organic compounds
5-Cyclopentyl-2-methyl-3-(3-methylphenylsulfonyl)-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, C21H22O3S, the five-membered ring adopts an with the ipso atom deviating by 0.596 (2) Å from the plane through the rest of the ring atoms. The dihedral angle between the mean planes of the benzofuran and m-tolyl moieties is 78.4 (1)°. In the crystal, molecules related by a glide plane are linked via C—H⋯O hydrogen bonds into chains along the a-axis direction. These chains are in turn connected by C—H⋯π interactions into layers parallel to the ac plane.
CCDC reference: 992719
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2012); Seo et al. (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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 992719
10.1107/S1600536814006187/ld2123sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006187/ld2123Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006187/ld2123Isup3.cml
3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-methyl-3-(3-methylphenylsulfanyl)-1-benzofuran (290 mg, 0.9 mmol) in dichloromethane (30 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 73%, m.p. 417–418 K; Rf = 0.48 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.All H atoms were positioned geometrically 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 and methylene, and 1.5Ueq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).
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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C21H22O3S | Dx = 1.307 Mg m−3 |
Mr = 354.45 | Melting point = 418–417 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3275 reflections |
a = 18.2293 (7) Å | θ = 2.6–28.0° |
b = 6.1955 (3) Å | µ = 0.20 mm−1 |
c = 15.9471 (8) Å | T = 173 K |
V = 1801.06 (14) Å3 | Block, colourless |
Z = 4 | 0.58 × 0.20 × 0.14 mm |
F(000) = 752 |
Bruker SMART APEXII CCD diffractometer | 3543 independent reflections |
Radiation source: rotating anode | 3115 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.031 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.4°, θmin = 2.2° |
ϕ and ω scans | h = −24→20 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −8→8 |
Tmin = 0.683, Tmax = 0.746 | l = −15→21 |
9604 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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.6298P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3543 reflections | Δρmax = 0.54 e Å−3 |
228 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1205 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (9) |
C21H22O3S | V = 1801.06 (14) Å3 |
Mr = 354.45 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 18.2293 (7) Å | µ = 0.20 mm−1 |
b = 6.1955 (3) Å | T = 173 K |
c = 15.9471 (8) Å | 0.58 × 0.20 × 0.14 mm |
Bruker SMART APEXII CCD diffractometer | 3543 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3115 reflections with I > 2σ(I) |
Tmin = 0.683, Tmax = 0.746 | Rint = 0.031 |
9604 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | Δρmax = 0.54 e Å−3 |
S = 1.04 | Δρmin = −0.24 e Å−3 |
3543 reflections | Absolute structure: Flack (1983), 1205 Friedel pairs |
228 parameters | Absolute structure parameter: 0.00 (9) |
1 restraint |
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 | 0.04477 (3) | 0.35807 (10) | 0.10257 (5) | 0.02864 (15) | |
O1 | 0.23298 (10) | 0.1800 (3) | 0.00693 (12) | 0.0330 (4) | |
O2 | 0.03032 (9) | 0.5860 (3) | 0.10602 (17) | 0.0364 (4) | |
O3 | −0.00242 (10) | 0.2226 (3) | 0.05328 (14) | 0.0384 (5) | |
C1 | 0.13426 (13) | 0.3255 (4) | 0.06741 (17) | 0.0279 (5) | |
C2 | 0.19660 (12) | 0.4600 (4) | 0.08929 (17) | 0.0268 (6) | |
C3 | 0.20851 (14) | 0.6445 (4) | 0.13714 (18) | 0.0296 (6) | |
H3 | 0.1686 | 0.7160 | 0.1636 | 0.035* | |
C4 | 0.27969 (14) | 0.7230 (4) | 0.14570 (18) | 0.0307 (6) | |
C5 | 0.33751 (12) | 0.6156 (4) | 0.1049 (2) | 0.0350 (6) | |
H5 | 0.3859 | 0.6701 | 0.1110 | 0.042* | |
C6 | 0.32665 (14) | 0.4335 (5) | 0.0562 (2) | 0.0361 (6) | |
H6 | 0.3659 | 0.3625 | 0.0285 | 0.043* | |
C7 | 0.25515 (14) | 0.3616 (4) | 0.05046 (19) | 0.0290 (5) | |
C8 | 0.15930 (14) | 0.1608 (4) | 0.01931 (18) | 0.0304 (6) | |
C9 | 0.29660 (16) | 0.9193 (5) | 0.1986 (2) | 0.0375 (6) | |
H9 | 0.3094 | 1.0402 | 0.1597 | 0.045* | |
C10 | 0.3623 (2) | 0.8851 (7) | 0.2584 (3) | 0.0622 (11) | |
H10A | 0.3591 | 0.7436 | 0.2870 | 0.075* | |
H10B | 0.4094 | 0.8935 | 0.2277 | 0.075* | |
C11 | 0.3549 (2) | 1.0726 (8) | 0.3217 (3) | 0.0695 (12) | |
H11A | 0.3658 | 1.0215 | 0.3792 | 0.083* | |
H11B | 0.3896 | 1.1900 | 0.3076 | 0.083* | |
C12 | 0.2784 (2) | 1.1510 (7) | 0.3164 (3) | 0.0742 (14) | |
H12A | 0.2772 | 1.3006 | 0.2945 | 0.089* | |
H12B | 0.2550 | 1.1488 | 0.3724 | 0.089* | |
C13 | 0.23894 (19) | 0.9984 (8) | 0.2568 (3) | 0.0744 (15) | |
H13A | 0.2166 | 0.8769 | 0.2879 | 0.089* | |
H13B | 0.1999 | 1.0754 | 0.2256 | 0.089* | |
C14 | 0.12535 (16) | −0.0293 (5) | −0.0228 (2) | 0.0396 (7) | |
H14A | 0.0774 | −0.0591 | 0.0026 | 0.059* | |
H14B | 0.1573 | −0.1553 | −0.0160 | 0.059* | |
H14C | 0.1190 | 0.0017 | −0.0826 | 0.059* | |
C15 | 0.04614 (13) | 0.2588 (5) | 0.20576 (18) | 0.0293 (6) | |
C16 | 0.07316 (15) | 0.3898 (5) | 0.26988 (19) | 0.0325 (6) | |
H16 | 0.0892 | 0.5319 | 0.2571 | 0.039* | |
C17 | 0.07705 (15) | 0.3171 (5) | 0.35138 (19) | 0.0356 (6) | |
C18 | 0.05211 (15) | 0.1092 (5) | 0.3682 (2) | 0.0392 (7) | |
H18 | 0.0534 | 0.0564 | 0.4241 | 0.047* | |
C19 | 0.02542 (16) | −0.0220 (5) | 0.3047 (2) | 0.0403 (7) | |
H19 | 0.0085 | −0.1631 | 0.3178 | 0.048* | |
C20 | 0.02297 (14) | 0.0489 (5) | 0.2224 (2) | 0.0351 (6) | |
H20 | 0.0060 | −0.0426 | 0.1787 | 0.042* | |
C21 | 0.1076 (2) | 0.4573 (6) | 0.4203 (2) | 0.0501 (8) | |
H21A | 0.0697 | 0.4824 | 0.4627 | 0.075* | |
H21B | 0.1234 | 0.5958 | 0.3967 | 0.075* | |
H21C | 0.1497 | 0.3849 | 0.4462 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0223 (2) | 0.0339 (3) | 0.0297 (3) | −0.0001 (2) | −0.0018 (3) | −0.0038 (3) |
O1 | 0.0291 (9) | 0.0375 (10) | 0.0324 (11) | 0.0016 (8) | 0.0024 (8) | −0.0091 (9) |
O2 | 0.0315 (8) | 0.0360 (9) | 0.0419 (11) | 0.0067 (7) | −0.0011 (10) | −0.0003 (12) |
O3 | 0.0270 (9) | 0.0482 (11) | 0.0399 (12) | −0.0067 (8) | −0.0046 (8) | −0.0062 (10) |
C1 | 0.0255 (11) | 0.0322 (13) | 0.0259 (13) | 0.0005 (10) | −0.0006 (10) | −0.0011 (11) |
C2 | 0.0236 (10) | 0.0308 (13) | 0.0258 (15) | 0.0002 (9) | −0.0010 (9) | 0.0047 (11) |
C3 | 0.0276 (12) | 0.0312 (14) | 0.0299 (15) | 0.0006 (10) | 0.0005 (10) | −0.0015 (12) |
C4 | 0.0306 (12) | 0.0320 (14) | 0.0297 (15) | −0.0032 (11) | −0.0063 (11) | 0.0053 (12) |
C5 | 0.0251 (10) | 0.0423 (14) | 0.0374 (15) | −0.0066 (10) | 0.0020 (14) | 0.0026 (15) |
C6 | 0.0267 (12) | 0.0438 (15) | 0.0379 (17) | 0.0004 (11) | 0.0062 (11) | −0.0012 (14) |
C7 | 0.0285 (12) | 0.0322 (13) | 0.0263 (13) | 0.0001 (10) | 0.0008 (10) | −0.0004 (12) |
C8 | 0.0300 (12) | 0.0339 (14) | 0.0275 (15) | 0.0005 (11) | 0.0010 (11) | 0.0014 (11) |
C9 | 0.0447 (15) | 0.0306 (14) | 0.0374 (17) | −0.0042 (12) | −0.0063 (13) | 0.0038 (13) |
C10 | 0.0471 (18) | 0.071 (3) | 0.068 (3) | 0.0007 (18) | −0.0165 (18) | −0.026 (2) |
C11 | 0.054 (2) | 0.083 (3) | 0.071 (3) | 0.004 (2) | −0.016 (2) | −0.040 (2) |
C12 | 0.054 (2) | 0.071 (3) | 0.098 (4) | −0.0056 (19) | −0.006 (2) | −0.048 (3) |
C13 | 0.0405 (18) | 0.081 (3) | 0.102 (4) | 0.0042 (18) | −0.008 (2) | −0.057 (3) |
C14 | 0.0441 (16) | 0.0411 (16) | 0.0335 (17) | 0.0001 (13) | −0.0023 (13) | −0.0110 (14) |
C15 | 0.0230 (11) | 0.0331 (13) | 0.0317 (15) | 0.0029 (10) | 0.0012 (10) | −0.0022 (12) |
C16 | 0.0326 (13) | 0.0328 (15) | 0.0320 (16) | −0.0003 (11) | 0.0037 (12) | −0.0052 (12) |
C17 | 0.0334 (13) | 0.0420 (16) | 0.0315 (16) | 0.0059 (12) | 0.0039 (12) | −0.0049 (13) |
C18 | 0.0353 (14) | 0.0450 (18) | 0.0373 (18) | 0.0044 (13) | 0.0022 (12) | 0.0063 (14) |
C19 | 0.0374 (14) | 0.0354 (16) | 0.048 (2) | 0.0006 (12) | 0.0003 (14) | 0.0080 (14) |
C20 | 0.0292 (12) | 0.0336 (14) | 0.0426 (18) | −0.0025 (11) | 0.0005 (12) | −0.0045 (13) |
C21 | 0.062 (2) | 0.056 (2) | 0.0327 (18) | 0.0023 (17) | −0.0065 (15) | −0.0102 (16) |
S1—O3 | 1.436 (2) | C11—C12 | 1.479 (5) |
S1—O2 | 1.4374 (18) | C11—H11A | 0.9900 |
S1—C1 | 1.737 (2) | C11—H11B | 0.9900 |
S1—C15 | 1.757 (3) | C12—C13 | 1.522 (5) |
O1—C8 | 1.363 (3) | C12—H12A | 0.9900 |
O1—C7 | 1.382 (3) | C12—H12B | 0.9900 |
C1—C8 | 1.356 (4) | C13—H13A | 0.9900 |
C1—C2 | 1.451 (3) | C13—H13B | 0.9900 |
C2—C7 | 1.376 (4) | C14—H14A | 0.9800 |
C2—C3 | 1.392 (4) | C14—H14B | 0.9800 |
C3—C4 | 1.392 (4) | C14—H14C | 0.9800 |
C3—H3 | 0.9500 | C15—C20 | 1.393 (4) |
C4—C5 | 1.406 (4) | C15—C16 | 1.395 (4) |
C4—C9 | 1.511 (4) | C16—C17 | 1.377 (4) |
C5—C6 | 1.383 (4) | C16—H16 | 0.9500 |
C5—H5 | 0.9500 | C17—C18 | 1.392 (4) |
C6—C7 | 1.381 (4) | C17—C21 | 1.507 (4) |
C6—H6 | 0.9500 | C18—C19 | 1.388 (5) |
C8—C14 | 1.490 (4) | C18—H18 | 0.9500 |
C9—C13 | 1.485 (5) | C19—C20 | 1.384 (5) |
C9—C10 | 1.546 (5) | C19—H19 | 0.9500 |
C9—H9 | 1.0000 | C20—H20 | 0.9500 |
C10—C11 | 1.545 (5) | C21—H21A | 0.9800 |
C10—H10A | 0.9900 | C21—H21B | 0.9800 |
C10—H10B | 0.9900 | C21—H21C | 0.9800 |
O3—S1—O2 | 119.03 (12) | C12—C11—H11B | 110.3 |
O3—S1—C1 | 108.55 (12) | C10—C11—H11B | 110.3 |
O2—S1—C1 | 107.38 (11) | H11A—C11—H11B | 108.6 |
O3—S1—C15 | 108.46 (13) | C11—C12—C13 | 106.1 (3) |
O2—S1—C15 | 108.09 (14) | C11—C12—H12A | 110.5 |
C1—S1—C15 | 104.38 (12) | C13—C12—H12A | 110.5 |
C8—O1—C7 | 106.7 (2) | C11—C12—H12B | 110.5 |
C8—C1—C2 | 107.7 (2) | C13—C12—H12B | 110.5 |
C8—C1—S1 | 125.89 (19) | H12A—C12—H12B | 108.7 |
C2—C1—S1 | 126.24 (19) | C9—C13—C12 | 105.1 (3) |
C7—C2—C3 | 119.3 (2) | C9—C13—H13A | 110.7 |
C7—C2—C1 | 104.2 (2) | C12—C13—H13A | 110.7 |
C3—C2—C1 | 136.5 (2) | C9—C13—H13B | 110.7 |
C2—C3—C4 | 119.1 (2) | C12—C13—H13B | 110.7 |
C2—C3—H3 | 120.5 | H13A—C13—H13B | 108.8 |
C4—C3—H3 | 120.5 | C8—C14—H14A | 109.5 |
C3—C4—C5 | 119.2 (3) | C8—C14—H14B | 109.5 |
C3—C4—C9 | 121.7 (3) | H14A—C14—H14B | 109.5 |
C5—C4—C9 | 119.1 (2) | C8—C14—H14C | 109.5 |
C6—C5—C4 | 122.6 (2) | H14A—C14—H14C | 109.5 |
C6—C5—H5 | 118.7 | H14B—C14—H14C | 109.5 |
C4—C5—H5 | 118.7 | C20—C15—C16 | 120.7 (3) |
C7—C6—C5 | 115.8 (2) | C20—C15—S1 | 120.1 (2) |
C7—C6—H6 | 122.1 | C16—C15—S1 | 119.2 (2) |
C5—C6—H6 | 122.1 | C17—C16—C15 | 121.3 (3) |
C2—C7—C6 | 124.0 (3) | C17—C16—H16 | 119.4 |
C2—C7—O1 | 111.1 (2) | C15—C16—H16 | 119.4 |
C6—C7—O1 | 124.9 (2) | C16—C17—C18 | 117.9 (3) |
C1—C8—O1 | 110.4 (2) | C16—C17—C21 | 121.2 (3) |
C1—C8—C14 | 135.2 (2) | C18—C17—C21 | 120.9 (3) |
O1—C8—C14 | 114.4 (2) | C19—C18—C17 | 121.0 (3) |
C13—C9—C4 | 118.0 (3) | C19—C18—H18 | 119.5 |
C13—C9—C10 | 102.0 (3) | C17—C18—H18 | 119.5 |
C4—C9—C10 | 113.1 (3) | C20—C19—C18 | 121.2 (3) |
C13—C9—H9 | 107.7 | C20—C19—H19 | 119.4 |
C4—C9—H9 | 107.7 | C18—C19—H19 | 119.4 |
C10—C9—H9 | 107.7 | C19—C20—C15 | 117.9 (3) |
C11—C10—C9 | 103.5 (3) | C19—C20—H20 | 121.1 |
C11—C10—H10A | 111.1 | C15—C20—H20 | 121.1 |
C9—C10—H10A | 111.1 | C17—C21—H21A | 109.5 |
C11—C10—H10B | 111.1 | C17—C21—H21B | 109.5 |
C9—C10—H10B | 111.1 | H21A—C21—H21B | 109.5 |
H10A—C10—H10B | 109.0 | C17—C21—H21C | 109.5 |
C12—C11—C10 | 106.9 (3) | H21A—C21—H21C | 109.5 |
C12—C11—H11A | 110.3 | H21B—C21—H21C | 109.5 |
C10—C11—H11A | 110.3 | ||
O3—S1—C1—C8 | −17.0 (3) | C7—O1—C8—C1 | 1.2 (3) |
O2—S1—C1—C8 | −146.9 (2) | C7—O1—C8—C14 | −179.5 (2) |
C15—S1—C1—C8 | 98.5 (3) | C3—C4—C9—C13 | 13.6 (5) |
O3—S1—C1—C2 | 168.0 (2) | C5—C4—C9—C13 | −165.6 (3) |
O2—S1—C1—C2 | 38.1 (3) | C3—C4—C9—C10 | 132.5 (3) |
C15—S1—C1—C2 | −76.5 (3) | C5—C4—C9—C10 | −46.7 (4) |
C8—C1—C2—C7 | 0.5 (3) | C13—C9—C10—C11 | −36.3 (4) |
S1—C1—C2—C7 | 176.3 (2) | C4—C9—C10—C11 | −164.1 (3) |
C8—C1—C2—C3 | −178.2 (3) | C9—C10—C11—C12 | 19.1 (5) |
S1—C1—C2—C3 | −2.4 (5) | C10—C11—C12—C13 | 5.2 (6) |
C7—C2—C3—C4 | −1.1 (4) | C4—C9—C13—C12 | 164.8 (3) |
C1—C2—C3—C4 | 177.5 (3) | C10—C9—C13—C12 | 40.2 (4) |
C2—C3—C4—C5 | 0.8 (4) | C11—C12—C13—C9 | −28.9 (5) |
C2—C3—C4—C9 | −178.4 (3) | O3—S1—C15—C20 | 17.8 (2) |
C3—C4—C5—C6 | 0.0 (5) | O2—S1—C15—C20 | 148.1 (2) |
C9—C4—C5—C6 | 179.2 (3) | C1—S1—C15—C20 | −97.8 (2) |
C4—C5—C6—C7 | −0.5 (5) | O3—S1—C15—C16 | −164.5 (2) |
C3—C2—C7—C6 | 0.5 (4) | O2—S1—C15—C16 | −34.2 (2) |
C1—C2—C7—C6 | −178.4 (3) | C1—S1—C15—C16 | 79.9 (2) |
C3—C2—C7—O1 | 179.2 (2) | C20—C15—C16—C17 | −0.7 (4) |
C1—C2—C7—O1 | 0.2 (3) | S1—C15—C16—C17 | −178.3 (2) |
C5—C6—C7—C2 | 0.3 (5) | C15—C16—C17—C18 | −0.9 (4) |
C5—C6—C7—O1 | −178.2 (3) | C15—C16—C17—C21 | 178.8 (3) |
C8—O1—C7—C2 | −0.9 (3) | C16—C17—C18—C19 | 1.2 (4) |
C8—O1—C7—C6 | 177.7 (3) | C21—C17—C18—C19 | −178.6 (3) |
C2—C1—C8—O1 | −1.1 (3) | C17—C18—C19—C20 | 0.3 (5) |
S1—C1—C8—O1 | −176.91 (19) | C18—C19—C20—C15 | −1.9 (4) |
C2—C1—C8—C14 | 179.9 (3) | C16—C15—C20—C19 | 2.1 (4) |
S1—C1—C8—C14 | 4.1 (5) | S1—C15—C20—C19 | 179.7 (2) |
Cg1 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3i | 0.95 | 2.49 | 3.263 (3) | 139 |
C13—H13B···Cg1ii | 0.99 | 2.99 | 3.671 (3) | 127 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y+1, z. |
Cg1 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3i | 0.95 | 2.49 | 3.263 (3) | 138.7 |
C13—H13B···Cg1ii | 0.99 | 2.99 | 3.671 (3) | 127.1 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y+1, z. |
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As a part of our ongoing study of 5-cyclopentyl-2-methyl-1-benzofuran derivatives containing phenylsulfonyl (Seo et al., 2011) and 4-bromophenylsulfonyl (Choi et al., 2012) substituents in the 3-position, we report here on the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.015 (2) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the six constituent atoms. The cyclopentyl ring has an envelope conformation. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 78.44 (8)°.
In the crystal structure (Fig. 2), the molecules are linked by C—H···O hydrogen bonds (Table 1) related by gliding plane a perpendicular to b-axis. The chains of C—H···O bonded molecules are stacked by C—H···π interactions (Table 1, Cg1 is the centroid of the C15–C20 3-methylphenyl-ring), resulting in a two-dimensional supramolecular layers.