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

In the title compound, C(18)H(17)FO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 82.12 (4)° with the plane of the benzofuran fragment. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the crystal structures of similar 2-methyl-3-phenyl­sulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,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

C18H17FO3S

M = 332.38

Monoclinic,

a = 10.9434 (6) Å

b = 11.3395 (6) Å

c = 13.0988 (7) Å

β = 100.252 (3)°

V = 1599.51 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 175 K

0.41 × 0.29 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.669, T max = 0.746

14304 measured reflections

3655 independent reflections

3109 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.02

3655 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.37 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/S1600536810012869/xu2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012869/xu2750Isup2.hkl

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

C18H17FO3S	F(000) = 696
Mr = 332.38	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6367 reflections
a = 10.9434 (6) Å	θ = 2.4–27.5°
b = 11.3395 (6) Å	µ = 0.23 mm−1
c = 13.0988 (7) Å	T = 175 K
β = 100.252 (3)°	Block, colourless
V = 1599.51 (15) Å3	0.41 × 0.29 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3655 independent reflections
Radiation source: rotating anode	3109 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.669, Tmax = 0.746	l = −16→16
14304 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.4509P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3655 reflections	Δρmax = 0.36 e Å−3
212 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0117 (15)

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
S	0.54221 (3)	0.13196 (3)	0.21925 (3)	0.02922 (13)
F	0.75485 (9)	−0.21439 (9)	−0.02852 (8)	0.0475 (3)
O1	0.44396 (10)	0.07695 (11)	0.26153 (9)	0.0415 (3)
O2	0.51752 (10)	0.23800 (9)	0.15885 (8)	0.0367 (3)
O3	0.79447 (10)	0.15165 (9)	0.47328 (8)	0.0300 (2)
C1	0.66335 (13)	0.16383 (12)	0.32124 (11)	0.0268 (3)
C2	0.75540 (12)	0.25570 (12)	0.32202 (10)	0.0244 (3)
C3	0.78117 (13)	0.34256 (12)	0.25361 (11)	0.0270 (3)
H3	0.7288	0.3527	0.1881	0.032*
C4	0.88480 (13)	0.41423 (13)	0.28261 (11)	0.0285 (3)
C5	0.96004 (13)	0.39900 (13)	0.38020 (11)	0.0302 (3)
H5	1.0300	0.4491	0.3993	0.036*
C6	0.93628 (13)	0.31367 (13)	0.44994 (11)	0.0297 (3)
H6	0.9877	0.3038	0.5159	0.036*
C7	0.83340 (13)	0.24398 (12)	0.41752 (10)	0.0257 (3)
C8	0.69246 (14)	0.10323 (13)	0.41204 (11)	0.0303 (3)
C9	0.91774 (15)	0.50549 (14)	0.20723 (12)	0.0356 (4)
H9	0.8483	0.5073	0.1462	0.043*
C10	1.0351 (2)	0.47032 (18)	0.16761 (16)	0.0548 (5)
H10A	1.1061	0.4728	0.2249	0.082*
H10B	1.0492	0.5253	0.1132	0.082*
H10C	1.0256	0.3902	0.1392	0.082*
C11	0.9299 (2)	0.62926 (15)	0.25374 (16)	0.0531 (5)
H11A	0.8558	0.6477	0.2832	0.080*
H11B	0.9381	0.6866	0.1994	0.080*
H11C	1.0036	0.6329	0.3085	0.080*
C12	0.64435 (18)	−0.00464 (15)	0.45463 (14)	0.0452 (4)
H12A	0.5675	−0.0294	0.4094	0.068*
H12B	0.6275	0.0117	0.5243	0.068*
H12C	0.7062	−0.0677	0.4584	0.068*
C13	0.60386 (13)	0.02725 (12)	0.14291 (11)	0.0274 (3)
C14	0.60321 (15)	−0.09153 (13)	0.16991 (12)	0.0342 (3)
H14	0.5684	−0.1159	0.2279	0.041*
C15	0.65382 (15)	−0.17364 (14)	0.11133 (13)	0.0375 (4)
H15	0.6546	−0.2551	0.1283	0.045*
C16	0.70315 (14)	−0.13427 (13)	0.02763 (13)	0.0332 (3)
C17	0.70304 (14)	−0.01834 (14)	−0.00155 (12)	0.0344 (3)
H17	0.7364	0.0049	−0.0606	0.041*
C18	0.65300 (14)	0.06423 (13)	0.05734 (12)	0.0309 (3)
H18	0.6523	0.1454	0.0394	0.037*

	U11	U22	U33	U12	U13	U23
S	0.0237 (2)	0.0283 (2)	0.0349 (2)	−0.00195 (13)	0.00319 (14)	−0.00717 (14)
F	0.0421 (6)	0.0428 (6)	0.0595 (7)	0.0017 (4)	0.0145 (5)	−0.0195 (5)
O1	0.0295 (6)	0.0473 (7)	0.0503 (7)	−0.0098 (5)	0.0138 (5)	−0.0133 (5)
O2	0.0336 (6)	0.0308 (6)	0.0412 (6)	0.0052 (4)	−0.0057 (5)	−0.0056 (5)
O3	0.0344 (6)	0.0300 (5)	0.0254 (5)	−0.0011 (4)	0.0047 (4)	0.0015 (4)
C1	0.0263 (7)	0.0248 (7)	0.0296 (7)	−0.0011 (5)	0.0061 (5)	−0.0042 (5)
C2	0.0238 (6)	0.0237 (7)	0.0254 (7)	0.0010 (5)	0.0033 (5)	−0.0044 (5)
C3	0.0282 (7)	0.0272 (7)	0.0238 (7)	−0.0006 (5)	0.0001 (5)	−0.0015 (5)
C4	0.0309 (7)	0.0270 (7)	0.0280 (7)	−0.0026 (6)	0.0060 (6)	−0.0031 (6)
C5	0.0276 (7)	0.0305 (7)	0.0317 (8)	−0.0043 (6)	0.0032 (6)	−0.0058 (6)
C6	0.0299 (7)	0.0317 (7)	0.0253 (7)	0.0021 (6)	−0.0009 (5)	−0.0044 (6)
C7	0.0296 (7)	0.0248 (7)	0.0229 (7)	0.0026 (5)	0.0055 (5)	−0.0014 (5)
C8	0.0318 (7)	0.0298 (7)	0.0307 (8)	−0.0016 (6)	0.0096 (6)	−0.0033 (6)
C9	0.0429 (9)	0.0341 (8)	0.0288 (7)	−0.0112 (7)	0.0035 (6)	0.0009 (6)
C10	0.0683 (13)	0.0476 (11)	0.0569 (12)	−0.0131 (9)	0.0341 (10)	−0.0023 (9)
C11	0.0834 (14)	0.0304 (9)	0.0503 (11)	−0.0054 (9)	0.0247 (10)	0.0037 (8)
C12	0.0516 (10)	0.0413 (9)	0.0444 (10)	−0.0111 (8)	0.0130 (8)	0.0077 (8)
C13	0.0245 (7)	0.0263 (7)	0.0302 (7)	−0.0030 (5)	0.0023 (5)	−0.0041 (6)
C14	0.0398 (8)	0.0281 (7)	0.0351 (8)	−0.0050 (6)	0.0080 (6)	−0.0006 (6)
C15	0.0423 (9)	0.0249 (7)	0.0445 (9)	−0.0006 (6)	0.0054 (7)	−0.0022 (7)
C16	0.0248 (7)	0.0340 (8)	0.0396 (9)	−0.0004 (6)	0.0029 (6)	−0.0126 (6)
C17	0.0315 (8)	0.0378 (8)	0.0349 (8)	−0.0083 (6)	0.0087 (6)	−0.0040 (6)
C18	0.0303 (7)	0.0269 (7)	0.0350 (8)	−0.0057 (6)	0.0046 (6)	−0.0004 (6)

S—O1	1.437 (1)	C9—C11	1.526 (2)
S—O2	1.438 (1)	C9—H9	1.0000
S—C1	1.744 (2)	C10—H10A	0.9800
S—C13	1.762 (1)	C10—H10B	0.9800
F—C16	1.355 (2)	C10—H10C	0.9800
O3—C8	1.368 (2)	C11—H11A	0.9800
O3—C7	1.386 (2)	C11—H11B	0.9800
C1—C8	1.361 (2)	C11—H11C	0.9800
C1—C2	1.448 (2)	C12—H12A	0.9800
C2—C7	1.390 (2)	C12—H12B	0.9800
C2—C3	1.394 (2)	C12—H12C	0.9800
C3—C4	1.392 (2)	C13—C14	1.393 (2)
C3—H3	0.9500	C13—C18	1.391 (2)
C4—C5	1.403 (2)	C14—C15	1.383 (2)
C4—C9	1.517 (2)	C14—H14	0.9500
C5—C6	1.387 (2)	C15—C16	1.380 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.369 (2)
C6—H6	0.9500	C17—C18	1.386 (2)
C8—C12	1.480 (2)	C17—H17	0.9500
C9—C10	1.521 (2)	C18—H18	0.9500
O1—S—O2	119.66 (7)	C9—C10—H10A	109.5
O1—S—C1	108.28 (7)	C9—C10—H10B	109.5
O2—S—C1	106.91 (7)	H10A—C10—H10B	109.5
O1—S—C13	108.33 (7)	C9—C10—H10C	109.5
O2—S—C13	107.74 (7)	H10A—C10—H10C	109.5
C1—S—C13	104.99 (7)	H10B—C10—H10C	109.5
C8—O3—C7	106.82 (11)	C9—C11—H11A	109.5
C8—C1—C2	107.62 (13)	C9—C11—H11B	109.5
C8—C1—S	126.33 (11)	H11A—C11—H11B	109.5
C2—C1—S	125.97 (11)	C9—C11—H11C	109.5
C7—C2—C3	118.96 (12)	H11A—C11—H11C	109.5
C7—C2—C1	104.63 (12)	H11B—C11—H11C	109.5
C3—C2—C1	136.39 (13)	C8—C12—H12A	109.5
C4—C3—C2	119.04 (13)	C8—C12—H12B	109.5
C4—C3—H3	120.5	H12A—C12—H12B	109.5
C2—C3—H3	120.5	C8—C12—H12C	109.5
C3—C4—C5	119.64 (13)	H12A—C12—H12C	109.5
C3—C4—C9	119.80 (13)	H12B—C12—H12C	109.5
C5—C4—C9	120.53 (13)	C14—C13—C18	121.08 (14)
C6—C5—C4	122.53 (13)	C14—C13—S	119.19 (11)
C6—C5—H5	118.7	C18—C13—S	119.73 (11)
C4—C5—H5	118.7	C15—C14—C13	119.29 (14)
C7—C6—C5	115.82 (13)	C15—C14—H14	120.4
C7—C6—H6	122.1	C13—C14—H14	120.4
C5—C6—H6	122.1	C16—C15—C14	118.36 (14)
C6—C7—O3	125.53 (13)	C16—C15—H15	120.8
C6—C7—C2	124.01 (13)	C14—C15—H15	120.8
O3—C7—C2	110.45 (12)	F—C16—C17	118.17 (14)
C1—C8—O3	110.44 (13)	F—C16—C15	118.35 (14)
C1—C8—C12	134.67 (15)	C17—C16—C15	123.48 (14)
O3—C8—C12	114.75 (13)	C16—C17—C18	118.29 (14)
C4—C9—C10	110.85 (14)	C16—C17—H17	120.9
C4—C9—C11	112.42 (13)	C18—C17—H17	120.9
C10—C9—C11	110.99 (15)	C17—C18—C13	119.49 (14)
C4—C9—H9	107.4	C17—C18—H18	120.3
C10—C9—H9	107.4	C13—C18—H18	120.3
C11—C9—H9	107.4

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.95	2.51	3.401 (2)	155
C10—H10B···Cg1ii	0.98	2.86	3.561 (2)	120
C11—H11B···Cg2ii	0.98	2.91	3.670 (2)	135
C17—H17···Cg2iii	0.95	2.89	3.528 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O3/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.95	2.51	3.401 (2)	155
C10—H10B⋯Cg1ii	0.98	2.86	3.561 (2)	120
C11—H11B⋯Cg2ii	0.98	2.91	3.670 (2)	135
C17—H17⋯Cg2iii	0.95	2.89	3.528 (2)	147

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