organic compounds
5-Ethyl-3-(2-fluorophenylsulfonyl)-2-methyl-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
In the title compound, C17H15FO3S, the 2-fluorophenyl ring makes a dihedral angle of 89.12 (8)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); 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, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812036872/fj2589sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036872/fj2589Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812036872/fj2589Isup3.cml
3-Chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-ethyl-3-(2-fluorophenylsulfanyl)-2-methyl-1-benzofuran (315 mg, 1.1 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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
(benzene) to afford the title compound as a colorless solid [yield 72%, m.p. 410–411 K; Rf = 0.61 (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.All H atoms were geometrically positioned and refined using a riding model, with C–H = 0.95 Å for aryl, 0.99 Å for the methylene, and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene, and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.
As a part of our ongoing study of 5-ethyl-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfonyl) (Choi et al. , 2010) and 3-(3-fluorophenylsulfonyl) (Choi et al. , 2011) substituents, we report herein the
of the title compound.The title compound crystallizes as the non-centrosymmetric
Cc in spite of having no asymmetric C atoms.In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (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 fragment is 89.12 (8)°. In the π interactions (Table 1, Cg is the centroid of the C12-C17 2-fluorophenyl ring).
(Fig. 2), molecules are connected by weak C—H···O and C—H···For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2011).
Data collection: APEX2 (Bruker, 2009); cell
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 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C17H15FO3S | F(000) = 664 |
Mr = 318.35 | Dx = 1.401 Mg m−3 |
Monoclinic, Cc | Melting point = 410–411 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.290 (2) Å | Cell parameters from 2955 reflections |
b = 16.171 (3) Å | θ = 2.3–27.5° |
c = 8.5612 (14) Å | µ = 0.24 mm−1 |
β = 105.045 (11)° | T = 173 K |
V = 1509.4 (5) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.30 × 0.27 mm |
Bruker SMART APEXII CCD diffractometer | 3129 independent reflections |
Radiation source: rotating anode | 2676 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.035 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.2°, θmin = 2.3° |
φ and ω scans | h = −13→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −21→19 |
Tmin = 0.545, Tmax = 0.746 | l = −11→11 |
7108 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.5589P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3129 reflections | Δρmax = 0.61 e Å−3 |
201 parameters | Δρmin = −0.35 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1271 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (8) |
C17H15FO3S | V = 1509.4 (5) Å3 |
Mr = 318.35 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 11.290 (2) Å | µ = 0.24 mm−1 |
b = 16.171 (3) Å | T = 173 K |
c = 8.5612 (14) Å | 0.38 × 0.30 × 0.27 mm |
β = 105.045 (11)° |
Bruker SMART APEXII CCD diffractometer | 3129 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2676 reflections with I > 2σ(I) |
Tmin = 0.545, Tmax = 0.746 | Rint = 0.035 |
7108 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.105 | Δρmax = 0.61 e Å−3 |
S = 1.06 | Δρmin = −0.35 e Å−3 |
3129 reflections | Absolute structure: Flack (1983), 1271 Friedel pairs |
201 parameters | Absolute structure parameter: −0.05 (8) |
2 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.14686 (6) | 0.71642 (4) | 0.27469 (7) | 0.03361 (16) | |
O1 | 0.13896 (19) | 0.47875 (12) | 0.1852 (2) | 0.0427 (5) | |
O2 | 0.2615 (2) | 0.75833 (13) | 0.2964 (3) | 0.0462 (5) | |
O3 | 0.0429 (2) | 0.74224 (14) | 0.1475 (2) | 0.0503 (6) | |
F1 | −0.07139 (15) | 0.64592 (12) | 0.3612 (2) | 0.0498 (4) | |
C1 | 0.1696 (2) | 0.61168 (16) | 0.2571 (3) | 0.0316 (5) | |
C2 | 0.2695 (2) | 0.56448 (15) | 0.3603 (3) | 0.0297 (5) | |
C3 | 0.3736 (2) | 0.58219 (17) | 0.4846 (3) | 0.0331 (5) | |
H3 | 0.3936 | 0.6377 | 0.5176 | 0.040* | |
C4 | 0.4472 (3) | 0.51754 (17) | 0.5588 (3) | 0.0366 (6) | |
C5 | 0.4155 (3) | 0.43570 (18) | 0.5073 (4) | 0.0455 (7) | |
H5 | 0.4655 | 0.3916 | 0.5608 | 0.055* | |
C6 | 0.3147 (3) | 0.41750 (18) | 0.3825 (4) | 0.0456 (7) | |
H6 | 0.2949 | 0.3623 | 0.3474 | 0.055* | |
C7 | 0.2437 (3) | 0.48350 (17) | 0.3110 (4) | 0.0364 (6) | |
C8 | 0.0946 (2) | 0.55781 (18) | 0.1554 (3) | 0.0375 (6) | |
C9 | 0.5622 (3) | 0.5333 (2) | 0.6926 (3) | 0.0463 (7) | |
H9A | 0.5547 | 0.5875 | 0.7426 | 0.056* | |
H9B | 0.5690 | 0.4904 | 0.7770 | 0.056* | |
C10 | 0.6777 (3) | 0.5328 (3) | 0.6354 (5) | 0.0625 (10) | |
H10A | 0.6869 | 0.4788 | 0.5880 | 0.094* | |
H10B | 0.7485 | 0.5433 | 0.7272 | 0.094* | |
H10C | 0.6726 | 0.5760 | 0.5537 | 0.094* | |
C11 | −0.0195 (3) | 0.5648 (2) | 0.0229 (4) | 0.0544 (8) | |
H11A | −0.0508 | 0.6215 | 0.0184 | 0.082* | |
H11B | −0.0812 | 0.5264 | 0.0429 | 0.082* | |
H11C | −0.0019 | 0.5510 | −0.0803 | 0.082* | |
C12 | 0.1073 (2) | 0.72538 (15) | 0.4600 (3) | 0.0278 (5) | |
C13 | 0.1835 (2) | 0.76928 (16) | 0.5882 (3) | 0.0350 (6) | |
H13 | 0.2585 | 0.7921 | 0.5772 | 0.042* | |
C14 | 0.1496 (3) | 0.77939 (18) | 0.7304 (3) | 0.0421 (7) | |
H14 | 0.2010 | 0.8096 | 0.8171 | 0.051* | |
C15 | 0.0410 (3) | 0.7457 (2) | 0.7474 (3) | 0.0427 (7) | |
H15 | 0.0180 | 0.7532 | 0.8456 | 0.051* | |
C16 | −0.0339 (3) | 0.70139 (18) | 0.6230 (4) | 0.0402 (6) | |
H16 | −0.1082 | 0.6778 | 0.6347 | 0.048* | |
C17 | 0.0007 (2) | 0.69186 (17) | 0.4819 (3) | 0.0335 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0419 (3) | 0.0300 (3) | 0.0335 (3) | 0.0059 (3) | 0.0181 (2) | 0.0064 (3) |
O1 | 0.0395 (11) | 0.0359 (11) | 0.0531 (11) | −0.0064 (9) | 0.0129 (9) | −0.0118 (9) |
O2 | 0.0523 (12) | 0.0343 (11) | 0.0632 (13) | −0.0018 (9) | 0.0352 (11) | 0.0056 (9) |
O3 | 0.0683 (16) | 0.0478 (13) | 0.0349 (10) | 0.0197 (11) | 0.0135 (10) | 0.0118 (9) |
F1 | 0.0375 (9) | 0.0586 (11) | 0.0550 (9) | −0.0101 (8) | 0.0147 (8) | −0.0151 (8) |
C1 | 0.0346 (14) | 0.0315 (12) | 0.0326 (12) | 0.0013 (10) | 0.0158 (10) | −0.0010 (10) |
C2 | 0.0329 (12) | 0.0235 (12) | 0.0368 (12) | 0.0006 (10) | 0.0162 (10) | −0.0004 (9) |
C3 | 0.0374 (14) | 0.0284 (13) | 0.0360 (12) | 0.0005 (11) | 0.0141 (11) | −0.0004 (10) |
C4 | 0.0390 (15) | 0.0349 (14) | 0.0379 (13) | 0.0045 (11) | 0.0137 (11) | 0.0038 (11) |
C5 | 0.0484 (17) | 0.0307 (15) | 0.0598 (18) | 0.0084 (13) | 0.0181 (14) | 0.0088 (13) |
C6 | 0.0481 (17) | 0.0252 (15) | 0.0667 (19) | −0.0008 (12) | 0.0206 (15) | −0.0022 (12) |
C7 | 0.0339 (14) | 0.0309 (13) | 0.0478 (14) | −0.0030 (11) | 0.0170 (11) | −0.0043 (11) |
C8 | 0.0373 (14) | 0.0402 (16) | 0.0371 (13) | 0.0011 (11) | 0.0137 (11) | −0.0037 (11) |
C9 | 0.0480 (17) | 0.0489 (19) | 0.0385 (14) | 0.0091 (14) | 0.0051 (13) | 0.0054 (13) |
C10 | 0.0399 (18) | 0.084 (3) | 0.058 (2) | −0.0033 (17) | 0.0042 (15) | −0.0094 (18) |
C11 | 0.0429 (18) | 0.068 (2) | 0.0491 (17) | 0.0014 (16) | 0.0051 (14) | −0.0069 (15) |
C12 | 0.0321 (12) | 0.0238 (12) | 0.0297 (11) | 0.0062 (10) | 0.0120 (9) | 0.0045 (8) |
C13 | 0.0311 (13) | 0.0289 (13) | 0.0444 (14) | 0.0033 (10) | 0.0087 (10) | −0.0004 (10) |
C14 | 0.0450 (16) | 0.0420 (16) | 0.0360 (14) | 0.0112 (13) | 0.0044 (13) | −0.0033 (11) |
C15 | 0.0531 (17) | 0.0437 (16) | 0.0353 (13) | 0.0148 (14) | 0.0186 (12) | 0.0055 (12) |
C16 | 0.0421 (15) | 0.0374 (15) | 0.0480 (15) | 0.0073 (12) | 0.0241 (13) | 0.0078 (11) |
C17 | 0.0308 (13) | 0.0324 (13) | 0.0376 (13) | 0.0035 (10) | 0.0094 (10) | −0.0002 (10) |
S1—O2 | 1.430 (2) | C9—C10 | 1.507 (5) |
S1—O3 | 1.440 (2) | C9—H9A | 0.9900 |
S1—C1 | 1.726 (3) | C9—H9B | 0.9900 |
S1—C12 | 1.762 (2) | C10—H10A | 0.9800 |
O1—C8 | 1.373 (4) | C10—H10B | 0.9800 |
O1—C7 | 1.379 (3) | C10—H10C | 0.9800 |
F1—C17 | 1.359 (3) | C11—H11A | 0.9800 |
C1—C8 | 1.361 (4) | C11—H11B | 0.9800 |
C1—C2 | 1.455 (4) | C11—H11C | 0.9800 |
C2—C7 | 1.384 (4) | C12—C17 | 1.377 (4) |
C2—C3 | 1.395 (3) | C12—C13 | 1.400 (3) |
C3—C4 | 1.383 (4) | C13—C14 | 1.377 (4) |
C3—H3 | 0.9500 | C13—H13 | 0.9500 |
C4—C5 | 1.411 (4) | C14—C15 | 1.383 (4) |
C4—C9 | 1.513 (4) | C14—H14 | 0.9500 |
C5—C6 | 1.376 (4) | C15—C16 | 1.377 (5) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.379 (4) | C16—C17 | 1.371 (4) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C8—C11 | 1.484 (4) | ||
O2—S1—O3 | 119.56 (14) | C10—C9—H9B | 108.9 |
O2—S1—C1 | 109.03 (12) | C4—C9—H9B | 108.9 |
O3—S1—C1 | 109.23 (13) | H9A—C9—H9B | 107.7 |
O2—S1—C12 | 106.06 (13) | C9—C10—H10A | 109.5 |
O3—S1—C12 | 108.04 (12) | C9—C10—H10B | 109.5 |
C1—S1—C12 | 103.74 (11) | H10A—C10—H10B | 109.5 |
C8—O1—C7 | 106.9 (2) | C9—C10—H10C | 109.5 |
C8—C1—C2 | 108.0 (2) | H10A—C10—H10C | 109.5 |
C8—C1—S1 | 127.0 (2) | H10B—C10—H10C | 109.5 |
C2—C1—S1 | 124.86 (18) | C8—C11—H11A | 109.5 |
C7—C2—C3 | 119.7 (2) | C8—C11—H11B | 109.5 |
C7—C2—C1 | 104.0 (2) | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 136.2 (2) | C8—C11—H11C | 109.5 |
C4—C3—C2 | 118.8 (2) | H11A—C11—H11C | 109.5 |
C4—C3—H3 | 120.6 | H11B—C11—H11C | 109.5 |
C2—C3—H3 | 120.6 | C17—C12—C13 | 118.3 (2) |
C3—C4—C5 | 119.4 (3) | C17—C12—S1 | 121.71 (19) |
C3—C4—C9 | 121.0 (3) | C13—C12—S1 | 120.02 (19) |
C5—C4—C9 | 119.5 (2) | C14—C13—C12 | 119.9 (3) |
C6—C5—C4 | 122.3 (3) | C14—C13—H13 | 120.0 |
C6—C5—H5 | 118.8 | C12—C13—H13 | 120.0 |
C4—C5—H5 | 118.8 | C13—C14—C15 | 120.2 (3) |
C5—C6—C7 | 116.6 (3) | C13—C14—H14 | 119.9 |
C5—C6—H6 | 121.7 | C15—C14—H14 | 119.9 |
C7—C6—H6 | 121.7 | C16—C15—C14 | 120.5 (3) |
C6—C7—O1 | 125.8 (3) | C16—C15—H15 | 119.8 |
C6—C7—C2 | 123.0 (3) | C14—C15—H15 | 119.8 |
O1—C7—C2 | 111.1 (2) | C17—C16—C15 | 118.8 (3) |
C1—C8—O1 | 109.9 (2) | C17—C16—H16 | 120.6 |
C1—C8—C11 | 135.5 (3) | C15—C16—H16 | 120.6 |
O1—C8—C11 | 114.5 (3) | F1—C17—C16 | 118.7 (2) |
C10—C9—C4 | 113.4 (3) | F1—C17—C12 | 118.9 (2) |
C10—C9—H9A | 108.9 | C16—C17—C12 | 122.4 (2) |
C4—C9—H9A | 108.9 | ||
O2—S1—C1—C8 | −140.5 (2) | C2—C1—C8—O1 | −0.1 (3) |
O3—S1—C1—C8 | −8.2 (3) | S1—C1—C8—O1 | −175.45 (18) |
C12—S1—C1—C8 | 106.8 (2) | C2—C1—C8—C11 | −179.2 (3) |
O2—S1—C1—C2 | 44.9 (2) | S1—C1—C8—C11 | 5.5 (5) |
O3—S1—C1—C2 | 177.2 (2) | C7—O1—C8—C1 | 1.0 (3) |
C12—S1—C1—C2 | −67.8 (2) | C7—O1—C8—C11 | −179.7 (2) |
C8—C1—C2—C7 | −0.8 (3) | C3—C4—C9—C10 | −98.5 (4) |
S1—C1—C2—C7 | 174.68 (19) | C5—C4—C9—C10 | 80.6 (4) |
C8—C1—C2—C3 | 179.4 (3) | O2—S1—C12—C17 | 179.8 (2) |
S1—C1—C2—C3 | −5.1 (4) | O3—S1—C12—C17 | 50.5 (2) |
C7—C2—C3—C4 | −1.7 (4) | C1—S1—C12—C17 | −65.4 (2) |
C1—C2—C3—C4 | 178.1 (3) | O2—S1—C12—C13 | 1.4 (2) |
C2—C3—C4—C5 | 0.0 (4) | O3—S1—C12—C13 | −127.9 (2) |
C2—C3—C4—C9 | 179.1 (2) | C1—S1—C12—C13 | 116.3 (2) |
C3—C4—C5—C6 | 1.5 (5) | C17—C12—C13—C14 | −1.3 (3) |
C9—C4—C5—C6 | −177.6 (3) | S1—C12—C13—C14 | 177.1 (2) |
C4—C5—C6—C7 | −1.2 (5) | C12—C13—C14—C15 | 0.5 (4) |
C5—C6—C7—O1 | −179.6 (3) | C13—C14—C15—C16 | 0.4 (4) |
C5—C6—C7—C2 | −0.5 (5) | C14—C15—C16—C17 | −0.5 (4) |
C8—O1—C7—C6 | 177.7 (3) | C15—C16—C17—F1 | 178.0 (2) |
C8—O1—C7—C2 | −1.5 (3) | C15—C16—C17—C12 | −0.4 (4) |
C3—C2—C7—C6 | 2.0 (4) | C13—C12—C17—F1 | −177.1 (2) |
C1—C2—C7—C6 | −177.8 (3) | S1—C12—C17—F1 | 4.6 (3) |
C3—C2—C7—O1 | −178.8 (2) | C13—C12—C17—C16 | 1.3 (4) |
C1—C2—C7—O1 | 1.4 (3) | S1—C12—C17—C16 | −177.1 (2) |
Cg is the centroid of the C12–C17 2-fluorophenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O3i | 0.95 | 2.53 | 3.420 (3) | 156 |
C16—H16···O2ii | 0.95 | 2.49 | 3.121 (4) | 124 |
C5—H5···Cgiii | 0.95 | 2.79 | 3.692 (3) | 159 |
Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) x+1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C17H15FO3S |
Mr | 318.35 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 173 |
a, b, c (Å) | 11.290 (2), 16.171 (3), 8.5612 (14) |
β (°) | 105.045 (11) |
V (Å3) | 1509.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.38 × 0.30 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.545, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7108, 3129, 2676 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.105, 1.06 |
No. of reflections | 3129 |
No. of parameters | 201 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.35 |
Absolute structure | Flack (1983), 1271 Friedel pairs |
Absolute structure parameter | −0.05 (8) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).
Cg is the centroid of the C12–C17 2-fluorophenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O3i | 0.95 | 2.53 | 3.420 (3) | 156 |
C16—H16···O2ii | 0.95 | 2.49 | 3.121 (4) | 124 |
C5—H5···Cgiii | 0.95 | 2.79 | 3.692 (3) | 159 |
Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) x+1/2, y−1/2, z. |
Acknowledgements
This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.
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As a part of our ongoing study of 5-ethyl-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfonyl) (Choi et al. , 2010) and 3-(3-fluorophenylsulfonyl) (Choi et al. , 2011) substituents, we report herein the crystal structure of the title compound.
The title compound crystallizes as the non-centrosymmetric space group Cc in spite of having no asymmetric C atoms.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (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 fragment is 89.12 (8)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C12-C17 2-fluorophenyl ring).