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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
CCDC reference: 236086
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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).
Crystal data top
C6H10O3S2 | F(000) = 204 |
Mr = 194.28 | Dx = 1.576 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 761 reflections |
a = 5.5919 (5) Å | θ = 2.6–25.5° |
b = 9.2507 (10) Å | µ = 0.60 mm−1 |
c = 7.9146 (9) Å | T = 150 K |
V = 409.41 (7) Å3 | Block, white |
Z = 2 | 0.12 × 0.12 × 0.10 mm |
Data collection top
Nonius KappaCCD diffractometer | 672 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.076 |
Graphite monochromator | θmax = 25.5°, θmin = 2.6° |
φ scans, and ω scans with κ offsets | h = −6→6 |
3121 measured reflections | k = −11→11 |
761 independent reflections | l = −9→9 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.16 | Δρmax = 0.27 e Å−3 |
761 reflections | Δρmin = −0.29 e Å−3 |
58 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.09 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 287 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.4 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.7090 (2) | 0.36431 (15) | 0.80083 (19) | 0.0466 (5) | |
O1 | 0.9651 (13) | 0.3655 (11) | 0.7621 (11) | 0.073 (3) | 0.50 |
O2 | 0.5815 (9) | 0.2289 (4) | 0.8227 (6) | 0.0657 (14) | |
C1 | 0.5848 (9) | 0.4496 (5) | 0.6167 (7) | 0.0388 (13) | |
C2 | 0.6317 (10) | 0.4823 (6) | 0.9686 (7) | 0.0470 (14) | |
C3 | 0.6853 (14) | 0.3898 (7) | 0.4581 (8) | 0.0669 (18) | |
H2A | 0.6747 | 0.4365 | 1.0775 | 0.056* | |
H2B | 0.7249 | 0.5729 | 0.9581 | 0.056* | |
H3A | 0.5545 | 0.3604 | 0.3832 | 0.100* | |
H3B | 0.7852 | 0.3057 | 0.4843 | 0.100* | |
H3C | 0.7826 | 0.4637 | 0.4020 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0502 (8) | 0.0419 (8) | 0.0476 (8) | 0.0083 (6) | −0.0123 (6) | −0.0111 (6) |
O1 | 0.030 (3) | 0.103 (7) | 0.085 (6) | 0.023 (4) | −0.020 (4) | −0.053 (6) |
O2 | 0.096 (4) | 0.037 (2) | 0.064 (3) | 0.0007 (19) | −0.029 (3) | 0.005 (2) |
C1 | 0.044 (3) | 0.038 (3) | 0.035 (3) | 0.001 (2) | 0.000 (2) | −0.010 (2) |
C2 | 0.069 (4) | 0.043 (3) | 0.029 (2) | 0.007 (3) | −0.014 (2) | −0.007 (2) |
C3 | 0.089 (5) | 0.065 (4) | 0.047 (3) | −0.001 (4) | 0.014 (3) | −0.020 (3) |
Geometric parameters (Å, º) top
S1—O1 | 1.464 (8) | C2—C2i | 1.509 (11) |
S1—O2 | 1.451 (5) | C2—H2A | 0.99 |
S1—C1 | 1.797 (5) | C2—H2B | 0.99 |
S1—C2 | 1.772 (5) | C3—H3A | 0.98 |
C1—C1i | 1.330 (10) | C3—H3B | 0.98 |
C1—C3 | 1.482 (7) | C3—H3C | 0.98 |
| | | |
O1—S1—O2 | 120.8 (5) | S1—C2—H2A | 109.3 |
O1—S1—C1 | 101.8 (4) | C2i—C2—H2B | 109.3 |
O1—S1—C2 | 113.0 (4) | S1—C2—H2B | 109.3 |
O2—S1—C1 | 106.6 (3) | H2A—C2—H2B | 107.9 |
O2—S1—C2 | 108.8 (3) | C1—C3—H3A | 109.5 |
C1—S1—C2 | 104.1 (2) | C1—C3—H3B | 109.5 |
C1i—C1—S1 | 125.70 (16) | H3A—C3—H3B | 109.5 |
C1i—C1—C3 | 122.2 (4) | C1—C3—H3C | 109.5 |
C3—C1—S1 | 112.1 (4) | H3A—C3—H3C | 109.5 |
C2i—C2—S1 | 111.8 (4) | H3B—C3—H3C | 109.5 |
C2i—C2—H2A | 109.3 | | |
| | | |
O2—S1—C1—C1i | 96.5 (7) | C2—S1—C1—C3 | 164.3 (4) |
O1—S1—C1—C1i | −136.1 (7) | O2—S1—C2—C2i | −62.0 (5) |
C2—S1—C1—C1i | −18.5 (8) | O1—S1—C2—C2i | 160.9 (6) |
O2—S1—C1—C3 | −80.8 (5) | C1—S1—C2—C2i | 51.3 (6) |
O1—S1—C1—C3 | 46.7 (6) | | |
Symmetry code: (i) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O1ii | 0.99 | 2.40 | 3.120 (10) | 130 |
C2—H2B···O2iii | 0.99 | 2.50 | 3.241 (7) | 131 |
C3—H3A···O1iv | 0.98 | 2.44 | 3.183 (11) | 133 |
Symmetry codes: (ii) −x+2, −y+1, z; (iii) −x+3/2, y+1/2, −z+2; (iv) x−1/2, −y+1/2, −z+1. |
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