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

In the title mol-ecule, C(21)H(15)FO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent are situated on the opposite sides of the plane through the benzofuran fragment. The benzofuran ring plane makes dihedral angles of 28.63 (6) and 31.55 (5)° with the 4-fluoro-phenyl and phenyl rings, respectively. Weak C-H⋯F and C-H⋯O hydrogen bonds and inter-molecular C-H⋯π inter-actions are present in the crystal structure. The title crystal was refined as an inversion twin with a 0.39 (7):0.61 (7) domain ratio.

Related literature

For the crystal structures of similar 3-alkyl­sulfanyl-2-(4-fluoro­phen­yl)-5-phenyl-1-benzofuran derivatives, see: Choi et al. (2009 ▶, 2010 ▶). 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 ▶). For hydrogen bonding, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C21H15FO2S

M = 350.39

Monoclinic,

a = 10.148 (2) Å

b = 7.117 (1) Å

c = 11.991 (2) Å

β = 110.047 (2)°

V = 813.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.40 × 0.40 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.917, T max = 0.947

4812 measured reflections

3226 independent reflections

3065 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.06

3226 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1308 Friedel pairs

Flack parameter: 0.39 (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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014613/fb2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014613/fb2185Isup2.hkl

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

C21H15FO2S	F(000) = 364
Mr = 350.39	Dx = 1.430 Mg m−3
Monoclinic, P21	Melting point = 506–507 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.148 (2) Å	Cell parameters from 3710 reflections
b = 7.117 (1) Å	θ = 2.3–28.3°
c = 11.991 (2) Å	µ = 0.22 mm−1
β = 110.047 (2)°	T = 173 K
V = 813.6 (2) Å3	Block, colourless
Z = 2	0.40 × 0.40 × 0.25 mm

Bruker SMART APEXII CCD diffractometer	3226 independent reflections
Radiation source: rotating anode	3065 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.019
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −8→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→8
Tmin = 0.917, Tmax = 0.947	l = −15→14
4812 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1094P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3226 reflections	Δρmax = 0.31 e Å−3
228 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1308 Friedel pairs
59 constraints	Flack parameter: 0.39 (7)
Primary atom site location: structure-invariant direct methods

Experimental. The measured sample has been cut from the larger crystal. The crystals, both the grown ones as well as the cut one, have not been examined under the polarization microscope.

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. The diffractions 1 0 0 and 0 0 1 as well as their equivalents have been excluded from the refinement because their respective intensities significantly differed from the calculated ones.

	x	y	z	Uiso*/Ueq
S	0.55747 (5)	0.51643 (8)	0.86742 (4)	0.03009 (13)
F	1.26845 (12)	0.4440 (2)	1.03910 (11)	0.0425 (3)
O1	0.70363 (13)	0.4548 (2)	0.60162 (10)	0.0280 (3)
O2	0.44274 (15)	0.6590 (2)	0.83904 (13)	0.0398 (4)
C1	0.59124 (17)	0.4753 (3)	0.73449 (15)	0.0251 (4)
C2	0.48587 (19)	0.4671 (3)	0.61728 (15)	0.0257 (4)
C3	0.33954 (18)	0.4703 (3)	0.57251 (15)	0.0256 (4)
H3	0.2883	0.4810	0.6234	0.031*
C4	0.27128 (18)	0.4572 (3)	0.44981 (15)	0.0255 (4)
C5	0.35234 (19)	0.4441 (3)	0.37470 (16)	0.0286 (4)
H5	0.3061	0.4352	0.2932	0.034*
C6	0.4975 (2)	0.4439 (3)	0.41758 (16)	0.0317 (4)
H6	0.5495	0.4366	0.3672	0.038*
C7	0.56102 (19)	0.4553 (3)	0.53979 (16)	0.0264 (4)
C8	0.71883 (19)	0.4670 (3)	0.72036 (15)	0.0255 (4)
C9	0.86341 (18)	0.4633 (3)	0.80353 (15)	0.0242 (4)
C10	0.97478 (18)	0.5278 (3)	0.76948 (16)	0.0278 (4)
H10	0.9566	0.5745	0.6932	0.033*
C11	1.11179 (18)	0.5224 (3)	0.84845 (17)	0.0317 (4)
H11	1.1857	0.5663	0.8265	0.038*
C12	1.13528 (19)	0.4503 (3)	0.96030 (17)	0.0291 (4)
C13	1.0289 (2)	0.3813 (3)	0.99652 (17)	0.0288 (4)
H13	1.0484	0.3314	1.0722	0.035*
C14	0.89299 (19)	0.3886 (3)	0.91741 (16)	0.0268 (4)
H14	0.8201	0.3432	0.9402	0.032*
C15	0.11547 (19)	0.4540 (3)	0.39950 (15)	0.0250 (4)
C16	0.0356 (2)	0.3732 (3)	0.46221 (16)	0.0281 (4)
H16	0.0806	0.3231	0.5373	0.034*
C17	−0.1097 (2)	0.3669 (3)	0.41369 (17)	0.0313 (4)
H17	−0.1610	0.3139	0.4568	0.038*
C18	−0.1788 (2)	0.4392 (3)	0.30148 (18)	0.0323 (4)
H18	−0.2760	0.4326	0.2686	0.039*
C19	−0.10197 (19)	0.5216 (3)	0.23840 (16)	0.0315 (4)
H19	−0.1478	0.5718	0.1635	0.038*
C20	0.04378 (18)	0.5288 (3)	0.28756 (15)	0.0277 (4)
H20	0.0944	0.5848	0.2448	0.033*
C21	0.4775 (2)	0.2943 (4)	0.8756 (2)	0.0421 (6)
H21A	0.4490	0.2925	0.9441	0.063*
H21B	0.5438	0.1952	0.8817	0.063*
H21C	0.3970	0.2765	0.8053	0.063*

	U11	U22	U33	U12	U13	U23
S	0.0302 (2)	0.0398 (3)	0.02136 (19)	0.0062 (2)	0.01031 (15)	−0.0019 (2)
F	0.0287 (6)	0.0505 (8)	0.0447 (7)	−0.0009 (6)	0.0080 (5)	0.0011 (6)
O1	0.0297 (7)	0.0328 (7)	0.0243 (6)	0.0016 (6)	0.0128 (5)	0.0010 (6)
O2	0.0390 (8)	0.0470 (10)	0.0350 (8)	0.0117 (7)	0.0148 (7)	−0.0033 (7)
C1	0.0285 (9)	0.0257 (11)	0.0232 (8)	0.0025 (7)	0.0116 (7)	−0.0012 (7)
C2	0.0336 (9)	0.0226 (10)	0.0228 (8)	0.0019 (7)	0.0120 (7)	0.0007 (7)
C3	0.0306 (9)	0.0244 (11)	0.0253 (8)	0.0003 (7)	0.0142 (7)	−0.0004 (7)
C4	0.0306 (9)	0.0213 (9)	0.0250 (8)	−0.0008 (8)	0.0100 (7)	0.0015 (8)
C5	0.0361 (10)	0.0289 (10)	0.0224 (8)	−0.0012 (8)	0.0122 (7)	−0.0009 (8)
C6	0.0364 (10)	0.0369 (11)	0.0269 (9)	0.0023 (9)	0.0173 (8)	0.0011 (9)
C7	0.0292 (9)	0.0247 (9)	0.0285 (9)	0.0011 (8)	0.0140 (7)	0.0003 (8)
C8	0.0322 (9)	0.0220 (10)	0.0253 (8)	0.0005 (7)	0.0135 (7)	0.0017 (7)
C9	0.0264 (9)	0.0198 (9)	0.0289 (8)	0.0020 (7)	0.0129 (7)	−0.0005 (8)
C10	0.0346 (9)	0.0241 (9)	0.0304 (8)	0.0022 (9)	0.0184 (7)	0.0027 (9)
C11	0.0311 (9)	0.0265 (10)	0.0439 (10)	−0.0006 (9)	0.0211 (8)	−0.0002 (10)
C12	0.0249 (9)	0.0264 (10)	0.0354 (9)	0.0025 (8)	0.0094 (7)	−0.0021 (9)
C13	0.0337 (11)	0.0249 (10)	0.0289 (9)	0.0027 (8)	0.0121 (8)	0.0015 (8)
C14	0.0292 (10)	0.0242 (10)	0.0310 (9)	0.0007 (7)	0.0154 (8)	0.0016 (8)
C15	0.0330 (9)	0.0196 (9)	0.0237 (8)	−0.0035 (8)	0.0114 (7)	−0.0042 (8)
C16	0.0374 (11)	0.0254 (10)	0.0234 (8)	−0.0021 (8)	0.0126 (8)	−0.0002 (8)
C17	0.0352 (10)	0.0285 (11)	0.0351 (10)	−0.0046 (8)	0.0183 (8)	−0.0027 (9)
C18	0.0265 (9)	0.0319 (11)	0.0385 (10)	−0.0017 (8)	0.0108 (8)	−0.0040 (9)
C19	0.0358 (9)	0.0270 (10)	0.0288 (8)	0.0016 (9)	0.0073 (7)	0.0011 (9)
C20	0.0342 (9)	0.0234 (9)	0.0273 (8)	−0.0040 (9)	0.0130 (7)	0.0017 (9)
C21	0.0451 (13)	0.0481 (15)	0.0405 (12)	0.0055 (11)	0.0242 (10)	0.0131 (11)

S—O2	1.4931 (16)	C10—H10	0.9300
S—C1	1.7660 (17)	C11—C12	1.379 (3)
S—C21	1.795 (2)	C11—H11	0.9300
F—C12	1.359 (2)	C12—C13	1.385 (3)
O1—C8	1.381 (2)	C13—C14	1.381 (3)
O1—C7	1.382 (2)	C13—H13	0.9300
C1—C8	1.364 (2)	C14—H14	0.9300
C1—C2	1.446 (2)	C15—C20	1.395 (3)
C2—C7	1.392 (2)	C15—C16	1.404 (3)
C2—C3	1.395 (2)	C16—C17	1.388 (3)
C3—C4	1.398 (2)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.386 (3)
C4—C5	1.416 (2)	C17—H17	0.9300
C4—C15	1.487 (2)	C18—C19	1.388 (3)
C5—C6	1.383 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.393 (2)
C6—C7	1.386 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C8—C9	1.464 (2)	C21—H21A	0.9600
C9—C14	1.399 (2)	C21—H21B	0.9600
C9—C10	1.404 (2)	C21—H21C	0.9600
C10—C11	1.389 (2)
O2—S—C1	106.52 (9)	C12—C11—H11	120.9
O2—S—C21	106.22 (10)	C10—C11—H11	120.9
C1—S—C21	97.72 (10)	F—C12—C11	119.20 (16)
C8—O1—C7	106.22 (13)	F—C12—C13	117.85 (18)
C8—C1—C2	107.14 (15)	C11—C12—C13	122.95 (18)
C8—C1—S	127.27 (14)	C14—C13—C12	118.27 (18)
C2—C1—S	125.19 (13)	C14—C13—H13	120.9
C7—C2—C3	119.90 (16)	C12—C13—H13	120.9
C7—C2—C1	105.03 (15)	C13—C14—C9	120.97 (17)
C3—C2—C1	135.07 (16)	C13—C14—H14	119.5
C2—C3—C4	118.80 (15)	C9—C14—H14	119.5
C2—C3—H3	120.6	C20—C15—C16	117.73 (17)
C4—C3—H3	120.6	C20—C15—C4	121.06 (15)
C3—C4—C5	119.18 (16)	C16—C15—C4	121.20 (16)
C3—C4—C15	120.16 (15)	C17—C16—C15	120.94 (18)
C5—C4—C15	120.66 (16)	C17—C16—H16	119.5
C6—C5—C4	122.70 (17)	C15—C16—H16	119.5
C6—C5—H5	118.7	C18—C17—C16	120.43 (18)
C4—C5—H5	118.7	C18—C17—H17	119.8
C5—C6—C7	116.31 (16)	C16—C17—H17	119.8
C5—C6—H6	121.8	C17—C18—C19	119.61 (18)
C7—C6—H6	121.8	C17—C18—H18	120.2
O1—C7—C6	126.11 (16)	C19—C18—H18	120.2
O1—C7—C2	110.78 (15)	C18—C19—C20	119.88 (17)
C6—C7—C2	123.10 (17)	C18—C19—H19	120.1
C1—C8—O1	110.83 (15)	C20—C19—H19	120.1
C1—C8—C9	133.51 (16)	C19—C20—C15	121.40 (17)
O1—C8—C9	115.64 (14)	C19—C20—H20	119.3
C14—C9—C10	118.91 (16)	C15—C20—H20	119.3
C14—C9—C8	120.10 (15)	S—C21—H21A	109.5
C10—C9—C8	120.96 (16)	S—C21—H21B	109.5
C11—C10—C9	120.69 (17)	H21A—C21—H21B	109.5
C11—C10—H10	119.7	S—C21—H21C	109.5
C9—C10—H10	119.7	H21A—C21—H21C	109.5
C12—C11—C10	118.19 (16)	H21B—C21—H21C	109.5
O2—S—C1—C8	133.81 (19)	C7—O1—C8—C9	178.29 (16)
C21—S—C1—C8	−116.67 (19)	C1—C8—C9—C14	27.8 (3)
O2—S—C1—C2	−38.02 (19)	O1—C8—C9—C14	−150.11 (18)
C21—S—C1—C2	71.50 (18)	C1—C8—C9—C10	−154.5 (2)
C8—C1—C2—C7	−0.3 (2)	O1—C8—C9—C10	27.6 (3)
S—C1—C2—C7	172.91 (16)	C14—C9—C10—C11	−1.7 (3)
C8—C1—C2—C3	−179.7 (2)	C8—C9—C10—C11	−179.48 (19)
S—C1—C2—C3	−6.5 (3)	C9—C10—C11—C12	0.7 (3)
C7—C2—C3—C4	1.4 (3)	C10—C11—C12—F	−179.86 (19)
C1—C2—C3—C4	−179.3 (2)	C10—C11—C12—C13	0.8 (3)
C2—C3—C4—C5	−1.0 (3)	F—C12—C13—C14	179.42 (18)
C2—C3—C4—C15	178.04 (17)	C11—C12—C13—C14	−1.2 (3)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C14—C9	0.1 (3)
C15—C4—C5—C6	−179.11 (19)	C10—C9—C14—C13	1.3 (3)
C4—C5—C6—C7	0.7 (3)	C8—C9—C14—C13	179.05 (18)
C8—O1—C7—C6	−179.6 (2)	C3—C4—C15—C20	149.0 (2)
C8—O1—C7—C2	−0.1 (2)	C5—C4—C15—C20	−32.0 (3)
C5—C6—C7—O1	179.1 (2)	C3—C4—C15—C16	−31.9 (3)
C5—C6—C7—C2	−0.3 (3)	C5—C4—C15—C16	147.1 (2)
C3—C2—C7—O1	179.75 (16)	C20—C15—C16—C17	0.5 (3)
C1—C2—C7—O1	0.3 (2)	C4—C15—C16—C17	−178.57 (19)
C3—C2—C7—C6	−0.8 (3)	C15—C16—C17—C18	0.6 (3)
C1—C2—C7—C6	179.71 (19)	C16—C17—C18—C19	−1.3 (3)
C2—C1—C8—O1	0.2 (2)	C17—C18—C19—C20	0.8 (3)
S—C1—C8—O1	−172.79 (14)	C18—C19—C20—C15	0.3 (3)
C2—C1—C8—C9	−177.7 (2)	C16—C15—C20—C19	−1.0 (3)
S—C1—C8—C9	9.2 (3)	C4—C15—C20—C19	178.14 (19)
C7—O1—C8—C1	−0.1 (2)

Cg1 and Cg2 are the centroids of the C15–C20 (5-phenyl) and the C9–14 (4-fluorophenyl) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.61	3.301 (3)	131
C21—H21A···O2ii	0.96	2.63	3.375 (3)	135
C21—H21B···Fiii	0.96	2.55	3.478 (3)	164
C10—H10···Cg1iv	0.93	2.86	3.450 (2)	122
C13—H13···Cg2iii	0.93	2.81	3.417 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15–C20 (5-phen­yl) and the C9–14 (4-fluoro­phen­yl) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.93	2.61	3.301 (3)	131
C21—H21A⋯O2ii	0.96	2.63	3.375 (3)	135
C21—H21B⋯Fiii	0.96	2.55	3.478 (3)	164
C10—H10⋯Cg1iv	0.93	2.86	3.450 (2)	122
C13—H13⋯Cg2iii	0.93	2.81	3.417 (2)	124

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .