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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 70| Part 11| November 2014| Page o1169
doi:10.1107/S1600536814022569

Crystal structure of 2-(3-fluoro­phen­yl)-5-iodo-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choia 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

Edited by P. McArdle, National University of Ireland, Ireland (Received 11 October 2014; accepted 14 October 2014; online 18 October 2014)

In the title compound, C15H10FIO2S, the dihedral angle between the planes of the benzo­furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 3-fluoro­phenyl ring is 29.63 (7)°. In the crystal, mol­ecules are linked into inversion dimers along the b-axis direction by two different pairs of C—H⋯O hydrogen bonds and I⋯O [3.228 (1) Å] contacts.

CCDC reference: 1029138

1. Related literature

For a related structure and background to benzo­furan derivatives, see: Choi & Lee (2014[Choi, H. D. & Lee, U. (2014). Acta Cryst. E70, o991-o992.]). For further synthetic details, see: Choi et al. (1999[Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 606-608.]). 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]

2. Experimental

2.1. Crystal data

  • C15H10FIO2S

  • Mr = 400.19

  • Triclinic, [P \overline 1]

  • a = 8.1348 (3) Å

  • b = 8.6378 (3) Å

  • c = 10.8350 (4) Å

  • α = 86.063 (1)°

  • β = 82.088 (1)°

  • γ = 66.408 (1)°

  • V = 690.99 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.48 mm−1

  • T = 173 K

  • 0.45 × 0.28 × 0.11 mm

2.2. 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 = 0.496, Tmax = 0.746

  • 12585 measured reflections

  • 3450 independent reflections

  • 3226 reflections with I > 2σ(I)

  • Rint = 0.028

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.021

  • wR(F2) = 0.054

  • S = 1.05

  • 3450 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.71 e Å−3

  • Δρmin = −0.59 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C6—H6⋯O1i 0.95 2.57 3.520 (2) 177
C11—H11⋯O2ii 0.95 2.55 3.372 (2) 145
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1029138

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814022569/qm2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022569/qm2109Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022569/qm2109Isup3.cml

checkCIF report


Comment top

As part of our continuing program for benzofuran derivatives (Choi & Lee, 2014), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.015 (2) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring is essentially planar, with a mean deviation of 0.002 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 3-fluorophenyl ring is 29.63 (7)°. In the crystal structure (Fig. 2), molecules are linked into inversion-related dimers along b-axis direction by two different pairs of C—H···O hydrogen bonds (Table 1) and I···O halogen-bondings (Politzer et al., 2007) between the iodine and the O atom of the sulfinyl group [I1···O2iii = 3.228 (2) Å, C4—I1···O2iii = 162.99 (6)°, symmetry code: (iii) - x + 1, - y + 2, - z + 2],

Related literature top

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014). For further synthetic details, see: Choi et al. (1999). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

The starting material 2-(3-fluorophenyl)-5-iodo-3-methylsulfanyl-1-benzofuran was prepared by literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(3-fluorophenyl)-5-iodo-3-methylsulfanyl-1-benzofuran (346 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 10 ml) 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 73% (263 mg); m.p. 453–454 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 (26 mg) in ethyl acetate (25 ml) 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, respectively. Uiso (H) = 1.2Ueq (C) for aryl and 1.5Ueq (C)) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).

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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
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.

Fig. 2. A view of the C—H···O and I···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, -y + 2, -z + 1; (ii) -x + 2, -y + 1, -z; (iii) -x + 1, -y + 2, -z + 2.]
2-(3-Fluorophenyl)-5-iodo-3-methylsulfinyl-1-benzofuran top
Crystal data top
C15H10FIO2SZ = 2
Mr = 400.19F(000) = 388
Triclinic, P1Dx = 1.923 Mg m−3
Hall symbol: -P 1Melting point = 454–453 K
a = 8.1348 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.6378 (3) ÅCell parameters from 8421 reflections
c = 10.8350 (4) Åθ = 2.6–28.4°
α = 86.063 (1)°µ = 2.48 mm−1
β = 82.088 (1)°T = 173 K
γ = 66.408 (1)°Block, colourless
V = 690.99 (4) Å30.45 × 0.28 × 0.11 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3450 independent reflections
Radiation source: rotating anode3226 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.9°
ϕ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −11→11
Tmin = 0.496, Tmax = 0.746l = −14→14
12585 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)] = 0.021Hydrogen site location: difference Fourier map
wR(F2) = 0.054H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0277P)2 + 0.2506P]
where P = (Fo2 + 2Fc2)/3
3450 reflections(Δ/σ)max = 0.002
182 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.59 e Å−3
Crystal data top
C15H10FIO2Sγ = 66.408 (1)°
Mr = 400.19V = 690.99 (4) Å3
Triclinic, P1Z = 2
a = 8.1348 (3) ÅMo Kα radiation
b = 8.6378 (3) ŵ = 2.48 mm−1
c = 10.8350 (4) ÅT = 173 K
α = 86.063 (1)°0.45 × 0.28 × 0.11 mm
β = 82.088 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3450 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3226 reflections with I > 2σ(I)
Tmin = 0.496, Tmax = 0.746Rint = 0.028
12585 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0210 restraints
wR(F2) = 0.054H-atom parameters constrained
S = 1.05Δρmax = 0.71 e Å−3
3450 reflectionsΔρmin = −0.59 e Å−3
182 parameters
Special details top

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.59 (s, 1H), 7.70 (dd, J =8.56 and 1.72 Hz, 1H), 7.46-7.62 (m, 3H), 7.36 (d, J =8.88 Hz, 1H), 6.16-7.22 (m, 1H), 3.11 (s, 3H).

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
I10.171392 (16)1.149394 (16)1.025925 (12)0.03179 (6)
S10.78329 (6)0.70139 (6)0.61226 (5)0.02565 (10)
F10.44813 (19)0.69674 (18)0.05731 (12)0.0428 (3)
O10.29753 (17)0.86217 (16)0.49979 (13)0.0257 (3)
O20.81435 (19)0.83024 (18)0.67958 (15)0.0322 (3)
C10.5521 (2)0.7849 (2)0.59123 (18)0.0236 (4)
C20.4042 (2)0.8963 (2)0.67518 (18)0.0229 (3)
C30.3844 (2)0.9583 (2)0.79446 (18)0.0245 (4)
H30.48510.93120.83930.029*
C40.2108 (2)1.0612 (2)0.84450 (18)0.0252 (4)
C50.0602 (3)1.1041 (2)0.77957 (19)0.0279 (4)
H5−0.05601.17530.81730.033*
C60.0793 (3)1.0437 (2)0.6614 (2)0.0280 (4)
H6−0.02091.07180.61580.034*
C70.2528 (2)0.9398 (2)0.61297 (18)0.0240 (4)
C80.4815 (2)0.7686 (2)0.48808 (18)0.0239 (4)
C90.5539 (2)0.6727 (2)0.37323 (18)0.0246 (4)
C100.7027 (3)0.5184 (2)0.36961 (19)0.0284 (4)
H100.76110.47570.44220.034*
C110.7657 (3)0.4272 (3)0.2604 (2)0.0298 (4)
H110.86800.32280.25830.036*
C120.6806 (3)0.4872 (3)0.1544 (2)0.0310 (4)
H120.72230.42500.07940.037*
C140.4675 (3)0.7348 (2)0.26611 (18)0.0259 (4)
H140.36610.83960.26660.031*
C130.5339 (3)0.6395 (3)0.16068 (19)0.0296 (4)
C150.7795 (3)0.5423 (3)0.7268 (2)0.0399 (5)
H15A0.89900.48630.75540.060*
H15B0.74830.45870.68980.060*
H15C0.68930.59490.79760.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02741 (8)0.03722 (9)0.02882 (8)−0.01142 (6)0.00213 (5)−0.00751 (6)
S10.01711 (19)0.0255 (2)0.0331 (2)−0.00688 (17)−0.00367 (17)−0.00041 (18)
F10.0462 (8)0.0463 (8)0.0316 (7)−0.0101 (6)−0.0147 (6)−0.0038 (6)
O10.0192 (6)0.0277 (7)0.0269 (7)−0.0050 (5)−0.0048 (5)−0.0025 (5)
O20.0279 (7)0.0310 (7)0.0421 (8)−0.0142 (6)−0.0108 (6)0.0011 (6)
C10.0189 (8)0.0222 (8)0.0287 (9)−0.0072 (7)−0.0034 (7)0.0005 (7)
C20.0187 (8)0.0212 (8)0.0283 (9)−0.0078 (7)−0.0032 (7)0.0020 (7)
C30.0205 (8)0.0259 (9)0.0272 (9)−0.0089 (7)−0.0043 (7)0.0010 (7)
C40.0232 (8)0.0245 (9)0.0279 (9)−0.0100 (7)−0.0014 (7)−0.0001 (7)
C50.0204 (8)0.0254 (9)0.0341 (10)−0.0059 (7)−0.0007 (7)−0.0007 (8)
C60.0184 (8)0.0292 (9)0.0340 (10)−0.0059 (7)−0.0063 (7)0.0000 (8)
C70.0218 (8)0.0235 (8)0.0254 (9)−0.0074 (7)−0.0045 (7)0.0004 (7)
C80.0181 (8)0.0215 (8)0.0295 (9)−0.0060 (7)−0.0019 (7)0.0019 (7)
C90.0228 (8)0.0258 (9)0.0280 (9)−0.0127 (7)−0.0025 (7)−0.0013 (7)
C100.0248 (9)0.0283 (9)0.0305 (10)−0.0085 (7)−0.0042 (7)−0.0010 (8)
C110.0225 (9)0.0270 (9)0.0363 (11)−0.0066 (7)−0.0002 (8)−0.0030 (8)
C120.0284 (9)0.0331 (10)0.0318 (10)−0.0128 (8)0.0008 (8)−0.0076 (8)
C140.0224 (8)0.0254 (9)0.0307 (9)−0.0101 (7)−0.0043 (7)0.0009 (7)
C130.0291 (9)0.0342 (10)0.0283 (10)−0.0148 (8)−0.0061 (8)0.0000 (8)
C150.0357 (11)0.0310 (11)0.0560 (14)−0.0147 (9)−0.0186 (10)0.0156 (10)
Geometric parameters (Å, º) top
I1—C42.0937 (19)C6—C71.385 (3)
I1—O2i3.2282 (16)C6—H60.9500
S1—O21.4906 (15)C8—C91.460 (3)
S1—C11.7660 (18)C9—C101.396 (3)
S1—C151.794 (2)C9—C141.402 (3)
F1—C131.360 (2)C10—C111.386 (3)
O1—C71.371 (2)C10—H100.9500
O1—C81.380 (2)C11—C121.385 (3)
C1—C81.364 (3)C11—H110.9500
C1—C21.447 (2)C12—C131.376 (3)
C2—C71.392 (3)C12—H120.9500
C2—C31.397 (3)C14—C131.370 (3)
C3—C41.389 (2)C14—H140.9500
C3—H30.9500C15—H15A0.9800
C4—C51.404 (3)C15—H15B0.9800
C5—C61.382 (3)C15—H15C0.9800
C5—H50.9500
C4—I1—O2i162.99 (6)C1—C8—C9135.08 (17)
O2—S1—C1107.27 (8)O1—C8—C9114.36 (16)
O2—S1—C15105.59 (11)C10—C9—C14119.72 (18)
C1—S1—C1597.77 (10)C10—C9—C8121.22 (18)
C7—O1—C8106.51 (14)C14—C9—C8119.02 (17)
C8—C1—C2107.22 (16)C11—C10—C9120.19 (19)
C8—C1—S1126.32 (14)C11—C10—H10119.9
C2—C1—S1126.23 (14)C9—C10—H10119.9
C7—C2—C3119.44 (16)C12—C11—C10120.41 (19)
C7—C2—C1104.72 (16)C12—C11—H11119.8
C3—C2—C1135.82 (17)C10—C11—H11119.8
C4—C3—C2116.96 (17)C13—C12—C11118.20 (18)
C4—C3—H3121.5C13—C12—H12120.9
C2—C3—H3121.5C11—C12—H12120.9
C3—C4—C5122.53 (18)C13—C14—C9117.96 (18)
C3—C4—I1118.63 (14)C13—C14—H14121.0
C5—C4—I1118.81 (13)C9—C14—H14121.0
C6—C5—C4120.71 (17)F1—C13—C14118.31 (18)
C6—C5—H5119.6F1—C13—C12118.15 (18)
C4—C5—H5119.6C14—C13—C12123.5 (2)
C5—C6—C7116.21 (18)S1—C15—H15A109.5
C5—C6—H6121.9S1—C15—H15B109.5
C7—C6—H6121.9H15A—C15—H15B109.5
O1—C7—C6124.79 (17)S1—C15—H15C109.5
O1—C7—C2111.03 (15)H15A—C15—H15C109.5
C6—C7—C2124.15 (18)H15B—C15—H15C109.5
C1—C8—O1110.51 (16)
O2—S1—C1—C8141.12 (17)C3—C2—C7—C60.5 (3)
C15—S1—C1—C8−109.83 (19)C1—C2—C7—C6178.84 (18)
O2—S1—C1—C2−32.64 (19)C2—C1—C8—O10.0 (2)
C15—S1—C1—C276.41 (18)S1—C1—C8—O1−174.78 (13)
C8—C1—C2—C7−0.4 (2)C2—C1—C8—C9−177.5 (2)
S1—C1—C2—C7174.33 (15)S1—C1—C8—C97.7 (3)
C8—C1—C2—C3177.6 (2)C7—O1—C8—C10.5 (2)
S1—C1—C2—C3−7.7 (3)C7—O1—C8—C9178.56 (16)
C7—C2—C3—C40.2 (3)C1—C8—C9—C1029.0 (3)
C1—C2—C3—C4−177.6 (2)O1—C8—C9—C10−148.40 (17)
C2—C3—C4—C5−0.6 (3)C1—C8—C9—C14−153.2 (2)
C2—C3—C4—I1177.44 (13)O1—C8—C9—C1429.3 (2)
O2i—I1—C4—C3−46.0 (3)C14—C9—C10—C110.4 (3)
O2i—I1—C4—C5132.10 (18)C8—C9—C10—C11178.10 (18)
C3—C4—C5—C60.3 (3)C9—C10—C11—C12−0.7 (3)
I1—C4—C5—C6−177.70 (15)C10—C11—C12—C130.5 (3)
C4—C5—C6—C70.3 (3)C10—C9—C14—C130.1 (3)
C8—O1—C7—C6−178.87 (18)C8—C9—C14—C13−177.66 (17)
C8—O1—C7—C2−0.8 (2)C9—C14—C13—F1178.38 (17)
C5—C6—C7—O1177.14 (18)C9—C14—C13—C12−0.3 (3)
C5—C6—C7—C2−0.7 (3)C11—C12—C13—F1−178.69 (18)
C3—C2—C7—O1−177.65 (16)C11—C12—C13—C140.0 (3)
C1—C2—C7—O10.7 (2)
Symmetry code: (i) −x+1, −y+2, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1ii0.952.573.520 (2)177
C11—H11···O2iii0.952.553.372 (2)145
Symmetry codes: (ii) −x, −y+2, −z+1; (iii) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.952.573.520 (2)177.1
C11—H11···O2ii0.952.553.372 (2)144.9
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+2, −y+1, −z+1.
 

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 70| Part 11| November 2014| Page o1169
doi:10.1107/S1600536814022569
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