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ISSN: 2056-9890

3-(2-Fluoro­phenyl­sulfon­yl)-2,5,7-tri­methyl-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 4 April 2014; accepted 9 April 2014; online 16 April 2014)

In the title compound, C17H15FO3S, the dihedral angle between the mean planes of the benzo­furan and 2-fluoro­phenyl rings is 87.61 (4) Å. In the crystal, mol­ecules are linked via pairs of C—H⋯π inter­actions into inversion-related dimers. These dimers are linked by C—H⋯O hydrogen bonds into supra­molecular chains running along the a-axis direction.

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, o1813.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1751.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3359.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15FO3S

  • Mr = 318.35

  • Triclinic, [P \overline 1]

  • a = 7.7658 (2) Å

  • b = 8.3529 (3) Å

  • c = 12.9732 (4) Å

  • α = 74.253 (2)°

  • β = 75.048 (2)°

  • γ = 66.046 (1)°

  • V = 729.66 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 173 K

  • 0.34 × 0.26 × 0.23 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 = 0.700, Tmax = 0.746

  • 13247 measured reflections

  • 3498 independent reflections

  • 3057 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.104

  • S = 1.04

  • 3498 reflections

  • 202 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16⋯O2i 0.95 2.58 3.462 (2) 155
C9—H9CCg1ii 0.98 2.79 3.612 (2) 142
Symmetry codes: (i) x-1, y, z; (ii) -x, -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


Comment top

As a part of our ongoing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010), 3-fluorophenylsulfonyl (Seo et al., 2011) and 4-methylphenylsulfonyl (Choi et al., 2012) substituents in the 3-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.004 (1) 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 87.61 (4)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring) into inversion-related dimers. These dimers are further linked by C—H···O hydrogen bonds (Table 1), forming supramolecular chains running along the a-axis direction.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012); Seo et al. (2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(2-fluorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (257 mg, 0.9 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 71%, m.p. 409–410 K; Rf = 0.52 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow vaporation 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, 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
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom numbering scheme The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O and C—H···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, z; (ii) - x, - y + 1, - z + 1; (iii) x + 1, y, z.]
3-(2-Fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran top
Crystal data top
C17H15FO3SZ = 2
Mr = 318.35F(000) = 332
Triclinic, P1Dx = 1.449 Mg m3
Hall symbol: -P 1Melting point = 410–409 K
a = 7.7658 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3529 (3) ÅCell parameters from 6186 reflections
c = 12.9732 (4) Åθ = 2.7–28.2°
α = 74.253 (2)°µ = 0.24 mm1
β = 75.048 (2)°T = 173 K
γ = 66.046 (1)°Block, colourless
V = 729.66 (4) Å30.34 × 0.26 × 0.23 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3498 independent reflections
Radiation source: rotating anode3057 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 28.0°, θmin = 1.7°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1110
Tmin = 0.700, Tmax = 0.746l = 1617
13247 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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.104H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.2699P]
where P = (Fo2 + 2Fc2)/3
3498 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C17H15FO3Sγ = 66.046 (1)°
Mr = 318.35V = 729.66 (4) Å3
Triclinic, P1Z = 2
a = 7.7658 (2) ÅMo Kα radiation
b = 8.3529 (3) ŵ = 0.24 mm1
c = 12.9732 (4) ÅT = 173 K
α = 74.253 (2)°0.34 × 0.26 × 0.23 mm
β = 75.048 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3498 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3057 reflections with I > 2σ(I)
Tmin = 0.700, Tmax = 0.746Rint = 0.023
13247 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.04Δρmax = 0.34 e Å3
3498 reflectionsΔρmin = 0.36 e Å3
202 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
S10.42141 (5)0.28123 (5)0.15133 (3)0.02646 (12)
F10.04064 (14)0.26625 (13)0.15747 (8)0.0372 (2)
O10.29698 (15)0.04837 (13)0.41192 (8)0.0261 (2)
O20.55334 (16)0.35762 (16)0.15685 (9)0.0370 (3)
O30.47053 (17)0.17497 (16)0.07064 (9)0.0368 (3)
C120.2034 (2)0.4608 (2)0.13354 (11)0.0248 (3)
C170.0368 (2)0.4340 (2)0.13746 (12)0.0281 (3)
C10.3680 (2)0.16080 (19)0.27862 (12)0.0248 (3)
C20.3203 (2)0.22449 (19)0.37943 (11)0.0236 (3)
C30.3066 (2)0.37738 (19)0.40990 (12)0.0261 (3)
H30.33640.47060.35730.031*
C40.2485 (2)0.3905 (2)0.51883 (12)0.0273 (3)
C50.2053 (2)0.2505 (2)0.59508 (12)0.0274 (3)
H50.16500.26250.66910.033*
C60.2185 (2)0.09579 (19)0.56803 (12)0.0249 (3)
C70.2774 (2)0.08988 (18)0.45848 (12)0.0232 (3)
C80.3499 (2)0.0012 (2)0.30262 (12)0.0264 (3)
C90.2271 (3)0.5540 (2)0.55619 (14)0.0358 (4)
H9A0.27970.63060.49610.054*
H9B0.29640.51840.61690.054*
H9C0.09140.61960.57990.054*
C100.1698 (2)0.0525 (2)0.64939 (12)0.0301 (3)
H10A0.06490.06890.63000.045*
H10B0.13060.02230.72190.045*
H10C0.28210.16320.64930.045*
C110.3704 (2)0.1314 (2)0.23854 (14)0.0351 (4)
H11A0.39140.08060.16090.053*
H11B0.25380.15920.25680.053*
H11C0.47960.24080.25540.053*
C130.1995 (2)0.6340 (2)0.11204 (12)0.0310 (3)
H130.31210.65520.10920.037*
C140.0312 (3)0.7759 (2)0.09474 (13)0.0387 (4)
H140.02820.89460.08060.046*
C150.1330 (3)0.7457 (2)0.09789 (13)0.0403 (4)
H150.24730.84390.08450.048*
C160.1318 (2)0.5737 (2)0.12045 (13)0.0359 (4)
H160.24470.55250.12410.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0237 (2)0.0311 (2)0.02292 (18)0.01123 (15)0.00111 (13)0.00301 (14)
F10.0387 (5)0.0397 (5)0.0406 (5)0.0238 (4)0.0086 (4)0.0022 (4)
O10.0260 (5)0.0235 (5)0.0277 (5)0.0094 (4)0.0034 (4)0.0036 (4)
O20.0288 (6)0.0478 (7)0.0361 (6)0.0216 (5)0.0062 (5)0.0025 (5)
O30.0379 (7)0.0392 (6)0.0272 (6)0.0096 (5)0.0022 (5)0.0111 (5)
C120.0262 (7)0.0287 (7)0.0183 (6)0.0106 (6)0.0031 (5)0.0023 (5)
C170.0305 (8)0.0335 (8)0.0214 (6)0.0147 (6)0.0026 (6)0.0037 (6)
C10.0227 (7)0.0255 (7)0.0249 (7)0.0085 (6)0.0036 (5)0.0035 (5)
C20.0198 (7)0.0255 (7)0.0242 (7)0.0079 (5)0.0045 (5)0.0021 (5)
C30.0267 (7)0.0238 (7)0.0277 (7)0.0107 (6)0.0059 (6)0.0010 (6)
C40.0257 (7)0.0267 (7)0.0304 (7)0.0090 (6)0.0059 (6)0.0066 (6)
C50.0257 (7)0.0320 (8)0.0242 (7)0.0099 (6)0.0043 (6)0.0055 (6)
C60.0198 (7)0.0267 (7)0.0257 (7)0.0079 (6)0.0045 (5)0.0010 (6)
C70.0205 (7)0.0211 (6)0.0281 (7)0.0070 (5)0.0060 (5)0.0035 (5)
C80.0218 (7)0.0273 (7)0.0281 (7)0.0070 (6)0.0039 (6)0.0053 (6)
C90.0420 (10)0.0316 (8)0.0375 (9)0.0158 (7)0.0056 (7)0.0095 (7)
C100.0307 (8)0.0308 (8)0.0276 (7)0.0141 (6)0.0041 (6)0.0003 (6)
C110.0369 (9)0.0337 (8)0.0369 (9)0.0136 (7)0.0005 (7)0.0141 (7)
C130.0393 (9)0.0323 (8)0.0228 (7)0.0171 (7)0.0049 (6)0.0015 (6)
C140.0528 (11)0.0294 (8)0.0276 (8)0.0112 (8)0.0075 (7)0.0007 (6)
C150.0381 (9)0.0427 (10)0.0255 (8)0.0001 (8)0.0070 (7)0.0046 (7)
C160.0266 (8)0.0508 (10)0.0261 (7)0.0107 (7)0.0037 (6)0.0064 (7)
Geometric parameters (Å, º) top
S1—O31.4327 (12)C6—C71.384 (2)
S1—O21.4336 (11)C6—C101.5023 (19)
S1—C11.7305 (15)C8—C111.477 (2)
S1—C121.7664 (15)C9—H9A0.9800
F1—C171.3430 (18)C9—H9B0.9800
O1—C81.3646 (18)C9—H9C0.9800
O1—C71.3820 (17)C10—H10A0.9800
C12—C131.386 (2)C10—H10B0.9800
C12—C171.387 (2)C10—H10C0.9800
C17—C161.376 (2)C11—H11A0.9800
C1—C81.361 (2)C11—H11B0.9800
C1—C21.449 (2)C11—H11C0.9800
C2—C71.3887 (19)C13—C141.383 (2)
C2—C31.393 (2)C13—H130.9500
C3—C41.388 (2)C14—C151.386 (3)
C3—H30.9500C14—H140.9500
C4—C51.406 (2)C15—C161.383 (3)
C4—C91.504 (2)C15—H150.9500
C5—C61.387 (2)C16—H160.9500
C5—H50.9500
O3—S1—O2118.79 (7)C1—C8—O1110.21 (13)
O3—S1—C1109.75 (7)C1—C8—C11135.02 (14)
O2—S1—C1108.30 (7)O1—C8—C11114.75 (13)
O3—S1—C12109.12 (7)C4—C9—H9A109.5
O2—S1—C12106.32 (7)C4—C9—H9B109.5
C1—S1—C12103.44 (7)H9A—C9—H9B109.5
C8—O1—C7107.16 (11)C4—C9—H9C109.5
C13—C12—C17118.81 (14)H9A—C9—H9C109.5
C13—C12—S1119.15 (12)H9B—C9—H9C109.5
C17—C12—S1122.02 (12)C6—C10—H10A109.5
F1—C17—C16119.00 (14)C6—C10—H10B109.5
F1—C17—C12118.90 (14)H10A—C10—H10B109.5
C16—C17—C12122.09 (15)C6—C10—H10C109.5
C8—C1—C2107.72 (13)H10A—C10—H10C109.5
C8—C1—S1127.53 (12)H10B—C10—H10C109.5
C2—C1—S1124.61 (11)C8—C11—H11A109.5
C7—C2—C3119.30 (13)C8—C11—H11B109.5
C7—C2—C1104.47 (12)H11A—C11—H11B109.5
C3—C2—C1136.22 (13)C8—C11—H11C109.5
C4—C3—C2118.53 (13)H11A—C11—H11C109.5
C4—C3—H3120.7H11B—C11—H11C109.5
C2—C3—H3120.7C14—C13—C12119.81 (15)
C3—C4—C5119.61 (14)C14—C13—H13120.1
C3—C4—C9120.90 (14)C12—C13—H13120.1
C5—C4—C9119.47 (14)C13—C14—C15120.32 (16)
C6—C5—C4123.54 (14)C13—C14—H14119.8
C6—C5—H5118.2C15—C14—H14119.8
C4—C5—H5118.2C16—C15—C14120.53 (16)
C7—C6—C5114.35 (13)C16—C15—H15119.7
C7—C6—C10122.18 (14)C14—C15—H15119.7
C5—C6—C10123.46 (14)C17—C16—C15118.42 (16)
O1—C7—C6124.88 (13)C17—C16—H16120.8
O1—C7—C2110.44 (12)C15—C16—H16120.8
C6—C7—C2124.67 (13)
O3—S1—C12—C13119.82 (12)C4—C5—C6—C70.3 (2)
O2—S1—C12—C139.42 (14)C4—C5—C6—C10179.14 (14)
C1—S1—C12—C13123.39 (12)C8—O1—C7—C6177.56 (13)
O3—S1—C12—C1758.37 (14)C8—O1—C7—C20.85 (15)
O2—S1—C12—C17172.39 (12)C5—C6—C7—O1178.51 (13)
C1—S1—C12—C1758.41 (13)C10—C6—C7—O10.4 (2)
C13—C12—C17—F1179.51 (13)C5—C6—C7—C20.3 (2)
S1—C12—C17—F11.30 (19)C10—C6—C7—C2178.56 (13)
C13—C12—C17—C160.2 (2)C3—C2—C7—O1179.19 (12)
S1—C12—C17—C16178.05 (12)C1—C2—C7—O10.22 (15)
O3—S1—C1—C87.65 (16)C3—C2—C7—C60.8 (2)
O2—S1—C1—C8138.77 (14)C1—C2—C7—C6178.20 (13)
C12—S1—C1—C8108.69 (14)C2—C1—C8—O11.05 (16)
O3—S1—C1—C2177.27 (12)S1—C1—C8—O1176.80 (10)
O2—S1—C1—C246.15 (14)C2—C1—C8—C11177.56 (16)
C12—S1—C1—C266.39 (13)S1—C1—C8—C111.8 (3)
C8—C1—C2—C70.50 (16)C7—O1—C8—C11.17 (15)
S1—C1—C2—C7176.40 (11)C7—O1—C8—C11177.74 (12)
C8—C1—C2—C3178.21 (16)C17—C12—C13—C140.2 (2)
S1—C1—C2—C32.3 (2)S1—C12—C13—C14178.09 (12)
C7—C2—C3—C40.6 (2)C12—C13—C14—C150.5 (2)
C1—C2—C3—C4177.95 (15)C13—C14—C15—C161.3 (2)
C2—C3—C4—C50.1 (2)F1—C17—C16—C15178.80 (14)
C2—C3—C4—C9178.71 (14)C12—C17—C16—C150.6 (2)
C3—C4—C5—C60.4 (2)C14—C15—C16—C171.3 (2)
C9—C4—C5—C6179.20 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O2i0.952.583.462 (2)155
C9—H9C···Cg1ii0.982.793.612 (2)142
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O2i0.952.583.462 (2)155.0
C9—H9C···Cg1ii0.982.793.612 (2)141.7
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+1.
 

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. & Lee, U. (2012). Acta Cryst. E68, o1751.  CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1813.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSeo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3359.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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