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

In the title compound, C(15)H(10)BrFO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 30.77 (6)° with the mean plane [mean deviation = 0.014 (1) Å] of the benzofuran ring system. In the crystal, mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds into inversion dimers. A Br⋯O contact [3.214 (1) Å] is also observed.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2007 ▶, 2010 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H10BrFO2S

M = 353.20

Triclinic,

a = 8.0494 (1) Å

b = 8.5317 (1) Å

c = 10.7110 (2) Å

α = 87.624 (1)°

β = 81.378 (1)°

γ = 66.709 (1)°

V = 667.87 (2) Å3

Z = 2

Mo Kα radiation

μ = 3.24 mm−1

T = 173 K

0.36 × 0.29 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.391, T max = 0.501

11667 measured reflections

3059 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.064

S = 1.07

3059 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.46 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/S1600536812016789/is5120sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016789/is5120Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016789/is5120Isup3.cml

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	Mo Kα radiation, λ = 0.71073 Å
a = 8.0494 (1) Å	Cell parameters from 7435 reflections
b = 8.5317 (1) Å	θ = 2.6–27.5°
c = 10.7110 (2) Å	µ = 3.24 mm−1
α = 87.624 (1)°	T = 173 K
β = 81.378 (1)°	Block, colourless
γ = 66.709 (1)°	0.36 × 0.29 × 0.25 mm
V = 667.87 (2) Å3

Bruker SMART APEXII CCD diffractometer	3059 independent reflections
Radiation source: rotating anode	2835 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.391, Tmax = 0.501	l = −13→13
11667 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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F2) = 0.064	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0304P)2 + 0.2245P] where P = (Fo2 + 2Fc2)/3
3059 reflections	(Δ/σ)max = 0.003
182 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.46 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	0.17500 (3)	1.14433 (2)	1.025572 (16)	0.03170 (8)
S1	0.78664 (6)	0.69925 (5)	0.60864 (4)	0.02294 (10)
F1	0.46013 (17)	0.70426 (15)	0.04748 (10)	0.0391 (3)
O1	0.29411 (16)	0.86282 (14)	0.50431 (11)	0.0227 (2)
O2	0.81884 (18)	0.83090 (16)	0.67671 (13)	0.0309 (3)
C1	0.5524 (2)	0.78361 (19)	0.59217 (15)	0.0207 (3)
C2	0.4029 (2)	0.89580 (19)	0.68141 (15)	0.0205 (3)
C3	0.3839 (2)	0.9576 (2)	0.80375 (15)	0.0224 (3)
H3	0.4859	0.9297	0.8475	0.027*
C4	0.2095 (2)	1.0613 (2)	0.85784 (16)	0.0236 (3)
C5	0.0559 (2)	1.1060 (2)	0.79601 (17)	0.0260 (4)
H5	−0.0611	1.1781	0.8375	0.031*
C6	0.0740 (2)	1.0455 (2)	0.67483 (17)	0.0254 (4)
H6	−0.0279	1.0741	0.6308	0.030*
C7	0.2488 (2)	0.9411 (2)	0.62143 (15)	0.0213 (3)
C8	0.4801 (2)	0.7684 (2)	0.48847 (15)	0.0209 (3)
C9	0.5542 (2)	0.6726 (2)	0.36924 (16)	0.0214 (3)
C10	0.4711 (2)	0.7376 (2)	0.26146 (16)	0.0235 (3)
H10	0.3691	0.8438	0.2646	0.028*
C11	0.5423 (3)	0.6428 (2)	0.15148 (16)	0.0264 (4)
C12	0.6896 (3)	0.4891 (2)	0.14076 (17)	0.0288 (4)
H12	0.7343	0.4279	0.0625	0.035*
C13	0.7716 (3)	0.4254 (2)	0.24751 (17)	0.0279 (4)
H13	0.8746	0.3197	0.2425	0.033*
C14	0.7036 (2)	0.5154 (2)	0.36110 (17)	0.0251 (4)
H14	0.7589	0.4701	0.4341	0.030*
C15	0.7821 (3)	0.5407 (2)	0.7231 (2)	0.0362 (5)
H15A	0.9036	0.4827	0.7483	0.054*
H15B	0.7470	0.4572	0.6862	0.054*
H15C	0.6931	0.5958	0.7974	0.054*

	U11	U22	U33	U12	U13	U23
Br1	0.02857 (12)	0.03822 (11)	0.02513 (11)	−0.01096 (8)	0.00206 (7)	−0.00900 (7)
S1	0.0157 (2)	0.02387 (19)	0.0279 (2)	−0.00585 (15)	−0.00481 (16)	0.00069 (15)
F1	0.0440 (7)	0.0454 (6)	0.0252 (6)	−0.0113 (5)	−0.0152 (5)	−0.0005 (5)
O1	0.0172 (6)	0.0260 (6)	0.0224 (6)	−0.0047 (5)	−0.0053 (4)	−0.0020 (4)
O2	0.0266 (7)	0.0292 (6)	0.0416 (8)	−0.0129 (5)	−0.0134 (6)	0.0013 (5)
C1	0.0163 (8)	0.0212 (7)	0.0238 (8)	−0.0065 (6)	−0.0034 (6)	0.0000 (6)
C2	0.0172 (8)	0.0205 (7)	0.0234 (8)	−0.0069 (6)	−0.0032 (6)	0.0009 (6)
C3	0.0192 (8)	0.0248 (8)	0.0233 (8)	−0.0081 (6)	−0.0050 (6)	0.0009 (6)
C4	0.0241 (9)	0.0245 (7)	0.0222 (8)	−0.0102 (7)	−0.0013 (7)	−0.0016 (6)
C5	0.0185 (8)	0.0243 (8)	0.0309 (9)	−0.0047 (6)	−0.0003 (7)	−0.0012 (7)
C6	0.0167 (8)	0.0264 (8)	0.0303 (9)	−0.0047 (6)	−0.0058 (7)	−0.0002 (7)
C7	0.0199 (8)	0.0213 (7)	0.0223 (8)	−0.0071 (6)	−0.0043 (6)	0.0004 (6)
C8	0.0162 (8)	0.0209 (7)	0.0237 (8)	−0.0053 (6)	−0.0035 (6)	0.0009 (6)
C9	0.0204 (8)	0.0237 (7)	0.0224 (8)	−0.0107 (6)	−0.0035 (6)	−0.0016 (6)
C10	0.0206 (8)	0.0244 (7)	0.0271 (9)	−0.0096 (6)	−0.0059 (7)	0.0006 (6)
C11	0.0278 (10)	0.0327 (9)	0.0227 (8)	−0.0147 (7)	−0.0084 (7)	0.0022 (7)
C12	0.0287 (10)	0.0329 (9)	0.0259 (9)	−0.0139 (8)	0.0000 (7)	−0.0065 (7)
C13	0.0234 (9)	0.0256 (8)	0.0319 (9)	−0.0069 (7)	−0.0018 (7)	−0.0046 (7)
C14	0.0234 (9)	0.0250 (8)	0.0264 (8)	−0.0077 (7)	−0.0071 (7)	0.0007 (6)
C15	0.0331 (11)	0.0301 (9)	0.0502 (12)	−0.0143 (8)	−0.0191 (9)	0.0156 (8)

Br1—C4	1.8994 (17)	C6—C7	1.382 (2)
S1—O2	1.4884 (13)	C6—H6	0.9500
S1—C1	1.7662 (17)	C8—C9	1.459 (2)
S1—C15	1.7951 (19)	C9—C14	1.398 (2)
F1—C11	1.3604 (19)	C9—C10	1.405 (2)
O1—C7	1.376 (2)	C10—C11	1.371 (2)
O1—C8	1.379 (2)	C10—H10	0.9500
C1—C8	1.362 (2)	C11—C12	1.372 (3)
C1—C2	1.449 (2)	C12—C13	1.389 (3)
C2—C7	1.393 (2)	C12—H12	0.9500
C2—C3	1.397 (2)	C13—C14	1.384 (2)
C3—C4	1.381 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.402 (2)	C15—H15A	0.9800
C5—C6	1.382 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
Br1···O2i	3.2137 (13)
C4—Br1—O2i	163.28 (5)	C1—C8—C9	134.47 (15)
O2—S1—C1	107.07 (7)	O1—C8—C9	114.71 (14)
O2—S1—C15	105.85 (9)	C14—C9—C10	119.48 (15)
C1—S1—C15	97.64 (9)	C14—C9—C8	121.18 (15)
C7—O1—C8	106.58 (12)	C10—C9—C8	119.32 (15)
C8—C1—C2	106.97 (14)	C11—C10—C9	117.81 (16)
C8—C1—S1	126.42 (13)	C11—C10—H10	121.1
C2—C1—S1	126.36 (12)	C9—C10—H10	121.1
C7—C2—C3	119.31 (15)	F1—C11—C10	117.89 (16)
C7—C2—C1	105.05 (14)	F1—C11—C12	118.26 (16)
C3—C2—C1	135.62 (15)	C10—C11—C12	123.84 (16)
C4—C3—C2	116.65 (15)	C11—C12—C13	118.18 (16)
C4—C3—H3	121.7	C11—C12—H12	120.9
C2—C3—H3	121.7	C13—C12—H12	120.9
C3—C4—C5	123.30 (16)	C14—C13—C12	120.14 (16)
C3—C4—Br1	118.41 (13)	C14—C13—H13	119.9
C5—C4—Br1	118.28 (13)	C12—C13—H13	119.9
C6—C5—C4	120.26 (16)	C13—C14—C9	120.54 (16)
C6—C5—H5	119.9	C13—C14—H14	119.7
C4—C5—H5	119.9	C9—C14—H14	119.7
C7—C6—C5	116.17 (16)	S1—C15—H15A	109.5
C7—C6—H6	121.9	S1—C15—H15B	109.5
C5—C6—H6	121.9	H15A—C15—H15B	109.5
O1—C7—C6	125.06 (15)	S1—C15—H15C	109.5
O1—C7—C2	110.60 (14)	H15A—C15—H15C	109.5
C6—C7—C2	124.30 (16)	H15B—C15—H15C	109.5
C1—C8—O1	110.79 (14)
O2—S1—C1—C8	139.58 (15)	C1—C2—C7—C6	178.75 (16)
C15—S1—C1—C8	−111.19 (16)	C2—C1—C8—O1	−0.06 (18)
O2—S1—C1—C2	−33.90 (16)	S1—C1—C8—O1	−174.57 (12)
C15—S1—C1—C2	75.34 (16)	C2—C1—C8—C9	−177.94 (18)
C8—C1—C2—C7	−0.52 (18)	S1—C1—C8—C9	7.5 (3)
S1—C1—C2—C7	174.00 (13)	C7—O1—C8—C1	0.63 (18)
C8—C1—C2—C3	177.77 (18)	C7—O1—C8—C9	178.96 (14)
S1—C1—C2—C3	−7.7 (3)	C1—C8—C9—C14	30.3 (3)
C7—C2—C3—C4	0.2 (2)	O1—C8—C9—C14	−147.50 (16)
C1—C2—C3—C4	−177.90 (18)	C1—C8—C9—C10	−151.18 (19)
C2—C3—C4—C5	−0.4 (3)	O1—C8—C9—C10	31.0 (2)
C2—C3—C4—Br1	178.50 (12)	C14—C9—C10—C11	−0.3 (3)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	−178.86 (15)
Br1—C4—C5—C6	−178.66 (13)	C9—C10—C11—F1	178.95 (15)
C4—C5—C6—C7	0.1 (3)	C9—C10—C11—C12	−0.2 (3)
C8—O1—C7—C6	−178.78 (16)	F1—C11—C12—C13	−179.08 (16)
C8—O1—C7—C2	−0.97 (18)	C10—C11—C12—C13	0.1 (3)
C5—C6—C7—O1	177.22 (15)	C11—C12—C13—C14	0.6 (3)
C5—C6—C7—C2	−0.3 (3)	C12—C13—C14—C9	−1.2 (3)
C3—C2—C7—O1	−177.70 (14)	C10—C9—C14—C13	1.0 (3)
C1—C2—C7—O1	0.92 (18)	C8—C9—C14—C13	179.54 (17)
C3—C2—C7—C6	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ii	0.95	2.55	3.356 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.55	3.356 (2)	142

Symmetry code: (i) .