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The title compound, C3H4OS2, possesses pseudo-twofold symmetry and consists of a twisted five-membered ring of three C and two S atoms, with a ketone O atom in an equatorial position.
Supporting information
CCDC reference: 245304
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.002 Å
- R factor = 0.020
- wR factor = 0.052
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.38
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. O1 .. 2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B .. O1 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. O1 .. 2.63 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: X-SEED (Barbour, 2001) and SHELXTL (Bruker, 2000); software used to prepare material for publication: PLATON (Spek, 2003).
Crystal data top
C3H4OS2 | F(000) = 248 |
Mr = 120.18 | Dx = 1.687 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3398 reflections |
a = 8.0397 (16) Å | θ = 2.0–27.5° |
b = 5.202 (1) Å | µ = 0.96 mm−1 |
c = 11.318 (2) Å | T = 110 K |
β = 90.426 (4)° | Prism, light yellow |
V = 473.31 (16) Å3 | 0.28 × 0.24 × 0.22 mm |
Z = 4 | |
Data collection top
Bruker SMART 1K CCD diffractometer | 1078 independent reflections |
Radiation source: fine-focus sealed tube | 985 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.6°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker 2003) | h = −10→10 |
Tmin = 0.775, Tmax = 0.817 | k = −5→6 |
3916 measured reflections | l = −14→14 |
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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.052 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0369P)2] where P = (Fo2 + 2Fc2)/3 |
1078 reflections | (Δ/σ)max = 0.001 |
71 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Experimental. The data collection covered approximately a hemisphere of reciprocal space, by a
combination of four sets of exposures; each set having a different φ angle
for the crystal and each exposure covering 0.3° in θ. Crystal decay was
monitored by analyzing duplicate reflections, and found to be less than 1%,
therefore no decay correction was applied. |
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 | |
S1 | 0.13718 (3) | 0.14801 (5) | 0.83292 (2) | 0.01694 (10) | |
S2 | 0.35705 (3) | −0.25126 (4) | 0.73070 (2) | 0.01553 (10) | |
O1 | 0.21994 (10) | 0.12268 (15) | 0.60746 (7) | 0.02131 (19) | |
C1 | 0.23395 (13) | 0.02702 (19) | 0.70416 (9) | 0.0151 (2) | |
C2 | 0.35068 (14) | −0.2365 (2) | 0.89078 (10) | 0.0160 (2) | |
C3 | 0.18252 (14) | −0.1259 (2) | 0.92678 (10) | 0.0164 (2) | |
H3B | 0.1838 (18) | −0.071 (3) | 1.0066 (13) | 0.021 (3)* | |
H2A | 0.4420 (17) | −0.138 (2) | 0.9207 (12) | 0.019 (3)* | |
H2B | 0.3649 (16) | −0.405 (2) | 0.9249 (12) | 0.016 (3)* | |
H3A | 0.0952 (18) | −0.246 (3) | 0.9163 (14) | 0.021 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01790 (15) | 0.01575 (16) | 0.01721 (16) | 0.00373 (10) | 0.00266 (11) | −0.00041 (9) |
S2 | 0.01521 (15) | 0.01560 (16) | 0.01579 (16) | 0.00291 (9) | 0.00094 (11) | −0.00117 (9) |
O1 | 0.0255 (4) | 0.0221 (4) | 0.0163 (4) | 0.0032 (3) | −0.0006 (3) | 0.0024 (3) |
C1 | 0.0130 (4) | 0.0150 (5) | 0.0174 (5) | −0.0008 (4) | 0.0007 (4) | −0.0013 (4) |
C2 | 0.0155 (5) | 0.0175 (5) | 0.0151 (5) | 0.0000 (4) | −0.0008 (4) | 0.0004 (4) |
C3 | 0.0164 (5) | 0.0175 (5) | 0.0155 (5) | −0.0006 (4) | 0.0024 (4) | 0.0012 (4) |
Geometric parameters (Å, º) top
S1—C1 | 1.7725 (11) | C3—C2 | 1.5274 (15) |
S1—C3 | 1.8128 (11) | C3—H3B | 0.947 (15) |
S2—C1 | 1.7779 (11) | C3—H3A | 0.948 (15) |
S2—C2 | 1.8143 (12) | C2—H2A | 0.956 (14) |
O1—C1 | 1.2068 (14) | C2—H2B | 0.965 (13) |
| | | |
C1—S1—C3 | 96.60 (5) | S1—C3—H3A | 107.5 (9) |
C1—S2—C2 | 96.57 (5) | H3B—C3—H3A | 108.7 (13) |
O1—C1—S1 | 124.10 (8) | C3—C2—S2 | 108.29 (8) |
O1—C1—S2 | 122.48 (8) | C3—C2—H2A | 112.5 (8) |
S1—C1—S2 | 113.42 (6) | S2—C2—H2A | 110.4 (8) |
C2—C3—S1 | 108.32 (7) | C3—C2—H2B | 109.8 (8) |
C2—C3—H3B | 111.3 (9) | S2—C2—H2B | 110.9 (8) |
S1—C3—H3B | 108.9 (9) | H2A—C2—H2B | 105.0 (11) |
C2—C3—H3A | 111.9 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O1i | 0.965 (13) | 2.635 (13) | 3.3455 (14) | 130.7 (10) |
C3—H3B···O1ii | 0.947 (15) | 2.613 (15) | 3.3342 (14) | 133.3 (12) |
C3—H3A···O1iii | 0.948 (15) | 2.635 (15) | 3.5087 (15) | 153.4 (11) |
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+3/2. |
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