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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-Cyclo­pentyl­sulfonyl-5-fluoro-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 30 May 2011; accepted 2 June 2011; online 18 June 2011)

There are two independent mol­ecules, A and B, in the asymmetric unit of the title compound, C14H15FO3S, in each of which the cyclo­pentyl ring adopts an envelope conformation. The benzofuran units in each mol­ecule are essentially planar, with mean deviations from the least-squares plane defined by the nine constituent ring atoms of 0.009 (2) Å for mol­ecule A and 0.013 (2) Å for mol­ecule B. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds. In the cyclo­pentyl ring of mol­ecule B, one C atom is disordered over two positions with site-occupancy factors of 0.60 (2) and 0.40 (2).

Related literature

For the pharmacological 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 a structural study of the related compound 5-bromo-3-cyclo­pentyl­sulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1386.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15FO3S

  • Mr = 282.32

  • Triclinic, [P \overline 1]

  • a = 10.0568 (8) Å

  • b = 10.2697 (8) Å

  • c = 13.2894 (10) Å

  • α = 95.033 (4)°

  • β = 109.140 (4)°

  • γ = 91.229 (4)°

  • V = 1289.82 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 173 K

  • 0.26 × 0.24 × 0.20 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 = 0.936, Tmax = 0.948

  • 21777 measured reflections

  • 5565 independent reflections

  • 4022 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.119

  • S = 1.03

  • 5565 reflections

  • 361 parameters

  • 20 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9C⋯O6i 0.98 2.45 3.348 (3) 152
C19—H19⋯O6ii 0.95 2.58 3.469 (3) 157
C23—H23A⋯O2iii 0.98 2.50 3.318 (3) 141
Symmetry codes: (i) x-1, y-1, z; (ii) x-1, y, z; (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 (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 moiety have attracted much attention due to their valuable biological properties such as antifungal, antimicrobial, antitumor and antiviral activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 3-cyclopentylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Seo et al., 2011), we report herein on the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. There are two independent unique molecules [labelled A & B] in which the benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å for A and 0.013 (2) Å for B, respectively, from the least-squares plane defined by the nine constituent atoms. The cyclopentyl rings of both molecules are in an envelope form. In the cyclopentyl ring of molecule B, C27 atom is disordered over two positions with site-occupancy factors, from refinement of 0.60 (2) (part 1) and 0.40 (8) (part 2). In the crystal packing (Fig. 2), molecules are linked by weak non-classical intermolecular C–H···O hydrogen bonds; the first one between a methyl H atom and the O atom of the sulfonyl group (Table 1; C9–H9C···O6i), the second one between a benzene H atom and the O atom of the sulfonyl group (Table 1; C19–H19···O6ii), and the third one between a methyl H atom and the O atom of the sulfonyl group (Table 1; C23–H23A···O2iii).

Related literature top

For the pharmacological 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 a structural study of the related compound, 5-bromo-3-cyclopentylsulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011).

Experimental top

3-chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-cyclopentylsulfanyl-5-fluoro-2-methyl-1-benzofuran (325 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 71%, m.p. 394-395 K; Rf = 0.49 (hexane-ethyl acetate, 4:1 v/v)]. 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, methylene, and 1.5Ueq(C) for methyl H atoms. The C27 atom of the cyclopentyl ring is disordered over two positions with site-ccupancy factors, from refinement of 0.60 (2) (part A) and 0.40 (2) (part B). The C–C distance sets were restrained to be with 0.003 Å using command DFIX and SADI, and thermal ellipsoid parameters of C27A and C27B set were restrained to 0.01 using commend ISOR.

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 interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1, y - 1, z; (ii) x - 1, y, z; (iii) x + 1, y, z; (iv) x + 1, y + 1, z.]
3-Cyclopentylsulfonyl-5-fluoro-2-methyl-1-benzofuran top
Crystal data top
C14H15FO3SZ = 4
Mr = 282.32F(000) = 592
Triclinic, P1Dx = 1.454 Mg m3
Hall symbol: -P 1Melting point = 394–395 K
a = 10.0568 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2697 (8) ÅCell parameters from 6383 reflections
c = 13.2894 (10) Åθ = 2.2–28.1°
α = 95.033 (4)°µ = 0.26 mm1
β = 109.140 (4)°T = 173 K
γ = 91.229 (4)°Block, colourless
V = 1289.82 (17) Å30.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
5565 independent reflections
Radiation source: rotating anode4022 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.042
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.6°
ϕ and ω scansh = 1211
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1313
Tmin = 0.936, Tmax = 0.948l = 1616
21777 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)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0514P)2 + 0.6137P]
where P = (Fo2 + 2Fc2)/3
5565 reflections(Δ/σ)max = 0.001
361 parametersΔρmax = 0.50 e Å3
20 restraintsΔρmin = 0.31 e Å3
Crystal data top
C14H15FO3Sγ = 91.229 (4)°
Mr = 282.32V = 1289.82 (17) Å3
Triclinic, P1Z = 4
a = 10.0568 (8) ÅMo Kα radiation
b = 10.2697 (8) ŵ = 0.26 mm1
c = 13.2894 (10) ÅT = 173 K
α = 95.033 (4)°0.26 × 0.24 × 0.20 mm
β = 109.140 (4)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
5565 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4022 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.948Rint = 0.042
21777 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04520 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.50 e Å3
5565 reflectionsΔρmin = 0.31 e Å3
361 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*/UeqOcc. (<1)
S10.23453 (6)0.33785 (5)0.23641 (4)0.03150 (15)
F10.81952 (14)0.46170 (14)0.28853 (11)0.0484 (4)
O10.40319 (15)0.10269 (14)0.07061 (11)0.0326 (4)
O20.09116 (17)0.32983 (18)0.16639 (13)0.0460 (4)
C10.3369 (2)0.2567 (2)0.17088 (16)0.0269 (4)
C20.4835 (2)0.28575 (19)0.18530 (15)0.0252 (4)
O30.30185 (18)0.46418 (15)0.27859 (14)0.0438 (4)
C30.5859 (2)0.3822 (2)0.24350 (16)0.0296 (5)
H30.56640.45240.28720.036*
C40.7165 (2)0.3693 (2)0.23369 (17)0.0311 (5)
C50.7522 (2)0.2698 (2)0.17204 (18)0.0344 (5)
H50.84560.26660.16990.041*
C60.6504 (2)0.1750 (2)0.11357 (17)0.0333 (5)
H60.67040.10510.06990.040*
C70.5185 (2)0.1872 (2)0.12172 (16)0.0280 (5)
C80.2955 (2)0.1465 (2)0.10210 (16)0.0305 (5)
C90.1621 (2)0.0657 (2)0.05858 (19)0.0411 (6)
H9A0.14350.03920.01770.062*
H9B0.08470.11660.06750.062*
H9C0.16970.01250.09710.062*
C100.2422 (2)0.2431 (2)0.34337 (17)0.0310 (5)
H100.20790.15100.31400.037*
C110.3910 (3)0.2436 (2)0.42411 (18)0.0396 (6)
H11A0.41330.15480.44600.048*
H11B0.46170.27480.39330.048*
C120.3888 (3)0.3373 (3)0.5190 (2)0.0514 (7)
H12A0.46120.31710.58600.062*
H12B0.40470.42930.50700.062*
C130.2438 (3)0.3130 (3)0.5228 (2)0.0510 (7)
H13A0.21740.38680.56430.061*
H13B0.23740.23150.55600.061*
C140.1491 (3)0.3006 (2)0.40645 (19)0.0405 (6)
H14A0.11710.38720.38390.049*
H14B0.06540.24140.39540.049*
S20.97507 (6)0.86902 (6)0.24244 (5)0.03691 (16)
F20.43771 (16)0.96231 (15)0.28861 (13)0.0589 (4)
O40.67248 (16)0.60770 (14)0.08407 (12)0.0359 (4)
O50.93729 (18)1.00229 (16)0.24654 (16)0.0536 (5)
O61.07814 (18)0.83460 (19)0.19339 (15)0.0534 (5)
C150.8217 (2)0.7728 (2)0.17896 (17)0.0308 (5)
C160.6865 (2)0.7948 (2)0.19121 (16)0.0290 (5)
C170.6327 (2)0.8908 (2)0.24526 (17)0.0332 (5)
H170.68840.96570.28530.040*
C180.4942 (3)0.8703 (2)0.23702 (19)0.0399 (6)
C190.4080 (3)0.7648 (2)0.1794 (2)0.0424 (6)
H190.31290.75660.17760.051*
C200.4606 (2)0.6713 (2)0.12428 (19)0.0387 (5)
H200.40390.59760.08300.046*
C210.5994 (2)0.6900 (2)0.13206 (17)0.0312 (5)
C220.8073 (2)0.6592 (2)0.11486 (17)0.0334 (5)
C230.9032 (3)0.5815 (3)0.0738 (2)0.0456 (6)
H23A0.91240.49620.10260.068*
H23B0.99600.62790.09610.068*
H23C0.86500.56860.00450.068*
C241.0323 (2)0.8246 (2)0.37518 (18)0.0367 (5)
H240.95270.83290.40440.044*
C251.1571 (3)0.9139 (3)0.4469 (2)0.0526 (7)
H25A1.21830.94080.40640.063*
H25B1.12460.99320.47790.063*
C261.2325 (3)0.8310 (2)0.5315 (2)0.0665 (9)
H26A1.18040.81850.58190.080*0.60 (2)
H26B1.32930.86720.57190.080*0.60 (2)
H26C1.19870.84600.59340.080*0.40 (2)
H26D1.33490.85420.55620.080*0.40 (2)
C27A1.2327 (6)0.7051 (8)0.4620 (8)0.060 (3)0.60 (2)
H27A1.30060.71390.42300.072*0.60 (2)
H27B1.25740.63060.50580.072*0.60 (2)
C27B1.1998 (14)0.6866 (3)0.4914 (7)0.050 (3)0.40 (2)
H27C1.28370.64530.48240.060*0.40 (2)
H27D1.16790.63920.54190.060*0.40 (2)
C281.0829 (3)0.6861 (2)0.3846 (2)0.0429 (6)
H28A1.02370.63180.41320.051*0.60 (2)
H28B1.08100.64390.31420.051*0.60 (2)
H28C1.012 (7)0.612 (7)0.354 (5)0.051*0.40 (2)
H28D1.134 (8)0.675 (7)0.343 (5)0.051*0.40 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0255 (3)0.0333 (3)0.0406 (3)0.0073 (2)0.0156 (2)0.0095 (2)
F10.0306 (8)0.0513 (8)0.0585 (9)0.0166 (6)0.0147 (7)0.0158 (7)
O10.0280 (8)0.0345 (8)0.0335 (8)0.0066 (6)0.0106 (7)0.0059 (6)
O20.0253 (9)0.0664 (12)0.0505 (10)0.0139 (8)0.0136 (8)0.0204 (9)
C10.0210 (10)0.0323 (11)0.0289 (11)0.0036 (8)0.0093 (8)0.0064 (9)
C20.0241 (11)0.0269 (10)0.0266 (10)0.0031 (8)0.0103 (8)0.0048 (8)
O30.0478 (10)0.0284 (8)0.0672 (11)0.0050 (7)0.0350 (9)0.0058 (8)
C30.0292 (12)0.0291 (11)0.0305 (11)0.0005 (9)0.0112 (9)0.0016 (9)
C40.0240 (11)0.0318 (11)0.0347 (11)0.0067 (9)0.0073 (9)0.0002 (9)
C50.0247 (11)0.0387 (12)0.0418 (13)0.0011 (9)0.0139 (10)0.0036 (10)
C60.0328 (12)0.0321 (11)0.0370 (12)0.0025 (9)0.0160 (10)0.0029 (9)
C70.0267 (11)0.0287 (11)0.0272 (10)0.0035 (9)0.0079 (9)0.0003 (8)
C80.0237 (11)0.0380 (12)0.0295 (11)0.0011 (9)0.0079 (9)0.0050 (9)
C90.0302 (13)0.0490 (14)0.0402 (13)0.0123 (11)0.0086 (10)0.0014 (11)
C100.0313 (12)0.0297 (11)0.0353 (11)0.0024 (9)0.0153 (9)0.0035 (9)
C110.0370 (13)0.0476 (14)0.0365 (12)0.0095 (11)0.0137 (10)0.0082 (10)
C120.0499 (16)0.0596 (17)0.0428 (14)0.0057 (13)0.0161 (12)0.0057 (12)
C130.0549 (17)0.0577 (17)0.0448 (15)0.0044 (13)0.0266 (13)0.0091 (12)
C140.0375 (14)0.0428 (13)0.0483 (14)0.0030 (11)0.0240 (11)0.0039 (11)
S20.0264 (3)0.0356 (3)0.0497 (4)0.0012 (2)0.0113 (3)0.0147 (3)
F20.0464 (9)0.0605 (10)0.0742 (11)0.0162 (8)0.0294 (8)0.0092 (8)
O40.0350 (9)0.0342 (8)0.0360 (8)0.0045 (7)0.0096 (7)0.0021 (7)
O50.0420 (10)0.0311 (9)0.0794 (13)0.0014 (8)0.0065 (9)0.0158 (9)
O60.0326 (10)0.0718 (13)0.0651 (12)0.0029 (9)0.0248 (9)0.0214 (10)
C150.0278 (12)0.0328 (11)0.0347 (11)0.0066 (9)0.0120 (9)0.0098 (9)
C160.0262 (11)0.0308 (11)0.0301 (11)0.0035 (9)0.0081 (9)0.0080 (9)
C170.0300 (12)0.0311 (11)0.0375 (12)0.0031 (9)0.0099 (10)0.0024 (9)
C180.0388 (14)0.0397 (13)0.0444 (14)0.0123 (11)0.0176 (11)0.0041 (11)
C190.0253 (12)0.0509 (15)0.0521 (15)0.0053 (11)0.0129 (11)0.0109 (12)
C200.0291 (12)0.0377 (13)0.0443 (13)0.0010 (10)0.0059 (10)0.0023 (10)
C210.0307 (12)0.0299 (11)0.0325 (11)0.0059 (9)0.0095 (9)0.0034 (9)
C220.0327 (12)0.0372 (12)0.0340 (12)0.0086 (10)0.0139 (10)0.0102 (9)
C230.0499 (16)0.0497 (15)0.0450 (14)0.0195 (12)0.0246 (12)0.0076 (11)
C240.0318 (12)0.0339 (12)0.0417 (13)0.0020 (10)0.0091 (10)0.0031 (10)
C250.0480 (16)0.0382 (14)0.0609 (17)0.0087 (12)0.0060 (13)0.0013 (12)
C260.0509 (18)0.0546 (18)0.069 (2)0.0086 (14)0.0089 (15)0.0162 (15)
C27A0.046 (3)0.050 (3)0.058 (4)0.016 (3)0.013 (3)0.009 (3)
C27B0.059 (6)0.040 (4)0.042 (4)0.011 (4)0.005 (4)0.000 (3)
C280.0407 (15)0.0318 (13)0.0478 (15)0.0022 (11)0.0034 (12)0.0050 (11)
Geometric parameters (Å, º) top
S1—O31.4289 (17)F2—C181.360 (3)
S1—O21.4329 (17)O4—C221.362 (3)
S1—C11.735 (2)O4—C211.379 (3)
S1—C101.774 (2)C15—C221.358 (3)
F1—C41.359 (2)C15—C161.442 (3)
O1—C81.355 (3)C16—C211.380 (3)
O1—C71.377 (2)C16—C171.390 (3)
C1—C81.356 (3)C17—C181.372 (3)
C1—C21.444 (3)C17—H170.9500
C2—C71.387 (3)C18—C191.375 (3)
C2—C31.392 (3)C19—C201.375 (3)
C3—C41.370 (3)C19—H190.9500
C3—H30.9500C20—C211.374 (3)
C4—C51.381 (3)C20—H200.9500
C5—C61.379 (3)C22—C231.471 (3)
C5—H50.9500C23—H23A0.9800
C6—C71.373 (3)C23—H23B0.9800
C6—H60.9500C23—H23C0.9800
C8—C91.478 (3)C24—C281.523 (3)
C9—H9A0.9800C24—C251.529 (3)
C9—H9B0.9800C24—H241.0000
C9—H9C0.9800C25—C261.484 (4)
C10—C111.528 (3)C25—H25A0.9900
C10—C141.543 (3)C25—H25B0.9900
C10—H101.0000C26—C27B1.522 (2)
C11—C121.524 (3)C26—C27A1.522 (2)
C11—H11A0.9900C26—H26A0.9900
C11—H11B0.9900C26—H26B0.9900
C12—C131.492 (4)C26—H26C0.9900
C12—H12A0.9900C26—H26D0.9900
C12—H12B0.9900C27A—C281.5166 (18)
C13—C141.520 (3)C27A—H27A0.9900
C13—H13A0.9900C27A—H27B0.9900
C13—H13B0.9900C27B—C281.5171 (18)
C14—H14A0.9900C27B—H27C0.9900
C14—H14B0.9900C27B—H27D0.9900
S2—O61.4292 (19)C28—H28A0.9900
S2—O51.4294 (18)C28—H28B0.9900
S2—C151.733 (2)C28—H28C0.99 (7)
S2—C241.771 (2)C28—H28D0.87 (7)
O3—S1—O2118.65 (11)F2—C18—C19117.8 (2)
O3—S1—C1107.46 (10)C17—C18—C19124.8 (2)
O2—S1—C1108.81 (10)C20—C19—C18119.4 (2)
O3—S1—C10109.46 (10)C20—C19—H19120.3
O2—S1—C10107.34 (10)C18—C19—H19120.3
C1—S1—C10104.18 (10)C21—C20—C19116.5 (2)
C8—O1—C7107.10 (15)C21—C20—H20121.7
C8—C1—C2107.13 (19)C19—C20—H20121.7
C8—C1—S1125.44 (16)C20—C21—O4125.7 (2)
C2—C1—S1127.23 (16)C20—C21—C16124.1 (2)
C7—C2—C3119.14 (19)O4—C21—C16110.18 (19)
C7—C2—C1104.77 (17)C15—C22—O4110.5 (2)
C3—C2—C1136.1 (2)C15—C22—C23134.7 (2)
C4—C3—C2115.69 (19)O4—C22—C23114.8 (2)
C4—C3—H3122.2C22—C23—H23A109.5
C2—C3—H3122.2C22—C23—H23B109.5
F1—C4—C3117.72 (19)H23A—C23—H23B109.5
F1—C4—C5117.06 (19)C22—C23—H23C109.5
C3—C4—C5125.22 (19)H23A—C23—H23C109.5
C6—C5—C4119.1 (2)H23B—C23—H23C109.5
C6—C5—H5120.5C28—C24—C25105.42 (19)
C4—C5—H5120.5C28—C24—S2113.88 (17)
C7—C6—C5116.5 (2)C25—C24—S2111.11 (17)
C7—C6—H6121.8C28—C24—H24108.8
C5—C6—H6121.8C25—C24—H24108.8
C6—C7—O1125.45 (19)S2—C24—H24108.8
C6—C7—C2124.39 (19)C26—C25—C24103.5 (2)
O1—C7—C2110.14 (18)C26—C25—H25A111.1
O1—C8—C1110.84 (17)C24—C25—H25A111.1
O1—C8—C9115.52 (19)C26—C25—H25B111.1
C1—C8—C9133.6 (2)C24—C25—H25B111.1
C8—C9—H9A109.5H25A—C25—H25B109.0
C8—C9—H9B109.5C25—C26—C27B110.6 (2)
H9A—C9—H9B109.5C25—C26—C27A99.5 (5)
C8—C9—H9C109.5C25—C26—H26A111.9
H9A—C9—H9C109.5C27B—C26—H26A88.1
H9B—C9—H9C109.5C27A—C26—H26A111.9
C11—C10—C14106.14 (18)C25—C26—H26B111.9
C11—C10—S1112.41 (15)C27B—C26—H26B122.4
C14—C10—S1110.05 (16)C27A—C26—H26B111.9
C11—C10—H10109.4H26A—C26—H26B109.6
C14—C10—H10109.4C25—C26—H26C109.7
S1—C10—H10109.4C27B—C26—H26C106.2
C12—C11—C10104.7 (2)C27A—C26—H26C129.9
C12—C11—H11A110.8H26B—C26—H26C94.1
C10—C11—H11A110.8C25—C26—H26D110.0
C12—C11—H11B110.8C27B—C26—H26D111.9
C10—C11—H11B110.8C27A—C26—H26D98.1
H11A—C11—H11B108.9H26A—C26—H26D122.4
C13—C12—C11103.0 (2)H26C—C26—H26D108.3
C13—C12—H12A111.2C28—C27A—C26104.3 (2)
C11—C12—H12A111.2C28—C27A—H27A110.9
C13—C12—H12B111.2C26—C27A—H27A110.9
C11—C12—H12B111.2C28—C27A—H27B110.9
H12A—C12—H12B109.1C26—C27A—H27B110.9
C12—C13—C14104.7 (2)H27A—C27A—H27B108.9
C12—C13—H13A110.8C26—C27A—H28D124 (3)
C14—C13—H13A110.8H27A—C27A—H28D78.9
C12—C13—H13B110.8H27B—C27A—H28D117.5
C14—C13—H13B110.8C28—C27B—C26104.3 (2)
H13A—C13—H13B108.9C28—C27B—H27C110.9
C13—C14—C10104.66 (19)C26—C27B—H27C110.9
C13—C14—H14A110.8C28—C27B—H27D110.9
C10—C14—H14A110.8C26—C27B—H27D110.9
C13—C14—H14B110.8H27C—C27B—H27D108.9
C10—C14—H14B110.8C27A—C28—C24103.9 (3)
H14A—C14—H14B108.9C27B—C28—C24107.6 (3)
O6—S2—O5118.23 (11)C27A—C28—H28A111.0
O6—S2—C15109.20 (11)C27B—C28—H28A88.1
O5—S2—C15107.56 (10)C24—C28—H28A111.0
O6—S2—C24109.04 (11)C27A—C28—H28B111.0
O5—S2—C24107.64 (11)C27B—C28—H28B127.7
C15—S2—C24104.28 (10)C24—C28—H28B111.0
C22—O4—C21107.03 (16)H28A—C28—H28B109.0
C22—C15—C16107.17 (19)C27A—C28—H28C137 (4)
C22—C15—S2127.18 (18)C27B—C28—H28C123 (4)
C16—C15—S2125.52 (17)C24—C28—H28C118 (4)
C21—C16—C17119.4 (2)H28A—C28—H28C45.4
C21—C16—C15105.14 (19)H28B—C28—H28C64.8
C17—C16—C15135.4 (2)C27A—C28—H28D76 (4)
C18—C17—C16115.7 (2)C27B—C28—H28D98 (5)
C18—C17—H17122.2C24—C28—H28D107 (5)
C16—C17—H17122.2H28A—C28—H28D137.9
F2—C18—C17117.4 (2)H28C—C28—H28D100 (6)
O3—S1—C1—C8165.58 (19)C24—S2—C15—C1676.3 (2)
O2—S1—C1—C835.9 (2)C22—C15—C16—C210.1 (2)
C10—S1—C1—C878.3 (2)S2—C15—C16—C21176.02 (16)
O3—S1—C1—C220.1 (2)C22—C15—C16—C17180.0 (2)
O2—S1—C1—C2149.75 (18)S2—C15—C16—C173.9 (4)
C10—S1—C1—C296.00 (19)C21—C16—C17—C181.7 (3)
C8—C1—C2—C70.0 (2)C15—C16—C17—C18178.2 (2)
S1—C1—C2—C7175.20 (16)C16—C17—C18—F2179.82 (19)
C8—C1—C2—C3179.9 (2)C16—C17—C18—C190.8 (4)
S1—C1—C2—C34.9 (4)F2—C18—C19—C20178.6 (2)
C7—C2—C3—C41.0 (3)C17—C18—C19—C200.5 (4)
C1—C2—C3—C4179.1 (2)C18—C19—C20—C210.7 (3)
C2—C3—C4—F1179.56 (18)C19—C20—C21—O4179.4 (2)
C2—C3—C4—C50.2 (3)C19—C20—C21—C160.3 (3)
F1—C4—C5—C6178.90 (19)C22—O4—C21—C20177.9 (2)
C3—C4—C5—C60.9 (4)C22—O4—C21—C161.3 (2)
C4—C5—C6—C70.2 (3)C17—C16—C21—C201.6 (3)
C5—C6—C7—O1179.5 (2)C15—C16—C21—C20178.4 (2)
C5—C6—C7—C21.1 (3)C17—C16—C21—O4179.21 (18)
C8—O1—C7—C6178.1 (2)C15—C16—C21—O40.8 (2)
C8—O1—C7—C20.5 (2)C16—C15—C22—O40.7 (2)
C3—C2—C7—C61.8 (3)S2—C15—C22—O4176.73 (15)
C1—C2—C7—C6178.4 (2)C16—C15—C22—C23178.4 (2)
C3—C2—C7—O1179.60 (17)S2—C15—C22—C232.4 (4)
C1—C2—C7—O10.3 (2)C21—O4—C22—C151.2 (2)
C7—O1—C8—C10.5 (2)C21—O4—C22—C23178.08 (18)
C7—O1—C8—C9177.92 (18)O6—S2—C24—C2847.9 (2)
C2—C1—C8—O10.3 (2)O5—S2—C24—C28177.32 (17)
S1—C1—C8—O1175.62 (14)C15—S2—C24—C2868.63 (19)
C2—C1—C8—C9177.7 (2)O6—S2—C24—C2570.9 (2)
S1—C1—C8—C92.4 (4)O5—S2—C24—C2558.5 (2)
O3—S1—C10—C1150.09 (18)C15—S2—C24—C25172.52 (18)
O2—S1—C10—C11179.88 (16)C28—C24—C25—C2629.6 (3)
C1—S1—C10—C1164.59 (18)S2—C24—C25—C26153.4 (2)
O3—S1—C10—C1467.98 (17)C24—C25—C26—C27B23.9 (8)
O2—S1—C10—C1462.05 (17)C24—C25—C26—C27A45.8 (5)
C1—S1—C10—C14177.34 (15)C25—C26—C27A—C2846.0 (9)
C14—C10—C11—C1217.1 (2)C27B—C26—C27A—C2874.3 (4)
S1—C10—C11—C12103.3 (2)C25—C26—C27B—C288.7 (12)
C10—C11—C12—C1336.0 (3)C27A—C26—C27B—C2874.2 (4)
C11—C12—C13—C1441.4 (3)C26—C27A—C28—C27B74.3 (4)
C12—C13—C14—C1030.6 (3)C26—C27A—C28—C2427.8 (10)
C11—C10—C14—C137.9 (2)C26—C27B—C28—C27A74.2 (4)
S1—C10—C14—C13129.75 (18)C26—C27B—C28—C2410.5 (12)
O6—S2—C15—C2217.4 (2)C25—C24—C28—C27A0.6 (7)
O5—S2—C15—C22146.8 (2)S2—C24—C28—C27A122.7 (6)
C24—S2—C15—C2299.1 (2)C25—C24—C28—C27B25.2 (8)
O6—S2—C15—C16167.32 (18)S2—C24—C28—C27B147.2 (8)
O5—S2—C15—C1637.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9C···O6i0.982.453.348 (3)152
C19—H19···O6ii0.952.583.469 (3)157
C23—H23A···O2iii0.982.503.318 (3)141
Symmetry codes: (i) x1, y1, z; (ii) x1, y, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H15FO3S
Mr282.32
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)10.0568 (8), 10.2697 (8), 13.2894 (10)
α, β, γ (°)95.033 (4), 109.140 (4), 91.229 (4)
V3)1289.82 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.26 × 0.24 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.936, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections
21777, 5565, 4022
Rint0.042
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.119, 1.03
No. of reflections5565
No. of parameters361
No. of restraints20
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.31

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
C9—H9C···O6i0.982.453.348 (3)152
C19—H19···O6ii0.952.583.469 (3)157
C23—H23A···O2iii0.982.503.318 (3)141
Symmetry codes: (i) x1, y1, z; (ii) x1, y, z; (iii) x+1, y, z.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS
First citationAslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195.  Web of Science CrossRef PubMed CAS
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
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
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
First citationSeo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1386.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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

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