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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 2| February 2011| Page o351
doi:10.1107/S1600536810049986

5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2,7-di­methyl-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 November 2010; accepted 30 November 2010; online 12 January 2011)

In the title compound, C16H12BrFO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 83.29 (5)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

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 our previous structural studies of related 3-[(4-fluoro­phen­yl)sulfin­yl]-5-halo-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, o1297.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1637.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o1876.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12BrFO2S

  • Mr = 367.23

  • Triclinic, [P \overline 1]

  • a = 7.6696 (1) Å

  • b = 8.6308 (1) Å

  • c = 12.3225 (2) Å

  • α = 96.084 (1)°

  • β = 91.510 (1)°

  • γ = 113.609 (1)°

  • V = 741.08 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.93 mm−1

  • T = 173 K

  • 0.26 × 0.16 × 0.13 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 = 0.583, Tmax = 0.746

  • 13338 measured reflections

  • 3422 independent reflections

  • 2976 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.074

  • S = 1.07

  • 3422 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13⋯O2i 0.95 2.41 3.259 (2) 148
Symmetry code: (i) 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049986/zq2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810049986/zq2078Isup2.hkl

checkCIF report


Comment top

A series of benzofuran ring system exhibit interesting potent pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-[(4-fluorophenyl)sulfinyl]-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report here the crystal structure of the title compound

In the title molecule, the benzofuran unit is essentially planar, with a mean deviation of 0.011 (1) Å from the least-squares plane defined by the nine constituent atoms (Fig. 1). The dihedral angle formed by the mean plane of the benzofuran fragment and the 4-fluorophenyl ring is 83.29 (5)°. The molecular packing is stabilized by weak intermolecular C—H···O hydrogen bonds between the 4-fluorophenyl H13 atom and the oxygen of the S═O unit (Table 1; C13—H13···O2i).

Related literature top

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 our previous structural studies of related 3-[(4-fluorophenyl)sulfinyl]-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-3-[(4-fluorophenyl)sulfanyl]-2,7-dimethyl-1-benzofuran (281 mg, 0.8 mmol) in dichloromethane (40 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 75%, m.p. 407–408 K; Rf = 0.67 (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 and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl 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 small spheres of arbitrary radius.
5-Bromo-3-(4-fluorophenylsulfinyl)-2,7-dimethyl-1-benzofuran top
Crystal data top
C16H12BrFO2SZ = 2
Mr = 367.23F(000) = 368
Triclinic, P1Dx = 1.646 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6696 (1) ÅCell parameters from 6925 reflections
b = 8.6308 (1) Åθ = 2.6–27.4°
c = 12.3225 (2) ŵ = 2.93 mm−1
α = 96.084 (1)°T = 173 K
β = 91.510 (1)°Block, colourless
γ = 113.609 (1)°0.26 × 0.16 × 0.13 mm
V = 741.08 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3422 independent reflections
Radiation source: rotating anode2976 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 1.7°
ϕ and ω scansh = −8→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −11→11
Tmin = 0.583, Tmax = 0.746l = −16→16
13338 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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.074H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0397P)2 + 0.2033P]
where P = (Fo2 + 2Fc2)/3
3422 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C16H12BrFO2Sγ = 113.609 (1)°
Mr = 367.23V = 741.08 (2) Å3
Triclinic, P1Z = 2
a = 7.6696 (1) ÅMo Kα radiation
b = 8.6308 (1) ŵ = 2.93 mm−1
c = 12.3225 (2) ÅT = 173 K
α = 96.084 (1)°0.26 × 0.16 × 0.13 mm
β = 91.510 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3422 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2976 reflections with I > 2σ(I)
Tmin = 0.583, Tmax = 0.746Rint = 0.029
13338 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.07Δρmax = 0.33 e Å−3
3422 reflectionsΔρmin = −0.56 e Å−3
192 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
Br1−0.07124 (3)0.06945 (2)0.199937 (19)0.04181 (9)
S10.18515 (6)0.85094 (6)0.34130 (4)0.02781 (11)
F10.6274 (2)0.6390 (2)0.64210 (12)0.0602 (4)
O10.32437 (18)0.74870 (16)0.04617 (10)0.0286 (3)
O2−0.01904 (19)0.75643 (19)0.36136 (12)0.0377 (3)
C10.2264 (3)0.7600 (2)0.21574 (14)0.0258 (4)
C20.1739 (2)0.5831 (2)0.17564 (14)0.0246 (4)
C30.0805 (2)0.4290 (2)0.21663 (15)0.0264 (4)
H30.03700.42410.28820.032*
C40.0547 (3)0.2838 (2)0.14748 (16)0.0290 (4)
C50.1195 (3)0.2869 (3)0.04259 (16)0.0306 (4)
H50.09750.1823−0.00110.037*
C60.2153 (2)0.4392 (3)0.00081 (15)0.0282 (4)
C70.2371 (2)0.5836 (2)0.07052 (14)0.0247 (4)
C80.3136 (3)0.8532 (2)0.13575 (15)0.0278 (4)
C90.2924 (3)0.4477 (3)−0.11043 (16)0.0371 (5)
H9A0.28460.5445−0.14200.056*
H9B0.21690.3418−0.15820.056*
H9C0.42580.4622−0.10360.056*
C100.3976 (3)1.0383 (3)0.12828 (18)0.0372 (5)
H10A0.36401.09830.19080.056*
H10B0.34771.05990.06010.056*
H10C0.53671.07930.12900.056*
C110.3197 (3)0.7776 (2)0.42827 (14)0.0266 (4)
C120.5103 (3)0.8142 (3)0.41325 (17)0.0339 (4)
H120.56840.87180.35360.041*
C130.6149 (3)0.7668 (3)0.48527 (18)0.0392 (5)
H130.74530.79040.47620.047*
C140.5250 (3)0.6845 (3)0.57035 (17)0.0392 (5)
C150.3374 (3)0.6460 (3)0.58663 (18)0.0432 (5)
H150.27980.58730.64590.052*
C160.2333 (3)0.6950 (3)0.51448 (16)0.0348 (4)
H160.10310.67170.52440.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04528 (14)0.02586 (12)0.05240 (15)0.01188 (9)0.00989 (10)0.00587 (9)
S10.0333 (2)0.0265 (2)0.0255 (2)0.01415 (19)0.00559 (18)0.00215 (18)
F10.0650 (9)0.0718 (10)0.0519 (8)0.0382 (8)−0.0190 (7)0.0048 (7)
O10.0308 (6)0.0331 (7)0.0241 (6)0.0142 (5)0.0064 (5)0.0068 (5)
O20.0312 (7)0.0510 (9)0.0346 (7)0.0200 (6)0.0082 (6)0.0056 (6)
C10.0290 (9)0.0263 (9)0.0236 (8)0.0124 (7)0.0040 (7)0.0042 (7)
C20.0240 (8)0.0293 (9)0.0230 (8)0.0135 (7)0.0009 (7)0.0031 (7)
C30.0270 (8)0.0279 (9)0.0255 (9)0.0120 (7)0.0018 (7)0.0053 (7)
C40.0267 (9)0.0270 (9)0.0346 (10)0.0124 (7)−0.0004 (7)0.0035 (8)
C50.0271 (9)0.0336 (10)0.0318 (10)0.0157 (8)−0.0040 (7)−0.0047 (8)
C60.0239 (8)0.0395 (11)0.0235 (8)0.0167 (8)−0.0019 (7)−0.0011 (8)
C70.0227 (8)0.0302 (9)0.0235 (8)0.0126 (7)0.0009 (7)0.0064 (7)
C80.0290 (9)0.0306 (10)0.0261 (9)0.0140 (7)0.0046 (7)0.0056 (7)
C90.0351 (10)0.0512 (13)0.0255 (9)0.0193 (9)0.0026 (8)−0.0012 (9)
C100.0433 (11)0.0316 (11)0.0391 (11)0.0152 (9)0.0136 (9)0.0122 (9)
C110.0300 (9)0.0232 (9)0.0234 (8)0.0087 (7)0.0027 (7)−0.0016 (7)
C120.0316 (9)0.0348 (11)0.0311 (10)0.0097 (8)0.0065 (8)0.0003 (8)
C130.0309 (10)0.0441 (12)0.0408 (12)0.0166 (9)−0.0021 (9)−0.0068 (9)
C140.0463 (12)0.0398 (12)0.0335 (11)0.0227 (10)−0.0119 (9)−0.0044 (9)
C150.0478 (12)0.0501 (13)0.0329 (11)0.0195 (10)0.0034 (9)0.0121 (10)
C160.0315 (10)0.0411 (11)0.0306 (10)0.0123 (8)0.0061 (8)0.0085 (8)
Geometric parameters (Å, º) top
Br1—C41.9047 (19)C8—C101.479 (3)
S1—O21.4896 (14)C9—H9A0.9800
S1—C11.7542 (18)C9—H9B0.9800
S1—C111.796 (2)C9—H9C0.9800
F1—C141.355 (2)C10—H10A0.9800
O1—C81.376 (2)C10—H10B0.9800
O1—C71.381 (2)C10—H10C0.9800
C1—C81.355 (3)C11—C161.377 (3)
C1—C21.440 (2)C11—C121.388 (3)
C2—C31.391 (2)C12—C131.379 (3)
C2—C71.395 (2)C12—H120.9500
C3—C41.379 (3)C13—C141.372 (3)
C3—H30.9500C13—H130.9500
C4—C51.396 (3)C14—C151.367 (3)
C5—C61.387 (3)C15—C161.385 (3)
C5—H50.9500C15—H150.9500
C6—C71.385 (3)C16—H160.9500
C6—C91.504 (3)
O2—S1—C1107.96 (8)C6—C9—H9B109.5
O2—S1—C11106.25 (9)H9A—C9—H9B109.5
C1—S1—C1197.50 (8)C6—C9—H9C109.5
C8—O1—C7106.70 (14)H9A—C9—H9C109.5
C8—C1—C2107.61 (16)H9B—C9—H9C109.5
C8—C1—S1123.11 (14)C8—C10—H10A109.5
C2—C1—S1129.25 (14)C8—C10—H10B109.5
C3—C2—C7119.70 (17)H10A—C10—H10B109.5
C3—C2—C1135.32 (17)C8—C10—H10C109.5
C7—C2—C1104.97 (16)H10A—C10—H10C109.5
C4—C3—C2116.19 (17)H10B—C10—H10C109.5
C4—C3—H3121.9C16—C11—C12120.99 (19)
C2—C3—H3121.9C16—C11—S1118.35 (15)
C3—C4—C5123.27 (18)C12—C11—S1120.50 (15)
C3—C4—Br1117.87 (14)C13—C12—C11119.71 (19)
C5—C4—Br1118.84 (14)C13—C12—H12120.1
C6—C5—C4121.43 (18)C11—C12—H12120.1
C6—C5—H5119.3C14—C13—C12118.06 (19)
C4—C5—H5119.3C14—C13—H13121.0
C7—C6—C5114.55 (17)C12—C13—H13121.0
C7—C6—C9122.55 (18)F1—C14—C15118.2 (2)
C5—C6—C9122.89 (18)F1—C14—C13118.4 (2)
O1—C7—C6124.99 (16)C15—C14—C13123.4 (2)
O1—C7—C2110.17 (15)C14—C15—C16118.3 (2)
C6—C7—C2124.84 (17)C14—C15—H15120.8
C1—C8—O1110.55 (16)C16—C15—H15120.8
C1—C8—C10132.90 (17)C11—C16—C15119.53 (19)
O1—C8—C10116.54 (16)C11—C16—H16120.2
C6—C9—H9A109.5C15—C16—H16120.2
O2—S1—C1—C8130.04 (16)C1—C2—C7—O10.42 (19)
C11—S1—C1—C8−120.12 (17)C3—C2—C7—C6−0.4 (3)
O2—S1—C1—C2−47.76 (19)C1—C2—C7—C6−179.62 (17)
C11—S1—C1—C262.07 (18)C2—C1—C8—O1−0.9 (2)
C8—C1—C2—C3−178.74 (19)S1—C1—C8—O1−179.16 (12)
S1—C1—C2—C3−0.7 (3)C2—C1—C8—C10180.0 (2)
C8—C1—C2—C70.3 (2)S1—C1—C8—C101.8 (3)
S1—C1—C2—C7178.39 (14)C7—O1—C8—C11.2 (2)
C7—C2—C3—C4−0.8 (2)C7—O1—C8—C10−179.57 (16)
C1—C2—C3—C4178.19 (19)O2—S1—C11—C16−17.77 (17)
C2—C3—C4—C51.0 (3)C1—S1—C11—C16−129.02 (16)
C2—C3—C4—Br1179.66 (12)O2—S1—C11—C12166.73 (15)
C3—C4—C5—C6−0.1 (3)C1—S1—C11—C1255.49 (16)
Br1—C4—C5—C6−178.75 (13)C16—C11—C12—C130.3 (3)
C4—C5—C6—C7−1.0 (3)S1—C11—C12—C13175.68 (15)
C4—C5—C6—C9178.10 (17)C11—C12—C13—C14−0.2 (3)
C8—O1—C7—C6179.06 (17)C12—C13—C14—F1−179.34 (18)
C8—O1—C7—C2−0.98 (19)C12—C13—C14—C150.6 (3)
C5—C6—C7—O1−178.80 (16)F1—C14—C15—C16178.93 (19)
C9—C6—C7—O12.1 (3)C13—C14—C15—C16−1.0 (3)
C5—C6—C7—C21.3 (3)C12—C11—C16—C15−0.7 (3)
C9—C6—C7—C2−177.84 (17)S1—C11—C16—C15−176.19 (16)
C3—C2—C7—O1179.65 (15)C14—C15—C16—C111.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.952.413.259 (2)148
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H12BrFO2S
Mr367.23
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.6696 (1), 8.6308 (1), 12.3225 (2)
α, β, γ (°)96.084 (1), 91.510 (1), 113.609 (1)
V (Å3)741.08 (2)
Z2
Radiation typeMo Kα
µ (mm−1)2.93
Crystal size (mm)0.26 × 0.16 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.583, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		13338, 3422, 2976
Rint0.029
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.074, 1.07
No. of reflections3422
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.33, −0.56

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
C13—H13···O2i0.952.413.259 (2)148.1
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

This work was supported by the Blue-Bio Industry RIC at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan City.

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ISSN: 2056-9890
Volume 67| Part 2| February 2011| Page o351
doi:10.1107/S1600536810049986
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