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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3504
https://doi.org/10.1107/S1600536811051178

2-(4-Fluoro­phen­yl)-3-iso­propyl­sulfinyl-5,6-methyl­enedi­­oxy-1-benzo­furan

Pil Ja Seo,a Hong Dae Choi,a Byeng Wha Sonb and Uk Leeb*

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 November 2011; accepted 28 November 2011; online 30 November 2011)

In the title compound, C18H15FO4S, the fluoro­benzene ring makes a dihedral angle of 4.3 (1)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations, with site-occupancy factors of 0.940 (3) and 0.060 (3).

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 the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o605.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1296.]).

[Scheme 1]

Experimental

Crystal data

  • C18H15FO4S

  • Mr = 346.36

  • Triclinic, [P \overline 1]

  • a = 6.2519 (1) Å

  • b = 9.6773 (2) Å

  • c = 12.9267 (2) Å

  • α = 90.122 (1)°

  • β = 94.726 (1)°

  • γ = 101.920 (1)°

  • V = 762.47 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 173 K

  • 0.45 × 0.21 × 0.14 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 = 0.898, Tmax = 0.967

  • 13552 measured reflections

  • 3488 independent reflections

  • 3171 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.101

  • S = 1.06

  • 3488 reflections

  • 229 parameters

  • 4 restraints

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5B⋯O4Ai 0.99 2.27 3.231 (2) 163
C18—H18A⋯O4Aii 0.98 2.49 3.354 (2) 147
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811051178/fj2487sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811051178/fj2487Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811051178/fj2487Isup3.cml

checkCIF report


Comment top

Recently, substituted benzofuran derivatives have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial 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 study of 5,6-(methylenedioxy)benzofuran derivatives containing either 3-methylsulfinyl (Choi et al., 2010a) or 3-ethylsulfinyl (Choi et al., 2010b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 4.3 (1)°. The O atom of the sulfinyl group is disordered over two positions with site-occupancy factors, from refinement, of 0.940 (3) (Part A) and 0.060 (3) (part B). The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methylene H atom and the O atom of the S═O unit (Table 1, first entry & Fig. 2), and the second one between a methyl H atom of the isopropyl group and the O atom of the S═O unit (Table 1, second entry & Fig. 2).

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 the crystal structures of related compounds, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-3-isopropylsulfanyl-5,6-methylenedioxy-1-benzofuran (251 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 437–438 K; Rf = 0.55 (hexane–ethyl acetate, 1:2 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 the aryl, 1.00 Å for the methine, 0.99 Å for the methylene, and 0.98 Å for the methyl H atoms. Uiso(H) =1.2Ueq(C) for the aryl, methine, and methylene H atoms, and 1.5Ueq(C) for the methyl H atoms. The O atom of sulfinyl group is disordered over two positions with site-ccupancy factors, from refinement of 0.940 (3) (part A) and 0.060 (3) (part B). The distance of S—O sets was restrained to 0.001 Å using command SADI and DELU.

Structure description top

Recently, substituted benzofuran derivatives have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial 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 study of 5,6-(methylenedioxy)benzofuran derivatives containing either 3-methylsulfinyl (Choi et al., 2010a) or 3-ethylsulfinyl (Choi et al., 2010b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 4.3 (1)°. The O atom of the sulfinyl group is disordered over two positions with site-occupancy factors, from refinement, of 0.940 (3) (Part A) and 0.060 (3) (part B). The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methylene H atom and the O atom of the S═O unit (Table 1, first entry & Fig. 2), and the second one between a methyl H atom of the isopropyl group and the O atom of the S═O unit (Table 1, second entry & Fig. 2).

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 the crystal structures of related compounds, see: Choi et al. (2010a,b).

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 small spheres of arbitrary radius. The O atom of the sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.940 (3) (Part A) and 0.060 (3) (part B).
[Figure 2] Fig. 2. A view of the C—H···O interactions (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; (ii) - x + 1, 1- y, - z.]
11-(4-fluorophenyl)-12-(propane-2-sulfinyl)-4,6,10- trioxatricyclo[7.3.0.03,7]dodeca-1(9),2,7-triene top
Crystal data top
C18H15FO4SZ = 2
Mr = 346.36F(000) = 360
Triclinic, P1Dx = 1.509 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2519 (1) ÅCell parameters from 7633 reflections
b = 9.6773 (2) Åθ = 2.6–27.5°
c = 12.9267 (2) ŵ = 0.24 mm−1
α = 90.122 (1)°T = 173 K
β = 94.726 (1)°Block, colourless
γ = 101.920 (1)°0.45 × 0.21 × 0.14 mm
V = 762.47 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3488 independent reflections
Radiation source: rotating anode3171 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.024
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.6°
φ and ω scansh = −7→8
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −12→12
Tmin = 0.898, Tmax = 0.967l = −15→16
13552 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) = 0.101H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.4198P]
where P = (Fo2 + 2Fc2)/3
3488 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.56 e Å−3
4 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C18H15FO4Sγ = 101.920 (1)°
Mr = 346.36V = 762.47 (2) Å3
Triclinic, P1Z = 2
a = 6.2519 (1) ÅMo Kα radiation
b = 9.6773 (2) ŵ = 0.24 mm−1
c = 12.9267 (2) ÅT = 173 K
α = 90.122 (1)°0.45 × 0.21 × 0.14 mm
β = 94.726 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3488 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3171 reflections with I > 2σ(I)
Tmin = 0.898, Tmax = 0.967Rint = 0.024
13552 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0394 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.06Δρmax = 0.56 e Å−3
3488 reflectionsΔρmin = −0.40 e Å−3
229 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)
S10.15386 (6)0.36031 (4)0.14314 (3)0.02733 (12)
F1−0.43070 (18)0.35212 (13)0.57633 (8)0.0438 (3)
O10.31016 (17)0.12210 (11)0.37742 (8)0.0264 (2)
O20.8622 (2)−0.09128 (13)0.23234 (10)0.0377 (3)
O30.8308 (2)0.03336 (14)0.08091 (10)0.0415 (3)
O4A0.2282 (2)0.32964 (14)0.04204 (9)0.0358 (4)0.940 (3)
O4B−0.0806 (7)0.3600 (18)0.1198 (15)0.030 (4)0.060 (3)
C10.2601 (2)0.25039 (15)0.23544 (11)0.0241 (3)
C20.4209 (2)0.16817 (15)0.21565 (12)0.0245 (3)
C30.5457 (3)0.15352 (16)0.13162 (12)0.0282 (3)
H30.53350.20300.06870.034*
C40.6853 (3)0.06270 (17)0.14767 (13)0.0289 (3)
C50.9256 (3)−0.07578 (18)0.12790 (14)0.0343 (4)
H5A1.0874−0.05060.12850.041*
H5B0.8725−0.16560.08820.041*
C60.7051 (3)−0.01235 (16)0.23908 (13)0.0279 (3)
C70.5854 (3)−0.00188 (16)0.32195 (12)0.0278 (3)
H70.5975−0.05300.38410.033*
C80.4441 (2)0.09170 (15)0.30558 (12)0.0248 (3)
C90.1973 (2)0.21924 (15)0.33327 (12)0.0247 (3)
C100.0418 (2)0.26129 (16)0.39856 (12)0.0249 (3)
C110.0148 (3)0.20327 (18)0.49683 (13)0.0308 (3)
H110.10530.14090.52220.037*
C12−0.1410 (3)0.23498 (19)0.55767 (13)0.0343 (4)
H12−0.15840.19540.62440.041*
C13−0.2699 (3)0.32515 (18)0.51912 (13)0.0309 (3)
C14−0.2463 (3)0.38780 (18)0.42458 (13)0.0311 (3)
H14−0.33540.45180.40100.037*
C15−0.0895 (3)0.35560 (17)0.36425 (12)0.0294 (3)
H15−0.07090.39820.29860.035*
C160.3187 (3)0.53086 (16)0.19013 (13)0.0289 (3)
H160.30110.54100.26580.035*
C170.2245 (4)0.6446 (2)0.1325 (2)0.0562 (6)
H17A0.30620.73800.15720.084*
H17B0.06970.63460.14520.084*
H17C0.23690.63460.05790.084*
C180.5593 (3)0.54184 (19)0.17658 (15)0.0365 (4)
H18A0.58140.54240.10240.055*
H18B0.60820.46080.20870.055*
H18C0.64430.62940.20990.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0300 (2)0.0256 (2)0.0255 (2)0.00633 (14)−0.00408 (14)0.00327 (14)
F10.0410 (6)0.0612 (7)0.0347 (6)0.0199 (5)0.0117 (4)−0.0051 (5)
O10.0268 (5)0.0275 (5)0.0268 (5)0.0092 (4)0.0047 (4)0.0070 (4)
O20.0415 (7)0.0373 (7)0.0412 (7)0.0215 (5)0.0103 (5)0.0049 (5)
O30.0502 (8)0.0434 (7)0.0398 (7)0.0246 (6)0.0185 (6)0.0069 (5)
O4A0.0480 (8)0.0365 (7)0.0234 (6)0.0108 (6)0.0003 (5)0.0014 (5)
O4B0.031 (3)0.022 (9)0.037 (10)0.006 (7)−0.004 (4)0.018 (7)
C10.0246 (7)0.0230 (7)0.0245 (7)0.0049 (5)0.0009 (5)0.0031 (5)
C20.0245 (7)0.0216 (7)0.0266 (7)0.0035 (5)0.0011 (6)0.0024 (5)
C30.0311 (8)0.0276 (7)0.0270 (8)0.0072 (6)0.0051 (6)0.0033 (6)
C40.0299 (8)0.0261 (7)0.0308 (8)0.0049 (6)0.0063 (6)−0.0013 (6)
C50.0355 (9)0.0305 (8)0.0390 (9)0.0108 (7)0.0053 (7)−0.0041 (7)
C60.0271 (7)0.0216 (7)0.0354 (8)0.0064 (6)0.0013 (6)−0.0002 (6)
C70.0281 (8)0.0250 (7)0.0309 (8)0.0073 (6)0.0022 (6)0.0053 (6)
C80.0234 (7)0.0234 (7)0.0272 (7)0.0038 (5)0.0033 (6)0.0020 (6)
C90.0233 (7)0.0227 (7)0.0277 (7)0.0050 (5)−0.0003 (6)0.0045 (6)
C100.0224 (7)0.0245 (7)0.0268 (7)0.0028 (5)0.0018 (5)0.0016 (6)
C110.0322 (8)0.0335 (8)0.0285 (8)0.0106 (6)0.0027 (6)0.0053 (6)
C120.0388 (9)0.0406 (9)0.0247 (8)0.0093 (7)0.0060 (7)0.0051 (7)
C130.0273 (8)0.0370 (8)0.0285 (8)0.0063 (6)0.0045 (6)−0.0073 (6)
C140.0284 (8)0.0341 (8)0.0325 (8)0.0110 (6)0.0005 (6)−0.0001 (6)
C150.0284 (8)0.0329 (8)0.0284 (8)0.0091 (6)0.0037 (6)0.0057 (6)
C160.0341 (8)0.0233 (7)0.0292 (8)0.0061 (6)0.0008 (6)0.0002 (6)
C170.0508 (12)0.0306 (9)0.0863 (17)0.0127 (8)−0.0105 (11)0.0137 (10)
C180.0325 (9)0.0340 (9)0.0409 (9)0.0021 (7)0.0025 (7)0.0068 (7)
Geometric parameters (Å, º) top
S1—O4B1.4716 (17)C7—H70.9500
S1—O4A1.4724 (13)C9—C101.456 (2)
S1—C11.7783 (15)C10—C151.398 (2)
S1—C161.8290 (16)C10—C111.399 (2)
F1—C131.3623 (18)C11—C121.382 (2)
O1—C81.3707 (18)C11—H110.9500
O1—C91.3847 (17)C12—C131.373 (2)
O2—C61.3712 (19)C12—H120.9500
O2—C51.437 (2)C13—C141.371 (2)
O3—C41.3740 (19)C14—C151.384 (2)
O3—C51.428 (2)C14—H140.9500
C1—C91.371 (2)C15—H150.9500
C1—C21.443 (2)C16—C181.510 (2)
C2—C81.393 (2)C16—C171.521 (2)
C2—C31.412 (2)C16—H161.0000
C3—C41.366 (2)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C61.398 (2)C17—H17C0.9800
C5—H5A0.9900C18—H18A0.9800
C5—H5B0.9900C18—H18B0.9800
C6—C71.371 (2)C18—H18C0.9800
C7—C81.395 (2)
O4B—S1—O4A104.0 (8)O1—C9—C10114.53 (13)
O4B—S1—C1124.7 (6)C15—C10—C11118.20 (15)
O4A—S1—C1107.07 (7)C15—C10—C9121.63 (14)
O4B—S1—C16114.1 (7)C11—C10—C9120.13 (14)
O4A—S1—C16107.44 (8)C12—C11—C10121.20 (15)
C1—S1—C1698.56 (7)C12—C11—H11119.4
C8—O1—C9107.04 (11)C10—C11—H11119.4
C6—O2—C5105.72 (13)C13—C12—C11118.27 (15)
C4—O3—C5106.07 (13)C13—C12—H12120.9
C9—C1—C2107.40 (13)C11—C12—H12120.9
C9—C1—S1127.89 (12)F1—C13—C14118.35 (15)
C2—C1—S1124.56 (11)F1—C13—C12118.79 (15)
C8—C2—C3120.03 (14)C14—C13—C12122.85 (15)
C8—C2—C1105.09 (13)C13—C14—C15118.45 (15)
C3—C2—C1134.88 (14)C13—C14—H14120.8
C4—C3—C2114.84 (14)C15—C14—H14120.8
C4—C3—H3122.6C14—C15—C10120.98 (15)
C2—C3—H3122.6C14—C15—H15119.5
C3—C4—O3126.86 (15)C10—C15—H15119.5
C3—C4—C6123.73 (15)C18—C16—C17112.60 (15)
O3—C4—C6109.37 (14)C18—C16—S1111.75 (12)
O3—C5—O2107.97 (13)C17—C16—S1107.09 (12)
O3—C5—H5A110.1C18—C16—H16108.4
O2—C5—H5A110.1C17—C16—H16108.4
O3—C5—H5B110.1S1—C16—H16108.4
O2—C5—H5B110.1C16—C17—H17A109.5
H5A—C5—H5B108.4C16—C17—H17B109.5
O2—C6—C7127.12 (15)H17A—C17—H17B109.5
O2—C6—C4109.74 (14)C16—C17—H17C109.5
C7—C6—C4123.13 (14)H17A—C17—H17C109.5
C6—C7—C8113.00 (14)H17B—C17—H17C109.5
C6—C7—H7123.5C16—C18—H18A109.5
C8—C7—H7123.5C16—C18—H18B109.5
O1—C8—C2110.64 (13)H18A—C18—H18B109.5
O1—C8—C7124.08 (13)C16—C18—H18C109.5
C2—C8—C7125.27 (14)H18A—C18—H18C109.5
C1—C9—O1109.82 (13)H18B—C18—H18C109.5
C1—C9—C10135.63 (14)
O4B—S1—C1—C9−43.3 (10)C3—C2—C8—C70.3 (2)
O4A—S1—C1—C9−164.61 (14)C1—C2—C8—C7−179.36 (14)
C16—S1—C1—C984.09 (15)C6—C7—C8—O1−178.87 (13)
O4B—S1—C1—C2131.6 (10)C6—C7—C8—C20.3 (2)
O4A—S1—C1—C210.31 (15)C2—C1—C9—O10.33 (16)
C16—S1—C1—C2−100.99 (13)S1—C1—C9—O1175.95 (10)
C9—C1—C2—C8−0.13 (16)C2—C1—C9—C10−178.34 (16)
S1—C1—C2—C8−175.93 (11)S1—C1—C9—C10−2.7 (3)
C9—C1—C2—C3−179.69 (16)C8—O1—C9—C1−0.41 (16)
S1—C1—C2—C34.5 (3)C8—O1—C9—C10178.57 (12)
C8—C2—C3—C4−0.7 (2)C1—C9—C10—C150.4 (3)
C1—C2—C3—C4178.84 (16)O1—C9—C10—C15−178.21 (13)
C2—C3—C4—O3−177.24 (15)C1—C9—C10—C11178.06 (17)
C2—C3—C4—C60.6 (2)O1—C9—C10—C11−0.6 (2)
C5—O3—C4—C3−175.24 (16)C15—C10—C11—C121.7 (2)
C5—O3—C4—C66.70 (18)C9—C10—C11—C12−176.06 (15)
C4—O3—C5—O2−10.48 (18)C10—C11—C12—C130.1 (3)
C6—O2—C5—O310.29 (17)C11—C12—C13—F1177.04 (15)
C5—O2—C6—C7175.46 (16)C11—C12—C13—C14−1.9 (3)
C5—O2—C6—C4−6.21 (17)F1—C13—C14—C15−177.15 (14)
C3—C4—C6—O2−178.41 (15)C12—C13—C14—C151.8 (3)
O3—C4—C6—O2−0.28 (18)C13—C14—C15—C100.1 (2)
C3—C4—C6—C70.0 (3)C11—C10—C15—C14−1.8 (2)
O3—C4—C6—C7178.12 (14)C9—C10—C15—C14175.91 (14)
O2—C6—C7—C8177.70 (14)O4B—S1—C16—C18−159.6 (8)
C4—C6—C7—C8−0.4 (2)O4A—S1—C16—C18−44.95 (14)
C9—O1—C8—C20.32 (16)C1—S1—C16—C1866.05 (13)
C9—O1—C8—C7179.57 (14)O4B—S1—C16—C17−35.9 (8)
C3—C2—C8—O1179.52 (13)O4A—S1—C16—C1778.81 (15)
C1—C2—C8—O1−0.12 (16)C1—S1—C16—C17−170.20 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O4Ai0.992.273.231 (2)163
C18—H18A···O4Aii0.982.493.354 (2)147
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC18H15FO4S
Mr346.36
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.2519 (1), 9.6773 (2), 12.9267 (2)
α, β, γ (°)90.122 (1), 94.726 (1), 101.920 (1)
V (Å3)762.47 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.45 × 0.21 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.898, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections		13552, 3488, 3171
Rint0.024
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.101, 1.06
No. of reflections3488
No. of parameters229
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.56, −0.40

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
C5—H5B···O4Ai0.992.273.231 (2)163
C18—H18A···O4Aii0.982.493.354 (2)147
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z.
 

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
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 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1296.  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

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3504
https://doi.org/10.1107/S1600536811051178
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