3-(3-Chloro-phenyl-sulfin-yl)-2,4,6,7-tetra-methyl-1-benzofuran.

In the title compound, C(18)H(17)ClO(2)S, the 3-chloro-phenyl ring makes a dihedral angle of 72.62 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits a slipped π-π inter-action between the 3-chloro-phenyl rings of adjacent mol-ecules [centroid-centroid distance = 3.751 (2) Å, inter-planar distance = 3.450 (2) Å and slippage = 1.472 (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 ▶, 2011 ▶).

Experimental

Crystal data

C18H17ClO2S

M = 332.83

Triclinic,

a = 7.4198 (1) Å

b = 7.9792 (1) Å

c = 14.5014 (2) Å

α = 105.965 (1)°

β = 95.732 (1)°

γ = 103.965 (1)°

V = 788.21 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 173 K

0.26 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.911

14786 measured reflections

3897 independent reflections

3622 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.099

S = 0.95

3897 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.36 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 datablock(s) global, I. DOI: 10.1107/S1600536812002887/ds2170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002887/ds2170Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002887/ds2170Isup3.cml

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

C18H17ClO2S	Z = 2
Mr = 332.83	F(000) = 348
Triclinic, P1	Dx = 1.402 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4198 (1) Å	Cell parameters from 9057 reflections
b = 7.9792 (1) Å	θ = 2.7–28.3°
c = 14.5014 (2) Å	µ = 0.38 mm−1
α = 105.965 (1)°	T = 173 K
β = 95.732 (1)°	Block, colourless
γ = 103.965 (1)°	0.26 × 0.25 × 0.25 mm
V = 788.21 (2) Å3

Bruker SMART APEXII CCD diffractometer	3897 independent reflections
Radiation source: rotating anode	3622 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.5°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.908, Tmax = 0.911	l = −19→19
14786 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) = 0.099	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0638P)2 + 0.3249P] where P = (Fo2 + 2Fc2)/3
3897 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.36 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
S1	0.53130 (4)	0.65049 (4)	0.33172 (2)	0.02082 (9)
Cl1	−0.00317 (6)	0.23558 (6)	0.46616 (3)	0.04572 (13)
O1	0.79660 (12)	0.52179 (12)	0.11618 (6)	0.02335 (19)
O2	0.36498 (14)	0.72242 (13)	0.32004 (7)	0.0282 (2)
C1	0.59030 (17)	0.55512 (16)	0.21874 (8)	0.0202 (2)
C2	0.48969 (16)	0.40937 (15)	0.13006 (8)	0.0191 (2)
C3	0.30551 (17)	0.29506 (16)	0.09430 (9)	0.0212 (2)
C4	0.27547 (18)	0.17027 (17)	0.00165 (9)	0.0236 (2)
H4	0.1518	0.0915	−0.0247	0.028*
C5	0.41627 (19)	0.15371 (17)	−0.05513 (9)	0.0232 (2)
C6	0.59915 (18)	0.26984 (17)	−0.02096 (9)	0.0220 (2)
C7	0.62560 (17)	0.39462 (16)	0.07062 (8)	0.0204 (2)
C8	0.77070 (17)	0.61729 (17)	0.20508 (9)	0.0227 (2)
C9	0.14666 (18)	0.30115 (19)	0.15074 (9)	0.0270 (3)
H9A	0.0265	0.2612	0.1053	0.040*
H9B	0.1654	0.4257	0.1926	0.040*
H9C	0.1445	0.2205	0.1911	0.040*
C10	0.3716 (2)	0.00812 (19)	−0.15260 (9)	0.0297 (3)
H10A	0.4041	0.0640	−0.2033	0.045*
H10B	0.2366	−0.0561	−0.1674	0.045*
H10C	0.4450	−0.0781	−0.1504	0.045*
C11	0.7563 (2)	0.26059 (19)	−0.07831 (10)	0.0285 (3)
H11A	0.8681	0.3618	−0.0442	0.043*
H11B	0.7166	0.2685	−0.1431	0.043*
H11C	0.7866	0.1454	−0.0850	0.043*
C12	0.93714 (19)	0.7651 (2)	0.26499 (10)	0.0317 (3)
H12A	1.0409	0.7140	0.2781	0.048*
H12B	0.9046	0.8265	0.3268	0.048*
H12C	0.9761	0.8526	0.2298	0.048*
C13	0.44562 (18)	0.44638 (16)	0.36349 (8)	0.0211 (2)
C14	0.55149 (19)	0.32357 (18)	0.35979 (9)	0.0264 (3)
H14	0.6695	0.3438	0.3384	0.032*
C15	0.4822 (2)	0.17083 (18)	0.38788 (10)	0.0305 (3)
H15	0.5528	0.0854	0.3851	0.037*
C16	0.3106 (2)	0.14177 (18)	0.42004 (10)	0.0298 (3)
H16	0.2625	0.0365	0.4385	0.036*
C17	0.21090 (19)	0.26868 (19)	0.42478 (9)	0.0276 (3)
C18	0.27641 (18)	0.42257 (18)	0.39725 (9)	0.0246 (3)
H18	0.2069	0.5092	0.4015	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.02414 (16)	0.01806 (15)	0.01927 (15)	0.00564 (11)	0.00480 (11)	0.00411 (11)
Cl1	0.0391 (2)	0.0496 (2)	0.0587 (3)	0.01101 (18)	0.02486 (18)	0.0286 (2)
O1	0.0202 (4)	0.0255 (4)	0.0230 (4)	0.0046 (3)	0.0058 (3)	0.0062 (3)
O2	0.0326 (5)	0.0247 (5)	0.0331 (5)	0.0151 (4)	0.0106 (4)	0.0104 (4)
C1	0.0211 (5)	0.0205 (5)	0.0193 (5)	0.0056 (4)	0.0043 (4)	0.0063 (4)
C2	0.0224 (6)	0.0177 (5)	0.0187 (5)	0.0062 (4)	0.0044 (4)	0.0074 (4)
C3	0.0224 (6)	0.0204 (5)	0.0217 (5)	0.0056 (4)	0.0054 (4)	0.0080 (4)
C4	0.0243 (6)	0.0204 (6)	0.0228 (6)	0.0022 (5)	0.0025 (4)	0.0055 (5)
C5	0.0306 (6)	0.0207 (6)	0.0190 (5)	0.0080 (5)	0.0049 (4)	0.0064 (4)
C6	0.0274 (6)	0.0222 (6)	0.0205 (5)	0.0093 (5)	0.0077 (4)	0.0096 (4)
C7	0.0207 (5)	0.0205 (5)	0.0214 (5)	0.0057 (4)	0.0040 (4)	0.0087 (4)
C8	0.0232 (6)	0.0231 (6)	0.0220 (5)	0.0069 (5)	0.0046 (4)	0.0068 (5)
C9	0.0215 (6)	0.0293 (6)	0.0255 (6)	0.0021 (5)	0.0064 (5)	0.0046 (5)
C10	0.0387 (7)	0.0249 (6)	0.0219 (6)	0.0073 (5)	0.0064 (5)	0.0027 (5)
C11	0.0311 (7)	0.0330 (7)	0.0247 (6)	0.0115 (5)	0.0118 (5)	0.0097 (5)
C12	0.0217 (6)	0.0333 (7)	0.0315 (7)	0.0010 (5)	0.0034 (5)	0.0027 (6)
C13	0.0265 (6)	0.0195 (5)	0.0163 (5)	0.0066 (4)	0.0034 (4)	0.0039 (4)
C14	0.0307 (6)	0.0254 (6)	0.0246 (6)	0.0113 (5)	0.0069 (5)	0.0066 (5)
C15	0.0421 (8)	0.0235 (6)	0.0288 (6)	0.0147 (6)	0.0068 (6)	0.0075 (5)
C16	0.0403 (7)	0.0216 (6)	0.0247 (6)	0.0040 (5)	0.0042 (5)	0.0075 (5)
C17	0.0294 (6)	0.0285 (6)	0.0228 (6)	0.0036 (5)	0.0064 (5)	0.0078 (5)
C18	0.0282 (6)	0.0258 (6)	0.0207 (6)	0.0088 (5)	0.0057 (5)	0.0070 (5)

S1—O2	1.4949 (9)	C9—H9C	0.9800
S1—C1	1.7531 (12)	C10—H10A	0.9800
S1—C13	1.8001 (13)	C10—H10B	0.9800
Cl1—C17	1.7401 (14)	C10—H10C	0.9800
O1—C8	1.3635 (14)	C11—H11A	0.9800
O1—C7	1.3851 (14)	C11—H11B	0.9800
C1—C8	1.3651 (17)	C11—H11C	0.9800
C1—C2	1.4594 (16)	C12—H12A	0.9800
C2—C7	1.3960 (16)	C12—H12B	0.9800
C2—C3	1.4018 (17)	C12—H12C	0.9800
C3—C4	1.3941 (17)	C13—C18	1.3823 (17)
C3—C9	1.5032 (16)	C13—C14	1.3897 (17)
C4—C5	1.4020 (17)	C14—C15	1.3886 (19)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.3970 (18)	C15—C16	1.388 (2)
C5—C10	1.5081 (17)	C15—H15	0.9500
C6—C7	1.3856 (17)	C16—C17	1.382 (2)
C6—C11	1.5025 (17)	C16—H16	0.9500
C8—C12	1.4797 (18)	C17—C18	1.3870 (19)
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800
O2—S1—C1	111.44 (6)	C5—C10—H10B	109.5
O2—S1—C13	105.69 (6)	H10A—C10—H10B	109.5
C1—S1—C13	99.12 (5)	C5—C10—H10C	109.5
C8—O1—C7	106.80 (9)	H10A—C10—H10C	109.5
C8—C1—C2	107.14 (10)	H10B—C10—H10C	109.5
C8—C1—S1	118.34 (9)	C6—C11—H11A	109.5
C2—C1—S1	134.45 (9)	C6—C11—H11B	109.5
C7—C2—C3	118.68 (11)	H11A—C11—H11B	109.5
C7—C2—C1	104.27 (10)	C6—C11—H11C	109.5
C3—C2—C1	137.04 (11)	H11A—C11—H11C	109.5
C4—C3—C2	116.04 (11)	H11B—C11—H11C	109.5
C4—C3—C9	120.50 (11)	C8—C12—H12A	109.5
C2—C3—C9	123.45 (11)	C8—C12—H12B	109.5
C3—C4—C5	124.13 (12)	H12A—C12—H12B	109.5
C3—C4—H4	117.9	C8—C12—H12C	109.5
C5—C4—H4	117.9	H12A—C12—H12C	109.5
C6—C5—C4	120.18 (11)	H12B—C12—H12C	109.5
C6—C5—C10	119.76 (11)	C18—C13—C14	121.49 (12)
C4—C5—C10	120.05 (12)	C18—C13—S1	117.34 (9)
C7—C6—C5	114.84 (11)	C14—C13—S1	121.06 (10)
C7—C6—C11	122.20 (12)	C15—C14—C13	118.97 (12)
C5—C6—C11	122.96 (11)	C15—C14—H14	120.5
O1—C7—C6	123.21 (11)	C13—C14—H14	120.5
O1—C7—C2	110.72 (10)	C16—C15—C14	120.63 (12)
C6—C7—C2	126.06 (11)	C16—C15—H15	119.7
O1—C8—C1	111.04 (11)	C14—C15—H15	119.7
O1—C8—C12	115.43 (11)	C17—C16—C15	118.86 (13)
C1—C8—C12	133.53 (12)	C17—C16—H16	120.6
C3—C9—H9A	109.5	C15—C16—H16	120.6
C3—C9—H9B	109.5	C16—C17—C18	121.86 (13)
H9A—C9—H9B	109.5	C16—C17—Cl1	119.46 (11)
C3—C9—H9C	109.5	C18—C17—Cl1	118.68 (11)
H9A—C9—H9C	109.5	C13—C18—C17	118.15 (12)
H9B—C9—H9C	109.5	C13—C18—H18	120.9
C5—C10—H10A	109.5	C17—C18—H18	120.9
O2—S1—C1—C8	125.23 (10)	C11—C6—C7—C2	−178.00 (11)
C13—S1—C1—C8	−123.83 (10)	C3—C2—C7—O1	177.83 (10)
O2—S1—C1—C2	−58.15 (13)	C1—C2—C7—O1	−1.15 (12)
C13—S1—C1—C2	52.78 (13)	C3—C2—C7—C6	−3.17 (18)
C8—C1—C2—C7	1.49 (13)	C1—C2—C7—C6	177.85 (11)
S1—C1—C2—C7	−175.39 (10)	C7—O1—C8—C1	0.63 (13)
C8—C1—C2—C3	−177.20 (13)	C7—O1—C8—C12	−178.36 (11)
S1—C1—C2—C3	5.9 (2)	C2—C1—C8—O1	−1.34 (14)
C7—C2—C3—C4	1.96 (16)	S1—C1—C8—O1	176.13 (8)
C1—C2—C3—C4	−179.49 (13)	C2—C1—C8—C12	177.39 (14)
C7—C2—C3—C9	−178.71 (11)	S1—C1—C8—C12	−5.1 (2)
C1—C2—C3—C9	−0.2 (2)	O2—S1—C13—C18	−17.61 (11)
C2—C3—C4—C5	0.39 (18)	C1—S1—C13—C18	−133.06 (10)
C9—C3—C4—C5	−178.96 (12)	O2—S1—C13—C14	166.23 (10)
C3—C4—C5—C6	−1.86 (19)	C1—S1—C13—C14	50.79 (11)
C3—C4—C5—C10	177.04 (12)	C18—C13—C14—C15	2.02 (19)
C4—C5—C6—C7	0.82 (17)	S1—C13—C14—C15	178.01 (10)
C10—C5—C6—C7	−178.09 (11)	C13—C14—C15—C16	−0.6 (2)
C4—C5—C6—C11	−179.50 (11)	C14—C15—C16—C17	−0.8 (2)
C10—C5—C6—C11	1.59 (18)	C15—C16—C17—C18	0.8 (2)
C8—O1—C7—C6	−178.65 (11)	C15—C16—C17—Cl1	−179.31 (10)
C8—O1—C7—C2	0.39 (13)	C14—C13—C18—C17	−2.01 (18)
C5—C6—C7—O1	−179.43 (10)	S1—C13—C18—C17	−178.15 (9)
C11—C6—C7—O1	0.88 (18)	C16—C17—C18—C13	0.59 (19)
C5—C6—C7—C2	1.68 (18)	Cl1—C17—C18—C13	−179.31 (9)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2i	0.98	2.60	3.5786 (16)	175
C12—H12A···O2ii	0.98	2.40	3.3159 (17)	155
C10—H10C···Cg1iii	0.98	2.79	3.615 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2i	0.98	2.60	3.5786 (16)	175
C12—H12A⋯O2ii	0.98	2.40	3.3159 (17)	155
C10—H10C⋯Cg1iii	0.98	2.79	3.615 (16)	142

Symmetry codes: (i) ; (ii) ; (iii) .