3-(4-Fluoro-phenyl-sulfin-yl)-2-methyl-1-benzofuran.

In the title compound, C(15)H(11)FO(2)S, the O atom and the 4-fluoro-phenyl group of the 4-fluoro-phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the 4-fluoro-phenyl ring is almost perpendicular to this plane [dihedral angle = 89.59 (5)°]. Inter-molecular C-H⋯F and C-H⋯O hydrogen bonds link the mol-ecules together in the crystal structure.

Related literature

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

Experimental

Crystal data

C15H11FO2S

M = 274.30

Orthorhombic,

a = 14.992 (1) Å

b = 10.4661 (8) Å

c = 16.008 (1) Å

V = 2511.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.50 × 0.50 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.880, T max = 0.937

14681 measured reflections

2878 independent reflections

2315 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.10

2878 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.32 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 I. DOI: 10.1107/S1600536810004411/bg2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004411/bg2329Isup2.hkl

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

C15H11FO2S	F(000) = 1136
Mr = 274.30	Dx = 1.451 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6779 reflections
a = 14.992 (1) Å	θ = 2.4–27.5°
b = 10.4661 (8) Å	µ = 0.26 mm−1
c = 16.008 (1) Å	T = 173 K
V = 2511.8 (3) Å3	Block, colourless
Z = 8	0.50 × 0.50 × 0.25 mm

Bruker SMART APEXII CCD diffractometer	2878 independent reflections
Radiation source: Rotating Anode	2315 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −18→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.880, Tmax = 0.937	l = −15→20
14681 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.101	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0443P)2 + 1.1695P] where P = (Fo2 + 2Fc2)/3
2878 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.31 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
S	0.65767 (3)	0.58401 (4)	0.06490 (3)	0.03017 (13)
F	0.44627 (8)	0.14149 (11)	0.17017 (8)	0.0492 (3)
O1	0.59892 (8)	0.88631 (11)	0.19868 (8)	0.0342 (3)
O2	0.75317 (9)	0.54319 (13)	0.06877 (8)	0.0394 (3)
C1	0.63870 (11)	0.69730 (16)	0.14353 (10)	0.0276 (3)
C2	0.66131 (10)	0.69382 (15)	0.23170 (10)	0.0265 (3)
C3	0.70180 (11)	0.60712 (17)	0.28570 (11)	0.0310 (4)
H3	0.7212	0.5278	0.2668	0.037*
C4	0.71236 (12)	0.64306 (18)	0.36876 (11)	0.0352 (4)
H4	0.7384	0.5862	0.4062	0.042*
C5	0.68456 (13)	0.76314 (19)	0.39714 (11)	0.0374 (4)
H5	0.6926	0.7844	0.4531	0.045*
C6	0.64547 (12)	0.85086 (18)	0.34404 (11)	0.0362 (4)
H6	0.6272	0.9310	0.3625	0.043*
C7	0.63504 (11)	0.81283 (16)	0.26195 (11)	0.0299 (4)
C8	0.60331 (11)	0.81418 (16)	0.12734 (11)	0.0306 (4)
C9	0.57041 (13)	0.87542 (19)	0.04971 (12)	0.0399 (4)
H9A	0.5808	0.8195	0.0032	0.060*
H9B	0.6015	0.9545	0.0410	0.060*
H9C	0.5076	0.8919	0.0547	0.060*
C10	0.59373 (11)	0.45389 (15)	0.10668 (10)	0.0274 (3)
C11	0.63578 (12)	0.33736 (17)	0.11793 (11)	0.0316 (4)
H11	0.6971	0.3304	0.1102	0.038*
C12	0.58623 (13)	0.23096 (17)	0.14081 (11)	0.0360 (4)
H12	0.6134	0.1521	0.1493	0.043*
C13	0.49582 (12)	0.24576 (16)	0.15059 (11)	0.0341 (4)
C14	0.45240 (12)	0.36075 (18)	0.14095 (11)	0.0359 (4)
H14	0.3912	0.3671	0.1494	0.043*
C15	0.50226 (12)	0.46665 (16)	0.11837 (11)	0.0329 (4)
H15	0.4748	0.5456	0.1111	0.040*

	U11	U22	U33	U12	U13	U23
S	0.0341 (2)	0.0313 (2)	0.0251 (2)	−0.00272 (17)	−0.00071 (16)	−0.00052 (16)
F	0.0562 (7)	0.0355 (6)	0.0558 (7)	−0.0171 (5)	−0.0002 (6)	0.0001 (5)
O1	0.0408 (7)	0.0264 (6)	0.0354 (6)	0.0025 (5)	−0.0010 (5)	0.0017 (5)
O2	0.0311 (6)	0.0435 (7)	0.0437 (7)	−0.0024 (5)	0.0071 (6)	−0.0052 (6)
C1	0.0280 (8)	0.0273 (8)	0.0276 (8)	−0.0023 (6)	−0.0021 (6)	0.0010 (6)
C2	0.0253 (8)	0.0270 (8)	0.0273 (8)	−0.0037 (6)	0.0007 (6)	0.0000 (6)
C3	0.0317 (9)	0.0301 (8)	0.0311 (9)	0.0002 (7)	−0.0003 (7)	0.0017 (7)
C4	0.0347 (9)	0.0397 (10)	0.0312 (9)	−0.0023 (7)	−0.0049 (7)	0.0057 (7)
C5	0.0409 (10)	0.0442 (10)	0.0270 (9)	−0.0082 (8)	−0.0001 (8)	−0.0041 (8)
C6	0.0422 (10)	0.0307 (9)	0.0357 (9)	−0.0039 (7)	0.0052 (8)	−0.0053 (7)
C7	0.0310 (9)	0.0266 (8)	0.0320 (9)	−0.0026 (6)	0.0005 (7)	0.0024 (7)
C8	0.0287 (8)	0.0294 (8)	0.0337 (9)	−0.0033 (7)	−0.0028 (7)	0.0019 (7)
C9	0.0414 (10)	0.0371 (10)	0.0412 (10)	0.0005 (8)	−0.0091 (8)	0.0097 (8)
C10	0.0311 (8)	0.0274 (8)	0.0236 (8)	−0.0021 (6)	−0.0033 (6)	−0.0037 (6)
C11	0.0306 (9)	0.0320 (9)	0.0324 (9)	0.0038 (7)	−0.0009 (7)	−0.0045 (7)
C12	0.0453 (10)	0.0265 (8)	0.0364 (9)	0.0037 (7)	−0.0036 (8)	−0.0042 (7)
C13	0.0422 (10)	0.0287 (8)	0.0314 (9)	−0.0099 (7)	−0.0028 (7)	−0.0040 (7)
C14	0.0276 (8)	0.0398 (10)	0.0402 (10)	−0.0024 (7)	−0.0023 (7)	−0.0042 (8)
C15	0.0304 (8)	0.0291 (9)	0.0393 (9)	0.0028 (7)	−0.0049 (7)	−0.0010 (7)

S—O2	1.4953 (14)	C6—C7	1.382 (2)
S—C1	1.7525 (17)	C6—H6	0.9300
S—C10	1.7948 (17)	C8—C9	1.483 (2)
F—C13	1.357 (2)	C9—H9A	0.9600
O1—C8	1.371 (2)	C9—H9B	0.9600
O1—C7	1.382 (2)	C9—H9C	0.9600
C1—C8	1.358 (2)	C10—C11	1.385 (2)
C1—C2	1.452 (2)	C10—C15	1.390 (2)
C2—C3	1.393 (2)	C11—C12	1.388 (3)
C2—C7	1.393 (2)	C11—H11	0.9300
C3—C4	1.391 (2)	C12—C13	1.373 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.400 (3)	C13—C14	1.377 (3)
C4—H4	0.9300	C14—C15	1.385 (3)
C5—C6	1.382 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
O2—S—C1	108.60 (8)	C1—C8—C9	132.78 (17)
O2—S—C10	106.21 (8)	O1—C8—C9	116.38 (15)
C1—S—C10	99.15 (8)	C8—C9—H9A	109.5
C8—O1—C7	106.58 (13)	C8—C9—H9B	109.5
C8—C1—C2	107.42 (15)	H9A—C9—H9B	109.5
C8—C1—S	122.38 (13)	C8—C9—H9C	109.5
C2—C1—S	130.04 (13)	H9A—C9—H9C	109.5
C3—C2—C7	119.34 (15)	H9B—C9—H9C	109.5
C3—C2—C1	136.18 (16)	C11—C10—C15	121.07 (16)
C7—C2—C1	104.45 (14)	C11—C10—S	118.27 (13)
C4—C3—C2	117.83 (16)	C15—C10—S	120.27 (13)
C4—C3—H3	121.1	C10—C11—C12	119.83 (16)
C2—C3—H3	121.1	C10—C11—H11	120.1
C3—C4—C5	121.28 (17)	C12—C11—H11	120.1
C3—C4—H4	119.4	C13—C12—C11	117.90 (16)
C5—C4—H4	119.4	C13—C12—H12	121.1
C6—C5—C4	121.55 (17)	C11—C12—H12	121.1
C6—C5—H5	119.2	F—C13—C12	118.42 (16)
C4—C5—H5	119.2	F—C13—C14	118.04 (16)
C5—C6—C7	116.21 (17)	C12—C13—C14	123.54 (16)
C5—C6—H6	121.9	C13—C14—C15	118.26 (16)
C7—C6—H6	121.9	C13—C14—H14	120.9
C6—C7—O1	125.51 (16)	C15—C14—H14	120.9
C6—C7—C2	123.78 (16)	C14—C15—C10	119.38 (16)
O1—C7—C2	110.70 (14)	C14—C15—H15	120.3
C1—C8—O1	110.84 (15)	C10—C15—H15	120.3
O2—S—C1—C8	125.82 (15)	C2—C1—C8—O1	−1.56 (19)
C10—S—C1—C8	−123.54 (15)	S—C1—C8—O1	−177.39 (11)
O2—S—C1—C2	−48.99 (17)	C2—C1—C8—C9	178.10 (18)
C10—S—C1—C2	61.65 (16)	S—C1—C8—C9	2.3 (3)
C8—C1—C2—C3	−176.81 (19)	C7—O1—C8—C1	1.47 (18)
S—C1—C2—C3	−1.4 (3)	C7—O1—C8—C9	−178.25 (15)
C8—C1—C2—C7	1.00 (18)	O2—S—C10—C11	−12.66 (15)
S—C1—C2—C7	176.41 (13)	C1—S—C10—C11	−125.19 (13)
C7—C2—C3—C4	1.4 (2)	O2—S—C10—C15	174.41 (13)
C1—C2—C3—C4	178.99 (18)	C1—S—C10—C15	61.88 (15)
C2—C3—C4—C5	−1.0 (3)	C15—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	0.1 (3)	S—C10—C11—C12	−172.52 (13)
C4—C5—C6—C7	0.4 (3)	C10—C11—C12—C13	0.7 (3)
C5—C6—C7—O1	−178.95 (16)	C11—C12—C13—F	177.80 (15)
C5—C6—C7—C2	0.1 (3)	C11—C12—C13—C14	−1.7 (3)
C8—O1—C7—C6	178.34 (17)	F—C13—C14—C15	−177.99 (15)
C8—O1—C7—C2	−0.79 (18)	C12—C13—C14—C15	1.5 (3)
C3—C2—C7—C6	−1.0 (3)	C13—C14—C15—C10	−0.3 (3)
C1—C2—C7—C6	−179.27 (16)	C11—C10—C15—C14	−0.6 (3)
C3—C2—C7—O1	178.14 (14)	S—C10—C15—C14	172.18 (13)
C1—C2—C7—O1	−0.12 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Fi	0.93	2.52	3.346 (2)	148
C9—H9B···O2ii	0.96	2.41	3.189 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Fi	0.93	2.52	3.346 (2)	148
C9—H9B⋯O2ii	0.96	2.41	3.189 (2)	138

Symmetry codes: (i) ; (ii) .