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The title compound, C
5H
4OS
3, contains discrete molecules
, which are linked into sheets by a combination of short S
S contacts [S
S = 3.512 (1) and 3.586 (1) Å] and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 277796
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.099
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C4 - C5 .. 8.22 su
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. O .. 2.70 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989 or 1994); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
5,6-dihydrothieno[2,3-
d][1,3]dithiol-2-one
top
Crystal data top
C5H4OS3 | F(000) = 360 |
Mr = 176.26 | Dx = 1.749 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 4.0743 (7) Å | θ = 8–12° |
b = 11.154 (2) Å | µ = 1.01 mm−1 |
c = 14.778 (4) Å | T = 294 K |
β = 94.651 (17)° | Needle, colourless |
V = 669.4 (2) Å3 | 0.38 × 0.16 × 0.08 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1132 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.0°, θmin = 3.7° |
ω–2θ scans | h = −5→5 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→14 |
Tmin = 0.825, Tmax = 0.949 | l = 0→18 |
1476 measured reflections | 5 standard reflections every 200 reflections |
1423 independent reflections | intensity decay: none |
Refinement top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0384P)2 + 1.0429P] where P = (Fo2 + 2Fc2)/3 |
1423 reflections | (Δ/σ)max < 0.001 |
82 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8992 (8) | 0.3713 (3) | 0.2422 (2) | 0.0309 (7) | |
S1 | 0.8260 (2) | 0.45795 (7) | 0.33978 (5) | 0.0302 (2) | |
S2 | 0.7734 (2) | 0.21974 (7) | 0.25081 (5) | 0.0328 (2) | |
S3 | 0.5720 (2) | 0.34529 (8) | 0.51140 (6) | 0.0394 (3) | |
C2 | 0.6687 (7) | 0.3399 (3) | 0.39890 (19) | 0.0244 (6) | |
C3 | 0.6432 (7) | 0.2321 (3) | 0.3594 (2) | 0.0248 (6) | |
C4 | 0.5310 (7) | 0.1270 (3) | 0.41925 (19) | 0.0238 (6) | |
H4A | 0.3476 | 0.0836 | 0.3888 | 0.029* | |
H4B | 0.7103 | 0.0716 | 0.4347 | 0.029* | |
C5 | 0.4267 (9) | 0.1926 (3) | 0.5043 (2) | 0.0382 (8) | |
H5A | 0.5125 | 0.1494 | 0.5581 | 0.046* | |
H5B | 0.1883 | 0.1923 | 0.5032 | 0.046* | |
O | 1.0221 (7) | 0.4119 (2) | 0.17777 (16) | 0.0450 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0349 (17) | 0.0320 (16) | 0.0269 (15) | 0.0042 (14) | 0.0089 (13) | 0.0018 (13) |
S1 | 0.0405 (5) | 0.0227 (4) | 0.0291 (4) | −0.0030 (3) | 0.0120 (3) | 0.0009 (3) |
S2 | 0.0451 (5) | 0.0297 (4) | 0.0246 (4) | −0.0001 (4) | 0.0091 (3) | −0.0053 (3) |
S3 | 0.0546 (6) | 0.0344 (5) | 0.0311 (4) | −0.0036 (4) | 0.0163 (4) | −0.0032 (4) |
C2 | 0.0292 (16) | 0.0237 (14) | 0.0208 (13) | −0.0012 (12) | 0.0053 (11) | 0.0018 (11) |
C3 | 0.0261 (15) | 0.0257 (14) | 0.0226 (13) | −0.0014 (12) | 0.0025 (11) | −0.0013 (12) |
C4 | 0.0282 (15) | 0.0215 (13) | 0.0225 (14) | −0.0043 (12) | 0.0061 (12) | −0.0026 (11) |
C5 | 0.042 (2) | 0.0388 (19) | 0.0345 (18) | −0.0058 (16) | 0.0098 (15) | 0.0067 (15) |
O | 0.0592 (16) | 0.0458 (14) | 0.0329 (13) | 0.0016 (13) | 0.0223 (12) | 0.0075 (11) |
Geometric parameters (Å, º) top
C1—O | 1.201 (4) | C2—C3 | 1.337 (4) |
C1—S2 | 1.774 (3) | C3—C4 | 1.559 (4) |
C1—S1 | 1.781 (3) | C4—C5 | 1.543 (4) |
S1—C2 | 1.732 (3) | C4—H4A | 0.9700 |
S2—C3 | 1.737 (3) | C4—H4B | 0.9700 |
S3—C2 | 1.740 (3) | C5—H5A | 0.9700 |
S3—C5 | 1.804 (4) | C5—H5B | 0.9700 |
| | | |
S1···S3i | 3.586 (1) | S3···S3i | 3.512 (1) |
S3···S1i | 3.586 (1) | | |
| | | |
O—C1—S2 | 123.9 (3) | C5—C4—C3 | 102.6 (2) |
O—C1—S1 | 123.1 (3) | C5—C4—H4A | 111.2 |
S2—C1—S1 | 113.04 (17) | C3—C4—H4A | 111.2 |
C2—S1—C1 | 95.08 (15) | C5—C4—H4B | 111.2 |
C3—S2—C1 | 95.85 (14) | C3—C4—H4B | 111.2 |
C2—S3—C5 | 90.60 (15) | H4A—C4—H4B | 109.2 |
C3—C2—S1 | 118.9 (2) | C4—C5—S3 | 112.6 (2) |
C3—C2—S3 | 115.6 (2) | C4—C5—H5A | 109.1 |
S1—C2—S3 | 125.26 (18) | S3—C5—H5A | 109.1 |
C2—C3—C4 | 116.4 (3) | C4—C5—H5B | 109.1 |
C2—C3—S2 | 117.1 (2) | S3—C5—H5B | 109.1 |
C4—C3—S2 | 126.2 (2) | H5A—C5—H5B | 107.8 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Oii | 0.97 | 2.58 | 3.517 (4) | 162 |
C5—H5A···Oiii | 0.97 | 2.70 | 3.578 (5) | 150 |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2. |
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