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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014382/su6116sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014382/su6116Isup2.hkl
Contains datablock I

CCDC reference: 245304

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](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

Computing details top

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).

1,3-dithiolan-2-one top
Crystal data top
C3H4OS2F(000) = 248
Mr = 120.18Dx = 1.687 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3398 reflections
a = 8.0397 (16) Åθ = 2.0–27.5°
b = 5.202 (1) ŵ = 0.96 mm1
c = 11.318 (2) ÅT = 110 K
β = 90.426 (4)°Prism, light yellow
V = 473.31 (16) Å30.28 × 0.24 × 0.22 mm
Z = 4
Data collection top
Bruker SMART 1K CCD
diffractometer
1078 independent reflections
Radiation source: fine-focus sealed tube985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker 2003)
h = 1010
Tmin = 0.775, Tmax = 0.817k = 56
3916 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.052All 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 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
S10.13718 (3)0.14801 (5)0.83292 (2)0.01694 (10)
S20.35705 (3)0.25126 (4)0.73070 (2)0.01553 (10)
O10.21994 (10)0.12268 (15)0.60746 (7)0.02131 (19)
C10.23395 (13)0.02702 (19)0.70416 (9)0.0151 (2)
C20.35068 (14)0.2365 (2)0.89078 (10)0.0160 (2)
C30.18252 (14)0.1259 (2)0.92678 (10)0.0164 (2)
H3B0.1838 (18)0.071 (3)1.0066 (13)0.021 (3)*
H2A0.4420 (17)0.138 (2)0.9207 (12)0.019 (3)*
H2B0.3649 (16)0.405 (2)0.9249 (12)0.016 (3)*
H3A0.0952 (18)0.246 (3)0.9163 (14)0.021 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01790 (15)0.01575 (16)0.01721 (16)0.00373 (10)0.00266 (11)0.00041 (9)
S20.01521 (15)0.01560 (16)0.01579 (16)0.00291 (9)0.00094 (11)0.00117 (9)
O10.0255 (4)0.0221 (4)0.0163 (4)0.0032 (3)0.0006 (3)0.0024 (3)
C10.0130 (4)0.0150 (5)0.0174 (5)0.0008 (4)0.0007 (4)0.0013 (4)
C20.0155 (5)0.0175 (5)0.0151 (5)0.0000 (4)0.0008 (4)0.0004 (4)
C30.0164 (5)0.0175 (5)0.0155 (5)0.0006 (4)0.0024 (4)0.0012 (4)
Geometric parameters (Å, º) top
S1—C11.7725 (11)C3—C21.5274 (15)
S1—C31.8128 (11)C3—H3B0.947 (15)
S2—C11.7779 (11)C3—H3A0.948 (15)
S2—C21.8143 (12)C2—H2A0.956 (14)
O1—C11.2068 (14)C2—H2B0.965 (13)
C1—S1—C396.60 (5)S1—C3—H3A107.5 (9)
C1—S2—C296.57 (5)H3B—C3—H3A108.7 (13)
O1—C1—S1124.10 (8)C3—C2—S2108.29 (8)
O1—C1—S2122.48 (8)C3—C2—H2A112.5 (8)
S1—C1—S2113.42 (6)S2—C2—H2A110.4 (8)
C2—C3—S1108.32 (7)C3—C2—H2B109.8 (8)
C2—C3—H3B111.3 (9)S2—C2—H2B110.9 (8)
S1—C3—H3B108.9 (9)H2A—C2—H2B105.0 (11)
C2—C3—H3A111.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O1i0.965 (13)2.635 (13)3.3455 (14)130.7 (10)
C3—H3B···O1ii0.947 (15)2.613 (15)3.3342 (14)133.3 (12)
C3—H3A···O1iii0.948 (15)2.635 (15)3.5087 (15)153.4 (11)
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z+3/2.
 

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