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The title compound, C6H10O3S2, has twofold imposed crystallographic symmetry in the solid state, with concomitant disorder of the three unique O atoms, so that in this trioxide, each S atom is effectively bonded to a unit-occupancy O atom and to a half-occupancy O atom. The six-membered 2,3-di­hydro-5,6-di­methyl-1,4-dithiine ring has a half-chair conform­ation, with the twofold axis passing through the mid-points of the C=C and C-C bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003356/bt6407sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003356/bt6407Isup2.hkl
Contains datablock I

CCDC reference: 236086

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.056
  • wR factor = 0.143
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.400 From the CIF: _refine_ls_abs_structure_Flack_su 0.300 PLAT032_ALERT_4_C Std Uncertainty in Flack Parameter too High .... 0.30 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.40 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.15 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT432_ALERT_2_C Short Inter X...Y Contact S1 .. O1 = 3.11 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.45 From the CIF: _reflns_number_total 761 Count of symmetry unique reflns 474 Completeness (_total/calc) 160.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 287 Fraction of Friedel pairs measured 0.605 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

(I) top
Crystal data top
C6H10O3S2F(000) = 204
Mr = 194.28Dx = 1.576 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 761 reflections
a = 5.5919 (5) Åθ = 2.6–25.5°
b = 9.2507 (10) ŵ = 0.60 mm1
c = 7.9146 (9) ÅT = 150 K
V = 409.41 (7) Å3Block, white
Z = 20.12 × 0.12 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
672 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.076
Graphite monochromatorθmax = 25.5°, θmin = 2.6°
φ scans, and ω scans with κ offsetsh = 66
3121 measured reflectionsk = 1111
761 independent reflectionsl = 99
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.0563P)2 + 0.467P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.143(Δ/σ)max = 0.002
S = 1.16Δρmax = 0.27 e Å3
761 reflectionsΔρmin = 0.29 e Å3
58 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.09 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 287 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.4 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.7090 (2)0.36431 (15)0.80083 (19)0.0466 (5)
O10.9651 (13)0.3655 (11)0.7621 (11)0.073 (3)0.50
O20.5815 (9)0.2289 (4)0.8227 (6)0.0657 (14)
C10.5848 (9)0.4496 (5)0.6167 (7)0.0388 (13)
C20.6317 (10)0.4823 (6)0.9686 (7)0.0470 (14)
C30.6853 (14)0.3898 (7)0.4581 (8)0.0669 (18)
H2A0.67470.43651.07750.056*
H2B0.72490.57290.95810.056*
H3A0.55450.36040.38320.100*
H3B0.78520.30570.48430.100*
H3C0.78260.46370.40200.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0502 (8)0.0419 (8)0.0476 (8)0.0083 (6)0.0123 (6)0.0111 (6)
O10.030 (3)0.103 (7)0.085 (6)0.023 (4)0.020 (4)0.053 (6)
O20.096 (4)0.037 (2)0.064 (3)0.0007 (19)0.029 (3)0.005 (2)
C10.044 (3)0.038 (3)0.035 (3)0.001 (2)0.000 (2)0.010 (2)
C20.069 (4)0.043 (3)0.029 (2)0.007 (3)0.014 (2)0.007 (2)
C30.089 (5)0.065 (4)0.047 (3)0.001 (4)0.014 (3)0.020 (3)
Geometric parameters (Å, º) top
S1—O11.464 (8)C2—C2i1.509 (11)
S1—O21.451 (5)C2—H2A0.99
S1—C11.797 (5)C2—H2B0.99
S1—C21.772 (5)C3—H3A0.98
C1—C1i1.330 (10)C3—H3B0.98
C1—C31.482 (7)C3—H3C0.98
O1—S1—O2120.8 (5)S1—C2—H2A109.3
O1—S1—C1101.8 (4)C2i—C2—H2B109.3
O1—S1—C2113.0 (4)S1—C2—H2B109.3
O2—S1—C1106.6 (3)H2A—C2—H2B107.9
O2—S1—C2108.8 (3)C1—C3—H3A109.5
C1—S1—C2104.1 (2)C1—C3—H3B109.5
C1i—C1—S1125.70 (16)H3A—C3—H3B109.5
C1i—C1—C3122.2 (4)C1—C3—H3C109.5
C3—C1—S1112.1 (4)H3A—C3—H3C109.5
C2i—C2—S1111.8 (4)H3B—C3—H3C109.5
C2i—C2—H2A109.3
O2—S1—C1—C1i96.5 (7)C2—S1—C1—C3164.3 (4)
O1—S1—C1—C1i136.1 (7)O2—S1—C2—C2i62.0 (5)
C2—S1—C1—C1i18.5 (8)O1—S1—C2—C2i160.9 (6)
O2—S1—C1—C380.8 (5)C1—S1—C2—C2i51.3 (6)
O1—S1—C1—C346.7 (6)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···O1ii0.992.403.120 (10)130
C2—H2B···O2iii0.992.503.241 (7)131
C3—H3A···O1iv0.982.443.183 (11)133
Symmetry codes: (ii) x+2, y+1, z; (iii) x+3/2, y+1/2, z+2; (iv) x1/2, y+1/2, z+1.
 

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