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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 66| Part 4| April 2010| Page o886
doi:10.1107/S1600536810008627

5-Chloro-3-ethyl­sulfinyl-2-(4-fluoro­phen­yl)-7-methyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seo,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 24 February 2010; accepted 6 March 2010; online 20 March 2010)

In the title compound, C17H14ClFO2S, the 4-fluoro­phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 8.32 (5)°. The crystal structure features a short Cl⋯O contact [3.092 (1) Å].

Related literature

For the crystal structures of similar 3-ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o323.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o402.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o629.]). For the pharmacological 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 a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data

  • C17H14ClFO2S

  • Mr = 336.79

  • Triclinic, [P \overline 1]

  • a = 7.3395 (1) Å

  • b = 10.5618 (2) Å

  • c = 11.2281 (2) Å

  • α = 65.357 (1)°

  • β = 85.232 (1)°

  • γ = 69.939 (1)°

  • V = 741.28 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 174 K

  • 0.32 × 0.28 × 0.19 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 = 0.879, Tmax = 0.926

  • 13016 measured reflections

  • 3440 independent reflections

  • 3292 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.06

  • 3440 reflections

  • 200 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.59 e Å−3

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: 10.1107/S1600536810008627/vm2020sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810008627/vm2020Isup2.hkl

checkCIF report


Comment top

Compounds containing benzofuran moiety show various pharmacological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds are widely occurring in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran analogues (Choi et al., 2010a,b,c), we report the crystal structure of 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 dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 8.32 (5)°. The crystal packing (Fig. 2) is stabilized by a Cl···O halogen bond between the chlorine and the oxygen of the S═O unit [Cl···O2i = 3.092 (1) Å; C4–Cl···O2i = 167.20 (6)°, symmetry code (i) - x, - y + 1, - z] (Politzer et al., 2007).

Related literature top

For the crystal structures of similar 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010a,b,c). For the pharmacological 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 a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-chloro-3-ethylsulfanyl-2-(4-fluorophenyl)-7-methyl-1-benzofuran (256 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 83%, m.p. 409-410 K; Rf = 0.64 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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, 0.99 Å for methylene, and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms, 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. C–Cl···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: i) - x, - y + 1, - z.]
5-Chloro-3-ethylsulfinyl-2-(4-fluorophenyl)-7-methyl-1-benzofuran top
Crystal data top
C17H14ClFO2SZ = 2
Mr = 336.79F(000) = 348
Triclinic, P1Dx = 1.509 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3395 (1) ÅCell parameters from 9795 reflections
b = 10.5618 (2) Åθ = 2.3–27.6°
c = 11.2281 (2) ŵ = 0.41 mm−1
α = 65.357 (1)°T = 174 K
β = 85.232 (1)°Block, colourless
γ = 69.939 (1)°0.32 × 0.28 × 0.19 mm
V = 741.28 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3440 independent reflections
Radiation source: Rotating Anode3292 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics monochromatorRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 2.0°
ϕ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −13→13
Tmin = 0.879, Tmax = 0.926l = −14→14
13016 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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.106H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.4567P]
where P = (Fo2 + 2Fc2)/3
3440 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.59 e Å−3
Crystal data top
C17H14ClFO2Sγ = 69.939 (1)°
Mr = 336.79V = 741.28 (2) Å3
Triclinic, P1Z = 2
a = 7.3395 (1) ÅMo Kα radiation
b = 10.5618 (2) ŵ = 0.41 mm−1
c = 11.2281 (2) ÅT = 174 K
α = 65.357 (1)°0.32 × 0.28 × 0.19 mm
β = 85.232 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3440 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3292 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 0.926Rint = 0.023
13016 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.06Δρmax = 0.56 e Å−3
3440 reflectionsΔρmin = −0.59 e Å−3
200 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
Cl−0.00786 (7)0.72104 (5)−0.07738 (4)0.03543 (13)
S0.36819 (5)0.18932 (4)0.42209 (3)0.02170 (12)
F0.58849 (19)0.15390 (14)1.03317 (10)0.0457 (3)
O10.20083 (15)0.56779 (11)0.46554 (10)0.0215 (2)
O20.21568 (18)0.18590 (14)0.34446 (12)0.0329 (3)
C10.2932 (2)0.37130 (16)0.41330 (14)0.0197 (3)
C20.1983 (2)0.50252 (16)0.29663 (14)0.0202 (3)
C30.1543 (2)0.53059 (17)0.16738 (15)0.0230 (3)
H30.18930.45370.13790.028*
C40.0568 (2)0.67697 (18)0.08464 (15)0.0245 (3)
C50.0001 (2)0.79229 (17)0.12610 (15)0.0242 (3)
H5−0.06830.89040.06520.029*
C60.0420 (2)0.76611 (16)0.25427 (15)0.0220 (3)
C70.1436 (2)0.61881 (16)0.33529 (14)0.0200 (3)
C80.2915 (2)0.41644 (16)0.51177 (14)0.0199 (3)
C90.3662 (2)0.34377 (17)0.64954 (14)0.0213 (3)
C100.4879 (2)0.19527 (18)0.70685 (15)0.0259 (3)
H100.52120.13850.65630.031*
C110.5603 (2)0.13041 (19)0.83696 (16)0.0301 (3)
H110.64070.02920.87650.036*
C120.5129 (3)0.2158 (2)0.90716 (15)0.0315 (4)
C130.3926 (3)0.3615 (2)0.85540 (16)0.0318 (4)
H130.36100.41710.90710.038*
C140.3184 (2)0.42539 (18)0.72601 (16)0.0266 (3)
H140.23410.52560.68880.032*
C15−0.0198 (2)0.88632 (18)0.30237 (17)0.0281 (3)
H15A−0.16190.93140.29200.034*
H15B0.03820.96200.25120.034*
H15C0.02380.84420.39530.034*
C160.5748 (2)0.19716 (18)0.32281 (16)0.0278 (3)
H16A0.60810.11950.28910.033*
H16B0.54140.29470.24660.033*
C170.7481 (2)0.17387 (19)0.40416 (17)0.0296 (3)
H17A0.71340.24890.43970.044*
H17B0.85740.18270.34870.044*
H17C0.78550.07500.47670.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0530 (3)0.0313 (2)0.0190 (2)−0.01523 (19)−0.00769 (17)−0.00508 (16)
S0.0252 (2)0.01716 (18)0.02138 (19)−0.00641 (14)−0.00133 (14)−0.00688 (14)
F0.0555 (7)0.0562 (7)0.0189 (5)−0.0214 (6)−0.0094 (5)−0.0055 (5)
O10.0236 (5)0.0192 (5)0.0188 (5)−0.0035 (4)−0.0010 (4)−0.0077 (4)
O20.0357 (6)0.0309 (6)0.0355 (7)−0.0144 (5)−0.0072 (5)−0.0127 (5)
C10.0193 (6)0.0173 (6)0.0194 (6)−0.0039 (5)−0.0003 (5)−0.0063 (5)
C20.0186 (6)0.0187 (7)0.0209 (7)−0.0049 (5)0.0005 (5)−0.0070 (5)
C30.0264 (7)0.0218 (7)0.0205 (7)−0.0076 (6)−0.0003 (5)−0.0085 (6)
C40.0278 (7)0.0259 (8)0.0185 (7)−0.0104 (6)−0.0024 (6)−0.0063 (6)
C50.0234 (7)0.0197 (7)0.0241 (7)−0.0062 (6)−0.0029 (6)−0.0040 (6)
C60.0192 (6)0.0192 (7)0.0245 (7)−0.0044 (5)0.0002 (5)−0.0078 (6)
C70.0189 (6)0.0204 (7)0.0187 (6)−0.0049 (5)−0.0002 (5)−0.0074 (5)
C80.0182 (6)0.0183 (6)0.0206 (7)−0.0047 (5)0.0011 (5)−0.0067 (5)
C90.0206 (6)0.0242 (7)0.0186 (7)−0.0098 (6)0.0013 (5)−0.0068 (6)
C100.0242 (7)0.0267 (8)0.0236 (7)−0.0069 (6)−0.0013 (6)−0.0083 (6)
C110.0269 (8)0.0306 (8)0.0242 (8)−0.0090 (6)−0.0033 (6)−0.0033 (6)
C120.0336 (8)0.0425 (10)0.0165 (7)−0.0195 (7)−0.0027 (6)−0.0043 (7)
C130.0400 (9)0.0387 (9)0.0233 (8)−0.0198 (8)0.0040 (7)−0.0143 (7)
C140.0315 (8)0.0269 (8)0.0218 (7)−0.0120 (6)0.0024 (6)−0.0089 (6)
C150.0292 (8)0.0204 (7)0.0297 (8)−0.0016 (6)0.0003 (6)−0.0109 (6)
C160.0284 (8)0.0271 (8)0.0257 (8)−0.0038 (6)0.0041 (6)−0.0137 (6)
C170.0260 (7)0.0267 (8)0.0358 (9)−0.0082 (6)0.0036 (6)−0.0136 (7)
Geometric parameters (Å, º) top
Cl—O2i3.092 (1)C9—C141.401 (2)
Cl—C41.743 (2)C9—C101.402 (2)
S—O21.493 (1)C10—C111.389 (2)
S—C11.770 (2)C10—H100.9500
S—C161.810 (2)C11—C121.374 (3)
F—C121.359 (2)C11—H110.9500
O1—C71.377 (2)C12—C131.376 (3)
O1—C81.380 (2)C13—C141.387 (2)
C1—C81.372 (2)C13—H130.9500
C1—C21.448 (2)C14—H140.9500
C2—C71.391 (2)C15—H15A0.9800
C2—C31.397 (2)C15—H15B0.9800
C3—C41.385 (2)C15—H15C0.9800
C3—H30.9500C16—C171.518 (2)
C4—C51.402 (2)C16—H16A0.9900
C5—C61.388 (2)C16—H16B0.9900
C5—H50.9500C17—H17A0.9800
C6—C71.393 (2)C17—H17B0.9800
C6—C151.498 (2)C17—H17C0.9800
C8—C91.465 (2)
C4—Cl—O2i167.20 (6)C11—C10—H10119.7
O2—S—C1106.41 (7)C9—C10—H10119.7
O2—S—C16107.18 (8)C12—C11—C10118.53 (16)
C1—S—C1697.87 (7)C12—C11—H11120.7
C7—O1—C8106.97 (11)C10—C11—H11120.7
C8—C1—C2107.05 (12)F—C12—C11118.63 (16)
C8—C1—S129.11 (11)F—C12—C13118.49 (16)
C2—C1—S123.49 (11)C11—C12—C13122.88 (15)
C7—C2—C3119.80 (13)C12—C13—C14118.44 (16)
C7—C2—C1105.17 (13)C12—C13—H13120.8
C3—C2—C1135.02 (14)C14—C13—H13120.8
C4—C3—C2116.20 (14)C13—C14—C9120.75 (15)
C4—C3—H3121.9C13—C14—H14119.6
C2—C3—H3121.9C9—C14—H14119.6
C3—C4—C5123.12 (14)C6—C15—H15A109.5
C3—C4—Cl119.13 (12)C6—C15—H15B109.5
C5—C4—Cl117.71 (12)H15A—C15—H15B109.5
C6—C5—C4121.36 (14)C6—C15—H15C109.5
C6—C5—H5119.3H15A—C15—H15C109.5
C4—C5—H5119.3H15B—C15—H15C109.5
C5—C6—C7114.70 (13)C17—C16—S110.04 (11)
C5—C6—C15122.68 (14)C17—C16—H16A109.7
C7—C6—C15122.61 (14)S—C16—H16A109.7
O1—C7—C2110.59 (12)C17—C16—H16B109.7
O1—C7—C6124.61 (13)S—C16—H16B109.7
C2—C7—C6124.79 (14)H16A—C16—H16B108.2
C1—C8—O1110.21 (12)C16—C17—H17A109.5
C1—C8—C9135.48 (13)C16—C17—H17B109.5
O1—C8—C9114.29 (12)H17A—C17—H17B109.5
C14—C9—C10118.79 (14)C16—C17—H17C109.5
C14—C9—C8119.28 (14)H17A—C17—H17C109.5
C10—C9—C8121.92 (13)H17B—C17—H17C109.5
C11—C10—C9120.58 (15)
Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC17H14ClFO2S
Mr336.79
Crystal system, space groupTriclinic, P1
Temperature (K)174
a, b, c (Å)7.3395 (1), 10.5618 (2), 11.2281 (2)
α, β, γ (°)65.357 (1), 85.232 (1), 69.939 (1)
V (Å3)741.28 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.41
Crystal size (mm)0.32 × 0.28 × 0.19
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.879, 0.926
No. of measured, independent and
observed [I > 2σ(I)] reflections		13016, 3440, 3292
Rint0.023
(sin θ/λ)max (Å−1)0.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.106, 1.06
No. of reflections3440
No. of parameters200
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.56, −0.59

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

 

References

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 First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
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ISSN: 2056-9890
Volume 66| Part 4| April 2010| Page o886
doi:10.1107/S1600536810008627
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