5-Ethyl-3-(4-Fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

In the title mol-ecule, C(17)H(15)FO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 74.06 (4)° with the mean plane of the benzofuran fragment. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits aromatic π-π inter-actions between the benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.629 (2) Å].

Related literature

For the crystal structures of similar 3-(4-fluoro­phenyl­sulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶). For the biological 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 ▶).

Experimental

Crystal data

C17H15FO3S

M = 318.35

Triclinic,

a = 8.0042 (1) Å

b = 9.7114 (2) Å

c = 11.3741 (2) Å

α = 66.487 (1)°

β = 82.998 (1)°

γ = 67.964 (1)°

V = 751.10 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.31 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.929, T max = 0.946

13998 measured reflections

3722 independent reflections

3264 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.04

3722 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036391/su2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036391/su2211Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15FO3S	Z = 2
Mr = 318.35	F(000) = 332
Triclinic, P1	Dx = 1.408 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0042 (1) Å	Cell parameters from 6492 reflections
b = 9.7114 (2) Å	θ = 2.5–28.2°
c = 11.3741 (2) Å	µ = 0.24 mm−1
α = 66.487 (1)°	T = 173 K
β = 82.998 (1)°	Block, colourless
γ = 67.964 (1)°	0.31 × 0.25 × 0.24 mm
V = 751.10 (2) Å3

Bruker SMART APEXII CCD diffractometer	3722 independent reflections
Radiation source: rotating anode	3264 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.929, Tmax = 0.946	l = −15→15
13998 measured reflections

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2601P] where P = (Fo2 + 2Fc2)/3
3722 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.53064 (4)	0.61417 (4)	0.69284 (3)	0.02667 (10)
F1	0.02306 (15)	0.28696 (12)	0.93170 (10)	0.0495 (3)
O1	0.26044 (14)	1.07835 (12)	0.57702 (10)	0.0326 (2)
O2	0.61844 (14)	0.55702 (13)	0.59437 (10)	0.0352 (2)
O3	0.63741 (14)	0.59481 (13)	0.79503 (10)	0.0354 (2)
C1	0.39955 (18)	0.81537 (16)	0.61842 (12)	0.0255 (3)
C2	0.29794 (17)	0.88735 (16)	0.49822 (12)	0.0261 (3)
C3	0.26704 (18)	0.83239 (17)	0.40981 (13)	0.0290 (3)
H3	0.3221	0.7221	0.4220	0.035*
C4	0.15386 (19)	0.94248 (19)	0.30318 (13)	0.0331 (3)
C5	0.0762 (2)	1.10491 (19)	0.28633 (15)	0.0381 (3)
H5	0.0007	1.1788	0.2126	0.046*
C6	0.1050 (2)	1.16199 (18)	0.37250 (15)	0.0371 (3)
H6	0.0517	1.2724	0.3600	0.045*
C7	0.21583 (18)	1.04904 (17)	0.47799 (13)	0.0295 (3)
C8	0.37157 (18)	0.93495 (17)	0.66117 (13)	0.0285 (3)
C9	0.1224 (2)	0.8853 (2)	0.20518 (15)	0.0438 (4)
H9A	0.0020	0.9550	0.1632	0.053*
H9B	0.1225	0.7745	0.2496	0.053*
C10	0.2631 (2)	0.8871 (2)	0.10352 (16)	0.0450 (4)
H10A	0.2596	0.9975	0.0562	0.067*
H10B	0.2381	0.8462	0.0441	0.067*
H10C	0.3828	0.8187	0.1444	0.067*
C11	0.4355 (2)	0.9415 (2)	0.77493 (15)	0.0372 (3)
H11A	0.4909	0.8320	0.8383	0.056*
H11B	0.3331	1.0027	0.8127	0.056*
H11C	0.5246	0.9942	0.7491	0.056*
C12	0.37463 (18)	0.51746 (15)	0.76302 (12)	0.0267 (3)
C13	0.3061 (2)	0.45940 (16)	0.69364 (13)	0.0314 (3)
H13	0.3415	0.4729	0.6081	0.038*
C14	0.1857 (2)	0.38180 (17)	0.75030 (15)	0.0358 (3)
H14	0.1357	0.3425	0.7044	0.043*
C15	0.1402 (2)	0.36313 (17)	0.87531 (15)	0.0350 (3)
C16	0.2084 (2)	0.41710 (18)	0.94653 (14)	0.0344 (3)
H16	0.1758	0.3997	1.0330	0.041*
C17	0.32586 (19)	0.49745 (17)	0.88873 (13)	0.0302 (3)
H17	0.3729	0.5387	0.9346	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.02624 (17)	0.02837 (17)	0.02451 (17)	−0.00613 (13)	−0.00164 (12)	−0.01197 (13)
F1	0.0537 (6)	0.0503 (6)	0.0491 (6)	−0.0316 (5)	0.0016 (5)	−0.0115 (5)
O1	0.0343 (5)	0.0282 (5)	0.0366 (5)	−0.0118 (4)	0.0075 (4)	−0.0151 (4)
O2	0.0347 (5)	0.0364 (5)	0.0325 (5)	−0.0060 (4)	0.0044 (4)	−0.0186 (4)
O3	0.0327 (5)	0.0419 (6)	0.0319 (5)	−0.0118 (4)	−0.0074 (4)	−0.0135 (4)
C1	0.0258 (6)	0.0270 (6)	0.0248 (6)	−0.0096 (5)	0.0020 (5)	−0.0112 (5)
C2	0.0233 (6)	0.0285 (6)	0.0239 (6)	−0.0093 (5)	0.0032 (5)	−0.0082 (5)
C3	0.0272 (6)	0.0331 (7)	0.0258 (6)	−0.0113 (5)	0.0014 (5)	−0.0101 (5)
C4	0.0253 (6)	0.0458 (8)	0.0250 (6)	−0.0145 (6)	0.0023 (5)	−0.0093 (6)
C5	0.0264 (7)	0.0427 (8)	0.0291 (7)	−0.0079 (6)	0.0000 (5)	−0.0020 (6)
C6	0.0296 (7)	0.0283 (7)	0.0391 (8)	−0.0049 (6)	0.0051 (6)	−0.0050 (6)
C7	0.0270 (6)	0.0294 (7)	0.0300 (7)	−0.0111 (5)	0.0064 (5)	−0.0101 (5)
C8	0.0270 (6)	0.0324 (7)	0.0300 (7)	−0.0134 (5)	0.0074 (5)	−0.0151 (5)
C9	0.0389 (8)	0.0638 (11)	0.0297 (8)	−0.0213 (8)	−0.0046 (6)	−0.0146 (7)
C10	0.0487 (9)	0.0479 (9)	0.0336 (8)	−0.0118 (8)	0.0014 (7)	−0.0161 (7)
C11	0.0411 (8)	0.0454 (8)	0.0375 (8)	−0.0199 (7)	0.0083 (6)	−0.0262 (7)
C12	0.0279 (6)	0.0235 (6)	0.0256 (6)	−0.0050 (5)	−0.0036 (5)	−0.0092 (5)
C13	0.0392 (8)	0.0273 (6)	0.0268 (6)	−0.0077 (6)	−0.0049 (6)	−0.0116 (5)
C14	0.0448 (8)	0.0291 (7)	0.0369 (8)	−0.0136 (6)	−0.0068 (6)	−0.0135 (6)
C15	0.0349 (7)	0.0283 (7)	0.0375 (8)	−0.0113 (6)	−0.0043 (6)	−0.0067 (6)
C16	0.0341 (7)	0.0367 (7)	0.0274 (7)	−0.0094 (6)	−0.0014 (6)	−0.0098 (6)
C17	0.0314 (7)	0.0326 (7)	0.0264 (6)	−0.0080 (5)	−0.0042 (5)	−0.0128 (5)

S1—O3	1.4366 (10)	C9—C10	1.512 (2)
S1—O2	1.4380 (10)	C9—H9A	0.9900
S1—C1	1.7302 (13)	C9—H9B	0.9900
S1—C12	1.7656 (14)	C10—H10A	0.9800
F1—C15	1.3542 (17)	C10—H10B	0.9800
O1—C8	1.3642 (17)	C10—H10C	0.9800
O1—C7	1.3811 (17)	C11—H11A	0.9800
C1—C8	1.3652 (18)	C11—H11B	0.9800
C1—C2	1.4496 (18)	C11—H11C	0.9800
C2—C7	1.3874 (19)	C12—C17	1.3905 (19)
C2—C3	1.3947 (19)	C12—C13	1.3909 (19)
C3—C4	1.3932 (19)	C13—C14	1.385 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.401 (2)	C14—C15	1.380 (2)
C4—C9	1.510 (2)	C14—H14	0.9500
C5—C6	1.380 (2)	C15—C16	1.375 (2)
C5—H5	0.9500	C16—C17	1.384 (2)
C6—C7	1.382 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.4802 (19)
O3—S1—O2	119.42 (6)	C4—C9—H9B	109.0
O3—S1—C1	109.13 (6)	C10—C9—H9B	109.0
O2—S1—C1	107.67 (6)	H9A—C9—H9B	107.8
O3—S1—C12	107.56 (6)	C9—C10—H10A	109.5
O2—S1—C12	107.33 (6)	C9—C10—H10B	109.5
C1—S1—C12	104.80 (6)	H10A—C10—H10B	109.5
C8—O1—C7	107.11 (10)	C9—C10—H10C	109.5
C8—C1—C2	107.43 (12)	H10A—C10—H10C	109.5
C8—C1—S1	126.92 (11)	H10B—C10—H10C	109.5
C2—C1—S1	125.65 (10)	C8—C11—H11A	109.5
C7—C2—C3	119.46 (13)	C8—C11—H11B	109.5
C7—C2—C1	104.60 (12)	H11A—C11—H11B	109.5
C3—C2—C1	135.93 (13)	C8—C11—H11C	109.5
C4—C3—C2	118.67 (13)	H11A—C11—H11C	109.5
C4—C3—H3	120.7	H11B—C11—H11C	109.5
C2—C3—H3	120.7	C17—C12—C13	121.14 (14)
C3—C4—C5	119.60 (14)	C17—C12—S1	118.90 (11)
C3—C4—C9	119.24 (15)	C13—C12—S1	119.93 (11)
C5—C4—C9	121.12 (14)	C14—C13—C12	119.42 (13)
C6—C5—C4	122.72 (14)	C14—C13—H13	120.3
C6—C5—H5	118.6	C12—C13—H13	120.3
C4—C5—H5	118.6	C15—C14—C13	118.15 (13)
C5—C6—C7	116.07 (14)	C15—C14—H14	120.9
C5—C6—H6	122.0	C13—C14—H14	120.9
C7—C6—H6	122.0	F1—C15—C16	117.89 (14)
O1—C7—C6	125.99 (13)	F1—C15—C14	118.60 (14)
O1—C7—C2	110.55 (12)	C16—C15—C14	123.51 (14)
C6—C7—C2	123.46 (14)	C15—C16—C17	118.15 (13)
O1—C8—C1	110.32 (12)	C15—C16—H16	120.9
O1—C8—C11	115.33 (12)	C17—C16—H16	120.9
C1—C8—C11	134.35 (14)	C16—C17—C12	119.59 (13)
C4—C9—C10	112.95 (14)	C16—C17—H17	120.2
C4—C9—H9A	109.0	C12—C17—H17	120.2
C10—C9—H9A	109.0
O3—S1—C1—C8	−11.72 (15)	C7—O1—C8—C1	0.22 (15)
O2—S1—C1—C8	−142.73 (12)	C7—O1—C8—C11	179.75 (11)
C12—S1—C1—C8	103.23 (13)	C2—C1—C8—O1	−0.33 (15)
O3—S1—C1—C2	168.62 (11)	S1—C1—C8—O1	179.95 (9)
O2—S1—C1—C2	37.61 (13)	C2—C1—C8—C11	−179.74 (15)
C12—S1—C1—C2	−76.43 (12)	S1—C1—C8—C11	0.6 (2)
C8—C1—C2—C7	0.31 (14)	C3—C4—C9—C10	−86.77 (18)
S1—C1—C2—C7	−179.97 (10)	C5—C4—C9—C10	91.01 (18)
C8—C1—C2—C3	−178.43 (15)	O3—S1—C12—C17	24.49 (13)
S1—C1—C2—C3	1.3 (2)	O2—S1—C12—C17	154.16 (11)
C7—C2—C3—C4	0.01 (19)	C1—S1—C12—C17	−91.56 (12)
C1—C2—C3—C4	178.61 (14)	O3—S1—C12—C13	−153.99 (11)
C2—C3—C4—C5	0.9 (2)	O2—S1—C12—C13	−24.32 (13)
C2—C3—C4—C9	178.68 (13)	C1—S1—C12—C13	89.96 (12)
C3—C4—C5—C6	−0.9 (2)	C17—C12—C13—C14	0.7 (2)
C9—C4—C5—C6	−178.63 (14)	S1—C12—C13—C14	179.12 (11)
C4—C5—C6—C7	−0.1 (2)	C12—C13—C14—C15	−0.9 (2)
C8—O1—C7—C6	179.79 (13)	C13—C14—C15—F1	−179.79 (13)
C8—O1—C7—C2	−0.01 (15)	C13—C14—C15—C16	−0.1 (2)
C5—C6—C7—O1	−178.77 (13)	F1—C15—C16—C17	−178.93 (13)
C5—C6—C7—C2	1.0 (2)	C14—C15—C16—C17	1.4 (2)
C3—C2—C7—O1	178.81 (11)	C15—C16—C17—C12	−1.6 (2)
C1—C2—C7—O1	−0.18 (14)	C13—C12—C17—C16	0.6 (2)
C3—C2—C7—C6	−1.0 (2)	S1—C12—C17—C16	−177.84 (10)
C1—C2—C7—C6	−179.99 (13)

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

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.40	3.3143 (17)	161
C11—H11C···Cgii	0.98	2.66	3.491 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.40	3.3143 (17)	161
C11—H11C⋯Cgii	0.98	2.66	3.491 (2)	143

Symmetry codes: (i) ; (ii) .