5-Bromo-3-(3-fluoro-phenyl-sulfin-yl)-2-methyl-1-benzofuran.

In the title compound, C(15)H(10)BrFO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 85.0 (1)° with the mean plane [r.m.s. deviation = 0.008 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and a Br⋯O contact [3.200 (3) Å]. The crystal structure also exhibits slipped π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.619 (4) Å and slippage of 1.389 (4) Å]. In the 3-fluoro-phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.583 (5) and 0.417 (5).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶, 2012 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H10BrFO2S

M = 353.20

Monoclinic,

a = 13.0488 (4) Å

b = 11.1874 (3) Å

c = 9.9295 (3) Å

β = 105.709 (2)°

V = 1395.39 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.10 mm−1

T = 173 K

0.25 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.494, T max = 0.746

13225 measured reflections

3460 independent reflections

2392 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.03

3460 reflections

192 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −1.10 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/S1600536812032394/kp2435sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032394/kp2435Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032394/kp2435Isup3.cml

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

C15H10BrFO2S	F(000) = 704
Mr = 353.20	Dx = 1.681 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3368 reflections
a = 13.0488 (4) Å	θ = 2.4–26.5°
b = 11.1874 (3) Å	µ = 3.10 mm−1
c = 9.9295 (3) Å	T = 173 K
β = 105.709 (2)°	Block, colourless
V = 1395.39 (7) Å3	0.25 × 0.24 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3460 independent reflections
Radiation source: rotating anode	2392 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.048
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.6°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→14
Tmin = 0.494, Tmax = 0.746	l = −13→12
13225 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.9756P] where P = (Fo2 + 2Fc2)/3
3460 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.61 e Å−3
14 restraints	Δρmin = −1.10 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	Occ. (<1)
Br1	0.78842 (3)	0.16727 (3)	0.52938 (5)	0.06445 (17)
S1	0.70738 (6)	0.67272 (7)	0.23040 (7)	0.03887 (19)
O1	0.93643 (16)	0.67342 (18)	0.5796 (2)	0.0384 (5)
O2	0.7178 (2)	0.5873 (2)	0.1208 (2)	0.0595 (7)
C1	0.8025 (2)	0.6387 (3)	0.3879 (3)	0.0333 (6)
C2	0.8265 (2)	0.5272 (3)	0.4624 (3)	0.0326 (6)
C3	0.7894 (2)	0.4090 (3)	0.4423 (3)	0.0385 (7)
H3	0.7343	0.3862	0.3625	0.046*
C4	0.8371 (3)	0.3279 (3)	0.5442 (4)	0.0426 (7)
C5	0.9200 (3)	0.3574 (3)	0.6612 (3)	0.0445 (8)
H5	0.9500	0.2978	0.7285	0.053*
C6	0.9583 (2)	0.4726 (3)	0.6796 (3)	0.0411 (7)
H6	1.0153	0.4945	0.7578	0.049*
C7	0.9100 (2)	0.5543 (3)	0.5793 (3)	0.0345 (6)
C8	0.8706 (2)	0.7221 (3)	0.4607 (3)	0.0352 (6)
C9	0.8858 (3)	0.8504 (3)	0.4392 (4)	0.0463 (8)
H9A	0.8629	0.8968	0.5096	0.069*
H9B	0.8435	0.8738	0.3456	0.069*
H9C	0.9613	0.8662	0.4482	0.069*
C10	0.5915 (2)	0.6284 (3)	0.2817 (3)	0.0387 (7)
C11	0.5255 (3)	0.5431 (3)	0.2057 (4)	0.0532 (9)
H11	0.5429	0.5013	0.1317	0.064*
C12	0.4339 (3)	0.5211 (4)	0.2412 (6)	0.0788 (15)	0.583 (5)
H12	0.3870	0.4631	0.1877	0.095*	0.583 (5)
C12'	0.4339 (3)	0.5211 (4)	0.2412 (6)	0.0788 (15)	0.42
F1'	0.3631 (4)	0.4412 (5)	0.1945 (7)	0.083 (2)	0.417 (5)
C13	0.4043 (3)	0.5740 (6)	0.3450 (6)	0.0877 (17)
H13	0.3394	0.5553	0.3661	0.105*
C14	0.4731 (3)	0.6561 (5)	0.4180 (4)	0.0805 (17)	0.583 (5)
F1	0.4478 (3)	0.6915 (4)	0.5278 (4)	0.0791 (15)	0.583 (5)
C14'	0.4731 (3)	0.6561 (5)	0.4180 (4)	0.0805 (17)	0.42
H14'	0.4556	0.6940	0.4944	0.097*	0.417 (5)
C15	0.5663 (3)	0.6885 (4)	0.3896 (3)	0.0542 (10)
H15	0.6111	0.7490	0.4414	0.065*

	U11	U22	U33	U12	U13	U23
Br1	0.0542 (2)	0.0364 (2)	0.0981 (4)	0.00465 (16)	0.0128 (2)	0.00779 (18)
S1	0.0434 (4)	0.0439 (4)	0.0301 (4)	0.0032 (3)	0.0112 (3)	0.0067 (3)
O1	0.0351 (10)	0.0423 (12)	0.0376 (11)	−0.0004 (9)	0.0096 (8)	−0.0034 (9)
O2	0.0720 (16)	0.0729 (18)	0.0372 (12)	0.0076 (14)	0.0210 (11)	−0.0055 (11)
C1	0.0307 (13)	0.0405 (16)	0.0317 (14)	0.0033 (12)	0.0134 (11)	0.0013 (12)
C2	0.0280 (12)	0.0398 (16)	0.0324 (14)	0.0050 (12)	0.0125 (11)	0.0011 (12)
C3	0.0323 (13)	0.0404 (17)	0.0427 (16)	0.0037 (13)	0.0099 (12)	−0.0013 (13)
C4	0.0384 (15)	0.0360 (17)	0.0557 (19)	0.0062 (13)	0.0163 (14)	0.0028 (14)
C5	0.0433 (17)	0.0472 (19)	0.0441 (17)	0.0180 (14)	0.0139 (14)	0.0079 (14)
C6	0.0365 (15)	0.050 (2)	0.0343 (15)	0.0097 (14)	0.0059 (12)	−0.0037 (13)
C7	0.0313 (13)	0.0379 (16)	0.0361 (15)	0.0031 (12)	0.0123 (11)	−0.0020 (12)
C8	0.0339 (14)	0.0410 (17)	0.0353 (15)	0.0030 (13)	0.0170 (12)	0.0021 (13)
C9	0.0479 (18)	0.0395 (18)	0.055 (2)	−0.0038 (14)	0.0197 (15)	0.0019 (15)
C10	0.0347 (14)	0.0477 (18)	0.0300 (14)	0.0053 (13)	0.0025 (11)	0.0084 (13)
C11	0.0481 (18)	0.051 (2)	0.055 (2)	0.0010 (16)	0.0041 (16)	0.0024 (16)
C12	0.044 (2)	0.083 (3)	0.101 (4)	−0.009 (2)	0.006 (2)	0.025 (3)
C12'	0.044 (2)	0.083 (3)	0.101 (4)	−0.009 (2)	0.006 (2)	0.025 (3)
F1'	0.068 (3)	0.070 (4)	0.101 (4)	−0.032 (3)	0.007 (3)	−0.012 (3)
C13	0.0324 (18)	0.139 (5)	0.090 (3)	−0.001 (2)	0.014 (2)	0.040 (3)
C14	0.042 (2)	0.151 (5)	0.050 (2)	0.012 (3)	0.0150 (17)	0.012 (3)
F1	0.057 (2)	0.120 (4)	0.069 (3)	0.005 (2)	0.0304 (19)	−0.028 (2)
C14'	0.042 (2)	0.151 (5)	0.050 (2)	0.012 (3)	0.0150 (17)	0.012 (3)
C15	0.0370 (16)	0.086 (3)	0.0367 (17)	0.0038 (17)	0.0056 (13)	−0.0030 (17)

Br1—C4	1.898 (3)	C6—H6	0.9500
Br1—O2i	3.200 (3)	C8—C9	1.472 (4)
S1—O2	1.482 (3)	C9—H9A	0.9800
S1—C1	1.755 (3)	C9—H9B	0.9800
S1—C10	1.792 (3)	C9—H9C	0.9800
O1—C8	1.371 (3)	C10—C11	1.367 (5)
O1—C7	1.377 (4)	C10—C15	1.378 (5)
C1—C8	1.355 (4)	C11—C12	1.357 (6)
C1—C2	1.441 (4)	C11—H11	0.9500
C2—C7	1.393 (4)	C12—C13	1.333 (7)
C2—C3	1.404 (4)	C12—H12	0.9500
C3—C4	1.376 (4)	C13—C14	1.349 (7)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.396 (5)	C14—F1	1.284 (4)
C5—C6	1.377 (5)	C14—C15	1.370 (5)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.373 (4)
C4—Br1—O2i	159.51 (11)	C1—C8—C9	133.6 (3)
O2—S1—C1	109.35 (14)	O1—C8—C9	115.8 (3)
O2—S1—C10	106.41 (16)	C8—C9—H9A	109.5
C1—S1—C10	97.72 (13)	C8—C9—H9B	109.5
C8—O1—C7	106.5 (2)	H9A—C9—H9B	109.5
C8—C1—C2	107.6 (2)	C8—C9—H9C	109.5
C8—C1—S1	122.0 (2)	H9A—C9—H9C	109.5
C2—C1—S1	130.4 (2)	H9B—C9—H9C	109.5
C7—C2—C3	119.0 (3)	C11—C10—C15	121.5 (3)
C7—C2—C1	104.6 (3)	C11—C10—S1	119.4 (3)
C3—C2—C1	136.4 (3)	C15—C10—S1	118.9 (3)
C4—C3—C2	116.6 (3)	C12—C11—C10	116.8 (4)
C4—C3—H3	121.7	C12—C11—H11	121.6
C2—C3—H3	121.7	C10—C11—H11	121.6
C3—C4—C5	123.4 (3)	C13—C12—C11	125.4 (4)
C3—C4—Br1	119.5 (2)	C13—C12—H12	117.3
C5—C4—Br1	117.1 (2)	C11—C12—H12	117.3
C6—C5—C4	120.2 (3)	C12—C13—C14	115.3 (4)
C6—C5—H5	119.9	C12—C13—H13	122.3
C4—C5—H5	119.9	C14—C13—H13	122.3
C7—C6—C5	116.6 (3)	F1—C14—C13	112.3 (4)
C7—C6—H6	121.7	F1—C14—C15	122.6 (4)
C5—C6—H6	121.7	C13—C14—C15	124.6 (4)
C6—C7—O1	125.2 (3)	C14—C15—C10	116.3 (4)
C6—C7—C2	124.2 (3)	C14—C15—H15	121.8
O1—C7—C2	110.6 (2)	C10—C15—H15	121.8
C1—C8—O1	110.7 (3)
O2—S1—C1—C8	127.1 (2)	C3—C2—C7—O1	178.8 (2)
C10—S1—C1—C8	−122.4 (3)	C1—C2—C7—O1	0.4 (3)
O2—S1—C1—C2	−51.6 (3)	C2—C1—C8—O1	−1.2 (3)
C10—S1—C1—C2	58.9 (3)	S1—C1—C8—O1	179.78 (19)
C8—C1—C2—C7	0.5 (3)	C2—C1—C8—C9	−179.9 (3)
S1—C1—C2—C7	179.4 (2)	S1—C1—C8—C9	1.2 (5)
C8—C1—C2—C3	−177.5 (3)	C7—O1—C8—C1	1.4 (3)
S1—C1—C2—C3	1.3 (5)	C7—O1—C8—C9	−179.7 (3)
C7—C2—C3—C4	2.1 (4)	O2—S1—C10—C11	−9.5 (3)
C1—C2—C3—C4	179.9 (3)	C1—S1—C10—C11	−122.3 (3)
C2—C3—C4—C5	−1.5 (5)	O2—S1—C10—C15	176.0 (3)
C2—C3—C4—Br1	177.6 (2)	C1—S1—C10—C15	63.1 (3)
O2i—Br1—C4—C3	−138.1 (3)	C15—C10—C11—C12	0.4 (5)
O2i—Br1—C4—C5	41.0 (5)	S1—C10—C11—C12	−174.0 (3)
C3—C4—C5—C6	0.0 (5)	C10—C11—C12—C13	−1.3 (7)
Br1—C4—C5—C6	−179.1 (2)	C11—C12—C13—C14	0.3 (7)
C4—C5—C6—C7	0.9 (5)	C12—C13—C14—F1	−170.9 (5)
C5—C6—C7—O1	179.6 (3)	C12—C13—C14—C15	1.7 (7)
C5—C6—C7—C2	−0.3 (5)	F1—C14—C15—C10	169.4 (4)
C8—O1—C7—C6	179.0 (3)	C13—C14—C15—C10	−2.5 (7)
C8—O1—C7—C2	−1.1 (3)	C11—C10—C15—C14	1.4 (5)
C3—C2—C7—C6	−1.3 (4)	S1—C10—C15—C14	175.8 (3)
C1—C2—C7—C6	−179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.95	2.50	3.429 (4)	167
C9—H9A···O2iii	0.98	2.44	3.269 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.50	3.429 (4)	167
C9—H9A⋯O2ii	0.98	2.44	3.269 (4)	142

Symmetry codes: (i) ; (ii) .