3-(4-Fluoro-phenyl-sulfin-yl)-2,4,5,6-tetra-methyl-1-benzo-furan.

In the title compound, C18H17FO2S, the dihedral angle between the plane of the benzo-furan ring system (r.m.s. deviation = 0.013 Å) and that of the 4-fluoro-phenyl ring is 74.30 (5)°. In the crystal, weak C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into columns extending in direction [100].

Related literature

For the crystal structures of related compounds, see: Choi et al. (2012 ▶); Seo et al. (2011a ▶,b ▶).

Experimental

Crystal data

C18H17FO2S

M = 316.38

Orthorhombic,

a = 7.8869 (2) Å

b = 11.0042 (2) Å

c = 17.5181 (4) Å

V = 1520.38 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.67 × 0.32 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.862, T max = 0.941

13898 measured reflections

3761 independent reflections

3369 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.094

S = 1.05

3761 reflections

203 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1812 Friedel pairs

Absolute structure parameter: −0.02 (7)

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/S1600536814014822/cv5468sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014822/cv5468Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014822/cv5468Isup3.cml

CCDC reference: 1009827

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

C18H17FO2S	Dx = 1.382 Mg m−3
Mr = 316.38	Melting point = 444–443 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3560 reflections
a = 7.8869 (2) Å	θ = 2.2–27.1°
b = 11.0042 (2) Å	µ = 0.23 mm−1
c = 17.5181 (4) Å	T = 173 K
V = 1520.38 (6) Å3	Block, colourless
Z = 4	0.67 × 0.32 × 0.27 mm
F(000) = 664

Bruker SMART APEXII CCD diffractometer	3761 independent reflections
Radiation source: rotating anode	3369 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.039
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→14
Tmin = 0.862, Tmax = 0.941	l = −23→23
13898 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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.0839P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3761 reflections	Δρmax = 0.21 e Å−3
203 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1812 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (7)

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	0.51230 (6)	0.40717 (5)	0.79515 (3)	0.03465 (13)
F1	−0.01469 (18)	0.65099 (13)	0.97462 (9)	0.0533 (4)
O1	0.34363 (18)	0.36849 (11)	0.58751 (7)	0.0285 (3)
O2	0.67580 (19)	0.47156 (18)	0.80968 (9)	0.0501 (4)
C1	0.4429 (3)	0.43098 (17)	0.70108 (10)	0.0284 (4)
C2	0.4022 (2)	0.53931 (16)	0.65691 (10)	0.0258 (4)
C3	0.4111 (2)	0.66591 (17)	0.66725 (10)	0.0290 (4)
C4	0.3498 (3)	0.73996 (17)	0.60784 (11)	0.0322 (4)
C5	0.2879 (3)	0.68941 (18)	0.53945 (11)	0.0320 (4)
C6	0.2837 (3)	0.56431 (17)	0.52893 (11)	0.0303 (4)
H6	0.2432	0.5291	0.4829	0.036*
C7	0.3410 (2)	0.49393 (15)	0.58838 (10)	0.0248 (4)
C8	0.4051 (2)	0.33292 (16)	0.65686 (10)	0.0292 (4)
C9	0.4869 (3)	0.7198 (2)	0.73820 (12)	0.0379 (5)
H9A	0.5548	0.6581	0.7645	0.057*
H9B	0.3960	0.7478	0.7720	0.057*
H9C	0.5595	0.7887	0.7244	0.057*
C10	0.3533 (3)	0.87599 (18)	0.61812 (15)	0.0465 (6)
H10A	0.4666	0.9068	0.6057	0.070*
H10B	0.3260	0.8961	0.6712	0.070*
H10C	0.2696	0.9135	0.5842	0.070*
C11	0.2277 (3)	0.7687 (2)	0.47404 (14)	0.0458 (6)
H11A	0.1927	0.7172	0.4312	0.069*
H11B	0.3202	0.8222	0.4577	0.069*
H11C	0.1313	0.8181	0.4909	0.069*
C12	0.4159 (3)	0.19987 (17)	0.66832 (12)	0.0401 (5)
H12A	0.5087	0.1670	0.6374	0.060*
H12B	0.3088	0.1620	0.6528	0.060*
H12C	0.4373	0.1825	0.7223	0.060*
C13	0.3505 (2)	0.49187 (17)	0.84426 (10)	0.0285 (4)
C14	0.1820 (3)	0.47592 (19)	0.82583 (10)	0.0318 (4)
H14	0.1518	0.4272	0.7832	0.038*
C15	0.0572 (3)	0.53021 (19)	0.86895 (11)	0.0352 (4)
H15	−0.0593	0.5205	0.8567	0.042*
C16	0.1075 (3)	0.59918 (18)	0.93053 (12)	0.0360 (5)
C17	0.2734 (3)	0.61688 (18)	0.94997 (13)	0.0381 (5)
H17	0.3029	0.6655	0.9928	0.046*
C18	0.3969 (3)	0.56253 (19)	0.90609 (11)	0.0349 (5)
H18	0.5132	0.5735	0.9182	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (2)	0.0469 (3)	0.02846 (19)	0.0087 (2)	−0.0041 (2)	0.0047 (2)
F1	0.0522 (9)	0.0416 (8)	0.0662 (9)	0.0090 (6)	0.0207 (7)	−0.0019 (7)
O1	0.0321 (7)	0.0232 (6)	0.0300 (6)	0.0017 (6)	−0.0017 (6)	−0.0008 (5)
O2	0.0249 (7)	0.0827 (12)	0.0429 (9)	0.0025 (8)	−0.0057 (6)	−0.0053 (8)
C1	0.0249 (9)	0.0339 (10)	0.0264 (8)	0.0038 (8)	−0.0003 (7)	0.0030 (7)
C2	0.0251 (10)	0.0258 (8)	0.0265 (8)	−0.0008 (7)	0.0039 (7)	0.0012 (7)
C3	0.0256 (10)	0.0282 (9)	0.0332 (9)	−0.0029 (8)	0.0096 (8)	−0.0016 (7)
C4	0.0300 (11)	0.0260 (9)	0.0406 (10)	−0.0015 (8)	0.0131 (9)	0.0041 (7)
C5	0.0287 (10)	0.0330 (10)	0.0344 (9)	0.0043 (8)	0.0077 (8)	0.0104 (8)
C6	0.0285 (10)	0.0353 (10)	0.0271 (8)	0.0013 (8)	0.0019 (8)	0.0032 (8)
C7	0.0230 (9)	0.0237 (8)	0.0277 (8)	0.0013 (7)	0.0031 (7)	0.0003 (7)
C8	0.0284 (10)	0.0274 (9)	0.0318 (9)	0.0047 (8)	0.0006 (8)	0.0040 (7)
C9	0.0397 (12)	0.0354 (11)	0.0385 (10)	−0.0108 (9)	0.0074 (9)	−0.0103 (9)
C10	0.0478 (14)	0.0286 (10)	0.0631 (14)	−0.0003 (10)	0.0213 (12)	0.0057 (10)
C11	0.0433 (13)	0.0459 (12)	0.0481 (12)	0.0081 (11)	0.0053 (10)	0.0209 (10)
C12	0.0431 (13)	0.0280 (10)	0.0491 (11)	0.0056 (9)	−0.0008 (10)	0.0028 (9)
C13	0.0283 (10)	0.0322 (9)	0.0249 (7)	0.0017 (8)	−0.0009 (8)	0.0055 (7)
C14	0.0288 (10)	0.0411 (11)	0.0255 (8)	−0.0032 (9)	−0.0038 (7)	0.0039 (7)
C15	0.0258 (10)	0.0417 (11)	0.0382 (10)	0.0012 (9)	−0.0017 (8)	0.0119 (9)
C16	0.0404 (13)	0.0286 (9)	0.0390 (10)	0.0021 (9)	0.0114 (9)	0.0078 (8)
C17	0.0432 (13)	0.0345 (10)	0.0366 (9)	−0.0108 (9)	0.0053 (10)	−0.0032 (8)
C18	0.0267 (10)	0.0456 (12)	0.0323 (9)	−0.0081 (9)	−0.0024 (8)	0.0038 (8)

S1—O2	1.4932 (17)	C9—H9C	0.9800
S1—C1	1.7560 (18)	C10—H10A	0.9800
S1—C13	1.799 (2)	C10—H10B	0.9800
F1—C16	1.361 (3)	C10—H10C	0.9800
O1—C8	1.365 (2)	C11—H11A	0.9800
O1—C7	1.381 (2)	C11—H11B	0.9800
C1—C8	1.361 (3)	C11—H11C	0.9800
C1—C2	1.457 (3)	C12—H12A	0.9800
C2—C7	1.387 (2)	C12—H12B	0.9800
C2—C3	1.407 (3)	C12—H12C	0.9800
C3—C4	1.408 (3)	C13—C14	1.379 (3)
C3—C9	1.501 (3)	C13—C18	1.383 (3)
C4—C5	1.408 (3)	C14—C15	1.377 (3)
C4—C10	1.508 (3)	C14—H14	0.9500
C5—C6	1.389 (3)	C15—C16	1.377 (3)
C5—C11	1.517 (3)	C15—H15	0.9500
C6—C7	1.374 (2)	C16—C17	1.366 (3)
C6—H6	0.9500	C17—C18	1.377 (3)
C8—C12	1.480 (3)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800
O2—S1—C1	110.99 (10)	C4—C10—H10B	109.5
O2—S1—C13	106.57 (10)	H10A—C10—H10B	109.5
C1—S1—C13	98.65 (9)	C4—C10—H10C	109.5
C8—O1—C7	106.39 (13)	H10A—C10—H10C	109.5
C8—C1—C2	107.33 (16)	H10B—C10—H10C	109.5
C8—C1—S1	118.95 (14)	C5—C11—H11A	109.5
C2—C1—S1	133.56 (14)	C5—C11—H11B	109.5
C7—C2—C3	119.05 (16)	H11A—C11—H11B	109.5
C7—C2—C1	104.00 (15)	C5—C11—H11C	109.5
C3—C2—C1	136.95 (17)	H11A—C11—H11C	109.5
C2—C3—C4	117.44 (17)	H11B—C11—H11C	109.5
C2—C3—C9	121.18 (18)	C8—C12—H12A	109.5
C4—C3—C9	121.36 (17)	C8—C12—H12B	109.5
C3—C4—C5	121.30 (16)	H12A—C12—H12B	109.5
C3—C4—C10	118.68 (19)	C8—C12—H12C	109.5
C5—C4—C10	120.02 (19)	H12A—C12—H12C	109.5
C6—C5—C4	120.84 (17)	H12B—C12—H12C	109.5
C6—C5—C11	117.55 (19)	C14—C13—C18	120.66 (19)
C4—C5—C11	121.59 (18)	C14—C13—S1	120.38 (15)
C7—C6—C5	116.75 (18)	C18—C13—S1	118.57 (15)
C7—C6—H6	121.6	C15—C14—C13	120.33 (18)
C5—C6—H6	121.6	C15—C14—H14	119.8
C6—C7—O1	124.06 (16)	C13—C14—H14	119.8
C6—C7—C2	124.57 (16)	C14—C15—C16	117.6 (2)
O1—C7—C2	111.37 (14)	C14—C15—H15	121.2
C1—C8—O1	110.92 (15)	C16—C15—H15	121.2
C1—C8—C12	133.95 (18)	F1—C16—C17	118.5 (2)
O1—C8—C12	115.13 (16)	F1—C16—C15	118.1 (2)
C3—C9—H9A	109.5	C17—C16—C15	123.4 (2)
C3—C9—H9B	109.5	C16—C17—C18	118.4 (2)
H9A—C9—H9B	109.5	C16—C17—H17	120.8
C3—C9—H9C	109.5	C18—C17—H17	120.8
H9A—C9—H9C	109.5	C17—C18—C13	119.6 (2)
H9B—C9—H9C	109.5	C17—C18—H18	120.2
C4—C10—H10A	109.5	C13—C18—H18	120.2
O2—S1—C1—C8	126.77 (17)	C8—O1—C7—C2	0.87 (19)
C13—S1—C1—C8	−121.68 (17)	C3—C2—C7—C6	−1.4 (3)
O2—S1—C1—C2	−58.4 (2)	C1—C2—C7—C6	178.85 (18)
C13—S1—C1—C2	53.1 (2)	C3—C2—C7—O1	178.97 (16)
C8—C1—C2—C7	0.3 (2)	C1—C2—C7—O1	−0.7 (2)
S1—C1—C2—C7	−174.90 (17)	C2—C1—C8—O1	0.2 (2)
C8—C1—C2—C3	−179.3 (2)	S1—C1—C8—O1	176.24 (13)
S1—C1—C2—C3	5.5 (4)	C2—C1—C8—C12	−179.5 (2)
C7—C2—C3—C4	2.7 (3)	S1—C1—C8—C12	−3.5 (3)
C1—C2—C3—C4	−177.7 (2)	C7—O1—C8—C1	−0.6 (2)
C7—C2—C3—C9	−175.95 (18)	C7—O1—C8—C12	179.11 (17)
C1—C2—C3—C9	3.6 (3)	O2—S1—C13—C14	162.46 (14)
C2—C3—C4—C5	−2.4 (3)	C1—S1—C13—C14	47.42 (16)
C9—C3—C4—C5	176.21 (18)	O2—S1—C13—C18	−24.61 (18)
C2—C3—C4—C10	178.38 (18)	C1—S1—C13—C18	−139.66 (16)
C9—C3—C4—C10	−3.0 (3)	C18—C13—C14—C15	−0.1 (3)
C3—C4—C5—C6	0.8 (3)	S1—C13—C14—C15	172.70 (15)
C10—C4—C5—C6	179.98 (19)	C13—C14—C15—C16	−0.5 (3)
C3—C4—C5—C11	−177.67 (19)	C14—C15—C16—F1	−178.51 (17)
C10—C4—C5—C11	1.5 (3)	C14—C15—C16—C17	0.7 (3)
C4—C5—C6—C7	0.6 (3)	F1—C16—C17—C18	178.83 (18)
C11—C5—C6—C7	179.10 (18)	C15—C16—C17—C18	−0.4 (3)
C5—C6—C7—O1	179.29 (17)	C16—C17—C18—C13	−0.2 (3)
C5—C6—C7—C2	−0.2 (3)	C14—C13—C18—C17	0.4 (3)
C8—O1—C7—C6	−178.71 (18)	S1—C13—C18—C17	−172.50 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2i	0.95	2.31	3.247 (3)	169
C17—H17···F1ii	0.95	2.50	3.083 (2)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.95	2.31	3.247 (3)	169
C17—H17⋯F1ii	0.95	2.50	3.083 (2)	120

Symmetry codes: (i) ; (ii) .