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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Cyclo­hexyl-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

(Received 21 March 2011; accepted 24 March 2011; online 31 March 2011)

In the title compound, C23H25FO2S, the cyclo­hexyl ring adopts a chair conformation. The 4-fluoro­phenyl ring makes a dihedral angle of 50.74 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by inter­molecular C—H⋯π inter­actions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res., 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For structural studies of related 2-aryl-5-cyclo­hexyl-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2011a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.]).

[Scheme 1]

Experimental

Crystal data
  • C23H25FO3S

  • Mr = 400.49

  • Monoclinic, P 21 /c

  • a = 16.2065 (3) Å

  • b = 8.4993 (2) Å

  • c = 15.4031 (3) Å

  • β = 110.411 (1)°

  • V = 1988.47 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 173 K

  • 0.35 × 0.25 × 0.16 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 = 0.935, Tmax = 0.969

  • 34421 measured reflections

  • 4536 independent reflections

  • 3857 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.118

  • S = 1.05

  • 4536 reflections

  • 255 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14ACgi 0.99 2.68 3.667 (2) 172
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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

Many compounds having a benzofuran skeleton exhibit potent biological properties such as antibacterial, antifungal, antitumor, antiviral and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 2-aryl-5-cyclohexyl-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2011a, b), we report herein on the molecular and crystal structures of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 50.74 (4)° with the mean plane of the benzofuran fragment. The crystal packing is stabilized by intermolecular C—H···π interactions between a cyclohexyl H atom and the benzene ring (Table 1; C14—H14A···Cgi, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 2-aryl-5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2011a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(4-fluorophenyl)-3-isopropylsulfanyl-1-benzofuran (331 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 (benzene) to afford the title compound as a colorless solid [yield 73%, m.p. 417–418 K; Rf = 0.66 (benzene)]. 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.

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.

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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

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 a small spheres of arbitrary radius.
5-Cyclohexyl-2-(4-fluorophenyl)-3-isopropylsulfonyl-1-benzofuran top
Crystal data top
C23H25FO3SF(000) = 848
Mr = 400.49Dx = 1.338 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9904 reflections
a = 16.2065 (3) Åθ = 2.7–27.5°
b = 8.4993 (2) ŵ = 0.19 mm1
c = 15.4031 (3) ÅT = 173 K
β = 110.411 (1)°Block, colourless
V = 1988.47 (7) Å30.35 × 0.25 × 0.16 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
4536 independent reflections
Radiation source: rotating anode3857 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.040
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.3°
ϕ and ω scansh = 2121
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1110
Tmin = 0.935, Tmax = 0.969l = 1919
34421 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)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.118H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0616P)2 + 0.8589P]
where P = (Fo2 + 2Fc2)/3
4536 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C23H25FO3SV = 1988.47 (7) Å3
Mr = 400.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.2065 (3) ŵ = 0.19 mm1
b = 8.4993 (2) ÅT = 173 K
c = 15.4031 (3) Å0.35 × 0.25 × 0.16 mm
β = 110.411 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
4536 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3857 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.969Rint = 0.040
34421 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.05Δρmax = 0.43 e Å3
4536 reflectionsΔρmin = 0.43 e Å3
255 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
S10.19580 (2)0.56351 (4)0.11644 (2)0.02585 (12)
F10.06671 (7)0.55451 (15)0.39156 (8)0.0526 (3)
O10.30601 (7)0.43713 (13)0.37816 (7)0.0286 (2)
O20.12420 (7)0.65463 (14)0.12504 (8)0.0355 (3)
O30.25519 (7)0.63717 (14)0.07757 (8)0.0337 (3)
C10.26010 (9)0.49468 (18)0.22631 (10)0.0250 (3)
C20.35310 (10)0.45605 (17)0.25534 (10)0.0254 (3)
C30.41687 (10)0.44682 (18)0.21347 (10)0.0271 (3)
H30.40250.47230.14980.032*
C40.50184 (10)0.39963 (18)0.26662 (11)0.0288 (3)
C50.52195 (10)0.3651 (2)0.36117 (11)0.0336 (4)
H50.58020.33330.39670.040*
C60.46071 (10)0.3755 (2)0.40410 (11)0.0330 (3)
H60.47510.35220.46800.040*
C70.37701 (10)0.42184 (18)0.34923 (10)0.0269 (3)
C80.23549 (10)0.48094 (18)0.30212 (10)0.0262 (3)
C90.57531 (10)0.38349 (19)0.22780 (11)0.0311 (3)
H90.60530.28100.25060.037*
C100.54480 (11)0.3797 (3)0.12306 (12)0.0440 (4)
H10A0.51450.47960.09780.053*
H10B0.50220.29270.09960.053*
C110.62254 (12)0.3564 (3)0.08978 (14)0.0464 (5)
H11A0.65020.25300.11130.056*
H11B0.60100.35670.02120.056*
C120.69027 (13)0.4850 (3)0.12594 (15)0.0476 (5)
H12A0.66440.58710.09890.057*
H12B0.74130.46370.10640.057*
C130.72119 (13)0.4951 (3)0.23060 (16)0.0555 (5)
H13A0.76130.58620.25180.067*
H13B0.75460.39880.25760.067*
C140.64422 (12)0.5131 (2)0.26502 (13)0.0426 (4)
H14A0.61610.61680.24540.051*
H14B0.66660.51000.33360.051*
C150.15393 (10)0.50362 (18)0.32210 (10)0.0274 (3)
C160.07583 (11)0.4297 (2)0.26997 (11)0.0357 (4)
H160.07370.36760.21800.043*
C170.00085 (11)0.4459 (2)0.29324 (12)0.0400 (4)
H170.05270.39540.25800.048*
C180.00630 (11)0.5370 (2)0.36879 (12)0.0360 (4)
C190.08251 (12)0.6103 (2)0.42288 (12)0.0367 (4)
H190.08410.67120.47520.044*
C200.15689 (11)0.5932 (2)0.39912 (11)0.0320 (3)
H200.21030.64280.43550.038*
C210.14993 (10)0.3924 (2)0.04907 (11)0.0321 (3)
H210.11140.33820.07830.039*
C220.09234 (11)0.4450 (2)0.04767 (11)0.0408 (4)
H22A0.12940.49110.07950.061*
H22B0.04990.52370.04290.061*
H22C0.06060.35410.08280.061*
C230.22097 (13)0.2779 (2)0.04729 (13)0.0449 (4)
H23A0.19360.18380.01230.067*
H23B0.25650.24820.11080.067*
H23C0.25880.32780.01760.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02457 (19)0.0289 (2)0.02323 (19)0.00035 (14)0.00727 (14)0.00259 (14)
F10.0401 (6)0.0691 (8)0.0599 (7)0.0072 (5)0.0317 (5)0.0005 (6)
O10.0284 (5)0.0351 (6)0.0225 (5)0.0022 (4)0.0092 (4)0.0014 (4)
O20.0306 (6)0.0400 (6)0.0352 (6)0.0087 (5)0.0105 (5)0.0045 (5)
O30.0323 (6)0.0383 (6)0.0308 (6)0.0037 (5)0.0114 (5)0.0073 (5)
C10.0246 (7)0.0265 (7)0.0239 (7)0.0002 (6)0.0083 (5)0.0001 (6)
C20.0259 (7)0.0245 (7)0.0237 (7)0.0011 (5)0.0060 (6)0.0024 (6)
C30.0274 (7)0.0289 (7)0.0245 (7)0.0022 (6)0.0085 (6)0.0026 (6)
C40.0254 (7)0.0289 (7)0.0309 (8)0.0024 (6)0.0085 (6)0.0040 (6)
C50.0262 (7)0.0378 (9)0.0314 (8)0.0009 (6)0.0035 (6)0.0015 (7)
C60.0328 (8)0.0373 (9)0.0246 (7)0.0018 (7)0.0047 (6)0.0008 (6)
C70.0276 (7)0.0278 (7)0.0259 (7)0.0010 (6)0.0099 (6)0.0027 (6)
C80.0276 (7)0.0255 (7)0.0243 (7)0.0002 (6)0.0075 (6)0.0010 (6)
C90.0269 (7)0.0274 (8)0.0387 (8)0.0003 (6)0.0109 (6)0.0009 (7)
C100.0317 (8)0.0627 (12)0.0408 (9)0.0071 (8)0.0168 (7)0.0154 (9)
C110.0415 (10)0.0555 (12)0.0514 (11)0.0043 (9)0.0278 (8)0.0123 (9)
C120.0436 (10)0.0474 (11)0.0614 (12)0.0017 (8)0.0304 (9)0.0042 (10)
C130.0354 (10)0.0700 (14)0.0628 (13)0.0184 (10)0.0193 (9)0.0085 (11)
C140.0360 (9)0.0482 (10)0.0440 (10)0.0148 (8)0.0143 (8)0.0112 (8)
C150.0305 (7)0.0289 (7)0.0246 (7)0.0011 (6)0.0122 (6)0.0019 (6)
C160.0345 (8)0.0464 (10)0.0280 (8)0.0034 (7)0.0132 (7)0.0063 (7)
C170.0307 (8)0.0544 (11)0.0346 (9)0.0046 (8)0.0110 (7)0.0023 (8)
C180.0333 (8)0.0422 (9)0.0387 (9)0.0074 (7)0.0204 (7)0.0064 (7)
C190.0444 (9)0.0350 (9)0.0370 (9)0.0030 (7)0.0223 (7)0.0034 (7)
C200.0343 (8)0.0330 (8)0.0304 (8)0.0023 (7)0.0135 (6)0.0033 (7)
C210.0332 (8)0.0369 (8)0.0255 (7)0.0078 (7)0.0094 (6)0.0034 (7)
C220.0298 (8)0.0606 (12)0.0275 (8)0.0037 (8)0.0044 (6)0.0036 (8)
C230.0535 (11)0.0387 (10)0.0366 (9)0.0040 (8)0.0084 (8)0.0087 (8)
Geometric parameters (Å, º) top
S1—O21.4391 (11)C11—H11B0.9900
S1—O31.4417 (11)C12—C131.515 (3)
S1—C11.7498 (15)C12—H12A0.9900
S1—C211.7910 (16)C12—H12B0.9900
F1—C181.3545 (18)C13—C141.524 (3)
O1—C81.3722 (17)C13—H13A0.9900
O1—C71.3774 (17)C13—H13B0.9900
C1—C81.364 (2)C14—H14A0.9900
C1—C21.452 (2)C14—H14B0.9900
C2—C71.391 (2)C15—C161.390 (2)
C2—C31.398 (2)C15—C201.396 (2)
C3—C41.393 (2)C16—C171.388 (2)
C3—H30.9500C16—H160.9500
C4—C51.408 (2)C17—C181.375 (3)
C4—C91.513 (2)C17—H170.9500
C5—C61.374 (2)C18—C191.375 (3)
C5—H50.9500C19—C201.384 (2)
C6—C71.382 (2)C19—H190.9500
C6—H60.9500C20—H200.9500
C8—C151.471 (2)C21—C231.515 (2)
C9—C101.514 (2)C21—C221.524 (2)
C9—C141.531 (2)C21—H211.0000
C9—H91.0000C22—H22A0.9800
C10—C111.530 (2)C22—H22B0.9800
C10—H10A0.9900C22—H22C0.9800
C10—H10B0.9900C23—H23A0.9800
C11—C121.511 (3)C23—H23B0.9800
C11—H11A0.9900C23—H23C0.9800
O2—S1—O3118.75 (7)C11—C12—H12B109.4
O2—S1—C1108.56 (7)C13—C12—H12B109.4
O3—S1—C1106.75 (7)H12A—C12—H12B108.0
O2—S1—C21107.78 (7)C12—C13—C14111.65 (17)
O3—S1—C21108.32 (7)C12—C13—H13A109.3
C1—S1—C21106.00 (7)C14—C13—H13A109.3
C8—O1—C7106.89 (11)C12—C13—H13B109.3
C8—C1—C2107.39 (13)C14—C13—H13B109.3
C8—C1—S1127.10 (12)H13A—C13—H13B108.0
C2—C1—S1125.27 (11)C13—C14—C9112.12 (16)
C7—C2—C3119.02 (13)C13—C14—H14A109.2
C7—C2—C1104.49 (13)C9—C14—H14A109.2
C3—C2—C1136.49 (14)C13—C14—H14B109.2
C4—C3—C2118.89 (14)C9—C14—H14B109.2
C4—C3—H3120.6H14A—C14—H14B107.9
C2—C3—H3120.6C16—C15—C20119.46 (14)
C3—C4—C5119.52 (14)C16—C15—C8121.58 (14)
C3—C4—C9123.13 (14)C20—C15—C8118.82 (14)
C5—C4—C9117.35 (14)C17—C16—C15120.57 (15)
C6—C5—C4122.60 (14)C17—C16—H16119.7
C6—C5—H5118.7C15—C16—H16119.7
C4—C5—H5118.7C18—C17—C16118.08 (16)
C5—C6—C7116.35 (14)C18—C17—H17121.0
C5—C6—H6121.8C16—C17—H17121.0
C7—C6—H6121.8F1—C18—C17118.50 (16)
O1—C7—C6125.56 (14)F1—C18—C19118.33 (15)
O1—C7—C2110.82 (13)C17—C18—C19123.17 (16)
C6—C7—C2123.60 (14)C18—C19—C20118.24 (15)
C1—C8—O1110.41 (13)C18—C19—H19120.9
C1—C8—C15136.08 (14)C20—C19—H19120.9
O1—C8—C15113.50 (12)C19—C20—C15120.46 (15)
C4—C9—C10114.42 (13)C19—C20—H20119.8
C4—C9—C14111.02 (14)C15—C20—H20119.8
C10—C9—C14109.81 (15)C23—C21—C22112.41 (14)
C4—C9—H9107.1C23—C21—S1111.55 (11)
C10—C9—H9107.1C22—C21—S1108.49 (12)
C14—C9—H9107.1C23—C21—H21108.1
C9—C10—C11111.03 (15)C22—C21—H21108.1
C9—C10—H10A109.4S1—C21—H21108.1
C11—C10—H10A109.4C21—C22—H22A109.5
C9—C10—H10B109.4C21—C22—H22B109.5
C11—C10—H10B109.4H22A—C22—H22B109.5
H10A—C10—H10B108.0C21—C22—H22C109.5
C12—C11—C10111.13 (16)H22A—C22—H22C109.5
C12—C11—H11A109.4H22B—C22—H22C109.5
C10—C11—H11A109.4C21—C23—H23A109.5
C12—C11—H11B109.4C21—C23—H23B109.5
C10—C11—H11B109.4H23A—C23—H23B109.5
H11A—C11—H11B108.0C21—C23—H23C109.5
C11—C12—C13111.19 (16)H23A—C23—H23C109.5
C11—C12—H12A109.4H23B—C23—H23C109.5
C13—C12—H12A109.4
O2—S1—C1—C820.02 (16)C5—C4—C9—C10164.58 (16)
O3—S1—C1—C8149.13 (14)C3—C4—C9—C14109.38 (17)
C21—S1—C1—C895.53 (15)C5—C4—C9—C1470.45 (19)
O2—S1—C1—C2153.56 (13)C4—C9—C10—C11177.68 (15)
O3—S1—C1—C224.45 (15)C14—C9—C10—C1156.7 (2)
C21—S1—C1—C290.89 (14)C9—C10—C11—C1257.9 (2)
C8—C1—C2—C70.18 (17)C10—C11—C12—C1355.8 (2)
S1—C1—C2—C7174.46 (11)C11—C12—C13—C1453.9 (2)
C8—C1—C2—C3179.77 (17)C12—C13—C14—C954.0 (2)
S1—C1—C2—C35.6 (3)C4—C9—C14—C13177.30 (16)
C7—C2—C3—C41.7 (2)C10—C9—C14—C1355.2 (2)
C1—C2—C3—C4178.29 (16)C1—C8—C15—C1653.2 (3)
C2—C3—C4—C51.1 (2)O1—C8—C15—C16128.01 (16)
C2—C3—C4—C9179.09 (14)C1—C8—C15—C20131.11 (19)
C3—C4—C5—C60.1 (3)O1—C8—C15—C2047.7 (2)
C9—C4—C5—C6179.98 (15)C20—C15—C16—C170.8 (3)
C4—C5—C6—C70.2 (3)C8—C15—C16—C17176.42 (16)
C8—O1—C7—C6178.35 (15)C15—C16—C17—C180.2 (3)
C8—O1—C7—C20.27 (17)C16—C17—C18—F1179.46 (16)
C5—C6—C7—O1178.87 (15)C16—C17—C18—C191.1 (3)
C5—C6—C7—C20.4 (2)F1—C18—C19—C20179.56 (15)
C3—C2—C7—O1179.99 (13)C17—C18—C19—C201.0 (3)
C1—C2—C7—O10.06 (17)C18—C19—C20—C150.0 (3)
C3—C2—C7—C61.4 (2)C16—C15—C20—C190.9 (2)
C1—C2—C7—C6178.59 (15)C8—C15—C20—C19176.63 (15)
C2—C1—C8—O10.36 (17)O2—S1—C21—C23172.18 (12)
S1—C1—C8—O1174.15 (11)O3—S1—C21—C2358.15 (14)
C2—C1—C8—C15179.15 (17)C1—S1—C21—C2356.11 (14)
S1—C1—C8—C154.6 (3)O2—S1—C21—C2263.47 (12)
C7—O1—C8—C10.39 (17)O3—S1—C21—C2266.20 (12)
C7—O1—C8—C15179.48 (12)C1—S1—C21—C22179.55 (11)
C3—C4—C9—C1015.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C14—H14A···Cgi0.992.683.667 (2)172
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H25FO3S
Mr400.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)16.2065 (3), 8.4993 (2), 15.4031 (3)
β (°) 110.411 (1)
V3)1988.47 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.35 × 0.25 × 0.16
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.935, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
34421, 4536, 3857
Rint0.040
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.118, 1.05
No. of reflections4536
No. of parameters255
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXL97.

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C14—H14A···Cgi0.992.683.667 (2)172
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS Google Scholar
First citationAslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res., 164, 191–195.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGalal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428.  Web of Science CrossRef PubMed CAS Google Scholar
First citationKhan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSoekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834.  Web of Science CrossRef PubMed CAS 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds