organic compounds
5-Bromo-3-(4-fluorophenylsulfinyl)-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, C15H10BrFO2S, the O atom and the 4-fluorophenyl group of the 4-fluorophenylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-fluorophenyl ring is approximately perpendicular to this plane [dihedral angle = 89.38 (6)°]. In the crystal, molecules are linked by a Br⋯Br contact [3.4816 (5) Å], and weak intermolecular C—S⋯π [3.499 (2) Å] and C—F⋯π [3.535 (2) Å] interactions.
Related literature
For the crystal structures of similar derivatives, see: Choi et al. (2010a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).
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, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536810016181/ng2767sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016181/ng2767Isup2.hkl
77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (303 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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
(silica gel, hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 401-402 K; Rf = 0.64 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å for aryl and 0.96 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms.
The compounds containing benzofuran skeleton show potent biological activities such as antifungal (Aslam et al.., 2006), antitumor and antiviral (Galal et al.., 2009), antimicrobial (Khan et al.., 2005) properties. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al.. 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-methyl-3-(4-fluorophenylsulfinyl)-1-benzofuran analogues (Choi et al.., 2010a,b), we report the
of the title compound (Fig. 1).The benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is almost perpendicular to the plane of the benzofuran fragment [89.38 (6)°] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by a Br···Br interaction at 3.4816 (5) Å. The molecular packing (Fig. 2) is further stabilized by a weak intermolecular C–S···π interaction between the sulfur and the 4-fluorophenyl ring of an adjacent molecule, with a C1–S···Cg1ii [3.499 (2) Å] (Cg1 is the centroid of the C10-C15 4-fluorophenyl ring), and by a weak intermolecular C–F···π interaction between the fluorine and the benzene ring of a neighbouring benzofuran system, with C13–F···Cg2iii [3.535 (2) Å] (Cg2 is the centroid of the C2-C7 benzene ring).
For the crystal structures of similar derivatives, see: Choi et al. (2010a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).
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, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C15H10BrFO2S | F(000) = 704 |
Mr = 353.20 | Dx = 1.704 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4955 reflections |
a = 11.4704 (4) Å | θ = 2.6–27.5° |
b = 6.1776 (2) Å | µ = 3.15 mm−1 |
c = 19.6420 (7) Å | T = 173 K |
β = 98.432 (2)° | Block, colourless |
V = 1376.78 (8) Å3 | 0.32 × 0.26 × 0.21 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 3148 independent reflections |
Radiation source: rotating anode | 2655 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.028 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −8→7 |
Tmin = 0.453, Tmax = 0.746 | l = −25→25 |
11827 measured 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)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0338P)2 + 0.5303P] where P = (Fo2 + 2Fc2)/3 |
3148 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
C15H10BrFO2S | V = 1376.78 (8) Å3 |
Mr = 353.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4704 (4) Å | µ = 3.15 mm−1 |
b = 6.1776 (2) Å | T = 173 K |
c = 19.6420 (7) Å | 0.32 × 0.26 × 0.21 mm |
β = 98.432 (2)° |
Bruker SMART APEXII CCD diffractometer | 3148 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2655 reflections with I > 2σ(I) |
Tmin = 0.453, Tmax = 0.746 | Rint = 0.028 |
11827 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.36 e Å−3 |
3148 reflections | Δρmin = −0.53 e Å−3 |
182 parameters |
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 | ||
Br | 0.50266 (2) | 0.78650 (4) | 0.558051 (12) | 0.04487 (9) | |
S | 0.93498 (4) | 0.16534 (9) | 0.60352 (3) | 0.03310 (13) | |
F | 0.72642 (13) | 0.0128 (3) | 0.31650 (7) | 0.0625 (4) | |
O1 | 0.69236 (13) | 0.0086 (2) | 0.71739 (7) | 0.0367 (3) | |
O2 | 0.97008 (13) | 0.3979 (3) | 0.60830 (8) | 0.0431 (4) | |
C1 | 0.80963 (16) | 0.1358 (3) | 0.64457 (9) | 0.0291 (4) | |
C2 | 0.70597 (16) | 0.2719 (3) | 0.63776 (9) | 0.0273 (4) | |
C3 | 0.66711 (16) | 0.4522 (3) | 0.59916 (10) | 0.0296 (4) | |
H3 | 0.7113 | 0.5128 | 0.5680 | 0.035* | |
C4 | 0.55947 (17) | 0.5382 (3) | 0.60907 (9) | 0.0308 (4) | |
C5 | 0.49100 (17) | 0.4492 (4) | 0.65478 (10) | 0.0343 (5) | |
H5 | 0.4188 | 0.5114 | 0.6594 | 0.041* | |
C6 | 0.52929 (19) | 0.2691 (4) | 0.69335 (10) | 0.0367 (5) | |
H6 | 0.4845 | 0.2076 | 0.7241 | 0.044* | |
C7 | 0.63708 (18) | 0.1851 (3) | 0.68398 (9) | 0.0299 (4) | |
C8 | 0.79788 (18) | −0.0166 (3) | 0.69259 (10) | 0.0329 (4) | |
C9 | 0.8737 (2) | −0.1974 (4) | 0.72202 (12) | 0.0460 (6) | |
H9A | 0.9422 | −0.2058 | 0.6993 | 0.069* | |
H9B | 0.8305 | −0.3307 | 0.7155 | 0.069* | |
H9C | 0.8975 | −0.1730 | 0.7703 | 0.069* | |
C10 | 0.86555 (15) | 0.1228 (3) | 0.51655 (10) | 0.0284 (4) | |
C11 | 0.81711 (18) | −0.0770 (4) | 0.49734 (11) | 0.0370 (5) | |
H11 | 0.8172 | −0.1863 | 0.5299 | 0.044* | |
C12 | 0.7688 (2) | −0.1142 (4) | 0.42988 (12) | 0.0436 (5) | |
H12 | 0.7342 | −0.2466 | 0.4164 | 0.052* | |
C13 | 0.77312 (18) | 0.0497 (4) | 0.38319 (11) | 0.0400 (5) | |
C14 | 0.82316 (19) | 0.2465 (4) | 0.40008 (11) | 0.0391 (5) | |
H14 | 0.8257 | 0.3529 | 0.3668 | 0.047* | |
C15 | 0.87026 (17) | 0.2836 (3) | 0.46836 (11) | 0.0332 (4) | |
H15 | 0.9048 | 0.4162 | 0.4815 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.04284 (15) | 0.03939 (15) | 0.05249 (15) | 0.01201 (10) | 0.00742 (10) | 0.00670 (10) |
S | 0.0217 (2) | 0.0377 (3) | 0.0401 (3) | −0.0009 (2) | 0.00528 (19) | 0.0033 (2) |
F | 0.0624 (9) | 0.0825 (12) | 0.0413 (7) | −0.0034 (8) | 0.0035 (6) | −0.0134 (7) |
O1 | 0.0403 (8) | 0.0406 (9) | 0.0311 (7) | 0.0008 (7) | 0.0112 (6) | 0.0085 (6) |
O2 | 0.0390 (8) | 0.0431 (9) | 0.0478 (9) | −0.0181 (7) | 0.0088 (7) | −0.0041 (7) |
C1 | 0.0260 (9) | 0.0304 (10) | 0.0309 (9) | −0.0018 (8) | 0.0041 (7) | 0.0009 (8) |
C2 | 0.0252 (9) | 0.0294 (10) | 0.0275 (9) | −0.0034 (8) | 0.0045 (7) | −0.0024 (8) |
C3 | 0.0276 (9) | 0.0298 (11) | 0.0323 (9) | −0.0024 (8) | 0.0076 (7) | 0.0019 (8) |
C4 | 0.0312 (10) | 0.0300 (11) | 0.0304 (9) | 0.0005 (8) | 0.0023 (8) | −0.0037 (8) |
C5 | 0.0270 (10) | 0.0450 (13) | 0.0319 (10) | 0.0022 (9) | 0.0076 (8) | −0.0072 (9) |
C6 | 0.0355 (11) | 0.0477 (14) | 0.0296 (10) | −0.0023 (10) | 0.0136 (8) | 0.0015 (9) |
C7 | 0.0339 (10) | 0.0317 (11) | 0.0248 (9) | −0.0024 (9) | 0.0063 (7) | 0.0001 (8) |
C8 | 0.0336 (11) | 0.0345 (11) | 0.0299 (9) | 0.0004 (9) | 0.0027 (8) | 0.0014 (8) |
C9 | 0.0523 (14) | 0.0442 (14) | 0.0402 (12) | 0.0076 (11) | 0.0027 (10) | 0.0124 (10) |
C10 | 0.0198 (8) | 0.0293 (10) | 0.0384 (10) | 0.0022 (8) | 0.0116 (7) | 0.0008 (8) |
C11 | 0.0366 (11) | 0.0294 (11) | 0.0472 (12) | −0.0027 (9) | 0.0137 (9) | 0.0025 (9) |
C12 | 0.0407 (12) | 0.0369 (13) | 0.0549 (13) | −0.0071 (10) | 0.0131 (10) | −0.0131 (11) |
C13 | 0.0329 (11) | 0.0516 (15) | 0.0368 (11) | 0.0042 (10) | 0.0095 (9) | −0.0071 (10) |
C14 | 0.0342 (11) | 0.0430 (13) | 0.0419 (11) | 0.0045 (10) | 0.0118 (9) | 0.0077 (10) |
C15 | 0.0259 (9) | 0.0294 (11) | 0.0459 (11) | −0.0003 (8) | 0.0100 (8) | 0.0020 (9) |
Br—C4 | 1.895 (2) | C6—C7 | 1.378 (3) |
Br—Bri | 3.4816 (5) | C6—H6 | 0.9300 |
S—O2 | 1.4910 (17) | C8—C9 | 1.480 (3) |
S—C1 | 1.7581 (19) | C9—H9A | 0.9600 |
S—C10 | 1.795 (2) | C9—H9B | 0.9600 |
F—C13 | 1.360 (2) | C9—H9C | 0.9600 |
O1—C8 | 1.378 (2) | C10—C15 | 1.379 (3) |
O1—C7 | 1.378 (2) | C10—C11 | 1.383 (3) |
C1—C8 | 1.353 (3) | C11—C12 | 1.379 (3) |
C1—C2 | 1.446 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.384 (3) | C12—C13 | 1.372 (3) |
C2—C7 | 1.395 (3) | C12—H12 | 0.9300 |
C3—C4 | 1.384 (3) | C13—C14 | 1.365 (3) |
C3—H3 | 0.9300 | C14—C15 | 1.389 (3) |
C4—C5 | 1.390 (3) | C14—H14 | 0.9300 |
C5—C6 | 1.381 (3) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | ||
C4—Br—Bri | 158.65 (6) | C1—C8—C9 | 133.19 (19) |
O2—S—C1 | 107.60 (10) | O1—C8—C9 | 116.30 (18) |
O2—S—C10 | 106.21 (9) | C8—C9—H9A | 109.5 |
C1—S—C10 | 98.20 (8) | C8—C9—H9B | 109.5 |
C8—O1—C7 | 106.71 (15) | H9A—C9—H9B | 109.5 |
C8—C1—C2 | 107.72 (17) | C8—C9—H9C | 109.5 |
C8—C1—S | 124.30 (16) | H9A—C9—H9C | 109.5 |
C2—C1—S | 127.87 (15) | H9B—C9—H9C | 109.5 |
C3—C2—C7 | 119.89 (18) | C15—C10—C11 | 120.69 (19) |
C3—C2—C1 | 135.47 (17) | C15—C10—S | 119.42 (16) |
C7—C2—C1 | 104.63 (17) | C11—C10—S | 119.65 (16) |
C2—C3—C4 | 117.02 (17) | C12—C11—C10 | 120.0 (2) |
C2—C3—H3 | 121.5 | C12—C11—H11 | 120.0 |
C4—C3—H3 | 121.5 | C10—C11—H11 | 120.0 |
C3—C4—C5 | 122.64 (19) | C13—C12—C11 | 118.1 (2) |
C3—C4—Br | 118.76 (14) | C13—C12—H12 | 121.0 |
C5—C4—Br | 118.60 (15) | C11—C12—H12 | 121.0 |
C6—C5—C4 | 120.57 (19) | F—C13—C14 | 118.4 (2) |
C6—C5—H5 | 119.7 | F—C13—C12 | 118.2 (2) |
C4—C5—H5 | 119.7 | C14—C13—C12 | 123.4 (2) |
C7—C6—C5 | 116.72 (18) | C13—C14—C15 | 118.1 (2) |
C7—C6—H6 | 121.6 | C13—C14—H14 | 120.9 |
C5—C6—H6 | 121.6 | C15—C14—H14 | 120.9 |
C6—C7—O1 | 126.41 (17) | C10—C15—C14 | 119.7 (2) |
C6—C7—C2 | 123.16 (19) | C10—C15—H15 | 120.2 |
O1—C7—C2 | 110.43 (17) | C14—C15—H15 | 120.2 |
C1—C8—O1 | 110.50 (17) | ||
O2—S—C1—C8 | −130.32 (18) | C1—C2—C7—O1 | 0.0 (2) |
C10—S—C1—C8 | 119.71 (19) | C2—C1—C8—O1 | 0.7 (2) |
O2—S—C1—C2 | 45.3 (2) | S—C1—C8—O1 | 177.08 (14) |
C10—S—C1—C2 | −64.66 (19) | C2—C1—C8—C9 | −179.4 (2) |
C8—C1—C2—C3 | 178.8 (2) | S—C1—C8—C9 | −3.1 (4) |
S—C1—C2—C3 | 2.6 (3) | C7—O1—C8—C1 | −0.7 (2) |
C8—C1—C2—C7 | −0.4 (2) | C7—O1—C8—C9 | 179.43 (18) |
S—C1—C2—C7 | −176.65 (15) | O2—S—C10—C15 | 9.31 (17) |
C7—C2—C3—C4 | 0.1 (3) | C1—S—C10—C15 | 120.42 (16) |
C1—C2—C3—C4 | −179.1 (2) | O2—S—C10—C11 | −176.30 (15) |
C2—C3—C4—C5 | −0.8 (3) | C1—S—C10—C11 | −65.20 (17) |
C2—C3—C4—Br | 179.50 (14) | C15—C10—C11—C12 | −2.5 (3) |
C3—C4—C5—C6 | 0.7 (3) | S—C10—C11—C12 | −176.83 (16) |
Br—C4—C5—C6 | −179.57 (16) | C10—C11—C12—C13 | 1.5 (3) |
C4—C5—C6—C7 | 0.0 (3) | C11—C12—C13—F | 179.44 (18) |
C5—C6—C7—O1 | 179.32 (19) | C11—C12—C13—C14 | 0.3 (3) |
C5—C6—C7—C2 | −0.7 (3) | F—C13—C14—C15 | 179.71 (18) |
C8—O1—C7—C6 | −179.6 (2) | C12—C13—C14—C15 | −1.1 (3) |
C8—O1—C7—C2 | 0.4 (2) | C11—C10—C15—C14 | 1.7 (3) |
C3—C2—C7—C6 | 0.6 (3) | S—C10—C15—C14 | 175.98 (15) |
C1—C2—C7—C6 | 180.00 (19) | C13—C14—C15—C10 | 0.1 (3) |
C3—C2—C7—O1 | −179.40 (17) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H10BrFO2S |
Mr | 353.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 11.4704 (4), 6.1776 (2), 19.6420 (7) |
β (°) | 98.432 (2) |
V (Å3) | 1376.78 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.15 |
Crystal size (mm) | 0.32 × 0.26 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.453, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11827, 3148, 2655 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.072, 1.05 |
No. of reflections | 3148 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.53 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
References
Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o543. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o564. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar
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The compounds containing benzofuran skeleton show potent biological activities such as antifungal (Aslam et al.., 2006), antitumor and antiviral (Galal et al.., 2009), antimicrobial (Khan et al.., 2005) properties. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al.. 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-methyl-3-(4-fluorophenylsulfinyl)-1-benzofuran analogues (Choi et al.., 2010a,b), we report the crystal structure of the title compound (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is almost perpendicular to the plane of the benzofuran fragment [89.38 (6)°] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by a Br···Br interaction at 3.4816 (5) Å. The molecular packing (Fig. 2) is further stabilized by a weak intermolecular C–S···π interaction between the sulfur and the 4-fluorophenyl ring of an adjacent molecule, with a C1–S···Cg1ii [3.499 (2) Å] (Cg1 is the centroid of the C10-C15 4-fluorophenyl ring), and by a weak intermolecular C–F···π interaction between the fluorine and the benzene ring of a neighbouring benzofuran system, with C13–F···Cg2iii [3.535 (2) Å] (Cg2 is the centroid of the C2-C7 benzene ring).