3-(4-Fluoro­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536810023834

3-(4-Fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran

H. D. Choi, P. J. Seo, B. W. Son and U. Lee

In the title compound, C₁₇H₁₅FO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.67 (5)° with the benzofuran plane. In the crystal, molecules are linked by weak intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810023834/ds2040sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810023834/ds2040Isup2.hkl Contains datablock I

CCDC reference: 786719

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.038
wR factor = 0.105
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         10

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Compounds containing a benzofuran moiety show potent pharmacological properties such as antifungal (Aslam et al.., 2006), antitumor and antiviral (Galal et al.., 2009), antimicrobial (Khan et al.., 2005) activities. These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al.. 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2,5-dimethyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al.., 2008a, b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 72.67 (5)° with the benzofuran plane. The crystal packing (Fig. 2) is stabilized by three intermolecular C—H···O hydrogen bonds; the first one between the methyl H atom and the oxygen of the O═S═O unit, with a C10—H10B···O2ⁱ, the second one between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit, with a C13—H13···O2ⁱⁱ, and the third one between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit, with a C17—H17···O3ⁱⁱⁱ, respectively (Table 1).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the crystal structures of related 2,5-dimethyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (538 mg, 2.4 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2,5,7-trimethy-1-benzofuran (343 mg, 1.2 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 8h, 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 (silica gel, hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 414-415 K; R_f = 0.41 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in diisopropyl ether at room temperature.

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

	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 a small spheres of arbitrary radius.
	Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 2, - z + 1; (iii) - x + 1, - y + 2, - z.]

3-(4-Fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅FO₃S	Z = 2
M_r = 318.35	F(000) = 332
Triclinic, P1	D_x = 1.413 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.2851 (2) Å	Cell parameters from 7810 reflections
b = 9.3762 (2) Å	θ = 2.4–27.5°
c = 11.2241 (3) Å	µ = 0.24 mm⁻¹
α = 70.441 (1)°	T = 173 K
β = 71.177 (1)°	Block, colourless
γ = 69.407 (1)°	0.23 × 0.21 × 0.19 mm
V = 748.07 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3449 independent reflections
Radiation source: rotating anode	3097 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.6°, θ_min = 2.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.948, T_max = 0.957	l = −14→14
13476 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0536P)² + 0.3586P] where P = (F_o² + 2F_c²)/3
3449 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₇H₁₅FO₃S	γ = 69.407 (1)°
M_r = 318.35	V = 748.07 (3) Å³
Triclinic, P1	Z = 2
a = 8.2851 (2) Å	Mo Kα radiation
b = 9.3762 (2) Å	µ = 0.24 mm⁻¹
c = 11.2241 (3) Å	T = 173 K
α = 70.441 (1)°	0.23 × 0.21 × 0.19 mm
β = 71.177 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3449 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3097 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.957	R_int = 0.026
13476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
3449 reflections	Δρ_min = −0.38 e Å⁻³
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

	x	y	z	U_iso*/U_eq
S	0.48710 (5)	0.89687 (4)	0.29416 (3)	0.02449 (12)
F	0.98555 (17)	1.27225 (14)	−0.00227 (13)	0.0583 (3)
O1	0.75715 (15)	0.45344 (12)	0.32852 (11)	0.0300 (2)
O2	0.39991 (14)	0.94794 (13)	0.41216 (10)	0.0304 (2)
O3	0.38323 (15)	0.91207 (14)	0.20728 (11)	0.0328 (3)
C1	0.60789 (19)	0.70192 (17)	0.33737 (14)	0.0254 (3)
C2	0.67369 (19)	0.62533 (16)	0.45489 (14)	0.0242 (3)
C3	0.6664 (2)	0.66868 (17)	0.56438 (14)	0.0271 (3)
H3	0.6038	0.7718	0.5750	0.033*
C4	0.7533 (2)	0.55674 (19)	0.65748 (15)	0.0299 (3)
C5	0.8449 (2)	0.40466 (18)	0.63998 (15)	0.0315 (3)
H5	0.9044	0.3309	0.7046	0.038*
C6	0.8531 (2)	0.35680 (17)	0.53365 (15)	0.0292 (3)
C7	0.76463 (19)	0.47267 (17)	0.44329 (14)	0.0262 (3)
C8	0.6618 (2)	0.59417 (18)	0.26597 (15)	0.0278 (3)
C9	0.7515 (3)	0.5984 (2)	0.77707 (17)	0.0415 (4)
H9A	0.7024	0.7123	0.7667	0.062*
H9B	0.8728	0.5666	0.7883	0.062*
H9C	0.6782	0.5434	0.8537	0.062*
C10	0.9501 (2)	0.19388 (19)	0.51553 (18)	0.0373 (4)
H10A	1.0603	0.1967	0.4485	0.056*
H10B	0.8753	0.1551	0.4886	0.056*
H10C	0.9779	0.1236	0.5977	0.056*
C11	0.6407 (3)	0.5985 (2)	0.13829 (17)	0.0382 (4)
H11A	0.7576	0.5774	0.0786	0.057*
H11B	0.5679	0.7027	0.1022	0.057*
H11C	0.5829	0.5183	0.1498	0.057*
C12	0.64455 (19)	1.00421 (17)	0.20516 (14)	0.0251 (3)
C13	0.7224 (2)	1.05360 (19)	0.27106 (15)	0.0309 (3)
H13	0.6959	1.0257	0.3634	0.037*
C14	0.8396 (2)	1.1442 (2)	0.20033 (18)	0.0381 (4)
H14	0.8957	1.1787	0.2429	0.046*
C15	0.8722 (2)	1.1827 (2)	0.06712 (18)	0.0386 (4)
C16	0.7969 (2)	1.1347 (2)	−0.00004 (17)	0.0400 (4)
H16	0.8233	1.1638	−0.0924	0.048*
C17	0.6816 (2)	1.0430 (2)	0.07044 (15)	0.0333 (3)
H17	0.6283	1.0068	0.0270	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.02610 (19)	0.02512 (19)	0.02153 (19)	−0.00398 (14)	−0.00822 (13)	−0.00554 (13)
F	0.0579 (7)	0.0490 (7)	0.0633 (8)	−0.0316 (6)	−0.0054 (6)	0.0012 (6)
O1	0.0343 (6)	0.0252 (5)	0.0327 (6)	−0.0066 (4)	−0.0092 (5)	−0.0100 (4)
O2	0.0309 (6)	0.0314 (6)	0.0254 (5)	−0.0035 (4)	−0.0054 (4)	−0.0092 (4)
O3	0.0340 (6)	0.0364 (6)	0.0301 (6)	−0.0077 (5)	−0.0148 (5)	−0.0058 (5)
C1	0.0276 (7)	0.0249 (7)	0.0237 (7)	−0.0065 (6)	−0.0074 (6)	−0.0056 (5)
C2	0.0247 (7)	0.0234 (7)	0.0237 (7)	−0.0078 (5)	−0.0057 (5)	−0.0034 (5)
C3	0.0296 (7)	0.0255 (7)	0.0252 (7)	−0.0068 (6)	−0.0066 (6)	−0.0055 (6)
C4	0.0329 (8)	0.0324 (8)	0.0235 (7)	−0.0116 (6)	−0.0075 (6)	−0.0022 (6)
C5	0.0325 (8)	0.0285 (8)	0.0289 (8)	−0.0109 (6)	−0.0100 (6)	0.0040 (6)
C6	0.0277 (7)	0.0221 (7)	0.0346 (8)	−0.0089 (6)	−0.0072 (6)	−0.0011 (6)
C7	0.0269 (7)	0.0246 (7)	0.0278 (7)	−0.0097 (6)	−0.0052 (6)	−0.0057 (6)
C8	0.0292 (7)	0.0273 (7)	0.0286 (7)	−0.0079 (6)	−0.0078 (6)	−0.0080 (6)
C9	0.0522 (11)	0.0445 (10)	0.0285 (8)	−0.0108 (8)	−0.0172 (8)	−0.0051 (7)
C10	0.0373 (9)	0.0231 (7)	0.0476 (10)	−0.0058 (6)	−0.0124 (7)	−0.0041 (7)
C11	0.0475 (10)	0.0396 (9)	0.0335 (9)	−0.0092 (8)	−0.0130 (7)	−0.0157 (7)
C12	0.0280 (7)	0.0223 (7)	0.0228 (7)	−0.0032 (5)	−0.0076 (5)	−0.0050 (5)
C13	0.0356 (8)	0.0306 (8)	0.0267 (7)	−0.0066 (6)	−0.0091 (6)	−0.0084 (6)
C14	0.0407 (9)	0.0346 (9)	0.0448 (10)	−0.0121 (7)	−0.0116 (8)	−0.0137 (7)
C15	0.0380 (9)	0.0279 (8)	0.0437 (10)	−0.0123 (7)	−0.0055 (7)	−0.0015 (7)
C16	0.0442 (10)	0.0428 (10)	0.0263 (8)	−0.0140 (8)	−0.0071 (7)	0.0010 (7)
C17	0.0381 (8)	0.0368 (8)	0.0248 (7)	−0.0100 (7)	−0.0109 (6)	−0.0042 (6)

Geometric parameters (Å, º) top

S—O2	1.4384 (11)	C9—H9A	0.9800
S—O3	1.4402 (11)	C9—H9B	0.9800
S—C1	1.7351 (15)	C9—H9C	0.9800
S—C12	1.7669 (15)	C10—H10A	0.9800
F—C15	1.3561 (19)	C10—H10B	0.9800
O1—C8	1.3647 (19)	C10—H10C	0.9800
O1—C7	1.3823 (18)	C11—H11A	0.9800
C1—C8	1.362 (2)	C11—H11B	0.9800
C1—C2	1.452 (2)	C11—H11C	0.9800
C2—C7	1.392 (2)	C12—C17	1.387 (2)
C2—C3	1.396 (2)	C12—C13	1.388 (2)
C3—C4	1.390 (2)	C13—C14	1.387 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.406 (2)	C14—C15	1.373 (3)
C4—C9	1.513 (2)	C14—H14	0.9500
C5—C6	1.384 (2)	C15—C16	1.374 (3)
C5—H5	0.9500	C16—C17	1.383 (2)
C6—C7	1.389 (2)	C16—H16	0.9500
C6—C10	1.503 (2)	C17—H17	0.9500
C8—C11	1.484 (2)

O2—S—O3	119.38 (7)	C4—C9—H9C	109.5
O2—S—C1	107.27 (7)	H9A—C9—H9C	109.5
O3—S—C1	109.18 (7)	H9B—C9—H9C	109.5
O2—S—C12	107.00 (7)	C6—C10—H10A	109.5
O3—S—C12	107.22 (7)	C6—C10—H10B	109.5
C1—S—C12	106.04 (7)	H10A—C10—H10B	109.5
C8—O1—C7	107.03 (11)	C6—C10—H10C	109.5
C8—C1—C2	107.63 (13)	H10A—C10—H10C	109.5
C8—C1—S	126.31 (12)	H10B—C10—H10C	109.5
C2—C1—S	126.04 (11)	C8—C11—H11A	109.5
C7—C2—C3	119.44 (13)	C8—C11—H11B	109.5
C7—C2—C1	104.30 (13)	H11A—C11—H11B	109.5
C3—C2—C1	136.26 (14)	C8—C11—H11C	109.5
C4—C3—C2	118.13 (14)	H11A—C11—H11C	109.5
C4—C3—H3	120.9	H11B—C11—H11C	109.5
C2—C3—H3	120.9	C17—C12—C13	121.50 (15)
C3—C4—C5	120.01 (14)	C17—C12—S	118.94 (12)
C3—C4—C9	120.21 (15)	C13—C12—S	119.50 (11)
C5—C4—C9	119.77 (15)	C14—C13—C12	119.12 (15)
C6—C5—C4	123.49 (14)	C14—C13—H13	120.4
C6—C5—H5	118.3	C12—C13—H13	120.4
C4—C5—H5	118.3	C15—C14—C13	118.22 (16)
C5—C6—C7	114.38 (14)	C15—C14—H14	120.9
C5—C6—C10	123.44 (15)	C13—C14—H14	120.9
C7—C6—C10	122.18 (15)	F—C15—C14	118.37 (16)
O1—C7—C6	124.84 (14)	F—C15—C16	118.03 (16)
O1—C7—C2	110.61 (13)	C14—C15—C16	123.59 (16)
C6—C7—C2	124.53 (14)	C15—C16—C17	118.18 (16)
C1—C8—O1	110.43 (13)	C15—C16—H16	120.9
C1—C8—C11	134.21 (15)	C17—C16—H16	120.9
O1—C8—C11	115.35 (13)	C16—C17—C12	119.37 (15)
C4—C9—H9A	109.5	C16—C17—H17	120.3
C4—C9—H9B	109.5	C12—C17—H17	120.3
H9A—C9—H9B	109.5

O2—S—C1—C8	157.19 (13)	C1—C2—C7—O1	−0.13 (16)
O3—S—C1—C8	26.50 (16)	C3—C2—C7—C6	−0.8 (2)
C12—S—C1—C8	−88.73 (15)	C1—C2—C7—C6	178.84 (14)
O2—S—C1—C2	−24.51 (15)	C2—C1—C8—O1	0.16 (17)
O3—S—C1—C2	−155.21 (12)	S—C1—C8—O1	178.72 (10)
C12—S—C1—C2	89.57 (13)	C2—C1—C8—C11	−179.06 (17)
C8—C1—C2—C7	−0.02 (16)	S—C1—C8—C11	−0.5 (3)
S—C1—C2—C7	−178.58 (11)	C7—O1—C8—C1	−0.25 (16)
C8—C1—C2—C3	179.48 (16)	C7—O1—C8—C11	179.14 (13)
S—C1—C2—C3	0.9 (3)	O2—S—C12—C17	−147.39 (12)
C7—C2—C3—C4	0.8 (2)	O3—S—C12—C17	−18.20 (14)
C1—C2—C3—C4	−178.62 (15)	C1—S—C12—C17	98.35 (13)
C2—C3—C4—C5	−0.1 (2)	O2—S—C12—C13	29.85 (14)
C2—C3—C4—C9	179.17 (14)	O3—S—C12—C13	159.04 (12)
C3—C4—C5—C6	−0.8 (2)	C1—S—C12—C13	−84.41 (13)
C9—C4—C5—C6	179.94 (15)	C17—C12—C13—C14	0.2 (2)
C4—C5—C6—C7	0.9 (2)	S—C12—C13—C14	−176.95 (12)
C4—C5—C6—C10	−179.56 (15)	C12—C13—C14—C15	0.7 (2)
C8—O1—C7—C6	−178.73 (14)	C13—C14—C15—F	179.52 (15)
C8—O1—C7—C2	0.24 (16)	C13—C14—C15—C16	−0.9 (3)
C5—C6—C7—O1	178.75 (13)	F—C15—C16—C17	179.80 (16)
C10—C6—C7—O1	−0.8 (2)	C14—C15—C16—C17	0.2 (3)
C5—C6—C7—C2	−0.1 (2)	C15—C16—C17—C12	0.7 (3)
C10—C6—C7—C2	−179.66 (14)	C13—C12—C17—C16	−0.9 (2)
C3—C2—C7—O1	−179.73 (12)	S—C12—C17—C16	176.28 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱ	0.98	2.56	3.363 (2)	139
C13—H13···O2ⁱⁱ	0.95	2.45	3.365 (2)	160
C17—H17···O3ⁱⁱⁱ	0.95	2.50	3.198 (2)	130

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FO₃S
M_r	318.35
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.2851 (2), 9.3762 (2), 11.2241 (3)
α, β, γ (°)	70.441 (1), 71.177 (1), 69.407 (1)
V (Å³)	748.07 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.948, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	13476, 3449, 3097
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.04
No. of reflections	3449
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).