Related literature
For the crystal structures of similar 3-methylsulfinyl-2-phenyl-1-benzofuran compounds, see: Choi et al. (2007a
,b
).
Experimental
Crystal data
C15H12O2S Mr = 256.32 Triclinic, ![[P \overline 1]](teximages/pk2109fi1.gif) a = 8.0185 (8) Å b = 9.4381 (9) Å c = 9.7749 (9) Å α = 115.574 (2)° β = 109.179 (2)° γ = 94.296 (2)° V = 609.51 (10) Å3 Z = 2 Mo Kα radiation μ = 0.26 mm−1 T = 173 (2) K 0.30 × 0.10 × 0.10 mm
|
Data collection
Bruker SMART CCD diffractometer Absorption correction: none 3185 measured reflections 2120 independent reflections 1878 reflections with I > 2σ(I) Rint = 0.030
|
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C15—H15C⋯O2i | 0.98 | 2.34 | 3.290 (3) | 164 | Symmetry code: (i) -x+1, -y+1, -z+1. | |
Data collection: SMART (Bruker, 2001
); cell refinement: 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
77% 3-Chloroperoxybenzoic acid (359 mg, 1.6 mmol) was added in small portions to a stirred solution of 3-methylsulfanyl-2-phenyl-1-benzofuran (360 mg, 1.5 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 2 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 under vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 1: 2 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 408–409 K; Rf = 0.79 (hexane-ethyl acetate, 1:2 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) δ 3.13 (s, 3H), 7.33–7.44 (m, 3H), 7.48–7.54 (m, 2H), 7.59 (d, J = 8.03 Hz, 1H), 7.84 (dd, J = 8.08 Hz and J = 1.48 Hz, 2H), 8.22 (d, J = 7.32 Hz, 1H); EI—MS 256 [M+].
All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms, 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms 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).
3-Methylsulfinyl-2-phenyl-1-benzofuran
top Crystal data top C15H12O2S | Z = 2 |
Mr = 256.32 | F(000) = 268 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0185 (8) Å | Cell parameters from 2383 reflections |
b = 9.4381 (9) Å | θ = 2.5–28.2° |
c = 9.7749 (9) Å | µ = 0.26 mm−1 |
α = 115.574 (2)° | T = 173 K |
β = 109.179 (2)° | Block, colorless |
γ = 94.296 (2)° | 0.30 × 0.10 × 0.10 mm |
V = 609.51 (10) Å3 | |
Data collection top Bruker SMART CCD diffractometer | 1878 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
Detector resolution: 10.0 pixels mm-1 | h = −8→9 |
ϕ and ω scans | k = −11→11 |
3185 measured reflections | l = −11→5 |
2120 independent reflections | |
Refinement top 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: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0341P)2 + 0.3746P] where P = (Fo2 + 2Fc2)/3 |
2120 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Crystal data top C15H12O2S | γ = 94.296 (2)° |
Mr = 256.32 | V = 609.51 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0185 (8) Å | Mo Kα radiation |
b = 9.4381 (9) Å | µ = 0.26 mm−1 |
c = 9.7749 (9) Å | T = 173 K |
α = 115.574 (2)° | 0.30 × 0.10 × 0.10 mm |
β = 109.179 (2)° | |
Data collection top Bruker SMART CCD diffractometer | 1878 reflections with I > 2σ(I) |
3185 measured reflections | Rint = 0.030 |
2120 independent reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.32 e Å−3 |
2120 reflections | Δρmin = −0.24 e Å−3 |
164 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 | x | y | z | Uiso*/Ueq | |
S | 0.33893 (6) | 0.23694 (6) | 0.35764 (6) | 0.02368 (16) | |
O1 | −0.05250 (18) | −0.15771 (15) | 0.17293 (16) | 0.0238 (3) | |
O2 | 0.4116 (2) | 0.33041 (18) | 0.54205 (18) | 0.0356 (4) | |
C1 | 0.1412 (3) | 0.0880 (2) | 0.2927 (2) | 0.0210 (4) | |
C2 | 0.0021 (3) | 0.1096 (2) | 0.3590 (2) | 0.0219 (4) | |
C3 | −0.0353 (3) | 0.2390 (3) | 0.4755 (3) | 0.0280 (5) | |
H3 | 0.0420 | 0.3457 | 0.5336 | 0.034* | |
C4 | −0.1883 (3) | 0.2063 (3) | 0.5031 (3) | 0.0321 (5) | |
H4 | −0.2170 | 0.2928 | 0.5807 | 0.039* | |
C5 | −0.3018 (3) | 0.0500 (3) | 0.4202 (3) | 0.0326 (5) | |
H5 | −0.4060 | 0.0329 | 0.4425 | 0.039* | |
C6 | −0.2666 (3) | −0.0807 (3) | 0.3064 (3) | 0.0291 (5) | |
H6 | −0.3429 | −0.1877 | 0.2500 | 0.035* | |
C7 | −0.1131 (3) | −0.0453 (2) | 0.2802 (2) | 0.0226 (4) | |
C8 | 0.1044 (2) | −0.0725 (2) | 0.1847 (2) | 0.0212 (4) | |
C9 | 0.1918 (3) | −0.1716 (2) | 0.0813 (2) | 0.0221 (4) | |
C10 | 0.1916 (3) | −0.3292 (2) | 0.0565 (3) | 0.0299 (5) | |
H10 | 0.1393 | −0.3695 | 0.1110 | 0.036* | |
C11 | 0.2669 (3) | −0.4265 (3) | −0.0468 (3) | 0.0370 (5) | |
H11 | 0.2666 | −0.5331 | −0.0624 | 0.044* | |
C12 | 0.3428 (3) | −0.3693 (3) | −0.1276 (3) | 0.0364 (5) | |
H12 | 0.3931 | −0.4370 | −0.1995 | 0.044* | |
C13 | 0.3451 (3) | −0.2136 (3) | −0.1033 (3) | 0.0315 (5) | |
H13 | 0.3986 | −0.1738 | −0.1575 | 0.038* | |
C14 | 0.2695 (3) | −0.1150 (2) | 0.0000 (2) | 0.0255 (4) | |
H14 | 0.2707 | −0.0083 | 0.0154 | 0.031* | |
C15 | 0.2300 (3) | 0.3619 (3) | 0.2805 (3) | 0.0352 (5) | |
H15A | 0.1334 | 0.3896 | 0.3203 | 0.053* | |
H15B | 0.1768 | 0.3027 | 0.1592 | 0.053* | |
H15C | 0.3203 | 0.4616 | 0.3200 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0189 (3) | 0.0221 (3) | 0.0235 (3) | 0.00303 (19) | 0.0068 (2) | 0.0072 (2) |
O1 | 0.0233 (7) | 0.0214 (7) | 0.0253 (7) | 0.0042 (5) | 0.0117 (6) | 0.0089 (6) |
O2 | 0.0311 (8) | 0.0359 (9) | 0.0232 (8) | −0.0025 (7) | 0.0057 (7) | 0.0058 (7) |
C1 | 0.0201 (10) | 0.0212 (10) | 0.0202 (10) | 0.0065 (8) | 0.0080 (8) | 0.0088 (8) |
C2 | 0.0204 (10) | 0.0264 (10) | 0.0206 (10) | 0.0093 (8) | 0.0080 (8) | 0.0122 (9) |
C3 | 0.0305 (11) | 0.0281 (11) | 0.0246 (11) | 0.0125 (9) | 0.0107 (9) | 0.0116 (9) |
C4 | 0.0357 (12) | 0.0421 (13) | 0.0277 (11) | 0.0238 (10) | 0.0181 (10) | 0.0185 (10) |
C5 | 0.0303 (12) | 0.0506 (14) | 0.0401 (13) | 0.0229 (10) | 0.0236 (10) | 0.0324 (12) |
C6 | 0.0256 (11) | 0.0365 (12) | 0.0348 (12) | 0.0106 (9) | 0.0138 (9) | 0.0235 (10) |
C7 | 0.0234 (10) | 0.0275 (10) | 0.0213 (10) | 0.0105 (8) | 0.0112 (8) | 0.0132 (9) |
C8 | 0.0187 (9) | 0.0235 (10) | 0.0208 (10) | 0.0035 (8) | 0.0067 (8) | 0.0113 (8) |
C9 | 0.0198 (9) | 0.0214 (10) | 0.0181 (10) | 0.0034 (8) | 0.0056 (8) | 0.0055 (8) |
C10 | 0.0334 (12) | 0.0255 (11) | 0.0309 (12) | 0.0068 (9) | 0.0163 (10) | 0.0113 (9) |
C11 | 0.0423 (13) | 0.0239 (11) | 0.0400 (14) | 0.0113 (10) | 0.0199 (11) | 0.0085 (10) |
C12 | 0.0317 (12) | 0.0366 (13) | 0.0305 (12) | 0.0101 (10) | 0.0167 (10) | 0.0041 (10) |
C13 | 0.0254 (11) | 0.0409 (12) | 0.0227 (11) | 0.0036 (9) | 0.0114 (9) | 0.0104 (9) |
C14 | 0.0235 (10) | 0.0277 (11) | 0.0213 (10) | 0.0048 (8) | 0.0070 (8) | 0.0103 (9) |
C15 | 0.0292 (11) | 0.0263 (11) | 0.0451 (14) | 0.0039 (9) | 0.0081 (10) | 0.0186 (11) |
Geometric parameters (Å, º) top S—O2 | 1.492 (2) | C6—H6 | 0.9500 |
S—C1 | 1.769 (2) | C8—C9 | 1.461 (3) |
S—C15 | 1.792 (2) | C9—C14 | 1.396 (3) |
O1—C7 | 1.384 (2) | C9—C10 | 1.400 (3) |
O1—C8 | 1.384 (2) | C10—C11 | 1.382 (3) |
C1—C8 | 1.358 (3) | C10—H10 | 0.9500 |
C1—C2 | 1.449 (3) | C11—C12 | 1.386 (3) |
C2—C7 | 1.394 (3) | C11—H11 | 0.9500 |
C2—C3 | 1.398 (3) | C12—C13 | 1.382 (3) |
C3—C4 | 1.381 (3) | C12—H12 | 0.9500 |
C3—H3 | 0.9500 | C13—C14 | 1.389 (3) |
C4—C5 | 1.394 (3) | C13—H13 | 0.9500 |
C4—H4 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.383 (3) | C15—H15A | 0.9800 |
C5—H5 | 0.9500 | C15—H15B | 0.9800 |
C6—C7 | 1.383 (3) | C15—H15C | 0.9800 |
| | | |
O2—S—C1 | 106.42 (9) | C1—C8—C9 | 134.62 (17) |
O2—S—C15 | 107.19 (10) | O1—C8—C9 | 114.80 (16) |
C1—S—C15 | 98.28 (10) | C14—C9—C10 | 118.74 (18) |
C7—O1—C8 | 106.40 (14) | C14—C9—C8 | 121.25 (17) |
C8—C1—C2 | 107.57 (17) | C10—C9—C8 | 119.95 (18) |
C8—C1—S | 125.35 (15) | C11—C10—C9 | 120.4 (2) |
C2—C1—S | 126.67 (14) | C11—C10—H10 | 119.8 |
C7—C2—C3 | 118.79 (18) | C9—C10—H10 | 119.8 |
C7—C2—C1 | 104.81 (16) | C10—C11—C12 | 120.3 (2) |
C3—C2—C1 | 136.38 (19) | C10—C11—H11 | 119.8 |
C4—C3—C2 | 117.8 (2) | C12—C11—H11 | 119.8 |
C4—C3—H3 | 121.1 | C13—C12—C11 | 119.9 (2) |
C2—C3—H3 | 121.1 | C13—C12—H12 | 120.1 |
C3—C4—C5 | 121.8 (2) | C11—C12—H12 | 120.1 |
C3—C4—H4 | 119.1 | C12—C13—C14 | 120.2 (2) |
C5—C4—H4 | 119.1 | C12—C13—H13 | 119.9 |
C6—C5—C4 | 121.76 (19) | C14—C13—H13 | 119.9 |
C6—C5—H5 | 119.1 | C13—C14—C9 | 120.40 (19) |
C4—C5—H5 | 119.1 | C13—C14—H14 | 119.8 |
C7—C6—C5 | 115.5 (2) | C9—C14—H14 | 119.8 |
C7—C6—H6 | 122.3 | S—C15—H15A | 109.5 |
C5—C6—H6 | 122.3 | S—C15—H15B | 109.5 |
C6—C7—O1 | 125.00 (18) | H15A—C15—H15B | 109.5 |
C6—C7—C2 | 124.38 (18) | S—C15—H15C | 109.5 |
O1—C7—C2 | 110.62 (16) | H15A—C15—H15C | 109.5 |
C1—C8—O1 | 110.58 (16) | H15B—C15—H15C | 109.5 |
| | | |
O2—S—C1—C8 | −130.84 (18) | C1—C2—C7—O1 | 0.4 (2) |
C15—S—C1—C8 | 118.42 (19) | C2—C1—C8—O1 | 1.2 (2) |
O2—S—C1—C2 | 40.85 (19) | S—C1—C8—O1 | 174.25 (13) |
C15—S—C1—C2 | −69.89 (19) | C2—C1—C8—C9 | −178.8 (2) |
C8—C1—C2—C7 | −1.0 (2) | S—C1—C8—C9 | −5.8 (3) |
S—C1—C2—C7 | −173.87 (15) | C7—O1—C8—C1 | −1.0 (2) |
C8—C1—C2—C3 | 177.6 (2) | C7—O1—C8—C9 | 179.06 (16) |
S—C1—C2—C3 | 4.7 (3) | C1—C8—C9—C14 | −38.8 (3) |
C7—C2—C3—C4 | −1.6 (3) | O1—C8—C9—C14 | 141.18 (18) |
C1—C2—C3—C4 | 179.9 (2) | C1—C8—C9—C10 | 144.1 (2) |
C2—C3—C4—C5 | 0.8 (3) | O1—C8—C9—C10 | −36.0 (3) |
C3—C4—C5—C6 | 0.3 (3) | C14—C9—C10—C11 | 0.0 (3) |
C4—C5—C6—C7 | −0.4 (3) | C8—C9—C10—C11 | 177.18 (19) |
C5—C6—C7—O1 | 179.56 (18) | C9—C10—C11—C12 | −0.3 (3) |
C5—C6—C7—C2 | −0.5 (3) | C10—C11—C12—C13 | 0.7 (4) |
C8—O1—C7—C6 | −179.69 (19) | C11—C12—C13—C14 | −0.9 (3) |
C8—O1—C7—C2 | 0.3 (2) | C12—C13—C14—C9 | 0.5 (3) |
C3—C2—C7—C6 | 1.5 (3) | C10—C9—C14—C13 | −0.1 (3) |
C1—C2—C7—C6 | −179.59 (19) | C8—C9—C14—C13 | −177.25 (18) |
C3—C2—C7—O1 | −178.49 (16) | | |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15C···O2i | 0.98 | 2.34 | 3.290 (3) | 164 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C15H12O2S |
Mr | 256.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.0185 (8), 9.4381 (9), 9.7749 (9) |
α, β, γ (°) | 115.574 (2), 109.179 (2), 94.296 (2) |
V (Å3) | 609.51 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
|
Data collection |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3185, 2120, 1878 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.090, 1.10 |
No. of reflections | 2120 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.24 |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15C···O2i | 0.98 | 2.34 | 3.290 (3) | 163.6 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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, o1291–o1292. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o2922. 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 our previous communications on the synthesis and structure of 3-methylsulfinyl-2-phenyl-1-benzofuran analogues, viz. 5-chloro-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007a) and 5-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007b). Here we report the crystal structure of 3-methylsulfinyl-2-phenyl-1-benzofuran (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 phenyl ring (C9—C14) makes a dihedral angle of 37.65 (8)° with the plane of the benzofuran fragment. The molecular packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the benzene rings from the adjacent molecules. The Cg···Cgii distance is 3.549 (2) Å (Cg is the centroid of C2—C7 benzene ring, symmetry code as in Fig. 2). The crystal structure is further stabilized by C—H···O (Fig. 2) interactions between a methyl H atom and the oxygen of the S=O unit, with a C15—H15C···O2i separation of 2.36 Å (Fig. 2 and Table 1; symmetry code as in Fig. 2).