organic compounds
2,5,7-Trimethyl-3-phenylsulfonyl-1-benzofuran
aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr
The title compound, C17H16O3S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring exhibits a dihedral angle of 81.16 (4)° with the plane of the benzofuran fragment. The is stabilized by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.874 (2) Å] and by C—H⋯π interactions between a phenyl H atom of the phenylsulfonyl substituent and the furan ring of adjacent molecules. In addition, the exhibits intra- and intermolecular C—H⋯O interactions.
Related literature
For the crystal structures of similar substituted benzofuran compounds, see: Choi et al. (2007a,b).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536808008477/zl2106sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008477/zl2106Isup2.hkl
3-Chloroperoxybenzoic acid (77%, 471 mg, 2.1 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 (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by δ 2.41 (s, 6H), 2.80 (s, 3H), 6.92 (s, 1H), 7.47–7.52 (m, 4H), 8.01 (d, J = 7.68 Hz, 2H); EI—MS 300 [M+].
(hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 399–400 K; Rf = 0.61 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz)All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms, 0.99 Å for methylene H atoms and 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic and methylene, Uiso(H) =1.5Ueq(C) for H atoms for methyl H atoms.
Data collection: SMART (Bruker, 2001); cell
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).C17H16O3S | F(000) = 632 |
Mr = 300.36 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 4291 reflections |
a = 9.2468 (7) Å | θ = 2.5–28.3° |
b = 8.4238 (7) Å | µ = 0.23 mm−1 |
c = 18.963 (2) Å | T = 173 K |
β = 91.535 (2)° | Block, colorless |
V = 1476.6 (2) Å3 | 0.40 × 0.40 × 0.10 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 2544 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 27.0°, θmin = 2.5° |
Detector resolution: 10.0 pixels mm-1 | h = −11→11 |
ϕ and ω scans | k = −7→10 |
8704 measured reflections | l = −24→23 |
3212 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)] = 0.037 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0467P)2 + 0.6422P] where P = (Fo2 + 2Fc2)/3 |
3212 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C17H16O3S | V = 1476.6 (2) Å3 |
Mr = 300.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.2468 (7) Å | µ = 0.23 mm−1 |
b = 8.4238 (7) Å | T = 173 K |
c = 18.963 (2) Å | 0.40 × 0.40 × 0.10 mm |
β = 91.535 (2)° |
Bruker SMART CCD diffractometer | 2544 reflections with I > 2σ(I) |
8704 measured reflections | Rint = 0.041 |
3212 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
3212 reflections | Δρmin = −0.38 e Å−3 |
193 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 | 0.71396 (5) | 0.59940 (5) | 0.11202 (2) | 0.02746 (13) | |
O1 | 1.04792 (13) | 0.77976 (15) | 0.01610 (7) | 0.0331 (3) | |
O2 | 0.77401 (15) | 0.57958 (16) | 0.18201 (6) | 0.0386 (3) | |
O3 | 0.63915 (14) | 0.46890 (14) | 0.07823 (7) | 0.0346 (3) | |
C1 | 0.84920 (18) | 0.6601 (2) | 0.05599 (9) | 0.0270 (4) | |
C2 | 0.84265 (18) | 0.6499 (2) | −0.02041 (9) | 0.0260 (4) | |
C3 | 0.74772 (19) | 0.5861 (2) | −0.07118 (9) | 0.0290 (4) | |
H3 | 0.6625 | 0.5321 | −0.0579 | 0.035* | |
C4 | 0.7809 (2) | 0.6035 (2) | −0.14184 (9) | 0.0330 (4) | |
C5 | 0.9071 (2) | 0.6844 (2) | −0.16049 (10) | 0.0346 (4) | |
H5 | 0.9266 | 0.6957 | −0.2092 | 0.042* | |
C6 | 1.00483 (19) | 0.7488 (2) | −0.11156 (10) | 0.0328 (4) | |
C7 | 0.96763 (19) | 0.7270 (2) | −0.04190 (9) | 0.0291 (4) | |
C8 | 0.97377 (19) | 0.7376 (2) | 0.07465 (9) | 0.0304 (4) | |
C9 | 0.59363 (18) | 0.7624 (2) | 0.11293 (9) | 0.0263 (4) | |
C10 | 0.48964 (19) | 0.7768 (2) | 0.05910 (9) | 0.0318 (4) | |
H10 | 0.4830 | 0.7005 | 0.0223 | 0.038* | |
C11 | 0.3956 (2) | 0.9051 (2) | 0.06032 (11) | 0.0402 (5) | |
H11 | 0.3232 | 0.9165 | 0.0242 | 0.048* | |
C12 | 0.4063 (2) | 1.0159 (2) | 0.11345 (12) | 0.0450 (5) | |
H12 | 0.3416 | 1.1035 | 0.1137 | 0.054* | |
C13 | 0.5111 (2) | 1.0004 (2) | 0.16670 (11) | 0.0428 (5) | |
H13 | 0.5180 | 1.0776 | 0.2032 | 0.051* | |
C14 | 0.6058 (2) | 0.8729 (2) | 0.16692 (10) | 0.0329 (4) | |
H14 | 0.6777 | 0.8615 | 0.2033 | 0.040* | |
C15 | 0.6791 (2) | 0.5378 (3) | −0.19827 (10) | 0.0461 (5) | |
H15A | 0.6497 | 0.4301 | −0.1853 | 0.069* | |
H15B | 0.7282 | 0.5348 | −0.2434 | 0.069* | |
H15C | 0.5934 | 0.6058 | −0.2027 | 0.069* | |
C16 | 1.1407 (2) | 0.8345 (2) | −0.13129 (12) | 0.0438 (5) | |
H16A | 1.1486 | 0.9339 | −0.1046 | 0.066* | |
H16B | 1.1370 | 0.8581 | −0.1819 | 0.066* | |
H16C | 1.2249 | 0.7675 | −0.1202 | 0.066* | |
C17 | 1.0431 (2) | 0.7849 (2) | 0.14286 (10) | 0.0398 (5) | |
H17A | 0.9787 | 0.7586 | 0.1814 | 0.060* | |
H17B | 1.0614 | 0.8994 | 0.1427 | 0.060* | |
H17C | 1.1348 | 0.7278 | 0.1495 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0317 (2) | 0.0259 (2) | 0.0248 (2) | 0.00101 (17) | 0.00055 (16) | 0.00232 (17) |
O1 | 0.0278 (6) | 0.0313 (7) | 0.0401 (7) | −0.0011 (5) | 0.0010 (5) | −0.0019 (6) |
O2 | 0.0440 (8) | 0.0429 (8) | 0.0287 (7) | 0.0047 (6) | −0.0027 (6) | 0.0058 (6) |
O3 | 0.0403 (7) | 0.0252 (6) | 0.0383 (7) | −0.0040 (5) | 0.0022 (6) | −0.0008 (5) |
C1 | 0.0264 (8) | 0.0274 (9) | 0.0273 (8) | 0.0029 (7) | −0.0003 (6) | −0.0001 (7) |
C2 | 0.0276 (8) | 0.0229 (8) | 0.0276 (8) | 0.0051 (7) | 0.0019 (6) | 0.0015 (7) |
C3 | 0.0301 (9) | 0.0280 (9) | 0.0289 (9) | 0.0026 (7) | 0.0005 (7) | 0.0000 (7) |
C4 | 0.0383 (10) | 0.0317 (9) | 0.0289 (9) | 0.0091 (8) | −0.0003 (7) | 0.0010 (8) |
C5 | 0.0430 (10) | 0.0332 (10) | 0.0281 (9) | 0.0124 (8) | 0.0082 (8) | 0.0045 (8) |
C6 | 0.0334 (10) | 0.0260 (9) | 0.0395 (10) | 0.0081 (7) | 0.0098 (8) | 0.0050 (8) |
C7 | 0.0287 (8) | 0.0238 (8) | 0.0348 (9) | 0.0043 (7) | 0.0007 (7) | −0.0003 (7) |
C8 | 0.0294 (9) | 0.0274 (9) | 0.0343 (9) | 0.0047 (7) | −0.0008 (7) | −0.0013 (7) |
C9 | 0.0253 (8) | 0.0252 (8) | 0.0286 (8) | −0.0030 (7) | 0.0045 (7) | 0.0023 (7) |
C10 | 0.0320 (9) | 0.0308 (9) | 0.0324 (9) | −0.0035 (7) | 0.0006 (7) | 0.0012 (8) |
C11 | 0.0303 (10) | 0.0424 (11) | 0.0480 (12) | 0.0021 (8) | 0.0011 (8) | 0.0113 (9) |
C12 | 0.0404 (11) | 0.0350 (11) | 0.0605 (13) | 0.0097 (9) | 0.0177 (10) | 0.0049 (10) |
C13 | 0.0488 (12) | 0.0338 (10) | 0.0465 (12) | 0.0003 (9) | 0.0147 (9) | −0.0076 (9) |
C14 | 0.0339 (9) | 0.0345 (10) | 0.0307 (9) | −0.0040 (8) | 0.0066 (7) | −0.0033 (8) |
C15 | 0.0492 (12) | 0.0601 (14) | 0.0285 (10) | 0.0059 (11) | −0.0055 (8) | −0.0026 (9) |
C16 | 0.0401 (11) | 0.0361 (11) | 0.0561 (13) | 0.0031 (9) | 0.0161 (10) | 0.0097 (9) |
C17 | 0.0359 (10) | 0.0416 (11) | 0.0413 (11) | 0.0006 (9) | −0.0096 (8) | −0.0055 (9) |
S—O2 | 1.4346 (13) | C9—C10 | 1.389 (2) |
S—O3 | 1.4401 (13) | C10—C11 | 1.388 (3) |
S—C1 | 1.7394 (17) | C10—H10 | 0.9500 |
S—C9 | 1.7674 (17) | C11—C12 | 1.375 (3) |
O1—C8 | 1.367 (2) | C11—H11 | 0.9500 |
O1—C7 | 1.384 (2) | C12—C13 | 1.387 (3) |
C1—C8 | 1.363 (2) | C12—H12 | 0.9500 |
C1—C2 | 1.451 (2) | C13—C14 | 1.386 (3) |
C2—C3 | 1.393 (2) | C13—H13 | 0.9500 |
C2—C7 | 1.396 (2) | C14—H14 | 0.9500 |
C3—C4 | 1.390 (2) | C15—H15A | 0.9800 |
C3—H3 | 0.9500 | C15—H15B | 0.9800 |
C4—C5 | 1.405 (3) | C15—H15C | 0.9800 |
C4—C15 | 1.511 (3) | C16—H16A | 0.9800 |
C5—C6 | 1.388 (3) | C16—H16B | 0.9800 |
C5—H5 | 0.9500 | C16—H16C | 0.9800 |
C6—C7 | 1.386 (2) | C17—H17A | 0.9800 |
C6—C16 | 1.505 (3) | C17—H17B | 0.9800 |
C8—C17 | 1.483 (2) | C17—H17C | 0.9800 |
C9—C14 | 1.386 (2) | ||
O2—S—O3 | 119.48 (8) | C11—C10—C9 | 118.54 (17) |
O2—S—C1 | 109.43 (8) | C11—C10—H10 | 120.7 |
O3—S—C1 | 107.29 (8) | C9—C10—H10 | 120.7 |
O2—S—C9 | 108.03 (8) | C12—C11—C10 | 120.53 (19) |
O3—S—C9 | 107.59 (8) | C12—C11—H11 | 119.7 |
C1—S—C9 | 103.94 (8) | C10—C11—H11 | 119.7 |
C8—O1—C7 | 106.96 (13) | C11—C12—C13 | 120.35 (19) |
C8—C1—C2 | 107.46 (15) | C11—C12—H12 | 119.8 |
C8—C1—S | 126.78 (14) | C13—C12—H12 | 119.8 |
C2—C1—S | 125.53 (13) | C14—C13—C12 | 120.26 (19) |
C3—C2—C7 | 119.27 (16) | C14—C13—H13 | 119.9 |
C3—C2—C1 | 136.18 (16) | C12—C13—H13 | 119.9 |
C7—C2—C1 | 104.55 (15) | C13—C14—C9 | 118.66 (18) |
C4—C3—C2 | 118.31 (17) | C13—C14—H14 | 120.7 |
C4—C3—H3 | 120.8 | C9—C14—H14 | 120.7 |
C2—C3—H3 | 120.8 | C4—C15—H15A | 109.5 |
C3—C4—C5 | 119.98 (17) | C4—C15—H15B | 109.5 |
C3—C4—C15 | 119.65 (18) | H15A—C15—H15B | 109.5 |
C5—C4—C15 | 120.36 (17) | C4—C15—H15C | 109.5 |
C6—C5—C4 | 123.47 (17) | H15A—C15—H15C | 109.5 |
C6—C5—H5 | 118.3 | H15B—C15—H15C | 109.5 |
C4—C5—H5 | 118.3 | C6—C16—H16A | 109.5 |
C7—C6—C5 | 114.32 (17) | C6—C16—H16B | 109.5 |
C7—C6—C16 | 122.04 (18) | H16A—C16—H16B | 109.5 |
C5—C6—C16 | 123.64 (17) | C6—C16—H16C | 109.5 |
O1—C7—C6 | 124.99 (16) | H16A—C16—H16C | 109.5 |
O1—C7—C2 | 110.38 (15) | H16B—C16—H16C | 109.5 |
C6—C7—C2 | 124.63 (17) | C8—C17—H17A | 109.5 |
C1—C8—O1 | 110.64 (15) | C8—C17—H17B | 109.5 |
C1—C8—C17 | 134.26 (17) | H17A—C17—H17B | 109.5 |
O1—C8—C17 | 115.10 (15) | C8—C17—H17C | 109.5 |
C14—C9—C10 | 121.66 (17) | H17A—C17—H17C | 109.5 |
C14—C9—S | 119.35 (14) | H17B—C17—H17C | 109.5 |
C10—C9—S | 118.98 (13) | ||
O2—S—C1—C8 | −24.52 (19) | C3—C2—C7—O1 | −179.24 (14) |
O3—S—C1—C8 | −155.54 (16) | C1—C2—C7—O1 | 0.79 (18) |
C9—S—C1—C8 | 90.68 (17) | C3—C2—C7—C6 | 1.4 (3) |
O2—S—C1—C2 | 161.63 (14) | C1—C2—C7—C6 | −178.60 (16) |
O3—S—C1—C2 | 30.61 (17) | C2—C1—C8—O1 | 0.6 (2) |
C9—S—C1—C2 | −83.18 (16) | S—C1—C8—O1 | −174.20 (12) |
C8—C1—C2—C3 | 179.23 (19) | C2—C1—C8—C17 | −179.81 (19) |
S—C1—C2—C3 | −5.9 (3) | S—C1—C8—C17 | 5.4 (3) |
C8—C1—C2—C7 | −0.81 (19) | C7—O1—C8—C1 | −0.07 (19) |
S—C1—C2—C7 | 174.03 (13) | C7—O1—C8—C17 | −179.78 (15) |
C7—C2—C3—C4 | −0.7 (2) | O2—S—C9—C14 | 20.07 (16) |
C1—C2—C3—C4 | 179.30 (18) | O3—S—C9—C14 | 150.32 (14) |
C2—C3—C4—C5 | −0.3 (3) | C1—S—C9—C14 | −96.11 (15) |
C2—C3—C4—C15 | −179.10 (17) | O2—S—C9—C10 | −160.35 (13) |
C3—C4—C5—C6 | 0.8 (3) | O3—S—C9—C10 | −30.10 (15) |
C15—C4—C5—C6 | 179.52 (17) | C1—S—C9—C10 | 83.47 (15) |
C4—C5—C6—C7 | −0.1 (3) | C14—C9—C10—C11 | −0.5 (3) |
C4—C5—C6—C16 | 179.55 (17) | S—C9—C10—C11 | 179.95 (13) |
C8—O1—C7—C6 | 178.91 (16) | C9—C10—C11—C12 | 0.5 (3) |
C8—O1—C7—C2 | −0.48 (18) | C10—C11—C12—C13 | −0.2 (3) |
C5—C6—C7—O1 | 179.76 (15) | C11—C12—C13—C14 | −0.1 (3) |
C16—C6—C7—O1 | 0.1 (3) | C12—C13—C14—C9 | 0.2 (3) |
C5—C6—C7—C2 | −0.9 (3) | C10—C9—C14—C13 | 0.1 (3) |
C16—C6—C7—C2 | 179.37 (16) | S—C9—C14—C13 | 179.70 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1i | 0.95 | 2.81 | 3.747 (3) | 169 |
C16—H16C···O3ii | 0.98 | 2.48 | 3.403 (2) | 158 |
C17—H17A···O2 | 0.98 | 2.42 | 3.135 (3) | 129 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H16O3S |
Mr | 300.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.2468 (7), 8.4238 (7), 18.963 (2) |
β (°) | 91.535 (2) |
V (Å3) | 1476.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.40 × 0.40 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8704, 3212, 2544 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.104, 1.04 |
No. of reflections | 3212 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.38 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg1i | 0.95 | 2.81 | 3.747 (3) | 168.7 |
C16—H16C···O3ii | 0.98 | 2.48 | 3.403 (2) | 157.9 |
C17—H17A···O2 | 0.98 | 2.42 | 3.135 (3) | 129.4 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z. |
References
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o1823–o1824. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o4042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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This work is related to earlier communications on the synthesis and structure of substituted benzofuran analogues, viz. 2,5-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2,5-dimethyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007b). Herein we report the molecular and crystal structure of the title compound, 2,5,7-trimethyl-3-phenylsulfonyl-1-benzofuran (Fig. 1).
The benzofuran unit is almost planar, with a mean deviation of 0.009 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 [81.16 (4) °] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the furan and the benzene rings from neighbouring molecules. The Cg1···Cg2ii distance is 3.874 (2)Å (Cg1 and Cg2 are the centroids of the O1/C8/C1/C2/C7 furan ring and the C2—C7 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions between a phenyl H atom of the phenylsulfonyl substituent and the furan ring of the benzofuran unit, with a C12—H12···Cgi separation of 2.81 Å (Fig. 2 and Table 1; Cg1 is the centroid of the O1/C8/C1/C2/C7 furan ring, symmetry code as in Fig. 2). Additionally, intra- and intermolecular C—H···O interactions in the structure were observed (Fig. 2 and Table 1; symmetry code as in Fig. 2).