3-(3-Chloro-phenyl-sulfin-yl)-2,4,6-trimethyl-1-benzofuran.

In the title compound, C(17)H(15)ClO(2)S, the 3-chloro-phenyl ring makes a dihedral angle of 71.46 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and a slipped π-π inter-action between the 3-chloro-phenyl rings of adjacent mol-ecules [centroid-centroid distance = 3.630 (2) Å, inter-planar distance = 3.375 (2) Å and slippage = 1.337 (2) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2010 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C17H15ClO2S

M = 318.80

Triclinic,

a = 6.7900 (2) Å

b = 8.1288 (3) Å

c = 14.6813 (5) Å

α = 76.763 (2)°

β = 84.145 (2)°

γ = 73.241 (2)°

V = 754.73 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 173 K

0.28 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.675, T max = 0.746

14017 measured reflections

3704 independent reflections

3182 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.05

3704 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.42 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 datablock(s) global, I. DOI: 10.1107/S160053681200027X/pv2502sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200027X/pv2502Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200027X/pv2502Isup3.cml

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

C17H15ClO2S	Z = 2
Mr = 318.80	F(000) = 332
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7900 (2) Å	Cell parameters from 6373 reflections
b = 8.1288 (3) Å	θ = 2.7–28.1°
c = 14.6813 (5) Å	µ = 0.39 mm−1
α = 76.763 (2)°	T = 173 K
β = 84.145 (2)°	Block, colourless
γ = 73.241 (2)°	0.28 × 0.25 × 0.21 mm
V = 754.73 (4) Å3

Bruker SMART APEXII CCD diffractometer	3704 independent reflections
Radiation source: rotating anode	3182 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.4°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.675, Tmax = 0.746	l = −19→19
14017 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.219P] where P = (Fo2 + 2Fc2)/3
3704 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.42 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	0.98398 (6)	0.23182 (6)	0.99982 (3)	0.04624 (14)
S1	0.46056 (6)	0.83926 (5)	0.83535 (3)	0.03407 (12)
O1	0.14598 (16)	0.96772 (15)	0.61039 (8)	0.0363 (3)
O2	0.65568 (19)	0.88857 (16)	0.83626 (9)	0.0443 (3)
C1	0.3829 (2)	0.8720 (2)	0.72075 (11)	0.0312 (3)
C2	0.4775 (2)	0.80409 (19)	0.63819 (10)	0.0300 (3)
C3	0.6724 (2)	0.7063 (2)	0.61075 (11)	0.0336 (3)
C4	0.6909 (2)	0.6719 (2)	0.52105 (12)	0.0368 (3)
H4	0.8208	0.6054	0.5009	0.044*
C5	0.5309 (3)	0.7288 (2)	0.45904 (11)	0.0367 (3)
C6	0.3406 (3)	0.8309 (2)	0.48513 (11)	0.0375 (3)
H6	0.2289	0.8745	0.4442	0.045*
C7	0.3229 (2)	0.8653 (2)	0.57378 (11)	0.0325 (3)
C8	0.1876 (2)	0.9692 (2)	0.69925 (11)	0.0336 (3)
C9	0.8536 (3)	0.6437 (3)	0.67277 (13)	0.0448 (4)
H9A	0.8515	0.5309	0.7141	0.067*
H9B	0.8462	0.7303	0.7106	0.067*
H9C	0.9813	0.6291	0.6340	0.067*
C10	0.5634 (3)	0.6788 (3)	0.36442 (12)	0.0464 (4)
H10A	0.5396	0.5633	0.3706	0.070*
H10B	0.7047	0.6741	0.3408	0.070*
H10C	0.4667	0.7665	0.3205	0.070*
C11	0.0176 (3)	1.0752 (2)	0.75130 (13)	0.0432 (4)
H11A	0.0667	1.0788	0.8111	0.065*
H11B	−0.0972	1.0217	0.7630	0.065*
H11C	−0.0288	1.1950	0.7141	0.065*
C12	0.5290 (2)	0.6027 (2)	0.86348 (10)	0.0302 (3)
C13	0.7090 (2)	0.5182 (2)	0.91058 (10)	0.0317 (3)
H13	0.7954	0.5830	0.9234	0.038*
C14	0.7601 (2)	0.3376 (2)	0.93850 (11)	0.0326 (3)
C15	0.6376 (2)	0.2399 (2)	0.92032 (11)	0.0339 (3)
H15	0.6762	0.1155	0.9394	0.041*
C16	0.4574 (3)	0.3280 (2)	0.87360 (11)	0.0355 (3)
H16	0.3716	0.2629	0.8606	0.043*
C17	0.4002 (2)	0.5095 (2)	0.84550 (11)	0.0339 (3)
H17	0.2753	0.5690	0.8145	0.041*

	U11	U22	U33	U12	U13	U23
Cl1	0.0373 (2)	0.0353 (2)	0.0654 (3)	−0.00594 (17)	−0.00790 (18)	−0.01169 (19)
S1	0.0379 (2)	0.0264 (2)	0.0417 (2)	−0.00941 (16)	0.00082 (15)	−0.01471 (16)
O1	0.0268 (5)	0.0343 (6)	0.0432 (6)	−0.0021 (4)	0.0024 (4)	−0.0087 (5)
O2	0.0469 (7)	0.0333 (6)	0.0612 (8)	−0.0190 (5)	−0.0072 (6)	−0.0144 (6)
C1	0.0296 (7)	0.0248 (7)	0.0394 (8)	−0.0070 (6)	0.0034 (6)	−0.0094 (6)
C2	0.0298 (7)	0.0223 (7)	0.0373 (7)	−0.0073 (6)	0.0040 (6)	−0.0072 (6)
C3	0.0305 (7)	0.0252 (7)	0.0434 (8)	−0.0060 (6)	0.0043 (6)	−0.0085 (6)
C4	0.0348 (8)	0.0281 (8)	0.0443 (8)	−0.0054 (6)	0.0103 (6)	−0.0105 (6)
C5	0.0432 (9)	0.0302 (8)	0.0367 (8)	−0.0127 (7)	0.0082 (6)	−0.0083 (6)
C6	0.0379 (8)	0.0339 (9)	0.0378 (8)	−0.0083 (7)	−0.0003 (6)	−0.0043 (6)
C7	0.0286 (7)	0.0254 (7)	0.0401 (8)	−0.0048 (6)	0.0045 (6)	−0.0061 (6)
C8	0.0307 (7)	0.0277 (8)	0.0417 (8)	−0.0075 (6)	0.0055 (6)	−0.0094 (6)
C9	0.0308 (8)	0.0460 (10)	0.0539 (10)	0.0006 (7)	0.0003 (7)	−0.0179 (8)
C10	0.0565 (11)	0.0459 (11)	0.0392 (9)	−0.0175 (9)	0.0098 (8)	−0.0144 (8)
C11	0.0331 (8)	0.0382 (9)	0.0551 (10)	−0.0038 (7)	0.0090 (7)	−0.0161 (8)
C12	0.0358 (7)	0.0257 (7)	0.0325 (7)	−0.0109 (6)	0.0039 (6)	−0.0124 (6)
C13	0.0338 (7)	0.0301 (8)	0.0365 (8)	−0.0126 (6)	0.0022 (6)	−0.0139 (6)
C14	0.0315 (7)	0.0315 (8)	0.0360 (7)	−0.0069 (6)	0.0035 (6)	−0.0137 (6)
C15	0.0429 (8)	0.0262 (8)	0.0358 (7)	−0.0111 (6)	0.0057 (6)	−0.0139 (6)
C16	0.0432 (8)	0.0341 (8)	0.0381 (8)	−0.0196 (7)	0.0034 (6)	−0.0161 (6)
C17	0.0367 (8)	0.0353 (8)	0.0348 (7)	−0.0139 (7)	−0.0002 (6)	−0.0130 (6)

Cl1—C14	1.7412 (16)	C9—H9A	0.9800
S1—O2	1.4928 (12)	C9—H9B	0.9800
S1—C1	1.7534 (16)	C9—H9C	0.9800
S1—C12	1.8009 (15)	C10—H10A	0.9800
O1—C8	1.3661 (19)	C10—H10B	0.9800
O1—C7	1.3863 (18)	C10—H10C	0.9800
C1—C8	1.360 (2)	C11—H11A	0.9800
C1—C2	1.459 (2)	C11—H11B	0.9800
C2—C7	1.389 (2)	C11—H11C	0.9800
C2—C3	1.406 (2)	C12—C13	1.384 (2)
C3—C4	1.394 (2)	C12—C17	1.389 (2)
C3—C9	1.502 (2)	C13—C14	1.380 (2)
C4—C5	1.393 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.384 (2)
C5—C6	1.390 (2)	C15—C16	1.386 (2)
C5—C10	1.513 (2)	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.386 (2)
C6—H6	0.9500	C16—H16	0.9500
C8—C11	1.486 (2)	C17—H17	0.9500
O2—S1—C1	111.41 (7)	H9A—C9—H9C	109.5
O2—S1—C12	106.01 (7)	H9B—C9—H9C	109.5
C1—S1—C12	98.39 (7)	C5—C10—H10A	109.5
C8—O1—C7	106.59 (12)	C5—C10—H10B	109.5
C8—C1—C2	107.12 (14)	H10A—C10—H10B	109.5
C8—C1—S1	118.56 (12)	C5—C10—H10C	109.5
C2—C1—S1	134.08 (12)	H10A—C10—H10C	109.5
C7—C2—C3	118.49 (14)	H10B—C10—H10C	109.5
C7—C2—C1	104.44 (13)	C8—C11—H11A	109.5
C3—C2—C1	137.02 (14)	C8—C11—H11B	109.5
C4—C3—C2	116.22 (15)	H11A—C11—H11B	109.5
C4—C3—C9	121.02 (14)	C8—C11—H11C	109.5
C2—C3—C9	122.75 (14)	H11A—C11—H11C	109.5
C5—C4—C3	124.16 (15)	H11B—C11—H11C	109.5
C5—C4—H4	117.9	C13—C12—C17	121.25 (14)
C3—C4—H4	117.9	C13—C12—S1	116.72 (11)
C6—C5—C4	119.45 (15)	C17—C12—S1	121.85 (12)
C6—C5—C10	120.21 (16)	C14—C13—C12	118.42 (13)
C4—C5—C10	120.34 (15)	C14—C13—H13	120.8
C7—C6—C5	116.27 (15)	C12—C13—H13	120.8
C7—C6—H6	121.9	C13—C14—C15	121.98 (15)
C5—C6—H6	121.9	C13—C14—Cl1	118.34 (12)
C6—C7—O1	123.93 (14)	C15—C14—Cl1	119.67 (12)
C6—C7—C2	125.32 (14)	C14—C15—C16	118.42 (14)
O1—C7—C2	110.75 (13)	C14—C15—H15	120.8
C1—C8—O1	111.09 (13)	C16—C15—H15	120.8
C1—C8—C11	133.38 (16)	C17—C16—C15	121.11 (14)
O1—C8—C11	115.53 (14)	C17—C16—H16	119.4
C3—C9—H9A	109.5	C15—C16—H16	119.4
C3—C9—H9B	109.5	C16—C17—C12	118.80 (15)
H9A—C9—H9B	109.5	C16—C17—H17	120.6
C3—C9—H9C	109.5	C12—C17—H17	120.6
O2—S1—C1—C8	−127.62 (13)	C1—C2—C7—C6	−178.73 (15)
C12—S1—C1—C8	121.46 (13)	C3—C2—C7—O1	−176.29 (13)
O2—S1—C1—C2	58.83 (17)	C1—C2—C7—O1	1.51 (16)
C12—S1—C1—C2	−52.10 (16)	C2—C1—C8—O1	1.05 (17)
C8—C1—C2—C7	−1.54 (16)	S1—C1—C8—O1	−174.11 (10)
S1—C1—C2—C7	172.54 (13)	C2—C1—C8—C11	−177.87 (17)
C8—C1—C2—C3	175.63 (17)	S1—C1—C8—C11	7.0 (3)
S1—C1—C2—C3	−10.3 (3)	C7—O1—C8—C1	−0.11 (17)
C7—C2—C3—C4	−2.9 (2)	C7—O1—C8—C11	179.01 (13)
C1—C2—C3—C4	−179.79 (16)	O2—S1—C12—C13	22.00 (13)
C7—C2—C3—C9	176.05 (15)	C1—S1—C12—C13	137.22 (12)
C1—C2—C3—C9	−0.8 (3)	O2—S1—C12—C17	−162.87 (12)
C2—C3—C4—C5	0.4 (2)	C1—S1—C12—C17	−47.65 (13)
C9—C3—C4—C5	−178.61 (16)	C17—C12—C13—C14	0.9 (2)
C3—C4—C5—C6	1.9 (2)	S1—C12—C13—C14	176.04 (11)
C3—C4—C5—C10	−177.54 (15)	C12—C13—C14—C15	0.3 (2)
C4—C5—C6—C7	−1.5 (2)	C12—C13—C14—Cl1	−178.73 (11)
C10—C5—C6—C7	177.93 (14)	C13—C14—C15—C16	−0.8 (2)
C5—C6—C7—O1	178.59 (14)	Cl1—C14—C15—C16	178.26 (12)
C5—C6—C7—C2	−1.1 (2)	C14—C15—C16—C17	0.1 (2)
C8—O1—C7—C6	179.30 (15)	C15—C16—C17—C12	1.1 (2)
C8—O1—C7—C2	−0.93 (16)	C13—C12—C17—C16	−1.6 (2)
C3—C2—C7—C6	3.5 (2)	S1—C12—C17—C16	−176.51 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2i	0.98	2.30	3.249 (2)	163.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2i	0.98	2.30	3.249 (2)	163

Symmetry code: (i) .