5-Fluoro-2-(4-methyl-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C16H13FO2S, the 4-methyl-phenyl ring makes a dihedral angle of 29.53 (4)° with the mean plane of the benzofuran fragment [r.m.s. deviation = 0.004 (1) Å]. In the crystal, mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds, forming inversion dimers that stack along the a axis.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009a ▶,b ▶).

Experimental

Crystal data

C16H13FO2S

M = 288.32

Triclinic,

a = 8.0407 (2) Å

b = 8.0838 (2) Å

c = 11.3517 (2) Å

α = 80.126 (1)°

β = 85.091 (1)°

γ = 66.773 (1)°

V = 667.88 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.53 × 0.40 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.701, T max = 0.746

12234 measured reflections

3307 independent reflections

3095 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.09

3307 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.24 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044844/su2522sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044844/su2522Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044844/su2522Isup3.cml

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

C16H13FO2S	Z = 2
Mr = 288.32	F(000) = 300
Triclinic, P1	Dx = 1.434 Mg m−3
Hall symbol: -P 1	Melting point < 418 K
a = 8.0407 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0838 (2) Å	Cell parameters from 7852 reflections
c = 11.3517 (2) Å	θ = 2.8–28.3°
α = 80.126 (1)°	µ = 0.25 mm−1
β = 85.091 (1)°	T = 173 K
γ = 66.773 (1)°	Block, colourless
V = 667.88 (3) Å3	0.53 × 0.40 × 0.24 mm

Bruker SMART APEXII CCD diffractometer	3307 independent reflections
Radiation source: rotating anode	3095 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.020
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.701, Tmax = 0.746	l = −15→15
12234 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.091	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.2225P] where P = (Fo2 + 2Fc2)/3
3307 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.24 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	0.33118 (4)	0.20343 (4)	0.41621 (3)	0.02410 (10)
O1	0.15249 (12)	0.70005 (11)	0.50374 (7)	0.02400 (18)
F1	−0.01539 (13)	0.79204 (12)	0.03932 (7)	0.0428 (2)
O2	0.21524 (13)	0.17958 (13)	0.33018 (10)	0.0378 (2)
C1	0.24601 (16)	0.43759 (15)	0.42709 (10)	0.0221 (2)
C9	0.30709 (16)	0.43979 (16)	0.64794 (10)	0.0223 (2)
C8	0.23981 (16)	0.51353 (15)	0.52688 (10)	0.0221 (2)
C7	0.10062 (16)	0.74208 (16)	0.38628 (10)	0.0226 (2)
C10	0.46136 (17)	0.28077 (17)	0.67089 (11)	0.0260 (2)
H10	0.5246	0.2185	0.6068	0.031*
C2	0.15628 (16)	0.58455 (15)	0.33364 (10)	0.0221 (2)
C14	0.21693 (17)	0.53140 (17)	0.74329 (11)	0.0260 (2)
H14	0.1117	0.6401	0.7292	0.031*
C3	0.11782 (17)	0.59876 (17)	0.21373 (11)	0.0267 (2)
H3	0.1527	0.4950	0.1745	0.032*
C12	0.43513 (19)	0.30326 (18)	0.88157 (11)	0.0294 (3)
C11	0.52340 (18)	0.21267 (18)	0.78664 (11)	0.0292 (3)
H11	0.6274	0.1029	0.8011	0.035*
C6	0.01006 (17)	0.91590 (17)	0.32716 (11)	0.0274 (3)
H6	−0.0244	1.0202	0.3658	0.033*
C13	0.28174 (19)	0.46301 (18)	0.85797 (11)	0.0299 (3)
H13	0.2203	0.5264	0.9221	0.036*
C5	−0.02757 (18)	0.92941 (18)	0.20837 (12)	0.0303 (3)
H5	−0.0899	1.0452	0.1629	0.036*
C16	0.53640 (17)	0.19025 (18)	0.33560 (12)	0.0293 (3)
H16A	0.5951	0.0708	0.3092	0.044*
H16B	0.6178	0.2069	0.3877	0.044*
H16C	0.5085	0.2859	0.2657	0.044*
C4	0.02649 (18)	0.77212 (19)	0.15608 (11)	0.0297 (3)
C15	0.5046 (2)	0.2319 (2)	1.00707 (13)	0.0438 (4)
H15A	0.6136	0.1200	1.0067	0.066*
H15B	0.4114	0.2057	1.0589	0.066*
H15C	0.5341	0.3235	1.0371	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.02488 (16)	0.01864 (15)	0.02810 (16)	−0.00752 (11)	0.00168 (11)	−0.00507 (11)
O1	0.0276 (4)	0.0198 (4)	0.0228 (4)	−0.0066 (3)	−0.0014 (3)	−0.0045 (3)
F1	0.0568 (6)	0.0438 (5)	0.0221 (4)	−0.0142 (4)	−0.0091 (4)	0.0014 (3)
O2	0.0297 (5)	0.0315 (5)	0.0574 (6)	−0.0110 (4)	−0.0052 (4)	−0.0204 (5)
C1	0.0231 (5)	0.0196 (5)	0.0228 (5)	−0.0074 (4)	0.0002 (4)	−0.0038 (4)
C9	0.0237 (5)	0.0230 (5)	0.0216 (5)	−0.0105 (4)	−0.0004 (4)	−0.0035 (4)
C8	0.0218 (5)	0.0197 (5)	0.0238 (5)	−0.0070 (4)	0.0009 (4)	−0.0037 (4)
C7	0.0227 (5)	0.0229 (5)	0.0221 (5)	−0.0087 (4)	−0.0005 (4)	−0.0037 (4)
C10	0.0249 (6)	0.0278 (6)	0.0240 (6)	−0.0082 (5)	0.0001 (4)	−0.0060 (4)
C2	0.0217 (5)	0.0209 (5)	0.0234 (5)	−0.0081 (4)	0.0006 (4)	−0.0031 (4)
C14	0.0275 (6)	0.0244 (6)	0.0260 (6)	−0.0094 (5)	0.0015 (5)	−0.0060 (4)
C3	0.0301 (6)	0.0275 (6)	0.0231 (5)	−0.0115 (5)	−0.0002 (5)	−0.0047 (4)
C12	0.0354 (7)	0.0332 (6)	0.0232 (6)	−0.0173 (5)	−0.0050 (5)	−0.0020 (5)
C11	0.0267 (6)	0.0289 (6)	0.0290 (6)	−0.0077 (5)	−0.0050 (5)	−0.0017 (5)
C6	0.0271 (6)	0.0214 (5)	0.0310 (6)	−0.0069 (5)	−0.0005 (5)	−0.0033 (5)
C13	0.0362 (7)	0.0327 (6)	0.0233 (6)	−0.0150 (6)	0.0024 (5)	−0.0083 (5)
C5	0.0295 (6)	0.0250 (6)	0.0308 (6)	−0.0070 (5)	−0.0031 (5)	0.0031 (5)
C16	0.0263 (6)	0.0314 (6)	0.0305 (6)	−0.0105 (5)	0.0036 (5)	−0.0091 (5)
C4	0.0324 (6)	0.0342 (7)	0.0210 (5)	−0.0125 (5)	−0.0030 (5)	−0.0002 (5)
C15	0.0576 (10)	0.0467 (9)	0.0260 (7)	−0.0186 (8)	−0.0123 (6)	−0.0012 (6)

S1—O2	1.4907 (10)	C3—C4	1.3738 (18)
S1—C1	1.7637 (11)	C3—H3	0.9500
S1—C16	1.7911 (13)	C12—C11	1.3897 (18)
O1—C7	1.3767 (14)	C12—C13	1.3937 (19)
O1—C8	1.3770 (14)	C12—C15	1.5082 (17)
F1—C4	1.3625 (14)	C11—H11	0.9500
C1—C8	1.3665 (16)	C6—C5	1.3839 (18)
C1—C2	1.4422 (16)	C6—H6	0.9500
C9—C10	1.3935 (17)	C13—H13	0.9500
C9—C14	1.4009 (16)	C5—C4	1.3917 (19)
C9—C8	1.4589 (16)	C5—H5	0.9500
C7—C6	1.3814 (16)	C16—H16A	0.9800
C7—C2	1.3945 (16)	C16—H16B	0.9800
C10—C11	1.3878 (17)	C16—H16C	0.9800
C10—H10	0.9500	C15—H15A	0.9800
C2—C3	1.3971 (16)	C15—H15B	0.9800
C14—C13	1.3835 (17)	C15—H15C	0.9800
C14—H14	0.9500
O2—S1—C1	106.91 (6)	C11—C12—C15	120.89 (13)
O2—S1—C16	105.80 (6)	C13—C12—C15	120.67 (12)
C1—S1—C16	97.50 (6)	C10—C11—C12	120.76 (12)
C7—O1—C8	106.64 (9)	C10—C11—H11	119.6
C8—C1—C2	107.14 (10)	C12—C11—H11	119.6
C8—C1—S1	126.89 (9)	C7—C6—C5	116.19 (11)
C2—C1—S1	125.80 (9)	C7—C6—H6	121.9
C10—C9—C14	118.99 (11)	C5—C6—H6	121.9
C10—C9—C8	121.35 (10)	C14—C13—C12	121.48 (12)
C14—C9—C8	119.65 (11)	C14—C13—H13	119.3
C1—C8—O1	110.59 (10)	C12—C13—H13	119.3
C1—C8—C9	133.89 (11)	C6—C5—C4	119.51 (12)
O1—C8—C9	115.52 (10)	C6—C5—H5	120.2
O1—C7—C6	125.11 (11)	C4—C5—H5	120.2
O1—C7—C2	110.54 (10)	S1—C16—H16A	109.5
C6—C7—C2	124.33 (11)	S1—C16—H16B	109.5
C11—C10—C9	120.55 (11)	H16A—C16—H16B	109.5
C11—C10—H10	119.7	S1—C16—H16C	109.5
C9—C10—H10	119.7	H16A—C16—H16C	109.5
C7—C2—C3	119.30 (11)	H16B—C16—H16C	109.5
C7—C2—C1	105.09 (10)	F1—C4—C3	117.81 (12)
C3—C2—C1	135.61 (11)	F1—C4—C5	117.39 (11)
C13—C14—C9	119.77 (12)	C3—C4—C5	124.80 (12)
C13—C14—H14	120.1	C12—C15—H15A	109.5
C9—C14—H14	120.1	C12—C15—H15B	109.5
C4—C3—C2	115.87 (11)	H15A—C15—H15B	109.5
C4—C3—H3	122.1	C12—C15—H15C	109.5
C2—C3—H3	122.1	H15A—C15—H15C	109.5
C11—C12—C13	118.44 (11)	H15B—C15—H15C	109.5
O2—S1—C1—C8	144.62 (11)	C8—C1—C2—C7	−0.31 (13)
C16—S1—C1—C8	−106.28 (12)	S1—C1—C2—C7	175.22 (9)
O2—S1—C1—C2	−30.03 (12)	C8—C1—C2—C3	179.87 (13)
C16—S1—C1—C2	79.07 (11)	S1—C1—C2—C3	−4.6 (2)
C2—C1—C8—O1	−0.23 (13)	C10—C9—C14—C13	−0.10 (18)
S1—C1—C8—O1	−175.69 (8)	C8—C9—C14—C13	−179.19 (11)
C2—C1—C8—C9	−179.10 (12)	C7—C2—C3—C4	0.33 (17)
S1—C1—C8—C9	5.4 (2)	C1—C2—C3—C4	−179.86 (13)
C7—O1—C8—C1	0.68 (13)	C9—C10—C11—C12	−1.2 (2)
C7—O1—C8—C9	179.78 (9)	C13—C12—C11—C10	0.7 (2)
C10—C9—C8—C1	29.5 (2)	C15—C12—C11—C10	−178.63 (13)
C14—C9—C8—C1	−151.45 (13)	O1—C7—C6—C5	179.08 (11)
C10—C9—C8—O1	−149.35 (11)	C2—C7—C6—C5	0.79 (19)
C14—C9—C8—O1	29.72 (15)	C9—C14—C13—C12	−0.41 (19)
C8—O1—C7—C6	−179.38 (11)	C11—C12—C13—C14	0.1 (2)
C8—O1—C7—C2	−0.89 (13)	C15—C12—C13—C14	179.43 (13)
C14—C9—C10—C11	0.90 (18)	C7—C6—C5—C4	−0.17 (19)
C8—C9—C10—C11	179.98 (11)	C2—C3—C4—F1	−179.35 (11)
O1—C7—C2—C3	−179.40 (10)	C2—C3—C4—C5	0.3 (2)
C6—C7—C2—C3	−0.90 (18)	C6—C5—C4—F1	179.26 (12)
O1—C7—C2—C1	0.74 (13)	C6—C5—C4—C3	−0.4 (2)
C6—C7—C2—C1	179.25 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.95	2.54	3.4138 (16)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.95	2.54	3.4138 (16)	154

Symmetry code: (i) .