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

In the title compound, C(15)H(10)ClFO(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, making a dihedral angle of 25.99 (4)°. The crystal structure is stabilized by a non-classical inter-molecular C-H⋯O hydrogen bond and a Cl⋯O halogen bond [3.244 (1) Å].

Related literature

For the crystal structures of similar 2-(4-halophen­yl)-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009 ▶). For the biological 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 bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H10ClFO2S

M = 308.74

Triclinic,

a = 7.8484 (2) Å

b = 8.3176 (2) Å

c = 10.7353 (2) Å

α = 95.637 (1)°

β = 91.975 (1)°

γ = 112.372 (1)°

V = 642.95 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 151 K

0.38 × 0.37 × 0.31 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.843, T max = 0.868

11361 measured reflections

2949 independent reflections

2799 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.06

2949 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.37 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/S1600536809039749/zq2011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039749/zq2011Isup2.hkl

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

C15H10ClFO2S	Z = 2
Mr = 308.74	F(000) = 316
Triclinic, P1	Dx = 1.595 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8484 (2) Å	Cell parameters from 8966 reflections
b = 8.3176 (2) Å	θ = 2.7–27.6°
c = 10.7353 (2) Å	µ = 0.47 mm−1
α = 95.637 (1)°	T = 151 K
β = 91.975 (1)°	Block, colourless
γ = 112.372 (1)°	0.38 × 0.37 × 0.31 mm
V = 642.95 (3) Å3

Bruker SMART APEXII CCD diffractometer	2949 independent reflections
Radiation source: Rotating Anode	2799 reflections with I > 2σ(I)
HELIOS	Rint = 0.023
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.843, Tmax = 0.868	l = −12→13
11361 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.043P)2 + 0.2884P] where P = (Fo2 + 2Fc2)/3
2949 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.36 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
S	0.18454 (4)	0.20468 (4)	0.59366 (3)	0.01959 (10)
Cl	0.58536 (5)	0.78256 (4)	1.01739 (3)	0.02696 (10)
F	−0.06796 (13)	0.22320 (12)	−0.01528 (8)	0.0373 (2)
O1	0.33377 (12)	0.68122 (11)	0.48927 (8)	0.01984 (19)
O2	0.32352 (14)	0.18415 (13)	0.68194 (10)	0.0292 (2)
C1	0.25897 (17)	0.42982 (16)	0.57709 (11)	0.0182 (2)
C2	0.36053 (17)	0.57316 (16)	0.67248 (12)	0.0181 (2)
C3	0.41614 (17)	0.58856 (17)	0.79952 (11)	0.0199 (2)
H3	0.3880	0.4888	0.8433	0.024*
C4	0.51439 (18)	0.75637 (17)	0.85853 (12)	0.0210 (3)
C5	0.55869 (18)	0.90590 (17)	0.79684 (12)	0.0224 (3)
H5	0.6274	1.0181	0.8415	0.027*
C6	0.50280 (18)	0.89127 (17)	0.67078 (12)	0.0219 (3)
H6	0.5305	0.9910	0.6270	0.026*
C7	0.40473 (17)	0.72374 (16)	0.61254 (11)	0.0184 (2)
C8	0.24675 (17)	0.50143 (16)	0.46942 (12)	0.0184 (2)
C9	0.16187 (17)	0.42847 (17)	0.34289 (11)	0.0185 (2)
C10	0.01060 (18)	0.26868 (18)	0.32117 (12)	0.0221 (3)
H10	−0.0400	0.2079	0.3902	0.026*
C11	−0.06688 (19)	0.19735 (18)	0.20057 (13)	0.0247 (3)
H11	−0.1679	0.0873	0.1854	0.030*
C12	0.00739 (19)	0.29133 (19)	0.10332 (12)	0.0244 (3)
C13	0.15404 (19)	0.45109 (18)	0.12037 (12)	0.0242 (3)
H13	0.2003	0.5126	0.0508	0.029*
C14	0.23250 (18)	0.52006 (17)	0.24092 (12)	0.0209 (3)
H14	0.3344	0.6296	0.2547	0.025*
C15	−0.01001 (19)	0.18735 (19)	0.68205 (14)	0.0275 (3)
H15A	−0.0655	0.0691	0.7067	0.041*
H15B	−0.1017	0.2104	0.6304	0.041*
H15C	0.0307	0.2731	0.7574	0.041*

	U11	U22	U33	U12	U13	U23
S	0.02235 (17)	0.01534 (16)	0.02005 (16)	0.00628 (12)	0.00176 (12)	0.00143 (11)
Cl	0.03404 (19)	0.02564 (18)	0.01697 (16)	0.00867 (14)	−0.00482 (12)	−0.00284 (12)
F	0.0440 (5)	0.0401 (5)	0.0167 (4)	0.0061 (4)	−0.0093 (4)	−0.0020 (4)
O1	0.0235 (4)	0.0174 (4)	0.0166 (4)	0.0059 (4)	−0.0014 (3)	0.0018 (3)
O2	0.0262 (5)	0.0258 (5)	0.0373 (6)	0.0108 (4)	−0.0019 (4)	0.0103 (4)
C1	0.0202 (6)	0.0162 (6)	0.0170 (5)	0.0060 (5)	0.0003 (4)	0.0007 (4)
C2	0.0187 (6)	0.0161 (6)	0.0190 (6)	0.0067 (5)	0.0007 (4)	0.0008 (4)
C3	0.0230 (6)	0.0189 (6)	0.0174 (6)	0.0081 (5)	−0.0001 (5)	0.0012 (5)
C4	0.0219 (6)	0.0232 (6)	0.0174 (6)	0.0094 (5)	−0.0014 (5)	−0.0012 (5)
C5	0.0227 (6)	0.0184 (6)	0.0227 (6)	0.0057 (5)	−0.0009 (5)	−0.0024 (5)
C6	0.0235 (6)	0.0171 (6)	0.0234 (6)	0.0060 (5)	0.0007 (5)	0.0026 (5)
C7	0.0191 (6)	0.0197 (6)	0.0160 (5)	0.0076 (5)	−0.0005 (4)	0.0013 (4)
C8	0.0179 (6)	0.0169 (6)	0.0189 (6)	0.0054 (5)	0.0011 (4)	0.0009 (4)
C9	0.0194 (6)	0.0209 (6)	0.0161 (5)	0.0093 (5)	−0.0002 (4)	0.0013 (4)
C10	0.0216 (6)	0.0240 (6)	0.0187 (6)	0.0064 (5)	0.0002 (5)	0.0041 (5)
C11	0.0222 (6)	0.0243 (6)	0.0231 (6)	0.0050 (5)	−0.0029 (5)	0.0006 (5)
C12	0.0272 (7)	0.0296 (7)	0.0150 (6)	0.0111 (5)	−0.0048 (5)	−0.0018 (5)
C13	0.0275 (7)	0.0281 (7)	0.0175 (6)	0.0108 (5)	0.0020 (5)	0.0051 (5)
C14	0.0214 (6)	0.0207 (6)	0.0199 (6)	0.0073 (5)	0.0010 (5)	0.0028 (5)
C15	0.0248 (7)	0.0276 (7)	0.0317 (7)	0.0100 (5)	0.0082 (5)	0.0087 (6)

S—O2	1.490 (1)	C6—C7	1.380 (2)
S—C1	1.766 (1)	C6—H6	0.9500
S—C15	1.792 (1)	C8—C9	1.458 (2)
Cl—C4	1.742 (1)	C9—C10	1.396 (2)
Cl—O2i	3.244 (1)	C9—C14	1.404 (2)
F—C12	1.358 (1)	C10—C11	1.385 (2)
O1—C7	1.376 (2)	C10—H10	0.9500
O1—C8	1.378 (2)	C11—C12	1.377 (2)
C1—C8	1.368 (2)	C11—H11	0.9500
C1—C2	1.444 (2)	C12—C13	1.377 (2)
C2—C7	1.395 (2)	C13—C14	1.383 (2)
C2—C3	1.396 (2)	C13—H13	0.9500
C3—C4	1.385 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.398 (2)	C15—H15B	0.9800
C5—C6	1.387 (2)	C15—H15C	0.9800
C5—H5	0.9500
O2—S—C1	107.25 (6)	C1—C8—C9	133.83 (12)
O2—S—C15	106.04 (7)	O1—C8—C9	115.54 (11)
C4—Cl—O2i	174.59 (5)	C10—C9—C14	119.21 (11)
C1—S—C15	97.55 (6)	C10—C9—C8	121.09 (11)
C7—O1—C8	106.71 (9)	C14—C9—C8	119.70 (11)
C8—C1—C2	106.97 (11)	C11—C10—C9	121.01 (12)
C8—C1—S	126.78 (10)	C11—C10—H10	119.5
C2—C1—S	126.01 (9)	C9—C10—H10	119.5
C7—C2—C3	119.43 (11)	C12—C11—C10	117.77 (12)
C7—C2—C1	105.20 (11)	C12—C11—H11	121.1
C3—C2—C1	135.37 (12)	C10—C11—H11	121.1
C4—C3—C2	116.72 (12)	F—C12—C11	118.33 (12)
C4—C3—H3	121.6	F—C12—C13	118.37 (12)
C2—C3—H3	121.6	C11—C12—C13	123.30 (12)
C3—C4—C5	123.13 (12)	C12—C13—C14	118.55 (12)
C3—C4—Cl	118.45 (10)	C12—C13—H13	120.7
C5—C4—Cl	118.42 (10)	C14—C13—H13	120.7
C6—C5—C4	120.34 (12)	C13—C14—C9	120.13 (12)
C6—C5—H5	119.8	C13—C14—H14	119.9
C4—C5—H5	119.8	C9—C14—H14	119.9
C7—C6—C5	116.26 (12)	S—C15—H15A	109.5
C7—C6—H6	121.9	S—C15—H15B	109.5
C5—C6—H6	121.9	H15A—C15—H15B	109.5
O1—C7—C6	125.40 (11)	S—C15—H15C	109.5
O1—C7—C2	110.47 (11)	H15A—C15—H15C	109.5
C6—C7—C2	124.12 (12)	H15B—C15—H15C	109.5
C1—C8—O1	110.63 (11)
O2—S—C1—C8	141.61 (12)	C1—C2—C7—C6	−179.94 (12)
C15—S—C1—C8	−108.94 (12)	C2—C1—C8—O1	0.03 (14)
O2—S—C1—C2	−31.99 (12)	S—C1—C8—O1	−174.55 (9)
C15—S—C1—C2	77.46 (12)	C2—C1—C8—C9	−179.35 (13)
C8—C1—C2—C7	−0.78 (13)	S—C1—C8—C9	6.1 (2)
S—C1—C2—C7	173.85 (9)	C7—O1—C8—C1	0.75 (13)
C8—C1—C2—C3	178.83 (14)	C7—O1—C8—C9	−179.75 (10)
S—C1—C2—C3	−6.5 (2)	C1—C8—C9—C10	26.5 (2)
C7—C2—C3—C4	−0.26 (18)	O1—C8—C9—C10	−152.84 (12)
C1—C2—C3—C4	−179.83 (13)	C1—C8—C9—C14	−153.67 (14)
C2—C3—C4—C5	−0.19 (19)	O1—C8—C9—C14	26.98 (16)
C2—C3—C4—Cl	179.52 (9)	C14—C9—C10—C11	1.87 (19)
C3—C4—C5—C6	0.6 (2)	C8—C9—C10—C11	−178.31 (12)
Cl—C4—C5—C6	−179.15 (10)	C9—C10—C11—C12	−1.6 (2)
C4—C5—C6—C7	−0.44 (19)	C10—C11—C12—F	−179.67 (12)
C8—O1—C7—C6	179.96 (12)	C10—C11—C12—C13	0.2 (2)
C8—O1—C7—C2	−1.27 (13)	F—C12—C13—C14	−179.31 (12)
C5—C6—C7—O1	178.59 (11)	C11—C12—C13—C14	0.8 (2)
C5—C6—C7—C2	−0.01 (19)	C12—C13—C14—C9	−0.49 (19)
C3—C2—C7—O1	−178.41 (11)	C10—C9—C14—C13	−0.81 (19)
C1—C2—C7—O1	1.27 (13)	C8—C9—C14—C13	179.37 (12)
C3—C2—C7—C6	0.37 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ii	0.95	2.56	3.4287 (16)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.95	2.56	3.4287 (16)	152

Symmetry code: (i) .