


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808019302/rn2045sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808019302/rn2045Isup2.hkl |
CCDC reference: 700431
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(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
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+].
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.
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).
![]() | Fig. 1. The molecular structure of the title compound, showing displacement ellipsoides drawn at the 30% probability level. |
C17H16O2S | F(000) = 600 |
Mr = 284.36 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P_2ybc | Cell parameters from 1802 reflections |
a = 18.393 (2) Å | θ = 3.1–24.3° |
b = 6.1515 (6) Å | µ = 0.22 mm−1 |
c = 13.054 (1) Å | T = 298 K |
β = 93.024 (2)° | Block, colorless |
V = 1474.9 (2) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 1611 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 27.0°, θmin = 1.1° |
Detector resolution: 10.0 pixels mm-1 | h = −18→23 |
ϕ and ω scans | k = −6→7 |
8615 measured reflections | l = −16→13 |
3215 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C17H16O2S | V = 1474.9 (2) Å3 |
Mr = 284.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.393 (2) Å | µ = 0.22 mm−1 |
b = 6.1515 (6) Å | T = 298 K |
c = 13.054 (1) Å | 0.20 × 0.10 × 0.10 mm |
β = 93.024 (2)° |
Bruker SMART CCD diffractometer | 1611 reflections with I > 2σ(I) |
8615 measured reflections | Rint = 0.066 |
3215 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3215 reflections | Δρmin = −0.20 e Å−3 |
184 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S | 0.33491 (5) | 0.75793 (15) | 0.41600 (7) | 0.0730 (3) | |
O1 | 0.12972 (11) | 0.7187 (3) | 0.31945 (14) | 0.0536 (5) | |
O2 | 0.34960 (15) | 0.7328 (5) | 0.52790 (19) | 0.1133 (11) | |
C1 | 0.24341 (15) | 0.6884 (5) | 0.3874 (2) | 0.0481 (7) | |
C2 | 0.20160 (15) | 0.5094 (4) | 0.42636 (19) | 0.0438 (7) | |
C3 | 0.21511 (17) | 0.3364 (5) | 0.4936 (2) | 0.0517 (7) | |
H3 | 0.2611 | 0.3158 | 0.5251 | 0.062* | |
C4 | 0.15868 (19) | 0.1960 (5) | 0.5125 (2) | 0.0577 (8) | |
C5 | 0.09051 (19) | 0.2308 (5) | 0.4641 (2) | 0.0653 (9) | |
H5 | 0.0534 | 0.1338 | 0.4775 | 0.078* | |
C6 | 0.07447 (16) | 0.4016 (5) | 0.3972 (2) | 0.0571 (8) | |
C7 | 0.13246 (15) | 0.5374 (4) | 0.38166 (19) | 0.0450 (7) | |
C8 | 0.19788 (17) | 0.8067 (5) | 0.3253 (2) | 0.0517 (7) | |
C9 | 0.37498 (15) | 0.5292 (5) | 0.3559 (2) | 0.0552 (8) | |
C10 | 0.36512 (17) | 0.5067 (6) | 0.2517 (3) | 0.0727 (10) | |
H10 | 0.3375 | 0.6073 | 0.2134 | 0.087* | |
C11 | 0.3964 (2) | 0.3347 (9) | 0.2050 (3) | 0.0974 (14) | |
H11 | 0.3891 | 0.3161 | 0.1345 | 0.117* | |
C12 | 0.4385 (2) | 0.1893 (8) | 0.2609 (5) | 0.1024 (14) | |
H12 | 0.4588 | 0.0715 | 0.2281 | 0.123* | |
C13 | 0.4510 (2) | 0.2152 (7) | 0.3637 (4) | 0.0973 (14) | |
H13 | 0.4807 | 0.1179 | 0.4009 | 0.117* | |
C14 | 0.41888 (19) | 0.3882 (7) | 0.4128 (3) | 0.0779 (11) | |
H14 | 0.4270 | 0.4084 | 0.4831 | 0.094* | |
C15 | 0.1696 (2) | 0.0106 (6) | 0.5874 (3) | 0.0864 (11) | |
H15A | 0.2207 | −0.0077 | 0.6043 | 0.130* | |
H15B | 0.1503 | −0.1207 | 0.5569 | 0.130* | |
H15C | 0.1449 | 0.0422 | 0.6486 | 0.130* | |
C16 | 0.00061 (18) | 0.4398 (7) | 0.3461 (3) | 0.0873 (12) | |
H16A | −0.0161 | 0.5825 | 0.3631 | 0.131* | |
H16B | −0.0329 | 0.3332 | 0.3695 | 0.131* | |
H16C | 0.0035 | 0.4280 | 0.2731 | 0.131* | |
C17 | 0.2083 (2) | 1.0024 (5) | 0.2620 (2) | 0.0760 (10) | |
H17A | 0.2548 | 1.0662 | 0.2803 | 0.114* | |
H17B | 0.1704 | 1.1056 | 0.2737 | 0.114* | |
H17C | 0.2063 | 0.9624 | 0.1908 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0663 (6) | 0.0763 (7) | 0.0762 (6) | −0.0265 (5) | 0.0011 (4) | −0.0218 (5) |
O1 | 0.0570 (13) | 0.0537 (13) | 0.0496 (12) | 0.0046 (10) | −0.0005 (9) | −0.0029 (10) |
O2 | 0.0903 (18) | 0.178 (3) | 0.0700 (17) | −0.0144 (18) | −0.0154 (14) | −0.0556 (17) |
C1 | 0.0577 (18) | 0.0457 (17) | 0.0409 (16) | −0.0104 (14) | 0.0017 (13) | −0.0058 (12) |
C2 | 0.0541 (17) | 0.0419 (16) | 0.0356 (14) | −0.0058 (13) | 0.0054 (12) | −0.0090 (12) |
C3 | 0.067 (2) | 0.0490 (17) | 0.0387 (16) | 0.0014 (15) | 0.0030 (14) | −0.0008 (13) |
C4 | 0.082 (2) | 0.0468 (19) | 0.0457 (18) | −0.0085 (16) | 0.0177 (16) | −0.0021 (13) |
C5 | 0.073 (2) | 0.061 (2) | 0.064 (2) | −0.0234 (18) | 0.0229 (17) | −0.0057 (17) |
C6 | 0.0527 (19) | 0.064 (2) | 0.0554 (19) | −0.0108 (16) | 0.0085 (15) | −0.0140 (16) |
C7 | 0.0528 (18) | 0.0443 (17) | 0.0379 (15) | −0.0011 (14) | 0.0025 (13) | −0.0060 (13) |
C8 | 0.069 (2) | 0.0433 (18) | 0.0434 (16) | −0.0031 (15) | 0.0072 (14) | −0.0056 (13) |
C9 | 0.0415 (17) | 0.072 (2) | 0.0522 (18) | −0.0146 (15) | 0.0024 (14) | 0.0029 (16) |
C10 | 0.051 (2) | 0.108 (3) | 0.058 (2) | 0.0070 (19) | −0.0011 (16) | −0.012 (2) |
C11 | 0.061 (2) | 0.144 (4) | 0.088 (3) | 0.006 (3) | 0.006 (2) | −0.033 (3) |
C12 | 0.082 (3) | 0.096 (3) | 0.132 (4) | −0.004 (3) | 0.038 (3) | −0.022 (3) |
C13 | 0.074 (3) | 0.089 (3) | 0.131 (4) | 0.008 (2) | 0.023 (3) | 0.033 (3) |
C14 | 0.067 (2) | 0.100 (3) | 0.067 (2) | −0.013 (2) | 0.0089 (19) | 0.018 (2) |
C15 | 0.132 (3) | 0.063 (2) | 0.066 (2) | −0.006 (2) | 0.026 (2) | 0.0133 (18) |
C16 | 0.054 (2) | 0.107 (3) | 0.100 (3) | −0.014 (2) | 0.001 (2) | −0.017 (2) |
C17 | 0.112 (3) | 0.052 (2) | 0.065 (2) | −0.0031 (19) | 0.015 (2) | 0.0073 (16) |
S—O2 | 1.480 (3) | C9—C14 | 1.376 (4) |
S—C1 | 1.757 (3) | C10—C11 | 1.364 (5) |
S—C9 | 1.789 (3) | C10—H10 | 0.9300 |
O1—C8 | 1.364 (3) | C11—C12 | 1.368 (6) |
O1—C7 | 1.379 (3) | C11—H11 | 0.9300 |
C1—C8 | 1.347 (4) | C12—C13 | 1.360 (6) |
C1—C2 | 1.450 (4) | C12—H12 | 0.9300 |
C2—C7 | 1.382 (4) | C13—C14 | 1.390 (6) |
C2—C3 | 1.393 (4) | C13—H13 | 0.9300 |
C3—C4 | 1.383 (4) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.390 (5) | C15—H15B | 0.9600 |
C4—C15 | 1.509 (4) | C15—H15C | 0.9600 |
C5—C6 | 1.388 (4) | C16—H16A | 0.9600 |
C5—H5 | 0.9300 | C16—H16B | 0.9600 |
C6—C7 | 1.378 (4) | C16—H16C | 0.9600 |
C6—C16 | 1.500 (4) | C17—H17A | 0.9600 |
C8—C17 | 1.479 (4) | C17—H17B | 0.9600 |
C9—C10 | 1.369 (4) | C17—H17C | 0.9600 |
O2—S—C1 | 107.90 (15) | C11—C10—H10 | 120.5 |
O2—S—C9 | 107.03 (16) | C9—C10—H10 | 120.5 |
C1—S—C9 | 97.32 (13) | C10—C11—C12 | 120.6 (4) |
C8—O1—C7 | 106.4 (2) | C10—C11—H11 | 119.7 |
C8—C1—C2 | 107.3 (2) | C12—C11—H11 | 119.7 |
C8—C1—S | 123.7 (2) | C13—C12—C11 | 120.8 (4) |
C2—C1—S | 129.0 (2) | C13—C12—H12 | 119.6 |
C7—C2—C3 | 119.4 (3) | C11—C12—H12 | 119.6 |
C7—C2—C1 | 104.5 (2) | C12—C13—C14 | 119.4 (4) |
C3—C2—C1 | 136.1 (3) | C12—C13—H13 | 120.3 |
C4—C3—C2 | 118.6 (3) | C14—C13—H13 | 120.3 |
C4—C3—H3 | 120.7 | C9—C14—C13 | 119.0 (4) |
C2—C3—H3 | 120.7 | C9—C14—H14 | 120.5 |
C3—C4—C5 | 119.4 (3) | C13—C14—H14 | 120.5 |
C3—C4—C15 | 120.8 (3) | C4—C15—H15A | 109.5 |
C5—C4—C15 | 119.8 (3) | C4—C15—H15B | 109.5 |
C6—C5—C4 | 124.0 (3) | H15A—C15—H15B | 109.5 |
C6—C5—H5 | 118.0 | C4—C15—H15C | 109.5 |
C4—C5—H5 | 118.0 | H15A—C15—H15C | 109.5 |
C7—C6—C5 | 114.3 (3) | H15B—C15—H15C | 109.5 |
C7—C6—C16 | 122.0 (3) | C6—C16—H16A | 109.5 |
C5—C6—C16 | 123.7 (3) | C6—C16—H16B | 109.5 |
C6—C7—O1 | 124.9 (3) | H16A—C16—H16B | 109.5 |
C6—C7—C2 | 124.4 (3) | C6—C16—H16C | 109.5 |
O1—C7—C2 | 110.7 (2) | H16A—C16—H16C | 109.5 |
C1—C8—O1 | 111.1 (2) | H16B—C16—H16C | 109.5 |
C1—C8—C17 | 132.9 (3) | C8—C17—H17A | 109.5 |
O1—C8—C17 | 115.9 (3) | C8—C17—H17B | 109.5 |
C10—C9—C14 | 121.1 (3) | H17A—C17—H17B | 109.5 |
C10—C9—S | 118.6 (3) | C8—C17—H17C | 109.5 |
C14—C9—S | 120.2 (3) | H17A—C17—H17C | 109.5 |
C11—C10—C9 | 119.1 (4) | H17B—C17—H17C | 109.5 |
O2—S—C1—C8 | 134.5 (3) | C3—C2—C7—C6 | −1.3 (4) |
C9—S—C1—C8 | −114.9 (3) | C1—C2—C7—C6 | 179.7 (3) |
O2—S—C1—C2 | −42.3 (3) | C3—C2—C7—O1 | 178.9 (2) |
C9—S—C1—C2 | 68.3 (3) | C1—C2—C7—O1 | −0.1 (3) |
C8—C1—C2—C7 | 0.5 (3) | C2—C1—C8—O1 | −0.6 (3) |
S—C1—C2—C7 | 177.7 (2) | S—C1—C8—O1 | −178.05 (18) |
C8—C1—C2—C3 | −178.3 (3) | C2—C1—C8—C17 | −178.2 (3) |
S—C1—C2—C3 | −1.1 (5) | S—C1—C8—C17 | 4.4 (5) |
C7—C2—C3—C4 | 0.8 (4) | C7—O1—C8—C1 | 0.6 (3) |
C1—C2—C3—C4 | 179.4 (3) | C7—O1—C8—C17 | 178.6 (2) |
C2—C3—C4—C5 | 0.1 (4) | O2—S—C9—C10 | 176.0 (2) |
C2—C3—C4—C15 | −177.9 (3) | C1—S—C9—C10 | 64.7 (3) |
C3—C4—C5—C6 | −0.5 (5) | O2—S—C9—C14 | −8.4 (3) |
C15—C4—C5—C6 | 177.5 (3) | C1—S—C9—C14 | −119.7 (3) |
C4—C5—C6—C7 | 0.0 (4) | C14—C9—C10—C11 | 3.5 (5) |
C4—C5—C6—C16 | −179.3 (3) | S—C9—C10—C11 | 179.0 (3) |
C5—C6—C7—O1 | −179.3 (2) | C9—C10—C11—C12 | −1.5 (6) |
C16—C6—C7—O1 | 0.0 (4) | C10—C11—C12—C13 | −1.1 (7) |
C5—C6—C7—C2 | 0.9 (4) | C11—C12—C13—C14 | 1.8 (6) |
C16—C6—C7—C2 | −179.8 (3) | C10—C9—C14—C13 | −2.8 (5) |
C8—O1—C7—C6 | 180.0 (3) | S—C9—C14—C13 | −178.2 (3) |
C8—O1—C7—C2 | −0.2 (3) | C12—C13—C14—C9 | 0.2 (6) |
Experimental details
Crystal data | |
Chemical formula | C17H16O2S |
Mr | 284.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 18.393 (2), 6.1515 (6), 13.054 (1) |
β (°) | 93.024 (2) |
V (Å3) | 1474.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8615, 3215, 1611 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.163, 1.01 |
No. of reflections | 3215 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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, π—π or C—H···π interactions between adjacent molecules are prevented by the steric influence of the three methyl groups in the molecule.