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

In the title compound, C(17)H(15)FO(3)S, the fluoro-phenyl ring makes a dihedral angle of 76.11 (5)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 5-alkyl-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofurans, see: Choi et al. (2010 ▶,c ▶).

Experimental

Crystal data

C17H15FO3S

M = 318.35

Orthorhombic,

a = 8.4395 (1) Å

b = 11.3701 (2) Å

c = 15.3559 (2) Å

V = 1473.52 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.35 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.920, T max = 0.962

14844 measured reflections

3665 independent reflections

3453 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.077

S = 1.09

3665 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1555 Friedel pairs

Flack parameter: −0.01 (6)

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/S1600536811015443/bh2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015443/bh2350Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015443/bh2350Isup3.cml

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

C17H15FO3S	Dx = 1.435 Mg m−3
Mr = 318.35	Melting point: 395 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6176 reflections
a = 8.4395 (1) Å	θ = 2.2–27.6°
b = 11.3701 (2) Å	µ = 0.24 mm−1
c = 15.3559 (2) Å	T = 173 K
V = 1473.52 (4) Å3	Block, colourless
Z = 4	0.35 × 0.25 × 0.16 mm
F(000) = 664

Bruker SMART APEXII CCD diffractometer	3665 independent reflections
Radiation source: rotating anode	3453 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→15
Tmin = 0.920, Tmax = 0.962	l = −19→20
14844 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.1728P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3665 reflections	Δρmax = 0.23 e Å−3
200 parameters	Δρmin = −0.30 e Å−3
0 restraints	Absolute structure: Flack (1983), 1555 Friedel pairs
0 constraints	Flack parameter: −0.01 (6)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
S1	0.55279 (4)	0.61633 (3)	0.30198 (2)	0.02203 (9)
F1	0.83613 (14)	0.24805 (9)	0.20382 (9)	0.0530 (3)
O1	0.45021 (12)	0.62846 (9)	0.55130 (7)	0.0262 (2)
O2	0.43231 (13)	0.56682 (11)	0.24756 (7)	0.0326 (3)
O3	0.59979 (14)	0.73710 (10)	0.29031 (8)	0.0320 (3)
C1	0.49455 (16)	0.59635 (12)	0.40936 (9)	0.0208 (3)
C2	0.41587 (16)	0.49312 (12)	0.44346 (9)	0.0203 (3)
C3	0.36195 (16)	0.38604 (13)	0.40976 (9)	0.0221 (3)
H3	0.3794	0.3663	0.3504	0.027*
C4	0.28224 (17)	0.30910 (13)	0.46495 (10)	0.0241 (3)
C5	0.25768 (18)	0.34013 (14)	0.55252 (11)	0.0278 (3)
H5	0.2020	0.2870	0.5891	0.033*
C6	0.31114 (19)	0.44473 (15)	0.58750 (11)	0.0278 (3)
H6	0.2944	0.4648	0.6468	0.033*
C7	0.39063 (17)	0.51841 (13)	0.53065 (10)	0.0227 (3)
C8	0.51210 (18)	0.67416 (13)	0.47591 (10)	0.0246 (3)
C9	0.2197 (2)	0.19327 (14)	0.43146 (11)	0.0300 (4)
H9A	0.2258	0.1931	0.3671	0.036*
H9B	0.1066	0.1860	0.4479	0.036*
C10	0.3089 (2)	0.08760 (15)	0.46610 (15)	0.0425 (5)
H10A	0.4204	0.0929	0.4488	0.064*
H10B	0.2625	0.0155	0.4422	0.064*
H10C	0.3016	0.0860	0.5298	0.064*
C11	0.5782 (2)	0.79444 (14)	0.48421 (12)	0.0351 (4)
H11A	0.6645	0.7941	0.5269	0.042*
H11B	0.4949	0.8484	0.5036	0.042*
H11C	0.6191	0.8203	0.4276	0.042*
C12	0.72448 (17)	0.52843 (13)	0.29036 (9)	0.0210 (3)
C13	0.70954 (19)	0.41921 (14)	0.25199 (11)	0.0272 (3)
H13	0.6099	0.3904	0.2327	0.033*
C14	0.8463 (2)	0.35391 (15)	0.24302 (12)	0.0322 (4)
C15	0.9925 (2)	0.39204 (16)	0.27131 (11)	0.0327 (4)
H15	1.0838	0.3439	0.2649	0.039*
C16	1.00295 (19)	0.50192 (15)	0.30918 (11)	0.0312 (3)
H16	1.1028	0.5301	0.3288	0.037*
C17	0.86942 (18)	0.57153 (13)	0.31887 (10)	0.0251 (3)
H17	0.8769	0.6473	0.3445	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.02206 (16)	0.02353 (17)	0.02051 (16)	0.00299 (14)	0.00042 (13)	0.00420 (14)
F1	0.0469 (6)	0.0286 (6)	0.0835 (9)	0.0008 (5)	0.0124 (6)	−0.0213 (6)
O1	0.0279 (5)	0.0269 (5)	0.0239 (5)	−0.0037 (5)	0.0046 (4)	−0.0048 (4)
O2	0.0275 (6)	0.0449 (7)	0.0254 (6)	0.0034 (5)	−0.0062 (5)	0.0003 (5)
O3	0.0394 (6)	0.0228 (5)	0.0337 (6)	0.0054 (5)	0.0075 (5)	0.0086 (5)
C1	0.0188 (6)	0.0215 (7)	0.0221 (7)	−0.0002 (5)	0.0015 (5)	0.0002 (5)
C2	0.0174 (6)	0.0217 (7)	0.0218 (7)	0.0023 (5)	0.0003 (5)	0.0016 (5)
C3	0.0209 (6)	0.0237 (7)	0.0216 (7)	0.0011 (6)	−0.0012 (5)	0.0008 (6)
C4	0.0195 (7)	0.0246 (8)	0.0282 (8)	−0.0002 (5)	−0.0018 (6)	0.0039 (6)
C5	0.0241 (8)	0.0310 (8)	0.0282 (8)	−0.0023 (6)	0.0045 (6)	0.0048 (6)
C6	0.0264 (7)	0.0334 (9)	0.0236 (8)	−0.0009 (6)	0.0056 (6)	0.0002 (6)
C7	0.0195 (6)	0.0247 (7)	0.0239 (7)	0.0007 (6)	0.0008 (5)	−0.0026 (6)
C8	0.0223 (7)	0.0266 (8)	0.0250 (7)	−0.0001 (6)	0.0026 (6)	−0.0011 (6)
C9	0.0302 (8)	0.0258 (8)	0.0341 (9)	−0.0071 (6)	−0.0021 (7)	0.0023 (7)
C10	0.0443 (10)	0.0253 (9)	0.0579 (13)	−0.0019 (7)	−0.0031 (9)	0.0033 (8)
C11	0.0406 (9)	0.0279 (8)	0.0368 (9)	−0.0094 (7)	0.0056 (8)	−0.0075 (7)
C12	0.0226 (6)	0.0204 (7)	0.0198 (7)	0.0005 (5)	0.0026 (5)	0.0043 (5)
C13	0.0262 (7)	0.0272 (8)	0.0281 (8)	−0.0038 (6)	0.0031 (6)	−0.0007 (6)
C14	0.0366 (9)	0.0231 (8)	0.0369 (9)	0.0007 (6)	0.0087 (8)	−0.0039 (6)
C15	0.0277 (7)	0.0301 (8)	0.0402 (9)	0.0067 (7)	0.0070 (7)	0.0047 (7)
C16	0.0228 (7)	0.0337 (8)	0.0372 (9)	−0.0014 (6)	−0.0036 (7)	0.0019 (7)
C17	0.0266 (7)	0.0229 (7)	0.0259 (8)	−0.0012 (6)	−0.0003 (6)	0.0008 (6)

S1—O2	1.4315 (12)	C9—C10	1.515 (2)
S1—O3	1.4405 (12)	C9—H9A	0.9900
S1—C1	1.7356 (14)	C9—H9B	0.9900
S1—C12	1.7692 (14)	C10—H10A	0.9800
F1—C14	1.3484 (19)	C10—H10B	0.9800
O1—C8	1.3723 (18)	C10—H10C	0.9800
O1—C7	1.3853 (18)	C11—H11A	0.9800
C1—C8	1.360 (2)	C11—H11B	0.9800
C1—C2	1.4466 (19)	C11—H11C	0.9800
C2—C7	1.386 (2)	C12—C13	1.380 (2)
C2—C3	1.399 (2)	C12—C17	1.389 (2)
C3—C4	1.391 (2)	C13—C14	1.379 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.406 (2)	C14—C15	1.378 (2)
C4—C9	1.509 (2)	C15—C16	1.381 (3)
C5—C6	1.381 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.385 (2)
C6—C7	1.383 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.483 (2)
O2—S1—O3	119.86 (7)	C4—C9—H9B	108.9
O2—S1—C1	107.58 (7)	C10—C9—H9B	108.9
O3—S1—C1	108.72 (7)	H9A—C9—H9B	107.7
O2—S1—C12	107.50 (7)	C9—C10—H10A	109.5
O3—S1—C12	107.48 (7)	C9—C10—H10B	109.5
C1—S1—C12	104.70 (7)	H10A—C10—H10B	109.5
C8—O1—C7	106.68 (12)	C9—C10—H10C	109.5
C8—C1—C2	107.81 (13)	H10A—C10—H10C	109.5
C8—C1—S1	126.72 (12)	H10B—C10—H10C	109.5
C2—C1—S1	125.46 (11)	C8—C11—H11A	109.5
C7—C2—C3	119.21 (13)	C8—C11—H11B	109.5
C7—C2—C1	104.59 (13)	H11A—C11—H11B	109.5
C3—C2—C1	136.17 (14)	C8—C11—H11C	109.5
C4—C3—C2	118.62 (14)	H11A—C11—H11C	109.5
C4—C3—H3	120.7	H11B—C11—H11C	109.5
C2—C3—H3	120.7	C13—C12—C17	122.18 (14)
C3—C4—C5	119.75 (14)	C13—C12—S1	118.45 (12)
C3—C4—C9	120.68 (14)	C17—C12—S1	119.36 (11)
C5—C4—C9	119.56 (14)	C14—C13—C12	116.78 (15)
C6—C5—C4	122.70 (15)	C14—C13—H13	121.6
C6—C5—H5	118.7	C12—C13—H13	121.6
C4—C5—H5	118.7	F1—C14—C15	118.59 (15)
C5—C6—C7	115.76 (15)	F1—C14—C13	118.16 (16)
C5—C6—H6	122.1	C15—C14—C13	123.25 (16)
C7—C6—H6	122.1	C14—C15—C16	118.35 (15)
C6—C7—O1	125.35 (14)	C14—C15—H15	120.8
C6—C7—C2	123.95 (14)	C16—C15—H15	120.8
O1—C7—C2	110.65 (13)	C15—C16—C17	120.67 (15)
C1—C8—O1	110.26 (13)	C15—C16—H16	119.7
C1—C8—C11	134.90 (15)	C17—C16—H16	119.7
O1—C8—C11	114.83 (13)	C16—C17—C12	118.77 (14)
C4—C9—C10	113.49 (14)	C16—C17—H17	120.6
C4—C9—H9A	108.9	C12—C17—H17	120.6
C10—C9—H9A	108.9
O2—S1—C1—C8	−140.71 (14)	C2—C1—C8—O1	0.08 (17)
O3—S1—C1—C8	−9.51 (16)	S1—C1—C8—O1	179.27 (10)
C12—S1—C1—C8	105.13 (15)	C2—C1—C8—C11	−178.45 (17)
O2—S1—C1—C2	38.35 (14)	S1—C1—C8—C11	0.7 (3)
O3—S1—C1—C2	169.55 (12)	C7—O1—C8—C1	−0.53 (16)
C12—S1—C1—C2	−75.81 (13)	C7—O1—C8—C11	178.32 (13)
C8—C1—C2—C7	0.40 (16)	C3—C4—C9—C10	109.92 (17)
S1—C1—C2—C7	−178.81 (11)	C5—C4—C9—C10	−71.0 (2)
C8—C1—C2—C3	178.42 (16)	O2—S1—C12—C13	−14.67 (14)
S1—C1—C2—C3	−0.8 (2)	O3—S1—C12—C13	−144.95 (12)
C7—C2—C3—C4	1.0 (2)	C1—S1—C12—C13	99.55 (13)
C1—C2—C3—C4	−176.79 (15)	O2—S1—C12—C17	164.54 (12)
C2—C3—C4—C5	0.0 (2)	O3—S1—C12—C17	34.25 (14)
C2—C3—C4—C9	179.12 (13)	C1—S1—C12—C17	−81.25 (13)
C3—C4—C5—C6	−0.7 (2)	C17—C12—C13—C14	0.0 (2)
C9—C4—C5—C6	−179.80 (15)	S1—C12—C13—C14	179.16 (13)
C4—C5—C6—C7	0.3 (2)	C12—C13—C14—F1	−178.39 (15)
C5—C6—C7—O1	178.16 (14)	C12—C13—C14—C15	0.9 (3)
C5—C6—C7—C2	0.8 (2)	F1—C14—C15—C16	178.19 (15)
C8—O1—C7—C6	−176.83 (14)	C13—C14—C15—C16	−1.1 (3)
C8—O1—C7—C2	0.81 (16)	C14—C15—C16—C17	0.4 (3)
C3—C2—C7—C6	−1.5 (2)	C15—C16—C17—C12	0.5 (2)
C1—C2—C7—C6	176.93 (14)	C13—C12—C17—C16	−0.7 (2)
C3—C2—C7—O1	−179.17 (11)	S1—C12—C17—C16	−179.84 (12)
C1—C2—C7—O1	−0.74 (16)

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

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.49	3.206 (2)	133
C13—H13···O3ii	0.95	2.51	3.395 (2)	155
C9—H9A···Cgiii	0.99	2.68	3.625 (2)	159

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
C6—H6⋯O2i	0.95	2.49	3.206 (2)	133
C13—H13⋯O3ii	0.95	2.51	3.395 (2)	155
C9—H9A⋯Cgiii	0.99	2.68	3.625 (2)	159

Symmetry codes: (i) ; (ii) ; (iii) .