organic compounds
5-Cyclopentyl-2-(4-fluorophenyl)-3-isopropylsulfonyl-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, C22H23FO3S, the cyclopentyl ring adopts an with the flap atom connected to the benzofuran residue. The 4-fluorophenyl ring makes a dihedral angle of 43.67 (3)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions, forming a three--dimensional network. The also exhibits slipped π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.883 (2) Å and slippage = 1.731 (2) Å].
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2011); Seo et al. (2011).
Experimental
Crystal data
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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 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812045916/fy2075sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045916/fy2075Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045916/fy2075Isup3.cml
3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-(4-fluorophenyl)-3-isopropylsulfanyl-1-benzofuran (283 mg, 0.8 mmol) in dichloromethane (40 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 67%, m.p. 397–398 K; Rf = 0.62 (benzene)]. 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 geometrically positioned and refined using a riding model, with C—H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine, methylene and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.
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).C22H23FO3S | F(000) = 816 |
Mr = 386.46 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/n | Melting point = 397–398 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4736 (3) Å | Cell parameters from 5864 reflections |
b = 19.6185 (7) Å | θ = 2.3–28.0° |
c = 10.8018 (3) Å | µ = 0.20 mm−1 |
β = 108.833 (1)° | T = 173 K |
V = 1900.12 (10) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.39 × 0.36 mm |
Bruker SMART APEXII CCD diffractometer | 4714 independent reflections |
Radiation source: rotating anode | 3948 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.030 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.3°, θmin = 2.1° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −22→26 |
Tmin = 0.678, Tmax = 0.746 | l = −14→14 |
18610 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)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6277P] where P = (Fo2 + 2Fc2)/3 |
4714 reflections | (Δ/σ)max = 0.001 |
246 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C22H23FO3S | V = 1900.12 (10) Å3 |
Mr = 386.46 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.4736 (3) Å | µ = 0.20 mm−1 |
b = 19.6185 (7) Å | T = 173 K |
c = 10.8018 (3) Å | 0.40 × 0.39 × 0.36 mm |
β = 108.833 (1)° |
Bruker SMART APEXII CCD diffractometer | 4714 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3948 reflections with I > 2σ(I) |
Tmin = 0.678, Tmax = 0.746 | Rint = 0.030 |
18610 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.40 e Å−3 |
4714 reflections | Δρmin = −0.35 e Å−3 |
246 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.81280 (3) | 0.528906 (17) | 0.27421 (3) | 0.02105 (10) | |
F1 | 0.90366 (12) | 0.18165 (5) | 0.46703 (11) | 0.0459 (3) | |
O1 | 0.48867 (10) | 0.43110 (5) | 0.35291 (10) | 0.0264 (2) | |
O2 | 0.93832 (11) | 0.48394 (5) | 0.32355 (11) | 0.0299 (2) | |
O3 | 0.83351 (11) | 0.60006 (5) | 0.30821 (10) | 0.0297 (2) | |
C1 | 0.66190 (14) | 0.50030 (7) | 0.31937 (13) | 0.0215 (3) | |
C2 | 0.53071 (14) | 0.54131 (7) | 0.30820 (13) | 0.0217 (3) | |
C3 | 0.49027 (15) | 0.60966 (7) | 0.28294 (13) | 0.0235 (3) | |
H3 | 0.5589 | 0.6419 | 0.2697 | 0.028* | |
C4 | 0.34694 (15) | 0.62964 (7) | 0.27761 (13) | 0.0251 (3) | |
C5 | 0.24785 (15) | 0.58109 (8) | 0.29843 (14) | 0.0275 (3) | |
H5 | 0.1506 | 0.5955 | 0.2939 | 0.033* | |
C6 | 0.28562 (15) | 0.51320 (8) | 0.32526 (14) | 0.0280 (3) | |
H6 | 0.2180 | 0.4809 | 0.3399 | 0.034* | |
C7 | 0.42847 (15) | 0.49561 (7) | 0.32929 (14) | 0.0238 (3) | |
C8 | 0.63093 (14) | 0.43500 (7) | 0.34624 (13) | 0.0229 (3) | |
C9 | 0.29291 (16) | 0.70217 (8) | 0.24587 (15) | 0.0292 (3) | |
H9 | 0.2007 | 0.7076 | 0.2709 | 0.035* | |
C10 | 0.2528 (2) | 0.72112 (9) | 0.10096 (16) | 0.0411 (4) | |
H10A | 0.3331 | 0.7074 | 0.0660 | 0.049* | |
H10B | 0.1587 | 0.6988 | 0.0487 | 0.049* | |
C11 | 0.2353 (2) | 0.79875 (9) | 0.09816 (17) | 0.0416 (4) | |
H11A | 0.1295 | 0.8115 | 0.0807 | 0.050* | |
H11B | 0.2706 | 0.8190 | 0.0295 | 0.050* | |
C12 | 0.3312 (2) | 0.82331 (9) | 0.2342 (2) | 0.0471 (5) | |
H12A | 0.4107 | 0.8543 | 0.2271 | 0.057* | |
H12B | 0.2692 | 0.8479 | 0.2778 | 0.057* | |
C13 | 0.3992 (2) | 0.75922 (9) | 0.31167 (18) | 0.0424 (4) | |
H13A | 0.5003 | 0.7506 | 0.3070 | 0.051* | |
H13B | 0.4056 | 0.7639 | 0.4046 | 0.051* | |
C14 | 0.70929 (15) | 0.36969 (7) | 0.37007 (14) | 0.0241 (3) | |
C15 | 0.85560 (16) | 0.36436 (7) | 0.45435 (14) | 0.0256 (3) | |
H15 | 0.9103 | 0.4044 | 0.4896 | 0.031* | |
C16 | 0.92156 (16) | 0.30085 (8) | 0.48691 (15) | 0.0298 (3) | |
H16 | 1.0204 | 0.2966 | 0.5456 | 0.036* | |
C17 | 0.83981 (18) | 0.24418 (8) | 0.43187 (16) | 0.0323 (3) | |
C18 | 0.69763 (19) | 0.24717 (8) | 0.34516 (16) | 0.0347 (3) | |
H18 | 0.6461 | 0.2069 | 0.3069 | 0.042* | |
C19 | 0.63156 (17) | 0.31065 (8) | 0.31509 (15) | 0.0306 (3) | |
H19 | 0.5325 | 0.3141 | 0.2566 | 0.037* | |
C20 | 0.74619 (16) | 0.52264 (8) | 0.09910 (14) | 0.0292 (3) | |
H20 | 0.6493 | 0.5477 | 0.0655 | 0.035* | |
C21 | 0.7201 (2) | 0.44906 (10) | 0.05634 (18) | 0.0481 (5) | |
H21A | 0.6878 | 0.4466 | −0.0394 | 0.072* | |
H21B | 0.6426 | 0.4296 | 0.0878 | 0.072* | |
H21C | 0.8128 | 0.4233 | 0.0929 | 0.072* | |
C22 | 0.8593 (2) | 0.55731 (9) | 0.04609 (17) | 0.0410 (4) | |
H22A | 0.9560 | 0.5344 | 0.0810 | 0.061* | |
H22B | 0.8698 | 0.6053 | 0.0729 | 0.061* | |
H22C | 0.8246 | 0.5545 | −0.0496 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01823 (16) | 0.01971 (18) | 0.02505 (17) | −0.00166 (12) | 0.00676 (12) | −0.00080 (12) |
F1 | 0.0517 (6) | 0.0212 (5) | 0.0596 (7) | 0.0103 (4) | 0.0106 (5) | 0.0027 (4) |
O1 | 0.0223 (5) | 0.0215 (5) | 0.0367 (6) | −0.0023 (4) | 0.0113 (4) | 0.0004 (4) |
O2 | 0.0193 (5) | 0.0320 (6) | 0.0380 (6) | 0.0034 (4) | 0.0090 (4) | 0.0067 (5) |
O3 | 0.0314 (5) | 0.0216 (5) | 0.0373 (6) | −0.0074 (4) | 0.0124 (4) | −0.0046 (4) |
C1 | 0.0190 (6) | 0.0198 (6) | 0.0253 (6) | −0.0007 (5) | 0.0065 (5) | −0.0015 (5) |
C2 | 0.0196 (6) | 0.0228 (7) | 0.0225 (6) | −0.0011 (5) | 0.0063 (5) | −0.0020 (5) |
C3 | 0.0231 (6) | 0.0216 (7) | 0.0260 (7) | −0.0002 (5) | 0.0082 (5) | −0.0008 (5) |
C4 | 0.0245 (6) | 0.0257 (7) | 0.0244 (7) | 0.0026 (5) | 0.0066 (5) | −0.0035 (5) |
C5 | 0.0199 (6) | 0.0332 (8) | 0.0298 (7) | 0.0020 (6) | 0.0087 (5) | −0.0046 (6) |
C6 | 0.0223 (7) | 0.0302 (8) | 0.0329 (7) | −0.0040 (6) | 0.0110 (6) | −0.0028 (6) |
C7 | 0.0235 (6) | 0.0204 (7) | 0.0270 (7) | −0.0007 (5) | 0.0077 (5) | −0.0010 (5) |
C8 | 0.0202 (6) | 0.0228 (7) | 0.0256 (7) | −0.0025 (5) | 0.0071 (5) | −0.0029 (5) |
C9 | 0.0256 (7) | 0.0268 (8) | 0.0355 (8) | 0.0056 (6) | 0.0103 (6) | −0.0023 (6) |
C10 | 0.0478 (10) | 0.0339 (9) | 0.0335 (9) | 0.0123 (8) | 0.0018 (7) | −0.0007 (7) |
C11 | 0.0459 (10) | 0.0343 (10) | 0.0449 (10) | 0.0155 (8) | 0.0150 (8) | 0.0075 (7) |
C12 | 0.0444 (10) | 0.0260 (9) | 0.0634 (12) | 0.0050 (7) | 0.0070 (9) | −0.0025 (8) |
C13 | 0.0415 (9) | 0.0304 (9) | 0.0444 (10) | 0.0063 (7) | −0.0014 (7) | −0.0084 (7) |
C14 | 0.0269 (7) | 0.0188 (7) | 0.0272 (7) | −0.0003 (5) | 0.0098 (5) | 0.0003 (5) |
C15 | 0.0266 (7) | 0.0218 (7) | 0.0287 (7) | −0.0017 (5) | 0.0092 (6) | −0.0014 (6) |
C16 | 0.0287 (7) | 0.0277 (8) | 0.0321 (8) | 0.0025 (6) | 0.0083 (6) | 0.0012 (6) |
C17 | 0.0413 (8) | 0.0188 (7) | 0.0381 (8) | 0.0067 (6) | 0.0148 (7) | 0.0020 (6) |
C18 | 0.0412 (9) | 0.0200 (8) | 0.0394 (9) | −0.0042 (6) | 0.0082 (7) | −0.0051 (6) |
C19 | 0.0298 (7) | 0.0233 (7) | 0.0346 (8) | −0.0019 (6) | 0.0047 (6) | −0.0026 (6) |
C20 | 0.0290 (7) | 0.0333 (8) | 0.0239 (7) | 0.0019 (6) | 0.0065 (6) | −0.0006 (6) |
C21 | 0.0667 (12) | 0.0422 (11) | 0.0345 (9) | −0.0129 (9) | 0.0150 (8) | −0.0137 (8) |
C22 | 0.0479 (10) | 0.0459 (10) | 0.0356 (9) | −0.0007 (8) | 0.0225 (7) | 0.0012 (7) |
S1—O2 | 1.4377 (10) | C11—H11A | 0.9900 |
S1—O3 | 1.4406 (11) | C11—H11B | 0.9900 |
S1—C1 | 1.7455 (13) | C12—C13 | 1.533 (2) |
S1—C20 | 1.7946 (14) | C12—H12A | 0.9900 |
F1—C17 | 1.3663 (17) | C12—H12B | 0.9900 |
O1—C8 | 1.3749 (15) | C13—H13A | 0.9900 |
O1—C7 | 1.3776 (17) | C13—H13B | 0.9900 |
C1—C8 | 1.3661 (19) | C14—C15 | 1.395 (2) |
C1—C2 | 1.4526 (18) | C14—C19 | 1.398 (2) |
C2—C7 | 1.3916 (18) | C15—C16 | 1.387 (2) |
C2—C3 | 1.3971 (19) | C15—H15 | 0.9500 |
C3—C4 | 1.3965 (18) | C16—C17 | 1.375 (2) |
C3—H3 | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.405 (2) | C17—C18 | 1.371 (2) |
C4—C9 | 1.514 (2) | C18—C19 | 1.385 (2) |
C5—C6 | 1.385 (2) | C18—H18 | 0.9500 |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—C7 | 1.3836 (18) | C20—C21 | 1.511 (2) |
C6—H6 | 0.9500 | C20—C22 | 1.528 (2) |
C8—C14 | 1.4613 (19) | C20—H20 | 1.0000 |
C9—C13 | 1.520 (2) | C21—H21A | 0.9800 |
C9—C10 | 1.533 (2) | C21—H21B | 0.9800 |
C9—H9 | 1.0000 | C21—H21C | 0.9800 |
C10—C11 | 1.531 (2) | C22—H22A | 0.9800 |
C10—H10A | 0.9900 | C22—H22B | 0.9800 |
C10—H10B | 0.9900 | C22—H22C | 0.9800 |
C11—C12 | 1.534 (3) | ||
O2—S1—O3 | 118.15 (6) | C13—C12—C11 | 106.26 (14) |
O2—S1—C1 | 110.68 (6) | C13—C12—H12A | 110.5 |
O3—S1—C1 | 107.26 (6) | C11—C12—H12A | 110.5 |
O2—S1—C20 | 108.42 (7) | C13—C12—H12B | 110.5 |
O3—S1—C20 | 107.92 (7) | C11—C12—H12B | 110.5 |
C1—S1—C20 | 103.38 (7) | H12A—C12—H12B | 108.7 |
C8—O1—C7 | 107.06 (10) | C9—C13—C12 | 104.50 (13) |
C8—C1—C2 | 107.48 (11) | C9—C13—H13A | 110.9 |
C8—C1—S1 | 127.76 (10) | C12—C13—H13A | 110.9 |
C2—C1—S1 | 123.69 (10) | C9—C13—H13B | 110.9 |
C7—C2—C3 | 119.27 (12) | C12—C13—H13B | 110.9 |
C7—C2—C1 | 104.57 (12) | H13A—C13—H13B | 108.9 |
C3—C2—C1 | 136.16 (12) | C15—C14—C19 | 119.42 (13) |
C4—C3—C2 | 118.62 (13) | C15—C14—C8 | 121.46 (13) |
C4—C3—H3 | 120.7 | C19—C14—C8 | 118.93 (13) |
C2—C3—H3 | 120.7 | C16—C15—C14 | 120.27 (13) |
C3—C4—C5 | 119.61 (13) | C16—C15—H15 | 119.9 |
C3—C4—C9 | 121.76 (13) | C14—C15—H15 | 119.9 |
C5—C4—C9 | 118.61 (12) | C17—C16—C15 | 118.14 (14) |
C6—C5—C4 | 122.97 (13) | C17—C16—H16 | 120.9 |
C6—C5—H5 | 118.5 | C15—C16—H16 | 120.9 |
C4—C5—H5 | 118.5 | F1—C17—C18 | 118.51 (14) |
C7—C6—C5 | 115.49 (13) | F1—C17—C16 | 117.95 (14) |
C7—C6—H6 | 122.3 | C18—C17—C16 | 123.54 (14) |
C5—C6—H6 | 122.3 | C17—C18—C19 | 117.95 (14) |
O1—C7—C6 | 125.26 (13) | C17—C18—H18 | 121.0 |
O1—C7—C2 | 110.72 (11) | C19—C18—H18 | 121.0 |
C6—C7—C2 | 124.02 (13) | C18—C19—C14 | 120.62 (14) |
C1—C8—O1 | 110.16 (12) | C18—C19—H19 | 119.7 |
C1—C8—C14 | 136.71 (12) | C14—C19—H19 | 119.7 |
O1—C8—C14 | 113.13 (11) | C21—C20—C22 | 112.09 (14) |
C4—C9—C13 | 117.50 (13) | C21—C20—S1 | 110.77 (11) |
C4—C9—C10 | 114.43 (12) | C22—C20—S1 | 108.30 (11) |
C13—C9—C10 | 101.96 (14) | C21—C20—H20 | 108.5 |
C4—C9—H9 | 107.5 | C22—C20—H20 | 108.5 |
C13—C9—H9 | 107.5 | S1—C20—H20 | 108.5 |
C10—C9—H9 | 107.5 | C20—C21—H21A | 109.5 |
C11—C10—C9 | 104.54 (13) | C20—C21—H21B | 109.5 |
C11—C10—H10A | 110.8 | H21A—C21—H21B | 109.5 |
C9—C10—H10A | 110.8 | C20—C21—H21C | 109.5 |
C11—C10—H10B | 110.8 | H21A—C21—H21C | 109.5 |
C9—C10—H10B | 110.8 | H21B—C21—H21C | 109.5 |
H10A—C10—H10B | 108.9 | C20—C22—H22A | 109.5 |
C10—C11—C12 | 105.45 (14) | C20—C22—H22B | 109.5 |
C10—C11—H11A | 110.7 | H22A—C22—H22B | 109.5 |
C12—C11—H11A | 110.7 | C20—C22—H22C | 109.5 |
C10—C11—H11B | 110.7 | H22A—C22—H22C | 109.5 |
C12—C11—H11B | 110.7 | H22B—C22—H22C | 109.5 |
H11A—C11—H11B | 108.8 | ||
O2—S1—C1—C8 | −26.55 (15) | C3—C4—C9—C13 | −43.8 (2) |
O3—S1—C1—C8 | −156.74 (12) | C5—C4—C9—C13 | 138.05 (15) |
C20—S1—C1—C8 | 89.36 (14) | C3—C4—C9—C10 | 75.76 (18) |
O2—S1—C1—C2 | 166.81 (11) | C5—C4—C9—C10 | −102.40 (16) |
O3—S1—C1—C2 | 36.62 (13) | C4—C9—C10—C11 | −168.08 (13) |
C20—S1—C1—C2 | −77.28 (12) | C13—C9—C10—C11 | −40.14 (16) |
C8—C1—C2—C7 | −0.33 (15) | C9—C10—C11—C12 | 25.31 (18) |
S1—C1—C2—C7 | 168.63 (10) | C10—C11—C12—C13 | −0.8 (2) |
C8—C1—C2—C3 | 179.94 (15) | C4—C9—C13—C12 | 165.45 (14) |
S1—C1—C2—C3 | −11.1 (2) | C10—C9—C13—C12 | 39.50 (17) |
C7—C2—C3—C4 | −1.0 (2) | C11—C12—C13—C9 | −24.25 (19) |
C1—C2—C3—C4 | 178.68 (15) | C1—C8—C14—C15 | 45.9 (2) |
C2—C3—C4—C5 | 0.4 (2) | O1—C8—C14—C15 | −133.59 (13) |
C2—C3—C4—C9 | −177.73 (13) | C1—C8—C14—C19 | −139.22 (17) |
C3—C4—C5—C6 | 0.4 (2) | O1—C8—C14—C19 | 41.31 (17) |
C9—C4—C5—C6 | 178.60 (13) | C19—C14—C15—C16 | −2.3 (2) |
C4—C5—C6—C7 | −0.5 (2) | C8—C14—C15—C16 | 172.62 (13) |
C8—O1—C7—C6 | 178.93 (13) | C14—C15—C16—C17 | 1.3 (2) |
C8—O1—C7—C2 | −0.37 (15) | C15—C16—C17—F1 | −178.20 (13) |
C5—C6—C7—O1 | −179.33 (13) | C15—C16—C17—C18 | 1.0 (2) |
C5—C6—C7—C2 | −0.1 (2) | F1—C17—C18—C19 | 176.99 (14) |
C3—C2—C7—O1 | −179.78 (12) | C16—C17—C18—C19 | −2.2 (3) |
C1—C2—C7—O1 | 0.43 (15) | C17—C18—C19—C14 | 1.2 (2) |
C3—C2—C7—C6 | 0.9 (2) | C15—C14—C19—C18 | 1.0 (2) |
C1—C2—C7—C6 | −178.88 (13) | C8—C14—C19—C18 | −173.99 (14) |
C2—C1—C8—O1 | 0.11 (15) | O2—S1—C20—C21 | 51.63 (13) |
S1—C1—C8—O1 | −168.26 (10) | O3—S1—C20—C21 | −179.29 (12) |
C2—C1—C8—C14 | −179.37 (15) | C1—S1—C20—C21 | −65.87 (13) |
S1—C1—C8—C14 | 12.3 (3) | O2—S1—C20—C22 | −71.66 (12) |
C7—O1—C8—C1 | 0.15 (15) | O3—S1—C20—C22 | 57.41 (12) |
C7—O1—C8—C14 | 179.77 (11) | C1—S1—C20—C22 | 170.83 (11) |
Cg1 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.60 | 3.3341 (17) | 135 |
C18—H18···O3ii | 0.95 | 2.48 | 3.2932 (19) | 144 |
C21—H21A···Cg1iii | 0.98 | 2.71 | 3.693 (2) | 177 |
Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H23FO3S |
Mr | 386.46 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.4736 (3), 19.6185 (7), 10.8018 (3) |
β (°) | 108.833 (1) |
V (Å3) | 1900.12 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.40 × 0.39 × 0.36 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.678, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18610, 4714, 3948 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.103, 1.03 |
No. of reflections | 4714 |
No. of parameters | 246 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.35 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).
Cg1 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.60 | 3.3341 (17) | 134.5 |
C18—H18···O3ii | 0.95 | 2.48 | 3.2932 (19) | 144.0 |
C21—H21A···Cg1iii | 0.98 | 2.71 | 3.693 (2) | 177.3 |
Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −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.
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. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS 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-1-benzofuran derivatives containing (2-phenyl-3-methylsulfinyl) (Choi et al., 2011) and {2-(4-fluorophenyl)-3-methylsulfinyl} (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 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an envelope conformation. The dihedral angle between the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 43.67 (3)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 2) also exhibits slipped π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2iv distance of 3.883 (2) Å and an interplanar distance of 3.476 (2) Å resulting in a slippage of 1.731 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring, iv: -x + 1, -y + 1, -z + 1).