organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 13 February 2014; accepted 24 March 2014; online 29 March 2014)

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.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o767.], 2012a[Choi, H. D., Seo, P. J. & Lee, U. (2012a). Acta Cryst. E68, o480.],b[Choi, H. D., Seo, P. J. & Lee, U. (2012b). Acta Cryst. E68, o1068.]).

[Scheme 1]

Experimental

Crystal data
  • C22H24O3S

  • Mr = 368.47

  • Triclinic, [P \overline 1]

  • a = 8.9729 (1) Å

  • b = 10.3462 (1) Å

  • c = 11.0978 (2) Å

  • α = 91.027 (1)°

  • β = 112.142 (1)°

  • γ = 96.920 (1)°

  • V = 945.09 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 173 K

  • 0.45 × 0.24 × 0.12 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.704, Tmax = 0.746

  • 17505 measured reflections

  • 4676 independent reflections

  • 3862 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.03

  • 4676 reflections

  • 237 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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 DA D—H⋯A
C17—H17⋯O2i 0.95 2.55 3.415 (2) 151
C13—H13BCg1ii 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.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012a,b).

Experimental top

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 column chromatography (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.

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] 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.]
5-Cyclohexyl-2-methyl-3-(3-methylphenylsulfonyl)-1-benzofuran top
Crystal data top
C22H24O3SZ = 2
Mr = 368.47F(000) = 392
Triclinic, P1Dx = 1.295 Mg m3
Hall symbol: -P 1Melting point = 428–429 K
a = 8.9729 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3462 (1) ÅCell parameters from 6413 reflections
c = 11.0978 (2) Åθ = 2.5–28.0°
α = 91.027 (1)°µ = 0.19 mm1
β = 112.142 (1)°T = 173 K
γ = 96.920 (1)°Block, colourless
V = 945.09 (2) Å30.45 × 0.24 × 0.12 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4676 independent reflections
Radiation source: rotating anode3862 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.027
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.0°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.704, Tmax = 0.746l = 1414
17505 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.117H-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 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C22H24O3Sγ = 96.920 (1)°
Mr = 368.47V = 945.09 (2) Å3
Triclinic, P1Z = 2
a = 8.9729 (1) ÅMo Kα radiation
b = 10.3462 (1) ŵ = 0.19 mm1
c = 11.0978 (2) ÅT = 173 K
α = 91.027 (1)°0.45 × 0.24 × 0.12 mm
β = 112.142 (1)°
Data collection top
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 = 0.746Rint = 0.027
17505 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
4676 reflectionsΔρmin = 0.36 e Å3
237 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.35800 (4)0.03292 (4)0.20843 (3)0.02902 (11)
O10.55693 (14)0.33589 (12)0.08723 (11)0.0373 (3)
O20.46948 (14)0.02883 (11)0.31363 (10)0.0359 (3)
O30.27359 (15)0.03917 (11)0.08444 (11)0.0405 (3)
C10.46417 (18)0.17522 (15)0.18450 (14)0.0290 (3)
C20.57504 (17)0.26991 (14)0.28633 (14)0.0275 (3)
C30.63168 (17)0.28333 (14)0.42235 (14)0.0279 (3)
H30.59800.21810.46940.033*
C40.73853 (18)0.39425 (15)0.48773 (15)0.0299 (3)
C50.78770 (19)0.48851 (16)0.41575 (16)0.0369 (4)
H50.86080.56360.46130.044*
C60.7337 (2)0.47625 (17)0.28097 (17)0.0389 (4)
H60.76820.54040.23330.047*
C70.62752 (19)0.36615 (16)0.22028 (15)0.0327 (3)
C80.45740 (19)0.22001 (16)0.06823 (15)0.0338 (3)
C90.79994 (18)0.41730 (15)0.63454 (14)0.0310 (3)
H90.89610.48680.66110.037*
C100.8576 (2)0.29841 (18)0.70674 (16)0.0426 (4)
H10A0.94310.26920.68100.051*
H10B0.76570.22660.68130.051*
C150.3672 (2)0.1726 (2)0.07082 (16)0.0449 (4)
H15A0.30050.08890.07580.067*
H15B0.44460.16130.11190.067*
H15C0.29700.23650.11630.067*
C160.21417 (17)0.08713 (14)0.26325 (14)0.0274 (3)
C170.24711 (17)0.09527 (14)0.39576 (14)0.0283 (3)
H170.34500.07000.45550.034*
C180.13676 (19)0.14042 (15)0.44124 (15)0.0325 (3)
C190.0052 (2)0.17699 (17)0.35005 (17)0.0391 (4)
H190.08110.20950.37950.047*
C200.0379 (2)0.16714 (18)0.21828 (17)0.0410 (4)
H200.13620.19180.15840.049*
C210.07095 (19)0.12176 (16)0.17273 (15)0.0350 (3)
H210.04880.11430.08200.042*
C220.1720 (2)0.1479 (2)0.58506 (17)0.0450 (4)
H22A0.23090.07590.62500.068*
H22B0.06960.14140.59860.068*
H22C0.23850.23120.62530.068*
C110.9247 (2)0.32679 (18)0.85430 (16)0.0436 (4)
H11A0.95570.24580.89760.052*
H11B1.02350.39210.88100.052*
C120.8014 (2)0.3777 (2)0.89752 (17)0.0467 (4)
H12A0.85070.40100.99260.056*
H12B0.70800.30850.88020.056*
C130.7425 (3)0.4959 (2)0.82666 (19)0.0627 (6)
H13A0.83350.56840.85250.075*
H13B0.65640.52370.85260.075*
C140.6753 (3)0.4684 (2)0.67829 (18)0.0586 (6)
H14A0.57640.40320.65110.070*
H14B0.64470.54970.63550.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0321 (2)0.03056 (19)0.02058 (18)0.00720 (14)0.00497 (14)0.00076 (13)
O10.0391 (6)0.0488 (7)0.0271 (6)0.0072 (5)0.0157 (5)0.0078 (5)
O20.0390 (6)0.0375 (6)0.0295 (6)0.0160 (5)0.0080 (5)0.0054 (5)
O30.0492 (7)0.0387 (6)0.0258 (6)0.0042 (5)0.0066 (5)0.0077 (5)
C10.0287 (7)0.0357 (8)0.0227 (7)0.0086 (6)0.0087 (5)0.0006 (6)
C20.0241 (7)0.0332 (7)0.0260 (7)0.0070 (5)0.0095 (5)0.0027 (6)
C30.0259 (7)0.0322 (7)0.0246 (7)0.0044 (5)0.0083 (5)0.0033 (5)
C40.0254 (7)0.0331 (8)0.0289 (7)0.0050 (6)0.0074 (6)0.0027 (6)
C50.0314 (8)0.0361 (8)0.0381 (9)0.0001 (6)0.0089 (7)0.0053 (7)
C60.0347 (8)0.0439 (9)0.0384 (9)0.0020 (7)0.0149 (7)0.0118 (7)
C70.0303 (7)0.0429 (9)0.0272 (7)0.0091 (6)0.0122 (6)0.0061 (6)
C80.0337 (8)0.0441 (9)0.0258 (7)0.0117 (6)0.0120 (6)0.0033 (6)
C90.0284 (7)0.0308 (7)0.0273 (7)0.0016 (6)0.0041 (6)0.0009 (6)
C100.0561 (11)0.0430 (9)0.0298 (8)0.0213 (8)0.0131 (7)0.0036 (7)
C150.0536 (11)0.0588 (11)0.0218 (8)0.0124 (9)0.0124 (7)0.0017 (7)
C160.0266 (7)0.0273 (7)0.0239 (7)0.0032 (5)0.0050 (5)0.0015 (5)
C170.0262 (7)0.0303 (7)0.0244 (7)0.0047 (5)0.0048 (5)0.0029 (5)
C180.0318 (7)0.0344 (8)0.0309 (8)0.0044 (6)0.0113 (6)0.0032 (6)
C190.0307 (8)0.0446 (9)0.0430 (9)0.0101 (7)0.0136 (7)0.0039 (7)
C200.0290 (8)0.0465 (9)0.0396 (9)0.0112 (7)0.0024 (7)0.0063 (7)
C210.0321 (8)0.0404 (8)0.0248 (7)0.0066 (6)0.0016 (6)0.0048 (6)
C220.0495 (10)0.0573 (11)0.0353 (9)0.0183 (8)0.0207 (8)0.0068 (8)
C110.0551 (11)0.0439 (10)0.0288 (8)0.0162 (8)0.0098 (7)0.0054 (7)
C120.0441 (10)0.0616 (12)0.0310 (9)0.0035 (8)0.0141 (7)0.0066 (8)
C130.0647 (13)0.0845 (16)0.0359 (10)0.0439 (12)0.0064 (9)0.0132 (10)
C140.0554 (12)0.0823 (15)0.0344 (9)0.0429 (11)0.0035 (8)0.0074 (9)
Geometric parameters (Å, º) top
S1—O31.4370 (11)C15—H15C0.9800
S1—O21.4396 (11)C16—C171.385 (2)
S1—C11.7356 (16)C16—C211.393 (2)
S1—C161.7619 (16)C17—C181.390 (2)
O1—C81.368 (2)C17—H170.9500
O1—C71.3821 (18)C18—C191.396 (2)
C1—C81.361 (2)C18—C221.504 (2)
C1—C21.451 (2)C19—C201.378 (2)
C2—C71.387 (2)C19—H190.9500
C2—C31.398 (2)C20—C211.380 (3)
C3—C41.394 (2)C20—H200.9500
C3—H30.9500C21—H210.9500
C4—C51.405 (2)C22—H22A0.9800
C4—C91.514 (2)C22—H22B0.9800
C5—C61.386 (2)C22—H22C0.9800
C5—H50.9500C11—C121.504 (3)
C6—C71.373 (2)C11—H11A0.9900
C6—H60.9500C11—H11B0.9900
C8—C151.488 (2)C12—C131.507 (3)
C9—C101.516 (2)C12—H12A0.9900
C9—C141.519 (2)C12—H12B0.9900
C9—H91.0000C13—C141.533 (3)
C10—C111.526 (2)C13—H13A0.9900
C10—H10A0.9900C13—H13B0.9900
C10—H10B0.9900C14—H14A0.9900
C15—H15A0.9800C14—H14B0.9900
C15—H15B0.9800
O3—S1—O2119.03 (7)C17—C16—C21121.58 (15)
O3—S1—C1108.30 (7)C17—C16—S1119.06 (11)
O2—S1—C1107.58 (7)C21—C16—S1119.36 (12)
O3—S1—C16108.82 (7)C16—C17—C18119.96 (13)
O2—S1—C16107.73 (7)C16—C17—H17120.0
C1—S1—C16104.43 (7)C18—C17—H17120.0
C8—O1—C7106.82 (12)C17—C18—C19118.09 (15)
C8—C1—C2107.39 (14)C17—C18—C22119.86 (14)
C8—C1—S1126.89 (12)C19—C18—C22122.05 (15)
C2—C1—S1125.71 (11)C20—C19—C18121.58 (16)
C7—C2—C3119.35 (14)C20—C19—H19119.2
C7—C2—C1104.61 (13)C18—C19—H19119.2
C3—C2—C1136.03 (14)C19—C20—C21120.49 (15)
C4—C3—C2118.79 (14)C19—C20—H20119.8
C4—C3—H3120.6C21—C20—H20119.8
C2—C3—H3120.6C20—C21—C16118.29 (15)
C3—C4—C5119.38 (14)C20—C21—H21120.9
C3—C4—C9121.55 (14)C16—C21—H21120.9
C5—C4—C9119.06 (14)C18—C22—H22A109.5
C6—C5—C4122.58 (15)C18—C22—H22B109.5
C6—C5—H5118.7H22A—C22—H22B109.5
C4—C5—H5118.7C18—C22—H22C109.5
C7—C6—C5116.20 (15)H22A—C22—H22C109.5
C7—C6—H6121.9H22B—C22—H22C109.5
C5—C6—H6121.9C12—C11—C10111.21 (15)
C6—C7—O1125.67 (15)C12—C11—H11A109.4
C6—C7—C2123.70 (15)C10—C11—H11A109.4
O1—C7—C2110.63 (14)C12—C11—H11B109.4
C1—C8—O1110.55 (14)C10—C11—H11B109.4
C1—C8—C15134.82 (16)H11A—C11—H11B108.0
O1—C8—C15114.63 (14)C11—C12—C13111.00 (16)
C4—C9—C10113.42 (13)C11—C12—H12A109.4
C4—C9—C14112.13 (13)C13—C12—H12A109.4
C10—C9—C14110.10 (15)C11—C12—H12B109.4
C4—C9—H9106.9C13—C12—H12B109.4
C10—C9—H9106.9H12A—C12—H12B108.0
C14—C9—H9106.9C12—C13—C14111.88 (17)
C9—C10—C11111.95 (14)C12—C13—H13A109.2
C9—C10—H10A109.2C14—C13—H13A109.2
C11—C10—H10A109.2C12—C13—H13B109.2
C9—C10—H10B109.2C14—C13—H13B109.2
C11—C10—H10B109.2H13A—C13—H13B107.9
H10A—C10—H10B107.9C9—C14—C13111.20 (15)
C8—C15—H15A109.5C9—C14—H14A109.4
C8—C15—H15B109.5C13—C14—H14A109.4
H15A—C15—H15B109.5C9—C14—H14B109.4
C8—C15—H15C109.5C13—C14—H14B109.4
H15A—C15—H15C109.5H14A—C14—H14B108.0
H15B—C15—H15C109.5
O3—S1—C1—C86.42 (17)C7—O1—C8—C15178.75 (14)
O2—S1—C1—C8136.29 (14)C3—C4—C9—C1046.6 (2)
C16—S1—C1—C8109.42 (15)C5—C4—C9—C10134.85 (16)
O3—S1—C1—C2174.83 (12)C3—C4—C9—C1478.8 (2)
O2—S1—C1—C244.96 (15)C5—C4—C9—C1499.67 (19)
C16—S1—C1—C269.33 (14)C4—C9—C10—C11177.73 (14)
C8—C1—C2—C70.28 (16)C14—C9—C10—C1155.7 (2)
S1—C1—C2—C7179.24 (12)O3—S1—C16—C17146.24 (12)
C8—C1—C2—C3178.68 (17)O2—S1—C16—C1715.91 (14)
S1—C1—C2—C30.3 (3)C1—S1—C16—C1798.28 (13)
C7—C2—C3—C40.6 (2)O3—S1—C16—C2134.28 (14)
C1—C2—C3—C4178.23 (16)O2—S1—C16—C21164.62 (12)
C2—C3—C4—C50.7 (2)C1—S1—C16—C2181.19 (13)
C2—C3—C4—C9177.82 (13)C21—C16—C17—C180.8 (2)
C3—C4—C5—C60.2 (2)S1—C16—C17—C18178.65 (11)
C9—C4—C5—C6178.34 (15)C16—C17—C18—C190.3 (2)
C4—C5—C6—C70.4 (3)C16—C17—C18—C22179.37 (15)
C5—C6—C7—O1178.77 (15)C17—C18—C19—C201.1 (3)
C5—C6—C7—C20.4 (2)C22—C18—C19—C20178.58 (17)
C8—O1—C7—C6178.71 (16)C18—C19—C20—C210.8 (3)
C8—O1—C7—C20.58 (17)C19—C20—C21—C160.3 (3)
C3—C2—C7—C60.0 (2)C17—C16—C21—C201.1 (2)
C1—C2—C7—C6179.13 (15)S1—C16—C21—C20178.35 (12)
C3—C2—C7—O1179.35 (13)C9—C10—C11—C1256.2 (2)
C1—C2—C7—O10.18 (17)C10—C11—C12—C1355.2 (2)
C2—C1—C8—O10.66 (17)C11—C12—C13—C1455.2 (2)
S1—C1—C8—O1179.60 (11)C4—C9—C14—C13177.83 (18)
C2—C1—C8—C15178.72 (18)C10—C9—C14—C1354.9 (2)
S1—C1—C8—C150.2 (3)C12—C13—C14—C955.4 (3)
C7—O1—C8—C10.77 (17)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.952.553.415 (2)151
C13—H13B···Cg1ii0.992.833.670 (2)143
C19—H19···Cg2iii0.952.853.705 (2)150
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.952.553.415 (2)151.1
C13—H13B···Cg1ii0.992.833.670 (2)142.7
C19—H19···Cg2iii0.952.853.705 (2)149.9
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x1, y, z.
 

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