5-Bromo-3-(4-fluoro-phenyl-sulfin-yl)-2,7-dimethyl-1-benzofuran.

In the title compound, C(16)H(12)BrFO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 83.29 (5)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

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 our previous structural studies of related 3-[(4-fluoro­phen­yl)sulfin­yl]-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C16H12BrFO2S

M = 367.23

Triclinic,

a = 7.6696 (1) Å

b = 8.6308 (1) Å

c = 12.3225 (2) Å

α = 96.084 (1)°

β = 91.510 (1)°

γ = 113.609 (1)°

V = 741.08 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.93 mm−1

T = 173 K

0.26 × 0.16 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.583, T max = 0.746

13338 measured reflections

3422 independent reflections

2976 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.07

3422 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.56 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 datablocks global, I. DOI: 10.1107/S1600536810049986/zq2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049986/zq2078Isup2.hkl

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

C16H12BrFO2S	Z = 2
Mr = 367.23	F(000) = 368
Triclinic, P1	Dx = 1.646 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6696 (1) Å	Cell parameters from 6925 reflections
b = 8.6308 (1) Å	θ = 2.6–27.4°
c = 12.3225 (2) Å	µ = 2.93 mm−1
α = 96.084 (1)°	T = 173 K
β = 91.510 (1)°	Block, colourless
γ = 113.609 (1)°	0.26 × 0.16 × 0.13 mm
V = 741.08 (2) Å3

Bruker SMART APEXII CCD diffractometer	3422 independent reflections
Radiation source: rotating anode	2976 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.7°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.583, Tmax = 0.746	l = −16→16
13338 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F2) = 0.074	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.2033P] where P = (Fo2 + 2Fc2)/3
3422 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.56 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	−0.07124 (3)	0.06945 (2)	0.199937 (19)	0.04181 (9)
S1	0.18515 (6)	0.85094 (6)	0.34130 (4)	0.02781 (11)
F1	0.6274 (2)	0.6390 (2)	0.64210 (12)	0.0602 (4)
O1	0.32437 (18)	0.74870 (16)	0.04617 (10)	0.0286 (3)
O2	−0.01904 (19)	0.75643 (19)	0.36136 (12)	0.0377 (3)
C1	0.2264 (3)	0.7600 (2)	0.21574 (14)	0.0258 (4)
C2	0.1739 (2)	0.5831 (2)	0.17564 (14)	0.0246 (4)
C3	0.0805 (2)	0.4290 (2)	0.21663 (15)	0.0264 (4)
H3	0.0370	0.4241	0.2882	0.032*
C4	0.0547 (3)	0.2838 (2)	0.14748 (16)	0.0290 (4)
C5	0.1195 (3)	0.2869 (3)	0.04259 (16)	0.0306 (4)
H5	0.0975	0.1823	−0.0011	0.037*
C6	0.2153 (2)	0.4392 (3)	0.00081 (15)	0.0282 (4)
C7	0.2371 (2)	0.5836 (2)	0.07052 (14)	0.0247 (4)
C8	0.3136 (3)	0.8532 (2)	0.13575 (15)	0.0278 (4)
C9	0.2924 (3)	0.4477 (3)	−0.11043 (16)	0.0371 (5)
H9A	0.2846	0.5445	−0.1420	0.056*
H9B	0.2169	0.3418	−0.1582	0.056*
H9C	0.4258	0.4622	−0.1036	0.056*
C10	0.3976 (3)	1.0383 (3)	0.12828 (18)	0.0372 (5)
H10A	0.3640	1.0983	0.1908	0.056*
H10B	0.3477	1.0599	0.0601	0.056*
H10C	0.5367	1.0793	0.1290	0.056*
C11	0.3197 (3)	0.7776 (2)	0.42827 (14)	0.0266 (4)
C12	0.5103 (3)	0.8142 (3)	0.41325 (17)	0.0339 (4)
H12	0.5684	0.8718	0.3536	0.041*
C13	0.6149 (3)	0.7668 (3)	0.48527 (18)	0.0392 (5)
H13	0.7453	0.7904	0.4762	0.047*
C14	0.5250 (3)	0.6845 (3)	0.57035 (17)	0.0392 (5)
C15	0.3374 (3)	0.6460 (3)	0.58663 (18)	0.0432 (5)
H15	0.2798	0.5873	0.6459	0.052*
C16	0.2333 (3)	0.6950 (3)	0.51448 (16)	0.0348 (4)
H16	0.1031	0.6717	0.5244	0.042*

	U11	U22	U33	U12	U13	U23
Br1	0.04528 (14)	0.02586 (12)	0.05240 (15)	0.01188 (9)	0.00989 (10)	0.00587 (9)
S1	0.0333 (2)	0.0265 (2)	0.0255 (2)	0.01415 (19)	0.00559 (18)	0.00215 (18)
F1	0.0650 (9)	0.0718 (10)	0.0519 (8)	0.0382 (8)	−0.0190 (7)	0.0048 (7)
O1	0.0308 (6)	0.0331 (7)	0.0241 (6)	0.0142 (5)	0.0064 (5)	0.0068 (5)
O2	0.0312 (7)	0.0510 (9)	0.0346 (7)	0.0200 (6)	0.0082 (6)	0.0056 (6)
C1	0.0290 (9)	0.0263 (9)	0.0236 (8)	0.0124 (7)	0.0040 (7)	0.0042 (7)
C2	0.0240 (8)	0.0293 (9)	0.0230 (8)	0.0135 (7)	0.0009 (7)	0.0031 (7)
C3	0.0270 (8)	0.0279 (9)	0.0255 (9)	0.0120 (7)	0.0018 (7)	0.0053 (7)
C4	0.0267 (9)	0.0270 (9)	0.0346 (10)	0.0124 (7)	−0.0004 (7)	0.0035 (8)
C5	0.0271 (9)	0.0336 (10)	0.0318 (10)	0.0157 (8)	−0.0040 (7)	−0.0047 (8)
C6	0.0239 (8)	0.0395 (11)	0.0235 (8)	0.0167 (8)	−0.0019 (7)	−0.0011 (8)
C7	0.0227 (8)	0.0302 (9)	0.0235 (8)	0.0126 (7)	0.0009 (7)	0.0064 (7)
C8	0.0290 (9)	0.0306 (10)	0.0261 (9)	0.0140 (7)	0.0046 (7)	0.0056 (7)
C9	0.0351 (10)	0.0512 (13)	0.0255 (9)	0.0193 (9)	0.0026 (8)	−0.0012 (9)
C10	0.0433 (11)	0.0316 (11)	0.0391 (11)	0.0152 (9)	0.0136 (9)	0.0122 (9)
C11	0.0300 (9)	0.0232 (9)	0.0234 (8)	0.0087 (7)	0.0027 (7)	−0.0016 (7)
C12	0.0316 (9)	0.0348 (11)	0.0311 (10)	0.0097 (8)	0.0065 (8)	0.0003 (8)
C13	0.0309 (10)	0.0441 (12)	0.0408 (12)	0.0166 (9)	−0.0021 (9)	−0.0068 (9)
C14	0.0463 (12)	0.0398 (12)	0.0335 (11)	0.0227 (10)	−0.0119 (9)	−0.0044 (9)
C15	0.0478 (12)	0.0501 (13)	0.0329 (11)	0.0195 (10)	0.0034 (9)	0.0121 (10)
C16	0.0315 (10)	0.0411 (11)	0.0306 (10)	0.0123 (8)	0.0061 (8)	0.0085 (8)

Br1—C4	1.9047 (19)	C8—C10	1.479 (3)
S1—O2	1.4896 (14)	C9—H9A	0.9800
S1—C1	1.7542 (18)	C9—H9B	0.9800
S1—C11	1.796 (2)	C9—H9C	0.9800
F1—C14	1.355 (2)	C10—H10A	0.9800
O1—C8	1.376 (2)	C10—H10B	0.9800
O1—C7	1.381 (2)	C10—H10C	0.9800
C1—C8	1.355 (3)	C11—C16	1.377 (3)
C1—C2	1.440 (2)	C11—C12	1.388 (3)
C2—C3	1.391 (2)	C12—C13	1.379 (3)
C2—C7	1.395 (2)	C12—H12	0.9500
C3—C4	1.379 (3)	C13—C14	1.372 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.396 (3)	C14—C15	1.367 (3)
C5—C6	1.387 (3)	C15—C16	1.385 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.385 (3)	C16—H16	0.9500
C6—C9	1.504 (3)
O2—S1—C1	107.96 (8)	C6—C9—H9B	109.5
O2—S1—C11	106.25 (9)	H9A—C9—H9B	109.5
C1—S1—C11	97.50 (8)	C6—C9—H9C	109.5
C8—O1—C7	106.70 (14)	H9A—C9—H9C	109.5
C8—C1—C2	107.61 (16)	H9B—C9—H9C	109.5
C8—C1—S1	123.11 (14)	C8—C10—H10A	109.5
C2—C1—S1	129.25 (14)	C8—C10—H10B	109.5
C3—C2—C7	119.70 (17)	H10A—C10—H10B	109.5
C3—C2—C1	135.32 (17)	C8—C10—H10C	109.5
C7—C2—C1	104.97 (16)	H10A—C10—H10C	109.5
C4—C3—C2	116.19 (17)	H10B—C10—H10C	109.5
C4—C3—H3	121.9	C16—C11—C12	120.99 (19)
C2—C3—H3	121.9	C16—C11—S1	118.35 (15)
C3—C4—C5	123.27 (18)	C12—C11—S1	120.50 (15)
C3—C4—Br1	117.87 (14)	C13—C12—C11	119.71 (19)
C5—C4—Br1	118.84 (14)	C13—C12—H12	120.1
C6—C5—C4	121.43 (18)	C11—C12—H12	120.1
C6—C5—H5	119.3	C14—C13—C12	118.06 (19)
C4—C5—H5	119.3	C14—C13—H13	121.0
C7—C6—C5	114.55 (17)	C12—C13—H13	121.0
C7—C6—C9	122.55 (18)	F1—C14—C15	118.2 (2)
C5—C6—C9	122.89 (18)	F1—C14—C13	118.4 (2)
O1—C7—C6	124.99 (16)	C15—C14—C13	123.4 (2)
O1—C7—C2	110.17 (15)	C14—C15—C16	118.3 (2)
C6—C7—C2	124.84 (17)	C14—C15—H15	120.8
C1—C8—O1	110.55 (16)	C16—C15—H15	120.8
C1—C8—C10	132.90 (17)	C11—C16—C15	119.53 (19)
O1—C8—C10	116.54 (16)	C11—C16—H16	120.2
C6—C9—H9A	109.5	C15—C16—H16	120.2
O2—S1—C1—C8	130.04 (16)	C1—C2—C7—O1	0.42 (19)
C11—S1—C1—C8	−120.12 (17)	C3—C2—C7—C6	−0.4 (3)
O2—S1—C1—C2	−47.76 (19)	C1—C2—C7—C6	−179.62 (17)
C11—S1—C1—C2	62.07 (18)	C2—C1—C8—O1	−0.9 (2)
C8—C1—C2—C3	−178.74 (19)	S1—C1—C8—O1	−179.16 (12)
S1—C1—C2—C3	−0.7 (3)	C2—C1—C8—C10	180.0 (2)
C8—C1—C2—C7	0.3 (2)	S1—C1—C8—C10	1.8 (3)
S1—C1—C2—C7	178.39 (14)	C7—O1—C8—C1	1.2 (2)
C7—C2—C3—C4	−0.8 (2)	C7—O1—C8—C10	−179.57 (16)
C1—C2—C3—C4	178.19 (19)	O2—S1—C11—C16	−17.77 (17)
C2—C3—C4—C5	1.0 (3)	C1—S1—C11—C16	−129.02 (16)
C2—C3—C4—Br1	179.66 (12)	O2—S1—C11—C12	166.73 (15)
C3—C4—C5—C6	−0.1 (3)	C1—S1—C11—C12	55.49 (16)
Br1—C4—C5—C6	−178.75 (13)	C16—C11—C12—C13	0.3 (3)
C4—C5—C6—C7	−1.0 (3)	S1—C11—C12—C13	175.68 (15)
C4—C5—C6—C9	178.10 (17)	C11—C12—C13—C14	−0.2 (3)
C8—O1—C7—C6	179.06 (17)	C12—C13—C14—F1	−179.34 (18)
C8—O1—C7—C2	−0.98 (19)	C12—C13—C14—C15	0.6 (3)
C5—C6—C7—O1	−178.80 (16)	F1—C14—C15—C16	178.93 (19)
C9—C6—C7—O1	2.1 (3)	C13—C14—C15—C16	−1.0 (3)
C5—C6—C7—C2	1.3 (3)	C12—C11—C16—C15	−0.7 (3)
C9—C6—C7—C2	−177.84 (17)	S1—C11—C16—C15	−176.19 (16)
C3—C2—C7—O1	179.65 (15)	C14—C15—C16—C11	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.41	3.259 (2)	148.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.41	3.259 (2)	148

Symmetry code: (i) .