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

In the title compound, C(15)H(10)BrFO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-bromo-phenyl ring is rotated out of the benzofuran plane [dihedral angle = 38.98 (8)°], while the structure is stabilized by an inter-molecular C-H⋯O hydrogen bond and a Br⋯O halogen bond [3.036 (2) Å] and has an inter-molecular C-H⋯π inter-action between the 4-bromo-phenyl H atom and the benzene ring of an adjacent benzofuran mol-ecule, as well as aromatic π-π inter-actions between the benzene rings of the benzofuran systems [centroid-centroid distance = 3.482 (3) Å].

Related literature

For the crystal structures of similar 2-(4-bromo­phen­yl)-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2007a ▶,b ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H10BrFO2S

M = 353.20

Triclinic,

a = 8.6909 (7) Å

b = 9.1765 (7) Å

c = 10.1308 (8) Å

α = 105.989 (1)°

β = 114.811 (1)°

γ = 99.423 (1)°

V = 667.91 (9) Å3

Z = 2

Mo Kα radiation

μ = 3.24 mm−1

T = 293 K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.461, T max = 0.720

5792 measured reflections

2861 independent reflections

2589 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.062

S = 1.05

2861 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536809030190/zs2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030190/zs2004Isup2.hkl

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

C15H10BrFO2S	Z = 2
Mr = 353.20	F(000) = 352
Triclinic, P1	Dx = 1.756 Mg m−3
Hall symbol: -P 1	Melting point = 442–443 K
a = 8.6909 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1765 (7) Å	Cell parameters from 4045 reflections
c = 10.1308 (8) Å	θ = 2.4–27.5°
α = 105.989 (1)°	µ = 3.24 mm−1
β = 114.811 (1)°	T = 293 K
γ = 99.423 (1)°	Block, colorless
V = 667.91 (9) Å3	0.40 × 0.20 × 0.10 mm

Bruker SMART CCD-detector diffractometer	2861 independent reflections
Radiation source: fine-focus sealed tube	2589 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.461, Tmax = 0.720	l = −12→12
5792 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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F2) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0263P)2 + 0.5235P] where P = (Fo2 + 2Fc2)/3
2861 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.52 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
Br	0.87777 (3)	0.07461 (3)	−0.19442 (3)	0.03165 (8)
S	0.83195 (6)	0.75073 (6)	0.37122 (6)	0.02170 (11)
F	0.27524 (19)	0.78610 (17)	0.54077 (16)	0.0402 (3)
O1	0.44103 (18)	0.34213 (15)	0.19174 (16)	0.0212 (3)
O2	0.8984 (2)	0.83704 (18)	0.54254 (17)	0.0315 (3)
C1	0.6353 (2)	0.5929 (2)	0.3021 (2)	0.0194 (4)
C2	0.4984 (3)	0.5994 (2)	0.3476 (2)	0.0200 (4)
C3	0.4642 (3)	0.7204 (3)	0.4402 (2)	0.0249 (4)
H3	0.5391	0.8260	0.4910	0.030*
C4	0.3134 (3)	0.6731 (3)	0.4513 (2)	0.0278 (4)
C5	0.1973 (3)	0.5170 (3)	0.3795 (3)	0.0285 (5)
H5	0.0969	0.4935	0.3914	0.034*
C6	0.2324 (3)	0.3962 (3)	0.2896 (2)	0.0262 (4)
H6	0.1586	0.2903	0.2410	0.031*
C7	0.3836 (3)	0.4430 (2)	0.2768 (2)	0.0210 (4)
C8	0.5949 (3)	0.4379 (2)	0.2100 (2)	0.0196 (4)
C9	0.6748 (2)	0.3554 (2)	0.1231 (2)	0.0194 (4)
C10	0.6747 (3)	0.1994 (2)	0.1089 (2)	0.0236 (4)
H10	0.6313	0.1507	0.1612	0.028*
C11	0.7387 (3)	0.1167 (2)	0.0176 (2)	0.0254 (4)
H11	0.7386	0.0130	0.0083	0.031*
C12	0.8029 (3)	0.1910 (2)	−0.0596 (2)	0.0219 (4)
C13	0.8077 (3)	0.3461 (2)	−0.0451 (2)	0.0217 (4)
H13	0.8534	0.3948	−0.0961	0.026*
C14	0.7437 (3)	0.4286 (2)	0.0465 (2)	0.0212 (4)
H14	0.7466	0.5330	0.0570	0.025*
C15	0.7267 (3)	0.8706 (3)	0.2720 (3)	0.0310 (5)
H15A	0.6331	0.8880	0.2950	0.047*
H15B	0.6768	0.8163	0.1604	0.047*
H15C	0.8138	0.9718	0.3075	0.047*

	U11	U22	U33	U12	U13	U23
Br	0.04037 (14)	0.03169 (13)	0.03461 (13)	0.01806 (10)	0.02714 (11)	0.01103 (10)
S	0.0186 (2)	0.0212 (2)	0.0202 (2)	0.00384 (18)	0.00880 (19)	0.00360 (19)
F	0.0428 (8)	0.0511 (9)	0.0360 (7)	0.0286 (7)	0.0263 (7)	0.0104 (6)
O1	0.0217 (7)	0.0186 (6)	0.0234 (7)	0.0064 (5)	0.0122 (6)	0.0062 (5)
O2	0.0288 (8)	0.0312 (8)	0.0212 (7)	−0.0001 (6)	0.0108 (6)	−0.0005 (6)
C1	0.0179 (9)	0.0206 (9)	0.0180 (9)	0.0065 (7)	0.0077 (7)	0.0065 (7)
C2	0.0199 (9)	0.0245 (10)	0.0172 (9)	0.0102 (8)	0.0086 (7)	0.0093 (8)
C3	0.0252 (10)	0.0266 (10)	0.0199 (10)	0.0111 (8)	0.0098 (8)	0.0053 (8)
C4	0.0306 (11)	0.0392 (12)	0.0200 (10)	0.0220 (10)	0.0137 (9)	0.0119 (9)
C5	0.0233 (10)	0.0449 (13)	0.0281 (11)	0.0186 (9)	0.0150 (9)	0.0206 (10)
C6	0.0221 (10)	0.0327 (11)	0.0276 (10)	0.0097 (8)	0.0123 (9)	0.0160 (9)
C7	0.0220 (10)	0.0253 (10)	0.0183 (9)	0.0119 (8)	0.0096 (8)	0.0098 (8)
C8	0.0192 (9)	0.0215 (9)	0.0185 (9)	0.0068 (7)	0.0088 (7)	0.0087 (7)
C9	0.0186 (9)	0.0206 (9)	0.0165 (9)	0.0070 (7)	0.0075 (7)	0.0053 (7)
C10	0.0266 (10)	0.0231 (10)	0.0253 (10)	0.0082 (8)	0.0153 (9)	0.0106 (8)
C11	0.0298 (11)	0.0204 (9)	0.0299 (11)	0.0106 (8)	0.0170 (9)	0.0095 (8)
C12	0.0208 (9)	0.0246 (10)	0.0199 (9)	0.0096 (8)	0.0112 (8)	0.0050 (8)
C13	0.0210 (9)	0.0238 (10)	0.0183 (9)	0.0046 (8)	0.0095 (8)	0.0072 (8)
C14	0.0229 (10)	0.0175 (9)	0.0196 (9)	0.0060 (7)	0.0084 (8)	0.0057 (7)
C15	0.0287 (11)	0.0232 (10)	0.0358 (12)	0.0059 (9)	0.0115 (10)	0.0121 (9)

Br—C12	1.897 (2)	C6—C7	1.384 (3)
Br—O2i	3.036 (2)	C6—H6	0.9300
S—C1	1.771 (2)	C8—C9	1.466 (3)
S—C15	1.796 (2)	C9—C14	1.398 (3)
F—C4	1.361 (2)	C9—C10	1.398 (3)
O1—C8	1.383 (2)	C10—C11	1.388 (3)
O1—C7	1.386 (2)	C10—H10	0.9300
C1—C8	1.359 (3)	C11—C12	1.387 (3)
C1—C2	1.449 (3)	C11—H11	0.9300
C2—C7	1.391 (3)	C12—C13	1.382 (3)
C2—C3	1.404 (3)	C13—C14	1.388 (3)
C3—C4	1.373 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.391 (3)	C15—H15A	0.9600
C5—C6	1.392 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C12—Br—O2i	165.46 (7)	C1—C8—C9	133.66 (18)
O2—S—C1	106.07 (9)	O1—C8—C9	115.03 (16)
O2—S—C15	107.01 (10)	C14—C9—C10	119.19 (18)
C1—S—C15	97.48 (10)	C14—C9—C8	120.39 (17)
C8—O1—C7	105.92 (14)	C10—C9—C8	120.34 (17)
C8—C1—C2	106.94 (17)	C11—C10—C9	120.58 (18)
C8—C1—S	125.96 (15)	C11—C10—H10	119.7
C2—C1—S	126.73 (15)	C9—C10—H10	119.7
C7—C2—C3	119.59 (18)	C12—C11—C10	119.00 (18)
C7—C2—C1	105.25 (16)	C12—C11—H11	120.5
C3—C2—C1	135.15 (19)	C10—C11—H11	120.5
C4—C3—C2	115.79 (19)	C13—C12—C11	121.53 (18)
C4—C3—H3	122.1	C13—C12—Br	119.15 (15)
C2—C3—H3	122.1	C11—C12—Br	119.28 (15)
F—C4—C3	117.9 (2)	C12—C13—C14	119.28 (18)
F—C4—C5	117.34 (19)	C12—C13—H13	120.4
C3—C4—C5	124.73 (19)	C14—C13—H13	120.4
C4—C5—C6	119.66 (19)	C13—C14—C9	120.40 (18)
C4—C5—H5	120.2	C13—C14—H14	119.8
C6—C5—H5	120.2	C9—C14—H14	119.8
C7—C6—C5	116.0 (2)	S—C15—H15A	109.5
C7—C6—H6	122.0	S—C15—H15B	109.5
C5—C6—H6	122.0	H15A—C15—H15B	109.5
C6—C7—O1	125.17 (18)	S—C15—H15C	109.5
C6—C7—C2	124.19 (18)	H15A—C15—H15C	109.5
O1—C7—C2	110.64 (16)	H15B—C15—H15C	109.5
C1—C8—O1	111.24 (16)
O2—S—C1—C8	−132.93 (17)	C1—C2—C7—O1	0.0 (2)
C15—S—C1—C8	116.90 (18)	C2—C1—C8—O1	0.0 (2)
O2—S—C1—C2	39.08 (19)	S—C1—C8—O1	173.31 (13)
C15—S—C1—C2	−71.09 (18)	C2—C1—C8—C9	176.90 (19)
C8—C1—C2—C7	0.0 (2)	S—C1—C8—C9	−9.8 (3)
S—C1—C2—C7	−173.23 (15)	C7—O1—C8—C1	0.0 (2)
C8—C1—C2—C3	179.5 (2)	C7—O1—C8—C9	−177.54 (15)
S—C1—C2—C3	6.3 (3)	C1—C8—C9—C14	−37.8 (3)
C7—C2—C3—C4	−1.2 (3)	O1—C8—C9—C14	139.07 (18)
C1—C2—C3—C4	179.4 (2)	C1—C8—C9—C10	145.6 (2)
C2—C3—C4—F	179.60 (17)	O1—C8—C9—C10	−37.6 (2)
C2—C3—C4—C5	0.6 (3)	C14—C9—C10—C11	−1.3 (3)
F—C4—C5—C6	−178.56 (18)	C8—C9—C10—C11	175.46 (18)
C3—C4—C5—C6	0.4 (3)	C9—C10—C11—C12	0.0 (3)
C4—C5—C6—C7	−0.8 (3)	C10—C11—C12—C13	1.3 (3)
C5—C6—C7—O1	−179.26 (17)	C10—C11—C12—Br	−176.36 (15)
C5—C6—C7—C2	0.2 (3)	C11—C12—C13—C14	−1.3 (3)
C8—O1—C7—C6	179.56 (19)	Br—C12—C13—C14	176.41 (14)
C8—O1—C7—C2	0.0 (2)	C12—C13—C14—C9	−0.1 (3)
C3—C2—C7—C6	0.8 (3)	C10—C9—C14—C13	1.3 (3)
C1—C2—C7—C6	−179.57 (18)	C8—C9—C14—C13	−175.41 (17)
C3—C2—C7—O1	−179.62 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2ii	0.96	2.36	3.251 (3)	155
C13—H13···Cgiii	0.93	2.74	3.366 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O2i	0.96	2.36	3.251 (3)	155
C13—H13⋯Cgii	0.93	2.74	3.366 (3)	125

Symmetry codes: (i) ; (ii) .