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ISSN: 2056-9890

5-Cyclo­hexyl-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-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 17 February 2011; accepted 21 February 2011; online 2 March 2011)

In the title compound, C21H21FO3S, the cyclo­hexyl ring adopts a chair conformation. The 4-fluoro­phenyl ring makes a dihedral angle of 77.71 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked through inter­molecular C—H⋯O hydrogen bonds and aromatic ππ inter­actions between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.578 (2) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); 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 our previous structural studies of related 3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzo­furan derivatives, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o1813.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2575.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21FO3S

  • Mr = 372.44

  • Triclinic, [P \overline 1]

  • a = 9.2014 (3) Å

  • b = 10.2563 (4) Å

  • c = 11.1105 (4) Å

  • α = 80.564 (2)°

  • β = 66.317 (2)°

  • γ = 71.825 (2)°

  • V = 911.41 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 173 K

  • 0.33 × 0.23 × 0.17 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 = 0.640, Tmax = 0.746

  • 15715 measured reflections

  • 3967 independent reflections

  • 3395 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.106

  • S = 1.03

  • 3967 reflections

  • 236 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯O3i 0.93 2.59 3.2970 (19) 133
C20—H20⋯O1ii 0.93 2.60 3.285 (2) 131
C21—H21⋯O2iii 0.93 2.42 3.3114 (19) 160
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

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 involving a benzofuran ring have attracted much attention owing to their interesting pharmacological properties such as antifungal, antimicrobial, antitumor and antiviral activities (Aslam et al., 2006; 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 program of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair conformation. The 4-fluorophenyl ring makes a dihedral angle of 77.71 (4)° with the mean plane of the benzofuran ring. The crystal packing (Fig. 2, Table 1) is stabilised by intermolecular C—H···O hydrogen bonds; the first one between a 4-fluorophenyl H atom and the oxygen of the OSO unit (Table 1; C17—H17···O3i), the second one between a 4-fluorophenyl H atom and the furan O atom (Table 1; C20—H20···O1i), the third one between a 4-fluorophenyl H atom and the oxygen of the OSO unit (Table 1; C21–H21···O2iii). The crystal packing (Fig. 3) is also stabilised by an aromatic ππ interaction between the furan rings of adjacent molecules, with a Cg···Cgidistance of 3.578 (2) Å (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For our previous structural studies of related 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b).

Experimental top

3-Chloroperoxybenzoic acid, 77% (426 mg, 1.9 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6 h, 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 colourless solid [yield 73%, m.p. 426–427 K; Rf = 0.68 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation 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 = 0.93 Å for aryl, 0.98 Å for methine, 0.97 Å for methylene and 0.96 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 (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 a small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C–H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x, - y + 1, - z + 1; (ii) x + 1, y, z; (iii) - x+ 1, - y + 1, - z + 1; (iv) x - 1, y, z.]
[Figure 3] Fig. 3. A view of the ππ interactions (dotted lines) in the crystal structure of the title compound. [Symmetry code: (i) - x, - y + 1, - z + 1.]
5-Cyclohexyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran top
Crystal data top
C21H21FO3SZ = 2
Mr = 372.44F(000) = 392
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2014 (3) ÅCell parameters from 6718 reflections
b = 10.2563 (4) Åθ = 2.5–27.5°
c = 11.1105 (4) ŵ = 0.21 mm1
α = 80.564 (2)°T = 173 K
β = 66.317 (2)°Block, colourless
γ = 71.825 (2)°0.33 × 0.23 × 0.17 mm
V = 911.41 (6) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3967 independent reflections
Radiation source: rotating anode3395 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.034
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.0°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1213
Tmin = 0.640, Tmax = 0.746l = 1414
15715 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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.106H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.3006P]
where P = (Fo2 + 2Fc2)/3
3967 reflections(Δ/σ)max = 0.001
236 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C21H21FO3Sγ = 71.825 (2)°
Mr = 372.44V = 911.41 (6) Å3
Triclinic, P1Z = 2
a = 9.2014 (3) ÅMo Kα radiation
b = 10.2563 (4) ŵ = 0.21 mm1
c = 11.1105 (4) ÅT = 173 K
α = 80.564 (2)°0.33 × 0.23 × 0.17 mm
β = 66.317 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3967 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3395 reflections with I > 2σ(I)
Tmin = 0.640, Tmax = 0.746Rint = 0.034
15715 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å3
3967 reflectionsΔρmin = 0.39 e Å3
236 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
S10.17745 (5)0.50397 (4)0.70139 (3)0.03247 (12)
F10.60299 (14)0.09412 (12)0.93389 (12)0.0614 (3)
O10.07799 (13)0.32075 (11)0.61095 (11)0.0385 (3)
O20.28066 (15)0.57220 (12)0.59295 (11)0.0417 (3)
O30.04350 (14)0.58296 (11)0.80566 (11)0.0418 (3)
C10.09922 (18)0.40980 (15)0.63832 (14)0.0309 (3)
C20.19131 (19)0.32218 (15)0.52695 (14)0.0313 (3)
C30.35461 (19)0.28136 (15)0.44039 (14)0.0330 (3)
H30.43400.31580.44580.040*
C40.3973 (2)0.18808 (16)0.34550 (14)0.0358 (3)
C50.2739 (2)0.14063 (17)0.33786 (16)0.0414 (4)
H50.30330.07960.27340.050*
C60.1113 (2)0.18053 (18)0.42166 (17)0.0425 (4)
H60.03070.14850.41520.051*
C70.0751 (2)0.27039 (16)0.51537 (15)0.0351 (3)
C80.06007 (19)0.40433 (15)0.68512 (15)0.0345 (3)
C90.2136 (2)0.46764 (19)0.79404 (17)0.0441 (4)
H9A0.19050.52420.84110.066*
H9B0.25580.39680.85280.066*
H9C0.29410.52290.75880.066*
C100.5742 (2)0.13649 (16)0.25294 (15)0.0388 (4)
H100.57520.07870.19050.047*
C110.6477 (2)0.25270 (16)0.17308 (15)0.0379 (4)
H11A0.58230.30440.12210.046*
H11B0.64280.31460.23270.046*
C120.8261 (2)0.19855 (17)0.08055 (16)0.0410 (4)
H12A0.82950.14670.01350.049*
H12B0.87070.27540.03710.049*
C130.9320 (2)0.10759 (18)0.15317 (18)0.0467 (4)
H13A0.94080.16240.21200.056*
H13B1.04200.06930.09030.056*
C140.8602 (2)0.00825 (19)0.23200 (19)0.0583 (6)
H14A0.92680.06080.28180.070*
H14B0.86330.06930.17240.070*
C150.6827 (3)0.0469 (2)0.32611 (18)0.0578 (6)
H15A0.68100.10060.39110.069*
H15B0.63850.02950.37200.069*
C160.30614 (19)0.38018 (15)0.77139 (14)0.0317 (3)
C170.2384 (2)0.33178 (17)0.90047 (15)0.0383 (4)
H170.12610.36430.94900.046*
C180.3384 (2)0.23538 (19)0.95594 (17)0.0451 (4)
H180.29560.20231.04230.054*
C190.5031 (2)0.18935 (18)0.88040 (18)0.0418 (4)
C200.5731 (2)0.23555 (18)0.75333 (18)0.0425 (4)
H200.68530.20180.70540.051*
C210.47341 (19)0.33341 (17)0.69787 (16)0.0380 (4)
H210.51790.36760.61210.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0357 (2)0.0309 (2)0.0242 (2)0.00993 (15)0.00282 (15)0.00406 (14)
F10.0580 (7)0.0651 (7)0.0675 (8)0.0096 (6)0.0381 (6)0.0045 (6)
O10.0357 (6)0.0430 (6)0.0352 (6)0.0116 (5)0.0113 (5)0.0005 (5)
O20.0492 (7)0.0392 (6)0.0311 (6)0.0191 (5)0.0055 (5)0.0024 (5)
O30.0423 (7)0.0381 (6)0.0338 (6)0.0055 (5)0.0030 (5)0.0123 (5)
C10.0320 (7)0.0300 (7)0.0244 (7)0.0058 (6)0.0061 (6)0.0017 (6)
C20.0383 (8)0.0287 (7)0.0234 (7)0.0077 (6)0.0100 (6)0.0011 (6)
C30.0385 (8)0.0319 (7)0.0246 (7)0.0094 (6)0.0076 (6)0.0024 (6)
C40.0465 (9)0.0311 (7)0.0239 (7)0.0096 (7)0.0082 (6)0.0008 (6)
C50.0599 (11)0.0370 (8)0.0280 (8)0.0156 (8)0.0140 (7)0.0041 (7)
C60.0528 (10)0.0434 (9)0.0378 (9)0.0184 (8)0.0193 (8)0.0024 (7)
C70.0389 (8)0.0353 (8)0.0293 (8)0.0097 (6)0.0125 (6)0.0020 (6)
C80.0371 (8)0.0316 (7)0.0293 (8)0.0065 (6)0.0103 (6)0.0018 (6)
C90.0323 (8)0.0485 (10)0.0398 (9)0.0063 (7)0.0046 (7)0.0040 (7)
C100.0493 (9)0.0333 (8)0.0253 (7)0.0097 (7)0.0042 (7)0.0074 (6)
C110.0438 (9)0.0334 (8)0.0310 (8)0.0074 (7)0.0116 (7)0.0008 (6)
C120.0445 (9)0.0400 (9)0.0321 (8)0.0111 (7)0.0086 (7)0.0006 (7)
C130.0452 (10)0.0423 (9)0.0433 (10)0.0000 (8)0.0129 (8)0.0103 (8)
C140.0573 (12)0.0407 (10)0.0444 (11)0.0086 (8)0.0046 (9)0.0026 (8)
C150.0613 (12)0.0428 (10)0.0350 (9)0.0066 (9)0.0022 (8)0.0068 (8)
C160.0339 (8)0.0348 (8)0.0248 (7)0.0130 (6)0.0051 (6)0.0051 (6)
C170.0347 (8)0.0483 (9)0.0248 (7)0.0129 (7)0.0022 (6)0.0037 (7)
C180.0496 (10)0.0547 (10)0.0290 (8)0.0177 (8)0.0120 (7)0.0031 (7)
C190.0451 (9)0.0420 (9)0.0468 (10)0.0128 (7)0.0247 (8)0.0027 (7)
C200.0301 (8)0.0481 (10)0.0458 (10)0.0118 (7)0.0071 (7)0.0090 (8)
C210.0351 (8)0.0440 (9)0.0293 (8)0.0160 (7)0.0014 (6)0.0041 (7)
Geometric parameters (Å, º) top
S1—O31.4336 (11)C10—H100.9800
S1—O21.4360 (11)C11—C121.524 (2)
S1—C11.7329 (16)C11—H11A0.9700
S1—C161.7599 (16)C11—H11B0.9700
F1—C191.3567 (19)C12—C131.512 (2)
O1—C81.3675 (19)C12—H12A0.9700
O1—C71.3793 (19)C12—H12B0.9700
C1—C81.361 (2)C13—C141.516 (3)
C1—C21.451 (2)C13—H13A0.9700
C2—C71.389 (2)C13—H13B0.9700
C2—C31.392 (2)C14—C151.525 (2)
C3—C41.395 (2)C14—H14A0.9700
C3—H30.9300C14—H14B0.9700
C4—C51.403 (2)C15—H15A0.9700
C4—C101.511 (2)C15—H15B0.9700
C5—C61.378 (2)C16—C211.387 (2)
C5—H50.9300C16—C171.390 (2)
C6—C71.374 (2)C17—C181.376 (2)
C6—H60.9300C17—H170.9300
C8—C91.481 (2)C18—C191.373 (2)
C9—H9A0.9600C18—H180.9300
C9—H9B0.9600C19—C201.369 (2)
C9—H9C0.9600C20—C211.381 (2)
C10—C151.529 (3)C20—H200.9300
C10—C111.530 (2)C21—H210.9300
O3—S1—O2119.61 (7)C12—C11—H11B109.2
O3—S1—C1108.35 (7)C10—C11—H11B109.2
O2—S1—C1107.95 (7)H11A—C11—H11B107.9
O3—S1—C16107.80 (7)C13—C12—C11111.76 (13)
O2—S1—C16107.38 (7)C13—C12—H12A109.3
C1—S1—C16104.78 (7)C11—C12—H12A109.3
C8—O1—C7107.23 (12)C13—C12—H12B109.3
C8—C1—C2107.66 (14)C11—C12—H12B109.3
C8—C1—S1125.98 (12)H12A—C12—H12B107.9
C2—C1—S1126.35 (12)C12—C13—C14111.51 (16)
C7—C2—C3119.17 (14)C12—C13—H13A109.3
C7—C2—C1104.49 (13)C14—C13—H13A109.3
C3—C2—C1136.33 (15)C12—C13—H13B109.3
C2—C3—C4118.99 (15)C14—C13—H13B109.3
C2—C3—H3120.5H13A—C13—H13B108.0
C4—C3—H3120.5C13—C14—C15111.21 (15)
C3—C4—C5119.14 (15)C13—C14—H14A109.4
C3—C4—C10120.85 (15)C15—C14—H14A109.4
C5—C4—C10120.00 (14)C13—C14—H14B109.4
C6—C5—C4122.90 (15)C15—C14—H14B109.4
C6—C5—H5118.5H14A—C14—H14B108.0
C4—C5—H5118.5C14—C15—C10111.44 (14)
C7—C6—C5116.07 (16)C14—C15—H15A109.3
C7—C6—H6122.0C10—C15—H15A109.3
C5—C6—H6122.0C14—C15—H15B109.3
C6—C7—O1125.83 (15)C10—C15—H15B109.3
C6—C7—C2123.71 (15)H15A—C15—H15B108.0
O1—C7—C2110.46 (13)C21—C16—C17121.00 (15)
C1—C8—O1110.16 (13)C21—C16—S1119.73 (12)
C1—C8—C9135.13 (15)C17—C16—S1119.26 (12)
O1—C8—C9114.70 (14)C18—C17—C16119.55 (15)
C8—C9—H9A109.5C18—C17—H17120.2
C8—C9—H9B109.5C16—C17—H17120.2
H9A—C9—H9B109.5C19—C18—C17118.27 (15)
C8—C9—H9C109.5C19—C18—H18120.9
H9A—C9—H9C109.5C17—C18—H18120.9
H9B—C9—H9C109.5F1—C19—C20117.78 (16)
C4—C10—C15111.52 (13)F1—C19—C18118.83 (16)
C4—C10—C11112.73 (13)C20—C19—C18123.39 (16)
C15—C10—C11110.17 (15)C19—C20—C21118.49 (15)
C4—C10—H10107.4C19—C20—H20120.8
C15—C10—H10107.4C21—C20—H20120.8
C11—C10—H10107.4C20—C21—C16119.29 (15)
C12—C11—C10111.90 (13)C20—C21—H21120.4
C12—C11—H11A109.2C16—C21—H21120.4
C10—C11—H11A109.2
O3—S1—C1—C84.02 (16)C7—O1—C8—C9179.75 (13)
O2—S1—C1—C8134.92 (14)C3—C4—C10—C1567.17 (19)
C16—S1—C1—C8110.87 (14)C5—C4—C10—C15111.92 (18)
O3—S1—C1—C2176.35 (12)C3—C4—C10—C1157.37 (19)
O2—S1—C1—C245.45 (15)C5—C4—C10—C11123.54 (16)
C16—S1—C1—C268.77 (14)C4—C10—C11—C12179.92 (14)
C8—C1—C2—C70.40 (16)C15—C10—C11—C1254.64 (18)
S1—C1—C2—C7179.91 (11)C10—C11—C12—C1354.48 (19)
C8—C1—C2—C3178.10 (16)C11—C12—C13—C1454.41 (19)
S1—C1—C2—C31.6 (3)C12—C13—C14—C1555.3 (2)
C7—C2—C3—C40.8 (2)C13—C14—C15—C1056.3 (2)
C1—C2—C3—C4177.49 (15)C4—C10—C15—C14178.45 (16)
C2—C3—C4—C51.5 (2)C11—C10—C15—C1455.6 (2)
C2—C3—C4—C10177.55 (13)O3—S1—C16—C21150.86 (13)
C3—C4—C5—C61.0 (2)O2—S1—C16—C2120.74 (15)
C10—C4—C5—C6178.11 (15)C1—S1—C16—C2193.88 (13)
C4—C5—C6—C70.3 (2)O3—S1—C16—C1728.49 (15)
C5—C6—C7—O1178.25 (14)O2—S1—C16—C17158.60 (13)
C5—C6—C7—C21.0 (2)C1—S1—C16—C1786.78 (14)
C8—O1—C7—C6178.84 (15)C21—C16—C17—C180.4 (2)
C8—O1—C7—C20.53 (16)S1—C16—C17—C18179.76 (13)
C3—C2—C7—C60.5 (2)C16—C17—C18—C190.5 (3)
C1—C2—C7—C6179.30 (15)C17—C18—C19—F1179.88 (15)
C3—C2—C7—O1178.90 (12)C17—C18—C19—C200.8 (3)
C1—C2—C7—O10.08 (16)F1—C19—C20—C21179.41 (14)
C2—C1—C8—O10.74 (17)C18—C19—C20—C210.0 (3)
S1—C1—C8—O1179.56 (10)C19—C20—C21—C160.9 (2)
C2—C1—C8—C9179.96 (16)C17—C16—C21—C201.1 (2)
S1—C1—C8—C90.3 (3)S1—C16—C21—C20179.53 (12)
C7—O1—C8—C10.79 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O3i0.932.593.2970 (19)133
C20—H20···O1ii0.932.603.285 (2)131
C21—H21···O2iii0.932.423.3114 (19)160
Symmetry codes: (i) x, y+1, z+2; (ii) x+1, y, z; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC21H21FO3S
Mr372.44
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.2014 (3), 10.2563 (4), 11.1105 (4)
α, β, γ (°)80.564 (2), 66.317 (2), 71.825 (2)
V3)911.41 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.33 × 0.23 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.640, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
15715, 3967, 3395
Rint0.034
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.106, 1.03
No. of reflections3967
No. of parameters236
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.39

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O3i0.932.593.2970 (19)133
C20—H20···O1ii0.932.603.285 (2)131
C21—H21···O2iii0.932.423.3114 (19)160
Symmetry codes: (i) x, y+1, z+2; (ii) x+1, y, z; (iii) x+1, y+1, z+1.
 

References

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