organic compounds
5-Cyclohexyl-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, C22H24O3S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran ring system and the benzene ring is 81.78 (4)°. In the crystal, molecules are linked via pairs of C—H⋯π interactions into inversion dimers. These dimers are further linked by C—H⋯π interactions into supramolecular chains running along the b-axis direction. In addition, C—H⋯O hydrogen bonds are observed between inversion-related dimers.
CCDC reference: 993236
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012a,b).
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: 993236
10.1107/S1600536814006448/kj2238sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006448/kj2238Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006448/kj2238Isup3.cml
3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-methyl-3-(3-methylphenylsulfanyl)-1-benzofuran (302 mg, 0.9 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
(hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 428–429 K; Rf = 0.57 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow vaporation 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 = 0.95 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 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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. | |
Fig. 2. A view of the C—H···O and C—H···π hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes : (i) - x + 1, - y, - z + 1; (ii) - x + 1, - y + 1, - z + 1; (iii) x - 1, y, z; (iv) x + 1, y, z.] |
C22H24O3S | Z = 2 |
Mr = 368.47 | F(000) = 392 |
Triclinic, P1 | Dx = 1.295 Mg m−3 |
Hall symbol: -P 1 | Melting point = 428–429 K |
a = 8.9729 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3462 (1) Å | Cell parameters from 6413 reflections |
c = 11.0978 (2) Å | θ = 2.5–28.0° |
α = 91.027 (1)° | µ = 0.19 mm−1 |
β = 112.142 (1)° | T = 173 K |
γ = 96.920 (1)° | Block, colourless |
V = 945.09 (2) Å3 | 0.45 × 0.24 × 0.12 mm |
Bruker SMART APEXII CCD diffractometer | 4676 independent reflections |
Radiation source: rotating anode | 3862 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.027 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.4°, θmin = 2.0° |
ϕ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −13→13 |
Tmin = 0.704, Tmax = 0.746 | l = −14→14 |
17505 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)] = 0.042 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.3454P] where P = (Fo2 + 2Fc2)/3 |
4676 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C22H24O3S | γ = 96.920 (1)° |
Mr = 368.47 | V = 945.09 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9729 (1) Å | Mo Kα radiation |
b = 10.3462 (1) Å | µ = 0.19 mm−1 |
c = 11.0978 (2) Å | T = 173 K |
α = 91.027 (1)° | 0.45 × 0.24 × 0.12 mm |
β = 112.142 (1)° |
Bruker SMART APEXII CCD diffractometer | 4676 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3862 reflections with I > 2σ(I) |
Tmin = 0.704, Tmax = 0.746 | Rint = 0.027 |
17505 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.27 e Å−3 |
4676 reflections | Δρmin = −0.36 e Å−3 |
237 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 | ||
S1 | 0.35800 (4) | 0.03292 (4) | 0.20843 (3) | 0.02902 (11) | |
O1 | 0.55693 (14) | 0.33589 (12) | 0.08723 (11) | 0.0373 (3) | |
O2 | 0.46948 (14) | −0.02883 (11) | 0.31363 (10) | 0.0359 (3) | |
O3 | 0.27359 (15) | −0.03917 (11) | 0.08444 (11) | 0.0405 (3) | |
C1 | 0.46417 (18) | 0.17522 (15) | 0.18450 (14) | 0.0290 (3) | |
C2 | 0.57504 (17) | 0.26991 (14) | 0.28633 (14) | 0.0275 (3) | |
C3 | 0.63168 (17) | 0.28333 (14) | 0.42235 (14) | 0.0279 (3) | |
H3 | 0.5980 | 0.2181 | 0.4694 | 0.033* | |
C4 | 0.73853 (18) | 0.39425 (15) | 0.48773 (15) | 0.0299 (3) | |
C5 | 0.78770 (19) | 0.48851 (16) | 0.41575 (16) | 0.0369 (4) | |
H5 | 0.8608 | 0.5636 | 0.4613 | 0.044* | |
C6 | 0.7337 (2) | 0.47625 (17) | 0.28097 (17) | 0.0389 (4) | |
H6 | 0.7682 | 0.5404 | 0.2333 | 0.047* | |
C7 | 0.62752 (19) | 0.36615 (16) | 0.22028 (15) | 0.0327 (3) | |
C8 | 0.45740 (19) | 0.22001 (16) | 0.06823 (15) | 0.0338 (3) | |
C9 | 0.79994 (18) | 0.41730 (15) | 0.63454 (14) | 0.0310 (3) | |
H9 | 0.8961 | 0.4868 | 0.6611 | 0.037* | |
C10 | 0.8576 (2) | 0.29841 (18) | 0.70674 (16) | 0.0426 (4) | |
H10A | 0.9431 | 0.2692 | 0.6810 | 0.051* | |
H10B | 0.7657 | 0.2266 | 0.6813 | 0.051* | |
C15 | 0.3672 (2) | 0.1726 (2) | −0.07082 (16) | 0.0449 (4) | |
H15A | 0.3005 | 0.0889 | −0.0758 | 0.067* | |
H15B | 0.4446 | 0.1613 | −0.1119 | 0.067* | |
H15C | 0.2970 | 0.2365 | −0.1163 | 0.067* | |
C16 | 0.21417 (17) | 0.08713 (14) | 0.26325 (14) | 0.0274 (3) | |
C17 | 0.24711 (17) | 0.09527 (14) | 0.39576 (14) | 0.0283 (3) | |
H17 | 0.3450 | 0.0700 | 0.4555 | 0.034* | |
C18 | 0.13676 (19) | 0.14042 (15) | 0.44124 (15) | 0.0325 (3) | |
C19 | −0.0052 (2) | 0.17699 (17) | 0.35005 (17) | 0.0391 (4) | |
H19 | −0.0811 | 0.2095 | 0.3795 | 0.047* | |
C20 | −0.0379 (2) | 0.16714 (18) | 0.21828 (17) | 0.0410 (4) | |
H20 | −0.1362 | 0.1918 | 0.1584 | 0.049* | |
C21 | 0.07095 (19) | 0.12176 (16) | 0.17273 (15) | 0.0350 (3) | |
H21 | 0.0488 | 0.1143 | 0.0820 | 0.042* | |
C22 | 0.1720 (2) | 0.1479 (2) | 0.58506 (17) | 0.0450 (4) | |
H22A | 0.2309 | 0.0759 | 0.6250 | 0.068* | |
H22B | 0.0696 | 0.1414 | 0.5986 | 0.068* | |
H22C | 0.2385 | 0.2312 | 0.6253 | 0.068* | |
C11 | 0.9247 (2) | 0.32679 (18) | 0.85430 (16) | 0.0436 (4) | |
H11A | 0.9557 | 0.2458 | 0.8976 | 0.052* | |
H11B | 1.0235 | 0.3921 | 0.8810 | 0.052* | |
C12 | 0.8014 (2) | 0.3777 (2) | 0.89752 (17) | 0.0467 (4) | |
H12A | 0.8507 | 0.4010 | 0.9926 | 0.056* | |
H12B | 0.7080 | 0.3085 | 0.8802 | 0.056* | |
C13 | 0.7425 (3) | 0.4959 (2) | 0.82666 (19) | 0.0627 (6) | |
H13A | 0.8335 | 0.5684 | 0.8525 | 0.075* | |
H13B | 0.6564 | 0.5237 | 0.8526 | 0.075* | |
C14 | 0.6753 (3) | 0.4684 (2) | 0.67829 (18) | 0.0586 (6) | |
H14A | 0.5764 | 0.4032 | 0.6511 | 0.070* | |
H14B | 0.6447 | 0.5497 | 0.6355 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0321 (2) | 0.03056 (19) | 0.02058 (18) | 0.00720 (14) | 0.00497 (14) | −0.00076 (13) |
O1 | 0.0391 (6) | 0.0488 (7) | 0.0271 (6) | 0.0072 (5) | 0.0157 (5) | 0.0078 (5) |
O2 | 0.0390 (6) | 0.0375 (6) | 0.0295 (6) | 0.0160 (5) | 0.0080 (5) | 0.0054 (5) |
O3 | 0.0492 (7) | 0.0387 (6) | 0.0258 (6) | 0.0042 (5) | 0.0066 (5) | −0.0077 (5) |
C1 | 0.0287 (7) | 0.0357 (8) | 0.0227 (7) | 0.0086 (6) | 0.0087 (5) | 0.0006 (6) |
C2 | 0.0241 (7) | 0.0332 (7) | 0.0260 (7) | 0.0070 (5) | 0.0095 (5) | 0.0027 (6) |
C3 | 0.0259 (7) | 0.0322 (7) | 0.0246 (7) | 0.0044 (5) | 0.0083 (5) | 0.0033 (5) |
C4 | 0.0254 (7) | 0.0331 (8) | 0.0289 (7) | 0.0050 (6) | 0.0074 (6) | 0.0027 (6) |
C5 | 0.0314 (8) | 0.0361 (8) | 0.0381 (9) | −0.0001 (6) | 0.0089 (7) | 0.0053 (7) |
C6 | 0.0347 (8) | 0.0439 (9) | 0.0384 (9) | 0.0020 (7) | 0.0149 (7) | 0.0118 (7) |
C7 | 0.0303 (7) | 0.0429 (9) | 0.0272 (7) | 0.0091 (6) | 0.0122 (6) | 0.0061 (6) |
C8 | 0.0337 (8) | 0.0441 (9) | 0.0258 (7) | 0.0117 (6) | 0.0120 (6) | 0.0033 (6) |
C9 | 0.0284 (7) | 0.0308 (7) | 0.0273 (7) | 0.0016 (6) | 0.0041 (6) | 0.0009 (6) |
C10 | 0.0561 (11) | 0.0430 (9) | 0.0298 (8) | 0.0213 (8) | 0.0131 (7) | 0.0036 (7) |
C15 | 0.0536 (11) | 0.0588 (11) | 0.0218 (8) | 0.0124 (9) | 0.0124 (7) | 0.0017 (7) |
C16 | 0.0266 (7) | 0.0273 (7) | 0.0239 (7) | 0.0032 (5) | 0.0050 (5) | 0.0015 (5) |
C17 | 0.0262 (7) | 0.0303 (7) | 0.0244 (7) | 0.0047 (5) | 0.0048 (5) | 0.0029 (5) |
C18 | 0.0318 (7) | 0.0344 (8) | 0.0309 (8) | 0.0044 (6) | 0.0113 (6) | 0.0032 (6) |
C19 | 0.0307 (8) | 0.0446 (9) | 0.0430 (9) | 0.0101 (7) | 0.0136 (7) | 0.0039 (7) |
C20 | 0.0290 (8) | 0.0465 (9) | 0.0396 (9) | 0.0112 (7) | 0.0024 (7) | 0.0063 (7) |
C21 | 0.0321 (8) | 0.0404 (8) | 0.0248 (7) | 0.0066 (6) | 0.0016 (6) | 0.0048 (6) |
C22 | 0.0495 (10) | 0.0573 (11) | 0.0353 (9) | 0.0183 (8) | 0.0207 (8) | 0.0068 (8) |
C11 | 0.0551 (11) | 0.0439 (10) | 0.0288 (8) | 0.0162 (8) | 0.0098 (7) | 0.0054 (7) |
C12 | 0.0441 (10) | 0.0616 (12) | 0.0310 (9) | −0.0035 (8) | 0.0141 (7) | −0.0066 (8) |
C13 | 0.0647 (13) | 0.0845 (16) | 0.0359 (10) | 0.0439 (12) | 0.0064 (9) | −0.0132 (10) |
C14 | 0.0554 (12) | 0.0823 (15) | 0.0344 (9) | 0.0429 (11) | 0.0035 (8) | −0.0074 (9) |
S1—O3 | 1.4370 (11) | C15—H15C | 0.9800 |
S1—O2 | 1.4396 (11) | C16—C17 | 1.385 (2) |
S1—C1 | 1.7356 (16) | C16—C21 | 1.393 (2) |
S1—C16 | 1.7619 (16) | C17—C18 | 1.390 (2) |
O1—C8 | 1.368 (2) | C17—H17 | 0.9500 |
O1—C7 | 1.3821 (18) | C18—C19 | 1.396 (2) |
C1—C8 | 1.361 (2) | C18—C22 | 1.504 (2) |
C1—C2 | 1.451 (2) | C19—C20 | 1.378 (2) |
C2—C7 | 1.387 (2) | C19—H19 | 0.9500 |
C2—C3 | 1.398 (2) | C20—C21 | 1.380 (3) |
C3—C4 | 1.394 (2) | C20—H20 | 0.9500 |
C3—H3 | 0.9500 | C21—H21 | 0.9500 |
C4—C5 | 1.405 (2) | C22—H22A | 0.9800 |
C4—C9 | 1.514 (2) | C22—H22B | 0.9800 |
C5—C6 | 1.386 (2) | C22—H22C | 0.9800 |
C5—H5 | 0.9500 | C11—C12 | 1.504 (3) |
C6—C7 | 1.373 (2) | C11—H11A | 0.9900 |
C6—H6 | 0.9500 | C11—H11B | 0.9900 |
C8—C15 | 1.488 (2) | C12—C13 | 1.507 (3) |
C9—C10 | 1.516 (2) | C12—H12A | 0.9900 |
C9—C14 | 1.519 (2) | C12—H12B | 0.9900 |
C9—H9 | 1.0000 | C13—C14 | 1.533 (3) |
C10—C11 | 1.526 (2) | C13—H13A | 0.9900 |
C10—H10A | 0.9900 | C13—H13B | 0.9900 |
C10—H10B | 0.9900 | C14—H14A | 0.9900 |
C15—H15A | 0.9800 | C14—H14B | 0.9900 |
C15—H15B | 0.9800 | ||
O3—S1—O2 | 119.03 (7) | C17—C16—C21 | 121.58 (15) |
O3—S1—C1 | 108.30 (7) | C17—C16—S1 | 119.06 (11) |
O2—S1—C1 | 107.58 (7) | C21—C16—S1 | 119.36 (12) |
O3—S1—C16 | 108.82 (7) | C16—C17—C18 | 119.96 (13) |
O2—S1—C16 | 107.73 (7) | C16—C17—H17 | 120.0 |
C1—S1—C16 | 104.43 (7) | C18—C17—H17 | 120.0 |
C8—O1—C7 | 106.82 (12) | C17—C18—C19 | 118.09 (15) |
C8—C1—C2 | 107.39 (14) | C17—C18—C22 | 119.86 (14) |
C8—C1—S1 | 126.89 (12) | C19—C18—C22 | 122.05 (15) |
C2—C1—S1 | 125.71 (11) | C20—C19—C18 | 121.58 (16) |
C7—C2—C3 | 119.35 (14) | C20—C19—H19 | 119.2 |
C7—C2—C1 | 104.61 (13) | C18—C19—H19 | 119.2 |
C3—C2—C1 | 136.03 (14) | C19—C20—C21 | 120.49 (15) |
C4—C3—C2 | 118.79 (14) | C19—C20—H20 | 119.8 |
C4—C3—H3 | 120.6 | C21—C20—H20 | 119.8 |
C2—C3—H3 | 120.6 | C20—C21—C16 | 118.29 (15) |
C3—C4—C5 | 119.38 (14) | C20—C21—H21 | 120.9 |
C3—C4—C9 | 121.55 (14) | C16—C21—H21 | 120.9 |
C5—C4—C9 | 119.06 (14) | C18—C22—H22A | 109.5 |
C6—C5—C4 | 122.58 (15) | C18—C22—H22B | 109.5 |
C6—C5—H5 | 118.7 | H22A—C22—H22B | 109.5 |
C4—C5—H5 | 118.7 | C18—C22—H22C | 109.5 |
C7—C6—C5 | 116.20 (15) | H22A—C22—H22C | 109.5 |
C7—C6—H6 | 121.9 | H22B—C22—H22C | 109.5 |
C5—C6—H6 | 121.9 | C12—C11—C10 | 111.21 (15) |
C6—C7—O1 | 125.67 (15) | C12—C11—H11A | 109.4 |
C6—C7—C2 | 123.70 (15) | C10—C11—H11A | 109.4 |
O1—C7—C2 | 110.63 (14) | C12—C11—H11B | 109.4 |
C1—C8—O1 | 110.55 (14) | C10—C11—H11B | 109.4 |
C1—C8—C15 | 134.82 (16) | H11A—C11—H11B | 108.0 |
O1—C8—C15 | 114.63 (14) | C11—C12—C13 | 111.00 (16) |
C4—C9—C10 | 113.42 (13) | C11—C12—H12A | 109.4 |
C4—C9—C14 | 112.13 (13) | C13—C12—H12A | 109.4 |
C10—C9—C14 | 110.10 (15) | C11—C12—H12B | 109.4 |
C4—C9—H9 | 106.9 | C13—C12—H12B | 109.4 |
C10—C9—H9 | 106.9 | H12A—C12—H12B | 108.0 |
C14—C9—H9 | 106.9 | C12—C13—C14 | 111.88 (17) |
C9—C10—C11 | 111.95 (14) | C12—C13—H13A | 109.2 |
C9—C10—H10A | 109.2 | C14—C13—H13A | 109.2 |
C11—C10—H10A | 109.2 | C12—C13—H13B | 109.2 |
C9—C10—H10B | 109.2 | C14—C13—H13B | 109.2 |
C11—C10—H10B | 109.2 | H13A—C13—H13B | 107.9 |
H10A—C10—H10B | 107.9 | C9—C14—C13 | 111.20 (15) |
C8—C15—H15A | 109.5 | C9—C14—H14A | 109.4 |
C8—C15—H15B | 109.5 | C13—C14—H14A | 109.4 |
H15A—C15—H15B | 109.5 | C9—C14—H14B | 109.4 |
C8—C15—H15C | 109.5 | C13—C14—H14B | 109.4 |
H15A—C15—H15C | 109.5 | H14A—C14—H14B | 108.0 |
H15B—C15—H15C | 109.5 | ||
O3—S1—C1—C8 | 6.42 (17) | C7—O1—C8—C15 | 178.75 (14) |
O2—S1—C1—C8 | 136.29 (14) | C3—C4—C9—C10 | 46.6 (2) |
C16—S1—C1—C8 | −109.42 (15) | C5—C4—C9—C10 | −134.85 (16) |
O3—S1—C1—C2 | −174.83 (12) | C3—C4—C9—C14 | −78.8 (2) |
O2—S1—C1—C2 | −44.96 (15) | C5—C4—C9—C14 | 99.67 (19) |
C16—S1—C1—C2 | 69.33 (14) | C4—C9—C10—C11 | 177.73 (14) |
C8—C1—C2—C7 | −0.28 (16) | C14—C9—C10—C11 | −55.7 (2) |
S1—C1—C2—C7 | −179.24 (12) | O3—S1—C16—C17 | 146.24 (12) |
C8—C1—C2—C3 | 178.68 (17) | O2—S1—C16—C17 | 15.91 (14) |
S1—C1—C2—C3 | −0.3 (3) | C1—S1—C16—C17 | −98.28 (13) |
C7—C2—C3—C4 | 0.6 (2) | O3—S1—C16—C21 | −34.28 (14) |
C1—C2—C3—C4 | −178.23 (16) | O2—S1—C16—C21 | −164.62 (12) |
C2—C3—C4—C5 | −0.7 (2) | C1—S1—C16—C21 | 81.19 (13) |
C2—C3—C4—C9 | 177.82 (13) | C21—C16—C17—C18 | −0.8 (2) |
C3—C4—C5—C6 | 0.2 (2) | S1—C16—C17—C18 | 178.65 (11) |
C9—C4—C5—C6 | −178.34 (15) | C16—C17—C18—C19 | −0.3 (2) |
C4—C5—C6—C7 | 0.4 (3) | C16—C17—C18—C22 | 179.37 (15) |
C5—C6—C7—O1 | 178.77 (15) | C17—C18—C19—C20 | 1.1 (3) |
C5—C6—C7—C2 | −0.4 (2) | C22—C18—C19—C20 | −178.58 (17) |
C8—O1—C7—C6 | −178.71 (16) | C18—C19—C20—C21 | −0.8 (3) |
C8—O1—C7—C2 | 0.58 (17) | C19—C20—C21—C16 | −0.3 (3) |
C3—C2—C7—C6 | 0.0 (2) | C17—C16—C21—C20 | 1.1 (2) |
C1—C2—C7—C6 | 179.13 (15) | S1—C16—C21—C20 | −178.35 (12) |
C3—C2—C7—O1 | −179.35 (13) | C9—C10—C11—C12 | 56.2 (2) |
C1—C2—C7—O1 | −0.18 (17) | C10—C11—C12—C13 | −55.2 (2) |
C2—C1—C8—O1 | 0.66 (17) | C11—C12—C13—C14 | 55.2 (2) |
S1—C1—C8—O1 | 179.60 (11) | C4—C9—C14—C13 | −177.83 (18) |
C2—C1—C8—C15 | −178.72 (18) | C10—C9—C14—C13 | 54.9 (2) |
S1—C1—C8—C15 | 0.2 (3) | C12—C13—C14—C9 | −55.4 (3) |
C7—O1—C8—C1 | −0.77 (17) |
Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O2i | 0.95 | 2.55 | 3.415 (2) | 151 |
C13—H13B···Cg1ii | 0.99 | 2.83 | 3.670 (2) | 143 |
C19—H19···Cg2iii | 0.95 | 2.85 | 3.705 (2) | 150 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O2i | 0.95 | 2.55 | 3.415 (2) | 151.1 |
C13—H13B···Cg1ii | 0.99 | 2.83 | 3.670 (2) | 142.7 |
C19—H19···Cg2iii | 0.95 | 2.85 | 3.705 (2) | 149.9 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
References
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As a part of our continuing study of 5-cyclohexyl-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2011), 4-bromophenylsulfonyl (Choi et al., 2012a) and 4-methylphenylsulfonyl (Choi et al., 2012b) substituents in 3-position, we report here the crystal structure of the title compound.
In the title molecule (Fig. 1), The cyclohexyl ring has a chair conformation. The benzofuran ring system is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 81.78 (4)°. In the crystal structure (Fig. 2), molecules are connected by pairs of C—H···π interactions into inversion dimers (Table 1; Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring). These dimers are further linked by C—H···π interactions into supramolecular chains running along the b-axis (Table 1; Cg2 is the centroid of the C2–C7 benzene ring). In addition, there are C–H···O hydrogen bonds (Table 1), resulting in inversion-related dimers.