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

In the title compound, C(20)H(12)ClFO(2)S, the O atom and the phenyl ring of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the phenyl ring is almost perpendicular to this plane [82.44 (5)°]. The 4-fluoro-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 20.83 (6)°.

Related literature

For the biological 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 5-halo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009 ▶).

Experimental

Crystal data

C20H12ClFO2S

M = 370.81

Triclinic,

a = 8.2551 (2) Å

b = 9.4707 (3) Å

c = 11.4914 (3) Å

α = 71.403 (2)°

β = 81.707 (2)°

γ = 71.909 (2)°

V = 808.39 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 173 K

0.17 × 0.15 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.935, T max = 0.978

14335 measured reflections

3722 independent reflections

2943 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.04

3722 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 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/S1600536811002686/rn2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002686/rn2082Isup2.hkl

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

C20H12ClFO2S	Z = 2
Mr = 370.81	F(000) = 380
Triclinic, P1	Dx = 1.523 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2551 (2) Å	Cell parameters from 5406 reflections
b = 9.4707 (3) Å	θ = 2.6–27.3°
c = 11.4914 (3) Å	µ = 0.39 mm−1
α = 71.403 (2)°	T = 173 K
β = 81.707 (2)°	Block, colourless
γ = 71.909 (2)°	0.17 × 0.15 × 0.06 mm
V = 808.39 (4) Å3

Bruker SMART APEXII CCD diffractometer	3722 independent reflections
Radiation source: rotating anode	2943 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 27.7°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.935, Tmax = 0.978	l = −15→14
14335 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.1974P] where P = (Fo2 + 2Fc2)/3
3722 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 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
Cl1	1.03501 (6)	0.73080 (5)	0.38102 (4)	0.04197 (14)
S1	0.62029 (5)	0.60069 (5)	0.86187 (4)	0.03045 (12)
F1	0.03640 (16)	1.10463 (14)	1.14539 (11)	0.0571 (3)
O1	0.52873 (15)	1.05149 (12)	0.68603 (10)	0.0308 (3)
O2	0.79096 (15)	0.50153 (14)	0.83462 (13)	0.0435 (3)
C1	0.6061 (2)	0.79137 (18)	0.76450 (15)	0.0268 (3)
C2	0.6984 (2)	0.82981 (18)	0.64745 (15)	0.0273 (3)
C3	0.8176 (2)	0.74611 (19)	0.57773 (15)	0.0293 (4)
H3	0.8542	0.6358	0.6037	0.035*
C4	0.8803 (2)	0.8308 (2)	0.46888 (16)	0.0314 (4)
C5	0.8269 (2)	0.9928 (2)	0.42678 (16)	0.0352 (4)
H5	0.8734	1.0459	0.3510	0.042*
C6	0.7069 (2)	1.0758 (2)	0.49497 (16)	0.0338 (4)
H6	0.6679	1.1860	0.4679	0.041*
C7	0.6461 (2)	0.99115 (18)	0.60439 (15)	0.0279 (3)
C8	0.5071 (2)	0.92768 (18)	0.78381 (15)	0.0278 (3)
C9	0.3831 (2)	0.97013 (19)	0.88009 (15)	0.0283 (4)
C10	0.2638 (2)	1.1155 (2)	0.85298 (17)	0.0378 (4)
H10	0.2632	1.1842	0.7720	0.045*
C11	0.1463 (2)	1.1617 (2)	0.94148 (18)	0.0434 (5)
H11	0.0651	1.2611	0.9227	0.052*
C12	0.1501 (2)	1.0603 (2)	1.05693 (17)	0.0388 (4)
C13	0.2645 (2)	0.9155 (2)	1.08844 (17)	0.0391 (4)
H13	0.2634	0.8479	1.1697	0.047*
C14	0.3814 (2)	0.8707 (2)	0.99897 (16)	0.0347 (4)
H14	0.4616	0.7708	1.0188	0.042*
C15	0.4679 (2)	0.56305 (17)	0.78808 (15)	0.0274 (3)
C16	0.2970 (2)	0.6120 (2)	0.82334 (17)	0.0340 (4)
H16	0.2621	0.6660	0.8837	0.041*
C17	0.1781 (2)	0.5810 (2)	0.7692 (2)	0.0449 (5)
H17	0.0602	0.6143	0.7919	0.054*
C18	0.2304 (3)	0.5017 (2)	0.6824 (2)	0.0478 (5)
H18	0.1481	0.4809	0.6452	0.057*
C19	0.4007 (3)	0.4522 (2)	0.64904 (19)	0.0470 (5)
H19	0.4355	0.3970	0.5895	0.056*
C20	0.5211 (2)	0.48253 (19)	0.70198 (17)	0.0371 (4)
H20	0.6389	0.4485	0.6794	0.045*

	U11	U22	U33	U12	U13	U23
Cl1	0.0389 (3)	0.0426 (3)	0.0377 (3)	−0.0065 (2)	0.01078 (19)	−0.0129 (2)
S1	0.0269 (2)	0.0251 (2)	0.0310 (2)	−0.00523 (17)	−0.00234 (17)	0.00144 (17)
F1	0.0572 (8)	0.0530 (7)	0.0476 (7)	−0.0058 (6)	0.0243 (6)	−0.0174 (6)
O1	0.0347 (6)	0.0239 (6)	0.0285 (6)	−0.0075 (5)	0.0045 (5)	−0.0038 (5)
O2	0.0259 (6)	0.0327 (7)	0.0566 (9)	0.0006 (5)	−0.0028 (6)	−0.0010 (6)
C1	0.0249 (8)	0.0252 (8)	0.0264 (8)	−0.0072 (6)	−0.0010 (6)	−0.0022 (6)
C2	0.0248 (8)	0.0263 (8)	0.0282 (8)	−0.0087 (7)	−0.0020 (6)	−0.0027 (7)
C3	0.0259 (8)	0.0259 (8)	0.0325 (9)	−0.0060 (7)	−0.0008 (7)	−0.0053 (7)
C4	0.0275 (8)	0.0349 (9)	0.0301 (9)	−0.0072 (7)	0.0023 (7)	−0.0101 (7)
C5	0.0367 (9)	0.0359 (9)	0.0288 (9)	−0.0132 (8)	0.0055 (7)	−0.0040 (7)
C6	0.0378 (10)	0.0268 (8)	0.0314 (9)	−0.0097 (7)	0.0020 (7)	−0.0023 (7)
C7	0.0281 (8)	0.0253 (8)	0.0279 (8)	−0.0072 (7)	0.0006 (7)	−0.0061 (7)
C8	0.0274 (8)	0.0262 (8)	0.0261 (8)	−0.0096 (7)	−0.0009 (7)	−0.0010 (6)
C9	0.0263 (8)	0.0285 (8)	0.0296 (9)	−0.0094 (7)	0.0009 (7)	−0.0074 (7)
C10	0.0354 (9)	0.0332 (9)	0.0343 (10)	−0.0046 (8)	0.0026 (8)	−0.0025 (8)
C11	0.0384 (10)	0.0351 (10)	0.0450 (11)	−0.0021 (8)	0.0072 (9)	−0.0078 (9)
C12	0.0358 (10)	0.0411 (10)	0.0389 (10)	−0.0118 (8)	0.0117 (8)	−0.0160 (8)
C13	0.0444 (11)	0.0379 (10)	0.0296 (9)	−0.0132 (8)	0.0057 (8)	−0.0045 (8)
C14	0.0364 (9)	0.0284 (9)	0.0329 (9)	−0.0055 (7)	0.0013 (7)	−0.0051 (7)
C15	0.0277 (8)	0.0194 (7)	0.0286 (8)	−0.0054 (6)	0.0018 (7)	−0.0008 (6)
C16	0.0289 (9)	0.0309 (9)	0.0382 (10)	−0.0064 (7)	0.0030 (7)	−0.0089 (8)
C17	0.0298 (9)	0.0388 (11)	0.0615 (13)	−0.0084 (8)	−0.0043 (9)	−0.0089 (10)
C18	0.0532 (13)	0.0326 (10)	0.0604 (13)	−0.0146 (9)	−0.0191 (11)	−0.0078 (9)
C19	0.0673 (14)	0.0312 (10)	0.0445 (11)	−0.0142 (10)	−0.0020 (10)	−0.0136 (9)
C20	0.0381 (10)	0.0257 (9)	0.0415 (10)	−0.0064 (8)	0.0075 (8)	−0.0084 (8)

Cl1—C4	1.7422 (17)	C9—C10	1.391 (2)
S1—O2	1.4845 (13)	C10—C11	1.379 (3)
S1—C1	1.7732 (16)	C10—H10	0.9500
S1—C15	1.7911 (17)	C11—C12	1.365 (3)
F1—C12	1.358 (2)	C11—H11	0.9500
O1—C7	1.3717 (19)	C12—C13	1.371 (3)
O1—C8	1.3788 (19)	C13—C14	1.381 (2)
C1—C8	1.363 (2)	C13—H13	0.9500
C1—C2	1.445 (2)	C14—H14	0.9500
C2—C3	1.390 (2)	C15—C20	1.379 (2)
C2—C7	1.391 (2)	C15—C16	1.385 (2)
C3—C4	1.381 (2)	C16—C17	1.381 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.396 (2)	C17—C18	1.379 (3)
C5—C6	1.378 (2)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.376 (3)
C6—C7	1.379 (2)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.380 (3)
C8—C9	1.461 (2)	C19—H19	0.9500
C9—C14	1.391 (2)	C20—H20	0.9500
O2—S1—C1	106.64 (7)	C11—C10—H10	119.4
O2—S1—C15	107.22 (8)	C9—C10—H10	119.4
C1—S1—C15	96.93 (7)	C12—C11—C10	118.01 (17)
C7—O1—C8	106.94 (12)	C12—C11—H11	121.0
C8—C1—C2	107.22 (14)	C10—C11—H11	121.0
C8—C1—S1	127.42 (13)	F1—C12—C11	118.74 (17)
C2—C1—S1	125.36 (12)	F1—C12—C13	118.13 (17)
C3—C2—C7	119.50 (15)	C11—C12—C13	123.13 (17)
C3—C2—C1	135.44 (15)	C12—C13—C14	118.27 (17)
C7—C2—C1	105.05 (14)	C12—C13—H13	120.9
C4—C3—C2	116.85 (15)	C14—C13—H13	120.9
C4—C3—H3	121.6	C13—C14—C9	120.76 (16)
C2—C3—H3	121.6	C13—C14—H14	119.6
C3—C4—C5	123.08 (16)	C9—C14—H14	119.6
C3—C4—Cl1	118.37 (13)	C20—C15—C16	121.39 (17)
C5—C4—Cl1	118.54 (13)	C20—C15—S1	120.46 (13)
C6—C5—C4	120.11 (16)	C16—C15—S1	118.11 (13)
C6—C5—H5	119.9	C17—C16—C15	118.85 (17)
C4—C5—H5	119.9	C17—C16—H16	120.6
C5—C6—C7	116.72 (15)	C15—C16—H16	120.6
C5—C6—H6	121.6	C18—C17—C16	120.02 (19)
C7—C6—H6	121.6	C18—C17—H17	120.0
O1—C7—C6	125.76 (14)	C16—C17—H17	120.0
O1—C7—C2	110.51 (14)	C19—C18—C17	120.58 (19)
C6—C7—C2	123.72 (16)	C19—C18—H18	119.7
C1—C8—O1	110.27 (14)	C17—C18—H18	119.7
C1—C8—C9	135.02 (15)	C18—C19—C20	120.14 (19)
O1—C8—C9	114.67 (14)	C18—C19—H19	119.9
C14—C9—C10	118.60 (16)	C20—C19—H19	119.9
C14—C9—C8	122.21 (15)	C15—C20—C19	119.01 (18)
C10—C9—C8	119.19 (15)	C15—C20—H20	120.5
C11—C10—C9	121.23 (17)	C19—C20—H20	120.5
O2—S1—C1—C8	−154.59 (15)	C7—O1—C8—C9	−179.06 (13)
C15—S1—C1—C8	95.06 (16)	C1—C8—C9—C14	22.4 (3)
O2—S1—C1—C2	26.14 (16)	O1—C8—C9—C14	−160.06 (15)
C15—S1—C1—C2	−84.21 (15)	C1—C8—C9—C10	−158.49 (19)
C8—C1—C2—C3	179.31 (18)	O1—C8—C9—C10	19.1 (2)
S1—C1—C2—C3	−1.3 (3)	C14—C9—C10—C11	0.4 (3)
C8—C1—C2—C7	0.04 (18)	C8—C9—C10—C11	−178.78 (17)
S1—C1—C2—C7	179.44 (12)	C9—C10—C11—C12	−0.1 (3)
C7—C2—C3—C4	1.3 (2)	C10—C11—C12—F1	179.39 (17)
C1—C2—C3—C4	−177.90 (17)	C10—C11—C12—C13	−0.1 (3)
C2—C3—C4—C5	−1.2 (3)	F1—C12—C13—C14	−179.41 (16)
C2—C3—C4—Cl1	177.97 (12)	C11—C12—C13—C14	0.1 (3)
C3—C4—C5—C6	0.3 (3)	C12—C13—C14—C9	0.1 (3)
Cl1—C4—C5—C6	−178.87 (14)	C10—C9—C14—C13	−0.4 (3)
C4—C5—C6—C7	0.5 (3)	C8—C9—C14—C13	178.74 (16)
C8—O1—C7—C6	−178.57 (16)	O2—S1—C15—C20	−13.01 (16)
C8—O1—C7—C2	0.94 (18)	C1—S1—C15—C20	96.85 (14)
C5—C6—C7—O1	179.02 (16)	O2—S1—C15—C16	164.67 (12)
C5—C6—C7—C2	−0.4 (3)	C1—S1—C15—C16	−85.46 (14)
C3—C2—C7—O1	179.98 (14)	C20—C15—C16—C17	−1.0 (2)
C1—C2—C7—O1	−0.61 (18)	S1—C15—C16—C17	−178.63 (14)
C3—C2—C7—C6	−0.5 (3)	C15—C16—C17—C18	0.4 (3)
C1—C2—C7—C6	178.91 (16)	C16—C17—C18—C19	0.3 (3)
C2—C1—C8—O1	0.54 (18)	C17—C18—C19—C20	−0.4 (3)
S1—C1—C8—O1	−178.84 (11)	C16—C15—C20—C19	0.8 (3)
C2—C1—C8—C9	178.16 (17)	S1—C15—C20—C19	178.43 (14)
S1—C1—C8—C9	−1.2 (3)	C18—C19—C20—C15	−0.1 (3)
C7—O1—C8—C1	−0.91 (18)