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organic compounds
5-Cyclopentyl-2-(3-fluorophenyl)-3-methylsulfinyl-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, C20H19FO2S, the benzofuran fragment is essentially planar, with a largest deviation from the mean plane of 0.026 (2) Å. The benzene ring makes a dihedral angle of 30.72 (12)° with this plane. The cyclopentyl group adopts an with the α-C atom as the flap. This atom is disordered over two sites with occupancy factors of 0.803 (16) and 0.197 (16). In the crystal, molecules are linked by weak C—H⋯O, C—H⋯π and C—F⋯π [3.257 (3) Å] interactions.
Related literature
For the crystal structures of related compounds, see: Choi et al. (2011); Seo et al. (2011
).
Experimental
Crystal data
|
Refinement
|
|
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/S1600536812025482/yk2058sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025482/yk2058Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812025482/yk2058Isup3.cml
3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran (293 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium hydrocarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane-ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 430-431 K; R f = 0.56 (hexane-ethyl acetate, 1:2 v/v)]. 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 positioned geometrically and refined using a riding model, with C—H = 0.95 Å for the aryl, 1.00 Å for the methine, 0.99 Å for the methylene, and 0.98 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for the aryl, methine, and methylene H atoms, and 1.5Ueq(C) for the methyl H atoms. The methyl group was allowed to rotate during the refinement.
The C10 atom of the cyclopentyl ring is disordered over two positions. The site occupancy factors were refined to 0.807 (16) (part A) and 0.193 (16) (part B). The distances of equivalent C-C pairs were restrained to 1.525 (4) Å and 0.001 Å using command DFIX and SADI, respectively, and displacement ellipsoids of C10A and C10B were restrained using command ISOR and DELU.
As a part of our ongoing study of 5-cyclopentyl-3-methylsulfinyl-1-benzofuran derivatives containing 2-phenyl (Choi et al., 2011) and 2-(4-fluorophenyl) (Seo et al., 2011) substituents, we report herein the
of the title compound.In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an π interactions (Table 1, Cg1 and Cg2 are the centroids of the C1–C3/C8/O1 furan ring and the C2–C7 benzene ring, respectively). The crystal packing (Fig. 2) also exhibits C—F···π interactions between the fluorine atom and the furan ring of an adjacent molecule, with a C16—F1···Cg1iii distance of 3.257 (3) Å.
with the C10 atom as a flop. This atom is disordered over two sites, C10A and C10B, with occupancy factors of 0.803 (16) and 0.197 (16), respectively. The dihedral angle between the 3-fluorophenyl group and the mean plane of the benzofuran fragment is 30.7 (1)°. In the molecules are connected by weak C—H···O and C—H···For the crystal structures of related compounds, see: Choi et al. (2011); Seo et al. (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, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C20H19FO2S | F(000) = 720 |
Mr = 342.41 | Dx = 1.379 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5280 reflections |
a = 6.1024 (3) Å | θ = 2.5–28.2° |
b = 25.3030 (11) Å | µ = 0.22 mm−1 |
c = 10.6840 (5) Å | T = 173 K |
β = 90.231 (1)° | Block, colourless |
V = 1649.69 (13) Å3 | 0.40 × 0.25 × 0.22 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 2905 independent reflections |
Radiation source: rotating anode | 2568 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.027 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
φ and ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −30→30 |
Tmin = 0.919, Tmax = 0.954 | l = −12→12 |
13224 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)] = 0.060 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.087P)2 + 2.8614P] where P = (Fo2 + 2Fc2)/3 |
2905 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 1.35 e Å−3 |
30 restraints | Δρmin = −0.55 e Å−3 |
C20H19FO2S | V = 1649.69 (13) Å3 |
Mr = 342.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.1024 (3) Å | µ = 0.22 mm−1 |
b = 25.3030 (11) Å | T = 173 K |
c = 10.6840 (5) Å | 0.40 × 0.25 × 0.22 mm |
β = 90.231 (1)° |
Bruker SMART APEXII CCD diffractometer | 2905 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2568 reflections with I > 2σ(I) |
Tmin = 0.919, Tmax = 0.954 | Rint = 0.027 |
13224 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 30 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.35 e Å−3 |
2905 reflections | Δρmin = −0.55 e Å−3 |
228 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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) | |
S1 | 0.49517 (11) | 0.72428 (3) | 0.41704 (6) | 0.0274 (2) | |
O1 | 0.5749 (3) | 0.56958 (7) | 0.45210 (17) | 0.0261 (4) | |
O2 | 0.4494 (4) | 0.74049 (8) | 0.28532 (19) | 0.0403 (6) | |
F1 | 1.2882 (3) | 0.56555 (10) | 0.6805 (2) | 0.0617 (6) | |
C1 | 0.3984 (4) | 0.57030 (11) | 0.3714 (2) | 0.0245 (6) | |
C2 | 0.6189 (4) | 0.62149 (11) | 0.4815 (2) | 0.0242 (6) | |
C3 | 0.4786 (4) | 0.65466 (11) | 0.4202 (2) | 0.0234 (6) | |
C4 | 0.1509 (5) | 0.63050 (11) | 0.2681 (3) | 0.0289 (6) | |
H4 | 0.1049 | 0.6654 | 0.2488 | 0.035* | |
C5 | 0.0407 (5) | 0.58719 (12) | 0.2184 (3) | 0.0344 (7) | |
C6 | 0.1179 (5) | 0.53590 (12) | 0.2453 (3) | 0.0356 (7) | |
H6 | 0.0429 | 0.5066 | 0.2096 | 0.043* | |
C7 | 0.2976 (5) | 0.52630 (11) | 0.3211 (3) | 0.0306 (6) | |
H7 | 0.3486 | 0.4915 | 0.3376 | 0.037* | |
C8 | 0.3310 (4) | 0.62182 (10) | 0.3474 (2) | 0.0233 (6) | |
C9 | −0.1701 (6) | 0.59386 (12) | 0.1427 (3) | 0.0448 (8) | |
H9A | −0.2944 | 0.5837 | 0.1984 | 0.054* | 0.803 (16) |
H9B | −0.2753 | 0.5944 | 0.2142 | 0.054* | 0.197 (16) |
C10A | −0.1826 (10) | 0.5586 (2) | 0.0271 (5) | 0.0527 (19) | 0.803 (16) |
H10A | −0.2053 | 0.5212 | 0.0505 | 0.063* | 0.803 (16) |
H10B | −0.0476 | 0.5615 | −0.0236 | 0.063* | 0.803 (16) |
C10B | −0.283 (3) | 0.5505 (2) | 0.0671 (11) | 0.035 (3) | 0.197 (16) |
H10C | −0.3989 | 0.5330 | 0.1167 | 0.043* | 0.197 (16) |
H10D | −0.1763 | 0.5236 | 0.0390 | 0.043* | 0.197 (16) |
C11 | −0.3803 (8) | 0.58042 (15) | −0.0439 (5) | 0.0776 (16) | |
H11A | −0.3541 | 0.5794 | −0.1352 | 0.093* | 0.803 (16) |
H11B | −0.5127 | 0.5593 | −0.0252 | 0.093* | 0.803 (16) |
H11C | −0.2866 | 0.5788 | −0.1192 | 0.093* | 0.197 (16) |
H11D | −0.5234 | 0.5637 | −0.0628 | 0.093* | 0.197 (16) |
C12 | −0.4100 (5) | 0.63712 (13) | 0.0002 (3) | 0.0377 (7) | |
H12A | −0.5526 | 0.6415 | 0.0428 | 0.045* | |
H12B | −0.4034 | 0.6619 | −0.0713 | 0.045* | |
C13 | −0.2206 (5) | 0.64710 (12) | 0.0912 (3) | 0.0377 (7) | |
H13A | −0.0923 | 0.6620 | 0.0472 | 0.045* | |
H13B | −0.2649 | 0.6717 | 0.1586 | 0.045* | |
C14 | 0.7931 (4) | 0.62945 (11) | 0.5734 (2) | 0.0258 (6) | |
C15 | 0.9653 (4) | 0.59298 (12) | 0.5813 (3) | 0.0297 (6) | |
H15 | 0.9718 | 0.5635 | 0.5263 | 0.036* | |
C16 | 1.1247 (5) | 0.60094 (13) | 0.6706 (3) | 0.0341 (7) | |
C17 | 1.1235 (5) | 0.64302 (14) | 0.7524 (3) | 0.0390 (8) | |
H17 | 1.2369 | 0.6474 | 0.8126 | 0.047* | |
C18 | 0.9526 (5) | 0.67855 (13) | 0.7442 (3) | 0.0380 (7) | |
H18 | 0.9485 | 0.7079 | 0.7995 | 0.046* | |
C19 | 0.7870 (5) | 0.67197 (12) | 0.6566 (3) | 0.0304 (6) | |
H19 | 0.6690 | 0.6964 | 0.6530 | 0.036* | |
C20 | 0.2521 (5) | 0.73842 (12) | 0.5038 (3) | 0.0339 (7) | |
H20A | 0.2213 | 0.7764 | 0.4998 | 0.051* | |
H20B | 0.2733 | 0.7279 | 0.5913 | 0.051* | |
H20C | 0.1286 | 0.7188 | 0.4679 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0324 (4) | 0.0216 (4) | 0.0281 (4) | −0.0040 (3) | −0.0031 (3) | 0.0021 (2) |
O1 | 0.0283 (10) | 0.0232 (9) | 0.0266 (10) | 0.0024 (7) | −0.0057 (8) | 0.0012 (7) |
O2 | 0.0606 (15) | 0.0312 (11) | 0.0290 (11) | −0.0028 (10) | 0.0000 (10) | 0.0099 (9) |
F1 | 0.0414 (12) | 0.0772 (16) | 0.0665 (15) | 0.0171 (11) | −0.0087 (10) | 0.0048 (12) |
C1 | 0.0263 (13) | 0.0261 (14) | 0.0210 (13) | 0.0024 (11) | −0.0039 (10) | 0.0022 (10) |
C2 | 0.0254 (13) | 0.0252 (13) | 0.0219 (13) | −0.0018 (10) | 0.0016 (10) | −0.0007 (10) |
C3 | 0.0270 (13) | 0.0226 (13) | 0.0205 (13) | −0.0010 (10) | −0.0019 (10) | 0.0010 (10) |
C4 | 0.0356 (15) | 0.0229 (14) | 0.0280 (14) | 0.0018 (11) | −0.0092 (12) | 0.0030 (11) |
C5 | 0.0420 (17) | 0.0282 (15) | 0.0330 (16) | −0.0005 (13) | −0.0125 (13) | 0.0015 (12) |
C6 | 0.0451 (18) | 0.0238 (14) | 0.0379 (17) | −0.0038 (12) | −0.0144 (14) | −0.0035 (12) |
C7 | 0.0387 (16) | 0.0218 (14) | 0.0313 (15) | 0.0026 (12) | −0.0070 (12) | 0.0010 (11) |
C8 | 0.0263 (13) | 0.0225 (13) | 0.0210 (13) | −0.0002 (10) | −0.0008 (10) | 0.0008 (10) |
C9 | 0.0461 (19) | 0.0373 (18) | 0.0509 (18) | −0.0018 (15) | −0.0180 (15) | 0.0010 (14) |
C10A | 0.050 (3) | 0.033 (2) | 0.075 (3) | 0.006 (2) | −0.039 (3) | −0.014 (2) |
C10B | 0.022 (7) | 0.034 (6) | 0.050 (6) | −0.006 (5) | 0.009 (5) | −0.004 (4) |
C11 | 0.084 (3) | 0.041 (2) | 0.107 (3) | 0.016 (2) | −0.072 (3) | −0.018 (2) |
C12 | 0.0324 (16) | 0.0392 (17) | 0.0416 (17) | 0.0035 (13) | −0.0108 (13) | −0.0001 (14) |
C13 | 0.0411 (17) | 0.0322 (16) | 0.0398 (17) | 0.0042 (13) | −0.0130 (14) | −0.0041 (13) |
C14 | 0.0231 (13) | 0.0308 (14) | 0.0236 (13) | −0.0023 (11) | −0.0011 (10) | 0.0047 (11) |
C15 | 0.0269 (14) | 0.0348 (16) | 0.0276 (14) | −0.0008 (12) | −0.0003 (11) | 0.0019 (12) |
C16 | 0.0223 (14) | 0.0446 (18) | 0.0354 (16) | 0.0027 (12) | −0.0020 (12) | 0.0099 (13) |
C17 | 0.0310 (16) | 0.055 (2) | 0.0313 (16) | −0.0076 (14) | −0.0098 (12) | 0.0031 (14) |
C18 | 0.0391 (17) | 0.0437 (18) | 0.0311 (16) | −0.0048 (14) | −0.0067 (13) | −0.0056 (13) |
C19 | 0.0298 (15) | 0.0341 (15) | 0.0274 (14) | −0.0005 (12) | −0.0022 (11) | −0.0008 (12) |
C20 | 0.0394 (17) | 0.0291 (15) | 0.0332 (16) | 0.0042 (13) | 0.0000 (13) | −0.0008 (12) |
S1—O2 | 1.491 (2) | C10B—C11 | 1.5254 (17) |
S1—C3 | 1.765 (3) | C10B—H10C | 0.9900 |
S1—C20 | 1.789 (3) | C10B—H10D | 0.9900 |
O1—C2 | 1.377 (3) | C11—C12 | 1.521 (5) |
O1—C1 | 1.377 (3) | C11—H11A | 0.9900 |
F1—C16 | 1.345 (4) | C11—H11B | 0.9900 |
C1—C7 | 1.380 (4) | C11—H11C | 0.9900 |
C1—C8 | 1.390 (4) | C11—H11D | 0.9900 |
C2—C3 | 1.364 (4) | C12—C13 | 1.528 (4) |
C2—C14 | 1.458 (4) | C12—H12A | 0.9900 |
C3—C8 | 1.449 (4) | C12—H12B | 0.9900 |
C4—C5 | 1.390 (4) | C13—H13A | 0.9900 |
C4—C8 | 1.402 (4) | C13—H13B | 0.9900 |
C4—H4 | 0.9500 | C14—C19 | 1.396 (4) |
C5—C6 | 1.410 (4) | C14—C15 | 1.401 (4) |
C5—C9 | 1.526 (4) | C15—C16 | 1.375 (4) |
C6—C7 | 1.383 (4) | C15—H15 | 0.9500 |
C6—H6 | 0.9500 | C16—C17 | 1.377 (5) |
C7—H7 | 0.9500 | C17—C18 | 1.379 (5) |
C9—C13 | 1.487 (4) | C17—H17 | 0.9500 |
C9—C10A | 1.5249 (16) | C18—C19 | 1.386 (4) |
C9—C10B | 1.5250 (17) | C18—H18 | 0.9500 |
C9—H9A | 1.0000 | C19—H19 | 0.9500 |
C9—H9B | 1.0000 | C20—H20A | 0.9800 |
C10A—C11 | 1.5254 (17) | C20—H20B | 0.9800 |
C10A—H10A | 0.9900 | C20—H20C | 0.9800 |
C10A—H10B | 0.9900 | ||
O2—S1—C3 | 106.38 (12) | C12—C11—C10A | 106.4 (3) |
O2—S1—C20 | 106.37 (14) | C12—C11—H11A | 110.5 |
C3—S1—C20 | 98.18 (13) | C10B—C11—H11A | 133.6 |
C2—O1—C1 | 106.34 (19) | C10A—C11—H11A | 110.5 |
O1—C1—C7 | 125.4 (2) | C12—C11—H11B | 110.5 |
O1—C1—C8 | 111.0 (2) | C10B—C11—H11B | 83.8 |
C7—C1—C8 | 123.6 (2) | C10A—C11—H11B | 110.5 |
C3—C2—O1 | 110.9 (2) | H11A—C11—H11B | 108.6 |
C3—C2—C14 | 133.8 (3) | C12—C11—H11C | 111.1 |
O1—C2—C14 | 115.2 (2) | C10B—C11—H11C | 112.7 |
C2—C3—C8 | 107.0 (2) | C10A—C11—H11C | 86.0 |
C2—C3—S1 | 126.0 (2) | H11B—C11—H11C | 128.0 |
C8—C3—S1 | 126.7 (2) | C12—C11—H11D | 111.1 |
C5—C4—C8 | 119.0 (3) | C10B—C11—H11D | 106.7 |
C5—C4—H4 | 120.5 | C10A—C11—H11D | 130.0 |
C8—C4—H4 | 120.5 | H11A—C11—H11D | 86.2 |
C4—C5—C6 | 119.2 (3) | H11C—C11—H11D | 109.2 |
C4—C5—C9 | 121.4 (3) | C11—C12—C13 | 105.2 (2) |
C6—C5—C9 | 119.3 (3) | C11—C12—H12A | 110.7 |
C7—C6—C5 | 123.0 (3) | C13—C12—H12A | 110.7 |
C7—C6—H6 | 118.5 | C11—C12—H12B | 110.7 |
C5—C6—H6 | 118.5 | C13—C12—H12B | 110.7 |
C1—C7—C6 | 116.0 (3) | H12A—C12—H12B | 108.8 |
C1—C7—H7 | 122.0 | C9—C13—C12 | 103.9 (2) |
C6—C7—H7 | 122.0 | C9—C13—H13A | 111.0 |
C1—C8—C4 | 119.3 (2) | C12—C13—H13A | 111.0 |
C1—C8—C3 | 104.8 (2) | C9—C13—H13B | 111.0 |
C4—C8—C3 | 135.9 (2) | C12—C13—H13B | 111.0 |
C13—C9—C5 | 118.0 (3) | H13A—C13—H13B | 109.0 |
C13—C9—C10A | 102.7 (3) | C19—C14—C15 | 119.4 (3) |
C5—C9—C10A | 113.8 (3) | C19—C14—C2 | 120.9 (2) |
C13—C9—C10B | 111.3 (3) | C15—C14—C2 | 119.6 (3) |
C5—C9—C10B | 125.4 (5) | C16—C15—C14 | 118.3 (3) |
C13—C9—H9A | 107.2 | C16—C15—H15 | 120.9 |
C5—C9—H9A | 107.2 | C14—C15—H15 | 120.9 |
C10A—C9—H9A | 107.2 | F1—C16—C15 | 118.7 (3) |
C10B—C9—H9A | 77.8 | F1—C16—C17 | 118.1 (3) |
C13—C9—H9B | 97.9 | C15—C16—C17 | 123.2 (3) |
C5—C9—H9B | 98.0 | C16—C17—C18 | 118.1 (3) |
C10A—C9—H9B | 126.7 | C16—C17—H17 | 121.0 |
C10B—C9—H9B | 97.2 | C18—C17—H17 | 121.0 |
C9—C10A—C11 | 103.2 (3) | C17—C18—C19 | 120.9 (3) |
C9—C10A—H10A | 111.1 | C17—C18—H18 | 119.5 |
C11—C10A—H10A | 111.1 | C19—C18—H18 | 119.5 |
C9—C10A—H10B | 111.1 | C18—C19—C14 | 120.1 (3) |
C11—C10A—H10B | 111.1 | C18—C19—H19 | 119.9 |
H10A—C10A—H10B | 109.1 | C14—C19—H19 | 119.9 |
C9—C10B—C11 | 103.2 (3) | S1—C20—H20A | 109.5 |
C9—C10B—H10C | 111.1 | S1—C20—H20B | 109.5 |
C11—C10B—H10C | 111.1 | H20A—C20—H20B | 109.5 |
C9—C10B—H10D | 111.1 | S1—C20—H20C | 109.5 |
C11—C10B—H10D | 111.1 | H20A—C20—H20C | 109.5 |
H10C—C10B—H10D | 109.1 | H20B—C20—H20C | 109.5 |
C12—C11—C10B | 105.9 (5) | ||
C2—O1—C1—C7 | −178.4 (3) | C4—C5—C9—C10B | 169.7 (9) |
C2—O1—C1—C8 | 0.9 (3) | C6—C5—C9—C10B | −14.5 (10) |
C1—O1—C2—C3 | −1.1 (3) | C13—C9—C10A—C11 | −40.4 (6) |
C1—O1—C2—C14 | 176.1 (2) | C5—C9—C10A—C11 | −169.1 (4) |
O1—C2—C3—C8 | 0.9 (3) | C10B—C9—C10A—C11 | 70.6 (5) |
C14—C2—C3—C8 | −175.6 (3) | C13—C9—C10B—C11 | 7.3 (14) |
O1—C2—C3—S1 | −172.60 (18) | C5—C9—C10B—C11 | −146.2 (7) |
C14—C2—C3—S1 | 10.9 (4) | C10A—C9—C10B—C11 | −70.6 (5) |
O2—S1—C3—C2 | 137.4 (2) | C9—C10B—C11—C12 | −24.6 (13) |
C20—S1—C3—C2 | −112.8 (3) | C9—C10B—C11—C10A | 70.6 (5) |
O2—S1—C3—C8 | −34.9 (3) | C9—C10A—C11—C12 | 22.9 (7) |
C20—S1—C3—C8 | 74.9 (3) | C9—C10A—C11—C10B | −70.6 (5) |
C8—C4—C5—C6 | −2.3 (4) | C10B—C11—C12—C13 | 33.3 (9) |
C8—C4—C5—C9 | 173.6 (3) | C10A—C11—C12—C13 | 2.6 (6) |
C4—C5—C6—C7 | 1.1 (5) | C5—C9—C13—C12 | 168.4 (3) |
C9—C5—C6—C7 | −174.9 (3) | C10A—C9—C13—C12 | 42.3 (4) |
O1—C1—C7—C6 | 177.9 (3) | C10B—C9—C13—C12 | 12.7 (9) |
C8—C1—C7—C6 | −1.3 (4) | C11—C12—C13—C9 | −27.9 (4) |
C5—C6—C7—C1 | 0.7 (5) | C3—C2—C14—C19 | 28.7 (5) |
O1—C1—C8—C4 | −179.2 (2) | O1—C2—C14—C19 | −147.7 (3) |
C7—C1—C8—C4 | 0.1 (4) | C3—C2—C14—C15 | −153.4 (3) |
O1—C1—C8—C3 | −0.3 (3) | O1—C2—C14—C15 | 30.2 (3) |
C7—C1—C8—C3 | 179.0 (3) | C19—C14—C15—C16 | −0.7 (4) |
C5—C4—C8—C1 | 1.7 (4) | C2—C14—C15—C16 | −178.7 (3) |
C5—C4—C8—C3 | −176.7 (3) | C14—C15—C16—F1 | 178.7 (3) |
C2—C3—C8—C1 | −0.4 (3) | C14—C15—C16—C17 | −0.2 (4) |
S1—C3—C8—C1 | 173.1 (2) | F1—C16—C17—C18 | −178.4 (3) |
C2—C3—C8—C4 | 178.2 (3) | C15—C16—C17—C18 | 0.5 (5) |
S1—C3—C8—C4 | −8.3 (5) | C16—C17—C18—C19 | 0.2 (5) |
C4—C5—C9—C13 | 17.8 (5) | C17—C18—C19—C14 | −1.1 (5) |
C6—C5—C9—C13 | −166.4 (3) | C15—C14—C19—C18 | 1.4 (4) |
C4—C5—C9—C10A | 138.2 (5) | C2—C14—C19—C18 | 179.2 (3) |
C6—C5—C9—C10A | −45.9 (5) |
Cg1 and Cg2 are the centroids of the C1–C3/C8/O1 furan ring and the C2–C7 benzene ring, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···O2i | 0.95 | 2.52 | 3.326 (4) | 143 |
C20—H20B···O2i | 0.98 | 2.47 | 3.279 (4) | 140 |
C9—H9A···Cg1ii | 1.00 | 2.76 | 3.626 (4) | 145 |
C15—H15···Cg2iii | 0.95 | 2.94 | 3.461 (4) | 116 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x−1, y, z; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H19FO2S |
Mr | 342.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 6.1024 (3), 25.3030 (11), 10.6840 (5) |
β (°) | 90.231 (1) |
V (Å3) | 1649.69 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.40 × 0.25 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.919, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13224, 2905, 2568 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.165, 1.02 |
No. of reflections | 2905 |
No. of parameters | 228 |
No. of restraints | 30 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.35, −0.55 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
Cg1 and Cg2 are the centroids of the C1–C3/C8/O1 furan ring and the C2–C7 benzene ring, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···O2i | 0.95 | 2.52 | 3.326 (4) | 142.6 |
C20—H20B···O2i | 0.98 | 2.47 | 3.279 (4) | 140.2 |
C9—H9A···Cg1ii | 1.00 | 2.76 | 3.626 (4) | 145.4 |
C15—H15···Cg2iii | 0.95 | 2.94 | 3.461 (4) | 116.1 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x−1, y, z; (iii) x+1, y, z. |
References
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. (2011). Acta Cryst. E67, o1000. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2591. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
As a part of our ongoing study of 5-cyclopentyl-3-methylsulfinyl-1-benzofuran derivatives containing 2-phenyl (Choi et al., 2011) and 2-(4-fluorophenyl) (Seo et al., 2011) substituents, we report herein the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an envelope conformation with the C10 atom as a flop. This atom is disordered over two sites, C10A and C10B, with occupancy factors of 0.803 (16) and 0.197 (16), respectively. The dihedral angle between the 3-fluorophenyl group and the mean plane of the benzofuran fragment is 30.7 (1)°. In the crystal structure, molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C1–C3/C8/O1 furan ring and the C2–C7 benzene ring, respectively). The crystal packing (Fig. 2) also exhibits C—F···π interactions between the fluorine atom and the furan ring of an adjacent molecule, with a C16—F1···Cg1iii distance of 3.257 (3) Å.