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ISSN: 2056-9890

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

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 13 May 2013; accepted 14 May 2013; online 18 May 2013)

In the title compound, C16H12ClFO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 16.43 (4)° with the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzo­furan fragment. In the crystal, mol­ecules are linked by pairs of Cl⋯O contacts [3.1839 (12) Å] into inversion dimers, which are further packed into stacks along the b axis by weak C—H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o706.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o886.]). 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
  • C16H12ClFO2S

  • Mr = 322.77

  • Triclinic, [P \overline 1]

  • a = 7.5374 (3) Å

  • b = 9.7388 (3) Å

  • c = 10.7979 (4) Å

  • α = 106.902 (2)°

  • β = 90.605 (2)°

  • γ = 110.598 (2)°

  • V = 704.24 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 173 K

  • 0.34 × 0.29 × 0.17 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 = 0.669, Tmax = 0.746

  • 13230 measured reflections

  • 3505 independent reflections

  • 3025 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.093

  • S = 1.04

  • 3505 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9A⋯O2i 0.98 2.52 3.2305 (17) 129
Symmetry code: (i) x, y-1, 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


Comment top

As a part of our continuing study of 5-chloro-7-methyl-1-benzofuran derivatives containing [2-(4-chlorophenyl)-3-methylsulfinyl] (Choi et al., 2010a) and [3-ethylsulfinyl-2-(4-fluorophenyl)] (Choi et al., 2010b) 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 0.012 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 16.43 (4)°. In the crystal structure (Fig. 2), molecules are connected by pairs of Cl···O halogen-bondings between the chlorine atom and the O atom of the SO unit [Cl1···O2ii = 3.1839 (12) Å, C4—Cl1···O2ii = 173.77 (6)°] (Politzer et al., 2007) into centrosymmetric dimers, which are further packed into stacks along the b axis by C—H···O hydrogen bonds (Table 1).

Related literature top

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

Experimental top

3-Chloroperoxybenzoic acid (77%, 291 mg, 1.3 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-fluorophenyl)-7-methyl-3-methylsulfanyl-1-benzofuran (368 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5 h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 462–463 K; Rf = 0.51 (hexane–ethyl acetate, 2:1 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 0.98Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens 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 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 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 Cl···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 - 1, z; (ii) - x, - y + 1, - z; (iii) x, y + 1, z; (iv) -x, - y, - z.]
5-Chloro-2-(4-fluorophenyl)-7-methyl-3-methylsulfinyl-1-benzofuran top
Crystal data top
C16H12ClFO2SZ = 2
Mr = 322.77F(000) = 332
Triclinic, P1Dx = 1.522 Mg m3
Hall symbol: -P 1Melting point = 462–463 K
a = 7.5374 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7388 (3) ÅCell parameters from 5632 reflections
c = 10.7979 (4) Åθ = 2.4–28.4°
α = 106.902 (2)°µ = 0.43 mm1
β = 90.605 (2)°T = 173 K
γ = 110.598 (2)°Block, colourless
V = 704.24 (4) Å30.34 × 0.29 × 0.17 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3505 independent reflections
Radiation source: rotating anode3025 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.0°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.669, Tmax = 0.746l = 1414
13230 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)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.093H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2009P]
where P = (Fo2 + 2Fc2)/3
3505 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C16H12ClFO2Sγ = 110.598 (2)°
Mr = 322.77V = 704.24 (4) Å3
Triclinic, P1Z = 2
a = 7.5374 (3) ÅMo Kα radiation
b = 9.7388 (3) ŵ = 0.43 mm1
c = 10.7979 (4) ÅT = 173 K
α = 106.902 (2)°0.34 × 0.29 × 0.17 mm
β = 90.605 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3505 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3025 reflections with I > 2σ(I)
Tmin = 0.669, Tmax = 0.746Rint = 0.029
13230 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.04Δρmax = 0.38 e Å3
3505 reflectionsΔρmin = 0.30 e Å3
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
Cl10.06877 (6)0.24551 (4)0.05566 (3)0.03248 (11)
S10.31257 (5)0.77726 (4)0.43961 (3)0.02701 (11)
F10.57470 (16)0.77811 (14)1.05273 (9)0.0546 (3)
O10.18785 (14)0.36631 (11)0.48724 (9)0.0232 (2)
O20.16474 (17)0.78460 (13)0.35249 (12)0.0385 (3)
C10.25080 (19)0.58204 (15)0.43038 (13)0.0224 (3)
C20.15601 (19)0.45115 (15)0.31599 (13)0.0218 (3)
C30.0986 (2)0.43012 (16)0.18618 (13)0.0243 (3)
H30.12240.51500.15380.029*
C40.0055 (2)0.27967 (16)0.10758 (13)0.0247 (3)
C50.0335 (2)0.15197 (16)0.15232 (13)0.0248 (3)
H50.10000.05100.09390.030*
C60.02366 (19)0.17061 (15)0.28075 (13)0.0230 (3)
C70.11853 (19)0.32240 (15)0.35776 (13)0.0213 (3)
C80.26620 (19)0.52538 (16)0.53022 (13)0.0229 (3)
C90.0088 (2)0.03846 (16)0.33323 (15)0.0297 (3)
H9A0.11140.02280.34280.045*
H9B0.10420.05550.27280.045*
H9C0.05500.06170.41850.045*
C100.34642 (19)0.59406 (16)0.66751 (13)0.0242 (3)
C110.4761 (2)0.74628 (18)0.71675 (15)0.0308 (3)
H110.51370.80720.66010.037*
C120.5504 (2)0.8094 (2)0.84709 (16)0.0356 (3)
H120.63590.91390.88130.043*
C130.4979 (2)0.7178 (2)0.92584 (14)0.0351 (4)
C140.3715 (2)0.5673 (2)0.88172 (15)0.0343 (3)
H140.33820.50690.93900.041*
C150.2938 (2)0.50556 (18)0.75203 (14)0.0275 (3)
H150.20400.40230.72010.033*
C160.5173 (2)0.79549 (19)0.35447 (18)0.0394 (4)
H16A0.48140.71530.26910.059*
H16B0.61640.78360.40520.059*
H16C0.56650.89760.34240.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0459 (2)0.0299 (2)0.01946 (17)0.01465 (16)0.00394 (14)0.00412 (14)
S10.0368 (2)0.01850 (17)0.02544 (19)0.01193 (14)0.00111 (14)0.00443 (14)
F10.0573 (7)0.0654 (8)0.0226 (5)0.0083 (6)0.0117 (5)0.0057 (5)
O10.0287 (5)0.0202 (5)0.0203 (5)0.0094 (4)0.0008 (4)0.0055 (4)
O20.0474 (7)0.0327 (6)0.0430 (7)0.0214 (5)0.0013 (5)0.0151 (5)
C10.0264 (6)0.0189 (6)0.0216 (6)0.0099 (5)0.0005 (5)0.0041 (5)
C20.0237 (6)0.0194 (6)0.0227 (6)0.0094 (5)0.0014 (5)0.0056 (5)
C30.0309 (7)0.0220 (7)0.0220 (6)0.0120 (6)0.0015 (5)0.0074 (5)
C40.0295 (7)0.0265 (7)0.0193 (6)0.0131 (6)0.0005 (5)0.0056 (5)
C50.0268 (7)0.0200 (6)0.0245 (7)0.0086 (5)0.0001 (5)0.0030 (5)
C60.0248 (6)0.0204 (6)0.0254 (7)0.0104 (5)0.0038 (5)0.0071 (5)
C70.0241 (6)0.0220 (6)0.0193 (6)0.0106 (5)0.0008 (5)0.0062 (5)
C80.0233 (6)0.0211 (6)0.0236 (6)0.0092 (5)0.0015 (5)0.0046 (5)
C90.0391 (8)0.0206 (7)0.0304 (7)0.0110 (6)0.0050 (6)0.0094 (6)
C100.0232 (6)0.0284 (7)0.0214 (6)0.0125 (5)0.0009 (5)0.0051 (5)
C110.0301 (7)0.0312 (8)0.0261 (7)0.0066 (6)0.0005 (6)0.0078 (6)
C120.0315 (8)0.0346 (8)0.0293 (8)0.0058 (6)0.0039 (6)0.0018 (7)
C130.0325 (8)0.0472 (10)0.0194 (7)0.0135 (7)0.0043 (6)0.0035 (6)
C140.0362 (8)0.0429 (9)0.0261 (7)0.0151 (7)0.0017 (6)0.0136 (7)
C150.0287 (7)0.0293 (7)0.0250 (7)0.0120 (6)0.0014 (5)0.0078 (6)
C160.0399 (9)0.0303 (8)0.0474 (10)0.0098 (7)0.0114 (7)0.0153 (7)
Geometric parameters (Å, º) top
Cl1—C41.7432 (14)C6—C91.4975 (18)
Cl1—O2i3.1839 (12)C8—C101.4597 (19)
S1—O21.4848 (11)C9—H9A0.9800
S1—C11.7628 (13)C9—H9B0.9800
S1—C161.7863 (17)C9—H9C0.9800
F1—C131.3541 (17)C10—C111.395 (2)
O1—C71.3749 (15)C10—C151.399 (2)
O1—C81.3771 (16)C11—C121.382 (2)
C1—C81.3669 (18)C11—H110.9500
C1—C21.4443 (19)C12—C131.370 (2)
C2—C71.3920 (18)C12—H120.9500
C2—C31.3971 (18)C13—C141.373 (2)
C3—C41.379 (2)C14—C151.382 (2)
C3—H30.9500C14—H140.9500
C4—C51.4004 (19)C15—H150.9500
C5—C61.3884 (19)C16—H16A0.9800
C5—H50.9500C16—H16B0.9800
C6—C71.3845 (19)C16—H16C0.9800
C4—Cl1—O2i173.77 (6)C6—C9—H9B109.5
O2—S1—C1107.35 (7)H9A—C9—H9B109.5
O2—S1—C16106.18 (8)C6—C9—H9C109.5
C1—S1—C1697.46 (7)H9A—C9—H9C109.5
C7—O1—C8106.81 (10)H9B—C9—H9C109.5
C8—C1—C2107.29 (12)C11—C10—C15118.93 (13)
C8—C1—S1127.30 (11)C11—C10—C8121.50 (13)
C2—C1—S1125.16 (10)C15—C10—C8119.56 (13)
C7—C2—C3119.26 (12)C12—C11—C10120.69 (14)
C7—C2—C1104.92 (12)C12—C11—H11119.7
C3—C2—C1135.81 (12)C10—C11—H11119.7
C4—C3—C2116.44 (12)C13—C12—C11118.45 (15)
C4—C3—H3121.8C13—C12—H12120.8
C2—C3—H3121.8C11—C12—H12120.8
C3—C4—C5123.30 (13)F1—C13—C12118.53 (15)
C3—C4—Cl1118.71 (10)F1—C13—C14118.54 (15)
C5—C4—Cl1117.99 (11)C12—C13—C14122.93 (14)
C6—C5—C4121.04 (13)C13—C14—C15118.52 (14)
C6—C5—H5119.5C13—C14—H14120.7
C4—C5—H5119.5C15—C14—H14120.7
C7—C6—C5114.78 (12)C14—C15—C10120.46 (14)
C7—C6—C9121.71 (12)C14—C15—H15119.8
C5—C6—C9123.49 (13)C10—C15—H15119.8
O1—C7—C6124.18 (11)S1—C16—H16A109.5
O1—C7—C2110.65 (12)S1—C16—H16B109.5
C6—C7—C2125.16 (12)H16A—C16—H16B109.5
C1—C8—O1110.30 (12)S1—C16—H16C109.5
C1—C8—C10134.92 (13)H16A—C16—H16C109.5
O1—C8—C10114.78 (11)H16B—C16—H16C109.5
C6—C9—H9A109.5
O2—S1—C1—C8140.84 (13)C1—C2—C7—O11.49 (15)
C16—S1—C1—C8109.57 (14)C3—C2—C7—C61.2 (2)
O2—S1—C1—C232.66 (14)C1—C2—C7—C6178.13 (13)
C16—S1—C1—C276.94 (13)C2—C1—C8—O10.18 (15)
C8—C1—C2—C70.79 (15)S1—C1—C8—O1174.61 (10)
S1—C1—C2—C7173.79 (10)C2—C1—C8—C10179.48 (14)
C8—C1—C2—C3179.96 (15)S1—C1—C8—C106.1 (2)
S1—C1—C2—C35.4 (2)C7—O1—C8—C11.10 (14)
C7—C2—C3—C40.47 (19)C7—O1—C8—C10179.45 (11)
C1—C2—C3—C4178.61 (15)C1—C8—C10—C1117.7 (2)
C2—C3—C4—C50.6 (2)O1—C8—C10—C11161.60 (13)
C2—C3—C4—Cl1179.68 (10)C1—C8—C10—C15162.80 (15)
C3—C4—C5—C61.1 (2)O1—C8—C10—C1517.93 (18)
Cl1—C4—C5—C6179.22 (10)C15—C10—C11—C120.5 (2)
C4—C5—C6—C70.36 (19)C8—C10—C11—C12179.93 (14)
C4—C5—C6—C9178.16 (13)C10—C11—C12—C131.8 (2)
C8—O1—C7—C6178.00 (13)C11—C12—C13—F1178.17 (15)
C8—O1—C7—C21.63 (14)C11—C12—C13—C141.5 (3)
C5—C6—C7—O1179.67 (12)F1—C13—C14—C15179.72 (14)
C9—C6—C7—O11.1 (2)C12—C13—C14—C150.0 (2)
C5—C6—C7—C20.8 (2)C13—C14—C15—C101.3 (2)
C9—C6—C7—C2179.31 (13)C11—C10—C15—C141.0 (2)
C3—C2—C7—O1179.17 (11)C8—C10—C15—C14178.50 (13)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2ii0.982.523.2305 (17)129
Symmetry code: (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC16H12ClFO2S
Mr322.77
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.5374 (3), 9.7388 (3), 10.7979 (4)
α, β, γ (°)106.902 (2), 90.605 (2), 110.598 (2)
V3)704.24 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.34 × 0.29 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.669, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
13230, 3505, 3025
Rint0.029
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.093, 1.04
No. of reflections3505
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.982.523.2305 (17)129.3
Symmetry code: (i) x, y1, z.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o706.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o886.  Web of Science CrossRef IUCr Journals
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
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