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The title compound, C11H10O4S, was prepared by oxidation of 2-methyl-5,6-methyl­enedi­oxy-3-methyl­sulfanyl-1-benzofuran using 3-chloro­perbenzoic acid. The 5,6-methyl­enedioxy­benzofuran ring system is almost planar. The crystal structure contains aromatic π—π stacking and CH2—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701375X/bx2071sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701375X/bx2071Isup2.hkl
Contains datablock I

CCDC reference: 646769

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.095
  • wR factor = 0.202
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.14 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C11 H10 O4 S
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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C11H10O4SF(000) = 496
Mr = 238.25Dx = 1.510 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p_2ynCell parameters from 3245 reflections
a = 5.0453 (5) Åθ = 2.5–27.9°
b = 12.642 (1) ŵ = 0.30 mm1
c = 16.508 (2) ÅT = 173 K
β = 95.556 (2)°Needle, colorless
V = 1047.98 (18) Å30.65 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
2023 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.093
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
Detector resolution: 10.00 pixels mm-1h = 66
φ and ω scansk = 1115
6212 measured reflectionsl = 2120
2261 independent reflections
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)] = 0.095Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.35 w = 1/[σ2(Fo2) + (0.0344P)2 + 3.5071P]
where P = (Fo2 + 2Fc2)/3
2261 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.46 e Å3
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
xyzUiso*/Ueq
S0.0088 (2)0.68631 (9)0.43950 (6)0.0228 (3)
O10.2102 (6)0.7178 (3)0.67368 (16)0.0234 (7)
O20.4040 (8)0.9863 (3)0.7567 (2)0.0423 (10)
O30.5856 (7)1.0046 (3)0.62387 (18)0.0323 (8)
O40.3039 (7)0.6888 (3)0.41868 (19)0.0339 (9)
C10.0492 (8)0.7245 (4)0.5427 (2)0.0184 (9)
C20.0948 (8)0.8015 (3)0.5854 (2)0.0194 (9)
C30.3026 (9)0.8740 (4)0.5638 (2)0.0217 (9)
H30.37730.88270.51040.026*
C40.3858 (9)0.9306 (4)0.6274 (2)0.0221 (9)
C50.5898 (10)1.0449 (4)0.7045 (3)0.0282 (10)
H5A0.54201.11920.70590.034*
H5B0.76691.03780.72200.034*
C60.2749 (9)0.9190 (4)0.7078 (2)0.0251 (10)
C70.0718 (9)0.8511 (4)0.7310 (2)0.0254 (10)
H70.00270.84410.78450.030*
C80.0127 (8)0.7931 (3)0.6663 (2)0.0197 (9)
C90.2279 (9)0.6754 (4)0.5977 (2)0.0230 (9)
C100.4201 (10)0.5895 (4)0.5914 (3)0.0307 (11)
H10A0.37690.53160.62550.037*
H10B0.59610.61460.60870.037*
H10C0.41300.56600.53590.037*
C110.1156 (10)0.8016 (4)0.3941 (3)0.0308 (11)
H11A0.07210.79890.33620.046*
H11B0.30550.80480.40600.046*
H11C0.03620.86330.41550.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0259 (6)0.0285 (6)0.0131 (5)0.0007 (5)0.0022 (4)0.0053 (4)
O10.0268 (16)0.0288 (18)0.0134 (13)0.0006 (13)0.0036 (11)0.0068 (12)
O20.054 (2)0.053 (2)0.0193 (16)0.017 (2)0.0041 (15)0.0172 (16)
O30.043 (2)0.035 (2)0.0184 (15)0.0111 (16)0.0044 (14)0.0067 (14)
O40.0323 (18)0.050 (2)0.0185 (15)0.0066 (17)0.0011 (13)0.0051 (15)
C10.022 (2)0.022 (2)0.0110 (17)0.0060 (17)0.0008 (15)0.0010 (15)
C20.023 (2)0.021 (2)0.0130 (18)0.0077 (18)0.0009 (15)0.0005 (16)
C30.028 (2)0.026 (2)0.0097 (17)0.0011 (19)0.0024 (15)0.0006 (16)
C40.023 (2)0.023 (2)0.019 (2)0.0013 (18)0.0041 (16)0.0016 (17)
C50.034 (3)0.030 (3)0.022 (2)0.002 (2)0.0056 (18)0.0044 (19)
C60.033 (2)0.029 (3)0.0125 (19)0.009 (2)0.0005 (17)0.0029 (17)
C70.034 (3)0.031 (3)0.0101 (18)0.010 (2)0.0050 (17)0.0021 (17)
C80.021 (2)0.023 (2)0.0134 (18)0.0057 (17)0.0042 (15)0.0043 (16)
C90.025 (2)0.024 (2)0.0185 (19)0.0072 (19)0.0014 (16)0.0045 (17)
C100.033 (3)0.033 (3)0.025 (2)0.005 (2)0.0027 (19)0.004 (2)
C110.031 (2)0.040 (3)0.022 (2)0.003 (2)0.0034 (18)0.006 (2)
Geometric parameters (Å, º) top
S—O41.495 (4)C3—H30.9300
S—C11.767 (4)C4—C61.397 (6)
S—C111.781 (5)C5—H5A0.9700
O1—C91.375 (5)C5—H5B0.9700
O1—C81.375 (5)C6—C71.363 (7)
O2—C61.379 (6)C7—C81.396 (6)
O2—C51.420 (6)C7—H70.9300
O3—C41.372 (6)C9—C101.466 (7)
O3—C51.427 (5)C10—H10A0.9600
C1—C91.366 (6)C10—H10B0.9600
C1—C21.439 (6)C10—H10C0.9600
C2—C81.397 (5)C11—H11A0.9600
C2—C31.412 (6)C11—H11B0.9600
C3—C41.370 (6)C11—H11C0.9600
O4—S—C1106.5 (2)C7—C6—O2127.5 (4)
O4—S—C11105.6 (2)C7—C6—C4123.6 (4)
C1—S—C1198.6 (2)O2—C6—C4108.9 (4)
C9—O1—C8107.4 (3)C6—C7—C8113.1 (4)
C6—O2—C5106.7 (3)C6—C7—H7123.4
C4—O3—C5106.3 (3)C8—C7—H7123.4
C9—C1—C2108.3 (4)O1—C8—C7124.6 (4)
C9—C1—S123.6 (4)O1—C8—C2110.4 (4)
C2—C1—S127.8 (3)C7—C8—C2125.0 (4)
C8—C2—C3120.0 (4)C1—C9—O1109.4 (4)
C8—C2—C1104.5 (4)C1—C9—C10133.5 (4)
C3—C2—C1135.5 (4)O1—C9—C10117.1 (4)
C4—C3—C2114.9 (4)C9—C10—H10A109.5
C4—C3—H3122.6C9—C10—H10B109.5
C2—C3—H3122.6H10A—C10—H10B109.5
C3—C4—O3127.0 (4)C9—C10—H10C109.5
C3—C4—C6123.3 (4)H10A—C10—H10C109.5
O3—C4—C6109.7 (4)H10B—C10—H10C109.5
O2—C5—O3108.2 (4)S—C11—H11A109.5
O2—C5—H5A110.1S—C11—H11B109.5
O3—C5—H5A110.1H11A—C11—H11B109.5
O2—C5—H5B110.1S—C11—H11C109.5
O3—C5—H5B110.1H11A—C11—H11C109.5
H5A—C5—H5B108.4H11B—C11—H11C109.5
O4—S—C1—C9136.9 (4)O3—C4—C6—C7179.9 (4)
C11—S—C1—C9113.8 (4)C3—C4—C6—O2179.5 (4)
O4—S—C1—C235.9 (4)O3—C4—C6—O20.0 (5)
C11—S—C1—C273.4 (4)O2—C6—C7—C8179.3 (4)
C9—C1—C2—C80.2 (5)C4—C6—C7—C80.6 (7)
S—C1—C2—C8173.9 (3)C9—O1—C8—C7177.4 (4)
C9—C1—C2—C3178.5 (5)C9—O1—C8—C21.3 (5)
S—C1—C2—C34.8 (8)C6—C7—C8—O1178.6 (4)
C8—C2—C3—C41.0 (6)C6—C7—C8—C20.1 (7)
C1—C2—C3—C4177.6 (5)C3—C2—C8—O1179.6 (4)
C2—C3—C4—O3179.0 (4)C1—C2—C8—O10.6 (5)
C2—C3—C4—C60.4 (7)C3—C2—C8—C70.9 (7)
C5—O3—C4—C3177.4 (5)C1—C2—C8—C7178.0 (4)
C5—O3—C4—C63.2 (5)C2—C1—C9—O11.0 (5)
C6—O2—C5—O35.1 (5)S—C1—C9—O1175.0 (3)
C4—O3—C5—O25.1 (5)C2—C1—C9—C10177.7 (5)
C5—O2—C6—C7176.9 (5)S—C1—C9—C103.7 (8)
C5—O2—C6—C43.2 (5)C8—O1—C9—C11.4 (5)
C3—C4—C6—C70.5 (8)C8—O1—C9—C10177.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cg1i0.962.933.841 (6)160
Symmetry code: (i) x1, y, z.
 

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