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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 6| June 2014| Page o659
doi:10.1107/S1600536814010459

2-(2-Fluoro­phen­yl)-5-iodo-7-methyl-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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 May 2014; accepted 8 May 2014; online 17 May 2014)

In the title compound, C16H12FIO2S, the dihedral angle between the plane of the benzo­furan ring system (r.m.s. deviation = 0.023 Å) and that of the 2-fluoro­phenyl ring is 39.78 (7)°. In the crystal, mol­ecules are linked via pairs of I⋯π contacts [3.812 (2) Å] and a π–π inter­action between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.821 (2) Å] into inversion dimers. These dimers are further linked by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.668 (2) Å]. The mol­ecules stack along the a-axis direction. In addition, C—H⋯O hydrogen bonds are observed between inversion-related dimers.

CCDC reference: 1001669

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1680.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1612.], 2014[Choi, H. D., Seo, P. J. & Lee, U. (2014). Acta Cryst. E70, o178.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12FIO2S

  • Mr = 414.22

  • Monoclinic, P 21 /c

  • a = 7.9460 (2) Å

  • b = 24.1545 (7) Å

  • c = 7.9685 (2) Å

  • β = 100.997 (1)°

  • V = 1501.32 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.28 mm−1

  • T = 173 K

  • 0.42 × 0.40 × 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 = 0.541, Tmax = 0.746

  • 14688 measured reflections

  • 3721 independent reflections

  • 3465 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.059

  • S = 1.12

  • 3721 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.47 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 2.49 3.355 (3) 151
C15—H15⋯O2ii 0.95 2.48 3.185 (3) 131
Symmetry codes: (i) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) 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 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: 1001669

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814010459/hb7228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010459/hb7228Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010459/hb7228Isup3.cml

checkCIF report


Comment top

As a part of our ongoing study of 5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2010), 3-fluorophenyl (Choi et al., 2012) and 4-methylphenyl (Choi et al., 2014) substituents in 2-position, we report here 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 0.019 (2) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 39.78 (7)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C4–I1···π contacts between the iodine atom and the furan ring of a neighbouring molecule with a C4–I1···Cg1iv = 3.812 (2) Å (Cg1 is the C1/C2/C7/O1/C8 furan ring), and by a π···π interaction between the benzene rings of neighbouring molecules, with a Cg2···Cg2iv distance of 3.821 (2) Å and an interplanar distance of 3.581 (2) Å resulting in a slippage of 1.333 (2) Å (Cg2 is the C2-C7 benzene ring), into inversion dimers. These dimers are further linked by π···π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2iii distance of 3.668 (2) Å and an interplanar distance of 3.375 (2) Å resulting in a slippage of 1.437 (2) Å. The molecules stack along the a-axis direction. In addition, C–H···O hydrogen bonds (Table 1) are observed between inversion-related dimers.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012, 2014).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(2-fluorophenyl)-5-iodo-7-methyl-3-methylsulfanyl-1-benzofuran (358 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 72%, m.p. 469-470 K; Rf = 0.48 (hexane-ethyl acetate, 1:1 v/v)]. Colourless blocks 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 aryl, 0.99 Å for methyl H atoms. Uiso (H) = 1.2Ueq (C) for aryl and 1.5Ueq (C) for methyl H atoms. The methyl groups were allowed to rotate, but not to tip, to best fit the electron density.

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
[Figure 1] Fig. 1. The molecular structure of the title molecule with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the C–H···O, I···π and π···π 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 + 1/2, z - 1/2; (ii) x - 1, y, z; (iii)- x + 1, - y + 1, - z + 1; (iv) - x + 1, - y + 1, - z + 2; (v) x + 1, - y + 1/2, z + 1/2; (vi) x + 1, y, z.]
2-(2-Fluorophenyl)-5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran top
Crystal data top
C16H12FIO2SF(000) = 808
Mr = 414.22Dx = 1.833 Mg m−3
Monoclinic, P21/cMelting point = 470–469 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.9460 (2) ÅCell parameters from 8240 reflections
b = 24.1545 (7) Åθ = 2.6–28.3°
c = 7.9685 (2) ŵ = 2.28 mm−1
β = 100.997 (1)°T = 173 K
V = 1501.32 (7) Å3Block, colourless
Z = 40.42 × 0.40 × 0.13 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3721 independent reflections
Radiation source: rotating anode3465 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.025
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.7°
ϕ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −32→27
Tmin = 0.541, Tmax = 0.746l = −10→10
14688 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)] = 0.026Hydrogen site location: difference Fourier map
wR(F2) = 0.059H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0242P)2 + 1.1461P]
where P = (Fo2 + 2Fc2)/3
3721 reflections(Δ/σ)max = 0.002
192 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C16H12FIO2SV = 1501.32 (7) Å3
Mr = 414.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9460 (2) ŵ = 2.28 mm−1
b = 24.1545 (7) ÅT = 173 K
c = 7.9685 (2) Å0.42 × 0.40 × 0.13 mm
β = 100.997 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3721 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3465 reflections with I > 2σ(I)
Tmin = 0.541, Tmax = 0.746Rint = 0.025
14688 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 1.12Δρmax = 0.47 e Å−3
3721 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
I10.836495 (19)0.586239 (6)1.028521 (19)0.02707 (6)
S10.69187 (7)0.33626 (2)0.73135 (7)0.02286 (12)
F10.54937 (17)0.31240 (6)0.36409 (19)0.0312 (3)
O10.31221 (18)0.43857 (6)0.56014 (19)0.0199 (3)
O20.8687 (2)0.35305 (8)0.7161 (2)0.0339 (4)
C10.5544 (3)0.39339 (9)0.6766 (3)0.0202 (4)
C20.5700 (3)0.44971 (9)0.7398 (3)0.0194 (4)
C30.6952 (3)0.48077 (9)0.8473 (3)0.0221 (4)
H30.80190.46510.89980.026*
C40.6553 (3)0.53565 (9)0.8730 (3)0.0214 (4)
C50.4976 (3)0.55926 (9)0.7989 (3)0.0223 (4)
H50.47640.59700.82150.027*
C60.3717 (3)0.52899 (9)0.6932 (3)0.0203 (4)
C70.4166 (3)0.47492 (9)0.6656 (3)0.0192 (4)
C80.4009 (3)0.38961 (9)0.5680 (3)0.0195 (4)
C90.1982 (3)0.55220 (10)0.6186 (3)0.0284 (5)
H9A0.17310.54560.49500.043*
H9B0.19730.59210.64080.043*
H9C0.11100.53400.67130.043*
C100.3059 (3)0.34517 (9)0.4659 (3)0.0205 (4)
C110.3805 (3)0.30761 (9)0.3698 (3)0.0240 (4)
C120.2887 (3)0.26551 (10)0.2777 (3)0.0311 (5)
H120.34330.24030.21380.037*
C130.1158 (3)0.26053 (11)0.2799 (3)0.0336 (6)
H130.05150.23100.22010.040*
C140.0361 (3)0.29845 (11)0.3690 (3)0.0298 (5)
H14−0.08360.29570.36690.036*
C150.1300 (3)0.34039 (10)0.4610 (3)0.0234 (4)
H150.07410.36630.52150.028*
C160.6912 (4)0.33410 (12)0.9561 (3)0.0344 (6)
H16A0.76730.30441.00920.052*
H16B0.57450.32700.97400.052*
H16C0.73150.36961.00810.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02576 (9)0.02477 (9)0.02996 (9)−0.00501 (5)0.00348 (6)−0.00525 (6)
S10.0252 (3)0.0190 (3)0.0238 (3)0.0066 (2)0.0033 (2)−0.0005 (2)
F10.0262 (7)0.0334 (8)0.0364 (8)0.0013 (6)0.0118 (6)−0.0074 (6)
O10.0192 (7)0.0182 (8)0.0213 (7)0.0021 (6)0.0018 (6)−0.0012 (6)
O20.0231 (8)0.0399 (10)0.0395 (10)0.0096 (7)0.0082 (7)0.0036 (8)
C10.0203 (10)0.0188 (10)0.0218 (10)0.0031 (8)0.0044 (8)−0.0002 (8)
C20.0205 (10)0.0174 (10)0.0209 (10)0.0010 (8)0.0050 (8)0.0005 (8)
C30.0200 (10)0.0214 (11)0.0242 (11)0.0012 (8)0.0028 (8)−0.0002 (8)
C40.0227 (10)0.0211 (11)0.0209 (10)−0.0032 (8)0.0050 (8)−0.0011 (8)
C50.0268 (11)0.0162 (10)0.0252 (11)0.0006 (8)0.0085 (9)−0.0002 (8)
C60.0212 (10)0.0192 (10)0.0214 (10)0.0036 (8)0.0060 (8)0.0025 (8)
C70.0189 (10)0.0200 (11)0.0192 (10)0.0000 (8)0.0049 (8)−0.0010 (8)
C80.0209 (10)0.0185 (10)0.0193 (10)0.0034 (8)0.0050 (8)0.0002 (8)
C90.0245 (11)0.0232 (12)0.0362 (13)0.0075 (9)0.0026 (10)0.0011 (9)
C100.0236 (10)0.0185 (11)0.0183 (10)0.0005 (8)0.0011 (8)0.0013 (8)
C110.0259 (11)0.0233 (12)0.0231 (11)0.0014 (9)0.0052 (9)−0.0010 (8)
C120.0400 (14)0.0257 (13)0.0286 (12)−0.0016 (10)0.0089 (10)−0.0084 (9)
C130.0404 (14)0.0299 (13)0.0289 (12)−0.0116 (11)0.0026 (10)−0.0069 (10)
C140.0257 (11)0.0348 (14)0.0279 (12)−0.0066 (10)0.0024 (9)0.0000 (10)
C150.0232 (10)0.0235 (11)0.0231 (11)0.0006 (8)0.0039 (8)0.0006 (8)
C160.0433 (14)0.0357 (14)0.0246 (12)0.0091 (11)0.0077 (10)0.0058 (10)
Geometric parameters (Å, º) top
I1—C42.102 (2)C8—C101.466 (3)
S1—O21.4898 (18)C9—H9A0.9800
S1—C11.763 (2)C9—H9B0.9800
S1—C161.793 (2)C9—H9C0.9800
F1—C111.356 (3)C10—C111.391 (3)
O1—C81.372 (3)C10—C151.396 (3)
O1—C71.378 (2)C11—C121.379 (3)
C1—C81.357 (3)C12—C131.383 (4)
C1—C21.448 (3)C12—H120.9500
C2—C71.389 (3)C13—C141.384 (4)
C2—C31.400 (3)C13—H130.9500
C3—C41.387 (3)C14—C151.383 (3)
C3—H30.9500C14—H140.9500
C4—C51.401 (3)C15—H150.9500
C5—C61.387 (3)C16—H16A0.9800
C5—H50.9500C16—H16B0.9800
C6—C71.383 (3)C16—H16C0.9800
C6—C91.502 (3)
O2—S1—C1108.46 (10)C6—C9—H9B109.5
O2—S1—C16105.79 (12)H9A—C9—H9B109.5
C1—S1—C1698.65 (11)C6—C9—H9C109.5
C8—O1—C7106.08 (16)H9A—C9—H9C109.5
C8—C1—C2106.99 (18)H9B—C9—H9C109.5
C8—C1—S1122.98 (17)C11—C10—C15117.4 (2)
C2—C1—S1129.91 (16)C11—C10—C8123.7 (2)
C7—C2—C3119.2 (2)C15—C10—C8118.9 (2)
C7—C2—C1104.70 (18)F1—C11—C12118.1 (2)
C3—C2—C1136.0 (2)F1—C11—C10119.4 (2)
C4—C3—C2116.5 (2)C12—C11—C10122.4 (2)
C4—C3—H3121.7C11—C12—C13118.9 (2)
C2—C3—H3121.7C11—C12—H12120.5
C3—C4—C5122.5 (2)C13—C12—H12120.5
C3—C4—I1119.52 (16)C12—C13—C14120.1 (2)
C5—C4—I1117.95 (16)C12—C13—H13119.9
C6—C5—C4121.7 (2)C14—C13—H13119.9
C6—C5—H5119.2C15—C14—C13120.2 (2)
C4—C5—H5119.2C15—C14—H14119.9
C7—C6—C5114.60 (19)C13—C14—H14119.9
C7—C6—C9122.3 (2)C14—C15—C10120.8 (2)
C5—C6—C9123.0 (2)C14—C15—H15119.6
O1—C7—C6123.72 (19)C10—C15—H15119.6
O1—C7—C2110.94 (18)S1—C16—H16A109.5
C6—C7—C2125.3 (2)S1—C16—H16B109.5
C1—C8—O1111.24 (18)H16A—C16—H16B109.5
C1—C8—C10135.1 (2)S1—C16—H16C109.5
O1—C8—C10113.59 (17)H16A—C16—H16C109.5
C6—C9—H9A109.5H16B—C16—H16C109.5
O2—S1—C1—C8132.80 (19)C3—C2—C7—C6−2.5 (3)
C16—S1—C1—C8−117.3 (2)C1—C2—C7—C6178.2 (2)
O2—S1—C1—C2−51.8 (2)C2—C1—C8—O1−2.2 (2)
C16—S1—C1—C258.1 (2)S1—C1—C8—O1174.07 (15)
C8—C1—C2—C72.1 (2)C2—C1—C8—C10−178.3 (2)
S1—C1—C2—C7−173.83 (18)S1—C1—C8—C10−2.0 (4)
C8—C1—C2—C3−177.0 (2)C7—O1—C8—C11.4 (2)
S1—C1—C2—C37.0 (4)C7—O1—C8—C10178.36 (17)
C7—C2—C3—C40.4 (3)C1—C8—C10—C11−44.0 (4)
C1—C2—C3—C4179.5 (2)O1—C8—C10—C11140.0 (2)
C2—C3—C4—C51.0 (3)C1—C8—C10—C15137.3 (3)
C2—C3—C4—I1−178.86 (15)O1—C8—C10—C15−38.6 (3)
C3—C4—C5—C6−0.6 (3)C15—C10—C11—F1176.76 (19)
I1—C4—C5—C6179.31 (16)C8—C10—C11—F1−1.9 (3)
C4—C5—C6—C7−1.3 (3)C15—C10—C11—C12−2.6 (3)
C4—C5—C6—C9176.9 (2)C8—C10—C11—C12178.7 (2)
C8—O1—C7—C6−179.5 (2)F1—C11—C12—C13−179.0 (2)
C8—O1—C7—C20.0 (2)C10—C11—C12—C130.4 (4)
C5—C6—C7—O1−177.70 (19)C11—C12—C13—C142.0 (4)
C9—C6—C7—O14.1 (3)C12—C13—C14—C15−2.2 (4)
C5—C6—C7—C22.9 (3)C13—C14—C15—C10−0.1 (4)
C9—C6—C7—C2−175.3 (2)C11—C10—C15—C142.5 (3)
C3—C2—C7—O1178.00 (18)C8—C10—C15—C14−178.8 (2)
C1—C2—C7—O1−1.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.952.493.355 (3)151
C15—H15···O2ii0.952.483.185 (3)131
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.952.493.355 (3)150.8
C15—H15···O2ii0.952.483.185 (3)131.3
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x−1, y, z.
 

Acknowledgements

This work was supported by Dong-eui University grant No. 2014AA013.

References

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ISSN: 2056-9890
Volume 70| Part 6| June 2014| Page o659
doi:10.1107/S1600536814010459
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