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

In the title compound, C(16)H(12)BrFO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment. The 4-fluoro-phenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 16.17 (5)°. The crystal structure exhibits an inter-molecular C-H⋯O hydrogen bond and a Br⋯O halogen inter-action [3.112 (2) Å].

Related literature

For the crystal structures of similar 2-(4-fluoro­phen­yl)-5-halo-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ▶,b ▶, 2010 ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For a review of halogen inter­actions, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H12BrFO2S

M = 367.23

Triclinic,

a = 7.5313 (6) Å

b = 9.8089 (7) Å

c = 10.9117 (8) Å

α = 106.567 (1)°

β = 92.634 (1)°

γ = 109.526 (1)°

V = 719.23 (9) Å3

Z = 2

Mo Kα radiation

μ = 3.01 mm−1

T = 173 K

0.60 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.586, T max = 0.746

6248 measured reflections

3083 independent reflections

2802 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.060

S = 1.05

3083 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.39 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/S160053680905418X/kp2245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905418X/kp2245Isup2.hkl

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

C16H12BrFO2S	Z = 2
Mr = 367.23	F(000) = 368
Triclinic, P1	Dx = 1.696 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5313 (6) Å	Cell parameters from 4231 reflections
b = 9.8089 (7) Å	θ = 2.3–27.4°
c = 10.9117 (8) Å	µ = 3.01 mm−1
α = 106.567 (1)°	T = 173 K
β = 92.634 (1)°	Block, colourless
γ = 109.526 (1)°	0.60 × 0.40 × 0.20 mm
V = 719.23 (9) Å3

Bruker SMART APEXII CCD diffractometer	3083 independent reflections
Radiation source: Rotating Anode	2802 reflections with I > 2σ(I)
HELIOS	Rint = 0.016
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.586, Tmax = 0.746	l = −13→13
6248 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)] = 0.023	Hydrogen site location: difference Fourier map
wR(F2) = 0.060	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0302P)2 + 0.3573P] where P = (Fo2 + 2Fc2)/3
3083 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.39 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	0.56892 (3)	0.75819 (2)	1.066631 (17)	0.02668 (7)
S	0.18420 (7)	0.22498 (5)	0.55788 (4)	0.02381 (11)
O1	0.31077 (18)	0.62985 (14)	0.50645 (12)	0.0214 (3)
O2	0.3359 (2)	0.21723 (16)	0.64548 (14)	0.0320 (3)
F	−0.0757 (2)	0.21942 (17)	−0.05951 (11)	0.0476 (4)
C1	0.2455 (3)	0.4180 (2)	0.56565 (17)	0.0207 (4)
C2	0.3406 (3)	0.5483 (2)	0.67945 (17)	0.0197 (3)
C3	0.3970 (3)	0.5713 (2)	0.81000 (17)	0.0217 (4)
H3	0.3726	0.4901	0.8427	0.026*
C4	0.4906 (3)	0.7202 (2)	0.88760 (17)	0.0216 (4)
C5	0.5318 (3)	0.8455 (2)	0.84171 (18)	0.0217 (4)
H5	0.5973	0.9434	0.8985	0.026*
C6	0.4760 (3)	0.8255 (2)	0.71248 (18)	0.0207 (4)
C7	0.3798 (2)	0.6748 (2)	0.63653 (17)	0.0193 (3)
C8	0.2316 (2)	0.4724 (2)	0.46474 (18)	0.0203 (4)
C9	0.1517 (3)	0.4038 (2)	0.32705 (17)	0.0215 (4)
C10	0.0209 (3)	0.2541 (2)	0.27673 (19)	0.0283 (4)
H10	−0.0167	0.1961	0.3316	0.034*
C11	−0.0534 (3)	0.1909 (3)	0.1460 (2)	0.0332 (5)
H11	−0.1376	0.0903	0.1121	0.040*
C12	0.0004 (3)	0.2802 (3)	0.06824 (19)	0.0318 (5)
C13	0.1276 (3)	0.4285 (3)	0.11316 (19)	0.0298 (4)
H13	0.1607	0.4860	0.0575	0.036*
C14	0.2051 (3)	0.4901 (2)	0.24326 (19)	0.0252 (4)
H14	0.2933	0.5895	0.2752	0.030*
C15	0.5111 (3)	0.9548 (2)	0.65832 (19)	0.0268 (4)
H15A	0.5531	0.9286	0.5760	0.040*
H15B	0.6076	1.0448	0.7168	0.040*
H15C	0.3952	0.9737	0.6475	0.040*
C16	−0.0164 (3)	0.2099 (3)	0.6426 (2)	0.0351 (5)
H16A	−0.0639	0.1111	0.6538	0.053*
H16B	−0.1150	0.2230	0.5936	0.053*
H16C	0.0222	0.2874	0.7258	0.053*

	U11	U22	U33	U12	U13	U23
Br	0.03804 (12)	0.02214 (11)	0.01767 (10)	0.01046 (8)	−0.00056 (7)	0.00439 (7)
S	0.0331 (3)	0.0152 (2)	0.0220 (2)	0.00897 (19)	0.00200 (19)	0.00445 (17)
O1	0.0269 (7)	0.0172 (6)	0.0193 (6)	0.0071 (5)	0.0009 (5)	0.0062 (5)
O2	0.0397 (8)	0.0274 (8)	0.0342 (8)	0.0167 (7)	0.0012 (6)	0.0128 (6)
F	0.0504 (8)	0.0559 (9)	0.0194 (6)	0.0055 (7)	−0.0086 (6)	0.0053 (6)
C1	0.0239 (9)	0.0164 (8)	0.0205 (9)	0.0066 (7)	0.0025 (7)	0.0052 (7)
C2	0.0223 (8)	0.0170 (8)	0.0208 (9)	0.0087 (7)	0.0039 (7)	0.0055 (7)
C3	0.0282 (9)	0.0175 (9)	0.0211 (9)	0.0095 (7)	0.0039 (7)	0.0075 (7)
C4	0.0260 (9)	0.0226 (9)	0.0174 (8)	0.0112 (7)	0.0019 (7)	0.0058 (7)
C5	0.0232 (9)	0.0159 (9)	0.0232 (9)	0.0071 (7)	0.0020 (7)	0.0026 (7)
C6	0.0222 (9)	0.0170 (9)	0.0239 (9)	0.0083 (7)	0.0051 (7)	0.0065 (7)
C7	0.0211 (8)	0.0186 (9)	0.0186 (8)	0.0076 (7)	0.0015 (7)	0.0062 (7)
C8	0.0200 (8)	0.0173 (9)	0.0221 (9)	0.0063 (7)	0.0034 (7)	0.0046 (7)
C9	0.0203 (8)	0.0242 (9)	0.0202 (9)	0.0095 (7)	0.0020 (7)	0.0059 (7)
C10	0.0276 (10)	0.0276 (10)	0.0253 (10)	0.0051 (8)	0.0010 (8)	0.0083 (8)
C11	0.0282 (10)	0.0311 (11)	0.0287 (11)	0.0026 (9)	−0.0032 (8)	0.0033 (9)
C12	0.0290 (10)	0.0415 (12)	0.0187 (9)	0.0108 (9)	−0.0018 (8)	0.0037 (9)
C13	0.0310 (10)	0.0368 (12)	0.0233 (10)	0.0117 (9)	0.0031 (8)	0.0130 (9)
C14	0.0259 (9)	0.0247 (10)	0.0242 (9)	0.0093 (8)	0.0022 (8)	0.0070 (8)
C15	0.0364 (11)	0.0192 (9)	0.0261 (10)	0.0102 (8)	0.0063 (8)	0.0087 (8)
C16	0.0333 (11)	0.0280 (11)	0.0443 (13)	0.0068 (9)	0.0101 (10)	0.0164 (10)

Br—C4	1.907 (2)	C6—C15	1.497 (3)
Br—O2i	3.112 (2)	C8—C9	1.463 (2)
S—O2	1.491 (2)	C9—C10	1.397 (3)
S—C1	1.768 (2)	C9—C14	1.401 (3)
S—C16	1.794 (2)	C10—C11	1.386 (3)
O1—C7	1.379 (2)	C10—H10	0.9300
O1—C8	1.381 (2)	C11—C12	1.368 (3)
F—C12	1.360 (2)	C11—H11	0.9300
C1—C8	1.368 (3)	C12—C13	1.375 (3)
C1—C2	1.445 (2)	C13—C14	1.386 (3)
C2—C7	1.394 (2)	C13—H13	0.9300
C2—C3	1.399 (2)	C14—H14	0.9300
C3—C4	1.378 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.403 (3)	C15—H15C	0.9600
C5—C6	1.391 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.389 (2)	C16—H16C	0.9600
C4—Br—O2i	173.44 (7)	C10—C9—C8	121.62 (17)
O2—S—C1	107.33 (9)	C14—C9—C8	119.58 (17)
O2—S—C16	105.95 (10)	C11—C10—C9	120.85 (19)
C1—S—C16	97.80 (9)	C11—C10—H10	119.6
C7—O1—C8	106.74 (13)	C9—C10—H10	119.6
C8—C1—C2	107.32 (16)	C12—C11—C10	118.3 (2)
C8—C1—S	127.08 (14)	C12—C11—H11	120.8
C2—C1—S	125.27 (14)	C10—C11—H11	120.8
C7—C2—C3	118.96 (16)	F—C12—C11	118.39 (19)
C7—C2—C1	105.04 (15)	F—C12—C13	118.55 (19)
C3—C2—C1	136.00 (17)	C11—C12—C13	123.06 (19)
C4—C3—C2	116.62 (16)	C12—C13—C14	118.48 (19)
C4—C3—H3	121.7	C12—C13—H13	120.8
C2—C3—H3	121.7	C14—C13—H13	120.8
C3—C4—C5	123.42 (17)	C13—C14—C9	120.46 (18)
C3—C4—Br	118.40 (14)	C13—C14—H14	119.8
C5—C4—Br	118.17 (14)	C9—C14—H14	119.8
C6—C5—C4	120.97 (17)	C6—C15—H15A	109.5
C6—C5—H5	119.5	C6—C15—H15B	109.5
C4—C5—H5	119.5	H15A—C15—H15B	109.5
C7—C6—C5	114.57 (16)	C6—C15—H15C	109.5
C7—C6—C15	121.86 (17)	H15A—C15—H15C	109.5
C5—C6—C15	123.54 (17)	H15B—C15—H15C	109.5
O1—C7—C6	124.01 (16)	S—C16—H16A	109.5
O1—C7—C2	110.54 (15)	S—C16—H16B	109.5
C6—C7—C2	125.44 (17)	H16A—C16—H16B	109.5
C1—C8—O1	110.33 (16)	S—C16—H16C	109.5
C1—C8—C9	135.27 (17)	H16A—C16—H16C	109.5
O1—C8—C9	114.40 (15)	H16B—C16—H16C	109.5
C10—C9—C14	118.79 (17)
O2—S—C1—C8	138.31 (17)	C1—C2—C7—O1	1.57 (19)
C16—S—C1—C8	−112.23 (18)	C3—C2—C7—C6	1.6 (3)
O2—S—C1—C2	−34.18 (18)	C1—C2—C7—C6	−177.92 (17)
C16—S—C1—C2	75.29 (18)	C2—C1—C8—O1	−0.4 (2)
C8—C1—C2—C7	−0.7 (2)	S—C1—C8—O1	−173.93 (13)
S—C1—C2—C7	172.99 (14)	C2—C1—C8—C9	−179.25 (19)
C8—C1—C2—C3	179.9 (2)	S—C1—C8—C9	7.2 (3)
S—C1—C2—C3	−6.4 (3)	C7—O1—C8—C1	1.32 (19)
C7—C2—C3—C4	−0.6 (3)	C7—O1—C8—C9	−179.53 (14)
C1—C2—C3—C4	178.7 (2)	C1—C8—C9—C10	17.4 (3)
C2—C3—C4—C5	−0.7 (3)	O1—C8—C9—C10	−161.47 (17)
C2—C3—C4—Br	179.49 (13)	C1—C8—C9—C14	−163.3 (2)
C3—C4—C5—C6	1.1 (3)	O1—C8—C9—C14	17.8 (2)
Br—C4—C5—C6	−179.08 (14)	C14—C9—C10—C11	0.7 (3)
C4—C5—C6—C7	−0.2 (3)	C8—C9—C10—C11	180.00 (18)
C4—C5—C6—C15	178.35 (17)	C9—C10—C11—C12	−1.8 (3)
C8—O1—C7—C6	177.69 (17)	C10—C11—C12—F	−178.57 (19)
C8—O1—C7—C2	−1.81 (19)	C10—C11—C12—C13	1.4 (3)
C5—C6—C7—O1	179.43 (16)	F—C12—C13—C14	−179.89 (18)
C15—C6—C7—O1	0.9 (3)	C11—C12—C13—C14	0.1 (3)
C5—C6—C7—C2	−1.1 (3)	C12—C13—C14—C9	−1.3 (3)
C15—C6—C7—C2	−179.68 (17)	C10—C9—C14—C13	0.8 (3)
C3—C2—C7—O1	−178.94 (15)	C8—C9—C14—C13	−178.44 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2ii	0.96	2.58	3.294 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O2i	0.96	2.58	3.294 (2)	131

Symmetry code: (i) .