Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059533/cv2356sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059533/cv2356Isup2.hkl |
CCDC reference: 673016
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.129
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.18 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 5.58 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For details of the preparation of the title compound, see: Yin et al. (2006, 2007). For the crystal structures of similar compounds, see: Chen et al. (2007); Gao et al. (2007). For applications of the title compound, see: Ellison et al. (1973); Yuguchi et al. (2004).
The title compound was prepared according to the method described by Yin et al. (2006). Crystals appropriate for data collection were obtained by slow evaporation from a CH2Cl2/CH3OH (1:1, v/v) solution at 283 K.
All H atoms were geometrically positioned (C—H 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq (methyl C).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
Fig. 1. The content of asymmetric unit of (I) showing the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level. |
C13H10O2S3 | F(000) = 1216 |
Mr = 294.41 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 6482 reflections |
a = 9.7994 (14) Å | θ = 2.3–28.3° |
b = 27.571 (4) Å | µ = 0.54 mm−1 |
c = 10.8814 (16) Å | T = 297 K |
β = 113.816 (2)° | Block, colourless |
V = 2689.6 (7) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART 4K CCD area-detector diffractometer | 5868 independent reflections |
Radiation source: fine-focus sealed tube | 5087 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −12→12 |
Tmin = 0.900, Tmax = 0.948 | k = −35→32 |
29719 measured reflections | l = −12→13 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0723P)2 + 0.9173P] where P = (Fo2 + 2Fc2)/3 |
5868 reflections | (Δ/σ)max = 0.001 |
327 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C13H10O2S3 | V = 2689.6 (7) Å3 |
Mr = 294.41 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.7994 (14) Å | µ = 0.54 mm−1 |
b = 27.571 (4) Å | T = 297 K |
c = 10.8814 (16) Å | 0.20 × 0.20 × 0.10 mm |
β = 113.816 (2)° |
Bruker SMART 4K CCD area-detector diffractometer | 5868 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 5087 reflections with I > 2σ(I) |
Tmin = 0.900, Tmax = 0.948 | Rint = 0.022 |
29719 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.41 e Å−3 |
5868 reflections | Δρmin = −0.25 e Å−3 |
327 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 | ||
C1 | 0.8777 (2) | 0.77555 (7) | 0.9581 (2) | 0.0472 (4) | |
C2 | 0.7685 (2) | 0.77154 (8) | 1.0017 (2) | 0.0514 (5) | |
H2 | 0.7468 | 0.7983 | 1.0426 | 0.062* | |
C3 | 0.6814 (3) | 0.72716 (8) | 0.9882 (2) | 0.0538 (5) | |
C4 | 0.5584 (2) | 0.72918 (8) | 1.0320 (2) | 0.0514 (5) | |
C5 | 0.5266 (3) | 0.76375 (9) | 1.1109 (2) | 0.0546 (5) | |
H5 | 0.5797 | 0.7924 | 1.1414 | 0.066* | |
C6 | 0.4014 (3) | 0.74909 (11) | 1.1383 (3) | 0.0700 (7) | |
H6 | 0.3636 | 0.7670 | 1.1899 | 0.084* | |
C7 | 0.3450 (3) | 0.70635 (11) | 1.0805 (3) | 0.0771 (8) | |
H7 | 0.2631 | 0.6918 | 1.0879 | 0.093* | |
C8 | 0.9616 (2) | 0.82346 (8) | 0.9849 (2) | 0.0484 (5) | |
C9 | 0.8910 (2) | 0.86269 (7) | 0.8925 (2) | 0.0455 (4) | |
C10 | 0.7624 (3) | 0.86089 (9) | 0.7771 (2) | 0.0592 (6) | |
H10 | 0.7021 | 0.8336 | 0.7487 | 0.071* | |
C11 | 0.7326 (3) | 0.90526 (11) | 0.7067 (3) | 0.0746 (8) | |
H11 | 0.6503 | 0.9106 | 0.6265 | 0.089* | |
C12 | 0.8367 (3) | 0.93903 (10) | 0.7685 (3) | 0.0777 (8) | |
H12 | 0.8345 | 0.9702 | 0.7351 | 0.093* | |
C13 | 1.0565 (3) | 0.76053 (11) | 0.8186 (3) | 0.0706 (7) | |
H13A | 1.0041 | 0.7867 | 0.7605 | 0.106* | |
H13B | 1.0911 | 0.7382 | 0.7698 | 0.106* | |
H13C | 1.1402 | 0.7732 | 0.8937 | 0.106* | |
C14 | 0.8364 (2) | 0.93124 (7) | 0.28464 (19) | 0.0406 (4) | |
C15 | 0.9289 (2) | 0.91501 (8) | 0.4059 (2) | 0.0460 (4) | |
H15 | 0.8959 | 0.8903 | 0.4452 | 0.055* | |
C16 | 1.0792 (2) | 0.93429 (7) | 0.4794 (2) | 0.0447 (4) | |
C17 | 1.1705 (2) | 0.91180 (7) | 0.6088 (2) | 0.0441 (4) | |
C18 | 1.1315 (3) | 0.87987 (9) | 0.6871 (2) | 0.0560 (5) | |
H18 | 1.0360 | 0.8676 | 0.6642 | 0.067* | |
C19 | 1.2562 (3) | 0.86837 (11) | 0.8071 (2) | 0.0734 (7) | |
H19 | 1.2510 | 0.8478 | 0.8729 | 0.088* | |
C20 | 1.3836 (3) | 0.89032 (10) | 0.8162 (2) | 0.0702 (7) | |
H20 | 1.4755 | 0.8861 | 0.8878 | 0.084* | |
C21 | 0.6899 (2) | 0.90491 (7) | 0.21273 (19) | 0.0410 (4) | |
C22 | 0.5692 (2) | 0.91621 (7) | 0.25324 (18) | 0.0402 (4) | |
C23 | 0.5668 (2) | 0.94842 (8) | 0.3484 (2) | 0.0468 (4) | |
H23 | 0.6487 | 0.9667 | 0.4027 | 0.056* | |
C24 | 0.4256 (2) | 0.95063 (9) | 0.3547 (2) | 0.0539 (5) | |
H24 | 0.4038 | 0.9705 | 0.4134 | 0.065* | |
C25 | 0.3249 (2) | 0.92002 (9) | 0.2642 (2) | 0.0556 (5) | |
H25 | 0.2265 | 0.9168 | 0.2544 | 0.067* | |
C26 | 0.7093 (3) | 0.98422 (12) | 0.0489 (3) | 0.0780 (8) | |
H26A | 0.6983 | 0.9558 | −0.0052 | 0.117* | |
H26B | 0.7164 | 1.0123 | −0.0003 | 0.117* | |
H26C | 0.6244 | 0.9873 | 0.0711 | 0.117* | |
O1 | 0.7101 (2) | 0.68979 (6) | 0.9424 (2) | 0.0768 (5) | |
O2 | 1.08117 (19) | 0.82733 (7) | 1.07963 (18) | 0.0719 (5) | |
O3 | 1.12945 (16) | 0.96742 (6) | 0.43439 (16) | 0.0576 (4) | |
O4 | 0.67672 (18) | 0.87642 (6) | 0.12342 (16) | 0.0575 (4) | |
S1 | 0.43580 (8) | 0.68155 (2) | 0.99352 (7) | 0.0719 (2) | |
S2 | 0.97234 (7) | 0.91905 (2) | 0.91322 (7) | 0.06458 (19) | |
S3 | 0.93242 (7) | 0.72952 (2) | 0.87829 (7) | 0.06165 (17) | |
S4 | 1.35647 (6) | 0.92628 (2) | 0.68299 (6) | 0.06146 (18) | |
S5 | 0.39848 (6) | 0.88857 (2) | 0.17198 (5) | 0.05342 (16) | |
S6 | 0.87586 (6) | 0.97902 (2) | 0.20071 (6) | 0.05825 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0487 (10) | 0.0406 (10) | 0.0460 (10) | −0.0015 (8) | 0.0126 (8) | 0.0032 (8) |
C2 | 0.0557 (12) | 0.0405 (11) | 0.0569 (12) | −0.0059 (9) | 0.0218 (10) | −0.0017 (9) |
C3 | 0.0598 (12) | 0.0433 (11) | 0.0563 (12) | −0.0070 (9) | 0.0212 (10) | 0.0011 (9) |
C4 | 0.0528 (11) | 0.0419 (11) | 0.0524 (11) | −0.0109 (8) | 0.0141 (9) | 0.0034 (9) |
C5 | 0.0510 (11) | 0.0528 (12) | 0.0610 (13) | −0.0143 (9) | 0.0235 (10) | −0.0053 (10) |
C6 | 0.0630 (15) | 0.0737 (17) | 0.0787 (17) | −0.0072 (13) | 0.0342 (13) | −0.0016 (14) |
C7 | 0.0554 (14) | 0.084 (2) | 0.0864 (19) | −0.0167 (13) | 0.0234 (13) | 0.0172 (15) |
C8 | 0.0455 (10) | 0.0469 (11) | 0.0490 (11) | −0.0066 (8) | 0.0150 (9) | 0.0013 (9) |
C9 | 0.0414 (9) | 0.0425 (10) | 0.0521 (11) | −0.0059 (8) | 0.0184 (8) | 0.0000 (8) |
C10 | 0.0500 (12) | 0.0547 (13) | 0.0604 (13) | −0.0071 (10) | 0.0094 (10) | 0.0107 (10) |
C11 | 0.0472 (12) | 0.0768 (17) | 0.0822 (17) | −0.0016 (12) | 0.0081 (12) | 0.0322 (14) |
C12 | 0.0544 (14) | 0.0590 (15) | 0.114 (2) | 0.0032 (11) | 0.0285 (14) | 0.0331 (15) |
C13 | 0.0684 (15) | 0.0782 (18) | 0.0718 (16) | −0.0030 (13) | 0.0351 (13) | −0.0022 (13) |
C14 | 0.0384 (9) | 0.0375 (9) | 0.0482 (10) | −0.0016 (7) | 0.0198 (8) | −0.0032 (8) |
C15 | 0.0439 (10) | 0.0453 (11) | 0.0489 (10) | −0.0059 (8) | 0.0189 (8) | 0.0008 (8) |
C16 | 0.0397 (9) | 0.0454 (11) | 0.0492 (10) | 0.0013 (8) | 0.0183 (8) | −0.0006 (8) |
C17 | 0.0414 (9) | 0.0443 (10) | 0.0451 (10) | −0.0011 (8) | 0.0159 (8) | −0.0064 (8) |
C18 | 0.0534 (12) | 0.0670 (14) | 0.0454 (11) | −0.0072 (10) | 0.0178 (9) | 0.0005 (10) |
C19 | 0.0780 (17) | 0.0847 (19) | 0.0460 (12) | −0.0150 (14) | 0.0132 (12) | 0.0078 (12) |
C20 | 0.0662 (15) | 0.0754 (17) | 0.0485 (12) | −0.0043 (13) | 0.0020 (11) | −0.0006 (12) |
C21 | 0.0413 (9) | 0.0376 (9) | 0.0421 (9) | −0.0026 (7) | 0.0147 (7) | 0.0006 (8) |
C22 | 0.0371 (9) | 0.0395 (9) | 0.0399 (9) | −0.0050 (7) | 0.0113 (7) | 0.0010 (7) |
C23 | 0.0453 (10) | 0.0438 (11) | 0.0484 (10) | −0.0015 (8) | 0.0158 (8) | −0.0029 (8) |
C24 | 0.0508 (11) | 0.0574 (13) | 0.0571 (12) | 0.0043 (9) | 0.0254 (10) | −0.0018 (10) |
C25 | 0.0418 (10) | 0.0674 (14) | 0.0584 (12) | 0.0021 (9) | 0.0212 (9) | 0.0077 (11) |
C26 | 0.0602 (14) | 0.0858 (19) | 0.0701 (16) | −0.0064 (13) | 0.0077 (12) | 0.0305 (14) |
O1 | 0.0985 (14) | 0.0438 (9) | 0.1046 (15) | −0.0114 (9) | 0.0580 (12) | −0.0118 (9) |
O2 | 0.0556 (9) | 0.0694 (11) | 0.0649 (10) | −0.0141 (8) | −0.0023 (8) | 0.0120 (8) |
O3 | 0.0433 (8) | 0.0595 (9) | 0.0660 (9) | −0.0073 (7) | 0.0177 (7) | 0.0125 (7) |
O4 | 0.0603 (9) | 0.0547 (9) | 0.0599 (9) | −0.0101 (7) | 0.0269 (7) | −0.0186 (7) |
S1 | 0.0713 (4) | 0.0563 (4) | 0.0768 (4) | −0.0220 (3) | 0.0182 (3) | −0.0003 (3) |
S2 | 0.0508 (3) | 0.0491 (3) | 0.0863 (4) | −0.0106 (2) | 0.0198 (3) | 0.0032 (3) |
S3 | 0.0664 (4) | 0.0504 (3) | 0.0718 (4) | −0.0007 (2) | 0.0317 (3) | −0.0043 (3) |
S4 | 0.0456 (3) | 0.0647 (4) | 0.0631 (3) | −0.0076 (2) | 0.0105 (2) | 0.0019 (3) |
S5 | 0.0424 (3) | 0.0632 (4) | 0.0513 (3) | −0.0128 (2) | 0.0155 (2) | −0.0078 (2) |
S6 | 0.0483 (3) | 0.0567 (3) | 0.0638 (3) | −0.0093 (2) | 0.0164 (2) | 0.0152 (3) |
C1—C2 | 1.339 (3) | C14—C15 | 1.340 (3) |
C1—C8 | 1.521 (3) | C14—C21 | 1.514 (3) |
C1—S3 | 1.740 (2) | C14—S6 | 1.733 (2) |
C2—C3 | 1.465 (3) | C15—C16 | 1.463 (3) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—O1 | 1.225 (3) | C16—O3 | 1.230 (2) |
C3—C4 | 1.465 (3) | C16—C17 | 1.467 (3) |
C4—C5 | 1.400 (3) | C17—C18 | 1.382 (3) |
C4—S1 | 1.714 (2) | C17—S4 | 1.716 (2) |
C5—C6 | 1.433 (3) | C18—C19 | 1.417 (3) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—C7 | 1.345 (4) | C19—C20 | 1.355 (4) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—S1 | 1.683 (3) | C20—S4 | 1.686 (3) |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—O2 | 1.213 (3) | C21—O4 | 1.215 (2) |
C8—C9 | 1.448 (3) | C21—C22 | 1.453 (3) |
C9—C10 | 1.375 (3) | C22—C23 | 1.372 (3) |
C9—S2 | 1.719 (2) | C22—S5 | 1.7225 (18) |
C10—C11 | 1.410 (3) | C23—C24 | 1.414 (3) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—C12 | 1.344 (4) | C24—C25 | 1.368 (3) |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—S2 | 1.691 (3) | C25—S5 | 1.692 (2) |
C12—H12 | 0.9300 | C25—H25 | 0.9300 |
C13—S3 | 1.808 (3) | C26—S6 | 1.799 (3) |
C13—H13A | 0.9600 | C26—H26A | 0.9600 |
C13—H13B | 0.9600 | C26—H26B | 0.9600 |
C13—H13C | 0.9600 | C26—H26C | 0.9600 |
C2—C1—C8 | 116.85 (19) | C14—C15—C16 | 123.25 (18) |
C2—C1—S3 | 124.61 (17) | C14—C15—H15 | 118.4 |
C8—C1—S3 | 118.52 (16) | C16—C15—H15 | 118.4 |
C1—C2—C3 | 123.4 (2) | O3—C16—C15 | 121.94 (18) |
C1—C2—H2 | 118.3 | O3—C16—C17 | 120.60 (18) |
C3—C2—H2 | 118.3 | C15—C16—C17 | 117.45 (18) |
O1—C3—C2 | 121.6 (2) | C18—C17—C16 | 130.37 (19) |
O1—C3—C4 | 121.2 (2) | C18—C17—S4 | 111.33 (16) |
C2—C3—C4 | 117.3 (2) | C16—C17—S4 | 118.29 (15) |
C5—C4—C3 | 129.90 (19) | C17—C18—C19 | 111.1 (2) |
C5—C4—S1 | 111.32 (17) | C17—C18—H18 | 124.4 |
C3—C4—S1 | 118.65 (17) | C19—C18—H18 | 124.4 |
C4—C5—C6 | 110.9 (2) | C20—C19—C18 | 113.2 (2) |
C4—C5—H5 | 124.5 | C20—C19—H19 | 123.4 |
C6—C5—H5 | 124.5 | C18—C19—H19 | 123.4 |
C7—C6—C5 | 112.0 (3) | C19—C20—S4 | 112.3 (2) |
C7—C6—H6 | 124.0 | C19—C20—H20 | 123.9 |
C5—C6—H6 | 124.0 | S4—C20—H20 | 123.9 |
C6—C7—S1 | 114.1 (2) | O4—C21—C22 | 122.99 (18) |
C6—C7—H7 | 123.0 | O4—C21—C14 | 119.72 (17) |
S1—C7—H7 | 123.0 | C22—C21—C14 | 117.27 (16) |
O2—C8—C9 | 123.44 (19) | C23—C22—C21 | 129.21 (17) |
O2—C8—C1 | 120.08 (19) | C23—C22—S5 | 111.39 (15) |
C9—C8—C1 | 116.48 (17) | C21—C22—S5 | 119.35 (14) |
C10—C9—C8 | 127.74 (19) | C22—C23—C24 | 112.33 (19) |
C10—C9—S2 | 110.96 (16) | C22—C23—H23 | 123.8 |
C8—C9—S2 | 121.18 (15) | C24—C23—H23 | 123.8 |
C9—C10—C11 | 112.2 (2) | C25—C24—C23 | 112.0 (2) |
C9—C10—H10 | 123.9 | C25—C24—H24 | 124.0 |
C11—C10—H10 | 123.9 | C23—C24—H24 | 124.0 |
C12—C11—C10 | 112.4 (2) | C24—C25—S5 | 112.74 (17) |
C12—C11—H11 | 123.8 | C24—C25—H25 | 123.6 |
C10—C11—H11 | 123.8 | S5—C25—H25 | 123.6 |
C11—C12—S2 | 113.1 (2) | S6—C26—H26A | 109.5 |
C11—C12—H12 | 123.4 | S6—C26—H26B | 109.5 |
S2—C12—H12 | 123.4 | H26A—C26—H26B | 109.5 |
S3—C13—H13A | 109.5 | S6—C26—H26C | 109.5 |
S3—C13—H13B | 109.5 | H26A—C26—H26C | 109.5 |
H13A—C13—H13B | 109.5 | H26B—C26—H26C | 109.5 |
S3—C13—H13C | 109.5 | C7—S1—C4 | 91.68 (13) |
H13A—C13—H13C | 109.5 | C12—S2—C9 | 91.37 (12) |
H13B—C13—H13C | 109.5 | C1—S3—C13 | 102.81 (12) |
C15—C14—C21 | 118.14 (17) | C20—S4—C17 | 92.08 (12) |
C15—C14—S6 | 124.49 (15) | C25—S5—C22 | 91.55 (10) |
C21—C14—S6 | 117.31 (14) | C14—S6—C26 | 103.40 (11) |
C8—C1—C2—C3 | −177.6 (2) | C16—C17—C18—C19 | −178.5 (2) |
S3—C1—C2—C3 | 0.5 (3) | S4—C17—C18—C19 | 0.4 (3) |
C1—C2—C3—O1 | 4.3 (4) | C17—C18—C19—C20 | −1.1 (4) |
C1—C2—C3—C4 | −175.8 (2) | C18—C19—C20—S4 | 1.3 (4) |
O1—C3—C4—C5 | 165.1 (2) | C15—C14—C21—O4 | −101.2 (2) |
C2—C3—C4—C5 | −14.8 (4) | S6—C14—C21—O4 | 76.3 (2) |
O1—C3—C4—S1 | −10.4 (3) | C15—C14—C21—C22 | 80.2 (2) |
C2—C3—C4—S1 | 169.69 (17) | S6—C14—C21—C22 | −102.33 (18) |
C3—C4—C5—C6 | −175.1 (2) | O4—C21—C22—C23 | −177.7 (2) |
S1—C4—C5—C6 | 0.7 (3) | C14—C21—C22—C23 | 0.8 (3) |
C4—C5—C6—C7 | −0.7 (3) | O4—C21—C22—S5 | −0.2 (3) |
C5—C6—C7—S1 | 0.4 (3) | C14—C21—C22—S5 | 178.31 (14) |
C2—C1—C8—O2 | 98.6 (3) | C21—C22—C23—C24 | 177.5 (2) |
S3—C1—C8—O2 | −79.6 (3) | S5—C22—C23—C24 | −0.2 (2) |
C2—C1—C8—C9 | −81.4 (3) | C22—C23—C24—C25 | 0.0 (3) |
S3—C1—C8—C9 | 100.4 (2) | C23—C24—C25—S5 | 0.1 (3) |
O2—C8—C9—C10 | 174.5 (2) | C6—C7—S1—C4 | 0.0 (2) |
C1—C8—C9—C10 | −5.5 (3) | C5—C4—S1—C7 | −0.39 (19) |
O2—C8—C9—S2 | −1.2 (3) | C3—C4—S1—C7 | 175.9 (2) |
C1—C8—C9—S2 | 178.76 (15) | C11—C12—S2—C9 | 0.7 (3) |
C8—C9—C10—C11 | −175.6 (2) | C10—C9—S2—C12 | −0.7 (2) |
S2—C9—C10—C11 | 0.5 (3) | C8—C9—S2—C12 | 175.7 (2) |
C9—C10—C11—C12 | 0.1 (4) | C2—C1—S3—C13 | 169.9 (2) |
C10—C11—C12—S2 | −0.6 (4) | C8—C1—S3—C13 | −12.07 (19) |
C21—C14—C15—C16 | 173.87 (18) | C19—C20—S4—C17 | −0.9 (2) |
S6—C14—C15—C16 | −3.4 (3) | C18—C17—S4—C20 | 0.30 (19) |
C14—C15—C16—O3 | 0.9 (3) | C16—C17—S4—C20 | 179.33 (18) |
C14—C15—C16—C17 | −177.61 (19) | C24—C25—S5—C22 | −0.19 (19) |
O3—C16—C17—C18 | 169.2 (2) | C23—C22—S5—C25 | 0.21 (17) |
C15—C16—C17—C18 | −12.3 (3) | C21—C22—S5—C25 | −177.70 (17) |
O3—C16—C17—S4 | −9.7 (3) | C15—C14—S6—C26 | −178.4 (2) |
C15—C16—C17—S4 | 168.90 (15) | C21—C14—S6—C26 | 4.32 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 0.93 | 2.52 | 3.448 (3) | 172 |
C5—H5···O4i | 0.93 | 2.54 | 3.416 (3) | 157 |
C20—H20···O4ii | 0.93 | 2.54 | 3.438 (3) | 162 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H10O2S3 |
Mr | 294.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 297 |
a, b, c (Å) | 9.7994 (14), 27.571 (4), 10.8814 (16) |
β (°) | 113.816 (2) |
V (Å3) | 2689.6 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.54 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.900, 0.948 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29719, 5868, 5087 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.129, 1.06 |
No. of reflections | 5868 |
No. of parameters | 327 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.25 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 0.93 | 2.52 | 3.448 (3) | 172.3 |
C5—H5···O4i | 0.93 | 2.54 | 3.416 (3) | 156.8 |
C20—H20···O4ii | 0.93 | 2.54 | 3.438 (3) | 162.4 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
1,4-Dicarbonyl compounds are widely used as synthetic building blocks for further elaboration into substituted cyclopentenones, such as jasmones, rethorolones, cuparenones, prostaglandins, and five-membered heterocyclic compounds, such as furans, pyrroles, thiophenes, pyridazines (Ellison et al., 1973; Yuguchi et al., 2004). As a continuation of our previous studies in this area, (Chen et al., 2007; Gao et al., 2007; Yin et al., 2007). We herein report the structure of the title compound (I) (Fig. 1).
There are two independent molecules in the asymmetric unit. The bond lengths of the C1—C2 and C14—C15 in two molecules are 1.339 (2) and 1.341 (2) Å, respectively, supporting their double-bond character. The torsion angles C2—C1—C8—C9 and C15—C14—C21—C22 are -81.4 (3) and 80.2 (2) %A, respectively, showing the difference in conformations of two molecules. In both molecules, there is a short intramolecular S···O distance of 2.768 (3) Å.
The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1).