5-Chloro-3-(4-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

In the title compound, C(15)H(10)ClFO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 75.83 (5)° with the plane of the benzofuran fragment. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers, which are further linked via an aromatic π-π inter-action between the benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.510 (2) Å].

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 the structures of related 3-(4-fluoro­phenyl­sulfon­yl)-5-halogeno-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C15H10ClFO3S

M = 324.74

Triclinic,

a = 7.341 (2) Å

b = 9.138 (2) Å

c = 11.347 (3) Å

α = 71.161 (12)°

β = 79.177 (11)°

γ = 69.108 (10)°

V = 670.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 173 K

0.32 × 0.32 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.673, T max = 0.746

11617 measured reflections

3098 independent reflections

2847 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.103

S = 1.08

3098 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.41 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/S1600536810032502/fk2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032502/fk2023Isup2.hkl

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

C15H10ClFO3S	Z = 2
Mr = 324.74	F(000) = 332
Triclinic, P1	Dx = 1.608 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.341 (2) Å	Cell parameters from 8342 reflections
b = 9.138 (2) Å	θ = 2.5–27.7°
c = 11.347 (3) Å	µ = 0.46 mm−1
α = 71.161 (12)°	T = 173 K
β = 79.177 (11)°	Block, colourless
γ = 69.108 (10)°	0.32 × 0.32 × 0.24 mm
V = 670.8 (3) Å3

Bruker SMART APEXII CCD diffractometer	3098 independent reflections
Radiation source: rotating anode	2847 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 = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.673, Tmax = 0.746	l = −14→14
11617 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2203P] where P = (Fo2 + 2Fc2)/3
3098 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.41 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
Cl	0.24730 (7)	0.91535 (6)	0.18345 (4)	0.04478 (15)
S	0.53086 (5)	0.60366 (4)	0.70560 (3)	0.02358 (12)
O1	0.22044 (16)	1.06562 (13)	0.64622 (10)	0.0287 (2)
O2	0.64062 (16)	0.58741 (14)	0.80400 (10)	0.0305 (3)
O3	0.63148 (17)	0.54999 (13)	0.59840 (10)	0.0316 (3)
C1	0.3925 (2)	0.80676 (17)	0.65127 (13)	0.0239 (3)
C2	0.3246 (2)	0.88838 (17)	0.52755 (13)	0.0233 (3)
C3	0.3365 (2)	0.84457 (19)	0.41916 (14)	0.0269 (3)
H3	0.4057	0.7394	0.4135	0.032*
C4	0.2404 (2)	0.9649 (2)	0.32022 (14)	0.0295 (3)
C5	0.1371 (2)	1.1238 (2)	0.32493 (15)	0.0321 (3)
H5	0.0756	1.2006	0.2557	0.038*
C6	0.1260 (2)	1.16749 (19)	0.43212 (16)	0.0306 (3)
H6	0.0585	1.2731	0.4374	0.037*
C7	0.2195 (2)	1.04713 (18)	0.53112 (14)	0.0252 (3)
C8	0.3252 (2)	0.91825 (18)	0.71784 (14)	0.0266 (3)
C9	0.3365 (3)	0.9110 (2)	0.84855 (15)	0.0357 (4)
H9A	0.4135	0.8034	0.8914	0.053*
H9B	0.2071	0.9365	0.8898	0.053*
H9C	0.3963	0.9886	0.8492	0.053*
C10	0.3594 (2)	0.50045 (17)	0.77249 (13)	0.0239 (3)
C11	0.2586 (2)	0.46848 (18)	0.69636 (14)	0.0278 (3)
H11	0.2814	0.5015	0.6099	0.033*
C12	0.1243 (2)	0.3871 (2)	0.75089 (17)	0.0338 (4)
H12	0.0533	0.3659	0.7022	0.041*
C13	0.0986 (3)	0.3385 (2)	0.87841 (17)	0.0355 (4)
C14	0.1979 (3)	0.3677 (2)	0.95508 (16)	0.0395 (4)
H14	0.1769	0.3318	1.0415	0.047*
C15	0.3287 (3)	0.4512 (2)	0.90095 (15)	0.0331 (3)
H15	0.3963	0.4745	0.9505	0.040*
F	−0.03024 (18)	0.25795 (15)	0.93220 (12)	0.0533 (3)

	U11	U22	U33	U12	U13	U23
Cl	0.0493 (3)	0.0579 (3)	0.0263 (2)	−0.0134 (2)	−0.01042 (18)	−0.01054 (19)
S	0.02279 (19)	0.02453 (19)	0.02076 (19)	−0.00504 (14)	−0.00356 (14)	−0.00462 (13)
O1	0.0298 (6)	0.0254 (5)	0.0308 (6)	−0.0077 (4)	−0.0021 (4)	−0.0093 (4)
O2	0.0275 (5)	0.0352 (6)	0.0283 (6)	−0.0104 (5)	−0.0088 (4)	−0.0041 (5)
O3	0.0311 (6)	0.0313 (6)	0.0261 (5)	−0.0037 (5)	0.0011 (4)	−0.0088 (4)
C1	0.0231 (7)	0.0255 (7)	0.0221 (7)	−0.0078 (5)	−0.0023 (5)	−0.0047 (5)
C2	0.0197 (6)	0.0244 (7)	0.0236 (7)	−0.0080 (5)	−0.0014 (5)	−0.0030 (5)
C3	0.0251 (7)	0.0292 (7)	0.0239 (7)	−0.0071 (6)	−0.0021 (6)	−0.0059 (6)
C4	0.0268 (7)	0.0377 (8)	0.0225 (7)	−0.0129 (6)	−0.0023 (6)	−0.0036 (6)
C5	0.0255 (7)	0.0339 (8)	0.0297 (8)	−0.0105 (6)	−0.0060 (6)	0.0038 (6)
C6	0.0254 (7)	0.0234 (7)	0.0372 (8)	−0.0072 (6)	−0.0028 (6)	−0.0011 (6)
C7	0.0221 (7)	0.0257 (7)	0.0276 (7)	−0.0100 (6)	−0.0005 (5)	−0.0053 (6)
C8	0.0240 (7)	0.0278 (7)	0.0280 (7)	−0.0095 (6)	−0.0013 (6)	−0.0070 (6)
C9	0.0400 (9)	0.0395 (9)	0.0296 (8)	−0.0107 (7)	−0.0023 (7)	−0.0150 (7)
C10	0.0254 (7)	0.0210 (6)	0.0233 (7)	−0.0046 (5)	−0.0044 (5)	−0.0053 (5)
C11	0.0281 (7)	0.0280 (7)	0.0269 (7)	−0.0040 (6)	−0.0053 (6)	−0.0108 (6)
C12	0.0331 (8)	0.0308 (8)	0.0426 (9)	−0.0080 (6)	−0.0100 (7)	−0.0156 (7)
C13	0.0322 (8)	0.0283 (8)	0.0461 (10)	−0.0143 (7)	−0.0036 (7)	−0.0050 (7)
C14	0.0460 (10)	0.0450 (10)	0.0271 (8)	−0.0225 (8)	−0.0039 (7)	−0.0002 (7)
C15	0.0391 (9)	0.0396 (9)	0.0246 (7)	−0.0186 (7)	−0.0068 (6)	−0.0052 (6)
F	0.0511 (7)	0.0503 (7)	0.0638 (8)	−0.0340 (6)	−0.0040 (6)	−0.0032 (6)

Cl—C4	1.7388 (17)	C6—H6	0.9300
S—O3	1.4336 (11)	C8—C9	1.480 (2)
S—O2	1.4365 (11)	C9—H9A	0.9600
S—C1	1.7344 (15)	C9—H9B	0.9600
S—C10	1.7534 (16)	C9—H9C	0.9600
O1—C8	1.3619 (18)	C10—C15	1.380 (2)
O1—C7	1.3716 (19)	C10—C11	1.392 (2)
C1—C8	1.360 (2)	C11—C12	1.380 (2)
C1—C2	1.448 (2)	C11—H11	0.9300
C2—C7	1.389 (2)	C12—C13	1.367 (3)
C2—C3	1.390 (2)	C12—H12	0.9300
C3—C4	1.383 (2)	C13—F	1.341 (2)
C3—H3	0.9300	C13—C14	1.373 (3)
C4—C5	1.392 (2)	C14—C15	1.371 (2)
C5—C6	1.378 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.377 (2)
O3—S—O2	119.62 (7)	C1—C8—O1	110.49 (13)
O3—S—C1	107.05 (7)	C1—C8—C9	134.07 (15)
O2—S—C1	108.80 (7)	O1—C8—C9	115.40 (13)
O3—S—C10	107.97 (7)	C8—C9—H9A	109.5
O2—S—C10	107.47 (7)	C8—C9—H9B	109.5
C1—S—C10	105.01 (7)	H9A—C9—H9B	109.5
C8—O1—C7	107.07 (11)	C8—C9—H9C	109.5
C8—C1—C2	107.35 (13)	H9A—C9—H9C	109.5
C8—C1—S	126.21 (12)	H9B—C9—H9C	109.5
C2—C1—S	126.43 (11)	C15—C10—C11	121.27 (15)
C7—C2—C3	119.30 (14)	C15—C10—S	118.69 (12)
C7—C2—C1	104.34 (13)	C11—C10—S	120.04 (12)
C3—C2—C1	136.33 (14)	C12—C11—C10	119.11 (15)
C4—C3—C2	116.80 (14)	C12—C11—H11	120.4
C4—C3—H3	121.6	C10—C11—H11	120.4
C2—C3—H3	121.6	C13—C12—C11	118.22 (15)
C3—C4—C5	123.19 (15)	C13—C12—H12	120.9
C3—C4—Cl	118.60 (13)	C11—C12—H12	120.9
C5—C4—Cl	118.21 (12)	F—C13—C12	118.62 (16)
C6—C5—C4	120.04 (15)	F—C13—C14	117.88 (16)
C6—C5—H5	120.0	C12—C13—C14	123.50 (16)
C4—C5—H5	120.0	C15—C14—C13	118.32 (16)
C7—C6—C5	116.73 (14)	C15—C14—H14	120.8
C7—C6—H6	121.6	C13—C14—H14	120.8
C5—C6—H6	121.6	C14—C15—C10	119.55 (15)
O1—C7—C6	125.32 (14)	C14—C15—H15	120.2
O1—C7—C2	110.74 (13)	C10—C15—H15	120.2
C6—C7—C2	123.93 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3i	0.93	2.48	3.335 (2)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O3i	0.93	2.48	3.335 (2)	153

Symmetry code: (i) .