | 0.5590 (3) | 0.0214 (10) | |
C7 | 0.1177 (8) | −0.4523 (6) | 0.7054 (3) | 0.0205 (10) | |
C8A | −0.0351 (15) | −0.5828 (13) | 0.8529 (8) | 0.030 (3) | 0.490 (17) |
H8A | −0.1689 | −0.6817 | 0.8160 | 0.036* | 0.49 |
H8B | 0.0057 | −0.6168 | 0.9169 | 0.036* | 0.49 |
C9A | −0.106 (2) | −0.4432 (14) | 0.8670 (5) | 0.031 (3) | 0.490 (17) |
H9A | 0.0357 | −0.3405 | 0.8942 | 0.037* | 0.49 |
H9B | −0.2168 | −0.4649 | 0.9161 | 0.037* | 0.49 |
C8B | 0.0429 (15) | −0.4891 (17) | 0.8747 (5) | 0.038 (4) | 0.510 (17) |
H8C | 0.0594 | −0.5481 | 0.9324 | 0.046* | 0.51 |
H8D | 0.1146 | −0.3628 | 0.8956 | 0.046* | 0.51 |
C9B | −0.1946 (15) | −0.5298 (13) | 0.8437 (8) | 0.032 (3) | 0.510 (17) |
H9C | −0.2785 | −0.5228 | 0.9006 | 0.039* | 0.51 |
H9D | −0.2623 | −0.6502 | 0.8106 | 0.039* | 0.51 |
C10 | −0.0491 (8) | −0.3979 (6) | 0.6958 (3) | 0.0210 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0487 (4) | 0.0416 (3) | 0.0244 (2) | 0.0114 (3) | −0.0044 (2) | 0.0068 (2) |
I2 | 0.0598 (3) | 0.0495 (3) | 0.0365 (2) | 0.0067 (2) | 0.00794 (19) | 0.01076 (18) |
S1 | 0.0301 (9) | 0.0439 (8) | 0.0255 (6) | 0.0239 (6) | 0.0136 (5) | 0.0174 (5) |
S2 | 0.0231 (8) | 0.0416 (8) | 0.0224 (5) | 0.0181 (6) | 0.0075 (4) | 0.0144 (5) |
S3 | 0.0381 (10) | 0.0571 (10) | 0.0433 (8) | 0.0318 (8) | 0.0224 (6) | 0.0355 (7) |
S4 | 0.0401 (10) | 0.0586 (10) | 0.0416 (7) | 0.0337 (8) | 0.0273 (7) | 0.0305 (7) |
S5 | 0.0244 (8) | 0.0399 (8) | 0.0181 (5) | 0.0188 (6) | 0.0060 (4) | 0.0105 (5) |
S6 | 0.0246 (8) | 0.0415 (8) | 0.0195 (5) | 0.0197 (6) | 0.0070 (4) | 0.0118 (5) |
S7 | 0.0349 (9) | 0.0502 (9) | 0.0230 (6) | 0.0250 (7) | 0.0089 (5) | 0.0182 (5) |
S8 | 0.0327 (9) | 0.0481 (9) | 0.0293 (6) | 0.0240 (7) | 0.0180 (5) | 0.0198 (6) |
C1 | 0.023 (3) | 0.030 (3) | 0.0167 (19) | 0.014 (2) | 0.0044 (17) | 0.0073 (17) |
C2 | 0.021 (3) | 0.036 (3) | 0.021 (2) | 0.014 (2) | 0.0085 (18) | 0.0151 (19) |
C3 | 0.037 (4) | 0.054 (4) | 0.032 (3) | 0.023 (3) | 0.014 (2) | 0.020 (3) |
C4 | 0.029 (4) | 0.039 (3) | 0.039 (3) | 0.010 (3) | 0.013 (2) | 0.018 (2) |
C5 | 0.025 (3) | 0.035 (3) | 0.022 (2) | 0.014 (2) | 0.0095 (18) | 0.0120 (19) |
C6 | 0.020 (3) | 0.034 (3) | 0.0171 (19) | 0.016 (2) | 0.0044 (17) | 0.0073 (18) |
C7 | 0.020 (3) | 0.027 (3) | 0.0148 (19) | 0.008 (2) | 0.0015 (16) | 0.0081 (17) |
C8A | 0.027 (8) | 0.036 (7) | 0.031 (6) | 0.011 (6) | 0.010 (5) | 0.021 (5) |
C9A | 0.044 (10) | 0.031 (8) | 0.025 (5) | 0.017 (7) | 0.014 (5) | 0.015 (5) |
C8B | 0.031 (7) | 0.065 (12) | 0.021 (5) | 0.018 (7) | 0.008 (4) | 0.014 (5) |
C9B | 0.031 (6) | 0.022 (7) | 0.043 (6) | 0.002 (5) | 0.016 (5) | 0.018 (5) |
C10 | 0.022 (3) | 0.027 (3) | 0.0155 (19) | 0.008 (2) | 0.0067 (17) | 0.0074 (17) |
I1—I2i | 2.9089 (8) | S8—C9A | 1.808 (5) |
I1—I2 | 2.9089 (8) | C1—C6 | 1.361 (6) |
S1—C1 | 1.737 (5) | C2—C5 | 1.327 (7) |
S1—C2 | 1.753 (5) | C3—C4 | 1.491 (7) |
S2—C1 | 1.741 (5) | C3—H3A | 1.0800 |
S2—C5 | 1.752 (5) | C3—H3B | 1.0800 |
S3—C2 | 1.747 (5) | C4—H4A | 1.0800 |
S3—C3 | 1.800 (4) | C4—H4B | 1.0800 |
S4—C5 | 1.752 (5) | C7—C10 | 1.349 (7) |
S4—C4 | 1.799 (4) | C8A—C9A | 1.494 (7) |
S5—C6 | 1.746 (5) | C8A—H8A | 1.0800 |
S5—C7 | 1.755 (5) | C8A—H8B | 1.0800 |
S6—C6 | 1.736 (5) | C9A—H9A | 1.0800 |
S6—C10 | 1.754 (4) | C9A—H9B | 1.0800 |
S7—C7 | 1.744 (4) | C8B—C9B | 1.495 (7) |
S7—C8A | 1.801 (5) | C8B—H8C | 1.0800 |
S7—C8B | 1.808 (5) | C8B—H8D | 1.0800 |
S8—C10 | 1.743 (5) | C9B—H9C | 1.0800 |
S8—C9B | 1.800 (5) | C9B—H9D | 1.0800 |
I2i—I1—I2 | 180.0 | C1—C6—S6 | 122.0 (4) |
C1—S1—C2 | 95.3 (2) | C1—C6—S5 | 122.8 (4) |
C1—S2—C5 | 94.8 (2) | S6—C6—S5 | 115.1 (2) |
C2—S3—C3 | 102.8 (2) | C10—C7—S7 | 128.6 (3) |
C5—S4—C4 | 99.6 (2) | C10—C7—S5 | 117.0 (3) |
C6—S5—C7 | 95.1 (2) | S7—C7—S5 | 114.4 (3) |
C6—S6—C10 | 95.3 (2) | C9A—C8A—S7 | 112.3 (7) |
C7—S7—C8A | 101.4 (4) | C9A—C8A—H8A | 109.2 |
C7—S7—C8B | 98.7 (4) | S7—C8A—H8A | 109.2 |
C8A—S7—C8B | 27.0 (5) | C9A—C8A—H8B | 109.1 |
C10—S8—C9B | 101.3 (4) | S7—C8A—H8B | 109.1 |
C10—S8—C9A | 99.6 (4) | H8A—C8A—H8B | 107.9 |
C9B—S8—C9A | 26.4 (4) | C8A—C9A—S8 | 115.3 (7) |
C6—C1—S1 | 121.7 (4) | C8A—C9A—H9A | 108.4 |
C6—C1—S2 | 123.1 (4) | S8—C9A—H9A | 108.4 |
S1—C1—S2 | 115.2 (2) | C8A—C9A—H9B | 108.4 |
C5—C2—S3 | 129.0 (4) | S8—C9A—H9B | 108.4 |
C5—C2—S1 | 116.8 (3) | H9A—C9A—H9B | 107.5 |
S3—C2—S1 | 114.2 (3) | C9B—C8B—S7 | 115.5 (7) |
C4—C3—S3 | 116.1 (3) | C9B—C8B—H8C | 108.4 |
C4—C3—H3A | 108.3 | S7—C8B—H8C | 108.4 |
S3—C3—H3A | 108.3 | C9B—C8B—H8D | 108.4 |
C4—C3—H3B | 108.3 | S7—C8B—H8D | 108.4 |
S3—C3—H3B | 108.3 | H8C—C8B—H8D | 107.5 |
H3A—C3—H3B | 107.4 | C8B—C9B—S8 | 111.0 (7) |
C3—C4—S4 | 114.6 (4) | C8B—C9B—H9C | 109.4 |
C3—C4—H4A | 108.6 | S8—C9B—H9C | 109.4 |
S4—C4—H4A | 108.6 | C8B—C9B—H9D | 109.4 |
C3—C4—H4B | 108.6 | S8—C9B—H9D | 109.4 |
S4—C4—H4B | 108.6 | H9C—C9B—H9D | 108.0 |
H4A—C4—H4B | 107.6 | C7—C10—S8 | 128.9 (3) |
C2—C5—S2 | 117.9 (3) | C7—C10—S6 | 116.9 (3) |
C2—C5—S4 | 128.0 (4) | S8—C10—S6 | 114.2 (3) |
S2—C5—S4 | 114.2 (3) | ||
C2—S1—C1—C6 | −176.7 (5) | C8A—S7—C7—C10 | 12.7 (7) |
C2—S1—C1—S2 | 4.2 (3) | C8B—S7—C7—C10 | −14.6 (7) |
C5—S2—C1—C6 | 176.8 (5) | C8A—S7—C7—S5 | −167.9 (5) |
C5—S2—C1—S1 | −4.0 (3) | C8B—S7—C7—S5 | 164.8 (5) |
C3—S3—C2—C5 | 5.1 (6) | C6—S5—C7—C10 | 4.1 (5) |
C3—S3—C2—S1 | −177.9 (3) | C6—S5—C7—S7 | −175.4 (3) |
C1—S1—C2—C5 | −2.7 (5) | C7—S7—C8A—C9A | −47.3 (9) |
C1—S1—C2—S3 | 179.9 (3) | C8B—S7—C8A—C9A | 39.6 (8) |
C2—S3—C3—C4 | −35.9 (5) | S7—C8A—C9A—S8 | 72.0 (13) |
S3—C3—C4—S4 | 65.6 (6) | C10—S8—C9A—C8A | −49.5 (10) |
C5—S4—C4—C3 | −54.2 (4) | C9B—S8—C9A—C8A | 46.7 (9) |
S3—C2—C5—S2 | 177.3 (3) | C7—S7—C8B—C9B | 51.7 (10) |
S1—C2—C5—S2 | 0.3 (6) | C8A—S7—C8B—C9B | −46.3 (8) |
S3—C2—C5—S4 | −3.9 (9) | S7—C8B—C9B—S8 | −73.9 (13) |
S1—C2—C5—S4 | 179.1 (3) | C10—S8—C9B—C8B | 47.9 (9) |
C1—S2—C5—C2 | 2.2 (5) | C9A—S8—C9B—C8B | −40.8 (8) |
C1—S2—C5—S4 | −176.7 (3) | S7—C7—C10—S8 | 0.9 (8) |
C4—S4—C5—C2 | 24.3 (6) | S5—C7—C10—S8 | −178.5 (3) |
C4—S4—C5—S2 | −156.8 (3) | S7—C7—C10—S6 | 179.9 (3) |
S1—C1—C6—S6 | −0.3 (7) | S5—C7—C10—S6 | 0.5 (6) |
S2—C1—C6—S6 | 178.8 (3) | C9B—S8—C10—C7 | −13.9 (7) |
S1—C1—C6—S5 | −178.1 (3) | C9A—S8—C10—C7 | 12.8 (7) |
S2—C1—C6—S5 | 1.0 (7) | C9B—S8—C10—S6 | 167.0 (5) |
C10—S6—C6—C1 | −170.3 (5) | C9A—S8—C10—S6 | −166.2 (5) |
C10—S6—C6—S5 | 7.6 (3) | C6—S6—C10—C7 | −4.9 (5) |
C7—S5—C6—C1 | 170.5 (5) | C6—S6—C10—S8 | 174.3 (3) |
C7—S5—C6—S6 | −7.4 (3) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C10H8S8·1.5I |
Mr | 574.99 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 200 |
a, b, c (Å) | 6.585, 9.038, 15.205 |
α, β, γ (°) | 94.90, 95.74, 110.00 |
V (Å3) | 839.1 |
Z | 2 |
Radiation type | Synchrotron, λ = 0.68870 Å |
µ (mm−1) | 3.81 |
Crystal size (mm) | 0.01 × 0.01 × 0.002 |
Data collection | |
Diffractometer | Princeton CCD (1024x1024 pixels) diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13912, 3230, 2746 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.081, 1.08 |
No. of reflections | 3230 |
No. of parameters | 198 |
No. of restraints | 20 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 2.28, −1.72 |
Computer programs: , DENZO (Otwinoski & Minor, 1993) & CCP4 (SCALA (Evans, 1997)), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1976).