5-Bromo-3-ethyl-sulfinyl-2-(4-fluoro-phen-yl)-7-methyl-1-benzofuran.

In the title compound, C(17)H(14)BrFO(2)S, the 4-fluoro-phenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 7.60 (4)°. The crystal structure is stabilized by a Br⋯O halogen-bonding inter-action [3.048 (1) Å].

Related literature

For the crystal structures of similar 3-ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010 ▶). 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 a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H14BrFO2S

M = 381.25

Triclinic,

a = 7.3446 (2) Å

b = 10.6107 (3) Å

c = 11.3132 (5) Å

α = 111.555 (2)°

β = 94.643 (2)°

γ = 108.900 (2)°

V = 755.49 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.87 mm−1

T = 174 K

0.31 × 0.26 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.471, T max = 0.674

13244 measured reflections

3493 independent reflections

3194 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.07

3493 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.58 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/S1600536810011906/ng2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011906/ng2754Isup2.hkl

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

C17H14BrFO2S	Z = 2
Mr = 381.25	F(000) = 384
Triclinic, P1	Dx = 1.676 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3446 (2) Å	Cell parameters from 8577 reflections
b = 10.6107 (3) Å	θ = 2.2–27.6°
c = 11.3132 (5) Å	µ = 2.87 mm−1
α = 111.555 (2)°	T = 174 K
β = 94.643 (2)°	Block, colourless
γ = 108.900 (2)°	0.31 × 0.26 × 0.15 mm
V = 755.49 (4) Å3

Bruker SMART APEXII CCD diffractometer	3493 independent reflections
Radiation source: Rotating Anode	3194 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.036
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→12
Tmin = 0.471, Tmax = 0.674	l = −13→14
13244 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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.068	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0335P)2 + 0.2459P] where P = (Fo2 + 2Fc2)/3
3493 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.58 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	0.20782 (3)	0.72623 (2)	1.086606 (16)	0.03206 (8)
S	0.05552 (6)	0.19539 (4)	0.57197 (4)	0.02301 (10)
F	0.24222 (19)	0.15769 (15)	−0.03546 (11)	0.0455 (3)
O1	0.27205 (17)	0.57068 (12)	0.53317 (11)	0.0219 (2)
O2	−0.10175 (19)	0.19674 (15)	0.64784 (14)	0.0345 (3)
C1	0.1662 (2)	0.37550 (18)	0.58283 (16)	0.0203 (3)
C2	0.2030 (2)	0.50589 (18)	0.69956 (16)	0.0209 (3)
C3	0.1867 (2)	0.53431 (19)	0.82812 (16)	0.0234 (3)
H3	0.1451	0.4580	0.8568	0.028*
C4	0.2345 (2)	0.67946 (19)	0.91155 (17)	0.0241 (3)
C5	0.2930 (2)	0.79348 (19)	0.87163 (17)	0.0240 (3)
H5	0.3218	0.8909	0.9329	0.029*
C6	0.3099 (2)	0.76755 (18)	0.74429 (17)	0.0222 (3)
C7	0.2652 (2)	0.62129 (18)	0.66271 (16)	0.0205 (3)
C8	0.2100 (2)	0.41988 (18)	0.48532 (16)	0.0203 (3)
C9	0.2121 (2)	0.34816 (19)	0.34813 (16)	0.0219 (3)
C10	0.2479 (3)	0.4298 (2)	0.27369 (17)	0.0268 (4)
H10	0.2651	0.5301	0.3121	0.032*
C11	0.2587 (3)	0.3664 (2)	0.14460 (18)	0.0320 (4)
H11	0.2851	0.4224	0.0945	0.038*
C12	0.2301 (3)	0.2198 (2)	0.09087 (16)	0.0312 (4)
C13	0.1893 (3)	0.1346 (2)	0.15890 (18)	0.0306 (4)
H13	0.1662	0.0333	0.1181	0.037*
C14	0.1825 (3)	0.1992 (2)	0.28841 (17)	0.0276 (4)
H14	0.1575	0.1420	0.3375	0.033*
C15	0.3686 (3)	0.8872 (2)	0.69820 (19)	0.0295 (4)
H15A	0.3548	0.9744	0.7611	0.044*
H15B	0.2831	0.8545	0.6129	0.044*
H15C	0.5064	0.9112	0.6904	0.044*
C16	0.2622 (3)	0.1950 (2)	0.66993 (18)	0.0287 (4)
H16A	0.3245	0.2902	0.7471	0.034*
H16B	0.2152	0.1168	0.7010	0.034*
C17	0.4128 (3)	0.1691 (2)	0.5895 (2)	0.0319 (4)
H17A	0.3523	0.0730	0.5152	0.048*
H17B	0.5264	0.1721	0.6439	0.048*
H17C	0.4571	0.2456	0.5575	0.048*

	U11	U22	U33	U12	U13	U23
Br	0.04146 (12)	0.02764 (11)	0.01931 (11)	0.00761 (8)	0.00969 (7)	0.00583 (8)
S	0.0257 (2)	0.0181 (2)	0.0225 (2)	0.00599 (16)	0.00715 (16)	0.00724 (17)
F	0.0572 (7)	0.0540 (8)	0.0207 (6)	0.0234 (6)	0.0151 (5)	0.0078 (5)
O1	0.0283 (6)	0.0189 (6)	0.0201 (6)	0.0103 (5)	0.0073 (4)	0.0083 (5)
O2	0.0304 (6)	0.0323 (7)	0.0360 (8)	0.0069 (6)	0.0163 (6)	0.0118 (6)
C1	0.0228 (7)	0.0185 (8)	0.0202 (8)	0.0096 (6)	0.0056 (6)	0.0072 (7)
C2	0.0208 (7)	0.0193 (8)	0.0224 (8)	0.0084 (6)	0.0047 (6)	0.0078 (7)
C3	0.0264 (8)	0.0227 (8)	0.0216 (8)	0.0090 (7)	0.0065 (6)	0.0101 (7)
C4	0.0251 (8)	0.0257 (9)	0.0199 (8)	0.0090 (7)	0.0069 (6)	0.0081 (7)
C5	0.0257 (8)	0.0192 (8)	0.0239 (8)	0.0091 (6)	0.0061 (6)	0.0050 (7)
C6	0.0231 (7)	0.0198 (8)	0.0249 (8)	0.0101 (6)	0.0057 (6)	0.0089 (7)
C7	0.0224 (7)	0.0225 (8)	0.0195 (8)	0.0115 (6)	0.0065 (6)	0.0091 (7)
C8	0.0208 (7)	0.0182 (8)	0.0224 (8)	0.0091 (6)	0.0046 (6)	0.0077 (7)
C9	0.0193 (7)	0.0253 (8)	0.0205 (8)	0.0093 (6)	0.0040 (6)	0.0084 (7)
C10	0.0286 (8)	0.0257 (9)	0.0224 (9)	0.0081 (7)	0.0049 (7)	0.0084 (7)
C11	0.0341 (9)	0.0382 (11)	0.0239 (9)	0.0105 (8)	0.0075 (7)	0.0157 (8)
C12	0.0291 (9)	0.0412 (11)	0.0184 (9)	0.0144 (8)	0.0069 (7)	0.0062 (8)
C13	0.0346 (9)	0.0291 (10)	0.0256 (9)	0.0161 (8)	0.0079 (7)	0.0049 (8)
C14	0.0314 (9)	0.0280 (9)	0.0241 (9)	0.0139 (7)	0.0087 (7)	0.0090 (8)
C15	0.0383 (9)	0.0227 (9)	0.0308 (10)	0.0143 (7)	0.0089 (8)	0.0122 (8)
C16	0.0382 (9)	0.0261 (9)	0.0262 (9)	0.0150 (8)	0.0067 (7)	0.0132 (8)
C17	0.0297 (9)	0.0298 (10)	0.0374 (11)	0.0122 (8)	0.0065 (8)	0.0148 (9)

Br—C4	1.900 (2)	C9—C10	1.397 (2)
Br—O2i	3.048 (1)	C9—C14	1.404 (2)
S—O2	1.495 (1)	C10—C11	1.387 (3)
S—C1	1.770 (2)	C10—H10	0.9500
S—C16	1.808 (2)	C11—C12	1.381 (3)
F—C12	1.361 (2)	C11—H11	0.9500
O1—C7	1.375 (2)	C12—C13	1.369 (3)
O1—C8	1.383 (2)	C13—C14	1.384 (3)
C1—C8	1.372 (2)	C13—H13	0.9500
C1—C2	1.445 (2)	C14—H14	0.9500
C2—C7	1.388 (2)	C15—H15A	0.9800
C2—C3	1.396 (2)	C15—H15B	0.9800
C3—C4	1.384 (2)	C15—H15C	0.9800
C3—H3	0.9500	C16—C17	1.517 (3)
C4—C5	1.396 (2)	C16—H16A	0.9900
C5—C6	1.388 (2)	C16—H16B	0.9900
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.391 (2)	C17—H17B	0.9800
C6—C15	1.496 (2)	C17—H17C	0.9800
C8—C9	1.460 (2)
C4—Br—O2i	170.73 (6)	C11—C10—H10	119.5
O2—S—C1	106.31 (8)	C9—C10—H10	119.5
O2—S—C16	107.61 (9)	C12—C11—C10	118.21 (18)
C1—S—C16	97.95 (8)	C12—C11—H11	120.9
C7—O1—C8	107.02 (12)	C10—C11—H11	120.9
C8—C1—C2	107.05 (14)	F—C12—C13	118.78 (18)
C8—C1—S	128.90 (13)	F—C12—C11	118.35 (17)
C2—C1—S	123.59 (12)	C13—C12—C11	122.88 (17)
C7—C2—C3	119.53 (15)	C12—C13—C14	118.59 (18)
C7—C2—C1	105.42 (14)	C12—C13—H13	120.7
C3—C2—C1	135.05 (16)	C14—C13—H13	120.7
C4—C3—C2	116.47 (15)	C13—C14—C9	120.82 (17)
C4—C3—H3	121.8	C13—C14—H14	119.6
C2—C3—H3	121.8	C9—C14—H14	119.6
C3—C4—C5	123.00 (16)	C6—C15—H15A	109.5
C3—C4—Br	118.94 (13)	C6—C15—H15B	109.5
C5—C4—Br	117.99 (13)	H15A—C15—H15B	109.5
C6—C5—C4	121.42 (16)	C6—C15—H15C	109.5
C6—C5—H5	119.3	H15A—C15—H15C	109.5
C4—C5—H5	119.3	H15B—C15—H15C	109.5
C5—C6—C7	114.64 (15)	C17—C16—S	109.86 (13)
C5—C6—C15	122.56 (16)	C17—C16—H16A	109.7
C7—C6—C15	122.79 (16)	S—C16—H16A	109.7
O1—C7—C2	110.53 (14)	C17—C16—H16B	109.7
O1—C7—C6	124.55 (15)	S—C16—H16B	109.7
C2—C7—C6	124.91 (15)	H16A—C16—H16B	108.2
C1—C8—O1	109.97 (14)	C16—C17—H17A	109.5
C1—C8—C9	135.84 (15)	C16—C17—H17B	109.5
O1—C8—C9	114.16 (14)	H17A—C17—H17B	109.5
C10—C9—C14	118.50 (16)	C16—C17—H17C	109.5
C10—C9—C8	119.51 (16)	H17A—C17—H17C	109.5
C14—C9—C8	121.98 (15)	H17B—C17—H17C	109.5
C11—C10—C9	120.97 (17)
O2—S—C1—C8	−132.95 (15)	C5—C6—C7—C2	1.6 (2)
C16—S—C1—C8	116.00 (16)	C15—C6—C7—C2	−177.44 (16)
O2—S—C1—C2	38.33 (15)	C2—C1—C8—O1	−0.13 (17)
C16—S—C1—C2	−72.72 (15)	S—C1—C8—O1	172.28 (12)
C8—C1—C2—C7	0.71 (17)	C2—C1—C8—C9	177.69 (17)
S—C1—C2—C7	−172.20 (12)	S—C1—C8—C9	−9.9 (3)
C8—C1—C2—C3	179.68 (18)	C7—O1—C8—C1	−0.51 (17)
S—C1—C2—C3	6.8 (3)	C7—O1—C8—C9	−178.85 (13)
C7—C2—C3—C4	0.2 (2)	C1—C8—C9—C10	173.69 (18)
C1—C2—C3—C4	−178.62 (17)	O1—C8—C9—C10	−8.5 (2)
C2—C3—C4—C5	1.1 (2)	C1—C8—C9—C14	−7.4 (3)
C2—C3—C4—Br	177.98 (12)	O1—C8—C9—C14	170.35 (14)
C3—C4—C5—C6	−1.1 (3)	C14—C9—C10—C11	−1.5 (3)
Br—C4—C5—C6	−178.01 (12)	C8—C9—C10—C11	177.43 (15)
C4—C5—C6—C7	−0.3 (2)	C9—C10—C11—C12	1.0 (3)
C4—C5—C6—C15	178.82 (16)	C10—C11—C12—F	−179.44 (15)
C8—O1—C7—C2	0.99 (17)	C10—C11—C12—C13	0.8 (3)
C8—O1—C7—C6	−177.55 (15)	F—C12—C13—C14	178.23 (16)
C3—C2—C7—O1	179.79 (14)	C11—C12—C13—C14	−2.0 (3)
C1—C2—C7—O1	−1.05 (17)	C12—C13—C14—C9	1.5 (3)
C3—C2—C7—C6	−1.7 (2)	C10—C9—C14—C13	0.3 (3)
C1—C2—C7—C6	177.48 (15)	C8—C9—C14—C13	−178.65 (15)
C5—C6—C7—O1	179.99 (14)	O2—S—C16—C17	170.98 (13)
C15—C6—C7—O1	0.9 (3)	C1—S—C16—C17	−79.03 (14)