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In the title compound, C17H15FO2S, the benzo­furan ring system, being essentially planar, with an r.m.s. deviation from the least-squares plane of 0.009 (2) Å, makes a dihedral angle of 79.02 (5)° with the plane of the 2-fluoro­phenyl group. In the crystal, mol­ecules are linked by pairs of weak C—H...O hydrogen bonds into centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813011495/yk2091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536813011495/yk2091Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813011495/yk2091Isup3.cml
Supplementary material

CCDC reference: 954867

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.099
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 69 Perc.
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 5 Informative message, check

Comment top

As a part of our continuing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (Choi et al., 2010) and 3-fluorophenylsulfinyl (Choi et al., 2011) substituents in 3-position, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 2-fluorophenyl ring and the mean plane of the benzofuran ring is 79.02 (5)°. In the crystal structure, molecules are connected by pairs of weak C—H..O hydrogen bonds into centrosymmetric dimers (Table 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(2-fluorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (315 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (benzene) to afford the title compound as a colorless solid [yield 76%, m.p. 394–395 K; Rf = 0.46 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
3-(2-Fluorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran top
Crystal data top
C17H15FO2SZ = 2
Mr = 302.35F(000) = 316
Triclinic, P1Dx = 1.399 Mg m3
Hall symbol: -P 1Melting point = 394–395 K
a = 6.0969 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9279 (16) ÅCell parameters from 3261 reflections
c = 11.2209 (16) Åθ = 2.4–26.4°
α = 78.167 (10)°µ = 0.24 mm1
β = 83.72 (1)°T = 173 K
γ = 79.722 (11)°Block, colourless
V = 717.92 (19) Å30.22 × 0.13 × 0.12 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2533 independent reflections
Radiation source: rotating anode2028 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.042
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 1.9°
ϕ and ω scansh = 77
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.640, Tmax = 0.746l = 1313
10389 measured 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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.099H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0383P)2 + 0.4211P]
where P = (Fo2 + 2Fc2)/3
2533 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C17H15FO2Sγ = 79.722 (11)°
Mr = 302.35V = 717.92 (19) Å3
Triclinic, P1Z = 2
a = 6.0969 (10) ÅMo Kα radiation
b = 10.9279 (16) ŵ = 0.24 mm1
c = 11.2209 (16) ÅT = 173 K
α = 78.167 (10)°0.22 × 0.13 × 0.12 mm
β = 83.72 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
2533 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2028 reflections with I > 2σ(I)
Tmin = 0.640, Tmax = 0.746Rint = 0.042
10389 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.05Δρmax = 0.22 e Å3
2533 reflectionsΔρmin = 0.27 e Å3
193 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S10.53792 (10)0.04652 (5)0.12189 (5)0.03178 (17)
F10.1918 (2)0.28030 (14)0.06722 (13)0.0503 (4)
O10.2735 (2)0.11435 (14)0.43943 (13)0.0326 (4)
O20.7672 (3)0.02603 (15)0.12725 (15)0.0427 (4)
C10.4627 (4)0.10282 (19)0.25824 (19)0.0281 (5)
C20.5593 (3)0.18749 (19)0.31335 (19)0.0271 (5)
C30.7316 (4)0.2583 (2)0.2813 (2)0.0304 (5)
H30.81940.25680.20610.037*
C40.7730 (4)0.3311 (2)0.3611 (2)0.0336 (5)
C50.6391 (4)0.3330 (2)0.4711 (2)0.0368 (6)
H50.66880.38450.52410.044*
C60.4664 (4)0.2636 (2)0.5060 (2)0.0346 (5)
C70.4356 (4)0.19125 (19)0.42355 (19)0.0288 (5)
C80.2952 (4)0.0620 (2)0.33726 (19)0.0299 (5)
C90.9605 (4)0.4073 (2)0.3309 (2)0.0440 (6)
H9A1.07490.36830.27560.066*
H9B1.02650.40940.40610.066*
H9C0.90260.49390.29120.066*
C100.3234 (5)0.2640 (3)0.6234 (2)0.0492 (7)
H10A0.16910.30100.60570.074*
H10B0.38000.31440.67250.074*
H10C0.32770.17690.66870.074*
C110.1356 (4)0.0245 (2)0.3341 (2)0.0366 (6)
H11A0.16040.05400.25620.055*
H11B0.01760.02060.34260.055*
H11C0.15840.09730.40140.055*
C120.5649 (4)0.1939 (2)0.02030 (19)0.0294 (5)
C130.3881 (4)0.2921 (2)0.0008 (2)0.0346 (5)
C140.4049 (4)0.4017 (2)0.0821 (2)0.0423 (6)
H140.28170.46870.09250.051*
C150.6056 (5)0.4119 (2)0.1500 (2)0.0446 (6)
H150.62110.48670.20850.053*
C160.7835 (4)0.3147 (2)0.1339 (2)0.0440 (6)
H160.92060.32270.18170.053*
C170.7641 (4)0.2053 (2)0.0484 (2)0.0357 (5)
H170.88760.13850.03720.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0403 (3)0.0285 (3)0.0280 (3)0.0103 (2)0.0039 (2)0.0080 (2)
F10.0343 (8)0.0617 (10)0.0483 (9)0.0033 (7)0.0032 (7)0.0023 (7)
O10.0354 (9)0.0332 (8)0.0275 (8)0.0073 (7)0.0059 (7)0.0048 (7)
O20.0483 (10)0.0361 (9)0.0379 (9)0.0035 (8)0.0052 (8)0.0067 (8)
C10.0319 (12)0.0261 (11)0.0257 (11)0.0066 (9)0.0011 (9)0.0037 (9)
C20.0319 (12)0.0233 (11)0.0245 (11)0.0028 (9)0.0011 (9)0.0027 (9)
C30.0317 (12)0.0270 (11)0.0307 (12)0.0039 (9)0.0004 (9)0.0033 (9)
C40.0373 (13)0.0235 (11)0.0391 (13)0.0023 (10)0.0096 (11)0.0024 (10)
C50.0505 (15)0.0259 (12)0.0358 (13)0.0007 (11)0.0128 (11)0.0097 (10)
C60.0440 (14)0.0291 (12)0.0276 (12)0.0012 (10)0.0051 (10)0.0030 (10)
C70.0327 (12)0.0240 (11)0.0278 (12)0.0032 (9)0.0008 (9)0.0025 (9)
C80.0342 (12)0.0277 (11)0.0270 (11)0.0043 (9)0.0013 (9)0.0047 (9)
C90.0496 (15)0.0326 (13)0.0524 (16)0.0118 (11)0.0112 (12)0.0057 (12)
C100.0671 (18)0.0478 (15)0.0320 (14)0.0038 (13)0.0026 (12)0.0138 (12)
C110.0349 (13)0.0336 (12)0.0411 (14)0.0109 (10)0.0023 (11)0.0047 (11)
C120.0374 (12)0.0309 (11)0.0232 (11)0.0120 (10)0.0001 (9)0.0080 (9)
C130.0356 (13)0.0423 (14)0.0280 (12)0.0100 (11)0.0009 (10)0.0087 (10)
C140.0545 (16)0.0352 (13)0.0369 (14)0.0031 (12)0.0116 (12)0.0055 (11)
C150.0632 (18)0.0378 (14)0.0334 (14)0.0194 (13)0.0013 (12)0.0003 (11)
C160.0510 (16)0.0504 (15)0.0334 (13)0.0245 (13)0.0090 (12)0.0067 (12)
C170.0386 (13)0.0374 (13)0.0329 (13)0.0105 (11)0.0038 (10)0.0103 (10)
Geometric parameters (Å, º) top
S1—O21.4800 (17)C9—H9A0.9800
S1—C11.750 (2)C9—H9B0.9800
S1—C121.794 (2)C9—H9C0.9800
F1—C131.351 (3)C10—H10A0.9800
O1—C81.367 (3)C10—H10B0.9800
O1—C71.382 (3)C10—H10C0.9800
C1—C81.353 (3)C11—H11A0.9800
C1—C21.447 (3)C11—H11B0.9800
C2—C71.380 (3)C11—H11C0.9800
C2—C31.388 (3)C12—C171.376 (3)
C3—C41.383 (3)C12—C131.380 (3)
C3—H30.9500C13—C141.370 (3)
C4—C51.405 (3)C14—C151.378 (4)
C4—C91.501 (3)C14—H140.9500
C5—C61.383 (3)C15—C161.374 (4)
C5—H50.9500C15—H150.9500
C6—C71.381 (3)C16—C171.386 (3)
C6—C101.498 (3)C16—H160.9500
C8—C111.480 (3)C17—H170.9500
O2—S1—C1108.67 (10)H9A—C9—H9C109.5
O2—S1—C12105.39 (10)H9B—C9—H9C109.5
C1—S1—C1299.10 (10)C6—C10—H10A109.5
C8—O1—C7106.29 (16)C6—C10—H10B109.5
C8—C1—C2107.28 (18)H10A—C10—H10B109.5
C8—C1—S1121.35 (17)C6—C10—H10C109.5
C2—C1—S1131.27 (16)H10A—C10—H10C109.5
C7—C2—C3119.3 (2)H10B—C10—H10C109.5
C7—C2—C1104.71 (18)C8—C11—H11A109.5
C3—C2—C1136.0 (2)C8—C11—H11B109.5
C4—C3—C2118.6 (2)H11A—C11—H11B109.5
C4—C3—H3120.7C8—C11—H11C109.5
C2—C3—H3120.7H11A—C11—H11C109.5
C3—C4—C5119.6 (2)H11B—C11—H11C109.5
C3—C4—C9120.3 (2)C17—C12—C13118.7 (2)
C5—C4—C9120.1 (2)C17—C12—S1118.60 (18)
C6—C5—C4123.4 (2)C13—C12—S1122.49 (17)
C6—C5—H5118.3F1—C13—C14118.8 (2)
C4—C5—H5118.3F1—C13—C12118.7 (2)
C7—C6—C5114.3 (2)C14—C13—C12122.5 (2)
C7—C6—C10121.8 (2)C13—C14—C15118.1 (2)
C5—C6—C10123.9 (2)C13—C14—H14120.9
C2—C7—C6124.8 (2)C15—C14—H14120.9
C2—C7—O1110.78 (18)C16—C15—C14120.6 (2)
C6—C7—O1124.4 (2)C16—C15—H15119.7
C1—C8—O1110.95 (19)C14—C15—H15119.7
C1—C8—C11133.3 (2)C15—C16—C17120.4 (2)
O1—C8—C11115.71 (19)C15—C16—H16119.8
C4—C9—H9A109.5C17—C16—H16119.8
C4—C9—H9B109.5C12—C17—C16119.6 (2)
H9A—C9—H9B109.5C12—C17—H17120.2
C4—C9—H9C109.5C16—C17—H17120.2
O2—S1—C1—C8114.62 (19)C8—O1—C7—C20.3 (2)
C12—S1—C1—C8135.63 (19)C8—O1—C7—C6178.7 (2)
O2—S1—C1—C261.2 (2)C2—C1—C8—O10.5 (2)
C12—S1—C1—C248.6 (2)S1—C1—C8—O1177.20 (14)
C8—C1—C2—C70.7 (2)C2—C1—C8—C11180.0 (2)
S1—C1—C2—C7176.90 (17)S1—C1—C8—C113.3 (4)
C8—C1—C2—C3179.6 (2)C7—O1—C8—C10.2 (2)
S1—C1—C2—C33.3 (4)C7—O1—C8—C11179.71 (18)
C7—C2—C3—C40.3 (3)O2—S1—C12—C1711.7 (2)
C1—C2—C3—C4179.4 (2)C1—S1—C12—C17124.08 (18)
C2—C3—C4—C50.8 (3)O2—S1—C12—C13173.87 (18)
C2—C3—C4—C9178.9 (2)C1—S1—C12—C1361.5 (2)
C3—C4—C5—C60.9 (3)C17—C12—C13—F1179.23 (19)
C9—C4—C5—C6178.8 (2)S1—C12—C13—F14.8 (3)
C4—C5—C6—C70.1 (3)C17—C12—C13—C141.6 (3)
C4—C5—C6—C10179.6 (2)S1—C12—C13—C14175.97 (18)
C3—C2—C7—C61.4 (3)F1—C13—C14—C15179.4 (2)
C1—C2—C7—C6178.4 (2)C12—C13—C14—C151.4 (4)
C3—C2—C7—O1179.60 (18)C13—C14—C15—C160.4 (4)
C1—C2—C7—O10.6 (2)C14—C15—C16—C170.4 (4)
C5—C6—C7—C21.3 (3)C13—C12—C17—C160.7 (3)
C10—C6—C7—C2179.2 (2)S1—C12—C17—C16175.30 (18)
C5—C6—C7—O1179.88 (19)C15—C16—C17—C120.3 (4)
C10—C6—C7—O10.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.952.473.308 (3)148
Symmetry code: (i) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC17H15FO2S
Mr302.35
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.0969 (10), 10.9279 (16), 11.2209 (16)
α, β, γ (°)78.167 (10), 83.72 (1), 79.722 (11)
V3)717.92 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.22 × 0.13 × 0.12
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.640, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
10389, 2533, 2028
Rint0.042
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.099, 1.05
No. of reflections2533
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.952.473.308 (3)147.7
Symmetry code: (i) x+2, y, z.
 

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