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The title compound, C16H12O4S, was prepared by oxidation of 5,6-methyl­enedi­oxy-3-methylsulfanylbenzofuran using m-chloro­perbenzoic acid. The 5,6-methyl­enedioxy­benzofuran ring system is approximately planar and the crystal structure involves aromatic π–π stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055784/bi2125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055784/bi2125Isup2.hkl
Contains datablock I

CCDC reference: 636142

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.118
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.45 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

5,6-Methylenedioxy-3-methylsulfinyl-2-phenyl-1-benzofuran top
Crystal data top
C16H12O4SF(000) = 624
Mr = 300.32Dx = 1.539 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4941 reflections
a = 7.4000 (5) Åθ = 2.5–28.3°
b = 15.777 (1) ŵ = 0.26 mm1
c = 11.3155 (8) ÅT = 173 K
β = 101.196 (1)°Plate, colourless
V = 1295.94 (15) Å30.51 × 0.32 × 0.09 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.0°, θmin = 2.2°
φ and ω scansh = 89
7774 measured reflectionsk = 2018
2833 independent reflectionsl = 1413
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0445P)2 + 1.6446P]
where P = (Fo2 + 2Fc2)/3
2833 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 1.14 e Å3
0 restraintsΔρmin = 0.47 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
S0.51198 (7)0.05257 (3)0.79213 (4)0.02243 (15)
O10.1269 (3)0.24499 (10)0.53721 (15)0.0340 (4)
O20.0136 (2)0.19707 (10)0.34281 (14)0.0308 (4)
O30.25918 (19)0.08537 (9)0.45181 (12)0.0197 (3)
O40.6019 (2)0.03175 (11)0.81984 (15)0.0337 (4)
C10.3846 (3)0.04853 (13)0.64262 (17)0.0189 (4)
C20.2978 (3)0.02611 (13)0.58253 (17)0.0186 (4)
C30.2742 (3)0.11107 (13)0.61696 (18)0.0224 (4)
H30.32210.13140.69380.027*
C40.1749 (3)0.16124 (13)0.52780 (19)0.0222 (4)
C50.0429 (3)0.27114 (14)0.4178 (2)0.0275 (5)
H5A0.07360.29900.41880.033*
H5B0.12260.31070.38680.033*
C60.1052 (3)0.13228 (13)0.41076 (18)0.0216 (4)
C70.1263 (3)0.05049 (13)0.37412 (18)0.0214 (4)
H70.08020.03110.29650.026*
C80.2239 (3)0.00058 (12)0.46547 (17)0.0189 (4)
C90.3573 (3)0.11363 (13)0.56109 (17)0.0185 (4)
C100.4055 (3)0.20388 (13)0.56394 (18)0.0192 (4)
C110.3868 (3)0.24948 (14)0.45584 (19)0.0248 (4)
H110.34460.22220.38280.030*
C120.4307 (3)0.33508 (14)0.4570 (2)0.0276 (5)
H120.41500.36500.38500.033*
C130.4977 (3)0.37633 (14)0.5651 (2)0.0277 (5)
H130.53050.43330.56540.033*
C140.5155 (3)0.33188 (14)0.6727 (2)0.0279 (5)
H140.55970.35930.74530.034*
C150.4678 (3)0.24684 (14)0.67250 (19)0.0249 (4)
H150.47730.21810.74520.030*
C160.3175 (3)0.05441 (16)0.8664 (2)0.0304 (5)
H16A0.36040.05680.95200.046*
H16B0.24530.00410.84620.046*
H16C0.24310.10330.84060.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0230 (3)0.0241 (3)0.0179 (3)0.00025 (19)0.00176 (18)0.00207 (19)
O10.0490 (11)0.0216 (8)0.0285 (8)0.0084 (7)0.0008 (7)0.0003 (6)
O20.0393 (9)0.0225 (8)0.0276 (8)0.0063 (7)0.0011 (7)0.0043 (6)
O30.0228 (7)0.0198 (7)0.0154 (7)0.0000 (5)0.0010 (5)0.0009 (5)
O40.0358 (9)0.0346 (9)0.0278 (8)0.0133 (7)0.0005 (7)0.0060 (7)
C10.0176 (9)0.0228 (10)0.0160 (9)0.0010 (7)0.0026 (7)0.0009 (7)
C20.0172 (9)0.0215 (10)0.0171 (9)0.0027 (7)0.0034 (7)0.0014 (7)
C30.0260 (10)0.0223 (10)0.0182 (9)0.0012 (8)0.0027 (8)0.0023 (8)
C40.0235 (10)0.0183 (10)0.0256 (10)0.0005 (8)0.0067 (8)0.0007 (8)
C50.0276 (11)0.0223 (11)0.0323 (12)0.0017 (8)0.0048 (9)0.0035 (9)
C60.0183 (9)0.0250 (10)0.0212 (10)0.0000 (8)0.0032 (7)0.0054 (8)
C70.0226 (10)0.0245 (10)0.0163 (9)0.0022 (8)0.0016 (7)0.0005 (8)
C80.0189 (9)0.0187 (9)0.0191 (9)0.0025 (7)0.0038 (7)0.0008 (7)
C90.0174 (9)0.0222 (10)0.0155 (9)0.0018 (7)0.0025 (7)0.0019 (7)
C100.0160 (9)0.0204 (10)0.0212 (10)0.0018 (7)0.0041 (7)0.0021 (7)
C110.0254 (11)0.0286 (11)0.0195 (10)0.0007 (8)0.0025 (8)0.0012 (8)
C120.0278 (11)0.0280 (11)0.0270 (11)0.0008 (9)0.0055 (9)0.0091 (9)
C130.0251 (11)0.0196 (10)0.0383 (12)0.0012 (8)0.0057 (9)0.0023 (9)
C140.0288 (11)0.0251 (11)0.0282 (11)0.0007 (9)0.0014 (9)0.0049 (9)
C150.0311 (11)0.0230 (10)0.0197 (10)0.0012 (8)0.0028 (8)0.0015 (8)
C160.0346 (12)0.0372 (13)0.0201 (10)0.0061 (10)0.0072 (9)0.0005 (9)
Geometric parameters (Å, º) top
S—O41.4930 (17)C6—C71.373 (3)
S—C11.771 (2)C7—C81.396 (3)
S—C161.802 (2)C7—H70.930
O1—C41.378 (3)C9—C101.467 (3)
O1—C51.434 (3)C10—C151.400 (3)
O2—C61.376 (2)C10—C111.403 (3)
O2—C51.436 (3)C11—C121.389 (3)
O3—C81.377 (2)C11—H110.930
O3—C91.381 (2)C12—C131.389 (3)
C1—C91.369 (3)C12—H120.930
C1—C21.446 (3)C13—C141.389 (3)
C2—C81.396 (3)C13—H130.930
C2—C31.416 (3)C14—C151.387 (3)
C3—C41.377 (3)C14—H140.930
C3—H30.930C15—H150.930
C4—C61.401 (3)C16—H16A0.960
C5—H5A0.970C16—H16B0.960
C5—H5B0.970C16—H16C0.960
O4—S—C1107.54 (10)O3—C8—C2110.58 (17)
O4—S—C16106.26 (11)O3—C8—C7124.02 (17)
C1—S—C1696.95 (10)C2—C8—C7125.40 (19)
C4—O1—C5105.92 (16)C1—C9—O3110.14 (17)
C6—O2—C5105.84 (16)C1—C9—C10135.24 (18)
C8—O3—C9106.94 (15)O3—C9—C10114.62 (16)
C9—C1—C2107.46 (17)C15—C10—C11118.48 (19)
C9—C1—S126.75 (16)C15—C10—C9121.76 (18)
C2—C1—S125.72 (15)C11—C10—C9119.75 (18)
C8—C2—C3120.00 (18)C12—C11—C10120.5 (2)
C8—C2—C1104.88 (17)C12—C11—H11119.8
C3—C2—C1135.11 (18)C10—C11—H11119.8
C4—C3—C2114.78 (18)C11—C12—C13120.5 (2)
C4—C3—H3122.6C11—C12—H12119.8
C2—C3—H3122.6C13—C12—H12119.8
C3—C4—O1127.12 (19)C14—C13—C12119.5 (2)
C3—C4—C6123.45 (19)C14—C13—H13120.3
O1—C4—C6109.42 (18)C12—C13—H13120.3
O1—C5—O2108.11 (17)C15—C14—C13120.4 (2)
O1—C5—H5A110.1C15—C14—H14119.8
O2—C5—H5A110.1C13—C14—H14119.8
O1—C5—H5B110.1C14—C15—C10120.6 (2)
O2—C5—H5B110.1C14—C15—H15119.7
H5A—C5—H5B108.4C10—C15—H15119.7
C7—C6—O2126.99 (19)S—C16—H16A109.5
C7—C6—C4123.31 (19)S—C16—H16B109.5
O2—C6—C4109.69 (18)H16A—C16—H16B109.5
C6—C7—C8113.04 (18)S—C16—H16C109.5
C6—C7—H7123.5H16A—C16—H16C109.5
C8—C7—H7123.5H16B—C16—H16C109.5
O4—S—C1—C9145.68 (18)C9—O3—C8—C7179.71 (18)
C16—S—C1—C9104.8 (2)C3—C2—C8—O3178.75 (17)
O4—S—C1—C231.0 (2)C1—C2—C8—O30.4 (2)
C16—S—C1—C278.54 (19)C3—C2—C8—C70.8 (3)
C9—C1—C2—C80.5 (2)C1—C2—C8—C7179.92 (19)
S—C1—C2—C8176.75 (15)C6—C7—C8—O3178.43 (18)
C9—C1—C2—C3178.5 (2)C6—C7—C8—C21.0 (3)
S—C1—C2—C34.3 (3)C2—C1—C9—O30.4 (2)
C8—C2—C3—C40.5 (3)S—C1—C9—O3176.79 (14)
C1—C2—C3—C4178.3 (2)C2—C1—C9—C10178.8 (2)
C2—C3—C4—O1178.0 (2)S—C1—C9—C104.0 (3)
C2—C3—C4—C61.4 (3)C8—O3—C9—C10.1 (2)
C5—O1—C4—C3173.8 (2)C8—O3—C9—C10179.25 (16)
C5—O1—C4—C66.7 (2)C1—C9—C10—C1513.5 (4)
C4—O1—C5—O210.1 (2)O3—C9—C10—C15165.68 (18)
C6—O2—C5—O19.6 (2)C1—C9—C10—C11167.5 (2)
C5—O2—C6—C7175.4 (2)O3—C9—C10—C1113.4 (3)
C5—O2—C6—C45.5 (2)C15—C10—C11—C120.5 (3)
C3—C4—C6—C71.2 (3)C9—C10—C11—C12179.58 (19)
O1—C4—C6—C7178.30 (19)C10—C11—C12—C131.5 (3)
C3—C4—C6—O2179.69 (19)C11—C12—C13—C141.9 (3)
O1—C4—C6—O20.8 (2)C12—C13—C14—C150.4 (3)
O2—C6—C7—C8178.86 (19)C13—C14—C15—C101.6 (3)
C4—C6—C7—C80.1 (3)C11—C10—C15—C142.1 (3)
C9—O3—C8—C20.2 (2)C9—C10—C15—C14178.9 (2)
 

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