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

In the title compound, C(17)H(15)FO(3)S, the 2-fluoro-phenyl ring makes a dihedral angle of 89.12 (8)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C17H15FO3S

M = 318.35

Monoclinic,

a = 11.290 (2) Å

b = 16.171 (3) Å

c = 8.5612 (14) Å

β = 105.045 (11)°

V = 1509.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.38 × 0.30 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.545, T max = 0.746

7108 measured reflections

3129 independent reflections

2676 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 1.06

3129 reflections

201 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1271 Friedel pairs

Flack parameter: −0.05 (8)

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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036872/fj2589sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036872/fj2589Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036872/fj2589Isup3.cml

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

C17H15FO3S	F(000) = 664
Mr = 318.35	Dx = 1.401 Mg m−3
Monoclinic, Cc	Melting point = 410–411 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.290 (2) Å	Cell parameters from 2955 reflections
b = 16.171 (3) Å	θ = 2.3–27.5°
c = 8.5612 (14) Å	µ = 0.24 mm−1
β = 105.045 (11)°	T = 173 K
V = 1509.4 (5) Å3	Block, colourless
Z = 4	0.38 × 0.30 × 0.27 mm

Bruker SMART APEXII CCD diffractometer	3129 independent reflections
Radiation source: rotating anode	2676 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 28.2°, θmin = 2.3°
φ and ω scans	h = −13→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→19
Tmin = 0.545, Tmax = 0.746	l = −11→11
7108 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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.5589P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3129 reflections	Δρmax = 0.61 e Å−3
201 parameters	Δρmin = −0.35 e Å−3
2 restraints	Absolute structure: Flack (1983), 1271 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (8)

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	0.14686 (6)	0.71642 (4)	0.27469 (7)	0.03361 (16)
O1	0.13896 (19)	0.47875 (12)	0.1852 (2)	0.0427 (5)
O2	0.2615 (2)	0.75833 (13)	0.2964 (3)	0.0462 (5)
O3	0.0429 (2)	0.74224 (14)	0.1475 (2)	0.0503 (6)
F1	−0.07139 (15)	0.64592 (12)	0.3612 (2)	0.0498 (4)
C1	0.1696 (2)	0.61168 (16)	0.2571 (3)	0.0316 (5)
C2	0.2695 (2)	0.56448 (15)	0.3603 (3)	0.0297 (5)
C3	0.3736 (2)	0.58219 (17)	0.4846 (3)	0.0331 (5)
H3	0.3936	0.6377	0.5176	0.040*
C4	0.4472 (3)	0.51754 (17)	0.5588 (3)	0.0366 (6)
C5	0.4155 (3)	0.43570 (18)	0.5073 (4)	0.0455 (7)
H5	0.4655	0.3916	0.5608	0.055*
C6	0.3147 (3)	0.41750 (18)	0.3825 (4)	0.0456 (7)
H6	0.2949	0.3623	0.3474	0.055*
C7	0.2437 (3)	0.48350 (17)	0.3110 (4)	0.0364 (6)
C8	0.0946 (2)	0.55781 (18)	0.1554 (3)	0.0375 (6)
C9	0.5622 (3)	0.5333 (2)	0.6926 (3)	0.0463 (7)
H9A	0.5547	0.5875	0.7426	0.056*
H9B	0.5690	0.4904	0.7770	0.056*
C10	0.6777 (3)	0.5328 (3)	0.6354 (5)	0.0625 (10)
H10A	0.6869	0.4788	0.5880	0.094*
H10B	0.7485	0.5433	0.7272	0.094*
H10C	0.6726	0.5760	0.5537	0.094*
C11	−0.0195 (3)	0.5648 (2)	0.0229 (4)	0.0544 (8)
H11A	−0.0508	0.6215	0.0184	0.082*
H11B	−0.0812	0.5264	0.0429	0.082*
H11C	−0.0019	0.5510	−0.0803	0.082*
C12	0.1073 (2)	0.72538 (15)	0.4600 (3)	0.0278 (5)
C13	0.1835 (2)	0.76928 (16)	0.5882 (3)	0.0350 (6)
H13	0.2585	0.7921	0.5772	0.042*
C14	0.1496 (3)	0.77939 (18)	0.7304 (3)	0.0421 (7)
H14	0.2010	0.8096	0.8171	0.051*
C15	0.0410 (3)	0.7457 (2)	0.7474 (3)	0.0427 (7)
H15	0.0180	0.7532	0.8456	0.051*
C16	−0.0339 (3)	0.70139 (18)	0.6230 (4)	0.0402 (6)
H16	−0.1082	0.6778	0.6347	0.048*
C17	0.0007 (2)	0.69186 (17)	0.4819 (3)	0.0335 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0419 (3)	0.0300 (3)	0.0335 (3)	0.0059 (3)	0.0181 (2)	0.0064 (3)
O1	0.0395 (11)	0.0359 (11)	0.0531 (11)	−0.0064 (9)	0.0129 (9)	−0.0118 (9)
O2	0.0523 (12)	0.0343 (11)	0.0632 (13)	−0.0018 (9)	0.0352 (11)	0.0056 (9)
O3	0.0683 (16)	0.0478 (13)	0.0349 (10)	0.0197 (11)	0.0135 (10)	0.0118 (9)
F1	0.0375 (9)	0.0586 (11)	0.0550 (9)	−0.0101 (8)	0.0147 (8)	−0.0151 (8)
C1	0.0346 (14)	0.0315 (12)	0.0326 (12)	0.0013 (10)	0.0158 (10)	−0.0010 (10)
C2	0.0329 (12)	0.0235 (12)	0.0368 (12)	0.0006 (10)	0.0162 (10)	−0.0004 (9)
C3	0.0374 (14)	0.0284 (13)	0.0360 (12)	0.0005 (11)	0.0141 (11)	−0.0004 (10)
C4	0.0390 (15)	0.0349 (14)	0.0379 (13)	0.0045 (11)	0.0137 (11)	0.0038 (11)
C5	0.0484 (17)	0.0307 (15)	0.0598 (18)	0.0084 (13)	0.0181 (14)	0.0088 (13)
C6	0.0481 (17)	0.0252 (15)	0.0667 (19)	−0.0008 (12)	0.0206 (15)	−0.0022 (12)
C7	0.0339 (14)	0.0309 (13)	0.0478 (14)	−0.0030 (11)	0.0170 (11)	−0.0043 (11)
C8	0.0373 (14)	0.0402 (16)	0.0371 (13)	0.0011 (11)	0.0137 (11)	−0.0037 (11)
C9	0.0480 (17)	0.0489 (19)	0.0385 (14)	0.0091 (14)	0.0051 (13)	0.0054 (13)
C10	0.0399 (18)	0.084 (3)	0.058 (2)	−0.0033 (17)	0.0042 (15)	−0.0094 (18)
C11	0.0429 (18)	0.068 (2)	0.0491 (17)	0.0014 (16)	0.0051 (14)	−0.0069 (15)
C12	0.0321 (12)	0.0238 (12)	0.0297 (11)	0.0062 (10)	0.0120 (9)	0.0045 (8)
C13	0.0311 (13)	0.0289 (13)	0.0444 (14)	0.0033 (10)	0.0087 (10)	−0.0004 (10)
C14	0.0450 (16)	0.0420 (16)	0.0360 (14)	0.0112 (13)	0.0044 (13)	−0.0033 (11)
C15	0.0531 (17)	0.0437 (16)	0.0353 (13)	0.0148 (14)	0.0186 (12)	0.0055 (12)
C16	0.0421 (15)	0.0374 (15)	0.0480 (15)	0.0073 (12)	0.0241 (13)	0.0078 (11)
C17	0.0308 (13)	0.0324 (13)	0.0376 (13)	0.0035 (10)	0.0094 (10)	−0.0002 (10)

S1—O2	1.430 (2)	C9—C10	1.507 (5)
S1—O3	1.440 (2)	C9—H9A	0.9900
S1—C1	1.726 (3)	C9—H9B	0.9900
S1—C12	1.762 (2)	C10—H10A	0.9800
O1—C8	1.373 (4)	C10—H10B	0.9800
O1—C7	1.379 (3)	C10—H10C	0.9800
F1—C17	1.359 (3)	C11—H11A	0.9800
C1—C8	1.361 (4)	C11—H11B	0.9800
C1—C2	1.455 (4)	C11—H11C	0.9800
C2—C7	1.384 (4)	C12—C17	1.377 (4)
C2—C3	1.395 (3)	C12—C13	1.400 (3)
C3—C4	1.383 (4)	C13—C14	1.377 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.411 (4)	C14—C15	1.383 (4)
C4—C9	1.513 (4)	C14—H14	0.9500
C5—C6	1.376 (4)	C15—C16	1.377 (5)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (4)	C16—C17	1.371 (4)
C6—H6	0.9500	C16—H16	0.9500
C8—C11	1.484 (4)
O2—S1—O3	119.56 (14)	C10—C9—H9B	108.9
O2—S1—C1	109.03 (12)	C4—C9—H9B	108.9
O3—S1—C1	109.23 (13)	H9A—C9—H9B	107.7
O2—S1—C12	106.06 (13)	C9—C10—H10A	109.5
O3—S1—C12	108.04 (12)	C9—C10—H10B	109.5
C1—S1—C12	103.74 (11)	H10A—C10—H10B	109.5
C8—O1—C7	106.9 (2)	C9—C10—H10C	109.5
C8—C1—C2	108.0 (2)	H10A—C10—H10C	109.5
C8—C1—S1	127.0 (2)	H10B—C10—H10C	109.5
C2—C1—S1	124.86 (18)	C8—C11—H11A	109.5
C7—C2—C3	119.7 (2)	C8—C11—H11B	109.5
C7—C2—C1	104.0 (2)	H11A—C11—H11B	109.5
C3—C2—C1	136.2 (2)	C8—C11—H11C	109.5
C4—C3—C2	118.8 (2)	H11A—C11—H11C	109.5
C4—C3—H3	120.6	H11B—C11—H11C	109.5
C2—C3—H3	120.6	C17—C12—C13	118.3 (2)
C3—C4—C5	119.4 (3)	C17—C12—S1	121.71 (19)
C3—C4—C9	121.0 (3)	C13—C12—S1	120.02 (19)
C5—C4—C9	119.5 (2)	C14—C13—C12	119.9 (3)
C6—C5—C4	122.3 (3)	C14—C13—H13	120.0
C6—C5—H5	118.8	C12—C13—H13	120.0
C4—C5—H5	118.8	C13—C14—C15	120.2 (3)
C5—C6—C7	116.6 (3)	C13—C14—H14	119.9
C5—C6—H6	121.7	C15—C14—H14	119.9
C7—C6—H6	121.7	C16—C15—C14	120.5 (3)
C6—C7—O1	125.8 (3)	C16—C15—H15	119.8
C6—C7—C2	123.0 (3)	C14—C15—H15	119.8
O1—C7—C2	111.1 (2)	C17—C16—C15	118.8 (3)
C1—C8—O1	109.9 (2)	C17—C16—H16	120.6
C1—C8—C11	135.5 (3)	C15—C16—H16	120.6
O1—C8—C11	114.5 (3)	F1—C17—C16	118.7 (2)
C10—C9—C4	113.4 (3)	F1—C17—C12	118.9 (2)
C10—C9—H9A	108.9	C16—C17—C12	122.4 (2)
C4—C9—H9A	108.9
O2—S1—C1—C8	−140.5 (2)	C2—C1—C8—O1	−0.1 (3)
O3—S1—C1—C8	−8.2 (3)	S1—C1—C8—O1	−175.45 (18)
C12—S1—C1—C8	106.8 (2)	C2—C1—C8—C11	−179.2 (3)
O2—S1—C1—C2	44.9 (2)	S1—C1—C8—C11	5.5 (5)
O3—S1—C1—C2	177.2 (2)	C7—O1—C8—C1	1.0 (3)
C12—S1—C1—C2	−67.8 (2)	C7—O1—C8—C11	−179.7 (2)
C8—C1—C2—C7	−0.8 (3)	C3—C4—C9—C10	−98.5 (4)
S1—C1—C2—C7	174.68 (19)	C5—C4—C9—C10	80.6 (4)
C8—C1—C2—C3	179.4 (3)	O2—S1—C12—C17	179.8 (2)
S1—C1—C2—C3	−5.1 (4)	O3—S1—C12—C17	50.5 (2)
C7—C2—C3—C4	−1.7 (4)	C1—S1—C12—C17	−65.4 (2)
C1—C2—C3—C4	178.1 (3)	O2—S1—C12—C13	1.4 (2)
C2—C3—C4—C5	0.0 (4)	O3—S1—C12—C13	−127.9 (2)
C2—C3—C4—C9	179.1 (2)	C1—S1—C12—C13	116.3 (2)
C3—C4—C5—C6	1.5 (5)	C17—C12—C13—C14	−1.3 (3)
C9—C4—C5—C6	−177.6 (3)	S1—C12—C13—C14	177.1 (2)
C4—C5—C6—C7	−1.2 (5)	C12—C13—C14—C15	0.5 (4)
C5—C6—C7—O1	−179.6 (3)	C13—C14—C15—C16	0.4 (4)
C5—C6—C7—C2	−0.5 (5)	C14—C15—C16—C17	−0.5 (4)
C8—O1—C7—C6	177.7 (3)	C15—C16—C17—F1	178.0 (2)
C8—O1—C7—C2	−1.5 (3)	C15—C16—C17—C12	−0.4 (4)
C3—C2—C7—C6	2.0 (4)	C13—C12—C17—F1	−177.1 (2)
C1—C2—C7—C6	−177.8 (3)	S1—C12—C17—F1	4.6 (3)
C3—C2—C7—O1	−178.8 (2)	C13—C12—C17—C16	1.3 (4)
C1—C2—C7—O1	1.4 (3)	S1—C12—C17—C16	−177.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3i	0.95	2.53	3.420 (3)	156
C16—H16···O2ii	0.95	2.49	3.121 (4)	124
C5—H5···Cgiii	0.95	2.79	3.692 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 2-fluoro­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3i	0.95	2.53	3.420 (3)	156
C16—H16⋯O2ii	0.95	2.49	3.121 (4)	124
C5—H5⋯Cg iii	0.95	2.79	3.692 (3)	159

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