5-Fluoro-2-methyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C16H13FO3S, the dihedral angle between the mean planes of the benzo-furan ring system and the 3-methyl-phenyl ring is 80.96 (4)°. In the crystal, mol-ecules are linked via pairs of π-π inter-actions between furan and benzene rings, with centroid-centroid distances of 3.758 (1) and 3.771 (1) Å. A similar inter-action is found between furan rings, with a centroid-centroid distance of 3.661 (1) Å between neighbouring mol-ecules. The mol-ecules stack along the a-axis direction. In addition, C-H⋯O and C-H⋯π hydrogen bonds are observed between inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C16H13FO3S

M = 304.32

Triclinic,

a = 7.4406 (1) Å

b = 9.1291 (2) Å

c = 11.2073 (2) Å

α = 82.891 (1)°

β = 73.301 (1)°

γ = 77.613 (1)°

V = 710.62 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.37 × 0.30 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.695, T max = 0.746

12591 measured reflections

3263 independent reflections

2868 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.07

3263 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.41 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814006321/bg2523sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006321/bg2523Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006321/bg2523Isup3.cml

CCDC reference: 993004

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H13FO3S	Z = 2
Mr = 304.32	F(000) = 316
Triclinic, P1	Dx = 1.422 Mg m−3
Hall symbol: -P 1	Melting point = 375–376 K
a = 7.4406 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1291 (2) Å	Cell parameters from 5506 reflections
c = 11.2073 (2) Å	θ = 2.9–27.5°
α = 82.891 (1)°	µ = 0.25 mm−1
β = 73.301 (1)°	T = 173 K
γ = 77.613 (1)°	Block, colourless
V = 710.62 (2) Å3	0.37 × 0.30 × 0.28 mm

Bruker SMART APEXII CCD diffractometer	3263 independent reflections
Radiation source: rotating anode	2868 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.695, Tmax = 0.746	l = −14→14
12591 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.056P)2 + 0.1689P] where P = (Fo2 + 2Fc2)/3
3263 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.41 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	0.87603 (5)	0.18979 (4)	0.70443 (3)	0.03242 (12)
F1	0.84714 (17)	0.30138 (12)	0.19261 (9)	0.0556 (3)
O1	0.69505 (15)	0.60973 (11)	0.60126 (11)	0.0391 (3)
O2	1.02286 (15)	0.10305 (12)	0.61294 (11)	0.0395 (3)
O3	0.91181 (16)	0.21354 (13)	0.81879 (11)	0.0432 (3)
C1	0.80671 (19)	0.36430 (15)	0.63233 (14)	0.0310 (3)
C2	0.79931 (18)	0.39130 (15)	0.50423 (14)	0.0295 (3)
C3	0.8409 (2)	0.30421 (15)	0.40267 (14)	0.0338 (3)
H3	0.8885	0.1990	0.4076	0.041*
C4	0.8087 (2)	0.38018 (17)	0.29498 (15)	0.0382 (3)
C5	0.7414 (2)	0.53393 (18)	0.28163 (16)	0.0404 (4)
H5	0.7240	0.5792	0.2037	0.048*
C6	0.7004 (2)	0.61985 (16)	0.38156 (16)	0.0389 (4)
H6	0.6545	0.7252	0.3756	0.047*
C7	0.7292 (2)	0.54522 (15)	0.49103 (15)	0.0333 (3)
C8	0.7415 (2)	0.49761 (17)	0.68625 (15)	0.0371 (3)
C9	0.7072 (3)	0.5457 (2)	0.81330 (18)	0.0531 (5)
H9A	0.5697	0.5784	0.8494	0.080*
H9B	0.7729	0.6292	0.8091	0.080*
H9C	0.7562	0.4613	0.8656	0.080*
C10	0.6704 (2)	0.10864 (15)	0.74169 (13)	0.0300 (3)
C11	0.6516 (2)	0.01107 (16)	0.66260 (14)	0.0354 (3)
H11	0.7496	−0.0155	0.5888	0.042*
C12	0.4846 (2)	−0.04647 (17)	0.69504 (16)	0.0404 (4)
H12	0.4678	−0.1138	0.6427	0.048*
C13	0.3430 (2)	−0.00721 (16)	0.80208 (16)	0.0373 (3)
H13	0.2298	−0.0480	0.8220	0.045*
C14	0.3615 (2)	0.09077 (15)	0.88184 (14)	0.0319 (3)
C15	0.5287 (2)	0.14767 (16)	0.85034 (13)	0.0311 (3)
H15	0.5465	0.2137	0.9034	0.037*
C16	0.2048 (2)	0.13571 (19)	0.99669 (14)	0.0414 (4)
H16A	0.1115	0.2202	0.9746	0.062*
H16B	0.2589	0.1658	1.0579	0.062*
H16C	0.1415	0.0505	1.0327	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.02348 (19)	0.0338 (2)	0.0379 (2)	−0.00384 (14)	−0.00764 (15)	0.00143 (14)
F1	0.0765 (8)	0.0477 (6)	0.0407 (5)	−0.0112 (5)	−0.0125 (5)	−0.0050 (4)
O1	0.0349 (6)	0.0270 (5)	0.0518 (6)	−0.0042 (4)	−0.0050 (5)	−0.0076 (4)
O2	0.0261 (5)	0.0355 (5)	0.0482 (6)	0.0016 (4)	−0.0033 (5)	0.0008 (5)
O3	0.0350 (6)	0.0538 (7)	0.0446 (6)	−0.0116 (5)	−0.0163 (5)	0.0018 (5)
C1	0.0224 (6)	0.0298 (7)	0.0390 (7)	−0.0061 (5)	−0.0045 (6)	−0.0022 (5)
C2	0.0202 (6)	0.0248 (6)	0.0407 (7)	−0.0046 (5)	−0.0047 (6)	0.0014 (5)
C3	0.0300 (7)	0.0251 (6)	0.0421 (8)	−0.0036 (5)	−0.0050 (6)	−0.0009 (6)
C4	0.0370 (8)	0.0356 (7)	0.0403 (8)	−0.0089 (6)	−0.0062 (7)	−0.0025 (6)
C5	0.0354 (8)	0.0374 (8)	0.0460 (9)	−0.0085 (6)	−0.0112 (7)	0.0091 (7)
C6	0.0309 (8)	0.0252 (7)	0.0568 (10)	−0.0034 (6)	−0.0106 (7)	0.0058 (6)
C7	0.0230 (7)	0.0253 (6)	0.0478 (8)	−0.0043 (5)	−0.0034 (6)	−0.0036 (6)
C8	0.0279 (7)	0.0357 (7)	0.0464 (8)	−0.0093 (6)	−0.0042 (6)	−0.0065 (6)
C9	0.0540 (11)	0.0512 (10)	0.0535 (10)	−0.0120 (8)	−0.0058 (9)	−0.0193 (8)
C10	0.0257 (7)	0.0277 (6)	0.0346 (7)	−0.0026 (5)	−0.0089 (6)	0.0033 (5)
C11	0.0317 (7)	0.0290 (7)	0.0405 (8)	0.0006 (6)	−0.0056 (6)	−0.0045 (6)
C12	0.0374 (8)	0.0281 (7)	0.0556 (10)	−0.0032 (6)	−0.0113 (7)	−0.0110 (6)
C13	0.0303 (7)	0.0280 (7)	0.0519 (9)	−0.0065 (6)	−0.0093 (7)	0.0009 (6)
C14	0.0282 (7)	0.0289 (7)	0.0354 (7)	−0.0022 (5)	−0.0090 (6)	0.0059 (5)
C15	0.0295 (7)	0.0311 (7)	0.0319 (7)	−0.0031 (5)	−0.0103 (6)	0.0008 (5)
C16	0.0314 (8)	0.0525 (9)	0.0358 (8)	−0.0078 (7)	−0.0045 (6)	0.0025 (7)

S1—O3	1.4319 (12)	C8—C9	1.478 (2)
S1—O2	1.4346 (11)	C9—H9A	0.9800
S1—C1	1.7394 (14)	C9—H9B	0.9800
S1—C10	1.7626 (14)	C9—H9C	0.9800
F1—C4	1.3575 (18)	C10—C11	1.385 (2)
O1—C8	1.368 (2)	C10—C15	1.389 (2)
O1—C7	1.3686 (18)	C11—C12	1.387 (2)
C1—C8	1.357 (2)	C11—H11	0.9500
C1—C2	1.441 (2)	C12—C13	1.377 (2)
C2—C3	1.393 (2)	C12—H12	0.9500
C2—C7	1.3954 (19)	C13—C14	1.393 (2)
C3—C4	1.372 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.386 (2)
C4—C5	1.390 (2)	C14—C16	1.499 (2)
C5—C6	1.371 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.377 (2)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
O3—S1—O2	119.73 (7)	C8—C9—H9A	109.5
O3—S1—C1	108.28 (7)	C8—C9—H9B	109.5
O2—S1—C1	107.74 (7)	H9A—C9—H9B	109.5
O3—S1—C10	108.10 (7)	C8—C9—H9C	109.5
O2—S1—C10	108.25 (7)	H9A—C9—H9C	109.5
C1—S1—C10	103.57 (6)	H9B—C9—H9C	109.5
C8—O1—C7	107.14 (11)	C11—C10—C15	121.75 (13)
C8—C1—C2	107.50 (13)	C11—C10—S1	120.15 (11)
C8—C1—S1	127.01 (12)	C15—C10—S1	118.09 (11)
C2—C1—S1	125.42 (11)	C10—C11—C12	117.64 (14)
C3—C2—C7	119.40 (14)	C10—C11—H11	121.2
C3—C2—C1	136.00 (13)	C12—C11—H11	121.2
C7—C2—C1	104.60 (13)	C13—C12—C11	120.88 (14)
C4—C3—C2	115.65 (13)	C13—C12—H12	119.6
C4—C3—H3	122.2	C11—C12—H12	119.6
C2—C3—H3	122.2	C12—C13—C14	121.61 (14)
F1—C4—C3	118.38 (14)	C12—C13—H13	119.2
F1—C4—C5	116.81 (15)	C14—C13—H13	119.2
C3—C4—C5	124.80 (15)	C15—C14—C13	117.73 (14)
C6—C5—C4	119.62 (15)	C15—C14—C16	120.97 (13)
C6—C5—H5	120.2	C13—C14—C16	121.30 (14)
C4—C5—H5	120.2	C14—C15—C10	120.38 (13)
C5—C6—C7	116.43 (13)	C14—C15—H15	119.8
C5—C6—H6	121.8	C10—C15—H15	119.8
C7—C6—H6	121.8	C14—C16—H16A	109.5
O1—C7—C6	125.55 (13)	C14—C16—H16B	109.5
O1—C7—C2	110.36 (13)	H16A—C16—H16B	109.5
C6—C7—C2	124.09 (14)	C14—C16—H16C	109.5
C1—C8—O1	110.40 (14)	H16A—C16—H16C	109.5
C1—C8—C9	134.70 (16)	H16B—C16—H16C	109.5
O1—C8—C9	114.88 (14)
O3—S1—C1—C8	−18.19 (15)	C1—C2—C7—C6	179.58 (13)
O2—S1—C1—C8	−149.03 (13)	C2—C1—C8—O1	−0.94 (16)
C10—S1—C1—C8	96.42 (14)	S1—C1—C8—O1	−178.00 (10)
O3—S1—C1—C2	165.25 (11)	C2—C1—C8—C9	177.59 (17)
O2—S1—C1—C2	34.41 (13)	S1—C1—C8—C9	0.5 (3)
C10—S1—C1—C2	−80.14 (13)	C7—O1—C8—C1	0.89 (16)
C8—C1—C2—C3	−178.42 (16)	C7—O1—C8—C9	−177.96 (13)
S1—C1—C2—C3	−1.3 (2)	O3—S1—C10—C11	−149.08 (12)
C8—C1—C2—C7	0.61 (15)	O2—S1—C10—C11	−18.00 (14)
S1—C1—C2—C7	177.72 (10)	C1—S1—C10—C11	96.18 (13)
C7—C2—C3—C4	0.2 (2)	O3—S1—C10—C15	32.04 (13)
C1—C2—C3—C4	179.12 (15)	O2—S1—C10—C15	163.13 (11)
C2—C3—C4—F1	179.80 (13)	C1—S1—C10—C15	−82.69 (12)
C2—C3—C4—C5	0.8 (2)	C15—C10—C11—C12	0.4 (2)
F1—C4—C5—C6	−179.85 (14)	S1—C10—C11—C12	−178.41 (11)
C3—C4—C5—C6	−0.8 (3)	C10—C11—C12—C13	0.1 (2)
C4—C5—C6—C7	−0.2 (2)	C11—C12—C13—C14	−0.2 (2)
C8—O1—C7—C6	179.87 (14)	C12—C13—C14—C15	−0.3 (2)
C8—O1—C7—C2	−0.49 (15)	C12—C13—C14—C16	178.60 (14)
C5—C6—C7—O1	−179.25 (14)	C13—C14—C15—C10	0.8 (2)
C5—C6—C7—C2	1.2 (2)	C16—C14—C15—C10	−178.06 (13)
C3—C2—C7—O1	179.16 (12)	C11—C10—C15—C14	−0.9 (2)
C1—C2—C7—O1	−0.07 (15)	S1—C10—C15—C14	177.93 (10)
C3—C2—C7—C6	−1.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	0.95	2.51	3.450 (2)	172
C6—H6···Cg3ii	0.95	2.76	3.556 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 3-methyl­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2i	0.95	2.51	3.450 (2)	172
C6—H6⋯Cg3ii	0.95	2.76	3.556 (2)	142

Symmetry codes: (i) ; (ii) .