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The title compound, C17H16O2S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenyl­sulfanyl-1-benzofuran with 3-chloro­peroxy­benzoic acid. The O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The phenyl ring is nearly perpendicular to the plane of the benzofuran unit [88.30 (9)°] and is tilted slightly towards it. No π–π or C—H...π inter­actions are observed between neighbouring mol­ecules in the crystal structure because of steric hindrance induced by the three methyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808019302/rn2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808019302/rn2045Isup2.hkl
Contains datablock I

CCDC reference: 700431

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.055
  • wR factor = 0.163
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 -- C14 .. 5.27 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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

Comment top

This work is related to the our communications on the synthesis and structures of 3-phenylsulfinyl-1-benzofuran analogues, viz. 2,5-dimethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007) and 2,4,6,7-tetramethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2008). Here we report the crystal structure of the title compound, 2,5,7-trimethyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9—C14) is almost perpendicular to the plane of the benzofuran ring system [88.30 (9)°] and is tilted slightly towards it. In the crystal structure, ππ or C—H···π interactions between adjacent molecules are prevented by the steric influence of the three methyl groups in the molecule.

Related literature top

For the crystal structures of similar 3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007, 2008).

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2,5,7-trimethyl-3-phenylsulfanyl-1-benzofuran (268 mg, 1.0 mmol) in dichloromethane (20 ml) at 273 K. After being stirred at room temperature for 2 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 82%, m.p. 393–394 K; Rf = 0.65 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz) δ 2.22 (s, 3H), 2.41 (s, 3H), 2.75 (s, 3H), 6.84 (d, J = 6.96 Hz, 2H), 7.43–7.51 (m, 3H), 7.67 (d, J = 6.60 Hz, 2H); EI—MS 284 [M+].

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H atoms and 0.96 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic and 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) 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, showing displacement ellipsoides drawn at the 30% probability level.
2,5,7-Trimethyl-3-phenylsulfinyl-1-benzofuran top
Crystal data top
C17H16O2SF(000) = 600
Mr = 284.36Dx = 1.281 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybcCell parameters from 1802 reflections
a = 18.393 (2) Åθ = 3.1–24.3°
b = 6.1515 (6) ŵ = 0.22 mm1
c = 13.054 (1) ÅT = 298 K
β = 93.024 (2)°Block, colorless
V = 1474.9 (2) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1611 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 27.0°, θmin = 1.1°
Detector resolution: 10.0 pixels mm-1h = 1823
ϕ and ω scansk = 67
8615 measured reflectionsl = 1613
3215 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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0668P)2 + 0.2115P]
where P = (Fo2 + 2Fc2)/3
3215 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C17H16O2SV = 1474.9 (2) Å3
Mr = 284.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.393 (2) ŵ = 0.22 mm1
b = 6.1515 (6) ÅT = 298 K
c = 13.054 (1) Å0.20 × 0.10 × 0.10 mm
β = 93.024 (2)°
Data collection top
Bruker SMART CCD
diffractometer
1611 reflections with I > 2σ(I)
8615 measured reflectionsRint = 0.066
3215 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 1.01Δρmax = 0.17 e Å3
3215 reflectionsΔρmin = 0.20 e Å3
184 parameters
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
S0.33491 (5)0.75793 (15)0.41600 (7)0.0730 (3)
O10.12972 (11)0.7187 (3)0.31945 (14)0.0536 (5)
O20.34960 (15)0.7328 (5)0.52790 (19)0.1133 (11)
C10.24341 (15)0.6884 (5)0.3874 (2)0.0481 (7)
C20.20160 (15)0.5094 (4)0.42636 (19)0.0438 (7)
C30.21511 (17)0.3364 (5)0.4936 (2)0.0517 (7)
H30.26110.31580.52510.062*
C40.15868 (19)0.1960 (5)0.5125 (2)0.0577 (8)
C50.09051 (19)0.2308 (5)0.4641 (2)0.0653 (9)
H50.05340.13380.47750.078*
C60.07447 (16)0.4016 (5)0.3972 (2)0.0571 (8)
C70.13246 (15)0.5374 (4)0.38166 (19)0.0450 (7)
C80.19788 (17)0.8067 (5)0.3253 (2)0.0517 (7)
C90.37498 (15)0.5292 (5)0.3559 (2)0.0552 (8)
C100.36512 (17)0.5067 (6)0.2517 (3)0.0727 (10)
H100.33750.60730.21340.087*
C110.3964 (2)0.3347 (9)0.2050 (3)0.0974 (14)
H110.38910.31610.13450.117*
C120.4385 (2)0.1893 (8)0.2609 (5)0.1024 (14)
H120.45880.07150.22810.123*
C130.4510 (2)0.2152 (7)0.3637 (4)0.0973 (14)
H130.48070.11790.40090.117*
C140.41888 (19)0.3882 (7)0.4128 (3)0.0779 (11)
H140.42700.40840.48310.094*
C150.1696 (2)0.0106 (6)0.5874 (3)0.0864 (11)
H15A0.22070.00770.60430.130*
H15B0.15030.12070.55690.130*
H15C0.14490.04220.64860.130*
C160.00061 (18)0.4398 (7)0.3461 (3)0.0873 (12)
H16A0.01610.58250.36310.131*
H16B0.03290.33320.36950.131*
H16C0.00350.42800.27310.131*
C170.2083 (2)1.0024 (5)0.2620 (2)0.0760 (10)
H17A0.25481.06620.28030.114*
H17B0.17041.10560.27370.114*
H17C0.20630.96240.19080.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0663 (6)0.0763 (7)0.0762 (6)0.0265 (5)0.0011 (4)0.0218 (5)
O10.0570 (13)0.0537 (13)0.0496 (12)0.0046 (10)0.0005 (9)0.0029 (10)
O20.0903 (18)0.178 (3)0.0700 (17)0.0144 (18)0.0154 (14)0.0556 (17)
C10.0577 (18)0.0457 (17)0.0409 (16)0.0104 (14)0.0017 (13)0.0058 (12)
C20.0541 (17)0.0419 (16)0.0356 (14)0.0058 (13)0.0054 (12)0.0090 (12)
C30.067 (2)0.0490 (17)0.0387 (16)0.0014 (15)0.0030 (14)0.0008 (13)
C40.082 (2)0.0468 (19)0.0457 (18)0.0085 (16)0.0177 (16)0.0021 (13)
C50.073 (2)0.061 (2)0.064 (2)0.0234 (18)0.0229 (17)0.0057 (17)
C60.0527 (19)0.064 (2)0.0554 (19)0.0108 (16)0.0085 (15)0.0140 (16)
C70.0528 (18)0.0443 (17)0.0379 (15)0.0011 (14)0.0025 (13)0.0060 (13)
C80.069 (2)0.0433 (18)0.0434 (16)0.0031 (15)0.0072 (14)0.0056 (13)
C90.0415 (17)0.072 (2)0.0522 (18)0.0146 (15)0.0024 (14)0.0029 (16)
C100.051 (2)0.108 (3)0.058 (2)0.0070 (19)0.0011 (16)0.012 (2)
C110.061 (2)0.144 (4)0.088 (3)0.006 (3)0.006 (2)0.033 (3)
C120.082 (3)0.096 (3)0.132 (4)0.004 (3)0.038 (3)0.022 (3)
C130.074 (3)0.089 (3)0.131 (4)0.008 (2)0.023 (3)0.033 (3)
C140.067 (2)0.100 (3)0.067 (2)0.013 (2)0.0089 (19)0.018 (2)
C150.132 (3)0.063 (2)0.066 (2)0.006 (2)0.026 (2)0.0133 (18)
C160.054 (2)0.107 (3)0.100 (3)0.014 (2)0.001 (2)0.017 (2)
C170.112 (3)0.052 (2)0.065 (2)0.0031 (19)0.015 (2)0.0073 (16)
Geometric parameters (Å, º) top
S—O21.480 (3)C9—C141.376 (4)
S—C11.757 (3)C10—C111.364 (5)
S—C91.789 (3)C10—H100.9300
O1—C81.364 (3)C11—C121.368 (6)
O1—C71.379 (3)C11—H110.9300
C1—C81.347 (4)C12—C131.360 (6)
C1—C21.450 (4)C12—H120.9300
C2—C71.382 (4)C13—C141.390 (6)
C2—C31.393 (4)C13—H130.9300
C3—C41.383 (4)C14—H140.9300
C3—H30.9300C15—H15A0.9600
C4—C51.390 (5)C15—H15B0.9600
C4—C151.509 (4)C15—H15C0.9600
C5—C61.388 (4)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.378 (4)C16—H16C0.9600
C6—C161.500 (4)C17—H17A0.9600
C8—C171.479 (4)C17—H17B0.9600
C9—C101.369 (4)C17—H17C0.9600
O2—S—C1107.90 (15)C11—C10—H10120.5
O2—S—C9107.03 (16)C9—C10—H10120.5
C1—S—C997.32 (13)C10—C11—C12120.6 (4)
C8—O1—C7106.4 (2)C10—C11—H11119.7
C8—C1—C2107.3 (2)C12—C11—H11119.7
C8—C1—S123.7 (2)C13—C12—C11120.8 (4)
C2—C1—S129.0 (2)C13—C12—H12119.6
C7—C2—C3119.4 (3)C11—C12—H12119.6
C7—C2—C1104.5 (2)C12—C13—C14119.4 (4)
C3—C2—C1136.1 (3)C12—C13—H13120.3
C4—C3—C2118.6 (3)C14—C13—H13120.3
C4—C3—H3120.7C9—C14—C13119.0 (4)
C2—C3—H3120.7C9—C14—H14120.5
C3—C4—C5119.4 (3)C13—C14—H14120.5
C3—C4—C15120.8 (3)C4—C15—H15A109.5
C5—C4—C15119.8 (3)C4—C15—H15B109.5
C6—C5—C4124.0 (3)H15A—C15—H15B109.5
C6—C5—H5118.0C4—C15—H15C109.5
C4—C5—H5118.0H15A—C15—H15C109.5
C7—C6—C5114.3 (3)H15B—C15—H15C109.5
C7—C6—C16122.0 (3)C6—C16—H16A109.5
C5—C6—C16123.7 (3)C6—C16—H16B109.5
C6—C7—O1124.9 (3)H16A—C16—H16B109.5
C6—C7—C2124.4 (3)C6—C16—H16C109.5
O1—C7—C2110.7 (2)H16A—C16—H16C109.5
C1—C8—O1111.1 (2)H16B—C16—H16C109.5
C1—C8—C17132.9 (3)C8—C17—H17A109.5
O1—C8—C17115.9 (3)C8—C17—H17B109.5
C10—C9—C14121.1 (3)H17A—C17—H17B109.5
C10—C9—S118.6 (3)C8—C17—H17C109.5
C14—C9—S120.2 (3)H17A—C17—H17C109.5
C11—C10—C9119.1 (4)H17B—C17—H17C109.5
O2—S—C1—C8134.5 (3)C3—C2—C7—C61.3 (4)
C9—S—C1—C8114.9 (3)C1—C2—C7—C6179.7 (3)
O2—S—C1—C242.3 (3)C3—C2—C7—O1178.9 (2)
C9—S—C1—C268.3 (3)C1—C2—C7—O10.1 (3)
C8—C1—C2—C70.5 (3)C2—C1—C8—O10.6 (3)
S—C1—C2—C7177.7 (2)S—C1—C8—O1178.05 (18)
C8—C1—C2—C3178.3 (3)C2—C1—C8—C17178.2 (3)
S—C1—C2—C31.1 (5)S—C1—C8—C174.4 (5)
C7—C2—C3—C40.8 (4)C7—O1—C8—C10.6 (3)
C1—C2—C3—C4179.4 (3)C7—O1—C8—C17178.6 (2)
C2—C3—C4—C50.1 (4)O2—S—C9—C10176.0 (2)
C2—C3—C4—C15177.9 (3)C1—S—C9—C1064.7 (3)
C3—C4—C5—C60.5 (5)O2—S—C9—C148.4 (3)
C15—C4—C5—C6177.5 (3)C1—S—C9—C14119.7 (3)
C4—C5—C6—C70.0 (4)C14—C9—C10—C113.5 (5)
C4—C5—C6—C16179.3 (3)S—C9—C10—C11179.0 (3)
C5—C6—C7—O1179.3 (2)C9—C10—C11—C121.5 (6)
C16—C6—C7—O10.0 (4)C10—C11—C12—C131.1 (7)
C5—C6—C7—C20.9 (4)C11—C12—C13—C141.8 (6)
C16—C6—C7—C2179.8 (3)C10—C9—C14—C132.8 (5)
C8—O1—C7—C6180.0 (3)S—C9—C14—C13178.2 (3)
C8—O1—C7—C20.2 (3)C12—C13—C14—C90.2 (6)

Experimental details

Crystal data
Chemical formulaC17H16O2S
Mr284.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)18.393 (2), 6.1515 (6), 13.054 (1)
β (°) 93.024 (2)
V3)1474.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8615, 3215, 1611
Rint0.066
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.163, 1.01
No. of reflections3215
No. of parameters184
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

 

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