5-Bromo-2-(4-fluoro-phen-yl)-3-phenyl-sulfinyl-1-benzofuran.

In the title compound, C(20)H(12)BrFO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 2.63 (6)° with the mean plane of the benzofuran fragment. The dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds, and slipped π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.719 (3) Å, inter-planar distance = 3.000 (3) Å and slippage = 1.520 (3) Å].

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-halo-2-(4-halophen­yl)-3-phenyl­sulfinyl-1-benzofuran deriv­atives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C20H12BrFO2S

M = 415.27

Triclinic,

a = 8.0090 (2) Å

b = 9.8607 (3) Å

c = 11.7209 (3) Å

α = 70.471 (2)°

β = 83.171 (2)°

γ = 69.583 (2)°

V = 817.59 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.66 mm−1

T = 173 K

0.29 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.513, T max = 0.649

15330 measured reflections

4102 independent reflections

3428 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.02

4102 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 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/S1600536811032387/zl2399sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032387/zl2399Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032387/zl2399Isup3.cml

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

C20H12BrFO2S	Z = 2
Mr = 415.27	F(000) = 416
Triclinic, P1	Dx = 1.687 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0090 (2) Å	Cell parameters from 5582 reflections
b = 9.8607 (3) Å	θ = 2.3–28.3°
c = 11.7209 (3) Å	µ = 2.66 mm−1
α = 70.471 (2)°	T = 173 K
β = 83.171 (2)°	Block, colourless
γ = 69.583 (2)°	0.29 × 0.19 × 0.18 mm
V = 817.59 (4) Å3

Bruker SMART APEXII CCD diffractometer	4102 independent reflections
Radiation source: rotating anode	3428 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.039
Detector resolution: 10.0 pixels mm-1	θmax = 28.5°, θmin = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.513, Tmax = 0.649	l = −15→15
15330 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F2) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.2246P] where P = (Fo2 + 2Fc2)/3
4102 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.35 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
Br1	1.00885 (3)	0.24519 (3)	−0.107040 (19)	0.03957 (9)
S1	0.63342 (6)	0.12842 (5)	0.38339 (4)	0.02592 (11)
F1	0.02314 (18)	0.62109 (15)	0.66048 (12)	0.0443 (3)
O2	0.8243 (2)	0.04378 (17)	0.36866 (14)	0.0362 (3)
O1	0.49496 (18)	0.57208 (14)	0.20182 (11)	0.0254 (3)
C2	0.6785 (2)	0.3543 (2)	0.16790 (16)	0.0229 (4)
C1	0.5920 (2)	0.3166 (2)	0.28359 (16)	0.0228 (4)
C3	0.7985 (3)	0.2720 (2)	0.09969 (17)	0.0256 (4)
H3	0.8443	0.1637	0.1280	0.031*
C4	0.8479 (3)	0.3543 (2)	−0.01080 (18)	0.0279 (4)
C5	0.7855 (3)	0.5135 (2)	−0.05501 (18)	0.0301 (4)
H5	0.8259	0.5651	−0.1311	0.036*
C6	0.6651 (3)	0.5955 (2)	0.01210 (18)	0.0287 (4)
H6	0.6194	0.7038	−0.0163	0.034*
C7	0.6142 (3)	0.5126 (2)	0.12269 (17)	0.0242 (4)
C8	0.4834 (3)	0.4504 (2)	0.30045 (16)	0.0228 (4)
C9	0.3606 (3)	0.4920 (2)	0.39482 (17)	0.0237 (4)
C10	0.3378 (3)	0.3843 (2)	0.50252 (19)	0.0312 (4)
H10	0.4015	0.2792	0.5148	0.037*
C11	0.2245 (3)	0.4274 (2)	0.59151 (19)	0.0332 (5)
H11	0.2097	0.3534	0.6649	0.040*
C12	0.1332 (3)	0.5797 (2)	0.57210 (19)	0.0301 (4)
C13	0.1499 (3)	0.6903 (2)	0.4678 (2)	0.0347 (5)
H13	0.0843	0.7948	0.4563	0.042*
C14	0.2647 (3)	0.6456 (2)	0.37981 (19)	0.0314 (4)
H14	0.2791	0.7209	0.3072	0.038*
C15	0.5071 (3)	0.0727 (2)	0.30151 (17)	0.0259 (4)
C16	0.5951 (3)	−0.0160 (2)	0.2292 (2)	0.0336 (5)
H16	0.7214	−0.0485	0.2233	0.040*
C17	0.4956 (4)	−0.0567 (3)	0.1652 (2)	0.0446 (6)
H17	0.5534	−0.1162	0.1138	0.054*
C18	0.3125 (4)	−0.0105 (3)	0.1765 (2)	0.0474 (6)
H18	0.2446	−0.0366	0.1311	0.057*
C19	0.2264 (3)	0.0733 (3)	0.2530 (2)	0.0450 (6)
H19	0.1006	0.1015	0.2622	0.054*
C20	0.3238 (3)	0.1155 (2)	0.3157 (2)	0.0334 (5)
H20	0.2660	0.1734	0.3682	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.03834 (14)	0.04542 (15)	0.03048 (13)	−0.01050 (10)	0.01344 (9)	−0.01439 (10)
S1	0.0273 (2)	0.0205 (2)	0.0210 (2)	−0.00211 (18)	0.00143 (19)	−0.00188 (17)
F1	0.0399 (7)	0.0455 (7)	0.0390 (7)	−0.0019 (6)	0.0137 (6)	−0.0202 (6)
O2	0.0258 (7)	0.0315 (7)	0.0387 (8)	0.0015 (6)	−0.0035 (6)	−0.0055 (6)
O1	0.0326 (7)	0.0201 (6)	0.0209 (6)	−0.0079 (5)	0.0021 (6)	−0.0048 (5)
C2	0.0243 (9)	0.0248 (9)	0.0187 (9)	−0.0092 (7)	0.0003 (7)	−0.0047 (7)
C1	0.0236 (9)	0.0226 (9)	0.0195 (9)	−0.0066 (7)	0.0007 (7)	−0.0047 (7)
C3	0.0242 (9)	0.0254 (9)	0.0241 (9)	−0.0065 (7)	0.0007 (8)	−0.0058 (7)
C4	0.0242 (9)	0.0345 (10)	0.0234 (9)	−0.0100 (8)	0.0038 (8)	−0.0080 (8)
C5	0.0331 (11)	0.0353 (11)	0.0220 (9)	−0.0171 (9)	0.0039 (8)	−0.0043 (8)
C6	0.0358 (11)	0.0259 (9)	0.0244 (10)	−0.0147 (8)	0.0007 (8)	−0.0035 (8)
C7	0.0268 (9)	0.0245 (9)	0.0214 (9)	−0.0097 (7)	−0.0001 (8)	−0.0061 (7)
C8	0.0280 (9)	0.0209 (8)	0.0190 (9)	−0.0091 (7)	−0.0012 (7)	−0.0040 (7)
C9	0.0235 (9)	0.0239 (9)	0.0226 (9)	−0.0059 (7)	−0.0022 (7)	−0.0073 (7)
C10	0.0352 (11)	0.0223 (9)	0.0309 (11)	−0.0052 (8)	0.0064 (9)	−0.0086 (8)
C11	0.0368 (11)	0.0292 (10)	0.0263 (10)	−0.0067 (9)	0.0069 (9)	−0.0063 (8)
C12	0.0240 (10)	0.0361 (11)	0.0297 (10)	−0.0047 (8)	0.0033 (8)	−0.0162 (9)
C13	0.0339 (11)	0.0261 (10)	0.0366 (12)	0.0006 (8)	0.0005 (9)	−0.0119 (9)
C14	0.0350 (11)	0.0233 (9)	0.0286 (10)	−0.0035 (8)	−0.0002 (9)	−0.0055 (8)
C15	0.0275 (10)	0.0174 (8)	0.0254 (10)	−0.0046 (7)	0.0025 (8)	−0.0013 (7)
C16	0.0375 (12)	0.0239 (9)	0.0374 (12)	−0.0103 (9)	0.0101 (9)	−0.0105 (9)
C17	0.0620 (17)	0.0308 (11)	0.0455 (14)	−0.0202 (11)	0.0068 (12)	−0.0150 (10)
C18	0.0621 (17)	0.0348 (12)	0.0478 (15)	−0.0278 (12)	−0.0128 (13)	0.0004 (11)
C19	0.0351 (12)	0.0371 (12)	0.0531 (15)	−0.0134 (10)	−0.0069 (11)	0.0017 (11)
C20	0.0294 (10)	0.0271 (10)	0.0347 (11)	−0.0054 (8)	0.0046 (9)	−0.0042 (9)

Br1—C4	1.895 (2)	C9—C14	1.399 (3)
S1—O2	1.4852 (15)	C10—C11	1.377 (3)
S1—C1	1.7698 (18)	C10—H10	0.9500
S1—C15	1.794 (2)	C11—C12	1.373 (3)
F1—C12	1.353 (2)	C11—H11	0.9500
O1—C7	1.371 (2)	C12—C13	1.369 (3)
O1—C8	1.382 (2)	C13—C14	1.378 (3)
C2—C3	1.389 (3)	C13—H13	0.9500
C2—C7	1.391 (3)	C14—H14	0.9500
C2—C1	1.441 (3)	C15—C16	1.380 (3)
C1—C8	1.368 (3)	C15—C20	1.385 (3)
C3—C4	1.376 (3)	C16—C17	1.387 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.397 (3)	C17—C18	1.380 (4)
C5—C6	1.380 (3)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.383 (4)
C6—C7	1.383 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.375 (3)
C8—C9	1.457 (3)	C19—H19	0.9500
C9—C10	1.392 (3)	C20—H20	0.9500
O2—S1—C1	106.67 (9)	C11—C10—H10	119.5
O2—S1—C15	106.92 (9)	C9—C10—H10	119.5
C1—S1—C15	96.40 (9)	C12—C11—C10	118.66 (19)
C7—O1—C8	106.92 (14)	C12—C11—H11	120.7
C3—C2—C7	119.62 (17)	C10—C11—H11	120.7
C3—C2—C1	135.37 (17)	F1—C12—C13	119.07 (18)
C7—C2—C1	105.00 (16)	F1—C12—C11	118.23 (18)
C8—C1—C2	107.45 (16)	C13—C12—C11	122.70 (19)
C8—C1—S1	128.60 (15)	C12—C13—C14	118.04 (19)
C2—C1—S1	123.90 (14)	C12—C13—H13	121.0
C4—C3—C2	116.94 (18)	C14—C13—H13	121.0
C4—C3—H3	121.5	C13—C14—C9	121.58 (19)
C2—C3—H3	121.5	C13—C14—H14	119.2
C3—C4—C5	123.30 (19)	C9—C14—H14	119.2
C3—C4—Br1	117.97 (15)	C16—C15—C20	121.5 (2)
C5—C4—Br1	118.73 (15)	C16—C15—S1	119.32 (16)
C6—C5—C4	119.88 (18)	C20—C15—S1	119.10 (16)
C6—C5—H5	120.1	C15—C16—C17	118.7 (2)
C4—C5—H5	120.1	C15—C16—H16	120.6
C5—C6—C7	116.77 (18)	C17—C16—H16	120.6
C5—C6—H6	121.6	C18—C17—C16	119.8 (2)
C7—C6—H6	121.6	C18—C17—H17	120.1
O1—C7—C6	125.82 (17)	C16—C17—H17	120.1
O1—C7—C2	110.70 (16)	C17—C18—C19	120.9 (2)
C6—C7—C2	123.48 (18)	C17—C18—H18	119.6
C1—C8—O1	109.92 (16)	C19—C18—H18	119.6
C1—C8—C9	135.27 (17)	C20—C19—C18	119.7 (2)
O1—C8—C9	114.80 (15)	C20—C19—H19	120.2
C10—C9—C14	117.93 (18)	C18—C19—H19	120.2
C10—C9—C8	122.43 (17)	C19—C20—C15	119.3 (2)
C14—C9—C8	119.61 (17)	C19—C20—H20	120.4
C11—C10—C9	121.09 (18)	C15—C20—H20	120.4
C3—C2—C1—C8	−178.7 (2)	C7—O1—C8—C9	−179.65 (16)
C7—C2—C1—C8	0.2 (2)	C1—C8—C9—C10	3.7 (4)
C3—C2—C1—S1	3.7 (3)	O1—C8—C9—C10	−177.40 (18)
C7—C2—C1—S1	−177.34 (14)	C1—C8—C9—C14	−178.2 (2)
O2—S1—C1—C8	−143.48 (18)	O1—C8—C9—C14	0.7 (3)
C15—S1—C1—C8	106.68 (19)	C14—C9—C10—C11	0.0 (3)
O2—S1—C1—C2	33.56 (19)	C8—C9—C10—C11	178.1 (2)
C15—S1—C1—C2	−76.27 (17)	C9—C10—C11—C12	0.1 (3)
C7—C2—C3—C4	0.3 (3)	C10—C11—C12—F1	−179.5 (2)
C1—C2—C3—C4	179.1 (2)	C10—C11—C12—C13	0.2 (3)
C2—C3—C4—C5	0.9 (3)	F1—C12—C13—C14	179.0 (2)
C2—C3—C4—Br1	−179.14 (14)	C11—C12—C13—C14	−0.6 (3)
C3—C4—C5—C6	−1.5 (3)	C12—C13—C14—C9	0.8 (3)
Br1—C4—C5—C6	178.56 (16)	C10—C9—C14—C13	−0.5 (3)
C4—C5—C6—C7	0.8 (3)	C8—C9—C14—C13	−178.7 (2)
C8—O1—C7—C6	−179.84 (19)	O2—S1—C15—C16	−8.11 (18)
C8—O1—C7—C2	0.7 (2)	C1—S1—C15—C16	101.52 (16)
C5—C6—C7—O1	−179.09 (19)	O2—S1—C15—C20	169.70 (15)
C5—C6—C7—C2	0.3 (3)	C1—S1—C15—C20	−80.67 (16)
C3—C2—C7—O1	178.60 (17)	C20—C15—C16—C17	3.0 (3)
C1—C2—C7—O1	−0.6 (2)	S1—C15—C16—C17	−179.24 (16)
C3—C2—C7—C6	−0.9 (3)	C15—C16—C17—C18	−1.1 (3)
C1—C2—C7—C6	179.93 (19)	C16—C17—C18—C19	−1.5 (3)
C2—C1—C8—O1	0.2 (2)	C17—C18—C19—C20	2.2 (3)
S1—C1—C8—O1	177.59 (14)	C18—C19—C20—C15	−0.3 (3)
C2—C1—C8—C9	179.1 (2)	C16—C15—C20—C19	−2.3 (3)
S1—C1—C8—C9	−3.5 (4)	S1—C15—C20—C19	179.90 (16)
C7—O1—C8—C1	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.58	3.460 (2)	154.
C19—H19···O2ii	0.95	2.55	3.413 (3)	150.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.58	3.460 (2)	154
C19—H19⋯O2ii	0.95	2.55	3.413 (3)	150

Symmetry codes: (i) ; (ii) .