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

In the title compound, C(16)H(13)FO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 38.75 (8)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the pharmacological 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-aryl-2-methyl-3-methyl­sulfinyl-1-benzofuran drivatives, see: Choi et al. (2006 ▶, 2009 ▶). For the synthesis of 2-methyl­benzofuran derivatives, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C16H13FO2S

M = 288.32

Monoclinic,

a = 15.101 (5) Å

b = 5.3150 (16) Å

c = 17.317 (5) Å

β = 93.606 (5)°

V = 1387.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.28 × 0.22 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.934, T max = 0.952

13601 measured reflections

3478 independent reflections

2437 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.137

S = 1.05

3478 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.22 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 datablock(s) global, I. DOI: 10.1107/S160053681103056X/qk2019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103056X/qk2019Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103056X/qk2019Isup3.cml

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

C16H13FO2S	F(000) = 600
Mr = 288.32	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2591 reflections
a = 15.101 (5) Å	θ = 2.6–26.4°
b = 5.3150 (16) Å	µ = 0.24 mm−1
c = 17.317 (5) Å	T = 173 K
β = 93.606 (5)°	Block, colourless
V = 1387.1 (7) Å3	0.28 × 0.22 × 0.21 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3478 independent reflections
Radiation source: rotating anode	2437 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.055
Detector resolution: 10.0 pixels mm-1	θmax = 28.5°, θmin = 1.4°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→7
Tmin = 0.934, Tmax = 0.952	l = −22→22
13601 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)] = 0.049	Hydrogen site location: difference Fourier map
wR(F2) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.2344P] where P = (Fo2 + 2Fc2)/3
3478 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.22 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	0.17563 (4)	0.58042 (10)	0.28834 (3)	0.04103 (18)
F1	0.55934 (10)	−0.3181 (3)	0.63856 (9)	0.0799 (5)
O1	0.06789 (11)	0.7798 (3)	0.47995 (8)	0.0601 (5)
O2	0.19330 (12)	0.3052 (3)	0.28237 (8)	0.0577 (5)
C1	0.14479 (13)	0.6338 (4)	0.38282 (10)	0.0361 (4)
C2	0.18189 (13)	0.5179 (4)	0.45385 (10)	0.0348 (4)
C3	0.25025 (13)	0.3517 (3)	0.47389 (10)	0.0324 (4)
H3	0.2843	0.2794	0.4353	0.039*
C4	0.26806 (13)	0.2925 (4)	0.55191 (10)	0.0348 (4)
C5	0.21503 (16)	0.3959 (4)	0.60763 (11)	0.0509 (6)
H5	0.2269	0.3515	0.6604	0.061*
C6	0.14668 (18)	0.5585 (5)	0.58852 (12)	0.0615 (7)
H6	0.1112	0.6273	0.6267	0.074*
C7	0.13179 (15)	0.6176 (4)	0.51116 (12)	0.0490 (6)
C8	0.07767 (15)	0.7839 (4)	0.40150 (11)	0.0472 (5)
C9	0.34346 (13)	0.1263 (4)	0.57592 (10)	0.0337 (4)
C10	0.36519 (15)	−0.0773 (4)	0.53163 (13)	0.0471 (5)
H10	0.3298	−0.1145	0.4858	0.056*
C11	0.43708 (18)	−0.2285 (5)	0.55224 (15)	0.0636 (7)
H11	0.4510	−0.3696	0.5216	0.076*
C12	0.48785 (15)	−0.1697 (5)	0.61814 (13)	0.0506 (6)
C13	0.46903 (15)	0.0255 (5)	0.66434 (13)	0.0518 (6)
H13	0.5048	0.0598	0.7102	0.062*
C14	0.39641 (16)	0.1737 (4)	0.64317 (12)	0.0499 (6)
H14	0.3822	0.3112	0.6752	0.060*
C15	0.01636 (16)	0.9524 (5)	0.35532 (14)	0.0584 (7)
H15A	0.0304	1.1280	0.3682	0.088*
H15B	−0.0449	0.9162	0.3672	0.088*
H15C	0.0231	0.9241	0.3001	0.088*
C16	0.28109 (15)	0.7332 (4)	0.29579 (13)	0.0502 (5)
H16A	0.3181	0.6581	0.3382	0.075*
H16B	0.2729	0.9127	0.3061	0.075*
H16C	0.3102	0.7128	0.2472	0.075*

	U11	U22	U33	U12	U13	U23
S1	0.0546 (3)	0.0466 (3)	0.0211 (2)	0.0092 (2)	−0.00313 (19)	−0.0005 (2)
F1	0.0614 (9)	0.1015 (12)	0.0772 (11)	0.0432 (9)	0.0076 (8)	0.0292 (9)
O1	0.0642 (10)	0.0827 (12)	0.0348 (8)	0.0421 (9)	0.0126 (7)	0.0095 (8)
O2	0.0964 (13)	0.0440 (9)	0.0328 (8)	0.0079 (8)	0.0051 (8)	−0.0095 (6)
C1	0.0391 (10)	0.0436 (11)	0.0250 (9)	0.0089 (8)	−0.0030 (7)	0.0015 (8)
C2	0.0405 (10)	0.0402 (10)	0.0236 (9)	0.0068 (8)	0.0020 (7)	−0.0002 (8)
C3	0.0397 (10)	0.0355 (9)	0.0221 (8)	0.0055 (8)	0.0030 (7)	−0.0021 (7)
C4	0.0414 (11)	0.0377 (10)	0.0255 (9)	0.0067 (8)	0.0030 (8)	0.0034 (8)
C5	0.0663 (15)	0.0639 (14)	0.0234 (9)	0.0235 (12)	0.0089 (9)	0.0072 (9)
C6	0.0748 (17)	0.0814 (18)	0.0303 (11)	0.0408 (14)	0.0184 (11)	0.0079 (11)
C7	0.0547 (13)	0.0611 (14)	0.0318 (10)	0.0276 (11)	0.0077 (9)	0.0044 (9)
C8	0.0509 (13)	0.0587 (14)	0.0317 (10)	0.0169 (11)	0.0019 (9)	0.0042 (9)
C9	0.0413 (10)	0.0338 (9)	0.0263 (9)	0.0012 (8)	0.0033 (7)	0.0064 (7)
C10	0.0562 (13)	0.0401 (11)	0.0437 (12)	0.0099 (10)	−0.0058 (10)	−0.0051 (9)
C11	0.0757 (18)	0.0549 (15)	0.0602 (15)	0.0304 (13)	0.0033 (13)	−0.0061 (12)
C12	0.0417 (12)	0.0598 (14)	0.0506 (13)	0.0160 (10)	0.0065 (10)	0.0224 (11)
C13	0.0521 (13)	0.0600 (14)	0.0416 (12)	0.0059 (11)	−0.0100 (10)	0.0124 (11)
C14	0.0655 (15)	0.0508 (12)	0.0319 (11)	0.0152 (11)	−0.0088 (10)	0.0006 (9)
C15	0.0558 (14)	0.0726 (17)	0.0465 (13)	0.0303 (13)	0.0010 (11)	0.0111 (11)
C16	0.0527 (13)	0.0530 (13)	0.0458 (12)	0.0110 (11)	0.0107 (10)	0.0078 (10)

S1—O2	1.4915 (17)	C8—C15	1.485 (3)
S1—C1	1.752 (2)	C9—C10	1.378 (3)
S1—C16	1.785 (2)	C9—C14	1.393 (3)
F1—C12	1.365 (2)	C10—C11	1.380 (3)
O1—C8	1.376 (2)	C10—H10	0.9500
O1—C7	1.379 (2)	C11—C12	1.370 (3)
C1—C8	1.345 (3)	C11—H11	0.9500
C1—C2	1.456 (2)	C12—C13	1.351 (3)
C2—C3	1.386 (3)	C13—C14	1.381 (3)
C2—C7	1.390 (3)	C13—H13	0.9500
C3—C4	1.397 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.404 (3)	C15—H15B	0.9800
C4—C9	1.480 (3)	C15—H15C	0.9800
C5—C6	1.371 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.380 (3)	C16—H16C	0.9800
C6—H6	0.9500
O2—S1—C1	106.43 (9)	C10—C9—C4	121.22 (17)
O2—S1—C16	106.77 (11)	C14—C9—C4	121.19 (18)
C1—S1—C16	98.46 (10)	C9—C10—C11	121.6 (2)
C8—O1—C7	106.32 (15)	C9—C10—H10	119.2
C8—C1—C2	107.68 (17)	C11—C10—H10	119.2
C8—C1—S1	124.69 (15)	C12—C11—C10	118.2 (2)
C2—C1—S1	127.56 (15)	C12—C11—H11	120.9
C3—C2—C7	119.61 (17)	C10—C11—H11	120.9
C3—C2—C1	136.24 (18)	C13—C12—F1	118.8 (2)
C7—C2—C1	104.13 (17)	C13—C12—C11	122.7 (2)
C2—C3—C4	118.74 (17)	F1—C12—C11	118.4 (2)
C2—C3—H3	120.6	C12—C13—C14	118.3 (2)
C4—C3—H3	120.6	C12—C13—H13	120.9
C3—C4—C5	119.56 (17)	C14—C13—H13	120.9
C3—C4—C9	120.27 (16)	C13—C14—C9	121.5 (2)
C5—C4—C9	120.16 (16)	C13—C14—H14	119.2
C6—C5—C4	122.28 (18)	C9—C14—H14	119.2
C6—C5—H5	118.9	C8—C15—H15A	109.5
C4—C5—H5	118.9	C8—C15—H15B	109.5
C5—C6—C7	116.87 (19)	H15A—C15—H15B	109.5
C5—C6—H6	121.6	C8—C15—H15C	109.5
C7—C6—H6	121.6	H15A—C15—H15C	109.5
O1—C7—C6	126.15 (19)	H15B—C15—H15C	109.5
O1—C7—C2	110.93 (17)	S1—C16—H16A	109.5
C6—C7—C2	122.92 (19)	S1—C16—H16B	109.5
C1—C8—O1	110.93 (17)	H16A—C16—H16B	109.5
C1—C8—C15	132.98 (19)	S1—C16—H16C	109.5
O1—C8—C15	116.06 (18)	H16A—C16—H16C	109.5
C10—C9—C14	117.57 (19)	H16B—C16—H16C	109.5
O2—S1—C1—C8	−137.1 (2)	C1—C2—C7—C6	−178.9 (2)
C16—S1—C1—C8	112.5 (2)	C2—C1—C8—O1	0.9 (3)
O2—S1—C1—C2	39.1 (2)	S1—C1—C8—O1	177.74 (16)
C16—S1—C1—C2	−71.2 (2)	C2—C1—C8—C15	178.8 (3)
C8—C1—C2—C3	−179.4 (2)	S1—C1—C8—C15	−4.3 (4)
S1—C1—C2—C3	3.8 (4)	C7—O1—C8—C1	−0.5 (3)
C8—C1—C2—C7	−0.9 (3)	C7—O1—C8—C15	−178.8 (2)
S1—C1—C2—C7	−177.67 (17)	C3—C4—C9—C10	−37.6 (3)
C7—C2—C3—C4	−1.3 (3)	C5—C4—C9—C10	143.6 (2)
C1—C2—C3—C4	177.1 (2)	C3—C4—C9—C14	140.8 (2)
C2—C3—C4—C5	1.9 (3)	C5—C4—C9—C14	−38.0 (3)
C2—C3—C4—C9	−176.79 (18)	C14—C9—C10—C11	−0.6 (3)
C3—C4—C5—C6	−1.3 (4)	C4—C9—C10—C11	177.9 (2)
C9—C4—C5—C6	177.4 (2)	C9—C10—C11—C12	−0.7 (4)
C4—C5—C6—C7	0.0 (4)	C10—C11—C12—C13	1.7 (4)
C8—O1—C7—C6	179.3 (3)	C10—C11—C12—F1	−179.7 (2)
C8—O1—C7—C2	−0.2 (3)	F1—C12—C13—C14	−179.8 (2)
C5—C6—C7—O1	−178.8 (2)	C11—C12—C13—C14	−1.2 (4)
C5—C6—C7—C2	0.7 (4)	C12—C13—C14—C9	−0.3 (4)
C3—C2—C7—O1	179.45 (19)	C10—C9—C14—C13	1.1 (3)
C1—C2—C7—O1	0.6 (3)	C4—C9—C14—C13	−177.4 (2)
C3—C2—C7—C6	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.36	3.245 (3)	156.
C16—H16B···O2ii	0.98	2.43	3.319 (3)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.36	3.245 (3)	156
C16—H16B⋯O2ii	0.98	2.43	3.319 (3)	151

Symmetry codes: (i) ; (ii) .