Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005489/cv6462sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005489/cv6462Isup2.hkl |
CCDC reference: 269549
Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C14H14N2S8 | F(000) = 960 |
Mr = 466.75 | Dx = 1.562 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5703 reflections |
a = 16.2850 (4) Å | θ = 2.2–28.1° |
b = 11.6795 (3) Å | µ = 0.90 mm−1 |
c = 10.7413 (3) Å | T = 180 K |
β = 103.635 (1)° | Needle, orange |
V = 1985.42 (9) Å3 | 0.25 × 0.15 × 0.15 mm |
Z = 4 |
Bruker–Nonius X8 APEX-II CCD diffractometer | 6059 independent reflections |
Radiation source: fine-focus sealed tube | 4352 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Thin–slice ω and φ scans | θmax = 30.5°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −23→23 |
Tmin = 0.762, Tmax = 0.877 | k = −13→16 |
28528 measured reflections | l = −15→14 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3 |
6059 reflections | (Δ/σ)max = 0.001 |
219 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
Experimental. INTENSITY STATISTICS FOR DATASET # 1 jj0504m.hkl Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma) Inf - 1.95 319 319 100.0 7.94 522.2 45.03 0.0220 0.0161 1.95 - 1.50 361 361 100.0 7.49 256.8 40.83 0.0275 0.0178 1.50 - 1.30 352 352 100.0 7.14 216.9 36.52 0.0312 0.0194 1.30 - 1.15 437 437 100.0 6.16 148.7 29.54 0.0390 0.0238 1.15 - 1.05 460 460 100.0 5.33 82.8 22.35 0.0551 0.0328 1.05 - 0.95 648 648 100.0 4.74 69.6 17.36 0.0612 0.0407 0.95 - 0.90 443 443 100.0 4.43 56.3 14.70 0.0741 0.0516 0.90 - 0.85 574 574 100.0 4.03 46.8 11.52 0.0850 0.0654 0.85 - 0.80 690 690 100.0 3.71 39.3 8.87 0.0967 0.0855 0.80 - 0.75 894 894 100.0 3.40 29.3 6.82 0.1195 0.1253 0.75 - 0.70 1173 1179 99.5 3.02 18.8 4.03 0.1663 0.2280 —————————————————————————— 0.80 - 0.70 2067 2073 99.7 3.19 23.3 5.24 0.1394 0.1722 Inf - 0.70 6351 6357 99.9 4.63 96.2 16.77 0.0401 0.0395 Merged [A], lowest resolution = 15.83 Angstroms, 1075 outliers downweighted |
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 | ||
S1 | −0.17392 (3) | 0.35540 (5) | −0.02047 (5) | 0.04003 (13) | |
S2 | −0.13585 (3) | 0.54078 (5) | 0.22979 (5) | 0.04287 (14) | |
S3 | 0.01281 (3) | 0.32411 (4) | 0.03609 (5) | 0.03603 (12) | |
S4 | 0.04628 (3) | 0.47519 (5) | 0.26231 (5) | 0.04028 (13) | |
S5 | 0.21607 (3) | 0.28518 (4) | 0.07437 (4) | 0.02994 (11) | |
S6 | 0.24788 (2) | 0.42905 (3) | 0.30558 (4) | 0.02344 (10) | |
S7 | 0.39763 (3) | 0.29674 (4) | 0.05426 (4) | 0.02887 (11) | |
S8 | 0.43428 (2) | 0.45419 (3) | 0.30962 (4) | 0.02489 (10) | |
N1 | 0.43824 (10) | 0.69766 (13) | 0.08123 (15) | 0.0357 (4) | |
N2 | 0.32877 (11) | 0.53975 (15) | −0.35829 (17) | 0.0455 (4) | |
C1 | −0.20090 (12) | 0.24379 (18) | 0.0780 (2) | 0.0469 (5) | |
H1A | −0.2519 | 0.2043 | 0.0309 | 0.070* | |
H1B | −0.2113 | 0.2772 | 0.1565 | 0.070* | |
H1C | −0.1542 | 0.1890 | 0.1001 | 0.070* | |
C2 | −0.11573 (13) | 0.4970 (2) | 0.3932 (2) | 0.0552 (6) | |
H2A | −0.1623 | 0.5219 | 0.4302 | 0.083* | |
H2B | −0.0628 | 0.5315 | 0.4411 | 0.083* | |
H2C | −0.1110 | 0.4134 | 0.3982 | 0.083* | |
C3 | −0.07437 (10) | 0.39201 (16) | 0.07425 (16) | 0.0298 (4) | |
C4 | −0.05933 (10) | 0.46108 (16) | 0.17692 (17) | 0.0323 (4) | |
C5 | 0.08856 (10) | 0.38830 (15) | 0.15956 (16) | 0.0270 (4) | |
C6 | 0.17242 (9) | 0.37182 (14) | 0.17564 (15) | 0.0241 (3) | |
C7 | 0.31780 (9) | 0.34461 (13) | 0.12513 (15) | 0.0225 (3) | |
C8 | 0.33280 (9) | 0.40976 (12) | 0.23174 (15) | 0.0194 (3) | |
C9 | 0.36023 (10) | 0.34665 (13) | −0.10856 (15) | 0.0230 (3) | |
H9A | 0.3920 | 0.3074 | −0.1641 | 0.028* | |
H9B | 0.2998 | 0.3265 | −0.1394 | 0.028* | |
C10 | 0.37057 (11) | 0.47547 (14) | −0.11944 (17) | 0.0304 (4) | |
H10A | 0.3347 | 0.5153 | −0.0704 | 0.036* | |
H10B | 0.4301 | 0.4968 | −0.0821 | 0.036* | |
C11 | 0.34659 (11) | 0.51200 (15) | −0.25376 (19) | 0.0314 (4) | |
C12 | 0.41654 (10) | 0.59108 (13) | 0.37697 (15) | 0.0246 (3) | |
H12A | 0.3814 | 0.5790 | 0.4395 | 0.029* | |
H12B | 0.4716 | 0.6220 | 0.4245 | 0.029* | |
C13 | 0.37351 (10) | 0.68051 (13) | 0.27946 (16) | 0.0255 (3) | |
H13A | 0.3131 | 0.6603 | 0.2491 | 0.031* | |
H13B | 0.3766 | 0.7559 | 0.3226 | 0.031* | |
C14 | 0.41062 (10) | 0.69068 (13) | 0.16910 (17) | 0.0249 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0236 (2) | 0.0558 (3) | 0.0339 (3) | −0.0129 (2) | −0.00675 (18) | 0.0105 (2) |
S2 | 0.0249 (2) | 0.0622 (3) | 0.0407 (3) | 0.0121 (2) | 0.0061 (2) | 0.0076 (3) |
S3 | 0.0237 (2) | 0.0537 (3) | 0.0298 (2) | −0.01220 (19) | 0.00431 (18) | −0.0105 (2) |
S4 | 0.0176 (2) | 0.0706 (4) | 0.0311 (3) | −0.0012 (2) | 0.00275 (18) | −0.0170 (2) |
S5 | 0.0250 (2) | 0.0354 (2) | 0.0294 (2) | −0.00534 (16) | 0.00645 (17) | −0.01004 (19) |
S6 | 0.01766 (17) | 0.0306 (2) | 0.0222 (2) | −0.00239 (14) | 0.00501 (15) | −0.00329 (17) |
S7 | 0.0262 (2) | 0.0374 (2) | 0.0239 (2) | 0.01246 (17) | 0.00759 (17) | 0.00396 (19) |
S8 | 0.01556 (17) | 0.02587 (19) | 0.0310 (2) | 0.00121 (14) | 0.00108 (15) | 0.00326 (18) |
N1 | 0.0431 (9) | 0.0357 (8) | 0.0307 (9) | −0.0009 (7) | 0.0136 (7) | 0.0046 (7) |
N2 | 0.0446 (10) | 0.0534 (10) | 0.0383 (10) | −0.0067 (8) | 0.0096 (8) | 0.0134 (9) |
C1 | 0.0385 (11) | 0.0565 (13) | 0.0456 (13) | −0.0205 (9) | 0.0101 (9) | 0.0066 (11) |
C2 | 0.0396 (12) | 0.0900 (17) | 0.0374 (12) | 0.0227 (11) | 0.0120 (9) | 0.0063 (12) |
C3 | 0.0183 (7) | 0.0430 (10) | 0.0264 (9) | −0.0079 (7) | 0.0018 (6) | 0.0069 (8) |
C4 | 0.0160 (7) | 0.0512 (11) | 0.0290 (9) | −0.0017 (7) | 0.0038 (7) | 0.0055 (9) |
C5 | 0.0195 (7) | 0.0384 (9) | 0.0230 (8) | −0.0073 (6) | 0.0051 (6) | −0.0026 (7) |
C6 | 0.0205 (7) | 0.0300 (8) | 0.0220 (8) | −0.0055 (6) | 0.0052 (6) | −0.0025 (7) |
C7 | 0.0210 (7) | 0.0241 (7) | 0.0230 (8) | 0.0017 (6) | 0.0063 (6) | 0.0022 (7) |
C8 | 0.0172 (7) | 0.0203 (7) | 0.0214 (8) | 0.0011 (5) | 0.0057 (6) | 0.0041 (6) |
C9 | 0.0245 (8) | 0.0262 (8) | 0.0183 (8) | 0.0015 (6) | 0.0050 (6) | −0.0026 (7) |
C10 | 0.0353 (9) | 0.0268 (8) | 0.0272 (9) | −0.0020 (7) | 0.0038 (7) | −0.0033 (7) |
C11 | 0.0287 (8) | 0.0289 (8) | 0.0364 (11) | −0.0041 (7) | 0.0076 (8) | 0.0017 (8) |
C12 | 0.0241 (8) | 0.0290 (8) | 0.0193 (8) | −0.0047 (6) | 0.0024 (6) | −0.0018 (7) |
C13 | 0.0285 (8) | 0.0256 (8) | 0.0241 (8) | 0.0004 (6) | 0.0095 (7) | 0.0002 (7) |
C14 | 0.0251 (8) | 0.0224 (8) | 0.0262 (9) | 0.0000 (6) | 0.0044 (7) | 0.0011 (7) |
S1—C3 | 1.7517 (16) | C1—H1C | 0.980 |
S1—C1 | 1.797 (2) | C2—H2A | 0.980 |
S2—C4 | 1.7536 (18) | C2—H2B | 0.980 |
S2—C2 | 1.783 (2) | C2—H2C | 0.980 |
S3—C5 | 1.7525 (16) | C3—C4 | 1.342 (2) |
S3—C3 | 1.7570 (18) | C5—C6 | 1.349 (2) |
S4—C5 | 1.7551 (18) | C7—C8 | 1.348 (2) |
S4—C4 | 1.7557 (16) | C9—C10 | 1.522 (2) |
S5—C6 | 1.7542 (17) | C9—H9A | 0.990 |
S5—C7 | 1.7601 (15) | C9—H9B | 0.990 |
S6—C6 | 1.7596 (15) | C10—C11 | 1.466 (2) |
S6—C8 | 1.7634 (15) | C10—H10A | 0.990 |
S7—C7 | 1.7461 (16) | C10—H10B | 0.990 |
S7—C9 | 1.8076 (16) | C12—C13 | 1.527 (2) |
S8—C8 | 1.7460 (15) | C12—H12A | 0.990 |
S8—C12 | 1.8060 (16) | C12—H12B | 0.990 |
N1—C14 | 1.140 (2) | C13—C14 | 1.457 (2) |
N2—C11 | 1.139 (2) | C13—H13A | 0.990 |
C1—H1A | 0.980 | C13—H13B | 0.990 |
C1—H1B | 0.980 | ||
C3—S1—C1 | 99.01 (9) | C8—C7—S7 | 123.13 (12) |
C4—S2—C2 | 100.77 (9) | C8—C7—S5 | 117.03 (12) |
C5—S3—C3 | 95.38 (8) | S7—C7—S5 | 118.80 (9) |
C5—S4—C4 | 95.65 (8) | C7—C8—S8 | 122.42 (12) |
C6—S5—C7 | 94.00 (7) | C7—C8—S6 | 116.73 (11) |
C6—S6—C8 | 94.00 (7) | S8—C8—S6 | 120.04 (9) |
C7—S7—C9 | 101.70 (7) | C10—C9—S7 | 112.03 (11) |
C8—S8—C12 | 103.43 (7) | C10—C9—H9A | 109.2 |
S1—C1—H1A | 109.5 | S7—C9—H9A | 109.2 |
S1—C1—H1B | 109.5 | C10—C9—H9B | 109.2 |
H1A—C1—H1B | 109.5 | S7—C9—H9B | 109.2 |
S1—C1—H1C | 109.5 | H9A—C9—H9B | 107.9 |
H1A—C1—H1C | 109.5 | C11—C10—C9 | 110.77 (14) |
H1B—C1—H1C | 109.5 | C11—C10—H10A | 109.5 |
S2—C2—H2A | 109.5 | C9—C10—H10A | 109.5 |
S2—C2—H2B | 109.5 | C11—C10—H10B | 109.5 |
H2A—C2—H2B | 109.5 | C9—C10—H10B | 109.5 |
S2—C2—H2C | 109.5 | H10A—C10—H10B | 108.1 |
H2A—C2—H2C | 109.5 | N2—C11—C10 | 179.2 (2) |
H2B—C2—H2C | 109.5 | C13—C12—S8 | 114.94 (11) |
C4—C3—S1 | 126.08 (14) | C13—C12—H12A | 108.5 |
C4—C3—S3 | 117.53 (12) | S8—C12—H12A | 108.5 |
S1—C3—S3 | 116.26 (10) | C13—C12—H12B | 108.5 |
C3—C4—S2 | 125.41 (13) | S8—C12—H12B | 108.5 |
C3—C4—S4 | 116.90 (13) | H12A—C12—H12B | 107.5 |
S2—C4—S4 | 117.66 (11) | C14—C13—C12 | 113.73 (14) |
C6—C5—S3 | 123.12 (13) | C14—C13—H13A | 108.8 |
C6—C5—S4 | 122.50 (13) | C12—C13—H13A | 108.8 |
S3—C5—S4 | 114.38 (9) | C14—C13—H13B | 108.8 |
C5—C6—S5 | 123.28 (13) | C12—C13—H13B | 108.8 |
C5—C6—S6 | 122.94 (13) | H13A—C13—H13B | 107.7 |
S5—C6—S6 | 113.69 (9) | N1—C14—C13 | 178.62 (18) |
C1—S1—C3—C4 | −81.57 (18) | C7—S5—C6—C5 | 162.52 (15) |
C1—S1—C3—S3 | 94.12 (12) | C7—S5—C6—S6 | −20.81 (10) |
C5—S3—C3—C4 | −2.20 (16) | C8—S6—C6—C5 | −162.89 (15) |
C5—S3—C3—S1 | −178.26 (10) | C8—S6—C6—S5 | 20.43 (10) |
S1—C3—C4—S2 | −6.5 (3) | C9—S7—C7—C8 | −125.92 (14) |
S3—C3—C4—S2 | 177.91 (10) | C9—S7—C7—S5 | 66.06 (10) |
S1—C3—C4—S4 | 175.33 (10) | C6—S5—C7—C8 | 13.19 (14) |
S3—C3—C4—S4 | −0.3 (2) | C6—S5—C7—S7 | −178.07 (10) |
C2—S2—C4—C3 | 127.20 (18) | S7—C7—C8—S8 | 0.5 (2) |
C2—S2—C4—S4 | −54.59 (14) | S5—C7—C8—S8 | 168.75 (8) |
C5—S4—C4—C3 | 2.64 (16) | S7—C7—C8—S6 | −169.17 (9) |
C5—S4—C4—S2 | −175.72 (11) | S5—C7—C8—S6 | −0.96 (17) |
C3—S3—C5—C6 | −176.72 (16) | C12—S8—C8—C7 | 148.65 (13) |
C3—S3—C5—S4 | 3.90 (11) | C12—S8—C8—S6 | −41.97 (11) |
C4—S4—C5—C6 | 176.57 (16) | C6—S6—C8—C7 | −11.76 (13) |
C4—S4—C5—S3 | −4.04 (11) | C6—S6—C8—S8 | 178.27 (9) |
S3—C5—C6—S5 | 0.5 (2) | C7—S7—C9—C10 | 73.88 (13) |
S4—C5—C6—S5 | 179.88 (10) | S7—C9—C10—C11 | 175.10 (12) |
S3—C5—C6—S6 | −175.82 (9) | C8—S8—C12—C13 | −59.12 (13) |
S4—C5—C6—S6 | 3.5 (2) | S8—C12—C13—C14 | −47.61 (17) |