3-(3-Chloro-phenyl-sulfin-yl)-2,5,7-trimethyl-1-benzofuran.

In the title compound, C(17)H(15)ClO(2)S, the 3-chloro-phenyl ring makes a dihedral angle of 84.48 (4)° with the mean plane [r.m.s. deviation = 0.004 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O, C-H⋯π and C-S⋯π [3.414 (2) Å] inter-actions. The crystal structure also exhibits weak π-π inter-actions between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.826 (2), inter-planar distance = 3.447 (2) and slippage = 1.660 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶, 2012 ▶).

Experimental

Crystal data

C17H15ClO2S

M = 318.80

Triclinic,

a = 6.1701 (1) Å

b = 11.6670 (2) Å

c = 12.1123 (3) Å

α = 112.965 (1)°

β = 99.114 (1)°

γ = 103.698 (1)°

V = 748.70 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 173 K

0.20 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.926, T max = 0.934

13458 measured reflections

3463 independent reflections

3136 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.07

3463 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 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/S1600536812008537/lr2053sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008537/lr2053Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008537/lr2053Isup3.cml

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

C17H15ClO2S	Z = 2
Mr = 318.80	F(000) = 332
Triclinic, P1	Dx = 1.414 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1701 (1) Å	Cell parameters from 7460 reflections
b = 11.6670 (2) Å	θ = 3.3–27.6°
c = 12.1123 (3) Å	µ = 0.40 mm−1
α = 112.965 (1)°	T = 173 K
β = 99.114 (1)°	Block, colourless
γ = 103.698 (1)°	0.20 × 0.19 × 0.18 mm
V = 748.70 (3) Å3

Bruker SMART APEXII CCD diffractometer	3463 independent reflections
Radiation source: rotating anode	3136 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.023
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.9°
φ and ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
Tmin = 0.926, Tmax = 0.934	l = −14→15
13458 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.096	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.2623P] where P = (Fo2 + 2Fc2)/3
3463 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.30 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	0.71046 (7)	0.15422 (4)	1.01673 (4)	0.03980 (13)
S1	0.62148 (6)	0.50385 (3)	0.83504 (3)	0.02455 (11)
O1	0.24560 (17)	0.38716 (10)	0.49273 (9)	0.0276 (2)
O2	0.87230 (17)	0.51728 (11)	0.85352 (10)	0.0334 (2)
C1	0.4848 (2)	0.42875 (13)	0.67382 (12)	0.0240 (3)
C2	0.5205 (2)	0.32070 (13)	0.57651 (12)	0.0236 (3)
C3	0.6609 (2)	0.24231 (14)	0.57050 (14)	0.0286 (3)
H3	0.7670	0.2559	0.6440	0.034*
C4	0.6425 (3)	0.14386 (15)	0.45483 (15)	0.0328 (3)
C5	0.4846 (3)	0.12593 (15)	0.34719 (14)	0.0338 (3)
H5	0.4745	0.0580	0.2689	0.041*
C6	0.3429 (3)	0.20295 (15)	0.34993 (13)	0.0303 (3)
C7	0.3683 (2)	0.29925 (14)	0.46700 (13)	0.0248 (3)
C8	0.3205 (2)	0.46457 (14)	0.61921 (13)	0.0253 (3)
C9	0.7918 (3)	0.05666 (19)	0.44441 (19)	0.0455 (4)
H9A	0.9141	0.0814	0.4073	0.068*
H9B	0.6954	−0.0356	0.3914	0.068*
H9C	0.8628	0.0675	0.5277	0.068*
C10	0.1747 (3)	0.18530 (18)	0.23546 (15)	0.0428 (4)
H10A	0.0170	0.1662	0.2447	0.064*
H10B	0.1809	0.1119	0.1618	0.064*
H10C	0.2166	0.2663	0.2252	0.064*
C11	0.2052 (3)	0.56436 (16)	0.66873 (15)	0.0338 (3)
H11A	0.0457	0.5201	0.6645	0.051*
H11B	0.2023	0.6129	0.6186	0.051*
H11C	0.2914	0.6259	0.7557	0.051*
C12	0.4908 (2)	0.36608 (13)	0.86309 (12)	0.0234 (3)
C13	0.6366 (2)	0.31970 (13)	0.92070 (12)	0.0245 (3)
H13	0.8008	0.3577	0.9432	0.029*
C14	0.5339 (3)	0.21551 (14)	0.94437 (13)	0.0275 (3)
C15	0.2958 (3)	0.16024 (15)	0.91376 (14)	0.0335 (3)
H15	0.2296	0.0886	0.9305	0.040*
C16	0.1544 (3)	0.21071 (16)	0.85821 (15)	0.0361 (3)
H16	−0.0097	0.1734	0.8368	0.043*
C17	0.2507 (3)	0.31488 (15)	0.83378 (14)	0.0311 (3)
H17	0.1541	0.3508	0.7975	0.037*

	U11	U22	U33	U12	U13	U23
Cl1	0.0494 (2)	0.0350 (2)	0.0403 (2)	0.01686 (18)	0.00730 (17)	0.02221 (18)
S1	0.02701 (19)	0.02439 (18)	0.01981 (17)	0.00680 (13)	0.00449 (12)	0.00919 (13)
O1	0.0276 (5)	0.0334 (5)	0.0249 (5)	0.0140 (4)	0.0052 (4)	0.0146 (4)
O2	0.0237 (5)	0.0406 (6)	0.0315 (5)	0.0026 (4)	0.0024 (4)	0.0184 (5)
C1	0.0247 (6)	0.0269 (6)	0.0217 (6)	0.0098 (5)	0.0062 (5)	0.0114 (5)
C2	0.0233 (6)	0.0262 (7)	0.0222 (6)	0.0081 (5)	0.0066 (5)	0.0116 (5)
C3	0.0268 (7)	0.0320 (7)	0.0301 (7)	0.0133 (6)	0.0072 (5)	0.0152 (6)
C4	0.0341 (8)	0.0313 (7)	0.0379 (8)	0.0150 (6)	0.0150 (6)	0.0158 (6)
C5	0.0425 (9)	0.0281 (7)	0.0271 (7)	0.0111 (6)	0.0129 (6)	0.0076 (6)
C6	0.0328 (7)	0.0315 (7)	0.0232 (7)	0.0068 (6)	0.0056 (6)	0.0118 (6)
C7	0.0249 (6)	0.0271 (6)	0.0246 (6)	0.0097 (5)	0.0067 (5)	0.0131 (5)
C8	0.0267 (6)	0.0284 (7)	0.0247 (6)	0.0111 (5)	0.0089 (5)	0.0139 (5)
C9	0.0517 (10)	0.0430 (9)	0.0514 (10)	0.0295 (8)	0.0222 (8)	0.0195 (8)
C10	0.0516 (10)	0.0425 (9)	0.0239 (7)	0.0109 (8)	−0.0015 (7)	0.0117 (7)
C11	0.0350 (8)	0.0372 (8)	0.0380 (8)	0.0207 (7)	0.0144 (6)	0.0186 (7)
C12	0.0257 (6)	0.0246 (6)	0.0180 (6)	0.0077 (5)	0.0064 (5)	0.0080 (5)
C13	0.0244 (6)	0.0257 (6)	0.0210 (6)	0.0082 (5)	0.0056 (5)	0.0084 (5)
C14	0.0355 (7)	0.0254 (6)	0.0211 (6)	0.0117 (6)	0.0073 (5)	0.0092 (5)
C15	0.0382 (8)	0.0283 (7)	0.0310 (7)	0.0046 (6)	0.0127 (6)	0.0129 (6)
C16	0.0251 (7)	0.0394 (8)	0.0380 (8)	0.0037 (6)	0.0094 (6)	0.0154 (7)
C17	0.0249 (7)	0.0383 (8)	0.0292 (7)	0.0096 (6)	0.0056 (5)	0.0154 (6)

Cl1—C14	1.7385 (15)	C9—H9A	0.9800
S1—O2	1.4892 (11)	C9—H9B	0.9800
S1—C1	1.7564 (14)	C9—H9C	0.9800
S1—C12	1.8023 (14)	C10—H10A	0.9800
O1—C8	1.3692 (17)	C10—H10B	0.9800
O1—C7	1.3839 (17)	C10—H10C	0.9800
C1—C8	1.3577 (19)	C11—H11A	0.9800
C1—C2	1.4427 (18)	C11—H11B	0.9800
C2—C3	1.3910 (19)	C11—H11C	0.9800
C2—C7	1.3924 (18)	C12—C13	1.3840 (19)
C3—C4	1.388 (2)	C12—C17	1.3880 (19)
C3—H3	0.9500	C13—C14	1.388 (2)
C4—C5	1.407 (2)	C13—H13	0.9500
C4—C9	1.510 (2)	C14—C15	1.379 (2)
C5—C6	1.390 (2)	C15—C16	1.388 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.383 (2)
C6—C10	1.504 (2)	C16—H16	0.9500
C8—C11	1.485 (2)	C17—H17	0.9500
O2—S1—C1	108.33 (6)	H9A—C9—H9C	109.5
O2—S1—C12	105.99 (6)	H9B—C9—H9C	109.5
C1—S1—C12	96.82 (6)	C6—C10—H10A	109.5
C8—O1—C7	106.60 (10)	C6—C10—H10B	109.5
C8—C1—C2	107.66 (12)	H10A—C10—H10B	109.5
C8—C1—S1	124.30 (11)	C6—C10—H10C	109.5
C2—C1—S1	128.05 (10)	H10A—C10—H10C	109.5
C3—C2—C7	119.35 (13)	H10B—C10—H10C	109.5
C3—C2—C1	136.00 (13)	C8—C11—H11A	109.5
C7—C2—C1	104.65 (12)	C8—C11—H11B	109.5
C4—C3—C2	118.57 (13)	H11A—C11—H11B	109.5
C4—C3—H3	120.7	C8—C11—H11C	109.5
C2—C3—H3	120.7	H11A—C11—H11C	109.5
C3—C4—C5	119.72 (14)	H11B—C11—H11C	109.5
C3—C4—C9	120.17 (15)	C13—C12—C17	121.99 (13)
C5—C4—C9	120.11 (15)	C13—C12—S1	118.00 (10)
C6—C5—C4	123.12 (14)	C17—C12—S1	119.90 (11)
C6—C5—H5	118.4	C12—C13—C14	117.46 (13)
C4—C5—H5	118.4	C12—C13—H13	121.3
C7—C6—C5	114.77 (13)	C14—C13—H13	121.3
C7—C6—C10	121.63 (15)	C15—C14—C13	122.02 (14)
C5—C6—C10	123.60 (15)	C15—C14—Cl1	118.97 (12)
C6—C7—O1	125.10 (13)	C13—C14—Cl1	119.01 (11)
C6—C7—C2	124.46 (13)	C14—C15—C16	119.08 (14)
O1—C7—C2	110.43 (12)	C14—C15—H15	120.5
C1—C8—O1	110.66 (12)	C16—C15—H15	120.5
C1—C8—C11	133.42 (13)	C17—C16—C15	120.50 (14)
O1—C8—C11	115.88 (12)	C17—C16—H16	119.8
C4—C9—H9A	109.5	C15—C16—H16	119.8
C4—C9—H9B	109.5	C16—C17—C12	118.90 (14)
H9A—C9—H9B	109.5	C16—C17—H17	120.6
C4—C9—H9C	109.5	C12—C17—H17	120.6
O2—S1—C1—C8	−139.54 (12)	C1—C2—C7—C6	−179.32 (13)
C12—S1—C1—C8	111.08 (13)	C3—C2—C7—O1	−179.80 (12)
O2—S1—C1—C2	40.95 (14)	C1—C2—C7—O1	0.13 (15)
C12—S1—C1—C2	−68.43 (13)	C2—C1—C8—O1	0.15 (16)
C8—C1—C2—C3	179.75 (16)	S1—C1—C8—O1	−179.45 (10)
S1—C1—C2—C3	−0.7 (2)	C2—C1—C8—C11	177.69 (15)
C8—C1—C2—C7	−0.17 (15)	S1—C1—C8—C11	−1.9 (2)
S1—C1—C2—C7	179.41 (11)	C7—O1—C8—C1	−0.07 (15)
C7—C2—C3—C4	−0.6 (2)	C7—O1—C8—C11	−178.08 (12)
C1—C2—C3—C4	179.46 (15)	O2—S1—C12—C13	14.09 (12)
C2—C3—C4—C5	0.2 (2)	C1—S1—C12—C13	125.42 (11)
C2—C3—C4—C9	−179.98 (15)	O2—S1—C12—C17	−169.67 (11)
C3—C4—C5—C6	0.1 (2)	C1—S1—C12—C17	−58.34 (12)
C9—C4—C5—C6	−179.69 (15)	C17—C12—C13—C14	2.4 (2)
C4—C5—C6—C7	0.0 (2)	S1—C12—C13—C14	178.57 (10)
C4—C5—C6—C10	179.59 (16)	C12—C13—C14—C15	−0.8 (2)
C5—C6—C7—O1	−179.78 (13)	C12—C13—C14—Cl1	−179.94 (10)
C10—C6—C7—O1	0.6 (2)	C13—C14—C15—C16	−0.4 (2)
C5—C6—C7—C2	−0.4 (2)	Cl1—C14—C15—C16	178.74 (12)
C10—C6—C7—C2	179.97 (14)	C14—C15—C16—C17	0.0 (2)
C8—O1—C7—C6	179.40 (13)	C15—C16—C17—C12	1.5 (2)
C8—O1—C7—C2	−0.04 (15)	C13—C12—C17—C16	−2.7 (2)
C3—C2—C7—C6	0.8 (2)	S1—C12—C17—C16	−178.83 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.55	3.2960 (16)	136
C11—H11B···Cg1ii	0.98	2.88	3.703	143

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
C13—H13⋯O2i	0.95	2.55	3.2960 (16)	136
C11—H11B⋯Cg1ii	0.98	2.88	3.703	143

Symmetry codes: (i) ; (ii) .