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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 68| Part 5| May 2012| Page o1470
doi:10.1107/S1600536812016789

5-Bromo-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seoa 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 17 April 2012; accepted 17 April 2012; online 21 April 2012)

In the title compound, C15H10BrFO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 30.77 (6)° with the mean plane [mean deviation = 0.014 (1) Å] of the benzofuran ring system. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers. A Br⋯O contact [3.214 (1) Å] is also observed.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2007[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1315-o1316.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o104.]). 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

  • C15H10BrFO2S

  • Mr = 353.20

  • Triclinic, [P \overline 1]

  • a = 8.0494 (1) Å

  • b = 8.5317 (1) Å

  • c = 10.7110 (2) Å

  • α = 87.624 (1)°

  • β = 81.378 (1)°

  • γ = 66.709 (1)°

  • V = 667.87 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.24 mm−1

  • T = 173 K

  • 0.36 × 0.29 × 0.25 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 = 0.391, Tmax = 0.501

  • 11667 measured reflections

  • 3059 independent reflections

  • 2835 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.064

  • S = 1.07

  • 3059 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.46 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 2.55 3.356 (2) 142
Symmetry code: (i) -x+2, -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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016789/is5120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016789/is5120Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016789/is5120Isup3.cml

checkCIF report


Comment top

As a part of our ongoing study of 5-bromo-3-methylsulfinyl-1-benzofuran derivatives containing 2-phenyl (Choi et al., 2007) and 2-(4-fluorophenyl) (Choi et al., 2010) 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 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 30.77 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C—H···O hydrogen bonds (Table 1), and by Br···O halogen-bondings between the bromine atom and the O atom of the S═O unit [Br1···O2i = 3.214 (1) Å, C4—Br1···O2i = 163.28 (5)°] (Politzer et al., 2007).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2007, 2010). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran (270 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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 73%, m.p. 447–448 K; Rf = 0.55 (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 (C—H = 0.95 Å for the aryl and 0.98 Å for the methyl H atoms) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl H atoms were optimized rotationally.

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.
[Figure 2] Fig. 2. A view of the C—H···O and Br···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 + 2, - z + 2 ; (ii) - x + 2, - y + 1, - z + 1.]
5-Bromo-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C15H10BrFO2SZ = 2
Mr = 353.20F(000) = 352
Triclinic, P1Dx = 1.756 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0494 (1) ÅCell parameters from 7435 reflections
b = 8.5317 (1) Åθ = 2.6–27.5°
c = 10.7110 (2) ŵ = 3.24 mm−1
α = 87.624 (1)°T = 173 K
β = 81.378 (1)°Block, colourless
γ = 66.709 (1)°0.36 × 0.29 × 0.25 mm
V = 667.87 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3059 independent reflections
Radiation source: rotating anode2835 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.038
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.9°
ϕ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −11→11
Tmin = 0.391, Tmax = 0.501l = −13→13
11667 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)] = 0.025Hydrogen site location: difference Fourier map
wR(F2) = 0.064H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0304P)2 + 0.2245P]
where P = (Fo2 + 2Fc2)/3
3059 reflections(Δ/σ)max = 0.003
182 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C15H10BrFO2Sγ = 66.709 (1)°
Mr = 353.20V = 667.87 (2) Å3
Triclinic, P1Z = 2
a = 8.0494 (1) ÅMo Kα radiation
b = 8.5317 (1) ŵ = 3.24 mm−1
c = 10.7110 (2) ÅT = 173 K
α = 87.624 (1)°0.36 × 0.29 × 0.25 mm
β = 81.378 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3059 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2835 reflections with I > 2σ(I)
Tmin = 0.391, Tmax = 0.501Rint = 0.038
11667 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.064H-atom parameters constrained
S = 1.07Δρmax = 0.36 e Å−3
3059 reflectionsΔρmin = −0.46 e Å−3
182 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
Br10.17500 (3)1.14433 (2)1.025572 (16)0.03170 (8)
S10.78664 (6)0.69925 (5)0.60864 (4)0.02294 (10)
F10.46013 (17)0.70426 (15)0.04748 (10)0.0391 (3)
O10.29411 (16)0.86282 (14)0.50431 (11)0.0227 (2)
O20.81884 (18)0.83090 (16)0.67671 (13)0.0309 (3)
C10.5524 (2)0.78361 (19)0.59217 (15)0.0207 (3)
C20.4029 (2)0.89580 (19)0.68141 (15)0.0205 (3)
C30.3839 (2)0.9576 (2)0.80375 (15)0.0224 (3)
H30.48590.92970.84750.027*
C40.2095 (2)1.0613 (2)0.85784 (16)0.0236 (3)
C50.0559 (2)1.1060 (2)0.79601 (17)0.0260 (4)
H5−0.06111.17810.83750.031*
C60.0740 (2)1.0455 (2)0.67483 (17)0.0254 (4)
H6−0.02791.07410.63080.030*
C70.2488 (2)0.9411 (2)0.62143 (15)0.0213 (3)
C80.4801 (2)0.7684 (2)0.48847 (15)0.0209 (3)
C90.5542 (2)0.6726 (2)0.36924 (16)0.0214 (3)
C100.4711 (2)0.7376 (2)0.26146 (16)0.0235 (3)
H100.36910.84380.26460.028*
C110.5423 (3)0.6428 (2)0.15148 (16)0.0264 (4)
C120.6896 (3)0.4891 (2)0.14076 (17)0.0288 (4)
H120.73430.42790.06250.035*
C130.7716 (3)0.4254 (2)0.24751 (17)0.0279 (4)
H130.87460.31970.24250.033*
C140.7036 (2)0.5154 (2)0.36110 (17)0.0251 (4)
H140.75890.47010.43410.030*
C150.7821 (3)0.5407 (2)0.7231 (2)0.0362 (5)
H15A0.90360.48270.74830.054*
H15B0.74700.45720.68620.054*
H15C0.69310.59580.79740.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02857 (12)0.03822 (11)0.02513 (11)−0.01096 (8)0.00206 (7)−0.00900 (7)
S10.0157 (2)0.02387 (19)0.0279 (2)−0.00585 (15)−0.00481 (16)0.00069 (15)
F10.0440 (7)0.0454 (6)0.0252 (6)−0.0113 (5)−0.0152 (5)−0.0005 (5)
O10.0172 (6)0.0260 (6)0.0224 (6)−0.0047 (5)−0.0053 (4)−0.0020 (4)
O20.0266 (7)0.0292 (6)0.0416 (8)−0.0129 (5)−0.0134 (6)0.0013 (5)
C10.0163 (8)0.0212 (7)0.0238 (8)−0.0065 (6)−0.0034 (6)0.0000 (6)
C20.0172 (8)0.0205 (7)0.0234 (8)−0.0069 (6)−0.0032 (6)0.0009 (6)
C30.0192 (8)0.0248 (8)0.0233 (8)−0.0081 (6)−0.0050 (6)0.0009 (6)
C40.0241 (9)0.0245 (7)0.0222 (8)−0.0102 (7)−0.0013 (7)−0.0016 (6)
C50.0185 (8)0.0243 (8)0.0309 (9)−0.0047 (6)−0.0003 (7)−0.0012 (7)
C60.0167 (8)0.0264 (8)0.0303 (9)−0.0047 (6)−0.0058 (7)−0.0002 (7)
C70.0199 (8)0.0213 (7)0.0223 (8)−0.0071 (6)−0.0043 (6)0.0004 (6)
C80.0162 (8)0.0209 (7)0.0237 (8)−0.0053 (6)−0.0035 (6)0.0009 (6)
C90.0204 (8)0.0237 (7)0.0224 (8)−0.0107 (6)−0.0035 (6)−0.0016 (6)
C100.0206 (8)0.0244 (7)0.0271 (9)−0.0096 (6)−0.0059 (7)0.0006 (6)
C110.0278 (10)0.0327 (9)0.0227 (8)−0.0147 (7)−0.0084 (7)0.0022 (7)
C120.0287 (10)0.0329 (9)0.0259 (9)−0.0139 (8)0.0000 (7)−0.0065 (7)
C130.0234 (9)0.0256 (8)0.0319 (9)−0.0069 (7)−0.0018 (7)−0.0046 (7)
C140.0234 (9)0.0250 (8)0.0264 (8)−0.0077 (7)−0.0071 (7)0.0007 (6)
C150.0331 (11)0.0301 (9)0.0502 (12)−0.0143 (8)−0.0191 (9)0.0156 (8)
Geometric parameters (Å, º) top
Br1—C41.8994 (17)C6—C71.382 (2)
S1—O21.4884 (13)C6—H60.9500
S1—C11.7662 (17)C8—C91.459 (2)
S1—C151.7951 (19)C9—C141.398 (2)
F1—C111.3604 (19)C9—C101.405 (2)
O1—C71.376 (2)C10—C111.371 (2)
O1—C81.379 (2)C10—H100.9500
C1—C81.362 (2)C11—C121.372 (3)
C1—C21.449 (2)C12—C131.389 (3)
C2—C71.393 (2)C12—H120.9500
C2—C31.397 (2)C13—C141.384 (2)
C3—C41.381 (2)C13—H130.9500
C3—H30.9500C14—H140.9500
C4—C51.402 (2)C15—H15A0.9800
C5—C61.382 (2)C15—H15B0.9800
C5—H50.9500C15—H15C0.9800
Br1···O2i3.2137 (13)
C4—Br1—O2i163.28 (5)C1—C8—C9134.47 (15)
O2—S1—C1107.07 (7)O1—C8—C9114.71 (14)
O2—S1—C15105.85 (9)C14—C9—C10119.48 (15)
C1—S1—C1597.64 (9)C14—C9—C8121.18 (15)
C7—O1—C8106.58 (12)C10—C9—C8119.32 (15)
C8—C1—C2106.97 (14)C11—C10—C9117.81 (16)
C8—C1—S1126.42 (13)C11—C10—H10121.1
C2—C1—S1126.36 (12)C9—C10—H10121.1
C7—C2—C3119.31 (15)F1—C11—C10117.89 (16)
C7—C2—C1105.05 (14)F1—C11—C12118.26 (16)
C3—C2—C1135.62 (15)C10—C11—C12123.84 (16)
C4—C3—C2116.65 (15)C11—C12—C13118.18 (16)
C4—C3—H3121.7C11—C12—H12120.9
C2—C3—H3121.7C13—C12—H12120.9
C3—C4—C5123.30 (16)C14—C13—C12120.14 (16)
C3—C4—Br1118.41 (13)C14—C13—H13119.9
C5—C4—Br1118.28 (13)C12—C13—H13119.9
C6—C5—C4120.26 (16)C13—C14—C9120.54 (16)
C6—C5—H5119.9C13—C14—H14119.7
C4—C5—H5119.9C9—C14—H14119.7
C7—C6—C5116.17 (16)S1—C15—H15A109.5
C7—C6—H6121.9S1—C15—H15B109.5
C5—C6—H6121.9H15A—C15—H15B109.5
O1—C7—C6125.06 (15)S1—C15—H15C109.5
O1—C7—C2110.60 (14)H15A—C15—H15C109.5
C6—C7—C2124.30 (16)H15B—C15—H15C109.5
C1—C8—O1110.79 (14)
O2—S1—C1—C8139.58 (15)C1—C2—C7—C6178.75 (16)
C15—S1—C1—C8−111.19 (16)C2—C1—C8—O1−0.06 (18)
O2—S1—C1—C2−33.90 (16)S1—C1—C8—O1−174.57 (12)
C15—S1—C1—C275.34 (16)C2—C1—C8—C9−177.94 (18)
C8—C1—C2—C7−0.52 (18)S1—C1—C8—C97.5 (3)
S1—C1—C2—C7174.00 (13)C7—O1—C8—C10.63 (18)
C8—C1—C2—C3177.77 (18)C7—O1—C8—C9178.96 (14)
S1—C1—C2—C3−7.7 (3)C1—C8—C9—C1430.3 (3)
C7—C2—C3—C40.2 (2)O1—C8—C9—C14−147.50 (16)
C1—C2—C3—C4−177.90 (18)C1—C8—C9—C10−151.18 (19)
C2—C3—C4—C5−0.4 (3)O1—C8—C9—C1031.0 (2)
C2—C3—C4—Br1178.50 (12)C14—C9—C10—C11−0.3 (3)
C3—C4—C5—C60.2 (3)C8—C9—C10—C11−178.86 (15)
Br1—C4—C5—C6−178.66 (13)C9—C10—C11—F1178.95 (15)
C4—C5—C6—C70.1 (3)C9—C10—C11—C12−0.2 (3)
C8—O1—C7—C6−178.78 (16)F1—C11—C12—C13−179.08 (16)
C8—O1—C7—C2−0.97 (18)C10—C11—C12—C130.1 (3)
C5—C6—C7—O1177.22 (15)C11—C12—C13—C140.6 (3)
C5—C6—C7—C2−0.3 (3)C12—C13—C14—C9−1.2 (3)
C3—C2—C7—O1−177.70 (14)C10—C9—C14—C131.0 (3)
C1—C2—C7—O10.92 (18)C8—C9—C14—C13179.54 (17)
C3—C2—C7—C60.1 (3)
Symmetry code: (i) −x+1, −y+2, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2ii0.952.553.356 (2)142
Symmetry code: (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC15H10BrFO2S
Mr353.20
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.0494 (1), 8.5317 (1), 10.7110 (2)
α, β, γ (°)87.624 (1), 81.378 (1), 66.709 (1)
V (Å3)667.87 (2)
Z2
Radiation typeMo Kα
µ (mm−1)3.24
Crystal size (mm)0.36 × 0.29 × 0.25
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.391, 0.501
No. of measured, independent and
observed [I > 2σ(I)] reflections		11667, 3059, 2835
Rint0.038
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.064, 1.07
No. of reflections3059
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.36, −0.46

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···O2i0.952.553.356 (2)142
Symmetry code: (i) −x+2, −y+1, −z+1.
 

References

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
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1315–o1316.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o104.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1470
doi:10.1107/S1600536812016789
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