organic compounds
of 2-ethyl-3-(4-fluorophenylsulfinyl)-5,7-dimethyl-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, C18H17FO2S, the dihedral angle between the planes of the benzofuran ring system (r.m.s. deviation = 0.004 Å) and the 4-fluorophenyl ring is 86.38 (6)°. The terminal C atom of the ethyl substituent is displaced by 1.444 (3) Å from the benzofuran ring system to the same side of the molecule as the 4-fluorophenyl ring. In the crystal, molecules are linked via pairs of C—H⋯π interactions into inversion-related dimers. These dimers are further linked by π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.715 (3) Å] and between the furan rings of neighbouring molecules [centroid–centroid distance = 3.598 (3) Å]. The molecules are stacked along the a-axis direction. In the sulfinyl group, the S and O atoms are disordered over two sets of sites, with site-occupancy factors of 0.797 (3) and 0.213 (3).
Keywords: crystal structure; benzofuran; 4-fluorophenyl; π–π interactions; sulfinyl group; natural products.
CCDC reference: 1020650
1. Related literature
For pharmaceutical properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Khan et al. (2005); Ono et al. (2002). For natural products with a benzofuran ring, see: Akgul & Anil (2003); Soekamto et al. (2003). For the synthesis of the starting material 2-ethyl-3-(4-fluorophenylsulfanyl)-5,7-dimethyl-1-benzofuran, see: Choi et al. (1999). For a related structure, see: Choi et al. (2010).
2. Experimental
2.1. Crystal data
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2.1.3. Refinement
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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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 1020650
10.1107/S1600536814019023/hb7276sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814019023/hb7276Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814019023/hb7276Isup3.cml
The starting material 2-ethyl-3-(4-fluorophenylsulfanyl)-5,7-dimethyl-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-ethyl-3-(4-fluorophenylsulfanyl)-5,7-dimethyl-1-benzofuran (270 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X × 10 ml) and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 74% (234 mg); m.p. 378-379 K; Rf = 0.59 (hexane-ethyl acetate, 2:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound (20 mg) in acetone (15 ml) at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl and 0.98 Å for methylene and 0.99 Å for methyl H atoms, respectively. Uiso (H) = 1.2Ueq (C) for aryl and methylene, and 1.5Ueq (C) for methyl H atoms. The positions of methyl and methylene hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).The S1 and O2 atoms of the sulfinyl group is disordered over two positions with site-occupancy factors, from ═O, C(pheny)–S and C(furan)–S pairs were restrained to 1.488 (1), 1.762 (1) and 1.788 (1) Å using command DFIX and DELU, and displacement ellipsoids of S1 and O2 set were restrained using SHELXL command EADP, respectively.
of 0.797 (3) (part A) and 0.213 (3) (part B). The distance of equivalent SData 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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C18H17FO2S | V = 775.29 (3) Å3 |
Mr = 316.38 | Z = 2 |
Triclinic, P1 | F(000) = 332 |
Hall symbol: -P 1 | Dx = 1.355 Mg m−3 |
a = 9.1523 (2) Å | Melting point = 379–378 K |
b = 9.5503 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 10.3099 (2) Å | µ = 0.22 mm−1 |
α = 65.666 (1)° | T = 173 K |
β = 81.636 (1)° | Block, colourless |
γ = 70.782 (1)° | 0.45 × 0.41 × 0.27 mm |
Bruker SMART APEXII CCD diffractometer | 3874 independent reflections |
Radiation source: rotating anode | 3481 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.028 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.5°, θmin = 2.2° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −12→12 |
Tmin = 0.907, Tmax = 0.942 | l = −13→13 |
14476 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)] = 0.063 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0799P)2 + 0.8614P] where P = (Fo2 + 2Fc2)/3 |
3874 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.94 e Å−3 |
17 restraints | Δρmin = −1.64 e Å−3 |
C18H17FO2S | γ = 70.782 (1)° |
Mr = 316.38 | V = 775.29 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.1523 (2) Å | Mo Kα radiation |
b = 9.5503 (2) Å | µ = 0.22 mm−1 |
c = 10.3099 (2) Å | T = 173 K |
α = 65.666 (1)° | 0.45 × 0.41 × 0.27 mm |
β = 81.636 (1)° |
Bruker SMART APEXII CCD diffractometer | 3874 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3481 reflections with I > 2σ(I) |
Tmin = 0.907, Tmax = 0.942 | Rint = 0.028 |
14476 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 17 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.94 e Å−3 |
3874 reflections | Δρmin = −1.64 e Å−3 |
209 parameters |
Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.62-7.67 (m, 2H), 7.15-7.21 (m, 2H), 6.85 (s, 2H), 3.13 (q, J =7.52 Hz, 2H), 2.43 (s, 3H), 2.24 (s, 3H), 1.44 (t, J = 7.52 Hz, 3H). |
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 | Occ. (<1) | |
S1A | 0.46524 (7) | 0.39880 (7) | 0.27750 (7) | 0.0245 (2) | 0.797 (3) |
O2A | 0.3828 (2) | 0.4499 (2) | 0.39425 (17) | 0.0291 (4) | 0.797 (3) |
S1B | 0.47017 (19) | 0.40209 (16) | 0.3147 (3) | 0.0245 (2) | 0.20 |
O2B | 0.3618 (7) | 0.4565 (9) | 0.1973 (6) | 0.0291 (4) | 0.20 |
F1 | 0.9355 (2) | 0.7389 (2) | 0.05373 (19) | 0.0497 (4) | |
O1 | 0.69201 (18) | −0.05783 (19) | 0.39017 (17) | 0.0278 (4) | |
C1 | 0.5858 (2) | 0.20046 (14) | 0.3595 (2) | 0.0255 (4) | |
C2 | 0.6924 (2) | 0.1271 (3) | 0.4764 (2) | 0.0250 (4) | |
C3 | 0.7407 (3) | 0.1777 (3) | 0.5674 (2) | 0.0278 (5) | |
H3 | 0.6994 | 0.2857 | 0.5605 | 0.033* | |
C4 | 0.8512 (3) | 0.0653 (3) | 0.6687 (2) | 0.0312 (5) | |
C5 | 0.9101 (3) | −0.0934 (3) | 0.6775 (2) | 0.0324 (5) | |
H5 | 0.9856 | −0.1675 | 0.7476 | 0.039* | |
C6 | 0.8642 (3) | −0.1485 (3) | 0.5895 (2) | 0.0286 (5) | |
C7 | 0.7543 (2) | −0.0323 (3) | 0.4904 (2) | 0.0262 (4) | |
C8 | 0.5892 (2) | 0.0857 (3) | 0.3131 (2) | 0.0264 (4) | |
C9 | 0.9111 (3) | 0.1158 (4) | 0.7667 (3) | 0.0416 (6) | |
H9A | 0.8504 | 0.2264 | 0.7538 | 0.062* | |
H9B | 1.0201 | 0.1105 | 0.7439 | 0.062* | |
H9C | 0.9016 | 0.0434 | 0.8657 | 0.062* | |
C10 | 0.9286 (3) | −0.3185 (3) | 0.5983 (3) | 0.0381 (6) | |
H10A | 0.8436 | −0.3642 | 0.6110 | 0.057* | |
H10B | 0.9986 | −0.3831 | 0.6794 | 0.057* | |
H10C | 0.9857 | −0.3192 | 0.5104 | 0.057* | |
C11 | 0.5104 (3) | 0.0881 (3) | 0.1959 (3) | 0.0334 (5) | |
H11A | 0.4131 | 0.1784 | 0.1735 | 0.040* | |
H11B | 0.4830 | −0.0132 | 0.2281 | 0.040* | |
C12 | 0.6102 (3) | 0.1066 (3) | 0.0612 (3) | 0.0388 (6) | |
H12A | 0.6319 | 0.2102 | 0.0252 | 0.058* | |
H12B | 0.5551 | 0.1027 | −0.0113 | 0.058* | |
H12C | 0.7078 | 0.0189 | 0.0832 | 0.058* | |
C13 | 0.61273 (19) | 0.4976 (2) | 0.2173 (2) | 0.0284 (4) | |
C14 | 0.6924 (3) | 0.4950 (3) | 0.0925 (2) | 0.0314 (5) | |
H14 | 0.6723 | 0.4362 | 0.0455 | 0.038* | |
C15 | 0.8004 (3) | 0.5770 (3) | 0.0365 (3) | 0.0334 (5) | |
H15 | 0.8551 | 0.5759 | −0.0489 | 0.040* | |
C16 | 0.8272 (3) | 0.6608 (3) | 0.1073 (3) | 0.0333 (5) | |
C17 | 0.7502 (3) | 0.6671 (3) | 0.2305 (3) | 0.0352 (5) | |
H17 | 0.7718 | 0.7258 | 0.2769 | 0.042* | |
C18 | 0.6402 (3) | 0.5856 (3) | 0.2857 (3) | 0.0329 (5) | |
H18 | 0.5839 | 0.5898 | 0.3698 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0258 (3) | 0.0285 (3) | 0.0181 (4) | −0.0026 (2) | −0.0041 (2) | −0.0109 (2) |
O2A | 0.0216 (8) | 0.0372 (10) | 0.0300 (9) | −0.0030 (7) | −0.0004 (5) | −0.0190 (8) |
S1B | 0.0258 (3) | 0.0285 (3) | 0.0181 (4) | −0.0026 (2) | −0.0041 (2) | −0.0109 (2) |
O2B | 0.0216 (8) | 0.0372 (10) | 0.0300 (9) | −0.0030 (7) | −0.0004 (5) | −0.0190 (8) |
F1 | 0.0540 (10) | 0.0477 (9) | 0.0512 (10) | −0.0292 (8) | 0.0032 (8) | −0.0135 (8) |
O1 | 0.0282 (8) | 0.0260 (7) | 0.0279 (8) | −0.0071 (6) | −0.0024 (6) | −0.0094 (6) |
C1 | 0.0242 (10) | 0.0257 (7) | 0.0229 (9) | −0.0056 (6) | −0.0007 (7) | −0.0073 (8) |
C2 | 0.0224 (9) | 0.0283 (10) | 0.0218 (9) | −0.0083 (8) | 0.0016 (7) | −0.0073 (8) |
C3 | 0.0278 (10) | 0.0322 (11) | 0.0253 (10) | −0.0119 (9) | 0.0034 (8) | −0.0118 (9) |
C4 | 0.0280 (11) | 0.0438 (13) | 0.0237 (10) | −0.0168 (10) | 0.0018 (8) | −0.0110 (9) |
C5 | 0.0266 (11) | 0.0389 (12) | 0.0236 (10) | −0.0112 (9) | −0.0033 (8) | −0.0025 (9) |
C6 | 0.0257 (10) | 0.0282 (10) | 0.0257 (10) | −0.0087 (8) | 0.0010 (8) | −0.0045 (8) |
C7 | 0.0245 (10) | 0.0291 (10) | 0.0238 (10) | −0.0097 (8) | 0.0006 (8) | −0.0083 (8) |
C8 | 0.0240 (10) | 0.0291 (10) | 0.0240 (10) | −0.0081 (8) | 0.0000 (8) | −0.0083 (8) |
C9 | 0.0429 (14) | 0.0578 (17) | 0.0311 (12) | −0.0218 (13) | −0.0025 (10) | −0.0183 (12) |
C10 | 0.0338 (12) | 0.0280 (11) | 0.0403 (13) | −0.0046 (9) | −0.0036 (10) | −0.0043 (10) |
C11 | 0.0333 (12) | 0.0385 (12) | 0.0318 (12) | −0.0107 (10) | −0.0057 (9) | −0.0152 (10) |
C12 | 0.0540 (16) | 0.0366 (13) | 0.0276 (11) | −0.0157 (11) | −0.0010 (11) | −0.0126 (10) |
C13 | 0.0288 (10) | 0.0226 (10) | 0.0265 (10) | −0.0019 (7) | −0.0031 (8) | −0.0060 (8) |
C14 | 0.0376 (12) | 0.0295 (11) | 0.0264 (10) | −0.0074 (9) | −0.0028 (9) | −0.0113 (9) |
C15 | 0.0375 (12) | 0.0328 (11) | 0.0259 (11) | −0.0084 (10) | 0.0011 (9) | −0.0097 (9) |
C16 | 0.0363 (12) | 0.0262 (11) | 0.0322 (12) | −0.0087 (9) | −0.0043 (9) | −0.0057 (9) |
C17 | 0.0461 (14) | 0.0261 (11) | 0.0330 (12) | −0.0053 (10) | −0.0081 (10) | −0.0129 (9) |
C18 | 0.0392 (12) | 0.0263 (10) | 0.0267 (11) | −0.0006 (9) | −0.0011 (9) | −0.0108 (9) |
S1A—O2B | 1.180 (3) | C8—C11 | 1.484 (3) |
S1A—O2A | 1.4943 (9) | C9—H9A | 0.9800 |
S1A—C1 | 1.7597 (10) | C9—H9B | 0.9800 |
S1A—C13 | 1.7918 (10) | C9—H9C | 0.9800 |
O2A—S1B | 1.182 (2) | C10—H10A | 0.9800 |
S1B—O2B | 1.4869 (10) | C10—H10B | 0.9800 |
S1B—C1 | 1.7633 (10) | C10—H10C | 0.9800 |
S1B—C13 | 1.7865 (10) | C11—C12 | 1.527 (4) |
F1—C16 | 1.353 (3) | C11—H11A | 0.9900 |
O1—C8 | 1.366 (3) | C11—H11B | 0.9900 |
O1—C7 | 1.387 (3) | C12—H12A | 0.9800 |
C1—C8 | 1.355 (3) | C12—H12B | 0.9800 |
C1—C2 | 1.445 (3) | C12—H12C | 0.9800 |
C2—C7 | 1.391 (3) | C13—C14 | 1.389 (3) |
C2—C3 | 1.395 (3) | C13—C18 | 1.395 (3) |
C3—C4 | 1.391 (3) | C14—C15 | 1.376 (4) |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.399 (4) | C15—C16 | 1.377 (4) |
C4—C9 | 1.513 (3) | C15—H15 | 0.9500 |
C5—C6 | 1.388 (3) | C16—C17 | 1.374 (4) |
C5—H5 | 0.9500 | C17—C18 | 1.388 (4) |
C6—C7 | 1.384 (3) | C17—H17 | 0.9500 |
C6—C10 | 1.502 (3) | C18—H18 | 0.9500 |
O2B—S1A—O2A | 98.8 (4) | H9A—C9—H9B | 109.5 |
O2B—S1A—C1 | 132.7 (4) | C4—C9—H9C | 109.5 |
O2A—S1A—C1 | 106.79 (11) | H9A—C9—H9C | 109.5 |
O2B—S1A—C13 | 113.2 (4) | H9B—C9—H9C | 109.5 |
O2A—S1A—C13 | 104.60 (11) | C6—C10—H10A | 109.5 |
C1—S1A—C13 | 98.06 (10) | C6—C10—H10B | 109.5 |
S1B—O2A—S1A | 11.31 (14) | H10A—C10—H10B | 109.5 |
O2A—S1B—O2B | 99.1 (3) | C6—C10—H10C | 109.5 |
O2A—S1B—C1 | 124.2 (2) | H10A—C10—H10C | 109.5 |
O2B—S1B—C1 | 112.3 (3) | H10B—C10—H10C | 109.5 |
O2A—S1B—C13 | 121.5 (2) | C8—C11—C12 | 112.6 (2) |
O2B—S1B—C13 | 99.4 (3) | C8—C11—H11A | 109.1 |
C1—S1B—C13 | 98.13 (12) | C12—C11—H11A | 109.1 |
S1A—O2B—S1B | 11.63 (11) | C8—C11—H11B | 109.1 |
C8—O1—C7 | 106.69 (17) | C12—C11—H11B | 109.1 |
C8—C1—C2 | 108.00 (14) | H11A—C11—H11B | 107.8 |
C8—C1—S1A | 120.39 (16) | C11—C12—H12A | 109.5 |
C2—C1—S1A | 131.60 (16) | C11—C12—H12B | 109.5 |
C8—C1—S1B | 132.68 (19) | H12A—C12—H12B | 109.5 |
C2—C1—S1B | 119.05 (19) | C11—C12—H12C | 109.5 |
S1A—C1—S1B | 13.29 (10) | H12A—C12—H12C | 109.5 |
C7—C2—C3 | 119.4 (2) | H12B—C12—H12C | 109.5 |
C7—C2—C1 | 104.31 (18) | C14—C13—C18 | 120.08 (16) |
C3—C2—C1 | 136.2 (2) | C14—C13—S1B | 130.30 (19) |
C4—C3—C2 | 118.0 (2) | C18—C13—S1B | 109.61 (19) |
C4—C3—H3 | 121.0 | C14—C13—S1A | 117.84 (16) |
C2—C3—H3 | 121.0 | C18—C13—S1A | 121.90 (17) |
C3—C4—C5 | 120.1 (2) | S1B—C13—S1A | 13.08 (10) |
C3—C4—C9 | 119.9 (2) | C15—C14—C13 | 120.4 (2) |
C5—C4—C9 | 120.0 (2) | C15—C14—H14 | 119.8 |
C6—C5—C4 | 123.6 (2) | C13—C14—H14 | 119.8 |
C6—C5—H5 | 118.2 | C14—C15—C16 | 118.4 (2) |
C4—C5—H5 | 118.2 | C14—C15—H15 | 120.8 |
C7—C6—C5 | 114.2 (2) | C16—C15—H15 | 120.8 |
C7—C6—C10 | 122.3 (2) | F1—C16—C17 | 118.7 (2) |
C5—C6—C10 | 123.5 (2) | F1—C16—C15 | 118.4 (2) |
C6—C7—O1 | 124.8 (2) | C17—C16—C15 | 122.9 (2) |
C6—C7—C2 | 124.7 (2) | C16—C17—C18 | 118.5 (2) |
O1—C7—C2 | 110.49 (18) | C16—C17—H17 | 120.8 |
C1—C8—O1 | 110.49 (18) | C18—C17—H17 | 120.8 |
C1—C8—C11 | 133.2 (2) | C17—C18—C13 | 119.7 (2) |
O1—C8—C11 | 116.23 (19) | C17—C18—H18 | 120.2 |
C4—C9—H9A | 109.5 | C13—C18—H18 | 120.2 |
C4—C9—H9B | 109.5 | ||
O2B—S1A—O2A—S1B | −169.5 (5) | C10—C6—C7—C2 | −179.1 (2) |
C1—S1A—O2A—S1B | 50.7 (4) | C8—O1—C7—C6 | −179.7 (2) |
C13—S1A—O2A—S1B | −52.6 (4) | C8—O1—C7—C2 | −0.5 (2) |
S1A—O2A—S1B—O2B | 8.3 (4) | C3—C2—C7—C6 | −0.5 (3) |
S1A—O2A—S1B—C1 | −116.6 (4) | C1—C2—C7—C6 | 179.3 (2) |
S1A—O2A—S1B—C13 | 115.3 (4) | C3—C2—C7—O1 | −179.77 (18) |
O2A—S1A—O2B—S1B | 8.1 (4) | C1—C2—C7—O1 | 0.1 (2) |
C1—S1A—O2B—S1B | 130.9 (7) | C2—C1—C8—O1 | −0.7 (2) |
C13—S1A—O2B—S1B | −102.0 (5) | S1A—C1—C8—O1 | 179.05 (14) |
O2A—S1B—O2B—S1A | −169.7 (5) | S1B—C1—C8—O1 | −174.62 (18) |
C1—S1B—O2B—S1A | −36.8 (6) | C2—C1—C8—C11 | −178.0 (2) |
C13—S1B—O2B—S1A | 66.1 (5) | S1A—C1—C8—C11 | 1.8 (4) |
O2B—S1A—C1—C8 | 13.3 (6) | S1B—C1—C8—C11 | 8.1 (4) |
O2A—S1A—C1—C8 | 133.10 (19) | C7—O1—C8—C1 | 0.8 (2) |
C13—S1A—C1—C8 | −118.93 (19) | C7—O1—C8—C11 | 178.54 (18) |
O2B—S1A—C1—C2 | −166.9 (5) | C1—C8—C11—C12 | 96.1 (3) |
O2A—S1A—C1—C2 | −47.2 (2) | O1—C8—C11—C12 | −81.0 (3) |
C13—S1A—C1—C2 | 60.8 (2) | O2A—S1B—C13—C14 | −158.4 (3) |
O2B—S1A—C1—S1B | −146.0 (6) | O2B—S1B—C13—C14 | −51.6 (4) |
O2A—S1A—C1—S1B | −26.3 (2) | C1—S1B—C13—C14 | 62.8 (3) |
C13—S1A—C1—S1B | 81.7 (2) | O2A—S1B—C13—C18 | 21.6 (3) |
O2A—S1B—C1—C8 | 115.2 (3) | O2B—S1B—C13—C18 | 128.4 (3) |
O2B—S1B—C1—C8 | −3.8 (4) | C1—S1B—C13—C18 | −117.2 (2) |
C13—S1B—C1—C8 | −107.5 (3) | O2A—S1B—C13—S1A | −139.2 (4) |
O2A—S1B—C1—C2 | −58.2 (3) | O2B—S1B—C13—S1A | −32.4 (4) |
O2B—S1B—C1—C2 | −177.2 (4) | C1—S1B—C13—S1A | 81.9 (2) |
C13—S1B—C1—C2 | 79.1 (2) | O2B—S1A—C13—C14 | −62.9 (4) |
O2A—S1B—C1—S1A | 139.6 (4) | O2A—S1A—C13—C14 | −169.35 (18) |
O2B—S1B—C1—S1A | 20.6 (4) | C1—S1A—C13—C14 | 80.87 (19) |
C13—S1B—C1—S1A | −83.1 (2) | O2B—S1A—C13—C18 | 112.2 (4) |
C8—C1—C2—C7 | 0.4 (2) | O2A—S1A—C13—C18 | 5.7 (2) |
S1A—C1—C2—C7 | −179.35 (18) | C1—S1A—C13—C18 | −104.0 (2) |
S1B—C1—C2—C7 | 175.26 (16) | O2B—S1A—C13—S1B | 133.5 (4) |
C8—C1—C2—C3 | −179.8 (2) | O2A—S1A—C13—S1B | 27.1 (2) |
S1A—C1—C2—C3 | 0.4 (4) | C1—S1A—C13—S1B | −82.7 (2) |
S1B—C1—C2—C3 | −4.9 (4) | C18—C13—C14—C15 | 0.9 (3) |
C7—C2—C3—C4 | 0.6 (3) | S1B—C13—C14—C15 | −179.1 (2) |
C1—C2—C3—C4 | −179.2 (2) | S1A—C13—C14—C15 | 176.07 (18) |
C2—C3—C4—C5 | −0.2 (3) | C13—C14—C15—C16 | 0.2 (4) |
C2—C3—C4—C9 | 178.0 (2) | C14—C15—C16—F1 | 178.7 (2) |
C3—C4—C5—C6 | −0.1 (4) | C14—C15—C16—C17 | −0.5 (4) |
C9—C4—C5—C6 | −178.4 (2) | F1—C16—C17—C18 | −179.4 (2) |
C4—C5—C6—C7 | 0.2 (3) | C15—C16—C17—C18 | −0.2 (4) |
C4—C5—C6—C10 | 179.5 (2) | C16—C17—C18—C13 | 1.2 (3) |
C5—C6—C7—O1 | 179.3 (2) | C14—C13—C18—C17 | −1.6 (3) |
C10—C6—C7—O1 | 0.0 (3) | S1B—C13—C18—C17 | 178.40 (19) |
C5—C6—C7—C2 | 0.1 (3) | S1A—C13—C18—C17 | −176.58 (17) |
Cg1 is the centroid of the C13–C18 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···Cg1i | 0.98 | 2.89 | 3.822 (2) | 159 |
Symmetry code: (i) −x+2, −y, −z+1. |
Cg1 is the centroid of the C13–C18 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···Cg1i | 0.98 | 2.89 | 3.822 (2) | 159 |
Symmetry code: (i) −x+2, −y, −z+1. |
Acknowledgements
The X-ray Centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzofuran compounds show various pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al.. 2009, Galal et al., 2009, Khan et al., 2005), and potential inhibitor of β-amyloid aggregation (Howlett et al., 1999, Ono et al., 2002). These benzofuran compounds are widely occurring in nature (Akgul & Anil, 2003, Soekamto et al., 2003). As a part of our ongoing project of 3-(4-fluorophenylsulfinyl)-5,7-dimethyl-1-benzofuran derivatives containing methyl substituent in 2-position (Choi et al., 2010), we report herein on the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.004 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is essentially planar, with a mean deviation of 0.005 (2) Å from the least-squares plane defined by the six constituent atoms. In the sulfinyl group, the S1 and O2 atoms are disordered over two positions with site-occupancy factors, from refinement of 0.797 (3) (part A) and 0.213 (3) (part B). The dihedral angle formed by the benzofuran ring and the 4-fluorophenyl ring is 86.38 (6)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C–H···π interactions (Table 1, Cg1 is the C13-C18 4-fluorophenyl ring) into inversion-related dimers. These dimers are further linked by π–π interactions between the benzene rings of neighbouring molecules with a Cg2···Cg2i distance of 3.715 (3) Å and an interplanar distance of 3.464 (3) Å resulting in a slippage of 1.342 (3) Å (Cg2 is the C2-C7 benzene ring), and between the furan rings of neighbouring molecules with a Cg3···Cg3ii distance of 3.598 (3) Å and an interplanar distance of 3.507 (3) Å resulting in a slippage of 0.804 (3) Å (Cg3 is the C1/C2/C7/O1/C8 furan ring). The molecules are stacked along the a-axis direction.